Factors influencing the antioxidant and pro-oxidant activity of polyphenols in oil-in-water emulsions

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 11, 2012, Pages 2906-2915

  Zhou, Lisa ^a   Elias, Ryan J ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

electron paramagnetic resonance; emulsions; hydrogen peroxide; hydroxyl radicals; lipid oxidation; polyphenols

Indexed keywords

2 ,2-BIPYRIDINE; ANTIOXIDANT ACTIVITIES; EPIGALLOCATECHIN-3-GALLATE; ETHYLENE DIAMINE TETRA-ACETIC ACID; FOOD SYSTEM; HEXADECANE; HYDROXYL RADICALS; IRON CHELATORS; LIPID DISPERSION; LIPID OXIDATION; LIPID SYSTEMS; NEUTRAL PH; NON-ENZYMATIC OXIDATION; O/W EMULSIONS; OIL-IN-WATER (O/W) EMULSION; OIL-IN-WATER EMULSIONS; OXIDATIVE STABILITY; POLYPHENOLS; PROOXIDANT; REACTIVE OXYGEN SPECIES;

EMULSIONS; FLAX; HYDROGEN PEROXIDE; MAGNETIC RESONANCE; OILSEEDS; OXIDANTS; OXIDATION; OXIDATION RESISTANCE; PARAFFINS; PARAMAGNETIC RESONANCE; PARAMAGNETISM;

PHENOLS;

ANTIOXIDANT; CATECHIN; DRUG DERIVATIVE; EPIGALLOCATECHIN GALLATE; OIL; OXIDIZING AGENT; POLYPHENOL; WATER;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; EMULSION; OXIDATION REDUCTION REACTION; PH;

ANTIOXIDANTS; CATECHIN; EMULSIONS; HYDROGEN-ION CONCENTRATION; MODELS, CHEMICAL; OILS; OXIDANTS; OXIDATION-REDUCTION; POLYPHENOLS; WATER;

EID: 84858780596     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf204939h     Document Type: Article

References (43)

