Oxidation of Wine Phenolics: A Critical Evaluation and Hypotheses

Oxidation reactions involving phenolics might change the chemical and sensory profile of wines. While oxidation is a long-standing problem in winemaking, a definitive understanding of its chemical mechanisms is lacking, and such an understanding could allow us to better predict and control wine aging. We briefly summarize and discuss the current knowledge on the chemistry of wine phenolic oxidation and propose, along with other researchers, a new, comprehensive scheme in which the Fenton reaction and hydroxyl radicals have an essential role. This hypothesis suggests that catalytic iron converts wine’s hydrogen peroxide into hydroxyl radical. This leads to a much stronger and less selective oxidant that could react with almost all wine components, in proportion to their concentration and with little selectivity for antioxidant properties. This reaction could produce many electrophilic oxidation products, mainly aldehydes and ketones, that could further modify the chemical composition and sensory perception of wine. While the brevity of this report precludes a full review of oxidation, our aim is to stimulate more study and debate on the mechanisms in wine oxidation chemistry.

[1]  M. Moutounet,et al.  Les apports d'oxygène au cours des traitements des vins. Bilan des observations sur site, 1ère partie. , 2001 .

[2]  V. Cheynier,et al.  New phenolic compounds formed by evolution of (+)-catechin and glyoxylic acid in hydroalcoholic solution and their implication in color changes of grape-derived foods. , 2000, Journal of agricultural and food chemistry.

[3]  V. L. Singleton Oxygen with Phenols and Related Reactions in Musts, Wines, and Model Systems: Observations and Practical Implications , 1987, American Journal of Enology and Viticulture.

[4]  H. Hill,et al.  [1] Chemistry of dioxygen , 1984 .

[5]  L. Butler,et al.  Rapid visual estimation and spectrophotometric determination of tannin content of sorghum grain , 1977 .

[6]  A. Waterhouse,et al.  A Standard Red Wine: Monomeric Phenolic Analysis of Commercial Cabernet Sauvignon Wines , 1999, American Journal of Enology and Viticulture.

[7]  A. Waterhouse The Phenolic Wine Antioxidants , 2001 .

[8]  A. K. Rodopulo [Oxidation of tartaric acid in wine in the presence of heavy metal salts (activation of oxygen by iron)]. , 1951, Izvestiia Akademii nauk SSSR. Seriia biologicheskaia.

[9]  G. Troup,et al.  Free radical scavenging abilities of beverages , 2007 .

[10]  H. Berg,et al.  Some Factors Involved in Browning of White Wines , 1956, American Journal of Enology and Viticulture.

[11]  Tetsushi Watanabe,et al.  Active oxygens generation by flavonoids. , 1998, Biological & pharmaceutical bulletin.

[12]  Y. Glories,et al.  (+)-Catechin—acetaldehyde condensation products in relation to wine-ageing , 1997 .

[13]  J. Oszmiański,et al.  Iron-Catalyzed Oxidation of (+)-Catechin in Model Systems , 1996 .

[14]  H. Fenton,et al.  LXXIII.—Oxidation of tartaric acid in presence of iron , 1894 .

[15]  P. Ribereau-gayon,et al.  Handbook of Enology , 2001 .

[16]  V. L. Singleton,et al.  Contributions of Grape Phenols to Oxygen Absorption and Browning of Wines , 1966 .

[17]  Núria Sagristà,et al.  Iron, Copper, and Manganese Influence on Wine Oxidation , 1995, American Journal of Enology and Viticulture.

[18]  M. Castellari,et al.  Evolution of Phenolic Compounds in Red Winemaking as Affected by Must Oxygenation , 1998, American Journal of Enology and Viticulture.

[19]  Véronique Cheynier,et al.  Effect of oxygenation on polyphenol changes occurring in the course of wine-making , 2002 .

[20]  C. F. Timberlake,et al.  Interactions Between Anthocyanins, Phenolic Compounds, and Acetaldehyde and Their Significance in Red Wines , 1976, American Journal of Enology and Viticulture.

