Oxysterols in biological systems: sources, metabolism and pathophysiological relevance

REFERENCES

• Brown AJ, Jessup W. Oxysterols and atherosclerosis. Atherosclerosis 1999; 142: 1–28.
   PubMed Web of Science ®Google Scholar
• Schroepfer GJ. Oxysterols: modulators of cholesterol metabolism and other processes. Physiol Rev 2000; 80: 361–554.
   PubMed Web of Science ®Google Scholar
• Bjorkhem I, Meaney S, Diczfalusy U. Oxysterols in human circulation: which role do they have? Curr Opin Lipidol 2002; 13: 247–253.
   PubMed Web of Science ®Google Scholar
• Bjorkhem I, Diczfalusy U. Oxysterols. Friends, foes or just fellow passengers?Arterioscler Thromb Vasc Biol 2002; 22: 734–742.
   PubMed Web of Science ®Google Scholar
• Diczfalusy U. Analysis of cholesterol oxidation products in biological samples. J AOAC Int 2004; 87: 467–473.
   PubMed Web of Science ®Google Scholar
• Lyons MA, Samman S, Gatto L, Brown AJ. Rapid hepatic metabolism of 7-ketocholesterol in vivo: implications for dietary oxysterols. J Lipid Res 1999; 40: 1846–1857.
   PubMed Web of Science ®Google Scholar
• Lyons MA, Brown AJ. 7-Ketocholesterol delivered to mice in chylomicron remnant-like particles is rapidly metabolised, excreted and does not accumulate in aorta. Biochim Biophys Acta 2001; 1530: 209–218.
   PubMed Web of Science ®Google Scholar
• Ando M, Tomoyori H, Imaizumi K. Dietary cholesterol-oxidation products accumulate in serum and liver in apolipoprotein E-deficient mice, but do not accelerate atherosclerosis. Br J Nutr 2002; 88: 339–345.
   PubMed Web of Science ®Google Scholar
• Meynier A, Lherminier J, Demaison-Meloche J, Ginies C, Grandgirard A, Demaison L. Effects of dietary oxysterols on coronary arteries in hyperlipidaemic hamsters. Br J Nutr 2002; 87: 447–458.
   PubMed Web of Science ®Google Scholar
• Tomoyori H, Carvajal O, Nakayama M et al. Lymphatic transport of dietary cholesterol oxidation products, cholesterol and triacylglycerols in rats. Biosci Biotech Biochem 2002; 66: 828–834.
   PubMed Web of Science ®Google Scholar
• Schweizer RAS, Zurcher M, Balazs Z, Dick B, Odermatt A. Rapid hepatic metabolism of 7-ketocholesterol by 1113-hydroxysteroid dehydrogenase type 1. Species-specific differences between the rat, human, and hamster enzyme. J Biol Chem 2004; 279: 18415–18424.
   PubMed Web of Science ®Google Scholar
• Wu Z, Martin KO, Javitt NB, Chiang JYL. Structure and functions of human oxysterol 7a-hydroxylase cDNAs and gene GYP 7B1. J Lipid Res 1999; 40: 2195–2203.
   PubMed Web of Science ®Google Scholar
• Norlin M, Andersson U, Bjorkhem I, Wikvall K. Oxysterol 7a-hydroxylase activity by cholesterol 7a-hydroxylase (CYP7A). J Biol Chem 2000; 275: 34046–34053.
   PubMed Web of Science ®Google Scholar
• Seckl JR, Walker BR. 11P-Hydroxysteroid dehydrogenase type 1 as a modulator of glucocorticoid action: from metabolism to memory. Trends Endocrinol Metab 2004; 15: 418–424.
   PubMed Web of Science ®Google Scholar
• Cai T-Q, Wong B, Mundt SS, Thieringer R, Wright SD, Hermanowski-Vosatka A. Induction of 1113-hydroxysteroid dehydrogenase type 1 but not -2 in human aortic smooth muscle cells by inflammatory stimuli. J Steroid Biochem Mol Biol 2001; 77: 117–122.
   PubMed Web of Science ®Google Scholar
• Thieringer R, Le Grand CB, Carbin L et al. 113-Hydroxysteroid dehydrogenase type 1 is induced in human monocytes upon differentiation to macrophages. J Immunol 2001; 167: 30–35.
   PubMed Web of Science ®Google Scholar
• Zhang TY, Ding X, Daynes RA. The expression of 1113-hydroxysteroid dehydrogenase type I by lymphocytes provides a novel means for intracrine regulation of glucocorticoid activities. J Immunol 2005; 174: 879–889.
