Electron spin resonance and luminescence spectroscopic observation and kinetic study of chemical and physical singlet oxygen quenching by resveratrol in methanol

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 22, 2010, Pages 11888-11895

  Jung, Mun Yhung ^a   Choi, Dong Seong ^a  

^a Woosuk University   (South Korea)

Author keywords

ESR; near IR fluorescence spectroscopy; quenching; Resveratrol; singlet oxygen

Indexed keywords

ELECTRON SPIN RESONANCE; ESR; ESR SPECTROSCOPY; FOOD SYSTEM; KINETIC STUDY; LIGHT ILLUMINATION; LUMINESCENCE EMISSION; METHYLENE BLUE; N-OXYL RADICALS; NEAR-INFRARED FLUORESCENCE; NEAR-IR FLUORESCENCE SPECTROSCOPY; PHOTOSENSITIZED OXIDATION; POSITIVE EVIDENCE; QUENCHING RATE CONSTANT; RESVERATROL; SINGLET OXYGEN; SPECTROFLUOROMETERS; TERPINENE; TETRAMETHYL;

FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; INFRARED DEVICES; METHANOL; OXYGEN; PHOTOOXIDATION; QUENCHING; RATE CONSTANTS; RESONANCE; SPIN DYNAMICS;

ELECTRON SPIN RESONANCE SPECTROSCOPY;

METHANOL; RESVERATROL; SINGLET OXYGEN; STILBENE DERIVATIVE;

ARTICLE; CHEMISTRY; ELECTRON SPIN RESONANCE; KINETICS; NEAR INFRARED SPECTROSCOPY; SPECTROFLUOROMETRY;

ELECTRON SPIN RESONANCE SPECTROSCOPY; KINETICS; METHANOL; SINGLET OXYGEN; SPECTROMETRY, FLUORESCENCE; SPECTROSCOPY, NEAR-INFRARED; STILBENES;

EID: 78649300234     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101587c     Document Type: Article

References (32)

