Mechanisms of Inactivation of Oxygen Species by Carotenoids

  • Norman I. Krinsky


Although carotenoid pigments have been implicated as anti-carcinogenic compounds for several years, based on both epidemiological evidence (1) as well as experiments in animals (2,3), the exact mechanism whereby this widely distributed class of componds functions is still poorly understood. What appears to be important however, is the fact that many of the effects of carotenoids in vivo and in vitro can be observed with pigments that do not function as precursors of vitamin A (retinol). For example, beta-carotene may exert its biological effects merely by functioning as a precursor of retinal and retinol. On the other hand, there are carotenoid pigments, such as canthaxanthin (4,4’-diketo-beta-carotene) which also exhibit anti-carcinogenic properties and cannot be converted to retinol (Figure 1). Under these circumstances, we must look at the properties of the intact molecules in order to understand their functions.


Singlet Oxygen Xanthine Oxidase Active Oxygen Species Peroxyl Radical Sister Chromatid Exchange 
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  1. 1.
    R. Peto, R. Doll, J.D. Buckley, and M.B. Sporn. Can dietary beta-carotene materially reduce human cancer rates? Nature 290, 201–208 (1981).PubMedCrossRefGoogle Scholar
  2. 2.
    M.M. Mathews-Roth. Carotenoids and cancer prevention — experimental and epidemiological studies. Pure Appi. Chem. 57, 717–722 (1985).CrossRefGoogle Scholar
  3. 3.
    L. Santamaria, L. Bianchi, A. Arnaboldi, L. Andreoni, and P. Bermond. Dietary carotenoids block photocarcinogenic enhancement by benzo(a)pyrene and inhibit its carcinogenesis in the dark. Experientla 39, 1043–1045 (1983).CrossRefGoogle Scholar
  4. 4.
    N.I. Krinsky, Biology and Photobiology of Singlet Oxygen, in Oxygen Radicals In Chemistry and Biology (W. Bors, M. Saran and D. Tait, Eds.) pp. 453–464. Walter de Gruyter, Berlin, 1984.CrossRefGoogle Scholar
  5. 5.
    I. Fridovich. Biological effects of the superoxide radical. Arch. Biochem. Biophys. 247, 1–11 (1986).PubMedCrossRefGoogle Scholar
  6. 6.
    A.I. Tauber and B.M. Babior, Neutrophil oxygen reduction: The enzymes and the products. Adv. Free Radical Biol. Med. 1, 265–307 (1985).CrossRefGoogle Scholar
  7. 7.
    C.S. Feote, and R.W. Denny. Chemistry of Singlet Oxygen. VII. Quenching by beta-carotene. J. Am. Chem. Soc. 90, 6233–6235 (1968).CrossRefGoogle Scholar
  8. 8.
    S.M. Anderson, and N.I. Krinsky. Protective action of carotenoid pigments against photodynamic damage to liposomes. Photochem. Photobiol. 18, 403–408 (1973).PubMedCrossRefGoogle Scholar
  9. 9.
    N.I. Krinsky. Carotenoid protection against oxidation. Pure Appl. Chem. 51, 649–660 (1979).CrossRefGoogle Scholar
  10. 10.
    J.R. Kanovsky and B. Axelrod, Singlet oxygen production by soybean lipoxygenase isozymes. J. Biol. Chem. 261, 1099–1104 (1986).Google Scholar
  11. 11.
    E. Cadenas. Oxidative stress and formation of excited species, in Oxidative Stress (H. Sies, Ed.) pp. 311–330. Academic Press, New York, 1985.Google Scholar
  12. 12.
    W. Bors, C. Michel and M. Saran. Inhibition of the bleaching of the carotenoid crocin. A rapid test for quantifying antioxidant activity. Biochim. Biophys. Acta 796, 312–319 (1984).Google Scholar
