The DOI matches its Crossref record; 6 of the 6 references it cites were found in a registry or an index.
Cytochrome P450–dependent metabolism of ω-6 and ω-3 long-chain polyunsaturated fatty acids
Abstract
Dietary fish oil omega-3 fatty acids (n-3 PUFAs), such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), protect against arrhythmia and sudden cardiac death using largely unknown mechanisms. EPA and DHA may serve as efficient alternative substrates of arachidonic acid (AA) metabolizing cytochrome P450 (CYP) enzymes. For many of the CYP isoforms, the n-3 PUFAs are the preferred substrates. Moreover, the CYP enzymes oxygenate EPA and DHA with largely different regioselectivities compared to AA. In particular, the omega-3 double bond that distinguishes EPA and DHA from AA is a preferred site of CYP-catalyzed epoxidation reactions. Given the pivotal role of CYP-dependent AA metabolites in the regulation of vascular, renal and cardiac functions, their replacement by unique sets of epoxy- and hydroxy-metabolites derived from EPA and DHA may have far-reaching physiological implications. The currently available data suggest that some of the vasculo- and cardioprotective effects attributed to dietary n-3 PUFAs may be mediated by CYP-dependent metabolites of EPA and DHA.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
In the citing paper
“Both EPA and DHA are also precursors to bioactive lipid metabolites, including specialized proresolving mediators36 and cytochrome P450–generated monoepoxides,37 that could contribute to lower CHD risk.”
From ω-3 Polyunsaturated Fatty Acid Biomarkers and Coronary Heart Disease: Pooling Project of 19 Cohort Studies (2016) · cites this paper as [37]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Resolving inflammation: dual anti-inflammatory and pro-resolution lipid mediators
Serhan, C. N., Chiang, N., & Van Dyke, T. E. (2008) · Nature Reviews Immunology · doi:10.1038/nri2294 · Cited by 2,932
The Inverse Relation between Fish Consumption and 20-Year Mortality from Coronary Heart Disease
Kromhout, D., Bosschieter, E. B., & Coulander, C. D. L. (1985) · New England Journal of Medicine · doi:10.1056/nejm198505093121901 · Cited by 2,177
Marchioli, R., Barzi, F., Bomba, E., Chieffo, C., Di Gregorio, D., Di Mascio, R., Franzosi, M. G., Geraci, E., Levantesi, G., Maggioni, A. P., et al. (2002) · Circulation · doi:10.1161/01.cir.0000014682.14181.f2 · Cited by 1,311
Thies, F., Garry, J. M., Yaqoob, P., Rerkasem, K., Williams, J., Shearman, C. P., Gallagher, P. J., Calder, P. C., & Grimble, R. F. (2003) · The Lancet · doi:10.1016/s0140-6736(03)12468-3 · Cited by 739 · cited 1×
“Importantly, n-3 PUFAs also protect against atrial fibrillation in cardiac surgical settings [9] and promote plaque stabilization [90].”
BackgroundLeaf, A., Kang, J. X., Xiao, Y.-F., & Billman, G. E. (2003) · Circulation · doi:10.1161/01.cir.0000069566.78305.33 · Cited by 605
Wada, M., DeLong, C. J., Hong, Y. H., Rieke, C. J., Song, I., Sidhu, R. S., Yuan, C., Warnock, M., Schmaier, A. H., Yokoyama, C., et al. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m703169200 · Cited by 400
Research works printed but not linked: 101
- 1999, results of the GISSI-Prevenzione trial. Gruppo Italiano per lo Studio della Sopravvivenza nell ‘Infarto miocardico, Lancet, 354, 447, 10.1016/S0140-6736(99)07072-5 · DOI · Paper page
- Abdukeyum, 2008, Dietary (n-3) long-chain polyunsaturated fatty acids inhibit ischemia and reperfusion arrhythmias and infarction in rat heart not enhanced by ischemic preconditioning, J Nutr, 138, 1902, 10.1093/jn/138.10.1902 · DOI
- Ai, 2007, Angiotensin II up-regulates soluble epoxide hydrolase in vascular endothelium in vitro and in vivo, Proc Natl Acad Sci USA, 104, 9018, 10.1073/pnas.0703229104 · DOI
- Ai, 2009, Soluble epoxide hydrolase plays an essential role in angiotensin II-induced cardiac hypertrophy, Proc Natl Acad Sci USA, 106, 564, 10.1073/pnas.0811022106 · DOI
- Bang, 1976, The composition of food consumed by Greenland Eskimos, Acta Med Scand, 200, 69, 10.1111/j.0954-6820.1976.tb08198.x · DOI
