title: Anthocyanone A: a quinone methide derivative resulting from malvidin 3-O-glucoside degradation.
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.
authors.affiliation: Faculté d'Oenologie de Bordeaux, Université Victor Segalen Bordeaux 2, UMR 1219 INRA, 351 Cours de la Libération, 33405 Talence Cedex, France.
authors.forename: Paulo
authors.initials: P
authors.lastname: Lopes
authors.forename: Tristan
authors.initials: T
authors.lastname: Richard
authors.forename: Cédric
authors.initials: C
authors.lastname: Saucier
authors.forename: Pierre-Louis
authors.initials: PL
authors.lastname: Teissedre
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Monti
authors.forename: Yves
authors.initials: Y
authors.lastname: Glories
mesh_terms: 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
chemical_list: C521179:8-glucopyranosyl-2,4-dihydroxy-6-oxocyclohexa-2,4-dienyl acetic acid; D000872:Anthocyanins; D003512:Cyclohexanones; D005960:Glucosides; C458419:malvidin-3-glucoside