  13. 13.
    W. Bors, M. Saran, and C. Michel. Radical intermediates involved in the bleaching of the carotenoid crocin. Hydroxyl radicals, superoxide anions and hydrated electrons. Int. J. Radiat. Biol. 41, 493–501 (1982).CrossRefGoogle Scholar
  14. 14.
    B.P. Klein, D. King, and S. Grossman. Cooxidation reactions of lipoxygenase in plant systems. Adv. Free Radical Biol. Med. 1, 308–343 (1985).CrossRefGoogle Scholar
  15. 15.
    J.E. Packer, J.S. Mahood, V.O. Mora-Arellano, T.F. Slater, R.L. Willson, and B.S. Wolfenden. Free radicals and singlet oxygen scavengers: reaction of a peroxy-radical with beta-carotene, diphenylfuran and 1,4-diazobicyclo(2,2,2)-octane. Biochem. Biophys. Res. Commun. 98, 901–906 (1981).PubMedCrossRefGoogle Scholar
  16. 16.
    E.W. Kellogg III and I. Fridovich, Superoxide, hydrogen peroxide, and singlet oxygen in lipid peroxidation by a xanthine oxidase system. J. Biol. Chem. 250, 8812–8817 (1975).PubMedGoogle Scholar
  17. 17.
    N.I. Krinsky. Carotenoid pigments: multiple mechanisms for coping with the stress of photosensitized oxidations. in Strategies of Microbial Life in Extreme Environments (M. Shilo, ed.) pp. 163–177, Dahlem Konferenzen, Berlin, 1979.Google Scholar
  18. 18.
    N.I. Krinsky, and S.M. Deneke. Interaction of oxygen and oxy-radicals with carotenoids. JNCI 69, 205–210 (1982).PubMedGoogle Scholar
  19. 19.
    R. Dixit, H. Mukhtar, and D.R. Bickers. Studies on the role of reactive oxygen species in mediating lipid peroxide formation in epidermal microsomes of rat skin. J. Invest. Dermatol. 81, 369–375 (1983).PubMedCrossRefGoogle Scholar
  20. 20.
    G.W. Burton, and K.W. Ingold. Beta-Carotene: an unusual type of lipid antioxidant. Science 224, 569–573 (1984).PubMedCrossRefGoogle Scholar
  21. 21.
    J.M. Albrich, C.A. Marthy, and J.K. Hurst, Biological reactivity of hypochlorous acid. Implications for microbicidal mechanisms of leukocyte myeloperoxidase. Proc. Natl. Acad. Sci. U.S.A. 78, 210–214 (1981).PubMedCrossRefGoogle Scholar
  22. 22.
    M. M. Mathews-Roth, Porphyrin photosensitiztion and carotenoid protection in mice; in vitro and in vivo studies. Photochem. Photobiol. 63–67 (1984).Google Scholar
  23. 23.
    N.I. Krinsky. Singlet excited oxygen as a mediator of the antibacterial action of leukocytes. Science 186,363–365 (1974).PubMedCrossRefGoogle Scholar
  24. 24.
    H. Rosen, and S.J. Klebanoff, Bactericidal activity of a superoxide anion-generating system. A model for the poljnnorphonuclear leukocyte. J. Exp. Med. 149, 27–39 (1979).PubMedCrossRefGoogle Scholar
  25. 25.
    A.B. Weitberg, S.A. Weitzman, E.P. Clark, and T.P. Stossel. Effects of antioxidants on oxidant-induced sister chromatid exchange formation. J. Clin. Invest. 75, 1835–1841 (1985).PubMedCrossRefGoogle Scholar
  26. 26.
    P.A. Rubin, S. Welankiwar, and N.I. Krinsky. Unpublished observations (1987).Google Scholar

Copyright information

© Plenum Press, New York 1987

Authors and Affiliations

  • Norman I. Krinsky
    • 1
  1. 1.Department of Biochemistry and PharmacologyTufts University School of MedicineBostonUSA

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