| Revision as of 13:25, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472451119 of page Eicosapentaenoic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 09:06, 27 December 2024 edit BunnysBot (talk | contribs)Bots9,311 editsm →Aerobic eukaryote pathway: Fix CW Errors with GenFixes (T1)Tag: AWB |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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| verifiedrevid = 443719931 |
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| verifiedrevid = 477000690 |
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| Name = Eicosapentaenoic acid |
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| Name = Eicosapentaenoic acid |
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| ImageFile = EPAnumbering.png |
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| ImageFile = EPAnumbering.png |
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| ImageSize = 400px |
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| ImageSize = 300px |
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| ImageName = Eicosapentaenoic acid |
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| ImageName = Eicosapentaenoic acid |
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| ImageFileL2 = Eicosapentaenoic acid spacefill.png |
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| ImageFile1 = Eicosapentaenoic acid spacefill.png |
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| ImageSize1 = 200px |
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| ImageFileR2 = Eicosapentaenoic acid2.png |
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| IUPACName = (5Z,8Z,11Z,14Z,17Z)-eicosa-<br /> 5,8,11,14,17-pentenoic acid |
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| PIN = (5''Z'',8''Z'',11''Z'',14''Z'',17''Z'')-Icosa-5,8,11,14,17-pentaenoic acid |
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| OtherNames = (5''Z'',8''Z'',11''Z'',14''Z'',17''Z'')-5,8,11,14,17-eicosapentaenoic acid |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| IUPHAR_ligand = 3362 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 393682 |
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| ChemSpiderID = 393682 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 28364 |
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| ChEBI = 28364 |
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| KEGG = C06428 |
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| PubChem = 446284 |
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| 3DMet = B00962 |
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| Beilstein = 1714433 |
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| SMILES = O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC |
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| MolarMass = 302.451 g/mol |
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| MolarMass = 302.451 g/mol |
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| HPhrases = {{H-phrases|314}} |
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'''Eicosapentaenoic acid''' ('''EPA'''; also '''icosapentaenoic acid''') is an ]. In physiological literature, it is given the name 20:5(''n''−3). It also has the ] '''timnodonic acid'''. In chemical structure, EPA is a ] with a 20-] chain and five '']'' ]s; the first double bond is located at the third carbon from the omega end. |
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EPA is a ] (PUFA) that acts as a precursor for ] (which inhibits ]), ], and ] ]s. EPA is both a precursor and the ] ] product of eicosapentaenoyl ethanolamide (EPEA: ]<sub>22</sub>]<sub>35</sub>]<sub>2</sub>; 20:5,''n''−3).<ref>{{cite journal | vauthors = Lucanic M, Held JM, Vantipalli MC, Klang IM, Graham JB, Gibson BW, Lithgow GJ, Gill MS | title = N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans | journal = Nature | volume = 473 | issue = 7346 | pages = 226–9 | date = May 2011 | pmid = 21562563 | pmc = 3093655 | doi = 10.1038/nature10007 | bibcode = 2011Natur.473..226L }}</ref> Although studies of ] supplements, which contain both ] (DHA) and EPA, have failed to support claims of preventing ] or ]s,<ref name="NYT-20150917-cz">{{cite news |last=Zimmer |first=Carl |name-list-style=vanc |author-link=Carl Zimmer |title=Inuit Study Adds Twist to Omega-3 Fatty Acids' Health Story |url=https://www.nytimes.com/2015/09/22/science/inuit-study-adds-twist-to-omega-3-fatty-acids-health-story.html |date=September 17, 2015 |work=] |access-date=October 11, 2015 |archive-date=January 9, 2019 |archive-url=https://web.archive.org/web/20190109042557/https://www.nytimes.com/2015/09/22/science/inuit-study-adds-twist-to-omega-3-fatty-acids-health-story.html |url-status=live }}</ref><ref name="NYT-20150330">{{cite news |last=O'Connor |first=Anahad |name-list-style=vanc |title=Fish Oil Claims Not Supported by Research |url=http://well.blogs.nytimes.com/2015/03/30/fish-oil-claims-not-supported-by-research/ |date=March 30, 2015 |work=The New York Times |access-date=October 11, 2015 |archive-date=May 28, 2018 |archive-url=https://web.archive.org/web/20180528110348/https://well.blogs.nytimes.com/2015/03/30/fish-oil-claims-not-supported-by-research/ |url-status=live }}</ref><ref name="JAMA-201403">{{cite journal | vauthors = Grey A, Bolland M | title = Clinical trial evidence and use of fish oil supplements | journal = JAMA Internal Medicine | volume = 174 | issue = 3 | pages = 460–2 | date = March 2014 | pmid = 24352849 | doi = 10.1001/jamainternmed.2013.12765 | url = http://archinte.jamanetwork.com/article.aspx?articleid=1787690 | doi-access = free | access-date = 2015-10-12 | archive-date = 2016-06-08 | archive-url = https://web.archive.org/web/20160608204741/http://archinte.jamanetwork.com/article.aspx?articleid=1787690 | url-status = live }}</ref> a recent multi-year study of Vascepa (], the ] ] of the ]), a prescription drug containing only EPA, was shown to reduce heart attack, stroke, and cardiovascular death by 25% relative to a placebo in those with statin-resistant hypertriglyceridemia.<ref>{{cite journal | vauthors = Bhatt DL, Steg PG, Miller M, Brinton EA, Jacobson TA, Ketchum SB, Doyle RT, Juliano RA, Jiao L, Granowitz C, Tardif JC, Ballantyne CM | title = Cardiovascular Risk Reduction with Icosapent Ethyl for Hypertriglyceridemia | journal = New England Journal of Medicine | volume = 380 | pages = 11–22 | date = January 3, 2019 | issue = 1 | doi = 10.1056/NEJMoa1812792 | pmid = 30415628 | doi-access = free }}</ref><ref name="REDUCE-IT">{{cite news |title=Vascepa® (icosapent ethyl) 26% Reduction in Key Secondary Composite Endpoint of Cardiovascular Death, Heart Attacks and Stroke Demonstrated in REDUCE-IT™ |url=https://investor.amarincorp.com/news-releases/news-release-details/vascepar-icosapent-ethyl-26-reduction-key-secondary-composite |date=November 10, 2018 |access-date=January 21, 2019 |archive-date=May 23, 2019 |archive-url=https://web.archive.org/web/20190523235050/https://investor.amarincorp.com/news-releases/news-release-details/vascepar-icosapent-ethyl-26-reduction-key-secondary-composite |url-status=dead }}</ref> |
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==Sources== |
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EPA is obtained in the human diet by eating ], e.g., ] liver, ], ], ], ] and ], various types of edible ], or by taking supplemental forms of fish oil or algae oil. It is also found in human ]. |
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Fish, like most vertebrates, can synthesize very little EPA from dietary ] (ALA).<ref>{{cite book|vauthors =((Committee on the Nutrient Requirements of Fish and Shrimp; National Research Council))|title=Nutrient requirements of fish and shrimp|date=2011|publisher=The National Academies Press|location=Washington, DC|isbn=978-0-309-16338-5}}</ref> Because of this extremely low conversion rate, fish primarily obtain it from the ] they consume.<ref name=vegan>{{cite web|url=http://www.vegetarian-dha-epa.co.uk/|title=Plant based sources of vegan & vegetarian Docosahexaenoic acid – DHA and Eicosapentaenoic acid EPA & Essential Fats|first=Yvonne|last=Bishop-Weston|name-list-style=vanc|access-date=2008-08-05|archive-url=https://web.archive.org/web/20130522103010/http://vegetarian-dha-epa.co.uk/|archive-date=2013-05-22|url-status=dead}}</ref> It is available to humans from some non-animal sources (e.g., commercially, from '']'',<ref>{{Cite journal|last1=Xie|first1=Dongming|last2=Jackson|first2=Ethel N.