Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum
Literature Information
Gui-Min Xue, Chen-Guang Zhao, Jin-Feng Xue, Hui Chen, Zhen-Zhu Zhao, Ying-Ying Si, Kun Du, Yan-Le Zhi, Wei-Sheng Feng
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 [3,3,1,01′,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 (IC50: 13.2 μM, 1; 9.8 μM, 2) via suppression of inflammatory cytokines IL-1β, IL-6, and iNOS.
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