Role of iron and hydroperoxides in the degradation of lycopene in oil-in-water emulsions

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 7, 2009, Pages 2993-2998

  Boon, Caitlin S ^a   McClements, D Julian ^a   Weiss, Jochen ^a   Decker, Eric A ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

Carotenoid; Emulsion; Hexadecane; Hydroperoxides; Iron; Lycopene; Surfactants

Indexed keywords

2-TERT-BUTYLHYDROQUINONE; ANTIOXIDANT; CAROTENOID; EDETIC ACID; HYDROGEN PEROXIDE; HYDROQUINONE DERIVATIVE; IRON; LYCOPENE; TERT BUTYLHYDROQUINONE;

ARTICLE; CHEMISTRY; DRUG STABILITY; EMULSION; LIGHT; OXIDATION REDUCTION REACTION; PH;

ANTIOXIDANTS; CAROTENOIDS; DRUG STABILITY; EDETIC ACID; EMULSIONS; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; HYDROQUINONES; IRON; LIGHT; OXIDATION-REDUCTION;

EID: 64549108930     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf803747j     Document Type: Article

References (31)

1. Mordi, R.; Walton, J. C.; Burton, G. W.; Hughes, L.; Ingold, K. U.; Lindsay, D. A.; Moffat, D. J. Oxidative degradation of beta-carotene and beta-apo-8′-carotenal. Tetrahedron 1993, 49, 911-928.
2. Henry, L. K.; Puspitasari-Nienaber, N. L.; Jaren-Galan, M.; van Breemen, R. B.; Catignani, G. L.; Schwartz, S. J. Effects of ozone and oxygen on the degradation of carotenoids in an aqueous model system, J. Agric. Food Chem. 2000, 48, 5008-5013.
3. Konovalov, V. V.; Kispert, L. D. AM1, 1NDO/S and optical studies of carbocations of carotenoid molecules. Acid induced isomerization. J. Chem. Soc, Perkin Trans. 2 1999, 1999, 901-909.
4. Mortensen, A.; Skibsted, L. H. Kinetics of photobleaching of beta-carotene in chloroform and formation of transient carotenoid species absorbing in the near infrared. Free Radical Res. 1996, 25, 355-368.
5. Mader, I. Beta-carotene: Thermal degradation, Science 1964, 144, 533-534.
6. Krinsky, N. I. The antioxidant and biological properties of the carotenoids. Ann. N.Y. Acad. Sci. 1998, 854, 443-447.
7. He, Z. F.; Kispert, L. D. Carotenoids in sol-gels: Incorporation, stability, and sensitivity to oxidant and acid. Chem. Mater. 2001, 13, 227-231.
8. Gao, Y. L.; Kispert, L. D. Reaction of carotenoids and ferric chloride: Equilibria, isomerization, and products. J. Phys. Chem.b 2003, 107, 5333-5338.
9. Gao, G. Q.; Deng, Y.; Kispert, L. D. Photoactivated ferric chloride oxidation of carotenoids by near-UV to visible light. J. Phys. Chem. B 1997, 101, 7844-7849.
10. Liebler, D. C.; McClure, T. D. Antioxidant reactions of beta-carotene: Identification of carotenoid-radical adducts. Chem. Res. Toxicol. 1996, 9, 8-11.
11. Woodall, A. A.; Lee, S. W. M.; Weesie, R. J.; Jackson, M. J.; Britton, G. Oxidation of carotenoids by free radicals: relationship between structure and reactivity. Biochim. Biophys. Acta 1997, 1336, 33-42.
12. Mortensen, A. Scavenging of benzylperoxyl radicals by carotenoids. Free Radical Res. 2002, 36, 211-216.
13. Haila, K. M.; Nielsen, B. R.; Heinonen, Marina, I.; Skibsted, Leif, H. Carotenoid reaction with free radicals in acetone and toluene at different oxygen partial pressures. Eur. Food Res. Technol. 1997, 204, 81-87.
14. Yamauchi, R.; Tsuchihashi, K.; Kato, K. Oxidation products of beta-carotene during the peroxidation of methyl linoleate in the bulk phase. Bwsci. Biotechnol. Biochem. 1998, 62, 1301-1306.
15. Yamauchi, R.; Miyake, N.; Inoue, H.; Kato, K. Products formed by peroxyl radical oxidation of beta-carotene. J. Agric. Food Chem. 1993, 41, 708-713.
16. Khachik, F.; Steck, A.; Niggli, U. A.; Pfander, H. Partial synthesis and structural elucidation of the oxidative metabolites of lycopene identified in tomato paste, tomato juice, and human serum. J. Agric. Food Chem. 1998, 46, 4874-4884.
17. Nguyen, M. L.; Schwartz, S. J. Lycopene: Chemical and biological properties. Food Technol. 1999, 53, 38-45.
18. Fairfield, K. M.; Fletcher, R. H. Vitamins for chronic disease prevention in adults. JAMA, J. Am. Med. Assoc. 2002, 287, 3116-3126.
19. Wilcox, J.; Catignani, G.; Lazarus, S. Tomatoes and cardiovascular health. Crit. Rev. Food Sci. Nutr. 2003, 43, 1-18.
20. Kun, Y.; Ssonko Lule, U.; Xiao-Lin, D. Lycopene: Its properties and relationship to human health. Food Rev. Int. 2006, 22, 309-333.
21. Chee, C. P.: Djordjevic. D.: Faraji, H.; Decker, E. A.: Hollender, R.; McClements, D. J.; Peterson, D. G.; Roberts, R. F.; Coupland, J. N. Sensory properties of vanilla and strawberry flavored ice cream supplemented with omega-3 fatty acids. Milk Sci. Int. 2007, 62, 66-69.
22. Chee, C. P.; Gallaher, J. J.; Djordjevic, D.; Faraji, H.; McClements, D. J.; Decker, E. A.; Hollender, R.; Peterson, D. G.; Roberts, R. F.: Coupland, J. N. Chemical and sensory analysis of strawberry flavoured yogurt supplemented with an algae oil emulsion. J. Dairy Res. 2005, 72, 311-316.
23. 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, 5072-5077.
24. McClements, D. J.; Decker, E. A. Lipid oxidation in oil-in-water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food systems. J. Food Sci. 2000, 65, 1270-1282.
25. Stookey, L. L. Ferrozine-a new spectrophotometric reagent for iron. Anal. Chem. 1970, 42, 779-781.
26. McClements, D. J. Food Emulsions: Principles, Practices, and Techniques; CRC Press: New York, 2005: p 609.
27. Kishk, Y. F. M.; Al-Sayed, H. M. A. Free-radical scavenging and antioxidative activities of some polysaccharides in emulsions. LWT-Food Sci. Technol. 2007, 40, 270-277.
28. Zumdahl, S. S. Applications of aqueous equilibria. In Chemistry. 2nd ed.; D.C. Heath and Company: Lexington, MA, 1989: pp 669-735.
29. Mancuso, J. R.; McClements, D. J.; Decker, E. A. Ability of iron to promote surfactant peroxide decomposition and oxidize alpha-tocopherol. J. Agric. Food Chem. 1999, 47, 4146-4149.
30. Rao, S. K.; Artz, W. E. Effect of extrusion on lipid oxidation. J. Food Sci. 1989, 54, 1580-1583.
31. Betts, A. T.; Uri, N. The conversion of metal catalysts into inhibitors of autoxidation. Makromol. Chem. 1966, 1966, 22-39.