Impact of glutathione on the formation of methylmethine-and carboxymethine-bridged (+)-catechin dimers in a model wine system

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 13, 2011, Pages 7410-7418

  Sonni, Francesca ^a   Moore, Evan G ^b   Clark, Andrew C ^c   Chinnici, Fabio ^a   Riponi, Claudio ^a   Scollary, Geoffrey R ^b,c  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF MELBOURNE   (Australia)

^c CHARLES STURT UNIVERSITY   (Australia)

Author keywords

(+) catechin; Browning; glutathione; glyoxylic acid; wine; xanthylium cation

Indexed keywords

(+)-CATECHIN; BROWNING; GLUTATHIONE; GLYOXYLIC ACIDS; XANTHYLIUM CATION;

ACETALDEHYDE; CARBONYL COMPOUNDS; CARBONYLATION; DIMERS; IRON COMPOUNDS; METAL IONS; WINE;

PHENOLS;

ACETALDEHYDE; CATECHIN; GLUTATHIONE; GLYOXYLIC ACID; GLYOXYLIC ACID DERIVATIVE;

ARTICLE; CHEMISTRY; DIMERIZATION; WINE;

ACETALDEHYDE; CATECHIN; DIMERIZATION; GLUTATHIONE; GLYOXYLATES; WINE;

EID: 79960046948     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf200968x     Document Type: Article

References (42)