- Barbosa-Sicard, 2005, Eicosapentaenoic acid metabolism by cytochrome P450 enzymes of the CYP2C subfamily, Biochem Biophys Res Commun, 329, 1275, 10.1016/j.bbrc.2005.02.103 · DOI
- Blanton, 2006, Nitric oxide/cytochrome P450 interactions in cyclosporin A-induced effects in the rat, J Hypertens, 24, 1865, 10.1097/01.hjh.0000242412.88653.f2 · DOI
- Calder, 2006, Polyunsaturated fatty acids and inflammation, Prostaglandins Leukot Essent Fatty Acids, 75, 197, 10.1016/j.plefa.2006.05.012 · DOI
- Calo, 2005, N-3 Fatty acids for the prevention of atrial fibrillation after coronary artery bypass surgery: a randomized, controlled trial, J Am Coll Cardiol, 45, 1723, 10.1016/j.jacc.2005.02.079 · DOI
- Campbell, 1996, Identification of epoxyeicosatrienoic acids as endothelium-derived hyperpolarizing factors, Circ Res, 78, 415, 10.1161/01.RES.78.3.415 · DOI
- Capdevila, 2002, Biochemical and molecular properties of the cytochrome P450 arachidonic acid monooxygenases, Prostaglandins Other Lipid Mediat, 68–69, 325, 10.1016/S0090-6980(02)00038-2 · DOI
- Cheng, 2008, 20-hydroxyeico-satetraenoic acid causes endothelial dysfunction via eNOS uncoupling, Am J Physiol Heart Circ Physiol, 294, H1018, 10.1152/ajpheart.01172.2007 · DOI
- Dhanasekaran, 2008, Multiple anti-apoptotic targets of the PI3K/Akt survival pathway are activated by epoxyeicosatrienoic acids to protect cardio-myocytes from hypoxia/anoxia, Am J Physiol Heart Circ Physiol, 294, H724, 10.1152/ajpheart.00979.2007 · DOI
- Dyerberg, 1978, Eicosapentaenoic acid and prevention of thrombosis and atherosclerosis?, Lancet, 2, 117, 10.1016/S0140-6736(78)91505-2 · DOI
- Fer, 2008, Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism, J Lipid Res, 49, 2379, 10.1194/jlr.M800199-JLR200 · DOI
- Fer, 2008, Metabolism of eicosapentaenoic and docosahexaenoic acids by recombinant human cytochromes P450, Arch Biochem Biophys, 471, 116, 10.1016/j.abb.2008.01.002 · DOI
- Fischer, 2008, Dietary n-3 polyunsaturated fatty acids and direct renin inhibition improve electrical remodeling in a model of high human renin hypertension, Hypertension, 51, 540, 10.1161/HYPERTENSIONAHA.107.103143 · DOI
- Fisslthaler, 1999, Cytochrome P450 2C is an EDHF synthase in coronary arteries, Nature, 401, 493, 10.1038/46816 · DOI
- Fleming, 2007, Epoxyeicosatrienoic acids, cell signaling and angiogenesis, Prostaglandins Other Lipid Mediat, 82, 60, 10.1016/j.prostaglandins.2006.05.003 · DOI
- Fleming, 2008, Vascular cytochrome p450 enzymes: physiology and pathophysiology, Trends Cardiovasc Med, 18, 20, 10.1016/j.tcm.2007.11.002 · DOI
- Funk, 2001, Prostaglandins and leukotrienes: advances in eicosanoid biology, Science, 294, 1871, 10.1126/science.294.5548.1871 · DOI · Paper page
- Gross, 2004, Cytochrome P450 ω-hydroxylase inhibition reduces infarct size during reperfusion via the sarcolemmal KATP channel, J Mol Cell Cardiol, 37, 1245
- Gross, 2007, Mechanisms by which epoxyeicosatrienoic acids (EETs) elicit cardioprotection in rat hearts, J Mol Cell Cardiol, 42, 687, 10.1016/j.yjmcc.2006.11.020 · DOI
- Gryglewski, 2008, Prostacyclin among prostanoids, Pharmacol Rep, 60, 3
- Gryglewski, 1979, Effects of all cis-5,8,11,14,17–eicosapentaenoic acid and PGH3 on platelet aggregation, Prostaglandins, 18, 453, 10.1016/S0090-6980(79)80063-5 · DOI
- Harmon, 2006, Oxygenation of ω-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production, Prostaglandins Leukot Essent Fatty Acids, 75, 169, 10.1016/j.plefa.2006.05.005 · DOI
- Harris, 2008, Omega-3 fatty acids and coronary heart disease risk:clinical and mechanistic perspectives, Atherosclerosis, 197, 12, 10.1016/j.atherosclerosis.2007.11.008 · DOI · Paper page
- Hata, 2004, Pharmacology and signaling of prostaglandin receptors: multiple roles in inflammation and immune modulation, Pharmacol Ther, 103, 147, 10.1016/j.pharmthera.2004.06.003 · DOI
- He, 2004, Accumulated evidence on fish consumption and coronary heart disease mortality: a meta-analysis of cohort studies, Circulation, 109, 2705, 10.1161/01.CIR.0000132503.19410.6B · DOI · Paper page
- Hercule, 2007, The vasodilator 17,18-epoxyeicosatetraenoic acid targets the pore-forming BK α channel subunit in rodents, Exp Physiol, 92, 1067, 10.1113/expphysiol.2007.038166 · DOI
