Impact of glutathione on the formation of methylmethine-and carboxymethine-bridged (+)-catechin dimers in a model wine system

Sonni, Francesca, Moore, Evan G., Clark, Andrew C., Chinnici, Fabio, Riponi, Claudio and Scolary, Geoffrey R. (2011) Impact of glutathione on the formation of methylmethine-and carboxymethine-bridged (+)-catechin dimers in a model wine system. Journal of Agricultural and Food Chemistry, 59 13: 7410-7418. doi:10.1021/jf200968x


Author Sonni, Francesca
Moore, Evan G.
Clark, Andrew C.
Chinnici, Fabio
Riponi, Claudio
Scolary, Geoffrey R.
Title Impact of glutathione on the formation of methylmethine-and carboxymethine-bridged (+)-catechin dimers in a model wine system
Journal name Journal of Agricultural and Food Chemistry   Check publisher's open access policy
ISSN 0021-8561
1520-5118
Publication date 2011-07
Year available 2011
Sub-type Article (original research)
DOI 10.1021/jf200968x
Volume 59
Issue 13
Start page 7410
End page 7418
Total pages 9
Place of publication Washington, DC United States
Publisher American Chemical Society
Collection year 2012
Language eng
Formatted abstract
This study was performed to assess the impact of glutathione on the reaction between (+)-catechin and carbonyl compounds in wine-related conditions. (+)-Catechin (0.50 mM) and either glyoxylic acid (0.25 mM) or acetaldehyde (0.25 mM) were added to a model wine system with 0.0, 0.25, and 2.5 mM of glutathione added. UPLC-DAD and LC-MS analysis showed that the formation of carbonyl-bridged (+)-catechin dimers was inhibited in the samples with a glutathione to carbonyl ratio of 10:1 compared to the samples without glutathione. At a ratio of 1:1, glutathione inhibited the acetaldehyde-bridged dimers but only had a minor impact on the glyoxylic acid-bridged dimers. Further investigations showed that this trend of inhibition by glutathione on the glyoxylic acid-derived dimer was independent of temperatures, 20 °C vs 45 °C, or the presence of metal ions, 0.2 mg/L copper(II) and 5 mg/L iron(II). 1H NMR analysis and LC-MS analysis provided evidence that glutathione inhibited dimer formation via different mechanisms depending on the carbonyl compound. For acetaldehyde-derived dimers, the main mode of inhibition was the ability of glutathione to form a (methyl-glutathionyl-methine)-(+)-catechin complex. Alternatively, the formation of a glutathione-glyoxylic acid addition product impeded the reaction between glyoxylic acid with (+)-catechin. These results demonstrate that glutathione, at sufficient concentration, can have a substantial impact on carbonyl-derived polymerization reactions in wine-like conditions
Keyword Browning
Wine
Xanthylium cation
Glutathione
Glyoxylic acid
Sulfur Dioxide Oxidation
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
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Created: Thu, 29 Aug 2013, 19:10:17 EST by Evan Moore on behalf of School of Chemistry & Molecular Biosciences