Eicosapentaenoic acid 1593775 223698672 2008-07-05T09:28:08Z DOI bot 6652755 Citation maintenance. Formatted: title. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{Chembox new | Name = Eicosapentaenoic acid | ImageFile = EPAnumbering.png | ImageSize = 400px | ImageName = Eicosapentaenoic acid | IUPACName = (5Z,8Z,11Z,14Z,17Z)-icosa-<br />&nbsp;5,8,11,14,17-pentaenoic acid | Section1 = {{Chembox Identifiers | CASNo = 1553-41-9 | SMILES = CCC=CCC=CCC=CCC=CCC=CCCCC(=O)O }} | Section2 = {{Chembox Properties | Formula = C<sub>20</sub>H<sub>30</sub>O<sub>2</sub> | MolarMass = 302.451 g/mol | MeltingPt = }} }} '''Eicosapentaenoic acid''' (EPA or also icosapentaenoic acid) is an [[omega-3 fatty acid]]. In physiological literature, it is given the name 20:5(n-3). It also has the trivial name '''timnodonic acid'''. In chemical structure, EPA is a [[carboxylic acid]] with a 20-[[carbon]] chain and five ''[[cis]]'' double bonds; the first double bond is located at the third carbon from the omega end. :''EPA and its [[Metabolites#Metabolites|metabolites]] act in the body largely by their interactions with the metabolites of [[arachidonic acid]]; see [[Essential fatty acid interactions]] for detail.'' EPA is a [[polyunsaturated]] [[fatty acid]] that acts as a precursor for [[prostaglandin|prostaglandin-3]] (which inhibits [[platelet]] aggregation), [[thromboxane]]-3, and [[leukotriene]]-5 groups (all [[eicosanoids]]). ==Sources== It is obtained in the human diet by [[Opsophagos|eating oily fish]] or [[fish oil]]&mdash;[[cod]] liver, [[herring]], [[mackerel]], [[salmon]], [[menhaden]] and [[sardine]]. It is also found in human [[breast milk]]. However, fish do not naturally produce EPA, but obtain it from the [[algae]] they consume.<ref>{{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|author=Yvonne Bishop-Weston|accessdate=2008-08-05}}</ref> It is available from some non-animal sources&mdash;[[spirulina (dietary supplement)|spirulina]] and [[microalgae]]. Microalgae 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|author=Jess Halliday |date=12/01/2007 |accessdate=2007-02-09}}</ref> EPA is not usually found in higher plants, but it has been reported in trace amounts in [[purslane]].<ref name=SimopoulosWild>{{cite journal|url=http://www.healthyeatingclub.org/APJCN/Volume11/vol11sup6/S163.pdf |author= Simopoulos, Artemis P |year=2002|title=Omega-3 fatty acids in wild plants, nuts and seeds |journal=Asia Pacific Journal of Clinical Nutrition|volume= 11 |issue=s6|pages= S163–S173| doi=10.1046/j.1440-6047.11.s.6.5.|accessdate=2007-02-09|format={{Dead link|date=May 2008}}|doi_brokendate=2008-06-22}}</ref> Microalgae, and supplements derrived from it, are excellent alternative sources of EPA and other fatty acids, since fish often contain toxins due to pollution.<ref>{{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|author=Yvonne Bishop-Weston|accessdate=2008-08-05}}</ref> The human body can (and in case of a purely vegetarian diet often must, unless the aforementioned [[algae]] or supplements derived from them are consumed) also convert [[α-linolenic acid]] (ALA) to EPA, but this is much less efficient than the resorption of EPA from food containing it, and ALA is itself an essential fatty acid, an appropriate supply of which must be ensured. Because EPA is also a [[Precursor (chemistry)|precursor]] to [[docosahexaenoic acid]] (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 DHA. Medical conditions like [[diabetes mellitus|diabetes]] or certain allergies may significantly limit the human body's capacity for metabolization of EPA from ALA.