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

Volumn 60, Issue 10, 2012, Pages 2647-2656

  Nikolantonaki, Maria ^a   Jourdes, Michael ^a   Shinoda, Kentaro ^b   Teissedre, Pierre Louis ^a   Quideau, Stéphane ^c   Darriet, Philippe ^a  

^a EA 4577   (France)

^b SUNTORY LTD   (Japan)

^c UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

oxidation; oxygen; phenolic compounds; polyphenoloxidase; reactivity; volatile thiols

Indexed keywords

ADDITION PRODUCTS; ADDUCT FORMATION; AGING PROCESS; CHEMICAL MECHANISM; CHEMICAL OXIDATION; ENZYMATIC OXIDATIONS; EPICATECHIN; FLAVAN-3-OLS; HPLC-MS; KINETIC STUDY; MODEL SOLUTION; NMR ANALYSIS; PHENOLIC COMPOUNDS; POLYPHENOL OXIDASE; REACTION MECHANISM; VOLATILE THIOLS;

CHEMICAL ANALYSIS; ORGANIC COMPOUNDS; OXIDATION; OXYGEN; REACTIVITY (NUCLEAR); SULFUR; SULFUR DIOXIDE; TRANSPORT PROPERTIES;

PHENOLS;

CAFTARIC ACID; CATECHOL OXIDASE; PHENOL DERIVATIVE; PLANT EXTRACT; THIOL DERIVATIVE; VEGETABLE PROTEIN; VOLATILE ORGANIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION; VITIS;

CATECHOL OXIDASE; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENOLS; PLANT EXTRACTS; PLANT PROTEINS; SULFHYDRYL COMPOUNDS; VITIS; VOLATILE ORGANIC COMPOUNDS;

VITACEAE;

EID: 84858330092     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf204295s     Document Type: Article

References (38)

