Antioxidant activities of carotenoids: Quantitative relationships between theoretical calculations and experimental literature data

Free Radical Research

Volumn 30, Issue 3, 1999, Pages 233-240

  Soffers, Ans E M F ^a   Van Haandel, Marjon J H ^a   Boersma, Marelle G ^a   Tyrakowska, Bozena ^a   Laane, Colja ^a   Rietjens, Ivonne M C M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Antioxidant activity; Calculated ionisation potential; Carotenoids; Lipid peroxidation; Quantitative structure activity relationship

Indexed keywords

CAROTENOID; FREE RADICAL; THIOBARBITURIC ACID REACTIVE SUBSTANCE;

ANTIOXIDANT ACTIVITY; ARTICLE; CALCULATION; CORRELATION FUNCTION; FRUIT; HUMAN; LIPID PEROXIDATION; MEDICAL LITERATURE; OXIDATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VEGETABLE;

EID: 0032912856     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715769900300251     Document Type: Article

References (31)

1. C.A. Rice-Evans, N.J. Miller and G. Paganga (1996) Structure - antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biology and Medicine, 20, 933-956.
2. G. Block (1992) The data support a role for antioxidants in reducing cancer risk. Nutrition Reviews, 50, 207-213.
3. G. Block and L. Langseth (1994) Antioxidant vitamins and disease prevention. Food Technology, July, 80-84.
4. M.M. Mathews-Roth (1983) Carotenoid pigment administration and delay in development of UV-B-induced rumors. Photochemistry and Photobiology, 37, 509-511.
5. G. Britton (1995) Structure and properties of carotenoids in relation to function. FASEB Journal, 9, 1551-1558.
6. J.A. Olson and N.I. Krinsky (1995) Introduction: the colorful, fascinating world of the carotenoids: important physiologic modulators. FASEB Journal, 9, 1547-1550.
7. W. Stahl and H. Sies (1996) Lycopene: A biologically important carotenoid for humans? Archives of Biochemistry and Biophysics, 336, 1-9.
8. J.E. Packer, J.S. Mahood, V.O. Mora-Arellano, T.F. Slater, R.L. Willson and R.S. Wolfenden (1981) Free radicals and singlet oxygen scavengers: reaction of a peroxy-radical with β-carotene, diphenyl furan and 1,4-diazobicyclo(2,2,2)-octane. Biochemical and Biophysical Research Communications, 98, 901-906.
9. N.I. Krinsky (1993) Actions of carotenoids in biological systems. Annual Review of Nutrition, 13, 561-587.
10. P. Palozza and N.I. Krinsky (1992) Antioxidant effects of carotenoids in vivo and in vitro: an overview. Methods in Enzymology, 213, 403-420.
11. N.J. Miller, J. Sampson, L.P. Candeias, P.M. Bramley and C.A. Rice-Evans (1996) Antioxidant activities of carotenes and xanthophylls. FEBS Letters, 384, 240-242.
12. S.A. Everett, M.F. Dennis, K.B. Patel, S. Maddix, S.C. Kundu and R.L. Willson (1996) Scavenging of nitrogen dioxide, thiyl, and sulfonyl free radicals by the nutritional antioxidant β-carotene. Journal of Biological Chemistry, 271, 3988-3994.
13. G.W. Burton and K.U. Ingold (1984) β-carotene: an unusual type of lipid antioxidant. Science, 224, 569-573.
14. 2• radical. Journal of the American Chemical Society, 117, 8322-8326.
15. D.C. Liebler and T.D. McClure (1996) Antioxidant reactions of β-carotene: identification of carotenoid-radical adducts. Chemical Research in Toxicology, 9, 8-11.
16. H. Esterbauer, J. Gebicki, H. Puhl and G. Jürgens (1992) The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radical Biology and Medicine, 13, 341-390.
17. A.A. Woodall, S. Wai-Ming Lee, R.J. Weesie, M.J. Jackson and G. Britton (1997) Oxidation of carotenoids by free radicals: relationship between structure and reactivity. Biochimica et Biophysica Acta, 1336, 33-42.
18. A. Mortensen and L.H. Skibsted (1997) Importance of carotenoid structure in radical-scavenging reactions. Journal of Agricultural Food Chemistry, 45, 2970-2977.
19. W. Stahl, A. Junghans, B. de Boer, E.S. Driomina, K. Briviba and H. Sies (1998) Carotenoid mixtures protect multilamellar liposomes against oxidative damage: synergistic effects of lycopene and lutein. FEBS Letters, 427, 305-308.
20. J. Terao (1989) Antioxidant activity of β-carotene-related carotenoids in solution. Lipids, 24, 659-661.
21. A. Mortensen, L.H. Skibsted, J. Sampson, C. Rice-Evans and S.A. Everett (1997) Comparative mechanisms and rates of free radical scavenging by carotenoid antioxidants. FEBS Letters, 418, 91-97.
22. A.A. Woodall, G. Britton and M.J. Jackson (1997) Carotenoids and protection of phospholipids in solution or in liposomes against oxidation by peroxyl radicals: Relationship between carotenoid structure and protective ability. Biochimica et Biophysica Acta, 1336, 575-586.
23. J.J.P. Stewart (1989) Optimization of parameters for semiempirical methods I. Method. Journal of Computational Chemistry, 10, 209-220.
24. N.H.P. Cnubben, S. Peelen, J.W. Borst, J. Vervoort, C. Veeger and I.M.C.M. Rietjens (1994) Molecular orbital based quantitative structure activity relationship for the cytochrome P450 catalyzed 4-hydroxylation of halogenated anilines. Chemical Research in Toxicology, 7, 590-598.
25. I.M.C.M. Rietjens, A.E.M.F. Soffers, G.J.E.J. Hooiveld, C. Veeger and J. Vervoort (1995) Quantitative structure activity relationships (QSARs) based on computer calculated parameters for the overall rate of glutathione S-transferase catalyzed conjugation of a series of fluoronitrobenzenes. Chemical Research in Toxicology, 8, 481-488.
26. A.E.M.F. Soffers, J.H.M. Ploemen, M.J.H. Moonen, T. Wobbes, B. Van Ommen, J. Vervoort, P.J. Van Bladeren, and I.M.C.M. Rietjens (1996) Regioselectivity and quantitative structure activity relationships (QSARs) for the conjugation of a series of fluoronitrobenzenes by purified glutathione S-transferase enzymes from rat and man. Chemical Research in Toxicology, 9, 638-646.
27. M.J.H. Van Haandel, I.M.C.M. Rietjens, A.E.M.F. Soffers, C. Veeger, J. Vervoort, S. Modi, M.S. Mondal, P.K. Patel and D.V. Behere (1996) Computer calculation-based quantitative structure-activity relationships for the oxidation of phenol derivatives by horseradish peroxidase compound II. Journal of Bioinorganic Chemistry, 1, 460-467.
28. I.M.C.M. Rietjens, A.E.M.F. Soffers, C. Veeger, and J. Vervoort (1993) Regioselectivity of cytochrome P450 catalyzed hydroxylation of fluorobenzenes predicted by calculated frontier orbital substrate characteristics. Biochemistry, 32, 4801-4812.
29. I. Fleming (Ed.) (1976) Frontier Orbitals and Organic Chemical Reactions. Chichester: John Wiley & Sons.
30. + radical cation assay. Free Radical Research, 26, 195-199.
31. G. Levin and S. Mokady (1994) Antioxidant activity of 9-cis compared to all-trarcs β-carotene in vitro. Free Radical Biology and Medicine, 17, 77-82.