Supporting information Figure S1 Phylogenetic

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-


8

58

GlcA methyl ester-


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-


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-


7

60

Ara(1→3)Rha(1→2)Glc(1→4)Ara-


15

60



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-


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-


2

58


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-


10

58


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


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-


15,19

58


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


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


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-


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-


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-


10 21 21 19

60 69 69 65

Xly(1→3)Rha(1→2)[Glc(1→4)]Ara-


19

65

Xly(1→3)Rha(1→2)[Glc(1→4)Glc(1 →4)]Ara-


19

65

GlcA-


2

59



10

59

H-


19

65


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


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)]-


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


H-

6

72



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-


19

30

Rha(1→2)Ara-


19

65



19

65



19

30



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-


19

65



19

65

Glc(1→4)Glc(1→4)[Rha(1→2)]Ara-


19

65


Glc-

17

65

Ara-


17

65



17

65



6

72

Glc(1→4)[Rha(1→2)]Ara-


15

59


-

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.

References 1. Hao DC, Xiao PG, Ma H, Peng Y, He CN. Mining chemodiversity from biodiversity: pharmacophylogeny of medicinal plants of the Ranunculaceae. Chin J Nat Med 2015;13:507-20. 2. Liu Y, Li Y, Yang W, Zhang L, Cao G. Anti-hepatoma activity in mice of a polysaccharide from the rhizome of Anemone raddeana. Int J Biol Macromol 2012;50:632-6. 3. Han LT, Li J, Huang F, Yu SG, Fang NB. Triterpenoid saponins from Anemone flaccida induce apoptosis activity in HeLa cells. J Asian Nat Prod Res 2009;11:122-7. 4. Liu Q, Zhu XZ, Feng RB, Liu Z, Wang GY, Guan XF, et al. Crude triterpenoid saponins from Anemone flaccida (Di Wu) exert anti-arthritic effects on type II collagen-induced arthritis in rats. Chin Med 2015;10:20. 5. Saito N, Toki K, Moriyama H, Shigihara A, Honda T. Acylated anthocyanins from the blue-violet flowers of Anemone coronaria. Phytochemistry 2002;60:365-73. 6. Kong X, Wu W, Yang Y, Wan H, Li X, Zhong M, et al. Total saponin from Anemone flaccida Fr. Schmidt abrogates osteoclast differentiation and bone resorption via the inhibition of RANKL-induced NF-κB, JNK and p38 MAPKs activation. J Transl Med 2015;13:91. 7. Guan YY, Liu HJ, Luan X, Xu JR, Lu Q, Liu YR, et al. Raddeanin A, a triterpenoid saponin isolated from Anemone raddeana, suppresses the angiogenesis and growth of human colorectal tumor by inhibiting VEGFR2 signaling. Phytomedicine 2015;22:103-10. 8. Xiao PG, Wang LW, Lv SJ, Qiu GS. Statistical analysis of the ethnopharmacologic data based on Chinese medicinal plants by electronic computer I. Magnoliidae. Chin J Integr Trad West Med 1986;6:253-6. 9. Sun YX, Liu JC, Liu DY. Phytochemicals and bioactivities of Anemone raddeana Regel: a review. Pharmazie 2011;66:813-21. 10. Wang W, Liu H, Song Y, Zhang B, Xu J. Bencaological studies on Changpu. Chin Trad Herb Drug1995;26:263-5. 11. He K, Jiang X. Sky islands of Southwest China. I. An overview of phylogeographic patterns. Chin Sci Bull 2014;59:585-97. 12. Gong HD. Investigation on traditional Tibetan medicine plant resources of Anemone in the Eastern of Qinghai-Tibet Plateau. J Anhui Agri Sci 2011;39:6388, 6391. 13. Li M, Lei ZQ, Zhong GY. Analysis of varieties and standards of Ranunculaceae medicinal plants used in Tibetan medicine. Trad Chin Drug Res Clin Pharmacol 2015;26:133-7.

