Marine natural products (2014) - C5NP00156K Supplementary ...

Electronic Supplementary Material (ESI) for Natural Product Reports. This journal is © The Royal Society of Chemistry 2016

Marine natural products (2014) - C5NP00156K Supplementary Information John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro and Michèle R. Prinsep 1

Introduction

2

1.1

3

Abbreviations

2

Additional reviews

3

Marine microorganisms and phytoplankton

3

3.1

Marine-sourced bacteria (excluding from mangroves)

5

3.2

Bacteria from mangroves

18

3.3

Marine-sourced fungi (excluding from mangroves)

20

3.4

Fungi from mangroves

40

3.5

Cyanobacteria

47

3.6

Dinoflagellates

49

4

Green algae

52

5

Brown algae

53

6

Red algae

54

7

Sponges

57

8

Cnidarians

77

9

Bryozoans

91

10

Molluscs

92

11

Tunicates (ascidians)

94

12

Echinoderms

96

13

Mangroves and the intertidal zone

100

14

Miscellaneous

104

15

Bibliography

105 1

1

Introduction

reference #, followed by Taxonomy, Location and Article title. Each section is

These annual reviews of marine natural product chemistry, initiated by the late

separated by a // symbol. The following indented line(s) provide information about

Professor D. John Faulkner in 1984 and continued by the New Zealand group since

each compound referred to in the Review for that publication. This information is

2003, have previously included the structures for all new MNPs for the review

provided in the following order, again separated by // (* is inserted where there are

year along with any revised structures. The number of new MNPs reported in 1984

no data): Compound number (italicised for those compounds highlighted in the

was 332, but by 2014 the number has risen to 1378. With the ever-increasing size

Review document), Compound name, Status (N for a new compound; M for new

creating difficulties for preparation of the annual review, the NPR Editorial Board

to marine; R for a revision (structure, stereochemistry, stereochemical assignment

suggested changing the format to focus on a selection of highlighted structures. To

etc)), Biological activity, Other information, and Secondary references (giving

maintain the usual comprehensive coverage of all new and revised MNPs, we have

a link to the original report for compounds with M or R status). To assist your

prepared this Supplementary Information (SI) document, showing all structures,

viewing these headings are noted in the footer at the bottom of each page. To

along with their names, taxonomic origins, locations for collections, biological

conserve space the Title and Location data may have been abbreviated, and are

activities and other useful information. Each page of the SI document contains at

not as complete as in the source, MarinLit. Most Main article bibliography

least one array of numbered structures. The numbers are those assigned in the

reference and Secondary SI reference numbers are hyperlinked to the relevant

Review document. For structures that have their absolute configurations fully

DOI or URL. Where those are not available (numbers not underlined), the full

described, the compound number in the diagrams is preceded with †. Below each

reference is given in a brief Bibliography at the end of this SI document.

structural array the relevant information for each reference and associated

Compound numbers are hyperlinked to a Chemspider entry where available.

compounds is listed. The first line contains the Main article bibliography

2

1.1 Abbreviations In the Biological activity section the following abbreviations have been used: A. hydrophilia

Aeromonas hydrophilia

M. luteus

Micrococcus luteus

A. salina.

Artemia salina

MOA

mechanism of action

AF

antifungal

mod.

moderate

AM/AB

antimicrobial/antibacterial

MRSA

Methicillin Resistant Staphlococcus aureus

B. amphitrite

Balanus amphitrite

M. smegmatis

Mycobacterium smegmatis

C. albicans

Candida albicans

P. falciparum

Plasmodium falciparum

cytotox.

cytotoxicity/cytotoxic

P. capsici

Phytophthora capsici

DPPH

2,2-diphenyl-1-picrylhydrazyl.

S. aureus

Staphlococcus aureus

E. coli

Escherichia coli

S. epidermidis.

Staphlococcus epidermidis

HTCL

Human Tumour Cell Line

stereochem.

stereochemistry

inhib.

inhibitor/inhibition

T. mentagrophytes

Trichophyton mentagrophytes

M. tuberculosis

Mycobacterium tuberculosis

TRP

Transient Receptor Potential

MDR

multidrug resistant

V. harveyi

Vibrio harveyi

2

Additional reviews

This listing is of reviews not included in the Review highlights section of the MNP

fish,s8 antimicrobial compounds from marine Pseudovibrio sp.,s9 antimicrobial

review. Their placement here does not necessarily imply a lesser importance of the

compounds from mangrove plants,s10 antiprotozoal compounds from

work described, but more likely that they may be of interest to only a smaller

macroalgae,s11 cytotoxic and cytolytic cnidarian venoms,s12 potential matrix

group of readers or have a more limited scope of coverage. General topics covered

metalloproteinase inhibitors from edible macroalgae,s13 antioxidant carotenoids

are recent advances in deep-sea natural products,s1 some MNPs with health

from marine bacteria,s14 MNPs with potential as hepatoprotective agents,s15 MNPs

benefitss2 or potential application in sports,s3 and the exploration of marine

with P-glycoprotein inhibitor properties,s16 MNPs targeting nuclear receptors,s17

resources for bioactive compounds.s4 MNPs with specific types of bioactivity are

recently described low molecular weight MNPs with anticancer potential,s18

reviewed in papers on selected antifungal and antiviral MNPs,s5 quorum quenching

neuroactive MNPs,s19 MNPs with neuroprotective effects from macroalgae,s20

agents as resources for antivirulence therapy,s6 potential mosquitocidal compounds

recent progress with microtubule stabilizers, some of which are MNPs,s21

from macroalgae,s7 antilipopolysaccharide activities of antimicrobial peptides from

microtubule-targeting MNPs,s22 an overview of potential anti-HPV and related 3

cancer agents from marine sources,s23 bioactive marine drugs and marine

and hydroquinone metabolites from the ascidian Aplidium spp.,s54 bioactive toxins

biomaterials for brain diseases,s24 quorum sensing MNPs for development of

from stinging jellyfish,s55 okadaic acid, yessotoxins, pectenotoxins, saxitoxins,

antibacterials,s25 MNP modulators of TRAIL induced apoptosis in cancer cells,s26

domoic acid, spirolides, palytoxins and azaspiracids from Italy,s56 bengamides and

and the effects of Trabectedin and plitidepsin on the tumour microenviroment.s27

bengazoles from Jaspis sponges,s57 zampanolide and dactylolide,s58 manzamine

Organism-focussed reviews include papers on Dinophysis toxins,s28 non-

alkaloids,s59 bryostatins in preclinical and clinical studies,s60 briarane diterpenoids

halogenated compounds from Laurencia algae,s29 bioactive MNPs from

from gorgonians between 2011 and 2013,s61 and cephalopod ink.s62 Chemical

actinobacteria,s30,s31 antitumour natural products from cnidarians,s32 chemical and

defensive symbioses in the marine environment has been reviewed.s63 A number of

biological aspects of octocorals from the Brazilian coast,s33 bioactives from

papers which, while not all are reviews, are useful to reference here as they

sponges between 2001 and 2010, 2013,

s35

s34

bioactive MNPs from echinoderms from 2009–

compounds from marine mussels and their effects on human health,

s36

describe advances in techniques or approaches to discovery that are relevant to MNP studies. These include papers on 'Marketed marine natural products in the

MNPs from mangrove actinomycetes,s37 bioactive extracts and compounds from

pharmaceutical and cosmeceutical industries: tips for success',s64 'Marine

Brazilian marine macroalgae,s38 macroalgae-derived bioactive peptides,s39

microorganism-invertebrate assemblages: perspectives to solve the “supply

antioxidant compounds from red algae,

s40

problem” in the initial steps of drug discovery',s65 'Chemoinformatic analysis as a

toxic MNPs from cyanobacteria of

potential importance to the agriculture sector,s41 microorganisms as sources of

tool for prioritization of trypanocidal marine derived lead compounds',s66 'Co-

nutraceuticals and functional foods,s42 and MNPs from microorganisms.s43

cultivation—a powerful emerging tool for enhancing the chemical diversity of

Reviews of classes of compounds or specifically named MNPs include papers on

microorganisms',s67 'A chemoinformatics approach to the discovery of lead-like

microorganism-derived macrolactins with antimicrobial or antitumour

molecules from marine and microbial sources en route to antitumor and antibiotic

properties,s44 the potential for metabolic engineering of carotenoids,s45 2,5-

drugs',s68 'Circular dichroism calculation for natural products',s69 the construction

diketopiperazines between 2009 and 2014,s46 antitumour alkaloids from marine

and use of natural product libraries,s70 and 'Bioprospecting from marine sediments

invertebrates,s47 halogenated alkaloids of Agelas sponges,s48 bioactive alkaloids

of New Brunswick, Canada: exploring the relationship between total bacterial

from ascidians,

s49

indole alkaloids as anti-infectives,

s50

antimicrobial peptides,

s51

diversity and actinobacteria diversity'.s71

cyclopeptides with potential biomedicine applications,s52 terpenoids,s53 quinone

4

3

Marine microorganisms and phytoplankton: OH

O

3.1 Marine-sourced bacteria (excluding from mangroves)

R

HO

O

O MeO

OH

N H

NMe 2 OH

N

OMe

O N

O

HO

N

N

H 3O6P 2O CN

HO

OMe

O O

†1 †2

R=H R = Me

OH

OH

O

O OH

HO O

†3

O

OH OH

O

O

O

HO OH †4

O

O

H N

HOOC

O

OH 5

OH

HOOC

O

O

N H

O 7

21 22

24

25

26

27

Key:

O

OH HOOC

N H

7

6

COOH

OH

COOH O

H N

OH

N H

O

COOMe

H N

O

H N

N H

O

OH HO

O

8

H N

O H N

N H O

N H O

COOH

OH

O n

HOOC

N H

8n=4 9n=5

COOH O

H N O

N H

O

H N O

N H

O

H N O

N H

OH

n

R1

10 n = 7, R1 = R 2 = H 11 n = 5, R1 = Me, R 2 = Et

Proteobacteria Entotheonella sp. // (Porifera, Discodermia calyx) Shikine-jima Is., Japan // Calyculin biogenesis from a pyrophosphate protoxin produced by a sponge symbiont 1 // phosphocalyculin A // N // * // Biosynthetic study. // * Proteobacteria Entotheonella sp. // (Porifera, Discodermia calyx) Shikine-jima Is., Japan // Phosphocalyculin C as a pyrophosphate protoxin of calyculin C in the marine sponge Discodermia calyx 2 // phosphocalyculin C // N // very potent (low nM) vs HTCL, 5000x less toxic than calyculin C // Likely protoxin form of calyculin C // * Actinobacteria Actinoalloteichus cyanogriseus // (sediment) Weihai, China // Cyanogramide with a new spiro[indolinone-pyrroloimidazole] skeleton from Actinoalloteichus cyanogriseus 3 // cyanogramide // N // MDR-reversing // * // s72 Actinobacteria Actinokineospora sp. // (Porifera, Spheciospongia vagabunda) Ras Mohamed, Egypt // Dereplication strategies for targeted isolation of new antitrypanosomal actinosporins A and B from a marine sponge associated-Actinokineospora sp. EG49 4 // actinosporin A // N // mod. antitrypanosomal activity // * // * 5 // actinosporin B // N // * // * // * Firmicutes Bacillus subtilis // (sediment) Gageocho reef, South Korea // Non-cytotoxic AF agents: isolation and structures of gageopeptides A–D from a Bacillus strain 109GGC020 6 // gageopeptide A // N // inhib. and lytic activity against P. capsici (0.02 uM). broad spectrum AB // * // * 7 // gageopeptide B // N // lytic activity against P. capsici (not as potent as 1), broad spectrum AB // * // * 8 // gageopeptide C // N // broad spectrum AB // * // * 9 // gageopeptide D // N // broad spectrum AB // * // * Firmicutes Bacillus subtilis // (sediment) Gageocho reef, South Korea // Gageostatins A–C, antimicrobial linear lipopeptides from a marine Bacillus subtilis 10 // gageostatin A // N // good AF, mod. AB activity, mod. cytotox. to HTCLs // * // * 11 // gageostatin B // N // good AF, mod. AB activity, mod. cytotox. to HTCLs // * // * 12 // gageostatin C // N // good AF, mod. AB activity, mod. cytotox. to HTCLs // * // * Main article bibliography reference // Taxonomy // Location // Article title Compound number // Compound name // Status // Biological activity // Other information // Secondary references

5

R2

3

Marine microorganisms and phytoplankton:

3.1 Marine-sourced bacteria (excluding from mangroves) COOR 3

COOH COOH O

O HOOC

H N

N H

COOH

O H N

N H O

O

O H N

N H O

O

N H

H N

HOOC

3

O

N H

O

12

OH

HOOC

H N

O H N

N H O

7

OH

N H

n

O

R1

R2

14 n = 7, R1 = R 2 = H, R 3 = Me 15 n = 4, R1 = Me, R 2 = Et, R 3 = H

13 NH 2 O

Cl NH CONH 2 O

NH

N H

O

H N

O

N H

O

N H

NH

O

29 30

32 34

Key:

O

O N H O

28

N H

NH 2

O

O HN

COOH

COOH O

O

COOH

Cl

HO

HOOC HOOC

O

†16

O

H N

17

7

18

O

NH O O COOH

N H

O

OMe

O O 2N

OMe

OH N H

†19

OH

O

HO

O

O

O

OH O

H N

HO

N

N

7

N H

N

O

O O N

O N

N H

HO

O

O

OH

NH

OMe OH 20

Firmicutes Bacillus subtilis // (sediment) Gageocho reef, South Korea // Gageotetrins A–C, noncytotoxic antimicrobial linear lipopeptides from a marine bacterium Bacillus subtilis 13 // gageotetrin A // N // inhib. of P. capsici (0.02 uM), good AB activity // * // * 14 // gageotetrin B // N // inhib. of P. capsici (0.02 uM), good AB activity // * // * 15 // gageotetrin C // N // inhib. of P. capsici (0.02 uM), good AB activity // * // * Actinobacteria Saccharomonospora sp. // (sediment) La Jolla, U.S.A. // Direct cloning and refactoring of a silent lipopeptide biosynthetic gene cluster yields the antibiotic taromycin A 16 // taromycin A // N // mod. AB activity (Ca conc. dependent) // * // * Actinobacteria Solwaraspora sp. // (Chordata, Trididemnum orbiculatum) Florida Keys, USA // Solwaric acids A and B, AB aromatic acids from a marine Solwaraspora sp. 17 // solwaric acid A // N // weak-mod. MRSA and MSSA activity // * // * 18 // solwaric acid B // N // weak-mod. MRSA and MSSA activity // * // * Actinobacteria Streptomyces sp. // (sand) Heron Is., Australia // Heronapyrrole D: a case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery 19 // heronapyrrole D // N // broad spectrum AB (Gram-positive) // Also synthesised. // * Actinobacteria Streptomyces sp. // (sediment) South Molle Is., Australia // Antimalarial and AB glycohexadepsipeptide-polyketide from an Australian marine-derived Streptomyces sp. (CMB-M0244) 20 // mollemycin A // N // potent (10-50 nM) and selective growth inhib. of certain Gram-(+) and Gram-(-) strains, potent (7-9 nM) inhib. of drug-sensitive and MDR P. falciparum // * // *

Main article bibliography reference // Taxonomy // Location // Article title Compound number // Compound name // Status // Biological activity // Other information // Secondary references

6

3



R1 N

R2

N

MeOOC

Cl

HO R

O H

N

Cl

Cl

Cl

Cl †21

R1 †22 R 1 †23 R 1 †24 R 1

N H = Me, R 2 = H = R 2 = Me = H, R 2 = Me = R2 = H

Cl

MeO

H

N N

N H

†25

HO 28

OH

NH OH

37

36 39

41

Key:

†30

H

†29

OH

R

HO H

OH

OH

H

O H

N H

N H 26 R = H 27 R = COOMe

N

OH

O N

H H

O

NH

HO OH

†31

O

O

O 32 R = Me 33 R = H

5

O

O 34

4

O

O

†35

4

Actinobacteria Streptomyces sp. // (sediment) Bay of Bengal, Indian Ocean // Indimicins A–E, bisindole alkaloids from the deep-sea-derived Streptomyces sp. SCSIO 03032 21 // indimicin A // N // * // * // * 22 // indimicin B // N // mod. cytotox. HTCL (MCF-7) // * // * 23 // indimicin C // N // * // * // * 24 // indimicin D // N // * // * // * 25 // indimicin E // N // * // * // * 26 // lynamicin F // N // * // * // * 27 // lynamicin G // N // * // * // * Actinobacteria Streptomyces sp. // (sediment) Bay of Bengal, Indian Ocean // Elucidating hydroxylation and methylation steps tailoring piericidin A1 biosynthesis 28 // piericidin E1 // N // * // * // s73 Actinobacteria Streptomyces sp. // (sediment) Bay of Bengal, Indian Ocean // Heronamides D–F, polyketide macrolactams from the deep-sea-derived Streptomyces sp. SCSIO 03032 29 // heronamide D // N // * // * // * 30 // heronamide E // N // * // * // * 31 // heronamide F // N // * // * // * Actinobacteria Streptomyces sp. // (Echinodermata, Acanthaster planci) Chuuk, Federated States of Micronesia // Violapyrones H and I, new cytotoxic compounds isolated from Streptomyces sp. associated with the marine starfish Acanthaster planci 32 // violapyrone H // N // mod. cytotox. HTCLs // * // * 33 // violapyrone I // N // mod. cytotox. HTCLs // * // * 34 // violapyrone B // M // mod. cytotox. HTCLs // * // s74 35 // violapyrone C // M // mod. cytotox. HTCLs // Synthesis and absolute configuration determined in ref. 42. // s74 s75


7

3


3.1 Marine-sourced bacteria (excluding from mangroves) OH O H

H N

H N

OH N MeO

H N

O N

H N

H

H N

O

H

N

MeO 36

H O H N

O

HO S O

O

H N

HO R

O

44

R=H †46 R = OH

O

HN

48

51

53 57

Key:

O

N N N † OH 47 R1 = R 2 = H, R 3 = OH OH †48 R = R = Me, R = H 1 2 3

O

N H HN

53

OH

H H HO

†55

H

OH

Me 2N

44

O O

O

N

O R

S

H

O

O HO

O N

H N

HO

N OMe

N

N

†45

O

O

41 R = H 42 R = Cl

HO

S

O

R 2O R3

40 R = Cl 43 R = H

O

H

HO

HO HO

39

R1 O

HO

O O

MeO

†38

O

O

R

N H N

MeO

37

OH R

O O

O O

O

O

O 49 R = Cl 50 R = Br

HO NMe 2

OH OH

O †51 †52

R

O

O

R = OH R=H

NH

HN

OH

O

HO HO

OH

†54

†56

OH

Actinobacteria Streptomyces venezuelae // Source not specified. // Elucidation of final steps of the marineosins biosynthetic pathway through identification and characterization of the corresponding gene cluster 36 // 23-hydroxyundecylprodiginine // N // * // * // s76 37 // 23-ketoundecylprodiginine // N // * // * // s76 38 // premarineosin A // N // potent antimalarial activity (nM) against several strain, mod. inhib. HepG2 // * // s77 39 // 16-ketopremarineosin A // N // * // * // * Actinobacteria Streptomyces sp. // (sediment) Oceanside, U.S.A. // Correction to “Merochlorins A–D, Cyclic Meroterpenoid Antibiotics Biosynthesized in Divergent Pathways with Vanadium-Dependent Chloroperoxidases” 40 // merochlorin A // R // * // Structural correction. Abs. config. initially assigned from crystal structrue but as space group was incorrect, rel. config. only is known. // * Actinobacteria Streptomyces sp. // * // A multitasking vanadium-dependent chloroperoxidase as an inspiration for the chemical synthesis of the merochlorins 41 // deschloro-merochlorin B // N // * // * // * 42 // iso-chloro-merochlorin B // N // * // * // * 43 // deschloro-merochlorin A // N // * // * // * Actinobacteria Serinicoccus sp. // (sediment) Palau // Seriniquinone, a select. anticanc. agent, induces cell death by autophagocytosis, targeting cancer-protective protein dermicidin 44 // seriniquinone // M // potent and selective antitumor activity // * // s78 Actinobacteria Actinoalloteichus cyanogriseus // (sediment) Weihai, China // Acyclic congeners from A. cyanogriseus provide insights into cyclic bipyridine glycoside formation 45 // cyanogriside E // N // mod. cytotox. HTCLs // Also from a mutant strain // * 46 // cyanogriside F // N // mod. cytotox. HTCLs // Also from a mutant strain // * 47 // cyanogriside G // N // mod. cytotox. HTCLs // Also from a mutant strain // * 48 // cyanogriside H // N // mod. cytotox. HTCLs // Also from a mutant strain // * Main article bibliography reference // Taxonomy // Location // Article title Compound number // Compound name // Status // Biological activity // Other information // Secondary references

8

3


58

59

60

61


Actinobacteria Actinomadura sp. // (Chordata, Ecteinascidia turbinata) Florida Keys, U.S.A. // Forazoline A: marine-derived polyketide with AF in vivo efficacy 49 // forazoline A // N // in vivo activity against Candida in mice, mod. activity against C. albicans // * // * 50 // forazoline B // N // mod. activity against C. albicans // from modified culture conditions with high concentration of KBr // * Actinobacteria Actinokineospora sp. // (Porifera, Spheciospongia vagabunda) Red Sea // Two new antioxidant actinosporin analogues from the calcium alginate beads culture of sponge-associated Actinokineospora sp. strain EG49 51 // actinosporin C // N // mod. antioxidant activity // * // * 52 // actinosporin D // N // mod. antioxidant activity // * // * Actinobacteria Actinokineospora sp., Actinobacteria Nocardiopsis sp. // (Porifera, Spheciospongia vagabunda) Red Sea, (Porifera Dysidea avara, Mediterranean Sea) // Production of induced secondary metabolites by a co-culture of sponge-associated actinomycetes, Actinokineospora sp. EG49 and Nocardiopsis sp. RV163 53 // 5a,6,11a,12-tetrahydro-5a,11a-dimethyl[1,4]benzoxazino[3,2-b][1,4]benzoxazine // M // * // * // s79 Actinobacteria Amycolatopsis sp. // (unidentified sponge) Micronesia // A new benzofuran glycoside and indole alkaloids from a sponge-associated rare actinomycete, Amycolatopsis sp. 54 // amycofuran // N // * // * // * 55 // amycocyclopiazonic acid // N // * // * // * 56 // amycolactam // N // cytotox HTCLs // * // * CONH 2

HO

O

O O O

N H

NH

H 2NOC

O

COOH

Key:

HN

NH

HN

64

O

N

O

O

N

NH HN O

HO

63

O

O

O

HN H N

O

O

OH

N

O †58

NH

O †59

N H

O

N H

HN N

HN

10

O

62

CONH 2

O

O

57

n

O

O

O

O 9

N 64

HO

OH

NH OH

H 2NOC OH

O

CONH 2

OH N H

OH

OH HN

O

O HN

HN

CONH 2 CONH 2

O R

HO

63

N O H 60 R = H, n = 8 61 R = H, n = 10 62 R = Me, n = 10

Fermicutes Bacillus amyloliquefaciens // (sediment) South China Sea // NMR spectroscopic and MS/MS spectrometric characterization of a new lipopeptide antibiotic bacillopeptin B1 produced by a marine sediment derived Bacillus amyloliquefaciens SH-B74 57 // bacillopeptin B1 // N // mod. AF activity against plant pathogens // * // * Firmicutes Bacillus amyloliquefaciens // (sediment) South China Sea // Two new cyclic tetrapeptides from deep-sea bacterium Bacillus amyloliquefaciens GAS 00152 58 // cyclo-(Leu-Pro-Ile-Pro) // N // weak cytotox. to HTCLs // * // * 59 // cyclo-(Phe-Pro-Tyr-Gly) // N // weak cytotox. to HTCLs // * // * Firmicutes Bacillus mojavensis // (Mollusca, Pinctada martensii) Weizhou Island // Production and characterization of iturinic lipopeptides as AF agents and biosurfactants produced by a marine Pinctada martensii-derived Bacillus mojavensis B0621A 60 // iso-C14 mojavensin // N // mod. AF actvity (Fusarium oxysporum) // MS characterisation only (no NMR) // * 61 // iso-C16 mojavensin // N // mod. AF actvity (Fusarium oxysporum) // MS characterisation only (no NMR) // * 62 // anteiso-C17 mojavensin // N // mod. AF actvity (Fusarium oxysporum) // MS characterisation only (no NMR) // * Main article bibliography reference // Taxonomy // Location // Article title Compound number // Compound name // Status // Biological activity // Other information // Secondary references

9

3


65

66


Firmicutes Bacillus subtilis // (Ochrophyta, Anthophycus longifolius) Mandapam, India // Polyketide family of novel AB 7-O-methyl-5′-hydroxy-3′-heptenoate–macrolactin from seaweed-associated Bacillus subtilis MTCC 10403 63 // 7-O-methyl-5′-hydroxy-3′-heptenoate−macrolactin // N // broad spectrum AB activity // Biosynthesis established. // * Firmicutes Bacillus sp., Actinobacteria Streptomyces sp. // Ieodo, South Korea // Antibacterial and antiyeast compounds from marine-derived bacteria 64 // lauramide diethanolamine // M // mod. AB activity // Isolated from Streptomyces sp. // s80 65 // glycosylated macrolactin A1 // N // mod. AB activity // Isolated from Bacillus sp. // * 66 // glycosylated macrolactin B1 // N // mod. AB activity // Isolated from Bacillus sp. // * O OH

OH HO

HO

OH

O

O

O

OH

O

O

65

†67

O O

O OH

O

O

HO OH

OH

O

†68

OH

66

†71

OHC

R= O

COOH

R=

N H

74

R=

R= O

SMe

OH

OH HN †70

N

SMe O

OH

†72

O O

†73

R=

CONH 2

CONH 2

R=

NHAc

HO OH

O O

O

R = CH 2OH OH

OH OH †69

R

N H

H N

O

CONH 2

N

N

N H

N H CONH 2

CONH 2

S

O 75

76

AcHN

COOH

O

HO

67

68

Key:

Firmicutes Bacillus sp. // (sediment) Pacific Ocean // Amicoumacins from the marine-derived bacterium Bacillus sp. with the inhibition of NO production 67 // bacillcoumacin A // N // * // * // * 68 // bacillcoumacin B // N // * // * // * 69 // bacillcoumacin C // N // * // * // * 70 // bacillcoumacin D // N // * // * // * 71 // bacillcoumacin E // N // * // * // * 72 // bacillcoumacin F // N // * // * // * 73 // bacillcoumacin G // N // potent inhib. of lipopolysaccharide induced NO production. // * // * Actinobacteria Dermacoccus abyssi // (sediment) Challenger Deep, Mariana Trench // Dermacozines H–J isolated from a deep-sea strain of Dermacoccus abyssi from Mariana Trench sediments 74 // dermacozine H // N // mod. radical scavenging activity (DPPH) // * // * 75 // dermacozine I // N // mod. radical scavenging activity (DPPH) // * // * 76 // dermacozine J // N // mod. radical scavenging activity (DPPH) // * // *


10

3


3.1 Marine-sourced bacteria (excluding from mangroves) O

NH

OH O

O

O

NH

O

O

O

OH 3

HN

77

NH 78

N H

OH

H

OH H N

N

O

H 2N

O

N 5

O

69

70

71 72 73 74

75

Key:

O

N H

N 81

OH

O

OH

OH

OH

OH OH

80

R

HO

OH O

HO O

O

HO

O OH

HO

O †82

O

OH

O HO

H

H

H

O

OH

O

H

9

O OH

O HO

OH

O

O

†79

HO

O

O 83

O

OH

MeO

O 3

O 3

O

OH O

OH 84

O

OH

O OMe

85

†86 †87

R= R=

Me Me

metagenomic clone derived Esherichia coli // (sediment) SW Indian Ocean // Two new cytotoxic indole alkaloids from a deep-sea sediment derived metagenomic clone 77 // metagenetriindole A // N // weak-mod. cytotox. to HTCLs // * // * 78 // metagenebiindole A // N // weak-mod. cytotox. to HTCLs // * // * Bacteroidetes Jejuia pallidilutea // (unspecified seaweed) Nabeta Bay, Japan // Identification of a novel carotenoid, 2′-isopentenylsaproxanthin, by Jejuia pallidilutea strain 11shimoA1 and its increased production under alkaline condition 79 // 2′-isopentenylsaproxanthin // N // * // * // * Actinobacteria Micrococcus sp. // (Porifera, Spheciospongia vagabunda) Red Sea // New AB xanthone from the marine sponge-derived Micrococcus sp. EG45 80 // microluside A // N // mod. AB activity // * // * Actinobacteria Micromonospora sp. // (unspecified shellfish) Suruga Bay, Japan // New hydroxamate metabolite, MBJ-0003, from Micromonospora sp. 29867 81 // MBJ-0003 // N // modest activity against HTCL (SKOV-3) // * // * Actinobacteria Micromonospora sp. // (unidentified sponge) Uranouchi Bay, Japan // Neomacquarimicin: a new macquarimicin analog from marine-derived actinomycete 82 // neomacquarimicin // N // * // * // * Actinobacteria Nocardiopsis sp. // (unidentified sponge) Yeonggeumjeong, Korea // Nocatriones A and B, photoprotective tetracenediones from a marine-derived Nocardiopsis sp. 83 // nocatrione A // N // downregulates MMP-1 production // * // * 84 // nocatrione B // N // downregulates MMP-1 production // * // * Actinobacteria Nocardiopsis sp. // (sediment) Hokkaido, Japan // Nocapyrones: α- and γ-Pyrones from a marine-derived Nocardiopsis sp. 85 // nocapyrone R // N // * // * // * 86 // (10R)-nocapyrone L // R // * // Exists as 2:3 mixture of (R)- and (S)-isomers. // s81 87 // (10S)-nocapyrone L // R // * // Exists as 2:3 mixture of (R)- and (S)-isomers. // s81


11

3

Marine microorganisms and phytoplankton: H N

O HO

R

77

78

79

Br

O H 91 R = OH 92 R =

6

N H

Br

93 R

COOH

O O

HO

N

N 89 R = H 90 R = Me

76

Br N

H N

R1

H N

O

N 88


O

OH

O

R2 95 R1 = Cl, R 2 = OH 96 R1 = OH, R 2 = Cl

OMe O

O O

N H

n

O

O OH

O

94

O

6

NH

N H

OH

97 n = 6 98 n = 7

99

H

NH 2

OH

100

Proteobacteria Pelomonas puraquae // (Cnidaria, Acropora sp.) South China Sea // Pelopuradazole, a new imidazole derivative alkaloid from the marine bacteria P. puraquae sp. nov. 88 // pelopuradazole // N // * // * // * 89 // 3H-imidazole-4-carboxylic acid // M // * // * // s82 90 // 2-methyl-3H-imidazole-4-carboxylic acid // M // * // * // s83 91 // pelopurin A // M // * // * // s84 92 // pelopurin B // M // * // * // s84 Proteobacteria Pseudoalteromonas sp. // (Rhodophyta, Neogoniolithon fosliei) location unspecified // A coralline algal-associated bacterium, Pseudoalteromonas strain J010, yields five new korormicins and a bromopyrrole 93 // 4′-((3,4,5-tribromo-1H-pyrrol-2-yl)methyl)phenol // N // mod. AB act. // * // * 94 // korormicin G // N // mod. AB act. // * // * 95 // korormicin H // N // mod. AB act. // * // * 96 // korormicin I // N // mod. AB act. // * // * 97 // korormicin J // N // mod. AB act. // * // * 98 // korormicin K // N // mod. AB act. // * // * Bacteroidetes Rapidithrix thailandica // (Biofilm on unspecified shell) Yong Ling beach, Thailand // A new AB amino phenyl pyrrolidone derivative from a novel marine gliding bacterium Rapidithrix thailandica 99 // 3-(2- amino-phenyl)-5-methoxy-1,5-dihydro-pyrrol-2-one // N // mod. but selective activity against VRE // * // * Actinobacteria Salinispora arenicola // * // Characterization of an orphan diterpenoid biosynthetic operon from Salinispora arenicola 100 // isopimara-8,15-dien-19-ol // M // * // * // s85 NH

NH

O

COOMe

COOMe

COOMe

N

N

N

N

N

N

N

COOH

COOH

N

COOMe

COOMe

N

N

N

N

O R

O

N

O

OH

N †101

N H

R= †102 R =

80

Key:

N

NH HO OMe OMe

OH

OH 103

†104

COOMe

105

COOMe

OH

OH 106

COOMe

107

COOMe

OH COOMe 108

OH HO 109

COOMe

OH 110

COOMe

Proteobacteria Shewanella piezotolerans // (sediment) west Pacific // Indole-based alkaloids from deep-sea bacterium Shewanella piezotolerans with antitumor activities 101 // shewanelline A // N // * // Enantiomer of 1b // * 102 // shewanelline B // N // * // Enantiomer of 1a // * 103 // shewanelline C // N // mod. cytotox. to HTCLs // Inseparable mixture of rotamers // * Main article bibliography reference // Taxonomy // Location // Article title Compound number // Compound name // Status // Biological activity // Other information // Secondary references

12

3



Actinobacteria Streptomyces sp. // (Porifera, Halichondria panicea) Baltic Sea, Germany // Nature’s lab for derivatization: new and revised structures of a variety of streptophenazines produced by a sponge-derived Streptomyces strain 104 // streptophenazine I // N // mod. inhib. phophodiesterase type 4B // * // * 105 // streptophenazine J // N // mod. inhib. phophodiesterase type 4B // * // * 106 // streptophenazine K // N // mod. inhib. phophodiesterase type 4B, mod. AB activity // * // * 107 // streptophenazine C // R // * // * // s86 108 // streptophenazine D // R // * // * // s86 109 // streptophenazine F // R // * // * // s86 110 // streptophenazine H // R // * // * // s86

81

OH

OMe

O

OH ∆1

R3

R2 HO 111

N H

O

H N

O H N

OH

N

OH H N †112

82

O

OH

O O

R1 COOEt

O

HN

H N

N H

O

NHCHO O

O

O

N

O

†113

R1 R1 †115 R 1 †116 R 1 †117 R 1 †118 R 1 †114

HO = R 3 = H, R 2 = Me = H, R 2 = R 3 = Me = OH, R 2 = H, R 3 = Me = OH, R 2 = R 3 = Me = OH, R 2 = R 3 = H = R 2 = R3 = H

∆2 COOR

NH OH

O

O

119 R = H 120 ∆2 saturated, R = H 121 ∆2 saturated, R = Me 122 ∆1,∆2 saturated, R = H ∆

O O H

NH

125

NH OH

O

COOH

†123 †124

5

∆ saturated 126

O †127

N H

H N

O HN

HN

O

O CONH 2

Actinobacteria Streptomyces anulatus // (Porifera, Aplysina aerophoba) Yongxing Is., South China Sea // A new glutarimide derivative from marine sponge-derived Streptomyces anulatus S71 111 // 3-[2-[2-hydroxy-3-methylphenyl-5-(hydroxymethyl)]-2-oxoethyl] glutarimide // N // * // * // * 83 Actinobacteria Streptomyces axinellae // (unspecified coral) South China Sea // Axinelline A, a new COX-2 inhibitor from Streptomyces axinellae SCSIO02208 112 // axinelline A // N // mod. COX-2 inhib. // * // * 84 Actinobacteria Streptomyces drozdowiczii // (sediment) South China Sea // New anti-infective cycloheptadepsipeptide congeners and absolute stereochemistry from the deep seaderived Streptomyces drozdowiczii SCSIO 10141 113 // marformycin A // N // mod.-good selective inhib. of Micrococcus luteus // * // * 114 // marformycin B // N // mod.-good selective inhib. of M. luteus. // * // * 115 // marformycin C // R // * // Absolute configuration determined. // s87 116 // marformycin D // R // * // Absolute configuration determined. // s87 117 // marformycin E // N // mod.-good selective inhib. of M. luteus // * // * 118 // marformycin F // N // mod.-good selective inhib. of M. luteus // * // * 85 Actinobacteria Streptomyces nitrosporeus // Mutated strain of Arctic species // Lipid-lowering effects of farnesylquinone and related analogues from the marine-derived Streptomyces nitrosporeus 119 // nitrosporeunol A // N // * // * // * 120 // nitrosporeunol B // N // * // * // * 121 // nitrosporeunol C // N // * // * // * 122 // nitrosporeunol D // N // * // * // * Key: Main article bibliography reference // Taxonomy // Location // Article title 13 Compound number // Compound name // Status // Biological activity // Other information // Secondary references