1. Roy, M. K.; Koide, M.; Rao, T. P.; Okubo, T.; Ogasawara, Y.; Juneja, L. R. ORAC and DPPH Assay Comparison to Assess Antioxidant Capacity of Tea Infusions: Relationship between Total Polyphenol and Individual Catechin Content Int. J. Food Sci. Nutr. 2010, 61 (2) 109-124
2. Nanjo, F.; Mori, M.; Goto, K.; Hara, Y. Radical Scavenging Activity of Tea Catechins and Their Related Compounds Biosci. Biotechnol. Biochem. 1999, 63 (9) 1621-1623 (Pubitemid 129555156)
3. Cai, Y. Z.; Mei, S.; Jie, X.; Luo, Q.; Corke, H. Structure-Radical Scavenging Activity Relationships of Phenolic Compounds from Traditional Chinese Medicinal Plants Life Sci. 2006, 78 (25) 2872-2888
4. Clark, W. M. Oxidation-Reduction Potentials of Organic Systems; The Williams & Wilkins Co.: Baltimore, 1960; p 584.
5. Chen, C. W.; Ho, C. T. Antioxidant Properties of Polyphenols Extracted from Green and Black Teas J Food Lipids 1995, 2 (1) 35-46
6. Medina, I.; Tombo, I.; Satué-Gracia, M. T.; German, J. B.; Frankel, E. N. Effects of Natural Phenolic Compounds on the Antioxidant Activity of Lactoferrin in Liposomes and Oil-in-Water Emulsions J. Agric. Food Chem. 2002, 50 (8) 2392-2399 (Pubitemid 34275315)
7. Frankel, E.; Huang, S. W.; Aeschbach, R. Antioxidant Activity of Green Teas in Different Lipid Systems J. Am. Oil Chem. Soc. 1997, 74 (10) 1309-1315 (Pubitemid 127555292)
8. Roedig-Penman, A.; Gordon, M. H. Antioxidant Properties of Catechins and Green Tea Extracts in Model Food Emulsions J. Agric. Food Chem. 1997, 45 (11) 4267-4270 (Pubitemid 127491617)
9. Huang, S. W.; Frankel, E. N. Antioxidant Activity of Tea Catechins in Different Lipid Systems J. Agric. Food Chem. 1997, 45 (8) 3033-3038 (Pubitemid 127481849)
10. Nakagawa, H.; Wachi, M.; Woo, J.-T.; Kato, M.; Kasai, S.; Takahashi, F.; Lee, I.-S.; Nagai, K. Fenton Reaction Is Primarily Involved in a Mechanism of (-)-Epigallocatechin-3-gallate to Induce Osteoclastic Cell Death Biochem. Biophys. Res. Commun. 2002, 292 (1) 94-101 (Pubitemid 34687334)
11. Makrigiorgos, G. M.; Bump, E.; Huang, C.; Baranowska-Kortylewicz, J.; Kassis, A. I. A Fluorimetric Method for the Detection of Copper-Mediated Hydroxyl Free Radicals in the Immediate Proximity of DNA Free Radic. Biol. Med. 1995, 18 (4) 669-678
12. Zhou, L.; Elias, R. J. Investigating the Hydrogen Peroxide Quenching Capacity of Proteins in Polyphenol-Rich Foods J. Agric. Food Chem. 2011, 59 (16) 8915-8922
13. Mahoney, J. R.; Graf, E. Role of Alpha-Tocopherol, Ascorbic Acid, Citric Acid and EDTA as Oxidants in Model Systems J. Food Sci. 1986, 51 (5) 1293-1296
14. 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 (2) 305-315
15. Bandy, B.; Walter, P. B.; Moon, J.; Davison, A. J. Reaction of Oxygen with 6-Hydroxydopamine Catalyzed by Cu, Fe, Mn, and V Complexes: Identification of a Thermodynamic Window for Effective Metal Catalysis Arch. Biochem. Biophys. 2001, 389 (1) 22-30 (Pubitemid 32911540)
16. Mira, L.; Fernandez, M. T.; Santos, M.; Rocha, R.; Florêncio, M. H.; Jennings, K. R. Interactions of Flavonoids with Iron and Copper Ions: A Mechanism for their Antioxidant Activity Free Radic. Res. 2002, 36 (11) 1199-1208 (Pubitemid 35230240)
17. Decker, E. A.; McClements, D. J.; Mancuso, J. R.; Tong, L.; Mei, L.; Sasaki, S.; Zeller, S. G.; Flatt, J. H., Impact of Emulsifiers on the Oxidative Stability of Lipid Dispersions High in Omega-3 Fatty Acids. In Omega-3 Fatty Acids; American Chemical Society: Washington DC, 2001; Vol. 788, pp 243-257. (Pubitemid 33620035)
18. Vile, G. F.; Winterbourn, C. C. Iron Binding to Microsomes and Liposomes in Relation to Lipid Peroxidation FEBS Lett. 1987, 215 (1) 151-154 (Pubitemid 17099154)
19. Huang, S. W.; Satué-Gracia, M. T.; Frankel, E. N.; German, J. B. Effect of Lactoferrin on Oxidative Stability of Corn Oil Emulsions and Liposomes J. Agric. Food Chem. 1999, 47 (4) 1356-1361 (Pubitemid 29217120)
20. Nuchi, C. D.; McClements, D. J.; Decker, E. A. Impact of Tween 20 Hydroperoxides and Iron on the Oxidation of Methyl Linoleate and Salmon Oil Dispersions J. Agric. Food Chem. 2001, 49 (10) 4912-4916 (Pubitemid 32988739)
