Carotenoid radical chemistry and antioxidant/pro-oxidant properties

Archives of Biochemistry and Biophysics

Volumn 430, Issue 1, 2004, Pages 37-48

  El Agamey, Ali ^a   Lowe, Gordon M ^b   McGarvey, David J ^a   Mortensen, Alan ^c   Phillip, Denise M ^b   Truscott, T George ^a   Young, Andrew J ^b  

^a KEELE UNIVERSITY   (United Kingdom)

^b LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^c CHR HANSEN A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

7,7' DIHYDRO BETA CAROTENE; ALPHA TOCOPHEROL; ANTIOXIDANT; ASCORBIC ACID; ASTAXANTHIN; BETA CAROTENE; BIXIN; CANTHAXANTHIN; CAROTENE; CAROTENOID; LYCOPENE; OXIDIZING AGENT; PEROXY RADICAL; PIGMENT; RADICAL; RETINOL; SEPTAPRENO BETA CAROTENE; SOLVENT; THIOCTIC ACID; UNCLASSIFIED DRUG; XANTHOPHYLL; ZEAXANTHIN; ZETA CAROTENE;

CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHEMISTRY; IN VITRO STUDY; MOLECULAR MECHANICS; OXIDATION; PRIORITY JOURNAL; REVIEW;

EID: 4344634650     PISSN: 00039861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.abb.2004.03.007     Document Type: Short Survey

References (118)

