Fitoterapia 2013;89:224-30. 30. Wang XY, Gao H, Zhang W, Li Y, .... Triterpenoid saponins form Anemone hupehensis. Phytochemistry 1997;44:333-5. 71.
Supporting information
Figure S1 Phylogenetic relationship of Anemone inferred from ITS+ atpB-rbcL spacer region, using maximum likelihood method.
Table S1 The oleanane-type triterpenoids isolated from Anemone species (A type). No.
Type
Compound name
R1
R2
Taxon
Ref.
1
A1
Oleanolic acid
H-
H-
58, 59
2 3 4 5
A1 A1 A1 A1
3-Acetyloleanolic acid 3-O-β-D-Glucopyranosyl oleanolic acid 3-O-α-L-Rhamnopyranosyl oleanolic acid Raddeanoside R0 (Fatsiaside A1)
H3COCGlcRhaAra-
HHHH-
6 7 8 9 10 11 12 13
A1 A1 A1 A1 A1 A1 A1 A1
3-O-β-D-Xylopyranosyl oleanolic acid 3-O-β-D-Glucuronopyranosyl oleanolic acid 3-O-β-D-Glucuronopyranosyl methyl ester oleanolic acid 3-O-α-L-Rhamnopyranosyl-(1→4)-β-D-glucopyranosyl oleanolic acid 3-O-α-L-Rhamnopyranosyl-(1→2)-β-D-glucopyranosyl oleanolic acid Raddeanoside R2 Flaccidin B (Flaccidoside I) Eleatheroside K (Eleutheroside K)
XylGlcAGlcA methyl esterRha(1→4)GlcRha(1→2)GlcGlc(1→2)AraGlc(1→2)XylRha(1→2)Ara-
HHHHHHHH-
14 15 16 17 18 19 20
A1 A1 A1 A1 A1 A1 A1
Rha(1→4)AraGlc(1→4)AraAra(f)(1→2)RhaRha(1→2)XylAra(f)(1→2)GlcAGal(1→3)GlcRha(1→4)GlcA-
HHHHHHH-
21
A1
Ara(1→4)GlcA-
H-
12
60
22 23 24
A1 A1 A1
Raddeanoside R1 (Raddeanin B) 3-O-β-D-Glucopyranosyl-(1→4)-α-L-arabinopyranosyl oleanolic acid Obtusilobin Giganteaside D Narcissiflorine 3-O-β-D-Galactopyranosyl-(1→3)-β-D-glucopyranosyl oleanolic acid 3-O-α-L-Rhamnopyranosyl-(1→4)-β-D-glucuronopyranosyl oleanolic acid 3-O-α-L-Arabinopyranosyl-(1→4)-β-D-glucuronopyranosyl oleanolic acid 3-O-β-D-Glucopyranosyl-(1→3)-β-D-galactopyranosyl oleanolic acid 3-O-α-L-Arabinopyranosyl-(1→3)-β-D-glucopyranosyl oleanolic acid 3-O-β-D-Glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)-α-L-
3,8,12,15,19 ,21 15 12 12 4,15,16,19,2 1 20 8 8 12 8 4,8,15‒17 3,8 7‒ 9,15,16,21 15 15 13 3,8 12 21 12
Glc(1→2)GalAra(1→4)GlcGlc(1→4)[Rha(1→2)]Ara-
HHH-
11 12 7
60 58 60
9,17 60 61 30, 62 58 63 63 60 60 60 18 64 60 60 60 60 17 62 60
25 26 27 28 29 30 31 32
A1 A1 A1 A1 A1 A1 A1 A1
33
A1
34 35 36 37
A1 A1 A1 A1
38
A1
39
A1
arabinopyranosyl oleanolic acid Narcissifloridine Obtusilobinin Hupehensis saponin A Prosapogenin CP4 Raddeanoside R3 (Raddeanin A) Raddeanoside R6 (Raddeanin E) Raddeanoside R22 3-O-α-L-Rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-Larabinopyranosyl oleanolic acid 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl oleanolic acid Huzhangoside A Narcissiflorinine Raddeanoside R13 3-O-α-L-Rhamnopyranosyl-(1→2)-[α-L-arabinopyranosyl]-β-Dglucopyranosyl oleanolic acid 3-O-α-L-Arabinopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→4)[α-L-arabinopyranosyl-(1→2)]-β-D-glucopyranosyl oleanolic acid Rivularinin
40
A1
Obtusilobicinin
41
A1
42
A1
43 44 45
A1 A1 A1
46
A1
3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-Dglucopyranosyl-(1→4)-α-L-arabinopyranosyl oleanolic acid 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl oleanolic acid Raddeanoside R23 Hupehensis saponin B 3-O-β-D-Xylopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→4)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl oleanolic acid 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)]-α-L-
Ara(f)(1→2)Rha(1→4)GlcAra(f)(1→2)[Rha(1→4)]GlcRib(1→3)Rha(1→2)GlcRib(1→3)Rha(1→2)AraRha(1→2)Glc(1→2)AraGlc(1→2)Rha(1→4)AraGlc(1→2)[Glc(1→4)]AraRha(1→2)Glc(1→4)Ara-
HHHHHHHH-
12 13 10 10,16,17,21 15 15 15 7
58 58 58 58 58 58 58 58
Xyl(1→3)Rha(1→2)Ara-
H-
7
58
