Kinetics for singlet oxygen formation by riboflavin photosensitization and the reaction between riboflavin and singlet oxygen

Journal of Food Science

Volumn 69, Issue 9, 2004, Pages

  Huang, R ^a   Choe, E ^a   Min, D B ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Degradation; Quenching; Reaction rate constant; Riboflavin; Singlet oxygen

Indexed keywords

EID: 10944254240     PISSN: 00221147     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1365-2621.2004.tb09924.x     Document Type: Article

References (42)

1. Bradley DG. 1991. Riboflavin-photosensitized singlet oxygen oxidation in milk products [DPhil Dissertation]. Columbus, Ohio: Ohio State Univ. 97 p.
2. Bradley DG, Lee HO, Min DB. 2003. Singlet oxygen detection in skim milk by electron spin resonance spectroscopy. J Food Sci 68(2):491-4.
3. Chen Y, Huang L, Qi F. 2001. Research and development on fortified soy milk. Shanghai Shuichan Daxue Xuebao 10(2):190-2.
4. Crank G, Pardijanto MS. 1995. Photooxidations and photosensitized oxidations of vitamin A and its palmitate ester. J Photochem Photobiol A: Chem 85(1/2):93-100.
5. Criado S, Castillo C, Yppolito R, Bertolotti S, Garcia NA. 2003. The role of 4- and 5-aminosalicylic acids in a riboflavin-photosensitized process. J Photochem Photobiol A: Chem 155(1-3):115-8.
6. de La Rochette A, Birlouez-Aragon I, Silva E, Morliere P. 2003. Advanced glycation endproducts as UVA photosensitizers of tryptophan and ascorbic acid: consequences for the lens. Biochim Biophys Acta 1621(3):235-41.
7. Edwards AM, Bueno C, Saldano A, Silva E, Kassab K, Polo L, Jori G. 1999. Photochemical and pharmacokinetic properties of selected flavins. J Photochem Photobiol B: Biol 48(1):36-41.
8. Foote CS. 1979. Quenching of singlet oxygen. In: Wasserman H, Murray RW, editors. Singlet oxygen. New York: Academic Press. p 139-71.
9. Foote CS. 1985. Chemistry of reactive oxygen species. In: Richardson TR, Finley JW, editors. Chemical changes in food processing. Westport, Conn.: AVI Publishing. p 17-31.
10. Fujita H, Matsuo I. 1994. In vitro phototoxic activities of new quinolone antibacterial agents: lipid peroxidative potentials. Photodermatol Photoimmunol Photomed 10(5):202-5.
11. Furuya EM, Warthesen JJ, Labuza TP. 1984. Effects of water activity, light intensity and physical structure of food on the kinetics of riboflavin photodegradation. J Food Sci 49(2):525-8.
12. Gliszczynska A, Koziolowa A. 1999. Riboflavin derivatives in food. In: Proceedings of the 13th Flavins and Flavoproteins Intl. Symposium; Konstanz, Germany; 29 Aug-4 Sept 1999. Berlin, Germany: Rudolf Weber. p 875-8.
13. Gorman AA, Rogers MAJ. 1989. Singlet oxygen. In: Scaiano JC, editor. Handbook of organic photochem. Boca Raton, Fla.: CRC Press p 2:229.
14. Grzelak A, Rychlik B, Bartosz G. 2001. Light-dependent generation of reactive oxygen species in cell culture media. Free Rad Biol Med 30(12):1418-25.
15. Haag WR, Mill T. 1987. Rate constants for interaction of singlet oxygen (1Dg) with azide ion in water. Photochem Photobiol 45(3):317-21.
16. Hall RD, Chignell CF. 1987. Steady-state near-infrared detection of singlet molecular oxygen: a Stern-Volmer quenching experiment with sodium azide. Photochem Photobiol 45(4):459-64.
17. Hurst JR, Schuster GB. 1983. Nonradiative relaxation of singlet oxygen in solution. J Am Chem Soc 105:5756-60.
18. Joshi PC. 1989. Ultraviolet radiation-induced photodegradation and singlet oxygen, superoxide anion radical production by riboflavin, lumichrome and lumiflavin. Indian J Biochem Biophys 26(3):186-9.
