Cholesterol hydroperoxides and their degradation mechanism

Sub-Cellular Biochemistry

Volumn 77, Issue , 2014, Pages 83-91

  Terao, Junji ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

6 secosterol; Cholesterol 5; Cholesterol hydroperoxides; Lipid rafts; Singlet molecular oxygen

Indexed keywords

7-KETOCHOLESTEROL; CHOLESTEROL; CHOLESTEROL DERIVATIVE; CHOLESTEROL HYDROPEROXIDE; FREE RADICAL; HYDROGEN PEROXIDE; LIPOSOME; REACTIVE OXYGEN METABOLITE; SINGLET OXYGEN;

ANALOGS AND DERIVATIVES; CHEMISTRY; METABOLISM; SIGNAL TRANSDUCTION;

CHOLESTEROL; FREE RADICALS; HYDROGEN PEROXIDE; KETOCHOLESTEROLS; LIPOSOMES; REACTIVE OXYGEN SPECIES; SIGNAL TRANSDUCTION; SINGLET OXYGEN;

EID: 84899780650     PISSN: 03060225     EISSN: None     Source Type: Journal    
DOI: 10.1007/978-94-007-7920-4_7     Document Type: Article

References (35)

1. Adachi J, Asano M, Ueno Y, Reily M, Mantle D, Peters TJ, Preedy VR (2000) 7α-and 7- β-Hydroperoxycholest-5-ene-3β-ol in muscle as indices of oxidative stress: response to ethanol dosage in rats. Alcohol Clin Exp Res 24:675-681
2. Anticoli S, Arciello M, Mancinetti A, De Martins M, Ginald L, Iuliano L, Balsano C (2009) 7-ketocholesterol and 5,6-secosterol modulate differently the stress-activated mitogen-activated protein kinase (MAPK) in liver cells. J Cell Physiol 222:586-595
3. Ariyoshi K, Adachi J, Asano M, Ueno Y, Rejendram R, Preedy V (2002) Effect of chronic ethanol feeding on oxysterol in rat liver. Free Radic Res 36:661-666
4. Berthier A, Lemaire-Ewing PC, Monier S, Athias A, Bessede G, de Barros J-PP, Laubrier A, Gambert P, Lizard G, Neel D (2004) Involvement of a calcium-dependent dephosphorylation of BAD associated with the localization of Trpc-1 within lipid rafts in 7-ketocholesterolinduced THP-1 cell apoptosis. Cell Death Differ 11:897-905
5. Brinkhourt J, Nara SJ, Pratt DA (2008) Hock cleavage of cholesterol 5α-hydroperoxides: an ozone-free pathway to the cholesterol ozonolysis products identified in arterial plaque and brain tissue. J Am Chem Soc 130:12224-12225
6. Brown AJ, Jessup W (1999) Oxysterol and atherosclerosis. Atherosclerosis 142:1-28
7. Freimer AA (1979) The reaction of singlet oxygen with olefins: the question of mechanism. Chem Rev 79:359-387
8. Girroti AW, Korytowski W (2000) Cholesterol as a singlet oxygen detector in biological system. Methods Enzymol 319:85-100
9. Korytowski W, Schmitt JC, Girotti AW (2010) Surprising inability of singlet oxygen-generated 6-hydroperoxycholesterol to induce damaging free radical lipid peroxidation in cell membranes. Photochem Photobiol 86:747-751
10. Korytowski W, Bachowski G, Girotti A (1992) Photoperoxidation of cholesterol in homogenious solution, isolated membranes and cells: comparison of the 5α-and 6-β-hydroperoxides as indicators of singlet oxygen intermediacy. Photochem Photobiol 56:1-8
11. Korytowski W, Geiger PG, Girotti AW (1996) Enzymatic reducibility to cytotoxicity for various cholesterol hydroperoxides. Biochemistry 35:8770-8779
12. Kriska T, Pilat A, Schmitt JC, Girotti AW (2010) Sterolcarrierprotein-2(SCP-2) involvement in cholesterol hydroperoxide cytotoxicity as revealed by SCP-2 inhibitor effects. J Lipid Res 51:3174-3184
13. Larsson DA, Baird S, Nyhalah JD, Yuan X-M, Li W (2006) Oxysterol mixtures, in atheromarelevant proportions, display synergistic and proapoptiotic effects. Free Radic Biol Med 41:902-910
14. Leonarduzzi G, Gamba P, Sottero B, Kadl A, Robbesyn F, Calogero RA, Biasi F, Chiarpotto E, Leitinger N, Sevanian A, Poli G (2005) Oxysterol-induced up-regulation of MCP-1 expression and synthesis in macrophage cells. Free Radic Biol Med 39:1152-1161
15. Lordan S, Mackrill JJ, O’Brien NM (2009) Oxysterol and mechanism of apoptotic signaling: implications in the pathology of degenerative diseases. J Nutr Biochem 20:321-336
