New bioactive coumarins from Kielmeyera albopunctata

J Nat Prod. 2003 May;66(5):634-7. doi: 10.1021/np020597r.

Abstract

The CH(2)Cl(2) extract of the stem bark of Kielmeyera albopunctata was subjected to a bioassay-linked LC-MS dereplication procedure using the KB cell line to afford the new coumarins 4-(1-methylpropyl)-5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)chromen-2-one (1), 9-(1-methylpropyl)-4-hydroxy-5-(4-hydroxy-3-methylbutyryl)-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro[2,3-f]chromen-7-one (2), and 5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)-4-phenylchromen-2-one (3). Coumarins 1 and 3 showed moderate cytotoxicity, while 2 was inactive at 20 microg/mL. Compound 1was active in vitro against the trypomastigote form of the parasite Trypanosoma cruzi, killing 80% of the parasites after 24 h contact at 4 degrees C when added at 125 microg/mL to infected murine blood.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Brazil
  • Chagas Disease / blood
  • Chagas Disease / drug therapy
  • Clusiaceae / chemistry*
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology
  • Humans
  • KB Cells / drug effects
  • Lung Neoplasms
  • Male
  • Mice
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Bark / chemistry
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Prostatic Neoplasms
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / isolation & purification*
  • Trypanocidal Agents / pharmacology
  • Trypanosoma cruzi / drug effects
  • Tumor Cells, Cultured / drug effects

Substances

  • 4-(1-methylpropyl)-5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)chromen-2-one
  • 5,7-dihydroxy-8-(4-hydroxy-3-methylbutyryl)-6-(3-methylbut-2-enyl)-4-phenylchromen-2-one
  • 9-(1-methylpropyl)-4-hydroxy-5-(4-hydroxy-3-methylbutyryl)-2-(1-hydroxy-1-methylethyl)-2,3-dihydrofuro(2,3-f)chromen-7-one
  • Antineoplastic Agents, Phytogenic
  • Coumarins
  • Trypanocidal Agents