Measuring protection of aromatic wine thiols from oxidation by competitive reactions vs wine preservatives with ortho-quinones

Food Chemistry

Volumn 163, Issue , 2014, Pages 61-67

  Nikolantonaki, Maria ^a   Magiatis, Prokopios ^b   Waterhouse, Andrew L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

Antioxidants; Ascorbic acid; Glutathione; Nucleophiles; Oxidation; Quinones; Reactivity; Sulphur dioxide; Wine

Indexed keywords

ADDITION REACTIONS; ANTIOXIDANTS; ASCORBIC ACID; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILES; OXIDATION; PEPTIDES; QUINONE; REACTION RATES; REACTIVITY (NUCLEAR); REDOX REACTIONS; SULFUR DETERMINATION; SULFUR DIOXIDE; WINE;

ANTIOXIDANT EFFECT; COMPETITIVE REACTIONS; GLUTATHIONES; NUCLEOPHILIC ADDITIONS; PRODUCT ISOLATION; PROTECTIVE ACTION; SECONDARY PRODUCT; TWO-ELECTRON REDUCTION;

REACTION INTERMEDIATES;

ASCORBIC ACID; FOOD PRESERVATIVE; GLUTATHIONE; PHLOROGLUCINOL; QUINONE DERIVATIVE; SULFUR DIOXIDE; TANNIN; THIOL DERIVATIVE; 4-METHYL-1,2-BENZOQUINONE; ANTIOXIDANT; BENZOQUINONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; ELECTROPHILICITY; ELECTROSPRAY MASS SPECTROMETRY; HETERONUCLEAR MULTIPLE BOND CORRELATION; LIMIT OF QUANTITATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE LIQUID CHROMATOGRAPHY; SYNTHESIS; WINE; ANALYSIS; CHEMISTRY; COMPARATIVE STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROCEDURES;

ANTIOXIDANTS; BENZOQUINONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FOOD PRESERVATIVES; MASS SPECTROMETRY; OXIDATION-REDUCTION; SULFHYDRYL COMPOUNDS; WINE;

EID: 84900821255     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2014.04.079     Document Type: Article

References (27)

