Formation of oxysterols during oxidation of low density lipoprotein by peroxynitrite, myoglobin, and copper

Journal of Lipid Research

Volumn 37, Issue 11, 1996, Pages 2361-2371

  Patel, Rakesh P ^a   Diczfalusy, Ulf ^b   Dzeletovic, Susanna ^b   Wilson, Michael T ^a   Darley Usmar, Victor M ^c,d  

^a UNIVERSITY OF ESSEX   (United Kingdom)

^b KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

^c UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^d University of Alabama at Birmingham   (United States)

Author keywords

atherosclerosis; cholesterol; copper; low density lipoprotein; myogl obin; oxysterols; peroxynitrite

Indexed keywords

24,25,27 HYDROXYCHOLESTEROL; 5,6ALPHA EPOXYCHOLESTEROL; 5,6BETA EPOXYCHOLESTEROL; 7 OXOCHOLESTEROL; 7ALPHA HYDROXYCHOLESTEROL; 7BETA HYDROXYCHOLESTEROL; ALPHA TOCOPHEROL; AMINO ACID; APOLIPOPROTEIN B; BUTYLCRESOL; CHOLESTANETRIOL; CHOLESTEROL; COPPER; FATTY ACID; LOW DENSITY LIPOPROTEIN; MYOGLOBIN; PEROXYNITRITE; PROPANE; RADICAL; STEROL; UNCLASSIFIED DRUG;

ARTICLE; ATHEROSCLEROSIS; CONTROLLED STUDY; CYTOTOXICITY; ELECTROPHORETIC MOBILITY; HUMAN; HYDROLYSIS; OXIDATION; PRIORITY JOURNAL; THIN LAYER CHROMATOGRAPHY;

EID: 0030454202     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (55)

