Chemical constituents of the bark of Dipteryx alata vogel, an active species against Bothrops jararacussu venom

Molecules. 2010 Nov 12;15(11):8193-204. doi: 10.3390/molecules15118193.

Abstract

The effect of four sub-extracts prepared from the lyophilized hydroalcoholic bark of Dipteryx alata (Leguminosae-Papilionoideae) dissolved in a methanol-water (80:20) mixture through a liquid-liquid partition procedure has been investigated against the neuromuscular blockade of the venom of the snake Bothrops jararacussu. The active CH₂Cl₂ sub-extract has been extensively analyzed for its chemical constituents, resulting in the isolation of four lupane-type triterpenoids: lupeol, lupenone, 28-hydroxylup-20(29)-en-3-one, betulin, nine isoflavonoids: 8-O-methylretusin, 7-hydroxy-5,6,4'-trimethoxyisoflavone, afrormosin, 7-hydroxy-8,3',4'-trimethoxyisoflavone, 7,3'-dihydroxy-8,4'-dimethoxyisoflavone, odoratin, 7,8,3'-trihydroxy-4'-methoxyisoflavone, 7,8,3'-trihydroxy-6,4'-dimethoxyisoflavone, dipteryxin, one chalcone: isoliquiritigenin, one aurone: sulfuretin and three phenolic compounds: vanillic acid, vanillin, and protocatechuic acid. Their chemical structures were elucidated on the basis of spectroscopic analysis, including HRMS, 1D- and 2D-NMR techniques.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bothrops / metabolism*
  • Crotalid Venoms / pharmacology*
  • Diaphragm / drug effects*
  • Dipteryx / chemistry*
  • In Vitro Techniques
  • Isoflavones / chemistry
  • Isoflavones / pharmacology
  • Magnetic Resonance Spectroscopy
  • Male
  • Mass Spectrometry
  • Mice
  • Molecular Structure
  • Neuromuscular Blockade
  • Pentacyclic Triterpenes / chemistry
  • Pentacyclic Triterpenes / pharmacology
  • Phrenic Nerve / drug effects
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Triterpenes / chemistry
  • Triterpenes / pharmacology

Substances

  • Crotalid Venoms
  • Isoflavones
  • Pentacyclic Triterpenes
  • Plant Extracts
  • Triterpenes
  • lupenone
  • afromosin
  • betulin
  • lupeol