21. Mancuso, J. R.; McClements, D. J.; Decker, E. A. The Effects of Surfactant Type, pH, and Chelators on the Oxidation of Salmon Oil-in-Water Emulsions J. Agric. Food Chem. 1999, 47 (10) 4112-4116 (Pubitemid 29506209)
22. Mei, L.; Decker, E. A.; McClements, D. J. Evidence of Iron Association with Emulsion Droplets and Its Impact on Lipid Oxidation J. Agric. Food Chem. 1998, 46 (12) 5072-5077 (Pubitemid 128489917)
23. 2+-Initiated Lipid Peroxidation in Liposomes: The Dual Function of Ferrous Ions, The Roles of the Pre-Existing Lipid Peroxides and the Lipid Peroxyl Radical Biochem. J. 2000, 352 (1) 27-36
24. Wolff, S. P.; Lester, P. [18] Ferrous Ion Oxidation in Presence of Ferric Ion Indicator Xylenol Orange for Measurement of Hydroperoxides Methods Enzymol. 1994, 233, 182-189
25. 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 (1) 132-137 (Pubitemid 38116630)
26. 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, 57 (4) 1349-1353
27. Shantha, N. C.; Decker, E. A. Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids J AOAC Int. 1994, 77 (2) 421-424
28. McDonald, R. E.; Hultin, H. O. Some Characteristics of the Enzymic Lipid Peroxidation System in the Microsomal Fraction of Flounder Skeletal Muscle J. Food Sci. 1987, 52 (1) 15-21
29. Zoski, C. G., Handbook of Electrochemistry, First ed.; Elsevier: Oxford, 2007; p 934.
30. Welch, K. D.; Davis, T. Z.; Aust, S. D. Iron Autoxidation and Free Radical Generation: Effects of Buffers, Ligands, and Chelators Arch. Biochem. Biophys. 2002, 397 (2) 360-369 (Pubitemid 34852304)
31. Graf, E.; Mahoney, J. R.; Bryant, R. G.; Eaton, J. W. Iron-Catalyzed Hydroxyl Radical Formation. Stringent Requirement for Free Iron Coordination Site J. Biol. Chem. 1984, 259 (6) 3620-4 (Pubitemid 14173396)
32. Braterman, P. S.; Song, J. I.; Peacock, R. D. Electronic Absorption Spectra of the Iron(II) Complexes of 2,2′-Bipyridine, 2,2′- Bipyrimidine, 1,10-Phenanthroline, and 2,2′:6′,2″-Terpyridine and Their Reduction Products Inorg. Chem. 1992, 31 (4) 555-559
33. Jovanovic, S. V.; Hara, Y.; Steenken, S.; Simic, M. G. Antioxidant Potential of Gallocatechins. A Pulse Radiolysis and Laser Photolysis Study J. Am. Chem. Soc. 1995, 117 (39) 9881-9888
34. Wood, P. M. the Potential Diagram for Oxygen at pH 7 Biochem. J. 1988, 253 (1) 287-289
35. Curcio, M.; Puoci, F.; Iemma, F.; Parisi, O. I.; Cirillo, G.; Spizzirri, U. G.; Picci, N. Covalent Insertion of Antioxidant Molecules on Chitosan by a Free Radical Grafting Procedure J. Agric. Food Chem. 2009, 57 (13) 5933-5938
36. Rivero-Pérez, M. D.; Muñiz, P.; González- Sanjosé, M. L. Contribution of Anthocyanin Fraction to the Antioxidant Properties of Wine Food Chem. Toxicol. 2008, 46 (8) 2815-2822
37. Halliwell, B.; Gutteridge, J. M. C.; Aruoma, O. I. the Deoxyribose Method: A Simple "Test-Tube" Assay for Determination of Rate Constants for Reactions of Hydroxyl Radicals Anal. Biochem. 1987, 165 (1) 215-219 (Pubitemid 17131019)
38. Ramos, C. L.; Pou, S.; Britigan, B. E.; Cohen, M. S.; Rosen, G. M. Spin Trapping Evidence for Myeloperoxidase-Dependent Hydroxyl Radical Formation by Human Neutrophils and Monocytes J. Biol. Chem. 1992, 267 (12) 8307-8312
39. Chen, Z.-Y.; Zhu, Q. Y.; Tsang, D.; Huang, Y. Degradation of Green Tea Catechins in Tea Drinks J. Agric. Food Chem. 2000, 49 (1) 477-482
40. Alamed, J.; McClements, D. J.; Decker, E. A. Influence of Heat Processing and Calcium Ions on the Ability of EDTA to Inhibit Lipid Oxidation in Oil-in-Water Emulsions Containing Omega-3 Fatty Acids Food Chem. 2006, 95 (4) 585-590 (Pubitemid 41436429)
41. Hu, M.; Julian McClements, D.; Decker, E. A. Impact of Chelators on the Oxidative Stability of Whey Protein Isolate-Stabilized Oil-in-Water Emulsions Containing [Omega]-3 Fatty Acids Food Chem. 2004, 88 (1) 57-62 (Pubitemid 38823010)
42. Maqsood, S.; Benjakul, S. Comparative Studies of Four Different Phenolic Compounds on in Vitro Antioxidative Activity and the Preventive Effect on Lipid Oxidation of Fish Oil Emulsion and Fish Mince Food Chem. 2010, 119 (1) 123-132
43. Mei, L.; McClements, D. J.; Decker, E. A. Lipid Oxidation in Emulsions As Affected by Charge Status of Antioxidants and Emulsion Droplets J. Agric. Food Chem. 1999, 47 (6) 2267-2273 (Pubitemid 29325109)