|last3=Zhu|first3=Quinn|date=February 2015|title=Sustainable source of omega-3 eicosapentaenoic acid from metabolically engineered Yarrowia lipolytica: from fundamental research to commercial production|journal=Applied Microbiology and Biotechnology|language=en|volume=99|issue=4|pages=1599–1610|doi=10.1007/s00253-014-6318-y|issn=0175-7598|pmc=4322222|pmid=25567511}}</ref> and from ] such as ''Nannochloropsis oculata'', ''Monodus subterraneus'', ''Chlorella minutissima'' and '']'',<ref>{{cite journal | journal = Journal of the American Oil Chemists' Society | date = 1998 | volume = 75 | issue = 3 | pages = 393–397 | title = Eicosapentaenoic acid and docosahexaenoic acid production potential of microalgae and their heterotrophic growth | first1 = Rema | last1 = Vazhappilly | first2 = Feng | last2 = Chen | name-list-style = vanc | doi=10.1007/s11746-998-0057-0| s2cid = 46917269 }}</ref><ref name="pmid22586907">{{cite journal | vauthors = Ratha SK, Prasanna R | title = Bioprospecting microalgae as potential sources of "Green Energy"—challenges and perspectives | journal = Applied Biochemistry and Microbiology | volume = 48 | issue = 2 | pages = 109–125 | date = February 2012 | pmid = 22586907 | doi = 10.1134/S000368381202010X| s2cid = 18430041 }}</ref> which are being developed as a commercial source).<ref name=water4>{{cite web|url=http://www.nutraingredients.com/news/ng.asp?n=73324-water-omega-algae|title=Water 4 to introduce algae DHA/EPA as food ingredient|first=Jess|last=Halliday|name-list-style=vanc|date=12 January 2007|access-date=2007-02-09|archive-date=2007-01-16|archive-url=https://web.archive.org/web/20070116005656/http://www.nutraingredients.com/news/ng.asp?n=73324-water-omega-algae|url-status=live}}</ref> EPA is not usually found in higher plants, but it has been reported in trace amounts in ].<ref>{{cite journal | url = http://apjcn.nhri.org.tw/server/APJCN/Volume11/vol11sup2/S163.pdf | last = Simopoulos | first = Artemis P | name-list-style = vanc | year = 2002 | title = Omega-3 fatty acids in wild plants, nuts and seeds | journal = Asia Pacific Journal of Clinical Nutrition | volume = 11 | issue = Suppl 2 | pages = S163–73 | doi = 10.1046/j.1440-6047.11.s.6.5.x | url-status = dead | archive-url = https://web.archive.org/web/20081217190429/http://apjcn.nhri.org.tw/server/APJCN/Volume11/vol11sup2/S163.pdf | archive-date = 2008-12-17 }}</ref> In 2013, it was reported that a genetically modified form of the plant ] produced significant amounts of EPA.<ref>{{cite journal | vauthors = Ruiz-Lopez N, Haslam RP, Napier JA, Sayanova O | title = Successful high-level accumulation of fish oil omega-3 long-chain polyunsaturated fatty acids in a transgenic oilseed crop | journal = The Plant Journal | volume = 77 | issue = 2 | pages = 198–208 | date = January 2014 | pmid = 24308505 | pmc = 4253037 | doi = 10.1111/tpj.12378 }}</ref><ref>{{cite journal | last = Coghlan | first = Andy | name-list-style = vanc | date = 4 January 2014 | title = Designed plant oozes vital fish oils | journal = New Scientist | volume = 221 | issue = 2950 | page = 12 | url = https://www.newscientist.com/article/mg22129503.000-designer-plants-have-vital-fish-oils-in-their-seeds.html#.Us3gItIUQUo | doi = 10.1016/s0262-4079(14)60016-6 | access-date = 26 August 2017 | archive-date = 1 June 2015 | archive-url = https://web.archive.org/web/20150601014206/http://www.newscientist.com/article/mg22129503.000-designer-plants-have-vital-fish-oils-in-their-seeds.html#.Us3gItIUQUo | url-status = live }}</ref> |
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The human body converts a portion of absorbed ] (ALA) to EPA. ALA is itself an essential fatty acid, and humans need an appropriate supply of it. The efficiency of the conversion of ALA to EPA, however, is much lower than the absorption of EPA from food containing it. Because EPA is also a ] to ] (DHA), ensuring a sufficient level of EPA on a diet containing neither EPA nor DHA is harder both because of the extra metabolic work required to synthesize EPA and because of the use of EPA to metabolize into DHA. Medical conditions like ] or certain allergies may significantly limit the human body's capacity for metabolization of EPA from ALA. |
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== Forms == |