19. Jung MY, Kim SK, Kim SY. 1995. Riboflavin-sensitized photooxidation of ascorbic acid: kinetics and amino acid effects. Food Chem 53(4):397-403.
20. Kanofsky JR. 1991. Quenching of singlet oxygen by human red cell ghosts. Photochem Photobiol 53(1):93-9.
21. Kim H, Kirschenbaum LJ, Kosenthal I, Riesz P. 1993. Photosensitized formation of ascorbate radicals by riboflavin: an ESR study. Photochem Photobiol 57(5):777-84.
22. King JM, Min DB. 1998. Riboflavin photosensitized singlet oxygen oxidation of vitamin D. J Food Sci 63(1):31-4.
23. Kumari MVH, Yoneda T, Hiramatsu M. 1996. Scavenging activity of β-catechin on reactive oxygen species generated by photosensitization of riboflavin. Biochem Molec Biol Intern 38(6):1163-70.
24. Lee KH, Jung MY, Kim SY. 1997. Quenching mechanism and kinetics of ascorbyl palmitate for the reduction of the photosensitized oxidation of oils. J Am Oil Chem Soc 74(9):1053-7.
25. Lee KH, Jung MY, Kim SY. 1998. Effect of ascorbic acid on the light-induced riboflavin degradation and color change in milks. J Agric Food Chem 46:407-10.
26. 2) by azide anion in solvent mixtures. Photochem Photobiol 74:760-4.
27. 2 [MSci Thesis]. Columbus, Ohio: Ohio State Univ. 150 p.
28. 2. J Food Biochem 24:477-92.
29. 2 in model system. J Food Sci 63:413-7.
30. Mahns A, Melchheier I, Suschek CV, Sies H, Klotz LO. 2003. Irradiation of cells with ultraviolet-A (320-400 nm) in the presence of cell culture medium elicits biological effects due to extracellular generation of hydrogen peroxide. Free Rad Res 37:391-7.
31. Mashiko S, Suzuki N, Koga S, Nakano M, Goto T, Ashino T, Mizumoto I, Inaba H, 1991. Measurement of rate constants for quenching singlet oxygen with a Cypridina luciferin analog (2-methyl-6-[p-methoxyphenyl]-3,7-dihydroimidazo[1, 2-a]pyrazin-3-one) and sodium azide. J Biolum Chemilum 6:69-72.
32. Min DB, Boff JM. 2002. Chemistry and reaction of singlet oxygen in foods. Comp Rev Food Sci Food Safety 1(1):58-72.
33. Rodgers MA, Snowden PT. 1982. Lifetime of singlet delta dioxygen in liquid water as determined by time-resolved infrared luminescence measurements. J Am Chem Soc 104:5541-3.
34. g) quenching by azide. J Photochem Photobiol A: Chem 66:153-7.
35. Singh JD, Chauhan GS, Suresh I, Mittal BK. 1996. Effect of fortification on sensory characteristics of soy milk. J Food Sci Technol 33:73-5.
36. SzczesniakT, Karabin L, Szczepankowska M, Wituch K. 1971. Biosynthesis of riboflavin by Ashbya gossypii. I. Influence of fats of animal origin on riboflavin production. Acta Microbiol Polon B: Microbiol Appl 3:29-34.
37. Tatsumi K, Ichikawa H, Wada S. 1992. Flavin-sensitized photooxidation of substituted phenols in natural water. J Contam Hydrol 9:207-19.
38. Toyosaki T, Hayashi A. 1993. Structural analysis of the products of milk riboflavin photolysis. Milchwissenschaft 48:607-9.
39. [USDA/ARS] U.S. Dept. of Agriculture, Agricultural Research Service. 2004. USDA Natl. Nutrient Database for Standard Reference. Release 17. Nutrient data laboratory home page. Available from: www.nal.usda.gov/fnic/foodcomp/. Accessed 8 Nov 2004.
40. Viteri G, Edwards AM, de la Fuente J, Silva E. 2003. Study of the interaction between triplet riboflavin and the α-, βH- and βL-crystallins of the eye lens. Photochem Photobiol 77:535-40.
41. Wishner LA. 1964. Light induced oxidation in milk. J Dairy Sci 47:216-21.
42. Yang WT, Lee JH, Min DB. 2002. Quenching mechanisms and kinetics of a-tocopherol and b-carotene on the photosensitizing effect of synthetic food colorant FD&C Red No. 3. J Food Sci 67:507-10.