1. Darriet, P.; Tominaga, T.; Lavigne, V.; Boidron, J. N.; Dubourdieu, D. Identification of a powerful aromatic component of Vitis vinifera L. var. Sauvignon wines: 4-mercapto-4-methylpentan-2-one Flavour Fragrance J. 1995, 10, 385-392
2. Tominaga, T.; Darriet, P.; Dubourdieu, D. Identification of 3-mercaptohexyl acetate in Sauvignon wine, a powerful aromatic compound exhibiting box-tree odor Vitis 1996, 35, 207-210
3. Bouchilloux, P.; Darriet, P.; Henry, R.; Lavigne-Cruege, V.; Dubourdieu, D. Identification of volatile and powerful odorous thiols in Bordeaux red wine varieties J. Agric. Food Chem. 1998, 46, 3095-3099 (Pubitemid 128478866)
4. Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines Flavour Fragrance J. 1998, 13, 159-162 (Pubitemid 28352101)
5. Kotseridis, Y.; Baumes, R. Identification of impact odorants in Bordeaux red grape juice, in the commercial yeast used for Its fermentation, and in the produced wine J. Agric. Food Chem. 2000, 48, 400-406 (Pubitemid 30120373)
6. Tominaga, T.; Baltenweck-Guyot, R.; Peyrot des Gachons, C.; Dubourdieu, D. Contribution of volatile thiols to the aromas of white wines made from several Vitis vinifera grape varieties Am. J. Enol. Vitic. 2000, 51, 178-181 (Pubitemid 30656749)
7. Fretz, C. B.; Luisier, J. L.; Tominaga, T.; Amado, R. 3-Mercaptohexanol: An aroma impact compound of Petite Arvine wine Am. J. Enol. Vitic. 2005, 56, 407-410 (Pubitemid 43015906)
8. Sarrazin, E.; Shinkaruk, S.; Tominaga, T.; Bennetau, B.; Frerot, E.; Dubourdieu, D. Odorous impact of volatile thiols on the aroma of young botrytized sweet wines: identification and quantification of new sulfanyl alcohols J. Agric. Food Chem. 2007, 55, 1437-44
9. Murat, M. L.; Tominaga, T.; Dubourdieu, D. Impact of some components on bordeaux roses and clairets aroma J. Int. Sci. Vigne Vin 2001, 35, 99-105 (Pubitemid 33684578)
10. Tominaga, T.; Darriet, P.; Dubourdieu, D. Identification of 3-mercaptohexyl acetate in Sauvignon wine, a powerful aromatic compound exhibiting box-tree odor Vitis 1996, 35, 207-210
11. Guth, H. Quantification and sensory studies of character impact odorants of different white wine varieties J. Agric. Food Chem. 1997, 45, 3027-3032 (Pubitemid 127481848)
12. Tominaga, T.; Murat, M. L.; Dubourdieu, D. Development of a method for analyzing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. cv. Sauvignon Blanc J. Agric. Food Chem. 1998, 46, 1044-1048 (Pubitemid 128488112)
13. Tominaga, T.; Blanchard, L.; Darriet, P.; Dubourdieu, D. A powerful aromatic volatile thiol, 2-furanmethanethiol, exhibiting roast coffee aroma in wines made from several Vitis vinifera grape varieties J. Agric. Food Chem. 2000, 48, 1799-1802 (Pubitemid 30331527)
14. Tominaga, T.; Guimbertau, G.; Dubourdieu, D. Role of certain volatile thiols in the bouquet of aged champagne wines J. Agric. Food. Chem. 2003, 51, 1016-1020
15. Jocelyn, P. C. Biochemistry of the SH group: The occurrence, chemical properties, metabolism and biological function of thiols and disulfides; Academic Press: London, U.K., 1972.
16. Blank, I.; Pascual, E. C.; Devaud, S.; Fay, L. B.; Stadler, R. H.; Yeretzian, C.; Goodman, B. A. Degradation of the coffee flavor compound furfuryl mercaptan in model Fenton-type reaction systems J. Agric. Food Chem. 2002, 50, 2356-2364 (Pubitemid 34275310)
17. Nikolantonaki, M.; Chichuc, I.; Teissedre, P. L.; Darriet, P. Reactivity of volatile thiols with polyphenols in a wine-model medium: Impact of oxygen, iron, and sulfur dioxide Anal. Chim. Acta 2010, 660, 102-109
18. Sarrazin, E.; Shinkaruk, S.; Pons, M.; Thibon, C.; Bennetau, B.; Darriet, P. Elucidation of the 1,3-sulfanylalcohol oxidation mechanism: An unusual identification of the disulfide of 3-sulfanylhexanol in sauternes botrytized wines J. Agric. Food Chem. 2010, 58, 10606-10613
19. Blanchard, L.; Darriet, P.; Dubourdieu, D. Reactivity of 3-mercaptohexanol in red wine: Impact of oxygen, phenolic fractions, and sulfur dioxide Am. J. Enol. Vitic. 2004, 55, 115-120 (Pubitemid 38927722)
20. Lopes, P.; Silva, M. A.; Pons, A.; Tominaga, T.; Lavigne, V.; Saucier, C.; Darriet, P.; Teissedre, P. L.; Dubourdieu, D. Impact of oxygen dissolved at bottling and transmitted through closures on the composition and sensory properties of a Sauvignon blanc wine during bottle storage J. Agric. Food Chem. 2009, 57, 10261-10270
21. Valero, E.; Sanchez-Ferrer, A.; Varon, R.; Garcia-Carmona, F. Evolution of grape polyphenol oxidase activity and phenolic content during maturation and vinification Vitis 1989, 28, 85-95
22. Kidron, M.; Harel, E.; Mayer, A. M. Catechol oxidase activity in grapes and wine Am. J. Enol. Vitic. 1978, 29, 30-35
23. Cheynier, V.; Trousdale, E.; Singleton, V.; Salgues, M.; Wylde, R. Characterization of 2- S -glutathionyl caftaric acid and its hydrolysis in relation to grape wines J. Agric. Food Chem. 1986, 34, 217-221
24. Charles-Bernard, M.; Kraehenbuehl, K.; Rytz, A.; Roberts, D. D. Interactions between volatile and nonvolatile coffee components. 1. Screening of nonvolatile components J. Agric. Food Chem. 2005, 53, 4417-4425 (Pubitemid 40855466)
25. Salgues, M.; Cheynier, V.; Gunata, Z.; Wylde, R. Oxidation of grape juice 2- S -glutathionyl caffeoyl tartaric acid by Botrytis cinerea laccase and characterization of a new substance: 2,5-di- S -glutathionyl caffeoyl tartaric acid J. Food Sci. 1986, 51, 1191-1194
26. Cilliers, J. J. L.; Singleton, V. L. Caffeic acid autoxidation and the effects of thiols J. Agric. Food Chem. 1990, 38, 1789-1796
27. Quideau, S.; Feldman, K. S.; Appel, H. M. Chemistry of gallotannin-derived o -quinones: Reactivity toward nucleophiles J. Org. Chem. 1995, 60, 4982-4983
28. Moridani, M. Y.; Scobie, H.; Salehi, P.; O'Brien, P. J. Catechin metabolism: Glutathione conjugate formation catalyzed by tyrosinase, peroxidase, and cytochrome P450 Chem. Res. Toxicol. 2001, 14, 841-848 (Pubitemid 32661339)
29. Tanaka, T.; Mine, C.; Inoue, K.; Matsuda, M.; Kouno, I. Synthesis of theaflavin from epicatechin and epigallocatechin by plant homogenates and role of epicatechin quinone in the synthesis and degradation of theaflavin J. Agric. Food Chem. 2002, 50, 2142-2148 (Pubitemid 34260024)
30. Laurie, V. F.; Zúñiga, M. C.; Carrasco-Sánchez, V.; Santos, L. S.; Cañete, Á.; Olea-Azar, C.; Ugliano, M.; Agosin, E. Reactivity of 3-sulfanyl-1-hexanol and catechol-containing phenolics in vitro Food Chem. 2012, 131, 1510-1516
31. Singleton, V. L.; Salgues, M.; Zaya, J.; Trousdale, E. Caftaric acid disappearance and conversion to products of enzymic oxidation in grape must and wine Am. J. Enol. Vitic. 1985, 36, 50-56
32. Cheynier, V.; Basire, N.; Rigaud, J. Mechanism of trans-caffeoyltartaric acid and catechin oxidation in model solutions containing grape polyphenoloxidase J. Agric. Food Chem. 1989, 37, 1069-1071
33. Sayavedra-Soto, L. A.; Montgomery, M. W. Inhibition of Polyphenoloxidase by Sulfite J. Food Sci. 1986, 51, 1531-1536
34. 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)
35. Munoz-Munoz, J. L.; García-Molina, F.; Molina-Alarcón, M.; Tudela, J.; García-Cánovas, F.; Rodríguez-López, J. N. Kinetic characterization of the enzymatic and chemical oxidation of the catechins in green tea J. Agric. Food Chem. 2008, 56, 9215-9224
36. 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)
37. 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. Vitic. 1974, 25, 119-126
38. Oszmianski, J.; Lee, C. Y. Enzymic oxidative reaction of catechin and chlorogenic acid in a model system J. Agric. Food Chem. 1990, 38, 1202-1204