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street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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Environmental Protection Agency(米国)環境保護庁
酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/29 13:56:19」(JST)

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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.

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 do not naturally produce EPA, but obtain it from the algae they consume.^[1] It is available to humans from some non-animal sources (e.g. commercially, from microalgae, which are being developed as a commercial source).^[2] EPA is not usually found in higher plants, but it has been reported in trace amounts in purslane.^[3] In 2013, it was reported that a genetically modified form of the plant Camelina produced significant amounts of EPA.^[4]^[5]

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

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.^[6] 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.^[7]^[8]

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.^[9]

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.^[10]

Research suggests that EPA improves the response of patients to chemotherapy, possibly by modulating the production of eicosanoid.^[11]

References

^ Yvonne Bishop-Weston. "Plant based sources of vegan & vegetarian Docosahexaenoic acid - DHA and Eicosapentaenoic acid EPA & Essential Fats". Retrieved 2008-08-05.
^ Jess Halliday (12 January 2007). "Water 4 to introduce algae DHA/EPA as food ingredient". Retrieved 2007-02-09.
^ 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.
^ 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.
^ 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]
^ NIH Medline Plus. "MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid". Retrieved February 14, 2006.
^ 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.
^ 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.
^ 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.
^ 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.
^ Hardman,W Elaine (2004). "(n-3)Fatty Acids and Cancer Therapy". Journal of Nutrition 134 (12): 3427S–3430S. PMID 15570049.

UpToDate Contents

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English Journal

Influence of encapsulated functional lipids on crystal structure and chemical stability in solid lipid nanoparticles: Towards bioactive-based design of delivery systems.

Salminen H1, Gömmel C2, Leuenberger BH3, Weiss J2.
Food chemistry.Food Chem.2016 Jan 1;190:928-37. doi: 10.1016/j.foodchem.2015.06.054. Epub 2015 Jun 19.
We investigated the influence of physicochemical properties of encapsulated functional lipids--vitamin A, β-carotene and ω-3 fish oil--on the structural arrangement of solid lipid nanoparticles (SLN). The relationship between the crystal structure and chemical stability of the incorporated bioacti
PMID 26213058

Eicosapentaenoic Acid as long-term secondary prevention after ischemic stroke.

Nakase T1, Sasaki M, Suzuki A.
Clinical and translational medicine.Clin Transl Med.2015 Dec;4(1):62. doi: 10.1186/s40169-015-0062-5. Epub 2015 Jun 11.
BACKGROUND: It is sometimes difficult to choose anti-thrombotic agents for secondary prevention in stroke patients at high bleeding risk. Recently, Eicosapentaenoic Acid (EPA) was reported to reduce the recurrence of stroke in hypercholesterolemic patients without increasing hemorrhagic risk. In thi
PMID 26084813

Selective transfer of polyunsaturated fatty acids from phytoplankton to planktivorous fish in large boreal lakes.

Strandberg U1, Hiltunen M1, Jelkänen E1, Taipale SJ1, Kainz MJ2, Brett MT3, Kankaala P1.
The Science of the total environment.Sci Total Environ.2015 Dec 1;536:858-65. doi: 10.1016/j.scitotenv.2015.07.010. Epub 2015 Aug 14.
Lake size influences various hydrological parameters, such as water retention time, circulation patterns and thermal stratification that can consequently affect the plankton community composition, benthic-pelagic coupling and the function of aquatic food webs. Although the socio-economical (particul
PMID 26282609

Japanese Journal

Wing (Ib) cells in frog taste discs detect dietary unsaturated fatty acids

Okada Yukio,Miyazaki Toshihiro,Fujiyama Rie,Toda Kazuo
Comparative Biochemistry and Physiology Part A: Molecular & Integrative Physiology 166(3), 434-440, 2013-11-00
… Applying arachidonic acid to the bath induced monophasic inward currents in 60% of wing cells and biphasic inward and outward currents in the other cells. … The intracellular dialysis of arachidonic acid did not induce an inward current; … Oleic, eicosapentaenoic and docosahexaenoic acids elicited the same inward currents as those of arachidonic acid. …
NAID 120005328272

Oxidized eicosapentaenoic acids more potently reduce LXRα-induced cellular triacylglycerol via suppression of SREBP-1c, PGC-1β and GPA than its intact form.

Nanthirudjanar Tharnath,Furumoto Hidehiro,Hirata Takashi,Sugawara Tatsuya
Lipids in health and disease 12, 2013-05-00
… Dietary polyunsaturated fatty acids (PUFA), especially eicosapentaenoic acid (EPA), improve lipid metabolism and contribute to the prevention of vascular diseases such as atherosclerosis. …
NAID 120005296013

The Assessment of Risk for Gastrointestinal Injury with Anticoagulant and Antiplatelet Drugs : The Possible Beneficial Effect of Eicosapentaenoic Acid for the Risk of Gastrointestinal Injury

Tanaka Mamoru,Tanaka Akihiro,Suemaru Katsuya [他]
Biological & pharmaceutical bulletin 36(2), 222-227, 2013-02-00
NAID 40019558431

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★リンクテーブル★

リンク元	「エイコサペンタエン酸」「EPA」

「エイコサペンタエン酸」

Eicosapentaenoic acid
Names
	IUPAC name (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid
Identifiers
CAS Registry Number	10417-94-4
ChEBI	CHEBI:28364
ChEMBL	ChEMBL460026
ChemSpider	393682
DrugBank	DB00159
	InChI 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- ; Key: JAZBEHYOTPTENJ-JLNKQSITSA-N ; 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 ;
IUPHAR/BPS	3362
Jmol-3D images	Image
	SMILES O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ;
UNII	AAN7QOV9EA
Properties
Chemical formula	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).
	verify (what is: /?)
	Infobox references

　　[★]

英: eicosapentaenoic acid EPA
同: イコサペンタエン酸 icosapentaenoic acid IPA
関: ω3脂肪酸、ω6脂肪酸

「EPA」

　　[★]

エイコサペンタエン酸 eicosapentaenoic acid 5,8,11,14,17-icosapentaenoate
Environmental Protection Agency

[vegan-1] Yvonne Bishop-Weston. "Plant based sources of vegan & vegetarian Docosahexaenoic acid - DHA and Eicosapentaenoic acid EPA & Essential Fats". Retrieved 2008-08-05.

[water4-2] Jess Halliday (12 January 2007). "Water 4 to introduce algae DHA/EPA as food ingredient". Retrieved 2007-02-09.

[3] 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.

[4] 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.

[5] 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]

[6] NIH Medline Plus. "MedlinePlus Herbs and Supplements: Omega-3 fatty acids, fish oil, alpha-linolenic acid". Retrieved February 14, 2006.

[7] 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.

[8] 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.

[9] 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.

[10] 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.

[11] Hardman,W Elaine (2004). "(n-3)Fatty Acids and Cancer Therapy". Journal of Nutrition 134 (12): 3427S–3430S. PMID 15570049.

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eicosapentaenoic acid