Betanin inhibits the myeloperoxidase/nitrite-induced oxidation of human low-density lipoproteins

Free Radical Research

Volumn 41, Issue 3, 2007, Pages 335-341

  Allegra, Mario ^a   Tesoriere, Luisa ^a   Livrea, Maria ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

Atherosclerosis; Betanin; Low density lipoproteins; Myeloperoxidase; Nitrite

Indexed keywords

BETALAIN; BETANIN; LIPID HYDROPEROXIDE; LOW DENSITY LIPOPROTEIN; MYELOPEROXIDASE; NITRITE; NITROGEN DIOXIDE; PEROXY RADICAL; SCAVENGER; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; OXIDATION; OXIDATION KINETICS;

BETACYANINS; FREE RADICAL SCAVENGERS; HUMANS; LIPOPROTEINS, LDL; NITRITES; NITROGEN DIOXIDE; OXIDATION-REDUCTION; PEROXIDASE;

EID: 33947138154     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760601038783     Document Type: Article

References (44)

1. Steinberg, D., Parthasarathy, S., Carew, TE, Khoo, JC and Witztum, JL (1989) Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N Engl J Med, 320, pp. 915-924.
2. Heinecke, JW (1998) Oxidants and antioxidants in the pathogenesis of atherosclerosis: Implications for the oxidized low density lipoprotein hypothesis. Atherosclerosis, 141, pp. 1-15.
3. Lusis, AJ (2000) Atherosclerosis. Nature, 407, pp. 233-241.
4. Daugherty, A., Dunn, JL, Rateri, DL and Heinecke, JW (1994) Myeloperoxidase, a catalyst for lipoprotein oxidation, is expressed in human atherosclerotic lesions. J Clin Invest, 94, pp. 437-444.
5. Heller, JI, Crowley, JR, Hazen, SL, Salvay, DM, Wagner, P., Pennathur, S. and Heinecke, JW (2000) p-Hydroxyphenylacetaldehyde, an aldehyde generated by myeloperoxidase, modifies phospholipid amino groups of low density lipoprotein in human atherosclerotic intima. J Biol Chem, 275, pp. 9957-9962.
6. Klebanoff, SJ (1980) Oxygen metabolism and the toxic properties of phagocytes. Ann Intern Med, 93, pp. 480-489.
7. Marquez, LA and Dunford, HB (1997) Mechanism of the oxidation of 3,5,3′,5′-tetramethylbenzidine by myeloperoxidase determined by transient- and steady-state kinetics. Biochemistry, 36, pp. 9349-9355.
8. Leeuwenburgh, C., Hardy, MM, Hazen, SL, Wagner, P., Oh-ishi, S., Steinbrecher, UP and Heinecke, JW (1997) Reactive nitrogen intermediates promote low density lipoprotein oxidation in human atherosclerotic intima. J Biol Chem, 272, pp. 1433-1436.
9. Savenkova, ML, Mueller, DM and Heinecke, JW (1994) Tyrosyl radical generated by myeloperoxidase is a physiological catalyst for the initiation of lipid peroxidation in low density lipoprotein. J Biol Chem, 269, pp. 20394-20400.
10. Leeuwenburgh, C., Rasmussen, JE, Hsu, FF, Mueller, DM, Pennathur, S. and Heinecke, JW (1997) Mass spectrometric quantification of markers for protein oxidation by tyrosyl radical, copper, and hydroxyl radical in low density lipoprotein isolated from human atherosclerotic plaques. J Biol Chem, 272, pp. 3520-3526.
11. Furtmuller, PG, Burner, U. and Obinger, C. (1998) Reaction of myeloperoxidase compound I with chloride, bromide, iodide, and thiocyanate. Biochemistry, 37, pp. 17923-17930.
12. Hazell, LJ and Stocker, R. (1993) Oxidation of low-density lipoprotein with hypochlorite causes transformation of the lipoprotein into a high-uptake form for macrophages. Biochem J, 290, pp. 165-172.
13. Hazell, LJ, Arnold, L., Flowers, D., Waeg, G., Malle, E. and Stocker, R. (1996) Presence of hypochlorite-modified proteins in human atherosclerotic lesions. J Clin Invest, 97, pp. 1535-1544.
14. Hazen, SL and Heinecke, JW (1997) 3-Chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima. J Clin Invest, 99, pp. 2075-2081.
15. Burner, U., Furtmuller, PG, Kettle, AJ, Koppenol, WH and Obinger, C. (2000) Mechanism of reaction of myeloperoxidase with nitrite. J Biol Chem, 275, pp. 20597-20601.
16. Eiserich, JP, Hristova, M., Cross, CE, Jones, AD, Freeman, BA, Halliwell, B. and van der Vliet, A. (1998) Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature, 391, pp. 393-397.
17. van der Vliet, A., Eiserich, JP, Halliwell, B. and Cross, CE (1997) Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide-dependent toxicity. J Biol Chem, 272, pp. 7617-7625.
18. Sampson, JB, Rosen, H. and Beckman, JS (1998) Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch Biochem Biophys, 356, pp. 207-213.
19. Byun, J., Mueller, DM, Fabjan, JS and Heinecke, JW (1999) Nitrogen dioxide radical generated by the myeloperoxidase-hydrogen peroxide-nitrite system promotes lipid peroxidation of low density lipoprotein. FEBS Lett, 455, pp. 243-246.