1. Cheynier, V. Flavonoids in Wine. In Flavonoids Chemistry, Biochemistry and Applications; Anderson, O. M., Markham, K. R., Eds.; CRC Taylor & Francis: London, U.K., 2006; pp 263-318.
2. 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)
3. Maury, C.; Clark, A. C.; Scollary, G. R. Determination of the impact of bottle colour and phenolic concentration on pigment development in white wine stored under external conditions Anal. Chim. Acta 2010, 660, 81-86
4. Saucier, C.; Guerra, C.; Pianet, I.; Laguerre, M.; Glories, Y. (+)-Catechin-acetaldehyde condensation products in relation to wine-ageing Phytochemistry 1997, 46, 229-234 (Pubitemid 27391130)
5. Timberlake, C. F.; Bridle, P. Interactions between anthocyanins, phenolic compounds, and acetaldehyde and their significance in red wines Am. J. Enol. Vitic. 1976, 27, 97-105
6. Wildenradt, H. L.; Singleton, V. L. The production of aldehydes as a result of oxidation of polyphenolic compounds and its relation to wine aging Am. J. Enol. Vit 1974, 25, 119-126
7. Clark, A. C.; Prenzler, P. D.; Scollary, G. R. Impact of the condition of storage of tartaric acid solutions on the production and stability of glyoxylic acid Food Chem. 2007, 102, 905-916 (Pubitemid 46108296)
8. Drinkine, J.; Glories, Y.; Saucier, C. (+)-Catechin-aldehyde condensations: competition between acetaldehyde and glyoxylic acid J. Agric. Food Chem. 2005, 53, 7552-7558 (Pubitemid 41413554)
9. Es-Safi, N.; Cheynier, V.; Moutounet, M. Implication of phenolic reactions in food organoleptic properties J. Food Comp. Anal. 2003, 16, 535-553 (Pubitemid 37080631)
10. Saucier, C.; Bourgeois, G.; Vitry, C.; Roux, D.; Glories, Y. Characterization of (+)-catechin-acetaldehyde polymers: a model for colloidal state of wine polyphenols J. Agric. Food Chem. 1997, 45, 1045-1049 (Pubitemid 127476867)
11. Drinkine, J.; Lopes, P.; Kennedy, J. A.; Teissedre, P.-L.; Saucier, C. Ethylidene-bridged flavan-3-ols in red wine and correlation with wine age J. Agric. Food Chem. 2007, 55, 6292-6299 (Pubitemid 47235689)
12. Mateus, N.; Carvalho, E.; Carvalho, A. R.; Melo, A.; González- Paramás, A. M.; Santos-Buelga, C.; Silva, A. M. S.; Rivas-Gonzalo, J. C.; De Fratas, V. A. P. Isolation and structural characterisation of new acetylated anthocyanin-vinyl-flavanol pigments occurring in aged red wines J. Agric. Food Chem. 2003, 51, 277-282
13. Escribano-Bailón, T.; Álvarez-García, M.; Rivas-Gonzalo, J. C.; Heredia, F. J.; Santos-Buelga, C. Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin J. Agric. Food Chem. 2001, 49, 1213-1217 (Pubitemid 32884936)
14. Es-Safi, N. E.; Guerneve, C.; Labarbe, B.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Structure of a new xanthylium salt derivative Tetra. Lett. 1999, 40, 5869-5872 (Pubitemid 29343843)
15. Es-Safi, N. E.; Guerneve, C.; Labarbe, B.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Xanthylium salts formation involved in wine colour changes Int. J. Food Sci. Technol. 2000, 35, 62-74
16. 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
17. 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)
18. Ribȩreau-Gayon, P.; Dubourdieu, D.; Donȩche, B.; Lonvaud, A. Handbook of Enology: The Microbiology of Wine and Vinifications; John Wiley and Sons Ltd.: Brisbane, Australia, 2006; pp 193-222.
19. Romano, P.; Suzzi, G. Sulfur Dioxide and Wine Microorganisms. In Wine Microbiology and Biotechnology; Fleet, G. H., Ed.; Harwood Academic Publishers: Victoria, Australia, 1993; pp 373-394.
20. Taylor, S. L.; Higley, N. A.; Bush, R. K. Sulphites in foods: uses, analytical methods, residues, fate, exposure assessment, metabolism, toxicity, and hypersensitivity Adv. Food Res. 1986, 30, 1-76
21. Rousis, I. G.; Lambropoulos, I.; Tzimas, P. Protection of volatiles in a wine with low sulfur dioxide by caffeic acid or glutathione Am. J. Enol. Vitic. 2007, 58, 274-278 (Pubitemid 47067163)
22. Ugliano, M.; Kwiatkowski, M. J.; Vidal, S.; Capone, D.; Siebert, T.; Dieval, J.-B.; Aagaard, O.; Waters, E. J. Evolution of 3-mercatohexanol, hydrogen sulfide, and methyl mercaptan during bottle storage of Sauvignon blanc wines. Effect of glutathione, copper, oxygen exposure, and closure-derived oxygen J. Agric. Food Chem. 2011, 59, 2564-2572
23. Patel, P.; Herbst-Johnstone, M.; Lee, S. A.; Garnener, R. C.; Weaver, R.; Nicolau, L.; Kilmartin, P. A. Influence of juice pressing conditions on polyphenols, antioxidants, and varietal aroma of Sauvignon blanc microferments J. Agric. Food Chem. 2010, 58, 7280-7288
24. n J. Agric. Food Chem. 2010, 58, 11483-11492
25. Cheynier, V.; Trousdale, E. K.; Singleton, V. L.; Salgues, M. J.; Wylde, R. Characterization of 2-glutathionylcaftaric acid and its hydrolysis in relation to grape wines J. Agric. Food Chem. 1986, 34, 217-221
26. Lavigne, V.; Pons, A.; Dubourdieu, D. Assay of glutathione in must and wines using capillary electrophoresis and laser-induced fluorescence detection. Changes in concentration in dry white wines during alcoholic fermentation and aging J. Chromatogr., A 2007, 1139, 130-135 (Pubitemid 44940787)
27. Sonni, F.; Clark, A. C.; Prenzler, P. D.; Riponi, C.; Scollary, G. R. Antioxidant action of glutathione and the ascorbic acid/glutathione pair in a model white wine J. Agric. Food Chem. 2011, 59, 3940-3949
28. 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)
29. Kera, Y.; Kiriyama, T.; Komura, S. Conjugation of acetaldehyde with cysteinylglycine, the first metabolite in glutathione breakdown by g-glutamyltranspeptidase Agents Actions 1985, 17, 48-52 (Pubitemid 16179294)
30. 2 catalyzed by L-hydroxy acid oxidase Bioorg. Chem. 1985, 13, 1-13
31. 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)
32. 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
33. 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
34. 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)
35. Liu, S.-Q.; Pilone, G. J. An overview of formation and roles of acetaldehyde in winemaking with emphasis on microbial implications Int. J. Food Sci. Technol. 2000, 35, 49-61
36. Marchand, S.; de Revel, G. A HPLC fluorescence-based method for glutathione derivatives quantification in must and wine Anal. Chim. Acta 2010, 660, 158-163
37. 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
38. Guyot, S.; Vercauteren, J.; Cheynier, V. Structural determination of colourless and yellow dimers resulting from (+)-catechin coupling catalysed by grape polyphenoloxidase Phytochemistry 1996, 42, 1279-1288 (Pubitemid 27063268)
39. Kanchuger, M. S.; Byers, L. D. Acyl substituent effects on thiohemiacetal equilibria J. Am. Chem. Soc. 1979, 101, 3005-3010
40. Burroughs, L. F.; Sparks, A. H. Sulphite-binding power of wines and ciders I. Equilibrium constants for the dissociation of carbonyl bisulphite compounds J. Sci. Food Agric. 1973, 24, 187-198
41. Betterton, E. A.; Erel, Y.; R., H. M. Aldehyde-bisulfite adducts: prediction of some of their thermodynamic and kinetic properties Environ. Sci. Technol. 1988, 22, 92-99 (Pubitemid 18026819)
42. Olson, T. M.; Hoffmann, M. R. Formation kinetics, mechanism, and thermodynamics of glyoxylic acid-S(IV) adducts J. Phys. Chem. 1988, 92, 4246-4253