- Hercule, 2009, Interaction between P450 eicosanoids and nitric oxide in the control of arterial tone in mice, Arterioscler Thromb Vasc Biol, 29, 54, 10.1161/ATVBAHA.108.171298 · DOI
- Hoagland, 2003, Inhibitors of 20-HETE formation promote salt-sensitive hypertension in rats, Hypertension, 42, 669, 10.1161/01.HYP.0000084634.97353.1A · DOI
- Honeck, 2000, Cytochrome P450-dependent renal arachidonic acid metabolism in desoxycorticosterone acetate-salt hypertensive mice, Hypertension, 36, 610, 10.1161/01.HYP.36.4.610 · DOI
- Hutchens, 2008, Soluble epoxide hydrolase gene deletion reduces survival after cardiac arrest and cardiopulmonary resuscitation, Resuscitation, 76, 89, 10.1016/j.resuscitation.2007.06.031 · DOI
- Imig, 2005, Epoxide hydrolase and epoxygenase metabolites as therapeutic targets for renal diseases, Am J Physiol Renal Physiol, 289, F496, 10.1152/ajprenal.00350.2004 · DOI
- Imig, 2002, Soluble epoxide hydrolase inhibition lowers arterial blood pressure in angiotensin II hypertension, Hypertension, 39, 690, 10.1161/hy0202.103788 · DOI
- Inceoglu, 2007, Soluble epoxide hydrolase inhibition reveals novel biological functions of epoxyeicosatrienoic acids (EETs), Prostaglandins Other Lipid Mediat, 82, 42, 10.1016/j.prostaglandins.2006.05.004 · DOI
- Ishizuka, 2008, 20-Hydroxyeicosatetraenoic acid stimulates nuclear factor-KB activation and the production of inflammatory cytokines in human endothelial cells, J Pharmacol Exp Ther, 324, 103, 10.1124/jpet.107.130336 · DOI
- Jiang, 2007, Cytochrome p450 epoxygenase promotes human cancer metastasis, Cancer Res, 67, 6665, 10.1158/0008-5472.CAN-06-3643 · DOI
- Jump, 2002, The biochemistry of n-3 polyunsaturated fatty acids, J Biol Chem, 277, 8755, 10.1074/jbc.R100062200 · DOI
- Jung, 2005, Soluble epoxide hydrolase is a main effector of angiotensin II-induced hypertension, Hypertension, 45, 759, 10.1161/01.HYP.0000153792.29478.1d · DOI
- Karlgren, 2004, Characterization and tissue distribution of a novel human cytochrome P450-CYP2U1, Biochem Biophys Res Commun, 315, 679, 10.1016/j.bbrc.2004.01.110 · DOI
- Keseru, 2008, Epoxyeicosatrienoic acids and the soluble epoxide hydrolase are determinants of pulmonary artery pressure and the acute hypoxic pulmonary vasoconstrictor response, FASEB J, 22, 4306, 10.1096/fj.08-112821 · DOI
- Kris-Etherton, 2002, Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease, Circulation, 106, 2747, 10.1161/01.CIR.0000038493.65177.94 · DOI · Paper page
- Lands, 2005, Dietary fat and health: the evidence and the politics of prevention: careful use of dietary fats can improve life and prevent disease, Ann NY Acad Sci, 1055, 179, 10.1196/annals.1323.028 · DOI · Paper page
- Lauterbach, 2002, Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators, Hypertension, 39, 609, 10.1161/hy0202.103293 · DOI
- Lavie, 2009, Omega-3 polyunsaturated fatty acids and cardiovascular diseases, J Am Coll Cardiol, 54, 585, 10.1016/j.jacc.2009.02.084 · DOI · Paper page
- Lee, 1999, Effects of epoxyeicosatrienoic acids on the cardiac sodium channels in isolated rat ventricular myocytes, J Physiol, 519, 153, 10.1111/j.1469-7793.1999.0153o.x · DOI
- Liclican, 2008, Failure to upregulate the adenosine2A receptor-epoxyeicosatrienoic acid pathway contributes to the development of hypertension in Dahl salt-sensitive rats, Am J Physiol Renal Physiol, 295, F1696, 10.1152/ajprenal.90502.2008 · DOI
- Loch, 2007, Prevention of hypertension in DOCA-salt rats by an inhibitor of soluble epoxide hydrolase, Cell Biochem Bio-phys, 47, 87, 10.1385/CBB:47:1:87 · DOI
- Loot, 2008, Role of cytochrome P450-dependent transient receptor potential V4 activation in flow-induced vasodilatation, Cardiovasc Res, 80, 445, 10.1093/cvr/cvn207 · DOI
- Lu, 2001, Activation of ATP-sensitive K+ channels by epoxyeicosatri-enoic acids in rat cardiac ventricular myocytes, J Physiol, 537, 811, 10.1113/jphysiol.2001.012896 · DOI
- Lu, 2002, Stereospecific activation of cardiac ATP-sensitive K+ channels by epoxyeicosatrienoic acids: a structural determinant study, Mol Pharmacol, 62, 1076, 10.1124/mol.62.5.1076 · DOI
