Spin-labelled lutein as a new antioxidant in protection against lipid peroxidation

Free Radical Research

Volumn 41, Issue 9, 2007, Pages 1053-1060

  Broniowska, Katarzyna A ^a   Kirilyuk, Igor ^b   Wisniewska, Anna ^a  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Alkyl radicals; Antioxidant activity; Carotenoids; Lutein; Nitroxide; Peroxyl radicals

Indexed keywords

2,2' AZOBIS(2,4 DIMETHYLVALERONITRILE); 3 CARBAMOYL 2,2,5,5 TETRAMETHYLPYRROLIDINE 1 OXYL; ANTIOXIDANT; FERRIC 8 QUINOLINOL; FREE RADICAL; LIPOSOME; NITROXIDE DERIVATIVE; PHOSPHATIDYLCHOLINE; QUINOLINOL DERIVATIVE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG; XANTHOPHYLL;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; EGG YOLK; ELECTRON SPIN RESONANCE; FENTON REACTION; LIPID PEROXIDATION; SPIN LABELING; STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; AZO COMPOUNDS; CYCLIC N-OXIDES; EGG YOLK; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HYDROXYQUINOLINES; LIPID PEROXIDATION; LIPOSOMES; LUTEIN; MALONDIALDEHYDE; MEMBRANES; NITRILES; PHOSPHATIDYLCHOLINES; PYRROLIDINES; SPIN LABELS; THIOBARBITURIC ACID REACTIVE SUBSTANCES;

EID: 34548329092     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760701463253     Document Type: Article

References (37)