20. Kostyuk, VA, Kraemer, T., Sies, H. and Schewe, T. (2003) Myeloperoxidase/ nitrite-mediated lipid peroxidation of low-density lipoprotein as modulated by flavonoids. FEBS Lett, 537, pp. 146-150.
21. Kris-Etherton, PM, Hecker, KD, Bonanome, A., Coval, SM, Binkoski, AE, Hilpert, KF, Griel, AE and Etherton, TD (2002) Bioactive compounds in foods: Their role in the prevention of cardiovascular disease and cancer. Am J Med, 113, pp. 71S-88S.
22. Piattelli, M. (1981) The betalains: Structure, biosynthesis and chemical taxonomy. The biochemistry of plants: A comprehensive treatise, pp. 557-575. Academic Press, New York
23. 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.
24. Kanner, J., Harel, S. and Granit, R. (2001) Betalains-a new class of dietary cationized antioxidants. J Agric Food Chem, 49, pp. 5178-5185.
25. 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.
26. 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 HPLC-electrospray ionization mass spectrometry. J Agric Food Chem, 50, pp. 2302-2307.
27. Kleinveld, HA, Hak-Lemmers, HL, Stalenhoef, AF and Demacker, PN (1992) Improved measurement of low-density-lipoprotein susceptibility to copper-induced oxidation: Application of a short procedure for isolating low-density lipoprotein. Clin Chem, 38, pp. 2066-2072.
28. Bradford, MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem, 72, pp. 248-254.
29. Allegra, M., Furtmuller, PG, Jantschko, W., Zederbauer, M., Tesoriere, L., Livrea, MA and Obinger, C. (2005) Mechanism of interaction of betanin and indicaxanthin with human myeloperoxidase and hypochlorous acid. Biochem Biophys Res Commun, 332, pp. 837-844.
30. Heinecke, JW, Daehnke 3rd, HL and Goldstein, JA (1993) Dityrosine, a specific marker of oxidation, is synthesized by the myeloperoxidase-hydrogen peroxide system of human neutrophils and macrophages. J Biol Chem, 268, pp. 4069-4077.
31. Wieland, E., Parthasarathy, S. and Steinberg, D. (1993) Peroxidase-dependent metal-independent oxidation of low density lipoprotein of low density lipoprotein in vitro: A model for in vivo oxidation?. Proc Natl Acad Sci USA, 90, pp. 5929-5933.
32. 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 hemolysis in humans. J Agric Food Chem, 53, pp. 1266-1270.
33. 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.
34. Brennan, ML, Shen, Z., Song, W., Frost, H., Vadseth, C., Narine, L., Lenkiewicz, E., Borchers, MT, Lusis, AJ, Lee, JJ, Lee, NA, Abu-Soud, HM, Ischiropoulos, H. and Hazen, SL (2002) A tale of two controversies: Defining both the role of peroxidases in nitrotyrosine formation in vivo using eosinophil peroxidase and myeloperoxidase-deficient mice, and the nature of peroxidase-generated reactive nitrogen species. J Biol Chem, 277, pp. 17415-17427.
35. Brennan, ML, Penn, MS, Van Lente, F., Nambi, V., Shishehbor, MH, Aviles, RJ, Goormastic, M., Pepoy, ML, McErlean, ES, Topol, EJ, Nissen, SE and Hazen, SL (2003) Prognostic value of myeloperoxidase in patients with chest pain. N Engl J Med, 349, pp. 1595-1604.
36. Zhang, R., Brennan, ML, Shen, Z., MacPherson, JC, Schmitt, D., Molenda, CE and Hazen, SL (2002) Myeloperoxidase functions as a major enzymatic catalyst for initiation of lipid peroxidation at sites of inflammation. J Biol Chem, 277, pp. 46116-46122.
37. Huie, RE (1994) The reaction kinetics of. Toxicology, 89, pp. 193-216.
38. Santanam, N. and Parthasarathy, S. (1995) Paradoxical actions of antioxidants in the oxidation of low density lipoprotein by peroxidases. J Clin Invest, 95, pp. 2594-2600.
39. Sies, H. and Murphy, ME (1991) Role of tocopherols in the protection of biological systems against oxidative damage. J Photochem Photobiol B, 8, pp. 211-218.
40. Burton, GW and Traber, MG (1990) Vitamin E: Antioxidant activity, biokinetics, and bioavailability. Annu Rev Nutr, 10, pp. 357-382.
41. Palozza, P. and Krinsky, NI (1991) The inhibition of radical-initiated peroxidation of microsomal lipids by both alpha-tocopherol and beta-carotene. Free Radic Biol Med, 11, pp. 407-414.
42. Tesoriere, L., Bongiorno, A., Pintaudi, AM, D'Anna, R., D'Arpa, D. and Livrea, MA (1996) Synergistic interactions between vitamin A and vitamin E against lipid peroxidation in phosphatidylcholine liposomes. Arch Biochem Biophys, 326, pp. 57-63.
43. Martinez-Parra, J. and Munoz, R. (1997) An approach to the characterization of betanine oxidation catalyzed by horseradish peroxidase. J Agric Food Chem, 45, pp. 2984-2988.
44. 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.