Oxidative stability of (-)-epigallocatechin gallate in the presence of thiols

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 43, 2012, Pages 10815-10821

  Unnadkat, Nausheel R ^a   Elias, Ryan J ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

oxidation; polyphenols; quinones; thiols

Indexed keywords

ACIDIC CONDITIONS; ADDUCT FORMATION; BENZOQUINONES; CHEMICAL INSTABILITY; ELECTROPHILES; EPIGALLOCATECHIN GALLATE; FOOD MATRIXES; FUNCTIONAL FOODS; GALLATE; GLUTATHIONES; HEALTH BENEFITS; OXIDATIVE STABILITY; PHENOLIC COMPOUNDS; POLYPHENOLS; QUINONES; THIOLS;

ADDITION REACTIONS; AMINO ACIDS; BIOACTIVITY; PHENOLS;

OXIDATION;

CATECHIN; DRUG DERIVATIVE; EPIGALLOCATECHIN GALLATE; POLYPHENOL; THIOL DERIVATIVE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; PH;

CATECHIN; HYDROGEN-ION CONCENTRATION; OXIDATION-REDUCTION; POLYPHENOLS; SULFHYDRYL COMPOUNDS;

EID: 84868151713     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf302939p     Document Type: Article

References (30)

1. Unno, T.; Sugimoto, A.; Kakuda, T. Scavenging effect of tea catechins and their epimers on superoxide anion radicals generated by a hypoxanthine anal xanthine oxidase system J. Sci. Food Agr. 2000, 80, 601-606
2. Sommer, A. P. Comment on the Special Issue-Green Tea and Cancer Mol. Nutr. Food Res. 2011, 1439-1439
3. Huang, Y. W.; Liu, Y.; Dushenkov, S.; Ho, C. T.; Huang, M. T. Anti-obesity effects of epigallocatechin-3-gallate, orange peel extract, black tea extract, caffeine and their combinations in a mouse model J. Funct. Food. 2009, 304-310
4. Danilewicz, J. C. Mechanism of Autoxidation of Polyphenols and Participation of Sulfite in Wine: Key Role of Iron Am. J. Enol. Viticult. 2011, 62, 319-328
5. Danilewicz, J. C. Interaction of sulfur dioxide, polyphenols, and oxygen in a wine-model system: Central role of iron and copper Am. J. Enol. Viticult. 2007, 58, 53-60
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. Viticult. 1974, 25, 119-126
7. Waterhouse, A. L.; Laurie, V. F. Oxidation of Wine Phenolics: A Critical Evaluation and Hypotheses Am. J. Enol. Viticult. 2006, 57, 306-313
8. Lambert, J. D.; Sang, S.; Yang, C. S. Possible Controversy over Dietary Polyphenols: Benefits vs Risks Chem. Res. Toxicol. 2007, 20, 583-585
9. 2 center dot: The forgotten radical DNA Cell Biol. 2002, 21, 251-257
10. Zhou, L.; Ryan, E. Investigating the Hydrogen Peroxide Quenching Capacity of Proteins in Polyphenol-Rich Foods J. Agric. Food Chem. 2011, 8915-8922
11. Hagerman, A. E.; Dean, R. T.; Davies, M. J. Radical chemistry of epigallocatechin gallate and its relevance to protein damage Arch. Biochem. Biophys. 2003, 414, 115-120
12. Severino, J. F.; Goodman, B. A.; Kay, C. W. M.; Stolze, K.; Tunega, D.; Reichenauer, T. G.; Pirker, K. F. Free radicals generated during oxidation of green tea polyphenols: Electron paramagnetic resonance spectroscopy combined with density functional theory calculations Free Radical Bio. Med. 2009, 1076-1088
13. Sang, S. M.; Lee, M. J.; Hou, Z.; Ho, C. T.; Yang, C. S. Stability of tea polyphenol (-)-epigallocatechin-3-gallate and formation of dimers and epimers under common experimental conditions J. Agric. Food Chem. 2005, 9478-9484
14. Cilliers, J. J. L.; Singleton, V. L. Characterization of the products of nonenzymic autoxidative phenolic reactions in a caffeic acid model system J. Agric. Food Chem. 1991, 1298-1303
15. Blanchard, L.; Darriet, P.; Dubourdieu, D. Reactivity of 3-mercaptohexanol in red wine: Impact of oxygen, phenolic fractions, and sulfur dioxide Am. J. Enol. Viticult. 2004, 55, 115-120
16. Sang, S. M.; Lambert, J. D.; Hong, J.; Tian, S. Y.; Lee, M. J.; Stark, R. E.; Ho, C. T.; Yang, C. S. Synthesis and structure identification of thiol conjugates of (-)-epigallocatechin gallate and their urinary levels in mice Chem. Res. Toxicol. 2005, 1762-1769
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. Mori, T.; Ishii, T.; Akagawa, M.; Nakamura, Y.; Nakayama, T. Covalent Binding of Tea Catechins to Protein Thiols: The Relationship between Stability and Electrophilic Reactivity Biosci. Biotechnol. Biochem. 2010, 2451-2456
19. 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. Viticult. 2008, 59, 128-136
20. Ellman, G. L. Tissue Sulfhydryl Groups Arch. Biochem. Biophys. 1959, 82, 70-77
21. Robyt, J.; White, B. Biochemical Techniques: Theory and Practice; Waveland Press, Inc.: Iowa State University, 1990; pp 237-239.
22. Lee, M.-J.; Lambert, J. D.; Prabhu, S.; Meng, X.; Lu, H.; Maliakal, P.; Ho, C.-T.; Yang, C. S. Delivery of Tea Polyphenols to the Oral Cavity by Green Tea Leaves and Black Tea Extract Cancer Epidemiol. Biomark. Prev. 2004, 13, 132-137
23. Hu, J.; Zhou, D.; Chen, Y. Preparation and Antioxidant Activity of Green Tea Extract Enriched in Epigallocatechin (EGC) and Epigallocatechin Gallate (EGCG) J. Agric. Food Chem. 2009, 1349-1353
24. Danilewicz, J. C. Mechanism of Autoxidation of Polyphenols and Participation of Sulfite in Wine: Key Role of Iron Am. J. Enol. Viticult. 2011, 3, 319-328
25. Charles-Bernard, M.; Roberts, D. D.; Kraehenbuehl, K. Interactions between volatile and nonvolatile coffee components. 2. Mechanistic study focused on volatile thiols J. Agric. Food Chem. 2005, 4426-4433
26. Gilbert, H. F. Thiol/Disulfide exchange and disulfide bond stability Biothiols 1995, 8-28
27. Jocylin, P. C. Biochemistry of the Sulfhydryl Group. In Academic Press: New York, 1972.
28. Cao, D.; Zhang, Y. J.; Zhang, H. H.; Zhong, L. W.; Qian, X. H. Systematic characterization of the covalent interactions between (-)-epigallocatechin gallate and peptides under physiological conditions by mass spectrometry Rapid Commun. Mass Sp. 2009, 1147-1157
29. Jongberg, S.; Gislason, N. E.; Lund, M. N.; Skibsted, L. H.; Waterhouse, A. L. Thiol-Quinone Adduct Formation in Myofibrillar Proteins Detected by LC-MS J. Agric. Food Chem. 2011, 6900-6905
30. Awad, H. M.; Boersma, M. G.; Boeren, S.; van Bladeren, P. J.; Vervoort, J.; Rietjens, I. Quenching of quercetin quinone/quinone methides by different thiolate scavengers: Stability and reversibility of conjugate formation Chem. Res. Toxicol. 2003, 16, 822-831