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Eicosapentaenoic acid
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[[File:Omega-3 EPA.jpg|alt=label film a bottle of omega 3 EPA fish oil supplements |thumb|Omega 3 EPA from fish oil. Image: [https://world.openfoodfacts.org/product/5600397302814/omega-3-epa-plus Open Food Facts]. ]] '''Eicosapentaenoic acid''' (EPA) is an [[Omega 3 fatty acid]] found in [[fish oil]]. A precursor to [[DHA]], it is anti-[[inflammation|inflammatory]] and may be neuroprotective. ==Immune system== EPA inhibits the production of [[arachidonic acid]] (AA) and its related pro-inflammatory [[Prostaglandin|prostaglandins]] by competing for the [[delta-5-desaturase]] enzyme that produces AA. The more EPA you have in your diet, the less AA you produce. EPA also competes with [[phospholipase A2]], necessary to release AA from cell membranes, a similar mechanism of action to [[corticosteroid]]s. The [[eicosanoid]]s produced from EPA are less active than those produced from AA. A high EPA/AA ratio is anti-inflammatory.{{Citation needed}} EPA inhibits the expression of pro-inflammatory mediators in [[microglia]], including [[nitric oxide]], [[prostaglandin E2]] and pro-inflammatory cytokines [[Interleukin 1|IL-1Ξ²]], [[Interleukin 6|IL-6]], and [[TNF-alpha|TNF-Ξ±]] in [[lipopolysaccharide]]-induced activation.<ref name="moon2007" /> Several studies have found both EPA and DHA inhibit [[microglia]] activation.<ref name="hjorth2012" /> In culture, EPA inhibits [[prostaglandin D2]], a [[prostaglandin]] found in large amounts in the [[brain]] and in [[mast cell]]s.<ref name="obata1999" /> ==Nervous system== EPA is found in very low levels in the brain (in contrast to DHA, which is the primary structural Omega 3 in the brain and found in abundance). However, EPA still has important [[nervous system|neurological]] and psychiatric effects. EPA inhibits [[Phospholipase A2]] (PLA2), an enzyme that breaks down [[Phospholipid|phospholipids]], the major component of cell membranes. Increased PLA2 activity has been observed in the [[cerebrospinal fluid]] of patients with [[Alzheimer's]]<ref name="chalbot2011" /> and [[multiple sclerosis]]. Some animal studies have found that [[fish oil]] increases [[dopamine]], which may be low in CFS patients.<ref name="fishoilrats1998" /><ref name="newbornratbrain2001" /><ref name="striataldopamine2011" /> ==Chronic fatigue syndrome== One study found CFS patients had low EPA/AA and Omega3/Omega 6 (Ο3/Ο6) ratios.<ref name="maes2005" /> EPA is [[fatty acid hypothesis|a theorized treatment]] for CFS owing to its immunomodulatory and anti-inflammatory effects. Trial results have been mixed. ==Autoimmune disease== A meta-analysis demonstrated significant improvements with fish oil supplementation for [[rheumatoid arthritis]] patients.<ref name="fortin1995" /> Oral supplementation of EPA and [[DHA]] induced prolonged remission of [[lupus]] in ten patients.<ref name="das1994" /> ==See also== *[[Fatty acid hypothesis]] *[[Eicosanoid]] ==References== <references> <ref name="moon2007">{{Citation| doi = 10.1016/j.intimp.2006.10.001| issn = 1567-5769| volume = 7 | issue = 2| pages = 222β229| last1 = Moon | first1 = Dong-Oh | last2 = Kim | first2 = Ki-Cheon | last3 = Jin | first3 = Cheng-Yun | last4 = Han | first4 = Min-Ho | last5 = Park | first5 = Cheol | last6 = Lee | first6 = Kyeong-Jun | last7 = Park | first7 = Yeong-Min | last8 = Choi | first8 = Yung Hyun | last9 = Kim | first9 = Gi-Young| title = Inhibitory effects of eicosapentaenoic acid on lipopolysaccharide-induced activation in BV2 microglia| journal = International Immunopharmacology| access-date = 2016-11-09| date = February 2007| url = http://www.sciencedirect.com/science/article/pii/S1567576906003067}}</ref> <ref name="hjorth2012">{{Citation| doi = 10.1097/MCO.0b013e32835017cc| issn = 1473-6519| volume = 15 | issue = 2| pages = 134β143| last1 = Hjorth | first1 = Erik | last2 = Freund-Levi | first2 = Yvonne| title = Immunomodulation of microglia by docosahexaenoic acid and eicosapentaenoic acid| journal = Current Opinion in Clinical Nutrition and Metabolic Care | date = March 2012 | pmid = 22316559}}</ref> <ref name="obata1999">{{Citation| doi = 10.1046/j.1365-2222.1999.00604.x| issn = 1365-2222| volume = 29 | issue = 8| pages = 1129β1135| last1 = Obata | last2 = Nagakura | last3 = Masaki | last4 = Maekawa | last5 = Yamashita | title = Eicosapentaenoic acid inhibits prostaglandin D2 generation by inhibiting cyclo-oxygenase-2 in cultured human mast cells| journal = Clinical & Experimental Allergy| access-date = 2016-11-09| date = 1999-08-01| url = http://onlinelibrary.wiley.com/doi/10.1046/j.1365-2222.1999.00604.x/abstract}}</ref> <ref name="chalbot2011">{{Citation| doi = 10.3233/JAD-2011-101959| issn = 1387-2877| volume = 25 | issue = 3| pages = 505β515| last1 = Chalbot | first1 = Sonia | last2 = Zetterberg | first2 = Henrik | last3 = Blennow | first3 = Kaj| last4 = Fladby | first4 = Tormod | last5 = Andreasen | first5 = Niels | last6 = Grundke-Iqbal | first6 = Inge | last7 = Iqbal | first7 = Khalid| title = Blood-Cerebrospinal Fluid Barrier Permeability in Alzheimerβs Disease| journal = Journal of Alzheimer's disease : JAD| access-date = 2016-11-09| date = 2011-01-01| url = http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3139450/| pmid = 21471645| pmc = 3139450}}</ref> <ref name="fishoilrats1998">{{Citation| issn = 0022-3166| volume = 128 | issue = 12| pages = 2512β2519| last1 = Chalon | first1 = Sylvie | last2 = Delion-Vancassel | first2 = Sylvie | last3 = Belzung | first3 = Catherine | last4 = Guilloteau | first4 = Denis | last5 = Leguisquet | first5 = Anne-Marie | last6 = Besnard | first6 = Jean-Claude | last7 = Durand | first7 = Georges| title = Dietary Fish Oil Affects Monoaminergic Neurotransmission and Behavior in Rats| journal = The Journal of Nutrition| access-date = 2016-11-09| date = 1998-12-01| url = http://jn.nutrition.org/content/128/12/2512 | pmid = 9868201}}</ref> <ref name="newbornratbrain2001">{{Citation| issn = 0022-3166| volume = 131 | issue = 1| pages = 118β122| last1 = Innis | first1 = Sheila M. | last2 = Owens | first2 = Sylvia de la Presa | title = Dietary Fatty Acid Composition in Pregnancy Alters Neurite Membrane Fatty Acids and Dopamine in Newborn Rat Brain| journal = The Journal of Nutrition| access-date = 2016-11-09| date = 2001-01-01| url = http://jn.nutrition.org/content/131/1/118 | pmid = 11208947}}</ref> <ref name="striataldopamine2011">{{Citation| doi = 10.1016/j.neulet.2011.04.009| issn = 0304-3940| volume = 496 | issue = 3| pages = 168β171| last1 = Shin | first1 = Samuel S. | last2 = Dixon | first2 = C. Edward| title = Oral fish oil restores striatal dopamine release after traumatic brain injury| journal = Neuroscience Letters| access-date = 2016-11-09| date = 2011-06-08| url = http://www.sciencedirect.com/science/article/pii/S0304394011004435}}</ref> <ref name="maes2005">{{Citation| issn = 0172-780X| volume = 26 | issue = 6| pages = 745β751| last1 = Maes | first1 = Michael | last2 = Mihaylova | first2 = Ivana | last3 = Leunis | first3 = Jean-Claude| title = In chronic fatigue syndrome, the decreased levels of omega-3 poly-unsaturated fatty acids are related to lowered serum zinc and defects in T cell activation| journal = Neuro Endocrinology Letters| date = December 2005 | pmid = 16380690}}</ref> <ref name="fortin1995">{{Citation| doi = 10.1016/0895-4356(95)00028-3| issn = 0895-4356| volume = 48 | issue = 11| pages = 1379β1390| last1 = Fortin | first1 = Paul R. | last2 = Lew | first2 = Robert A. | last3 = Liang | first3 = Matthew H. | last4 = Wright | first4 = Elizabeth A. | last5 = Beckett | first5 = Laurel A. | last6 = Chalmers | first6 = Thomas C. | last7 = Sperling | first7 = Richard I.| title = Validation of a meta-analysis: The effects of fish oil in rheumatoid arthritis| journal = Journal of Clinical Epidemiology| access-date = 2016-11-09| date = 1995-11-01| url = http://www.sciencedirect.com/science/article/pii/0895435695000283}}</ref> <ref name="das1994">{{Citation| doi = 10.1016/0952-3278(94)90136-8| issn = 0952-3278| volume = 51 | issue = 3| pages = 207β213| last = Das | first = U.N. | title = Beneficial effect of eicosapentaenoic and docosahexaenoic acids in the management of systemic lupus erythematosus and its relationship to the cytokine network| journal = Prostaglandins, Leukotrienes and Essential Fatty Acids| access-date = 2016-11-09| date = 1994-09-01| url = http://www.sciencedirect.com/science/article/pii/0952327894901368}}</ref> </references> [[Category:Potential treatments]] [[Category:Supplements]] [[Category:Fatty acids]] [[Category:Eicosanoids]] [[Category:Free fatty acids]] [[Category:Polyunsaturated fatty acids]]
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