New dammarane and malabaricane triterpenes from Caloncoba echinata

J Nat Prod. 2002 Dec;65(12):1764-8. doi: 10.1021/np0201826.

Abstract

Three novel triterpenes, (11R,20R)-11,20-dihydroxy-24-dammaren-3-one (1), (17S,20R,24R)-17,25-dihydroxy-20,24-epoxy-14(18)-malabaricen-3-one (2), and (17R,20S,24R)-17,25-dihydroxy-20,24-epoxy-14(18)-malabaricen-3-one (3), were isolated from leaves of Caloncoba echinata. The structures were established using mainly 800 MHz NOESY and HMBC connectivities. The absolute stereochemistry of C-11 in 1 and that of C-17 in 2 were established by the Mosher method. The stereochemistry of the side chains of the malabaricanes is compatible with their biosynthesis by a cascade opening of diepoxides. The isolated triterpenes inhibited growth of Plasmodium falciparum parasites in vitro apparently via incorporation into erythrocyte membrane, as suggested by transformation of erythrocytes into stomatocytes at a concentration level at which the growth inhibition was observed.

MeSH terms

  • Animals
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology
  • Chromatography, High Pressure Liquid
  • Dammaranes
  • Erythrocytes / drug effects
  • Ghana
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Plasmodium falciparum / drug effects*
  • Salicaceae / chemistry*
  • Stereoisomerism
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • 11,20-dihydroxy-24-dammaren-3-one
  • 17,25-dihydroxy-20,24-epoxy-14(18)-malabaricen-3-one
  • Antimalarials
  • Triterpenes