Anthocyanone A: a quinone methide derivative resulting from malvidin 3-O-glucoside degradation

J Agric Food Chem. 2007 Apr 4;55(7):2698-704. doi: 10.1021/jf062875o. Epub 2007 Mar 6.

Abstract

A new compound resulting from the oxidative degradation of maldivin 3-O-glucoside under acid conditions was detected in a wine model solution stored under 90 and 25 degrees C. It was isolated by semipreparative HPLC, and its structure was elucidated by UV-vis spectra, mass spectrometry (LC/MS), and NMR spectroscopy (1-D and 2-D). The compound was identified as 8-beta-d-glucopyranosyl-2,4-dihydroxy-6-oxo-cyclohexa-2,4-dienyl acetic acid (anthocyanone A), which results from nucleophilic attack of hydrogen peroxide to maldivin 3-O-glucoside through a Baeyer-Villiger oxidation followed by other oxidations steps.

MeSH terms

  • Anthocyanins / chemistry*
  • Chromatography, High Pressure Liquid
  • Cyclohexanones / analysis*
  • Cyclohexanones / chemistry*
  • Glucosides / analysis*
  • Glucosides / chemistry*
  • Hydrogen-Ion Concentration
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction
  • Wine / analysis

Substances

  • 8-glucopyranosyl-2,4-dihydroxy-6-oxocyclohexa-2,4-dienyl acetic acid
  • Anthocyanins
  • Cyclohexanones
  • Glucosides
  • malvidin-3-glucoside