Structure and total synthesis of aspernigerin: a novel cytotoxic endophyte metabolite.

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 microM, respectively. A feasible total synthetic route for aspernigerin (1) has been established for further pharmacological research.

• Authors: Li Shen, Yong-Hao Ye, Xiao-Ting Wang, Hai-Liang Zhu, Chen Xu, Yong-Cun Song, Hai Li, Ren-Xiang Tan
• Journal: Chemistry (Weinheim an der Bergstrasse, Germany) (Chemistry) Vol. 12 Issue 16 Pg. 4393-6 (May 24 2006) ISSN: 0947-6539 [Print] Germany
• PMID: 16555343 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Piperazines
• Quinolines
• aspernigerin

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Aspergillus niger (metabolism)
• Cell Line, Tumor
• Crystallography, X-Ray
• HeLa Cells
• Humans
• Magnetic Resonance Spectroscopy
• Molecular Conformation
• Molecular Structure
• Piperazines (chemical synthesis, chemistry, pharmacology)
• Quinolines (chemical synthesis, chemistry, pharmacology)