   PubMed Web of Science ®Google Scholar
• Raunio H, Hakkola J, Pelkonen O. Regulation of CYP3A genes in the human respiratory tract. Chemico-Biol Interact 2005; 151: 53–62.
   PubMed Web of Science ®Google Scholar
• Huff MW, Telford DE. Lord of the rings - the mechanism for oxidosqualene: lanosterol cyclase becomes crystal clear. Trends Pharmacol Sci 2005; 26: 335–340.
   PubMed Web of Science ®Google Scholar
• Smith LL. Cholesterol autoxidation 1981-1986. Chem Phys Lipids 1987; 44: 87–125.
   PubMed Web of Science ®Google Scholar
• Brown AJ, Watts GF, Burnett JR, Dean RT, Jessup W. Sterol 27-hydroxylase acts on 7-ketocholesterol in human atherosclerotic lesions and macrophages in culture. J Biol Chem 2000; 275: 27627–27633.
   PubMed Web of Science ®Google Scholar
• Diestel A, Aktas O, Hackel D et al. Activation of microglial poly(ADP-ribose)-polymerase-1 by cholesterol breakdown products during neuroinflammation: a link between demyelination and neuronal damage. J Exp Med 2003; 198: 1729–1740.
   PubMed Web of Science ®Google Scholar
• Babiker A, Andersson O, Lund E et al. Elimination of cholesterol in macrophages and endothelial cells by the sterol 27-hydroxylase mechanism. Comparison with high density lipoprotein-mediated reverse cholesterol transport. J Biol Chem 1997; 272: 26253–26261.
   PubMed Web of Science ®Google Scholar
• Gelissen IC, Rye K-A, Brown AJ, Dean RT, Jessup W. Oxysterol efflux from macrophage foam cells: the essential role of acceptor phospholipid. J Lipid Res 1999; 40: 1636–1646.
   PubMed Web of Science ®Google Scholar
• Brown AJ, Mander EL, Gelissen IC, Kritharides L, Dean RT, Jessup W. Cholesterol and oxysterol metabolism and subcellular distribution in macrophage foam cells: accumulation of oxidized esters in lysosomes. J Lipid Res 2000; 41: 226–236.
   PubMed Web of Science ®Google Scholar
• Dzeletovic S, Breuer O, Lund E, Diczfalusy U. Determination of cholesterol oxidation products in human plasma by isotope dilution-mass spectrometry. Anal Biochem 1995; 225: 73–80.
   PubMed Web of Science ®Google Scholar
• Rimner A, Al Makdessi S, Sweidan H et al. Relevance and mechanism of oxysterol stereospecificity in coronary artery disease. Free Radic Biol Med 2005; 38: 535–544.
   PubMed Web of Science ®Google Scholar
• Prunet C, Petit JM, Ecarnot-Laubriet A et al. High circulating levels of 713- and 7a-hydroxycholesterol and presence of apoptotic and oxidative markers in arterial lesions of normocholesterolemic atherosclerotic patients undergoing endarterectomy. Pathol Biol 2006; 54: 22–32.
   PubMed Web of Science ®Google Scholar
• Leoni V, Lutjohann D, Masterman T. Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res 2005; 46: 191–195.
   PubMed Web of Science ®Google Scholar
• Lutjohann D, Breuer O, Ahlborg G et al. Cholesterol homeostasis in human brain: evidence for an age-dependent flux of 24S-hydroxycholesterol from the brain into the circulation. Proc Natl Acad Sci USA 1996; 93: 9799–9804.
   PubMed Web of Science ®Google Scholar
• von Bahr S, Movin T, Papadogiannakis Net al. Mechanism of accumulation of cholesterol and cholestanol in tendons and the role of sterol 27-hydroxylase (CYP2741). Arterioscler Thromb Vasc Biol 2002; 22: 1129–1135.
   PubMed Web of Science ®Google Scholar
• Iuliano L, Micheletta F, Natoli S et al. Measurement of oxysterols and a-tocopherol in plasma and tissue samples as indices of oxidant stress status. Anal Biochem 2003; 312: 217–223.
   PubMed Web of Science ®Google Scholar
• Girao H, Mota MC, Ramalho J, Pereira P. Cholesterol oxides accumulate in human cataracts. Exp Eye Res 1998; 66: 645–652.
