A novel glutathione-hydroxycinnamic acid product generated in oxidative wine conditions

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 49, 2012, Pages 12186-12195

  Bouzanquet, Quentin ^a,b   Barril, Celia ^b   Clark, Andrew C ^b   Dias, Daniel A ^c   Scollary, Geoffrey R ^b,c  

^a Laboratoire Biosol   (France)

^b CHARLES STURT UNIVERSITY   (Australia)

^c UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

4 (E) 2 (S) glutathionyl ethenyl catechol; ascorbic acid; GEC; glutathione; hydroxycinnamic acid; oxidation; wine

Indexed keywords

ACID PRODUCTS; ASCORBIC ACIDS; CAFFEIC ACIDS; CHLOROGENIC ACIDS; CINNAMIC ACIDS; COUMARIC ACID; CRITICAL COMPONENT; GEC; GLUTATHIONES; LC-MS/MS; OXIDATION MECHANISMS; RADICAL MECHANISM; TARTARIC ACIDS; TRACE AMOUNTS; WHITE WINES;

ETHANOL; ORGANIC ACIDS; OXIDATION; PHENOLS; STYRENE; WINE;

PEPTIDES;

4 ((E) 2' (S) GLUTATHIONYL ETHENYL)CATECHOL; 4-((E)-2'-(S)-GLUTATHIONYL ETHENYL)CATECHOL; ALCOHOL; ASCORBIC ACID; CATECHIN; CATECHOL DERIVATIVE; CHLOROGENIC ACID; COUMARIC ACID; DRUG DERIVATIVE; GLUTATHIONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; TANDEM MASS SPECTROMETRY; WINE;

ASCORBIC ACID; CATECHIN; CATECHOLS; CHLOROGENIC ACID; COUMARIC ACIDS; ETHANOL; GLUTATHIONE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; TANDEM MASS SPECTROMETRY; WINE;

EID: 84870869539     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf3034072     Document Type: Article

References (54)