Rib(1→3)Rha(1→2)XylAra(f)(1→2)Rha(1→4)GlcARha(1→2)[Glc(1→4)]AraRha(1→4)[Ara(1→2)]Glc-
HHHH-
16 12 15 13
58 58 58 58
Ara(1→2)Rha(1→4)[Ara(1→2)]Glc-
H-
12
58
Ara(f)(1→2)Rha(1→4)Glc(1→4)Glc Ara(f)(1→2)[Ara(f)(1→2)Rha(1→4) ]GlcXyl(1→3)Rha(1→2)Glc(1→4)Ara-
H-
16
58
H-
13
58
H-
7
58
Xyl(1→3)Rha(1→2)[Glc(1→4)]Ara-
H-
7,17,19
30
Ara(1→3)Rha(1→2)[Glc(1→4)]AraGlc(1→3)Rib(1→3)Rha(1→2)AraXyl(1→2)Rha(1→4)[Glc(1→4)]Ara-
HHH-
15 10 7
58 58 58
Xyl(1→3)Rha(1→2)[Glc(1→4)Glc(1 →4)]Ara-
H-
19
58
47 48 49
A1 A1 A1
50 51 52 53
A1 A1 A1 A1
54 55 56 57
A1 A1 A1 A1
58 59 60 61
A1 A1 A1 A1
62
A1
63
A1
64 65 66 67 68
A1 A1 A1 A1 A1
arabinopyranosyl oleanolic acid Lucyoside H 3-O-α-L-Arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranoside 3-O-β-D-Glucopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-β-D-glucopyranoside Giganteasides G Mateglycoside D Clematichinenoside A 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)]-α-Larabinopyranosyl oleanolic acid 28-O-β-D-glucopyranoside Asteryunnanoside F Flaccidoside VII Hemsgiganoside B Oleanolic acid 3-O-β-D-glucuronopyranosyl 28-O-βD-glucopyranosyl-(1→6)-β-D-glucopyranoside Raddeanoside R7 (Raddeanin F) Raddeanoside R4 (Raddeanin C) Anhuienside C 3-O-α-L-Rhamnopyranosyl-(1→2)-β-D-glucopyranosyl olean-12-en-28-oic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester 3-O-β-D-Glucopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-{β-D-glucopyranosyl-(1→6) -β-D-glucopyranoside} 3-O-α-L-Rhamnopyranosyl-(1→2)-α-L-arabinofurnosyl olean-12-en-28-oic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester Tomentoside D Raddeanoside R5 (Raddeanin D) Raddeanoside R14 Anemoside A Cussonoside B
GlcAraGlc(1→2)Ara-
GlcGlcGlc-
8 17 17
59 65 65
Rha(1→2)XylRha(1→2)AraRib(1→3)Rha(1→2)XylXyl(1→3)Rha(1→2)[Glc(1→4)Glc(1 →4)]Ara-
GlcGlcGlcGlc-
8 8 21 17
59 59 58 65
H Xyl GlcAGlcA-
Glc(1→6)GlcGlc(1→6)GlcGlc(1→6)GlcGlc(1→6)Glc-
8 8 8 8
59 59 59 66
Glc(1→2)AraRha(1→4)AraRha(1→2)XylRha(1→2)Glc-
Rha(1→4)GlcRha(1→2)GlcGlc(1→6)GlcGlc(1→6)Glc-
3,15 15 3,8 8
58 58 58 59
Glc(1→2)Ara-
Glc(1→6)Glc-
17
65
Rha(1→2)Ara-
Glc(1→6)Glc-
8
59
Ara(1→2)XylRha(1→2)Glc(1→2)AraRha(1→2)[Glc(1→4)]AraRib(1→3)Rha(1→2)AraH-
Glc(1→4)GlcRha(1→4)GlcGlc(1→6)GlcRha(1→4)GlcRha(1→4)Glc(1→6)Glc-
21 15
58 58 58 58 58
9,15 16
3,4,8,9,17,1 9
69 70 71 72
A1 A1 A1 A1
73
A1
74
A1
75
A1
76 77 78 79 80
A1 A1 A1 A1 A1
81 82 83 84 85
A1 A1 A1 A1 A1
86
A1
Ciwujianoside C3 Anhuienside D Nipponoside B Oleanolic acid 3-O-β-D-glucuronopyranosyl 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-[3-O-Sulfonato]-β-D-glucuronopyranosyl olean-12-en-28-oic acid 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester monosodium salt Oleanolic acid 3-O-β-D-glucopyranosyl-(6′-butyryl) 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside Oleanolic acid 3-O-β-D-glucuronopyranose methyl ester 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside Anhuienside E Ciwujianoside A1 Begoniifolide A Raddeanoside R19b Hederasaponin B (Hederagenin B)
AraXylGlcGlcA-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
4,17 3 8 8
58 58 59 59
(3′-NaSO3)-GlcA-
Rha(1→4)Glc(1→6)Glc-
2
67
(6′-butyryl)-Glc-
Rha(1→4)Glc(1→6)Glc-
8
58
GlcA methyl ester-
Rha(1→4)Glc(1→6)Glc-
8
58
Rha(1→2)GlcGlc(1→2)AraGlc(1→3)AraGlc(1→4)AraRha(1→2)Ara-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
58, 68 58 58 58 69
FlaccidosideⅡ Flaccidoside Ⅲ Flaccidoside V Flaccidoside VI 3-O-α-L-Rhamnopyranosyl-(1→2)-β-D-glucuronopyranosyl olean-12-en-28-oic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester 3-O-β-D-Xylopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside
