The influence of stereochemistry of antioxidants and flavanols on oxidation processes in a model wine system: ascorbic acid, erythorbic acid, (+)-catechin and (-)-epicatechin.

Andrew Clark, Jochen Vestner, Celia Barril, Chantal Maury, Paul Prenzler, Geoffrey R. Scollary

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Abstract

The stereochemical influence of antioxidant and flavanol compounds on oxidation processes in a model wine system was studied. The diastereoisomers, ascorbic acid and erythorbic acid, were used as antioxidants in a model wine system containing either (+)-catechin or (')-epicatechin as the oxidizable flavanol compound. Samples were stored at 45 °C for a period of 14 days and analyzed by UV/visible spectrometry, CIELab, UPLC-PDA, and LC-MS. The results showed that less brown oxidative coloration occurred for samples with erythorbic acid for a given flavanol compound, while (+)-catechin provided less yellow coloration for a given antioxidant. Although erythorbic acid was degraded faster than ascorbic acid, it was associated with less decay in the accompanying flavanol compound. Xanthylium cation pigments were identified as the major contributor to color development. Furthermore, the production of pigment precursors, previously identified as furanone-substituted flavanols, was confirmed in all cases and their corresponding xanthylium cation pigments were lower in the presence of erythorbic acid than ascorbic acid. The results demonstrate that erythorbic acid is more efficient at minimizing oxidative color development than ascorbic acid in the model wine system.
Original languageEnglish
Pages (from-to)1004-1011
Number of pages8
JournalJournal of Agricultural and Food Chemistry
Volume58
Issue number2
DOIs
Publication statusPublished - Jan 2010

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Stereochemistry
Wine
Catechin
stereochemistry
epicatechin
flavanols
catechin
Ascorbic Acid
wines
Antioxidants
ascorbic acid
oxidation
antioxidants
Oxidation
Pigments
acids
color
pigments
Cations
cations

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title = "The influence of stereochemistry of antioxidants and flavanols on oxidation processes in a model wine system: ascorbic acid, erythorbic acid, (+)-catechin and (-)-epicatechin.",
abstract = "The stereochemical influence of antioxidant and flavanol compounds on oxidation processes in a model wine system was studied. The diastereoisomers, ascorbic acid and erythorbic acid, were used as antioxidants in a model wine system containing either (+)-catechin or (')-epicatechin as the oxidizable flavanol compound. Samples were stored at 45 °C for a period of 14 days and analyzed by UV/visible spectrometry, CIELab, UPLC-PDA, and LC-MS. The results showed that less brown oxidative coloration occurred for samples with erythorbic acid for a given flavanol compound, while (+)-catechin provided less yellow coloration for a given antioxidant. Although erythorbic acid was degraded faster than ascorbic acid, it was associated with less decay in the accompanying flavanol compound. Xanthylium cation pigments were identified as the major contributor to color development. Furthermore, the production of pigment precursors, previously identified as furanone-substituted flavanols, was confirmed in all cases and their corresponding xanthylium cation pigments were lower in the presence of erythorbic acid than ascorbic acid. The results demonstrate that erythorbic acid is more efficient at minimizing oxidative color development than ascorbic acid in the model wine system.",
author = "Andrew Clark and Jochen Vestner and Celia Barril and Chantal Maury and Paul Prenzler and Scollary, {Geoffrey R.}",
note = "Imported on 12 Apr 2017 - DigiTool details were: month (773h) = Jan 2010; Journal title (773t) = Journal of Agricultural and Food Chemistry. ISSNs: 0021-8561;",
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T1 - The influence of stereochemistry of antioxidants and flavanols on oxidation processes in a model wine system

T2 - ascorbic acid, erythorbic acid, (+)-catechin and (-)-epicatechin.

AU - Clark, Andrew

AU - Vestner, Jochen

AU - Barril, Celia

AU - Maury, Chantal

AU - Prenzler, Paul

AU - Scollary, Geoffrey R.

N1 - Imported on 12 Apr 2017 - DigiTool details were: month (773h) = Jan 2010; Journal title (773t) = Journal of Agricultural and Food Chemistry. ISSNs: 0021-8561;

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N2 - The stereochemical influence of antioxidant and flavanol compounds on oxidation processes in a model wine system was studied. The diastereoisomers, ascorbic acid and erythorbic acid, were used as antioxidants in a model wine system containing either (+)-catechin or (')-epicatechin as the oxidizable flavanol compound. Samples were stored at 45 °C for a period of 14 days and analyzed by UV/visible spectrometry, CIELab, UPLC-PDA, and LC-MS. The results showed that less brown oxidative coloration occurred for samples with erythorbic acid for a given flavanol compound, while (+)-catechin provided less yellow coloration for a given antioxidant. Although erythorbic acid was degraded faster than ascorbic acid, it was associated with less decay in the accompanying flavanol compound. Xanthylium cation pigments were identified as the major contributor to color development. Furthermore, the production of pigment precursors, previously identified as furanone-substituted flavanols, was confirmed in all cases and their corresponding xanthylium cation pigments were lower in the presence of erythorbic acid than ascorbic acid. The results demonstrate that erythorbic acid is more efficient at minimizing oxidative color development than ascorbic acid in the model wine system.

AB - The stereochemical influence of antioxidant and flavanol compounds on oxidation processes in a model wine system was studied. The diastereoisomers, ascorbic acid and erythorbic acid, were used as antioxidants in a model wine system containing either (+)-catechin or (')-epicatechin as the oxidizable flavanol compound. Samples were stored at 45 °C for a period of 14 days and analyzed by UV/visible spectrometry, CIELab, UPLC-PDA, and LC-MS. The results showed that less brown oxidative coloration occurred for samples with erythorbic acid for a given flavanol compound, while (+)-catechin provided less yellow coloration for a given antioxidant. Although erythorbic acid was degraded faster than ascorbic acid, it was associated with less decay in the accompanying flavanol compound. Xanthylium cation pigments were identified as the major contributor to color development. Furthermore, the production of pigment precursors, previously identified as furanone-substituted flavanols, was confirmed in all cases and their corresponding xanthylium cation pigments were lower in the presence of erythorbic acid than ascorbic acid. The results demonstrate that erythorbic acid is more efficient at minimizing oxidative color development than ascorbic acid in the model wine system.

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