New 23-Spirocholestane Derivatives from Ypsilandra thibetica

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 1–3 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.

Key words

Ypsilandra thibetica - Liliaceae - 23-spirocholestane glycosides - anti-HIV-1 activity

• 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