7-Hydroperoxycholesterol and its products in oxidized low density lipoprotein and human atherosclerotic plaque

Journal of Lipid Research

Volumn 38, Issue 9, 1997, Pages 1730-1745

  Brown, Andrew J ^a   Leong, Su Lin ^a   Dean, Roger T ^a   Jessup, Wendy ^a  

^a HEART RESEARCH INSTITUTE   (Australia)

Author keywords

27 hydroxycholesterol; 7 ketocholesterol; Atherosclerosis; Cholesterol oxidation products cholesterol oxides; Lipid peroxides; Oxidized LDL

Indexed keywords

7 OXOCHOLESTEROL; CHOLESTEROL; CHOLESTEROL DERIVATIVE; CYTOTOXIN; LIPID; LIPID PEROXIDE; LOW DENSITY LIPOPROTEIN; OXIDIZED LOW DENSITY LIPOPROTEIN; STEROL DERIVATIVE;

ANIMAL CELL; ARTICLE; ATHEROGENESIS; ATHEROSCLEROTIC PLAQUE; CAROTID ENDARTERECTOMY; CHEMOLUMINESCENCE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; LIPID ANALYSIS; LIPID METABOLISM; MOUSE; NONHUMAN; OXIDATION; PERITONEUM MACROPHAGE; PRIORITY JOURNAL; STEROL ANALYSIS;

ANIMALS; ARTERIOSCLEROSIS; CHOLESTEROL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COPPER; HUMANS; LIPID PEROXIDES; LIPOPROTEINS, LDL; MACROPHAGES, PERITONEAL; MICE; OXIDATION-REDUCTION;

EID: 0030820068     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (56)

