Increase of EPA-derived hydroxy, epoxy and dihydroxy fatty acid levels in human plasma after a single dose of long-chain omega-3 PUFA

Prostaglandins and Other Lipid Mediators

Volumn 109-111, Issue , 2014, Pages 23-31

  Schuchardt, Jan Philipp ^a   Schneider, Inga ^a   Willenberg, Ina ^b   Yang, Jun ^c   Hammock, Bruce D ^c   Hahn, Andreas ^a   Schebb, Nils Helge ^b  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b UNIVERSITY OF VETERINARY MEDICINE HANNOVER   (Germany)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Arachidonic acid; Eicosanoids; Eicosapentaenoic acid; Oxylipins

Indexed keywords

ARACHIDONIC ACID; CYTOCHROME P450; DIHYDROXY FATTY ACID; DOCOSAPENTAENOIC ACID; EPOXY FATTY ACID; FATTY ACID; HYDROXY FATTY ACID; ICOSAPENTAENOIC ACID; ICOSATETRAENOIC ACID; OMEGA 3 FATTY ACID; OXYLIPIN; PHOSPHOLIPID; UNCLASSIFIED DRUG;

ADULT; ARTICLE; BIOLOGICAL ACTIVITY; BODY MASS; DIET SUPPLEMENTATION; FAT INTAKE; FATTY ACID BLOOD LEVEL; HUMAN; HUMAN EXPERIMENT; HUMAN TISSUE; LIPID COMPOSITION; MALE; NORMAL HUMAN; PHOSPHOLIPID BLOOD LEVEL; SHORT COURSE THERAPY; BLOOD; CHEMISTRY; CLINICAL TRIAL; ESTERIFICATION; KINETICS;

ADULT; EICOSAPENTAENOIC ACID; ESTERIFICATION; FATTY ACIDS, OMEGA-3; HEALTHY VOLUNTEERS; HUMANS; KINETICS; MALE; OXYLIPINS; PHOSPHOLIPIDS;

EID: 84901621091     PISSN: 10988823     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.prostaglandins.2014.03.001     Document Type: Article

References (36)

