Impact of circulating esterified eicosanoids and other oxylipins on endothelial function

Current Atherosclerosis Reports

Volumn 11, Issue 6, 2009, Pages 403-410

  Shearer, Gregory C ^a   Newman, John W ^b  

^a UNIVERSITY OF SOUTH DAKOTA   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; ESTER DERIVATIVE; HIGH DENSITY LIPOPROTEIN; ICOSAPENTAENOIC ACID; KETONE DERIVATIVE; LIPOPROTEIN; LIPOPROTEIN LIPASE; LOW DENSITY LIPOPROTEIN; OXYGEN; OXYLIPIN; PHOSPHOLIPID; POLYUNSATURATED FATTY ACID; TRIACYLGLYCEROL LIPASE;

ATHEROGENESIS; ATHEROSCLEROSIS; ATHEROSCLEROTIC PLAQUE; CARDIOVASCULAR RISK; CYTOTOXICITY; DISEASE COURSE; ENDOTHELIAL DYSFUNCTION; ENDOTHELIUM CELL; ENZYME ACTIVITY; ENZYME MECHANISM; ESTERIFICATION; HEART PROTECTION; HUMAN; HYPERLIPIDEMIA; HYPERTENSION; INFLAMMATION; LIPID METABOLISM; LIPID PEROXIDATION; LIPID TRANSPORT; LIPOLYSIS; NONHUMAN; OXIDATIVE STRESS; PATHOPHYSIOLOGY; PROTEIN EXPRESSION; PROTEIN LIPID INTERACTION; REVIEW; VASCULAR DISEASE; VASCULAR ENDOTHELIUM; VASODILATATION;

ATHEROSCLEROSIS; EICOSANOIDS; ENDOTHELIUM, VASCULAR; HUMANS; INFLAMMATION; OXYLIPINS;

EID: 70449483370     PISSN: 15233804     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11883-009-0061-3     Document Type: Review

References (52)

