Importance of Carotenoid Structure in Radical-Scavenging Reactions

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 8, 1997, Pages 2970-2977

  Mortensen, Alan ^a   Skibsted, Leif H ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Antioxidant synergism; Astaxanthin; Canthaxanthin; Carotenoid radicals; Echinenone; Lutein; Lycopene; Phenoxyl radical; Zeaxanthin; apo 8 carotenal; Carotene

Indexed keywords

EID: 0001271178     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970010s     Document Type: Article

References (31)

1. Böhm, F.; Tinkler, J. H.; Truscott, T. G. Carotenoids protect against cell membrane damage by the nitrogen dioxide radical. Nature Medicine 1995, 1, 98-99.
2. Böhm, F.; Edge, R.; Land, E. J.; McGarvey, D. J.; Truscott, T. G. Carotenoids enhance vitamin E antioxidant efficiency. J. Am. Chem. Soc. 1997, 119, 621-622.
3. Burton, G. W.; Ingold, K. U. β-Carotene: An unusual type of lipid antioxidant. Science 1984, 224, 569-573.
4. Everett, S. A.; Dennis, M. F.; Patel, K. B.; Maddix, S.; Kundu, S. C.; Willson, R. L. Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β-carotene. J. Biol. Chem. 1996, 271, 3988-3994.
5. Everett, S. A.; Kundu, S. C.; Maddix, S.; Willson, R. L. Mechanisms of free radical scavenging by the nutritional antioxidant β-carotene. Biochem. Soc. Trans. 1995, 23, 230S.
6. Gerster, H. The potential role of lycopene for human health. J. Am. Coll. Nutr. 1997, 16, 109-126.
7. Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; Blackwell: Oxford, 1991.
8. 2. radical. J. Am. Chem. Soc. 1995, 117, 8322-8326.
9. Johnston, L. J.; Mathivanan, N.; Negri, F.; Siebrand, W.; Zerbetto, F. Assignment and vibrational analysis of the 600 nm absorption band in the phenoxyl radical and some of its derivatives. Can. J. Chem. 1993, 71, 1655-1662.
10. Jørgensen, K.; Skibsted, L. H. Carotenoid scavenging of radicals. Effect of carotenoid structure and oxygen partial pressure on antioxidalive activity. Z. Lebensm.-Unters. Forsch 1993, 196, 423-429.
11. Jørgensen, L. V.; Andersen, H. J.; Skibsted, L. H. Kinetics of reduction of hypervalent iron in myoglobin by crocin in aqueous solution. Free Radical Res. 1997, in press.
12. Krinsky, N. I. The biological properties of carotenoids. Pure Appl. Chem. 1994, 66, 1003-1010.
13. Liebler, D. C.; McClure, T. D. Antioxidant reactions of β-carotene: Identification of carotenoid-radical adducts. Chem. Res. Toxicol. 1996, 9, 8-11.
14. Mahoney, L. R.; Weiner, S. A. A mechanistic study of the dimerization of phenoxyl radicals. J. Am. Chem. Soc. 1972, 94, 585-590.
15. Miller, N. J.; Sampson, J.; Candeias, L. P.; Bramley, P. M.; Rice-Evans, C. A. Antioxidant activities of carotenes and xanthophylls. FEBS Lett. 1996, 384, 240-242.
16. Mortensen, A.; Skibsted, L. H. Kinetics of photobleaching of β-carotene in chloroform and formation of transient carotenoid species absorbing in the near infrared. Free Radical Res. 1996a, 25, 355-368.
17. Mortensen, A.; Skibsted, L. H. Kinetics of parallel electron transfer from β-carotene to phenoxyl radical and adduct formation between phenoxyl radical and β-carotene. Free Radical Res. 1996b, 25, 515-523.
18. Mortensen, A.; Skibsted, L. H. Free radical transients in photobleaching of xanthophylls and carotenes. Free Radical Res. 1997a, 26, 549-563.
19. Mortensen, A.; Skibsted, L. H. Real time detection of reactions between radicals of lycopene and tocopherol homologues. Free Radical Res. 1997b, in press.
20. -. J. Am. Chem. Soc. 1975, 97, 912-913.
21. 40 carotenoids. J. Agric. Food Chem. 1996, 44, 2106-2113.
22. Palozza, P.; Krinsky, N. I. Antioxidant effects of carotenoids in vivo and in vitro: An overview. Methods Enzymol. 1992a, 213, 403-420.
23. Palozza, P.; Krinsky, N. I. β-Carotene and α-tocopherol are synergistic antioxidants. Arch. Biochem. Biophys. 1992b, 297, 184-187.
24. Palozza, P.; Krinsky, N. I. Antioxidant properties of carotenoids. In Retinoids: From basic science to clinical applications; Livrea, M. A., Vidali, G., Eds.; Birkhäuser Verlag: Basel, Switzerland, 1994.
25. Qin, Y.; Wheeler, R. A. Similarities and differences between phenoxyl and tyrosine phenoxyl radical structures, vibrational frequencies, and spin densities. J. Am. Chem. Soc. 1995, 117, 6083-6092.
26. Simic, M. G.; Dizdaroglu, M. Formation of radiation-induced crosslinks between thymine and tyrosine: possible model for crosslinking of DNA and proteins by ionizing radiation. Biochemistry 1985, 24, 233-236.
27. Tew, D.; Ortiz de Montellano, P. R. The myoglobin protein radical. J. Biol. Chem. 1988, 263, 17880-17886.
28. Tripathi, G. N. R.; Schuler, R. H. The resonance Raman spectrum of phenoxyl radical. J. Chem. Phys. 1984, 81, 113-121.
29. Tyurin, V. A.; Carta, G.; Tyurina, Y. Y.; Banni, S.; Day, B. W.; Corongiu, F. P.; Kagan, V. E. Peroxidase-catalyzed oxidation of β-carotene in HL-60 cells and in model systems: involvement of phenoxyl radical. Lipids 1997, 32, 131-142.
30. Weiner, S. A. A steady state technique for measuring phenoxy radical termination constants. J. Am. Chem. Soc. 1972, 94, 581-584.
31. Woodall, A. A.; Britton, G.; Jackson, M. J. Dietary supplementation with carotenoids: effects on α-tocopherol levels and susceptibility of tissues to oxidative stress. Br. J. Nutr. 1996, 76, 307-317.