1. T. Adachi, H. Nonogi, T. Fuke, M. Ikuzawa, K. Fujita, and T. Izumi et al. On the combination of sulphite with food ingredients (aldehydes, ketones and sugars). II Zeitschrift für Lebensmittel-Untersuchung und Forschung 168 3 1979 200 205
2. R. Arakawa, M. Yamaguchi, H. Hotta, T. Osakai, and T. Kimoto Product analysis of caffeic acid oxidation by on-line electrochemistry/electrospray ionization mass spectrometry Journal of the American Society for Mass Spectrometry 15 8 2004 1228 1236 (Pubitemid 38970067)
3. C. Barril, A.C. Clark, P.D. Prenzler, P. Karuso, and G.R. Scollary Formation of pigment precursor (+)-1″-methylene-6″-hydroxy-2H-furan- 5″-one-catechin isomers from (+)-catechin and a degradation product of ascorbic acid in a model wine system Journal of Agricultural and Food Chemistry 57 20 2009 9539 9546
4. C. Barril, A.C. Clark, and G.R. Scollary Chemistry of ascorbic acid and sulfur dioxide as an antioxidant system relevant to white wine Analytica Chimica Acta 732 2012 186 193
5. L. Blanchard, P. Darriet, and D. Dubourdieu Reactivity of 3-mercaptohexanol in red wine: Impact of oxygen, phenolic fractions, and sulfur dioxide American Journal of Enology and Viticulture 55 2 2004 115 120 (Pubitemid 38927722)
6. Q. Bouzanquet, C. Barril, A.C. Clark, D.A. Dias, and G.R. Scollary A novel glutathione-hydroxycinnamic acid product generated in oxidative wine conditions Journal of Agricultural and Food Chemistry 60 49 2012 12186 12195
7. 2 levels and aromas in a Sauvignon Blanc wine Journal of Agricultural and Food Chemistry 53 26 2005 10006 10011 (Pubitemid 43081210)
8. Lavigne Cruège, V., Pons, A., Chone, X., & Dubourdieu, D. (2003). Rôle du glutathion sur l'évolution aromatique des vins blancs secs. In: 7e Symposium international d'Oenologie, Bordeaux.
9. J.C. Danilewicz, and P.J. Wallbridge Further studies on the mechanism of interaction of polyphenols, oxygen, and sulfite in wine American Journal of Enology and Viticulture 61 2 2010 166 175
10. G.L. Ellman Tissue sulfhydryl groups Archives of Biochemistry and Biophysics 82 1959 70 77
11. A. Escudero, E. Asensio, J. Cacho, and V. Ferreira Sensory and chemical changes of young white wines stored under oxygen. An assessment of the role played by aldehydes and some other important odorants Food Chemistry 77 3 2002 325 331 (Pubitemid 34518426)
12. P. Fernandez-Zurbano, V. Ferreira, C. Pena, A. Escudero, F. Serrano, and J. Cacho Prediction of oxidative browning in white wines as a function of their chemical composition Journal of Agricultural and Food Chemistry 43 11 1995 2813 2817
13. N.S. Isaacs, and R. van Eldik A mechanistic study of the reduction of quinones by ascorbic acid Journal of the Chemical Society, Perkin Transactions 2 8 1997 1465 1468
14. E.C. Kritzinger, F.F. Bauer, and W.J. du Toit Role of glutathione in winemaking: A review Journal of Agricultural and Food Chemistry 61 2 2012 269 277
15. Lavigne, V., & Dubourdieu, D. (2002). Role of glutathione on development of aroma defects in dry white wines. In: 13th international enology symposium, Montpellier).
16. M. Nikolantonaki, and P. Darriet Identification of ethyl 2-sulfanylacetate as an important off-odor compound in white wines Journal of Agricultural and Food Chemistry 59 18 2011 10191 10199
17. M. Nikolantonaki, M. Jourdes, K. Shinoda, P.-L. Teissedre, S. Quideau, and P. Darriet Identification of adducts between an odoriferous volatile thiol and oxidized grape phenolic compounds: Kinetic study of adduct formation under chemical and enzymatic oxidation conditions Journal of Agricultural and Food Chemistry 60 10 2012 2647 2656
18. M. Nikolantonaki, and A.L. Waterhouse A method to quantify quinone reaction rates with wine relevant nucleophiles: A key to the understanding of oxidative loss of varietal thiols Journal of Agricultural and Food Chemistry 60 34 2012 8484 8491
19. C.M. Oliveira, A.C. Silva Ferreira, P. Guedes de Pinho, and T.A. Hogg Development of a potentiometric method to measure the resistance to oxidation of white wines and the antioxidant power of their constituents Journal of Agricultural and Food Chemistry 50 7 2002 2121 2124 (Pubitemid 34260020)
20. A. Pons, V.R. Lavigne, Y. Landais, P. Darriet, and D. Dubourdieu Identification of a sotolon pathway in dry white wines Journal of Agricultural and Food Chemistry 58 12 2010 7273 7279
21. P. Poupard, S. Guyot, S. Bernillon, and C.M.G.C. Renard Characterisation by liquid chromatography coupled to electrospray ionisation ion trap mass spectrometry of phloroglucinol and 4-methylcatechol oxidation products to study the reactivity of epicatechin in an apple juice model system Journal of Chromatography A 1179 2 2008 168 181
22. J.A. Rossi Jr., and V.L. Singleton Flavor effects and adsorptive properties of purified fractions of grape-seed phenols American Journal of Enology and Viticulture 17 4 1966 240 246
23. I.G. Roussis, I. Lambropoulos, and P. Tzimas Protection of volatiles in a wine with low sulfur dioxide by caffeic acid or glutathione American Journal of Enology and Viticulture 58 2 2007 274 278 (Pubitemid 47067163)
24. F. Sonni, A.C. Clark, P.D. Prenzler, C. Riponi, and G.R. Scollary Antioxidant action of glutathione and the ascorbic acid/glutathione pair in a model white wine Journal of Agricultural and Food Chemistry 59 8 2011 3940 3949
25. M. Ugliano, M. Kwiatkowski, S.p. Vidal, D. Capone, T. Siebert, and J.-B. Dieval et al. Evolution of 3-mercaptohexanol, hydrogen sulfide, and methyl mercaptan during bottle storage of Sauvignon blanc wines. Effect of glutathione, copper, oxygen exposure, and closure-derived oxygen Journal of Agricultural and Food Chemistry 59 6 2011 2564 2572
26. R. Walker Sulphiting agents in foods: Some risk/benefit considerations Food Additives and Contaminants 2 1 1985 5 24 (Pubitemid 15105167)
27. A.L. Waterhouse, and V.F. Laurie Oxidation of wine phenolics: A critical evaluation and hypotheses American Journal of Enology and Viticulture 57 3 2006 306 313 (Pubitemid 44496961)