Rha(1→2)XylGlc(1→2)XylRha(1→2)QuiGlc(1→2)Glc Rha(1→2)GlcA-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
3,8 4,17,20 4 15 3,7,8,15,17, 18,21 3,8 3,8,9 8 8 8
Xyl(1→2)Ara-
Rha(1→4)Glc(1→6)Glc-
17
65
68 58 59 59 59
87 88 89 90 91 92 93 94 95 96 97
A1 A1 A1 A1 A1 A1 A1 A1 A1 A1 A1
98
A1
99
A1
100
A1
101 102 103 104
A1 A1 A1 A1
Koreanaside 1 Raddeanoside R18 (Begoniifolide D) Raddeanoside R8 Hederacholichiside E Raddeanoside R15 Huzhangoside B Sieboldianoside B Anhuienside F Huzhangoside C Tomentoside C 3-O-β-D-Glucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-α-L-Rhamnopyranosyl-(1→2)-β-D-Glucopyranosyl-(1→4)-α-Larabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-α-L-Arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-DGlucopyranosyl-(1→4)-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl 28-O-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranosyl oleanolic acid Raddeanoside R17 Raddeanoside R16 Hupehensis saponin D 3-O-β-D-Glucopyranosyl-(1→4)-β-D-ribopyranosyl-(1→3)-α-Lrhamnopyranosyl-(1→2)-β-D-xylopyranosyl 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyr anosyl-(1→6)-β-D-glucopyranosyl oleanolic acid
Xyl(1→3)AraGlc(1→2)[Glc(1→4)]AraRha(1→2)Glc(1→2)AraRha(1→2)[Glc(1→4)]AraAra(1→3)Rha(1→2)AraRib(1→3)Rha(1→2)AraXyl(1→3)Rha(1→2)AraGlc(1→3)Rha(1→2)XylRib(1→3)Rha(1→2)XylGal(1→3)Rha(1→2)XylGlc(1→4)Rha(1→2)Ara-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
21 4 9,15 7,15,17‒19 15 10,16,21 7,17,19 3,8 16,21 21 15
58 58 58 29 58 58 58 58 58 58 60
Rha(1→2)Glc(1→4)Ara-
Rha(1→4)Glc(1→6)Glc-
7
60
Ara(1→3)Rha(1→2)Glc(1→4)Ara-
Rha(1→4)Glc(1→6)Glc-
15
60
Xyl(1→3)Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
30
Glc(1→4)Glc(1→3)Rha(1→2)AraAra(1→3)Rha(1→2)[Glc(1→4)]AraGlc(1→3)Rib(1→3)Rha(1→2)AraGlc(1→4)Rib(1→3)Rha(1→2)Xyl-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
15 15 10 21
60 58 60 58
105
A1
106
A1
107
A1
108
A1
109
A1
110
A1
111
A1
112
A1
113
A1
3-O-[3-O-Sulfonato]-β-D-glucuronopyranosyl olean-12-en-28-oic acid 28-O-4-O-acety-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester monosodium salt Oleanolic acid 3-O-β-D-glucuronopyranosyl 28-O-βD-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside 3-O-[3-O-Sulfonato]-β-D-glucuronopyranosyl olean-12-en-28-oic acid 28-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranosyl ester monosodium salt Raddeanoside R10
(3′-NaSO3)-GlcA-
Ac(1→4)Rha(1→4)Glc(1 →6)Glc-
2
58
GlcA-
Glc(1→3)Rha(1→4)Glc(1 →6)Glc-
2
58
(3′-NaSO3)-GlcA-
Glc(1→3)Rha(1→4)Glc(1 →6)Glc-
2
58
Rha(1→2)Glc(1→2)Ara-
15
58
Oleanolic acid 3-O-β-D-ribopyranosyl-(1→3)-α-Lrhamnopyranosyl-(1→2)-α-L-arabinopyranosyl 28-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside Oleanolic acid 3-O-β-D-ribopyranosyl-(1→3)-α-Lrhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopy ranosyl 28-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside Raddeanoside R11
Rib(1→3)Rha(1→2)Ara-
Glc(1→3)Rha(1→4)Glc(1 →6)GlcGlc(1→3)Rha(1→4)Glc(1 →6)Glc-
10
58
Rib(1→3)Rha(1→2)[Glc(1→4)]Ara-
Glc(1→3)Rha(1→4)Glc(1 →6)Glc-
10
58
Rha(1→2)Glc(1→2)Ara-
12,15
58
3-O-α-L-Rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside 3-O-α-L-Rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-Larabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-D-
Rha(1→2)Ara-
Glc(1→6)Glc(1→3)Rha(1 →4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc(1 →4)Rha(1→4)Glc(1→6)G lc-
15,19
58
Rha(1→4)Glc(1→6)Glc(1 →4)Rha(1→4)Glc(1→6)G lc-
15
58
Rha(1→2)Glc(1→2)Ara-
114
A1
115
A1
glucopyranosyl-(1→6)-β-D-glucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside Raddeanoside R19a
