Studies on the Chinese crude drug "shoma." IX. Three novel cyclolanostanol xylosides, cimicifugosides H-1, H-2 and H-5, from cimicifuga rhizome.
Three new cyclolanostanol xylosides were isolated from a batch of commercial Cimicifuga Rhizome, cimicifugoside H-1 (1), C35H52O9, mp 260-262 degrees C, [alpha]D -43.5 degrees, cimicifugoside H-2 (2), C35H54O10, mp 227-229 degrees C, [alpha]D -38.8 degrees, and cimicifugoside H-5 (3), C35H52O10, mp 262-264 degrees C, [alpha]D -22.9 degrees, 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-11 beta-hydroxy-3-beta-(beta-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.
Koeda
M
M
Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan.
Aoki
Y
Y
Sakurai
N
N
Nagai
M
M
D018712:Analgesics, Non-Narcotic / Q000737:chemistry*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D007810:Lanosterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification; D014315:Triterpenes
D018712:Analgesics, Non-Narcotic; D004365:Drugs, Chinese Herbal; D006027:Glycosides; D012503:Saponins; D014315:Triterpenes; C010807:xylosides; D007810:Lanosterol; C096066:26-deoxyactein; C031436:cimicifugoside; C096064:actein