Antioxidant and prooxidant properties of carotenoids.

The ability of dietary carotenoids such as beta-carotene and lycopene to act as antioxidants in biological systems is dependent upon a number of factors. While the structure of carotenoids, especially the conjugated double bond system, gives rise to many of the fundamental properties of these molecules, it also affects how these molecules are incorporated into biological membranes. This, in turn, alters the way these molecules interact with reactive oxygen species, so that the in vivo behavior may be quite different from that seen in solution. The effectiveness of carotenoids as antioxidants is also dependent upon their interaction with other coantioxidants, especially vitamins E and C. Carotenoids may, however, lose their effectiveness as antioxidants at high concentrations or at high partial pressures of oxygen. It is unlikely that carotenoids actually act as prooxidants in biological systems; rather they exhibit a tendency to lose their effectiveness as antioxidants.

[1]  D. Albanes,et al.  The effect of vitamin E and beta carotene on the incidence of lung cancer and other cancers in male smokers. , 1994, The New England journal of medicine.

[2]  A. Young,et al.  Carotenoid-dependent oligomerization of the major chlorophyll a/b light harvesting complex of photosystem II of plants. , 1997, Biochemistry.

[3]  G. Omenn,et al.  Effects of a combination of beta carotene and vitamin A on lung cancer and cardiovascular disease. , 1996, The New England journal of medicine.

[4]  P. Di Mascio,et al.  Lycopene as the most efficient biological carotenoid singlet oxygen quencher. , 1989, Archives of biochemistry and biophysics.

[5]  P. Palozza,et al.  Prooxidant activity of β-carotene under 100% oxygen pressure in rat liver microsomes , 1995 .

[6]  G. Britton,et al.  Oxidation of carotenoids by free radicals: relationship between structure and reactivity. , 1997, Biochimica et biophysica acta.

[7]  B. S. Alam,et al.  Lipid Peroxide, α-Tocopherol and Retinoid Levels in Plasma and Liver of Rats Fed Diets Containing β-Carotene and 13-cis-Retinoic Acid , 1983 .

[8]  P. Palozza Prooxidant actions of carotenoids in biologic systems. , 2009, Nutrition reviews.

[9]  Proposed Mechanisms for the Formation of Synthetic and Naturally Occurring Metabolites of Lycopene in Tomato Products and Human Serum , 1998 .

[10]  W. Stahl,et al.  Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene. , 2000, Archives of biochemistry and biophysics.

[11]  W. Schalch,et al.  The singlet oxygen and carotenoid interaction. , 1991, Journal of photochemistry and photobiology. B, Biology.

[12]  K. Ingold,et al.  beta-Carotene: an unusual type of lipid antioxidant. , 1984, Science.

[13]  F. Wilkinson,et al.  Electronic Energy Transfer from Sinclet Molecular Oxygen to Carotenoids , 1978 .

[14]  F. Khachik,et al.  Metabolites of dietary carotenoids as potential cancer preventive agents , 1997 .

[15]  W. Pryor,et al.  Beta carotene and its oxidation products have different effects on microsome mediated binding of benzo[a]pyrene to DNA. , 1999, Free radical biology & medicine.

[16]  L. Skibsted,et al.  Comparative mechanisms and rates of free radical scavenging by carotenoid antioxidants , 1997, FEBS letters.

[17]  W. Stahl,et al.  Singlet Oxygen Quenching Abilities of Carotenoids , 1997 .

[18]  D. Liebler,et al.  Peroxyl radical oxidation of beta-carotene: formation of beta-carotene epoxides. , 1991, Chemical research in toxicology.

[19]  Andrew J. Young,et al.  The Photochemistry of Carotenoids , 1999, Advances in Photosynthesis and Respiration.

[20]  A. Young,et al.  Excited‐State Energy Level Does Not Determine the Differential Effect of Violaxanthin and Zeaxanthin on Chlorophyll Fluorescence Quenching in the Isolated Light‐Harvesting Complex of Photosystem II , 1998 .

[21]  J. C. Smith,et al.  Identification, quantification, and relative concentrations of carotenoids and their metabolites in human milk and serum. , 1997, Analytical chemistry.

[22]  M. Mathews-Roth Carotenoids and Photoprotection * , 1997 .

[23]  S. Grundy,et al.  Preservation of the endogenous antioxidants in low density lipoprotein by ascorbate but not probucol during oxidative modification. , 1991, The Journal of clinical investigation.

[24]  E. Land,et al.  Interactions between Carotenoids and the CCl3O2.bul. Radical , 1995 .

[25]  T. G. Truscott,et al.  β‐Carotene with vitamins E and C offers synergistic cell protection against NOx , 1998, FEBS letters.

