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Chemical Compound Review

AGN-PC-00KBM2     icosa-5,8,11,14,17-pentaenoic acid

Synonyms: AG-D-16069, AG-L-61493, KBioGR_000048, KBioSS_000048, ACMC-20mqw3, ...
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Disease relevance of Eicosapentaenoic acid


Psychiatry related information on Eicosapentaenoic acid

  • The evidence base supports a dietary recommendation of approximately 500 mg/d of EPA and DHA for cardiovascular disease risk reduction [6].

High impact information on Eicosapentaenoic acid

  • LTB4-stimulated neutrophil chemotaxis and IP3 formation correlated significantly (P < 0.0001); each response correlated closely and negatively with the EPA content of the neutrophil phosphatidylinositol (PI) pool (P = 0.0003 and P = 0.0005, respectively) [7].
  • We show that oxidized, but not native unoxidized, EPA significantly inhibited human neutrophil and monocyte adhesion to endothelial cells in vitro by inhibiting endothelial adhesion receptor expression [8].
  • In vivo, oxidized, but not native, EPA markedly reduced leukocyte rolling and adhesion to venular endothelium of lipopolysaccharide (LPS)-treated mice [8].
  • Therefore, the beneficial effects of omega-3 fatty acids may be explained by a PPAR alpha-mediated anti-inflammatory effect of oxidized EPA [8].
  • This occurred via a PPAR alpha-dependent mechanism because oxidized EPA had no such effect in LPS-treated PPAR alpha-deficient mice [8].

Chemical compound and disease context of Eicosapentaenoic acid


Biological context of Eicosapentaenoic acid

  • EPA and HMB also attenuated phosphorylation of p42/44 mitogen-activated protein kinase by PIF, thought to be important in PIF-induced proteasome expression [10].
  • Conversely, DHA supplementation induced a doubling of the number of cells undergoing apoptosis (labeled by TUNEL), whereas EPA treatment was much less effective [11].
  • It is concluded from the results of the present study that the anti-tumoral effect of EPA is related mainly to its inhibition of cell proliferation, whereas that of DHA corresponds with its induction of apoptosis [11].
  • Platelet (co-)incubation with EPA, but not DCHA, provoked dose-dependent synthesis of n-3-lipid-derived thromboxane: kinetics of formation and absolute quantities of TxA3 approximated 20% of the respective TxA2 data upon stimulation with AA [12].
  • We investigated the influence of free EPA and DCHA on platelet thromboxane (Tx) A2 and A3 formation by using a recently developed high performance liquid chromatography-ELISA technique for separate quantification of the stable hydrolysis products TxB2 and TxB3 [12].

Anatomical context of Eicosapentaenoic acid

  • The inhibition of the summed formation of LTB4 plus LTB5 in calcium ionophore-stimulated neutrophils and in zymosan-stimulated neutrophils did not correlate significantly with the EPA content of the PI pool [7].
  • RESULTS: Dietary SDA increased EPA and docosapentaenoic acid concentrations but not DHA concentrations in erythrocyte and in plasma phospholipids [13].
  • Adipose tissue fatty acid profiles analyzed in three samples taken from each subject at 1-y intervals showed no within-subject differences for EPA and DHA [14].
  • CONCLUSIONS: Consumption of < or = 600 mg DHA and 140 mg EPA/d for 4 wk increased n-3 PUFA concentrations in relevant tissues but did not cause perturbations in cytokine concentrations in human milk [15].
  • Analysis of changes in phospholipid fatty acids in tumor-cell membranes after both treatments with EPA and DHA showed a significant reduction in arachidonic-acid levels [11].

Associations of Eicosapentaenoic acid with other chemical compounds


Gene context of Eicosapentaenoic acid

  • Oral/enteral supplementation of EPA ethyl ester (1.8 g/d) significantly reduced the postoperative IL-6 production (P < 0.05 at 1, 2, and 6 h after operation), and improved cell-mediated immune function 3 wk after operation (P = 0.05) [20].
  • After adjustment for smoking exposure and other possible confounders, the prevalence odds of COPD were inversely related to the DHA (but not to the EPA) content of plasma lipid components in most of the models [16].
  • Of the omega-3 PUFAs tested, alpha-linolenic acid (ALA) dramatically reduced FAS activity in a dose-dependent manner (up to 61%). omega-3 PUFA docosahexaenoic acid (DHA) demonstrated less marked but still significant inhibitory effects on FAS activity (up to 37%), whereas eicosapentaenoic acid (EPA) was not effective [21].
  • Here the authors present data which suggests that PGs including thromboxane B2 (TXB2) and their precursors such as dihomo-gamma linolenic acid (DGLA), arachidonic acid (AA) and eicosapentaenoic acid (EPA) can inhibit T-cell proliferation and influence their ability to secrete IL-2, IL-4, IL-6 and TNF in vitro [22].
  • In addition, both ALA and EPA enhanced the formation of superoxide anion, hydrogen peroxide and lipid peroxides, and caused a reduction in the levels of antioxidant enzymes: SOD, catalase and glutathione peroxidase and induced significant damage to DNA in SP 2/0 cells [23].

