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从其 4-O-乙酰衍生物的实验和预测手性光学研究推断出茵芋苷 D 中 seco-桉烷内酯的绝对构型。

Absolute configuration of seco-eudesmanolide inuloxin D from experimental and predicted chiroptical studies of its 4-O-acetyl derivative.

机构信息

Department of Chemistry, Vanderbilt University, Nashville, Tennessee, USA.

Department of chemical Sciences, University of Naples Federico II, Naples, Italy.

出版信息

Chirality. 2021 May;33(5):233-241. doi: 10.1002/chir.23301. Epub 2021 Feb 17.

DOI:10.1002/chir.23301
PMID:33598968
Abstract

Sesquitepenoids inuloxins A-D, belonging to different subgroups, were isolated from Dittrichia viscosa and showed potential biocontrol of some parasitic plants as Pelipanche, Orobanche, and Cuscuta species. The absolute configurations of the first three inuloxins A-C were previously determined by using experimental and computational chiroptical spectroscopic methods. The absolute configuration of inuloxin D remains to be established. The bioactive inuloxin E, closely related to inuloxin D, was recently isolated from the same plant organic extract. The same relative configuration of inuloxin D was assigned to inuloxin E by comparison of their NMR spectroscopic data. The absolute configurations of inuloxin D and inuloxin E are suggested in this work by analysis of the experimental and predicted chiroptical properties of the 4-O-acetyl derivative of inuloxin D.

摘要

倍半帖烯类独丽花素 A-D,分属于不同的亚组,从独丽花中分离得到,对列当、肉苁蓉和菟丝子等寄生植物具有潜在的生物防治作用。前三个独丽花素 A-C 的绝对构型先前通过使用实验和计算手性光谱方法确定。独丽花素 D 的绝对构型仍有待确定。最近从同一植物有机提取物中分离到与其密切相关的生物活性独丽花素 E。通过比较它们的 NMR 光谱数据,将独丽花素 E 的相对构型分配给独丽花素 D。通过分析独丽花素 D 的 4-O-乙酰衍生物的实验和预测的手性性质,本工作提出了独丽花素 D 和独丽花素 E 的绝对构型。

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