Mechanism of deactivation of triplet-excited riboflavin by ascorbate, carotenoids, and tocopherols in homogeneous and heterogeneous aqueous food model systems

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 15, 2007, Pages 6285-6291

  Cardoso, Daniel R ^a   Olsen, Karsten ^b   Skibsted, Leif H ^b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Ascorbate; Carotenoids; Chemical quenching; Laser flash photolysis; Riboflavin; Tocopherols

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; CAROTENOID; RIBOFLAVIN; TOCOPHEROL; WATER;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; FOOD ANALYSIS; LIGHT; PHOTOLYSIS; SOLUTION AND SOLUBILITY;

ANTIOXIDANTS; ASCORBIC ACID; CAROTENOIDS; FOOD ANALYSIS; LIGHT; PHOTOLYSIS; RIBOFLAVIN; SOLUTIONS; TOCOPHEROLS; WATER;

EID: 34547769937     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf063497q     Document Type: Article

References (26)

1. Bradley, R. L. J. Effect of light on alteration of nutritional value and flavour of milk: a review. J. Food Prat. 1980, 43, 314-320.
2. Skibsted, L. H. Light-induced changes in dairy products. Bull. Int. Dairy Found. 2000, 346, 4-9.
3. Mortensen, G.; Bertelsen, G.; Mortensen, B. K.; Stapelfeldt, H. Light-induced changes in packaged cheeses - a review. Int. Dairy J. 2004, 14, 85-102.
4. Huvaere, K.; Andersen, M. L.; Storme, M.; Bocxlaer, J. V.; Skibsted, L. H.; De Keukeleire, D. Flavin induced photodecompostion of sulfur-containing acids is decisive in the formation of beer lightstruck flavor. Photochem. Photobiol. Sci. 2006, 5, 961-969.
5. Criado, S.; Pajares, A.; Gianotli, J.; Stettler, G.; Escalada, J. P.; Bertolotti, S.; Amat-Guerri, F.; Garcia, N. Kinetic study of the riboflavin sensitized photooxygenation of two hydroxyquinones of biological interest. J. Photochem. Photobiol. B. 2003, 71, 19- 25.
6. Martin, C. B.; Tsao, M.-L.; Hadad, C. M.; Platz, M. S. The reaction of triplet flavin with indole. A study of the cascade of reactive intermediates using density functional theory and time resolved infrared spectroscopy. J. Am. Chem. Soc. 2002, 124, 7226-7234.
7. Heelis, P. F. The photophysical and photochemical properties of flavins (isoalloxazines). Chem. Soc. Rev. 1982, 11, 15-39.
8. Martin, C. B.; Shi, X. F.; Tsao, M. L.; Karweik, D.; Brooke, J.; Hadad, C. M.; Platz, M. S. The photochemistry of riboflavin tetraacetate and nucleosides. A study using density functional theory, laser flash photolysis, fluorescence, UV-vis, and time resolved infrared spectroscopy. J. Phys. Chem. B 2002, 106, 10263-10271.
9. Goldsmith, M. R.; Rogers, P. J.; Cabral, N. M.; Ghiggino, K. P.; Roddick, F. A. Riboflavin triplet quenchers inhibit lightstruck flavor formation in beer. J. Am. Soc. Brew. Chem. 2005, 63, 177-184.
10. Haggi, E.; Bertolotti, S.; Garcia, N. A. Modelling the environmental degradation of water contaminants. Kinetics and mechanism of the riboflavin-sensitised-photooxidation of phenolic compounds. Chemosphere 2004, 55, 1501-1507.
11. Li, T.; King, J. M.; Min, D. B. Quenching mechanism and kinetics of carotenoids in riboflavin photosensitized singlet oxidation of vitamin D2. J. Food Biochem. 2000, 24, 477-492.
