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Pyrrole Derivatives and Diterpene Alkaloids from the South China Sea Sponge Agelas nakamurai
Author(s) -
Chu MeiJun,
Tang XuLi,
Qin GuoFei,
Sun YanTing,
Li Lei,
Voogd Nicole J.,
Li PingLin,
Li GuoQiang
Publication year - 2017
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201600446
Subject(s) - diterpene , chemistry , stereochemistry , pyrrole , diastereomer , sponge , enantiomer , antibacterial activity , organic chemistry , bacteria , botany , genetics , biology
Two pairs of new non‐brominated racematic pyrrole derivatives, (±)‐nakamurine D ( 1 ) and (±)‐nakamurine E ( 2 ), two new diterpene alkaloids, isoagelasine C ( 16 ) and isoagelasidine B ( 21 ), together with 13 known pyrrole derivatives ((±)‐ 3 – 15 ), five known diterpene alkaloids ( 17 – 20 , 22 ) were isolated from the South China Sea sponge Agelas nakamurai . The racemic mixtures, compounds 1 – 4 , were resolved into four pairs of enantiomers, (+)‐ 1 and (−)‐ 1 , (+)‐ 2 and (−)‐ 2 , (+)‐ 3 and (−)‐ 3 , and (+)‐ 4 and (−)‐ 4 , by chiral HPLC . The structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses, quantum chemical calculations, quantitative measurements of molar rotations, application of van't Hoff 's principle of optical superposition, and comparison with the literature data. The NMR and MS data of compound 3 are reported for the first time, as the structure was listed in SciFinder Scholar with no associated reference. These non‐brominated pyrrole derivatives were found in this species for the first time. Compound 18 showed valuable cytotoxicities against HL ‐60, K562, and HCT ‐116 cell lines with IC 50 values of 12.4, 16.0, and 19.8 μ m , respectively. Compounds 16 – 19 , 21 , and 22 showed potent antifungal activities against Candida albicans with MIC values ranging from 0.59 to 4.69 μg/ml. Compounds 16 – 19 exhibited moderate antibacterial activities against Proteusbacillus vulgaris ( MIC values ranging from 9.38 to 18.75 μg/ml).