Subscribe to RSS
DOI: 10.1055/s-0031-1280373
© Georg Thieme Verlag KG Stuttgart · New York
Spirostanol Saponins Derivated from the Seeds of Trigonella foenum-graecum by β-Glucosidase Hydrolysis and Their Inhibitory Effects on Rat Platelet Aggregation
Publication History
received July 23, 2011
revised October 19, 2011
accepted October 31, 2011
Publication Date:
29 November 2011 (online)

Abstract
Nine spirostanol saponins (1–9) and seven mixtures of 25R and 25S spirostanol saponin isomers (10–16) were obtained from the seeds of Trigonella foenum-graecum after enzymatic hydrolysis of the furostanol saponin fraction by β-glucosidase. Their structures were determined by NMR and MS spectroscopy. Among them, 1-4, 6, 8, and 9 were new compounds and five, 11b, 12a, 13b, 14a, and 14b, were new structures observed from seven mixtures. In addition, the inhibitory effects of all saponins on rat platelet aggregation were evaluated.
Key words
Trigonella foenum-graecum - Leguminosae - spirostanol saponins - enzymatic hydrolysis - inhibitory platelet aggregation activity
References
- 1 The Pharmacopoeia Commission of PRC .Pharmacopoeia of the People's Republic of China. 2010 edition, Volume 1 Beijing: China Medical Science Press; 2010: 225-226
MissingFormLabel
- 2
Gupta R K, Jain D C, Thakur R S.
Furostanol glycosides from Trigonella foenum-graecum seeds.
Phytochemistry.
1984;
23
2605-2607
MissingFormLabel
- 3
Gupta R K, Jain D C, Thakur R S.
Trigofoenoside E-1, a new furostanol saponin from Trigonella foenum-graecum.
Indian J Chem Sect B.
1985;
24
1215-1217
MissingFormLabel
- 4
Gupta R K, Jain D C, Thakur R S.
Furostanol glycosides from Trigonella foenum-graecum seeds.
Phytochemistry.
1985;
24
2399-2401
MissingFormLabel
- 5
Gupta R K, Jain D C, Thakur R S.
Two furostanol saponins from Trigonella feonum-graecum.
Phytochemistry.
1986;
25
2205-2207
MissingFormLabel
- 6
Yoshikawa M, Murakami T, Komatsu H, Murakami N, Yamahara J, Matsuda H.
Medicinal food stuffs. IV. Fenugreek seed. (1): structures of trigoneosides Ia, Ib,
II a, II b, III a, III b, new furostanol saponins from the seeds of Indian Trigonella foenum-graecum L.
Chem Pharm Bull.
1997;
45
81-87
MissingFormLabel
- 7
Yoshikawa M, Murakami T, Komatsu H, Yamahara J, Matsuda H.
Medicinal food stuffs. VIII. Fenugreek seed. (2): structures of trigoneosides IV a,
Va, Vb, VI, VII b and VIII b from the seeds of Indian Trigonella foenum-graecum L.
Heterocycles.
1998;
47
397-405
MissingFormLabel
- 8
Murakami T, Kishi A, Matsuda H, Yoshikawa M.
Medicinal food stuffs. XVII. Fenugreek seed. (3): structures of new furostanol type
steroidal saponins, trigoneosides Xa, Xb, XI b, XII a, XII b and XIII a from the seeds
of Egyptian Trigonella foenum-graecum L.
Chem Pharm Bull.
2000;
48
994-1000
MissingFormLabel
- 9
Fu Y L, Yu Z Y, Tang X M, Zhao Y, Yuan X L, Wang S, Ma B P, Cong Y W.
Pennogenin glycosides with a spirostanol structure are strong platelet agonists: structural
requirement for activity and mode of platelet agonist synergism.
J Thromb Haemost.
2008;
6
524-533
MissingFormLabel
- 10
Guo L, Su J, Deng B W, Yu Z Y, Kang L P, Zhao Y, Shan Y J, Chen J P, Ma B P, Cong Y W.