- Matthan, 2005, A systematic review and metaanalysis of the impact of ω-3 fatty acids on selected arrhythmia outcomes in animal models, Metab Clin Exp, 54, 1557, 10.1016/j.metabol.2005.05.026 · DOI
- McGiff, 1999, 20–HETE and the kidney: resolution of old problems and new beginnings, Am J Physiol, 277, R607
- Monti, 2008, Soluble epoxide hydrolase is a susceptibility factor for heart failure in a rat model of human disease, Nat Genet, 40, 529, 10.1038/ng.129 · DOI
- Morin, 2009, Relaxing effects of 17(18)-EpETE on arterial and airway smooth muscles in human lung, Am J Physiol Lung Cell Mol Physiol, 296, L130, 10.1152/ajplung.90436.2008 · DOI
- Motoki, 2008, Soluble epoxide hydrolase inhibition and gene deletion are protective against myocardial ischemia-reperfusion injury in vivo, Am J Physiol Heart Circ Physiol, 295, H2128, 10.1152/ajpheart.00428.2008 · DOI
- Mozaffarian, 2008, Fish and n-3 fatty acids for the prevention of fatal coronary heart disease and sudden cardiac death, Am J Clin Nutr, 87, 1991S, 10.1093/ajcn/87.6.1991S · DOI · Paper page
- Muller, 2007, Mouse Cyp4a isoforms: enzymatic properties, gender- and strain-specific expression, and role in renal 20-hydroxyeicosatetraenoic acid formation, Biochem J, 403, 109, 10.1042/BJ20061328 · DOI
- Muller, 2004, A peroxisome proliferator-activated receptor-a activator induces renal CYP2C23 activity and protects from angiotensin II-induced renal injury, Am J Pathol, 164, 521, 10.1016/S0002-9440(10)63142-2 · DOI
- Nguyen, 1999, Kinetic profile of the rat CYP4A isoforms: arachidonic acid metabolism and isoform-specific inhibitors, Am J Physiol, 276, R1691
- Nithipatikom, 2006, Effects of selective inhibition of cytochrome P-450 ω-hydroxylases and ischemic preconditioning in myocardial protection, Am J Physiol Heart Circ Physiol, 290, H500, 10.1152/ajpheart.00918.2005 · DOI
- Nithipatikom, 2004, Inhibition of cytochrome P450 ω-hydroxylase: a novel endogenous cardioprotective pathway, Circ Res, 95, e65, 10.1161/01.RES.0000146277.62128.6f · DOI
- Node, 1999, Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids, Science, 285, 1276, 10.1126/science.285.5431.1276 · DOI
- Peters-Golden, 2007, Leukotrienes, N Engl J Med, 357, 1841, 10.1056/NEJMra071371 · DOI
- Revermann, 2009, Inhibition of the soluble epoxide hydrolase attenuates monocrotaline-induced pulmonary hypertension in rats, J Hypertens, 27, 322, 10.1097/HJH.0b013e32831aedfa · DOI
- Roman, 2002, P-450 metabolites of arachidonic acid in the control of cardiovascular function, Physiol Rev, 82, 131, 10.1152/physrev.00021.2001 · DOI
- Roman, 1997, Renal P450 metabolites of arachidonic acid and the development of hypertension in Dahl salt-sensitive rats, Am J Hypertens, 10, 63S, 10.1016/S0895-7061(97)00077-0 · DOI
- Russo, 2009, Dietary n-6 and n-3 polyunsaturated fatty acids: from biochemistry to clinical implications in cardiovascular prevention, Biochem Pharmacol, 77, 937, 10.1016/j.bcp.2008.10.020 · DOI
- Schwarz, 2005, Human CYP1A1 variants lead to differential eicosapentaenoic acid metabolite patterns, Biochem Bio-phys Res Commun, 336, 779, 10.1016/j.bbrc.2005.08.172 · DOI
- Schwarz, 2004, Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: highly stereoselective formation of 17(R),18(S)-epoxyeicosatetraenoic acid, Biochem Pharmacol, 67, 1445, 10.1016/j.bcp.2003.12.023 · DOI
- Seubert, 2004, Enhanced postischemic functional recovery in CYP2J2 transgenic hearts involves mitochondrial ATP-sensitive K+ channels and p42/p44 MAPK pathway, Circ Res, 95, 506, 10.1161/01.RES.0000139436.89654.c8 · DOI
- Seubert, 2006, Role of soluble epoxide hydrolase in postischemic recovery of heart contractile function, Circ Res, 99, 442, 10.1161/01.RES.0000237390.92932.37 · DOI
- Seubert, 2007, Role of epoxyeicosatrienoic acids in protecting the myocardium following ischemia/reperfusion injury, Prostaglandins Other Lipid Mediat, 82, 50, 10.1016/j.prostaglandins.2006.05.017 · DOI
- Simopoulos, 2008, The importance of the omega-6/omega-3 fatty acid ratio in cardiovascular disease and other chronic diseases, Exp Biol Med (Maywood), 233, 674, 10.3181/0711-MR-311 · DOI
- Simpkins, 2009, Soluble epoxide inhibition is protective against cerebral ischemia via vascular and neural protection, Am J Pathol, 174, 2086, 10.2353/ajpath.2009.080544 · DOI