   PubMed Web of Science ®Google Scholar
• Gloor BP, Rokos L, Kaldarar-Pedotti S. Cell cycle time and life-span of cells in the mouse eye. Measurements during the postfetal period using repeated 3H-thymidine injections. Dev Ophthal 1985; 12: 70–129.
   PubMedGoogle Scholar
• Cenedella RJ. Posttranscriptional regulation of 3-hydroxy-3-methylglutaryl coenzyme A reductase in lens epithelial cells by mevalonate-derived nonsterols. Exp Eye Res 1997; 65: 63–72.
   PubMed Web of Science ®Google Scholar
• Moghadasian MH. Cerebrotendinous xanthomatosis: clinical course, genotypes and metabolic backgrounds. Clin Invest Med 2004; 27: 42–50.
   PubMed Web of Science ®Google Scholar
• Kucuk O, Lis LJ, Dey Tel al. The effects of cholesterol oxidation products in sickle and normal red blood cell membranes. Biochim Biophys Acta 1992; 1103: 296–302.
   PubMed Web of Science ®Google Scholar
• Teng JI, Smith LL. High-performance liquid chromatographic analysis of human erythrocyte oxysterols as 44-3-ketone derivatives. J Chromatogr A 1995; 691: 247–254.
   PubMed Web of Science ®Google Scholar
• Abo K, Mio T, Sumino K. Comparative analysis of plasma and erythrocyte 7-ketocholesterol as a marker for oxidative stress in patients with diabetes mellitus. Clin Biochem 2000; 33: 541–547.
   PubMed Web of Science ®Google Scholar
• Muskiet FD, Muskiet FAJ. Lipids, fatty acids and trace elements in plasma and erythrocytes of pediatric patients with homozygous sickle cell disease. Clin Chim Acta 1984; 142: 1–10.
   PubMed Web of Science ®Google Scholar
• Ketomaki A, Gylling H, Miettinen TA. Non-cholesterol sterols in serum, lipoproteins, and red cells in statin-treated FH subjects off and on plant stanol and sterol ester spreads. Clin Chim Acta 2005; 353: 75–86.
   PubMed Web of Science ®Google Scholar
• Takahashi K, Takeya M, Sakashita N. Multifunctional role of macrophages in the development and progression of atherosclerosis in humans and experimental animals. Med Electron Microsc 2002; 35: 179–203.
   PubMedGoogle Scholar
• Maor I, Kaplan M, Hayek T, Vaya J, Hoffman A, Aviram M. Oxidized monocyte-derived macrophages in aorticatherosclerotic lesion from apolipoprotein E-deficient mice and from human carotid artery contain lipid peroxides and oxysterols. Biochem Biophys Res Commun 2000; 269: 775–780.
   PubMed Web of Science ®Google Scholar
• Mattsson L, Bondjers G, Wiklund O. Isolation of cell populations from arterial tissue, using monoclonal antibodies and magnetic microspheres. Atherosclerosis 1991; 89: 25–34.
   PubMed Web of Science ®Google Scholar
• Naito M, Nomura H, Esaki T, Iguchi A. Characteristics of macrophage-derived foam cells isolated from atherosclerotic lesions of rabbits. Atherosclerosis 1997; 135: 241–247.
   PubMed Web of Science ®Google Scholar
• Biasi F, Leonarduzzi G, Vizio B et al. Oxysterol mixtures prevent proapoptotic effects of 7-ketocholesterol in macrophages: implications for proatherogenic gene modulation. FASEB J2004; 18: 693–695.
   PubMed Web of Science ®Google Scholar
• Babiker A, Diczfalusy U. Transport of side-chain oxidized oxysterols in the human circulation. Biochim Biophys Acta 1998; 1392: 333–339.
   PubMed Web of Science ®Google Scholar
• Boissonneault GA, Hennig B, Wang Yet al. Effects of oxysterol-enriched low-density lipoprotein on endothelial barrier function in culture. Am Nutr Metab 1991; 35: 226–232.
   Web of Science ®Google Scholar
• Rodriguez IR, Alam S, Lee JW. Cytotoxicity of oxidized low-density lipoprotein in cultured RPE cells is dependent on the formation of 7-ketocholesterol. Invest Ophthalmol Vis Sci 2004; 45: 2830–2837.
   PubMed Web of Science ®Google Scholar
• Gelissen IC, Brown AJ, Mander EL, Kritharides L, Dean RT, Jessup W. Sterol efflux is impaired from macrophage foam cells selectively enriched with 7-ketocholesterol. J Biol Chem 1996; 271: 17852–17860.