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Commercially available dietary supplements are most often derived from fish oil and are typically delivered in the triglyceride, ethyl ester, or phospholipid form of EPA. There is debate among supplement manufacturers about the relative advantages and disadvantages of the different forms. One form found naturally in algae, the polar lipid form, has been shown to have improved bioavailability over the ethyl ester or triglyceride form.<ref>{{cite journal | pmid=23855409 | year=2013 | last1=Kagan | first1=M. L. | last2=West | first2=A. L. | last3=Zante | first3=C. | last4=Calder | first4=P. C. | title=Acute appearance of fatty acids in human plasma--a comparative study between polar-lipid rich oil from the microalgae Nannochloropsis oculata and krill oil in healthy young males | journal=Lipids in Health and Disease | volume=12 | page=102 | doi=10.1186/1476-511X-12-102 | pmc=3718725 | doi-access=free }}</ref> Similarly, DHA or EPA in the ] (LPC) form was found to be more efficient than triglyceride and ]s (PC) in a 2020 study.<ref>{{cite journal |last1=Sugasini |first1=D |last2=Yalagala |first2=PCR |last3=Goggin |first3=A |last4=Tai |first4=LM |last5=Subbaiah |first5=PV |title=Enrichment of brain docosahexaenoic acid (DHA) is highly dependent upon the molecular carrier of dietary DHA: lysophosphatidylcholine is more efficient than either phosphatidylcholine or triacylglycerol. |journal=The Journal of Nutritional Biochemistry |date=December 2019 |volume=74 |pages=108231 |doi=10.1016/j.jnutbio.2019.108231 |pmid=31665653 |pmc=6885117}}</ref> |
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{| class="wikitable sortable" style="width: auto;" |
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! Base |
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! EPA |
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! ] |
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| ] |
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! ] (LPC, or lysoPC) |
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| LPC-EPA, or lysoPC-EPA |
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! ] (PC) |
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| EPA-PC |
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! ] (PL) |
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| EPA-PL |
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! ] (TG) or triacylglycerol (TAG) |
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| EPA-TG, or EPA-TAG |
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! Re-esterified ] (rTG), or re-esterified triacylglycerol (rTAG) |
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| EPA rTG, or r-TAG |
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== Biosynthesis == |
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=== Aerobic eukaryote pathway === |
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]]] |
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Aerobic eukaryotes, specifically microalgae, ]es, ], and most animals (including humans), perform biosynthesis of EPA usually as a series of desaturation and elongation reactions, catalyzed by the sequential action of desaturase and elongase ]s. This pathway, originally identified in ''Thraustochytrium'', applies to these groups:<ref name=Qiu>{{Cite journal|date=2003-02-01|last=Qiu |first=Xiao |title=Biosynthesis of docosahexaenoic acid (DHA, 22:6-4, 7,10,13,16,19): two distinct pathways|journal=Prostaglandins, Leukotrienes and Essential Fatty Acids |volume=68|issue=2|pages=181–186|doi=10.1016/S0952-3278(02)00268-5|issn=0952-3278|pmid=12538082}}</ref> |
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# a desaturation at the sixth carbon of ] by a ] to produce ] (SDA, 18:4 ω-3), |
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# elongation of the ] by a Δ6 elongase to produce ] (ETA, 20:4 ω-3), |
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# desaturation at the fifth carbon of ] by a ] to produce eicosapentaenoic acid (EPA, 20:5 ω-3), |
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{{clear}} |
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=== Polyketide synthase pathway === |
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] |
