Novel isolation of stilbenoids with enantiomeric and meso forms from a cyperus rhizome

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• 作者：Tetsuro Ito ; ^{teito@gifu-pu.ac.jp} ; Hidetatsu Endo ; Masayoshi Oyama ; Munekazu Iinuma
• 关键词：Absolute structure ; Racemate ; Meso compound ; Stilbene trimer ; Cyperus rhizome ; Optical separation
• 刊名：Phytochemistry Letters
• 出版年：2012
• 期刊代码：P8_18743900
• 类别：abs
• 出版时间：June, 2012
• 卷：5
• 期：2
• 页码：267-270
• 文件大小：324 K

摘要

Three stereoisomeric stilbene trimers bearing an (E)-2,3,5,6-tetraphenyl-4-styryl-2,3,5,6-tetrahydrobenzo[1,2-b:5,4-b鈥瞉difuran skeleton, (+)- and (鈭?-(E)-cyperusphenol A (1, 2) and (E)-mesocyperusphenol A (3), were isolated from a cyperus rhizome. Moreover, the geometrical isomers (4-6) were identified as the artifacts of their (E)-forms (1-3). The isolated products are the first instance of the co-occurrence of racemates (1, 2: new compounds) and a meso isomer (3), which resembles the C₂ symmetrical structure of an oligostilbenoid. These structures were characterized by NMR and CD spectroscopy. This is the first report that shows the occurrence of a racemate of a stilbenoid in the same plant material and the achievement of the optical separation of stilbene oligomers.