文献类型：期刊文献

英文题名：Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

作者：Shen, Shou-Mao[1,2];Yang, Qing[2,3];Zang, Yi[2];Li, Jia[2,4,5];Liu, Xueting[6];Guo, Yue-Wei[1,2]

机构：[1]Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China;[3]Nanchang Univ, Sch Pharmaceut Sci, Nanchang 330006, Jiangxi, Peoples R China;[4]Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Shandong, Peoples R China;[5]Pilot Natl Lab Marine Sci & Technol, Open Studio Druggabil Res Marine Nat Prod, Qingdao, Peoples R China;[6]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China

年份：2022

卷号：18

起止页码：916

外文期刊名：BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000834412200001)】；

基金：This work was financially supported by the National Natural Science Foundation of China (No. 81991521) and the SKLDR/SIMM Project (No. SIMM2013ZZ-06).

语种：英文

外文关键词：Acanthella cavernosa; anti-inflammatory; biosynthetic pathway; chiral separation; marine sponge; sesquiterpenoid

摘要：One new aromadendrane-type sesquiterpenoid, namely ximaocavernosin P [(+)-1], and three new cadinane-type sesquiterpenoids, namely (+)-maninsigin D [(+)-4], (+)- and (-)-ximaocavernosin Q [(+)- and (-)-5], together with five related known ones [2, 3, (-)-4, 6, and 7], were isolated from the Hainan sponge Acanthella cavernosa. Compounds 4 and 5 were isolated as racemic forms, which were further separated to the corresponding enantiomers [(+)-4/(-)-4 and (+)-5/(-)-5], respectively, by using chiral-phase HPLC. The structures of new compounds were elucidated by extensive spectroscopic analysis and comparison with the reported data. In addition, the absolute configuration of optically pure (+)-1 and 2 were determined by time-dependent density functional theory/electronic circular dichroism (TDDFT-ECD) calculations or X-ray diffraction analysis. A plausible biosynthetic pathway of these sesquiterpenoids and their internal correlation were proposed and discussed. In an in vitro bioassay, (+)-aristolone (3) exhibited promising anti-inflammatory activity by the inhibition of LPS-induced TNF-alpha and CCL2 release in RAW 264.7 macrophages.