Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense

Phytochemistry. 2007 May;68(9):1312-20. doi: 10.1016/j.phytochem.2007.02.006. Epub 2007 Mar 29.

Abstract

The bioassay-guided purification of an n-hexane extract from the leaves of Piper hostmannianum var. berbicense led to the isolation of four monoterpene or prenyl-substituted dihydrochalcones (1a, 1b, 2, 3) as well as the known compounds 2',6'-dihydroxy-4'-methoxydihydrochalcone (4), linderatone (5), strobopinin (6), adunctin E (7) and (-)-methyllinderatin (8). Their structures were established on the basis of NMR and X-ray analysis. (-)-Methyllinderatin, linderatone and 2',6'-dihydroxy-4'-methoxydihydrochalcone exhibited the most potent antiplasmodial activity with IC50 values of 5.64, 10.33 and 12.69 microM, respectively against both chloroquine-sensitive and resistant strains of Plasmodium falciparum (F32,FcB1). The activity of (-)-methyllinderatin was confirmed in vivo against Plasmodium vinckei petteri in mice (80% of reduction of parasitemia) at a dose of 20 mg/kg/day.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology
  • Chalcones / chemistry
  • Chalcones / isolation & purification*
  • Chalcones / pharmacology*
  • Female
  • Flavanones / chemistry
  • Flavanones / isolation & purification*
  • Flavanones / pharmacology*
  • Malaria / drug therapy
  • Mice
  • Models, Molecular
  • Molecular Structure
  • Piper / chemistry*
  • Plasmodium / drug effects

Substances

  • Antimalarials
  • Chalcones
  • Flavanones