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

文献类型：期刊论文

作者Shen, Shou-Mao5,6; Yang, Qing4,5; Zang, Yi5; Li, Jia2,3,5; Liu, Xueting1; Guo, Yue-Wei5,6
刊名BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
出版日期2022-07-25
卷号18页码:916-925
关键词Acanthella cavernosa anti-inflammatory biosynthetic pathway chiral separation marine sponge sesquiterpenoid
ISSN号1860-5397
DOI10.3762/bjoc.18.91
通讯作者Liu, Xueting(liuxueting@ecust.edu.cn) ; Guo, Yue-Wei(ywguo@simm.ac.cn)
英文摘要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.
WOS关键词MARINE SPONGE ; NATURAL-PRODUCTS ; ANTIFOULING ACTIVITY ; SOFT CORAL ; BIOSYNTHESIS ; TERPENOIDS ; GENOME ; CONSTITUENTS ; LARVAE
资助项目National Natural Science Foundation of China[81991521] ; SKLDR/SIMM Project[SIMM2013ZZ-06]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000834412200001
出版者BEILSTEIN-INSTITUT
源URL[http://119.78.100.183/handle/2S10ELR8/301911]  
专题新药研究国家重点实验室
通讯作者Liu, Xueting; Guo, Yue-Wei
作者单位1.East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China
2.Pilot Natl Lab Marine Sci & Technol, Open Studio Druggabil Res Marine Nat Prod, Qingdao, Peoples R China
3.Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Shandong, Peoples R China
4.Nanchang Univ, Sch Pharmaceut Sci, Nanchang 330006, Jiangxi, Peoples R China
5.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
6.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
推荐引用方式
GB/T 7714		 Shen, Shou-Mao,Yang, Qing,Zang, Yi,et al. Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,2022,18:916-925.
APA Shen, Shou-Mao,Yang, Qing,Zang, Yi,Li, Jia,Liu, Xueting,&Guo, Yue-Wei.(2022).Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa.BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,18,916-925.
MLA Shen, Shou-Mao,et al."Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa".BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 18(2022):916-925.

入库方式： OAI收割

来源：上海药物研究所

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