1. Goldstein, J. L., and M. S. Brown. 1977. The low-density lipoprotein pathway and its relation to atherosclerosis. Annu. Rev. Biochem. 46: 897-930.
2. Palinski, W., M. E. Rosenfeld, S. Ylä-Herttuala, G. C. Gurtner, S. S. Socher, S. W. Butler, S. Parthasarathy, T. E. Carew, D. Steinberg, and J. L. Witztum. 1989. Low density lipoprotein undergoes oxidative modification in vivo. Proc. Natl. Acad. Sci. USA. 86: 1372-1376.
3. Steinberg, D., S. Parthasarathy, T. E. Carew, and J. L. Witztum. 1989. Beyond cholesterol: modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320: 915-924.
4. Ylä-Hertualla, S., W. Palinski, M. E. Rosenfeld, S. Parthasarathy, T. E. Carew, S. Butler, J. L. Witztum, and D. Steinberg. 1989. Evidence for the presence of oxidatively modified low density lipoprotein in atherosclerotic lesions of rabbit and man. J. Clin. Invest. 84: 1086-1095.
5. Steinbrecher, U. P., H. Zhang, and M. Lougheed. 1990. Role of oxidatively modified LDL in atherosclerosis. Free Radical Biol. & Med. 9: 155-168.
6. Björkhem, I., A. Henriksson-Freyschuss, O. Breuer, U. Diczfalusy, L. Berglund, and P. Henriksson. 1991. The antioxidant butylated hydroxytoluene protects against atherosclerosis. Aterioscler. Thromb. 11: 15-22.
7. Carew, T. E., D. C. Schwenke, and D. Steinberg. 1987. Antiatherogenic effect of probucol unrelated to its hypocholesterolemic effect: evidence that antioxidants in vivo can selectively inhibit low density lipoprotein degradation in macrophage rich fatty streaks and slow the progression of atherosclerosis in the watanabe heritable hyperlipidemic rabbit. Proc. Natl. Acad. Sci. USA. 84: 7725-7729.
8. Hodis, H. N., W. J. Mack, L. LaBree, L. Cashin-Hemphill, A. Sevanian, R. Johnson, and S. P. Azen. 1995. Serial coronary angiographic evidence that antioxidant vitamin intake reduces progression of coronary artery atherosclerosis. J. Am. Med. Assoc. 273: 1849-1854.
9. Rajavashisth, T. B., A. Andalibi, M. C. Territo, J. A. Berliner, M. Navab, A. M. Fogelman, and A. J. Lusis. Induction of endothelial cell expression of granulocyte and macrophage colony stimulating factors by modified low density lipoproteins. Nature. 344: 254-257.
10. Fong, L. G., T. A. T. Fong, and A. D. Cooper. 1991. Inhibition of lipopolysaccharide-induced interleukin-1β mRNA expression in mouse macrophages by oxidized low density lipoprotein. J. Lipid Res. 32: 1899-1910.
11. Berliner, J. A., M. C. Territo, A. Sevanian, S. Ranin, S. A. Kim, B. Bamshad, M. Esterson, and A. M. Fogelman. 1990. Minimally modified low density lipoprotein stimulates monocyte endothelial interactions. J. Clin. Invest. 85: 1230-1266.
12. Evenson, S. A., K. S. Galdal, and E. Nilsen. 1983. LDL-induced cytotoxicity and its inhibition by antioxidant treatment to cultured human endothelial cells and fibroblasts. Atherosclerosis. 49: 23-30.
13. Cathcart, M. K., D. W. More, and G. M. Chisolm. 1985. Monocytes and neutrophils oxidize low density lipoprotein making it cytotoxic. J. Leukocyte Biol. 38: 341-350.
14. Chisolm, G. M., G. Ma, K. C. Irwin, L. L. Martin, K. G. Gunderson, L. F. Linberg, D. W. Morel, and P. E. DiCorleto. 1994. 7β-Hydroxyperoxy cholest-5-en-3β-ol, a component of human atherosclerotic lesions, is the primary cytotoxin of oxidized human low density lipoprotein. Proc. Natl. Acad. Sci. USA. 91: 11452-11456.
15. Hughes, H., B. Matthews, M. L. Lenz, and J. R. Guyton. 1994. Cytotoxicity of oxidized LDL to porcine aortic smooth muscle cells is associated with the oxysterols 7-ketocholesterol and 7-hydroxycholesterol. Arterioscler. Thromb. 14: 1177-1185.
16. Björkhem, I., O. Andersson, U. Diczfalusy, B. Sevastik, R-J. Xiu, C. Duan, and E. Lund. 1994. Atherosclerosis and sterol 27-hydroxylase: evidence for a role of this enzyme in elimination of cholesterol from human macrophages. Proc. Natl. Acad. Sci. USA. 91: 8592-8596.
17. Smith, L. L., and B. H. Johnson. 1989. Biological activity of oxysterols. Free Radical Biol. & Med. 7: 285-332.
18. Jacobson, M. S. 1987. Gholesterol oxides in Indian ghee: possible cause of unexplained high risk of atherosclerosis in Indian immigrant populations. Lancet. 2: 656-658.
19. Thomas, C. E., and R. L. Jackson. 1991. Lipid hydroperoxide involvement in copper-dependent and -independent oxidation of low density lipoproteins. J. Pharmacol. Exp. Ther. 256: 1182-1188.
20. Hogg, N., G. Rice-Evans, V. M. Darley-Usmar, M. T. Wilson, G. Paganga, and L. Bourne. 1994. The role of lipid hydroperoxides in the myoglobin dependent oxidation of LDL. Arch. Biochem. Biophys. 313: 313-318.
21. Ehrenwald, E., G. M. Chisolm, and P. L. Fox. 1994. Intact human ceruloplasmin oxidatively modifies low density lipoprotein. J. Clin. Invest. 93: 1493-1501.
22. Ylä-Herttuala, S., M. E. Rosenfeld, S. Parthasarathy, C. K. Glass, E. Sigal, J. L. Witztum, and D. Steinberg. 1990. Localization of 15-lipoxygenase mRNA and protein with epitopes of oxidized low density lipoprotein in macrophage rich areas of atherosclerotic lesions. Proc. Natl. Acad. Sci. USA. 87: 6959-6964.
23. Darley-Usmar, V. M., N. Hogg, V. J. O'Leary, M. T. Wilson, and S. Moncada. 1992. The simultaneous generation of superoxide and nitric oxide can initiate lipid peroxidation in human low density lipoprotein. Free Radical Res. Commun. 17: 9-20.
24. Beckman, J. S., Y. Z. Ye, P. G. Anderson, J. Chen, M. A. Accavitti, M. M. Tarpey, and R. C. White. 1994. Extensive nitration of protein tyrosines in human atherosclerosis detected by immunohistochemistry. Biol. Chem. Hoppe-Seyler. 375: 81-88.
