Inhibition of endothelial- and neuronal-type, but not inducible-type, nitric oxide synthase by the oxidized cholesterol metabolite secosterol aldehyde: Implications for vascular and neurodegenerative diseases

Journal of Clinical Biochemistry and Nutrition

Volumn 50, Issue 1, 2012, Pages 84-89

  Lai, Ying Ling ^a,b   Tomono, Susumu ^a   Miyoshi, Noriyuki ^a   Ohshima, Hiroshi ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

Author keywords

Endothelial type NOS; Inducible type NOS; Neuronal type NOS; Oxidized cholesterol metabolites; Secosterol A

Indexed keywords

25 HYDROXYCHOLESTEROL; 7 OXOCHOLESTEROL; CALMODULIN; CHOLESTEROL 5BETA,6BETA OXIDE; CHOLESTEROL DERIVATIVE; ENDOTHELIAL NITRIC OXIDE SYNTHASE; INDUCIBLE NITRIC OXIDE SYNTHASE; LYSINE; NEURONAL NITRIC OXIDE SYNTHASE; SCHIFF BASE; SECOSTEROL A; SECOSTEROL ALDEHYDE; SECOSTEROL B; UNCLASSIFIED DRUG;

ARTICLE; ATHEROSCLEROSIS; CONTROLLED STUDY; DEGENERATIVE DISEASE; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; LONG TERM POTENTIATION; MEMORY DISORDER; METABOLITE; NONHUMAN; OZONOLYSIS; PATHOGENESIS; PROTEIN MODIFICATION; SIGNAL TRANSDUCTION; VASCULAR DISEASE;

EID: 84855369763     PISSN: 09120009     EISSN: None     Source Type: Journal    
DOI: 10.3164/jcbn.11-31     Document Type: Article

References (33)