116 117 118 119 120 121 122 123 124
A2 A2 A2 A2 A2 A2 A2 A2 A2
Hederagenin Hederagenin 3-O-β-D-glucopyranoside Hederagenin 3-O-α-L-arabinopyranoside 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranosyl hederagenin 3-O-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl hederagenin 3-O-β-D-Xylopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin Kalopanaxsaponin A Leontoside B
125
A2
126
A2
127 128 129 130 131 132
A2 A2 A2 A2 A2 A2
133
A2
3-O-β-D-Glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]-β-Dgalactopyranosyl hederagenin 3-O-β-D-Glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-α-Larabinopyranosyl hederagenin Sapindoside B Pulsatiloside D Prosapogenin CP6 Clemargenoside G Hupehensis saponin C 3-O-β-D-Glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl hederagenin 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl hederagenin
Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc(1 →4)Rha(1→4)Glc(1→6)G lc-
15,19
58
Rha(1→2)Glc(1→2)Ara-
15
58
HGlcAraGal(1→2)GlcGlc(1→2)AraGlc(1→2)GlcXyl(1→2)AraRha(1→2)AraGlc(1→4)Ara-
Rha(1→4)Glc(1→6)Glc(1 →3)Rha(1→4)Glc(1→6)G lc(1→3)Rha(1→4)Glc(1→ 6)GlcHHHHHHHHH-
58 60 52 60 60 60 65 30 42
Glc(1→2)[Glc(1→6)]Gal-
H-
17‒19 11 14,17,19,21 11 14 14 17 17‒19 4,14,15,18,1 9 11
Glc(1→4)Glc(1→2)Ara-
H-
14
60
Xyl(1→3)Rha(1→2)AraRha(1→2)[Glc(1→4)]AraRib(1→3)Rha(1→2)AraRib(1→3)Rha(1→2)XylGlc(1→3)Rib(1→3)Rha(1→2)AraGlc(1→3)Rha(1→2)[Glc(1→4)]Ara-
HHHHHH-
17 17‒19 10,16,17 21 10 10
65 30 60 58 58 58
Xyl(1→3)Rha(1→2)[Glc(1→4)]Ara-
H-
19
58
60
134 135
A2 A2
136 137 138
A2 A2 A2
139
A2
140
A2
141 142
A2 A2
143 144 145
A2 A2 A2
146
A2
147 148 149 150 151 152 153 154
A2 A2 A2 A2 A2 A2 A2 A2
Tomentoside Aa 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)]-α-Larabinopyranosyl hederagenin Hederagenin-28-O-β-D-glucopyranosyl ester HN-saponin F 3-O-β-D-Glucopyranosyl-(1→2)-β-D-galactopyranosyl hederagenin 28-O-β-D-glucopyranoside 3-O-β-D-Glucopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranoside 3-O-β-D-Ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranoside Akebia sapononin D 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside Pulsatiloside C Begoniifolide C Cauloside D
Rib(1→3)Rha(1→2)[Glc(1→4)]AraXyl(1→3)Rha(1→2)[Glc(1→4)Glc(1 →4)]Ara-
HH-
21 19
58 30
HAraGlc(1→2)Gal-
GlcGlcGlc-
17 17,20 11
60 58 60
Glc(1→2)Ara-
Glc-
17
65
Rib(1→3)Rha(1→2)Ara-
Glc-
17
65
AraRha(1→2)[Glc(1→4)]Ara-
Glc(1→6)GlcGlc(1→6)Glc-
17,20 6
58 58
HCH3OCOCH2COAra-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
58 58 30
3-O-β-D-Glucopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside Cauloside F Leontoside D Kalopanaxsaponin B Hederacholichiside F Huzhangoside D Clematiganoside A Sieboldianoside A 3-O-β-D-Glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→6)]-β-Dgalactopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-
Glc-
Rha(1→4)Glc(1→6)Glc-
17,20 4 4,16,17,19,2 0 11
Glc(1→2)AraGlc(1→4)AraRha(1→2)AraRha(1→2)[Glc(1→4)]AraRib(1→3)Rha(1→2)AraRib(1→3)Rha(1→2)XylXyl(1→3)Rha(1→2)AraGlc(1→2)[Glc(1→6)]Gal-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
17,20 15,19 7,17‒19 18,19 10,16,17,21 21 17,19 11
60 60 60 58 58 69 65 60
60
155
A2
156 157 158 159
A2 A2 A2 A2
160
A2
161
A2
162
A2
163
A2
164
A2
165
A2
glucopyranoside 3-O-β-D-Glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-α-Larabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside Hupehensis saponin E Tomentoside A Tomentoside B 3-O-β-D-Glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-[α-Lrhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyra nosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Glucuronopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside 3-O-β-D-Ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside Hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-
