A novel glutathione-hydroxycinnamic acid product generated in oxidative wine conditions

Bouzanquet, Q, Barril, C, Clark, A, Dias, D and Scollary, G 2012, 'A novel glutathione-hydroxycinnamic acid product generated in oxidative wine conditions', Journal of Agricultural and Food Chemistry, vol. 60, no. 49, pp. 12186-12195.


Document type: Journal Article
Collection: Journal Articles

Title A novel glutathione-hydroxycinnamic acid product generated in oxidative wine conditions
Author(s) Bouzanquet, Q
Barril, C
Clark, A
Dias, D
Scollary, G
Year 2012
Journal name Journal of Agricultural and Food Chemistry
Volume number 60
Issue number 49
Start page 12186
End page 12195
Total pages 10
Publisher American Chemical Society
Abstract This study characterizes a novel glutathione-substituted dihydroxyphenyl compound formed during the oxidation of white wine and model wine solutions, which may contribute to the synergistic role of glutathione and hydroxycinnamic acids in delaying oxidative coloration. The critical components for the formation of the compound were found to be hydroxycinnamic acids and glutathione, while ascorbic acid enabled the product to accumulate to higher concentrations. The presence of the wine components important in other wine oxidation mechanisms, (+)-catechin, ethanol and/or tartaric acid, was not essential for the formation of this new compound. Via LC-MS/MS, HR-MS and 1H NMR (1D and 2D NMR) analyses, the major isomer of the compound formed from glutathione and caffeic acid was found to be 4-[(E)-2'-(S)-glutathionyl ethenyl]-catechol (GEC). Equivalent products were also confirmed via LC-MS/MS for other hydroxycinnamic acids (i.e., ferulic and coumaric acids). Only trace amounts of GEC were formed with the quinic ester of caffeic acid (i.e., chlorogenic acid), and no equivalent product was found for cinnamic acid. GEC was detected in a variety of white wines supplemented with glutathione and caffeic acid. A radical mechanism for the formation of the styrene-glutathione derivatives is proposed.
Subject Wine Chemistry and Wine Sensory Science
Analytical Chemistry not elsewhere classified
Keyword(s) ascorbic acid
glutathione
wine
oxidation
4-[(E)-2'S)-glutathionyl ethenyl]-catechol
hydroxycinnamic acid
GEC
DOI - identifier 10.1021/jf3034072
Copyright notice © 2012 American Chemical Society
ISSN 1520-5118
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