- Singh, 2007, Vascular cytochrome P450 4A expression and 20-hydroxyeicosatetraenoic acid synthesis contribute to endothelial dysfunction in androgeninduced hypertension, Hypertension, 50, 123, 10.1161/HYPERTENSIONAHA.107.089599 · DOI
- Singh, 2008, Renal vascular cytochrome P450-derived eicosanoids in androgen-induced hypertension, Pharmacol Rep, 60, 29
- Smith, 2005, Attenuation of tobacco smoke-induced lung inflammation by treatment with a soluble epoxide hydrolase inhibitor, Proc Natl Acad Sci USA, 102, 2186, 10.1073/pnas.0409591102 · DOI
- Spector, 2009, Arachidonic acid cytochrome P450 epoxygenase pathway, J Lipid Res, 50, S52, 10.1194/jlr.R800038-JLR200 · DOI
- Spiecker, 2005, Vascular protective effects of cytochrome p450 epoxygenase-derived eicosanoids, Arch Biochem Biophys, 433, 413, 10.1016/j.abb.2004.10.009 · DOI
- Stark, 2005, Oxygenation of polyunsaturated long chain fatty acids by recombinant CYP4F8 and CYP4F12 and catalytic importance of Tyr-125 and Gly-328 of CYP4F8, Arch Biochem Biophys, 441, 174, 10.1016/j.abb.2005.07.003 · DOI
- Sun, 2006, Low Na intake suppresses expression of CYP2C23 and arachidonic acid-induced inhibition of ENaC, Am J Physiol Renal Physiol, 291, F1192, 10.1152/ajprenal.00112.2006 · DOI
- Terano, 1984, Biosynthesis and biological activity of leukotriene B5, Prostaglandins, 27, 217, 10.1016/0090-6980(84)90075-3 · DOI
- Van Rollins, 1988, Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes, Biochim Biophys Acta, 966, 133, 10.1016/0304-4165(88)90137-7 · DOI
- VanRollins, 1984, Oxidation of docosahexaenoic acid by rat liver microsomes, J Biol Chem, 259, 5776, 10.1016/S0021-9258(18)91081-1 · DOI
- von Schacky, 2009, Use of red blood cell fatty-acid profiles as biomarkers in cardiac disease, Biomark Med, 3, 25, 10.2217/17520363.3.1.25 · DOI
- von Schacky, 2007, Cardiovascular benefits of omega-3 fatty acids, Cardiovasc Res, 73, 310, 10.1016/j.cardiores.2006.08.019 · DOI
- Wang, 2003, Up-regulation of endothelial nitric-oxide synthase by endothelium-derived hyperpolarizing factor involves mitogen-activated protein kinase and protein kinase C signaling pathways, J Pharmacol Exp Ther, 307, 753, 10.1124/jpet.103.052787 · DOI
- Wang, 2006, Endothelial dysfunction and hypertension in rats transduced with CYP4A2 adenovirus, Circ Res, 98, 962, 10.1161/01.RES.0000217283.98806.a6 · DOI
- Wu, 1996, Molecular cloning and expression of CYP2J2, a human cytochrome P450 arachidonic acid epoxygenase highly expressed in heart, J Biol Chem, 271, 3460, 10.1074/jbc.271.7.3460 · DOI
- Xiao, 2007, Cyclic AMP-dependent modulation of cardiac L-type Ca2+ and transient outward K+ channel activities by epoxyeicosatrienoic acids, Prostaglandins Other Lipid Mediat, 82, 11, 10.1016/j.prostaglandins.2006.05.023 · DOI
- Xiao, 1998, Cytochrome P450: a novel system modulating Ca2+ channels and contraction in mammalian heart cells, J Physiol, 508, 777, 10.1111/j.1469-7793.1998.777bp.x · DOI
- Xiao, 2004, Enhancement of cardiac L-type Ca2+ currents in transgenic mice with cardiac-specific overexpression of CYP2J2, Mol Pharmacol, 66, 1607, 10.1124/mol.104.004150 · DOI
- Xu, 2006, Prevention and reversal of cardiac hypertrophy by soluble epoxide hydrolase inhibitors, Proc Natl Acad Sci USA, 103, 18733, 10.1073/pnas.0609158103 · DOI
- Yang, 2007, Cytochrome P-450 epoxygenases protect endothelial cells from apoptosis induced by tumor necrosis factor-a via MAPK and PI3K/Akt signaling pathways, Am J Physiol Heart Circ Physiol, 293, H142, 10.1152/ajpheart.00783.2006 · DOI
- Yang, 2008, Characterization of epoxyeicosatrienoic acid binding site in U937 membranes using a novel radiolabeled agonist, 20-125I-14,15-epoxyeicosa-8(Z)-enoic acid, J Pharmacol Exp Ther, 324, 1019, 10.1124/jpet.107.129577 · DOI
- Ye, 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, 10.1124/jpet.303.2.768 · DOI
- Yu, 2000, Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids, Circ Res, 87, 992, 10.1161/01.RES.87.11.992 · DOI
- Zhang, 2001, EET homologs potently dilate coronary microvessels and activate BKCa channels, Am J Physiol Heart Circ Physiol, 280, H2430, 10.1152/ajpheart.2001.280.6.H2430 · DOI