1. Gruszecki W.I. Carotenoids in membranes. Frank H.A., Young A.J., Britton G., Cogdell R.J. The Photochemistry of Carotenoids. first ed.:1999;363-379 Kluwer Academic Publishers, Dordrecht
2. Potter J.D. Cancer Lett. 114:1997;329
3. Van Poppel G., Van den Berg H. Cancer Lett. 114:1997;195
4. Ziegler R.G., Mayne S.T., Swanson C.A. Cancer Causes Control. 7:1996;157
5. Witte J.S., Longnecker M.P., Bird C.L., Lee E.R., Frankl H.D., Haile R.W. Am. J. Epidemiol. 144:1996;1015
6. Potischman N., Brinton L.A. Cancer Causes Control. 7:1996;113
7. Helzsouer K.J., Alberg A.J., Norkus E.P., Morris J.S., Hoffman S.C., Comstock G.W. J. Natl. Cancer Inst. 88:1996;32
8. Nowak R. Science. 264:1994;500
9. Rice-Evans C.A., Sampson J., Bramley P.M., Holloway D.E. Free Radic. Res. 26:1997;381
10. Burton G.W., Ingold K.U. Science. 224:1984;569
11. Hill T.J., Land E.J., McGarvey D.J., Schalch W., Tinkler J.H., Truscott T.G. J. Am. Chem. Soc. 117:1995;8322
12. Everett S.A., Dennis M.F., Patel K.B., Maddix S., Kundu S.C., Willson R.L. J. Biol. Chem. 271(8):1996;3988
13. Mortensen A., Skibsted L.H. Free Radic. Res. 25(6):1996;515
14. Conn P.F., Schalch W., Truscott T.G. J. Photochem. Photobiol. B: Biol. 11:1991;41
15. DiMascio P., Kaiser S., Sies H. Arch. Biochem. Biophys. 274:1989;532
16. Lowe G.M., Booth L.A., Young A.J., Bilton R.F. Free Radic. Res. 30:1999;141
17. Woods J.A., Bilton R.F., Young A.J. FEBS Lett. 449:1999;255
18. Palozza P. Nutr. Rev. 56(9):1998;257
19. Palozza P., Calviello G., Serini S., Maggiano N., Lanza P., Ranelletti F.O., Bartoli G.M. Free Radic. Biol. Med. 30:2001;1000
20. Eichler O., Sies H., Stahl W. Photochem. Photobiol. 75:2002;503
21. The Alpha-Tocopherol, Beta Carotene Cancer Prevention Study Group, New Engl. J. Med. 330 (1994) 1029
22. Omenn G.S., Goodman G.E., Thornquist M.D., Balmes J., Cullen M.R., Glass A., Keogh J.P., Meyskens F.L., Valanis B., Williams J.H., Barnhart S., Hammar S. New Engl. J. Med. 334:1996;1150
23. Mayne S.T. FASEB J. 10:1996;690
24. Mayne S.T., Handelman G.J., Beecher G. J. Natl. Cancer Inst. 88:1996;1513
25. Gaziano J.M. Nutr. Rev. 54:1996;175
26. Zhang P., Omaye S.T. Food Chem. Toxicol. 39:2001;239-246
27. Zhang P., Omaye S.T. Toxicol. In Vitro. 15:2001;13-24
28. Moini H., Packer L., Saris N.E.L. Toxicol. Appl. Pharmacol. 182:2002;84-90
29. Young A.J., Lowe G.M. Arch. Biochem. Biophys. 385:2001;20
30. A.J. Young, G. Lowe, Carotenoid antioxidant activity, in: N. Krinsky, S.T. Mayne, H. Sies (Eds.), Carotenoids in Health and Disease, Marcel Dekker, New York (in press) (2004)
31. Lowe G.M., Vlismas K., Young A.J. Mol. Aspects Med. 24:2003;363-369
32. Woodall A.A., Britton G., Jackson M.J. Biochim. Biophys. Acta. 1336:1997;575
33. Woodall A.A., Lee S.W.M., Weesie R.J., Jackson M.J., Britton G. Biochim. Biophys. Acta. 1336:1997;33
34. Farombi E.O., Britton G. Redox Rep. 4:1999;61
35. Farombi E.O., Britton G. Food Chem. 64:1999;315
36. Edge R., Truscott T.G. Carotenoid radicals and the interaction of carotenoids with active oxygen species. Frank H.A., Young A.J., Britton G., Cogdell R.J. The Photochemistry of Carotenoids. first ed.:1999;223-234 Kluwer Academic Publishers, Dordrecht
37. Britton G. FASEB J. 9:1995;1551
38. Polyakov N.E., Kruppa A.I., Leshina T.V., Konovalova T.A., Kispert L.D. Free Radic. Biol. Med. 31:2001;43
39. Edge R., Land E.J., McGarvey D.J., Mulroy L., Truscott T.G. J. Am. Chem. Soc. 120(17):1998;4087
40. Mordi R.C., Walton J.C., Burton G.W., Hughes L., Ingold K.U., Lindsay D.A., Moffatt D.J. Tetrahedron. 49(4):1993;911
