Kinetics of the lipoperoxyl radical-scavenging activity of indicaxanthin in solution and unilamellar liposomes

Free Radical Research

Volumn 41, Issue 2, 2007, Pages 226-233

  Tesoriere, L ^a   Allegra, M ^a   Butera, D ^a   Gentile, C ^a   Livrea, M A ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZOBIS(2 AMIDINOPROPANE); 2,2' AZOBIS(2,4 DIMETHYLVALERONITRILE); ALPHA TOCOPHEROL; BETALAIN; INDICAXANTHIN; LINOLEIC ACID; LIPOPEROXYL RADICAL; LIPOSOME; METHANOL; PEROXY RADICAL; PHOSPHATIDYLCHOLINE; RADICAL; SCAVENGER; UNCLASSIFIED DRUG; 2,2'-AZOBIS(2,4-DIMETHYLVALERONITRILE); 2,2'-AZOBIS(2-AMIDINOPROPANE); AMIDINE; ANTIOXIDANT; AZO COMPOUND; BETAXANTHIN; DIPALMITOYLPHOSPHATIDYLCHOLINE; LINOLEIC ACID METHYL ESTER; LIPID PEROXIDE; NITRILE; PYRIDINE DERIVATIVE; SOLVENT;

ANTIOXIDANT ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; LIPID OXIDATION; NONHUMAN; SOYBEAN; STOICHIOMETRY; CHEMICAL STRUCTURE; COMPARATIVE STUDY; DOSE RESPONSE; DRUG POTENTIATION; IN VITRO STUDY; KINETICS; LIPID BILAYER; LIPID PEROXIDATION; METABOLISM; OXIDATION REDUCTION REACTION; SOLUTION AND SOLUBILITY; SUSPENSION;

GLYCINE MAX;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; ALPHA-TOCOPHEROL; AMIDINES; ANTIOXIDANTS; AZO COMPOUNDS; BETAXANTHINS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SYNERGISM; FREE RADICAL SCAVENGERS; KINETICS; LINOLEIC ACIDS; LIPID BILAYERS; LIPID PEROXIDATION; LIPID PEROXIDES; LIPOSOMES; METHANOL; MOLECULAR STRUCTURE; NITRILES; OXIDATION-REDUCTION; PHOSPHATIDYLCHOLINES; PYRIDINES; SOLUTIONS; SOLVENTS; SUSPENSIONS;

EID: 34247588311     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760601026614     Document Type: Article

References (39)

