1995 Volume 43 Issue 5 Pages 771-776
Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C35H52O9, mp 260-262°C, [α]D -43.5°, cimicifugoside H-2 (2), C35H54O10, mp 227-229°C, [α]D -38.8°, and cimicifugoside H-5 (3), C35H52O10, mp 262-264°C, [α]D -22.9°, together with known glycosides, actein and 27-deoxyactein. Their structures were determined on the basis of chemical and spectrometric evidence including an X-ray crystallographic analysis. The structure of cimicifugoside H-1 (1) was established as (20R, 24R)-24, 25-epoxy-11β-hydroxy-3-β-(β-D-xylopyranosyloxy)-9, 19-cyclolanost-7-ene-16, 23-dione. Cimicifugoside H-5 (3) is the 15-hydroxylated derivative of 1. Since 1 changed into cimicifugoside H-2 (2) on treatment with p-toluenesulfonic acid, 2 has a 24R, 25-diol structure derived from 1 by opening its epoxy ring.