1. Wentworth P Jr., Nieva J, Takeuchi C, et al. Evidence for ozone formation in human atherosclerotic arteries. Science 2003; 302: 1053-1056. (Pubitemid 37386200)
2. Zhang Q, Powers ET, Nieva J, et al. Metabolite-initiated protein misfolding may trigger Alzheimer's disease. Proc Natl Acad Sci USA 2004; 101: 4752-4757.
3. Bosco DA, Fowler DM, Zhang Q, et al. Elevated levels of oxidized cholesterol metabolites in Lewy body disease brains accelerate alpha-synuclein fibrilization. Nat Chem Biol 2006; 2: 249-253.
4. Gumulka J, Smith LL. Ozonization of cholesterol. J Am Chem Soc 1983; 105: 1972-1979.
5. Jaworski K, Smith LL. Ozonization of cholesterol in nonparticipating solvents. J Org Chem 1988; 53: 545-554.
6. Paryzek Z, Martynow J, Swoboda W. The reaction of cholesterol with ozone and alcohols: a revised mechanism and structure of the principal product. J Chem Soc, Perkin Trans 1990; 1: 1222-1223.
7. Babior BM, Takeuchi C, Ruedi J, Gutierrez A, Wentworth P Jr. Investigating antibody-catalyzed ozone generation by human neutrophils. Proc Natl Acad Sci USA 2003; 100: 3031-3034. (Pubitemid 36358199)
8. Nieva J, Wentworth P Jr. The antibody-catalyzed water oxidation pathway-a new chemical arm to immune defense? Trends Biochem Sci 2004; 29: 274-278. (Pubitemid 38591322)
9. Brinkhorst J, Nara SJ, Pratt DA. Hock cleavage of cholesterol 5alphahydroperoxide: an ozone-free pathway to the cholesterol ozonolysis products identified in arterial plaque and brain tissue. J Am Chem Soc 2008; 130: 12224-12225.
10. g)] as well as ozone with cholesterol. Chem Res Toxicol 2009; 22: 875-884.
11. Wentworth AD, Song BD, Nieva J, Shafton A, Tripurenani S, Wentworth PJ. The ratio of cholesterol 5,6-secosterols formed from ozone and singlet oxygen offers insight into the oxidation of cholesterol in vivo. Chem Commun (Camb). 2009; 7: 3098-3100.
12. 2-chloride system. Biochem Biophys Res Commun 2009; 383: 222-227.
13. Tomono S, Miyoshi N, Shiokawa H, et al. Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway. J Lipid Res 2011; 52: 87-97.
14. Sathishkumar K, Haque M, Perumal TE, Francis J, Uppu RM. A major ozonation product of cholesterol, 3β-hydroxy-5-oxo-5,6-secocholestan-6-al, induces apoptosis in H9c2 cardiomyoblasts. FEBS Lett 2005; 579: 6444-6450. (Pubitemid 41612166)
15. Sathishkumar K, Murthy SN, Uppu RM. Cytotoxic effects of oxysterols produced during ozonolysis of cholesterol in murine GT1-7 hypothalamic neurons. Free Radic Res 2007; 41: 82-88. (Pubitemid 44896877)
16. Sathishkumar K, Gao X, Raghavamenon AC, Parinandi N, Pryor WA, Uppu RM. Cholesterol secoaldehyde induces apoptosis in H9c2 cardiomyoblasts through reactive oxygen species involving mitochondrial and death receptor pathways. Free Radic Biol Med 2009; 47: 548-558.
17. Stewart CR, Wilson LM, Zhang Q, et al. Oxidized cholesterol metabolites found in human atherosclerotic lesions promote apolipoprotein C-II amyloid fibril formation. Biochemistry 2007; 46: 5552-5561. (Pubitemid 46717277)
18. Usui K, Hulleman JD, Paulsson JF, Siegel SJ, Powers ET, Kelly JW. Sitespecific modification of Alzheimer's peptides by cholesterol oxidation products enhances aggregation energetics and neurotoxicity. Proc Natl Acad Sci USA 2009; 106: 18563-18568.
19. Förstermann U, Closs EI, Pollock JS, et al. Nitric oxide synthase isozymes. Characterization, purification, molecular cloning, and functions. Hypertension 1994; 23: 1121-1131. (Pubitemid 24180877)
20. Alderton WK, Cooper CE, Knowles RG. Nitric oxide synthases: structure, function and inhibition. Biochem J 2001; 357: 593-615. (Pubitemid 32735142)
21. Russell DW. The enzymes, regulation, and genetics of bile acid synthesis. Annu Rev Biochem 2003; 72: 137-174. (Pubitemid 36930444)
22. Schroepfer GJ Jr. Oxysterols: modulators of cholesterol metabolism and other processes. Physiol Rev 2000; 80: 361-554.
23. Sevanian A, McLeod LL. Cholesterol autoxidation in phospholipid membrane bilayers. Lipids 1987; 22: 627-636.
24. Sevanian A, Berliner J, Peterson H. Uptake, metabolism, and cytotoxicity of isomeric cholesterol-5,6-epoxides in rabbit aortic endothelial cells. J Lipid Res 1991; 32: 147-155.
25. O'Callaghan YC, Woods JA, O'Brien NM. Comparative study of the cyto-toxicity and apoptosis-inducing potential of commonly occurring oxysterols. Cell Biol Toxicol 2001; 17: 127-137. (Pubitemid 32681048)
26. Smith LL. Review of progress in sterol oxidations: 1987-1995. Lipids 1996; 31: 453-487. (Pubitemid 26161248)
27. Rodriguez IR, Larrayoz IM. Cholesterol oxidation in the retina: implications of 7KCh formation in chronic inflammation and age-related macular degeneration. J Lipid Res 2010; 51: 2847-2862.
28. Lai YL, Aoyama S, Nagai R, Miyoshi N, Ohshima H. Inhibition of L-arginine metabolizing enzymes by L-arginine-derived advanced glycation end products. J Clin Biochem Nutr 2010; 46: 177-185.
29. Mineo C, Deguchi H, Griffin JH, Shaul PW. Endothelial and antithrombotic actions of HDL. Circ Res 2006; 98: 1352-1364. (Pubitemid 43948059)
30. Shaul PW, Smart EJ, Robinson LJ, et al. Acylation targets endothelial nitric-oxide synthase to plasmalemmal caveolae. J Biol Chem 1996; 271: 6518-6522. (Pubitemid 26095467)
31. García-Cardeña G, Oh P, Liu J, Schnitzer JE, Sessa WC. Targeting of nitric oxide synthase to endothelial cell caveolae via palmitoylation: implications for nitric oxide signaling. Proc Natl Acad Sci USA 1996; 93: 6448-6453. (Pubitemid 26230326)
32. Simons K, Ehehalt R. Cholesterol, lipid rafts, and disease. J Clin Invest 2002; 110: 597-603. (Pubitemid 34988781)
33. Liu JP, Tang Y, Zhou S, Toh BH, McLean C, Li H. Cholesterol involvement in the pathogenesis of neurodegenerative diseases. Mol Cell Neurosci 2010; 43: 33-42.