1. Stary, H. C., A. B. Chandler, R. E. Dinsmore, V. Fuster, S. Glagov, W. Insull, Jr., M. E. Rosenfield, C. J. Schwartz, W. D. Wagner, and R. W. Wissler. 1995. A definition of advanced types of atherosclerotic lesions and a histological classification of atherosclerosis. A report from the Committee on Vascular Lesions of the Council on Arteriosclerosis, American Heart Association. Arterioscler. Thromb. Vasc. Biol. 15: 1512-1531.
2. Steinberg, D., S. Pathasarathy, T. E. Carew, J. C. Khoo, and J. L. Witzum. 1989. Beyond cholesterol: modification of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 320: 915-924.
3. Garner, B., and W. Jessup. 1996. Cell-mediated oxidation of low-density lipoprotein: the elusive mechanism(s). Redox Report. 2: 97-104.
4. Steinbrecher, U. P., and M. Lougheed. 1992. Scavenger receptor-independent stimulation of cholesterol esterification in macrophages by low density lipoprotein extracted from human aortic intima. Arterioscler. Thromb. 12: 608-625.
5. Brown, A. J., R. T. Dean, and W. Jessup. 1996. Free and esterified oxysterol: formation during copper-oxidation of low density lipoprotein and uptake by macrophages. J. Lipid Res. 37: 320-335.
6. 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.
7. Tanaka, M., and S. Kanamaru. 1993. Capillary gas chromatography quantification of cholesterol in copper-oxidised low-density lipoproteins. Biol. Pharm. Bull. 16: 538-543.
8. Carpenter, K. L., G. M. Wilkins, B. Fussell, 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.
9. 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.
10. Mori, T. A., K. D. Croft, I. B. Puddey and L. J. Beilin. 1996. Analysis of native and oxidized low density lipoprotein using GC-MS with selective ion monitoring. Redox Rep. 2: 25-34.
11. Patel, R. P., U. Diczfalusy, S. Dzeletovic, M. T. Wilson, and V. M. Darley-Usmar. 1996. Formation of oxysterols during oxidation of low density lipoprotein by peroxynitrite, myoglobin, and copper. J. Lipid Res. 37: 2361-2371.
12. 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-Hydroperoxycholest-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.
13. Malavasi, B., M. F. Rasetti, P. Roma, R. Fogliatto, P. Allevi, A. E. Catapano, and G. Galli. 1992. Evidence for the presence of 7-hydroperoxycholest-5-en-3β-ol in oxidised human LDL. Chem. Phys. Lipids. 62: 209-214.
14. Park, P. S. W., and P. B. Addis. 1991. Methods of analysis of cholesterol oxides. In Biological Effects of Cholesterol Oxides. S-K. Peng, and R. J. Morin, editors. CRC Press, Boca Raton, FL. 33-70.
15. Brooks, C. J. W., W. A. Harland, and G. Steel. 1966. Squalene, 26-hydroxycholesterol and 7-ketocholesterol in human atheromatous plaques. Biochim. Biophys. Acta. 125: 623-626.
16. van Lier, J. E., and L. L. Smith. 1967. Sterol metabolism. I. 26-Hydroxycholesterol in the human aorta. Biochemistry. 6: 3269-3278.
17. Carpenter, K. L., S. E. Taylor, J. A. Ballantine, B. Fussell, B. Halliwell, and M. J. Mitchinson. 1993. Eipids and oxidised lipids in human atheroma and normal aorta. Biochim. Biophys. Acta. 1167: 121-130.
18. 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: 8582-8596.
19. Carpenter, K. H. L., S. E. Taylor, C. van der Veen, B. K. Williamson, J. A. Ballantine, and M. J. Mitchinson. 1995. Eipids and oxidised lipids in human atherosclerotic lesions at different stages of development. Biochim. Biophys. Acta. 1256: 141-150.
20. Suarna, C., R. T. Dean, J. May, and R. Stocker. 1995. Human atherosclerotic plaque contains both oxidized lipids and relatively large amounts of α-tocopherol and ascorbate. Arterioscler. Thromb. Vasc. Biol. 15: 1616-1624.
21. Schenck, G. O., K. Gollnick, and O. A. Neumuller. 1957. Darstellung von Steroid-Hydroperoxyden mittels phototoxischer Photosensibilisatoren. Liebigs Ann. Chem. 603: 46-59.
22. 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.
23. Deykin, D., and D. S. Goodman. 1962. The hydrolysis of long-chain fatty acids of cholesterol with rat liver enzymes. J. Biol. Chem. 237: 3649-3656.
24. Kritharides, L., W. Jessup, J. Gifford, and R. T. Dean. 1993. A method for defining the stages of low density lipoprotein oxidation by the separation of cholesterol- and cholesteryl ester-oxidation products using HPLC. Anal. Biochem. 213: 79-89.
25. van Reyk, D., A. J. Brown, W. Jessup, and R. T. Dean. 1995. Batch-to-batch variation of Chelex-100 confounds metal-catalysed oxidation. Free Radical Res. 23: 533-535.
26. Kritharides, L., W. Jessup, E. L. Mander, and R. T. Dean. 1995. Apolipoprotein A-I-mediated efflux of sterols from oxidized LDL-loaded macrophages. Arterioscler. Thromb. Vasc. Biol. 15: 276-289.
27. Hodis, H. N., D. W. Crawford, and A. Sevanian. 1991. Cholesterol feeding increases plasma and aortic tissue cholesterol oxide levels in parallel: further evidence for the role of cholesterol oxidation in atherosclerosis. Atherosclerosis. 89: 117-126.
28. Jonus, A. 1986. Reconstitution of high-density lipoproteins. Methods Enzymol. 128: 553-582.
29. Suzuki, K., N. Sakata, A. Kitani, M. Hara, T. Hirose, W. Hirose, K. Norioka, M. Hariga, M. Kawagoe, and H. Nakaimira. 1990. Characterization of human monocytic cell line, U937, in taking up acetylated low-density lipoprotein and cholesteryl ester accumulation. A flow cytometric and HPLC study. Biochim. Biophys. Acta. 1042: 210-216.
