Structure and total synthesis of aspernigerin: a novel cytotoxic endophyte metabolite.
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 microM, respectively. A feasible total synthetic route for aspernigerin (1) has been established for further pharmacological research.
Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, P. R. China.
Li
L
Shen
Yong-Hao
YH
Ye
Xiao-Ting
XT
Wang
Hai-Liang
HL
Zhu
Chen
C
Xu
Yong-Cun
YC
Song
Hai
H
Li
Ren-Xiang
RX
Tan
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001234:Aspergillus niger / Q000378:metabolism; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D010879:Piperazines; D011804:Quinolines; C521450:aspernigerin