Visible-light-promoted degradation of the antioxidants propyl gallate and t-butylhydroquinone: Mechanistic aspects

Redox Report

Volumn 17, Issue 3, 2012, Pages 131-138

  Criado, Susana ^a   Allevi, Carolina ^a   García, Norman A ^a  

^a DEPARTAMENTO DE QUÍMICA   (Argentina)

Author keywords

Antioxidants; Photooxidation; Propyl gallate; Reactive Oxygen Species; Riboflavin; t buthylhydroquinone

Indexed keywords

DISSOLVED OXYGEN; GALLIC ACID PROPYL ESTER; HYDROGEN PEROXIDE; HYDROXIDE; REACTIVE OXYGEN METABOLITE; RIBOFLAVIN; ROSE BENGAL; SINGLET OXYGEN; TERT BUTYLHYDROQUINONE;

ANTIOXIDANT ACTIVITY; ARTICLE; DRUG DEGRADATION; DRUG TRANSFORMATION; LIGHT; OXYGEN CONSUMPTION; PHOTODEGRADATION; PRIORITY JOURNAL;

ANIMALS; ANTIOXIDANTS; FLUOROIMMUNOASSAY; HYDROGEN PEROXIDE; HYDROQUINONES; HYDROXYL RADICAL; LIGHT; LUMINESCENT MEASUREMENTS; PHOTOLYSIS; PROPYL GALLATE; ROSE BENGAL; SINGLET OXYGEN;

EID: 84863792858     PISSN: 13510002     EISSN: 17432928     Source Type: Journal    
DOI: 10.1179/12Z.00000000018     Document Type: Article

References (42)