41. Liebler D.C., McClure T.D. Chem. Res. Toxicol. 9:1996;8
42. Kennedy T.A., Liebler D.C. Chem. Res. Toxicol. 4:1991;290
43. Samokyszyn V.M., Marnett L.J. J. Biol. Chem. 262(29):1987;14119
44. Mordi R.C., Walton J.C., Burton G.W., Hughes L., Ingold K.U., Lindsay D.A. Tetrahed. Lett. 32(33):1991;4203
45. Baker D.L., Krol E.S., Jacobsen N., Liebler D.C. Chem. Res. Toxicol. 12:1999;535
46. Adhikari S., Kapoor S., Chattopadhyay S., Mukherjee T. Biophys. Chem. 88:2000;111
47. Mortensen A., Skibsted L.H. J. Agric. Food Chem. 45(8):1997;2970
48. Mortensen A., Skibsted L.H. Free Radic. Res. 25(4):1996;355
49. Mortensen A. Asian Chem. Lett. 4:2000;135
50. Mortensen A., Skibsted L.H. FEBS Lett. 426:1998;392
51. Mortensen A. J. Photochem. Photobiol. B: Biol. 61:2001;62
52. D'Aquino M., Dunster C., Willson R.L. Biochem. Biophys. Res. Commun. 161(3):1989;1199
53. Mortensen A. Free Radic. Res. 36:2002;211
54. Handelman G.J., Van Kuijk F.J.G.M., Chatterjee A., Krinsky N.I. Free Radic. Biol. Med. 10:1991;427
55. El-Tinay A.H., Chichester C.O. J. Org. Chem. 35(7):1970;2290
56. Mortensen A., Skibsted L.H., Sampson J., Rice-Evans C., Everett S.A. FEBS Lett. 418:1997;91
57. Lafferty J., Roach A.C., Sinclair R.S., Truscott T.G. J. Chem. Soc. Farad. Trans. I. 73:1977;416
58. Bensasson R.V., Land E.J., Truscott T.G. Excited states and free radicals in biology and medicine. 1993;Oxford University Press, Oxford. pp. 201-227
59. Jeevarajan A.S., Kispert L.D., Wu X. Chem. Phys. Lett. 219:1994;427
60. Jeevarajan J.A., Wei C.C., Jeevarajan A.S., Kispert L.D. J. Phys. Chem. 100:1996;5637
61. Ding R., Grant J.L., Metzger R.M., Kispert L.D. J. Phys. Chem. 92:1988;4600
62. Grant J.L., Kramer V.J., Ding R., Kispert L.D. J. Am. Chem. Soc. 110:1988;2151
63. Martin H.D., Ruck C., Schmidt M., Sell S., Beutner S., Mayer B., Walsh R. Pure Appl. Chem. 71(12):1999;2253
64. Krinsky N.I., Yeum K.-J. Biochem. Biophys. Res. Commun. 305:2003;754-760
65. Mortensen A., Skibsted L.H. Free Radic. Res. 26:1997;549
66. Packer J.E., Mahood J.S., Mora-Arellano V.O., Slater T.F., Willson R.L., Wolfenden B.S. Biochem. Biophys. Res. Commun. 98:1981;901-906
67. Mortensen A., Skibsted L.H., Truscott T.G. Arch. Biochem. Biophys. 385:2001;13
68. Yaping Z., Suping Q., Wenli Y., Zheng X., Hong S., Side Y., Dapu W. Food Chem. 77(2):2002;209-212
69. Wenen Z., Side Y., Qiang W., Suping Q., Wenfeng W., Yashan H. Sci. China Ser. B. 46(1):2003;57-63
70. El-Agamey A., McGarvey D.J. J. Am. Chem. Soc. 125:2003;3330-3340
71. El-Agamey A., McGarvey D.J. Free Radic. Res. 36(Suppl. S):2002;97-100
72. Dizdaroglu M., von Sonntag C., Schulte-Frohlinde D. J. Am. Chem. Soc. 97:1975;2277
73. Giese B., Burger J., Kang T.W., Kesselheim C., Wittmer T. J. Am. Chem. Soc. 114:1992;7322
74. Gugger A., Batra R., Rzadek P., Rist G., Giese B. J. Am. Chem. Soc. 119:1997;8740
75. Glatthar R., Spichty M., Gugger A., Batra R., Damm W., Mohr M., Zipse H., Giese B. Tetrahedron. 56:2000;4117
76. S.L. Murov, I. Carmichael, G.L. Hug, Handbook of Photochemistry, second ed., rev. and expanded, Marcel Dekker, New York, 1993
77. Weast R.C., Astle M.J. CRC Handbook of Chemistry and Physics. 61st ed.:1981;CRC Press, Boca Raton. E56-E58
78. Burke M., Edge R., Land E.J., McGarvey D.J., Truscott T.G. FEBS Lett. 500:2001;132
79. Jonsson M. J. Phys. Chem. 100:1996;6814-6818
80. Das T.N., Dhanasekaran T., Alfassi Z.B., Neta P. J. Phys. Chem. A. 102:1998;280-284
81. Woods J.A., Bilton R.F., Young A.J. FEBS Lett. 449:1999;255-258
