The carotenoids as anti-oxidants - A review

Journal of Photochemistry and Photobiology B: Biology

Volumn 41, Issue 3, 1997, Pages 189-200

  Edge, R ^a   McGarvey, D J ^a   Truscott, T G ^a  

^a KEELE UNIVERSITY   (United Kingdom)

Author keywords

Anti oxidant; Carotenoids; Pro oxidant; Radicals; Singlet oxygen; Xanthophylls

Indexed keywords

CAROTENOID; FREE RADICAL; SINGLET OXYGEN; XANTHOPHYLL;

ANTIOXIDANT ACTIVITY; ARTICLE; BIOLOGY; CONTROLLED STUDY; DRUG MECHANISM; LIPID PEROXIDATION; PHOTOCHEMISTRY; PRIORITY JOURNAL;

EID: 0031459777     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(97)00092-4     Document Type: Review

References (77)

1. W. Stahl and H. Sies, Lycopene - A biologically important carotenoid for humans, Arch. Biochem. Biophys., 336 (1996) 1-9.
2. H. Gerster, The potential role of lycopene for human health, J. Am. College Nutr., 16 (1997) 109-126.
3. R. Peto, R. Doll, I.D. Buckley and M.B. Sporn, Can dietary β-carotene materially reduce human cancer rates?, Nature, 290 (1981) 201-208.
4. H.S. Garewal, Carotenoids in oral cancer prevention, Ann. New York Acad. Sci., 691 (1993) 139-147.
5. E.R. Greenberg, J.A. Baron, T.A. Stuket, MM. Stevens, J.S. Mandel, S.K. Spencer, P.M. Elias, N. Lowe, D.W. Nierenberg, G. Bayrd, J.C. Vance, D.H. Freeman, Jr., W.E. Clendenning, T. Kwan and The Skin Cancer Prevention Study Group, A clinical trial of β-carotene to prevent basel-cell and squamous cell cancers of the skin, New Eng. J. Med., 323 ( 1990) 789-795.
6. S.T. Mayne and R.S. Parker, Antioxidant activity of dietary canthax-anthin, Nutr. Cancer, 12 (1989) 225-236.
7. M.M. Mathews-Roth and N.I. Krinsky, Carotenoids affect development of UV-B induced skin cancer, Photochem.Photobiol., 46 (1987) 507-509.
8. C.S. Foote and R.W. Denny, Chemistry of singlet oxygen. VIII. Quenching by β-carotene, J. Am. Chem. Soc., 90 (1968 ) 6233-6235.
9. P.F. Conn, W. Schalch and T.G. Truscott, The singlet oxygen and carotenoid interaction, J. Photochem. Photobiol. B: Biol., 11 (1991) 41-47.
10. g) by carotenoid derivatives: kinetic analysis by near infra-red luminescence, New J. Chem., 18 (1994) 535-539.
11. J.H. Tinkler, F. Böhm, W. Schalch and T.G. Truscott, Dietary carotenoids protect human cells from damage, J. Photochem. Photobiol. B: Biol., 26 (1994) 283-285.
12. G.W. Burton and K.U. Ingold, β-carotene: An unusual type of lipid antioxidant, Science, 224 (1984) 569-573.
13. K. Jørgensen and L.H. Skibsted, Carotenoid scavenging of radicals, Z. Lebensm. Unters. Forsch., 196 (1993) 423-429.
14. F. Böhm, J.H. Tinkler and T.G. Truscott, Carotenoids protect against cell membrane damage by the nitrogen dioxide radical, Nature Med., 1 (1995) 98-99.
15. · radical, J. Am. Chem. Soc., 117 ( 1995) 8322-8326.
16. S.M. Anderson and N.I. Krinsky, Protective action of carotenoid pigments against photodynamic damage to liposomes, Photochem. Photobiol., 18 (1973) 403-408.
17. L. Packer, Antioxidant action of Carotenoids in vitro and in vivo protection against oxidation of human low-density lipoproteins, Ann. New York Acad. Sci., 691 (1993) 48-60.
18. G.S. Omenn, G.E. Goodman, M.D. Thornquist, J. Balmes, M.R. Cullen, A. Glass, J.P. Keogh, F.L. Meyskens, B. Valanis, J.H. Williams, Jr., S. Barnhart and S. Hammar, Effects of a combination of β-carotene and vitamin A on lung cancer and cardiovascular disease, New Eng. J. Med., 334 (1996) 1150-1155.
