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Table 1 Steroidal saponins (aglycones) in T. terrestris

From: A review of traditional pharmacological uses, phytochemistry, and pharmacological activities of Tribulus terrestris

No. Chemicals Aglycones R1 R2 R3 R4 R5 R6 25-C Refs.
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]
  1. Ra: O-β -d-Gal-(1 → 4)-β -d-Glc; Rb: O-Glc/Rha = 2:1; Rc: O-β -d-Gal-[(1 → 2)-β -d-Xyl]-(1 → 4)-β -d-Glc-(1 → 2)-β -d-Glc; Rd: O-β -d-Gal-(1 → 4)-β -d-Glc-[(1 → 3)-β -d-Xyl]-(1 → 2)-β-D—Glc; Re: O-β -d-Gal-[(1 → 2)-α -l-Rha]-(1 → 4)-β -d-Glc-[(1 → 3)-β -d-Xyl-(1 → 2)-β-Xyl; Rf: O-β -d-Gal-(1 → 4)-β -d-Glc-(1 → 2)-β -d-Gal; Rg: O-β -d-Gal-[(1 → 2)-α -l-Rha]-(1 → 4)-β -d-Glc; Rh: O-β -d-Gal; Ri: O-β-Gal-(1 → 4)-β-Glc-(1 → 2)-β -d-Glc; Rj: O-β -d-Gal-(1 → 4)-β -d-Glc-(1 → 3)-β -d-Xyl; Rk: O-β -d-Gal-(1 → 4)-β -d-Glc-[(1 → 2)-β -d-Gal]-(1 → 3)-β -d-Xyl; Rl: O-β -d-Glc; Rm: O-β -d-Gal-[(1 → 2)-α -l-Rha]-(1 → 4)-β -d-Glc-[(1 → 3)-β -d-Xyl]-(1 → 2)-β -d-Xyl; Rn: O-β -d-Gal-[(1 → 4)-β -d-Glc]–[(1 → 2)-α -l-Rha]; Ro: O-β -d-Glc-(1 → 2)-β -d-Glc; Rp: O-β -d-Glc-[(1 → 2)-α -l-Rha]-(1 → 4)-α -l-Rha; Rq: O-β -d-Glc-[(1 → 2)-α -l-Rha]-(1 → 3)-β -d-Glc; Rr: O-β -d-Glc-(1 → 3)-α -l-Rha; Rs: O-β -d-Glc-[(1 → 2)-α -l-Rha]-(1 → 4)-SO3Na; Rt: O-β -d-Glc-[(1 → 2)-α -l-Rha]-(1 → 6)-OAc; Ru: O-β -d-Gal-(1 → 2)-β -d-Glc; Rv: O-β -d-Glc-(1 → 4)-β -d-Glc-[(1 → 2)-β -d-Gal]-(1 → 3)-β -d-Xyl; Rw: O-β -d-Glc-(1 → 6)-β -d-G; Rx: O-β -d-Gal-(1 → 4)-β -d-Glc-[(1 → 3)-β -d-Xyl]-(1 → 2)-β -d-A; Ry: O-β -d-Gal-(1 → 4)-β -d-Glc-[(1 → 3)-β -d-Xyl]-(1 → 2)-β -d-Xyl