Identification of free radical intermediates in oxidized wine using electron paramagnetic resonance spin trapping

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 10, 2009, Pages 4359-4365

  Elias, Ryan J ^a,c   Andersen, Mogens L ^b   Skibsted, Leif H ^b   Waterhouse, Andrew L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

1 hydroxyethyl radicals; Copper; EPR; Fenton reaction; Hydroperoxyl radicals; Hydroxyl radicals; Iron; Metal catalysis; Methyl radicals; Oxidation; Spin adducts; Spin trapping; Sulfite radicals; Wine

Indexed keywords

1 HYDROXYETHYL RADICAL; 1-HYDROXYETHYL RADICAL; ALCOHOL; FREE RADICAL; HYDROXYL RADICAL; SULFITE;

ARTICLE; CHEMISTRY; ELECTRON SPIN RESONANCE; OXIDATION REDUCTION REACTION; SPIN TRAPPING; WINE;

ELECTRON SPIN RESONANCE SPECTROSCOPY; ETHANOL; FREE RADICALS; HYDROXYL RADICAL; OXIDATION-REDUCTION; SPIN TRAPPING; SULFITES; WINE;

EID: 66149097306     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8035484     Document Type: Article

References (32)

1. Singleton, V. L.; Trousdale, E.; Zaya, J. Oxidation of wines. 1. Young white wines periodically exposed to air. Am. J. Enol. Vitic. 1979, 30, 49-54.
2. Atanasova, V.; Fulcrand, H.; Cheynier, W.; Moutounet, M. Effect of oxygenation on polyphenol changes occurring in the course of wine-making. Anal. Chim. Acta 2002, 458, 15-27.
3. Castellari, M.; Arfelli, G.; Riponi, C.; Amati, A. Evolution of phenolic compounds in red winemaking as affected by must oxygenation. Am. J. Enol. Vitic. 1998, 49, 91-94.
4. Cilliers, J. J. L.; Singleton, V. L. Nonenzymic autoxidative reactions of caffeic acid in wine. Am. J. Enol. Vitic. 1990, 41, 84-86.
5. Wildenradt, H. L.; Singleton, V. L. Production of aldehydes as a result of oxidation of polyphenols compounds and its relation to wine aging. Am. J. Enol. Vitic. 1974, 25,119-126.
6. 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.
7. 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.
8. Ough, C. S.; Amerine, M. A.Methodsfor Analysis of Musts and Wines, 2nd ed.; J. Wiley: New York, 1988; p x, 377.
9. Laurie, V. F.; Waterhouse, A. L. Oxidation of glycerol in the presence of hydrogen peroxide and iron in model solutions and wine. Potential effects on wine color. J. Agric. Food Chem. 2006, 54, 4668-4673.
10. Waterhouse, A. L.; Laurie, V. F. Oxidation of wine phenolics: A critical evaluation and hypotheses. Am. J. Enol. Vitic. 2006, 57, 306-313.
11. 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.
12. Buettner, G. R. Spin trapping: ESR parameters of spin adducts. Free Radical Biol. Med. 1987, 3, 259-303.
13. Andersen, M. L.; Skibsted, L. H. Electron spin resonance spin trapping identification of radicals formed during aerobic forced aging of beer. J. Agric. Food Chem. 1998, 46, 1272-1275.
14. Frederiksen, A. M.; Festersen, R. M.; Andersen, M. L. Oxidative reactions during early stages of beer brewing studied by electron spin resonance and spin trapping. J. Agric. Food Chem. 2008, 56, 8514-8520
15. Uchida, M.; Ono, M. Determination of hydrogen peroxide in beer and its role in beer oxidation. J. Am. Soc. Brew. Chem. 1999,57, 145-150.