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Marine bacteria and the microalgae '']'' use an anerobic ] (PKS) pathway to synthesize DHA.<ref name=Qiu/> The PKS pathway includes six enzymes namely, 3-ketoacyl synthase (KS), 2 ketoacyl-]-reductase (KR), dehydrase (DH), enoyl reductase (ER), dehydratase/2-trans 3-cos isomerase (DH/2,3I), dehydratase/2-trans, and 2-cis isomerase (DH/2,2I). The biosynthesis of EPA varies in marine species, but most of the marine species' ability to convert C18 ] to LC-PUFA is dependent on the fatty acyl desaturase and elongase enzymes. The molecule basis of the enzymes will dictate where the double bond is formed on the resulting molecule.<ref>{{cite journal |last1=Monroig |first1=Óscar |last2=Tocher |first2=Douglas |last3=Navarro |first3=Juan |title=Biosynthesis of Polyunsaturated Fatty Acids in Marine Invertebrates: Recent Advances in Molecular Mechanisms |journal=Marine Drugs |date=2013-10-21 |volume=11 |issue=10 |pages=3998–4018 |doi=10.3390/md11103998 |pmid=24152561 |pmc=3826146|doi-access=free }}</ref> |
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The proposed polyketide synthesis pathway of EPA in '']'' (a marine bacterium) is a repetitive reaction of reduction, dehydration, and condensation that uses acetyl-CoA and malonyl-CoA as building blocks. The mechanism of α-linolenic acid to EPA involves the condensation of malonyl-CoA to the pre-existing α-linolenic acid by KS. The resulting structure is converted by NADPH dependent reductase, KR, to form an intermediate that is dehydrated by the DH enzyme. The final step is the NADPH-dependent reduction of a double bond in trans-2-enoyl-ACP via ER enzyme activity. The process is repeated to form EPA.<ref>{{cite journal |last1=Moi |first1=Ibrahim Musa |last2=Leow |first2=Adam Thean Chor |last3=Ali |first3=Mohd Shukuri Mohamad |last4=Rahman |first4=Raja Noor Zaliha Raja Abd. |last5=Salleh |first5=Abu Bakar |last6=Sabri |first6=Suriana |title=Polyunsaturated fatty acids in marine bacteria and strategies to enhance their production |url=https://www.researchgate.net/publication/325068654 |journal=Applied Microbiology and Biotechnology |date=July 2018 |volume=102 |issue=14 |pages=5811–5826 |doi=10.1007/s00253-018-9063-9|pmid=29749565 |s2cid=13680225 }}</ref> |
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{{clear}} |
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==Clinical significance== |
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{{Further|Essential fatty acid interactions}} |
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] is a rich source of EPA.]] |
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The US ]'s MedlinePlus lists medical conditions for which EPA (alone or in concert with other ω-3 sources) is known or thought to be an effective treatment.<ref>{{cite web|url=https://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-fishoil.html |title=MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid |author=NIH Medline Plus |access-date=February 14, 2006 |url-status=dead |archive-url=https://web.archive.org/web/20060208023339/http://www.nlm.nih.gov/medlineplus/druginfo/natural/patient-fishoil.html |archive-date=February 8, 2006 }}</ref> Most of these involve its ability to lower ]. |
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Intake of large doses (2.0 to 4.0 g/day) of long-chain omega−3 fatty acids as prescription drugs or dietary supplements are generally required to achieve significant (> 15%) lowering of triglycerides, and at those doses the effects can be significant (from 20% to 35% and even up to 45% in individuals with levels greater than 500 mg/dL). |
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Dietary supplements containing EPA and DHA lower triglycerides in a dose dependent manner; however, DHA appears to raise ] (the variant which drives atherosclerosis, sometimes inaccurately called "bad cholesterol") and ] values (a measurement/estimate of the cholesterol mass within LDL-particles), while EPA does not. This effect has been seen in several ] that combined hundreds of individual clinical trials in which both EPA and DHA were part of a high dose omega−3 supplement, but it is when EPA and DHA are given separately that the difference can be seen clearly.