Anthocyanone A: a quinone methide derivative resulting from malvidin 3-O-glucoside degradation.
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.
Lopes
Paulo
P
Faculté d'Oenologie de Bordeaux, Université Victor Segalen Bordeaux 2, UMR 1219 INRA, 351 Cours de la Libération, 33405 Talence Cedex, France.
Richard
Tristan
T
Saucier
Cédric
C
Teissedre
Pierre-Louis
PL
Monti
Jean-Pierre
JP
Glories
Yves
Y
D000872:Anthocyanins / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003512:Cyclohexanones / Q000032:analysis* / Q000737:chemistry*; D005960:Glucosides / Q000032:analysis* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D014920:Wine / Q000032:analysis
C521179:8-glucopyranosyl-2,4-dihydroxy-6-oxocyclohexa-2,4-dienyl acetic acid; D000872:Anthocyanins; D003512:Cyclohexanones; D005960:Glucosides; C458419:malvidin-3-glucoside