Planta Med 2019; 85(18): 1490
DOI: 10.1055/s-0039-3399900
Main Congress Poster
Poster Session 1
© Georg Thieme Verlag KG Stuttgart · New York

Isolation, structure elucidation, and absolute configuration of Germacrane isomers from Carpesium divaricatum

Z-M Zou
1   Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College,, 100193, Beijing P. R. China
,
T Zhang
1   Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College,, 100193, Beijing P. R. China
,
Q-B Zhang
1   Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College,, 100193, Beijing P. R. China
› Author Affiliations
Further Information

Publication History

Publication Date:
20 December 2019 (online)

 

Germacranolides are one of the main classes of sesquiterpene lactones, for which road bioactivities have been reported, including cytotoxicity, anti-inflammatory and anti-malaria. Most of them were isolated from the genus Carpesium. The parent nucleus of the germacranolides contains a 5-membered γ-lactone ring fused to a circular 10-membered carbocycle, with different post-modifications to produce complex and diverse structural features. In addition, these germacranolides contain as many as nine stereogenic centers, creating the problem of stereochemical configuration. However, their absolute configurations have rarely been studied.

To investigate the chemical constituents from the whole herb of Carpesium divaricatum (Asteraceae), a folk medicine used by the Tu nationality in China; to find more germacranolides with diverse structure to determine their absolute configuration.

101 compounds were isolated from the whole herb of Carpesium divaricatum. Among them, 56 were germacranolides including 11 sets of isomers with 5 subtypes. NMR, HRESIMS, ECD calculation and X-diffraction were applied to identify their structures and absolute configurations.

49 new compounds were obtained and 30 of them were germacranolides. Some of them have cytotoxic and anti-inflammatory properties. These findings present knowledge on the structurally diverse and biologically important germacranolides. We also clarified the confusion that exist in the absolute configuration of germacranolides.

 

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