25. Daugherty, A., J. L. Dunn, D. L. Rateri, J. W. Heinecke. 1994. Myeloperoxidase a catalyst for lipoprotein oxidation is expressed in human atherosclerotic lesions. J. Clin. Invest. 94: 437-444.
26. 2. Arch. Biochem. Biophys. 262: 221-231.
27. Chung, B. H., T. Wilkinson, J. C. Geer, and J. P. Segrest. 1980. Preparative and quantitative isolation of plasma lipoprotein: rapid single discontinuous density gradient ultracentrifugation in a vertical rotor. J. Lipid Res. 21: 284-291.
28. Beckman, J. S., T. W. Beckman, J. Chen, P. A. Marshall, and B. A. Freeman. 1990. Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. USA. 87: 1620-1624.
29. Jessup, W., S. M. Rankin, C. V. DeWhalley, J. R. S. Hoult, J. Scott, and D. S. Leake. 1990. α-Tocopherol consumption during low density lipoprotein oxidation. Biochem. J. 265: 399-405.
30. Dzeletovic, S., O. Breuer, E. Lund, and U. Diczfalusy. 1995. Determination of cholesterol oxidation products in human plasma by isotope dilution-mass spectrometry. Anal. Biochem. 225: 73-80.
31. Dzeletovic, S., A. Babiker, E. Lund, and U. Diczfalusy. 1995. Time course of oxysterol formation during in vitro oxidation of low density lipoprotein. Chem. Phys. Lipids. 78: 119-128.
32. Schenk, G. O., K. Gollnick, and O. A. Neumüller. 1957. Darstellung von Steroid-Hydroperoxyden mittels phototoxischer Photosensibilisatoren. Liebigs Ann. Chem. 603: 46-59.
33. Schenk, G. O., O. A. Neumüller, and W. Eisfeld. 1958. Neuartige Allyl-Umlagerung von Steroid-Hydroperoxyden. Zur photosensibilisierten Autoxydation der Steroide, II. Angew. Chem. 70: 595.
34. 2+-stimulated oxidation of low-density lipoprotein. Arch. Biochem. Biophys. 315: 244-254.
35. Sato, K., E. Niki, and H. Shimasaki. 1990. Free radical-mediated oxidation of low density lipoprotein and its synergistic inhibition by vitamin E and vitamin C. Arch. Biochem. Biophys. 279: 402-405.
36. Esterbauer, H., M. Dieber-Rotheneder, G. Waeg, G. Striegl, and G. Jürgens. 1990. Biochemical, structural, functional properties of oxidized low density lipoprotein. Chem. Res. Toxicol. 3: 77-92.
37. Carpenter, K. L. H., G. M. Wilkins, B. Fussel, J. A. Ballantine, S. E. Taylor, M.J. Mitchinson, and D. S. Leake. 1994. Production of oxidized lipids during modification of low density lipoprotein by macrophages or copper. Biochem. J. 304: 625-633.
38. Smith, L. L. 1981. Cholesterol Autoxidation. Plenum Press, New York.
39. Sattler, W., J. Christison, and R. Stocker. 1995. Cholesteryl ester hydroperoxide reducing activity associated with isolated high density and low density lipoprotein. Free Radical Biol. Med. 18: 421-429.
40. Wu, G-S., R. A. Stein, and J. F. Mead. 1982. Autoxidation of phosphatidylcholine liposomes. Lipids. 17: 403-413.
41. Radi, R., J. S. Beckman, K. M. Bush, and B. A. Freeman. 1991. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 288: 481-487.
42. Iwatsuki, I., E. Niki, D. Stone, and V. M. Darley-Usmar. 1995. α-Tocopherol-mediated peroxidation in the copper (II)-dependent and metmyoglobin-induced oxidation of human low density lipoprotein: the influence of lipid hydroperoxides. FEBS Lett. 360: 271-276.
43. Hogg, N., J. Joseph, and B. Kalyanaraman. 1994. The oxidation of α-tocopheral and trolox by peroxynitrite. Arch. Biochem. Biophys. 314: 153-158.
44. Zhang, H., H. J. K. Basra, and U. P. Steinbrecher. 1990. Effects of oxidatively modified LDL on cholesterol esterification of cultured macrophages. J. Lipid Res. 31: 1361-1369.
45. 2+ ions: identification of major products and their effects. Biochem. Biophys. Res. Commun. 176: 431-440.
46. Jialal, I., D. A. Freeman, and S. M. Grundy. 1991. Varying susceptibility of different low density lipoproteins to oxidative modification. Arterioscler. Thromb. 11: 482-488.
47. Malavasi, B., M. F. Rasetti, P. Roma, R. Fogliatto, P. Allevi, A. L. Catapano, and G. Galli. 1992. Evidence for the presence of 7-hydroperoxycholest-5-en-3β-ol in oxidized human LDL. Chem. Phys. Lipids. 62: 209-214.
48. Caruso, D., M. F. Rasetti, L. De Angelis, and G. Galli. 1996. Identification of 3β-hydroxy-5α-cholest-6-ene-5-hydroperoxide in human oxidized LDL. Chem. Phys. Lipids. 79: 181-186.
49. Smith, L. L. 1996. Review of progress in sterol oxidations: 1987-1995. Lipids. 31: 453-487.
50. Bachowski, G. J., J. P. Thomas, and A. W. Girotti. 1988. Ascorbate-enhanced lipid peroxidation in photooxidized cell membranes: cholesterol product analysis as a probe of reaction mechanism. Lipids. 23: 580-586.
51. 2-isoprostanes during oxidation of low density lipoprotein and plasma by peroxynitrite. Circ. Res. 77: 335-341.
52. Hazell, L. J., J. M. van den Berg, and R. Stocker. 1994. Oxidation of low density lipoprotein by hypochlorite causes aggregation that is mediated by modification of lysine residues rather than lipid oxidation. Biochem. J. 302: 297-304.
53. Coffey, M. D., R. A. Cole, S. M. Colles, and G. M. Chisolm. 1995. In vitro cell injury by oxidized low density lipoprotein involves lipid hydroperoxide induced formation of alkoxyl, lipid and peroxyl radicals. J. Clin. Invest. 96: 1866-1870.
54. Blache, D., C. Rodriguez, and J. Davignon. 1995. Pro-oxidant effects of 7-hydroperoxycholest-5-en-3β-ol on the copper-initiated oxidation of low density lipoprotein. FEBS Lett. 357: 135-139.
55. Aupeix, K., D. Weltin, J. E. Mejia, M. Christ, J. Marchal, J. M. Freyssinet, and P. P. Bischoff. 1995. Oxysterol-induced apoptosis in human monocytic cell lines. Immunobiology. 194: 415-428.