Glc(1→4)Glc(1→2)Ara-
Rha(1→4)Glc(1→6)Glc-
14
60
Glc(1→3)Rib(1→3)Rha(1→2)AraRib(1→3)Rha(1→2)[Glc(1→4)]AraRib(1→3)Rha(1→2)[Glc(1→4)]XylGlc(1→4)Glc(1→4)[Rha(1→2)]Ara-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
10 21 21 19
60 69 69 65
Xly(1→3)Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
65
Xly(1→3)Rha(1→2)[Glc(1→4)Glc(1 →4)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
65
GlcA-
Glc(1→3)Rha(1→4)Glc(1 →6)Glc-
2
59
Rib(1→3)Rha(1→2)Ara-
Glc(1→3)Rha(1→4)Glc(1 →6)Glc-
10
59
H-
Rha(1→4)Glc(1→6)Glc(1 →4)Rha(1→4)Glc(1→6)G lc-
19
65
Xyl(1→3)Rha(1→2)Ara-
Rha(1→4)Glc(1→6)Glc(1
19
65
→4)Rha(1→4)Glc(1→6)G lc-
166
A2
arabinopyranosyl hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside Hupehensis saponin F
167
A2
Hupehensis saponin G
Rib(1→3)Rha(1→2)Ara-
168 169
A3 A3
170 171 172 173
A3 A3 A3 A3
174 175
A3 A3
176 177
A3 A3
178 179 180 181 182
A4 A4 A4 A4 A5
Raddeanoside Ra 27-Hydroxyoleanolic acid 3-O-β-D-glucopyranosyl (1→2)-α-L-arabinopyranoside Raddeanoside R12 Raddeanoside R20 Raddeanoside Rb Hydroxyoleanolic acid 3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside Raddeanoside R21 Hydroxyoleanolic acid 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-28-O-α-Lrhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1→6)-β-D-glucopyranoside Raddeanoside R9 Hydroxyoleanolic acid 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl-28-O-α-Lrhamnopyranosyl-(1→4)-β-D-glucopyranosyl (1→6)-β-D-glucopyranoside Begoniifolide B Tetrasepaloside Anhuienside A Anhuienside B 3β-[(O-β-D-glucopyranosyl-(1→4)-O-[a-L-rhamnopyranosyl-(1→2)]-
Rib(1→3)Rha(1→2)Ara-
10
70
10
70
Glc(1→4)AraGlc(1→2)Ara-
Rha(1→4)Glc(1→6)Glc(1 →3)Rha(1→4)Glc(1→6)G lcGlc(1→6)Rha(1→4)Glc(1 →6)Glc(1→3)Rha(1→4)G lc(1→6)GlcHH-
15,19 15
42 42
Rha(1→2)AraRha(1→2)[Glc(1→4)]araAra(1→3)Rha(1→2)AraRha(1→2)Glc(1→2)Ara-
HHHH-
15 15 15,19 15
60 71 42 58
Rha(1→2)AraGlc(1→4)Ara-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
15 15
71 58
Rha(1→2)Glc(1→2)AraRha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
15 15
60 42
CH3OOCH2COC(2′,3′-monoaccetonide)-Rib(f)Glc(1→2)GlcGlc(1→2)GlcRha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)GlcHRha(1→4)Glc(1→6)GlcRha(1→4)Glc(1→6)Glc-
10 20 3 3 6
58 58 58 58 72
183
A6
184
A6
185 186 187
A7 A8 A8
188
A8
189
A8
190
A8
191
A8
192
A8
α-L-arabinopyranosyl)oxy]-2β-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester 3β-[(O-β-D-Glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)] -α-L-arabinopyranosyl)oxy]-2β,23-dihydroxyolean-12-en-28-oic acid 3β-[(O-β-D-Glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)] -α-L-arabinopyranosyl)oxy]-2β,23-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester Anemonerivulariside A Siaresinolic acid 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyra-nosyl siaresinolic acid 3-O-β-D-Glucopyranosyl-(1→4)-α-L-arabinopyranosyl siaresinolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester 3-O-α-L-Rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl siaresinolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-α-L-Rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl(1→4)]-α-Larabinopyranosyl siaresinolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl siaresinolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl siaresinolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester
Rha(1→2)[Glc(1→4)]Ara-
H-
6
72
Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
6
72
Rib(1→3)Rha(1→2)AraHXyl(1→3)Rha(1→2)[Glc(1→4)]Ara-
HH-
16 19 19
73 30 30
Glc(1→4)Ara-
Rha(1→4)Glc(1→6)Glc-
19
30
Rha(1→2)Ara-
Rha(1→4)Glc(1→6)Glc-
19
65
Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
65
Xyl(1→3)Rha(1→2)Ara-
Rha(1→4)Glc(1→6)Glc-
19
30
Xyl(1→3)Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
30
193
A8
194
A9
195
A9
196
A10
197
A10
198
A10
199
A11
200
A11
201
A12
3-O-β-D-Glucopyranosyl(1→4)-β-D-glucopyranosyl(1→4)-[α-Lrhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl siaresinolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-α-L-Rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-Larabinopyranosyl 21α-hydroxy oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-[α-Lrhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl 21α-hydroxy oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl gypsogenin 28-O-β-D-glucopyranoside 3-O-α-L-Arabinopyranosyl gypsogenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3-O-β-D-Xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-Dglucopyranosyl-(1→4)]-α-L-arabinopyranosyl gypsogenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-Dglucopyranoside 3β-[(O-β-D-Glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)] -α-L-arabinopyranosyl)oxy]-23-hydroxyolean-18-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester 3-O-β-D-Glucopyranosyl-(1→4)-O-[α-L-rhamnopyranosyl-(1→2)]-αL-arabinopyranosyl 23-hydroxyolean-18-en oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D -glucopyranoside Anemoside B
Glc(1→4)Glc(1→4)[Rha(1→2)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
65
Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
65
Glc(1→4)Glc(1→4)[Rha(1→2)]Ara-
Rha(1→4)Glc(1→6)Glc-
19
65
Xyl(1→3)Rha(1→2)[Glc(1→4)]Ara-
Glc-
17
65
Ara-
Rha(1→4)Glc(1→6)Glc-
17
65
Xyl(1→3)Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
17
65
Rha(1→2)[Glc(1→4)]Ara-
Rha(1→4)Glc(1→6)Glc-
6
72
Glc(1→4)[Rha(1→2)]Ara-
Rha(1→4)Glc(1→6)Glc-
15
59
Rib(1→3)Rha(1→2)Ara-
-
16
74
Table S2 Other types of triterpenoids isolated from Anemone species (B‒D types). No.
Type
Compound name
R1
R2
R3
Taxon
Ref.
202 203 204 205 206 207 208 209 210 211 212
B1 B1 B1 B1 B2 B3 B4 C C C C
HHHOHHHRha(1→2)XylHHHAra-
HOOCCH3HOCH2HOOCHHGlc(1→6)GlcCH3HOCH2HOOCRha(1→4)Glc(1→6)Glc-OOC-
CH3CH3CH3HOCH2-
5 5 5 5 21 21 8 15 15 15,21 17
75 75 75 75 62 62 59 9 9 62 65
213 214
D D
Ursolic acid α-Amyrin acetate 28-Hydroxy-α-Amyrin acetate 2α,23-Dihydroxy-ursolic acid 2α,3β,23-Trihydroxyurs-12-en-28-oic acid 18-Hydroxyursolic acid Flaccidoside IV Lupeol Betulin Betulinic acid 3β-O-α-L-Arabinopyranosyl betulinic acid 28-O-α-Lrhamnopyranosyl-(1→4)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranoside Cimigenol-3-O-β-D-xylopyranoside Cimigenol-3-O-β-D-xylopyrano(1→3)-β-Dxylopyran-oside
XylXyl(1→3)Xyl-
-
-
1 1
76 76
Taxon: 1: Anemone altaica; 2: A. amurensis; 3: A. anhuiensis; 4: A. begoniifolia; 5:A. cathayensis; 6: A. coronaria; 7: A. davidii; 8: A. flaccida; 9: A. hofengensis; 10: A. hupehensis; 11: A. multifida; 12: A. narcissiflora; 13: A. obtusiloba; 14: A. pulsatilla; 15: A. raddeana; 16: A. rivularis; 17: A. rivularis var. flore-minore; 18: A. rupestris; 19: A. taipaiensis; 20: A. tetrasepala; 21: A. tomentosa. Abbreviations: Glc: β-D-Glucopyranosyl; Rha: α-L-Rhamnopyranosyl; Xyl: β-D-Xylopyranosyl; Ara: α-L-Arabinopyranosyl; Gal: β-D-Galactopyranosyl; GlcA: β-D-Glucuronopyranosyl; Rib: β-D-Ribopyranosyl; Qui: β-D-Quinovopyranosyl.
