Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum

文献情報

出版日 2021-11-19

DOI 10.1039/D1QO01404H

インパクトファクター 5.281

著者

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

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要旨

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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Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Fissisternoids A and B, two 2′,5′-quinodihydrochalcone-based meroterpenoid enantiomers with unusual carbon skeletons from Fissistigma bracteolatum

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