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Callicarpins, Two Classes of Rearranged ent-Clerodane Diterpenoids from Callicarpa Plants Blocking NLRP3 Inflammasome-Induced Pyroptosis
- 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.
- Subjects :
- Pharmacology
Circular dichroism
biology
Bicyclic molecule
Stereochemistry
Organic Chemistry
Pyroptosis
Pharmaceutical Science
Callicarpa
Inflammasome
biology.organism_classification
Terpenoid
Analytical Chemistry
chemistry.chemical_compound
Complementary and alternative medicine
chemistry
Drug Discovery
medicine
Molecular Medicine
Secretion
Undecane
medicine.drug
Subjects
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