Antioxidant action of glutathione and the ascorbic acid/glutathione pair in a model white wine

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 8, 2011, Pages 3940-3949

  Sonni, Francesca ^a   Clark, Andrew C ^b   Prenzler, Paul D ^b   Riponi, Claudio ^a   Scollary, Geoffrey R ^b,c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b CHARLES STURT UNIVERSITY   (Australia)

^c UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

ascorbic acid; dihydroxybenzaldehyde; glutathione; o quinone; oxidation; vinyl catechol; white wine

Indexed keywords

ASCORBIC ACIDS; DIHYDROXYBENZALDEHYDE; GLUTATHIONES; O-QUINONE; VINYL CATECHOL; WHITE WINE;

DEGRADATION; KETONES; MAMMALS; ORGANIC ACIDS; OXIDATION; OXYGEN; PHENOLS; POLYMERS; SULFUR; SULFUR DIOXIDE;

WINE;

ANTIOXIDANT; ASCORBIC ACID; GLUTATHIONE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COLOR; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ULTRAVIOLET SPECTROPHOTOMETRY; WINE;

ANTIOXIDANTS; ASCORBIC ACID; CHROMATOGRAPHY, LIQUID; COLOR; GLUTATHIONE; MASS SPECTROMETRY; MODELS, CHEMICAL; SPECTROPHOTOMETRY, ULTRAVIOLET; WINE;

EID: 79955033114     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf104575w     Document Type: Article

References (34)

