Summary: A class of compounds named after and generally derived from C20 fatty acids (EICOSANOIC ACIDS) that includes PROSTAGLANDINS; LEUKOTRIENES; THROMBOXANES, and HYDROXYEICOSATETRAENOIC ACIDS. They have hormone-like effects mediated by specialized receptors (RECEPTORS, EICOSANOID).

Top Publications

  1. Szklenar M, Kalkowski J, Stangl V, Lorenz M, Ruhl R. Eicosanoids and docosanoids in plasma and aorta of healthy and atherosclerotic rabbits. J Vasc Res. 2013;50:372-82 pubmed publisher
    b>Eicosanoids and docosanoids have been shown to be involved in atherosclerosis...
  2. Kim G, Nalini M, Kim Y, Lee D. Octopamine and 5-hydroxytryptamine mediate hemocytic phagocytosis and nodule formation via eicosanoids in the beet armyworm, Spodoptera exigua. Arch Insect Biochem Physiol. 2009;70:162-76 pubmed publisher
    ..In addition, eicosanoids also mediate these cellular immune reactions in various insects, resulting in clearing the bacteria circulating ..
  3. Claudiano G, Petrillo T, Manrique W, Castro M, Loureiro B, Marcusso P, et al. Acute aerocystitis in Piaractus mesopotamicus: participation of eicosanoids and pro-inflammatory cytokines. Fish Shellfish Immunol. 2013;34:1057-62 pubmed publisher
    ..There was no significant difference between the different doses of the drugs tested. The results suggest that eicosanoids and pro-inflammatory cytokines participate in chemical mediation in acute inflammation in pacus.
  4. Nachat Kappes R, Pinel A, Combe K, Lamas B, Farges M, Rossary A, et al. Effects of enriched environment on COX-2, leptin and eicosanoids in a mouse model of breast cancer. PLoS ONE. 2012;7:e51525 pubmed publisher
  5. Greineisen W, Shimoda L, Maaetoft Udsen K, Turner H. Insulin-containing lipogenic stimuli suppress mast cell degranulation potential and up-regulate lipid body biogenesis and eicosanoid secretion in a PPAR?-independent manner. J Leukoc Biol. 2012;92:653-65 pubmed publisher
    ..Thus, chronic exposure to metabolic stimuli, such as insulin, may be a determinant of the proinflammatory potential of the mast cell. ..
  6. Shrestha S, Kim Y. Various eicosanoids modulate the cellular and humoral immune responses of the beet armyworm, Spodoptera exigua. Biosci Biotechnol Biochem. 2009;73:2077-84 pubmed
    Cyclooxygenase (COX) and lipoxygenase (LOX) can catalyze the oxidation of C20 fatty acids to produce certain eicosanoids, which play roles in mediating immune responses in insects...
  7. Eder A, Koegl E, von Duvillard S, Sinzinger H, Berent R. Influence of cigarette smoking on synthesis of eicosanoids, isoprostanes and lipoxygenase metabolites in apical periodontitis. Arch Oral Biol. 2012;57:1133-40 pubmed publisher
    Arachidonic acid (AA) is metabolized to eicosanoids and isoprostanes (IPs) via different pathways. The presence of granuloma in apical periodontitis (AP) is linked with inflammation and the synthesis of metabolites of AA...
  8. O Donnell V, Maskrey B, Taylor G. Eicosanoids: generation and detection in mammalian cells. Methods Mol Biol. 2009;462:5-23 pubmed
    b>Eicosanoids are 20-carbon lipids generated by the oxidation of arachidonic acid that are involved in physiological signaling in virtually all organ systems...
  9. Panigrahy D, Edin M, Lee C, Huang S, Bielenberg D, Butterfield C, et al. Epoxyeicosanoids stimulate multiorgan metastasis and tumor dormancy escape in mice. J Clin Invest. 2012;122:178-91 pubmed publisher
    ..Thus, our data indicate a central role for EETs in tumorigenesis, offering a mechanistic link between lipid signaling and cancer and emphasizing the critical importance of considering possible effects of EET-modulating drugs on cancer. ..

