Anthocyanone A:  A Quinone Methide Derivative Resulting from Malvidin 3-O-Glucoside Degradation

Paulo Lopes,† Tristan Richard,‡ Cédric Saucier,*† Pierre-Louis Teissedre,† Jean-Pierre Monti,‡ and Yves Glories†
Facult d'Oenologie de Bordeaux, Universit Victor Segalen Bordeaux2 UMR 1219 INRA, 351 Cours de la Libration, 33405 Talence Cedex, France, and GESVAB, EA 3675, Universit Victor Segalen Bordeaux2, 146 rue Lo Saignat, Bordeaux, 33076, France
J. Agric. Food Chem., 2007, 55 (7), pp 2698–2704
DOI: 10.1021/jf062875o
Publication Date (Web): March 6, 2007
Copyright © 2007 American Chemical Society
†

 Faculté d'Oenologie de Bordeaux.

,
‡

 GESVAB, EA 3675.

,
*

 Corresponding author. E-mail:  saucier@oenologie.u-bordeaux2.fr. Fax:  33-5-40-00-646.

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 °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-β-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.

Keywords: Maldivin 3-O-glucoside; Anthocyanone A; syringic acid; mass spectrometry; NMR

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History

  • Published In Issue April 04, 2007
  • Received for review October 6, 2006. Revised manuscript received January 16, 2007. Accepted January 18, 2007.

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