Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana.
Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argemone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[ c]phenanthridine (+/-)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 microg/mL and 14.6, respectively.
Chang
Yuh-Chwen
YC
Department of Chemical Engineering, Kao Yuan Institute of Technology, Kaohsiung, Taiwan, ROC.
Hsieh
Pei-Wen
PW
Chang
Fang-Rong
FR
Wu
Ru-Rong
RR
Liaw
Chih-Chuang
CC
Lee
Kuo-Hsiung
KH
Wu
Yang-Chang
YC
D000470:Alkaloids / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D019380:Anti-HIV Agents / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D031674:Argemone; D053119:Benzophenanthridines; D001600:Berberine Alkaloids; D015658:HIV Infections / Q000188:drug therapy; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D010616:Phenanthrenes / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D013329:Structure-Activity Relationship
C473637:6-acetonyldihydrochelerythrine; D000470:Alkaloids; D019380:Anti-HIV Agents; D053119:Benzophenanthridines; D001600:Berberine Alkaloids; D010616:Phenanthrenes; D010936:Plant Extracts; C009093:protopine