1. Danilewicz, J. C. Mechanism of autoxidation of polyphenols and participation of sulfite in wine: key role of iron Am. J. Enol. Vitic. 2011, 62 (3) 319-328
2. RibeÌreau-Gayon, P.; Dubourdieu, D.; DoneÌche, B.; Lonvaud, A. In Handbook of Enology. The Microbiology of Wine and Vinifications; Wiley: Hoboken, NJ, 2006; Vol. 1, pp 193-203, 212-216.
3. Romano, P.; Suzzi, G. Sulfur dioxide and wine microorganisms. In Wine Microbiology and Technology; Fleet, G. H., Ed.; Harwood Academic Publishers: Victoria, Australia, 1993; pp 373-394.
4. 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
5. Barril, C.; Clark, A. C.; Scollary, G. R. Chemistry of ascorbic acid and sulfur dioxide as an antioxidant system relevant to white wine Anal. Chim. Acta 2012, 732, 186-193
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, 51 (6) 479-498
7. 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 processess in a model wine system: ascorbic acid, erythorbic acid, (+)-catechin and epicatechin J. Agric. Food Chem. 2010, 58 (2) 1004-1011
8. 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
9. Skouroumounis, G. K.; Kwiatkowski, M. J.; Francis, I. L.; Oakey, H.; Capone, D. L.; Peng, Z.; Duncan, B.; Sefton, M. A.; Waters, E. J. The influence of ascorbic acid on the composition, colour and flavour properties of a Riesling and a wooded Chardonnay wine over five years storage Aust. J. Grape Wine Res. 2005, 11, 355-368
10. Ugliano, M.; Kwiatkowski, M. J.; Vidal, S.; Capone, D.; Siebert, T.; Dieval, J.-B.; Aagaard, O.; Waters, E. J. 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 J. Agric. Food Chem. 2011, 59 (6) 2564-2572
11. Singleton, V. L.; Salgues, M. J.; Zaya, J.; Trousdale, E. K. Caftaric acid disappearance and conversion to products of enzymic oxidation in grape must and wine Am. J. Enol. Vit. 1985, 36 (1) 50-56
12. Pierpoint, W. S. The enzymic oxidation of chlorogenic acid and some reactions of the quinone produced Biochem. J. 1966, 98, 567
13. Sonni, F.; Moore, E. G.; Clark, A. C.; Chinnici, F.; Riponi, C.; Scollary, G. R. Impact of glutathione on the formation of methylmethine- and carboxymethine-bridged (+)-catechin dimers in a model wine system J. Agric. Food Chem. 2011, 59 (13) 7410-7418
14. 13C-NMR and X-ray absorption studies of copper(I) glutathione complexes Eur. J. Biochem. 1996, 236, 697-705
15. Smith, R. C.; Reed, V. D.; Hill, W. E. Oxidation of thiols by copper(II) Phosphorus, Sulfur Silicon Relat. Elem. 2006, 90, 147-154
16. Speisky, H.; Gómez, M.; Carrasco-Pozo, C.; Pastene, E.; Lopez-Alarcón, C.; Olea-Azar, C. Cu(I)-glutathione complex: a potential source of superoxide radicals generation Bioorg. Med. Chem. 2008, 16 (13) 6568-6574
17. 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
18. Cheynier, V.; Trousdale, E. K.; Singleton, V. L.; Salgues, M. J.; Wylde, R. Characterization of 2- S -glutathionylcaftaric acid and its hydroxylsis in relation to grape wines J. Agric. Food Chem. 1986, 34, 217-221
19. Fujimoto, A.; Masuda, T. Chemical interaction between polyphenols and a cysteinyl thiol under radical oxidation conditions J. Agric. Food Chem. 2012, 60, 5142-5151
20. Gislason, N. E.; Currie, B. L.; Waterhouse, A. L. Novel antioxidant reactions of cinnamates in wine J. Agric. Food Chem. 2011, 59, 6221-6226
21. 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 reactions with (+)-catechin Food Chem. 2007, 105, 968-975
22. 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
23. Cilliers, J. J. L.; Singleton, V. L. Nonenzymatic autoxidative phenolic browning reactions in a caffeic acid model system J. Agric. Food Chem. 1989, 37, 890-896
24. Cilliers, J. J. L.; Singleton, V. L. Characterisation of the products of nonenzymic autoxidative phenolic reactions in a caffeic acid model system J. Agric. Food Chem. 1991, 39, 1298-1303
25. Fulcrand, H.; Cheminat, A.; Brouillard, R.; Cheynier, V. Characterisation of compounds obtained by chemical oxidation of caffeic acid in acidic conditions Phytochemistry 1994, 35, 499-505
26. Tazaki, H.; Taguchi, D.; Hayashida, T.; Nabeta, K. Stable isotope-labelling studies on the oxidative coupling of caffeic acid via o -quinone Biosci., Biotechnol., Biochem. 2001, 65, 2613-2621
27. Zoecklein, B. W.; Fugelsang, K. C.; Gump, B. H.; Nury, F. S. In Wine Analysis and Production; Chapman and Hall: New York, 1995; pp 117.
28. Ough, C. S.; Amerine, M. A. In Methods for Analysis of Musts and Wines; Wiley: New York, 1988; pp 213-219.
29. 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
30. du Toit, W. J.; Lisjak, K.; Stander, M.; Prevoo, D. Using LC-MSMS to assess glutathione levels in South African white grape juices and wines made with different levels of oxygen J. Agric. Food Chem. 2007, 55, 2765-2769
