Alkaloids and polyketides from the South China Sea sponge Agelas aff. nemoechinata

被引:15
作者
An, Liang [1 ,3 ]
Song, Wenjuan [1 ,2 ]
Tang, Xuli [4 ]
de Voogd, Nicole J. [5 ]
Wang, Qi [1 ,2 ]
Chu, Meijun [1 ,2 ]
Li, Pinglin [1 ,2 ]
Li, Guoqiang [1 ,2 ]
机构
[1] Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Drugs, Qingdao 266003, Peoples R China
[2] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao, Shandong, Peoples R China
[3] Qingdao Huanghai Pharmaceut Co Ltd, Qingdao 266101, Peoples R China
[4] Ocean Univ China, Coll Chem & Chem Engn, Qingdao 266100, Peoples R China
[5] Natl Museum Nat Hist, NL-2300 RA Leiden, Netherlands
基金
中国国家自然科学基金;
关键词
B METHYL-ESTER; BROMOPYRROLE ALKALOIDS; BIOLOGICAL EVALUATION; METABOLITES; DERIVATIVES; MAURITIANA; LONGAMIDE;
D O I
10.1039/c6ra27026c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A chemical investigation of the South China Sea sponge Agelas aff. nemoechinata yielded three pairs of new enantiotopic pyrrole alkaloids nemoechines A-C (1-3), one new diterpene-adenine alkaloid nemoechine D (8), and one new polyketide nemoechioxide A (10), together with nine known analogues (4-7, 9, 11-14). Compounds 1-3 were initially obtained as racemates and were further separated by chiral HPLC chromatography to afford the three pairs of enantiomers. Their structures including absolute configurations of compounds 1-3 were elucidated on the basis of comprehensive spectroscopic analysis and quantum chemical calculation. Nemoechine A (1), possessing an unusual cyclopentane-fused imidazole ring system, represents the first monomeric precursor of nagelamide J. Compounds 8 and 9 showed cytotoxicity against HL-60 cell lines with IC50 values of 9.9 and 0.9 mu M, respectively, and compound 9 was also cytotoxic against HeLa cell lines with IC50 value of 8.9 mu M.
引用
收藏
页码:14323 / 14329
页数:7
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