Table 1 Steroidal saponins (aglycones) in T. terrestris

1

Tigogenin

I

OH

H

H

H

H

H

R

[7]

2

Neotigogenin

I

OH

H

H

H

H

H

S

[8]

3

Tigogenin-3-O-β -d-glc(1 → 4)-β -d-gal (A)

I

Ra

H

H

H

H

H

R

[9]

4

Terrestrosin F

I

Rb

H

H

H

H

H

R

[10]

5

Desgalactotigonin

I

Rc

H

H

H

H

H

R

[9, 11]

6

Gitonin (B)

I

Rd

H

H

H

H

H

R

[11]

7

Tigogenin-3-O-β -d-xyl-(1 → 2)-[β -d-xyl-(1 → 3)]-β -d-glc(1 → 4)-[α -l-rha(1 → 2)]-β -d-gal (C)

I

Re

H

H

H

H

H

R

[9, 11, 12]

8

Tribulosin

I

Re

H

H

H

H

H

S

[13]

9

Terrestrosin A

I

Rf

H

H

H

H

H

R,S

[11]

10

Terrestrosin B

I

Rg

H

H

H

H

H

R,S

[11]

11

Gitogenin

I

OH

OH

H

H

H

H

R

[7, 14]

12

Neogitogenin

I

OH

OH

H

H

H

H

S

[15]

13

Gitogenin-3-O-β -d-glc(1 → 4)-β -d-gal

I

Ra

OH

H

H

H

H

R

[16]

14

F-gitonin

I

Rd

OH

H

H

H

H

R

[11]

15

Desglccolanatigonin

I

Rd

OH

H

H

H

H

R

[11]

16

25R,S-5α-spiro-2α,3β-dihydroxyl-3-O-β -d-glc-(1 → 4)-β -d-gal

I

Ra

OH

H

H

H

H

R,S

[16]

17

Terrestrosin E

I

Rf

OH

H

H

H

H

R,S

[11, 16]

18

Hecogenin

I

OH

H

=O

H

H

H

R

[7, 17]

19

Neohecogenin sapogenin

I

OH

H

=O

H

H

H

S

[17]

20

Agovoside A

I

Rh

H

=O

H

H

H

R

[12]

21

Hecogenin-3-O-β -d-glc-(1 → 4)-β -d-gal (D)

I

Ra

H

=O

H

H

H

R

[9, 18]

22

Hecogenin-3-O-β -d-glc-(1 → 2)-β -d-glc(1 → 4)-β -d-gal (E)

I

Ri

H

=O

H

H

H

R

[9]

23

Hecogenin-3-O-β -d-xyl-(1 → 3)-β -d-glc(1 → 4)-β -d-gal (F)

I

Rj

H

=O

H

H

H

R

[9]

24

Hecogenin-3-O-β -d-glc-(1 → 2)-[3-O-β -d-xyl]-β -d-glc-(1 → 4)-β -d-gal (G)

I

Rd

H

=O

H

H

H

R

[9, 12]

25

Terrestrosin D

I

Rk

H

=O

H

H

H

R

[11, 12]

26

Hecogenin-3-O-β -d-xyl-(1 → 2)-[β -d-xyl-(1 → 3)]-β -d-glc(1 → 4)-[α -l-rha-(1 → 2)]-β -d-gal (H)

I

Re

H

=O

H

H

H

R

[12]

27

Neohecogenin-3-O-β -d-glc

I

Rl

H

=O

H

H

H

S

[8]

28

Terreside B

I

Ra

H

=O

H

H

H

S

[19]

29

Terreside A

I

Ri

H

=O

H

H

H

R

[19]

30

Tettestrosin C

I

Rf

H

=O

H

H

H

R,S

[11, 13]

31

25R,S-5α-spiro-12-one-3-O-β -d-xyl-(1 → 2)-[β -d-xyl-(1 → 3)]-β -d-glc(1 → 4)-[α -l-rha(1 → 2)]-β -d-gal

I

Re

H

=O

H

H

H

R,S

[20]

32

Hecogenone

I

=O

H

=O

H

H

H

R

[7]

33

25R-5α-spiro-3,6,12-triketo

I

=O

H

=O

=O

H

H

R

[7]

34

Sarsasaponin

I

OH

H

H

H

H

H

S

[21]

35

Isoterrestrosin B(I)

I

Rg

H

H

H

H

H

S

[21]

36

Chlorogenin

I

OH

H

H

OH

H

H

R

[22]

37

Terrestrinin U

I

H

Rm

H₂

H

Rl

H

S

[23]