3


86

123 // nitrosporeunol E // N // * // * // * 124 // nitrosporeunol F // N // * // * // * 125 // nitrosporeunol G // N // * // * // * 126 // 2-methyl-8-hydroxybenzeneheptanoic acid // M // antihyperlipidemic activity // * // s88 Actinobacteria Streptomyces scopuliridis // (sediment) South China Sea // Cyclic hexapeptides from the deep South China Sea-derived Streptomyces scopuliridis SCSIO ZJ46 active against pathogenic Gram-positive bacteria 127 // desotamide B // N // mod. AB activity // * // * 128 // desotamide C // N // * // * // * 129 // desotamide D // N // * // * // * NHR O

OH

O

OH

HO O

OH

HO

NH

87

88 89 90

Key:

R = CHO R=H

COOR1

HO

HN

O

130 R = Me 131 R = H

HO

COO

O

OH

N

S

O

OH

N

S

133

O

H N O CONH 2

R4 HO

F

O

HO O

HO O

COOH

COOH

O

R HO

HN OH

†129

HO

O

NH

O

O

HO

N H

†128


132

COOH

R2 OR 3 134 R1 = Me, R 2 = R 3 = H, R 4 = OH 135 R1 = R 4 = H, R 2 = OH, R 3 = Me 136 R1 = R 2 = R 3 = H, R 4 = OH

137

138

O

Actinobacteria Streptomyces tempisquensis // (sediment) Playa Grande, Costa Rica // Baulamycins A and B, broad-spectrum antibiotics identified as inhibitors of siderophore biosynthesis in Staphylococcus aureus and Bacillus anthracis 130 // baulamycin A // N // inhib. siderophore biosynthetic enzymes. broad spectrum AB // * // * 131 // baulamycin B // N // inhib. siderophore biosynthetic enzymes. broad spectrum AB // * // * Actinobacteria Streptomyces violans // (Magnoliophyta, Saliconia sp.) Rushan County, China. // A new polyunsaturated acid from the marine-derived Streptomyces violans 132 // (2E,4Z,6E,8Z)-5,9-dimethyl-10-oxododeca-2,4,6,8-tetraenoic acid // N // mod. AB activity // * // * Actinobacteria Streptomyces xinghaiensis // Xinghai Bay, China // Fluoroacetate biosynthesis from the marine-derived bacterium Streptomyces xinghaiensis NRRL B-24674 133 // fluoroacetate // M // * // * // s89 Actinobacteria Streptomyces sp. // (sediment) Jimei, China // p-Terphenyl O-β-glucuronides, DNA topoisomerase inhibitors from Streptomyces sp. LZ35ΔgdmAI 134 // echoside A // N // topoisomerase I inhib. (good), topoisomerase II inhib. (mod.), modest AB // * // * 135 // echoside B // N // topoisomerase II inhib. (mod.). // * // * 136 // echoside C // N // topoisomerase II inhib. (good). modest AB // * // * 137 // echoside D // N // * // * // * 138 // echoside E // N // * // * // *


14

3


OH

NHCOOMe

O

H O

O

O

O O

NH 2


HO

OMe

OH

†141

H OH

O

O

O

O

NHCOOMe

O

H O

O

OH

O

HO

Cl

Cl

Br OH

O

R

O

H

Br

O †143

HO

H

O

OH

O

O

O

NO 2

OH 139

OH

NH

OH

HO

O

O

†142

O

†144

R = Cl R = Br

HO

O

H

H OH

O

O †145

CHO

Br

140

O HO O

O

O HO

OH

MeO

O

O

HN O

O

OH

†146

O RHN

N H

H N O

OH

O N H †147 †148

H N O R = Ac R = COEt

OH

R1 OOC

R2

OH

OH

O

N H 149 R1 = Me, R 2 = OH 150 R1 = H, R 2 = OH 151 R1 = R 2 = H

OH HO

COOH

152

†153

91

Actinobacteria Streptomyces sp. // (Mollusca, Lienardia totopotens) Mactan Is., Philippines // Structure and activity of lobophorins from a turrid mollusk-associated Streptomyces sp. 139 // lobophorin H // N // * // * // * 140 // lobophorin I // N // AB. strongly cytotox. to HTCLs. // * // * 92 Actinobacteria Streptomyces sp. // (sediment) Uranouchi Bay, Japan // Structure and biological activity of 8-deoxyheronamide C from a marine-derived Streptomyces sp.: heronamides target saturated hydrocarbon chains in lipid membranes 141 // 8-deoxyheronamide C // N // Binds to cell membranes. // * // s90 93 Actinobacteria Streptomyces? // (sediment) La Jolla, U.S.A. // Napyradiomycin derivatives, produced by a marine-derived actinomycete, illustrate cytotoxicity by induction of apoptosis 142 // napyradiomycin CNQ525.510B // N // induces apoptosis in HCT-116 cells // * // * 143 // napyradiomycin CNQ525.538 // N // induces apoptosis in HCT-116 cells // * // * 144 // napyradiomycin CNQ525.554 // N // induces apoptosis in HCT-116 cells // * // * 145 // napyradiomycin CNQ525.600 // N // induces apoptosis in HCT-116 cells // * // * 94 Actinobacteria Streptomyces sp. // (Chordata, Molgula manhattensis) Minato-ku, Japan // Hyaluromycin, a new hyaluronidase inhibitor of polyketide origin from marine Streptomyces sp. 146 // hyaluromycin // N // inhib. hyaluronidase // * // * 95 Actinobacteria Streptomyces sp. // (sediment) Hatsu-shima, Japan // Lower homologues of ahpatinin, aspartic protease inhibitors, from a marine Streptomyces sp. 147 // ahpatinin Ac // N // potent pepsin inhib. mod. cathepsin B inhib. // * // * 148 // ahpatinin Pr // N // potent pepsin inhib. mod. cathepsin B inhib. // * // * Key:


15

3


96


Actinobacteria Streptomyces sp. // (sediment) Kiawah Is., USA // Carpatamides A–C, cytotoxic arylamine derivatives from a marine-derived Streptomyces sp. 149 // carpatamide A // N // mod. cytotox. to HTCLs // * // * 150 // carpatamide B // N // * // * // * 151 // carpatamide C // N // mod. cytotox. to HTCLs // * // * Actinobacteria Streptomyces sp. // (sediment) Anmyeon Is., South Korea // Anmindenols A and B, inducible nitric oxide synthase inhibitors from a marine-derived Streptomyces sp. 152 // anmindenol A // N // mod. inhib. of NO production // * // * 153 // anmindenol B // N // mod. inhib. of NO production // * // *

97

MeO

O

MeO R O

n

MeO

N H

O Cl N H O

O

O

OH OH

†154

O

O

OH OH

HO

O

OH

O

O OH

Me 2N OH

†155

OH

O

OH

O

HN

O

O

N H 156 157 158 159

O

m

O

OH

O

O

O

O

N H

O n=m=3 n = 3, m = 1 n = 1, m = 3 n=m=1

N

HO

O

O HO

4'

NO 2

6' †160

R R †162 R †163 R †161

= Me, (4'Z,6'Z) = H, (4'E,6'E) = Me, (4'E,6'E) = Me, (4'Z,6'E)

NHMe S N 164 R = OMe 165 R = NH 2 166 R = OH

COR

Cl NH 2

98

Actinobacteria Streptomyces sp. // (sediment) East Siberian continental margin, Arctic Ocean // New benzoxazine secondary metabolites from an Arctic actinomycete 154 // arcticoside // N // good inhib. of isocitrate lyase in Candida. // * // * 155 // C-1027 chromophore-V // N // weak inhib. of isocitrate lyase in Candida, strong cytotox. to HTCLS // * // * 99 Actinobacteria Streptomyces sp. // Birds Head, Indonesia // Diazaquinomycins E–G, novel diaza-anthracene analogs from a marine-derived Streptomyces sp. 156 // diazoquinomycin E // N // weak-mod. cytotox. to HTCLs // * // * 157 // diazoquinomycin F // N // * // * // * 158 // diazoquinomycin G // N // * // * // * 159 // diazoquinomycin A // M // * // * // s91 100 Actinobacteria Streptomyces sp. // (sediment) Jeju Is., South Korea // Lajollamycins, nitro group-bearing spiro-β-lactone-γ-lactams obtained from a marine-derived Streptomyces sp. 160 // lajollamycin // R // mod. inhib. of isocitrate lyase in Candida // configuration established. // s92 161 // lajollamycin B // N // mod. inhib. of isocitrate lyase in Candida // * // * 162 // lajollamycin C // N // mod. inhib. of isocitrate lyase in Candida // * // * 163 // lajollamycin D // N // mod. inhib. of isocitrate lyase in Candida // * // * 101 Actinobacteria Streptomyces sp. // (sediment) Jaebu Is., South Korea // Anithiactins A–C, modified 2-phenylthiazoles from a mudflat-derived Streptomyces sp. 164 // anithiactin A // N // mod. inhib. of acetylcholinesterase // Also synthesised. // * 165 // anithiactin B // N // mod. inhib. of acetylcholinesterase // * // * 166 // anithiactin C // N // mod. inhib. of acetylcholinesterase // * // *

Key:


16

3

Marine microorganisms and phytoplankton: NH

3.1 Marine-sourced bacteria (excluding from mangroves) OH

OH

OH

N O Me 2N

O

O

H N

N N

O

O

172 ∆

O

R2

O

R1 R1 R1 R1

= R 3 = H, R 2 = SMe = R 2 = Me, R 3 = H = H, R 2 = R 3 = Me = H, R 2 = R 3 = Me, ∆ saturated

O O

OH

R3 N H

O

O

OH HO

OH

O O

O

NH

H

H N

H O H O

173

O R

7

O

O

HO

HN OH

H N H

OH

175 R = OH 176 R = H

HO O

N H

H

174 OH

R2

R1 H

H H

O

N 168 169 170 171

HO

H

N

R1

H N

N

MeO

HO

O

OH HN

O

†167

OH

HO O

O O

HO

O

R3

O

O

COOH O

OH †177

†178

R1 = R 2 = H, R 3 = OH †179 R = R = H, R = OH 1 3 2 †180 R = OH, R = R = H 1 2 3

102 Actinobacteria Streptomyces sp. // (seawater) Iriomote Is., Japan // Anti-mycobacterial nucleoside antibiotics from a marine derived Streptomyces sp. TPU1236A 167 // streptcytosine A // N // mod. inhib. of M. smegmatis. // * // * 168 // streptcytosine B // N // * // * // * 169 // streptcytosine C // N // * // * // * 170 // streptcytosine D // N // * // * // * 171 // streptcytosine E // N // * // * // * 103 Actinobacteria Streptomyces sp. // (sediment) Point Estero, U.S.A. // An NF-κB-based high-throughput screen identifies piericidins as inhibitors of the Yersinia pseudotuberculosis… 172 // Mer-A 2026B // M // inhib. type III secretion system (virulence causing) in Yersinia tuberculosis. // * // s93 104 Actinobacteria Verrucosispora sp. // (unspecified sponge) East China Sea // Compounds from marine-derived Verrucosispora sp. FIM06054 and their potential antitumour activities 173 // FW054-1 // N // mod. cytotox. to HTCLs. // * // * 105 Proteobacteria Vibrio campbellii, Proteobacteria Vibrio harveyi // ATCC BAA-1116 // Biosynthesis of amphi-enterobactin siderophores by Vibrio harveyi BAA-1116: identification .. 174 // Amphi-enterobactin C12-OH // N // * // Biosynthetic study. // * 108 Proteobacteria Pseudoalteromonas sp. // (Cnidaria, Leptogorgia alba) Otoque Is., Panama // Microbiota of healthy corals are active against fungi in a light-dependent manner 175 // * // R // * // Revised config. at C6 // s94 176 // * // R // * // Revised config. at C7 // s94 112 Actinobacteria Streptomyces sp. // (sediment) Santa Barbara, U.S.A. // Corrigendum: Anthracimycin, a potent anthrax antibiotic from a marine-derived actinomycete 177 // anthracimycin // R // * // Revised config. (Incorrect diagram in original report). // s95 115 Actinobacteria Streptomyces sp. // (sediment) Kochi Harbour, Japan // Stereoselective total synthesis and structural elucidation of (−)-indoxamycins A–F 178 // indoxamycin B // R // * // * // s96 s97 179 // indoxamycin D // R // * // * // s96 180 // indoxamycin E // R // * // * // s96 Key: Main article bibliography reference // Taxonomy // Location // Article title 17 Compound number // Compound name // Status // Biological activity // Other information // Secondary references

3


Bacteria from mangroves R

OH

OH

OH

OH

3.2

OH

O

H

O

R1 O OH

O

O O

181

OH

O O

R3

O O

O 182

O

O

O O

O

O

O

O

O O

OH R2 183 R1 = Me, R 2 = OH, R 3 = H 185 R1 = R 3 = H, R 2 = OH 186 R1 = Me, R 2 = H, R 3 = OH

OH

OMe

184

OH

187

O

N

N

N

OH †193

OH

OH

OH

N †194

OH

R1

O

HO O

N H O

OH

O

N

198

O O

Me Me Me

†192

H N

OHC

O

HN

3

OH

O O †195 R = iPr, R = H 1 2 †196 R = R = Me 1 2 †197 R = Et, R = Me 1 2

O

OH 188

OH

†189

OHC R2

O

OH

O HN

O

(3E), R = †190 (3Z), R = †191 (3E), R =

O

OH

O

O

O

O

O

H

O

OH

O

H

N

MeS O

H HO

NH HN

H O H

OH

N

HO

200

N

OH

O 199

168 Actinobacteria Lechevalieria aerocolonigenes // (mangrove sediment) Iriomote Is., Japan // Mangromicins A and B: structure and antitrypanosomal activity of two new cyclopentadecane compounds from Lechevalieria aerocolonigenes K10-0216 181 // mangromicin A // N // good antitrypanosomal activity // * // * 182 // mangromicin B // N // mod. antitrypanosomal activity. // * // * 169 Actinobacteria Lechevalieria aerocolonigenes // (mangrove sediment) Iriomote Is., Japan // Mangromicins, six new anti-oxidative agents isolated from a culture broth of the actinomycete, Lechevalieria aerocolonigenes K10-0216 183 // mangromicin D // N // radical scavenging activity vs DPPH and NO // * // * 184 // mangromicin E // N // radical scavenging activity vs DPPH and NO // * // * 185 // mangromicin F // N // radical scavenging activity vs DPPH and NO // * // * 186 // mangromicin G // N // radical scavenging activity vs DPPH and NO // * // * 187 // mangromicin H // N // radical scavenging activity vs DPPH and NO // * // * 188 // mangromicin I // N // radical scavenging activity vs DPPH and NO // * // * 170 Actinobacteria Streptomyces sp. // (Tracheophyta, Bruguiera gymnorrhiza) unspecified location // Biosynthetic code for divergolide assembly in a bacterial mangrove endophyte 189 // divergolide E // N // * // * // * 190 // divergolide F // N // * // * // * 191 // divergolide G // N // * // * // * 192 // divergolide H // N // * // * // *

Key:


18

O

3


3.2

Bacteria from mangroves

173 Actinobacteria Jishengella endophytica // (Tracheophyta, Xylocarpus granatum root), Hainan Province, China // Alkaloids from the mangrove-derived actinomycete Jishengella endophytica 161111 193 // 2-(furan-2-yl)-6-(2S,3S,4-trihydroxybutyl)pyrazine // N // * // * // * 194 // 2-(furan-2-yl)-5-(2S,3S,4-trihydroxybutyl)pyrazine // M // * // * // s98 195 // (S)-4-isobutyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde // M // * // * // s99 196 // (S)-4-isopropyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde // M // * // * // s99 197 // (4S)-4-(2-methylbutyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde // M // * // * // s99 198 // (S)-4-benzyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c] [1,4]oxazine-6-carbaldehyde // M // * // * // s100 174 Actinobacteria Micromonospora sp. // (sediment) Butre river, Ghana // Butremycin, the 3-hydroxyl derivative of ikarugamycin and a protonated aromatic tautomer of 5′-methylthioinosine from a Ghanaian Micromonospora sp. K310 199 // butremycin // N // * // * // * 200 // * // N // * // * // * COOH

O R

O

OH

NH

OH OH

O

N

HN NH

HN HOOC OH

O

N H

O 203

201 R = H 202 R =OH

175 Actinobacteria Streptomyces sp. // (Tracheophyta, Kandelia candel leaves) Longhai, Zhangzhou, China // Juanlimycins A and B, ansamycin macrodilactams from Streptomyces sp. 201 // juanlimycin A // N // * // * // * 202 // juanlimycin B // N // * // * // * 176 Actinobacteria Verrucosispora sp. // (mangrove sediment) Butre River, Ghana // Butrepyrazinone, a new pyrazinone with an unusual methylation pattern from a Ghanaian Verrucosispora sp. K51G 203 // butrepyrazinone // M // * // * // s101

Key:


19

3


3.3

OH

O O

O O

O


O

204

OH

N O

O

O H O

HO

O

HO

H †206

H

O O

O

N

N O

HN

N

AcO

H OAc

205

H N

COR1

H N

HO

O

O

HN

†209

O

R1 = OMe, R 2 = CH 2SMe †210 R = OMe, R = CH SO Me 1 2 2 2 †211 R = NH , R = H 1 2 2

O

OAc

N H

N

†208

O

R2

O

O NH O O N

HN

207

†212

181 Ascomycota Aspergillus similanensis // (Porifera, Rhabdermia sp.) Similan Islands,Thailand // New isocoumarin derivatives and meroterpenoids from sponge-associated fungus Aspergillus similanensis sp. nov. KUFA 0013 204 // similanpyrone A // N // * // * // * 205 // similanpyrone B // N // * // * // * 206 // chevalone E // N // exhibits synergism with antibiotic against MRSA // * // * 207 // pyripyropene S // M // * // * // s102 187 Ascomycota Aspergillus versicolor // (seawater) SE Pacific Ocean // Activation of dormant secondary metabolite production by introducing neomycin resistance into the deep-sea fungus, Aspergillus versicolor ZBY-3 208 // phenethyl 5-oxo-L-prolinate // M // * // Dormant metabolite induction// s103 s104 189 Ascomycota Aspergillus sp. // (Cnidaria, Muricella abnormaliz) Xisha islands, S. China Sea // Lumazine peptides penilumamides B–D and the cyclic pentapeptide asperpeptide A from a gorgonian-derived Aspergillus sp. fungus 209 // penilumamide B // N // * // Biosynthetic study // * 210 // penilumamide C // N // * // * // * 211 // penilumamide D // N // * // * // * 212 // asperpeptide A // N // mod. AB activity // * // * X

R MeHN

OH

H OH

OMe

†213

R= †214 R =

Me Me

N H

O

H COOH †215 R = O †216 R = OH ,H

O

COOMe

O

OH

O

OH

O OH

R

O

MeO

O

Br †217 †218

OH R=H R = Br

OH

OH

219 R = OMe 220 R = Cl

COOMe

OH

O

COOMe

R2

R R1

OH

O

221 R1 222 R1 223 R1 224 R1 225 R1

HO O R3 = OH, R 2 = OH , R 3 = H OH = H, R 2 = R 3 = OH , R 3 = H = OH, R 2 = OH = OH, R 2 = R 3 = OH , R 3 = OH = OH, R 2 =

OH

O

226

190 Ascomycota Aspergillus sp. // (Cnidaria, Muricella abnormaliz) Xisha Islands, S. China Sea // anti-respiratory syncytial virus prenylated dihydroquinolone derivatives from the gorgonian-derived fungus Aspergillus sp. XS-20090B15 213 // 22-O-(N-Me-L-valyl)aflaquinolone B // N // * // * // * 214 // 22-O-(N-Me-L-valyl)-21-epi-aflaquinolone B // N // potent inhib. of human respiratory synctial virus (RSV) // * // * 194 Basidiomycota Chondrostereum sp. // (Cnidaria, Sarcophyton tortuosum) Hainan Sanya National Coral Reef Reserve, China // Induced marine fungus Chondrostereum sp. as a means of producing new sesquiterpenoids chondrosterins I and J by using gycerol as the carbon source 215 // chondrosterin I // N // * // * // * 216 // chondrosterin J // N // potent activity vs 2 HTCLs // * // * Key:


20

3


3.3


195 Ascomycota Curvularia lunata // (Cnidaria, Palythoa haddoni) Weizhou coral reef, China // Brominated resorcylic acid lactones from the marine-derived fungus Cochliobolus lunatus induced by histone deacetylase inhibitors 217 // 5-bromozeaenol // N // * // From chemical epigenetic modification // * 218 // 3,5-dibromozeaenol // N // * // From chemical epigenetic modification // * 196 Ascomycota Engyodontium album // (sediment) S. China Sea // Cytotoxic polyketides from the deep-sea-derived fungus Engyodontium album DFFSCS021 219 // engyodontiumone A // N // * // * // * 220 // engyodontiumone B // N // * // * // * 221 // engyodontiumone C // N // * // * // * 222 // engyodontiumone D // N // * // * // * 223 // engyodontiumone E // N // * // Racemic mixture. // * 224 // engyodontiumone F // N // * // Racemic mixture. // * 225 // engyodontiumone G // N // * // Racemic mixture. // * 226 // engyodontiumone H // N // * // mod. cytotox. vs HTCL (U937), mild AB activity // * 227 // 2-methoxyl cordyol C // N // * // * // * 228 // engyodontiumone I // N // * // * // * 229 // engyodontiumone J // N // * // * // * O OMe HO

O

N OH

N COOH O

HO HOOC

OH

O 231 R1 = OMe, R 2 = H 232 R1 = OMe, R 2 = CH 2OH 234 R1 = R 2 = H

O H

OH

O N

O

†230

O

O

OH

N O

O CONHMe

O O

235

N

N

O 233

O

N

N

N H

OH

228 (7E) 229 (7Z)

R1 S N

N

N

7

O

O

R2

NH

227

R1

SR1

OH

OR 2 237 R1 = R 2 = H 238 R1 = Me, R 2 = Ac

NH N

O O

O †239

NH 236

198 Ascomycota, Class Eurotiomycetes // (Chordata, Lissoclinum patella) Papua New Guinea // Oxazinin A, a pseudodimeric natural product of mixed biosynthetic origin from a filamentous fungus 230 // oxazonin A // N // antimycobacterial activity (good), antagnoist of TRP channels (modest) // Racemic mixture. // * 199 Ascomycota Neosartorya pseudofischeri // (Echinodermata, Acanthaster planci) Hainan Sanya National Coral Reef Reserve, China // Exploring the chemodiversity and biological activities of the secondary metabolites from the marine fungus Neosartorya pseudofischeri 231 // neosartin A // N // * // Racemic mixture. Produced in GlyPy media. // * 232 // neosartin B // N // * // Racemic mixture. Produced in GlyPy media. // * 233 // neosartin C // N // * // Produced in GluPy media. // * 234 // 1,2,3,4-tetrahydro-2,3-dimethyl-1,4-dioxopyrazino[1,2-a]indole // M // * // Produced in GlyPy media. // s105 235 // 1,2,3,4-tetrahydro-2-methyl-3-methylene-1,4-dioxopyrazino[1,2-a]indole // M // * // Produced in GlyPy media. // s106 Key:


21

O

3


3.3


236 // N-methyl-1H-indole-2-carboxamide // M // * // Produced in GlyPy media. // s107 237 // reduced gliotoxin // M // * // Produced in GluPy media. // s108 238 // 6-acetylbis(methylthio)gliotoxin // M // * // Produced in GlyPy media. // s109 200 Ascomycota Paecilomyces variotii // (Rhodophyta, Grateloupia turuturu) Qingdao, China // Varioxepine A, a 3H-oxepine-containing alkaloid with a new oxa-cage from the marine algal-derived endophytic fungus Paecilomyces variotii 239 // varioxepine A // N // potent inhib. of Fusarium graminearum. mod.-good AB activity // * // * AcO O O

HO

O

O 2N

O

O

OH

OR1

O

R2

HN

O

H R H †240 R = OH †242 R = H

H

†241

O

X

O

245

OH

†243

MeOOC

O

†250

HO

246

O

OH OH

254

OH HO

OH

RO R=H †248 R = Me H

HO

N H †255 R = H †258 R = OH

R O

O

O

O N H

OH †256

OH

†249

MeO

COOMe O

O 253

H

H †247

OH

OR 4 R1 = Me, R 2 = OH, R 3 = R 4 = H †252 R = R = H, R = OMe, R = Me 1 2 3 4 †251

OH

H OH

O

H HO

X = OH ,H X=O

OMe

OH

OH O

OH HO

O R3

O

HO

OH

AcO

HO

H

†244

O

OH O

HO H

HN

O

O

N NH

N O

O

OMe O O

OH

O

†257

OH

202 Ascomycota Penicillium citrinum // source unspecified. // Total synthesis and isolation of citrinalin and cyclopiamine congeners 240 // 17-hydroxycitrinalin B // N // * // * // * 241 // citrinalin C // N // * // * // * 242 // citrinalin B // R // * // First synthesis. // s110 203 Ascomycota Penicillium sp. // (sediment) Geomun-do Is., South Korea // Penicillipyrones A and B, meroterpenoids from a marine-derived Penicillium sp. fungus 243 // penicillipyrone A // N // * // * // * 244 // penicillipyrone B // N // induction of quinone reductase in murine cancer cells. // * // * 204 Ascomycota Acremonium polychromum // (Cnidaria, Annella sp.) Similan islands, Thailand // Acremonoside, a phenolic glucoside from the sea fan-derived fungus Acremonium polychromum PSU-F125 245 // acremonoside // N // * // * // * 205 Ascomycota Arthrinium sp. // (unidentified sponge) Xisha Islands, China // A new naphthalene glycoside from the sponge-derived fungus Arthrinium sp. ZSDS1-F3 246 // 1,8-dihydroxynaphthol-1-O-α-L-rhamnopyranoside // N // * // * // * 206 Ascomycota Ascotricha sp. // (sediment) Fenghua County, China // Caryophyllene sesquiterpenes from the marine-derived fungus Ascotricha sp. ZJ-M-5 by the one strain–many compounds strategy 247 // (+)-6-O-demethylpestalotiopsin A // N // good cytotox. vs 2 HTCLs // * // * 248 // (+)-6-O-demethylpestalotiopsin C // N // good cytotox. vs 2 HTCLs // * // * 249 // (−)-6-O-demethylpestalotiopsin B // N // * // * // * 207 Ascomycota Astrocystis sp. // (Tracheophyta, Nypa sp. ) Hat Khanom-Mu Ko Thale Tai National Park,, Thailand // Bioactive polyketides from the fungus Astrocystis sp. BCC 22166 250 // astrophthalide // N // * // * // * Key:


22

3


3.3


251 // 5,7-dihydroxy-O-methylmellein // N // * // * // * 252 // 5,6-dimethoxymellein // N // * // * // * 253 // astropyrone // N // * // * // * 254 // astrophenone // M // * // Commercially available. // * 213 Ascomycota Aspergillus flavus // (Arthropoda, Penaeus vannamei) Lianyungang, China // Indole diterpenoids and isocoumarin from the fungus, Aspergillus flavus, isolated from the prawn, Penaeus vannamei 255 // 2R,4bR,6aS,12bS,12cS,14aS)-4b-deoxy-β-aflatrem // N // arrest of cell cycle in A549 cells. mod. PKC-beta inhib. mod. S. aureus inhib. // * // * 256 // (2R,4bS,6aS,12bS,12cR)-9-isopentenyl paxilline D // N // arrest of cell cycle in A549 cells // * // * 257 // (S)-(−)-6,8-di-O-methylcitreoisocoumarin // N // * // * // * 258 // β-aflatrem // M // * // * // s111 259 // pasapaline // M // * // * // s112 s113 260 // leporin B // M // * // * // s114 261 // leporin A // M // * // * // s115 H H

H

O

O H

O †260 †261

N

O

OH

O 263

O

OH

O 2N O

N

N

O

O

H

O

262

H

HO

COOMe

OMe

N H

NR

O

HN

O

HN

R=H OR R = Me

O

NH

O

H †259

HN

O

O N H

O

†264

O

N

265 R = H 266 R = COCH 2Ac 267 R = COCH 2COOMe

COOMe

268

O

214 Ascomycota Aspergillus flavipes // (Arthropoda, Ligia oceanica) Zhoushan, China // A new cyclopeptide metabolite of marine gut fungus from Ligia oceanica 262 // * // N // * // * // * 263 // N-benzoyl-phenylalanine methyl ester // M // * // * // s116 215 Ascomycota Aspergillus ochraceus // (Rhodophyta, Coelarthrum sp.) Paracel Islands, China // Cytotoxic and antiviral nitrobenzoyl sesquiterpenoids from the marine-derived fungus Aspergillus ochraceus Jcma1F17 264 // 6β,9α-dihydroxy-14-p-nitrobenzoylcinnamolide // N // mod. activity vs 10 HTCLs and two viruses // * // * 216 Ascomycota Aspergillus oryzae // (sediment) Langqi Is., China // Speradines B–E, four novel tetracyclic oxindole alkaloids from the marine-derived fungus Aspergillus oryzae 265 // speradine B // N // * // * // * 266 // speradine C // N // * // * // * 267 // speradine D // N // * // * // * 268 // speradine E // N // * // * // * OH O

O O

O

H HO N

O 269

Key:

O

O

OH

OH

H O

N

OH

O

H

O

OH 271

O

O

OH O

N

NH H

N

HOOC

HO O

272

N O

O 273 O

OH

274

HO HO

COOMe

275

270 OH


23

3


3.3


217 Ascomycota Aspergillus terreus // (Chordata, Chelon haematocheilus) Yellow River estuary, China // New rubrolides from the marine-derived fungus Aspergillus terreus 269 // rubrolide R // N // * // * // * 270 // rubrolide S // N // * // * // * 218 Ascomycota Aspergillus oryzae // (sediment) Min River estuary, China // Speradines F–H, three new oxindole alkaloids from the marine-derived fungus Aspergillus oryzae 271 // speradine F // N // * // * // * 272 // speradine G // N // * // * // * 273 // speradine H // N // * // * // * 219 Ascomycota Aspergillus sydowii // (unidentified sponge) Xisha Islands, China // antimicrobial and antiviral sesquiterpenoids from sponge-associated fungus, Aspergillus sydowii 274 // aspergillusene C // N // * // * // * 220 Ascomycota Aspergillus terreus // (unidentified sponge) Naozhu Sea, China // Structures and antiviral activities of butyrolactone derivatives isolated from Aspergillus terreus 275 // butyrolactone VIII // N // * // * // * HO

O

O

HO O

R1

O

O

O

O

O HO O

OH

O

OH

H

O

O

O O

R2

OH

282

O

O

HO R1 R2

H O

O

O

OH

OMe

HO MeO

R3 R1 = OH, R 2 = R 3 = OMe †277 R = OMe, R = OH, R = H 1 2 3 279 R1 = R 2 = OMe, R 3 = H †276

†280

O

278

H 281

O

HO

H †283

OMe O OH 284 R1 = OH, R 2 = H 285 R1 = OAc, R 2 = H 286 R1 = H, R 2 = OMe

221 Ascomycota Aspergillus terreus // Cnidaria, Echinogorgia aurantiaca) S. China Sea // Territrem and butyrolactone derivatives from a marine-derived fungus Aspergillus terreus 276 // territrem D // N // * // * // * 277 // territrem E // N // * // * // * 278 // 11a-dehydroxyisoterreulactone A // N // * // * // * 279 // arisugacin A // M // * // * // s117 280 // isobutyrolactone V // N // * // * // * 281 // isobutyrolactone II // N // * // Racemic mixture. // * 222 Ascomycota Aspergillus tubingensis // (Porifera, Ircinia variabilis) Mediterranean Sea // Sensitivity of Neurospora crassa to a marine-derived Aspergillus tubingensis anhydride exhibiting antifungal activity that is mediated by the MAS1 protein 282 // tubingenoic anhydride A // N // * // * // * 223 Ascomycota Aspergillus ustus // Chlorophyta, Codium fragile) Zhoushan Is., China // Ergosteroid derivatives from an algicolous strain of Aspergillus ustus 283 // isocyathisterol // N // modest AB activity // * // * 224 Ascomycota Aspergillus versicolor // (Porifera, Hymeniacidon perleve) Bohai Sea, China // Three new sterigmatocystin analogues from marine-derived fungus Aspergillus versicolor 284 // sterigmatocystin hemiacetal // M // * // * // s118 285 // acyl-hemiacetal sterigmatocystin // N // * // * // * 286 // 5-methoxydihydrosterigmatocystin // M // mod. AB activity // * // s119 Key:


24

3


OMe HO


OMe

O

O

OH

O N

N R1

O HO

3.3

287 O

HO

OH

O

O

NH R2

OH

†290

R1 †291 R 1 †292 R 1 †293 R 1

288

N

HO

N

O N †298

†294

N N

HO

O

OMe

O

OH OMe

N

O

H N H

296

†297

N

O H O

N

O

O HN

N †299

O O

N H

N H

H O

N

OMe

O

O O

OH

N

O

H

O

O

O

†295

H

N

O

H

N

HO

H O

N

N

R3 O = R 2 = R3 = H = R 2 = H, R 3 = Me = H, R 2 = OH, R 3 = Me = R 2 = OH, R 3 = Me

O O

HN

NH

N

N

O

O

O

AcN †289

O O

HN

N

O

N

O

N H

†300

†301

O

225 Ascomycota Aspergillus versicolor // (Porifera, Hymeniacidon perleve) Bohai Sea, China // Cytotoxic polyphenols from a sponge-associated fungus Aspergillus versicolor Hmp-48 287 // 4,6-dimethoxy-2,9-dimethyldibenzo[b,e][1,4]dioxine-1,7-diol // N // mod. inhib. vs HL-60 HTCL // * // * 288 // 3-(3-hydroxy-5-methylphenoxy)-5-methyl-4-(3-methylbut-2-en-1-yl)phenol // N // mod. inhib. vs HL-60 HTCL // Same as compd 3 in ref. s120. Concurrent pubs. // s120 289 // (3S)-3,4-dihydro-5-(3-hydroxy-5-methylphenoxy)-2,2,7-trimethyl-2H-chromen-3-ol // N // mod. inhib. vs HL-60 HTCL // * // * 226 Ascomycota Aspergillus versicolor // (sediment) Yellow Sea // Psychrophilins E–H and versicotide C, cyclic peptides from the marine-derived fungus Aspergillus versicolor ZLN-60 290 // psychrophilin E // N // * // * // * 291 // psychrophilin F // N // * // * // * 292 // psychrophilin G // N // potent lipid lowering effects // * // * 293 // psychrophilin H // N // * // * // * 294 // versicotide C // N // * // * // * 227 Ascomycota Aspergillus versicolor // (sediment) S. China Sea // Prenylated indole diketopiperazines from the marine-derived fungus Aspergillus versicolor 295 // versicamide A // N // * // * // * 296 // versicamide B // N // * // * // * 297 // versicamide C // N // * // * // * 298 // versicamide D // N // * // * // * 299 // versicamide E // N // * // * // * 300 // versicamide F // N // * // * // * 301 // versicamide G // N // * // * // *

Key:


25

3

Marine microorganisms and phytoplankton: O HO N

O

NH

3.3


O HO

NH

N

O

OMe O

O N

O

O

O

HO O

O

MeO

OH †304 X = 2H †305 X = O

OMe OH

302

HO

NH O †306

O O

O

O

H

N OH

307

COOMe

O

O

X

OH

O

OH

OH

O

HO

OH

OH

O HO

OH

OMe

O

O

O

†309

†308

HO

COOMe

H O

H

OH 310

O

303

228 Ascomycota Aspergillus versicolor // (Cnidaria, Dichotella gemmacea) Xisha Islands, China // Nucleoside derivatives from the marine-derived fungus Aspergillus versicolor 302 // kipukasin H // M // * // * // * 303 // kipukasin I // M // * // * // * 229 Ascomycota Aspergillus wentii // (Ochrophyta, Sargassum fusiforme) Nanao Is., China // Aspewentins A–C, norditerpenes from a cryptic pathway in an algicolous strain of Aspergillus wentii 304 // aspewentin A // N // good cytotox. vs two phytoplankton // * // * 305 // aspewentin B // N // mod. cytotox. vs 1 zooplankton and 1 phytoplankton // * // * 306 // aspewentin C // N // mod. cytotox. vs 1 phytoplankton // * // * 230 Ascomycota Aspergillus sp. // (Porifera, Tethya aurantium) Rovinj, Croatia // Marine bacterial inhib.s from the sponge-derived fungus Aspergillus sp. 307 // * // N // selective inhib. of Vibrio species// * // * 308 // * // N // broad spectrum AB // * // * 231 Ascomycota Aspergillus sp. // (Cnidaria, Dichotella gemmacea) S. China Sea // A new anthraquinone derivative from a gorgonian-derived fungus Aspergillus sp. 309 // 8-O-methylnidurufin // N // mod. AB activity // * // * 232 Ascomycota Aspergillus sp. // (unspecified sponge) Ishigaki Is., Japan // Terretonin G, a new sesterterpenoid antibiotic from marine-derived Aspergillus sp. OPMF00272 310 // terretonin G // N // mod. activity vs Gram-positive bacteria // * // *

H

O MeO

HO

N

O

N

N N H

H

O

N †311

O

H

H

O

O †312

OR

O O O †313

O

O

O

O

O

HO

HN SMe O

OH

O

H

HN

N

OH

OH

H

O

O O †314

SMe O

HO

MeO †315

R=H †316 R = Me

OH

†317

233 Ascomycota Aspergillus sp. // (sediment) Shorncliffe, Australia // Shornephine A: structure, chemical stability, and P-glycoprotein inhib properties of a rare diketomorpholine from an Australian marine-derived Aspergillus sp. 311 // shornephine A // N // P-glycoprotein inhib. (MDR reversing) // Acid labile methanolysis. // * 312 // 15b-β-methoxy-5-N-acetyladreemin // N // * // * // * 234 Ascomycota Aspergillus sp. // (Arthropoda, Ligia oceanica) Dinghai, China // Methylthio-aspochalasins from a marine-derived fungus Aspergillus sp. 313 // aspochalasin V // N // mod. cytotox. vs 2 HTCLs // * // * Key:


26

3


3.3


314 // aspochalasin W // N // * // * // * 235 Ascomycota Aspergillus sp. // (Chlorophyta, Enteromorpha prolifera) Jinjiang Saltern, China // Three new asperentin derivatives from the algicolous fungus Aspergillus sp. F00785 315 // 6-O-α-D-ribosylasperentin // N // * // * // * 316 // 6-O-α-D-ribosyl-8-O-methylasperentin // N // * // * // * 317 // 5-hydroxyl-6-O-methylasperentin // N // * // * // * R1

HO

OMe R2

HO

OH O

HO O

O O

†318

R1 R1 †322 R 1 †323 R 1

O

†319

O

O

†320 †321

324 O

OH

= R2 = = R 2 = OH = OMe , R 2 = OH = H, R 2 =

OH

OH O

O

OH

H H

H

†326

O

†325

H

COOH

HO

O

HO

OH

327

OH

236 Ascomycota Aspergillus sp. // (sediment) Lau Basin hydrothermal vent, SW Pacific Ocean // Nine new and five known polyketides derived from a deep sea-sourced Aspergillus sp. 318 // aspiketolactonol // N // weak inhib. vs HTCLs // * // * 319 // aspilactonol A // N // weak inhib. vs HTCLs // * // * 320 // aspilactonol B // N // weak inhib. vs HTCLs // Diastereoisomeric with 321 and 322 // * 321 // aspilactonol C // N // weak inhib. vs HTCLs // Diastereoisomeric with 320 and 322 // * 322 // aspilactonol D // N // weak inhib. vs HTCLs // Diastereoisomeric with 320 and 321. // * 323 // aspilactonol E/F // N // weak inhib. vs HTCLs // Epimeric mixture. // * 324 // (S)-2-(2′-hydroxyethyl)-4-methyl-γ-butyrolactone // M // * // * // s121 325 // aspyronol // N // weak inhib. vs HTCLs // * // * 326 // epiaspinonediol // N // weak inhib. vs HTCLs // * // * 237 Ascomycota Aspergillus sp. // (Phaeophyta, Sargassum sp.) Helgoland, Germany // A new cytotoxic steroid from co-fermentation of two marine alga-derived micro-organisms 327 // 7β-hydroxycholesterol-1β-carboxylic acid // N // * // From co-culture with unidentified bacterium. // * R2

O

N

O

HO O

H N

NH

O

O

O

HN

HO O

O

O

†335

O O

N

HN

O

O

HN

O R1 R1 = Me, R 2 = OH †329 R = H, R = OH 1 2 †330 R = R = H 1 2 †328

†331

O

N H

OH NH 2 O

R1 H O

OH

HN O

MeO

†337

O

R = Me R=H

OH 333

OH

OH

O HO

N HN

†334

O O

OR NH 2

†332

OH NH 2

HN

OH

NH

O O

O

O

O N H †338

COOH

†339

R1 = †340 R = 1 †341 R = 1

R2 OH , R 2 = OH OH , R 2 = OH OH , R 2 = OH

N

O N

H 342

†336

238 Ascomycota Beauveria felina // (unidentified bryozoan) unspecified location // Cyclohexadepsipeptides of the isaridin class from the marine-derived fungus Beauveria felina EN-135 328 // isaridin G // N // * // * // * 329 // desmethylisaridin G // N // * // * // * Key:


27

3


3.3


330 // desmethylisaridin C1 // N // mod. inhib. of E. coli // * // * 239 Ascomycota Beauveria felina // (unidentified bryozoan) unspecified location // Cyclodepsipeptides and other O-containing heterocyclic metabolites from Beauveria felina EN-135, a marine-derived entomopathogenic fungus 331 // iso-isariin D // N // mod. cytotox. to A. salina // * // * 332 // felinone A // N // weak cytotox. to A. salina // * // * 333 // felinone B // N // weak cytotox. to A. salina // Same as 389. Concurrent publications. // s122 240 Ascomycota Cladosporium sphaerospermum // (sediment) Pacific Ocean // Cladosins A–E, hybrid polyketides from a deep-sea-derived fungus, Cladosporium sphaerospermum 334 // cladosin A // N // * // Tautomeric mixture. // * 335 // cadosin B // N // * // Tautomeric mixture. // * 336 // cladosin C // N // * // Tautomeric mixture. // * 337 // cladosin D // N // * // Tautomeric mixture. // * 338 // cladosin E // N // * // * // * 241 Ascomycota Cochliobolus lunatus, Ascomycota Curvularia lunata // (Cnidaria, Palythoa haddoni) Weizhou, S. China Sea // Antifouling and fungicidal resorcylic acid lactones from the sea anemone-derived fungus Cochliobolus lunatus 339 // cochliomycin D // N // potent activity vs B. amphitrite larvae// Diastereoisomer of 340 and 341. // * 340 // cochliomycin E // N // * // Diastereoisomer of 339 and 341. // * 341 // cochliomycin F // N // potent activity vs B. amphitrite larvae // Diastereoisomer of 339 and 340. // * 242 Ascomycota Curvularia sp. // (Chordata, Agyrosomus argentatus) Yellow Sea // Curvulamine, a new AB alkaloid incorporating two undescribed units from a Curvularia species 342 // curvulamine // N // potent and selective AB activity // Biosynthetic study. // * H X OH

R

HO

OH

HO

H

H H

R = OH, X = O †344 R = OH, X = OH ,H †345 R = H, X = OH ,H

HO

H H †346

HO

COOEt

H

N H

OO

O †343

H

HO

NH

348

HO

OH OH 347

OH

O †349

HO

H

N H

O

†350

OH

OMe

OH OH

243 Ascomycota Dendrodochium sp. // (Echinodermata, Holothuria nobilis) S. China Sea // Polyhydroxy cyclohexanols from a Dendrodochium sp. fungus associated with the sea cucumber Holothuria nobilis Selenka 343 // dendrodochol A // N // modest AF activity // * // * 344 // dendrodochol B // N // * // * // * 345 // dendrodochol C // N // modest AF activity // * // * 346 // dendrodochol D // N // * // * // * 244 Ascomycota Diaporthaceae sp. // (unspecified sponge) Sikao, Thailand // An AB cytochalasin derivative from the marine-derived fungus Diaporthaceae sp. PSU-SP2/4 347 // diaporthalasin // N // significant AB activity vs S. aureus and MRSA // * // * 348 // diaporthacol // N // * // * // * 245 Ascomycota Dichotomomyces cejpeii // (Porifera, Callyspongia sp. cf. C. flammea) Bear Is., Australia // Indoloditerpenes from a marine-derived fungal strain of Dichotomomyces cejpii with antagonistic activity at GPR18 and cannabinoid receptors 349 // emindole SB beta-mannoside // N // antagonist of cannabinoid receptor (subtype CB2) // * // * Key: Main article bibliography reference // Taxonomy // Location // Article title 28 Compound number // Compound name // Status // Biological activity // Other information // Secondary references

3


3.3


350 // 27-O-methylasporyzin C // N // antagonist of G protein-coupled receptor (GPR18) // * // * OMe O HO O

OH

OH O

R1 OR 2

OH

OH

O

O

OH

O

OH †356

OH

OH

O

OH †357

OH

O

O O

HO 355

R1 = Cl, R 2 = H R1 = OMe, R 2 = Me †354 R = OH, R = Ac 1 2

OH

OH

HO

O

†351

OMe O

HO O

O

OH

HO O

R

MeSOC

MeO

†358

R=H 359 R = OH

OH

OMe

†352

†353

OH

246 Ascomycota Emericella sp. // (sediment) S. China Sea // New prenylxanthones from the deep-sea derived fungus Emericella sp. SCSIO 05240 351 // emerixanthone A // N // * // * // * 352 // emerixanthone B // N // * // * // * 353 // emerixanthone C // N // * // * // * 354 // emerixanthone D // N // * // * // * 247 Ascomycota Eurotium amstelodami // (unidentified marine animal) Sungsan coast, Korea // Anti-inflammatory activity of questinol isolated from marine-derived fungus Eurotium amstelodami in lipopolysaccharide-stimulated RAW 264.7 355 // questinol // M // inhib. of production of pro-inflammatory cytokines // * // s123 248 Ascomycota Eurotium cristatum // (Phaeophyta, Sargassum thunbergii) Qingdao, China // Anthraquinone derivatives and an orsellinic acid ester from the marine alga-derived endophytic fungus Eurotium cristatum EN-220 356 // 3-O-(α-D-ribofuranosyl)questinol // N // * // * // * 357 // cristatumside A // N // * // * // * 249 Ascomycota Eurotium rubrum // (Cnidaria, Sarcophyton sp.) Xuwen National Coral Reef Nature Reserve, S. China Sea // Eurothiocin A and B, sulfur-containing benzofurans from a soft coral-derived fungus Eurotium rubrum SH-823 358 // eurothiocin A // N // potent competitive -glucosidase inhibiton // * // * 359 // eurothiocin B // N // potent competitive  -glucosidase inhibiton // * // * †360

∆1

∆2

R1

R2

OH

O O

OH

R1 R1 †362 R 1 †363 R 1 †364 R 1 †365 R 1 †366 R 1 †367 R 1 †368 R 1 †369 R 1 †361

= = = = = = = = = =

H, R 2 = H, R 2 = H , R2 = H, R 2 = H , R2 = H, R 2 = H , R2 = H, R 2 = H , R2 = H , R2 =

OMe , OMe , OMe , OMe , OMe , OMe , OMe , OMe , OMe , OMe ,

∆1, ∆2 saturated ∆1, ∆2 saturated ∆1, ∆2 saturated ∆1, ∆2 saturated ∆2 saturated ∆2 saturated ∆2 saturated ∆2 saturated ∆1 saturated ∆1 saturated

OH

AcO HO

OMe

O

OH

OH

H

OMe †370 †371

R= R=

H H

OAc HO

OAc HO

H N

AcO HO

R

R HO

OH

H

†373

H HO

OH 374 R = OAc 375 R = H

O

OH

OH

H

H HO HO

HO 377

†376

†372

OH

250 Ascomycota Eurotium sp. // (Cnidaria, Subergorgia suberosa) Xisha Islands, S. China Sea // Dihydroisocoumarin derivatives with antifouling activities from a gorgonian-derived Eurotium sp. fungus 360 // (+)-eurotiumide A // N // potent broad spectrum AB activity // * // * 361 // (–)-eurotiumide A // N // potent broad spectrum AB activity // * // * 362 // (+)-eurotiumide B // N // strong antifouling activity vs B. amphitrite larval settlement, broad spectrum AB activity // * // * 363 // (–)-eurotiumide B // N // strong antifouling activity vs B. amphitrite larval settlement, broad spectrum AB activity // * // * Key:


29

3


3.3


364 // (+)-eurotiumide C // N // broad spectrum AB activity // * // * 365 // (–)-eurotiumide C // N // broad spectrum AB activity. // * // * 366 // (+)-eurotiumide D // N // strong antifouling activity vs B. amphitrite larval settlement, broad spectrum AB activity // * // * 367 // (–)-eurotiumide D // N // strong antifouling activity vs B. amphitrite larval settlement, broad spectrum AB activity // * // * 368 // (+)-eurotiumide E // N // not tested // * // * 369 // (–)-eurotiumide E // N // not tested // * // * 370 // (±)-eurotiumide F // N // broad spectrum AB activity // * // * 371 // (±)-eurotiumide G // N // broad spectrum AB activity // * // * 253 Ascomycota Hansfordia sinuosae // (Porifera, Niphates sp.) S. China Sea // Punctaporonins H–M: caryophyllene-type sesquiterpenoids from the sponge-associated fungus Hansfordia sinuosae 372 // punctaporonin H // N // * // * // * 373 // punctaporonin I // N // * // * // * 374 // punctaporonin J // N // * // * // * 375 // punctaporonin K // N // good lipid lowering activity // * // * 376 // punctaporonin L // N // * // * // * 377 // punctaporonin M // N // * // * // * OH OH

H N

O OH

O

O

O O HO

O HO

HO Cl

O

378

OH HO

HO Cl

HO O OH

OH

O

O

O HN 381

O

O

O

380

OH

O

O O

Cl 379

NH

O

N H

NH

RO

OH OH

O

OH O

O

O

OH R = Ac †383 R = H †382

R1 O

R 2O

OH

OH R1 = Ac, R 2 = H †385 R = H, R = Ac 1 2 †384

AcO

OH

HO †386

OH

254 Ascomycota Humicola fuscoatra // (sediment) Tutuila, American Samoa // Study of marine natural products including resorcyclic acid lactones from Humicola fuscoatra that reactivate latent HIV-1 expression in an in vitro model of central memory CD4+ T cells 378 // radicicol B // N // * // * // * 379 // radicicol C // N // * // * // * 380 // radicicol D // N // * // * // * 255 Acomycota Isaria felina // coast of Vietnam, S. China Sea // Oxirapentyns F–K from the marine-sediment-derived fungus Isaria felina KMM 4639 381 // isoisariin B // M // * // * // s124 382 // oxirapentyn F // N // * // * // * 383 // oxirapentyn G // N // * // * // * 384 // oxirapentyn H // N // * // * // * 385 // oxirapentyn I // N // * // * // * 386 // oxirapentyn J // N // * // * // * 387 // oxirapentyn K // N // * // * // * 388 // isariketide // N // mod. cytotox. vs HTCL (HL-60) // * // * 389 // acremine S // N // * // Same as 333. Concurrent publications. // s125

Key:


30

3


OH

N COOMe

AcO MeOOC

O

O


O

O

O

AcO

3.3

OH

389

388

O

†390

OH

OH

H

O

396

†393

OH

O

O NH

O

O

397

N O

398

O

OH

HO

O

O

O N

N O

OH †392

391

O

O HO

O

OH

O

O

O

†394

HO

N H

O HO O

OH

HOOC

O

N

OH

O H

CHO N

OH

N

O

†387

HO

HO

N

OH O

COOH

O

O

HO

HOOC O

O

Cl

5

399

†395

179 Ascomycota Neosartorya laciniosa, Ascomycota Neosartorya paulistensis // (N. laciniosa ex diseased coral), (N. paulistensis ex Porifera, Chondrilla australiensis) Ao Nuan Lan Is., Thailand // Antibacterial and antibiofilm activities of tryptoquivalines and meroditerpenes isolated from the marine-derived fungi N. paulistensis, N. laciniosa, N. tsunodae, and the soil fungi N. fischeri and N. siamensis 390 // tryptoquivaline T // N // * // Ex N. laciniosa. // * 391 // sartorypyrone C // N // * // Ex N. paulistensis. // * 256 Ascomycota Nigrospora oryzae, Ascomycota Khuskia oryzae // (Cnidaria, Verrucella umbraculum) Sanya City, China // Alkaloids and citrinins from marine-derived fungus Nigrospora oryzae SCSGAF 0111 392 // nigrospine // N // * // * // * 393 // nigrospin A // N // * // * // * 394 // nigrospin B // N // weak AF activity // * // * 395 // nigrospin C // N // weak AF activity // * // * 257 Ascomycota Paecilomyces formosus, Ascomycota Paecilomyces formosa, Ascomycota Paecilomyces variotii // (driftwood) Kasai Rinkai Park, Japan // Formosusin A, a novel specific inhib. of mammalian DNA polymerase β from the fungus Paecilomyces formosus 396 // formosusin A // N // * // * // * 397 // formosusin B // N // specific inhib. of mammalian DNA polymerase b (pol b) // * // * 398 // formosusin C // N // * // * // * 258 Ascomycota Paraconiothyrium sp. // (unspecified Chordata specimen) Guatemala // The marine fungal metabolite, AD0157, inhibits angiogenesis by targeting the Akt signaling pathway 399 // AD0157 // N // potent angiogenesis inhib. // * // *

Key:


31

3


3.3


O O

R 3O

N

N H H

HN

N

N

O †400

H N

O R2

O H HN O

O

MeO

401

N

MeO N

H

COOH

O

OH

O

†406 †407

O

HO

OH OH

408

O

O

R= R=

H H

COOH

O

OH

N NH

O O

411

COOH

O

†409

O

R

O

HO

OH

O

OH

HO

†410

OH

405

R1 = OH, R 2 = R 3 = H †403 R = R = H, R = OH 1 3 2 †404 R = H, R = OH, R = 1 2 3

MeOOC

O

O OH

†402

HO

O

O

R O

R1

HO

O

OH HO

H N

O O

N

HO

H

N

O

HOOC

O

N

HO

†412

R

R= †413 R =

N H

CONH 2 OH OH

259 Ascomycota Penicillium adametzioides // (unidentified sponge) Wenchang, China // N-Formyllapatin A, a new N-formylspiroquinazoline derivative from the marine-derived fungus Penicillium adametzioides AS-53 400 // N-formyllapatin A // N // * // * // * 401 // lapatin B // M // mod. inhib. of V. harveyi // * // s126 260 Ascomycota Penicillium brefeldianum // (sediment) Pearl River estuary, S. China Sea // Prenylated indolediketopiperazine peroxides and related homologues from the marine sediment-derived fungus Penicillium brefeldianum SD-273 402 // 24-hydroxyverruculogen // N // * // * // * 403 // 26-hydroxyverruculogen // N // * // * // * 404 // 13-O-prenyl-26-hydroxyverruculogen // N // mod. cytotox. to A. salina // * // * 261 Ascomycota Penicillium chrysogenum // (unspecified source) North Sea coast, China // Secondary metabolites of the marine fungus Penicillium chrysogenum 405 // 2-(2-hydroxypropanamido)benzoic acid // N // antiinflammatory and analgesic effects with no ulcerogenic effect // * // * 262 Ascomycota Penicillium chrysogenum // (sediment) S. China Sea // Sorbicatechols A and B, antiviral sorbicillinoids from the marine-derived fungus Penicillium chrysogenum PJX-17 406 // sorbicatechol A // N // modest antiviral activity vs H1N1 // * // * 407 // sorbicatechol B // N // modest antiviral activity vs H1N1 // * // * 263 Ascomycota Penicillium citrinum // (Magnoliaphyta, Salicornia herbacea) Dafeng harbor, Yancheng, China // A PKS I gene-based screening approach for the discovery of a new polyketide from Penicillium citrinum Salicorn 46 408 // penicitriketo // N // mod. radical scavenging activity (DPPH) // * // * 264 Ascomycota Penicillium citrinum // (Cnidaria, Echinogorgia aurantiaca) Sanya, China // Three new polyketides from marine-derived fungus Penicillium citrinum SCSGAF 0167 409 // penicitrinol G // N // * // * // * 410 // penicitrinol H // N // * // * // * 411 // 2,11-dihydroxy-1- methoxycarbonyl-9-carboxylxanthone // N // * // * // * 265 Ascomycota Penicillium commune // (seawater) Qingdao, China // Structure and absolute configuration of penicilliumine, a new alkaloid from Penicillium commune 366606 412 // (+)-penicilliumine // N // * // * // * 413 // (−)-penicilliumine // N // * // * // * Key:


32

3

Marine microorganisms and phytoplankton: OMe O

O

O

R1

O

OH

O

†414

R2 HO

X

O

R1 O

H

OMe

COOR 2 R1 = OH, R 2 = nBu †418 R = OH, R = H 1 2 †419 R = H, R = nBu 1 2 †420 R = R = H 1 2

OR1

OH †427 R = H, R = 1 2 428 R1 = Ac, R 2 =

OH OAc

O

O

R3

H

O COOH

OMe

O

R = OH †422 R = H

O

O

O

†421

O

O

H

OMe

O

423

HO

O

H

H

O

424 R = OH R=H

O

O

O

OMe

†425

H

O AcO

AcO O

O O

430

O

COOH

OH

OMe

O

O COOMe

O OH

O

R4

OH

H †426

HO

HO

O 429 X = O, R1 = R 2 = OAc , R 3 = OH, R 4 = OAc †431 X = OH ,H, R1 = OH , R 2 = R 4 = H, R 3 = OH OH ,H, R1 = OH , R 2 = R 3 = H, R 4 = OAc 432 X =

R

O

O

†417

415 R1 = H 416 R1 = OH

R

HO

O

O

H

R2

R

O

O

H HO


OMe

HO O

3.3

OAc

HO

O

OAc

433

O

†434

S HO

COOMe †435

O

S HO

COOMe

266 Ascomycota Penicillium echinulatum // (Rhodophyta, Chondrus ocellatus) Pingtan Is., China // Meroterpenes from an algicolous strain of Penicillium echinulatum 414 // arisugacin K // N // mod. inhib. of E. coli // * // * 415 // arisugacin G // M // * // * // s127 416 // arisugacin C // M // modest cytotox. to A. salina // * // s127 267 Ascomycota Penicillium thomii, Ascomycota Penicillium lividum // Lazurnaya Bay, Russia // Meroterpenoids from the alga-derived fungi P. thomii Maire and P. lividum Westling 417 // austalide H acid butyl ester // N // inhib. AP-1 dependent transcription without cytotox.. inhib. mollusk enzyme. // * // * 418 // austalide H acid // N // inhib. AP-1 dependent transcription without cytotox., inhib. mollusk enzyme // * // * 419 // austalide P acid butyl ester // N // inhib. mollusk enzyme // * // * 420 // austalide P acid // N // inhib. mollusk enzyme // * // * 421 // austalide Q acid // N // inhib. mollusk enzyme // * // * 422 // 13-deoxyaustalide Q acid // N // * // * // * 423 // 17-O-demethylaustalide B // N // * // * // * 424 // 13-O-deacetylaustalide I // N // inhib. AP-1 dependent transcription without cytotox., inhib. mollusk enzyme // * // * 425 // 13-deacetoxyaustalide I // N // inhib. AP-1 dependent transcription without cytotox., inhib. mollusk enzyme // * // * 426 // (17S)-dihydroaustalide K // N // * // * // * 268 Ascomycota Penicllium thomii, Ascomycota Penicillium lividum // (Phaeophyta, Sargassum miyabei) Lazurnaya Bay, Russia // Sargassopenillines A–G, 6,6-spiroketals from the alga-derived fungi Penicillium thomii and Penicillium lividum 427 // sargassopenilline A // N // mod. inibition of radical scavenging (DPPH) // * // * 428 // sargassopenilline B // N // * // * // * 429 // sargassopenilline C // N // inhib. transcription of oncogenic nuclear factor AP-1// * // * 430 // sargassopenilline D // N // modest inhib. of macrophage adhesion // * // * 431 // sargassopenilline E // N // mod. inibition of radical scavenging (DPPH), mod. cytotox. to mammalian cell line // * // * 432 // sargassopenilline F // N // modest inhib. of macrophage adhesion // * // * 433 // sargassopenilline G // N // * // * // * Key:


33

3


3.3


269 Ascomycota Penicillium oxalicum // (Cnidaria, Muricella flexuosa) Sanya, China. // Dihydrothiophene-condensed chromones from a marine-derived fungus Penicillium oxalicum and their structure–bioactivity relationship 434 // oxalicumone D // N // mod.-selective activity vs HTCLs // * // * 435 // oxalicumone E // N // good-mod. activity vs HTCLs // * // * OH

O

OH

OH

O

OH HO

O

OR

OH

O

COOH

OH

CHO

COOMe

R H

NH HO 3SO 436 R = H O 437 R = OH

O †438 R = OH †439 R = H

R R

H N

OH

N H

O OH

442

H N

H

OH

O

O 449

N O

450

HO

H N

HO

H O

O R

O

OH

HN N

O

†453

8

O OH

O

O

CONH 2

O N H

CONH 2

O

H N

O 8

O

OH R= R= OH 448 R = OMe

†447

NH

5

451 R = H 452 R =OH

†446

HO H

N O

O O

HO

O

445

O NH

O

O

H H

†443

5

O

R

N H

R

R=H †444 R = Me

OH

5

O 440 R = H 441 R = Me

OH

N H †458

O

CONH 2 CONH 2

H N

O

O 454 R = 455 R = †456 R = †457 R =

N R H CONH 2 OEt OMe CONH 2 CONH 2

OH

270 Ascomycota Penicillium oxalicum // (sediment) Bohai Bay, China // Two new compounds from a marine-derived fungus Penicillium oxalicum 436 // emodin-3-O-sulphate // N // * // * // * 437 // citreorosein-3-O-sulphate // N // * // * // * 271 Ascomycota Penicillium oxalicum // (Cnidaria, Muricella flexuosa) S. China Sea // Cyclopentane-condensed chromones from marine-derived fungus Penicillium oxalicum 438 // coniochaetone G // N // * // * // * 439 // coniochaetone H // N // * // * // * 440 // coniochaetone I // N // * // * // * 441 // coniochaetone J // N // * // * // * 442 // coniochaetone K // N // * // * // * 272 Ascomycota Penicillium paneum // (sediment) S. China Sea // Prenylated indole alkaloid derivatives from marine sediment-serived fungus Penicillium paneum SD-44 443 // penipaline A // N // * // * // * 444 // penipaline B // N // modest cytotox. vs 2 HTCLs // * // * 445 // penipaline C // N // modest cytotox. vs 2 HTCLs // * // * 273 Ascomycota Penicillium purpurogenum // wild-type ex Bohai Bay, China // Three new and eleven known unusual C25 steroids: activated production of silent metabolites in a marine-derived fungus by chemical mutagenesis strategy using diethyl sulphate 446 // antineocyclocitrinol A // N // weak cytotox. to HTCLs // ex Mutant. // * 447 // antineocyclocitrinol B // N // weak cytotox. to HTCLs // ex Mutant. // * 448 // 23-O-methylantineocyclocitrinol // N // weak cytotox. to HTCLs // ex Mutant. // *

Key:


34

3


3.3


274 Ascomycota Penicillium purpurogenum // wild-type ex Bohai Bay, China // A practical strategy to discover new antitumor compounds by activating silent metabolite production in fungi by diethyl sulphate mutagenesis 449 // penicimutanolone // N // mod. cytotox. vs HTCLs // ex Mutant. Isolated as 6:1 isomeric mixture. // * 450 // penicimutanolone // N // mod. cytotox. vs HTCLs // ex Mutant. Isolated as 6:1 isomeric mixture. // * 451 // penicimutanin A // N // mod. cytotox. vs HTCLs // ex Mutant. // * 452 // penicimutanin B // N // mod. cytotox. vs HTCLs // ex Mutant. // * 453 // penicimutatin // N // mod. cytotox. vs HTCLs // ex Mutant. // * 275 Ascomycota Penicillium purpurogenum // wild-type ex Bohai Bay, China // Seven new and two known lipopeptides as well as five known polyketides: the activated production of silent metabolites in a marine-derived fungus by chemical mutagenesis strategy using diethyl sulphate 454 // penicimutalide A/B // N // weak cytotox. vs HTCLs // ex Mutant. // * 455 // penicimutalide C/D // N // weak cytotox. vs HTCLs // ex Mutant. // * 456 // penicimutalide E // N // weak cytotox. vs HTCLs // ex Mutant. // * 457 // penicimutalide F // N // weak cytotox. vs HTCLs // ex Mutant. // * 458 // penicimutalide G // N // weak cytotox. vs HTCLs // ex Mutant. // * HO

RO

COOH

OH

HO

O

HO

O †464 R = H †465 R = Me

OH

†459

OH

NHPO 3H 2

O

O AcO

O

HO O

OH

HO

O

OAc

O

R3

OH

R HO

R1

461 OH

OAc O

O OH

O †462

R = OH O †463 R = H

HO †466

O

OR5

O R2

R4

467 R1 468 R1 469 R1 470 R1 471 R1 472 R1 473 R1 474 R1 475 R1 476 R1

= R2 = R3 = R 4 = R5 = H =Cl, R 2 = R 3 = R 4 = R 5 = H = R 3 = R 4 = R 5 = H, R 2 = Cl Cl = R 3 = R 5 = H, R 2 = R 4 = Cl = R 2 = Cl, R 3 = R 4 = R 5 = H = R 2 = R 4 = Cl, R 3 = R 5 = H HO = R 2 = R 4 = Cl, R 3 = H, R 5 = Me = R 2 = R 3 = Cl, R 4 = R 5 = H = R 2 = R 3 = R 4 = Cl, R 5 = H = R 2 = R 3 = R 4 = Cl, R 5 = Me

O O

O Cl R1

477 R1 478 R1 479 R1 R 2 480 R 1 481 R1

= H, R 2 = Cl, R 3 = Me = R 2 = Cl, R 3 = Me = R 2 = R3 = H = R 3 = H, R 2 = Cl = R 2 = Cl, R 3 = H

OR3

460

276 Ascomycota Penicillium roqueforti // (seawater) La Laja beach, Canary Islands // Evidence of a new intermediate compound of the chitin biogenesis found in a marine-derived fungus 459 // 2-deoxy-2-phosphamino-α-D-glucopyranose // N // * // * // * 277 Ascomycota Penicillium lividum, Ascomycota Penicillium thomii // (sediment) Lazurnaya Bay, Russia // Spiroketals from marine isolates of the fungi Penicillium thomii KMM 4645 and P. lividum KMM 4663 460 // daldinin D // M // * // * // s128 278 Ascomycota Penicillium sp. // (Echinodermata, Brisaster latifrons) Sea of Okhotsk // Tanzawaic acid derivatives from a marine isolate of Penicillium sp. (SF-6013) with antiinflammatory and PTP1B inhibitory activities 461 // (2E,4Z)-tanzawaic acid D // N // inhib. of NO production // * // * 279 Ascomycota Pseudallescheria boydii // (Echinodermata, Acanthaster planci) Hainan Sanya National Coral Reef Reserve, China // Pseudaboydins A and B: novel isobenzofuranone derivatives from marine fungus Pseudallescheria boydii associated with starfish Acanthaster planci 462 // pseudaboydin A // N // mod. cytotox. vs HTCLs // * // * 463 // pseudaboydin B // N // * // * // * 464 // (R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-5-hydroxybenzofuran // M // * // * // s129 465 // (R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-5-methoxybenzofuran // M // * // * // s130 Key:


35

3


3.3


280 Ascomycota Spicaria elegans, Ascomycota Mariannaea elegans // (sediment) Jiaozhou Bay, China // Eleganketal A, a highly oxygenated dibenzospiroketal from S. elegans KLA03 466 // eleganketal // N // * // * // * 281 Ascomycota Spiromastix sp. // (sediment) South Atlantic Ocean // Spiromastixones A–O, AB chlorodepsidones from a deep-sea-derived Spiromastix sp. fungus 467 // spiromastixone A // N // mod.-good inhib. of Gram-positive bacteria // * // * 468 // spiromastixone B // N // mod.-good inhib. of Gram-positive bacteria // * // * 469 // spiromastixone C // N // mod.-good inhib. of Gram-positive bacteria // * // * 470 // spiromastixone D // N // mod.-good inhib. of Gram-positive bacteria // * // * 471 // spiromastixone E // N // mod.-good inhib. of Gram-positive bacteria // * // * 472 // spiromastixone F // N // mod.-good inhib. of Gram-positive bacteria, potent inhib. of MRSA and MRSE // * // * 473 // spiromastixone G // N // mod.-good inhib. of Gram-positive bacteria, potent inhib. of MRSA and MRSE // * // * 474 // spiromastixone H // N // mod.-good inhib. of Gram-positive bacteria, potent inhib. of MRSA and MRSE // * // * 475 // spiromastixone I // N // mod.-good inhib. of Gram-positive bacteria, potent inhib. of MRSA and MRSE // * // * 476 // spiromastixone J // N // mod.-good inhib. of Gram-positive bacteria, potent inhib. of MRSA and MRSE, inhib. of VRE // * // * 477 // spiromastixone K // N // mod.-good inhib. of Gram-positive bacteria, // * // * 478 // spiromastixone L // N // mod.-good inhib. of Gram-positive bacteria, // * // * 479 // spiromastixone M // N // mod.-good inhib. of Gram-positive bacteria, // * // * 480 // spiromastixone N // N // mod.-good inhib. of Gram-positive bacteria, // * // * 481 // spiromastixone O // N // mod.-good inhib. of Gram-positive bacteria, // * // * O

O

O NR 4

HO

NH

OH

H O

NH O

O

O R1 R2

HO

H †482

OH

HO

HO

R3 †483 R = R = H, R = OH , R 4 = (CH 2) 4COOH 1 3 2 †484 R = R = H, R = OH , R 3 = OH 1 4 2 †490 R = OH , R 2 = OH , R 3 = R 4 = H 1 †491 R = OH , R 2 = OH , R 3 = R 4 = H 1 †492 R = OH , R 2 = OAc , R 3 = R 4 = H 1

NH

O H

O

O

HO

O R

O

O

OH

H

NR 2

HO

O

HO

NR HO

NH HO O

NH

O

O

HO

O

OH

OH O

O

HN HO

†485

O O

H

†486

R1 †487

R1 = R1 = †489 R = 1 †488

H

HO

H

OH , R 2 = H OH , R 2 = H OH , R 2 = (CH 2) 2OH

†493

HO

H †494 †495

H †496

R=H R = (CH 2) 2OH

R=H †497 R = OH

282 Ascomycota Stachybotrys chartarum // (Porifera, Niphates recondita) Weizhou Island, China // Chartarlactams A–P, phenylspirodrimanes from the sponge-associated fungus Stachybotrys chartarum with antihyperlipidemic activities 482 // chartarlactam A // N // * // * // * 483 // chartarlactam B // N // * // * // * 484 // chartarlactam C // N // * // * // * 485 // chartarlactam D // N // antihyperlipidemic activity // * // * 486 // chartarlactam E // N // antihyperlipidemic activity// * // * 487 // chartarlactam F // N // antihyperlipidemic activity // * // * 488 // chartarlactam G // N // * // * // * 489 // chartarlactam H // N // * // * // * Key:


36

3


3.3


490 // chartarlactam I // N // * // * // * 491 // chartarlactam J // N // * // * // * 492 // chartarlactam K // N // antihyperlipidemic activity// * // * 493 // chartarlactam L // N // antihyperlipidemic activity // * // * 494 // chartarlactam M // N // * // * // * 495 // chartarlactam N // N // antihyperlipidemic activity // * // * 496 // chartarlactam O // N // antihyperlipidemic activity // * // * 497 // chartarlactam P // N // * // * // * O

O

X OH

OH

HN

O

OH

HN

OH HN

OH

OH

†498

O OH

R2

HN

HN OH

O

R1

OR

O

OH

499 X = O, R = H 500 X = O, R = SO3H 501 X = NH, R = SO3H

†502

R1 =

Me, R 2 =

†504

R1 =

Me , R 2 =

OH

O

HO †505

†503

OH

283 Ascomycota Stachybotrys chartarum // (Porifera, Niphates sp.) Beibuwan Bay, China // Isoindolinone-type alkaloids from the sponge-derived fungus Stachybotrys chartarum 498 // chartarutine A // N // * // * // * 499 // chartarutine B // N // mod. inhib. of HIV-1 // * // * 500 // chartarutine C // N // * // * // * 501 // chartarutine D // N // * // * // * 502 // chartarutine E // N // * // * // * 503 // chartarutine F // N // * // * // * 504 // chartarutine G // N // mod. inhib. of HIV-1 // * // * 505 // chartarutine H // N // mod. inhib. of HIV-1 // * // * H

HO HO

H

O

H

HO

H

O COOH H

OH H

O

O

AcO O O

HO

HO

HO

N NH 506

507 O

H O

O

R

OH O

AcO

N 508 R = iPr 509 R = Ph

O

O

511

COOH

9

O

HO

HO

O

COOH

5

O 514

O O

N

COOH O

510

OH

OAc

513 O

512

284 Ascomycota Stachybotrys sp. // (driftwood) Helgoland, North Sea, Germany // Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347 506 // stachyin A // N // good AB activity, modest cytotox. vs 2 HTCLs // * // * 507 // stachyin B // N // * // * // * 508 // * // M // * // * // s131 509 // * // M // * // * // s131 Key:


37

3


3.3


285 Ascomycota Talaromyces trachyspermus // (Porifera, Clathria reinwardti) Kram Is., Thailand // Spiculisporic acid E, a new spiculisporic acid derivative and ergosterol derivatives from the marine-sponge associated fungus Talaromyces trachyspermus (KUFA 0021). 510 // 3-acetyl ergosterol 5,8-endoperoxide // M // * // Possible artefact. // s132 511 // spiculisporic acid E // N // * // * // * 286 Ascomycota Trichoderma citrinoviride // (sediment) Langqi Is., China // Novel cytotoxic metabolites from the marine-derived fungus Trichoderma citrinoviride 512 // trichoderiol C // N // * // * // * 513 // citrinoviric acid // N // weak cytotox. vs HTCL (A-375) // * // * 514 // penicillenol D // N // weak cytotox. vs HTCL (A-375) // * // * OH O

RO

O

O

H

COOMe

OH

H

N H †515

O

OH

MeO

HO

H

O

OH

H

OH O

H

516 R = H 517 R = O

OMe

OH

OH OH

OH

O

OH

H

H

OH

OH OH

518

RO

NH

O

N

HO

N

†519

N

OH 520

O

521

O

H

O †522 †523

287 Ascomycota Trichoderma harzianum // (Porifera, Halichondria okadai) Osaka bay, Japan // Tandyukisin, a novel ketoaldehyde decalin derivative, produced by a marine sponge-derived Trichoderma harzianum 515 // tandyukisin // N // weak cytotox. vs 3 HTCLs // * // * 288 Ascomycota Trichoderma sp. // (unspecified source) Fram Strait, Greenland Sea // Two new antibiotic pyridones produced by a marine fungus, Trichoderma sp. strain MF106 516 // trichodin A // N // modest inhib. of S. epidermidis // * // * 517 // * // N // * // * // * 289 Ascomycota Verticillium tenerum // (unknown alga) Santa Barbara, U.S.A. // Phytochemical studies of Verticillium teneru and Acremonium 518 // 2-(D-glycer-1',2'-dihydroxyethyl)furan // M // * // * // s133 290 Ascomycota Xylaria sp. // (endophyte of unpsecified mangrove) Hong Kong // Xylanthraquinone, a new anthraquinone from the fungus Xylaria sp. 2508 from the S. China Sea 519 // xylanthraquinone // N // * // * // * 291 Ascomycota Xylariaceae sp. // (Cnidaria, Melitodes squamata) S. China Sea // Alkaloids from Xylariaceae sp., a marine-derived fungus. 520 // 5-(2’-hydroxypropyl)pyridin-3-ol // N // * // Racemic mixture. // * 292 Ascomycota, Order Xylariales // (unidentified sponge) Indonesia // Xylarianaphthol-1, a novel dinaphthofuran derivative, activates p21 promoter in a p53-independent manner 521 // xylarianaphthol-1 // N // Activation of p21 promoter activity. // * // * 294 Ascomycota Aspergillus sp. // * // Total synthesis and structural revision of (−)-protubonine A and (−)-protubonine B 522 // protubonine A // R // * // First synthesis. // s134 523 // protubonine // R // * // First synthesis. // s134

Key:


38

R=H R = Ac

3


O

H

3.3


H N

N

OH

O

O

COOMe

O

O

N N H

H

O O

O

OH

NH

H

†525

COOMe

Cl

HN

H

HN

†524

COOMe

H N

HN

O

O O

NH

O

HO

OH

OH MeOOC

OH

NH †527

526

OH

296 Ascomycota Eurotium cristatum // * // Total synthesis and structural revision of (+)-cristatumin C 524 // cristatumin C // R // * // First synthesis. // s135 298 Ascomycota Penicillium oxalicum // // Total synthesis of (±)-oxalicumone C and chiral resolution and elucidation of its absolute configuration 525 // (S)-oxalicumone C // R // * // First synthesis. // s136 300 Ascomycota Aspergillus clavatus // Kueishantao hydrothermal vent, Taiwan // Zn-driven discovery of a hydrothermal vent fungal metabolite clavatustide C, and an experimental study of the anti-cancer mechanism of clavatustide B 526 // clavatustide C // M // * // * // s137 302 * // * // Synthesis of marine natural product (−)-pericosine E 527 // (–)-pericosine E // R // * // Occurs as enantiomeric mixture in nature. // s138

Key:


39

3


3.4


OH

NHAc O

O

N

O

OH

O

N

N O O O O

NH

O

N

OH

OH

O

†530

OH R = nBu †533 R = Me

535

534

†532

†531

OH OMe

OH

O

O O

HO

O

O

HO

O O OH

HO

O †539

†540

O

O HO

O

O

537 R = Me, X = OMe,H O 538 R = CH 2CH(OH)CH 2OH, X = O

HO OH

OH

O

O

5

O

OH

X OH

O

O

OH

ROOC O

O

†536

N

†528

MeO OH O

O

N H

COOMe O

O

†529

O O

ROOC O

HN

O

O

N

O O O

HN

HN

HO

O

N

NH

NH HN

OH

O OH

HO

OH

O O 542

O

HO

†543

541

348 Ascomycota Phomopsis sp., Ascomycota Alternaria sp. // (unspecified mangrove) Leizhou Peninsula, China // A new cyclopeptide with antifungal activity from the co-culture broth of two marine mangrove fungi 528 // Cyclo-( L -leucyl-trans-4-hydroxy- L -prolyl- D -leucyl-trans-4-hydroxy-L-proline) // N // mod.-high inhib. vs 4 crop threatening fungi. // * // * 349 Ascomycota Phomopsis sp., Ascomycota Alternaria sp. // (unspecified mangrove) Leizhou Peninsula, China // Two new cyclopeptides from the co-culture broth of two marine mangrove fungi and their antifungal activity 529 // cyclo(D -Pro- L -Tyr- L -Pro- L -Tyr) // N // mod.-high inhib. vs 4 crop threatening fungi // * // * 530 // cyclo(Gly- L -Phe- L -Pro- L -Tyr) // N // mod.-high inhib. vs 4 crop threatening fungi // * // * 350 Ascomycota Aspergillus sp. // (Phaeophyta. Sargassum sp.) Helgoland, Germany // Psychrophilin E, a new cyclotripeptide, from co-fermentation of two alga-derived Aspergillus spp. 531 // psychrophilin E // N // weak cytotox. vs 4 HTCLs // * // * 353 Ascomycota Aspergillus flavipes // (Tracheophyta, Acanthus ilicifolius, leaves) Daya Bay,China // New phenyl derivatives from endophytic A. flavipes derived of Acanthus ilicifolius 532 // flavipesin A // N // good AB activity // * // * 533 // flavipesin B // N // * // * // * 534 // 3,4-diphenylfuran-2(5H)-one // M // * // * // s139 535 // phenguignardic acid methyl ester // M // * // * // s140 354 Ascomycota Diaporthe sp. // (Tracheophyta, Rhizophora stylosa, leaves) Hainan Province, China // Diaporine, a novel endophyte-derived regulator of macrophage differentiation 536 // diaporine // N // polarise tumour associated macrophages (TABs) // * // * 355 Ascomycota Dothiorella sp. // (Tracheophyta, Aegiceras corniculatum, bark) Jiulong River estuary, China // Two new polyketides from mangrove endophytic fungus Dothiorella sp. 537 // dothiorelone F // N // * // * // * 538 // dothiorelone I // N // * // * // * Key:


40

3


3.4


358 Ascomycota Penicillium dipodomyicola // (Tracheophyta, Acanthus ilicifolius, stem) S. China Sea, China // Peniphenones A–D from the mangrove fungus Penicillium dipodomyicola HN4-3A as inhibitors of M. tuberculosis phosphatase Mptp 539 // (−)-peniphenone A // N // * // * // * 540 // (+)-peniphenone A // N // * // * // * 541 // peniphenone B // N // strong inhib. of M. tuberculosis protein tyrosine phosphatase B (MptpB) // * // * 542 // peniphenone C // N // * // * // * 543 // peniphenone D // N // * // * // * MeOOC

O

OH

O

O

O †544

O

O

O MeO

†545

OH CHO

OH

O

HO

OMe

O

OH

OMe O

MeOOC

OH O

O

O

HO MeO

OH X

OH

OH

OMe O

O 546

OH

R

O O

OH

H 547

†548

†549

†554 †550

X = 2H, R = †551 X = 2H, R = †552 X = O, R = †553 X = O, R =

OH OH OH OH

CHO

HOOC

O †556

OH

O

O 557

COOH

HO

OH 555

360 Ascomycota Penicillium sp., Actinobacteria Streptomyces fradiae // (Tracheophyta, Aegiceras corniculatum, sediment) Wenchang, China // Phenolic polyketides from the co-cultivation of marine-derived Penicillium sp. WC-29-5 and Streptomyces fradiae 007 544 // (9R,14S)-epoxy-11-deoxyfunicone // M // mod. cytotox. vs HTCL (H1975) // * // s141 545 // (9S,14R)-epoxy-11-deoxyfunicone // N // mod. cytotox. vs 2 HTCLs// * // * 361 Ascomycota Penicillium sp. // (Tracheophyta, Avicennia marina) Fujian, China // antiproliferative metabolites from the endophytic fungus Penicillium sp. FJ-1 isolated from a mangrove Avicennia marina 546 // 4-(2’,3’-dihydroxy-3’-methyl-butanoxy)-phenethanol // N // modest cytotox. vs two HTCLs // * // * 547 // 15-hydroxy-6α,12-epoxy-7β,10αH,11βH-spiroax-4-ene-12-one // N // inhib. tum. growth human xenograft osteosarcoma. potent cytotox. vs HTCLs (especially MG-63) // * // * 362 Ascomycota Pestalotiopsis vaccinii // (Tracheophyta, Kandelia candel) southern China // Eight new polyketide metabolites from the fungus Pestalotiopsis vaccinii endogenous with the mangrove plant Kandelia candel (L.) Druce 548 // vaccinol A // N // * // * // * 549 // vaccinol B // N // * // * // * 550 // vaccinol C // N // * // * // * 551 // vaccinol D // N // * // * // * 552 // vaccinol E // N // * // * // * 553 // vaccinol F // N // * // * // * 554 // vaccinol G // N // * // * // * 555 // vaccinal A // N // potent COX-2 inhib., modest inhib. of anti-enterovirus (EV71) // * // * 363 Ascomycota Acremonium strictum, Ascomycota Sarocladium strictum // (Tracheophyta, Rhizopora apiculata) CatBa Is., Vietnam // Polyketides from the mangrove-derived endophytic fungus Acremonium strictum 556 // 6′-hydroxypestalotiopsone C // N // * // * // * 557 // * // N // * // * // * Key:


41

3


3.4


558 // acropyrone // N // * // * // * 559 // waol acid // N // * // * // * 560 // pestalotiopene C // N // * // * // * R2 R1

OH

4

HO

HO

O

HO

O

HO

HO

COOH CHO

COOH

5

O

Cl

OH OH

O

O

HO O

OH

O O

OH †565

COOH

O

OH

HO

O

OH

OH

O O

O

N

OH †567

OH

O

O

OH

OH

N 569 HOOC

OH

O †564

O

OH

O

O

OMe

H

†560

OH

OH

OH

561 R1 = H, R 2 = CHO 562 R1 = R 2 = CHO 563 R1 = CHO, R 2 = H

OH

HO

OMe

OH

O

OH

O

HO O

OH 558

OMe

O

H

OH

†559

O

H

HO

O

O

HO

OH OH HO

OH

O

R1 O

Cl

R2

HO

†566

N H

OH

OH

O

OH

OH

OH

OH O

H

O

NHAc

NHAc

†568

NHAc

O

O

HO O

O

†570

O

O

†571

O

O

572 R1 = R 2 = H 573 R1 = Ac, R 2 = COOH

O

O

†574

O

O

H OH OR †576 R = H †577 R = Ac

†578

N H H

NH O

N H 580

579

†575

364 Ascomycota Alternaria sp. // (Tracheophyta, Alternaria sp., root) Leizhou peninsula, China // Three new resveratrol derivatives from the mangrove endophytic fungus Alternaria sp. 561 // resveratrodehyde A // N // cytotox. vs 3 HTCLs, mod. radical scavenging activity (DPPH) // * // * 562 // resveratrodehyde B // N // cytotox. vs 3 HTCLs // * // * 563 // resveratrodehyde C // N // cytotox. vs 3 HTCLs, mod. radical scavenging activity (DPPH) // * // * 365 Ascomycota Alternaria sp. // (Tracheophyta, Excoecaria agallocha, root) Shankou, China. // Alterporriol-type dimers from the mangrove endophytic fungus, Alternaria sp. (SK11), and their MptpB inhib.s 564 // alterporriol S // N // * // * // * 366 Ascomycota Daldinia eschscholtzii // (Tracheophyta, Scaevola sericea, branch) Haikou, China // Five new secondary metabolites produced by a marine-associated fungus, Daldinia eschscholzii 565 // daldiniside A // N // * // * // * 566 // daldiniside B // N // * // * // * 567 // daldiniside C // N // * // * // * 568 // 1-(3-indolyl)-2R,3-dihydroxypropan-1-one // N // * // * // * 569 // 3-ethyl-2,5-pyrazinedipropanoic acid // N // * // * // *

Key:


42

3


3.4


367 Ascomycota Guignardia sp. // (Tracheophyta, Kandelia candel, fruit) Daya Bay, China // Guignardins A–F, spirodioxynaphthalenes from the endophytic fungus Guignardia sp. KcF8 as a new class of PTP1B and SIRT1 inhib.s 570 // guignardin A // N // * // * // * 571 // guignardin B // N // mod. inhib. of S. aureus // * // * 572 // guignardin C // N // inhib. of human protein tyrosine phosphatase 1B and silent information regulator T1 (SIRT1), mod. inhib. of S. aureus // * // * 573 // guignardin D // N // * // * // * 574 // guignardin E // N // cytotox. vs 10 HTCLs // * // * 575 // guignardin F // N // cytotox. vs 10 HTCLs // * // * 368 Ascomycota Penicillium bilaiae // (Tracheophyta, Lumnitzera racemosa, soil) Hainan Is., China // Penicibilaenes A and B, sesquiterpenes with a tricyclo[6.3.1.1,5]dodecane skeleton from the marine isolate of Penicillium bilaiae MA-267 576 // penicibilaene A // N // potent inhib. of plant pathogenic fungus C. gloeosporoides // * // * 577 // penicibilaene B // N // potent inhib. of plant pathogenic fungus C. gloeosporoides// * // * 369 Ascomycota Penicillium brocae // (Tracheophyta, Avicennia marina, leaves) Hainan Is., China // Brocaeloids A–C, 4-oxoquinoline and indole alkaloids with C-2 reversed prenylation from the mangrove-derived endophytic fungus Penicillium brocae 578 // brocaeloid A // N // * // * // * 579 // brocaeloid B // N // modest cytotox. vs A. salina // * // * 580 // brocaeloid C // N // * // * // * O

O

H

X

O N

R OH

H

S S

H N

O R = OMe, X = O H X †582 R = H, X = O †583 R = OH, X = OH, H †581

O

O

OH N

MeO OH

H

S S

H

OH N

OH

N

OH

H

S S

H

H

O

†585 †586

O OH

OH OH

HO

X= X=O

N

OH

O OH , H H OH

HO

N

N

O

O †584

O O

H N

H

H

†587

†588

HO

O

OH †589

370 Ascomycota Penicillium brocae // (Tracheophyta, Avicennia marina) Hainan Is., China // Brocazines A–F, cytotox. bisthiodiketopiperazine derivatives from Penicillium brocae MA-231, an endophytic fungus derived from the marine mangrove plant Avicennia marina 581 // brocazine A // N // good cytotox. vs 9 HTCLs // * // * 582 // brocazine B // N // good cytotox. vs 9 HTCLs // * // * 583 // brocazine C // N // * // * // * 584 // brocazine D // N // * // * // * 585 // brocazine E // N // good cytotox. vs 9 HTCLs // * // * 586 // brocazine F // N // good cytotox. vs 9 HTCLs // * // * 371 Ascomycota Penicillium sclerotiorum // (Tracheophyta, Bruguiera sclerotiorum, stem) Zhanjiang, China // (+)-Cyclopenol, a new naturally occurring 7-membered 2,5-dioxopiperazine alkaloid from the fungus Penicillium sclerotiorum endogenous with the Chinese mangrove Bruguiera gymnorrhiza 587 // (+)-cyclopenol // N // * // * // * 372 Ascomycota Penicillium sp. // (Tracheophyta, Kandelia candel, root) Shankou, China // A new polyketide from the mangrove endophytic fungus Penicillium sp. sk14JW2P 588 // (+)-13-hydroxylpalitantin // N // * // * // *

Key:


43

3


3.4


373 Ascomycota Penicillium sp. // (Tracheophyta, Bruguiera gymnorrhiza) Techeng Is., China // Penibruguieramine A, a novel pyrrolizidine alkaloid from the endophytic fungus Penicillium sp. GD6 associated with Chinese mangrove Bruguiera gymnorrhiza 589 // penibruguieramine A // N // * // * // * O

O

N N

N N O

H

H

HN N

O H

N H

O

†590

O

O O

N H

O

†591

OH

O

O

†592

O

O

H †593

O MeOOC OH

O

OH MeO

†594

COOH

O MeOOC OH

O †600

599

O

H

H H 596

595

601

HO

H

OH

O HO

OH R2 602 R1 = CH 2OH, R 2 = H 603 R1 = CHO, R 2 = OH

HO

OAc H OH †597

O

CHO OH

R1

HO

H

AcO

O N

O HO

NH

HN

HO

HO

O

H

O

598

O O

OH

OAc O

COOH

HO

H

O

MeO

OH

O O

O

OAc MeO

HOOC

N O

O

N H

O

O

O O

H

605

OH

CHO 604

OH

CHO OH

OSO3H

606

374 Ascomycota Penicillium sp. // (Mangrove sediment) Sanya City, China // New prenylated indole alkaloids from fungus Penicillium sp. derived of mangrove soil sample 590 // mangrovamide A // N // * // * // * 591 // mangrovamide B // N // * // * // * 592 // mangrovamide C // N // * // * // * 375 Ascomycota Penicillium sp. // (seawater) Zhanjiang Mangrove National Nature Reserve, China // Meroterpenes and azaphilones from marine mangrove endophytic fungus Penicillium 303# 593 // * // N // weak cytotox. vs 4 HTCLs // * // * 594 // * // N // weak cytotox. vs 4 HTCLs // * // * 595 // * // N // weak cytotox. vs 4 HTCLs // * // * 376 Ascomycota Penicillium sp. // Tracheophyta, Bruguiera gymnorrhiza, bark) Zhanjiang, China // A new cyclic peptide and a new steroid from the fungus Penicillium sp. GD6 isolated from the mangrove Bruguiera gymnorrhiza 596 // 5,5′-epoxy-MKN-349A // N // * // * // * 597 // 11-O-acetyl-NGA0187 // N // * // * // * 377 Ascomycota Penicillium sp. // (Tracheophyta, Bruguiera gymnorrhiza, sediment) Hainan Is., China // Diphenyl ether and benzophenone derivatives from the marine mangrove-derived fungus Penicillium sp. MA-37 598 // iso-monodictyphenone // N // mod. activity vs A. hydrophilia, weak cytotox. vs A. salina // * // * 599 // penikellide A // N // weak cytotox. vs A. salina // * // * 600 // penikellide B // N // weak cytotox. vs A. salina // * // * 378 Ascomycota Penicillium sp. // * // Secondary metabolites and AB activities of a Bruguiera sexangula var. Rhynchopetala -derived fungus Penicillium sp. (J41221) 601 // 11-oxo-12α-acetoxy-4,4-dimethyl-24-methylene-5α-cholesta-8,14-diene-2α,3β-diol // M // * // * // s142 Key:


44

3


3.4


379 Ascomycota Pestalotiopsis sp. // (Tracheophyta, Aegiceras corniculatum, stem) Nansha mangrove wetland, China // Pestalols A–E, new alkenyl phenol and benzaldehyde derivatives from endophytic fungus Pestalotiopsis sp. AcBC2 isolated from the Chinese mangrove plant Aegiceras corniculatum 602 // pestalol A // N // weak inhib. vs 2 viruses // * // * 603 // pestalol B // N // inhib. of tuberculosis. weak cytotox. vs 10 HTCLs, weak inhib. vs 2 viruses // * // * 604 // pestalol C // N // weak cytotox. vs 10 HTCLs // * // * 605 // pestalol D // N // weak inhib. vs 2 viruses // * // * 606 // pestalol E // N // weak inhib. vs 2 viruses // * // * SMe

SMe

O

O O

OH

H

N OH

H

N

NH OH

NH

H

HO O MeS

O †607

OH

H

†608

NS SN

COOH O

HO H

H

O

O

O

OH

O

HO

OH

HO

OMe

OMe

O O

O

O

HO

O

O

O

O

OH

610 †609

O

O

O

O

O

O †613

612

†614

OH

OH †615

611

380 Ascomycota Phoma sp. // (Tracheophyta, Kandelia candel, fruit) Wenchang, China // Thiodiketopiperazines from the marine-derived fungus Phoma sp. OUCMDZ-1847 607 // phomazine A // N // * // * // * 608 // phomazine B // N // weak cytotox. vs HTCL (MGC-803) // * // * 609 // phomazine C // N // * // * // * 381 Ascomycota Phomopsis sp. // (Mangrove sediment) ZhuHai, China // A new isochroman derivative from the marine fungus Phomopsis sp. (No. Gx-4) 610 // (3R,4S)-3,4-dihydro-8-hydroxy-4-methoxy-3-methylisocoumarin // N // * // * // * 382 Ascomycota Phomopsis sp. // (Tracheophyta, Kandelia candel, leaves) Fugong, Chinal // Phomopsidone A, a novel depsidone metabolite from the mangrove endophytic fungus Phomopsis sp. A123 611 // phomopsidone A // N // * // * // * 612 // 7-methyl-6-methoxy-3-oxo-1,3-dihydroisobenzofuran-4-carboxylic acid // M // * // * // s143 383 Basidiomycota Pseudolagarobasidium acaciicola // (Tracheophyta, Bruguiera gymnorrhiza) Unspecified location. // Tricyclic and spirobicyclic norsesquiterpenes from the endophytic fungus Pseudolagarobasidium acaciicola 613 // acaciicolin A // N // * // * // * 614 // spiroacaciicolide A // N // * // * // * 615 // 3-epi-steperoxide A // N // good cytotox. vs 8 HTCLs // * // * OH

OH

OH

O

H

H

H

H

O O

O

O

OH OH

O

O

OR

O O

617 R = H 618 R = Me

O

OH 619

Key:

H

H

H O

616

HO

OH

O

O

O

R OH

620 R 621 R 622 R 623 R

O

O

=H OH = OH = = OMe

MeO

COOH O

OH OR

O

625 R = H 626 R = Me

624


45

3


3.4


384 Ascomycota Rhytidhysteron sp. // (Tracheophyta, Azima sarmentosa, leaves) Samutsakhon province, Thailand // Spirobisnaphthalenes from the mangrove-derived fungus Rhytidhysteron sp. AS21B 616 // rhytidone A // N // * // * // * 617 // rhytidone B // N // * // * // * 618 // rhytidone C // N // weak cytotox. vs 2 HTCLs // * // * 385 Ascomycota Rhytidhysteron sp. // (Tracheophyta, Azima sarmentosa, leaves) Samutsakhon Province, Thailand // Rhytidenones A–F, spirobisnaphthalenes from Rhytidhysteron sp. AS21B, an endophytic fungus 619 // rhytidenone A // N // * // * // * 620 // rhytidenone B // N // * // * // * 621 // rhytidenone C // N // good antiinflammatory activity (NO production inhib.) // Probable artefact of isolation of 624 // * 622 // rhytidenone D // N // modest antiinflammatory activity (NO production inhib.) // Probable artefact of isolation of 624 // * 623 // rhytidenone E // N // * // Probable artefact of isolation of 624 // * 624 // rhytidenone F // N // * // * // * 386 Ascomycota Stemphylium sp. // (Tracheophyta, Bruguiera sexangula, leaves) S. China Sea // Antibacterial α-pyrone derivatives from a mangrove-derived fungus Stemphylium sp. 625 // infectopyrone A // N // mod. broad spectrum AB activity // * // * 626 // infectopyrone B // N // mod. broad spectrum AB activity // * // * OH O

OH

O

O

MeO

MeO O

†627

OH

O

OH

OH

OAc OH OAc

O MeO

OH

O

O

†628

†629

OH MeO

H

OH OH

OH

O

H

O OH

MeO OH

R

O OH

O OH

O

MeO

O

OH

O

OH

OH

OH

HO O

O OH OMe

H

O

O

OH

635

HO

HO

OAc †630

HO

HO

631 R = OH 632 R = H

O

OMe

OMe

OH

OH

OH

O

O

OH

OMe 633

†634

O

OH

O

OH

387 Ascomycota Stemphylium sp. // (Tracheophyta, Bruguiera sexangula var. Rhynchopetala) S. China Sea // Bioactive anthraquinone derivatives from the mangrove-derived fungus Stemphylium sp. 33231 627 // auxarthrol C // N // * // * // * 628 // macrosporin 2-O-(6′-acetyl)-α-D-glucopyranoside // N // modest cytotox. vs A. salina // * // * 629 // 2-O-acetylaltersolanol B // N // * // * // * 630 // 2-O-acetylaltersolanol L // N // * // * // * 631 // alterporriol T // N // * // * // * 632 // alterporriol U // N // * // * // * 633 // alterporriol V // N // * // * // * 634 // alterporriol W // N // * // * // * 388 Ascomycota sp. Family Xylariaceae // Sanya, China // Xylaolide A, a new lactone from the fungus Xylariaceae sp. DPZ-SY43 635 // xylaolide A // N // * // * // * Key:


46

OH

3


3.5

Cyanobacteria

OH

O OMe MeO

OH

636 O

O

O

O

H N

N

O HO

637

OH

N H

O HN

O

O O †638

O

HO

O

H N

O

N H

N

OMe MeO

O

O

O

N

N H

O

O N

N

O

N

N

O

OH

O O

H N OH

H N

O

N

†639

640

O

O

389 Cyanobacteria Leptolyngbya sp. // Ishigaki Is., Japan // An inhibitor of the adipogenic differentiation of 3T3-L1 cells, yoshinone A, and its analogs, isolated from Leptolyngbya sp. 636 // yoshinone A // N // inhib. of differentiation of 3T3-4 cells to adipocytes// * // * 637 // yoshinones B1 & B2 // N // * // Diasteroisomers // * 390 Cyanobacteria Lyngbya sp. // Kuraha, Japan // Kurahamide, a cyclic depsipeptide analog of dolastatin 13 from a marine cyanobacterial assemblage of Lyngbya sp. 638 // kurahamide // N // potent protease inhib. (elastase and chymotrypsin), mod. cytotox. (2 HTCLs) // * // * 391 Cyanobacteria Lyngbya sp. // Kuraha, Japan // Kurahyne, an acetylene-containing lipopeptide from a marine cyanobacterial assemblage of Lyngbya sp. 639 // kurahyne // N // cytotox. (2 HTCLs) // induces apoptosis // * 392 Cyanobacteria Moorea bouillonii // Pigeon Is., Papua New Guinea // Mooreamide A: a cannabinomimetic lipid from the marine cyanobacterium Moorea bouillonii 640 // mooreamide A // N // cannabinoid recptor (CB1) binding ligand // * // * OH

HO

OH

HO

OH

OH

O

O

HOOC HO

OMe O

R O

OH

†641 †642

R = Br HO R=H

HN

O

O

O

OH

O

N

N H

H 2NOC HO

N H

O

O

O

NH

HO O

H N

N H

O

HO

O

OH

O

R

OH

9

HN

O

O

NH

COOH

H 2NOC

N H

O

N

O

HO

O

O

OH

R

9

O

O

N H

CONH 2 HO

643 R = Cl 645 R = H

O

O

O N H

O

H N

N H

O

HO

HO

O

H N

HO

O

OH

HOOC

O

HO

HO

O

H N

HO

HO

OH

O

O O OMe

O

HO

OH

O

N H

CONH 2

O

OH

644 R = Cl 646 R = H

OH

395 Cyanobacteria Trichodesmium erythraeum // Pulau Seringat Kias, Singapore // Anti-chikungunya viral activities of aplysiatoxin-related compounds from the marine T. erythraeum 641 // 3-methoxyaplysiatoxin // N // * // * // * 642 // 3-methoxydebromoaplysiatoxin // N // good inhibition of Chikungunya virus (CHIKV) // * // * Key:


47

3


3.5

Cyanobacteria

396 Cyanobacteria Anabaena cylindrica // Rügen Is., Germany // Balticidins A–D, antifungal hassallidin-like lipopeptides from the Baltic Sea cyanobacterium Anabaena cylindrica Bio33 643 // balticidin A // N // inhib. of Candida // * // * 644 // balticidin B // N // inhib. of Candida // * // * 645 // balticidin C // N // inhib. of Candida // * // * 646 // balticidin D // N // inhib. of Candida // * // * O HO O

O

O

O

N

O

OH

R

†647

N

OH

O NH

O

H N OH

OMe

OH

H N

O N

N H

O

COOMe

N

N

O

N

H N

N

O

O

O

HO N H

O

H N

O

H N

N O

CONH 2 Me

†652

O

N H †649

†648

†650

R = Me R=H

651

397 Cyanobacteria Lyngbya sp. // Ishigaki Is., Japan // Biselyngbyolide B, a novel ER stress-inducer isolated from the marine cyanobacterium Lyngbya sp. 647 // biselyngbyolide B // N // potent inhib. (2 HTCLs), ER stress induction // induces apoptosis // * 398 Cyanobacteria Lyngbya sp. // Kuraha Beach, Japan // Maedamide, a novel chymotrypsin inhibitor from a marine cyanobacterial assemblage of Lyngbya sp. 648 // maedamide // N // Selective inhib. of chymotrypsin. Strong cytotox. (2 HTCLs) // * // * 400 Cyanobacteria Moorea producens // Kahala Beach, Hawaii // Two new lyngbyatoxin derivatives from the cyanobacterium, Moorea producens 649 // 2-oxo-3(R)-hydroxy-lyngbyatoxin A // N // weak but acute cytotox. vs A. salina // * // * 650 // 2-oxo-3(R)-hydroxy-13-N-desmethyl-lyngbyatoxin A // N // weak but acute cytotox. vs A. salina // * // * 399 Cyanobacteria Moorea producens // Kahala Beach, Hawaii // A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens 651 // 12-epi-lyngbyatoxin A // M // mod. cytotox. ( 2 HTCLs), cytotox. to shrimp, Palaemon paucidens // known syn. deriv. // s144 401 Cyanobacteria Oscillatoria nigroviridis // Lawrence Reef, Colombia // Almiramide D, cytotoxic peptide from the marine cyanobacterium Oscillatoria nigroviridis 652 // almiramide D // N // weak cytox (5 HTCLs), potent cytotox. vs fibroblasts // * // * CONH 2 R

O

N

N

O

O

N H

CONH 2 O

H N

N O

O O

N

OH O N

O

N H O

†653

COOMe

R = Me †654 R = H

COOMe

O H N

N O

H N

H

OH

H

H

O

O

O †655

O

H

†656

O

†657

402 Cyanobacteria Symploca sp. // Kimbe Bay,New Britain, Papua New Guinea// Lipopeptides from the tropical marine cyanobacterium Symploca sp. 653 // tasiamide C // N // * // * // * 654 // tasiamide D // N // * // * // * 655 // tasiamide E // N // * // * // * 404 Cyanobacteria Oscillatoria sp. // * // Coibacins A and B: total synthesis and stereochemical revision 656 // coibacin A // R // * // stereochem. detmn. // s145 657 // coibacin B // R // * // stereochem. detmn. // s145 Key:


48

3


3.6

Dinoflagellates

OH OH

OH

HO 3SO

OH OH

O O

O O

†658

OH

O

HO H

O

O

O

HO OH

O

H N

OH

O

OH

HO O

HO

659

OH

HO

O

HO

O

O O

O

660

COOH

HO

426 Dinophyta Amphidinium sp. // Iriomote Is., Japan // Amphirionin-4 with potent proliferation-promoting activity on bone marrow stromal cells from a marine dinoflagellate Amphidinium species 658 // amphirionin-4 // N // potent growth promoter of ST-2 cells // biosyn. study // * 427 Dinoflagellata Dinophysis acuminata // Masan Bay. Korea // Acuminolide A: structure and bioactivity of a new polyether macrolide from dinoflagellate Dinophysis acuminata 659 // acuminolide A // N // stim. of actomyosin ATPase activity // * // * 428 Dinophyta Prorocentrum belizeanum // La Reunion Island // Belizentrin, a highly bioactive macrocycle from the dinoflagellate Prorocentrum belizeanum 660 // belizentrin // N // potent lethal effects on neuronal cells // * // * OH

O

OH

OH

OH

OH

OH

OH OH

HO

OH

OH

OH

OH

OH

O

O O

HO OH

RO

O O

OH

OH

O

OH

O

O

OH

OH

O O

O

O

O 661 R = H 662 R = SO3Na

OH

OH 663

HO

O

OH

664

429 Dinophyta Amphidinium carterae // CCMP121, Provasoli-Guillard NCMA) // Antifungal amphidinol 18 and its 7-sulfate derivative from the marine dinoflagellate Amphidinium carterae 661 // amphidinol 18 // N // modest activity vs C. albicans // * // * 662 // amphidinol 19 // N // * // * // * 430 Dinophyta Amphidinium sp. // Iriomote Is., Japan // Amphirionin-5, a novel linear polyketide from a cultured marine dinoflagellate Amphidinium species with a potent cell proliferation-promoting activity 663 // amphirionin-5 // N // growth promoter of ST-2 cells // * // * 431 Dinophyta Amphidinium sp. // Iriomote Is., Japan // Iriomoteolide-13a, a cytotoxic 22-membered macrolide from a marine dinoflagellate Amphidinium species 664 // iriomoteolide-13a // N // potent cytotox. vs HeLa // * // *

Key:


