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Toonaolides A–X, limonoids from Toona ciliata: Isolation, structural elucidation, and bioactivity against NLRP3 inflammasome.
- Source :
-
Bioorganic Chemistry . Dec2020, Vol. 105, pN.PAG-N.PAG. 1p. - Publication Year :
- 2020
-
Abstract
- • Twenty-four new limonoids were obtained from Toona ciliata. • Their structures were determined by spectroscopic analysis, quantum chemistry calculations, and X-ray diffraction. • Several compounds showed significant anti-NLRP3 inflammasome activity. Twenty-four new limonoids, toonaolides A−X (1 – 24), characterized with an α , β -unsaturated- γ -lactone A-ring were isolated from the twigs of Toona ciliata. Their structures and absolute configurations were elucidated by spectroscopic data, X-ray diffraction crystallography, and quantum chemistry calculations. Most of the isolated compounds (except 9 , 18 , and 24 which possessed the maleimide ring) featured the rare 21-hydroxybutenolide or 23-hydroxybutenolide moieties. In particular, compound 1 has an unprecedented limonoid architecture with 6/6 cis -fused A/B ring system and 2 has an unusual tetrahydrofuran ring B skeleton, featuring a 7/5/6/5 ring system. The biological evaluation showed that compounds 9 , 11 , 12 , 14 , and 18 exhibited significantly anti-NLRP3 inflammasome activity with IC 50 values ranging from 3.2 to 9.7 μM. Analysis of IL-1 β and caspase-1 expression revealed that compounds 11 and 12 are selective inhibitors of NLRP3 inflammasome, which could ameliorate cell pyroptosis by blocking NLRP3 inflammasome activation. [ABSTRACT FROM AUTHOR]
- Subjects :
- *LIMONOIDS
*CILIATA
*QUANTUM chemistry
*X-ray crystallography
*X-ray diffraction
Subjects
Details
- Language :
- English
- ISSN :
- 00452068
- Volume :
- 105
- Database :
- Academic Search Index
- Journal :
- Bioorganic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 147584425
- Full Text :
- https://doi.org/10.1016/j.bioorg.2020.104363