<ref>http://www.foodsforlife.org.uk/nutrition/vegetarian-DHA-EPA.html</ref> ==Clinical significance== The US [[National Institute of Health]]'s MedlinePlus lists a large number of conditions in which EPA (alone or in concert with other ω-3 sources) is known or thought to be effective.<ref name=medline>{{cite web|url=http://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| accessmonthday= February 14 |accessyear=2006}} </ref> Most of these involve its ability to lower [[inflammation]]. Among [[omega-3 fatty acids]], in particular EPA is thought to possess beneficial potential in mental conditions, such as [[schizophrenia]].<ref name="pmid11356585">{{cite journal |author=Peet M, Brind J, Ramchand CN, Shah S, Vankar GK |title=Two double-blind placebo-controlled pilot studies of eicosapentaenoic acid in the treatment of schizophrenia | url=http://jerrycott.com/user/peet.pdf |journal=[[Schizophrenia Research]] |volume=49 |issue=3 |pages=243–51 |year=2001 |pmid=11356585 |doi= 10.1016/S0920-9964(00)00083-9|accessdate=2007-12-21}}</ref><ref>Song C., Zhao S. ''Omega-3 fatty acid eicosapentaenoic acid. A new treatment for psychiatric and neurodegenerative diseases: a review of clinical investigations.'' University of Prince Edward Island, Department of Biomedical Sciences, AVC, 550 University Avenue, Charlottetown, PE, Canada. cai.song@nrc.gc.ca (Expert Opin Investig Drugs. 2007 Oct;16(10):1627-38.) [http://www.ncbi.nlm.nih.gov/pubmed/17922626?ordinalpos=1&itool=EntrezSystem2.PEntrez.Pubmed.Pubmed_ResultsPanel.Pubmed_RVDocSum Pub-Med]</ref> Several studies report an additional reduction in scores on symptom scales used to assess the severity of symptoms, when additional EPA is taken. Recent studies have suggested that EPA may effect depression, and importantly, suicidal behavior. One such study,<ref>{{cite journal |author=Huan M, Hamazaki K, Sun Y, Itomura M, Liu H, Kang W, Watanabe S, Terasawa K, Hamazaki T. |title=Suicide attempt and n-3 fatty acid levels in red blood cells: a case control study in China | journal= Biological psychiatry |volume=56 |issue=7 |pages=490–6 |year=2004 |pmid=1540784|doi=10.1016/j.biopsych.2004.06.028|url=http://www.journals.elsevierhealth.com/periodicals/bps/article/PIIS0006322304007061/abstract |format=abstract}}</ref> took blood samples of 100 suicide-attempt patients and compared the blood samples to those of controls and found that levels of Eicosapentaenoic acid were significantly lower in the washed red blood cells of the suicide-attempt patients. EPA has inhibitory effect on [[CYP2C9]] and [[CYP2C19]] hepatic enzymes. At high dose, it may also inhibit the activity of [[CYP2D6]] and [[CYP3A4]], important enzymes involved in drug metabolism.<ref name="pmid16978661">{{cite journal |author=Yao HT, Chang YW, Lan SJ, Chen CT, Hsu JT, Yeh TK |title=The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes |journal=Life Sci. |volume=79 |issue=26 |pages=2432–40 |year=2006 |pmid=16978661 |doi=10.1016/j.lfs.2006.08.016 }}</ref> ==See also== * [[Chlorella]] * [[Cyanobacteria]] * [[Docosahexaenoic acid]] * [[List of omega-3 fatty acids]] * [[Polyunsaturated fatty acid]]s * [[Snake oil]] * [[Wakame]] ==References== [[Image:Röding, Iduns kokbok.jpg|thumb|right|250px|Salmon is a rich source of EPA.]] <references/> {{Eicosanoids}} {{Fatty acids}} [[Category:Fatty acids]] [[Category:Carboxylic acids]] [[da:Icosapentaensyre]] [[de:Eicosapentaensäure]] [[es:Ácido eicosapentaenoico]] [[fr:Acide éicosapentaènoïque]] [[nl:Eicosapentaeenzuur]] [[ja:エイコサペンタエン酸]] [[pl:Kwas eikozapentaenowy]] [[pt:Ácido eicosapentaenóico]] [[sv:EPA (fettsyra)]]