Reactivity of Cork Extracts with (+)-Catechin and Malvidin-3-O-glucoside in Wine Model Solutions: Identification of a New Family of Ellagitannin-Derived Compounds (Corklins)

J Agric Food Chem. 2017 Oct 4;65(39):8714-8726. doi: 10.1021/acs.jafc.7b02845. Epub 2017 Sep 25.

Abstract

The aim of this study was to evaluate the reactivity of phenolic compounds extracted from cork stoppers to wine model solutions with two major wine components, namely, (+)-catechin and malvidin-3-O-glucoside. Besides the formation of some compounds already described in the literature, these reactions also yielded a new family of ellagitannin-derived compounds, named herein as corklins. This new family of compounds that were found to result from the interaction between ellagitannins in alcoholic solutions and (+)-catechin were structurally characterized by mass spectroscopy, nuclear magnetic resonance, and computational methods.

Keywords: (+)-catechin; NMR; cork stoppers; corklins; ethanol; malvidin-3-O-glucoside; vescalagin; wine.

MeSH terms

  • Anthocyanins / chemistry*
  • Catechin / chemistry*
  • Food Packaging / instrumentation
  • Glucosides / chemistry*
  • Hydrolyzable Tannins / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Phenols / chemistry*
  • Quercus / chemistry*
  • Wine / analysis*

Substances

  • Anthocyanins
  • Glucosides
  • Hydrolyzable Tannins
  • Phenols
  • ellagitannin
  • malvidin-3-glucoside
  • Catechin