[26]  G. Britton,et al.  Structure and properties of carotenoids in relation to function , 1995, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[27]  M. Havaux,et al.  The protective function of the xanthophyll cycle in photosynthesis , 1994, FEBS letters.

[28]  G. Britton,et al.  Carotenoids and protection of phospholipids in solution or in liposomes against oxidation by peroxyl radicals: relationship between carotenoid structure and protective ability. , 1997, Biochimica et biophysica acta.

[29]  M. Russell,et al.  Retinoid signaling and activator protein-1 expression in ferrets given beta-carotene supplements and exposed to tobacco smoke. , 1999, Journal of the National Cancer Institute.

[30]  R. Leblanc,et al.  Increased heat emission and its relationship to the xanthophyll cycle in pea leaves exposed to strong light stress , 1991 .

[31]  M. Sporn,et al.  Can dietary beta-carotene materially reduce human cancer rates? , 1981, Nature.

[32]  Andrew J. Young,et al.  Aggregation of higher plant xanthophylls: Differences in absorption spectra and in the dependency on solvent polarity , 1993 .

[33]  N. Krinsky,et al.  Characterization of products formed during the autoxidation of β-carotene , 1991 .

[34]  S. Mayne,et al.  Beta‐carotene, carotenoids, and disease prevention in humans , 1996, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[35]  M. Havaux,et al.  Thylakoid membrane stability to heat stress studied by flash spectroscopic measurements of the electrochromic shift in intact potato leaves: influence of the xanthophyll content , 1996 .

[36]  W. Stahl,et al.  Carotenoid mixtures protect multilamellar liposomes against oxidative damage: synergistic effects of lycopene and lutein , 1998, FEBS letters.

[37]  N. Krinsky,et al.  β-Carotene and α-tocopherol are synergistic antioxidants , 1992 .

[38]  J. Palmgren,et al.  Alpha-Tocopherol and beta-carotene supplements and lung cancer incidence in the alpha-tocopherol, beta-carotene cancer prevention study: effects of base-line characteristics and study compliance. , 1996, Journal of the National Cancer Institute.

[39]  W. Subczynski,et al.  Effect of polar carotenoids on the oxygen diffusion-concentration product in lipid bilayers. An EPR spin label study. , 1991, Biochimica et biophysica acta.

[40]  D. Liebler,et al.  [45] Epoxide products of β-carotene antioxidant reactions , 1992 .

[41]  S. Mayne,et al.  Beta-Carotene and lung cancer promotion in heavy smokers--a plausible relationship? , 1996, Journal of the National Cancer Institute.

[42]  R. Crystal,et al.  Characterization of the lower respiratory tract inflammation of nonsmoking individuals with interstitial lung disease associated with chronic inhalation of inorganic dusts. , 1987, The American review of respiratory disease.

[43]  P. Palozza,et al.  Effect of beta-carotene and canthaxanthin on tert-butyl hydroperoxide-induced lipid peroxidation in murine normal and tumor thymocytes. , 1996, Archives of biochemistry and biophysics.

[44]  H. Gruchow,et al.  The influence of smoking on vitamin C status in adults. , 1989, American journal of public health.

[45]  M. Havaux Carotenoids as membrane stabilizers in chloroplasts , 1998 .

[46]  D. Liebler,et al.  Reactions of beta-carotene with cigarette smoke oxidants. Identification of carotenoid oxidation products and evaluation of the prooxidant/antioxidant effect. , 1999, Chemical research in toxicology.

[47]  G. Lindblom,et al.  Orientation of β‐carotene and retinal in lipid bilayers , 1981 .

[48]  E. Land,et al.  Relative One-Electron Reduction Potentials of Carotenoid Radical Cations and the Interactions of Carotenoids with the Vitamin E Radical Cation , 1998 .

[49]  Y. K. Levine,et al.  Study of the orientational ordering of carotenoids in lipid bilayers by resonance-Raman spectroscopy. , 1984, Biophysical journal.

[50]  M. Mathews-Roth,et al.  Carotenoids in Erythropoietic Protoporphyria and Other Photosensitivity Diseases , 1993, Annals of the New York Academy of Sciences.

[51]  A. Young,et al.  Lycopene and beta-carotene protect against oxidative damage in HT29 cells at low concentrations but rapidly lose this capacity at higher doses. , 1999, Free radical research.

[52]  T. G. Truscott,et al.  Beta-carotene and disease: a suggested pro-oxidant and anti-oxidant mechanism and speculations concerning its role in cigarette smoking. , 1996, Journal of photochemistry and photobiology. B, Biology.

[53]  A. Young,et al.  β‐Carotene enhances hydrogen peroxide‐induced DNA damage in human hepatocellular HepG2 Cells , 1999, FEBS letters.