12. Cardoso, D. R.; Franco, D. W.; Olsen, K.; Andersen, M. L.; Skibsted, L. H. Reactivity of bovine whey proteins, peptides and amino acids towards triplet riboflavin. A laser flash photolysis study. J. Agric. Food Chem. 2004, 52, 6602-6606.
13. Jung, M. Y.; Kim, K.; S.; Kim, S. Y. Riboflavin-sensitized photooxidation of ascorbic acid: kinetics and amino acids effects. Food Chem. 1995, 53, 397-403.
14. Havemose, M. S.; Weisbjerg, M. R.; Bredie, W. L. P.; Nielsen, J. H. Influence of feeding different types of roughage on the oxidative stability of milk. Int. Dairy J. 2004, 14, 563-570.
15. Cardoso, D. R.; Homem-de-Mello, P.; Olsen, K.; da Silva, A. B. F.; Franco, D. W.; Skibsted, L. H. Deactivation of triplet-excited riboflavin by purine derivatives. Important role of uric acid in light-induced oxidation of milk sensitized by riboflavin. J. Agric. Food Chem. 2005, 53, 2679-3684.
16. Stratton, S. P.; Liebler, D. C.; Determination of singlet oxygen-specific versus radical mediated lipid peroxidation in photosensitized oxidation of lipid bilayers: effect of β-carotene and α-tocopherol. Biochemistry 1997, 36, 12911-12920.
17. Lu, C. Y.; Lin, W. Z.; Wang, W. F.; Han, Z. H.; Yao, S.; Lin, N. Y. Riboflavin (VB2) photosensitized oxidation of 2′-deoxyguanosine-5′- monophosphate (dGMP) in aqueous solution: a transient intermediates study. Phys. Chem. Chem. Phys. 2000, 2, 329-334.
18. Hansen, E.; Skibsted, L. H. Light-induced oxidative changes in a model dairy spread cheese. Wavelength dependence of quantum yield and inner-filter protection by β-carotene. J. Agric. Food Chem. 2000, 48, 3090-3094.
19. Becker, E. M.; Cardoso, D. R.; Skibsted, L. H. Deactivation of riboflavin triplet-excited state by phenolic antioxidants: mechanism behind protective effects in photooxidation of milk-based beverages. Eur. Food Res. Technol. 2005, 221, 382-386.
20. Wright, J. S.; Johnson, E. R.; DiLabio, G. A. Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants. J. Am. Chem. Soc. 2001, 123, 1173-1183.
21. Mukai, K.; Daifuku, K.; Okabe, K.; Tanigaki, T.; Inoue, K. Structure-activity relationship in the quenching reaction of singlet oxygen by tocopherol (vitamin E) derivatives and related phenols. Finding of linear correlation between the rates of quenching of singlet oxygen and scavenging of peroxyl and phenoxyl radicals in solution. J. Org. Chem. 1991, 56, 4188-4192.
22. Havemose, M. S.; Weisbjerg, M. R.; Bredie, W. L. P.; Nielsen, J. H. Influence of feeding different types of roughage on the oxidative stability of milk. Int. Dairy J. 2004, 14, 563-570.
23. Luk'yanchikova, I. A.; Ivlev, D. V.; Kiselev, M. G.; Al'per, G. A. Concentration dependence of the viscosity of tert-butanol-water mixtures: physical experiment and computer simulation. Russian J. Gen. Chem. 2004, 74, 1156-1162.
24. Kramer, K. A.; Liebler, D. C. UVB induced photooxidation of vitamin E. Chem. Res. Toxicol. 1997, 10, 219-224.
25. Krol, E. S.; Escalante, D. D. J.; Liebler, D. C. Mechanism of dimer and trimer formation from ultraviolet-irradiated α-tocopherol. Lipids 2001, 36, 49-55.
26. Kristensen, D.; Hedegaard, R. V.; Nielsen, J. H.; Skibsted, L. H. Oxidative stability of buttermilk as influenced by the fatty acid composition of cows milk manipulated by diet. J. Dairy Res. 2004, 71, 46-50.