Extraction, detection, and quantification of flavano-ellagitannins and ethylvescalagin in a Bordeaux red wine aged in oak barrels

J Agric Food Chem. 2006 Sep 20;54(19):7349-54. doi: 10.1021/jf061724i.


An extraction procedure and an analytical method have been developed to detect and quantify for the first time a series of ellagitannin derivatives formed in wine during aging in oak barrels. The method involves a preliminary purification step on XAD7 HP resin followed by a second purification step on TSK 40 HW gel. The resulting extract is analyzed for compound identification and quantitative determination by high-performance liquid chromatography-electrospray ionization-mass spectrometry in single ion recording mode. Reference compounds, which are accessible through hemisynthesis from the oak C-glycosidic ellagitannin vescalagin, were used to build calibration curves, and chlorogenic acid was selected as an internal standard. This method enabled us to estimate the content of four flavano-ellagitannins and that of another newly identified wine polyphenol, beta-1-O-ethylvescalagin, in a Bordeaux red wine aged for 18 months in oak barrels. All five ellagitannin derivatives are derived from the nucleophilic substitution reaction of vescalagin with the grape flavan-3-ols catechin and epicatechin or ethanol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / analysis*
  • Biphenyl Compounds / chemistry
  • Catechin / chemistry
  • Catechols / analysis*
  • Catechols / chemistry
  • Chromatography, High Pressure Liquid
  • Ethanol / chemistry
  • Food Handling / methods*
  • Hydrolyzable Tannins / analysis*
  • Hydrolyzable Tannins / chemistry
  • Quercus*
  • Spectrometry, Mass, Electrospray Ionization
  • Time Factors
  • Wine / analysis*
  • Wood


  • Biphenyl Compounds
  • Catechols
  • Hydrolyzable Tannins
  • vescalagin
  • Ethanol
  • Catechin