14. Pentso TT. Jing Zhu Ben Cao. Mao JZ, translator. Shanghai: Shanghai Scientific and Technical Publishers; 2012. 15. Kumar K, Sharma YP, Manhas RK, Bhatia H. Ethnomedicinal plants of Shankaracharya hill, Srinagar, J&K, India. J Ethnopharmacol 2015;170:255-74. 16. Lv CN, Fan L, Wang J, Qin RL, Xu TY, Lei TL, et al. Two new triterpenoid saponins from rhizome of Anemone amurensis. J Asian Nat Prod Res 2015;17:132-7. 17. Cao P, Wu FE, Ding LS. Advances in the studies on the chemical constituents and biologic activities for Anemone species. Nat Prod Res Dev 2004;16:581-4. 18. Zou ZJ, Liu HX, Yang JS. Phytochemical components and pharmacological activities of the genus Anemone. Chin Pharm J 2004;39:493-5. 19. Hao DC, Gu XJ, Xiao PG. Medicinal plants: Chemistry, biology and omics. Oxford: Elsevier-Woodhead; 2015. 20. Hao DC, Gu XJ, Xiao PG, Peng Y. Chemical and biological research of Clematis medicinal resources. Chin Sci Bull 2013;58:1120-9. 21. Hao DC, Gu XJ, Xiao PG, Liang ZG, Xu LJ, Peng Y. Recent advance in chemical and biological studies on Cimicifugeae pharmaceutical resources. Chin Herb Med 2013;5:81-95. 22. Shi B, Liu W, Gao L, Chen C, Hu Z, Wu W. Chemical composition, antibacterial and antioxidant activity of the essential oil of Anemone rivularis. J Med Plant Res 2012;6:4221-4. 23. Jürgens A, Dötterl S. Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Anemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species. Am J Bot 2004;91:1969-80. 24. Wang MK, Ding LS, Wu FE. Antitumor effects of raddeanin A on S180, H22 and U14 cell xenografts in mice. Chin J Cancer 2008;27:910-3. 25. Xue G, Zou X, Zhou JY, Sun W, Wu J, Xu JL, et al. Raddeanin A induces human gastric cancer cells apoptosis and inhibits their invasion in vitro. Biochem Biophys Res Commun 2013;439:196-202. 26. Li J, Tang H, Zhang Y, Tang C, Li B, Wang Y, et al. Saponin 1 induces apoptosis and suppresses NF-κB‒mediated survival signaling in glioblastoma multiforme (GBM). PLoS One 2013;8:e81258. 27. Ji C, Cheng G, Tang H, Zhang Y, Hu Y, Zheng M, et al. Saponin 6 of Anemone taipaiensis inhibits proliferation and induces apoptosis of U87 MG cells. Chin J Cell Mol Immunol 2015;31:484-6. 28. Ji CC, Tang HF, Hu YY, Zhang Y, Zheng MH, Qin HY, et al. Saponin 6 derived from Anemone taipaiensis induces U87 human malignant glioblastoma cell apoptosis via regulation of FAS and BCL‑2 family proteins. Mol Med Rep 2016;14:380-6. 29. Wang X, Zhang W, Gao K, Lu Y, Tang H, Sun X. Oleanane-type saponins from Anemone taipaiensis and their cytotoxic activities. Fitoterapia 2013;89:224-30. 30. Wang XY, Gao H, Zhang W, Li Y, Cheng G, Sun XL, et al. Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis. Bioorg Med Chem Lett 2013;23:5714-20. 31. Wang Y, Tang H, Zhang Y, Li J, Li B, Gao Z, et al. Saponin B, a novel cytostatic compound purified from Anemone taipaiensis, induces apoptosis in a human glioblastoma cell line. Int J Mol Med 2013;32:1077-84. 32. Han LT, Fang Y, Li MM, Yang HB, Huang F. The antitumor effects of triterpenoid saponins from the Anemone flaccida and the underlying mechanism. Evid Based Complement Alternat Med 2013;2013:517931. 33. Han LT, Fang Y, Cao Y, Wu FH, Liu E, Mo GY, et al. Triterpenoid saponin flaccidoside II from Anemone flaccida triggers apoptosis of NF1-associated malignant peripheral nerve sheath tumors via the MAPK-HO-1 pathway. Onco Targets Ther 2016;9:1969-79. 34. Chang IC, Chiang TI, Lo C, Lai YH, Yue CH, Liu JY, et al. Anemone altaica induces apoptosis in human osteosarcoma cells. Am J Chin Med 2015;43:1031-42. 35. Sun Y, Li M, Liu J. Haemolytic activities and adjuvant effect of Anemone raddeana saponins (ARS) on the immune responses to ovalbumin in mice. Int Immunopharmacol 2008;8:1095-102. 36. Lee TH, Huang NK, Lai TC, Yang AT, Wang GJ. Anemonin, from Clematis crassifolia, potent and selective inducible nitric oxide synthase inhibitor. J Ethnopharmacol 2008;116:518-27. 37. Liu C, Yang Y, Sun D, Wang C, Wang H, Jia S, et al. Total saponin from Anemone flaccida Fr. Schmidt prevents bone destruction in experimental rheumatoid arthritis via inhibiting