1. S.J. Nicholls S.L. Hazen 2009 Myeloperoxidase, modified lipoproteins, and atherogenesis J Lipid Res 50 Suppl S346 S351 10.1194/jlr.R800086-JLR200 19091698
2. M.W. Buczynski D.S. Dumlao E.A. Dennis 2009 Thematic Review Series: Proteomics. An integrated omics analysis of eicosanoid biology J Lipid Res 50 1015 1038 10.1194/jlr.R900004-JLR200 1:CAS:528:DC%2BD1MXms1ehtrg%3D 19244215
3. V.B. O'Donnell B. Maskrey G.W. Taylor 2009 Eicosanoids: generation and detection in mammalian cells Methods Mol Biol 462 5 23 19160658
4. R. Zhang M.L. Brennan Z. Shen, et al. 2002 Myeloperoxidase functions as a major enzymatic catalyst for initiation of lipid peroxidation at sites of inflammation J Biol Chem 277 46116 46122 10.1074/jbc.M209124200 1:CAS:528:DC%2BD38XovFKiur8%3D 12359714 (Pubitemid 35417600)
5. A.A. Spector 2009 Arachidonic acid cytochrome P450 epoxygenase pathway J Lipid Res 50 Suppl S52 S56 10.1194/jlr.R800038-JLR200 18952572
6. J.W. Newman G.A. Kaysen B.D. Hammock G.C. Shearer 2007 Proteinuria increases oxylipid concentrations in VLDL and HDL but not LDL particles in the rat J Lipid Res 48 1792 1800 10.1194/jlr.M700146-JLR200 1:CAS:528: DC%2BD2sXot1OgtLw%3D 17496268 (Pubitemid 47311996)
7. J.M. Proudfoot A.E. Barden W.M. Loke, et al. 2009 HDL is the major lipoprotein carrier of plasma F2-isoprostanes J Lipid Res 50 716 722 10.1194/jlr.M800607-JLR200 1:CAS:528:DC%2BD1MXks1Witr8%3D 19050315
8. A.A. Spector A.W. Norris 2007 Action of epoxyeicosatrienoic acids on cellular function Am J Physiol 292 C996 C1012 10.1152/ajpcell.00402.2006 1:CAS:528:DC%2BD2sXjsFeqs74%3D (Pubitemid 46442641)
9. C.R. Lee K.E. North M.S. Bray, et al. 2006 Genetic variation in soluble epoxide hydrolase (EPHX2) and risk of coronary heart disease: The Atherosclerosis Risk in Communities (ARIC) study Hum Mol Genet 15 1640 1649 10.1093/hmg/ddl085 1:CAS:528:DC%2BD28XktlSitr8%3D 16595607 (Pubitemid 43904830)
10. Q. Wei P.A. Doris M.V. Pollizotto, et al. 2007 Sequence variation in the soluble epoxide hydrolase gene and subclinical coronary atherosclerosis: interaction with cigarette smoking Atherosclerosis 190 26 34 10.1016/j.atherosclerosis.2006.02.021 1:CAS:528:DC%2BD28XhtlartLfF 16545818 (Pubitemid 44920229)
11. C.R. Lee K.E. North M.S. Bray, et al. 2007 CYP2J2 and CYP2C8 polymorphisms and coronary heart disease risk: the Atherosclerosis Risk in Communities (ARIC) study Pharmacogenet Genomics 17 349 358 10.1097/FPC. 0b013e32809913ea 1:CAS:528:DC%2BD2sXktFagt78%3D 17429317 (Pubitemid 46608542)
12. P.Y. Liu Y.H. Li T.H. Chao, et al. 2007 Synergistic effect of cytochrome P450 epoxygenase CYP2J2*7 polymorphism with smoking on the onset of premature myocardial infarction Atherosclerosis 195 199 206 10.1016/j. atherosclerosis.2006.11.001 1:CAS:528:DC%2BD2sXhtF2hurzJ 17126841 (Pubitemid 47561938)
13. B. Ercan L. Ayaz D. Cicek L. Tamer 2008 Role of CYP2C9 and CYP2C19 polymorphisms in patients with atherosclerosis Cell Biochem Function 26 309 313 10.1002/cbf.1437 1:CAS:528:DC%2BD1cXlsF2ht74%3D (Pubitemid 351613170)
14. Y. Zhang C.L. Oltman T. Lu, et al. 2001 EET homologs potently dilate coronary microvessels and activate BK(Ca) channels Am J Physiol Heart Circ Physiol 280 H2430 H2440 1:CAS:528:DC%2BD3MXksFCmu7o%3D 11356595
