文章基本信息

标题：Isolation, Structure Elucidation, and Absolute Configuration of Germacrane Isomers from Carpesium divaricatum
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作者：Tao Zhang ; Jia-Huan Chen ; Jin-Guang Si 等
期刊名称：Scientific Reports
电子版ISSN：2045-2322
出版年度：2018
卷号：8
期号：1
页码：12418
DOI：10.1038/s41598-018-30782-2
语种：English
出版社：Springer Nature
摘要：Five sets of germacrane isomers ( 1 / 8/17 , 2 / 7/10/11/13/16/18 , 3 / 4/5/14/20 , 6 / 12/15 , and 9 / 19 ) with different skeletal types, including seven new ones ( 1 – 3 , 8 – 9 , and 15 – 16 ) were isolated from the whole plant of Carpesium divaricatum . Among them, there are six pairs of stereoisomers ( 1 / 8 , 2 / 13 , 4 / 14 , 6 / 12 , 7 / 11 and 10/11 ). The planar structures and relative configurations of the new compounds were elucidated by detailed spectroscopic analysis. The absolute configurations of 4 , 10 , 11 , and 17 were established by circular dichroism (CD) spectra and X-ray crystallographic analyses, and the stereochemistry of the new compounds 1 – 3 , 8 – 9 , and 15 – 16 were determined by similar CD spectra with 4 , 10 , 11 , and 17 , respectively. The confusion in the literature about subtypes I and II of germacranolides was clarified in this paper. The NMR data of 10 – 11 , and the absolute configurations of the known compounds 4 – 6 , 13 – 14 , and 17 – 20 were reported for the first time. Compounds 13 , 17 , and 18 showed cytotoxicity against human cervical (HeLa), colon (LoVo) and stomach cancer (BGC-823) cell lines with IC₅₀ values in the range 4.72–13.68 μ M compared with the control cis -platin (7.90–15.34 μ M).