In:
Organic Chemistry Frontiers, Royal Society of Chemistry (RSC), Vol. 9, No. 1 ( 2022), p. 190-196
Abstract:
Two pairs of meroterpenoid enantiomers, (±)-fissisternoids A (1) and B (2), along with their putative biogenetic precursor 3 were isolated from the branches and leaves of Fissistigma bracteolatum . Compound 1 represents an unprecedented meroterpenoid featuring a unique tricyclo [3,3,1,0 1′,5′ ] decane central framework, and compound 2 possesses a rare 6/6/5/4 tetracyclic carbon skeleton, both of which were derived from quinodihydrochalcone and monoterpenoid via a key [4 + 2] Diels–Alder cyclization and Prins reaction. Their structures and absolute configurations were established using spectroscopic data, X-ray diffraction, and electronic circular dichroism calculations. Compounds 1 and 2 exhibit anti-inflammatory activity (IC 50 : 13.2 μM, 1; 9.8 μM, 2) via suppression of inflammatory cytokines IL-1β, IL-6, and iNOS.
Type of Medium:
Online Resource
ISSN:
2052-4129
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2022
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