15. D. Ye D. Zhang C. Oltman, et al. 2002 Cytochrome p-450 epoxygenase metabolites of docosahexaenoate potently dilate coronary arterioles by activating large-conductance calcium-activated potassium channels J Pharmacol Exp Ther 303 768 776 10.1124/jpet.303.2.768 1:CAS:528:DC%2BD38XotlCns7c%3D 12388664 (Pubitemid 35231254)
16. A. Ulu B.B. Davis H.J. Tsai, et al. 2008 Soluble epoxide hydrolase inhibitors reduce the development of atherosclerosis in apolipoprotein e-knockout mouse model J Cardiovasc Pharmacol 52 314 323 10.1097/FJC. 0b013e318185fa3c 1:CAS:528:DC%2BD1cXht1Knsr3F 18791465
17. X. Fang S. Hu B. Xu, et al. 2006 14,15-Dihydroxyeicosatrienoic acid activates peroxisome proliferator-activated receptor-alpha Am J Physiol Heart Circ Physiol 290 H55 H63 10.1152/ajpheart.00427.2005 1:CAS:528: DC%2BD28XhsVKjtLs%3D 16113065
18. S. Suzuki A. Oguro M. Osada-Oka, et al. 2008 Epoxyeicosatrienoic acids and/or their metabolites promote hypoxic response of cells J Pharmacol Sci 108 79 88 10.1254/jphs.08122FP 1:CAS:528:DC%2BD1cXht1amtr%2FL 18776712
19. R. Slim B.D. Hammock M. Toborek, et al. 2001 The role of methyl-linoleic acid epoxide and diol metabolites in the amplified toxicity of linoleic acid and polychlorinated biphenyls to vascular endothelial cells Toxicol Appl Pharmacol 171 184 193 10.1006/taap.2001.9131 1:CAS:528:DC%2BD3MXhslSmt7o%3D 11243918 (Pubitemid 32217669)
20. U. Yasar A.M. Bennet E. Eliasson, et al. 2003 Allelic variants of cytochromes P450 2C modify the risk for acute myocardial infarction Pharmacogenetics 13 715 720 10.1097/00008571-200312000-00002 1:CAS:528:DC%2BD3sXptlelsb8%3D 14646690 (Pubitemid 38429249)
21. M.H. Shishehbor R. Zhang H. Medina, et al. 2006 Systemic elevations of free radical oxidation products of arachidonic acid are associated with angiographic evidence of coronary artery disease Free Radical Biol Med 41 1678 1683 10.1016/j.freeradbiomed.2006.09.001 1:CAS:528:DC%2BD28XhtFersr7M (Pubitemid 44634239)
22. C. Whatling W. McPheat M. Herslof 2007 The potential link between atherosclerosis and the 5-lipoxygenase pathway: investigational agents with new implications for the cardiovascular field Expert Opin Invest Drugs 16 1879 1893 10.1517/13543784.16.12.1879 1:CAS:528:DC%2BD2sXhtlGmu77K
23. P. Patel C. Cossette J.R. Anumolu, et al. 2008 Structural requirements for activation of the 5-oxo-6E,8Z, 11Z,14Z-eicosatetraenoic acid (5-oxo-ETE) receptor: identification of a mead acid metabolite with potent agonist activity J Pharmacol Exper Ther 325 698 707 10.1124/jpet.107.134908 1:CAS:528: DC%2BD1cXlsVOjtL0%3D (Pubitemid 351574804)
24. J. Wittwer M. Hersberger 2007 The two faces of the 15-lipoxygenase in atherosclerosis Prostaglandins Leukotrienes Essential Fatty Acids 77 67 77 10.1016/j.plefa.2007.08.001 1:CAS:528:DC%2BD2sXhtFGrtrvI (Pubitemid 47539103)
25. R. Natarajan J.L. Nadler 2004 Lipid inflammatory mediators in diabetic vascular disease Arterioscler Thromb Vasc Biol 24 1542 1548 10.1161/01.ATV. 0000133606.69732.4c 1:CAS:528:DC%2BD2cXntVCrtb0%3D 15166011 (Pubitemid 39180875)
26. J. Barlic P.M. Murphy 2007 An oxidized lipid-peroxisome proliferator-activated receptor gamma-chemokine pathway in the regulation of macrophage-vascular smooth muscle cell adhesion Trends Cardiovasc Med 17 269 274 10.1016/j.tcm.2007.09.004 1:CAS:528:DC%2BD2sXhtlajtrvE 18021937 (Pubitemid 350087697)