<ref>{{cite journal |last1=AbuMweis |first1=S |last2=Jew |first2=S |last3=Tayyem |first3=R |last4=Agraib |first4=L |title=Eicosapentaenoic acid and docosahexaenoic acid containing supplements modulate risk factors for cardiovascular disease: a meta-analysis of randomised placebo-control human clinical trials. |journal=Journal of Human Nutrition and Dietetics |date=February 2018 |volume=31 |issue=1 |pages=67–84 |doi=10.1111/jhn.12493 |pmid=28675488|s2cid=8793334 |doi-access=free }}</ref><ref>{{cite journal |last1=Chen |first1=H |last2=Deng |first2=G |last3=Zhou |first3=Q |last4=Chu |first4=X |last5=Su |first5=M |last6=Wei |first6=Y |last7=Li |first7=L |last8=Zhang |first8=Z |title=Effects of eicosapentaenoic acid and docosahexaenoic acid versus α-linolenic acid supplementation on cardiometabolic risk factors: a meta-analysis of randomized controlled trials. |journal=Food & Function |date=26 March 2020 |volume=11 |issue=3 |pages=1919–1932 |doi=10.1039/c9fo03052b |pmid=32175534|s2cid=212730542 }}</ref> For example, in a study by Schaefer and colleagues of Tufts Medical School, patients were given either 600 mg/day DHA alone, 600 or 1800 mg/day EPA alone, or placebo for six weeks. The DHA group showed a significant 20% drop in triglycerides and an 18% increase in LDL-C, but in the EPA groups modest drops in triglyceride were not considered statistically significant and no changes in LDL-C levels were found with either dose.<ref>{{cite journal |last1=Asztalos |first1=IB |last2=Gleason |first2=JA |last3=Sever |first3=S |last4=Gedik |first4=R |last5=Asztalos |first5=BF |last6=Horvath |first6=KV |last7=Dansinger |first7=ML |last8=Lamon-Fava |first8=S |last9=Schaefer |first9=EJ |title=Effects of eicosapentaenoic acid and docosahexaenoic acid on cardiovascular disease risk factors: a randomized clinical trial. |journal=Metabolism: Clinical and Experimental |date=November 2016 |volume=65 |issue=11 |pages=1636–1645 |doi=10.1016/j.metabol.2016.07.010 |pmid=27733252}}</ref> |
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Ordinary consumers commonly obtain EPA and DHA from foods such as fatty fish,{{efn|1=Cooked salmon contain 500–1,500 mg DHA and 300–1,000 mg EPA per 100 grams of fish. See page: ].}} fish oil dietary supplements,{{efn|1=Omega−3 dietary oil supplements have no standard doses and generally salmon oil has more DHA than EPA while other white fishes have more EPA than DHA. One producer, , for example reports per serving DHA 220 mg and EPA 180 mg for their salmon oil (total omega−3 = 600 mg), but DHA 144 mg and EPA 356 mg for pollock fish oil (total omega−3 = 530 mg). Equivalent products from another producer, , reports DHA 180 mg and EPA 150 mg for their salmon oil product (total omega−3 = 420 mg), but DHA 204 mg and EPA 318 mg for fish oil derived from anchovy, sardine, and mackerel (total omega−3 = 600 mg). For information and comparison purposes only, no endorsements are implied. }} and less commonly from ] supplements{{efn|1=Many plant sources of omega−3s are rich in ALA but completely lack EPA and DHA. The exception is algae derived oils. Because there are more commercially-grown algae sources of DHA than EPA, algae omega−3 supplements typically contain more DHA than EPA. For example, reports per serving DHA 390 mg and EPA 195 mg (total omega−3 = 715 mg), reports DHA 300 mg and EPA 150 mg (total omega−3 = 550 mg) and so on, but reports EPA 250 mg (total omega−3 = 254 mg). For information and comparison purposes only, no endorsements are implied.}} in which the omega−3 doses are lower than those in clinical experiments. A Cooper Center Longitudinal Study that followed 9253 healthy men and women over 10 years revealed that those who took fish oil supplements did not see raised LDL-C levels.<ref>{{cite journal |last1=Harris |first1=WS |last2=Leonard |first2=D |last3=Radford |first3=NB |last4=Barlow |first4=CE |last5=Steele |first5=MR |last6=Farrell |first6=SW |last7=Pavlovic |first7=A |last8=Willis |first8=BL |last9=DeFina |first9=LF |title=Increases in erythrocyte DHA are not associated with increases in LDL-cholesterol: Cooper center longitudinal study. |journal=Journal of Clinical Lipidology |date=January 2021 |volume=15 |issue=1 |pages=212–217 |doi=10.1016/j.jacl.2020.11.011 |pmid=33339757|s2cid=229325648 }}</ref> In fact, there was a very slight ''decrease'' of LDL-C which was statistically significant but too small to be of any clinical significance. These individuals took fish oil supplements of their own choosing, and it should be recognized that the amounts and ratios of EPA and DHA vary according to the source of fish oil. |
