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Callicarpins, Two Classes of Rearranged ent-Clerodane Diterpenoids from Callicarpa Plants Blocking NLRP3 Inflammasome-Induced Pyroptosis

Authors :
Xiao-Nian Li
Ruihan Zhang
De-Bing Pu
Xiao-Li Li
Wei-Lie Xiao
Xing-Jie Zhang
Yan Yang
Jun-Bo Gao
De-Wen Bi
Jing Lin
Source :
Journal of Natural Products. 83:2191-2199
Publication Year :
2020
Publisher :
American Chemical Society (ACS), 2020.

Abstract

Callicarpins A-D (1-4), possessing an unprecedented A-homoent-clerodane scaffold with a bicyclo[5.4.0]undecane ring system, and callicarpins E-G (5-7), with 5/6-fused ent-clerodane diterpenoid skeletons, were isolated from Callicarpaarborea and C. integerrim. Their structures were elucidated by comprehensive spectroscopic data, X-ray crystal diffraction, chemical derivatization, and electronic circular dichroism (ECD) data. Putative biosynthetic pathways for these callicarpins are proposed. Compounds 2, 3b, and 6-8 showed potent inhibitory effects against the NLRP3 inflammasome with IC50 values from 1.4 to 5.3 μM, and 2 significantly blocked NLRP3 inflammasome-induced pyroptosis by inhibiting Casp-1 activation and IL-1β secretion in J774A.1 cells.

Details

ISSN :
15206025 and 01633864
Volume :
83
Database :
OpenAIRE
Journal :
Journal of Natural Products
Accession number :
edsair.doi...........11005db83095853baa7f3d6aaa4e21e1
Full Text :
https://doi.org/10.1021/acs.jnatprod.0c00288