Table S3 Other constituents isolated from Anemone species. No.
Type
Compound name
Substituent group
Taxon
Ref.
215 216 217 218 219 220 221 222 223 224 225 226 227 228 229 230 231
Ⅰ Ⅰ Ⅰ Ⅰ Ⅰ Ⅰ Ⅰ Ⅰ Ⅰ Ⅰ Ⅰ Ⅱ Ⅱ Ⅱ Ⅱ Ⅱ Ⅱ
R1=R2=R3=R4=R5=H R1=R2=R3=R5=H; R4=OCH2CH3 R1=R4=OCH3; R2=CH3; R3=R5=H R1=R2=H; R3=R4=OCH3; R5=OH R1=R2=OCH3; R3=R5=H; R4=CH3 R1=R2=H; R3=R5=OCH3; R4=OH R1=OCH3; R2=CH3; R3=R4=O-CH2-O; R5=H R1=R2=R5=H; R3=R4=OH R1=R4=OCH3; R2=CH3; R3=OH; R5=H R1=R4=OCH3; R2=CHO; R3=OH; R5=H R1=Rha; R2=Gal R1=Rha; R2=OH R=H
5 21 21 21 21 21 21 1 15 15 8 18 18 6 6 6 6
75 58 27,77 58 27,77 58 77 78 39 39 63 79 79 80 80 80 80
232
Ⅱ
R1=H; R2=GlcA; R3=H
6
5
233
Ⅱ
R2=GlcA; R3=H
6
5
234
Ⅱ
R2=GlcA; R3=H
6
5
235
Ⅱ
R2=H; R3=H
6
5
236
Ⅱ
R2=GlcA; R3=OH
6
5
237 238
Ⅲ Ⅲ
Coumarin 7-Ethyl-coumarin 4,7-Dimethoxyl-5-methylcoumarin Fraxidin 4,5-Dimethoxyl-7-methylcoumarin Isofraxidin 4-Methoxyl-5-methyl-6,7-methylenedioxy-coumarin Esculetin 4, 7-Dimethoxyl-5-methyl-6-hydroxycoumarin 4, 7-Dimethoxyl-5-formyl-6-hydroxycoumarin Oxypeucedanin hydrate Quercetin-3-galactoside-7-rhamnoside Quercetin-7-rhamnoside Pelargonidin 3-[2-(xylosyl)-galactoside] Pelargonidin 3-[2-(xylosyl)-6-(malonyl) galactoside] Pelargonidin 3-[2-(xylosyl)-6-(methyl-malonyl) -galactoside] (6′′-O-(Pelargonidin 3-[2-(xylosyl)-galactosyl])) ((4-glucosyl) caffeoyl)-tartaryl) malonate Delphinidin 3-[2-(2-(caffeoyl) glucosyl) galactoside]-7-[6-(caffeoyl) glucoside]-3′-[glucuronide] Delphinidin 3-[2-(2-(caffeoyl) glucosyl)-6-(malonyl) galactoside]-7-[6-(caffeoyl) glucoside]-3′-[glucuronide] Delphinidin 3-[2-(2-(caffeoyl) glucosyl)-6-(2-(tartaryl) malonyl) galactoside]-7-[6-(caffeoyl) glucoside]-3′-[glucuronide] Delphinidin 3-[2-(2-(caffeoyl) glucosyl)-6-(2-(tartaryl) malonyl) galactoside]-7-[6-(caffeoyl)-glucoside] Cyanidin 3-[2-(2-(caffeoyl) glucosyl)-6-(2-(tartaryl) malonyl)galactoside]-7-[6-(caffeoyl)glucoside]-3′-[glucuronide] Anemonolide Ardicren
R=Rha(1→4)Glc(1→4)[Glc(1→2)]Ara-
16 5
74 75
239 240 241 242
Ⅲ Ⅲ Ⅲ Ⅳ
243 244 245 246 247 248 249 250 251 252 253 254 255 256 257 258 259 260 261 262 263 264 265 266 267 268 269 270
Ⅳ Ⅳ Ⅴ Ⅴ Ⅴ Ⅴ Ⅴ Ⅴ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅵ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ
Protoanemonin Anemonin Ranunculin (7S,8R,7′R,8′S)4,9,4′,7′-Tetrahydroxy-3,3′-dimethoxy-7′-O-n-butyl-7,9′epoxylignan 9-O-β-D-glucopyranoside (+)-Isolariciresinoil-9-O-β-D-glucopyranoside (+)-Pinoresinol-4-O-β-D-glucopyranoside β-Sitosterol Daucosterol Stigmasterol 3-O-β-D-Glucopyranosyl stigmasterol Ergosterol peroxide (22E,24R)-5α,8α-Epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol Carboxymethyl isoferulate Ferulic acid Isoferulic acie Cinnamic acid Caffeic acid 1-O-Caffeoyl-β-D-glucopyranoside 6-O-Feruloyl-D-glucopyranose Coumaric acid Mono-feruloyltartaric acid Chlorogenic acid Glucosyringic acid 4-Hydroxy-benzoic acid 3-Hydroxy-4-methoxy-benzoic acid Protocatechuic aldehyde 4′-O-Methylequisetum pyrone γ-Terpineol 4-Tert-butylphenetole 2,6-Di-tert-butyl-4-methylphenol Benzeneacetaldehyde Phenylethyl alcohol
