Kinetic study of the quenching reaction of singlet oxygen by carotenoids and food extracts in solution. development of a singlet oxygen absorption capacity (SOAC) assay method

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 18, 2010, Pages 9967-9978

  Ouchi, Aya ^a   Aizawa, Koichi ^b   Iwasaki, Yuko ^b   Inakuma, Takahiro ^b   Terao, Junji ^c   Nagaoka, Shin Ichi ^a   Mukai, Kazuo ^a  

^a EHIME UNIVERSITY   (Japan)

^b KAGOME CO   (Japan)

^c UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

carotene; astaxanthin; carotenoids; endoperoxide; foods; kinetic study; lycopene; quenching rate; Singlet oxygen; SOAC value

Indexed keywords

ASTAXANTHIN; CAROTENOIDS; ENDOPEROXIDES; FOODS; KINETIC STUDY; LYCOPENES; QUENCHING RATE; SINGLET OXYGEN; SOAC VALUE;

ABSORPTION; GAS GENERATORS; KINETIC THEORY; OXYGEN; QUENCHING;

RATE CONSTANTS;

ANTIOXIDANT; CAROTENOID; PLANT EXTRACT; SCAVENGER; SINGLET OXYGEN;

ARTICLE; CARROT; CHEMISTRY; FOOD ANALYSIS; FRUIT; KINETICS; METHODOLOGY; PLANT ROOT; TOMATO;

ANTIOXIDANTS; CAROTENOIDS; DAUCUS CAROTA; FOOD ANALYSIS; FREE RADICAL SCAVENGERS; FRUIT; KINETICS; LYCOPERSICON ESCULENTUM; PLANT EXTRACTS; PLANT ROOTS; SINGLET OXYGEN;

DAUCUS CAROTA; LYCOPERSICON ESCULENTUM;

EID: 77956637093     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101947a     Document Type: Article

References (46)