1. Rice-Evans, CA and Miller, NJ (1985) Antioxidants: The case of fruit and vegetables in the diet. Br Food J, 97, pp. 35-40.
2. Ames, B., Shigenaga, MK and Hagen, TM (1993) Oxidants, antioxidants and the degenerative disease of aging. Proc Nat Acad Sci, 90, pp. 7915-7922.
3. Lampe, JW (1999) Health effects of vegetables and fruits: Assessing mechanism of action in human experimental studies. Am J Clin Nutr, 70, pp. 475-490.
4. Hertog, MGL, Feskens, EJM, Hollman, PCH, Katan, MB and Kromhout, D. (1993) Dietary antioxidants, flavonoids and the risk of coronary heart disease: The Zutphen elderly study. Lancet, 342, pp. 1007-1011.
5. Middleton Jr, E., Kandaswami, C. and Theoharides, TC (2000) The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol Rev, 52:4, pp. 673-751.
6. Wang, H., Nair, MG, Strasburg, GM, Chang, YC, Booren, AM, Gray, JI and DeWitt, DL (1999) Antioxidant and antiinflammatory activities of anthocyanins and their aglycon, cyanidin, from tart cherries. J Nat Prod, 62:5, p. 802.
7. Steglich, W. and Strack, D. (1990) Betalains. The alkaloids, chemistry and pharmacology, pp. 1-62. Academic Press, London
8. Escribano, J., Pedreno, MA, Garcia-Carmona, F. and Munoz, R. (1998) Characterization of the antiradical activity of betalains from Beta vulgaris L. roots. Phytochem Anal, 9, pp. 124-127.
9. Pedreno, MA and Escribano, J. (2000) Studying the oxidation and the antiradical activity of betalain from beetroot. J Biol Educ, 35, pp. 49-51.
10. Kanner, J., Harel, S. and Granit, R. (2001) Betalains. A new class of dietary antioxidants. J Agric Food Chem, 49, pp. 5178-5185.
11. Cai, Y., Sun, M. and Corke, H. (2003) Antioxidant activity of betalains from plants of the amaranthaceae. J Agric Food Chem, 51, pp. 2288-2294.
12. Butera, D., Tesoriere, L., Gaudio, F Di, Bongiorno, A., Allegra, M., Pintaudi, AM, Kohen, R. and Livrea, MA (2002) Antioxidant activities of Sicilian prickly pear (Opuntia ficus indica) fruit extracts and reducing properties of its betalains: Betanin and indicaxanthin. J Agric Food Chem, 50, pp. 6895-6901.
13. Piattelli, M. (1981) The betalains: Structure, biosynthesis and chemical taxonomy. The biochemistry of plants: A comprehensive treatise, 7, pp. 557-575. Academic Press, New York
14. Belitz, HD and Grosch, W. (1987) Food chemistry, p. 177. Springer-Verlag, Berlin, Germany
15. Lin, JC and Olcott, HS (1995) Ethoxyquin nitroxide. J Agric Food Chem, 23, pp. 798-800.
16. Tesoriere, L., Butera, D., D'Arpa, D., Gaudio, F Di, Allegra, M., Gentile, C. and Livrea, MA (2003) Increased resistance to oxidation of betalain-enriched human low density lipoproteins. Free Radic Res, 37, pp. 689-696.
17. Tesoriere, L., Butera, D., Allegra, M., Fazzari, M. and Livrea, MA (2005) Distribution of betalain pigments in red blood cells after consumption of cactus pear fruits, and increased resistance of the cells to ex vivo-induced oxidative haemolysis in humans. J Agric Food Chem, 53, pp. 1266-1270.
18. Tesoriere, L., Allegra, M., Butera, D., Gentile, C. and Livrea, MA (2006) Cytoprotective effects of the antioxidant phytochemical indicaxanthin in β-thalassemia red blood cells. Free Radic Res, 40, pp. 753-761.
19. Gentile, C., Tesoriere, L., Allegra, M., Livrea, MA and D'Alessio, P. (2004) Antioxidant betalains from cactus pear (Opuntia ficus-indica) inhibit endothelial ICAM-1 expression. Ann NY Acad Sci, 1028, pp. 481-486.
20. Stintzing, FC, Schieber, A. and Carle, R. (2002) Identification of betalains from yellow beet (Beta vulgaris L.) and cactus pear [Opuntia ficus-indica (L.) Mill.] by high-performance liquid chromatography-electrospray ionization mass spectrometry. J Agric Food Chem, 50, pp. 2302-2307.
21. Piattelli, M., Minale, L. and Prota, G. (1964) Isolation structure and absolute configuration of indicaxanthin. Tetrahedron, 20, pp. 2325-2329.
22. Burton, GW and Ingold, KU (1981) Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. J Am Chem Soc, 103, pp. 6472-6477.
23. Barclay, LRC and Ingold, KU (1981) Autoxidation of biological molecules. 2. Autoxidation of a model membrane. Comparison of the autoxidation of egg lecithin phosphatidylcholine in water and in chlorobenzene. J Am Chem Soc, 103, pp. 6478-6485.
24. Niki, E., Saito, T., Kawakami, A. and Kamiya, Y. (1984) Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. J Biol Chem, 259, pp. 4177-4182.
25. Pryor, WA and Castle, L. (1984) Chemical methods for detection of lipid hydroperoxides. Methods in enzymology, 105, pp. 203-208. Academic Press, San Diego,CA
26. Kagan, VE, Shvedova, AA, Novikov, KN and Kozlov, YP (1973) Light-induced free radical oxidation of membrane lipids in photoreceptors of frog retina. Biochim Biophys Acta, 330, pp. 76-79.
27. Hiramitsu, T. and Armstrong, D. (1991) Preventive effect of antioxidants on lipid peroxidation in the retina. Ophthalmic Res, 23, pp. 196-203.
28. Buettner, G. (1993) The pecking order of free radicals and antioxidants: Lipid peroxidation, α-tocopherol, and ascorbate. Arch Biochem Biophys, 300, pp. 535-543.
29. Lockart, B., Bonhomme, N., Roger, A., Dorey, G., Casara, P. and Lestage, P. (2001) Protective effect of the antioxidant 6-ethoxy-2,2-pentamethylen-1,2-dihydroquinoline (S 33113) in models of cerebral neurodegeneration. Eur J Pharmacol, 416, pp. 59-68.
30. Koppenol, WH (1990) Oxyradical reactions: From bond-dissociation energies to reduction potentials. FEBS Lett, 264, pp. 165-167.
31. Patel, RP, Boersma, BJ, Crawford, JH, Hogg, N., Kirk, M., Kalyanaraman, B., Parks, DA, Barnes, S. and Darley-Usmar, V. (2001) Antioxidant mechanisms of isoflavones in lipid systems: Paradoxical effects of peroxyl radical scavenging. Free Radic Biol Med, 31, pp. 1570-1581.
32. Motoyama, T., Masayuki, M., Mino, M., Takahashi, M. and Niki, E. (1989) Synergistic inhibition of oxidation in dispersed phosphatidylcholine liposomes by a combination of vitamin E and cysteine. Arch Biochem Biophys, 270, pp. 655-661.
33. Barclay, LRC (1988) The cooperative antioxidant role of glutathione oxidation of liposomes initiated in the aqueous phase and in the lipid phase. J Biol Chem, 263, pp. 16138-16142.
34. Doba, T., Burton, GW and Ingold, KU (1985) Antioxidant and co-antioxidant activity of vitamin C. The effect of vitamin C, either alone or in the presence of vitamin E or a water-soluble vitamin E analogue, upon the peroxidation of aqueous multilamellar phospholipids liposomes. Biochim Biophys Acta, 835, pp. 298-303.
35. Ingold, KU, Bowry, VW, Stocker, R. and Walling, C. (1993) Autoxidation of lipids and antioxidation by alpha-tocopherol and ubiquinol in homogeneous solution and in aqueous dispersions of lipids: Unrecognized consequences of lipid particle size as exemplified by oxidation of human low density lipoprotein. Proc Natl Acad Sci USA, 90, pp. 45-49.
36. Constantinescu, A., Han, D. and Packer, L. (1993) Vitamin E recycling in human erythrocyte membranes. J Biol Chem, 268, pp. 10906-10913.
37. Kagan, VE, Serbinova, EA, Forte, T., Scita, G. and Packer, L. (1992) Recycling of vitamin E in human low density lipoproteins. J Lipid Res, 33, pp. 385-397.
38. Terao, J., Piscula, M. and Yao, Q. (1994) Protective effect of epicatechin, epicatechin gallate and quercetin on lipid peroxidation in phospholipid bilayers. Arch Biochem Biophys, 308, pp. 278-284.
39. Tesoriere, L., Allegra, M., Butera, D. and Livrea, MA (2004) Absorption, excretion, and distribution of dietary antioxidant betalains in LDLs: Potential health effects of betalains in humans. Am J Clin Nutr, 80, pp. 941-945.