27. W.F. Stenson C.W. Parker 1979 12-L-hydroxy-5,8,10,14-eicosatetraenoic acid, a chemotactic fatty acid, is incorporated into neutrophil phospholipids and triglyceride Prostaglandins 18 285 292 10.1016/0090-6980(79)90115-1 1:CAS:528:DyaE1MXlslagsb0%3D 118490 (Pubitemid 10226035)
28. X. Fang N.L. Weintraub L.L. Stoll A.A. Spector 1999 Epoxyeicosatrienoic acids increase intracellular calcium concentration in vascular smooth muscle cells Hypertension 34 1242 1246 1:CAS:528:DC%2BD3cXivFCksQ%3D%3D 10601125
29. J.M. Seubert D.C. Zeldin K. Nithipatikom G.J. Gross 2007 Role of epoxyeicosatrienoic acids in protecting the myocardium following ischemia/reperfusion injury Prostaglandins Other Lipid Mediators 82 50 59 10.1016/j.prostaglandins.2006.05.017 1:CAS:528:DC%2BD28Xht12ktLzE 17164132 (Pubitemid 44880163)
30. A.A. Spector X. Fang G.D. Snyder N.L. Weintraub 2004 Epoxyeicosatrienoic acids (EETs): metabolism and biochemical function Progress Lipid Res 43 55 90 10.1016/S0163-7827(03)00049-3 1:CAS:528:DC%2BD3sXptVemtL4%3D (Pubitemid 37433867)
31. N.L. Weintraub X. Fang T.L. Kaduce, et al. 1997 Potentiation of endothelium-dependent relaxation by epoxyeicosatrienoic acids Circ Res 81 258 267 1:CAS:528:DyaK2sXkvFyksb4%3D 9242187
32. Y. Zhu E.B. Schieber J.C. McGiff M. Balazy 1995 Identification of arachidonate P-450 metabolites in human platelet phospholipids Hypertension 25 854 859 1:CAS:528:DyaK2MXlvVemt70%3D 7721444
33. H. Jiang A.G. Zhu M. Mamczur, et al. 2008 Hydrolysis of cis- and trans-epoxyeicosatrienoic acids by rat red blood cells J Pharmacol Exper Ther 326 330 337 10.1124/jpet.107.134858 1:CAS:528:DC%2BD1cXotlylt7s%3D (Pubitemid 351872119)
34. A. Karara S. Wei D. Spady, et al. 1992 Arachidonic acid epoxygenase: structural characterization and quantification of epoxyeicosatrienoates in plasma Biochem Biophys Res Commun 182 1320 1325 10.1016/0006-291X(92)91877-S 1:CAS:528:DyaK38XitFWksLg%3D 1540175
35. G.C. Shearer J.W. Newman 2008 Lipoprotein lipase releases esterified oxylipins from very low-density lipoproteins Prostaglandins Leukotrienes Essential Fatty Acids 79 215 222 10.1016/j.plefa.2008.09.023 1:CAS:528:DC%2BD1cXhsVKrtLfJ
36. L. Eiselein D.W. Wilson M.W. Lame J.C. Rutledge 2007 Lipolysis products from triglyceride-rich lipoproteins increase endothelial permeability, perturb zonula occludens-1 and F-actin, and induce apoptosis Am J Physiol Heart Circ Physiol 292 H2745 H2753 10.1152/ajpheart.00686.2006 1:CAS:528: DC%2BD2sXmvF2lurs%3D 17259442 (Pubitemid 47084523)
37. L. Wang A.R. Sapuri-Butti H.H. Aung, et al. 2008 Triglyceride-rich lipoprotein lipolysis increases aggregation of endothelial cell membrane microdomains and produces reactive oxygen species Am J Physiol Heart Circ Physiol 295 H237 H244 10.1152/ajpheart.01366.2007 1:CAS:528:DC%2BD1cXoslygu7w%3D 18487440
38. L. Wang R. Gill T.L. Pedersen, et al. 2009 Triglyceride-rich lipoprotein lipolysis releases neutral and oxidized FFAs that induce endothelial cell inflammation J Lipid Res 50 204 213 10.1194/jlr.M700505-JLR200 1:CAS:528:DC%2BD1MXhsVCmsb4%3D 18812596
39. M. Takahashi Y. Hiyama M. Yokoyama, et al. 2008 In vivo arterial lipoprotein lipase expression augments inflammatory responses and impairs vascular dilatation Arterioscler Thromb Vasc Biol 28 455 462 10.1161/ATVBAHA.107.153239 1:CAS:528:DC%2BD1cXit1Olsbs%3D 18258818