16. Uchida, M.; Ono, M. Improvement for oxidative flavor stability of beer-Role of OH-radical in beer oxidation. J. Am. Soc. Brew. Chem. 1996, 54, 198-204.
17. Uchida, M.; Suga, S.; Ono, M. Improvement for oxidative flavor stability of beer-Rapid prediction method for beer flavor stability by electron spin resonance spectroscopy. J. Am. Soc. Brew. Chem. 1996, 54, 205-211.
18. Glidewell, S. M.; Deighton, N.; Goodman, B. A.; Troup, G. J.; Hutton, D. R.; Hewitt, D. G.; Hunter, C. R. Free radical scavenging abilities of beverages. Int. J. Food Sci. Technol. 1995, 30, 535-537.
19. Troup, G. J.; Hunter, C. R. EPR free radicals, wine, and the industry-Some achievements. Alcohol Wine Health Dis. 2002, 957, 345-347.
20. Troup, G. J.; Hutton, D. R.; Hewitt, D. G.; Hunter, C. R. Freeradicals in red wine, but not in white. Free Radical Res. 1994, 20, 63-68.
21. Persson, D. P.; Hansen, T. H.; Holm, P. E.; Schjoerring J. K.; Hansen, H. C. B.; Nielsen, J.; Cakmak, I.; Husted, S. Multi-elemental speciation analysis of barley genotypes differing in tolerance to cadmium toxicity using SEC-ICP-MS and ESI-TOF-MS. J. Anal. At. Spectrom. 2006, 21, 996-1005.
22. Duling, D. R. Simulation of multiple isotropic spin-trap EPRspectra. J. Magn. Reson. Ser. B 1994,104, 105-110.
23. Asmus, K. D.; Mockel, H.; Henglein, A. Pulse radiolytic study of site of oh radical attack on aliphatic alcohols in aqueoussolution. J. Phys. Chem. 1973, 77, 1218-1221.
24. Mason, R. P.; Kadiiska, M. B. Biomedical EPR, part A: Free radicals, metals, medicine, and physiology. Biological Magnetic Resonance; Springer US: New York, 2004; Vol. 23, pp 93-109.
25. Brandt, C.; Fabian, I.; Vaneldik, R. Kinetics and mechanism of the iron(III)-catalyzed autoxidation of sulfur(IV) oxides in aqueous-solution- Evidence for the redox cycling of iron in the presence of oxygen and modeling of the overall reactionmechanism. Inorg. Chem. 1994, 33, 687-701.
26. Brandt, C.; Vaneldik, R. Transition-metal-catalyzed oxidation of sulfur(IV) oxides-Atmospheric-relevant processes and mechanisms. Chem. Rev. 1995, 95, 119-190.
27. Khan, N.; Wilmot, C. M.; Rosen, G. M.; Demidenko, E.; Sun, J.; Joseph, J.; O'Hara, J.; Kalyanaraman, B.; Swartz, H. M. Spin traps: In vitro toxicity and stability of radical adducts. Free Radical Biol. Med. 2003, 34, 1473-1481
28. Zhao, H.; Joseph, J.; Zhang, H.; Karoui, H.; Kalyanaraman, B. Synthesis and biochemical applications of a solid cyclic nitrone spin trap: A relatively superior trap for detecting superoxide anions and glutathiyl radicals. Free Radical Biol. Med. 2001, 31, 599-606.
29. 3- radicals in aqueous solution. J. Phys. Chem. A 1999, 103, 3581-3588.
30. Bandy, B.; Davison, A. J. Interactions between metals, ligands, and oxygen in the autoxidation of 6-hydroxydopamine- Mechanisms by which metal chelation enhances inhibition by superoxide-dismutase. Arch. Biochem. Biophys. 1987, 259, 305-315.
31. Gee, P.; Davison, A. J. 6-Hydroxydopamine does not reduce molecular-oxygen directly, but requires a coreductant. Arch. Biochem. Biophys. 1984, 231, 164-168.
32. Gee, P.; Davison, A. J. Autoxidation of 6-hydroxydopamine involves a ternary reductant-metal-oxygen complex. 1rcs Med. Sci.-Biochem. 1984, 12, 127-1127