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

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 5/6fused 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 IC 50 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.

Antifungal and Antimicroalgal Trichothecene Sesquiterpenes from the Marine Algicolous Fungus Trichoderma brevicompactum A-DL-9-2

“…Crystallographic analysis was performed according to previous procedures. , The data have been deposited at the Cambridge Crystallographic Data Centre with deposition nos. CCDC2016558, CCDC2016560, and CCDC2016561, which can be obtained free of charge from the Cambridge Crystallographic Data Centre via (or from the CCDC, 12 Union Road, Cambridge CB21EZ, U.K.; fax: + 44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).…”

“…Crystallographic analysis was performed according to previous procedures. 24,27 Antifungal and Antimicroalgal Assays. Antifungal evaluation against five phytopathogenic fungi (B. cinerea, C. miyabeanus, F. oxysporum f. sp.…”

Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

“…All non-hydrogen atoms were refined anisotropically with SHELXL-97 and SHELXL-2014 using full-matrix least-squares, and refinements of the H atoms in calculated positions were performed using a riding model. Molecular graphics were calculated with PLATON [37]. Crystallographic data have been deposited in the Cambridge Crystallographic Data Centre as CCDC 2,024,007 for 1.…”

Callintegers A and B, Unusual Tricyclo[4.4.0.09,10]tetradecane Clerodane Diterpenoids from Callicarpa integerrima with Inhibitory Effects on NLRP3 Inflammasome Activation

“…Terpenoids are abundant in medicinal plants and have a great potential to provide both novel structures and diverse biological activities. Phytochemical investigation has revealed that the genus Callicarpa is rich in diterpenes. − Research on the chemical composition of C. bodinieri , C. arborea , C. rubella , and C. nudiflora has uncovered several types of terpenoids, such as clerodane and abietane diterpenoids, ,− some of which exhibited inhibitory anti-NLRP3 inflammasome activity and moderate inhibitory effects on spleen tyrosine kinase (SYK). The above-mentioned reports provide a theoretical basis for further studies on the diterpene of Callicarpa species.…”