1. Wei, H.; Cai, Q.; Rahn, R.; Zhang, X. Singlet oxygen involvement in ultraviolet (254 nm) radiation-induced formation of 8-hydroxy-deoxyguanosine in DNA Free Radical Biol. Med. 1997, 23, 148-154
2. Davis, M. J. Singlet oxygen-mediated damage to proteins and its consequences Biochem. Biophys. Res. Commun. 2003, 305, 761-770
3. Kim, J.; Rodriguez, M. E.; Guo, M.; Kenney, M. E.; Oleinick, N. L.; Anderson, V. E. Oxidative modification of cytochrome c by singlet oxygen Free Radical Biol. Med. 2008, 44, 1700-1711
4. Yasaei, P. M.; Yang, G. C.; Warner, C. R.; Daniel, D. H.; Ku, Y. Singlet oxygen oxidation of lipids resulting from photochemical sensitizers in the presence of antioxidants J. Am. Oil Chem. Soc. 1996, 73, 1177-1181
5. Jung, M. Y.; Min, D. B. ESR Study of the singlet oxygen quenching and protective activity of trolox on the photodecomposition of riboflavin and lumiflavin in aqueous buffer solutions J. Food Sci. 2009, 74, C449-C455
6. Lee, J. H.; Min, D. B. Changes of headspace volatiles in milk with riboflavin photosensitization J. Food Sci. 2009, 74, C563-C568
7. Rawls, H. R.; van Santen, P. J. A possible role for singlet oxygen in the initiation of fatty acid autooxidation J. Am. Oil Chem. Soc. 1970, 47, 121-125
8. Basu-Modak, S.; Tyrrell, R. M. Singlet oxygen: a primary effector in the ultraviolet A/near-visible light induction of the human heme oxygenase gene Cancer Res. 1993, 53, 4505-4510
9. Grether-Beck, S.; Olaizola-Horn, S.; Schmitt, H.; Grewe, M.; Jahnke, A.; Johnson, J. P.; Briviba, K.; Sies, H.; Krutmann, J. Activation of transcription factor AP-2 mediates UVA radiation and singlet oxygen-induced expression of the human intercellular adhesion molecule 1 gene Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14586-14591
10. Klotz, L. O.; Kröncke, K. D.; Sies, H. Singlet oxygen-induced signaling effects in mammalian cells Photochem. Photobiol. Sci. 2003, 2, 88-94
11. Baier, J.; Maisch, T.; Maier, M.; Landthaler, M.; Bäumler, W. Direct detection of singlet oxygen generated by UVA irradiation in human cells and skin J. Invest. Dermatol. 2007, 127, 1498-1506
12. Hideg, E.; Tamás, K. T.; Hideg, K.; Vass, I. Photoinhibition of photosynthesis in vivo results in singlet oxygen production detection via nitroxide-induced fluorescence quenching in broad bean leaves Biochemistry 1998, 37, 11405-11411
13. Halliwell, B.; Gutteridge, J. M. C. Measurement of reactive species. In Free Radicals in Biology and Medicine, 4 th ed.; Halliwell, B.; Gutteridge, J. M. C., Eds.; Oxford Science Publications: London, U.K., 2007; pp 268 - 270.
14. Cantos, E.; Garcia-Viguera, C.; de Pascual-Teresa, S.; Tomas-Barberan, F. A. Effect of postharvest ultraviolet irradiation on resveratrol and other phenolics of cv. Napoleon table grapes J. Agric. Food Chem. 2000, 48, 4606-4612
15. Rimando, A. M.; Kalt, W.; Magee, J. B.; Dewey, J.; Ballington, J. R. Resveratrol, pterostilbene, and piceatannol in Vaccinium berries J. Agric. Food Chem. 2004, 52, 4713-4719
16. Olas, B.; Wachowicz, B. Resveratrol and vitamin C as antioxidants in blood platelets Thromb. Res. 2002, 106, 143-148
17. Olas, B.; Wachowicz, B.; Saluk-Juszczak, J.; Zielinski, T. Effect of resveratrol, a natural polyphenolic compound, on platelet activation induced by endotoxin or thrombin Thromb. Res. 2002, 107, 141-145
18. Rimando, A. M.; Cuendet, M.; Desmarchelier, C.; Mehta, R. G.; Pezzuto, J. M.; Duke, S. O. Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol J. Agric. Food Chem. 2002, 50, 3453-3457
19. Sparrow, J. R.; Vollmer-Snarr, H. R.; Zhou, J.; Jang, Y. P.; Jockusch, S.; Itagaki, Y.; Nakanishi, K. A2E-epoxides damage DNA in retinal pigment epithelial cells J. Biol. Chem. 2003, 278, 18207-18213
20. Lion, Y.; Delmelle, M.; Van De Vorst, A. New method of detecting singlet oxygen production Nature 1976, 263, 442-443
21. Oh, Y. S.; Jang, E. S.; Bock, J. Y.; Yoon, S. H.; Jung, M. Y. 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 photosensitization J. Food Sci. 2006, 71, C260-C268
22. Suh, H.; Lee, H.; Jung, J. Mycosporine glycine protects biololical systems against photodynamic damage by quenching singlet oxygen with a high efficiency Photochem. Photobiol. 2003, 78, 109-113
23. Wilkinson, F.; Helman, W. P.; Ross, A. B. Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised complication J. Phys. Chem. Ref. Data 1995, 24, 663-1021
24. Kim, J. I.; Lee, J. H.; Choi, D. S.; Won, B. M.; Jung, M. Y.; Park, J. Y. Kinetic study of the quenching reaction of singlet oxygen by common synthetic antioxidants (tert -butylhydroxyanisole, tert -di-butylhydroxytoluene, and tert -butylhydroquinone) as compared with α-tocopherol J. Food Sci. 2009, 74, C362-C369
25. Foote, C. S.; Ching, T. Y.; Geller, G. G. Chemistry of singlet oxygen-XVIII. Rates of reaction and quenching of α-tocopherol and singlet oxygen Photochem. Photobiol. 1974, 20, 511-513
26. Jung, M. Y.; Kim, S. K.; Kim, S. Y. Riboflavin-sensitized photooxidation of ascorbic acid: kinetics and amino acid effects Food Chem. 1995, 53, 397-403
27. Kim, J. Y.; Choi, D. S.; Jung, M. Y. Antiphoto-oxidative activity of sesamol in methylene blue- and chlorophyll-sensitized photooxidation of oil J. Agric. Food Chem. 2003, 51, 3460-3465
28. 2) by 9,10-dicyanoanthracene and acridine: quantum yields in acetonitrile J. Photochem. Photobiol. 1993, 72, 1-7
29. -2: peroxidation of hydrophobic substrates in pure organic solvents Tetrahedron Lett. 2002, 43, 8731-8734
30. Criado, S.; Carolina, A.; Claudio, C.; Garcia, N. A. Visible-light promoted degradation of the commercial antioxidants butylated hydroxyanisol (BHA) and butylated hydroxytoluene (BHT): a kinetic study Redox Rep. 2007, 12, 282-288
31. He, S.; Jiang, L.; Wu, B.; Pan, Y.; Sun, C. Pallidol, a resveratrol dimer from red wine, is a selective singlet oxygen quencher Biochem. Biophys. Res. Commun. 2009, 379, 283-287
32. Lee, J. H.; Jung, M. Y. Direct spectroscopic observation of singlet oxygen quenching and kinetic studies of physical and chemical singlet oxygen quenching rate constants of synthetic antioxidants (BHA, BHT and TBHQ) in methanol J. Food Sci. 2010, 75, C506-C513