Stereochemistry of flavonoidal alkaloids from Dracocephalum rupestre
Stereochemistry of flavonoidal alkaloids from Dracocephalum rupestre
复制标题
青兰黄酮生物碱的立体化学
DOI：
10.1016/j.phytochem.2008.01.013
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发表时间：
2008-04-01
期刊：
影响因子：
3.8
通讯作者：
Lou, Hong-Xiang
中科院分区：
文献类型：
--
作者：
Ren, Dong-Mei;Guo, Huai-Fang;Lou, Hong-Xiang
通过对岩生青兰地上部分的植物化学研究，分离得到四组黄酮类生物碱，即青兰素A-D。根据大量的光谱分析，它们被鉴定为黄烷酮与吡咯烷-2-酮的缀合物。这两个立体中心使每组的龙头素同时成为两对映体。所有的16个异构体被成功地通过手性HPLC分离，并确定其立体化学特征的CD数据和单晶X-射线衍射分析的一个立体异构体。推广了两个立体中心的手性贡献的相加关系。通过减去它们各自的贡献，提出了吡咯烷-2-酮环中手性碳的CD贡献。(C)2008爱思唯尔有限公司版权所有。
Phytochemical studies on the aerial parts of Dracocephalum rupestre led to the isolation of four groups of flavonoidal alkaloids, dracocephins A-D. They were elucidated as conjugates of flavanone with pyrrolidin-2-one on the basis of extensive spectroscopic analysis. The two stereogenic centers rendered each group of the dracocephins as two pairs of enantiomers simultaneously. All of the sixteen isomers were separated successfully by chiral HPLC and their stereochemical features were determined by their CD data and single-crystal X-ray diffraction analysis of one stereoisomer. The additive relation of the chiroptical contributions resulting from the two stereogenic centers was generalized. The CD contribution of the chiral carbon in the pyrrolidin-2-one ring was proposed by subtraction of their respective contributions. (C) 2008 Elsevier Ltd. All rights reserved.