Weakly antimalarial flavonol arabinofuranosides from Calycolpus warszewiczianus

J Nat Prod. 2006 May;69(5):826-8. doi: 10.1021/np050484i.

Abstract

Three new flavonol arabinosides (2-4) were isolated from the young leaves of Calycolpus warszewiczianus. The structures were determined as myricetin-3-O-alpha-L-3' '-acetylarabinofuranoside (2), myricetin-3-O-alpha-L-3' ',5' '-diacetylarabinofuranoside (3), and 5-galloylquercetin-3-O-alpha-L-arabinofuranoside (4). Molecular structures were elucidated using NMR spectroscopy in combination with IR and MS data. Two known compounds, myricetin-3-O-alpha-L-arabinofuranoside (1) and (-)-epi-catechin (5), were also isolated. The compounds were tested in vitro against a chloroquine-resistant strain of Plasmodium falciparum, Leishmania mexicana, and Trypanosoma cruzi parasites. Compound 4 demonstrated weak activity against a chloroquine-resistant strain of P. falciparum (14.5 microM), whereas none of the compounds demonstrated activity against L. mexicana and T. cruzi at the concentrations of 40 and 50 microg/mL, respectively, and no cytotoxicity was detected against mammalian cells below 100 microg/mL.

Publication types

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

MeSH terms

  • Animals
  • Antimalarials* / chemistry
  • Antimalarials* / isolation & purification
  • Antimalarials* / pharmacology
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / isolation & purification
  • Antiprotozoal Agents / pharmacology
  • Arabinose* / analogs & derivatives
  • Arabinose* / chemistry
  • Arabinose* / isolation & purification
  • Arabinose* / pharmacology
  • Chloroquine / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Resistance
  • Flavonols* / chemistry
  • Flavonols* / isolation & purification
  • Flavonols* / pharmacology
  • Leishmania mexicana / drug effects
  • Molecular Structure
  • Myrtaceae / chemistry*
  • Panama
  • Plants, Medicinal / chemistry*
  • Plasmodium falciparum / drug effects
  • Trypanosoma cruzi / drug effects

Substances

  • Antimalarials
  • Antiprotozoal Agents
  • Flavonols
  • Chloroquine
  • Arabinose