Cited by
Sorted by citations
Items 101–145 of 145
Influence of different supplementation on platelet aggregation in patients with rheumatoid arthritis
Tomić-Smiljanić, M., Vasiljevic, D., Lučić-Tomić, A., Andjelkovic, N., Jakovljevic, V., Bolovich, S., & Veselinović, M. (2019) · Clinical Rheumatology · doi:10.1007/s10067-019-04569-3 · Cited by 11
Maki, K. C., Johns, C., Harris, W. S., Puder, M., Freedman, S. D., Thorsteinsson, T., Daak, A. A., Rabinowicz, A. L., & Sancilio, F. D. (2017) · Clinical Therapeutics · doi:10.1016/j.clinthera.2017.01.019 · Cited by 12
Kim, S., Oh, H., Kim, Y.-C., Jeong, G., & Lee, S. (2016) · Evidence-Based Complementary and Alternative Medicine · doi:10.1155/2016/5198743 · Cited by 11
Maksymchuk, O., & Kashuba, V. (2019) · Pharmacological Reports · doi:10.1016/j.pharep.2019.04.011 · Cited by 10
Arakawa, K., Himeno, H., Kirigaya, J., Otomo, F., Matsushita, K., Nakahashi, H., Shimizu, S., Nitta, M., Yano, H., Endo, M., et al. (2015) · Journal of Cardiology · doi:10.1016/j.jjcc.2015.03.009 · Cited by 10
Braeckman, R., Stirtan, W., & Soni, P. N. (2014) · Clinical drug investigation · doi:10.1007/s40261-014-0252-8 · Cited by 10
Pre(peri)-natal ω-3 PUFA deficiency-induced hypertension and its broader implications
Das, U. (2012) · Hypertension Research · doi:10.1038/hr.2011.225 · Cited by 10
Bioactive oxylipins in type 2 diabetes mellitus patients with and without hypertriglyceridemia
Xiao, Y., Pietzner, A., Rohwer, N., Jung, A., Rothe, M., Weylandt, K. H., & Elbelt, U. (2023) · Frontiers in Endocrinology · doi:10.3389/fendo.2023.1195247 · Cited by 9
Click chemistry-based enrichment strategy for tracing cellular fatty acid metabolism by LC-MS/MS
Yang, R.-J., Zou, J., Liu, J.-Y., Dai, J.-K., & Wan, J.-B. (2023) · Journal of Pharmaceutical Analysis · doi:10.1016/j.jpha.2023.05.001 · Cited by 8
Changes to PUFA-PPAR pathway during mesaconitine induced myocardial coagulative necrosis
Chen, Q., Deng, X., Zhang, K., Kang, Y., Jiao, M., Zhang, J., Wang, C., & Li, F. (2023) · Food and Chemical Toxicology · doi:10.1016/j.fct.2023.113831 · Cited by 12
Effect of fish oil on monoepoxides derived from fatty acids during cardiac surgery1[S]
Akintoye, E., Wu, J. H. Y., Hou, T., Song, X.-L., Yang, J., Hammock, B., & Mozaffarian, D. (2016) · Journal of Lipid Research · doi:10.1194/jlr.p062398 · Cited by 8
Nowak, M., Tardivel, S., Sayegrih, K., Robert, V., Abreu, S., Chaminade, P., Vicca, S., Grynberg, A., & Lacour, B. (2011) · Journal of Atherosclerosis and Thrombosis · doi:10.5551/jat.7062 · Cited by 8
Pharmacokinetics and Safety Profile of Omega-3 Polyunsaturated Fatty Acids
Tamargo, J. L., & Tamargo, M. (2016) · Springer eBooks · doi:10.1007/978-3-319-40458-5_39 · Cited by 7
Arms Race Between Plants and Animals: Biotransformation System
Steinberg, C. (2012) · Springer eBooks · doi:10.1007/978-94-007-2072-5_4 · Cited by 7
Recent insights into function, structure and modification of cytochrome P450 153 a family
Wang, L.-L., Xu, Z., Zhang, Y., Wang, R.-M., Wang, J.-Q., Yang, S., Su, J., & Li, Y. (2023) · Molecular Biology Reports · doi:10.1007/s11033-023-08553-8 · Cited by 6
Windisch, H. S., & Fink, P. (2019) · BMC Genomics · doi:10.1186/s12864-019-6268-y · Cited by 6
Influence of CYP1A1*2C on High Triglyceride Levels in Female Mexican Indigenous Tarahumaras
Bailón-Soto, C. E., Galavíz-Hernández, C., Lazalde-Ramos, B. P., Hernández-Velázquez, F. D., Salas-Pacheco, J. M., Lares-Assef, I., & Sosa‐Macías, M. (2014) · Archives of Medical Research · doi:10.1016/j.arcmed.2014.05.007 · Cited by 5
Xing, C.-F., Tang, M.-Y., Yang, J., Wang, S., Xu, Q.-H., Feng, W., Mu, Y.-P., Li, F., & Zhao, A. Z. (2023) · Biochemical Pharmacology · doi:10.1016/j.bcp.2023.115775 · Cited by 5
Šušnjara, P., Mihaljević, Z., Stupin, A., Kolobarić, N., Matić, A., Jukić, I., Kralik, Z., Kralik, G., Miloloža, A., Pavošević, T., et al. (2023) · Nutrients · doi:10.3390/nu15071599 · Cited by 5
“If the ratio goes to higher concentrations of n-3 PUFAs, then the production of anti-inflammatory and vasodilator mediators such as prostaglandins series 3 (PGI3), leukotrienes series 5 (LTB5), and thromboxane series 3 (TXA3) dominates [39].”