1. Straub, O. Key to Carotenoids, 2 nd ed.; Birkhäuser: Basle, Switzerland, 1987.
2. Olson, J. A. Biological actions of carotenoids J. Nutr. 1989, 119, 94-95
3. Mangels, A. R.; Holden, J. M.; Beecher, G. R.; Forman, M. R.; Lanza, E. Carotenoid content of fruits and vegetables: an evaluation of analytic data J. Am. Diet. Assoc. 1993, 93, 284-296
4. Holden, J. M.; Eldridge, A. L.; Beecher, G. R.; Buzzard, I. M.; Bhagwat, S.; Davis, C. S.; Douglass, L. W.; Gebhardt, S.; Haytwitz, D.; Schakel, S. Carotenoids content of U.S. food: an update of database J. Food Compos. Anal. 1999, 12, 169-196
5. Aizawa, K.; Inakuma, T. Quantitation of carotenoids in commonly consumed vegetables in Japan Food Sci. Technol. Res. 2007, 13, 247-252
6. Kritchevsky, S. B. β-Carotene, carotenoids and the prevention of coronary heart disease J. Nutr. 1999, 129, 5-8 and references are cited therein
7. Mathews-Roth, M. M. Carotenoids and cancer prevention-experimental and epidemiological studies Pure Appl. Chem. 1985, 57, 717-722
8. Ziegler, R. G. Vegetables, fruits, and carotenoids and the risk of cancer Am. J. Clin. Nutr. 1991, 53, 251s-259s
9. Blot, W. J.; Li, J.-Y.; Taylor, P. R.; Guo, W.; Dawsey, S.; Wang, G.-O.; Yang, C. S.; Zheng, S.-F.; Gail., M.; Li, G.-Y.; Yu, Y.; Liu, B.-Q.; Tangrea, J.; Sun., Y.-H.; Liu, F.; Fraumeni, J. F., Jr.; Zhang, Y.-H.; Li, B. Nutrition intervention trials in Linxian, China: supplementation with specific vitamin/mineral combinations, cancer incidence, and disease-specific mortality in the general population J. Natl. Cancer Inst. 1993, 85, 1483-1492
10. Khachik, F.; Beecher, G. R.; Smith, J. C., Jr. Lutein, lycopene, and their oxidative metabolites in chemoprevention of cancer J. Cell. Biochem. 1995, 59 (s22) 236-246
11. International Agency for Research on Cancer. WHO IARC Handbooks on Cancer Prevention, Vol. 2, Carotenoids; IARC: Lyon, France, 1998
12. Peto, R.; Doll, R.; Buckley, J. D.; Sporn, M. B. Can dietary β-carotene materially reduce human cancer rates? Nature 1981, 290, 201-208
13. Hennekens, C. H.; Buring, J. E.; Manson, J. E.; Stampfer, M.; Rosner, B.; Cook, N. R.; Belanger, C.; LaMotte, F.; Gaziano, J. M.; Ridker, P. M.; Willett, W.; Peto, R. Lack of effect of long-term supplementation with β-carotene on the incidence of malignant neoplasmas and cardiovascular disease New Engl. J. Med. 1996, 334, 1145-1149
14. Gann, P. H.; Ma, J.; Giovannucci, E.; Willett, W.; Sacks, F. M.; Hennekens, C. H.; Stampfer, M. J. Lower prostate cancer risk in men with elevated plasma lycopene levels: results of a prospective analysis Cancer Res. 1999, 59, 1225-1230
15. Giovannucci, E. Tomato products, lycopene, and prostate cancer: a review of the epidemiological literature J. Nutr. 2005, 135, 2030S-2031S
16. Sies, H.; Stahl, W.; Sundquist, A. R. Antioxidant functions of vitamins. Vitamin E and C, β-carotene, and other carotenoids Ann. N.Y. Acad. Sci. 1992, 669, 7-20
17. Foote, C. S.; Denny, R. W. Chemistry of singlet oxygen VII. Quenching by β-carotene J. Am. Chem. Soc. 1968, 90, 6233-6235
18. Di Mascio, P.; Kaiser, S.; Sies, H. Lycopene as the most efficient biological carotenoid singlet oxygen quencher Arch. Biochem. Biophys. 1989, 274, 532-538
19. Di Mascio, P.; Sundquist, A. R.; Devasagayam, T. P. A.; Sies, H. Assay of lycopene and other carotenoids as singlet oxygen quenchers Methods Enzymol. 1992, 213, 429-438
20. 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
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. Mukai, K.; Itoh, S.; Daifuku, K.; Morimoto, H.; Inoue, K. Kinetic study of the quenching reaction of singlet oxygen by biological hydroquinones and related compounds Biochim. Biophys. Acta 1993, 1183, 323-326
23. Mukai, K.; Nagai, S.; Ohara, K. Kinetic study of the quenching reaction of singlet oxygen by tea catechins in ethanol solution Free Radical Biol. Med. 2005, 39, 752-761
24. Nagai, S.; Ohara, K.; Mukai, K. Kinetic study of the quenching reaction of singlet oxygen by flavonoids in ethanol solution J. Phys. Chem. B 2005, 109, 4234-4240
