Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana.

Abstract

Fractionation of the chloroform extract from the aerial part of Argemone mexicana led to the isolation of two benzophenanthridine-type alkaloids, N-demethyloxysanguinarine and pancorine; three benzylisoquinoline-type alkaloids, (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxyisoquinoline, (+)-higenamine and (+)-reticuline. Among them, N-demethyloxysanguinarine is a new compound, and (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxy-isoquinoline was isolated form a natural source for the first time, to which was assigned a trivial name, (+)-argenaxine. In addition, six known non-alkaloidal compounds were also isolated and identified. All compounds were characterized on the basis of their spectral data and chemical evidences. Some isolated alkaloids from this species were evaluated for their cytotoxicity to human nasopharyngeal carcinoma (HONE-1) and human gastric cancer (NUGC) cell lines. Chelerythrine was found to exhibit significant activity against NUGC cell line, while angoline inhibited both types. (+)-Argenaxine showed moderate activity against the NUGC cell line.

• Authors: Yuh-Chwen Chang, Fang-Rong Chang, Ashraf T Khalil, Pei-Wen Hsieh, Yang-Chang Wu
• Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences (Z Naturforsch C J Biosci) 2003 Jul-Aug Vol. 58 Issue 7-8 Pg. 521-6 ISSN: 0939-5075 [Print] Germany
• PMID: 12939038 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkaloids
• Isoquinolines
• Phenanthridines
• Plant Extracts

Topics

• Alkaloids (chemistry, isolation & purification, toxicity)
• Argemone (chemistry)
• Cell Survival (drug effects)
• Humans
• Isoquinolines (chemistry, isolation & purification, toxicity)
• Models, Molecular
• Molecular Structure
• Nasopharyngeal Neoplasms
• Phenanthridines (chemistry, isolation & purification, toxicity)
• Plant Components, Aerial (chemistry)
• Plant Extracts (chemistry, isolation & purification, toxicity)
• Stomach Neoplasms
• Tumor Cells, Cultured