40. J.D. Coleman K.S. Prabhu J.T. Thompson, et al. 2007 The oxidative stress mediator 4-hydroxynonenal is an intracellular agonist of the nuclear receptor peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta) Free Radical Biol Med 42 1155 1164 10.1016/j.freeradbiomed.2007.01.003 1:CAS:528:DC%2BD2sXjsVGhtLc%3D (Pubitemid 46428510)
41. K.O. Badellino M.L. Wolfe M.P. Reilly D.J. Rader 2008 Endothelial lipase is increased in vivo by inflammation in humans Circulation 117 678 685 10.1161/CIRCULATIONAHA.107.707349 1:CAS:528:DC%2BD1cXhtVKisrk%3D 18212282
42. M.G. McCoy G.S. Sun D. Marchadier, et al. 2002 Characterization of the lipolytic activity of endothelial lipase J Lipid Res 43 921 929 1:CAS:528:DC%2BD38XksFWgsro%3D 12032167
43. W. Ahmed G. Orasanu V. Nehra, et al. 2006 High-density lipoprotein hydrolysis by endothelial lipase activates PPARalpha: a candidate mechanism for high-density lipoprotein-mediated repression of leukocyte adhesion Circ Res 98 490 498 10.1161/01.RES.0000205846.46812.be 1:CAS:528:DC%2BD28Xhs1Gqsb4%3D 16439686 (Pubitemid 43755307)
44. A. Alipour J.W. Elte H.C. van Zaanen, et al. 2008 Novel aspects of postprandial lipemia in relation to atherosclerosis Atheroscler Suppl 9 39 44 10.1016/j.atherosclerosissup.2008.05.007 1:CAS:528:DC%2BD1cXhtVygu7fO 18595782
45. E. Esteve W. Ricart J.M. Fernandez-Real 2005 Dyslipidemia and inflammation: an evolutionary conserved mechanism Clin Nutr (Edinburgh, Scotland) 24 16 31 1:CAS:528:DC%2BD2MXos1Kjtw%3D%3D
46. E.M. de Goma R.L. deGoma D.J. Rader 2008 Beyond high-density lipoprotein cholesterol levels evaluating high-density lipoprotein function as influenced by novel therapeutic approaches J Am Coll Cardiol 51 2199 2211 10.1016/j.jacc.2008.03.016 (Pubitemid 351754991)
47. B.J. Ansell M. Navab S. Hama, et al. 2003 Inflammatory/antiinflammatory properties of high-density lipoprotein distinguish patients from control subjects better than high-density lipoprotein cholesterol levels and are favorably affected by simvastatin treatment Circulation 108 2751 2756 10.1161/01.CIR.0000103624.14436.4B 1:CAS:528:DC%2BD3sXptV2jurw%3D 14638544 (Pubitemid 37498976)
48. R.J. Bisoendial G.K. Hovingh J.H. Levels, et al. 2003 Restoration of endothelial function by increasing high-density lipoprotein in subjects with isolated low high-density lipoprotein Circulation 107 2944 2948 10.1161/01.CIR.0000070934.69310.1A 12771001 (Pubitemid 36736637)
49. T. Mizutani M. Masuda E. Nakai, et al. 2008 Genuine functions of P-glycoprotein (ABCB1) Curr Drug Metab 9 167 174 10.2174/138920008783571756 1:CAS:528:DC%2BD1cXjsFyiur4%3D 18288958
50. G.C. Shearer J.V. Pottala J.A. Spertus W.S. Harris 2009 Red blood cell fatty acid patterns and acute coronary syndrome PLoS ONE 4 e5444 10.1371/journal.pone.0005444 19421317
51. S.D. Harmon X. Fang T.L. Kaduce, et al. 2006 Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production Prostaglandins Leukotrienes Essential Fatty Acids 75 169 177 10.1016/j.plefa.2006.05.005 1:CAS:528:DC%2BD28XptFChtrs%3D (Pubitemid 44292521)
52. K.V. Lemley 2007 An introduction to biomarkers: applications to chronic kidney disease Pediatr Nephrol (Berlin) 22 1849 1859 10.1007/s00467-007-0455-9 (Pubitemid 47506224)