Meroterpenoids Possessing Diverse Rearranged Skeletons with Anti-inflammatory Activity from the Mangrove-Derived Fungus Penicillium sp. HLLG-122  

作　　者：Yu-Yue Qin Wan-Shan Li Xuan Zhang Zhang-Xin Yu Xiao-Bao Li Han-Yi Chen Yan-Ru Lv Chang-Ri Han Guang-Ying Chen 

机构地区：[1]Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education and Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province,College of Chemistry and Chemical Engineering,Hainan Normal University,Haikou,Hainan,571158 China [2]Key Laboratory of Medicinal and Edible Plants Resources of Hainan Province,Hainan Vocational University of Science and Technology,Haikou,Hainan,571126 China

出　　处：《Chinese Journal of Chemistry》2023年第19期2507-2517,共11页中国化学（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.22177023 and 41866005);the Key Sci-ence and Technology Program of Hainan Province(No.ZDKJ202008);the Hainan Provincial Natural Science Foundation of China(221RC1054);the Specific Research Fund of the Innovation Platform for Academicians of Hainan Province(YSPTZX202030);the Innovation Platform for Academicians of Hainan Province,the Central Government Guides Local Science and Technology Devel-opment(ZY2022HN08);the research was also supported by the Innovative Research Project of Hainan Graduate Students(Qhyb2022-105).

摘　　要：Fifteen new meroterpenoids, littoreanoids A—O (1—15), including three rearranged skeleton meroterpenoids (1—3), were isolated from the mangrove-derived fungus Penicillium sp. HLLG-122. Compound 1 was a novel berkeleyacetal-derived meroterpenoid featuring an unusual spirocyclic 2-oxaspiro[5.5]undeca-4,7-dien-3-one moiety. Compound 2 possessed an unusual 6/6/6/6/6 pentacyclic system with a novel 1-hydroxy-7,7-dimethyl-2-oxabicyclo[2.2.2]octan-5-yl acetate moiety. Compound 3 was an unusual 6/7/6/5/6/5/4 polycyclic systems containing a β-lactone ring. The structures and absolute configurations of new compounds were elucidated by HRESIMS, NMR spectroscopy, single crystal X-ray diffraction analysis, and electronic circular dichroism calculations. The plausible biosynthetic pathways of 1—3 were also proposed. Compounds 6 and 11 exhibited anti-inflammatory effects with IC_(50) values of 30.41 and 19.02 μmol/L, respectively. The bioactive compound 11 was selected for the investigation of preliminary mechanism using molecular docking and Western blotting experiments. Compound 11 could suppress the levels of TNF-α and IL-6, and down-regulate the protein expression of iNOS and COX-2 in RAW 264.7 cells.

关 键 词：Penicillium sp TERPENOIDS Structural elucidation Anti-inflammatory activities Conformation analysis Natural products 

分 类 号：O62[理学—有机化学]