49

3


3.6

OH

Dinoflagellates OH

OH

OH

OH

NaO 3SO

NaO 3SO OH

O

OH

OH

OH

OH

O

HO

OH

OH

OH OH OH

OH

OH

OH

OH

O

OH

OH

OH

OH

†667 †669

OH 666

OH

O

HO O

HO OH

OH

OH

HO OH

OH OH

OH

OH OH

O

OH

X OH

OH

OH

HO O

HO

OH

O X=O X = OH ,H

X O

O

O

HO

OH

OH OH

†668

OH

665

†670

O X=O X = OH ,H

OH

432 Dinophyta Amphidinium sp. // Ishigaki Is., Japan // Amdigenols E and G, long carbon-chain polyol compounds, isolated from the marine dinoflagellate Amphidinium sp. 665 // amdigenol E // N // inhib. of N-type Ca channel opening // * // * 666 // amdigenol G // N // inhib. of N-type Ca channel opening // * // * 433 Dinophyta Amphidinium sp. // Ishigaki Is., Japan // Amphidinins C–F, amphidinolide Q analogues from marine dinoflagellate Amphidinium sp. 667 // amphidinin C // N // modest ABl activity, modest inhib. of T. mentagrophytes // * // * 668 // amphidinin D // N // modest inhib. of T. mentagrophytes // * // * 669 // amphidinin E // N // modest cytox vs P388 cells // * // * 670 // amphidinin F // N // modest inhib. of T. mentagrophytes // * // * HN

COOH

HN O

O O OH

OH

O

O

O

O O

O

O O

COOH 671

OH

OH

O

O

672

434 Dinophyta Azadinium spinosum // North Sea // Isolation, structure elucidation, relative LC-MS response, and in vitro toxicity of azaspiracids from the dinoflagellate Azadinium spinosum 671 // AZA33 // N // potent cytox to Jurkat T lymphocytes // * // * 672 // AZA34 // N // potent cytox to Jurkat T lymphocytes // * // *

Key:


50

3


3.6

O

O O

O

COOH

O

O

O

COOH

HO

OH

O O O

OH

H 2N

OH OH

OH O

O

OH

COOH

O

O

OH

OH

OH O

OH

OH

HO

HO

OH

HO

OH O

O

673

O

O

OH

O

O

O

OH

HO

O HO

Dinoflagellates

OH

O

NH

O

HO OH

OH

674 O

N H

OH OH

OH

O OH

O

OH

OH

OH

N H O

O

O

H

O

OH

OH

OH

OH

OH

†677

OH 676

OH

OH

OH OH

O

O †675

HO

OH O

O HO

O

OH

O

OH

OH

OH

435 Dinophyta Karenia brevisulcata // Wellington Harbour, New Zealand // Brevisulcatic acids, marine ladder-frame polyethers from the red tide dinoflagellate Karenia brevisulcata in New Zealand 673 // brevisulcatic acid-1 // N // cytotox. vs neuro-2a cells // MOA is activation of Na channels (as per brevetoxins and ciguatoxins?). // * 674 // brevisulcatic acid-4 // N // potent cytotox. vs neuro-2a cells // MOA is activation of Na channels (as per brevetoxins and ciguatoxins?). // * 436 Miozoa Vulcanodinium rugosum // South China Sea // Pinnatoxin H: a new pinnatoxin analogue from a South China Sea Vulcanodinium rugosum isolate. 675 // pinnatoxin H // N // high acute toxicity to mice // * // * 437 Dinophyta Ostreopsis cf. ovata // coast of Catalonia, Spain // The novel ovatoxin-g and isobaric palytoxin (so far referred to as putative palytoxin) from Ostreopsis cf. ovata (NW Mediterranean Sea): structural insights by LC-high resolution MSn 676 // ovatoxin-g // N // * // tentative structure assignment only. // * 439 Dinophyta Amphidinium sp. // Ishigaki Is., Japan // Absolute configuration of amphidinin A 677 // amphidinin A // R // * // * // s146

Key:


51

4

Green algae O O

N H

O

H N

COOMe 678

HN

N H 679

COOMe

HO

N H 680

H N

COOMe

448 Chlorophyta Caulerpa racemosa // Zhanjiang, China // Racemosins A and B, two novel bisindole alkaloids from the green alga Caulerpa racemosa 678 // racemosin A // N // neuroprotective against Ab25-35-induced SH-SY5Y cell damage // * // * 679 // racemosin B // N // weakly neuroprotective against Ab25-35-induced SH-SY5Y cell damage // * // * 449 Chlorophyta Caulerpa racemosa // Zhanjiang, China // Racemosin C, a novel minor bisindole alkaloid with protein tyrosine phosphatase-1B inhibitory activity from the green alga Caulerpa racemosa 680 // racemosin C // N // inhib. of hPTP1B. IC50 5.86 mM // * // *

Key:


52

5

Brown algae OAc

OAc

H

OAc

H OH

NH 2 9 †681

OH

HO H HO

HO

OH

H

HO

689

CHO

684

683

682

685

H

686

OH

H

H

H

AcO

R

690

691

692 R = 693 R =

AcO H

AcO H HO

687

OH

H AcO

OH

688 X H

AcO H

AcO

O

O O

O

H

H HO

H

H

HO

H

H HO

H

O O

OAc

HO

H

OH OH

HO

HO

AcO 694

O

H

695 X = OH,H 696 X = O

H

H

HO O

697

455 Ochrophyta Xiphophora chondrophylla // Hen and Chicken Islands, New Zealand // Identification and bioactivity of 3-epi-xestoaminol C isolated from the New Zealand brown alga Xiphophora chondrophylla 681 // 3-epi-xestoaminol C // N // bioactivity against a range of microorganisms evaluated // absolute configuration determined // * 456 Ochrophyta Dictyota plectens // Xuwen coast, Zhanjiang, China // Diterpenes from a Chinese collection of the brown alga Dictyota plectens 682 // (1S*,2S*,3E,5Z,7E,11R*,12R*)-2-acetoxy-12-hydroxydolabella-3,5,7-trien-9-one // N // evaluated against HIV-1, H5N1and LPS-induced NO production // * // * 683 // (1S*,2S*,3E,5Z,7Z,11R*,12R*)-2-acetoxy-12-hydroxydolabella-3,5,7-trien-9-one // N // evaluated against HIV-1, H5N1and LPS-induced NO production // * // * 684 // (1S*,2S*,3S*,4Z,6Z,8R*,11R*,12R*)-2-acetoxy-12-hydroxydolasta-4,6-dien-9-one // N // evaluated against HIV-1, H5N1and LPS-induced NO production // * // * 685 // 9α-hydroxydictyol E // N // evaluated against HIV-1, H5N1and LPS-induced NO production // * // * 686 // isodictyol E // N // evaluated against HIV-1, H5N1and LPS-induced NO production // * // * 687 // 3β-acetoxydilophol // N // evaluated against HIV-1, H5N1and LPS-induced NO production // * // * 688 // 19-acetyl-4-hydroxydictyodiol // N // evaluated against HIV-1, H5N1and LPS-induced NO production // * // * 457 Ochrophyta Dictyota sp. // Carqueiranne, France // Anti-microfouling properties of compounds isolated from several Mediterranean Dictyota spp. 689 // (1R*,3E,7E*,11S*,12S*)-9-acetoxy-3,7,18-dolabellatrien-17-al // N // * // * // * 690 // * // N // * // * // * 691 // 3-acetoxy-dictyotatriol A // N // * // * // * 460 Ochrophyta Dictyota pfaffii // Atol das Rocas, Brazil // Dolabelladienols A–C, new diterpenes isolated from Brazilian brown alga Dictyota pfaffii 692 // dolabelladienol A // N // evaluated in anti-HIV-1 assay system // * // * 693 // dolabelladienol B // N // evaluated in anti-HIV-1 assay system // * // * 694 // dolabelladienol C // N // evaluated in anti-HIV-1 assay system // * // * 462 Ochrophyta Sargassum siliquastrum // Cheju Is., Korea // Isolation of two new meroterpenoids from Sargassum siliquastrum 695 // sargachromanol Q // N // tested agaisnt 4 HTCLs // * // * 696 // sargachromanol R // N // active agaisnt 3 HTCLs. IC50 // * // * 463 Ochrophyta Sargassum thunbergii // Nanji Is., China // Thunberol, a new sterol from the Chinese brown alga Sargassum thunbergii 697 // thunberol // N // IC50 against PTP1B 2.24 g/mL // first natural sterol with 3-hydroxy-2,5-diene-4-keto grouping // *

Key:


53

6

Red algae OH

HO 3S

HO HO

O

HO

O HO

O

O

O

OH

OH

HO

O

O

4

12

O

†699

Cl

O

O Br

OAc

C 708

Br

Cl

O

HO

Cl

Br O

X

Cl

712

Cl

714 Cl

Br Br

Br

Br

C Br

Cl

HO

Cl

R2

OH O

R4

Br

R3 R1 = R 4 = Cl, R 2 = R 3 = Br †716 R = R = Cl, R = R = Br 1 2 3 4 †717 R = R = Br, R = R = Cl 1 4 2 3 †715

Cl 713

Br 705 X = O 706 X = OH ,H 707 X = OMe ,H

Cl R1

OH

C

Br 711

Br

Br

C 710

Br

700 701 ∆ saturated

O

O

O

Br

HO R1 = Br, R 2 = Et †703 R = Et, R = Br 1 2 704 R1 = Br, R 2 = Et, ∆ saturated

OH

709

OH

†702

O

Cl

Cl

10

O O

5

4

R2

O

OH

C

∆

5

OH

OH

OH

Cl O

∆

R1

O

O

HO

O

O 698

O

O

P

Br O

Cl 718

Br

478 Rhodophyta Chondrus crispus // Nova Scotia // Lipids isolated from the cultivated red alga Chondrus crispus inhibit nitric oxide production 698 // * // N // * // commercial scale cultivation of edible C. crispus. // * 479 Rhodophyta Palmaria palmata // Nova Scotia // Polar lipids from the marine macroalga Palmaria palmata inhibit lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells 699 // * // N // inhib. of LPS-i-NO in RAW264.7 cells // commercial scale cultivation of edible P. palmata // * 700 // * // N // inhib. of LPS-i-NO in RAW264.7 cells // commercial scale cultivation of edible P. palmata // * 701 // * // N // inhib. of LPS-i-NO in RAW264.7 cells // commercial scale cultivation of edible P. palmata // * 480 Rhodophyta Laurencia sp. // Omeazaki, Japan // Omaezallene from red alga Laurencia sp.: structure elucidation, total synthesis, and antifouling activity 702 // omaezallene // N // potent antifouling activity // total synth. // * 703 // (12Z)-omaezallene // N // potent antifouling activity // total synth. // * 704 // 10,11-dihydro-omaezallene // N // * // * // * 481 Rhodophyta Laurencia marilzae // Tenerife, Canary Is. // Stereochem. determination of 5-memb. cyclic ether acetogenins using a spin-spin coupling constant approach and DFT calcs 705 // marilzafurollene A // N // * // J-based method used for config. determn. // * 706 // marilzafurollene B // N // * // J-based method used for config. determn. // * 707 // marilzafurollene C // N // * // J-based method used for config. determn. // * 708 // marilzafurollene D // N // * // J-based method used for config. determn. // * 709 // 12-acetoxy-marilzafurenyne // N // * // J-based method used for config. determn. // * 482 Rhodophyta Laurencia chondrioides // Kefalonia Is., Greece // An integrated approach using UHPLC–PDA–HRMS and 2D HSQC NMR for the metabolic profiling of the red alga Laurencia: dereplication and tracing of natural products 710 // marilzallene B // N // * // rapid dereplication using UHPLC–PDA–HRMS, 2D HSQC NMR, software and databases // * 711 // chondrioallene // N // * // rapid dereplication using UHPLC–PDA–HRMS, 2D HSQC NMR, software and databases // * 483 Rhodophyta Plocamium hamatum, P. costatum // Flinders Reef, & Pandalowie Bay, Australia // Accelerated identification of halogenated monoterpenes from Australian specimens of the red algae Plocamium hamatum and Plocamium costatum 712 // * // N // * // rapid derep. using LC-UV-MS-SPE-NMR // * 713 // * // N // * // rapid derep. using LC-UV-MS-SPE-NMR // * Key:


54

6

Red algae 714 // costatol B // N // * // rapid derep. using LC-UV-MS-SPE-NMR // * 715 // costatol C // N // * // rapid derep. using LC-UV-MS-SPE-NMR // * 716 // costatol D // N // * // rapid derep. using LC-UV-MS-SPE-NMR // * 717 // costatol E // N // * // rapid derep. using LC-UV-MS-SPE-NMR // * 718 // costatone B // N // * // rapid derep. using LC-UV-MS-SPE-NMR // * O

Br

Br

R3

Br O 719

OH

R1

720

OH

OH

R2 R1 †721 R = R =H, R = 1 2 3 †722 R = R =H, R = 1 2 3 723 R1 = R 2 =Br, R 3 = O

Br

HO

OH

726

Cl †727

HO

728

OH

725

OOH OOH H

Br O

Br 732

731

Br

O 724

OH

OH

Cl

Br

O

R2

OH OH 729 R1 = Me, R 2 = 730 R1 = OMe, R 2 = Me

AcO

HO

Br

HO

O 733

HO

Br

O S

Br

734

N H

HO

484 Rhodophyta L. okamurae // Nanji Is., China // A seco-laurane sesquiterpene and related laurane derivatives from the red alga Laurencia okamurai Yamada 719 // seco-laurokamurone // N // * // unusual seco-sesquiterpene // * 720 // laurepoxyene // N // strong AF activity // * // * 721 // 3β-hydroperoxyaplysin // N // strong AF activity, mod. cytox. A549 cells // * // * 722 // 3α-hydroperoxy-3-epiaplysin // N // strong AF activity // * // * 723 // 8,10-dibromoisoaplysin // N // * // * // * 724 // laurokamurene D // N // * // * // * 725 // (5S)-5-acetoxy-β-bisabolene // N // * // * // * 485 Rhodophyta L. dendroidea // SE Coast, Brazil // Sesquiterpenes from the Brazilian red alga Laurencia dendroidea J. Agardh 726 // dendroidone // N // * // * // * 727 // dendrodiol // N // * // * // * 486 Rhodophyta L. obtusa // Jeddah, Saudi Arabia // New cytotoxic laurene-, cuparene-, and laurokamurene-type sesquiterpenes from the red alga Laurencia obtusa 728 // laur-2-ene-3,12-diol // N // mod. cytotox. KB and MCF-7 cells // * // * 729 // cuparene-3,12-diol // N // mod. cytotox. KB cells // * // * 730 // 8,11-dihydro-1-methoxylaurokamuren-12-ol // N // * // * // * 487 Rhodophyta L. glandulifera, Mollusca Aplysia punctata // Loutraki Bay, Crete, & Nea Makri, Greece // Glandulaurencianols A–C, brominated diterpenes from the red alga, Laurencia glandulifera and the sea hare, Aplysia punctata 731 // glandulaurencianol A // N // * // * // * 732 // glandulaurencianol B // N // * // * // * 733 // glandulaurencianol C // N // * // new diterpene skeleton // * 488 Rhodophyta L. brongniartii // Kenting, Taiwan // Cytotoxic, anti-inflammatory, and antibacterial sulfur-containing polybromoindoles from the Formosan red alga Laurencia brongniartii 734 // * // N // * // * // * Key:


55

6

Red algae O O Br

COOMe

Br O

N

Br

Br

Br

HN

N

R

Br

Br

Br R HO

Br

HO OH

Br

735

OH HO OH

Br OH

Br

736 R = Br 737 R = H

OH OH

Br

Br

†738 †739

R=H R = Br

489 Rhodophyta Symphyocladia latiuscula // Qingdao Coast, China // Antifungal bromophenols from marine red alga Symphyocladia latiuscula 735 // * // N // * // * // * 736 // * // N // * // * // * 737 // * // N // * // weak AF activity // * 490 Rhodophyta Asparagopsis taxiformis // Mayotte, W. Indian Ocean // Mahorones, highly brominated cyclopentenones from the red alga Asparagopsis taxiformis 738 // mahorone // N // modest AB activity // first example natural 2,3-dibromocyclopentenones // * 739 // 5-bromomahorone // N // modest AB activity // first example natural 2,3-dibromocyclopentenones // *

Key:


56

7

Sponges OH O 15

14

NH

H N

O

O NH

SO3H X

N H

OH

O

HO 3S

OH

O

HO 17

740

OH

742 X = O OH,H X=

14

OH

OH

741

OH R1

OH

9

749

OH

∆

†750

OH

O

OH

OH O

†746

745

O

∆2

∆2

5

6

14

†743

HO 3S

748

5

†744

O

H N

R2

OH

OH ∆

∆

9

R1 = OH , R 2 = COOH 751 R1 = OH, R 2 = COOH, ∆1 saturated 752 R1 = OH, R 2 = COOH, ∆2 saturated †753 R = OH , R 2 = H 1

∆ saturated

747

14

5

754 R = OH, ∆ saturated 755 R = H

5

R

OH

504 Porifera Petrosia sp. // Jeddah, Saudi Arabia // Cytotoxic effects of three new metabolites from Red Sea marine sponge, Petrosia sp. 740 // N-((3S,E)-1,3-dihydroxytetracos-4-en-2-yl)stearamide // N // IC50 40 μg/mL DNA binding using methyl green displacement // * // * 505 Porifera Echinoclathria gibbosa // Hurghada, Egypt // New compounds from the Red Sea marine sponge Echinoclathria gibbosa 741 // echinoclathriamide // N // * // * // * 506 Porifera Coscinoderma sp. // Weno Is., Chuuk State, Micronesia // Suvanine sesterterpenes and deacyl irciniasulfonic acids from a tropical Coscinoderma sp. sponge 742 // deacyl irciniasulfonic acid C // N // mod. to weak AB activity and vs HTCL, ATPase // * // 743 // sodium deacyl irciniasulfonate D // N // mod. to weak AB activity and vs HTCL, ATPase // * // * 507 Porifera family Spongiidae // Unten Port, Okinawa // Taurospongins B and C, new acetylenic fatty acid derivatives from a marine sponge of the family Spongiidae 744 // taurospongin B // N // * // * // * 745 // taurospongin C // N // weak AB activity // * // * 508 Porifera Callyspongia sp. // Pingtung, Taiwan // Cytotoxic polyacetylenes from a Formosan marine sponge Callyspongia sp. 746 // callysponyne A // N // low µM activity vs 7 HTCL // * // * 747 // callysponyne B // N // low µM activity vs 7 HTCL // * // * 509 Porifera Siphonochalina siphonella // Sharm Obhur, Saudi Arabia // Cytotoxic polyacetylenes from the Red Sea sponge Siphonochalina siphonella 748 // callyspongenol-D // N // mod. activity vs HTCL // * // * 749 // callyspongendiol // N // weak activity vs HTCL // * // * 510 Porifera Petrosia sp. // Hachijo Is., Japan // Structural reappraisal of corticatic acids, biologically active linear polyacetylenes, from a marine sponge of the genus Petrosia 750 // corticatic acid A // R // * // Structure revised from more detailed FAB-MS studies // s147 751 // corticatic acid F // N // * // * // * 752 // corticatic acid G // N // * // * // * 753 // corticatynol A // N // * // * // * 511 Porifera Petrosia sp. // Pingtung, Taiwan // Structure elucidation and cytotoxic evaluation of new polyacetylenes from a marine sponge Petrosia sp. 754 // petrosianyne A // N // weak inhib. of 5 HTCLs // * // * 755 // petrosianyne B // N // weak inhib. of 3 HTCLs // * // * Key:


57

7

Sponges

5

OH

R3

R1

I

COOMe COOMe

1

Br

756 (1E) 757 (1Z)

Br

R2 R4 758 R1 = R 2 = R 3 = R 4 = H 759 R1 = R 2 = H, R 3 = OH, R 4 = Br Br 760 R1 = R 2 = H, R 3 = OH, R 4 = 761 R1 = Br, R 2 = OH, R 3 = R 4 = H 762 R1 = Br, R 2 = OH, R 3 = R 4 = H

COOMe

763

O

Br

765

OH OH

O

COOMe

764

7

7

Br

†766

OH

512 Porifera Placospongia sp. // Tong-Yong City, S. Korea // Placotylene A, an inhibitor of the receptor activator of nuclear factor-κB ligand-induced osteoclast differentiation, from a Korean sponge Placospongia sp. 756 // placotylene A // N // suppresses RANKL-induced osteoclast differentiation at > 1 μM, and inhibited NFATTc1 translation // * // * 757 // placotylene B // N // * // * // * 513 Porifera Xestospongia testudinaria // Weizhou Is., China // Brominated polyunsat. lipids from Chinese sponge Xestospongia testudinaria as a new class of pancreatic lipase inhibitors 758 // xestonariene A // N // 23.8% inhib. of pancreatic lipase at 50 μM // * // * 759 // xestonariene B // N // 40.1% inhib. of pancreatic lipase at 50 μM // * // * 760 // xestonariene C // N // 11.9% inhib. of pancreatic lipase at 50 μM // * // * 761 // xestonariene D // N // 43.9% inhib. of pancreatic lipase at 50 μM // * // * 762 // xestonariene E // N // 32.8% inhib. of pancreatic lipase at 50 μM // * // * 763 // xestonariene F // N // * // * // * 764 // xestonariene G // N // * // * // * 765 // xestonariene H // N // * // * // * 515 Porifera Petrosia sp. // * // Chemoenzymatic synthesis and HPLC analysis of the stereoisomers of miyakosyne A [(4E,24E)-14-methyloctacosa-4,24-diene-1,27-diyne-3,26-diol], a cytotoxic metabolite of a marine sponge Petrosia sp., to determine the absolute configuration of its major component as 3R,14R,26R 766 // miyakosyne A // R // * // 96:4 Mixture of 14R:14S diastereomers, det. by synthesis // s148 O ∆

HO

O

OH

OH

OMe COOH

OH

O †768

O

†769

∆ saturated

O O

COOMe

O

770 MeO

COOMe

O

MeO

O HO

R=

R COOMe

O

773

COOMe

COOMe

772 R = OH 40

OH

NH 2

767

N

O O

36

†771

O O

H

9

42

Cl

774

H N

Br

775

COOMe

776

O

SO3Na

517 Porifera Hemimycale sp. // Torres Is., Vanuatu // Strength by joining methods: combining synthesis with NMR, IR, and vibrational circular dichroism spectroscopy for the determination of the relative configuration in hemicalide 767 // hemicalide // R // * // Rel. config. at C36-46 assigned by synthesis and VCD spectra // s149 Key:


58

7

Sponges

518

Porifera Plakortis simplex // Yongxing Is., S. China Sea // Endoperoxide polyketides from a Chinese Plakortis simplex: further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes 768 // haterumadioxin A methyl ester // M // mod. antimalarial activity // Known semi-synthetically // * 769 // haterumadioxin B methyl ester // N // mod. antimalarial activity // * // * 770 // * // N // * // * // * 771 // * // N // mod. antimalarial activity // * // * 772 // * // N // mod. antimalarial activity // * // * 773 // * // N // mod. antimalarial activity // * // * 519 Porifera Dysidea sp. // Biak, W. Papua, Indonesia // Two new compounds from an Indonesian sponge Dysidea sp. 774 // biaketide // N // weak activity vs HTCL // * // * 775 // debromoantazirine // N // weak activity vs HTCL // * // * 520 Porifera Anoxycalyx joubini // Trawled (279 m), E. Weddell Sea, Antarctica // Occurrence of a taurine derivative in an Antarctic glass sponge. 776 // glassponsine // N // * // * // * CONH 2 OH O

H 2NOC O

HO

NH

N

O

O

N H †777

H N

CONH 2

O

OH

O H N

N H OH

H N

N H

O

O

CONH 2

O

NH

OH

O

H 2NOC

O

HN

N

H N

N H O

O

R3 H N

O N H NH 2

O

OMe

O N H

O

N O

O

O HOOC

HN H N O

CONH 2

Cl

HN

O N

MeO

O OEt

O

O R2

O

CONH 2

†778

R=H 779 R = OH

O

R1

O

NHCHO O

O

NH 2

OH

H N

HO O

OH

H N O

NH O

H O

COOH

N H

H N

N H

NH

O

R

N H

†780

R1 = OH, R 2 = R 3 = Me R1 = OH, R 2 = H, R 3 = Me †783 R = H, R = R = Me 1 2 3 784 R1 = OH, R 2 = Me, R 3 = H †781

O

NH

O N CONH 2

OH

522 Porifera Discodermia japonica // Sagami Bay, Japan // Revised structure of cyclolithistide A, a cyclic depsipeptide from the marine sponge Discodermia japonica 777 // cyclolithistide A // R // * // * // s150 523 Porifera Homophymia lamellosa // Saint Marie Is., Madagascar // Isolation and structures of pipecolidepsins A and B, cytotoxic cyclic depsipeptides from Madagascan H. lamellosa 778 // pipecolidepsin A // N // potent activity vs 3 HTCLs // * // * 779 // pipecolidepsin B // N // potent activity vs 3 HTCLs // * // * 525 Porifera Ecionemia acervus // Tulear, Madagascar // Stellatolides, new cyclodepsipeptide family from E. acervus: isoln., solid-phase total synth., full struct. assign. of stellatolide A 780 // stellatolide A // N // potent activity vs 3 HTCLs // * // * 781 // stellatolide B // N // potent activity vs 3 HTCLs // * // * 782 // stellatolide C // N // potent activity vs 3 HTCLs // * // * 783 // stellatolide D // N // potent activity vs 3 HTCLs // * // * 784 // stellatolide E // N // potent activity vs 3 HTCLs // * // * 785 // stellatolide F // N // potent activity vs 3 HTCLs // * // * 786 // stellatolide G // N // potent activity vs 3 HTCLs // * // * Key:


59

7

Sponges

526 Porifera Pipestela candelabra // Houghton Reef, Australia // Potent cytotoxic peptides from the Australian marine sponge Pipestela candelabra 787 // milnamide E // N // potent activity vs HTCLs // * // * 788 // milnamide F // N // mod. activity vs HTCLs // * // * 789 // milnamide G // N // mod. activity vs HTCLs, 39% inhib. of NFF cells at 10 μM // * // * 790 // hemiasterlin D // N // potent activity vs HTCLs // * // * CONH 2

CONH 2 OH

OH

O

H 2NOC

N H O

HN

O H N

O

OMe

O H N

N H NH 2

O

R

O

N H

OH

MeO

O

N H

H N

N H O

HN

O

O O

H N

N H

O

O

N H

O

O MeO

N

O

NH O N N H

785 R = H 786 R = OH

782

N

COOH

O †789

OH

R2

OH

N

N H CONH 2

R1

O

X = 2H 788 X = O

O

N H

COOH

†787

X

O O

N

N H

N

N H

HN

N

CONH 2

O

O

NH

O

OMe

O

OH

COOH N

O

H 2NOC

HN

HO

OH

O O

O

O

HO

N H NH 2Me

N

N

COOH

OMe

O

N HN

O O

NH

O

HN

O HN

O

NH

NH

O

O

COOH

NH

H N

790

N H

H 2NOCHN

O

HN O

NHCONH 2

O

R1 = Me, R 2 = H †792 R = R = H 1 2 †793 R = R = Me 1 2

O O

NH

O N

NH 795

N

†791

O

O

NH N

N

O

HN O

NH

OH HN

O N

O

O

O

O

†794

527 Porifera Discodermia kiiensis // Shikine Is., Japan // Lipodiscamides A–C, new cytotoxic lipopeptides from Discodermia kiiensis 791 // lipodiscamide A // N // mod. activity vs HTCLs // * // * 792 // lipodiscamide B // N // mod. activity vs HTCLs // * // * 793 // lipodiscamide C // N // mod. activity vs HTCLs // * // * 528 Porifera Stylissa caribica // Sweetings Cay, Bahamas // Structures and solution conformational dynamics of stylissamides G and H from the Bahamian sponge Stylissa caribica 794 // stylissamide G // N // * // LC-MS/MS analysis of 10 S. caribica samples indicated source was unique chemo-morph // * 795 // stylissamide H // N // mod. activity vs HTCL // LC-MS/MS analysis of 10 S. caribica samples indicated source was unique chemo-morph // * Key:


60

7

Sponges

H N

HN

H N

N O

O

N

O

O

N HN O

O CONH 2

NH

N H

O

HN

N H

O

O

NH

NH

N H

O

HN

O HN

O NH

N H

N

O

O

NH

O N

†799

†798

O

O

HN

N

†796

OH

O

O HN

O HN

N O

O

N

N H

O

NH

O

O

O NH

N

N O

HO

NH

O

O

O

N

O

HN

O

HN

N

O

O

O

O

†800

†797

529 Porifera Reniochalina stalagmitis // Yongxing Is., S. China Sea // Reniochalistatins A–E, cyclic peptides from the marine sponge Reniochalina stalagmitis 796 // reniochalistatin A // N // * // * // * 797 // reniochalistatin B // N // * // * // * 798 // reniochalistatin C // N // * // * // * 799 // reniochalistatin D // N // * // * // * 800 // reniochalistatin E // N // * // * // * OH

COOH HN O

CO 2

N

HN

S

O O

N

O O

O

O

HN

N H

NHR HO

O R = COCH 2NH 2 802 R = H

OH Br

530

Key:

XDCPGEGEQCDVEFNPCCPPLTCIPGDPYGICYII N

OH OH O

H 2NOC H N

N H

O

†801

804 NH

N

O NH

XGCAFEGESCNVEFYPCCPGLGLTCIPGNPDGTCYYL O

HO

N

O

OH

O

HO O

N

H N

N H

N H

HO

O HN

O

O S

NH HN

O

O

H N

805 O

H N O CONH 2

O N H

OH NH

XGCAGPGEECIVGFYDCCPGYRCYPGDPGGICY 806

OH

803

Porifera Suberites waedoensis // Chuja Is., S. Korea // New cyclic cystine bridged peptides from the sponge Suberites waedoensis 801 // chujamide A // N // weak activity vs HTCLs // * // * 802 // chujamide B // N // weak activity vs HTCLs, mod. vs Na+/K+ ATPase // * // * Main article bibliography reference // Taxonomy // Location // Article title Compound number // Compound name // Status // Biological activity // Other information // Secondary references

61

7

Sponges

531 Porifera Theonella swinhoei // Hurghada, Egypt // Theonellamide G, a potent antifungal and cytotoxic bicyclic glycopeptide from the Red Sea marine sponge Theonella swinhoei 803 // theonellamide G // N // mod. AB activity and vs HTCL // * // * 532 Porifera Asteropus sp // Geoje Island, S. Korea // Asteropsins B–D, sponge-derived knottins with potential utility as a novel scaffold for oral peptide drugs 804 // asteropsin B // N // stable to chymotrypsin, elastase and pepsin digest for >4 hrs // * // * 805 // asteropsin C // N // stable to chymotrypsin, elastase and pepsin digest for >4 hrs // * // * 806 // asteropsin D // N // stable to chymotrypsin, elastase and pepsin digest for >4 hrs // * // * OH OH

HN

O

N OH

H

Br H 2NOCO

R N

N H

H

O

OH

N

H

OH O

H

N

N

O

S

†810 †811

O R= R=

N H

H

OH

N

N

N 808

O

R

†809

HN

N

N H

OH

N

N

N

H

N H

OH

N

N 807

N H

H

H

N H

N O

812

H H

803 R = H 814 R = Me

O †815

COOH HO

†816

533 Porifera Callyspongia sp. // Ambon, Indonesia // Callyspongiolide, a cytotoxic macrolide from the marine sponge Callyspongia sp. 807 // callyspongiolide // N // very potent (nM) activity vs three HTCLs // * // * 537 Porifera Callyspongia sp. // Hainan Is., China // A new diketopiperazine from South China Sea marine sponge Callyspongia sp. 808 // callysponine A // N // * // * // * 538 Porifera Acanthostrongylophora ingens // Hoga Is., S.E. Sulawesi // Acanthocyclamine A from the Indonesian marine sponge Acanthostrongylophora ingens 809 // (–)-acanthocyclamine A // N // * // Abs. config. established by X-ray crystallography // * 539 Porifera Acanthostrongylophora ingens // Mantehage, N. Sulawesi // Acanthomanzamines A–E with new manzamine frameworks from the marine sponge Acanthostrongylophora ingens 810 // acanthomanzamine A // N // mod. cytoxicity vs HTCL and inhib. of proteasome action; also modest inhib. of cholesterol accumulation at 20 µM // * // * 811 // acanthomanzamine B // N // mod. cytoxicity vs HTCL and inhib. of proteasome action; also potent inhib. of cholesterol accumulation at 20 µM // * // * 812 // acanthomanzamine C // N // * // * // * 813 // acanthomanzamine D // N // weak cytoxicity vs HTCL and potent inhib. of proteasome action; also strong inhib. of cholesterol accumulation at 20 µM // * // * 814 // acanthomanzamine E // N // weak cytoxicity vs HTCL and mod. inhib. of proteasome action; also strong inhib. of cholesterol accumulation at 20 µM // * // * 540 Porifera Acanthostrongylop. ingens // Bajotalawaan, N. Sulawesi // Acantholactam and pre-neo-kauluamine, manzamine-related alkaloids from the Indonesian marine sponge Acanthostrongylophora ingens 815 // acantholactam // N // weak activity vs HTCL, weak proteasome inhib., no inhib. of cholesterol ester accumulation at 20 μM // * // * 816 // pre-neo-kauluamine // N // mod. activity vs HTCL, potent proteasome inhib., 91% inhib. of cholesterol ester accumulation at 20 μM // * // *

Key:


62

7

Sponges R N

NHMe 6

m n

4

819

N

N

9

9

820

822

N

OH HOOC HN

823

N

O

O N HO

N H MeS

O N H

824

N

OH

825

HO

OR

MeOOC

R COOH OH

HO

OH O

N H

N 827

HO NH 2

HO

O

NH

HO

N H 13

H 2N

H N COOH

826

OH

N

OHC

N H

9

OH

N

HO

CHO

N

4

821

N

817 R = OH, n = 3, m = 9 818 R = H, n = 7, m = 5

N

3

828

O O

N NH

HO

N S

X

HN N H

N

N H

OH

829

N

830 R = COOH, X = 2H 832 R = COOH, X = O 833 R = H, X = O

O

N

N H

N 834 R = SO3H H 835 R = H

O 831

N

N

541 Porifera Topsentia sp. // Lingshui Bay, China // Topsendines A–F, new 3-alkylpyridine alkaloids from a Hainan sponge Topsentia sp. 817 // topsendine A // N // 85.9% inhib. of delayed rectifier K+ currents in rat dissociated hippocampal neurons at 100 μM // * // * 818 // topsendine B // N // * // * // * 819 // topsendine C // N // 87.1% inhib. of delayed rectifier K+ currents in rat dissociated hippocampal neurons at 100 μM // * // * 820 // topsendine D // N // * // * // * 821 // topsendine E // N // 76.2% inhib. of delayed rectifier K+ currents in rat dissociated hippocampal neurons at 100 μM // * // * 822 // topsendine F // N // * // * // * 823 // 2-methyl-12-(pyridine-3-yl)dodecanal // M // * // Previously known synthetic compound // s151 542 Porifera Axinyssa aculeata // Okinawa // Protoaculeine B, a putative N-terminal residue for the novel peptide toxin aculeines 824 // protoaculeine B // N // * // * // * 543 Porifera Hyrtios erecta // Lingshui Bay, China // Hainanerectamines A–C, alkaloids from the Hainan sponge Hyrtios erecta 825 // hainanerectamine A // N // * // * // * 826 // hainanerectamine B // N // weak cytotox. vs 1 HTCL // * // * 827 // hainanerectamine C // N // weak cytotox. vs 1 HTCL // * // * 544 Porifera Hyrtios sp. // Kerama Is., Okinawa // Hyrtimomines, indole alkaloids from Okinawan marine sponges Hyrtios spp. 828 // hyrtimomine F // N // weak AB activity // * // * 829 // hyrtimomine G // N // weak AB activity // * // * 830 // hyrtimomine H // N // * // * // * 831 // hyrtimomine I // N // weak AB activity // * // * 832 // hyrtimomine J // N // weak AB activity // * // * 833 // hyrtimomine K // N // * // * // * 545 Porifera Luffariella variabilis // N. Sulawesi, Indonesia // Variabines A and B: new β-carboline alkaloids from the marine sponge Luffariella variabilis 834 // variabine A // N // * // First reported sulfated β-carboline // * 835 // variabine B // N // mod. inhib. of chymotrypsin-like activity of proteasome and Ubc13-Uev-1A // * // * Key:


63

7

Sponges R2

OMe

O

HOOC

R1

MeO

N N

O

N N H

836

O

O

N H

837

MeO O

OMe O

OMe

N 838

O

N NH

844

N R

EtO O

N 845

MeO EtO

R1

N N

N 839 R1 = Me, R 2 = H 840 R1 = H, R 2 = Me

841

N

N 842 R1 = H, R 2 = Me 843 R1 = Me, R 2 = H

N

N

N

R2

N

H 2N

N

OMe O

HN

N

OMe

N

OMe MeO

OMe

OMe N

846 R = 847 R = 848 R = iPr 849 R = OEt

HN

R

850 R = 851 R = 852 R = (CH 2) 3COOEt

546 Porifera Hyrtios sp. // Swain Reef, Australia // Isolation, structure determination and cytotoxicity studies of tryptophan alkaloids from an Australian marine sponge Hyrtios sp. 836 // 6-oxofascaplysin // N // weak activity vs HTCL // MS-guided isolation // * 837 // secofascaplysic acid // N // weak activity vs HTCL // MS-guided isolation // * 549 Porifera Aaptos sp. // Kupang, Indonesia // Aaptamines, marine spongean alkaloids, as anti-dormant mycobacterial substances 838 // 2-methoxy-3-oxoaaptamine // N // mod. antimycobacterial activity against both active and dormant M. smegmatis // * // * 550 Porifera Aaptos aaptos // Yongxing Is./Seven Connected Islets, S. China Sea // Aaptamine derivatives with antifungal and anti-HIV-1 activities from the South China Sea sponge Aaptos aaptos 839 // 2-isobutyl-11-methoxy-3H-[1,6]naphthyridino[6,5,4-def]quinoxalin-3-one // N // * // * // * 840 // 2-(sec-butyl)-11-methoxy-3H-[1,6]naphthyridino[6,5,4-def]quinoxalin-3-one // N // * // * // * 841 // 9-ethoxy-8,9-dimethoxy-9H-benzo[de][1,6]naphthyridine // N // weak AF activity // Probable artefact of isolation // * 842 // 2-(sec-butyl)-10-methoxyimidazo[4,5,1-ij]pyrido[2,3,4-de]quinolone // N // weak AF activity // * // * 843 // 2-isobutyl-10-methoxyimidazo[4,5,1-ij]pyrido[2,3,4-de]quinolone // N // weak AF activity // * // * 551 Porifera Aaptos aaptos // Yongxing Is./Seven Connected Islets, S. China Sea // Cytotoxic aaptamine derivatives from the South China Sea sponge Aaptos aaptos 844 // piperidine[3,2-b]demethyl(oxy)-aaptamine // N // * // * // * 845 // 9-amino-2-ethoxy-8-methoxy-3H-benzo[de]-[1,6]naphthyridin-3-one // N // potent inhib. of 6 HTCLs // Probable artefact of isolation // * 846 // 2-(sec-butyl)-7,8-dimethoxybenzo[de]imidazo[4,5,1-ij][1,6]-naphthyridin-10(9H)-one // N // * // * // * 847 // 2-isobutyl-7,8-dimethoxybenzo[de]imidazo[4,5,1-ij][1,6]-naphthyridin-10(9H)-one // N // * // * // * 848 // 2-isopropyl-7,8-dimethoxybenzo[de]imidazo[4,5,1-ij][1,6]-naphthyridin-10(9H)-one // N // * // * // * 849 // 2-ethoxy-7,8-dimethoxybenzo[de]imidazo[4,5,1-ij][1,6]-naphthyridin-10(9H)-one // N // * // Probable artefact of isolation // * 850 // 3-(2-methylbutylamino)demethyl(oxy)aaptamine // N // * // * // * 851 // 3-isobutylaminodemethyl(oxy)-aaptamine // N // potent inhib. of 6 HTCLs // * // * 852 // 3-(N-4-ethylbutanoate)aminodemethyl(oxy)aaptamine // N // * // Probable artefact of isolation // *

Key:


64

7

Sponges NH 2

HO ∆

H N

N

H N

H 2N

R

N

N

X

O

OH

H N

N H O 864 X = NH 2+ 865 X = O

†854 †855

NH

N H O 866 R = Et 867 R = Me

NH

N

HN HN H

H

NH

NH 2 H

OH R = Et R = H, ∆ sat.