BackgroundGao, S., Cui, K., Li, Y., Pang, Y., Fang, W. H., Mai, K., & Ai, Q. (2021) · Aquaculture · doi:10.1016/j.aquaculture.2021.736641 · Cited by 6
Stereodefined synthesis of the four possible stereoisomers of 5,18-diHETE
Suganuma, Y., Tanabe, S., Sugihara, Y., & Kobayashi, Y. (2018) · Tetrahedron · doi:10.1016/j.tet.2018.01.053 · Cited by 6
Li, H.-X., Wang, R.-X., Li, X.-R., Guo, T., Wu, Y., Guo, S.-X., Sun, L.-P., Yang, Z.-Y., Yang, X.-J., & Jiang, W.-P. (2011) · Lipids · doi:10.1007/s11745-010-3503-3 · Cited by 5
Xia, G., Zhou, G.-D., Jiang, W.-W., Chu, C., Wang, L.-H., & Moorthy, B. (2024) · International Journal of Molecular Sciences · doi:10.3390/ijms25073781 · Cited by 4
“Materials for DNA extraction [80–83], RNA extraction [84], and 32 P-postlabeling analysis [80,85,86] have been reported previously.”
MethodIizasa, S., Nagao, K., Tsuge, K., Nagano, Y., & Yanagita, T. (2023) · PLoS ONE · doi:10.1371/journal.pone.0295591 · Cited by 4
Maksymchuk, O., Shysh, A., & Stroy, D. (2022) · Frontiers in Endocrinology · doi:10.3389/fendo.2022.1004564 · Cited by 4
“Enzymes of the cytochrome P450 superfamily, especially CYP2E1, play the main role in the metabolism of omega PUFAs (16).”
BackgroundShymanskyi, I., Kеtsa, О. V., Marchenko, M. M., & Veliky, M. M. (2018) · The Ukrainian Biochemical Journal · doi:10.15407/ubj90.04.036 · Cited by 5
Bao, Q., Liu, Y.-J., Song, H., Yang, N., Ai, D., Zhu, Y., & Zhang, X. (2018) · Clinical and Experimental Pharmacology and Physiology · doi:10.1111/1440-1681.12825 · Cited by 4
Yu, M., Li, Z.-M., Cui, Y.-Y., Rong, T., Tian, Z., Deng, D., Liu, Z.-C., Zhang, R., & Ma, X.-Y. (2024) · Animals · doi:10.3390/ani14223192 · Cited by 3
“It is worth noting that, although our results showed that the mechanism of causing muscle to be rich in unsaturated fatty acids may be related to metabolism and gene expressions in the liver, more systematic studies are needed to confirm this.”
Asulin, M., Gorodetzer, N., Fridman, R., Ben-Shushan, R. S., Cohen, Z., Beyer, A. M., Chuyun, D., Gutterman, D., & Szuchman-Sapir, A. (2024) · Biochemical and Biophysical Research Communications - BBRC · doi:10.1016/j.bbrc.2024.149585 · Cited by 3
The Fish Oil Story – Back to Greenland?
Gajos, G. (2011) · Cardiology · doi:10.1159/000329826 · Cited by 2
Effects of Mediterranean Diet on the Metabolome
Martinez, J. A., Keun, H. C., & Siskos, A. (2016) · Springer eBooks · doi:10.1007/978-3-319-27969-5_10 · Cited by 3
CYP450 network shifts in MASLD/MASH: from pathogenesis to nutrition-informed modulation
Koç, S., Toydemir, S., Vardar, G., Öter, G. N., & Yusufoğlu, B. (2026) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2026.110459 · Cited by 3
Sule, R. O., Morisseau, C., Yang, J., Hammock, B., & Gomes, A. V. (2024) · Scientific Reports · doi:10.1038/s41598-024-69557-3 · Cited by 2
Kriyt, V., Sladkova, Y., Sannikov, M. V., & Pyatibrat, A. (2020) · doi:10.35627/2219-5238/2020-331-10-65-74 · Cited by 2
Gabrielsson, B. G., Andersson, N., & Undeland, I. (2014) · Wiley eBooks · doi:10.1002/9781118855102.ch7 · Cited by 3
Enzymatic Oxidation of Polyunsaturated Fatty Acids
MURPHY, S. A., Al‐Aasswad, N. M. I., & Nicolaou, A. (2015) · Oxidative stress and disease · doi:10.1201/b18138-5 · Cited by 2
Metabolism of polyunsaturated fatty acids and their oxylipins
Greupner, T. (2019) · doi:10.15488/4445 · Cited by 2
“Fischer R, Konkel A, Mehling H, Blossey K, Gapelyuk A, Wessel N, et al. Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYPepoxygenase pathway.”