osteoclastogenesis. Rejuvenation Res 2015;18:528-42. 38. Kong X, Yang Y, Wu W, Wan H, Li X, Zhong M, et al. Triterpenoid saponin W3 from Anemone flaccida suppresses osteoclast differentiation through inhibiting activation of MAPKs and NF-κB pathways. Int J Biol Sci 2015;11:1204-14. 39. Ren FZ, Chen SH, Zheng ZH, Zhang XX, Li LH, Dong AH. Coumarins of Anemone raddeana Regel and their biological activity. Acta Pharm Sin 2012;47:206-9. 40. Lu J, Sun Q, Sugahara K, Sagara Y, Kodama H. Effect of six compounds isolated from rhizome of Anemone raddeana on the superoxide generation in human neutrophil. Biochem Biophys Res Commun 2001;280:918-22. 41. Yamashita K, Lu H, Lu J, Chen G, Yokoyama T, Sagara Y, et al. Effect of three triterpenoids, lupeol, betulin, and betulinic acid on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils. Clin Chim Acta 2002;325:91-6. 42. Wei S, He W, Lu J, Wang Z, Yamashita K, Yokoyama M, et al. Effects of five oleanolic acid triterpenoid saponins from the rhizome of Anemone raddeana on stimulus-induced superoxide generation, phosphorylation of proteins and translocation of cytosolic compounds to cell membrane in human neutrophils. Fitoterapia 2012;83:402-7. 43. Hao DC, Xiao PG, Liu M, Peng Y, He CN. Pharmaphylogeny vs. pharmacophylogenomics: molecular phylogeny, evolution and drug discovery. Acta Pharm Sin 2014;49:1387-94. 44. Hao DC, Xiao PG, Liu LW, Peng Y, He CN. Essentials of pharmacophylogeny: knowledge pedigree, epistemology and paradigm shift. China J Chin Mater Med 2015;40:3335-42. 45. Hao DC, Xiao PG. Genomics and evolution in traditional medicinal plants: road to a healthier life. Evol Bioinform Online 2015;11:197-212. 46. Wang W, Lu AM, Ren Y, Endress ME, Chen ZD. Phylogeny and classification of Ranunculales: evidence from four molecularloci and morphological data. Perspect Plant Ecol Evol Syst 2009;11:81-110. 47. Cossard G, Sannier J, Sauquet H, Damerval C, de Craene LR, Jabbour F, et al. Subfamilial and tribal relationships of Ranunculaceae: evidence from eight molecular markers. Plant Syst Evol 2016;302:419-431. 48. Hoot SB, Meyer KM, Manning JC. Phylogeny and reclassification of Anemone (Ranunculaceae), with an emphasis on austral species. Syst Bot 2012;37:139-52. 49. Zhan C, Li X, Zhao Z, Yang T, Wang X, Luo B, et al. Comprehensive analysis of the triterpenoid saponins biosynthetic pathway in Anemone flaccida by transcriptome and proteome profiling. Front Plant Sci 2016;7:1094. 50. Laura M, Borghi C, Bobbio V, Allavena A. The effect on the transcriptome of Anemone coronaria following infection with rust (Tranzschelia discolor). PLoS One 2015;10:e0118565. 51. Hagel JM, Morris JS, Lee EJ, Desgagné-Penix I, Bross CD, Chang L, et al. Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants. BMC Plant Biol 2015;15:227. 52. Hao DC, Ma P, Mu J, Chen SL, Xiao PG, Peng Y, et al. De novo characterization of the root transcriptome of a traditional Chinese medicinal plant Polygonum cuspidatum. Sci China Life Sci 2012;55:452-66. 53. Han F, Peng Y, Xu L, Xiao PG. Identification, characterization, and utilization of single copy genes in 29 angiosperm genomes. BMC Genomics 2014;15:504. 54. Hagel JM, Mandal R, Han B, Han J, Dinsmore DR, Borchers CH, et al. Metabolome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants. BMC Plant Biol 2015;15:220. 55. Wang WT, Liu B. A new section with a new species of Anemone (Ranunculaceae) from Mt. Xiaowutai, China. J Syst Evol 2008;46:738-41. 56. Yuan Q, Yang QE. Anemone xingyiensis (Ranunculaceae), a new species from Guizhou, China. Bot Studi 2009;50:493-8. 57. Wang WT. Three new species of Anemone (Ranunculaceae) from Xizang. Plant Diversity Resour 2014;36:449-52. 58. Wang Y. Studies on the saponin constituents of Anemone tomentosa [dissertation]. Xi’an: Fourth Military Medical University; 2012. 59. Tang JQ. Studies on triterpenoid saponins of the rhizomes of Anemone flaccida [dissertation]. Guangzhou: Jinan University; 2013.