[21]  V. L. Singleton,et al.  Caftaric Acid Disappearance and Conversion to Products of Enzymic Oxidation in Grape Must and Wine , 1985, American Journal of Enology and Viticulture.

[22]  C. Fraga,et al.  Influence of oligomer chain length on the antioxidant activity of procyanidins. , 2000, Biochemical and biophysical research communications.

[23]  D. Dubourdieu,et al.  Reactivity of 3-Mercaptohexanol in Red Wine: Impact of Oxygen, Phenolic Fractions, and Sulfur Dioxide , 2004, American Journal of Enology and Viticulture.

[24]  V. Cheynier,et al.  Competition between (+)-catechin and (-)-epicatechin in acetaldehyde-induced polymerization of flavanols. , 1999, Journal of agricultural and food chemistry.

[25]  G. Troup,et al.  Free radicals in red wine, but not in white? , 1994, Free radical research.

[26]  C. F. Timberlake,et al.  Isolation, Identification, and Characterization of New Color-Stable Anthocyanins Occurring in Some Red Wines , 1997 .

[27]  D. Makris,et al.  Heat-induced, metal-catalyzed oxidative degradation of quercetin and rutin (Quercetin 3-O-rhamnosylglucoside) in aqueous model systems. , 2000, Journal of agricultural and food chemistry.

[28]  V. L. Singleton,et al.  Oxidation of Wines. I. Young White Wines Periodically Exposed to Air , 1979, American Journal of Enology and Viticulture.

[29]  L. Skibsted,et al.  Electron spin resonance spin trapping identification of radicals formed during aerobic forced aging of beer , 1998 .

[30]  O. Wilde,et al.  “Food Additives” , 1951 .

[31]  D. Frank,et al.  Trace metal studies of selected white wines: an alternative approach , 2002 .

[32]  P. Prenzler,et al.  Ascorbic acid-induced browning of (+)-catechin in a model wine system. , 2001, Journal of agricultural and food chemistry.

[33]  M. Ono,et al.  Technological Approach to Improve Beer Flavor Stability: Analysis of the Effect of Brewing Processes on Beer Flavor Stability by the Electron Spin Resonance Method , 2000 .

[34]  V. Cheynier,et al.  Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3-O-glucoside in a model solution system. , 1999, Journal of agricultural and food chemistry.

[35]  M. Ono,et al.  Technological Approach to Improve Beer Flavor Stability: Adjustments of Wort Aeration in Modern Fermentation Systems Using the Electron Spin Resonance Method , 2000 .

[36]  T. Osawa,et al.  Detection of Free Radicals in Beer Oxidation , 1988 .

[37]  John C. Danilewicz,et al.  Review of Reaction Mechanisms of Oxygen and Proposed Intermediate Reduction Products in Wine: Central Role of Iron and Copper , 2003, American Journal of Enology and Viticulture.

[38]  M. Ono,et al.  Improvement for oxidative flavor stability of beer: role of OH-radical in beer oxidation , 1996 .

[39]  P. Ribereau-gayon,et al.  The chemistry of wine stabilization and treatments , 2006 .

[40]  K. Unoura,et al.  Oxidation of Ethanol Induced by Simple Polyphenols : Prooxidant Property of Polyphenols , 2004 .

[41]  V. Cheynier,et al.  A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. , 1998, Phytochemistry.

[42]  V. Cheynier,et al.  Study of the acetaldehyde induced polymerisation of flavan-3-ols by liquid chromatography-ion spray mass spectrometry , 1996 .

[43]  K. Kano,et al.  Kinetic analysis and mechanistic aspects of autoxidation of catechins. , 2002, Biochimica et biophysica acta.

[44]  V. L. Singleton,et al.  The Production of Aldehydes as a Result of Oxidation of Polyphenolic Compounds and its Relation to Wine Aging , 1974, American Journal of Enology and Viticulture.