Stereoisomeric Composition of Natural Myrtucommulone A

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• 作者：Marcus Hans ; Ma毛l Charpentier ; Volker Huch ; Johann Jauch ; Torsten Bruhn ; Gerhard Bringmann ; Dietmar Quandt
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：October 23, 2015
• 年：2015
• 卷：78
• 期：10
• 页码：2381-2389
• 全文大小：486K
• ISSN：1520-6025

文摘

Myrtucommulone A (MC A) (1), isolated from Myrtus communis (myrtle), shows the same pharmacological activity for inhibition of inflammation and induction of apoptosis as synthetic MC A, which consists of three stereoisomers, i.e., two enantiomers and one meso form. This led to the question of whether the natural MC A is a pure stereoisomer or a mixture of stereoisomers. The specific rotation and electronic circular dichroism (ECD) data of natural MC A (1) as well as of a pentacyclic derivative 4 revealed that naturally occurring MC A (1) consists of the racemate and the meso form in a 1:1 ratio. A probable precursor of MC A (1), nor-semimyrtucommulone (5), was also isolated from myrtle as a racemate. The absolute configurations of the enantiomers of 1 and 5 were determined using a combination of experimental and quantum-chemical calculated ECD spectra.