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Omega−3 fatty acids, particularly EPA, have been studied for their effect on ] (ASD). Some have theorized that, since omega−3 fatty acid levels may be low in children with autism, supplementation might lead to an improvement in symptoms. While some uncontrolled studies have reported improvements, well-controlled studies have shown no statistically significant improvement in symptoms as a result of high-dose omega−3 supplementation.<ref name=":0">{{cite journal | vauthors = Bent S, Bertoglio K, Hendren RL | title = Omega-3 fatty acids for autistic spectrum disorder: a systematic review | journal = Journal of Autism and Developmental Disorders | volume = 39 | issue = 8 | pages = 1145–54 | date = August 2009 | pmid = 19333748 | pmc = 2710498 | doi = 10.1007/s10803-009-0724-5 }}</ref><ref>{{cite journal | vauthors = Mankad D, Dupuis A, Smile S, Roberts W, Brian J, Lui T, Genore L, Zaghloul D, Iaboni A, Marcon PM, Anagnostou E | title = A randomized, placebo controlled trial of omega-3 fatty acids in the treatment of young children with autism | journal = Molecular Autism | volume = 6 | pages = 18 | date = 2015-03-21 | pmid = 25798215 | pmc = 4367852 | doi = 10.1186/s13229-015-0010-7 | doi-access = free }}</ref> |
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In addition, studies have shown that omega−3 fatty acids may be useful for treating ].<ref>{{cite journal |last1=Freeman |first1=Marlene P. |last2=Hibbeln |first2=Joseph R. |last3=Wisner |first3=Katherine L. |last4=Davis |first4=John M. |last5=Mischoulon |first5=David |last6=Peet |first6=Malcolm |last7=Keck |first7=Paul E. |last8=Marangell |first8=Lauren B. |last9=Richardson |first9=Alexandra J. |last10=Lake |first10=James |last11=Stoll |first11=Andrew L. |title=Omega-3 fatty acids: evidence basis for treatment and future research in psychiatry |journal=The Journal of Clinical Psychiatry |date=December 2006 |volume=67 |issue=12 |pages=1954–1967 |doi=10.4088/jcp.v67n1217 |pmid=17194275 |url=https://pubmed.ncbi.nlm.nih.gov/17194275/ |issn=1555-2101 |access-date=2022-10-13 |archive-date=2020-09-20 |archive-url=https://web.archive.org/web/20200920045905/https://pubmed.ncbi.nlm.nih.gov/17194275/ |url-status=live }}</ref><ref>{{cite web |last1=Ilardi |first1=Stephen |title=Therapeutic Lifestyle Change. A new treatment for depression |url=http://tlc.ku.edu/elements |website=Therapeutic Lifestyle Change (TLC) |date=28 April 2015 |access-date=9 November 2019 |language=en |quote=We were never designed for the sedentary, indoor, sleep-deprived, socially-isolated, fast-food-laden, frenetic pace of modern life. |archive-date=9 November 2019 |archive-url=https://web.archive.org/web/20191109184424/http://tlc.ku.edu/elements |url-status=live }}</ref> |
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EPA and DHA ]s (all forms) may be absorbed less well, thus work less well, when taken on an empty stomach or with a low-fat meal.<ref name="NLApt2-2015">{{cite journal | vauthors = Jacobson TA, Maki KC, Orringer CE, Jones PH, Kris-Etherton P, Sikand G, La Forge R, Daniels SR, Wilson DP, Morris PB, Wild RA, Grundy SM, Daviglus M, Ferdinand KC, Vijayaraghavan K, Deedwania PC, Aberg JA, Liao KP, McKenney JM, Ross JL, Braun LT, Ito MK, Bays HE, Brown WV, Underberg JA | title = National Lipid Association Recommendations for Patient-Centered Management of Dyslipidemia: Part 2 | journal = Journal of Clinical Lipidology | volume = 9 | issue = 6 Suppl | pages = S1–122.e1 | year = 2015 | pmid = 26699442 | doi = 10.1016/j.jacl.2015.09.002 | doi-access = free }}</ref> |
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== Notes == |
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{{notelist}} |
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== References == |
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{{Reflist|25em}} |
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== External links == |
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* in the ] |
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*; ] (20:5, n-3); EPEA. - ] |
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{{Eicosanoids}} |
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{{Fatty acids}} |
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{{Mood stabilizers }} |
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{{Authority control}} |
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] |
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] |