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Absolute configuration of seco‐eudesmanolide inuloxin D from experimental and predicted chiroptical studies of its 4‐O‐acetyl derivative
Chirality ( IF 2 ) Pub Date : 2021-02-17 , DOI: 10.1002/chir.23301
Jordan L Johnson 1 , Ernesto Santoro 1 , Roukia Zatout 2, 3 , Ana G Petrovic 4 , Alessio Cimmino 2 , Stefano Superchi 5 , Antonio Evidente 2 , Nina D Berova 6 , Prasad L Polavarapu 1
Affiliation  

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.

中文翻译:

从其 4-O-乙酰基衍生物的实验和预测手性研究中得到的 seco-eudesmanolide inuloxin D 的绝对构型

Dittrichia viscosa中分离出属于不同亚组的倍半萜类菊糖素 A-D并显示出对一些寄生植物如 Pelipanche、Orobanche 和 Cuscuta 物种的潜在生物防治。前三种菊糖素 A-C 的绝对构型先前是通过使用实验和计算手性光谱方法确定的。菊糖素 D 的绝对构型仍有待确定。与菊糖素 D 密切相关的生物活性菊糖素 E 是最近从同一植物有机提取物中分离出来的。通过比较它们的 NMR 光谱数据,将菊糖素 D 的相同相对构型分配给菊糖素 E。在这项工作中,通过分析菊糖素 D 的 4-O-乙酰基衍生物的实验和预测的手性特性,建议了菊糖素 D 和菊糖素 E 的绝对构型。
更新日期:2021-04-08
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