LC/MS/NMR analysis of isomeric divanilloylquinic acids from the root bark of Fagara zanthoxyloides Lam

Phytochemistry. 2004 Apr;65(8):1145-51. doi: 10.1016/j.phytochem.2004.02.025.

Abstract

Gradient HPLC coupled to DAD/UV, MS/MS and NMR has been applied to the rapid structure determination of three new isomeric divanilloylquinic acids from Fagara zanthoxyloides collected in Burkina Faso: 3,4-O-divanilloylquinic acid, 3,5-O-divanilloylquinic acid and 4,5-O-divanilloylquinic acid. Furthermore these new compounds named burkinabins A-C could play a useful role in sickle cell disease, as the active agents of Fagara zanthoxyloïdes are said to be unidentified aromatic compounds with carboxylic acid grouping (Adesanya, S.A., Sofowora, A., 1983. Biological standardisation of Zanthoxylum roots for antisickling activity. Planta Med. 48, 27-33).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anemia, Sickle Cell / metabolism
  • Antisickling Agents / chemistry
  • Antisickling Agents / isolation & purification
  • Antisickling Agents / pharmacology
  • Chromatography, High Pressure Liquid / methods
  • Cromolyn Sodium / pharmacology
  • Humans
  • Isomerism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular / methods
  • Plant Bark / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Roots / chemistry
  • Quinic Acid / analogs & derivatives*
  • Quinic Acid / chemistry
  • Quinic Acid / isolation & purification
  • Quinic Acid / pharmacology
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Vanillic Acid / analogs & derivatives*
  • Vanillic Acid / chemistry
  • Vanillic Acid / isolation & purification
  • Vanillic Acid / pharmacology
  • Zanthoxylum / chemistry*

Substances

  • Antisickling Agents
  • Plant Extracts
  • Quinic Acid
  • Vanillic Acid
  • Cromolyn Sodium