Steroids from the Roots ofCynanchum 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.

Peroxy natural products

“…The compound showed dosedependent relaxation on aortic rings with endothelium contracted by phenylepherine or KCI. 396 The structures of a series of peroxy function containing pregnane glycosides including periperoxides A-E 635-639 397 and previously reported periplocosides A-K 398,399 have been revised to be orthoester group bearing ones using 2D NMR techniques as well as chemical transformations and X-ray crystallographic diffraction analysis. …”

Immunosuppressive C21 steroidal glycosides from the root of Cynanchum atratum

“…The molecular formula of 6 was deduced as C 28 (Tables 1, 3) were consistent with those of anhydrohirundigenin, a more primitive and unusual pregnane skeleton than glaucogenin C in the view of biogenetic pathway [26,28,30]. A β-D-oleandropyranose unit was confirmed by 1 H, 1 H-COSY, HSQC, and NOESY experiments and the acid hydrolysis as described in Sections 2.4 and 2.5.…”

Three New Steroidal Glycosides from the Roots ofCynanchum stauntonii

“…The known compound anhydrohirundigenin monothevetoside ( 4 ) [1] was identified by comparison of their spectroscopic data ( 1 H and 13 C NMR, MS) with the literature values.…”

“…The dried-up roots of C. stauntonii , along with that of another species of the same genus, C. glaucescens (Decne.) Hand.-Mazz., has been used as antitussives and expectorants to treat diseases in the history of China [1]. Both of which are given the name of “Bai-qian” in traditional Chinese medicine (TCM) [2].…”

“…It is known that C 21 steroids and their glycosides are of considerable bioactivities, such as hypolipidemic and antitumor activities. However, chemical investigation into the title plant is very rare up to now with, to the best of our knowledge, only three papers have reported several steroids, including four ones by our group eight years ago [1]. The ongoing investigations in our group intend to enrich the information about the chemical constituents and their bioactivities of this plant which has led to the isolation and elucidation of some known and new steroidal glycosides [5].…”