31. Fracassetti, D.; Lawrence, N.; Tredoux, A. G. J.; Tirelli, A.; Nieuwoudt, H. H.; du Toit, W. J. Quantification of glutathione, catechin and caffeic acid in grape juice and wine by a novel ultra-performance liquid chromagraphy method Food Chem. 2011, 128, 1136-1142
32. Hao, R. Y.; Liu, Y. L.; Wang, Z. Y.; Zhana, R. R. Construction of self-cloning, indigenous wine strains of Saccharomyces cerevisiae with enhanced glycerol and glutathione production Biotechnol. Lett. 2012, 34, 1711-1717
33. Kritzinger, E. C. Winemaking practices affecting glutathione concentrations in white wine. Ph.D. Thesis, Stellenbosch University, Stellenbosch, March 2012.
34. 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
35. Thakur, S. S.; Balaram, P. Fragmentation of peptide disulfides under conditions of negative ion mass spectrometery: studies of oxidized glutathione and contryphan J. Am. Soc. Mass Spectrom. 2008, 19, 358-366
36. Bolton, J. L.; Acay, N. M.; Vukomanovic, V. Evidence that 4-Allyl- o -quinones spontaneously rearrange to their more electrophilic quinone methides: potential bioactive mechanism for the hepatocarcinogen safrole Chem. Res. Toxicol. 1994, 7, 443-450
37. Betés-Saura, C.; Andrés-Lacueva, C.; Lamuela- Raventós, R. M. Phenolics in white free run juices and wines from Penedés by high-performance liquid chromatography: Changes during vinification J. Agric. Food Chem. 1996, 44, 3040-3046
38. Inoue, H.; Otsu, T. Sulfur-containing vinyl monomers. XII. Charge-transfer complexes of thioethylene derivatives with π-electron acceptors J. Polym. Sci. 1976, 14, 833-844
39. Augusto, O.; de Menezes, S. L.; Linares, E.; Romero, N.; Radi, R.; Denicola, A. EPR detection of glutathiyl and hemoglobin-cysteinyl radicals during the interaction of peroxynitrite with human erythrocytes Biochemistry 2002, 41, 14323-14328
40. Huvaere, K.; Andersen, M. L.; Storme, M.; Bocxlaer, J. V.; Skibsted, L. H.; De Keukeleire, D. Flavin-induced photodecomposition of sulfur-containing amino acids is decisive in the formation of beer lightstruck flavor Photochem. Photobiol. Sci. 2006, 5, 961-969
41. Muraoka, S.; Miura, T. Salicylic acid-induced inactivation of creatine kinase in the presence of lactoperoxidase and hydrogen peroxide Chem.-Biol. Int. 2005, 151, 63-70
42. El-Ayaan, U.; Linert, W. A kinetic study of the reaction between glutathione and iron(III) in the pH range from 1 to 3 J. Coord. Chem. 2002, 55 (11) 1309-1314
43. Hamed, M. Y.; Silver, J.; Wilson, M. T. Studies of the reactions of ferric iron with glutathione and some related thiols Inorg. Chim. Acta 1983, 78, 1-11
44. Oswald, A. A.; Hudson, B. E.; Rodgers, G.; Noel, F. Organic sulfur compounds. VII. Some addition and co-oxidation reactions of thiols with 2,5-dimethyl-2,4-hexadiene J. Org. Chem. 1962, 27, 2439-2448
45. Stock, B. H.; Schreiber, J.; Guenat, C.; Mason, R. P.; Bend, J. R.; Eling, T. E. Evidence for a free radical mechanism of stryene-glutathione conjugate formation catalyzed by prostaglandin H synthase and horseradish peroxidase J. Biol. Chem. 1986, 261 (34) 15915-15922
46. Hamed, M. Y.; Silver, J. Studies on the reactions of ferric ion with glutathione and some related thiols. Part II. Complex formation in the pH range three to seven Inorg. Chim. Acta 1983, 80, 115-122
47. 1 complexes J. Chem. Soc., Perkins Trans. 2 1999, 1115-1121
48. Jiménez, I.; Speisky, H. Effects of copper ions on the free radical-scavenging properties of reduced glutathione: implications of a complex formation J. Trace Elem. Med. Biol. 2000, 14 (3) 161-167
49. Everett, S. A.; Dennis, M. F.; Patel, K. B.; Maddix, S.; Kundu, S. C.; Willson, R. L. Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β-carotene J. Biol. Chem. 1996, 271 (8) 3988-3994
50. Aldabalde, V.; Risso, M.; Derrudi, M. L.; Geymonat, F.; Seoane, G.; Gamenara, D.; Saenz-Méndez, P. Organocatalyzed decarboxylation of naturally occcurring cinnamic acids: potential role in flavoring chemicals production Open J. Phys. Chem. 2011, 1, 85-93
51. 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
52. Penna, N. G.; Daudt, C. E.; Henriques, J. A. P. Performance of hydroxycinnamic esters during white wine vinification Pesqui. Agropecu. Bras. 2001, 26, 983-989
53. Castro, C. C.; Gunning, C.; Oliveira, C. M.; Couto, J. A.; Teixeira, J. A.; Martins, R. C.; Ferreira, A. C. S. Saccharomyces cerevisiae oxidative response evaluation by cyclic voltammetry and gas chromatography-mass spectrometry J. Agric. Food Chem. 2012, 60, 7252-7261
54. 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