Steroids from the Roots of Cynanchum stauntonii

Abstract

A chemical investigation of the roots of Cynanchum stauntonii has resulted in the characterization of a new hydroperoxide with a 13,14 : 14,15-disecopregnane-type skeleton, named stauntonine (1), together with three related compounds, anhydrohirundigenin (2), anhydrohirundigenin monothevetoside (3), and glaucogenin-C mono-D-thevetoside (4). Their structures were established by spectroscopic methods, including X-ray crystallographic diffraction analysis of stauntonine that confirmed its relative stereochemistry. The compound 1 showed dose-dependent relaxation on aortic rings with endothelium contracted by phenylepherine or KCl

Key words

Cynanchum stauntonii - Asclepiadaceae - steroids - stauntonine - 13,14 : 14,15-disecopregnane - vasodilating activity

References

• 1 Xie Z W, Liu M L, Lou Z Q. Pharmacognostical studies of the Chinese drugs Pai-ch’ien and Pai-wei.  Acta Pharm Sinica. 1959;  7 175-88
• 2 Qiu S X, Zhang Z X, Zhou J. Steroidal glycosides from the root of Cynanchum versicolor .  Phytochemistry. 1989;  28 3175-8
• 3 Sugama K, Hayashi K, Mitsuhashi H, Kaneko K. Studies on the constituents of Asclepiadaceae plants. LXVI. The structures of three new glycosides, cynapanosides A, B, and C, from the Chinese drug ”Xu-Chang-Qing,” Cynanchum paniculatum Kitagawa.  Chem Pharm Bull. 1986;  34 4500-7
• 4 Qiu S X. Studies on the chemical constituents of Cynanchum stauntonii (Decne.) Schlt. ex Levl.  Journal of Chinese Materia Medica. 1994;  19 488-9
• 5 Kennard O, Fawcett J K, Watson D G, Ann Kerr K, Stockel K, Stocklin W. et al .Hirundigenin and anhydrohirundigenin, two natural 15-oxasteroids of plant origin. Chemical and X-ray investigation. Tetrahedron Lett 1968: 3799-804
• 6 Nakagawa T, Hayashi K, Mitsuhashi H. Studies on the constituents of Asclepiadaceae plants. LIII. The structures of glaucogenin-A, -B, and -C mono-D-thevetoside from the Chinese drug ”Pai-ch’ien,” Cynanchum glaucescens Hand-Mazz.  Chem Pharm Bull. 1983;  31 870-8
• 7 El-Feraly F S, Chan Y M. Peroxycostunolide and peroxyparthenolide: two cytotoxic germacranolide hydroperoxide from Magnolia grandiflora. Structural revision of verlotorin and artemorin. Tetrahedron Lett 1977: 1973-6
• 8 Lou H X, Li X, Zhu T R. C₂₁ steroidal constituents from Cynanchum hancockianum .  Acta Pharm Sinica. 1992;  27 595-602