Impact of Glutathione on the Formation of Methylmethine- and Carboxymethine-Bridged (+)-Catechin Dimers in a Model Wine System
AuthorSonni, F; Moore, EG; Clark, AC; Chinnici, F; Riponi, C; Scollary, GR
Source TitleJOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
PublisherAMER CHEMICAL SOC
Document TypeJournal Article
CitationsSonni, F., Moore, E. G., Clark, A. C., Chinnici, F., Riponi, C. & Scollary, G. 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), pp.7410-7418. https://doi.org/10.1021/jf200968x.
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C1 - Journal Articles Refereed
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). (1)H 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.
KeywordsInstrumental Methods (excl. Immunological and Bioassay Methods); Analytical Chemistry not elsewhere classified; Wine Chemistry and Wine Sensory Science; Wine Grapes; Beverages (excl. Fruit Juices); Expanding Knowledge in the Chemical Sciences
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