Article

Studies on the Chinese Crude Drug "Shoma." IX. Three Novel Cyclolanostanol Xylosides, Cimicifugosides H-1, H-2 and H-5, from Cimicifuga Rhizome.

Mamoru KOEDAFaculty of Pharmaceutical Sciences, Hoshi University, Tokyo, JapanYoshinobu AokiFaculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi UniversityNobuko SakuraiFaculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi UniversityMasahiro NagaiFaculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi University, Faculty of Phrmaceutical Sciences, Hoshi University

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Abstract

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.

Identifiers

DOI: 10.1248/cpb.43.771

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Cited by 40 references

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