ESR study of the singlet oxygen quenching and protective activity of trolox on the photodecomposition of riboflavin and lumiflavin in aqueous buffer solutions

Journal of Food Science

Volumn 74, Issue 6, 2009, Pages

  Jung, Mun Yhung ^a   Min, David B ^b  

^a Woosuk University   (South Korea)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

ESR; Lumiflavin; Photodegradation; Riboflavin; Singlet oxygen; Trolox

Indexed keywords

6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID; ANTIOXIDANT; ASCORBIC ACID; CHROMAN DERIVATIVE; LUMIFLAVINE; RIBOFLAVIN; RIBOFLAVIN DERIVATIVE; SINGLET OXYGEN; TROLOX C;

ARTICLE; CHEMISTRY; ELECTRON SPIN RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT; PH; PHOTOLYSIS; TIME;

ANTIOXIDANTS; ASCORBIC ACID; CHROMANS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTRON SPIN RESONANCE SPECTROSCOPY; FLAVINS; HYDROGEN-ION CONCENTRATION; LIGHT; PHOTOLYSIS; RIBOFLAVIN; SINGLET OXYGEN; TIME FACTORS;

EID: 70350136234     PISSN: 00221147     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1750-3841.2009.01230.x     Document Type: Article

References (30)

1. Ahmad I, FasihullahQ, Vaid FHM. 2004a. A study of simultaneous photolysis and photoaddition reactions of riboflavin in aqueous solution. J Photochem Photobiol B: Biol 75:13-20.
2. Ahmad I, Fashihullah Q, Noor A, Ansari IA, Ali QNM. 2004b. Photolysis of riboflavin in aqueous solution: a kinetic study. Int J Pharm 280:199-208.
3. Ajayi OA, George BO, Ipadeola T. 1993. Clinical trial of riboflavin in sickle cell disease. East Afr Med J 70:418-421
4. Bisby RH, Morgan CG, Hamblett I, Gorman AA. 1999. Quenching of singlet oxygen by Trolox C, ascorbic acid, and amino acids: effects of pH and temperature. J Phys Chem A 103:7454-7459
5. Choe E, Huang R, Min DB. 2005. Chemical reactions and stability of riboflavin in foods. J Food Sci 70:R28-36.
6. 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 155:115-118
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 48:36-41.
8. Gliszczynska A, Koziolowa A. 1999. Flavins and flavoproteins. In: Proceedings of the 13th International Symposium, Konstanz, Germany, Aug 29-Sept 4, p 875-878
9. Grzelak A, Rychlik B, Bartosz G. 2001. Light-dependent generation of reactive oxygen species in cell culture media. Free Radical Biol Med 30:1418-1425
10. Gutierrez I, Criado S, Bertolotti S, Garcia NA. 2001. Dark and photoinduced interactions between Trolox, a polar-solvent-soluble model for vitaimin E, and riboflavin. J Photochem Photobiol 62:133-139
11. Huang R, Choe E, Min DB. 2004a. Effects of riboflavin photosensitized oxidation on the volatile compounds of soymilk. J Food Sci 69:C733-8.
12. Huang R, Choe E, Min DB. 2004b. Kinetics for singlet oxygen formation by riboflavin photosensitization and the reaction between riboflavin and singlet oxygen. J Food Sci 69:C726-32.
13. Huang R, Kim HJ, Min DB. 2006. Photosensitizing effect of riboflavin, lumiflavin and lumichrome on the generation of volatiles in soymilk. J Agric Food Chem 54:2359-2364
14. Jung MY, Oh YS, Kim DK, Kim HJ, Min DB. 2007. Photoinduced generation of 2,3- butanedione from riboflavin. J Agric Food Chem 55:170-174
15. Kim H, Kirschenbaum LJ, Rosenthal I, Riesz P. 1993. Photosensitized formation of ascorbate radicals by riboflavin: an ESR study. Photochem Photobiol 57:777-784
16. Kim JI, Lee JH, Choi DS, Won BM, Jung MY, Park J. 2009. Kinetic study of the quenching reaction of singlet oxygen by common synthetic antioxidants (tertbutylhydroxylanisol, tert-di-butylhydroxytoluene, and tert- butylhydroquinone) as compared with alpha-tocopherol. J Food Sci 73:C362-9.
17. Koopman WJH, Verkaart S, van Emst-de VSE, Grefte S, Smeitink JAM, Nijtmans LGJ, Willems PHGM. 2008. Mitigation of NADH: ubiquinone oxidoreductase deficiency by chronic Trolox treatment. Biochim Biophys Acta 1777:853-859
18. Lee SW, Chang PS, Lee JH. 2008. Effects of riboflavin photosensitization on the changes of isoflavones in soymilk. J Food Sci 73:C551-5.
19. Lion Y, Demelle M, van de Vorst A. 1976. New method of detecting singlet oxygen production. Nature 263:442-443
20. Lucius R, Mentlein R, Sievers J. 1998. Riboflavin-mediated axonal degeneration of postnatal retinal ganglion cells in vitro is related to the formation of free radicals. Free Radical Biol Med 24:798-808.
21. Min DB, Boff JM. 2002. Chemistry and reaction of singlet oxygen in foods. Comp Rev Food Sci Food Safety 1:58-72.
22. Oh YS, Jang ES, Bock JY, Yoon SH, Jung MY. 2006. Singlet oxygen quenching activities of various fruit and vegetable juices and protective effects of apple and pear juices against hematolysis and protein oxidation induced by methylene blue and photosensitization. J Food Sci 71:C260-8.
23. Sharma SS, Sayyed SG. 2006. Effects of Trolox on nerve dys function, thermal hyperalgesia and oxidative stress in experimental diabetic neuropathy. Clin Exp Pharmacol Physiol 33:1022-1028
24. Sikorska E, Herance JR, Borudelande JL, Khmelinskii IV, Williams SL, Worrall DR, Nowacka G, Komasa A, Siorski M. 2005. Spectroscopy and photophysics of flavinrelated compounds: 3-ethyl-lumiflavin. J Photochem Photobiol A: Chem 170:267-272 (Pubitemid 40305413)
25. Suh H, Lee H, Jung J. 2003. Mycosporine glycine protects biological systems against photodynamic damage by quenching singlet oxygen with a high efficiency. Photochem Photobiol 78:109-113
26. Szczesniak T, Karabin L, Szczepankowska M, Wituch K. 1971. Biosynthesis of riboflavin by Ashbya gossypii. I. Influence of fats of animal origin on riboflavin production. ActaMicrobiol PolB 3:29-34.
27. [USDA] U.S. Dept. of Agriculture. 2004. National Nutrient Database for Standard Reference, Release 16. Nutrient Lists.
28. Yang S, Lee S, Chung H, Lee JH. 2008. Stability of isoflavone diazein and genistein in riboflavin, chlorophyll b, ormethylene blue photosensitization. J Food Sci 73:C100-5.
29. Yettella RR,MinDB. 2008.Quenchingmechanisms and kinetics of Trolox and ascorbic acid on the riboflavin-photosensitized oxidation of tryptophan and tyrosine. J Agric Food Chem 56:10887-10892
30. Yoshimura A, Ohno T. 1988. Lumiflavin-sensitized photooxidation of indole. Photochem Photobiol 48:561-565