Studies on the Chinese Crude Drug "Shoma."VI. Shengmanol Xyloside, a New Genuine Natural Product of Some Cimicifuga Glycosides

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Abstract
A new genuine natural product of Cimicifuga triterpenol glycoside, named shengmanol xyloside (7) C35H56O9, mp [melting point] 244-245.5.degree. C, .**GRAPHIC**. -10.2.degree., was isolated from the fresh underground parts of C. japonica. The xyloside (7) turned, on a mild treatment with p-toluenesulfonic acid in methanol, into 25-O-methylcimigenol xyloside (6). On enzymatic hydrolysis, 7 yielded its genuine genin, shengmanol (14), C30H48O5.cntdot.1/2H2O, mp 153.5-154.5.degree. C, .**GRAPHIC**. + 0.5.degree. C, which afforded cimigol (17) on alkali treatment. The xyloside (7) afforded a pentaacetate (16), which was identical with the peracetate of acetyl shengmanol xyloside (2). On the basis of chemical and spectral data, the structure of shengmanol xyloside (7) was proposed to be (23R, 24S)-3.beta.,15.alpha.,16.alpha.-trihydroxy-16,23;24,25-diepoxy-9,19-cyclolanostane 3-O-.beta.-D-xylopyranoside. The contents of cimigenol xyloside (1), acetyl shengmanol xyloside (2), 24-O-acetyl-hydroshengmanol xyloside (3) and shengmanol xyloside (7) in the fresh underground parts of C. japonica were estimated on the basis of the high-performance liquid chromatography equipped with a RI [refractive index] detector. The total content of 2, 3 and 7 was .apprx. 2 1/2 times as much as that of 1, suggesting that the chemically unstable xylosides 2, 3 and 7 are genuine glycosides of some Cimicifuga triterpenol xylosides such as 1 and 6.

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