Efficacy of chitosan in inhibiting the oxidation of (+)-catechin in white wine model solutions

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 40, 2014, Pages 9868-9875

  Chinnici, Fabio ^a   Natali, Nadia ^a   Riponi, Claudio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

(+) catechin; chitosan; oxidation; sulfite; varietal thiols; white wine

Indexed keywords

OXIDATION;

(+)-CATECHIN; MODEL SOLUTION; SULFITE; VARIETAL THIOLS; WHITE WINES;

CHITOSAN;

CATECHIN; CHITOSAN; FOOD ADDITIVE; METAL; PHENOL DERIVATIVE; SOLUTION AND SOLUBILITY; SULFITE; THIOL DERIVATIVE;

CHEMISTRY; COLOR; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; METABOLISM; OXIDATION REDUCTION REACTION; PROCEDURES; SOLUTION AND SOLUBILITY; WINE;

CATECHIN; CHITOSAN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLOR; FOOD ADDITIVES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; METALS; OXIDATION-REDUCTION; PHENOLS; SOLUTIONS; SULFHYDRYL COMPOUNDS; SULFITES; WINE;

EID: 84907931048     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf5025664     Document Type: Article

References (41)

1. Tao, Y.; García, J. F.; Sun, D.-W. Advances in wine aging technologies for enhancing wine quality and accelerating wine aging process Crit. Rev. Food Sci. Nutr. 2014, 54, 817-835
2. Gómez-Plaza, E.; Cano-López, M. A review on micro-oxygenation of red wines: Claims, benefits and the underlying chemistry Food Chem. 2011, 125, 1131-1140
3. Waterhouse, A. L.; Laurie, V. F. Oxidation of wine phenolics: A critical evaluation and hypotheses Am. J. Enol. Vitic. 2006, 57, 306-313
4. Oliveira, C. M.; Ferreira, A. C. S.; De Freitas, V.; Silva, A. M. S. Oxidation mechanisms occurring in wines Food Res. Int. 2011, 44, 1115-1126
5. Bueno, M.; Culleré, L.; Cacho, J.; Ferreira, V. Chemical and sensory characterization of oxidative behavior in different wines Food Res. Int. 2010, 43, 1423-1428
6. Ugliano, M. Oxygen contribution to wine aroma evolution during bottle aging J. Agric. Food Chem. 2013, 61, 6125-6136
7. Herbst-Johnstone, M.; Nicolau, L.; Kilmartin, P. A. P. A. Stability of varietal thiols in commercial Sauvignon Blanc wines Am. J. Enol. Vitic. 2011, 62, 495-502
8. 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
9. 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
10. Es-Safi, N.-E.; Le Guernevé, C.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Xanthylium salts formation involved in wine colour changes Int. J. Food Sci. Technol. 2000, 35, 63-74
11. Es-Safi, N.-E.; Le Guernevé, C.; Fulcrand, H.; Cheynier, V.; Moutounet, M. New polyphenolic compounds with xanthylium skeletons formed through reaction between (+)-catechin and glyoxylic acid J. Agric. Food Chem. 1999, 47, 5211-5217
12. Barril, C.; Clark, A. C.; Prenzler, P. D.; Karuso, P.; Scollary, G. R. 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
13. Danilewicz, J. C. Mechanism of autoxidation of polyphenols and participation of sulfite in wine: Key role of iron Am. J. Enol. Vitic. 2011, 62, 319-328
14. 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
15. Sayavedra-Soto, L. A.; Montgomery, M. W. Inhibition of polyphenoloxidase by sulfite J. Food Sci. 1986, 51, 1531-1536
16. Ough, C. S.; Were, L. Sulfur dioxide and sulfites. In Antimicrobials in Food, 3 rd ed.; Davidson, P. M.; Sofos, J. N.; Branen, A. L., Eds.; CRC Press (Taylor and Francis Group): Boca Raton, FL, 2005; pp 143-160.
17. European Food Safety Authority (EFSA). Opinion of the Scientific Panel on Dietetic Products, Nutrition and Allergies on a Request from the Commission Relating to the Evaluation of Allergenic Foods for Labelling Purposes; EFSA: Parma, Italy, 2004; http://www.efsa.europa.eu/de/efsajournal/doc/32.pdf (accessed March 14, 2014).
