Herpotrichones A and B, Two Intermolecular [4 + 2] Adducts with Anti-Neuroinflammatory Activity from a Herpotrichia Species

Herpotrichones A and B (1 and 2), two intermolecular [4 + 2] adducts with an unprecedented pentacyclic 6/6/6/6/3 skeleton, were isolated from Herpotrichia sp. SF09, an isopod-associated fungus, along with a new shunt product protrichone (3). Their structures were elucidated by the analysis of spectr...

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Published in:Organic letters 2020-01, Vol.22 (2), p.405-409
Main Authors: Han, Wen-Bo, Wang, Guang-Yi, Tang, Jiang-Jiang, Wang, Wen-Ji, Liu, Han, Gil, Roberto R, Navarro-Vázquez, Armando, Lei, Xinxiang, Gao, Jin-Ming
Format: Article
Language:English
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Summary:Herpotrichones A and B (1 and 2), two intermolecular [4 + 2] adducts with an unprecedented pentacyclic 6/6/6/6/3 skeleton, were isolated from Herpotrichia sp. SF09, an isopod-associated fungus, along with a new shunt product protrichone (3). Their structures were elucidated by the analysis of spectroscopic data, residual dipolar coupling (RDC)-based computer-assisted 3D structure elucidation (CASE-3D), and single-crystal X-ray diffraction in combination with electronic circular dichroism (ECD) calculations. Compounds 1 and 2 were assessed to be potent anti-neuroinflammatory agents in lipopolysaccharide (LPS)-induced BV-2 microglial cells with the half maximal inhibitory concentration (IC50) values of 0.41 and 0.11 μM, respectively.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04099