1. Krinsky, NI. (1989) Antioxidant functions of carotenoids. Free Radic Biol Med, 7, pp. 617-635.
2. Conn, PF, Schalch, W. and Truscott, TG. (1991) The singlet oxygen and carotenoid interaction. J Photochem Photobiol B: Biol, 11, pp. 41-47.
3. Cantrell, A., McGarvey, DJ, Truscott, TG, Rancan, F. and Böhm, F. (2003) Singlet oxygen quenching by dietary carotenoids in a model membrane environment. Arch Biochem Biophys, 412, pp. 47-54.
4. Wrona, M., Korytowski, W., Rozanowska, M., Sarna, T. and Truscott, TG. (2003) Cooperation of antioxidants in protection against photosensitized oxidation. Free Radic Biol Med, 35, pp. 1319-1329.
5. Liebler, DC and McClure, TD. (1996) Antioxidant reactions of β-carotene: Identification of carotenoid-radical adducts. Chem Res Toxicol, 9, pp. 8-11.
6. Mortensen, A., Skibsted, LH and Truscott, TG. (2001) The interaction of dietary carotenoids with radical species. Arch Biochem Biophys, 385, pp. 13-19.
7. Woodall, AA, Lee, SW-M, Weesie, RJ, Jackson, MJ and Britton, G. (1997) Oxidation of carotenoids by free radicals: Relationship between structure and reactivity. Biochim Biophys Acta, 1336, pp. 33-42.
8. Woodall, AA, Britton, G. and Jackson, MJ. (1997) Carotenoids and protection of phospholipids in solution or in liposomes against oxidation by peroxyl radicals: Relationship between carotenoid structure and protective ability. Biochim Biophys Acta, 1336, pp. 575-586.
9. Stahl, W., Junghans, A., de Boer, B., Driomina, ES, Briviba, K. and Sies, H. (1998) Carotenoid mixtures protect multilamellar liposomes against oxidative damage: Synergistic effects of lycopene and lutein. FEBS Lett, 427, pp. 305-308.
10. Sujak, A., Gabrielska, J., Grudzinski, W., Borc, R., Mazurek, P. and Gruszecki, WI. (1999) Lutein and zeaxanthin as protectors of lipid membranes against oxidative damage: The structural aspects. Arch Biochem Biophys, 371, pp. 301-307.
11. Kirschfeld, K. (1982) Carotenoid pigments: Their possible role in protecting against photooxidation in eyes and photoreceptor cells. Proc R Soc Lond B, 216, pp. 71-85.
12. Rapp, LM, Maple, SS and Choi, JH. (2000) Lutein and zeaxanthin concentrations in rod outer segment membranes from perifoveal and peripheral human retina. Invest Ophthalmol Vis Sci, 41, pp. 1200-1209.
13. Wisniewska, A. and Subczynski, WK. (2006) Accumulation of macular xanthophylls in unsaturated membrane domains. Free Radic Biol Med, 40, pp. 1820-1826.
14. Wisniewska, A. and Subczynski, WK. (2006) Distribution of macular xanthophylls between domains in a model of photoreceptor outer segment membranes. Free Radic Biol Med, 41, pp. 1257-1265.
15. Gruszecki, WI and Sielewiesiuk, J. (1990) Orientation of xanthophylls in phosphatidylcholine multibilayer. Biochim Biophys Acta, 1023, pp. 405-412.
16. Nilsson, UA, Olsson, LI, Carlin, G. and Bylund, FA. (1989) Inhibition of lipid peroxidation by spin labels. Relationship between structure and function. J Biol Chem, 264, pp. 11131-11135.
17. Miura, Y., Utsumi, H. and Hamada, A. (1993) Antioxidant activity of nitroxide radicals in lipid peroxidation of rat liver microsomes. Arch Biochem Biophys, 300, pp. 148-156.
18. Mitchell, JB, Xavier, S., DeLuca, AM, Sowers, AL, Cook, JA, Krishna, MC, Hahn, SM and Russo, A. (2003) A low molecular weight antioxidant decreases weight and lowers tumor incidence. Free Radic Biol Med, 34, pp. 93-102.
19. Samuni, AM and Barenholz, Y. (2003) Site-activity relationship of nitroxide radical's antioxidative effect. Free Radic Biol Med, 34, pp. 177-185.
20. Hideg, K. and Hankovszky, OH (1989) Biological magnetic resonance. Vol. 8. Spin labelling. Theory and applications, pp. 427-488. Plenum Press, New York; London
21. Wisniewska, A. and Subczynski, WK. (1998) Effect of polar carotenoids on the shape of the hydrophobic barrier of phospholipid bilayers. Biochim Biophys Acta, 1368, pp. 235-246.
22. MacDonald, RC, MacDonald, RI, Menco, BP, Takeshita, K., Subbarao, NK and Hu, LR. (1991) Small-volume extrusion apparatus for preparation of large, unilamellar vesicles. Biochim Biophys Acta, 1061, pp. 297-303.
23. Hyde, JS and Subczynski, WK (1989) Biological magnetic resonance. Vol. 8. Spin labelling. Theory and applications, pp. 399-425. Plenum Press, New York; London
24. Korytowski, W., Wrona, M. and Girotti, AW. (1999) Radiolabeled cholesterol as a reporter for assessing one-electron turnover of lipid hydroperoxides. Anal Biochem, 270, pp. 123-132.
25. Halliwell, B. and Gutteridge, JMC. (1999) Free Radicals in Biology and Medicine, Oxford University Press, New York
26. Suttnar, J., Cermak, J. and Dyr, JE. (1997) Solid-phase extraction in malondialdehyde analysis. Anal Biochem, 249, pp. 20-23.
27. Griffith, OH, Dehlinger, PJ and Van, SP. (1974) Shape of the hydrophobic barrier of phospholipids bilayers (evidence for water penetration into biological membranes). J Membr Biol, 15, pp. 159-192.
28. Subczynski, WK, Wisniewska, A., Yin, J-J, Hyde, JS and Kusumi, A. (1994) Hydrophobic barriers of lipid bilayer membranes formed by reduction of water penetration by alkyl chain unsaturation and cholesterol. Biochemistry, 33, pp. 7670-7681.
29. Marsh, D. (1981) Membrane spectroscopy. Molecular biology, biochemistry and biophysics, 31, pp. 51-142. Springer-Verlag, Berlin
30. Niki, E. (1990) Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Methods Enzymol, 186, pp. 100-108.
31. Beckwith, ALJ, Bowry, VW and Ingold, KU. (1992) Kinetics of nitroxide radical trapping. 1. Solvent effects. J Am Chem Soc, 114, pp. 4983-4992.
32. Kocherginsky, N. and Swartz, HM (1995) Nitroxide spin labels. Reactions in biology and chemistry, pp. 25-65. CRC Press, Boca Raton; New York; London; Tokyo
33. Damiani, E., Belaid, C., Carloni, P. and Greci, L. (2003) Comparison of antioxidant activity between aromatic indolinoic nitroxides and natural and synthetic antioxidants. Free Radic Res, 37, pp. 731-741.
34. Damiani, E., Kalinska, B., Canapa, A., Canestrari, S., Wozniak, M., Olmo, E. and Greci, L. (2000) The effects of nitroxide radicals on oxidative DNA damage. Free Radic Biol Med, 28, pp. 1257-1265.
35. Offer, T. and Samuni, A. (2002) Nitroxides inhibit peroxyl radical-mediated DNA scission and enzyme inactivation. Free Radic Biol Med, 32, pp. 872-881.
36. Blough, NV. (1988) Electron paramagnetic resonance measurements of photochemical radical production in humic substances. 1. Effects of O2 and charge on radical scavenging by nitroxides. Environ Sci Technol, 22, pp. 77-82.
37. Damiani, E., Castagna, R., Astolfi, P. and Greci, L. (2005) Aromatic and aliphatic mono- and bis-nitroxides: A study on their radical scavenging abilities. Free Radic Res, 39, pp. 325-336.