Three New Saponins from Tribulus terrestris

Abstract

Three new steroidal saponins 1 - 3, together with five known steroidal saponins, L-mannitol and an inorganic salt were isolated from Tribulus terrestris L. (Zygophyllaceae). The structures of the new steroidal saponins were elucidated as hecogenin 3-O-β-xylopyranosyl(1→3)-β-glucopyranosyl(1→4)-β-galactopyranoside (1), hecogenin 3-O-β-glucopyranosyl(1→2)-β-glucopyranosyl(1→4)-β-galactopyranoside (2) and 3-O-{β-xylopyranosyl(1→2)-[β-xylopyranosyl(1→3)]-β-glucopyranosyl(1→4)-[α-rhamnopyranosyl(1→2)]-β-galactopyranosyl}-26-O-β-glucopyranosyl-22-methoxy-(3β,5α,25R)-furostan-3,26-diol (3). Structure elucidation was accomplished by 1D and 2D NMR spectra (¹³C-¹H COSY, HMQC, HMBC, ¹H-¹H COSY, TOCSY, and NOESY), mass spectrometry (FABMS, ESIMS) and chemical methods.

Key words

Tribulus terrestris - Zygophyllaceae - steroidal saponins

References

• 1 Jiangsu New Medical College.. Dictionary of Chinese Herbal Medicine,. pp. 1274-6, Shanghai People's Publishing House, China; 1977
• 2 Chui  S Z,, Liao  C X,, Jiao  Q P,, Zhu  H M,, Chen  S Y,, Chou  Z J.. Xinnao shutong for coronary heart disease in 41 patients.  New Drugs and Clinical Remedies. 1992;;  11 202-4
• 3 Lu  S B,, Lu  B J,, Shen  M Z,, Rong  Y Z.. The clinic report of Xinnao shutong on myocardial infarction.  Acta Universitatis Medicinalis Secondae Shanghai. 1994;;  14 (1) 78-9
• 4 Yang  X Y,, Hang  B F,, Jiang  R,, Yao  Y M,, Chen  H Z.. Xinnao shutong therapy in 50 patients with cerebral arteriosclerosis and the sequelae of cerebral thrombosis.  New Drugs and Clinical Remedies. 1991;;  10 92-5
• 5 Wang  Y,, Ohtani  K,, Kasai  R,, Yamasaki  K.. Steroidal saponins from fruits of Tribulus terrestris. .  Phytochemistry. 1997;;  45 811-7
• 6 Wu  G,, Jiang  S H,, Jiang  F X,, Zhu  D Y,, Wu  H M,, Jiang  S K.. Steroidal glycosides from Tribulus terrestris. .  Phytochemistry. 1996;;  42 1677-81
• 7 Wang  Y,, Ohtani  K,, Kasai  R,, Yamasaki  K.. Steroidal saponins from fruits of Tribulus terrestris. .  Phytochemistry. 1996;;  42 1417-22
• 8 Ren  Y J,, Chen  H S,, Yang  G J,, Zhu  H.. Isolation and identification of a new derivative of cinnamic amide from Tribulus terrestris. .  Acta Pharmaceutica Sinica. 1994;;  29 204-6
• 9 Wang  Y,, Lu  Y R.. Studies on the constituents of Tribulus terrestris. .  Xi Bei Yao Xue Za Zhi. 1990;;  5 (4) 14-7
• 10 Mahato  S B,, Sahu  N P,, Ganguly  A N,, Miyahara  K,, Kawasaki  T J.. Steroidal glycosides of Tribulus terrestris Linn.  Chem. Soc. Perkin Trans. I. 1981;;  2405-10
• 11 Xu  Y X,, Chen  H S,, Liu  W Y,, Gu  Z B,, Liang  H Q.. Two sapogenins from Tribulus terrestris. .  Phytochemistry. 1998;;  49 199-201
• 12 Zhao  P P,, Li  B M,, He  L Y.. Studies on the method of determination of combined sugars in glycosides.  Acta Pharmaceutica Sinica. 1987;;  22 70-4
• 13 Pant  G,, Sati  O P,, Miyahaha  K,, Kawasaki  T.. Spirostanol glycosides from Agave cantala. .  Phytochemistry. 1986;;  25 1491-4
• 14 Dong  J X,, Han  G Y.. The active constituents from Anemarrhena asphodeloides Bunge.  Acta Pharmaceutica Sinica. 1992;;  27 26-32
• 15 Li  X C,, Wang  D Z,, Yang  C R.. Steroidal saponins from Chlorophytum malayense. .  Phytochemistry. 1990;;  29 3893-8
• 16 Dirk  C,, Van Setten  G,, ten Hove  J,, Wiertz  J HJ,, Kamerling  J P,, van de Werken  G.. Multiple-stage tandem mass spectrometry for structural characterization of saponins.  Anal. Chem.. 1998;;  70 4401-9