19. K. Peterson, Natural cancer prevention trial halted, Science. 271 (1996) 471.
20. The α-tocopherol, β-carotene cancer prevention study group, The effect of vitamin E and (β-carotene on the incidence of lung cancer and other cancers in male smokers, New Eng. J. Med., 330 (1994) 1029-1035.
21. K.M. Haila, B.R. Nielsen, M.I. Heinonen and L.H. Skibsted, Carotenoid reaction with free radicals in acetone and toluene at different oxygen partial pressures. An ESR spin-trapping study of structureactivity relationships, Lebensm. Unters Forsch., in press.
22. J. Piette, Biological consequences associated with DNA oxidation mediated by singlet oxygen, J. Photochem. Photobiol. B: Biol., 11 (1991) 241-260.
23. A.W. Girotti, Photodynamic lipid peroxidation in biological systems, Photochem. Photobiol., 51 (1990) 497-509.
24. A. Farmillo and F. Wilkinson, On the mechanism of quenching of singlet oxygen in solution, Photochem. Photohiol., 18 (1973) 447-450.
25. D.C. Liebler, Antioxidant reactions of carotenoids, Ann. New York Acad. Sci., 691 (1993) 20-31.
26. P. Di Mascio and H. Sies, Quantification of singlet oxygen generated by thermolysis of 3,3′-( 1.4-naphthylene) dipropionate - monomol and dimol photoemmision and the effects of 1,4-diazabicyclo-[2.2.2] octane, J. Am. Chem. Soc., III (1989) 2909-2914.
27. T.P.A. Devasagayam, T. Werner, H. Ippendorf, H.-D. Martin and H. Sies, Synthetic carotenoids, novel polyene polyketones and new capsorubin isomers as efficient quenchers of singlet molecular oxygen, Photochem. Photobiol., 55 (1992) 511-514.
28. J.N. Murrell and A.J. Harget (eds.), Semi-empirical self-consistent field molecular orbital theory of molecules, Wiley, New York, 1972.
29. J. Teraoka, H. Hashimoto, S. Matsudaira and Y. Koyama, Resonance Raman spectra of excited triplet states of β-carotene isomers, Chem. Lett., (1985) 311-314.
30. W. Schalch, Carotenoids in the retina, in I. Emerit and B. Chance (eds.), Free Radicals and Ageing, Birkhauser Verlag, Basel, Switzerland, 1992, pp. 280-298.
31. W. Stahl and H. Sies, Physical quenching of singlet oxygen and cistrans isomerisation, Ann. New York Acad. Sci., 691 (1993) 10-19.
32. H. Auweter, H. Bettermann, S. Beutner, C. Köpsel, E. Lüddecke. B. Mayer and H.-D. Martin, Novel H-and J-aggregation of carotenoids: Influence of structure, geometry and functional groups, Abstract. 11th Int. Symp. on Carotenoids, Leiden, p. 86.
33. P. Murasecco-Suardi, E. Oliveros, A.M. Braun and H.-J. Hansen, Singlet oxygen quenching by carotenoids: Steady state luminescence experiments, Helvetica Chimica Acta, 71 (1988) 1005-1010.
34. P. Di Mascio, S. Kaiser and H. Sies, Lycopene as the most efficient biological carotenoid singlet oxygen quencher. Arch. Biochem. Biophys., 274 (1989) 532-538.
35. P. Di Mascio, A.R. Sundquist, T.P.A. Devasagayam and H. Sies. Assay of lycopene and oher carotenoids as singlet oxygen quenchers. Methods in Enzymology, 213 (1992) 429-438.
36. M.A.J. Rodgers and A.L. Bates, Kinetic and spectroscopic features of some carotenoid triplet states: Sensitization by singlet oxygen. Photochem. Photobiol., 31 (1980) 533-537.
37. M.M. Mathews-Roth and N.I. Krinsky, Failure of conjugated octaene carotenoids to protect a mutant of Sarcina Lutea against lethal photosensitization, Photochem. Photobiol., 11 (1970) 555-557.