25. Fukuzawa, K.; Inokami, Y.; Tokumura, A.; Terao, J.; Suzuki, A. Rate constants for quenching singlet oxygen and activities for inhibiting lipid peroxidation of carotenoids and α-tocopherol in liposomes Lipids 1998, 33, 751-756
26. Lim, B. P.; Nagao, A.; Terao, J.; Tanaka, K.; Suzuki, T.; Takama, K. Antioxidant activity of xanthophylls on peroxyl radical-mediated phospholipid peroxidation Biochim. Biophys. Acta 1992, 1126, 178-184
27. Cao, G.; Alessio, H. M.; Cutler, R. G. Oxygen-radical absorbance capacity assay for antioxidants Free Radical Biol. Med. 1993, 14, 303-311
28. Wang, H.; Cao, G.; Prior, R. L. Total antioxidant capacity of fruits J. Agric. Food Chem. 1996, 44, 701-705
29. Ou, B.; Hampsch-Woodill, M.; Prior, R. L. Development and validation of an improved oxygen radical absobance capacity assay using fluorescein as the fluorescent probe J. Agric. Food Chem. 2001, 49, 4619-4626
30. Huang, D.; Ou, B.; Hampsch-Woodill, M.; Flanagan, J. A.; Deemer, E. K. Development and validation of oxygen radical absorbance capacity assay for lipophilic antioxidants using randomly methylated β-cyclodextrin as the solubility enhancer J. Agric. Food Chem. 2002, 50, 1815-1821
31. Davies, M. J.; Truscott, R. J. W. Photo-oxidation of proteins and its role in cataractogenesis J. Photochem. Photobiol. B: Biol. 2001, 63, 114-125
32. Davies, M. J. Singlet oxygen-mediated damage to proteins and its consequences Biochem. Biophys. Res. Commun. 2003, 305, 761-770
33. Fieser, L. F.; Gates, M. D., Jr. Synthetic experiments utilizing perinaphthanone-7 J. Am. Chem. Soc. 1940, 62, 2335-2341
34. Marvel, C. S.; Wilson, B. D. Synthetic studies in the dihydropyrene series J. Org. Chem. 1958, 23, 1483-1486
35. g) carriers for biological media J. Photochem. Photobiol. B: Biol. 1996, 36, 31-39 and references are sited therein.
36. Aubry, J. M.; Cazin, B.; Duprat, F. Chemical sources of singlet oxygen. 3. Peroxidation of water-soluble singlet oxygen carriers with the hydrogen peroxide-molybdate system J. Org. Chem. 1989, 54, 726-728
37. Wu, X.; Gu, L.; Holden, J.; Haytowitz, D. B.; Gebhardt, S. E.; Beecher, G.; Prior, R. L. Development of a database for total antioxidant capacity in foods: a preliminary study J. Food Compos. Anal. 2004, 17, 407-422
38. Britton, G. Chapter 2, UV/Visible Spectroscopy. Carotenoids, Vol. 1B: Spectroscopy, Britton, G.; Liaaen-Jensen, S.; Pfander, H., Eds.; Birkhäuser Verlag: Basel, Switzerland, 1995; pp 13-62.
39. Beutner, S.; Bloedorn, B.; Frixel, S.; Blanco, I. H.; Hoffmann, T.; Martin, H.-D.; Mayer, B.; Noack, P.; Ruck, C.; Schmidt, M.; Schulke, I.; Sell, S.; Ernst, H.; Haremza, S.; Seybold, G.; Sies, H.; Stahl, W.; Walsh, R. Quantitative assessment of antioxidant properties of natural colorants and phytochemicals: carotenoids, flavonoids, phenols and indigoids. The role of β-carotene in antioxidant functions J. Sci. Food Agric. 2001, 81, 559-568
40. Young, R. H.; Wehrly, K.; Martin, R. L. Solvent effects in dye-sensitized photooxidation reactions J. Am. Chem. Soc. 1971, 93, 5774-5779
41. Thomas, M. J.; Foote, C. S. Chemistry of singlet oxygen XXVI. Photooxygenation of phenols Photochem. Photobiol. 1978, 27, 683-693
42. Nowakowska, M. β-Carotene inhibited photooxidation of polystyrene. 1. Effect of β-carotene on photochemical reactivity of anthracene in hexane solution Makromol. Chem. 1980, 181, 1013-1020
43. Krasnovsky, A. A., Jr.; Paramonova, L. I. Interaction of singlet oxygen with carotenoids: rate constants of physical and chemical quenching. Translated from Biofizika 1983, 28, 725-729. Biophysics 1983, 28, 769-774.
44. Shiozaki, H.; Nakazumi, H.; Takamura, Y.; Kitao, T. Mechanism and rate constants for the quenching of singlet oxygen by nickel complexes Bull. Chem. Soc. Jpn. 1990, 63, 2653-2658
45. Stratton, S. P.; Schaefer, W. H.; Liebler, D. C. Isolation and identification of singlet oxygen oxidation products of β-carotene Chem. Res. Toxicol. 1993, 6, 542-547
46. Fiedor, J.; Fiedor, L.; Haessner, R.; Scheer, H. Cyclic endoperoxides of β-carotene, potential pro-oxidants, as products of chemical quenching of singlet oxygen Biochim. Biophys. Acta 2005, 1709, 1-4