花生五烯酸

二十碳五烯酸
	IUPAC名; (5Z,8Z,11Z,14Z,17Z)-icosa-; 5,8,11,14,17-pentaenoic acid; 順,順,順,順,順-5,8,11,14,17-二十碳五烯酸
識別
CAS號	10417-94-4
ChemSpider	393682
SMILES	O=C(O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC;
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-;
InChIKey	JAZBEHYOTPTENJ-JLNKQSITBZ
ChEBI	28364
DrugBank	DB00159
IUPHAR配體	3362
性質
化學式	C20H30O2
摩爾質量	302.451 g·mol⁻¹
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

花生五烯酸，也成為全順式二十碳五烯酸（英語：Eicosapentaenoic acid, EPA）是有五個雙鍵的多元不飽和脂肪酸（C₂₀H₃₀O₂），是一種ω-3脂肪酸。

來源

在人類飲食中，這種脂肪酸主要來源於食用脂肪含量高的魚類和魚油，例如鱈魚肝、青魚、鯖魚、鮭魚、鯡魚、沙丁魚和多種可食用海草和浮游植物；在人類母乳中亦存在此種脂肪酸。

但是魚類自身並不合成EPA，而是通過食用海藻攝取^[1]。人類也可通過非動物性來源獲取EPA，例如微藻類。此類植物亦被培養成為一個商業化的EPA來源^[2]。EPA在高大植物中不常見，但是有報道稱馬齒莧含微量EPA^[3]。2013年曾有報道指出亞麻薺屬植物的一種基因改造變種含有大量EPA^[4]^[5]。

人體能夠利用α-亞麻酸（ALA）合成自身所需的EPA。ALA是人體的一種必需脂肪酸，必須確保充足的攝入。但是，將ALA轉化至EPA的效率遠低於從食物中直接攝取，因為EPA本身也用於進一步合成二十二碳六烯酸（DHA）。人體很難從不含EPA和DHA的食物中間接獲取足夠量的EPA，因為：1.身體需要額外的代謝過程來合成EPA; 2.EPA同時又被用於合成DHA。某些疾病或者特殊條件會顯着地降低身體從ALA合成EPA的能力，例如糖尿病或者一些過敏反應。

臨床意義

美國國家衛生研究院的MedlinePlus數據庫列出了EPA（單獨使用或聯合其他omega-3脂肪酸使用）能夠有效治療的疾病^[6]。大多數情況下EPA被證明對發炎症狀有效。

在所有omega-3脂肪酸中，EPA被認為對一些精神方面的疾病有潛在的療效，例如精神分裂症^[7]^[8]。

有研究表明EPA有可能對改進抑鬱狀態有幫助。2009年的一個綜合研究發現攝取更高EPA:DHA比例的omega-3補充劑的病人較少出現抑鬱症狀^[9]。

對人體健康的影響

總體效果

攝入脂肪酸對慢性病的影響被廣泛認可，這些疾病包括肥胖症、糖尿病、癌症、關節炎、哮喘和心血管疾病^[10]。

對神經系統的影響

足夠的脂肪酸攝入（特別是EPA和DHA）對胎兒神經系統發育成熟的重要性如今已被證明^[11]。

炎症

一個研究表明魚油（通常含有較高的EPA和DHA含量）可以通過影響多種發炎反應的機理而預防這類疾病^[12]。

心血管疾病

對於心血管方面的疾病，EPA和DHA被證明對改進以下症狀有效^[13]:

癌症

多個研究表明，EPA或DHA攝入對乳腺癌或者前列腺癌的影響取決於同時攝入的omega-6脂肪酸和抗氧化劑^[14]^[15]。EPA亦對預防直腸結腸癌有效果^[16]。