30. Ozawa, N., S. Yamazaki, K. Chiba, H. Aoyama, H. Tomisawa, M. Tateishi, and T. Watabe. 1991. Occurrence of cholesterol 7α and 7β-hydroperoxides in rat skin as aging markers. Biochem. Biophys. Res. Commun. 178: 242-247.
31. Yamamoto, Y., M. Brodsky, J. Baker, and B. Ames. 1987. Detection and characterization of lipid hydroperoxides at picomole levels by high-performance liquid chromatography. Anal. Biochem. 160: 7-13.
32. Sevanian, A., and L. L. McLeod. 1987. Cholesterol autoxidation in phospholipid membrane bilayers. Lipids. 22: 627-636.
33. Brown, A. J., D. C. K. Roberts, J. E. Pritchard, and A. S. Truswell. 1991. A mixed Australian fish diet and fish oil supplementation: impact upon the plasma lipid profile of healthy men. Am. J. Clin. Nutr. 52: 825-833.
34. Korytowski, W., P. G. Geiger, and A. W. Girotti. 1996. Enzymatic reduction in relation to cytotoxicity for various cholesterol hydroperoxides. Biochemistry. 35: 8670-8679.
35. Koenig, T. 1973. The decompositions of peroxides and azoalkanes. In Free Radicals. J. K. Kochi. John Wiley & Sons, New York. 113-148.
36. Sevanian, A., H. N. Hodis, J. Hwang, L. L. McLeod, and H. Peterson. 1995. Characterization of endothelial cell injury by cholesterol oxidation products found in oxidized LDL. J. Lipid Res. 36: 1971-1986.
37. Leake, D. S., and S. M. Rankin. 1990. The oxidative modification of low-density lipoprotein by macrophages. Biochem. J. 270: 741-748.
38. Ansari, G. A. S., and L. L. Smith. 1990. Cholesterol epoxides: formation and measurement. Methods Enzymol. 186: 438-443.
39. Colles, S. M., K. C. Irwin, and G. M. Chisolm. 1996. Roles of multiple oxidized LDL lipids in cellular injury: dominance of 7β-hydroperoxycholesterol. J. Lipid Res. 37: 2018-2028.
40. Porter, N. 1992. Alky hydroperoxides. In Organic Peroxides. J. Ando, editor. Wiley & Sons, Chichester. 102-155.
41. Maiorino, M., J. P. Thomas, A. W. Girotti, and F. Ursini. 1991. Reactivity of phospholipid hydroperoxide glutathione peroxidase with membrane and lipoprotein lipid hydroperoxides. Free Radical Res. Commun. 12-13: 131-135.
42. Fu, S., S. Gebicki, W. Jessup, J. M. Gebicki, and R. T. Dean. 1995. Biological fate of amino acid, peptide and protein hydroperoxides. Biochem. J. 311: 821-827.
43. Maiorino, M., A. Roveri, and F. Ursini. 1992. Antioxidant effects of Ebselen (PZ51): peroxidase mimetic activity on phospholipid and cholesterol hydroperoxide vs free radical scavenger activity. Arch. Biochem. Biophys. 295: 404-409.
44. Gelissen, I. C., A. J. Brown, E. L. Mander, L. Kritharides, R. T. Dean, and W. Jessup. 1996. Sterol efflux is impaired from macrophage foam cells selectively enriched with 7-ketocholesterol. J. Biol. Chem. 271: 17852-17860.
45. Smith, L. L., J. I. Teng, Y. Y. Lin, P. K. Seitz, and M. F. McGehee. 1981. Sterol metabolism - XLVII. Oxidized cholesterol esters in human tissues. J. Steroid Biochem. 14: 889-900.
46. Addis, P. B., and P. S. W. Park. 1992. Cholesterol oxide content in food. In Biological Effects of Cholesterol Oxides. S-K. Peng, and R. J. Morin, editors. CRC Press, Boca Raton, FL. 71-88.
47. Song, W., W. M. Pierce, Y. Saeki, R. N. Redinger, and R. A. Prough. 1996. Endogenous 7-oxoxcholesterol is an enzymatic product: characterisation of 7α-hydroxycholesterol dehydrogenase activity of hamster liver microsomes. Arch. Biochem. Biophys. 328: 272-278.
48. Smith, L. L. 1981. Cholesterol Autoxidation. Plenum Press, New York.
49. Hodis, H. N., A. Chauhan, S. Hashimoto, D. W. Crawford, and A. Sevanian. 1992. Probucol reduces plasma and aortic wall oxysterol levels in cholesterol-fed rabbits independently of its plasma cholesterol lowering effect. Atherosclerosis. 96: 125-134.
50. Stalenhoef, A. F. H., H. A. Kleinfeld, T. G. Kosmeijer-Schuil, P. N. M. Demacker, and M. B. Katan. 1993. In vivo oxidised cholesterol in atherosclerosis. Atherosclerosis. 98: 113-114.
51. 2 inhalation technique and mass isotopomer distribution analysis to study oxygenation of cholesterol in rat. J. Biol. Chem. 270: 20278-20284.
52. Sevanian, A., R. Seraglia, P. Traldi, P. Rossato, F. Ursini, and H. Hodis. 1994. Analysis of plasma cholesterol oxidation products using gas and high-performance liquid chromatography/mass spectrometry. Free Radical Biol. Med. 17: 397-409.
53. Gardner, H. W. 1987. Reactions of hydroperoxides -products of high molecular weight. In Autoxidation of Unsaturated Lipids. H. W-S. Chan, editor. Academic Press, London. 51-93.
54. Hughes, H., B. Mathews, M. L. Lenz, and J. R. Guyton. 1994. Cytotoxicity of oxidised LDL to porcine aortic smooth muscle cells is associated with the oxysterols 7-ketocholesterol and 7-hydroxycholesterol. Arterioscler. Thromb. 14: 1177-1185.
55. Clare, K., S. J. Hardwick, K. L. H. Carpenter, N. Weeratunge, and M. J. Mitchinson. 1995. Toxicity of oxysterols to human monocyte-macrophages. Atherosclerosis. 118: 67-75.
56. Kilsdonk, E. P. C., D. W. Morel, W. J. Johnson, and G. H. Rothblat. 1995. Inhibition of cellular cholesterol efflux by 25-hydroxycholesterol. J. Lipid Res. 36: 505-516.