82. Everett S.A., Kundu S.C., Maddix S., Willson R.L. Biochem. Soc. Trans. 23:1995;230S
83. Bobrowski K., Das P.K. J. Phys. Chem. 89:1985;5079
84. Edge R., McGarvey D.J., Truscott T.G. J. Photochem. Photobiol. B: Biol. 41:1997;189
85. Böhm F., Edge R., McGarvey D.J., Truscott T.G. FEBS Lett. 436:1998;387
86. Böhm F., Tinkler J.H., Truscott T.G. Nat. Med. 1:1995;98
87. Burke M., Edge R., Land E.J., Truscott T.G. J. Photochem. Photobiol. B: Biol. 60:2001;1
88. Chauvet J.-P., Viovy R., Land E.J., Santus R., Truscott T.G. J. Phys. Chem. 87:1983;592
89. Khopde S.M., Priyadarsini K.I., Bhide M.K., Sastry M.D., Mukherjee T. Res. Chem. Intermed. 29:2003;495-502
90. Zhang P., Omaye S.T. Toxicology. 146:2000;37
91. D.C. Liebler, Antioxidant reactions of carotenoids, in: L.M. Canfield, N.I. Krinsky, J.A. Olson (Eds.), Carotenoids in Human Health, Ann. New York Acad. Sci., The New York Academy of Sciences, New York, 691 (1993) 20-31
92. Kennedy T.A., Liebler D.C. J. Biol. Chem. 267(7):1992;4658
93. Vile G.F., Winterbourn C.C. FEBS Lett. 238(2):1988;353
94. Tsuchihashi H., Kigoshi M., Iwatsuki M., Niki E. Arch. Biochem. Biophys. 323(1):1995;137
95. Palozza P., Luberto C., Calviello G., Ricci P., Bartoli G.M. Free Radic. Biol. Med. 22(6):1997;1065
96. Simic M.G. Methods Enzymol. 213:1992;444
97. Dawe E.A., Land E.J. J. Chem. Soc. Farad. Trans. I. 71:1975;2162
98. Gao Y., Kispert L.D. J. Phys. Chem. B. 107:2003;5333
99. Gao Y., Webb S., Kispert L.D. J. Phys. Chem. B. 107:2003;13237
100. Tallman K.A., Pratt D.A., Porter N.A. J. Am. Chem. Soc. 123:2001;11827
101. Zhang P., Omaye S.T. J. Nutr. Biochem. 12:2001;38-45
102. Edge R., Truscott T.G. The Spectrum. 13(1):2000;12
103. Miller N.J., Sampson J., Candeias L.P., Bramley P.M., Rice-Evans C.A. FEBS Lett. 384:1996;240
104. Mortensen A., Skibsted L.H. FEBS Lett. 417:1997;261
105. Edge R., Land E.J., McGarvey D.J., Burke M., Truscott T.G. FEBS Lett. 471:2000;125
106. Böhm F., Edge R., Land E.J., McGarvey D.J., Truscott T.G. J. Am. Chem. Soc. 119:1997;621
107. Mortensen A., Skibsted L.H. Free Radic. Res. 27:1997;229
108. Halliwell B., Gutteridge J.M.C. Free Radicals in Biology and Medicine. third ed.:1999;Oxford University Press, Oxford. pp. 86-306
109. Packer J.E., Slater T.F., Willson R.L. Nature. 278:1979;737
110. Edge R., Truscott T.G. Nutrition. 13:1997;992
111. Offord E.A., Gautier J.-C., Avanti O., Scaletta C., Runge F., Krämer K., Applegate L.A. Free Radic. Biol. Med. 32(12):2002;1293
112. Cantrell A., McGarvey D.J., Truscott T.G., Rancan F., Böhm F. Arch. Biochem. Biophys. 412:2003;47-54
113. Ruban A.V., Horton P., Young A.J. J. Photochem. Photobiol. B. 21:1993;229-234
114. Martin H.-D., Jäger C., Ruck C., Schmidt M., Walsh R., Paust J. J. Prakt. Chem. 341:1999;302-308
115. Beutner S., Bloedorn B., Frixel S., Blanco I.H., Hoffmann T., Martin H.-D., Mayer B., Noack P., Ruck C., Schmidt M., Schülke I., Sell S., Ernst H., Haremza S., Seybold G., Sies H., Stahl W., Walsh R. J. Sci. Food Agric. 81:2001;559-568
116. Nagler L.G., Lankin V.Z., Kozachenko A.I., Gurevich S.M. Biochemistry-Moscow. 68:2003;203-208
117. Borel P., Grolier P., Armand M., Partier A., Lafont H., Lairon D., Azais-Braesco V. J. Lipid Res. 37:1996;250-261
118. L. Packer, Antioxidant action of carotenoids in vitro and in vivo and protection against oxidation of human low-density lipoproteins, in: L.M. Canfield, N.I. Krinsky, J.A. Olson (Eds.), Carotenoids in Human Health, Ann. New York Acad. Sci., The New York Academy of Sciences, New York, 691 (1993) 48-59