   PubMed Web of Science ®Google Scholar
• Fu X, Menke JG, Chen Yet al. 27-Hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem 2001; 276: 38378–38387.
   PubMed Web of Science ®Google Scholar
• Goldstein JL, DeBose-Boyd RA, Brown MS. Protein sensors for membrane sterols. Cell 2006; 124: 35–46.
   PubMed Web of Science ®Google Scholar
• Janowski BA, Shan B, Russell DW. The hypocholesterolemic agent LY295427 reverses suppression of sterol regulatory element-binding protein processing mediated by oxysterols. J Biol Chem 2001; 276: 45408–45416.
   PubMed Web of Science ®Google Scholar
• Adams CM, Reitz J, De Brabander JK et al. Cholesterol and 25-hydroxycholesterol inhibit activation of SREBPs by different mechanisms, both involving SCAP and Insigs. J Biol Chem 2004; 279: 52772–52780.
   PubMed Web of Science ®Google Scholar
• Brown AJ, Sun L, Feramisco JD, Brown MS, Goldstein JL. Cholesterol addition to ER membranes alters conformation of SCAP, the SREBP escort protein that regulates cholesterol metabolism. Mol Cell 2002; 10: 237–245.
   PubMed Web of Science ®Google Scholar
• Repa JJ, Mangelsdorf DJ. The liver X receptor gene team: potential new players in atherosclerosis. Nat Med 2002; 8: 1243–1248.
   PubMed Web of Science ®Google Scholar
• Janowski BA, Willy PJ, Rama Devi T, Falck JR, Mangelsdorf DJ. An oxysterol signalling pathway mediated by the nuclear receptor LXRa. Nature 1996; 383: 728–731.
   PubMed Web of Science ®Google Scholar
• Lehmann JM, Kliewer SA, Moore LB et al. Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway. J Biol Chem 1997; 272: 3137–3140.
   PubMed Web of Science ®Google Scholar
• Janowski BA, Grogan MJ, Jones SA et al. Structural requirements of ligands for the oxysterol liver X receptors LXRa and LXRP. Proc Natl Acad Sci USA 1999; 96: 266–271.
   PubMed Web of Science ®Google Scholar
• Song C, Liao S. Cholestanoic acid is a naturally occuring ligand for liver X receptor a. Endocrinology 2000; 141: 4180–4184.
   PubMed Web of Science ®Google Scholar
• Wong J, Quinn CM, Brown AJ. Statins inhibit synthesis of an oxysterol ligand for liver X receptor in human macrophages with consequences for cholesterol flux. Arterioscler Thromb Vasc Biol 2004; 24: 2365–2371.
   PubMed Web of Science ®Google Scholar
• 011ckonen VM, Levine TP. Oxysterol binding proteins: in more than one place at one time? Biochem Cell Biol 2004; 82: 87-98.
   Google Scholar
• Bjorkhem I. Do oxysterols control cholesterol homeostasis? J Clin Invest 2002; 110: 725–730.
   PubMed Web of Science ®Google Scholar
• Mattsson Hult'en L, Lindmark H, Diczfalusy U et al. Oxysterols present in atherosclerotic tissue decrease the expression of lipoprotein lipase messenger RNA in human monocyte-derived macrophages. J Clin Invest 1996; 97: 461–468.
   PubMed Web of Science ®Google Scholar
• Brown AJ, Leong S-L, Dean RT, Jessup W. 7-hydroperoxycholesterol and its products in oxidised low density lipoprotein and human atherosclerotic plaque. J Lipid Res 1997; 38: 1730–1745.
   PubMed Web of Science ®Google Scholar
• Garner B, Dean RT, Jessup W. Human macrophage-mediated oxidation of low-density lipoprotein is delayed and independent of superoxide production. Biochem J1994; 301: 421-428.
   Google Scholar
• Chung BH, Segrest JP, Ray MJ et al. Single vertical spin density gradient ultracentrifugation. Methods Enzymol 1986; 128: 181–209.
   PubMed Web of Science ®Google Scholar
• Kritharides L, Jessup W, Mander EL, Dean RT. Apolipoprotein A-I-mediated efflux of sterols from oxidised LDL-loaded macrophages. Arterioscler Thromb Vasc Biol 1995; 15: 276–289.
   PubMed Web of Science ®Google Scholar
• van Reyk DM, Jessup W. The macrophage in atherosclerosis: modulation of cell function by sterols. J Leukoc Biol 1999; 66: 557–561.
   PubMed Web of Science ®Google Scholar