38

Terrestrinin I

I

Ra

H

=O

H

Rl

H

S

[24]

39

23S,25S-5α-spiro-24-one-3β,23-diol-3-O-[α -l-rha-(1 → 2)]-O-[β -d-glc-(1 → 4)]-β -d-gal

I

Rn

H

H

H

=O

OH

S

[25]

40

24S,25S-5α-spiro-3β,24-diol-3-O-[α -l-rha-(1 → 2)]-O-[β -d-glc-(1 → 4)]-β -d-gal

I

Rn

H

H

H

OH

H

S

[25]

41

23S,24R,25R-5α-spiro-3β,23,24-triol-3-O-[α -l-rha-(1 → 2)]-[β -d-glc-(1 → 4)]-β -d-gal

I

Rn

H

H

H

OH

OH

R

[26]

42

23S,24R,25S-5α-spiroe-3β,23,24-triol-3-O-[α -l-rha-(1 → 2)-[β -d-glc-(1 → 4)]-β -d-gal

I

Rn

H

H

H

OH

OH

S

[26]

43

Diosgenin

II

OH

H

R

[14]

44

Yamogenin

II

OH

H

S

[10]

45

Trillin

II

Rl

H

R

[27]

46

Trillarin

II

Ro

H

R

[27]

47

Dioscin

II

Rp

H

R

[28]

48

Gracillin

II

Rq

H

R

[27]

49

Diosgenin-3-O-α -l-rha-(1 → 3)-β -d-glc

II

Rr

H

R

[27]

50

Tribestin

II

Rs

H

R

[28]

51

Ruscogenin

II

OH

OH

R

[14]

52

Saponin C

II

OH

Rt

R

[29]

53

25R-spiro-3,5-diene

III

H

R

[14]

54

25R-spiro-3,5-dien-12one

III

=O

R

[17]

55

25R-spiro-4-ene-3,12-dione

IV

=O

H

H

H

R

[7, 17]

56

25R-spiro-4-ene-3,6,12-trione

IV

=O

H

=O

H

R

[7]

57

25R-spiro-24-hydroxy-3,12-dione

IV

=O

H

H

OH

R

[17]

58

25R-spiro-2α,3β-hydroxy-4-ene-12one

IV

OH

OH

H

H

R

[17]

59

25R-5α-furo-22-methoxy-3β,26-dihydroxy-O-β -d-glc-3-O-β -d-xyl-(1 → 2)-[β-d-xyl-(1 → 3)]-β -d-glc(1 → 4)-[α -l-rha(1 → 2)]-β -d-gal (J)

V

Re

H

H

OCH₃

Rl

R

[9, 12, 21]

60

Neoprotodioscin

V

Rp

H

H

OH

Rl

R

[29]

61

Neoprototribestin

V

Rs

H

H

OH

Rl

R

[24]

62

Terrestrinin B

V

Re

H

H

OH

Rl

S

[12]

63

Tettestrosin H

V

Rf

H

H

OH

Rl

R,S

[16]

64

Terrestroneoside A

V

Re

H

H

OCH₃

Rl

Uncertain

[30]

65

Terrestrosin F

V

Ra

OH

H

OH

Rl

R

[16]

66

25R,S-5α-furo-2α,3β,22α,26-tetrahydroxy-O-β -d-glc-(1 → 4)-β -d-gal

V

Ra

OH

H

OH

Rl

R,S

[16]

67

Terrestrosin G

V

Rf

OH

H₂

OH

Rl

R,S

[16]

68

25R,5α-furo-12-one-3β,22α,26-trihydroxy-O-β -d-glc-3-O-β -d-glc-(1 → 2)-β -d-gal

V

Ru

H

=O

OH

Rl

R

[31]

69

25S,5α-furo-12-one-3β,22α,26-trihydroxy-O-β -d-glc-3-O-β -d-glc-(1 → 2)-β -d-gal

V

Ru

H

=O

OH

Rl

S

[20]

70

25S,5α-furo-12-one-3β,22α,26-trihydroxy-O-β -d-glc-3-O-β -d-glc-(1 → 4)-[α -l-rha-(1 → 2)]-β -d-gal

V

Rg

H

=O

OH

Rl

S

[20]

71

Terrestrosin I

V

Rf

H

=O

OH

Rl

R,S

[16]

72

5α-furo-12-one-3β,22,26-trihydroxy-O-β -d-glc-3-O-β -d-xyl-(1 → 3)-[β -d-gal-(1 → 2)]-β -d-glc(1 → 4)-β -d-glc

V

Rv

H

=O

OH

Rl

Uncertain

[18]

