Koeda M, Aoki Y, Sakurai N, Nagai M
Faculty of Pharmaceutical Sciences, Hoshi University, Tokyo, Japan.
Chem Pharm Bull (Tokyo). 1995 May;43(5):771-6. doi: 10.1248/cpb.43.771.
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.
从一批市售升麻根茎中分离出三种新的环羊毛甾烷醇木糖苷，升麻糖苷H-1（1），C35H52O9，熔点260 - 262℃，[α]D -43.5°；升麻糖苷H-2（2），C35H54O10，熔点227 - 229℃，[α]D -38.8°；升麻糖苷H-5（3），C35H52O10，熔点262 - 264℃，[α]D -22.9°，以及已知糖苷，升麻素和27 - 脱氧升麻素。它们的结构是根据化学和光谱证据包括X射线晶体学分析确定的。升麻糖苷H-1（1）的结构确定为（20R，24R）-24,25 - 环氧 - 11β - 羟基 - 3 - β -（β - D - 吡喃木糖氧基）-9,19 - 环羊毛甾 - 7 - 烯 - 16,23 - 二酮。升麻糖苷H-5（3）是1的15 - 羟基化衍生物。由于1在用对甲苯磺酸处理时转变为升麻糖苷H-2（2），所以2具有通过打开其环氧环由1衍生而来的24R，25 - 二醇结构。