16. Massey JB (2006) Membrane and protein interactions of oxysterols. Curr Opin Lipidol 17:296-301
17. Minami Y, Yokoi S, Setoyama M, Bando N, Takeda S, Kawai Y, Terao J (2007) Combination of TLC blotting and gas chromatography-mass spectrometry for analysis of peroxidized cholesterol. Lipids 42:1055-1063
18. Minami Y, Kawabata K, Kubo Y, Arase S, Hirasaka K, Nikawa T, Bando N, Kawai Y, Terao J (2009) Peroxidized cholesterol-induced matrix metalloproteinase-9 activation and its suppression by dietary β-carotene in photoaging of hairless mouse skin. J Nutr Biochem 20:389-398
19. Miyamoto S, Arai H, Terao J (2010) Enzymatic antioxidant defenses. In: Aldini G, Yeum K-J, Niki E, Russell RM (eds) Biomarkers for antioxidant defenses and oxidative damage. Principles and practical applications. Wiley-Blackwell Publishing, Hoboken NJ, USA, pp 21-33
20. Niki E (2005) Lipid peroxidation: mechanisms, inhibition, and biological effects. Biochem Biophys Res Comm 338:668-676
21. Niki E (2009) Lipid peroxidation: physiological levels and dual biological effects. Free Radic Biol Med 47:469-484
22. Olkkonen VM, Hynynen R (2009) Interactions of oxysterols with membranes and proteins. Mol Asp Med 30:123-133
23. Olsher M, Yoon S-I, Chong L-G (2005) Role of sterol superlattice in free radical-induced sterol oxidation in lipid membranes. Biochemistry 44:2080-2087
24. Otaegui-Arrazola A, Carrno-Nenendez M, Ansorena D, Astiasaran I (2010) Oxysterols: a world to explore. Food Chem Toxicol 48:3289-3303
25. Saito Y, Yoshida Y, Niki E (2007) Cholesterol is more susceptible to oxidation than linoleate in cultured cells under oxidative stress induced by selenium deficiency and free radicals. FEBS Lett 581:4349-4354
26. Steffen Y, Wiswedel I, Petyer D, Schewe T, Sies H (2006) Cytotoxicity of myeloperoxidase/nitrite-oxidized low-density lipoprotein toward endothelial cells is due to a high 7β-hydroxy cholesterol to 7-ketocholesterol ratio. Free Radic Biol Med 41:1139-1150
27. Takeuchi C, Galve R, Nieva J, Witter DP, Wentworth AD, Yroseth RP, Lerner RA, Wentworth P (2006) Proatherogenic effects of the cholesterol ozonolysis products, atheronal-A and atheronal-B. Biochemistry 45:7162-7170
28. Uemi M, Ronsein GE, Fernanda M, Prado M, Motta FD, Miyamoto S, Medeiros MG, DiMascio PD (2011) Cholesterol hydroperoxides generates singlet molecular oxygen [O2 1Δg]: near-IR emission. 18O-labelled hydroperoxides, and mass spectrometry. Chem Res Toxicol 24:887-895
29. van Reyk D, Brown A, Hult’en LM, Dean R, Jessup W (2006) Oxysterol in biological systems: sources, metabolism and pathophysiological releavance. Redox Rep 11:255-262
30. Vejux A, Guyot S, Montange T, Riedinger J-M, Kahn E, Lizard G (2009) Phospholipidosis and down-regulation of the PI3-K/PDK-1/Akt signaling pathway are vitamin E inhibitable events associated with 7-ketocholesterol-induced apoptosis. J Nutr Biochem 20:45-61
31. Vever-Bizet C, Dellinger M, Braut D, Rougee M, Bensasson RV (1989) Singlet molecular oxygen quenching by saturated and unsaturated fatty-acids and by cholesterol. Photochem Photobiol 50:321-325
32. Vila A, Korytowski W, Girotti AW (2001) Spontaneous intermembrane transfer of various cholesterol-derived hydroperoxide species; kinetic studies with model membranes and cell. Biochemistry 40:14715-14726
33. Yamazaki S, Ozawa N, Hiratsuka A, Watabe T (1999) Increase in cholesterol 7-hydroperoxides in lipids of human skin by sunlight exposure. Free Radic Biol Med 26:1126-1133
34. Yaqoob P (2009) The nutritional significance of lipid rafts. Ann Rev Nutr 29:257-282
35. Yoshida Y, Saito Y, Hayakawa M, Habuchi Y, Imai Y, Sawai Y, Niki E (2007) Level of lipid peroxidation in human plasma and erythrocytes: comparison between fatty acid and cholesterol. Lipids 42:439-449