856

H H 857 R = 858 R =

H

H H

H

NH

Br

H N

∆

N Br NH 2

O 868 NH 869 ∆ saturated

H

H

859

H

H 861 R 862 R 863 R

860

∆

H N

Br N H O

X HN

870 X = MeO,H 871 X = O

H = Et =H = Et, ∆ saturated

O

NH

Br Br

Br

N

R

Br

COOR SO3

N

NH 2

NH 2

R N

RO

O

Br

N

HN NH H H H

NH

O

N O O 853

NH 2

NH 2

NH N H

HN

Br

SO3

H H N

O H H N

Br N H O

NH 2 872

N H

552 Porifera Ancorina geodides // Budget Head, Tasmania, Australia // Struct. determ. of pentacyclic pyridoacridine alkaloids from Australian A. geodides, Cnemidocarpa stolonifera 853 // ancorine A // N // weak activity against HTCLs // From Ancorina geodides // * 555 Porifera Monanchora pulchra // Urup Is, Russia // Urupocidin A: a new, inducing iNOS expression bicyclic guanidine alkaloid from the marine sponge Monanchora pulchra 854 // urupocidin A // N // increased iNOS expression and hence NO production in RAW 264.7 cells at 10 µM // First marine alkaloid stimulator of NO production // * 855 // urupocidin B // N // * // * // * 556 Porifera Acanthella cavernosa // S.W. Australia // Tricyclic guanidine alkaloids from the marine sponge Acanthella cavernosa that stabilize the tumor suppressor PDCD4 856 // mirabilin K // N // * // * // * 557 Porifera Biemna laboutei // Salary Bay, Madagascar // Netamines H–N, tricyclic alkaloids from the marine sponge Biemna laboutei and their antimalarial activity 857 // netamine H // N // * // mirablin A also isolated in underivatised form for the first time // * 858 // netamine I // N // * // mirablin A also isolated in underivatised form for the first time // * 859 // netamine J // N // * // mirablin A also isolated in underivatised form for the first time // * 860 // netamine K // N // mod. antimalarial activity // mirablin A also isolated in underivatised form for the first time // * 861 // netamine L // N // * // mirablin A also isolated in underivatised form for the first time // * 862 // netamine M // N // mod. activity vs HTCL // mirablin A also isolated in underivatised form for the first time // * 863 // netamine N // N // * // mirablin A also isolated in underivatised form for the first time // * 558 Porifera Callyspongia sp. // Great Australian Bight // Callyspongisines A–D: bromopyrrole alkaloids from an Australian marine sponge, Callyspongia sp. 864 // callyspongisine A // N // * // * // * 865 // callyspongisine B // N // * // likely degradation/storage artefact // * 866 // callyspongisine C // N // * // likely degradation/storage artefact // * 867 // callyspongisine D // N // * // likely degradation/storage artefact // * 559 Porifera Agelas sp. // Kerama Is., Okinawa // Bromopyrrole alkaloids from a marine sponge Agelas sp. 868 // 2-bromokeramadine // N // * // * // * 869 // 2-bromo-9,10-dihydrokeramadine // N // weak AB activity // * // * 870 // tauroacidin C // N // * // * // * 871 // tauroacidin D // N // * // * // * 872 // mukanadin G // M // mod. AB activity // * // s152 Key: Main article bibliography reference // Taxonomy // Location // Article title 65 Compound number // Compound name // Status // Biological activity // Other information // Secondary references

7

Sponges H N

Br

NH 2 HN

NH Br

NH

O

HN H 2N Br

R1

N NH 3

N N H H 873 R = Me 874 R = H

O

HN

R2

HOOC

NH

HN

NH

R1 = R1 = †877 R = 1 †876

Br

R †887 R = H 888 R = Br

NH 2

O

N H

COOH

NH

H , R2 = H , R2 = H , R2 =

O

Br

OMe

R1

R1

HN R2

†878

R1 = R 2 = H R1 =H, R 2 = Br †880 R = R = Br 1 2 †879

Br

HN

HN H N

H H H

Br NH

OH

O

O

Br

O

HO

MeO

HN

COOH Br

R2

Br

Br

Br

HO

886

NHAc

885

†881

R1 = R 2 = H †882 R =H, R = Br 1 2 †883 R = R = Br 1 2

Br HO

889

HN

O

Br

N H

HO HOOC N

884

O OMe

MeO

N H

NH

NH †875

N H

COOH

O

Br

NH

NH

Br

HN

O

H 2N

HN

O

Br

RO

Br

HN NH

Br

NH

HN

H N

HN

NHMe 2 N

O Br

890

560 Porifera Agelas sp. // Kerama Is., Okinawa // Agelamadins A and B, dimeric bromopyrrole alkaloids from a marine sponge Agelas sp. 873 // agelamadin A // N // mod. AB activity // Isolated as a racemate // * 874 // agelamadin B // N // mod. AB activity // Isolated as a racemate // * 561 Porifera Agelas sp. // Kerama Is., Okinawa // Agelamadins C–E, bromopyrrole alkaloids comprising oroidin and 3-hydroxykynurenine from a marine sponge Agelas sp. 875 // agelamadin C // N // weak AB activity vs Cryptococcus neoformans // * // * 876 // agelamadin D // N // weak AB activity vs C. neoformans // * // * 877 // agelamadin E // N // weak AB activity vs C. neoformans // * // * 571 * // * // Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence 878 // sceptrin // R // * // * // s153 879 // bromosceptrin // R // * // * // s154 880 // dibromosceptrin // R // * // * // * 881 // ageliferin // R // * // * // s155 882 // bromoageliferin // R // * // * // s155 883 // dibromoageliferin // R // * // * // s155 572 Porifera Callyspongia sp. // Heron Is., Queensland, Australia // ApoE secretion modulating bromotyrosine derivative from the Australian marine sponge Callyspongia sp. 884 // callyspongic acid // N // * // * // * 885 // 3,5-dibromo-4-methoxyphenylpyruvic acid // N // increased ApoE secretion at 40 μM // * // * 886 // N-acetyl-3-bromo-4-hydroxylphenylethamine // N // * // * // * 573 Porifera Aplysinella sp. // Sykes Reef, Great Barrier Reef, Australia // Aplysinellamides A–C, bromotyrosine-derived metabolites from an Australian Aplysinella sp. marine sponge 887 // aplysinellamide A // N // * // * // * 888 // aplysinellamide B // N // * // * // * 889 // aplysinellamide C // N // * // * // * 890 // aplysinellamide-1-N-oxide // N // * // * // * Key:


66

7

Sponges OH

HO

OH

HO

OH

HO

O N

HN O O

N

O

O

O

N

O

N

N 1

894 (1Z) 895 (1E)

N

O

O

OH

896

HO N

NH

N N

O

OH N

NHMe †897

N

N

HO

N H

HO

O N

O

N

OH

OH

891 OH

892

893 OH

HO

HO 3SO

898

O

∆

R1

R2

OH H

R2

899 R1 = OH, R 2 = COOH, X = N(CH 2) 2SO3H, ∆ saturated 900 R1 = OH, R 2 = COOH, X = O, ∆ saturated 901 R1 = OSO3H, R 2 = Me, X = O

902

R1

HO

OSO3H

SO3H

NH 2

X OH

OH

NH

O

O

903

904 R1 = NHCH 2CH 2SO3H, R 2 = H 905 R1 = H, R 2 = NHCH 2CH 2SO3H

574 Porifera Dendrilla nigra // Tuticorin, India // Denigrins A–C: new antitubercular 3,4-diarylpyrrole alkaloids from Dendrilla nigra. 891 // denigrin A // N // mod. to weak AB activity // * // * 892 // denigrin B // N // mod. to weak AB activity // * // * 893 // denigrin C // N // mod. to weak AB activity // * // * Porifera Haliclona sp. // Hainan Is., China // Two new thyminenol derivatives from the marine sponge Haliclona sp. 894 // cis-thyminenol // N // * // * // * 895 // trans-thyminenol // N // * // * // * 504 Porifera Petrosia sp. // Jeddah, Saudi Arabia // Cytotoxic effects of three new metabolites from Red Sea marine sponge, Petrosia sp. 896 // 3,7-dimethyl-2-(methylamino)-3H-purin-6(7H)-one // N // IC50 68 μg/mL DNA binding using methyl green displacement // * // * 576 Porifera Phoriospongia sp. // Port Phillip Bay, Victoria, Australia // Isolation and synthesis of N-acyladenine and adenosine alkaloids from a southern Australian marine sponge, Phoriospongia sp. 897 // phorioadenine A // N // weak nemotocidal activ. vs Haemonchus contortus // Synth. used to establish abs. config. of MNP, related adenosine compd also detected by LCMS // * 577 Porifera Dragmacidon coccineum // Hurghada, Egypt // Dragmacidoside: a new nucleoside from the Red Sea sponge Dragmacidon coccinea 898 // dragmacidoside // N // * // * // * 578 Porifera Aka (Siphonodictyon) coralliphagum // San Salvador, Bahamas // New sesquiterpene hydroquinones from the Caribbean sponge Aka coralliphagum 899 // siphonodictyal E1 // N // * // * // * 900 // siphonodictyal E2 // N // * // * // * 901 // siphonodictyal E3 // N // mod. AB activity // * // * 902 // siphonodictyal E4 // N // low activity versus HTCL // * // * 903 // cyclosiphonodictyol A // N // mod. AB and low activity vs HTCL // * // * Porifera Dysidea sp. // Scott Reef, W. Australia // Tauroarenarones A and B, new taurine-containing meroterpenoids from the marine sponge Dysidea sp. 904 // tauroarenarone A // N // * // * // * 905 // tauroarenarone B // N // * // * // * Key:


67

7

Sponges O O

NH

OEt

O

O R1

R1

R2

R2

O

O

O H H

O

H

O HO

R1 = NHCH 2CHMe 2, R 2 = H NH

R 2 = H, R1 =

909 R1 = H, R 2 = NMe 2 910 R1 = NMe 2, R 2 = H 911 R1 = H, R 2 = NHCH 2CHMe 2 912 R1 = H, R 2 = NH

914 R1 915 R1 916 R1 917 R1

OH

H

H

†920

†908

H

O

†906 †907

H

H

†921

†922

= H, R 2 = NHMe =NHMe, R 2 = H = H, R 2 = NMe 2 =NHCH 2CHMe 2, R 2 = H

918 R 2 = H, R1 =

NH

919 R1 = NH(CH 2) 2Ph, R 2 = H

913 R1 = NH(CH 2) 2Ph, R 2 = H

580 Porifera Dysidea sp. // Yongxing Is., S. China Sea // Dysidinoid A, an unusual meroterpenoid with anti-MRSA activity from the South China Sea aponge Dysidea sp. 906 // dysidinoid A // N // mod. antibacterial (MIC 8 µg/mL vs MRSA) // * // * 581 Porifera Dysidea fragilis // Pointe De Senti Joal, Senegal // Dysidaminones A–M, cytotoxic and NF-kB inhibitory sesquiterpene aminoquinones from the South China Sea sponge Dysidea fragilis 907 // dysidaminone A // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 908 // dysidaminone B // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 909 // dysidaminone C // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 910 // dysidaminone D // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 911 // dysidaminone E // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 912 // dysidaminone F // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 913 // dysidaminone G // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 914 // dysidaminone H // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 915 // dysidaminone I // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 916 // dysidaminone J // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 917 // dysidaminone K // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 918 // dysidaminone L // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 919 // dysidaminone M // N // mod. activity vs HTCLs and NF-κB // 18-amino group key SAR // * 582 Porifera Dysidea avara // Yongxing Is., S. China Sea // Dysideanones A–C, unusual sesquiterpene quinones from the South China Sea sponge Dysidea avara 920 // dysideanone A // N // * // 6/6/6/6 tetracyclic structure unprecedented // * 921 // dysideanone B // N // low µM activity against HTCL and various microbial species // 6/6/6/6 tetracyclic structure unprecedented // * 922 // dysideanone C // N // * // * // *

Key:


68

7

Sponges R

HN

923 R =

OH

O

O

O

924 R =

O O

O

O

O

S

OH

HO

OH

O

O H

O

O

OH

6

N H

O OH 925 R = 926 R = CH 2SMe 927 R = iPr

NH

O †930

O

†931

OH

O 932

OH

OH

933

583 Porifera Dactylospongia metachromia // Ambon, Indonesia // Cytotoxic and protein kinase inhibiting nakijiquinones and nakijiquinols from the sponge Dactylospongia metachromia 923 // 5-epi-nakijiquinone S // N // low µM activity HTCL, no inhib. of protein kinases // * // * 924 // 5-epi-nakijiquinone Q // N // low µM activity HTCL, no inhib. of protein kinases // * // * 925 // 5-epi-nakijiquinone T // N // low µM activity HTCL, no inhib. of protein kinases // * // * 926 // 5-epi-nakijiquinone U // N // low µM activity HTCL, no inhib. of protein kinases // * // * 927 // 5-epi-nakijiquinone N // N // low µM activity HTCL, no inhib. of protein kinases // * // * 928 // 5-epi-nakijinol C // N // inactive vs HTCL, potent low µM inhib. of 16 protein kinases // * // * 929 // 5-epi-nakijinol D // N // inactive vs HTCL, potent low µM inhib. of 16 protein kinases // * // * 584 Porifera Xestospongia sp. // Likpan, N. Sulawesi, Indonesia // 1-Hydroxyethylhalenaquinone: a new proteasome inhibitor from the marine sponge Xestospongia sp. 930 // 1-hydroxyethylhalenaquinone // N // potent inhib. of chymotrypsin-like activity of proteasome // * // * 585 Porifera Xestospongia vansoesti // Palawan Is., Philippines // Indoleamine 2,3-dioxygenase inhibitors isolated from the sponge Xestospongia vansoesti: structure elucidation, analogue synthesis, and biological activity 931 // xestolactone A // N // weak inhib. of IDO // * // * 932 // xestosaprol O // N // mod. inhib. of IDO // SAR study of analogues shows 3-OH detrimental to IDO inhib. // * 586 Porifera Sarcotragus sp. inosulus // Porto-Conte Bay, Sardinia, Italy // Isolation of hydroxyoctaprenyl-1',4'-hydroquinone, a new octaprenylhydroquinone from the marine sponge Sarcotragus spinosulus and evaluation of its pharmacological activity on acetylcholine and glutamate release in the rat central nervous system 933 // hydroxyoctaprenyl-1’,4’-hydroquinone // N // effect neurotransmission by enhancing Ca2+-dependent glutamate release in nerve synaptosomes // * // *

Key:


69

7

Sponges

934

O

OHCHN

OR

OHCHN OH

OHCHN

OHCHN

935

936 R = H H 937 R = Me

H

OH

OHCHN OH

938 R = H H 939 R = Me

OR

OHCHN

O OHCHN

940

H

H R 946

O O

947

HO

O

OR

OHCHN 943 R = 944 R = 945 R =

941 R = H H 942 R = Me

OH

O

R

OH OH H OH OMe OH

OH

O OMe

N

948 R = CH 2CHMe 2 949 R = CHMeCH 2Me 950 R = CH 2Ph

R

951

O

N

O MeO 952 R = 953 R =

O

HN OH OH

O

OAc

954

CN

955

587 Porifera Axinyssa sp. // Andaman Sea, Thailand // Formamidobisabolene-based derivatives from a sponge Axinyssa sp. 934 // axinyssine A // N // * // * // * 935 // axinyssine B // N // * // * // * 936 // axinyssine C // N // weak AB activity // * // * 937 // axinyssine D // N // * // * // * 938 // axinyssine E // N // * // * // * 939 // axinyssine F // N // weak AB activity // * // * 940 // axinyssine G // N // weak AB activity // * // * 941 // axinyssine H // N // weak AB activity // * // * 942 // axinyssine I // N // * // * // * 943 // axinyssine J // N // * // * // * 944 // axinyssine K // N // * // * // * 945 // axinyssine L // N // weak AB activity // * // * 946 // 6-acetyl-3-methyl-3- formamidocyclohexane // M // * // * // s156 588 Porifera Ircinia sp. // Tongyeong City, S. Korea // Sesquiterpenoids with PPARδ agonistic effect from a Korean marine sponge Ircinia sp. 947 // * // N // mod. agonist of hPPARδ // * // * 948 // * // N // * // * // * 949 // * // N // * // * // * 950 // * // N // mod. agonist of hPPARδ // * // * 951 // * // N // * // * // * 952 // * // N // * // * // * 953 // * // N // * // * // * 589 Porifera Axinyssa sp. // Pingtung, Taiwan // New nitrogenous bisabolene-type sesquiterpenes from a Formosan sponge Axinyssa sp. 954 // axinysaline A // N // mod. activity vs 2 HTCL // * // * 955 // axinysaline B // N // * // * // *

Key:


70

7

Sponges MeO

O

NHCHO

OH

H O

NHCHO

H

H

H

H

H HO

HO

956

OH

957

R

HO

OH

958

OH

959 R = 960 R =

R OH OH

961 R = 962 R =

OH OH

O O O O

O O MeOOC †966 †965

O

964 O

O

MeOOC

963

COOH

R= †967 R =

R OH OH

†968

R= †969 R =

OH OH

HO R

O

H

MeOOC

MeOOC

O

O

OH

HO †970

R 971 R = 972 R =

N H

OH HO H OH

H

OH 973

590 Porifera Dysidea cinerea // Lang Co Beach, Vietnam // Muurolane-type sesquiterpenes from marine sponge Dysidea cinerea 956 // (4R,5R)-muurol-1(6),10(14)-diene-4,5-diol // N // * // * // * 957 // (4R,5R)-muurol-1(6)-ene-4,5-diol // N // * // * // * 958 // (4R,5R,10R)-10-methoxymuurol-1(6)-ene-4,5-diol // N // * // * // * 959 // (4S)-4-hydroxy-1,10-seco-muurol-5-ene-1,10-dione // N // * // * // * 960 // (4R)-4-hydroxy-1,10-seco-muurol-5-ene-1,10-dione // N // * // * // * 961 // (6S,10S)-6,10-dihydroxy-7,8-seco-2,8-cyclo-muurol-4(5),7(11)-diene-12-oic acid // N // * // * // * 962 // (6R,10S)-6,10-dihydroxy-7,8-seco-2,8-cyclo-muurol-4(5),7(11)-diene-12-oic acid // N // * // * // * 591 Porifera Topsentia sp. // Jeju Is., S. Korea // Four sesquiterpenes isolated from a marine sponge Topsentia species 963 // * // N // * // * // * 964 // * // M // * // * // s157 592 Porifera Diacarnus megaspinorhabdosa // Woody Is., S. China Sea // Relative and absolute stereochemistry of diacarperoxides: antimalarial norditerpene endoperoxides from marine sponge Diacarnus megaspinorhabdosa 965 // diacarperoxide H // N // mod. to weak activity against P. falciparum (W2) // * // * 966 // diacarperoxide I // N // mod. activity against P. falciparum (W2 and D6) // * // * 967 // diacarperoxide J // N // mod. activity against P. falciparum (W2 and D6) // * // * 968 // diacarperoxide K // N // * // * // * 969 // diacarperoxide L // N // * // * // * 970 // diacardiol B // N // * // * // * 593 Porifera Spongia sp. // Bunaken Marine Park, Sulawesi // Spongiapyridine and related spongians isolated from an Indonesian Spongia sp. 971 // 18-nor-3,17-dihydroxyspongia-3,13(16),14-trien-2-one // N // * // * // * 972 // 18-nor-3,5,17-trihydroxyspongia-3,13(16),14-trien-2-one // N // mod. aromatase inhib. and weak QR1 inducer // * // * 973 // spongiapyridine // N // * // * // *

Key:


71

7

Sponges O N

COOH

R N COOH O COOH 975

†983

COOH 974 R = COOH H N 976 R = N

HN

O

986

OH

CHO

979 R = CH 2Ph

NH 2

O

OHC

X

980 R = CH(Me)CH 2Me N

977 R = CH 2NH 2 978 R = iPr

H

COR 981 R = CH 2iPr 982 R = COOMe

†984

X = O, R = NH 2 †985 X = NH, R = OH

OH

987

CHO

594 Porifera Darwinella oxeata // Port Hardy, D'Urville Is. New Zealand // The oxeatamides: nitrogenous spongian diterpenes from the New Zealand marine sponge Darwinella oxeata 974 // oxeatamide A // N // * // * // * 975 // iso-oxeatamide A // N // * // * // * 976 // oxeatamide B // N // * // * // * 977 // oxeatamide C // N // * // * // * 978 // oxeatamide D // N // * // * // * 979 // oxeatamide E // N // * // * // * 980 // oxeatamide F // N // * // * // * 981 // oxeatamide G // N // * // * // * 982 // oxeatamide A 23-methyl ester // N // * // Probable artefact of isolation // * 595 Porifera Hippospongia lachne // Yongxing Is./Seven Connected Islets, S. China Sea // New hippolide derivatives with protein tyrosine phosphatase 1B inhibitory activity from the marine sponge Hippospongia lachne 983 // * // N // mod. cytoxicity against HTCL // * // * 984 // * // N // * // * // * 985 // * // N // low cytoxicity against HTCL // * // * 986 // * // N // low cytoxicity against HTCL // * // * 987 // * // N // mod. cytoxicity against HTCL // * // *

Key:


72

7

Sponges HO OH

O

OH

O

OSO3Na

OSO3

OMe

O N

H

N

N

N

N

995

H

O NH

OH

992 X = 2H, Y = O, R =

989 X = O, Y = 2H, R =

988

994

H

R

H 2

H

N

X

H O

H

Y

H

H

OAc

H

COOH

OH

COOH 993 X = 2H, Y = O, R =

S

991 X = O, Y = 2H, R =

NH

O O

990 X = O, Y = 2H, R =

OAc

∆

SO3H

H

SO3H

H

H


H

H

H

OMe

998

506 Porifera Coscinoderma sp. // Weno Is., Chuuk State, Micronesia // Suvanine sesterterpenes and deacyl irciniasulfonic acids from a tropical Coscinoderma sp. sponge 988 // suvanine N,N-dimethyl-1,3-dimethylherbipoline salt // N // mod. to weak AB activity and vs HTCL, ATPase // * // * 989 // coscinolactam C // N // mod. to weak AB activity and vs HTCL, ATPase // * // * 990 // coscinolactam D // N // mod. to weak AB activity and vs HTCL, ATPase // * // * 991 // coscinolactam E // N // mod. to weak AB activity and vs HTCL, ATPase // * // * 992 // coscinolactam F // N // mod. to weak AB activity and vs HTCL, ATPase // * // * 993 // coscinolactam G // N // mod. to weak AB activity and vs HTCL, ATPase // * // * 596 Porifera Hyrtios sp., Petrosaspongia sp. // Vanua Levu outter reef, Fiji // Scalarane sesterterpenes from Thorectidae sponges as inhibitors of TDP-43 nuclear factor 994 // 16-epi-scalarafuran // N // low affinity binding to TDP-43 // * // * 995 // * // N // high affinity binding to TDP-43 // * // * 996 // Petrosaspongiolactam A // N // high affinity binding to TDP-43 // * // * 997 // petrosaspongiolactam B // N // low affinity binding to TDP-43 // * // * 998 // petrosaspongiolactam C // N // low affinity binding to TDP-43 // * // * O O R1

OAc

O

OAc

7

H

Key:

H

OR 2

H

H O

O H

H H

999 R1 = OH, R 2 = H 1000 R1 = H, R 2 = Ac 1001 R1 = R 2 = H

H

O

O O

O

OAc H

NH

OH

OH

O

OH

HO

O

O

1002 H H

H

H

H

H

1004

H OH

H

OR1

O

H R2

1005

1003


†1006

Me R1 = Me, R 2 = Me R1 = Me, R 2 = 1008 R1 = H, R 2 = Me

†1007

73

7

Sponges

597 Porifera Scalarispongia sp. // Dokdo, S. Korea // Cytotoxic sesterterpenoids isolated from the marine sponge Scalarispongia sp. 999 // 16-O-deacetyl-12,16-epi-scalarolbutanolide // N // * // * // * 1000 // * // N // weak inihibito of 6 HTCLs // * // * 1001 // * // N // weak inihibito of 6 HTCLs // * // * 1002 // * // N // weak inihibito of 6 HTCLs // * // * 598 Porifera Hyrtios erectus // Yongxing Is., S. China Sea // Two new scaralane-type sesterterpenoids isolated from the marine sponge Hyrtios erectus 1003 // scalarinether // N // * // * // * 1004 // hydroxy-16-deacetyl-12-epi-scalarafuran acetate // N // * // * // * 599 Porifera Hyrtios sp. // Woody Is./Rocky Is., S. China Sea // Scalarane sesterterpenes from the Paracel Islands marine sponge Hyrtios sp. 1005 // sesterstamide // N // weak antileishmanial activity // * // * 600 Porifera Clathria gombawuiensis // Gageo-do, S. Korea // Gombaspiroketals A–C, sesterterpenes from the sponge Clathria gombawuiensis 1006 // gombaspiroketal A // N // potent activity vs HTCLs, weak AB and mod. ATPase activity // * // * 1007 // gombaspiroketal B // N // potent activity vs HTCLs, weak AB and ATPase activity // * // * 1008 // gombaspiroketal C // N // potent activity vs HTCLs, weak AB and ATPase activity // * // *

O

HO

HO

H

H

O

O

H

OOH

O

OH

O

H O

O

O

H

H Br 1011

OH

H

H

†1010

H

HO

1012

H

O

O

H

1014

HO

R3

H

OH 20

H HN

OH R1

O O

H

H 1015

AcO

H

1013

H

H

H

H O

HO

H

H

HO

O

H

O

H

†1009

OH

OH

HO

H 1016

HO

H

R2

H H 2N

1017 R1 = R 2 = H, R 3 =

R

H

H

H 1020 R = H 1021 R = OAc

H

O

HO

HO

1022 O

1018 R1 = R 2 = OH, R 3 = 1019 R1 = R 2 = H, R 3 =

601 Porifera Phorbas sp. // Gageo Is., S. Korea // Phorbaketals L–N, cytotoxic sesterterpenoids isolated from the marine sponge of the genus Phorbas 1009 // phorbaketal L // N // mod. to weak activity vs HTCLs // * // * 1010 // phorbaketal M // N // mod. to weak activity vs HTCLs // * // * 1011 // phorbaketal N // N // mod. to weak activity vs HTCLs // * // * Key:


74

7

Sponges

602 Porifera Haliclona simulans // Kilkieran Bay, Galway, Ireland // Isolation and identification of antitrypanosomal and antimycobacterial active steroids from Haliclona simulans 1012 // 24-vinyl-cholest-9-ene-3β,24-diol // N // mod. to weak AB activity and weak activity vs HTCL // * // * 1013 // 20-methyl-pregn-6-en-3β-ol, 5α,8α-epidioxy // N // mod. to weak AB activity and weak activity vs HTCL // * // * 504 Porifera Petrosia sp. // Jeddah, Saudi Arabia // Cytotoxic effects of three new metabolites from Red Sea marine sponge, Petrosia sp. 1014 // 3β,7β,9α-trihydroxycholest-5-en // N // IC50 78 μg/mL DNA binding using methyl green displacement // * // * 505 Porifera Echinoclathria gibbosa // Hurghada, Egypt // New compounds from the Red Sea marine sponge Echinoclathria gibbosa 1015 // β-sitosterol-3-O-(3Z)-pentacosenoate // N // weakly active vs 3 HTCLs // * // * 1016 // 5α-pregna-3β-acetoxy-12β,16β-diol-20-one // N // * // * // * 603 Porifera Theonella swinhoei, T. conica // Amami-oshima Is., Japan // Insights on pregnane-X-receptor modulation. Natural and semisynthetic steroids from Theonella marine sponges 1017 // preconicasterol // N // mod. PXR agonist (EC50 = 21 µM) // From T. conica // * 1018 // 24-dehydroconicasterol D // N // * // From T.swinhoei // * 1019 // 25-dehydrotheonellasterol // N // * // From T.swinhoei // * 604 Porifera Corticium niger // Calumpan Peninsula, Philippines // Steroidal alkaloids from the marine sponge Corticium niger that inhibit growth of human colon carcinoma cells 1020 // plakinamine N // N // weak activity against 60 HTCLs // * // * 1021 // plakinamine O // N // mod. activity against 60 HTCLs // * // * 605 Porifera Ircinia sp. // Yeongdeok-Gun, S. Korea // An antibacterial 9,11-secosterol from a marine sponge Ircinia sp. 1022 // * // N // modest AB activity // * // * O

∆ ∆

H

O

H

H

†1026

H

O

O

HO

H

O

HO

O

H OH

1031

O

HO

O 1029 (13E) 1030 (13Z)

O

O

R

OH

H HO

O

H

HO

13

OH

AcO O

NH HN

COOH 1028

H

O

†1027

H

O

O


H

O

O

H

HO

H HO

O O

OH

MeO O

9

1032

O 1033 R = 1034 R = COOH

N

†1025

606 Porifera Plakortis cfr.lita // Bunaken Marine Park of Manado, Indonesia // Incisterols, highly degraded marine sterols, are a new chemotype of PXR agonists 1023 // incisterol A5 // N // agonist of PXR transactivation at 10 μM in HepG2 cells // * // * 1024 // incisterol A6 // N // agonist of PXR transactivation at 10 μM in HepG2 cells // * // * 607 Porifera Theonella swinhoei // Xisha Is., S. China Sea // New steroids with a rearranged skeleton as (h)p300 inhibitors from the sponge Theonella swinhoei 1025 // swinhoeisterol A // N // mod. activity vs HTCLs and (h)p300 histone deacetylase // * // * 1026 // swinhoeisterol B // N // mod. activity vs HTCLs and (h)p300 histone deacetylase // * // * 608 Porifera Cinachyrella sp. // Oshima-shinsone, Japan // Cinanthrenol A, an estrogenic steroid containing phenanthrene nucleus, from a marine sponge Cinachyrella sp. 1027 // cinanthrenol A // N // potent (nM) activity vs HTCLs and competitive binding vs estradiol against estrogen receptor // * // *

Key:


75

7

Sponges

609 Porifera Jaspis stellifera // S. China Sea // Jaspiferins C–F, four new isomalabaricane-type triterpenoids from the South China Sea sponge Jaspis stellifera 1028 // jaspiferin C // N // * // * // * 1029 // jaspiferin D // N // * // * // * 1030 // jaspiferin E // N // * // * // * 1031 // jaspiferin F // N // * // * // * 610 Porifera Siphonochalina siphonella // Sharm Obhur, Saudi Arabia // Cytotoxic neviotane triterpene-type from the red sea sponge Siphonochalina siphonella 1032 // neviotine C // N // weakly active vs 3 HTCLs // Readily tautomersises to neviotine A // * 645 Porifera Fascaplysinopsis sp. // Madagascar // The taumycin A macrocycle: asymmetric total synthesis and revision of relative stereochemistry 1033 // taumycin A // R // * // * // s158 1034 // taumycin B // R // * // * // s158 OMe

OMe O O O

N

COOH

O

HO OH

N H

O

O

O

OH

HO 11

1035 N

N H

9 †1036

N

Br Br

Br OMe

1037

Br OH

H

†1038

H

†1039

651 Porifera Topsentia sp. // * // Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter 1035 // topsentolide A2 // R // * // * // s159 657 Porifera Amphimedon sp. // // (−)-(2S,3R,Z)-Nakinadine A: first asymmetric synthesis and absolute configuration assignment 1036 // nakinadine A // R // * // * // s160 666 Porifera Verongia sp. // * // Synthesis and assignment of the absolute stereochemistry of (+)-hemifistularin 3 1037 // (+)-hemifistularin-3 // R // * // Synthesis used to establish abs. config. of MNP // s161 673 Porifera Euryspongia sp. // * // Synthesis of the sesquiterpenes albicanol, drimanol, and drimanic acid, and the marine sesquiterpene hydroquinone deoxyspongiaquinol 1038 // deoxyspongiaquinol // R // * // Abs. config. established by synthesis // s162 1039 // deoxyspongiaquinone // R // * // Abs. config. established by synthesis // s162