1. C. Arnold, A. Konkel, R. Fischer, and W.H. Schunck Cytochrome P450-dependent metabolism of omega-6 and omega-3 long-chain polyunsaturated fatty acids Pharmacol Rep 62 3 2010 536 547
2. M.W. Buczynski, D.S. Dumlao, and E.A. Dennis Thematic review series: proteomics. An integrated omics analysis of eicosanoid biology J Lipid Res 50 6 2009 1015 1038
3. W.S. Powell, S. Gravel, and F. Gravelle Formation of a 5-oxo metabolite of 5,8,11,14,17-eicosapentaenoic acid and its effects on human neutrophils and eosinophils J Lipid Res 36 12 1995 2590 2598 (Pubitemid 26029615)
4. C.N. Serhan Novel eicosanoid and docosanoid mediators: resolvins, docosatrienes, and neuroprotectins Curr Opin Clin Nutr Metab Care 8 2 2005 115 121 (Pubitemid 40289470)
5. C. Morisseau, B. Inceoglu, and K. Schmelzer et al. Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids J Lipid Res 51 12 2010 3481 3490
6. C.A. Rouzer, and L.J. Marnett Cyclooxygenases: structural and functional insights J Lipid Res 50 Suppl. 2009 S29 S34
7. B. Samuelsson, S.E. Dahlén, J.A. Lindgren, C.A. Rouzer, and C.N. Serhan Leukotrienes and lipoxins: structures, biosynthesis, and biological effects Science 237 4819 1987 1171 1176 (Pubitemid 17131222)
8. O. Rådmark, and B. Samuelsson 5-Lipoxygenase: mechanisms of regulation J Lipid Res 50 Suppl. 2009 S40 S45
9. R.J. Roman P-450 metabolites of arachidonic acid in the control of cardiovascular function Physiol Rev 82 1 2002 131 185 (Pubitemid 34654217)
10. J.H. Capdevila, and J.R. Falck Biochemical and molecular properties of the cytochrome P450 arachidonic acid monooxygenases Prostaglandins Other Lipid Mediat 68-69: 2002 325 344 (Pubitemid 35247405)
11. C. Morisseau, and B.D. Hammock Impact of soluble epoxide hydrolase and epoxyeicosanoids on human health Annu Rev Pharmacol Toxicol 53 2013 37 58
12. H. Yin, L. Xu, and N.A. Porter Free radical lipid peroxidation: mechanisms and analysis Chem Rev 111 10 2011 5944 5972
13. C.M. Spickett, I. Wiswedel, W. Siems, K. Zarkovic, and N. Zarkovic Advances in methods for the determination of biologically relevant lipid peroxidation products Free Radic Res 44 10 2010 1172 1202
14. E. Niki Lipid peroxidation products as oxidative stress biomarkers Biofactors 34 2 2008 171 180
15. C. Westphal, A. Konkel, and W. Schunck CYP-eicosanoids - a new link between omega-3 fatty acids and cardiac disease? Prostaglandins Other Lipid Mediat 96 1-4 2011 99 108
16. L.N. Agbor, M.T. Walsh, J.R. Boberg, and M.K. Walker Elevated blood pressure in cytochrome P4501A1 knockout mice is associated with reduced vasodilation to omega-3 polyunsaturated fatty acids Toxicol Appl Pharmacol 264 3 2012 351 360
17. F. Jung, C. Schulz, and F. Blaschke et al. Effect of cytochrome P450-dependent epoxyeicosanoids on Ristocetin-induced thrombocyte aggregation Clin Hemorheol Microcirc 52 2-4 2012 403 416
18. G. Zhang, D. Panigrahy, and L.M. Mahakian et al. Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis Proc Natl Acad Sci USA 110 16 2013 6530 6535
19. G.C. Shearer, W.S. Harris, T.L. Pedersen, and J.W. Newman Detection of omega-3 oxylipins in human plasma and response to treatment with omega-3 acid ethyl esters J Lipid Res 51 8 2010 2074 2081
20. A.H. Keenan, T.L. Pedersen, K. Fillaus, M.K. Larson, G.C. Shearer, and J.W. Newman Basal omega-3 fatty acid status affects fatty acid and oxylipin responses to high-dose n3-HUFA in healthy volunteers J Lipid Res 53 8 2012 1662 1669
21. S.L. Lundström, J. Yang, J.D. Brannan, J.Z. Haeggström, B.D. Hammock, and P. Nair Lipid mediator serum profiles in asthmatics significantly shift following dietary supplementation with omega-3 fatty acids Mol Nutr Food Res 57 8 2013 1378 1389
22. J.P. Schuchardt, S. Schmidt, and G. Kressel et al. Modulation of blood oxylipin levels by long-chain omega-3 fatty acid supplementation in hyper- and normolipidemic men Prostaglandins Leukot Essent Fatty Acids 90 2-3 2014 27 37
23. W.E. Kaminski, E. Jendraschak, R. Kiefl, and C. von Schacky Dietary omega-3 fatty acids lower levels of platelet-derived growth factor mRNA in human mononuclear cells Blood 81 7 1993 1871 1879 (Pubitemid 23101602)
24. E.G. Bligh, and W.J. Dyer A rapid method of total lipid extraction and purification Can J Biochem Physiol 37 8 1959 911 917
25. J.W. Newman, G.A. Kaysen, B.D. Hammock, and G.C. Shearer Proteinuria increases oxylipid concentrations in VLDL and HDL but not LDL particles in the rat J Lipid Res 48 8 2007 1792 1800 (Pubitemid 47311996)
26. C. Arnold, M. Markovic, K. Blossey, G. Wallukat, R. Fischer, and R. Dechend Arachidonic acid-metabolizing cytochrome P450 enzymes are targets of {omega}-3 fatty acids J Biol Chem 285 43 2010 32720 32733
27. J.P. Schuchardt, S. Schmidt, G. Kressel, H. Dong, I. Willenberg, and B.D. Hammock Comparison of free serum oxylipin concentrations in hyper- vs. normolipidemic men Prostaglandins Leukot Essent Fatty Acids 89 1 2013 19 29
28. E.A. Miles, and P.C. Calder Influence of marine n-3 polyunsaturated fatty acids on immune function and a systematic review of their effects on clinical outcomes in rheumatoid arthritis Br J Nutr 107 Suppl 2 2012 S171 S184
29. C. Samieri, C. Féart, and L. Letenneur et al. Low plasma eicosapentaenoic acid and depressive symptomatology are independent predictors of dementia risk Am J Clin Nutr 88 3 2008 714 721
30. P. Lin, and K. Su A meta-analytic review of double-blind, placebo-controlled trials of antidepressant efficacy of omega-3 fatty acids J Clin Psychiatry 68 7 2007 1056 1061 (Pubitemid 47340326)
31. J. Delgado-Lista, P. Perez-Martinez, J. Lopez-Miranda, and F. Perez-Jimenez Long chain omega-3 fatty acids and cardiovascular disease: a systematic review Br J Nutr 107 Suppl. 2 2012 S201 S213
32. D. Mozaffarian, and J.H.Y. Wu Omega-3 fatty acids and cardiovascular disease: effects on risk factors, molecular pathways, and clinical events J Am Coll Cardiol 58 20 2011 2047 2067
33. H. Jiang, A.G. Zhu, and M. Mamczur et al. Hydrolysis of cis- and trans-epoxyeicosatrienoic acids by rat red blood cells J Pharmacol Exp Ther 326 1 2008 330 337 (Pubitemid 351872119)
34. G.C. Shearer, and J.W. Newman Lipoprotein lipase releases esterified oxylipins from very low-density lipoproteins Prostaglandins Leukot Essent Fatty Acids 79 6 2008 215 222
35. G.C. Shearer, and J.W. Newman Impact of circulating esterified eicosanoids and other oxylipins on endothelial function Curr Atheroscler Rep 11 6 2009 403 410
36. J. Cao, K.A. Schwichtenberg, N.Q. Hanson, and M.Y. Tsai Incorporation and clearance of omega-3 fatty acids in erythrocyte membranes and plasma phospholipids Clin Chem 52 12 2006 2265 2272 (Pubitemid 44925001)