Two New Protopines Argemexicaines A and B and the Anti-HIV Alkaloid 6-Acetonyldihydrochelerythrine from Formosan Argemone mexicana

Abstract

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 μg/mL and 14.6, respectively.

Key words

Argemone mexicana - Papaveraceae - argemexicaine A - argemexicaine B - protopine - benzo[c]phenanthridine - (±)-6-acetonyldihydrochelerythrine - anti-HIV activity

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