Steroidal Glycosides from Reineckia carnea herba and Their Antitussive Activity

Abstract

Two new steroidal glycosides, 1α,3α-dihydroxy-5β-pregn-16-en-20-one 3-O-α-L-rhamnopyranoside (1) and 1β,3β,27-trihydroxycholest-16-en-22-one 1,3-di-O-α-L-rhamnoside (2), along with seven known steroidal glycosides (3–9), were isolated from Reineckia carnea herba. Their structures were determined by detailed analysis of their 1D- and 2D-NMR and MS spectra. Compound 9 was isolated for the first time from the Reineckia genus. Except for 8, compounds 2, 3, 4, 5, 6, 7, and 9 displayed clear in vitro antitussive activity.

Key words

Reineckia carnea - Liliaceae - steroidal glycosides - antitussive

• References

• 1 Zhang Y, Du J, Qiu DW. Overview of the research of Miao drug Reineckia carnea . J Guiyang Coll Tradit Chin Med 2003; 11: 205
• 2 Han N, Chang CL, Wang YC, Huang T, Liu ZH, Yin J. The in vivo expectorant and antitussive activity of extract and fractions from Reineckia carnea . J Ethnopharmacol 2010; 131: 220-223
• 3 Zhang Y, Du J, Xu JY, Wang L, Zhang LP. Pharmacological study of total saponins from Reineckia carnea on hemolysis, relieving a cough, abolishing phlegm and anti-inflammation. Med J Chin People Armed Police Forces 2006; 17: 282-284
• 4 Xu X, Zheng FH. Chemical constituents in aerial part of Reineckia carnea . China J Chin Mater Med 2008; 33: 2347-2349
• 5 Zhou X, Liu H, Zhao C, Gong XJ, Zhang JX. Studies on chemical constituents of herbs of Reineckia carnea . China J Chin Mater Med 2008; 33: 2794-2796
• 6 Mimaki Y, Takaashi Y, Kuroda M, Sashida Y. Steroidal glucosides from leaves of Cordyline stricta . Phytochemistry 1997; 45: 1229-1234
• 7 Agrawai PK, Jain DC, Gufta RK, Thakur RS. Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry 1985; 24: 2479-2496
• 8 Ohtsuki T, Koyano T, Kowithayakorn T, Sakai S, Kawahara N, Goda Y, Yamaguchi N, Ishibashi M. New chlorogenin hexasaccharide isolated from Agave fourcroydes with cytotoxic and cell cycle inhibitory activities. Bioorg Med Chem 2004; 12: 3841-3845
• 9 Zhang ZQ, Chen JC, Yan J, Qiu MH. Three steroids with unique structural feature of 5β-spirostan-1β,3β,17α-trihydroxyl from Reineckia carnea . Chem Pharm Bull 2011; 59: 53-56
• 10 Zhang ZQ, Chen JC, Zhou L, Qiu MH. Two new cholestane bisdesmosides from Reineckia carnea . Helv Chim Acta 2007; 90: 612-622
• 11 Liu H, Xiong Z, Li F, Qu G, Kobayashi H, Yao X. Two new pregnane glycosides from Dioscorea futschauensis R. KUNTH. Chem Pharm Bull 2003; 51: 1089-1091
• 12 Konishi T, Kiyosawa S, Shoji J. Studies on the constituents of Aspidistra elatior Blume. II. On the steroidal glycosides of the leaves. Chem Pharm Bull 1984; 32: 1451-1460
• 13 Zhang ZQ, Chen JC, Zhang XM, Li ZR, Qiu MH. Two new spirostanol saponins from Reineckia carnea . Helv Chim Acta 2008; 91: 1494-1499
• 14 Liu H. Study on the chemical constituents of Reineckia carnea [dissertation]. Guizhou: Guizhou University; 2008
• 15 Kanmoto T, Mimaki Y, Sashida Y, Nikaido T, Koike K, Ohmoto T. Steroidal constituents from the underground parts of Reineckea carnea and their inhibitory activity on cAMP phosphodiesterase. Chem Pharm Bull 1994; 42: 926-931
• 16 Li S, Wang D, Kuang HX. Chemical constituents study on Gymnadenia conopsea . Chin Tradit Herb Drugs 2001; 32: 18