BackgroundInfluentialDietary Fatty Acids, Redox Signaling, and the Heart
Beam, J., Botta, A. M., Barendregt, R., & Ghosh, S. (2014) · Springer eBooks · doi:10.1007/978-3-642-30018-9_44 · Cited by 3
Regulation of P450-derived epoxy fatty acids in cardiovascular diseases
Edin, M. L., Graves, J. P., & Zeldin, D. C. (2025) · Redox Biochemistry and Chemistry · doi:10.1016/j.rbc.2025.100064 · Cited by 1
“P450s also metabolize linoleic acid (LA), and the omega-3 fatty acids epoxyeicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) to epoxy, dihydroxy and hydroxy oxylipins that have important physiological functions [118, 119] (Table 2).”
Rapid screening system to identify unspecific peroxygenase activity
Schramm, M., Avilés, C. R. C., Kalmbach, J., Schmidtke, K.-U., Kiebist, J., Kellner, H., Hofrichter, M., & Scheibner, K. (2025) · Clinical Hemorheology and Microcirculation · doi:10.1177/13860291241306566 · Cited by 1
“…by veratryl alcohol (VA), 2,6-dimethoxyphenol (DMP) and 5-nitrobenzodioxole (NBD), while r Ani UPO followed the order ABTS > DMP > NBD ∼ VA. – 14,33,34 For all tested substrates, the formation of oxygenated products could be observed by an indicative mass increase of 16 m/z compared to the…”
Yang, Y., Wu, H.-Y., Xu, X.-Y., Morisseau, C., Lee, K. S. S., Hammock, B., Chen, J., & Zhao, L. (2025) · Nutrients · doi:10.3390/nu17060936 · Cited by 1
“N -3 epoxy fatty acids (EpFAs), such as epoxyeicosatetraenoic acids (EEQs) and epoxy-docosapentaenoic acids (EDPs), are produced from eicosapentaenoic acid (EPA) and do-cosahexaenoic acid (DHA) by CYP450s, respectively [7,8].”
Eicosanoid biosynthesizing enzymes in Prototheria.
Kakularam, K. R., Gündem, E., Stehling, S., Rothe, M., Heydeck, D., & Kuhn, H. (2024) · Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids · doi:10.1016/j.bbalip.2024.159569 · Cited by 1
ω-3 Fatty Acids and Nonalcoholic Fatty Liver Disease
Depner, C., Lytle, K., Tripathy, S., & Jump, D. (2014) · doi:10.1201/b17315-17 · Cited by 1
Fatty Acids and the Brain Health
Longhi, R. (2019) · Omega Fatty Acids in Brain and Neurological Health · doi:10.1016/b978-0-12-815238-6.00028-6 · Cited by 1
Maksymchuk, O., & Chashchyn, M. (2013) · Fiziolohichnyĭ zhurnal · doi:10.15407/fz59.04.067
Metadata
- Authors
- Arnold, C., Konkel, A., Fischer, R., & Schunck, W.-H.
- Affiliations
- Max Delbrück Center (DE)
- Corresponding author
- Schunck, Wolf-Hagen
- Venue
- Pharmacological Reports
- Published
- 2010-05
- Volume
- 62
- Issue
- 3
- Pages
- 536-547
- ISSN
- 1734-1140 (ISSN-L)
- OpenAlex
- W1998719368
- Cited by
- 174
- References
- 111
- Citations by year
- 2026: 2 · 2025: 10 · 2024: 6 · 2023: 13 · 2022: 9 · 2021: 8 · 2020: 10 · 2019: 10 · 2018: 12 · 2017: 13 · 2016: 10 · 2015: 11 · 2014: 19 · 2013: 12 · 2012: 15
- FWCI
- 1.47
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Pharmacological Reports (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Nursing › Nutrition and Dietetics › Fatty Acid Research and Health
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
- Health Sciences › Medicine › Pharmacology (medical) › Inflammatory mediators and NSAID effects
- Keywords
- cytochrome P450, omega-3 fatty acids, omega-6 fatty acids, eicosapentaenoic acid, docosahexaenoic acid, arachidonic acid metabolism, fatty acid epoxidation, regioselectivity, epoxy fatty acids, hydroxy fatty acids, fish oil, cardioprotection, vascular protection, sudden cardiac death, cardiac arrhythmias
- MeSH terms
- Cytochrome P-450 CYP2J2, Animals, Cardiotonic Agents, Cardiovascular Diseases, Cytochrome P-450 Enzyme System, Docosahexaenoic Acids, Epoxide Hydrolases, Humans, Hydroxyeicosatetraenoic Acids, Eicosapentaenoic Acid, Fatty Acids, Omega-3, Arachidonic Acid, Death, Sudden, Cardiac, Cytochrome P-450 CYP1A1, Cytochrome P-450 CYP2E1, Fatty Acids, Omega-6
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review