Analytical, diagnostic and therapeutic context of Eicosapentaenoic acid


  1. Differences exist in the relationships between dietary linoleic and alpha-linolenic acids and their respective long-chain metabolites. Mantzioris, E., James, M.J., Gibson, R.A., Cleland, L.G. Am. J. Clin. Nutr. (1995) [Pubmed]
  2. Dietary echium oil increases plasma and neutrophil long-chain (n-3) fatty acids and lowers serum triacylglycerols in hypertriglyceridemic humans. Surette, M.E., Edens, M., Chilton, F.H., Tramposch, K.M. J. Nutr. (2004) [Pubmed]
  3. Supplementation with an algae source of docosahexaenoic acid increases (n-3) fatty acid status and alters selected risk factors for heart disease in vegetarian subjects. Conquer, J.A., Holub, B.J. J. Nutr. (1996) [Pubmed]
  4. Quantitative high-performance liquid chromatography/electrospray ionization tandem mass spectrometric analysis of 2- and 3-series prostaglandins in cultured tumor cells. Yang, P., Felix, E., Madden, T., Fischer, S.M., Newman, R.A. Anal. Biochem. (2002) [Pubmed]
  5. The effects of infusion of trieicosapentaenoyl-glycerol emulsion on extravascular lung water during myocardial ischemia and reperfusion in dogs. Izuoka, T., Kimura, Y., Hamazaki, T., Tamura, T., Kitashiro, S., Sugiura, T., Jikuhara, T., Iwasaka, T. Lipids (1997) [Pubmed]
  6. n-3 fatty acid dietary recommendations and food sources to achieve essentiality and cardiovascular benefits. Gebauer, S.K., Psota, T.L., Harris, W.S., Kris-Etherton, P.M. Am. J. Clin. Nutr. (2006) [Pubmed]
  7. Dietary omega-3 polyunsaturated fatty acids inhibit phosphoinositide formation and chemotaxis in neutrophils. Sperling, R.I., Benincaso, A.I., Knoell, C.T., Larkin, J.K., Austen, K.F., Robinson, D.R. J. Clin. Invest. (1993) [Pubmed]
  8. Oxidized omega-3 fatty acids in fish oil inhibit leukocyte-endothelial interactions through activation of PPAR alpha. Sethi, S., Ziouzenkova, O., Ni, H., Wagner, D.D., Plutzky, J., Mayadas, T.N. Blood (2002) [Pubmed]
  9. Low-dose eicosapentaenoic or docosahexaenoic acid administration modifies fatty acid composition and does not affect susceptibility to oxidative stress in rat erythrocytes and tissues. Calviello, G., Palozza, P., Franceschelli, P., Bartoli, G.M. Lipids (1997) [Pubmed]
  10. Mechanism of the attenuation of proteolysis-inducing factor stimulated protein degradation in muscle by beta-hydroxy-beta-methylbutyrate. Smith, H.J., Wyke, S.M., Tisdale, M.J. Cancer Res. (2004) [Pubmed]
  11. Dietary supplementation with eicosapentaenoic and docosahexaenoic acid inhibits growth of Morris hepatocarcinoma 3924A in rats: effects on proliferation and apoptosis. Calviello, G., Palozza, P., Piccioni, E., Maggiano, N., Frattucci, A., Franceschelli, P., Bartoli, G.M. Int. J. Cancer (1998) [Pubmed]
  12. Fish oil fatty acids and human platelets: dose-dependent decrease in dienoic and increase in trienoic thromboxane generation. Krämer, H.J., Stevens, J., Grimminger, F., Seeger, W. Biochem. Pharmacol. (1996) [Pubmed]
  13. Metabolism of stearidonic acid in human subjects: comparison with the metabolism of other n-3 fatty acids. James, M.J., Ursin, V.M., Cleland, L.G. Am. J. Clin. Nutr. (2003) [Pubmed]
  14. Omega-3 fatty acids in adipose tissue of obese patients with non-insulin-dependent diabetes mellitus reflect long-term dietary intake of eicosapentaenoic and docosahexaenoic acid. Popp-Snijders, C., Blonk, M.C. Am. J. Clin. Nutr. (1995) [Pubmed]
