Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana

Planta Med. 2003 Feb;69(2):148-52. doi: 10.1055/s-2003-37710.

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

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkaloids / administration & dosage
  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Alkaloids / therapeutic use
  • Anti-HIV Agents / administration & dosage
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Anti-HIV Agents / therapeutic use
  • Argemone*
  • Benzophenanthridines
  • Berberine Alkaloids*
  • HIV Infections / drug therapy
  • HIV-1 / drug effects*
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Phenanthrenes / administration & dosage
  • Phenanthrenes / pharmacology*
  • Phenanthrenes / therapeutic use
  • Phytotherapy*
  • Plant Extracts / administration & dosage
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Extracts / therapeutic use
  • Structure-Activity Relationship

Substances

  • 6-acetonyldihydrochelerythrine
  • Alkaloids
  • Anti-HIV Agents
  • Benzophenanthridines
  • Berberine Alkaloids
  • Phenanthrenes
  • Plant Extracts
  • protopine