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{{further|Essential fatty acid interactions}}
{{further|Essential fatty acid interactions}}
[[Image:Röding, Iduns kokbok.jpg|thumb|right|250px|[[Salmon]] is a rich source of EPA.]]
[[Image:Röding, Iduns kokbok.jpg|thumb|right|250px|[[Salmon]] is a rich source of EPA.]]
The US [[National Institute of Health]]'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=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| accessdate= February 14, 2006 }}{{Dead link|date=October 2015}}</ref> Most of these involve its ability to lower [[inflammation]].
The US [[National Institute of Health]]'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=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 |accessdate=February 14, 2006 |deadurl=yes |archiveurl=https://web.archive.org/20060208023339/http://www.nlm.nih.gov:80/medlineplus/druginfo/natural/patient-fishoil.html |archivedate=February 8, 2006 }}</ref> Most of these involve its ability to lower [[inflammation]].


Among [[omega-3 fatty acids]], it is thought that EPA in particular may possess some beneficial potential in mental conditions, such as [[schizophrenia]].<ref>{{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 |
Among [[omega-3 fatty acids]], it is thought that EPA in particular may possess some beneficial potential in mental conditions, such as [[schizophrenia]].<ref>{{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 |

Revision as of 14:51, 10 January 2016

Eicosapentaenoic acid
Eicosapentaenoic acid
Names
IUPAC name
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.117.069 Edit this at Wikidata
UNII
  • InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15- checkY
    Key: JAZBEHYOTPTENJ-JLNKQSITSA-N checkY
  • InChI=1/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
    Key: JAZBEHYOTPTENJ-JLNKQSITBZ
  • O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
Properties
C20H30O2
Molar mass 302.451 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 is a polyunsaturated fatty acid (PUFA) that acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 eicosanoids. Studies of fish oil supplements, which contain EPA, have failed to support claims of preventing heart attacks or strokes.[1][2][3]

Sources

It is obtained in the human diet by eating oily fish or fish oil, e.g. cod liver, herring, mackerel, salmon, menhaden and sardine, and various types of edible seaweed and phytoplankton. It is also found in human breast milk.

However, fish can either synthesize EPA from fatty acids precursors found in their alimentation[4] or obtain it from the algae they consume.[5] It is available to humans from some non-animal sources (e.g. commercially, from microalgae, which are being developed as a commercial source).[6] EPA is not usually found in higher plants, but it has been reported in trace amounts in purslane.[7] In 2013, it was reported that a genetically modified form of the plant Camelina produced significant amounts of EPA.[8][9]

The human body converts alpha-linolenic acid (ALA) to EPA. ALA is itself an essential fatty acid, an appropriate supply of which must be ensured. 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 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 into DHA. Medical conditions like diabetes or certain allergies may significantly limit the human body's capacity for metabolization of EPA from ALA.

Clinical significance

Further information: Essential fatty acid interactions
Salmon is a rich source of EPA.

The US National Institute of Health'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.[10] Most of these involve its ability to lower inflammation.

Among omega-3 fatty acids, it is thought that EPA in particular may possess some beneficial potential in mental conditions, such as schizophrenia.[11][12]

Studies have suggested that EPA may be efficacious in treating depression. A 2009 meta-analysis found that people taking omega-3 supplements with a higher EPA:DHA ratio experienced fewer depressive symptoms.[13]

EPA has an inhibitory effect on CYP2C9 and CYP2C19 hepatic enzymes. At a high dose, it may also inhibit the activity of CYP2D6 and CYP3A4, important enzymes involved in drug metabolism.[14]

Research suggests that EPA improves the response of patients to chemotherapy, possibly by modulating the production of eicosanoid.[15]

References

  1. ^ Zimmer, Carl (September 17, 2015). "Inuit Study Adds Twist to Omega-3 Fatty Acids' Health Story". New York Times. Retrieved October 11, 2015.
  2. ^ O'Connor, Anahad (March 30, 2015). "Fish Oil Claims Not Supported by Research". New York Times. Retrieved October 11, 2015.
  3. ^ Grey, Andrew; Bolland, Mark (March 2014). "Clinical Trial Evidence and Use of Fish Oil Supplements". JAMA Internal Medicine. 174 (3): 460–462. doi:10.1001/jamainternmed.2013.12765. Retrieved October 11, 2015.
  4. ^ Committee on the Nutrient Requirements of Fish and Shrimp; National Research Council (2011). Nutrient requirements of fish and shrimp. Washington, DC: The National Academies Press. ISBN 0-309-16338-2.{{cite book}}: CS1 maint: multiple names: authors list (link)
  5. ^ Yvonne Bishop-Weston. "Plant based sources of vegan & vegetarian Docosahexaenoic acid - DHA and Eicosapentaenoic acid EPA & Essential Fats". Retrieved 2008-08-05.
  6. ^ Jess Halliday (12 January 2007). "Water 4 to introduce algae DHA/EPA as food ingredient". Retrieved 2007-02-09.
  7. ^ Simopoulos, Artemis P (2002). "Omega-3 fatty acids in wild plants, nuts and seeds" (PDF). Asia Pacific Journal of Clinical Nutrition. 11 (Suppl 2): S163–73. doi:10.1046/j.1440-6047.11.s.6.5.x.
  8. ^ Ruiz-Lopez, N.; Haslam, R. P.; Napier, J. A.; Sayanova, O. (January 2014). "Successful high-level accumulation of fish oil omega-3 long-chain polyunsaturated fatty acids in a transgenic oilseed crop". The Plant Journal. 77 (2): 198–208. doi:10.1111/tpj.12378.
  9. ^ Coghlan, Andy (4 January 2014) "Designed plant oozes vital fish oils"' New Scientist, volume 221, issue 2950, page 12, also available on the Internet at [1]
  10. ^ NIH Medline Plus. "MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid". Archived from the original on February 8, 2006. Retrieved February 14, 2006. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  11. ^ Peet M, Brind J, Ramchand CN, Shah S, Vankar GK (2001). "Two double-blind placebo-controlled pilot studies of eicosapentaenoic acid in the treatment of schizophrenia" (PDF). Schizophrenia Research. 49 (3): 243–51. doi:10.1016/S0920-9964(00)00083-9. PMID 11356585.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  12. ^ Song C, Zhao S (Oct 2007). "Omega-3 fatty acid eicosapentaenoic acid. A new treatment for psychiatric and neurodegenerative diseases: a review of clinical investigations". Expert Opin Investig Drugs. 16 (10): 1627–38. doi:10.1517/13543784.16.10.1627. PMID 17922626.
  13. ^ Martins, JG (Oct 2009). "EPA but not DHA appears to be responsible for the efficacy of omega-3 long chain polyunsaturated fatty acid supplementation in depression: evidence from a meta-analysis of randomized controlled trials". Journal of the American College of Nutrition. 28 (5): 525–42. doi:10.1080/07315724.2009.10719785. PMID 20439549.
  14. ^ Yao HT, Chang YW, Lan SJ, Chen CT, Hsu JT, Yeh TK (2006). "The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes". Life Sci. 79 (26): 2432–40. doi:10.1016/j.lfs.2006.08.016. PMID 16978661.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  15. ^ Hardman,W Elaine (2004). "(n-3)Fatty Acids and Cancer Therapy". Journal of Nutrition. 134 (12): 3427S–3430S. PMID 15570049.
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