參考來源

^ Yvonne Bishop-Weston. "Plant based sources of vegan & vegetarian Docosahexaenoic acid - DHA and Eicosapentaenoic acid EPA & Essential Fats". Retrieved 2008-08-05.
^ Jess Halliday (12/01/2007). "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". Asia Pacific Journal of Clinical Nutrition 11 (Suppl 2): S163–73.
^ 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.
^ Coghlan, Andy (4 January 2014) "Designed plant oozes vital fish oils"' New Scientist, volume 221, issue 2950, page 12.
^ 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". Schizophrenia Research 49 (3): 243–51.
^ 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.
^ 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.
^ Recent trends in the advanced analysis of bioactive fatty acids.Ruiz-Rodriguez A, Reglero G, Ibañez E.Departamento de Caracterización de Alimentos, Instituto de Fermentaciones Industriales, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain.
^ Ghisolfi J., 1997. Acides gras, croissance fœtale et grossesse. Arch Pediatr 1997;4 (suppl 2):133s-5s.
^ Fish oil lipid emulsions and immune response: what clinicians need to know.Waitzberg DL, Torrinhas RS.Faculdade de Medicina da Universidade de São Paulo, Avenida Dr Arnaldo, 455-2 degrees andar, sala 2108, CEP: 01245-903, São Paulo, SP, Brasil; PMID 19605803 [archive] [PubMed - in process]
^ Cardiovascular disease prevention and treatment.von Schacky C.Preventive Cardiology, Medizinische Clinic and Policlinic Innenstadt, University of Munich, Ziemssensstr. 1, D-80336 Munich, Germany; Omegametrix, Am Klopferspitz 19, D-82152 Martinsried, Germany. PMID 19520557 [archive] [PubMed - as supplied by publisher]
^ Bagga D, Anders KH, Wang HJ, Glaspy JA. Long-chain n-3-to-n-6 polyunsaturated fatty acid ratios in breast adipose tissue from women with and without breast cancer. Nutr Cancer 42, (2002) 180-5.
^ Leitzmann MF, Stampfer MJ, Michaud DS, Augustsson KA, Colditz GC, Willett WC, Giovannucci EL., 2004. Dietray intake of n-3 and n-6 fatty acids and the risk of prostate cancer. Am J Clin Nutr; 80 : 204-216.
^ Courtney, E.D., Matthews, S., Finlayson,C., Di Pierro, D., Belluzzi, A., Roda, E., Kang, J.Y., and Leicester, R.J., 2007. Eicosapentaenoic acid (EPA) reduces crypt cell proliferation and increases apoptosis in normal colonic mucosa in subjects with a history of colorectal adenomas. Int. J Colorectal Dis.

參見

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

[2] Jess Halliday (12/01/2007). "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". Asia Pacific Journal of Clinical Nutrition 11 (Suppl 2): S163–73.

[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.

[5] Coghlan, Andy (4 January 2014) "Designed plant oozes vital fish oils"' New Scientist, volume 221, issue 2950, page 12.

[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". Schizophrenia Research 49 (3): 243–51.

[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.

[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.

[10] Recent trends in the advanced analysis of bioactive fatty acids.Ruiz-Rodriguez A, Reglero G, Ibañez E.Departamento de Caracterización de Alimentos, Instituto de Fermentaciones Industriales, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain.

[11] Ghisolfi J., 1997. Acides gras, croissance fœtale et grossesse. Arch Pediatr 1997;4 (suppl 2):133s-5s.

[12] Fish oil lipid emulsions and immune response: what clinicians need to know.Waitzberg DL, Torrinhas RS.Faculdade de Medicina da Universidade de São Paulo, Avenida Dr Arnaldo, 455-2 degrees andar, sala 2108, CEP: 01245-903, São Paulo, SP, Brasil; PMID 19605803 [archive] [PubMed - in process]

[13] Cardiovascular disease prevention and treatment.von Schacky C.Preventive Cardiology, Medizinische Clinic and Policlinic Innenstadt, University of Munich, Ziemssensstr. 1, D-80336 Munich, Germany; Omegametrix, Am Klopferspitz 19, D-82152 Martinsried, Germany. PMID 19520557 [archive] [PubMed - as supplied by publisher]

[14] Bagga D, Anders KH, Wang HJ, Glaspy JA. Long-chain n-3-to-n-6 polyunsaturated fatty acid ratios in breast adipose tissue from women with and without breast cancer. Nutr Cancer 42, (2002) 180-5.

[15] Leitzmann MF, Stampfer MJ, Michaud DS, Augustsson KA, Colditz GC, Willett WC, Giovannucci EL., 2004. Dietray intake of n-3 and n-6 fatty acids and the risk of prostate cancer. Am J Clin Nutr; 80 : 204-216.

[16] Courtney, E.D., Matthews, S., Finlayson,C., Di Pierro, D., Belluzzi, A., Roda, E., Kang, J.Y., and Leicester, R.J., 2007. Eicosapentaenoic acid (EPA) reduces crypt cell proliferation and increases apoptosis in normal colonic mucosa in subjects with a history of colorectal adenomas. Int. J Colorectal Dis.

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