Key:


76

8

Cnidarians

O N

O

O N

HN

N HO

O

OH

O N

N

1041 (10E) 1042 (10Z)

N

10

OHC

1044 (10E) 1045 (10Z)

N

O ∆

R 2O

N

N

R1

O

MeHNOC

N

10

R3

NH NH

N O NH 2 H R1 = R 3 = H, R 2 = Me, ∆ saturated †1048 R = Br, R = R = H, ∆ saturated 1 2 3 1049 R1 = Br, R 2 = R 3 = H †1050 R = R = Br, R = Me, ∆ saturated 1 3 2 1051 R1 = R 3 = Br, R 2 = Me †1047

†1040

O N

O N

N N

1043

MeHNOC N

N OHC

N

O 1046

683 Cnidaria Menella kanisa // Xieyang Is., China // A new diketopiperazine from the gorgonian coral Menella kanisa 1040 // menazepine A // N // * // * // * 684 Cnidaria Echinogorgia pseudossapo // Daya Bay, China // Six new tetraprenylated alkaloids from the South China Sea gorgonian Echinogorgia pseudossapo 1041 // malonganenone L // N // PDE4D IC50 8.5 µM // * // * 1042 // malonganenone M // N // * // * // * 1044 // malonganenone O // N // * // * // * 1045 // malonganenone P // N // * // * // * 1046 // malonganenone Q // N // PDE4D IC50 20.3 µM // * // * 685 Cnidaria Parazoanthus axinellae // Villefranche-sur-Mer, France // Metabolome consistency: additional parazoanthines from the Mediterranean zoanthid Parazoanthus axinellae 1047 // parazoanthine F // N // * // structure by MS-MS, ECD // * 1048 // parazoanthine G // N // * // structure by MS-MS, ECD // * 1049 // parazoanthine H // N // * // structure by MS-MS // * 1050 // parazonathine I // N // * // structure by MS-MS, ECD // * 1051 // parazoanthine J // N // * // structure by MS-MS // *

Key:


77

8

Cnidarians O

O O

H

O

H

H

H

HO

H

HO

OH

O

N

OH

O

O

OH

HO

OH

O

X O

O

1053

1052

H

OH

O

H 2N

OH

H N

H

O

O

O H

O

OH

H

OH

O

OH

OH

O R

O

HO

OH OH

1054 R = OH, X = O 1055 R = H, X = 2H O

O

H

O

O H

O

H OH

H

H O N

O

OH

H

O

H

O O

H

N

O

O

HN

HO OH

OH

N H OH

OH OH

HO

HO

O

OH

33

42 †1059

O

OH

O

N

1058

OH

OH

25

OH

O

O

OH

O OH

O †1057

OH

OH O

O

O 1056

O

OH

OH O

H

OH

R= †1060 R =

Me Me

HO

OH O

47

HO

HO

R

OH

OH

50

OH

OH OH

OH

OH

686 Cnidaria Zoanthus sp. // Punta del Hidalgo, Tenerife // Zoaramine, a zoanthamine-like alkaloid with a new skeleton 1052 // zoaramine // N // * // * // * 1053 // zoarenone // N // * // * // * 687 Cnidaria Zoanthus sp. // Punta del Hidalgo, Tenerife // New oxidized zoanthamines from a Canary Islands Zoanthus sp. 1054 // 2-hydroxy-11-ketonorzoanthamide B // N // * // * // * 1055 // norzoanthamide B // N // * // * // * 1056 // 15-hydroxynorzoanthamine // N // * // * // * 688 Cnidaria Zoanthus kuroshio // Taiwan // Kuroshines A and B, new alkaloids from Zoanthus kuroshio 1057 // kuroshine A // N // * // Absolute configuration X-ray. // * 1058 // kuroshine B // N // * // * // * 689 Cnidaria Palythoa toxica, Cnidaria Palythoa tuberculosa // Hawaii // Stereoisomers of 42-hydroxy palytoxin from Hawaiian Palythoa toxica and P. tuberculosa: stereostructure elucidation, detection, and biological activities 1059 // (42S)-hydroxy-(50R)-palytoxin // N // cytotox. // note structure in paper missing C-7 OH group. // * 1060 // (42S)-hydroxy-(50S)-palytoxin // R // cytotox. // note structure in paper missing C-7 OH group. // s163

Key:


OH

78

8

Cnidarians O

O

HO OEt O

O

O

COOMe

1061

OH

COOMe

O

OH

O

O 1062

O

O

O

COOR1

HO

1063

1064 1065 1066 1067

R1 R1 R1 R1

R2 = Me, R 2 = H = R2 = H = Me, R 2 = OMe = H, R 2 = OMe

O 1068 n =4 1069 n =2

O

O

OMe COOMe

O

HO

O

n

O

H

†1070

†1071

H

O

1072

692 Cnidaria Subergorgia suberosa // Zhanjian., S. China Sea. // Tortuosenes A and B, new diterpenoid metabolites from the Formosan soft coral Sarcophyton tortuosum 1061 // (5R)-5-(1-ethoxypropyl)-5-hydroxy-3,4-dimethylfuran-2(5H)-one // N // B. amphitrite settlement inhib. // mixture of epimers. // * 693 Cnidaria Sinularia sp. // Dongluo Is., China // Sinulolides A–H, new cyclopentenone and butenolide derivatives from soft coral Sinularia sp. 1062 // sinulolide A // N // * // core absolute via ECD. // * 1063 // sinulolide B // N // * // core absolute via ECD. // * 1064 // sinulolide C // N // * // * // * 1065 // sinulolide D // N // * // * // * 1066 // sinulolide E // N // weak NF-kB inhib. // * // * 1067 // sinulolide F // N // * // * // * 1068 // sinulolide G // N // * // * // * 1069 // sinulolide H // N // * // * // * 694 Cnidaria Subergorgia suberosa // Naozhou Is., S. China Sea // Suberosanones A–C, new metabolites possessing cyclopentenone system from the South China Sea gorgonian coral Subergorgia suberosa 1070 // suberosanone A // N // inactive antifouling, AB // absolute via calculated ECD, ent-sinularone C // s164 1071 // suberosanone B // N // inactive antifouling, AB // absolute via calculated ECD, ent-sinularone D // s164 1072 // suberosanone C // N // inactive antifouling, AB // * // * OH

O

OH

1073

HO O

O

HO

OH

H H

HO 1076 1077 1079 1084 1088

∆

R1 R1 R1 R1

R2 = R 2 = OH = OH, R 2 = H, ∆ saturated = R2 = H = R 2 = H, ∆ saturated

R2 1078 1080 1085 1086 1087

R1 R1 R1 R1 R1

OH = R 2 = OH, R 3 = OH OH = R 2 = H, R 3 = = OH, R 2 = H, R 3 = OH = OH, R 2 = H, R 3 = OH = R 2 = H, R 3 = OH

HO

O

R3

O 1074 R = 1075 R =

HO

OAc

R

O

R1

R1

O

HO 1081

1082

H

1083

H

1090

1089

695 Cnidaria Pseudopterogorgia rigida, Antillogorgia rigida // Bahamas Islands // Bisabolane and chamigrane sesquiterpenes from the soft coral Pseudopterogorgia rigida 1073 // * // N // * // * // * 1074 // (9R*)-1,9-epoxy-4-hydroxy-α-curcumene // N // * // * // * 1075 // (9S*)-1,9-epoxy-4-hydroxy-α-curcumene // N // * // * // * 1076 // acetyl-β-bisabolol // N // * // * // * 1077 // * // N // * // * // * 1078 // 9-hydroxy-curcuhydroquinone // N // * // * // * 1079 // 10-hydroxy-10,11-dihydrocurcuphenol // N // * // * // * Key:


79

8

Cnidarians 1080 // (7R*,9S*)-bisacumol // M // * // rhizome NP // s165 1081 // * // M // * // from oil and plant leaves, cytotoxic // s166 1082 // α-pipitzol // M // * // * // s167 1083 // β-pipitzol // M // * // * // s167 1084 // * // M // * // synthetic // s168 1085 // * // M // * // synthetic // s169 1086 // * // M // * // synthetic // s169 1087 // * // M // * // rhizome NP and synthetic // s170 1088 // * // M // * // synthetic // s171 1089 // * // M // * // synthetic // s172 1090 // * // M // * // synthetic // s173

O ∆

H

H O

H OH

1091

OEt

H

H H

1092

1093

OH

R

COOH

OH H

COOH X

O

O

H

H

AcO

H

H

O O

1094 R = H 1095 R = OH, ∆ saturated

1096 X = O 1097 X = OH ,H

H

OH 1098

1099

H

H

1100

H

H SH

H

H H

O 1101

696 Cnidaria Rumphella antipathes // Pingtung, Taiwan // Rumphellols A and B, new caryophyllene sesquiterpenoids from a Formosan gorgonian coral, Rumphella antipathies 1091 // rumphellol A // N // weak inhib. superoxide formation and elastase release // * // * 1092 // rumphellol B // N // weak inhib. superoxide formation and elastase release // * // * 697 Cnidaria Rumphella antipathes // Pingtung, Taiwan // Rumphellaoic acid A, a novel sesquiterpenoid from the Formosan gorgonian coral Rumphella antipathies 1093 // rumphellaoic acid A // N // weak inhib. elastase release // * // * 698 Cnidaria Rumphella antipathes // Pingtung, Taiwan // Rumphellaones B and C, new 4,5-seco-caryophyllane sesquiterpenoids from Rumphella antipathies 1094 // rumphellaone B // N // * // * // * 1095 // rumphellaone C // N // weak inhib. superoxide formation and elastase release // * // * 699 Cnidaria Lemnalia philippinensis // Lanyu, Taiwan // Oxygenated eremophilane- and neolemnane-derived sesquiterpenoids from the soft coral Lemnalia philippinensis 1096 // philippinlin C // N // not cytotox. (3 HTCL) // * // * 1097 // philippinlin D // N // not cytotox. (3 HTCL) // * // * 1098 // philippinlin E // N // not cytotox. (3 HTCL) // * // * 700 Cnidaria Menella kanisa // Weizhou Is., S. China Sea // A new sesquiterpene from the Hainan gorgonian Menella kanisa Grassoff 1099 // menecubebane A // N // toxic to brine shrimp // * // * 701 Cnidaria Nephthea erecta // Green Is., Taiwan // Kelsoenethiol and dikelsoenyl ether, two unique kelsoane-type sesquiterpenes, from the Formosan soft coral Nephthea erecta 1100 // kelsoenethiol // N // moderate cytotox. (2 cell lines) // * // * 1101 // dikelsoenyl ether // N // * // * // *

Key:


80

8

Cnidarians H

X

H

AcO H

H

HO 1104

OH

H

O

O

HO

HO 1105 OH

OH

1106

OMe

O

H

H

O

OHC

H

OH

OH

O

1107

O

H

O O

†1108

1102 X = OMe ,H 1103 X = O

†1109

1110

O

702 Cnidaria // Shag Rocks, South Georgia // Shagenes A and B, new tricyclic sesquiterpenes produced by an undescribed Antarctic octocoral 1102 // shagene A // N // antileishmanial activity // * // * 1103 // shagene B // N // inactive // * // * 703 Cnidaria Dendronephthya sp. // Hurghada, Egypt // Dendronephthols A–C, new sesquiterpenoids from the Red Sea soft coral Dendronephthya sp. 1104 // dendronephthol A // N // modest cytotox. (L5187Y) // * // * 1105 // dendronephthol B // N // * // * // * 1106 // dendronephthol C // N // modest cytotox. (L5187Y) // * // * 704 Cnidaria Sinularia kavarattiensis // Mandapam coast, India // Chemical examination of the soft coral Sinularia kavarattiensis and evaluation of anti-microbial activity 1107 // * // N // mild AB activity // * // * 705 Cnidaria Echinogorgia sassapo // Weizhou Islands, S. China Sea // Sesquiterpenoids and steroids from gorgonian Echinogorgia sassapo reticulate 1108 // (1S,5S,8S)-8-methoxy-menelloide B // N // * // absolute via computed ECD. // * 706 Cnidaria Anthogorgia ochracea // Weizhou Islands, S. China Sea // Ochracenoids A and B, guaiazulene-based analogues from gorgonian Anthogorgia ochracea collected from the South China Sea 1109 // ochracenoid A // N // inactive in range of assays // absolute via computed ECD. // * 1110 // ochracenoid B // N // inactive in range of assays // * // * O

MeO

O

O

O

OH

O

O

OAc O

O

O

OH

H

R

R

1111 R = H 1112 R = Me

O

H

O

O O

HO

MeO OH

O H

H

O

1113

O

H 1114

OH

708 Cnidaria Anthogorgia caerulea // Beibu Gulf, S. China Sea // Two new avermectin derivatives from the Beibu Gulf gorgonian Anthogorgia caerulea 1111 // avermectin B1c // N // B. amphitrite settlement inhib. // * // * 1112 // avermectin B1e // N // B. amphitrite settlement inhib. // * // * 709 Cnidaria Lobophytum crassum // Dongsha Atoll, Taiwan // Secocrassumol, a seco-cembranoid from the Dongsha Atoll soft coral Lobophytum crassum 1113 // secocrassumol // N // antiviral (HCMV) // partial absolute config: C-8 ECD, C-12 Moshers. // * 710 Cnidaria Sinularia gyrosa // Dongsha Atoll, Taiwan // Sinugyrosanolide A, an unprecedented C-4 norcembranoid, from the Formosan soft coral Sinularia gyrosa 1114 // sinugyrosanolide A // N // modest cytotox. (P388) // * // * Key:


81

8

Cnidarians COOMe

COOMe OH

O

R

O

HO

HO

HO

O 1115 R = 1116 R =

OH OH

R 1117 R = 1118 R =

R 2O AcO

O

O

OH

R1 O

O

O

1119

OH OH

HO O

O

1120 R = 1121 R =

Me Me

O

O

O

O

1125

1124

1122 R1 = Ac, R 2 = H 1123 R1 = H, R 2 = Ac

O O OH

O

O

O

O

1126

O

O 1127

O

O

Cl

HO O

OH

O

R

HO

HO

H

H

O OH

1132

COOMe

HO

HO 1131

O 1128

OMe

O

AcO

1129

O

O

OAc

HO HO

1130 1133

1134

711 Cnidaria Lobophytum crassum // Con Co, Vietnam // New anti-inflammatory cembranoid diterpenoids from the Vietnamese soft coral Lobophytum crassum 1115 // lobocrasol A // N // NF-kB inhib. // * // * 1116 // lobocrasol B // N // NF-kB inhib. // * // * 1117 // lobocrasol C // N // * // * // * 1118 // lobocrasol D // N // * // * // * 712 Cnidaria Eunicea pinta // San Andres Is., Colombia // Pintoxolanes A–C, highly functionalized 3,14-oxa-bridged cembranoids from the Caribbean gorgonian coral Eunicea pinta 1119 // pintoxolane A // N // weakly cytotox. (NCI) // * // * 1120 // pintoxolane B // N // * // * // * 1121 // pintoxolane C // N // * // * // * 713 Cnidaria Sarcophyton crassocaule // Dongsha, Taiwan // Bioactive cembranoids, sarcocrassocolides P–R, from the Dongsha Atoll soft coral Sarcophyton crassocaule 1122 // sarcocrassocolide P // N // weakly cytotox., potent inhib. of iNOS expression // * // * 1123 // sarcocrassocolide Q // N // weakly cytotox., potent inhib. of iNOS expression // * // * 1124 // sarcocrassocolide R // N // weakly cytotox., potent inhib. of iNOS expression // * // * 714 Cnidaria Sarcophyton glaucum // N. of Jeddah, Saudi Arabia // Three new cembranoid-type diterpenes from Red Sea soft coral Sarcophyton glaucum: isolation and antiproliferative activity against HepG2 cells 1125 // sarcophytolol // N // weakly cytotox. (4 HTCL) // * // * 1126 // sarcophytolide B // N // weakly cytotox. (4 HTCL) // * // * 1127 // sarcophytolide C // N // weakly cytotox. (4 HTCL) // * // * 715 Cnidaria Sarcophyton ehrenbergi // Off Hurghada, Red Sea // New terpenes from the Egyptian soft coral Sarcophyton ehrenbergi 1128 // 7-keto-8α-hydroxy-deepoxysarcophine // N // weakly cytotox. (MCF7) // * // * 1129 // 7β-chloro-8α-hydroxy-12-acetoxy-deepoxysarcophine // N // weakly cytotox. (MCF7) // * // * 1130 // (E)-methyl-3-(5-butyl-1-hydroxy-2,3-dimethyl-4-oxocyclopent-2-enyl) acrylate // N // weakly cytotox. (MCF7) // * // * 716 Cnidaria Sarcophyton sp. // Dongshan Is., China // Four new cembranoids from the soft coral Sarcophyton sp. 1131 // sarcophyton A // N // inactive (MCF-7) // * // * 1132 // sarcophyton B // N // inactive (MCF-7) // * // * 1133 // sarcophyton C // N // inactive (MCF-7) // * // * 1134 // sarcophyton D // N // inactive (MCF-7) // * // * Key:


82

8

Cnidarians O HO

HO O

HO

O

O

O

O

HO

O

O

O

OH

HO

OH

COOMe AcO

OH HO

†1137

S

HO

OH

H 1139

O

S S

H

OH

H

1136

1135

OH

OH

1140 OH

1138

717 Cnidaria Sarcophyton aurantium // Safaga, Egypt // Cytotoxic cembranoids from the Red Sea soft coral, Sarcophyton auritum 1135 // 2-epi-sarcophine // N // weakly cytotox. (2 HTCL) // * // * 1136 // (1R,2E,4S,6E,8R,11R,12R)-2,6-cembradiene-4,8,11,12-tetrol // N // weakly cytotox. (2 HTCL) // * // * 718 Cnidaria Sinularia sp. // Sanya Bay, China // Novel cytotoxic nine-membered macrocyclic polysulfur cembranoid lactones from the soft coral Sinularia sp. 1137 // sinulariaoid A // N // cytotox. (4 HTCL) including 2 resistant lines // absolute config via X-ray analysis. // * 1138 // sinulariaoid B // N // inactive // * // * 1139 // sinulariaoid C // N // inactive // * // * 1140 // sinulariaoid D // N // inactive // * // * O

MeOOC

O OH OH

HO

OH

R

O X

HO 1142 AcO

1143

HO

HOOC 1144

H

OH

H O

OH

O

O †1141

HO

H

OH

HO

H

1145

†1146

O

H

1148 R = OH 1149 R = H

OAc ,H X= 1147 X = O

719 Cnidaria Sinularia numerosa // Sansiantai, Taiwan // Numerosol A–D, new cembranoid diterpenes from the soft coral Sinularia numerosa 1141 // numerosol A // N // * // absolute config Moshers // * 1142 // numerosol B // N // * // * // * 1143 // numerosol C // N // * // * // * 1144 // numerosol D // N // * // * // * 720 Cnidaria Sinularia kavarattiensis // Rameshwaram, India // Bioactive cembrane derivatives from the Indian Ocean soft coral, Sinularia kavarattiensis 1145 // kavaranolide // N // * // * // * 721 Cnidaria Sarcophyton tortuosum // Lanyu Is., Taiwan // Tortuosenes A and B, new diterpenoid metabolites from the Formosan soft coral Sarcophyton tortuosum 1146 // tortuosene A // N // inhibit superoxide formation // absolute config calculated ECD. // * 1147 // tortuosene B // N // inhibit elastase release // * // * 722 Cnidaria Sinularia arborea // S. coast of Taiwan // Discovery of novel diterpenoids from Sinularia arborea 1148 // sinularbol A // N // weak inhib. superoxide formation and elastase release // * // * 1149 // sinularbol B // N // weak inhib. superoxide formation and elastase release // * // * Key:


83

8

Cnidarians O O

OAc R3

R5 HO 1150

R1 O

O

†1151

R1 †1152 R 1 †1153 R 1 †1154 R 1

OAc

OAc OAc

OAc

iBuCOO

OH

OAc

OAc

AcO

R2 H

OCOiBu

O

iBuCOO

OR 4

OH O

H AcO

AcO

O

O

H

O

O

Cl

OH O

AcO

†1155 O = R 4 = Ac, R 2 = H, R 3 = R 5 = OCOCH 2CHMe 2, = R 4 = Ac, R 2 = OCOCH 2CHMe 2, R 3 = OAc, R 5 = OH = H, R 2 = OH, R 3 = OCOCH 2CHMe 2, R 4 = Ac, R 5 = OAc = COCH 2CHMe 2, R 2 = R 3 = OAc, R 4 = COCH 2OH, R 5 = Cl

O

H HO 1156

Cl O O

AcO

O

H AcO 1157

O

Cl

OH

Cl O O

Cl H HO 1158

O O

723 Cnidaria Pennatula aculeata // Dinawan Is., Malaysia // 2-Acetoxyverecynarmin C, a new briarane COX inhibitory diterpenoid from Pennatula aculeata 1150 // 2-acetoxyverecynarmin C // N // COX-1/2 inhib. // * // * 724 Cnidaria Dichotella gemmacea // S. China Sea // Briarane diterpenoids from the gorgonian Dichotella gemmacea 1151 // gemmacolide AS // N // * // absolute config via CD // * 1152 // gemmacolide AT // N // * // absolute config via CD // * 1153 // gemmacolide AU // N // * // absolute config via CD // * 1154 // gemmacolide AV // N // weakly cytotox. (A549) // absolute config via CD // * 1155 // gemmacolide AW // N // mod. cytotox. (MG63) // absolute config via CD // * 1156 // gemmacolide AX // N // * // * // * 1157 // gemmacolide AY // N // * // * // * 725 Cnidaria Briareum sp. // Southern Taiwan // Briarenolide J, the first 12-chlorobriarane diterpenoid from an octocoral Briareum sp. (Briareidae) 1158 // briarenolide J // N // mild inhib. superoxide generation and elastase release // * // * OAc

OAc

R

OAc

OAc Cl

HO OH O

H AcO

†1159

R = OAc †1160 R = Cl †1161 R = OMe

O O

H AcO 1162

O O

726 Cnidaria Junceella gemmacea // S. China Sea // Briarane diterpenes from the South China Sea gorgonian coral, Junceella gemmacea 1159 // junceellolide M // N // * // * // * 1160 // junceellolide N // N // * // * // * 1161 // junceellolide O // N // * // * // * 1162 // junceellolide P // N // * // * // * Key:


84

8

Cnidarians AcO

R1

AcO

AcO

R2

R1

R2

AcO

OAc

OAc

OAc

OAc

OR

∆

I

AcO

AcO

OMe

OAc

R1 I OAc

OAc

OAc

OAc

R O H HO

O 1163 R1 = H, R 2 = OH 1166 R1 = OAc, R 2 = H

OH

Cl O

O

O

O

O Cl H HO

H AcO

O

OH O

O

O

1169

O 1167 R = Me 1168 R = Me, ∆ saturated 1170 R = H

O 1164 R1 = H, R 2 = OH 1165 R1 = OAc, R 2 = H

H AcO

OAc R2

Cl

O

O

H AcO

O

1171 R = H 1172 R = OAc

H AcO

O 1173 R1 = OAc, R 2 = OMe 1174 R1 = OCOEt, R 2 = Cl

O

H

O

O

H

O

1175

O

O

1176

O

727 Cnidaria Junceella fragilis // Meishan Is., China // Fragilisinins A–L, new briarane-type diterpenoids from gorgonian Junceella fragilis 1163 // fragilisinin A // N // * // absolute config via X-ray crystal structure. // * 1164 // fragilisinin B // N // * // * // * 1165 // fragilisinin C // N // * // * // * 1166 // fragilisinin D // N // * // * // * 1167 // fragilisinin E // N // B. amphitrite settlement inhib. // * // * 1168 // fragilisinin F // N // B. amphitrite settlement inhib. // * // * 1169 // fragilisinin G // N // * // * // * 1170 // fragilisinin H // N // * // * // * 1171 // fragilisinin I // N // * // * // * 1172 // fragilisinin J // N // B. amphitrite settlement inhib. // * // * 1173 // fragilisinin K // N // * // * // * 1174 // fragilisinin L // N // * // * // * 728 Cnidaria Ellisella dollfusi // Xisha, S. China Sea // New briarane-type diterpenoids from gorgonian Ellisella dollfusi from the South China Sea 1175 // dollfusilin A // N // * // * // * 1176 // dollfusilin B // N // * // * // * OAc

OAc

O

RO

O

H

AcO O

R=H O 1178 R = COCH 2Me

OAc

O

Cl

OH AcO

†1177

OAc

H AcO 1179

O O

Cl Me 2CHCH 2COO

OH HO AcO 1180

Cl

OH

O AcO O

O

OAc

OAc

O

O

OAc HO

OH

OR 2

O

1181

O O

Cl

OH

R1 O AcO

O

O 1182 R1 = CO(CH 2) 4Me, R 2 = H 1183 R1 = R 2 = Ac

OH

RO HO 1184 R =H 1185 R = OH 1186 R = Ac

O O

729 Cnidaria Briareum violaceum // Pingtung, Taiwan // New briarane diterpenoids from Taiwanese soft coral Briareum violacea 1177 // briaviolide A // N // * // X-ray crystal structure. // * 1178 // briaviolide B // N // * // * // * 1179 // briaviolide C // N // * // * // * 1180 // briaviolide D // N // * // * // * 1181 // briaviolide E // N // weak inhib. superoxide formation and elastase release // * // * 1182 // briaviolide F // N // * // * // * Key:


85

8

Cnidarians 1183 // briaviolide G // N // * // * // * 1184 // briaviolide H // N // * // * // * 1185 // briaviolide I // N // weak inhib. superoxide formation and elastase release // * // * 1186 // briaviolide J // N // * // * // * O

OAc AcO

MeO H

H

OH

AcO

AcO

H

OOH

1189 R = H 1190 R = Ac

OAc

R1 O

O

OH

OAc 1191

OAc

H

O R 2O

R

H

H

OO

O

OMe H

H

H

OAc

1188

O

H O

H

OAc

1187

HO

O

O

O

OH OR

H

OH OH

OAc 1192 R1 = Ac, R 2 = COnPr 1193 R1 = COnPr, R 2 = Ac

H 1194

1195 R = 1196 R =

OAc OH OH

730 Cnidaria Anthogorgia caerulea // Beibu Gulf, S. China Sea // Two new diterpenoids from the Beibu Gulf gorgonian Anthogorgia caerulea 1187 // anthogonoid A // N // B. amphitrite settlement inhib. // * // * 1188 // antsimplexin A // N // B. amphitrite settlement inhib. // * // * 731 Cnidaria Muricella sibogae // Weizhou Is., S. China Sea // Two new eunicellin-based diterpenoids from the South China Sea gorgonian Muricella sibogae Nutting 1189 // sibogin A // N // * // * // * 1190 // sibogin B // N // * // * // * 732 Cnidaria Cladiella sp. // Peng-Hu Is, Taiwan // Cladieunicellin J, a new hydroperoxyeunicellin from Cladiella sp. 1191 // cladieunicellin J // N // * // * // * 733 Cnidaria Klyxum molle // Peng-Hu Is, Taiwan // Klymollins T–X, bioactive eunicellin-based diterpenoids from the soft coral Klyxum molle 1192 // klymollin T // N // * // * // * 1193 // klymollin U // N // * // * // * 1194 // klymollin V // N // * // * // * 1195 // klymollin W // N // * // * // * 1196 // klymollin X // N // reduced inducton of IL-6 // * // * HO

R2 OH OAc

H

R1

H 7

O H

O

H

H OCOnPr

OAc

OH OAc

1197

OR 3 1198 R1 = OH, R 2 = H, R 3 = Ac 1201 R1 = H, R 2 = OH, R 3 = Ac 1199 R1 = OAc, R 2 = H, R 3 = Ac 1212 R1 = R 2 = H, R 3 = COnPr 1200 R1 = OAc, R 2 = OH, R 3 = COnPr

734 Cnidaria Cladiella sp. // Peng-Hu Is, Taiwan // Cladieunicellins M–Q, new eunicellins from Cladiella sp. 1197 // cladieunicellin M // N // weakly cytotox. (Molt 4) // * // * 1198 // cladieunicellin N // N // * // structure same as klymollin Q // s174 1199 // cladieunicellin O // N // weakly cytotox. (Molt 4) // * // * 1200 // cladieunicellin P // N // * // * // * 1201 // cladieunicellin Q // N // weakly cytotox. (Molt 4) // * // * 1212 // litophynin I diacetate // R // * // revised to 7S. // s175 Key:


86

8

Cnidarians R2 R1 O

H

OH

HO

HO OR3

H

AcO

O

OH OH

H

OH R

H

H OCOnPr 1204

1202 R1 = R 2 = H, R 3 = Me 1203 R1 =Ac, R 2 = OAc, R 3 = H

OH AcO

H

H

OAc

OCOnPr 1205 R = H 1206 R = OAc

OH

H

1207

OH

O H

H 1209

1208

O

OH O

H OH

H

H

O

H OAc

AcO

OMe

O

O

H

OCOnPr

AcO

H OAc

O

O

H

O

AcO

OH

H

1210

OCOnPr O

OH

1211

O

735 Cnidaria Cladiella krempfi // Peng-Hu Is, Taiwan // Krempfielins N–P, new anti-inflammatory eunicellins from a Taiwanese soft coral Cladiella krempfi 1202 // krempfielin N // N // strong inhib. of elastase release // * // * 1203 // krempfielin O // N // * // * // * 1204 // krempfielin P // N // * // * // * 736 Cnidaria Cladiella krempfi // Peng-Hu Is, Taiwan // Krempfielins Q and R, two new eunicellin-based diterpenoids from the soft coral Cladiella krempfi 1205 // krempfielin Q // N // * // * // * 1206 // krempfielin R // N // * // * // * 737 Cnidaria Cladiella hirsuta // Peng-Hu Is, Taiwan // Eunicellin-based diterpenoids, hirsutalins N–R, from the Formosan soft coral Cladiella hirsuta 1207 // hirsutalin N // N // * // * // * 1208 // hirsutalin O // N // * // * // * 1209 // hirsutalin P // N // * // * // * 1210 // hirsutalin Q // N // * // * // * 1211 // hirsutalin R // N // mod. cytotox. (2 cell lines) // * // * O O

O H

O 1213

H OAc

O

HO

O

Y HO

OAc

O

H HO

O

O H OAc

1214

O MeO

OH

H

X O

H

O

1215

MeOOC 1216

1217 X = 2H, Y = O 1218 X = O, Y = 2H

739 Cnidaria Cespitularia sp. // Zamami Is., Okinawa // Structure and bioactivity of a trisnorditerpenoid and a diterpenoid from an Okinawan soft coral, Cespitularia sp. 1213 // * // N // cytotox. (HCT116) // * // * 1214 // * // N // * // * // * 740 Cnidaria Xenia elongata // cultured specimens. // Mode of action of diterpene and characterization of related metabolites from the soft coral, Xenia elongata 1215 // * // N // * // * // * 1216 // * // N // * // * // * 741 Cnidaria Cespitularia taeniata // Taiwan // Cespitulones A and B, cytotoxic diterpenoids of a new structure class from the soft coral Cespitularia taeniata 1217 // cespitulone A // N // cytotox. (2 HTCL) // 6S Moshers. // * 1218 // cespitulone B // N // * // * // * Key:


87

8

Cnidarians R R HO ∆

R1 O

H

OAc O

∆

H COOMe

H

H HO

O R = Me ∆ saturated 1220 R = COOMe ∆ saturated 1223 R = Me

†1219

HO X COOR 4

O †1221

R= 1222 R =

H

R 2O OH OH

O

1224 1225 1226 1227 1228 1229 1230 1231 1234 1235 1236

R1 R1 R1 R1 R1 R1 R1 R1 R1 R1 R1

OR 3 = H, R 2 = R 3 = Ac, R 4 = Me, X = OAc,H = R 2 = R 3 = Ac, R 4 = Me, X = OAc,H = R 2 = Ac, R 3 = H, R 4 = Me, X = OAc,H = R 2 = R 3 = Ac, R 4 = Me, X = O = R 3 = H ,R 2 = Ac, R 4 = Me, X = O = H, R 2 = R 3 = Ac, R 4 = Me, X = O = R 3 = R 4 = H, R 2 = Ac, X = O = R 4 = H, R 2 = R 3 = Ac, X = O = R 3 = Ac, R 2 = H, R 4 = Me, X = 2H = H, R 2 = R 3 = Ac, R 4 = Me, X = 2H = R 2 = R 3 = Ac, R 4 = Me, X = 2H

AcO

OAc 1232 ∆ saturated 1233

H

RO 1237 R = Me R = Ac

†1238

742 Cnidaria Sarcophyton trocheliophorum // Yalong Bay, China // Sarsolenane and capnosane diterpenes from the Hainan soft coral Sarcophyton trocheliophorum as PTP1B inhibitors 1219 // dihydrosarsolenone // N // * // absolute config calculated ECD. // * 1220 // methyl dihydrosarsolenoneate // N // * // * // * 1221 // sarsolilide B // N // inhibit PTP1B // absolute config calculated ECD. // * 1222 // sarsolilide C // N // * // * // * 1223 // sarsolenone // R // * // config at C-2 revised. // s176 744 Cnidaria Sarcophyton ehrenbergi // Yang Meikeng, China // Prostaglandin derivatives: nonaromatic phosphodiesterase-4 inhibitors from the soft coral Sarcophyton ehrenbergi 1224 // sarcoehrendin A // N // * // * // * 1225 // sarcoehrendin B // N // phosphodiesterase-4 inhib. // * // * 1226 // sarcoehrendin C // N // * // * // * 1227 // sarcoehrendin D // N // phosphodiesterase-4 inhib. // * // * 1228 // sarcoehrendin E // N // * // * // * 1229 // sarcoehrendin F // N // phosphodiesterase-4 inhib. // * // * 1230 // sarcoehrendin G // N // * // * // * 1231 // sarcoehrendin H // N // phosphodiesterase-4 inhib. // * // * 1232 // sarcoehrendin I // N // * // * // * 1233 // sarcoehrendin J // N // phosphodiesterase-4 inhib. // * // * 1234 // 9α,15α-diacetoxy-11α-hydroxy-(5Z,13E)-prostadienoic acid methyl ester // M // phosphodiesterase-4 inhib. // * // s177 1235 // (5Z,9α,11α,13E,15S)-11,15-bis(acetoxy)-9-hydroxyprosta-5,13-dien-1-oic acid methyl ester // M // phosphodiesterase-4 inhib. // * // s178 1236 // 9,11,15-triacetoxy PGF2α methyl ester // M // phosphodiesterase-4 inhib. // * // s179 745 Cnidaria Scleronephthya flexilis // Southern Taiwan // Pregnane-type steroids from the Formosan soft coral Scleronephthya flexilis 1237 // 3β-methoxy-5,20-pregnadiene // N // * // * // * 1238 // * // R // * // absolute config via X-ray // s180

Key:


88

8

Cnidarians HO

R

HO R

H

O

O

H

H HO

OH

1244

H

H HO

OH

1239 R =

HO

H

OH

HO

OH H

H

RO H

H

OH

1241 R = H 1242 R =

H H

1247

1240 R =

HO

H

H

H HO

H

H

H

H OH

1245 R = H 1246 R = Ac

HO

O 1248

H

HO †1249

H H OH

O

R=

OAc

1250 R =

OAc

1251 R =

OAc

H H

OH 1252 R =

HO

HO

OAc

OH

H 1253

OAc

1243 R =

746 Cnidaria Subergorgia suberosa // Weizhou Is., China // Bioactive 9,11-secosteroids from gorgonian Subergorgia suberosa collected from the South China Sea 1239 // (5αH)-24-nor-9,11-seco-3β,6α,11-trihydroxycholest-7-en-9-one // N // * // * // * 1240 // (5αH,24R)-trihydroxy-24-methyl-9.11-seco-5α-cholest-7en-9-one // N // K562 15 uM, zebrafish embryo cytotox. (mixture with 1241) // * // * 1241 // (5αH,24S)-trihydroxy-24-methyl-9.11-seco-5α-cholest-7en-9-one // R // * // 24R corrected to 24S. // s181 1242 // (5αH,22E,24ζ)-24-ethyl-3β,6α,11-trihydroxy-24-methyl-9.11-seco-5α-cholest-7en-9-one // N // K562 8 uM, zebrafish embryo cytotox.. // * // * 1243 // (5αH,22E)-3β,6α,11-trihydroxy-24-methyl-9.11-seco-5α-cholest-7en-9-one // N // K562 13 uM, zebrafish embryo cytotox. // * // * 747 Cnidaria Sarcophyton trocheliophorum, Cnidaria Sinularia flexibilis // Yalong Bay, China // 9,11-Secosteroids and polyhydroxylated steroids from two South China Sea soft corals Sarcophyton trocheliophorum and Sinularia flexibilis 1244 // 25(26)-dehydrosarcomilasterol // N // weakly cytotox. // * // * 1245 // 7α-hydroxy-crassarosterol A // N // weakly cytotox. and PTP1B inhib. // * // * 1246 // 11-acetoxy-7α-hydroxy-crassarosterol A // N // weakly cytotox. // * // * 748 Cnidaria Verrucella umbraculum // Weizhou Is., S. China Sea // Polyhydroxylated sterols from the South China Sea gorgonian Verrucella umbraculum 1247 // verumbsteroid A // N // moderately cytotox. to 5 HTCLs // 3S (Moshers) // * 1248 // verumbsteroid B // N // * // * // * 749 Cnidaria Echinogorgia rebekka // Weizhou Is., S. China Sea // Antiviral C-25 epimers of 26-acetoxy steroids from the South China Sea gorgonian Echinogorgia rebekka 1249 // echrebsteroid A // N // antiviral (RSV) // absolute config (Moshers) // * 1250 // echrebsteroid B // N // antiviral (RSV) // * // * 1251 // echrebsteroid C // N // antiviral (RSV) // * // * 1252 // echrebsteroid D // N // antiviral (RSV) // * // * 750 Cnidaria Sarcophyton pauciplicatum // Hai Phong, Vietnam // NF-κB inhibitory activity of polyoxygenated steroids from the Vietnamese soft coral Sarcophyton pauciplicatum 1253 // sarcophanol A // N // NF-kB inhib. // * // *

Key:


89

8

Cnidarians X R

OAc

HO

H 1254 R = H 1255 R = Me

H H H HO

H

H HO 1257 1258 1259 1260 1261

R1 R1 R1 R1 R1

H

O

H

1256

H

H

H

1266 X = 1267 X =

H

HO

1264

O

1262

OH

HO

O H

O HO

H

H

OH

H

H

H H

H H

H 1263

O O X

H

HO OAc = OH, R 2 = H, n = 1, ∆ saturated = H, R 2 = OH, n = 1, ∆ saturated = OH, R 2 = H, n = 1 = OH, R 2 = H, n = 0 = H, R 2 = OH, n = 1 O

H

H

O

H

H

H

O

HO

H

n

R1

H

OH

H

H HO

O

∆

R2

H H

OH

OH

1265

O

H

O

H

O

Y

HO 1268 1269 1270 1271

OH X= X= X= X=

H

O, O, O, O,

Y= O Y= O Y = OAc ,H OAc ,H Y=

751 Cnidaria Echinogorgia sassapo reticulata // Dongshan Is., China // Novel polyhydroxylated steroids from the East China Sea gorgonian Echinogorgia sassapo reticulata with suppressive activity of leukotriene C4 generation and degranulation in bone marrow-derived mast cells 1254 // sassapol A // N // * // * // * 1255 // sassapol A // N // * // * // * 1256 // 7-oxo-5-cholesten-3β,19-diol // M // antiinflammatory inhib. of LTC4 generation // * // s182 752 Cnidaria Leptogorgia punicea // Aranhas Is., S. Brazil // Polyoxygenated steroids from the octocoral Leptogorgia punicea and in vitro evaluation of their cytotoxic activity 1257 // punicinol A // N // cytotox. to A549 HTCL // * // * 1258 // punicinol B // N // cytotox. to A549 HTCL // * // * 1259 // punicinol C // N // weakly cytotox. to A549 HTCL // * // * 1260 // punicinol D // N // weakly cytotox. to A549 HTCL // * // * 1261 // punicinol E // N // weakly cytotox. to A549 HTCL // * // * 753 Cnidaria Subergorgia suberosa // Naozhou Is., S. China Sea // Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa 1262 // 16,22-epoxy-20β,23S-dihydroxycholest-1-ene-3-one // N // barnacle cyprid settlement inhib. // * // * 1263 // 20β,23S-dihydroxycholest-1-ene-3,22-dione // N // barnacle cyprid settlement inhib. // * // * 1264 // 15β,17α-dihydroxypregna-4, 6-diene-3,20-dione // N // * // * // * 1265 // 11α-hydroxypregna-4-ene-3,6,20-trione // M // * // previously reported in a patent. // s183 754 Cnidaria Anthopleura midori // Shanwei, China // Polyoxygenated 24,28-epoxyergosterols inhibiting the proliferation of glioma cells from sea anemone Anthopleura midori 1266 // 24(R),28-epoxyergost-5-en-3β-ol // M // cytotox. rat glioma cell line // previously reported synthetic compound. // s184 1267 // 24(S),28-epoxyergost-5-en-3β-ol // M // cytotox. rat glioma cell line // previously reported synthetic compound. // s184 1268 // 24(R),28-epoxyergost-3-one-5α,6α-diol // N // cytotox. rat glioma cell line // * // * 1269 // 24(S),28-epoxyergost-3-one-5α,6α-diol // N // * // * // * 1270 // 24(R),28-epoxyergost-3-acetyl-3β,5α,6α-triol // N // cytotox. rat glioma cell line // * // * 1271 // 24(S),28-epoxyergost-3-acetyl-3β,5α,6α-triol // N // * // * // * Key:


90

9

Bryozoans OH Br

R1 OH Br

O R2

RO

N H O

Br

Br

HN

H N

HO

O

N

Br

†1272

Br

R1 = Br, R 2 = H R1 = H, R 2 = Br †1274 R = R = Br 1 2 †1273

N H

Br

HN

HN OH

N

Br

Br

O NH

Br

O

Br H N

Br

Br

Br

Br N H

†1275

R=H †1276 R = Me

Br

Br N H

Br

1277

Br

Br

Br

N H

O

Br

N

OMe O

MeO

1278

Br

Br

1279

Br

N

N

N

O

R OH

OH

OH ∆1

†1284

HO 6

HN †1281

∆2

O

OH

∆2 saturated †1285 ∆ ,∆ saturated 1 2

11

∆

Br

H

OH

Br

1280

OH

H

6

Br

H

HN

H O

n †1282 †1283

n = 11 n = 13

H HO

H

HO †1286 R = H OH 1287 R = Me 1289 ∆ saturated, R = Et

H

H

H

HO HO

O

†1288

H

OH HO

O OH

H 1290

794 Bryozoa Aspidostoma giganteum // Gulf of San Jorge, Patagonia // Bromopyrrole alkaloids isolated from the Patagonian bryozoan Aspidostoma giganteum 1272 // aspidostomide A // N // * // * // * 1273 // aspidostomide B // N // * // * // * 1274 // aspidostomide C // N // * // * // * 1275 // aspidostomide D // N // * // * // * 1276 // aspidostomide E // N // * // * // * 1277 // aspidostomide F // N // * // * // * 1278 // aspidostomide G // N // * // * // * 1279 // aspidostomide H // N // * // * // * 1280 // aspidazide A // N // * // * // * 795 Bryozoa Bugula neritina // Daya Bay, China // Neritinaceramides A–E, new ceramides from the marine bryozoan Bugula neritina inhabiting South China Sea and their cytotoxicity 1281 // neritinaceramide A // N // * // * // * 1282 // neritinaceramide B // N // * // * // * 1283 // neritinaceramide C // N // * // * // * 1284 // neritinaceramide D // N // * // * // * 1285 // neritinaceramide E // N // * // * // * 796 Bryozoa Bugula neritina // Daya Bay, China // New 3β,6β-dihydroxy and 3β,5α,6β-trihydroxy sterols from marine bryozoan Bugula neritina in South China Sea and their cytotoxicity 1286 // (22E)-cholest-4,22-diene-3β,6β-diol // N // * // * // * 1287 // (22E,24S)-24-methylcholest-4,22-diene-3β,6β-diol // M // * // * // s185 1288 // (23S,24R)-dimethylcholest-7-ene-3β,5α,6β-triol // N // * // * // * 1289 // * // M // * // * // s186 1290 // * // M // * // * // s187 Key:


91

10

Molluscs Y

O

O O

OR

OH

9

∆

HN

O

OMe O O

CHO

37

H

13

O

COOH

O

O OH

O OH

O N

OH

11

O

X 1292 R = Ac 1293 R = Ac, ∆ saturated 1294 R = H, ∆ saturated

1291

1295 X = Y = O 1296 Y = O, X = OH ,H 1297 X = O, Y = OH ,H †1298 X = OH ,H, Y = OH ,H

COOR 2

H

O

N

MeO OH

NH 2

1301

O N

O N

OH

O

7

O

O

OH

1299 1300

OMe

O

O

5

OH

O OAc

N

MeO

1302 O

N

OH

CHO

R1

N H

N 1303 O 1304 1305 1306

R1 R1 R1 R1

= R2 = H = OH, R 2 = H = H, R 2 = Me = OH, R 2 = Me

799 Mollusca Mytilus edulis, Cassostrea gigas // * // Epimers of azaspiracids: isolation, structural elucidation, relative LCMS response, and in vitro toxicity of 37-epi-azaspiracid-1 1291 // 37-epi-azaspiracid-1 // N // cytotox. // * // * 800 Mollusca Thuridilla hopei // Roca Vecchia, Lecce, Italy // Identification of thuridillin-related aldehydes from Mediterranean sacoglossan mollusk Thuridilla hopei 1292 // nor-thuridillonal // N // * // * // * 1293 // dihydro-nor-thuridillonal // N // * // * // * 1294 // deacetyl-dihydro-nor-thuridillonal // N // * // * // * 803 Mollusca Peltodoris atromaculata, Porifera Haliclona fulva // Punta Pizzaco, Gulf of Naples // Sequestered fulvinol-related polyacetylenes in Peltodoris atromaculata 1295 // fulvindione // N // cytotox. (6 HTCL) // * // * 1296 // fulvinone // N // * // * // * 1297 // fulvinone // N // * // * // * 1298 // isofulvinol // N // cytotox. (6 HTCL) // Absolute configuration (MTPA) // * 1299 // hydroxydehydroisofulvinol // N // cytotox. (6 HTCL) // * // * 804 Mollusca Jorunna funebris, Porifera Xestospongia sp. // Linshui Bay, China // New isoquinolinequinone alkaloids from the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp. 1300 // fennebricin A // N // * // * // * 1301 // fennebricin B // N // * // * // * 1302 // N-formyl-1,2-dihydrorenierol // N // * // * // * 805 Mollusca Pleurobranchus areolata // Ilha do Papagaio, Brazil // Rodriguesic acids, modified diketopiperazines from the gastropod mollusc Pleurobranchus areolatus 1303 // rodriguesic acid // N // * // * // * 1304 // rodriguesic acid hydroxamate // N // * // * // * 1305 // rodriguesic acid Me ester // N // * // Maybe artefactual. // * 1306 // hydroxamate of 1305 // N // * // Maybe artefactual. // * Key:


92

10

Molluscs OH

Br

OH

H

CCDWENCDHLCSCCD* 1311

Br

HO 1307

Cl

OAc

†1309

SCCARNPACRHNHPC 1312

Br

Br GCCSHPACSVNNPDIC* Cl 1308

1310

CIWPWC 1313

807 Mollusca Aplysia oculifera // S. of Safaga City, Egypt // New cytotoxic halogenated sesquiterpenes from the Egyptian sea hare, Aplysia oculifera 1307 // oculiferane // N // cytotox. (5 HTCL) // X-ray structure. // * 1308 // epi-obtusane // N // cytotox. (5 HTCL) // X-ray structure. // * 808 Mollusca Aplysia dactylomela // Mona Is., Puerto Rico // Dactyloditerpenol acetate, a new prenylbisabolane-type diterpene from Aplysia dactylomela with significant in vitro anti-neuroinflammatory activity 1309 // dactyloditerpenol acetate // N // anti-neuroinflammatory // Absolute via Kishi method. // * 820 Mollusc Conus bandanus // Iffa-Credo, France // Isolation, purification and functional characterization of alpha-BnIA from Conus bandanus venom 1310 // -BnIA // N // // * // * 823 Mollusc Conus bandanus // Nha Trang bay, Vietnam // Characterization of a novel Conus bandanus conopeptide belonging to the M-superfamily containing bromotryptophan 1311 // BnIIID // N // * // * // * 824 Mollusc Conus australis // Tamil Nadu, India. // Discovery of a new subclass of α-conotoxins in the venom of Conus australis 1312 // -AusIA // N // // * // * 825 Mollusc Conus virgo // Tamil Nadu, India. // Conformational analysis of a 20-membered cyclic peptide disulfide from Conus virgo with a wpw segment: evidence for an aromatic–proline sandwich 1313 // Vi804 // N // * // * // *

Key:


93

11

Tunicates (ascidians) OH O

R

O 8

O

12

O

O O

O

6

NHR R=H 1321 R = CH 2COOH

†1316

8

OH

6

1318

†1317

R = Me NH 2 †1319 R = H

1320 R = H 1322 R = CH 2COOH

NH 2

NHR

12

O

O

1315

16

Br

OH

O

OH

OH

OH

OH

12

1314 OR1

OAc

iBuCOO

MeOOC

O

O MeOOC iBuCOO

Br

MeO

O

O

OH

OR 2 O

O AcO 1325

EtCOO

OH

O

O

O

1323 R1 = COEt, R 2 = Ac 1324 R1 = Ac, R 2 = H

O

O

O COOEt

AcO

O

1327

N

Br O

O

O

O 1329

Br

O MeO O

Br

O

1328

N N

O

COOMe OH

1326

Br

O

O

O

N O

Br

O

AcO

N H

4

1330

Br

N OAc

EtCOO

832 Chordata Didemnum sp. // Nabq/Sharm El-Sheikh, Egypt // Didemnacerides A and B: two new glycerides from Red Sea ascidian Didemnum species 1314 // didemnaceride A // N // * // * // * 1315 // didemnaceride B // N // * // * // * 833 Chordata Pseudodistoma sp. // Chuja-do, Korea // Amino alcohols from the ascidian Pseudodistoma sp. 1316 // pseudoaminol A // N // mildly cytotox. and AB // * // * 1317 // pseudoaminol B // N // mildly cytotox. and AB // * // * 1318 // pseudoaminol C // N // mildly cytotox. // * // * 1319 // pseudoaminol D // N // mildly cytotox. // * // * 1320 // pseudoaminol E // N // * // * // * 1321 // pseudoaminol F // N // * // * // * 1322 // pseudoaminol G // N // * // * // * 834 Chordata Didemnum sp. // Nabq, Egypt // Didemnaketals D and E, bioactive terpenoids from a Red Sea ascidian Didemnum species 1323 // didemnaketal D // N // mildly AB // * // * 1324 // didemnaketal E // N // mildly AB // * // * 835 Chordata Didemnum sp. // Nabq, Egypt // Didemnaketals F and G, new bioactive spiroketals from a Red Sea ascidian Didemnum species 1325 // didemnaketal F // N // mildly cytotox. // * // * 1326 // didemnaketal G // N // mildly cytotox. // * // * 836 Chordata Synoicum pulmonaria // Tromso, Norway // Isolation and synthesis of pulmonarins A and B, acetylcholinesterase inhibitors from the colonial ascidian Synoicum pulmonaria 1327 // pulmonarin A // N // mild AChE inhib. // * // * 1328 // pulmonarin B // N // mild AChE inhib. // * // * 837 Chordata Synoicum sp. // Visakhapatnam coast, India // Rubrolide R: a new furanone metabolite from the ascidian Synoicum of the Indian Ocean 1329 // rubrolide R // N // * // duplicate name // s188 552 Chordata Cnemidocarpa stolonifera // Peel Is., Australia // Structure determination of pentacyclic pyridoacridine alkaloids from Australian Ancorina geodides and C. stolonifera 1330 // cnemidine A // N // moderate cytotox. PC3. // * // * Key:


94

11

Tunicates (ascidians) O

NH 2 H N

H H HO

NaO 3SO

R

H N

1331 R = 1332 R =

OH OH

HN O

†1333

MeS

H 2N

N

N

H

O N

O

OH

OH

†1334

MeS

8

O

OH

OH

Br

N H

O H N

N H

Br

N

N

20

O O

OH NH 2

†1335 †1336

S (8Z) (8E)

MeOOC

OH O

O 10 O

S

HO O

O

O O

O OAc

MeOOC

OCOEt

†1337

O

O †1338

HO

OMe OH

838 Chordata Phallusia fumigata // Bay of Pozzuoli, Italy // Phallusiasterols A and B: two new sulfated sterols from the Mediterranean tunicate Phallusia fumigata and their effects as modulators of the PXR receptor 1331 // phallusiasterol A // N // PXR agonist // * // * 1332 // phallusiasterol B // N // * // * // * 839 Chordata Didemnum sp. // Little San Salvador Is., Bahamas // Salvadenosine, a 5′-deoxy-5′-(methylthio) nucleoside from the Bahamian tunicate Didemnum sp 1333 // salvadenosine // N // * // confirmed by synthesis. // * 1334 // hamiguanosinol // R // * // revised by synthesis // s189 841 Chordata Diazona cf formosa // East Timor // Tanjungides A and B: new antitumoral bromoindole derived compounds from Diazona cf formosa. Isolation and total synthesis 1335 // tanjungide A // N // strongly cytotox. HTCL // confirmed by synthesis. // * 1336 // tanjungide B // N // mod. cytotox. HTCL // confirmed by synthesis. // * 845 * // * // Total synthesis and structure revision of didemnaketal B 1337 // didemnaketal B // R // * // total synthesis; revision of structure. // s190 852 * // * // Total synthesis and stereochemical reassignment of mandelalide A 1338 // mandelalide A // R // * // * // s191

Key:


95

12

Echinoderms R2

OH SO3H

HO O

1339

O

HO

O

O

R3 H

H

O

X O

OH O

O

OH

HO

O

HO

OH 1340

OH

HO

H HO

OH

O

O

OH

OH

H O

H

OMe

O

O

O

OH OH

HO OMe

OAc ,H, R1 = H, R 2 = OAc. R 3 =

1345 X =

OAc ,H, R1 = R 2 = H. R 3 =

OH O

1346 X = O, R1 = R 2 = H. R 3 = 1347 X = O, R1 = R 2 = H. R 3 = 1348 X =

OAc ,H, R1 = CH 2OH, R 2 = OAc. R 3 =

H OH

OH O

OH R1

O

O

1344 X =

OH

O

HO

O

O

O

OH

OH

HO OH OH

OH 1341

OAc ,H, R1 = H, R 2 = OAc. R 3 =

OMe

OH

OH

O

O

HO

O

1343 X =

H

OH

O

O

OH

HO

HO

H O

OH

H

1342

866 Echinodermata Brisaster latifrons // Sea of Okhotsk // A new sulfonic acid derivative, (Z)-4-methylundeca-1,9-diene-6-sulfonic acid, isolated from the cold water sea urchin inhibits inflammatory responses through JNK/p38 MAPK and NF-κB inactivation in RAW 264.7 1339 // (Z)-4-methylundeca-1,9-diene-6-sulfonic acid // N // anti-inflammatory // * // * 867 Echinodermata Scaphechinus mirabilis // Peter the Great Bay, Sea of Japan // Mirabiquinone, a new unsymmetrical binaphthoquinone from the sea urchin Scaphechinus mirabilis 1340 // mirabiquinone // N // Antioxidant (DPPH) // * // * 868 Echinodermata Acanthaster planci // Van Phong Bay, Vietnam // Minor steroidal triglycoside planciside D from the tropical starfish Acanthaster planci 1341 // planciside D // N // * // * // * Echinodermata Stichopus chloronotus // Cat Ba, Haiphong, Vietnam // Triterpene saponins from the sea cucumber Stichopus chloronotus 1342 // stichloroside F // N // * // * // * 869 Echinodermata Cladolabes schmeltzii // Nha Trang Gulf, South China Sea // Triterpene glycosides from the sea cucumber Cladolabes schmeltzii. II. Structure and biological action of cladolosides A1-A6 1343 // cladoloside A1 // N // cytotox. and hemolytic // * // * 1344 // cladoloside A2 // N // cytotox. and hemolytic // * // * 1345 // cladoloside A3 // N // cytotox. and hemolytic // * // * 1346 // cladoloside A4 // N // cytotox. and hemolytic // * // * 1347 // cladoloside A5 // N // * // * // * 1348 // cladoloside A6 // N // cytotox. and hemolytic // * // *

Key:


96

12

Echinoderms ∆

O

O

H NaO 3SO NaO 3SO O O

MeO

1349 ∆ saturated 1350

OH

O

O O

OH

OH

OH

H

O

O

O

H O

HO

HO

HO

OAc

O

O

O

H OH

O

O O

O

O O

H

OH

OH OH OH

O O

HO

O

O

OH

OH

OH

OH HO

NaO 3SO

1352

O

OH

HO

OMe

OMe

OH

O

O

O 1353

OH O

OMe OH

OH

1354 ∆7,8 saturated, 8betaH 1355 ∆9,11 saturated, 9betaH

OH

OH OH

O

OH O

1351

OH OH

OH

O

OH O

O

OH OH

O

H O

O

OH

HO

OH

O HO

O O

OH

OH O

OMe

O

O

O

O

7

O

OH H

OH

H HO

HO

O

O

H

O

O

O

H

H NaO 3SO

9

H OH

H OH O

O

OH

O

OMe

HO

OH

OH

O

O

O OH HO

OH OH

HO

OH

871 Echinodermata Eupentacta fraudatrix // Troitsa Bay, Sea of Japan // Cucumariosides F1 and F2, two new triterpene glycosides from the sea cucumber Eupentacta fraudatrix and their LC-ESI MS/MS identification in the starfish Patiria pectinifera, a predator of the sea cucumber 1349 // cucumarioside F1 // N // * // Also detected in predator Patiria pectinifera // * 1350 // cucumarioside F2 // N // * // Also detected in predator Patiria pectinifera // * 872 Echinodermata Pseudocnus dubiosus // South Atlantic Ocean // Pseudocnoside A, a new cytotoxic and antiproliferative triterpene glycoside from the sea cucumber Pseudocnus dubiosus leoninus 1351 // pseudocnoside A // N // mild cytotox. (2 HTCLs) // * // * 873 Echinodermata Stichopus variegatus // South China Sea, Hainan, China // Variegatusides: new non-sulphated triterpene glycosides from the sea cucumber Stichopus variegates Semper 1352 // variegatuside C // N // AF // * // * 1353 // variegatuside D // N // AF // * // * 1354 // variegatuside E // N // AF // * // * 1355 // variegatuside F // N // AF // * // * Key:


97

12

Echinoderms R2

OH H 1356 R1 = H, R 2 =

H H NaO 3SO

H

O

H

HO

OH 1358 R1 = CH 2OH, R 2 =

O

OH

OH

H

1372

OH HO

O

1359 R1 = CH 2OH, R 2 = OH

OH

O

O

H NaO 3SO

O

O

O OH

OH OH

OH

O H

1357 R1 = H, R 2 = OH

R1

O

O

O

1360 R1 = CH 2OH, R 2 =

OH

OH OH

1361 R1 = CH 2OH, R 2 =

O

OH

874 Echinodermata Leptasterias ochotensis // Bolshoy Shantar, Sea of Okhotsk // Asterosaponins from the Far Eastern starfish Leptasterias ochotensis and their anticancer activity 1372 // (23S)-6α,23-dihydroxy-5α-cholesta-9(11),20(21)-dien-3β-yl sulfate // N // * // * // * 1356 // leptasterioside B // N // cytotox., inhib. colony formation of 2 HTCLs // * // * 1357 // leptasterioside A // N // cytotox., inhib. colony formation of 2 HTCLs // * // * 1358 // leptasterioside C // N // cytotox., inhib. colony formation of 2 HTCLs // * // * 1359 // leptasterioside D // N // * // * // * 1360 // leptasterioside E // N // * // * // * 1361 // leptasterioside F // N // * // * // *

Key:


98

12

Echinoderms HO

O

O

R2

H

O

O

HO

OH

O

OMe

R4 R2

O

R1

HO

1366 R1 = OH, R 2 = R 3 = H, R 4 = O

OH

O

OH

O

OMe

O OH

O OH

H OH

O O

O

OH

OH O

1364 R1 = H, R 2 = R 3 = OH, R 4 = 1365 R1 = H, R 2 = OH, R 3 = OAc, R 4 =

R3

OMe OH

OH O

O

H

H

O OH

OH

1362 R1 = OH, R 2 =

OH O

O

1363 R1 = H, R 2 =

OH O

HO

H

HO

OH OH

OH

O R1

O O

LRKLMLQR

OH 1368 R1 = R 2 = R 3 = H, R 4 =

HO OH

O

1367 R1 = R 3 = H, R 2 = OH, R 4 =

O

1373

1369 R1 = R 2 = R 3 = H, R 4 = OH 1370 R = OH, R = R = H, R = 1 2 3 4

OH

HO HO

1371 R1 = R 2 = R 3 = H, R 4 =

OH

875 Echinodermata Bohadschia cousteaui // Red Sea, Gulf of Aqaba. // Analysis of saponins as bioactive zoochemicals from the marine functional food sea cucumber Bohadschia cousteaui 1362 // cousteside A // N // AF // * // * 1363 // cousteside B // N // AF // * // * 1364 // cousteside C // N // AF // * // * 1365 // cousteside D // N // AF // * // * 1366 // cousteside E // N // AF // * // * 1367 // cousteside F // N // AF // * // * 1368 // cousteside G // N // AF // * // * 1369 // cousteside H // N // AF // * // * 1370 // cousteside I // N // AF // * // * 1371 // cousteside J // N // AF // * // * 878 Echinodermata Echinometra lucunter // Sao Sebastiao, SP, Brazil. // Echinometrin: a novel mast cell degranulating peptide from the coelomic liquid of Echinometra lucunter 1373 // Echinometrin // N // pro-inflammatory // * // *

Key:


99

13


O

HO HO

R

O

O

O

O HO

MeO

1376

HO

R1

OH MeO

OH

O

OH OH

O

O O

O

O

HO

1377

HO

O

O

OH

OH HO O

OH

OH OH

HO

OH O O

OH OH

1381

H

HO O

†1382

R2

O

OH R3

1378 R1 = R 2 = OH, R 3 = H 1379 R1 = R 2 = H, R 3 = OH

N

O

O

OH

OH

O

OH

1380

O

O

OH

OH OH

OH O

O

O OH

OH O

O

OH OH

O

HO

OH O

OH

OH O

OH

OH

O

O OH

O

Cl OH OH

OH

OH

O

OH

OH

OH 1374 R = 1375 R =

O

OH

O

R1

1383 1384 1385 1386 1387

R1 R1 R1 R1 R1

OR 2 = R2 = H = H, R 2 = (CH 2) 2O(CH 2) 2OH = OMe, R 2 = (CH 2) 2O(CH 2) 2OH = OMe, R 2 = H = H, R 2 = Me

907 Tracheophyta Avicennia marina // Beihai city, China // Four new jacaranone analogs from the fruits of a Beibu Gulf mangrove Avicennia marina 1374 // marinoid F // N // * // * // * 1375 // marinoid G // N // * // * // * 1376 // marinoid H // N // * // * // * 1377 // marinoid I // N // antioxidant // * // * 908 Tracheophyta Avicennia marina // Beihai city, China // New antioxidative secondary metabolites from the fruits of a Beibu Gulf mangrove, Avicennia marina 1378 // marinoid L // N // antioxidant // * // * 1379 // marinoid K // N // antioxidant // * // * 1380 // marinoid L // N // * // * // * 1381 // marinoid M // N // * // * // * 909 Tracheophyta Ceriops decandra // Godavari estuary, India // Decandrinin, an unprecedented C9-spiro-fused 7,8-seco-ent-abietane from the Godavari mangrove Ceriops decandra 1382 // decandrinin // N // * // * // * 910 Tracheophyta Micromelum falcatum // Wenchang, China // Five new phenethyl cinnamides from the mangrove associates Micromelum falcatum 1383 // micrometam A // N // * // * // * 1384 // micrometam B // N // * // * // * 1385 // micrometam C // N // * // * // * 1386 // micrometam D // N // * // * // * 1387 // micrometam E // N // * // * // *

Key:


100

13

Mangroves and the intertidal zone R5 OH

OH

O

O

OR 3

R4

MeO

O MeO

H H

R1

H H

OH H H

∆

H H

O OH 1388

1389 1390 1391 1392 1394

O

OH

H

O

H O

HO

OCOiPr

R1

R2 OR1 1395 R1 = COiPr, R 2 = H 1399 R1 = Ac, R 2 = OH

1394

O

MeOOC

OR 2

O

O

O

1396 R1 = H, R 2 = COiPr 1397 R1 = OH, R 2 = COiPr 1398 R1 = OH, R 2 =

O

O O

O

HO

N

O

O

MeOOC

O

1400

OAc OAc

O

H OH OAc 1401

O

O

N

O

OH

O

O

OH O

O

= R 3 = H, R 2 = Ac, R 4 = OMe , R 5 = OH = R 2 = R 3 = H, R 4 = OMe , R 5 = OAc OH , ∆ saturated = R 2 = H, R 3 = Me, R 4 = OMe , R 5 = = OAc, R 2 = H, R 3 = Me, R 4 = OMe , R 5 = OH OH = H, R 2 = Ac, R 3 = H, R 4 = OMe , R 5 =

HO

H

O

H

O

H

O

O

O

OR 2

O

H MeOOC

R1 R1 R1 R1 R1

H

O

MeOOC O

O

H

H O

O

O

O

O

H

O

O O H

OMe †1402

MeOOC

MeOOC O †1403

O 1404

911 Tracheophyta Xylocarpus granatum // Dongzhai, China // Apotirucallane protolimonoids from the Chinese mangrove Xylocarpus granatum Koenig 1388 // xylogranatumine A // N // * // * // * 1389 // xylogranatumine B // N // * // * // * 1390 // xylogranatumine C // N // * // * // * 1391 // xylogranatumine D // N // * // * // * 1392 // xylogranatumine E // N // * // * // * 1393 // xylogranatumine F // N // weakly cytotox. // * // * 1394 // xylogranatumine G // N // * // * // * 912 Tracheophyta Xylocarpus rumphii // Kudee Is., Thailand // Weakly anti-inflammatory limonoids from the seeds of Xylocarpus rumphii 1395 // xylorumphiin E // N // * // * // * 1396 // xylorumphiin F // N // * // * // * 1397 // 2-hydroxyxylorumphiin F // N // inhibit NO production // * // * 1398 // xylorumphiin G // N // * // X-ray structure. // * 1399 // xylorumphiin H // N // * // * // * 1400 // xylorumphiin I // N // inhibit NO production // * // * 1401 // xylorumphiin J // N // * // * // * 913 Tracheophyta Xylocarpus granatum // Dongzhai, China // Bioactive rearranged limonoids from the Chinese mangrove Xylocarpus granatum Koenig 1402 // xylogranatopyridine A // N // mild PTP1B inhibition // X-ray structure. Abs. confg. ECD DFT calc. // * 1403 // xylogranatopyridine B // N // * // * // * 1404 // prexylogranatopyridine // N // * // * // * Key:


101

O

13


O

O

O

O MeOOC H

O

O

O

MeOOC

N H H

O O

HO

1405

O O

O

H

MeOOC

OH O

1406

O

H

1407 R = Ac OR 1408 R = CH(Me)CH 2Me O

O

H

H

COOMe OH

H

O

O

∆

O

COOMe

O

H

H

OH

1411 R = Me 1412 R =

O

H O

H

O

COOMe OH

H

1413 R = Me 1414 R =

OCOR

O

O O

O

OH

COOMe H

O H 1415 R = 1416 R = iPr

O

O H

OAc

O

H

COOMe

O H

OCOR

O

O

O H

OCOR

O

COOMe O

OH O

H O

O

O

1417

H OAc

OAc

1418


914 Tracheophyta Xylocarpus granatum // Hainan Is., China // Xylomexicanins E-H, new limonoids from Xylocarpus granatum 1405 // xylomexicanin E // N // * // * // * 1406 // xylomexicanin F // N // mildly cytotox. // * // * 1407 // xylomexicanin G // N // * // * // * 1408 // xylomexicanin H // N // * // * // * 915 Tracheophyta Xylocarpus granatum // Krishna estuary, India // Limonoids with an oxygen bridge between C(1) and C(29) from the seeds of a Krishna mangrove, Xylocarpus granatum 1409 // granatumin L // N // * // X-ray structure. // * 1410 // granatumin M // N // * // * // * 1411 // granatumin N // N // * // * // * 1412 // granatumin O // N // * // * // * 1413 // granatumin P // N // * // * // * 1414 // granatumin Q // N // * // * // * 1415 // granatumin R // N // * // * // * 1416 // granatumin S // N // * // * // * 1417 // granatumin T // N // * // * // * 1418 // granatumin U // N // * // * // *

Key:


102

13

Mangroves and the intertidal zone O

O

O

R1

COOMe OH

H

O

H

MeOOC O

O

O

H

O H OCOR 2 †1419

R1 = H, R 2 = Me †1420 R = H, R = iPr 1 2 †1421 R = H, R = 1 2 †1422

HO

H O 1423 O

R1 = OH, R 2 =

916 Tracheophyta Xylocarpus granatum // Krishna estuary, India // Absolute configurations of new limonoids from a Krishna mangrove, Xylocarpus granatum 1419 // granatumin V // N // * // * // * 1420 // granatumin W // N // * // * // * 1421 // granatumin X // N // * // * // * 1422 // granatumin Y // N // * // X-ray structure. // * 917 Tracheophyta Xylocarpus granatum // Hainan Is., China // A new limonoid from Xylocarpus granatum 1423 // xylocartin C // N // * // * // *

Key:


103

14

Miscellaneous

OH OH

OH HO

O HO

HO HO

O

OSO 3H 1424

O

MeO

HO 3SO

OH

N

HO HN

OH

N OH HN

1427

OH

NH 2

O

HN O

O 1426

O

N

N

O

OH

COOH

S

O

O

HO OH

OH

OH O

N H

NH HN

OHO 6

HO 1428

OH

1425

928 Tracheophyta Thalassia hemprichii // south Marsa Alam coast, Egypt // A new 8-hydroxy flavone O-xyloside sulfate and antibacterial activity from the Egyptian seagrass Thalassia hemprichii 1424 // isoscutellarein 7-O-β-xyloside-2''-O-sulfate // N // mod. AB activity // * // * 929 Tracheophyta Thalassodendron ciliatum // Magawish city Hurghada, Egypt // Anti-influenza A virus activity of a new dihydrochalcone diglycoside isolated from the Egyptian seagrass Thalassodendron ciliatum (Forsk.) den Hartog 1425 // thalassodendrone // N // mild anti-influenza activity. // * // * 930 Annelida Thelepus crispus // the coast of Friday Harbor, WA, USA // Thelepamide: an unprecedented ketide-amino acid from Thelepus crispus, a marine annelid worm 1426 // thelepamide // N // weakly cytotox. // * // * 933 Arthropoda Vargula hilgendorfii // Chita, Aichi, Japan // Identification of 3-enol sulfate of Cypridina luciferin, Cypridina luciferyl sulfate, in the sea-firefly Cypridina (Vargula) hilgendorfii 1427 // Cypridina luciferyl sulfate // N // * // * // * 934 Chordata Takifugu pardalis // * // Isolation of 6-deoxytetrodotoxin from the pufferfish, Takifugu pardalis, and a comparison of the effects of the C-6 and C-11 hydroxy groups of tetrodotoxin on its activity 1428 // 6-deoxytetrodotoxin // N // NaV channel blocker. // * // *

Key:


104

15

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