Coumarins from Galipea panamensis and Their Activity against Leishmania panamensis

J Nat Prod. 2010 May 28;73(5):1012-4. doi: 10.1021/np100146y.

Abstract

Two new coumarin compounds (1 and 2), phebalosin (3), its derived artifact murralongin (4), and murrangatin acetonide (5) were isolated from the leaves of Galipea panamensis. The structures of 1 and 2 were assigned as 7-{[(2R*)-3,3-dimethyloxiran-2-yl]methoxy}-8-[(2R*,3R*)-3-isopropenyloxiran-2-yl]-2H-chromen-2-one and 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one, respectively, on the basis of their spectroscopic data (primarily NMR and MS). Compounds 1-3 were tested against axenic amastigote forms of Leishmania panamensis and displayed 50% effective concentrations (EC(50)) of 9.9, 10.5, and 14.1 microg/mL, respectively. These three compounds also displayed cytotoxicity (IC(50)) at concentrations of 9.7, 33.0, and 20.7 microg/mL, respectively, on human promonocytic U-937 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification*
  • Antiprotozoal Agents / pharmacology*
  • Colombia
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Leishmania / drug effects*
  • Molecular Structure
  • Monocyte-Macrophage Precursor Cells / drug effects
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Rutaceae / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 7-(((2R*)-3,3-dimethyloxiran-2-yl)methoxy)-8-((2R*,3R*)-3-isopropenyloxiran-2-yl)-2H-chromen-2-one
  • 7-methoxy-8-(4-methyl-3-furyl)-2H-chromen-2-one
  • Antiprotozoal Agents
  • Coumarins
  • phebalosin