Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana.
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.
Chang
Yuh-Chwen
YC
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
Chang
Fang-Rong
FR
Khalil
Ashraf T
AT
Hsieh
Pei-Wen
PW
Wu
Yang-Chang
YC
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D031674:Argemone / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects*; D006801:Humans; D007546:Isoquinolines / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D008958:Models, Molecular; D015394:Molecular Structure; D009303:Nasopharyngeal Neoplasms; D010617:Phenanthridines / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D035261:Plant Components, Aerial / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D013274:Stomach Neoplasms; D014407:Tumor Cells, Cultured
D000470:Alkaloids; D007546:Isoquinolines; D010617:Phenanthridines; D010936:Plant Extracts