Planta Med 2013; 79(12): 1063-1067
DOI: 10.1055/s-0032-1328719
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

New 23-Spirocholestane Derivatives from Ypsilandra thibetica

Bai-Bo Xie
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
,
Chang-Xiang Chen
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
,
Yong-Hui Guo
2   Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing, P. R. China
,
Yu-Ye Li
3   Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, P. R. China
,
Ya-Juan Liu
3   Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, P. R. China
,
Wei Ni
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
,
Liu-Meng Yang
3   Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, P. R. China
,
Ning-Bo Gong
2   Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing, P. R. China
,
Yong-Tang Zheng
3   Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, P. R. China
,
Rui-Rui Wang
3   Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences & Yunnan Province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, P. R. China
,
Yang Lü
2   Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing, P. R. China
,
Hai-Yang Liu
1   State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
› Author Affiliations
Further Information

Publication History

received 23 January 2013
revised 10 May 2013

accepted 20 May 2013

Publication Date:
01 July 2013 (online)

Abstract

Three new unusual 23-spirocholestane derivatives, ypsilanogenin (1), ypsilanogenin 3-O-β-D-glucopyranoside (2), and 4′-acetylypsilanogenin 3-O-β-D-glucopyranoside (3), were isolated from the whole plants of Ypsilandra thibetica. The structures of compounds 13 were deduced by spectroscopic and chemical methods, and the structure of 1 was further confirmed by a single-crystal diffraction analysis. All isolates were evaluated for their inhibitory activities against HIV-1.

Supporting Information

 
  • References

  • 1 Hou KZ. Dictionary of the families and genera of Chinese seed plants. 2nd. edition. Beijing: Science Press; 1982: 521-522
  • 2 Jiangsu New Medicinal College. Dictionary of traditional Chinese materia medica. Shanghai: Shanghai Scientific and Technological Press; 1977: 1841-1841
  • 3 Yunnan Food and Drug Administration. The Yunnan Chinese materia medica standards, Volume 6 (Yi Nationality Medicine, III). Kunming: Yunnan Scientific and Technological Press; 2010: 5-6
  • 4 Xie BB, Liu HY, Ni W, Chen CX, Lü Y, Wu L, Zheng QT. Five new steroidal compounds from Ypsilandra thibetica . Chem Biodivers 2006; 3: 1211-1218
  • 5 Xie BB, Liu HY, Ni W, Chen CX. Ypsilandrosides C–G, five new spirostanol saponins from Ypsilandra thibetica . Steroids 2009; 74: 950-955
  • 6 Lu Y, Chen CX, Ni W, Hua Y, Liu HY. Spirostanol tetraglycosides from Ypsilandra thibetica . Steroids 2010; 75: 982-987
  • 7 Lu Y, Xie BB, Chen CX, Ni W, Hua Y, Liu HY. Ypsilactosides A and B, two new C22-steroidal lactone glycosides from Ypsilandra thibetica . Helv Chim Acta 2011; 94: 92-97
  • 8 Liu HY, Chen CX, Lu Y, Yang JY, Ni W. Steroidal and pregnane glycosides from Ypsilandra thibetica . Nat Prod Bioprospect 2012; 2: 11-15
  • 9 Zhang XD, Chen CX, Yang JY, Ni W, Liu HY. New minor spirostane glycosides from Ypsilandra thibetica . Helv Chim Acta 2012; 95: 1087-1093
  • 10 Hara S, Okabe H, Mihashi K. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates. Chem Pharm Bull 1987; 35: 501-506
  • 11 Shingu K, Mito K, Yahara S, Nohara T, Ono M, Kawasaki T, Nakano K, Tomimatsu T, Haratake M, Marubayashi N, Ueda I. A novel cholestane derivative as root growth inhibitor from Heloniopsis japonica . Tetrahedron Lett 1992; 33: 2529-2530
  • 12 Sheldrick GM. SHELXL97, Program for crystal structure solution. Göttingen: University of Göttingen; 1997
  • 13 Wang RR, Yang LM, Wang YH, Pang W, Tam SC, Tien P, Zheng YT. Sifuvirtide, a potent HIV fusion inhibitor peptide. Biochem Biophys Res Commun 2009; 382: 540-544