60. Ding Y. Studies on the chemical constituents of Anemone rivularis var. flore-minore [dissertation]. Xi’an: Fourth Military Medical University; 2011. 61. Zou ZJ. Studies on the chemical constituents of Anemone altaica, Hemistepta lyrata and Euphorbia latifolia [dissertation]. Beijing: Peking Union Medical College; 2006. 62. Hu HB, Zheng XD, Jian YF, Liu JX, Zhu JH. Constituents of the root of Anemone tomentosa. Arch Pharm Res 2011;34:1097-105. 63. Zhang LT. The study on chemical compounds from Anemone flaccida and Duchesnea indica [dissertation]. Tianjin: Tianjin University; 2007. 64. Hou AW. Studies on the fingerprint and chemical composition from two related plants of Anemone fiaccida [dissertation]. Wuhan: Hubei University of Traditional Chinese Medicine; 2012. 65. Wang XY. Studies on bioactive constituents from three medical plants collected on Taibai mountain [dissertation]. Xi’an: Fourth Military Medical University; 2014. 66. Su YQ. Chemical constituents and structure activity relationship of A. flaccida [dissertation]. Wuhan: Hubei University of Traditional Chinese Medicine; 2007. 67. Zhang Y, Huang X, Wang L, Wang Y, Wang Y, Ye W. New triterpenoid saponins from the rhizomes of Anemone amurensis. Chin J Chem 2012;30:1249-54. 68. Bing FH, Han LT, Zhang GB, Yi YD. Chemical constituents of rhizome of Anemone flaccida and their immuno-suppressive activities in vitro. J China Pharm Univ 2008;39:496-499. 69. Wang Y, Kang W, Hong LJ, Hai WL, Wang XY, Tang HF, et al. Triterpenoid saponins from the root of Anemone tomentosa. J Nat Med 2013;67:70-7. 70. Wang MK, Wu FE, Chen YZ. Triterpenoid saponins form Anemone hupehensis. Phytochemistry 1997;44:333-5. 71. Lu J, Xu B, Gao S, Fan L, Zhang H, Liu R, et al. Structure elucidation of two triterpenoid saponins from rhizome of Anemone raddeana Regel. Fitoterapia 2009;80:345-8. 72. Mimaki Y, Watanabe K, Matsuo Y, Sakagami H. Triterpene glycosides from the tubers of Anemone coronaria. Chem Pharm Bull 2009;57:724-9. 73. Anh Minh CT, Khoi NM, Thuong PT, Hwang IH, Kim DW, Na MK. A new saponin and other constituents from Anemone rivularis Buch.-Ham. Biochem Syst Ecol 2012;44:270-4. 74. Liao X, Li BG, Wang MK, Ding LS, Pan YJ, Chen YZ. The chemical constituents from Anemone rivularis. Chem J Chin Univ 2001;22:1338-41. 75. Gong WZ. Chemical constituents and bioactivity of Anemone cathayensis [dissertation]. Beijing: Minzu University of China; 2011. 76. Zou ZJ, Yang JS. Studies on the chemical constituents of the roots of Anemone altaica. J Chin Med Mater 2008;31:49-51. 77. Wang JR, Peng SL, Wang MK, Feng JT, Ding LS. Chemical constituents of the Anemone tomentosa root. Acta Bot Sin 1999;41:107-10. 78. Wang YZ, Zeng G, Zhang M, Liu Y. Chemical constituents from rhizoma of Anemone altaica. Chin Trad Herb Drug 2014;45:1219-22. 79. Liao X, Chen YZ, Ding LS, Li BG. Chemical constituents from Anemone rupestris ssp. Gelida. Nat Prod Res Dev 1999;11:1-6. 80. Toki K, Saito N, Shigihara A, Honda T. Anthocyanins from the scarlet flowers of Anemone coronaria. Phytochemistry 2001;56:711-5. 81. Varitimidis C, Petrakis PV, Vagias C, Roussis V. Secondary metabolites and insecticidal activity of Anemone pavonina. Z Naturforsch C 2006;61:521-6. 82. Zou ZJ, Yang JS. Studies on chemical constituents of rhizoma Anemones altaicae. Mod Chin Med 2008;23:10-1. 83. Zhang Y, Huang XJ, Wang Y, Ye WC. Non-saponin compounds from the rhizomes of Anemone amurensis. Food Industr 2014;35:99-101. 84. Ju Y, Jia ZJ, Zhu ZQ. Chemical constituents of Anemone altaica. Chin Trad Herb Drug 1986;17:388-9. 85. Zou ZJ, Yang JS. Chemical constituents from the roots of Anemone altaica. West China J Pharm Sci 2008;23:265-6. 86. Shao JH, Zhao CC, Liu MX. Separation and structural identification on the anti-tumor activity of Anemone rivularis. J Yangzhou Univ (Nat Sci Ed) 2011;14:48-50. 87. Yan ZK, Liu SY, Zhang YL, Ni XZ, Jia L. Preliminary study on the insecticidical activity and chemical components of Anemone hupehensis L. Acta Bot Boreali-Occident Sin 1990;10:141-8.