18. Santos, M. M. C.; Nunes, C.; Saraiva, J. A.; Coimbra, M. A. Chemical and physical methodologies for the replacement/reduction of sulfur dioxide use during winemaking: Review of their potentialities and limitations Eur. Food Res. 2012, 234, 1-12
19. Comuzzo, P.; Zironi, R. Biotechnological strategies for controlling wine oxidation Food Eng. Rev. 2013, 5, 217-229
20. Luo, Y.; Wang, Q. Recent advances of chitosan and its derivatives for novel applications in food science J. Food Process. Beverages 2013, 1, 13
21. Dutta, P. K.; Dutta, J.; Tripathi, V. S. Chitin and chitosan: Chemistry, properties and applications J. Sci. Ind. Res. 2004, 63, 20-31
22. Yen, M.-T.; Yang, J.-H.; Mau, J.-L. Antioxidant properties of chitosan from crab shells Carbohydr. Polym. 2008, 74, 840-844
23. Chien, P.-J.; Sheu, F.; Huang, W.-T.; Su, M.-S. Effect of molecular weight of chitosans on their antioxidative activities in apple juice Food Chem. 2007, 102, 1192-1198
24. European Union (EU) Commission regulation (EU) 53/2011 of 21 January 2011 Off. J. Eur. Union 2011, L19/1-L19/6
25. Quintela, S.; Villarán, M. C.; López De Armentia, I.; Elejalde, E. Ochratoxin A removal from red wine by several oenological fining agents: bentonite, egg albumin, allergen-free adsorbents, chitin and chitosan Food Addit. Contam., Part A 2012, 29, 1168-1174
26. Bornet, A.; Teissedre, P. L. L. Chitosan, chitin-glucan and chitin effects on minerals (iron, lead, cadmium) and organic (ochratoxin A) contaminants in wines Eur. Food Res. Technol. 2007, 226, 681-689
27. Bornet, A.; Teissedre, P. L. Intérêt de l'utilisation de chitine, chitosane et de leurs dérivés en œnologie J. Int. Sci. Vigne Vin 2005, 39, 199-207
28. Spagna, G.; Barbagallo, R. N.; Pifferi, P. G. Fining treatments of white wines by means of polymeric adjuvants for their stabilization against browning J. Agric. Food Chem. 2000, 48, 4619-4627
29. Spagna, G.; Pifferi, P. G.; Rangoni, C.; Mattivi, F.; Nicolini, G.; Palmonari, R. The stabilization of white wines by adsorption of phenolic compounds on chitin and chitosan Food Res. Int. 1996, 29, 241-248
30. Da Silva, M. A. C. R.; Nunes, C. S. C.; Maricato, E. S. O.; Da Cunha, A. M. M. V.; Barroso, S. A. L. V. M.; Da Silva, J. A. L. Winemaking process without sulfur dioxide addition using chitosan-based films. EU Patent CA2854282 A1, May 10, 2013.
31. Chinnici, F.; Sonni, F.; Natali, N.; Riponi, C. Oxidative evolution of (+)-catechin in model white wine solutions containing sulfur dioxide, ascorbic acid or gallotannins Food Res. Int. 2013, 51, 59-65
32. Ellman, G. L. Tissue sulfhydryl groups Arch. Biochem. Biophys. 1959, 82, 70-77
33. International Organization of Vine and Wine (OIV). Compendium of International Methods of Wine and Must Analysis; OIV: Paris, France, 2013.
34. 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
35. Fedrizzi, B.; Versini, G.; Lavagnini, I.; Nicolini, G.; Magno, F. Gas chromatography-mass spectrometry determination of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in wine: A comparison of headspace solid phase microextraction and solid phase extraction methods Anal. Chim. Acta 2007, 596, 291-297
36. 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, 7410-7418
37. Elias, R. J.; Waterhouse, A. L. Controlling the fenton reaction in wine J. Agric. Food Chem. 2010, 58, 1699-1707
38. Milhome, M. A. L.; de Keukeleire, D.; Ribeiro, J. P.; Nascimento, R. F.; Carvalho, T. V.; Queiroz, D. C. Removal of phenol and conventional pollutants from aqueous effluent by chitosan and chitin Quim. Nova 2009, 32, 2122-2127
39. 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
40. 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, 162, 159-162
41. Xing, R.; Liu, S.; Guo, Z.; Yu, H.; Wang, P.; Li, C.; Li, Z.; Li, P. Relevance of molecular weight of chitosan and its derivatives and their antioxidant activities in vitro Bioorg. Med. Chem. 2005, 13, 1573-1577