1. Singleton, V. L. Oxygen with phenols and related reactions in musts, wines and model systems: observations and practical implications Am. J. Enol. Vitic. 1987, 38, 69-77
2. Ferreira, A. C. S.; Hogg, T.; de Pinho, P. G. Identification of key odorants related to the typical aroma of oxidation-spoiled white wines J. Agric. Food Chem. 2003, 51, 1377-1381
3. OBrien, V.; Colby, C.; Nygaard, M. Managing oxygen ingress at bottling Wine Ind. J. 2009, 24, 24-29
4. Lopes, P.; Saucier, C.; Teissedre, P.-L.; Glories, Y. Main routes of oxygen ingress through different closures into wine bottles J. Agric. Food Chem. 2007, 55, 5167-5170 (Pubitemid 47056072)
5. Danilewicz, J. C.; Seccombe, J. T.; Whelan, J. Mechanism of interaction of polyphenols, oxygen and sulfur dioxide in model wine and wine Am. J. Enol. Vitic. 2008, 59, 128-136 (Pubitemid 351874266)
6. Bradshaw, M. P.; Barril, C.; Clark, A. C.; Prenzler, P. D.; Scollary, G. R. Ascorbic acid: a review of its chemistry and reactivity in relation to a wine environment. Crit. Rev. Food Sci. Nutr. 2011, (doi: 10.1080/10408391003690559).
7. Bradshaw, M. P.; Prenzler, P. D.; Scollary, G. R.; Cheynier, V. Defining the ascorbic acid crossover from anti-oxidant to pro-oxidant in a model wine matrix containing (+)-catechin J. Agric. Food Chem. 2003, 51, 4126-4132
8. Barril, C.; Clark, A. C.; Scollary, G. R. Understanding the contribution of ascorbic acid to the pigment development in model white wine systems using liquid chromatography with diode array and mass spectrometry detection techniques Anal. Chim. Acta 2008, 621, 44-51
9. Barril, C.; Clark, A. C.; Karuso, P.; Prenzler, P. D. Formation of pigment precursor (+)-1′′-methylene-6′′-hydroxy-2 H -furan-5′′-one-catechin isomers from (+)-catechin and a degradation product of ascorbic acid in a model wine system J. Agric. Food Chem. 2009, 57, 9539-9546
10. Clark, A. C.; Pedretti, F.; Prenzler, P. D.; Scollary, G. R. Impact of ascorbic acid on the oxidative colouration and associated reactions of a model wine solution containing (+)-catechin, caffeic acid and iron Aust. J. Grape Wine Res. 2008, 14, 238-249
11. Jackson, R. S. Wine Science. Principles and Applications; Academic Press: Burlington, MA, 2008; pp 316 and 697.
12. Makhotkina, O.; Kilmartin, P. A. Uncovering the influence of antioxidants on polyphenol oxidation in wines using an electrochemical method: cyclic voltammetry J. Electroanal. Chem. 2009, 633, 165-174
13. Cheynier, V. F.; Van Hulst, W. J. Oxidation of trans -caftaric acid and 2- S -glutathionylcaftaric acid in model solutions J. Agric. Food Chem. 1988, 36, 10-15
14. Winterbourn, C. C.; Metodiewa, D. Reactivity of biologically important thiol compounds with superoxide and hydrogen peroxide Free Radical Biol. Med. 1999, 27, 322-328 (Pubitemid 29395424)
15. Kanchuger, M. S.; Byers, L. D. Acyl substituent effects on thiohemiacetal equilibria J. Am. Chem. Soc. 1979, 101, 3005-3010
16. 2 catalyzed by L-hydroxy acid oxidase Bioorg. Chem. 1985, 13, 1-13
17. Cilliers, J. J. L.; Singleton, V. L. Caffeic acid autoxidation and the effects of thiols J. Agric. Food Chem. 1990, 38, 1789-1796
18. Simpson, R. F. Factors affecting oxidative browning of white wine Vitis 1982, 21, 233-239
19. Danilewicz, J. C. Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: central role of iron and copper Am. J. Enol. Vitic. 2003, 54, 73-85 (Pubitemid 36689421)
20. Clark, A. C.; Scollary, G. R. Copper(II)-mediated oxidation of (+)-catechin in a model white wine system Aust. J. Grape Wine Res. 2002, 8, 186-195 (Pubitemid 135710956)
21. Clark, A. C.; Vestner, J.; Barril, C.; Maury, C.; Prenzler, P. D.; Scollary, G. R. The influence of stereochemistry of antioxidants and flavanols on oxidation processes in a model wine system: ascorbic acid, erythorbic acid, (+)-catechin and (-)-epicatechin J. Agric. Food Chem. 2010, 58, 1004-1011
22. Zoecklein, B. W.; Fugelsang, K. C.; Gump, B. H.; Nury, F. S. Wine Analysis and Production; Champman and Hall: New York, 1995; p 117.
23. Ough, C. S.; Amerine, M. A. Methods for analysis of musts and wines, Wiley: New York, 1988; pp 213 - 219.
24. Danilewicz, J. C. Interaction of sulfur dioxide, polyphenols, and oxygen in a wine-model system: central role of iron and copper Am. J. Enol. Vitic. 2007, 58, 53-60 (Pubitemid 46761184)
25. du Toit, W. J.; Lisjak, K.; Stander, M.; Prevoo, D. Using LC-MSMS to assess glutathione leves in South African white grape juices and wines made with different levels of oxygen J. Agric. Food Chem. 2007, 55, 2765-2769 (Pubitemid 46668276)
26. Miller, J. N.; Miller, J. C. Statistics for Analytical Chemistry; Elllis Horwood: New York, 1993; pp 43 and 55.
27. Moridani, M. Y.; Scobie, H.; Salehi, P.; OBrien, P. J. Catechin metabolism: Glutathione conjugate formation catalysed by tyrosinase, peroxidase, and cytochrome P450 Chem. Res. Toxicol. 2001, 14, 841-848 (Pubitemid 32661339)
28. Clark, A. C.; Prenzler, P. D.; Scollary, G. R. The role of copper(II) in the bridging reactions of (+)-catechin by glyoxylic acid in a model white wine J. Agric. Food Chem. 2003, 51, 6204-6210
29. Fulcrand, H.; Cheynier, V.; Oszmianski, J.; Moutounet, M. An oxidised tartaric acid residue as a new bridge potentially competing with acetaldehyde in flavan-3-ol condensation Phytochemistry 1997, 46, 223-227 (Pubitemid 27391129)
30. n J. Agric. Food Chem. 2010, 58, 11483-11492
31. Lutter, M.; Clark, A. C.; Prenzler, P. D.; Scollary, G. R. Oxidation of caffeic acid in a wine-like medium: production of dihydroxybenzaldehyde and its subsequent reaction with (+)-catechin Food Chem. 2007, 105, 968-975 (Pubitemid 47069734)
32. George, N.; Clark, A. C.; Prenzler, P. D.; Scollary, G. R. Factors influencing the production and stability of xanthylium cation pigments in a model white wine system Aust. J. Grape Wine Res. 2006, 12, 57-68
33. Schwarz, M.; Wabnitz, T. C.; Winterhalter, P. Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines J. Agric. Food Chem. 2003, 51, 3682-3687
34. T Food Chem. 2008, 107, 1393-1398 (Pubitemid 350166756)