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(-)-迷迭香醇的绝对立体结构重新研究:来自高山红景天的单萜糖苷、迷迭香苷、迷迭香苷A、B和C的结构

Reinvestigation of absolute stereostructure of (-)-rosiridol: structures of monoterpene glycosides, rosiridin, rosiridosides A, B, and C, from Rhodiola sachalinensis.

作者信息

Yoshikawa Masayuki, Nakamura Seikou, Li Xuezheng, Matsuda Hisashi

机构信息

Kyoto Pharmaceutical University, Kyoto, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2008 May;56(5):695-700. doi: 10.1248/cpb.56.695.

DOI:10.1248/cpb.56.695
PMID:18451561
Abstract

Three new (-)-rosiridol glycosides, rosiridosides A, B, and C, were isolated from the roots of Rhodiola sachalinensis together with rosiridin [(-)-rosiridol 1-O-beta-D-glucopyranoside]. In the course of the structure elucidation of those new glycosides, the absolute configuration of the 4-position in (-)-rosiridol was reinvestigated. On the basis of the application of the modified Mosher's method for (-)- and (+)-rosiridol derivatives, the absolute configuration of the 4-position in (-)-rosiridol should be revised to be S orientation from the recently assigned R form, so that the absolute stereostructures of rosiridosides A, B, and C and rosiridin were determined.

摘要

从库页红景天的根部分离出三种新的(-)-罗西瑞醇糖苷,即罗西瑞糖苷A、B和C,以及罗西瑞定[(-)-罗西瑞醇1-O-β-D-吡喃葡萄糖苷]。在对这些新糖苷进行结构解析的过程中,对(-)-罗西瑞醇中4位的绝对构型进行了重新研究。基于对(-)-和(+)-罗西瑞醇衍生物应用改进的莫舍尔方法,(-)-罗西瑞醇中4位的绝对构型应从最近指定的R构型修正为S构型,从而确定了罗西瑞糖苷A、B和C以及罗西瑞定的绝对立体结构。

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