Further polyoxygenated cembranoids from South China Sea soft coral Sarcophyton ehrenbergi

被引:14
|
作者
Li, Geng [1 ,4 ]
Li, Heng [2 ,4 ]
Tang, Wei [2 ,4 ]
Yao, Li-Gong [1 ]
Liang, Lin-Fu [3 ]
Guo, Yue-Wei [1 ,3 ,4 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, Lab Immunopharmacol, Shanghai 201203, Peoples R China
[3] Cent South Univ Forestry & Technol, Coll Mat Sci & Engn, 498 South Shaoshan Rd, Changsha 410004, Peoples R China
[4] Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
关键词
Soft coral; Sarcophyton ehrenbergi; Cembrane-type diterpenoids; Modified Mosher's method; ECD calculation; TNF-alpha inhibitory activity; ENANTIOSELECTIVE TOTAL-SYNTHESIS; NATURAL-PRODUCTS; DITERPENES; METABOLITES; CHEMISTRY;
D O I
10.1016/j.bioorg.2020.103993
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Eleven new cembrane diterpenes, namely, sarcoehrenins A-J (1-9, 11) and (2S,11S,12S)-isosarcophytoxide (10), along with six known compounds, gibberosene B (12), (13S)-cembra-1,3,7,11-tetraen-13-ol (13), (+)-sarcophtol (14), cembrene-C (15), (1R,4R,2E,7E,11E)-cembra-2,7,11-trien-4-ol (16) and (1S,4R,2E,7E,11E)cembratrien-4-ol (17) were isolated from the soft coral Sarcophyton ehrenbergi collected from Weizhou Island, Beibu Gulf, South China Sea. The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. The absolute configuration of compound 2 was established by the modified Mosher's method in association with TDDFT ECD calculation, while the absolute configuration of compound 3 was assigned by TDDFT ECD approach. In in vitro bioassays, compounds 13 and 17 showed potent TNF-alpha inhibitory activities being similar to that of positive control dexamethasone. A preliminary structural-activity relationship was also described.
引用
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页数:9
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