38. J. Haley. The photochemistry of carotenoids, M.Phil. Thesis, Keele University, UK, 1993.
39. N.I. Krinsky and S.M. Deneke, The interaction of oxygen and oxyradicals with carotenoids, J. Nat. Cancer Inst., 69 (1982) 205-210.
40. P. Wörner, H. Patscheke and W. Paschen, Response of platelets exposed to potassium tetraperoxochromate, an extracellular source of singlet oxygen, hydroxyl radicals, Superoxide anion and hydrogen peroxide, Hoppe-Seylers Z. Physiol. Chem., 360 (1970) 559-570.
41. A. Telfer, S. Dhami, S.M. Bishop, D. Phillips and J. Barber, β-carotene quenches singlet oxygen formed by isolated photosystem II reaction centers, Biochem., 33 (1994) 14469-14474.
42. W. Miki, Biological functions and activities of animal carotenoids, Pure and Appl. Chem., 63 (1991) 141-146.
43. R.C. Mordi, J.C. Walton, G.W. Burton, L. Hughes, K.U. Ingold and D.A. Lindsay, Exploratory study of β-carotene autoxidation, Tett. Lett., 32 (1991) 4203-4206.
44. 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 β-carotene, diphenyl furan and 1,4-diazobicyclo-(2,2,2)-octane, Biochem. Biophys. Res. Comm., 98 (1981) 901-906.
45. T.F. Slater (ed.), Biochemical mechanisms of liver injury, Academic Press, New York, 1978, pp. 745.
46. R.L. Willson, Biology of vitamin E, in R. Porter and J. Whelan ( eds. ), Ciba Foundation Symposium No. 101, Pitman Books, London, 1983, pp. 19.
47. J.A. Jeevarajan, C.C. Wei, A.S. Jeevarajan and L.D. Kispert, Optical absorption spectra of dications of carotenoids, J. Phys. Chem., 100 (1996) 5637-5641.
48. S.A. Everett, S.C. Kundu, S. Maddix and R.L. Willson, Mechanisms of free-radical scavenging by the nutritional antioxidant β-carotene, Biochem. Soc. Trans., 23 (1995) 230S.
49. S.A. Everett, M.A. Dennis, K.B. Patel, S. Maddix, S.C. Kundu and R.L. Willson, Scavenging of nitrogen dioxide, thiyl and sulphonyl free radicals by the nutritional antioxidant β-carotene, J. Biol. Chem., 271 (1996) 3988-3994.
50. x, to be published.
51. A. Mortensen and L.H. Skibsted, Kinetics of photobleaching of β-carotene in chloroform and formation of transient carotenoid species absorbing in the near infra-red, Free Rad. Res., 25 (1996) 355-368.
52. A. Mortensen and L.H. Skibsted, Kinetics of parallel electron transfer from β-carolene to phenoxyl radical and adduct formation between phenoxyl radical and β-carotene, Free Rad. Res., 25 (1996) 515-523.
53. A. Mortensen and L.H. Skibsted, Formation of transient free radical carotenoid species, Abstract, 11th Int. Symp. on Carotenoids, Leiden (1996) 68.
54. C.R. Lambert, H.S. Black and T.G. Truscott, Reactivity of butylatedhydroxytoluene, Free Rad. Biol. Med., 21 (1996) 395-400.
55. F. Böhm, R. Edge, E.J. Land, D.J. McGarvey and T.G. Truscott, Carotenoids enhance vitamin E antioxidant efficiency. J. Am. Chem. Soc., 119 (1997) 621-622.
56. D.C. Liebler and T.D. McClure, Antioxidant reactions of β-carotene: Identification of carotenoid-radical adducts, Chem. Res. Toxicol., 9 (1996) 8-11.
57. P.P. Conn, C.R. Lambert, E.J. Land, W. Schalen and T.G. Truscott, Carotene-oxygen radical interactions, Free Rad. Res. Commun., 16 (1992) 401-408.
58. E.A. Dawe and E.J. Land, Radical ions derived from hotosynthetic polyenes, J. Chem. Soc., Farad. Trans. 1, 71 (1975) 2162-2169.
59. J.A. Jeevarajan, C.C. Wei and L.D. Kispert, Geometrical isomerization of carotenoids in dichloromethane, J. Chem. Soc., Perkin Trans. 2, (1994) 861-869.
