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 microg/mL and 14.6, respectively.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkaloids / administration & dosage
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Alkaloids / chemistry
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Alkaloids / pharmacology*
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Alkaloids / therapeutic use
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Anti-HIV Agents / administration & dosage
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Anti-HIV Agents / chemistry
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Anti-HIV Agents / pharmacology*
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Anti-HIV Agents / therapeutic use
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Argemone*
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Benzophenanthridines
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Berberine Alkaloids*
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HIV Infections / drug therapy
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HIV-1 / drug effects*
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Humans
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Inhibitory Concentration 50
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Magnetic Resonance Spectroscopy
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Phenanthrenes / administration & dosage
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Phenanthrenes / pharmacology*
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Phenanthrenes / therapeutic use
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Phytotherapy*
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Plant Extracts / administration & dosage
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Plant Extracts / chemistry
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Plant Extracts / pharmacology*
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Plant Extracts / therapeutic use
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Structure-Activity Relationship
Substances
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6-acetonyldihydrochelerythrine
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Alkaloids
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Anti-HIV Agents
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Benzophenanthridines
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Berberine Alkaloids
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Phenanthrenes
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Plant Extracts
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protopine