-
15 15 14,15 17
9 9 81 60
R=H R=Glc R=H R=Glc R1=OH; R2=OCH3; R3=H R1=OCH3; R2=OH; R3=H R1=OH; R2=R3=H R1=R2=OH; R3=H R1=R2=OH; R3=Glc R1=OH; R2=OCH3; R3=Glc R1=OH; R2=R3=H R1=H; R2=OH R1=OH; R2=OCH3 R=CHO R=CH2OH
1 1 1,21 1,2,21 21 21 16,21 16 1 1,16 1 1 1,16 16 1 16 1 1 1 16 16 1 2 15 15 15 15,16 15
78 78 82 83 77 77 77 73 61 84 61 85 86 73 78 86 78 78 78 86 86 85 83 87 87 87 22 87
271 272 273 274 275 276 277 278 279 280 281 282 283 284 285 286 287 288 289 290 291 292
Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅶ Ⅷ
293 294 295 296 297 298 299 300 301 302
Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ
Benzaldehyde Benzyl alcohol (R) Acetophenone (M) 2,4-Dihydroxy-3-methylacetophenne (E)-4-Phenyl-3-buten-2-one 3-BHA Myristicin 2-Methyl hexadecane 7,9-Dimethyl hexadecane Nonadecanol Heptanoic acid (R) 2,3-Dimethyl heptane (M) 3-Ethyl-2-methyl hexane (M) 5-Methyl undecane (R) 2,4-Dimethyl undecane (M) 4,5-Diethyl octane (R) 5,6-Dimethyl decane 2,4-Dodecadienal (R) Patchouli alcohol (M) 3-(6,6-Dimethyl-5-oxohept-2-enyl)-cyclohexanone Caryophyllene (2S,3S,4R,8E)-2-[(2′R)-2′-Hydroxy-tetracosanoyl]-1,3,4-trihydroxy-8oeta decene Aralia cerebroside Cirsiumaldehyde 1,6,9,13-tetraoxadispiro [4,2,4,2] tetradecane-2,10-dione Adenine Adenosine Uridine 2,3,4,9-Tetrahydro-1H-pyridine pyrido [3,4-b] indole-3-carboxylic acid Phenylalanine Thymidine 13(S)-Hydroxy-7-oxo-labda-8,14-diene-19-oic acid-β-D-galactosyl ester
R1=CHO; R2=R3=R4=H R1=CH2OH; R2=R3=R4=H R1=COCH3; R2=R3=R4=H R1=COCH3; R2=R4=OH; R3=CH3 -
16 16 16 16 16 16 16 15 15 15 16 16 16 16 16 16 16 16 16 16 16 1
22 22 22 22 22 22 22 87 87 87 22 22 22 22 22 22 22 22 22 22 22 85
-
1 1 1 1 1 1 1 1 1 17
85 82 61 78 61 61 78 78 78 60
303 304 305 306 307 308 309 310 311 312 313 314 315
Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ Ⅷ
Tomentoside Linoleic acid Hexanoic acid 5-Hydroxy-4-oxo-pentanoic acid Succinic acid Palmic acid Monoethyl malonate Triacontane Methyl β-D-glucopyranoside β-D-Glucopyranosyl α-D-Glucopyranosyl Methyl-O-α-D-fructofuranoside β-D-Galactitol
R=CH2OH R=OH R=OCH3 -
21 15 15 1 1 1 8 1 1 2 2 2 2
62 9 9 61,84 61 61 63 61 61 83 83 83 83
Ⅰ: coumarins; Ⅱ: flavonoids; Ⅲ: lactones; Ⅳ: lignans; Ⅴ: steroids; Ⅵ: phenolic compounds; Ⅶ: essential oils; Ⅷ: other compounds.
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