Active pharmaceutical ingredients and mechanisms underlying phasic myometrial contractions
stimulated with the saponin extract from Paris polyphylla Sm. var. yunnanensis used for abnormal uterine bleeding.
Hum Reprod.
2008;
23
964-971
MissingFormLabel
- 11
Mitaine-Offer A C, Pénez N, Miyamoto T, Delaude C, Mirjoletd J F, Duchamp O, Lacaille-Dubois M A.
Acylated triterpene saponins from the roots of Securidaca longepedunculata.
Phytochemistry.
2010;
71
90-94
MissingFormLabel
- 12
Agrawal P K, Jain D C, Gupta R K, Thakur R S.
Carbon-13NMR spectroscopy of steroidal saponins and steroidal saponins.
Phytochemistry.
1985;
24
2479-2496
MissingFormLabel
- 13
Kudo K, Miyahara K, Marubayashi N, Kawasaki T.
Characterization of a mini compound, which accompanies the usual 22α (R)-O, 25β (S)-spirostanol glycoside, as a novel type of 22β (R)-O, 25α (S) analog.
Chem Pharm Bull.
1984;
32
4229-4232
MissingFormLabel
- 14
Agrawal P K.
NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides.
Phytochemistry.
1992;
31
3307-3330
MissingFormLabel
- 15
Hayes P Y, Jahidin A H, Lehmann R, Penman K, Kitching W, De-Voss J J.
Steroidal saponin from the root of Asparagus racemosus.
Phytochemistry.
1985;
69
796-804
MissingFormLabel
- 16
Pettit G R, Zhang Q W, Pinilla V, Hoffmann H, Knight J C, Doubek D L, Chapuis J C, Pettit R K, Schmidt J M.
Antineoplastic agents 534. Isolation and structure of sansevistatins 1 and 2 from
the African Sansevieria ehrenbergii.
J Nat Prod.
2005;
68
729-733
MissingFormLabel
- 17
Mimaki Y, Watanabe K, Sakagami H, Sashida Y.
Steroidal glycosides from the leaves of Cestrum nocturnum.
J Nat Prod.
2002;
65
1863-1868
MissingFormLabel
- 18
Yu H S, Zhang J, Kang L P, Han L F, Zou P, Zhao Y, Xiong C Q, Tan D W, Song X B, Yu K, Ma B P.
Three new saponins from the fresh rhizomes of Polygonatum kingianum.
Chem Pharm Bull.
2009;
57
1-4
MissingFormLabel
- 19
Shim S H, Lee E J, Kim J S, Kang S S, Ha H, Lee H Y, Kim C, Lee J H, Son K H.
Rat growth-hormone release stimulators from fenugreek seeds.
Chem Biodivers.
2008;
5
1753-1761
MissingFormLabel
- 20
Wang Y B, Zhang Y C, Zhu Z Y, Zhu S L, Li Y X, Li M, Yu B.
Exploration of the correlation between the structure, hemolytic activity, and cytotoxicity
of steroid saponins.
Bioorg Med Chem.
2007;
15
2528-2532
MissingFormLabel
- 21
Jin J M, Liu X K, Teng R W, Yang C R.
Enzymatic degradation of parvifloside.
Acta Bot Sin.
2002;
44
1243-1249
MissingFormLabel
- 22
Zheng Q A, Zhang Y J, Li H Z, Yang C R.
Steroidal saponins from fresh stem of Dracaena cochinchinensis.
Steroids.
2004;
69
111-119
MissingFormLabel
1 These authors contributed equally to this work.
Prof. Dr. Bai-Ping Ma
Department of Biotechnology
Beijing Institute of Radiation Medicine
No. 27 Taiping Road, Haidian District
Beijing 100850
People's Republic of China
Phone: +86 10 68 21 00 77 Ext. 93 02 65
Fax: +86 10 68 21 46 53
Email: mabaiping@sina.com