花生五烯酸

花生五烯酸
	IUPAC名; (5Z,8Z,11Z,14Z,17Z)-icosa-; 5,8,11,14,17-pentaenoic acid; 顺,顺,顺,顺,顺-5,8,11,14,17-二十碳五烯酸
识别
CAS号	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配体	3362
性质
化学式	C20H30O2
摩尔质量	302.451 g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

花生五烯酸，也称为二十碳五烯酸（英语：Eicosapentaenoic acid, EPA）是有五个双键的多元不饱和脂肪酸（C₂₀H₃₀O₂），是一种ω-3脂肪酸。

来源

在人类饮食中，这种脂肪酸主要来源于食用脂肪含量高的鱼类和鱼油，例如鳕鱼肝、青鱼、鲭鱼、鲑鱼、鲱鱼、沙丁鱼和多种可食用海草和浮游植物；在人类母乳中亦存在此种脂肪酸。

但是鱼类自身并不合成EPA，而是通过食用海藻摄取^[1]。人类也可通过非动物性来源获取EPA，例如微藻类。此类植物亦被培养成为一个商业化的EPA来源^[2]。EPA在高大植物中不常见，但是有报道称马齿苋含微量EPA^[3]。2013年曾有报道指出亚麻荠属植物的一种基因改造变种含有大量EPA^[4]^[5]。

人体能够利用α-亚麻酸（ALA）合成自身所需的EPA。ALA是人体的一种必需脂肪酸，必须确保充足的摄入。但是，将ALA转化至EPA的效率远低于从食物中直接摄取，因为EPA本身也用于进一步合成二十二碳六烯酸（DHA）。人体很难从不含EPA和DHA的食物中间接获取足够量的EPA，因为：1.身体需要额外的代谢过程来合成EPA; 2.EPA同时又被用于合成DHA。某些疾病或者特殊条件会显著地降低身体从ALA合成EPA的能力，例如糖尿病或者一些过敏反应。

临床意义

美国国家卫生研究院的MedlinePlus数据库列出了EPA（单独使用或联合其他omega-3脂肪酸使用）能够有效治疗的疾病^[6]。大多数情况下EPA被证明对发炎症状有效。

在所有omega-3脂肪酸中，EPA被认为对一些精神方面的疾病有潜在的疗效，例如精神分裂症^[7]^[8]。

有研究表明EPA有可能对改进抑郁状态有帮助。2009年的一个综合研究发现摄取更高EPA:DHA比例的omega-3补充剂的病人较少出现抑郁症状^[9]。

对人体健康的影响

总体效果

摄入脂肪酸对慢性病的影响被广泛认可，这些疾病包括肥胖症、糖尿病、癌症、关节炎、哮喘和心血管疾病^[10]。

对神经系统的影响

足够的脂肪酸摄入（特别是EPA和DHA）对胎儿神经系统发育成熟的重要性如今已被证明^[11]。

炎症

一个研究表明鱼油（通常含有较高的EPA和DHA含量）可以通过影响多种发炎反应的机理而预防这类疾病^[12]。

心血管疾病

对于心血管方面的疾病，EPA和DHA被证明对改进以下症状有效^[13]:

癌症

多个研究表明，EPA或DHA摄入对乳腺癌或者前列腺癌的影响取决于同时摄入的omega-6脂肪酸和抗氧化剂^[14]^[15]。EPA亦对预防直肠结肠癌有效果^[16]。

参考来源

^ 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.

参见

[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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