Identification by mass spectrometry of new compounds arising from the reactions involving malvidin-3-glucoside-(O)-catechin, catechin and malvidin-3-glucoside

Rapid Commun Mass Spectrom. 2012 Sep 30;26(18):2123-30. doi: 10.1002/rcm.6330.

Abstract

Rationale: The aim of this work was to study the putative reactions that could occur in red wines between malvidin-3-glucoside-(O)-catechin (mv3glc-(O)-cat) adduct and catechin (cat) or malvidin-3-glucoside (mv3glc) in presence of acetaldehyde.

Methods: Mv3glc-(O)-cat adduct (1 mM) was incubated with catechin (or mv3glc) in the presence of acetaldehyde (molar ratio of 1:4:10) in 12% ethanol/water at pH 3.2, protected from light and placed in the oven at 30 °C. The formation of the new compounds was monitored by liquid chromatography-diode-array detection/electrospray ionization mass spectrometry (LC-DAD/ESI-MS) analysis in the positive and negative ion mode.

Results: The LC-DAD/ESI-MS characterization allowed the confirmation of the structures of the methylmethine-linked cat-mv3glc-(O)-cat ([M-H](-) m/z 1097) and mv3glc-mv3glc-(O)-cat ([M](+) m/z 1301) adducts.

Conclusions: The studies performed in model solutions showed that the colorless mv3glc-(O)-cat adduct can undergo some of the characteristic reactions of anthocyanins and flavan-3-ols that occur in red wine in the presence of acetaldehyde forming new methylmethine-bridged compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / analysis
  • Anthocyanins / chemistry*
  • Catechin / chemistry*
  • Chromatography, High Pressure Liquid
  • Flavonoids / chemistry*
  • Glucosides / chemistry*
  • Hot Temperature
  • Mass Spectrometry / methods*
  • Wine / analysis

Substances

  • Anthocyanins
  • Flavonoids
  • Glucosides
  • catechin-(4,8)-malvidin-3-O-glucoside
  • malvidin-3-glucoside
  • Catechin
  • Acetaldehyde