1. Fasseas MK, Mountzouris KC, Tarantilis PA, Polissou M, Zervas G. Antioxidant activity in meat treated with oregano and sage essential oils. Food Chem 2007;106:1188-94.
2. Alamed J, Chaiyasit W, McClements DJ, Decker EA. Relationships between free radical scavenging and antioxidant activity in foods. J Agric Food Chem 2009;57:2969-76.
3. Pazos M, Alonso A, Sánchez I, Medina I. Hydroxytyrosol prevents oxidative deterioration in foodstuffs rich in fish lipids. J Agric Food Chem 2008;56:3334-40.
4. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Some naturally occurring and synthetic food components. Vol. 40 Lyon: IARC Press; 1986. p. 123-206.
5. Guan Y, Chu Q, Fu L, Wu T, Ye J. Determination of phenolic antioxidants by micellar electrokinetic capillary chromatography with electrochemical detection. Food Chem 2005;94:157-62.
6. Albini A, Fasani E. Drugs. Photochemistry and photostability. Cambridge, UK: The Royal Society of Chemistry; 1998.
7. Criado S, Allevi C, Ceballos C, García NA. Visible-light-promoted degradation of the comercial antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). A kinetic study. Redox Rep 2007;12:283-8.
8. Heelis PF. The photophysical and photochemical properties of flavin (isoalloxazines). Chem Soc Rev 1982;11:15-39.
9. Silva E, Ugarte R, Andrade A, Edwards AM. Riboflavin-sensitized photoprocesses of tryptophan. J Photochem Photobiol B: Biol 1994;23:43-8.
10. Silva E, Ruckert V, Lissi E, Abuin E. Effects of pH and ionic micelles on the riboflavin-sensitized photoprocesses of tryptophan. J Photochem Photobiol B: Biol 1991;11:57-68.
11. Choe E, Huang R, Min DB. Chemical reactions and stability of riboflavin in foods. J Food Sci 2005;70:28-36.
12. Foote CS, Ching TY. Chemistry of singlet oxygen XXI. Kinetics of bilirubin photooxygenation. J Am Chem Soc 1975;97: 6209-14.
13. Neckers DC. Rose Bengal. J Photochem Photobiol A: Chem 1989;47:1-29.
14. Criado S, Bertolotti SG, García NA. Kinetic aspects of the Rose Bengal sensitized photooxygenation of tryptophan alkyl esters. Ground state and photopromoted dye-tryptophan derivative interactions. J Photochem Photobiol B: Biol 1996;34:79-86.
15. Nonell S, Moncayo L, Trull F, et al. Solvent influence on the photodynamic degradation of Trolox, a water-soluble model compound for vitamin E. J Photochem Photobiol B: Biol 1995;29:157-62.
16. Fritz BJ, Matsui K, Kasai S, Yoshimura A. Triplet lifetime of some flavins. Photochem Photobiol 1987;45:539-41.
17. Wilkinson F, Helman W, Ross AB. Rate constants for the decay of the lowest electronically excited singlet state molecular oxygen in solution. An expanded and revised compilation. J Phys Chem Ref Data 1995;24:663-1021.
18. 2) photosensitized oxidation of 2′-deoxyguanosine-5′-monophosphate (dGMP) in aqueous solution: a transient intermediates study. Phys Chem Chem Phys 2000;2:329-34.
19. Baxter RM, Carey JH. Evidence for photochemical generation of superoxide ion in humic waters. Nature 1983;306:575-6.
20. Zang LY, Misra HP. Superoxide radical production during the autoxidation of 1-methyl-4-phenyl-2,3-dihydroxypyridinium perchlorate. J Biol Chem 1992;267:17547-52.
21. Iuliano L, Pratico D, Ghiselli A, Bonavita MS, Violi F. Reaction of dipyridamole with hydroxyl radical. Lipids 1992;27:349-53.
22. Tratniek PG, Hoignè J. Oxidation of substituted phenols in the environment: a QSAR analysis of rate constants for reaction with singlet oxygen. Environ Sci Technol 1991;25:1596-604.
23. Silva E, Herrera L, Edwards AM, De la Fuente J, Lissi E. Enhancement of riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by uronic acid. Photochem Photobiol 2005;81:206-11.
24. Silva E, Edwards AM, Pacheco D. Visible light-induced photooxidation of glucose sensitized by riboflavin. J Nutr Biochem 1999;10:181-5.
25. Cohen G, Heikkila RE. The generation of hydrogen peroxide, superoxide radical and hydroxyl radical by 6-hydroxydopamine, dialuric acid and related cytotoxic agents. J Biol Chem 1974;249: 2447-53.
26. Frati E, Khatib AM, Front P, Panasyuk A, Aprile F, Mitrovic RD. Degradation of hyaluronic acid by photosensitized riboflavin in vitro. Modulation of the effect by transition metals, radicals quenchers and metal chelators. Free Radical Bio Med 1997;22:1139-44.
27. Criado S, García NA. A Comparative kinetic and mechanistic study between Tetrahydrozoline and Naphazoline toward photogenerated reactive oxygen species. Photochem Photobiol 2010; 86:23-30.
28. Bertolotti SG, Previtali CM, Rufs AM, Encinas MV. Riboflavin/triethanolamine as photoinitiator system of vinyl polymerization. A mechanistic study by laser flash photolysis. Macromolecules 1999;32:2920-4.
29. Haggi E, Bertolotti S, Miskoski S, Amat-Guerri F, García NA. Environmental photodegradation of pyrimidine fungicides. Kinetics of the visible-light-promoted interactions between riboflavin and 2-amino-4-hydroxy-6-methylpyrimidine. Can J Chem 2002;80:62-7.
30. Lu C, Bucher G, Sander W. Photoinduced interaction between oxidized and reduced lipoic acid and riboflavin (vitamin B2). Phys Chem Phys 2004;5:47-56.
31. Lu CY, Wang WF, Lin WZ, Han ZH, Yao SD, Lin NY. Generation and photosensitization properties of the oxidized radicals of riboflavin: a laser flash photolysis study. J Photochem Photobiol B: Biol 1999;52:111-6.
32. Kanofsky JR. Singlet oxygen production from the reaction of superoxide ion in aprotic solvents: implications for hydrophobic biochemistry. Free Rad Res Commun 1991;87:12-3.
33. Koizumi M, Kato S, Mataga N, Matsuura T, Isui I. Photosensitized reactions. Kyoto: Kagakudogin; 1978.
34. Calvert J, Pitts J. Photochemistry. New York: John Wiley & Sons; 1966.
35. Murov SL. Handbook of photochemistry. New York: M. Decker; 1973. p. 89.
36. Land EJ, Swallow AJ. One-electron reactions in biochemical systems as studied by pulse radiolysis. II Riboflavin. Biochemistry 1969;8:2117-25.
37. Pajares A, Gianotti J, Stettler G, Bertolotti SG, Criado S, Posadaz A, et al. Modelling the natural photodegradation of water contaminants: a kinetic study on the light-induced interactions between riboflavin and 4-hydroxypyridine. J Photochem Photobiol A: Chem 2001;139:199-204.
38. Chacon JN, McLearie J, Sinclair RS. Singlet oxygen yields and radical contributions in the dye-sensitised photooxidation in methanol of esters of polyunsaturated fatty acids (oleic, linoleic, linolenic and arachidonic). Photochem Photobiol 1988;47: 647-56.
39. García NA. Singlet molecular oxygen mediated photodegradation of aquatic phenolic pollutants. A kinetic and mechanistic overview. J. Photochem Photobiol B: Biol 1994;22:185-96.
40. g)]-mediated photoreactions. Photochem Photobiol 2005;81:325-32.
41. Thomas MJ, Foote CS. Chemistry of singlet oxygen XXVI. Photooxygenations of phenols. Photochem Photobiol 1978;27: 683-93.
42. Wright A, Bubb WA, Hawkins CL, Davies M. Singlet oxygenmediated protein oxidation: evidence for the formation of reactive side chain peroxides on tyrosine residues. Photochem Photobiol 2002;76:35-46.