  15. A randomized trial of supplementation with docosahexaenoic acid-rich tuna oil and its effects on the human milk cytokines interleukin 1 beta, interleukin 6, and tumor necrosis factor alpha. Hawkes, J.S., Bryan, D.L., Makrides, M., Neumann, M.A., Gibson, R.A. Am. J. Clin. Nutr. (2002) [Pubmed]
  16. Docosahexaenoic acid and smoking-related chronic obstructive pulmonary disease. The Atherosclerosis Risk in Communities Study Investigators. Shahar, E., Boland, L.L., Folsom, A.R., Tockman, M.S., McGovern, P.G., Eckfeldt, J.H. Am. J. Respir. Crit. Care Med. (1999) [Pubmed]
  17. Ligand-operated synthesis of 4-series and 5-series leukotrienes in human neutrophils: critical dependence on exogenous free fatty acid supply. Grimminger, F., Dürr, U., Seeger, W. Mol. Pharmacol. (1992) [Pubmed]
  18. Moderate fish-oil supplementation reverses low-platelet, long-chain n-3 polyunsaturated fatty acid status and reduces plasma triacylglycerol concentrations in British Indo-Asians. Lovegrove, J.A., Lovegrove, S.S., Lesauvage, S.V., Brady, L.M., Saini, N., Minihane, A.M., Williams, C.M. Am. J. Clin. Nutr. (2004) [Pubmed]
  19. The effect on human tumor necrosis factor alpha and interleukin 1 beta production of diets enriched in n-3 fatty acids from vegetable oil or fish oil. Caughey, G.E., Mantzioris, E., Gibson, R.A., Cleland, L.G., James, M.J. Am. J. Clin. Nutr. (1996) [Pubmed]
  20. n-3 versus n-6 polyunsaturated fatty acids in critical illness. Tashiro, T., Yamamori, H., Takagi, K., Hayashi, N., Furukawa, K., Nakajima, N. Nutrition (Burbank, Los Angeles County, Calif.) (1998) [Pubmed]
  21. Overexpression and hyperactivity of breast cancer-associated fatty acid synthase (oncogenic antigen-519) is insensitive to normal arachidonic fatty acid-induced suppression in lipogenic tissues but it is selectively inhibited by tumoricidal alpha-linolenic and gamma-linolenic fatty acids: a novel mechanism by which dietary fat can alter mammary tumorigenesis. Menendez, J.A., Ropero, S., Mehmi, I., Atlas, E., Colomer, R., Lupu, R. Int. J. Oncol. (2004) [Pubmed]
  22. Effect of prostaglandins and their precursors on the proliferation of human lymphocytes and their secretion of tumor necrosis factor and various interleukins. Kumar, G.S., Das, U.N. Prostaglandins Leukot. Essent. Fatty Acids (1994) [Pubmed]
  23. Free radical-dependent suppression of growth of mouse myeloma cells by alpha-linolenic and eicosapentaenoic acids in vitro. Kumar, G.S., Das, U.N. Cancer Lett. (1995) [Pubmed]
  24. The effect of dietary docosahexaenoic acid on plasma lipoproteins and tissue fatty acid composition in humans. Nelson, G.J., Schmidt, P.C., Bartolini, G.L., Kelley, D.S., Kyle, D. Lipids (1997) [Pubmed]
  25. Pilot-plant-scale outdoor mixotrophic cultures of Phaeodactylum tricornutum using glycerol in vertical bubble column and airlift photobioreactors: studies in fed-batch mode. Fernández Sevilla, J.M., Cerón García, M.C., Sánchez Mirón, A., Belarbi, e.l. .H., García Camacho, F., Molina Grima, E. Biotechnol. Prog. (2004) [Pubmed]
  26. Supplementation of {omega}-3 Fatty acids in parenteral nutrition beneficially alters phospholipid Fatty Acid pattern. Senkal, M., Geier, B., Hannemann, M., Deska, T., Linseisen, J., Wolfram, G., Adolph, M. JPEN. Journal of parenteral and enteral nutrition (2007) [Pubmed]
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