73

Terrestrinin R

V

H

Rm

=O

OH

Rl

R

[23]

74

Terrestrinin S

V

H

Rm

=O

OH

Rl

S

[23]

75

Terrestrinin F

V

OH

H

=O

OH

Rl

R

[24]

76

26-O-β -d-glc-25R-5α-furo-2α,3β,22α,26-tetraol-3-O-β -d-glc-(1 → 2)-O-β -d-glc-(1 → 4)-β -d-gal

V

Ri

OH

H

CH₃

Rl

R

[25]

77

Pseudoprotodioscin(K)

VI

Rp

OH

H

Rl

R

[21]

78

Methyl pseudo-diosgenin

VI

Rp

OCH₃

H

Rl

R

[32]

79

Prototribestin

VI

Rs

OH

H

Rl

R

[32]

80

Methyprototribestin

VI

Rs

OCH₃

H

Rl

R

[32]

81

Protogracillin

VI

Rq

OH

H

Rl

R

[8]

82

Terrestrosin J

VI

Rf

OH

H

Rl

R,S

[16]

83

Tribol

VI

Rp

H

OH

H

R

[28]

84

Terrestrinin K

VI

Rm

OH

H

Rl

R

[23]

85

Terrestrosin K

VII

Rf

H

=O

H

CH₃

R

[16]

86

25R,S-5α-furo-12-one-20,22-ene-3β,26-dihydroxy-O-β -d-glc-3-O-β -d-glc-(1 → 4)-β -d-gal

VII

Ra

H

=O

H

CH₃

Rl

R,S

[31]

87

25R,S-5α-furo-12-one-20,22-ene-3β,26-dihydroxy-O-β -d-gal-(1 → 2)-β -d-glc-(1 → 4)-β -d-gal

VII

Rf

H

=O

H₂

CH₃

Rl

R,S

[16]

88

5α-furo-12-one-20,22-ene-3β,26-dihydroxy-O-β -d-glc-3-O-β -d-xyl-(1 → 3)-[β -d-gal-(1 → 2)]-β -d-glc-(1 → 4)-β -d-glc

VII

Rv

H

=O

H₂

CH₃

Rl

Uncertain

[18]

89

Tribulosaponin A(L)

VII

Rp

H

H

H₂

CH₃

Rl

S

[21]

90

Tribulosaponin B(M)

VII

Rg

H

H

H₂

CH₃

Rl

S

[21]

91

26-O-β -d-glc-25R-5α-furo-20(22)-en-2α,3β,26-triol-3-O-β -d-glc-(1 → 2)-O-β-glc-(1 → 4)-β -d-gal

VII

Rn

H

=O

H

OCH₃

Rl

R

[25]

92

26-O-β -d-glc-25R-5α-furo-12-one-3β,22α,26-triol-3-O-β -d-glc-(1 → 2)-β -d-glc-(1 → 4)-β -d-gal

VII

Ri

H

=O

H

OH

Rl

R

[33]

93

26-O-β -d-glc-25S-5α-furo-22-methoxy-2α,3β, 26-triol-3-O-β -d-glc-(1 → 2)-β -d-glc-(1 → 4)-β -d-gal

VII

Ri

OH

H

H

OCH₃

Rl

S

[33]

94

Terrestrinin A

VIII

Rl

S

[12]

95

Terrestrinin Q

VIII

Rl

R

[23]

96

Terrestrinin C

IX

OH

OH

=O

H₂

Rl

R

[24]

97

Terrestrinin D

IX

=O

H

=O

H₂

Rl

R

[24]

98

Terrestrinin E

IX

=O

H

=O

=O

Rl

R

[24]

99

Terrestrinin G

IX

=O

H

OH

H₂

Rl

R

[24]

100

Terrestrinin H

IX

=O

H

=O

H₂

Rv

R

[24]

101

Terrestrinin J

X

Rm

OH

Rl

R

[23]

102

Terrestrinin L

XI

Rm

OH

Rl

R

[23]

103

Terrestrinin M

XI

Rx

OH

Rl

R

[23]

104

Terrestrinin N

XI

Ry

OH

Rl

R

[23]

105

Terrestrinin O

XII

Ry

H

Rl

R

[23]

106

26-O-β -d-glc-25R-5α-furo-20(22)-en-2α,3β, 26-triol-3-O-β -d-glc-(1 → 2)-O-β -d-glc-(1 → 4)-β -d-gal

XII

Ri

OH

Rl

R

[25]

107

Terrestrinin P

XIII

Rm

Rl

R

[23]

108

Terrestrinin T

XIV

Rm

Rl

R

[23]