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Structure and Total Synthesis of Aspernigerin: A Novel Cytotoxic Endophyte Metabolite
Author(s) -
Shen Li,
Ye YongHao,
Wang XiaoTing,
Zhu HaiLiang,
Xu Chen,
Song YongCun,
Li Hai,
Tan RenXiang
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501423
Subject(s) - hela , cytotoxic t cell , stereochemistry , endophyte , chemistry , metabolite , cervical carcinoma , alkaloid , carcinoma cell , biology , biochemistry , cell , botany , in vitro , genetics , cervical cancer , cancer
Abstract Aspernigerin ( 1 ), a novel cytotoxic alkaloid consisting of an unprecedented structural framework has been isolated from the extract of a culture of Aspergillus niger IFB‐E003, an endophyte in Cyndon dactylon . Its structure was elucidated on the basis of comprehensive NMR spectral analysis and confirmed by single‐crystal X‐ray analysis. Aspernigerin ( 1 ) has been shown to be cytotoxic to the tumor cell lines nasopharynyeal epidermoid KB, cervical carcinoma Hela, and colorectal carcinoma SW1116 with corresponding IC 50 values of 22, 46, and 35 μ M , respectively. A feasible total synthetic route for aspernigerin ( 1 ) has been established for further pharmacological research.