60. G.F. Vile and C.C. Winterborne, Inhibition of adriamycin-promoted microsomal lipid peroxidation by β-carotene, α-tocopherol and retinol at high and low oxygen partial pressures, FEBS Lett., 238 (1988) 353-356.
61. H. Tsuchihashi, M. Kigoshi, M. Iwatsuki and E. Niki, Action of β-carotene as an antioxidant against lipid peroxidation, Arch. Biochem. Biophys., 323 (1995) 137-147.
62. G. Levin and S. Mokady, Antioxidant activity of 9-cis compared to all-trans-β-carotene in vitro, Free Rad. Biol. Med., 17 (1994) 77-82.
63. N.J. Miller, J. Sampson, L.P. Candeias, P.M. Bramley and C.A. Rice-Evans, Antioxidant activities of carotenes and xanthophylls, FEBS Lett., 384 (1996) 240-242.
64. E.J. Rouseau, A.J. Davison and B. Dünn, Protection by β-carotene and related compounds against oxygen-mediated cytotoxicity and genotoxicity: Implications for carcinogenesis and anticarcinogenesis, Free Rad. Biol. Med., 13 (1992) 407-433.
65. T.A. Kennedy and D.C. Liebler, Peroxyl radical scavenging by βcarotene in lipid bilayers, J. Biol. Chem., 267 (1992) 4658-4663.
66. P. Palozza and N.I. Krinsky, The inhibition of radical-initialed peroxidation of microsomal lipids by both α-tocopherol and β-carotene, Free Rad. Biol. Med., 11 (1991) 407-414.
67. P. Palozza and N.I. Krinsky, β-carotene and α-tocopherol are synergistic antioxidants, Arch. Biochem. Biophys., 297 (1992) 184-187.
68. E. Niki, N. Noguchi, H. Tsuchihashi and N. Gotoh, Interaction amoung vitamin C, vitamin E and β-carotene, Am.J. Cline. Nutr., 62 (1995) 1322S-1326S.
69. R.V. Cooney, P.J. Harwood, L.J. Custer and A.A. Franke, Lightmediated conversion of nitrogen dioxide to nitric oxide by carotenoids, Environ. Health Perspect., 102 (1994) 460-462.
70. L. Valgimigli, M. Lucarini, G.F. Pedulli and K.U. Ingold, Does β-carotene really protect vitamin E from oxidation, J. Am. Chem. Soc., in press (1997).
71. S.T. Mayne, D.T. Janerich, P. Greenwald, S. Chorost, C. Tucci, M.B. Zaman, M.R. Melamed, M. Kiely and M.F. McKneally, Dietary βcarotene and lung cancer risk in U.S. smokers, J. Natl. Cancer Inst., 86 (1994) 33-38.
72. M.B. Davies, J. Austin and D.A. Partridge, Vitamin C: Its chemistry and biochemistry, Royal Soc. Chem., Cambridge, 1991, pp. 107.
73. G. Britton, Structure and properties of carotenoids in relation to function. FASEB Journal, (1995) 1551-1558.
74. J.H. Tinkler, S.M. Tavender, A.W. Parker, D.J. McGarvey, L. Mulroy and T.G. Truscott, Investigation of carotenoid radical cations and triplet states by laser flash photolysis and time-resolved resonance Raman spectroscopy: Observation of competitive energy and electron transfer, J. Am. Chem. Soc., 118 (1996) 1756-1761.
75. T.G. Truscott, β-Carotene and disease: a suggested pro-oxidant and anti-oxidant mechanism and speculations concerning its role in cigarette smoking, J. Photochem. Photobiol. B: Biol., 35 (1996) 233-235.
76. J.S. Bertram, The chemoprevention of cancer by dietary carotenoids: studies in mouse and human cells, Pure Appl. Chem., 88 (1994) 1025-1032.
77. W. Stahl, S. Nicolai, K. Briviba, M. Hanusch, G. Broszeit, M. Peters, H.D. Martin, H. Sies, Biological activities of natural and synthetic carotenoids: Induction of gap junctional communication and singlet oxygen quenching, Carcinogenesis. 18 (1997) 89-92.