More Information


  1. Shearer G, Newman J. Impact of circulating esterified eicosanoids and other oxylipins on endothelial function. Curr Atheroscler Rep. 2009;11:403-10 pubmed
    b>Eicosanoids, including epoxyeicosatrienoic acids, hydroxyeicosatetraenoic acids, and other oxylipins derived from polyunsaturated fatty acids, have emerging roles in endothelial inflammation and subsequent atherosclerosis...
  2. Blaho V, Buczynski M, Brown C, Dennis E. Lipidomic analysis of dynamic eicosanoid responses during the induction and resolution of Lyme arthritis. J Biol Chem. 2009;284:21599-612 pubmed publisher
    b>Eicosanoids and other bioactive lipid mediators are indispensable regulators of biological processes, as demonstrated by the numerous inflammatory diseases resulting from their dysregulation, including cancer, hyperalgesia, ..
  3. Masoodi M, Eiden M, Koulman A, Spaner D, Volmer D. Comprehensive lipidomics analysis of bioactive lipids in complex regulatory networks. Anal Chem. 2010;82:8176-85 pubmed publisher
    ..A multistep procedure was implemented to extract eicosanoids and other bioactive lipids from the biological matrix, chromatographically separate them using fast reversed-..
  4. Panigrahy D, Kaipainen A, Greene E, Huang S. Cytochrome P450-derived eicosanoids: the neglected pathway in cancer. Cancer Metastasis Rev. 2010;29:723-35 pubmed publisher
    ..In this review, the emerging role in cancer of cytochrome P450 metabolites, notably 20-HETE and EETs, are discussed. ..
  5. Schuck R, Theken K, Edin M, Caughey M, Bass A, Ellis K, et al. Cytochrome P450-derived eicosanoids and vascular dysfunction in coronary artery disease patients. Atherosclerosis. 2013;227:442-8 pubmed publisher
    ..These findings lay the foundation for future clinical research in this area. ..
  6. Capra V, Bäck M, Barbieri S, Camera M, Tremoli E, Rovati G. Eicosanoids and their drugs in cardiovascular diseases: focus on atherosclerosis and stroke. Med Res Rev. 2013;33:364-438 pubmed publisher
    b>Eicosanoids are biologically active lipids in both physiologic and pathophysiologic situations...
  7. Yang R, Chiang N, Oh S, Serhan C. Metabolomics-lipidomics of eicosanoids and docosanoids generated by phagocytes. Curr Protoc Immunol. 2011;Chapter 14:Unit 14.26 pubmed publisher
    ..Prostaglandins, thromboxane, and leukotrienes are well-known eicosanoids that play critical roles in hemodynamics and inflammation...
  8. Kaspera R, Totah R. Epoxyeicosatrienoic acids: formation, metabolism and potential role in tissue physiology and pathophysiology. Expert Opin Drug Metab Toxicol. 2009;5:757-71 pubmed publisher
    ..A better understanding of the regulation of EET levels and their mechanism of action on various receptors will accelerate research aiming at developing therapeutic agents that target EET formation or metabolism pathways. ..
  9. Sun Y, Wang Y, LI J, Zhu S, Tang H, Xia Z. Macrophage migration inhibitory factor counter-regulates dexamethasone-induced annexin 1 expression and influences the release of eicosanoids in murine macrophages. Immunology. 2013;140:250-8 pubmed publisher
    ..suggest that MIF counter-regulates Dex-induced annexin 1 expression, further influencing the activation of cPLA2? and the release of eicosanoids. These findings will add new insights into the mechanisms of MIF counter-regulation of GC.
  10. Ong S, Whitworth J. How do glucocorticoids cause hypertension: role of nitric oxide deficiency, oxidative stress, and eicosanoids. Endocrinol Metab Clin North Am. 2011;40:393-407, ix pubmed publisher
    ..This review highlights the role of nitric oxide-redox imbalance and their interactions with arachidonic acid metabolism in glucocorticoid-induced hypertension in humans and experimental animal models. ..
  11. Wang C, Zhao J, Liu H, Shao C, Liu Q, Liu Y, et al. Two new eicosanoids with a unique isovalerianic acid ester moiety from the South China Sea gorgonian Dichotella gemmacea. Lipids. 2011;46:81-5 pubmed publisher
    Two new eicosanoids with a unique isovalerianic acid ester group at C-12, named dichotellates A (1) and B (2), were isolated from the gorgonian Dichotella gemmacea collected from the South China Sea using bioassay-guided fractionation...
  12. Bui P, Imaizumi S, Beedanagari S, Reddy S, Hankinson O. Human CYP2S1 metabolizes cyclooxygenase- and lipoxygenase-derived eicosanoids. Drug Metab Dispos. 2011;39:180-90 pubmed publisher
  13. Greene E, Huang S, Serhan C, Panigrahy D. Regulation of inflammation in cancer by eicosanoids. Prostaglandins Other Lipid Mediat. 2011;96:27-36 pubmed publisher
    ..These lipid mediators are collectively referred to as eicosanoids and are generated by distinct enzymatic systems initiated by cyclooxygenases (COX 1 and 2), lipoxygenases (5-..
  14. Sterz K, Scherer G, Ecker J. A simple and robust UPLC-SRM/MS method to quantify urinary eicosanoids. J Lipid Res. 2012;53:1026-36 pubmed publisher
    b>Eicosanoids are key mediators and regulators of inflammation and oxidative stress often used as biomarkers for diseases and pathological conditions such as cardiovascular and pulmonary diseases and cancer...
  15. Basu S, Nachat Kappes R, Caldefie Chezet F, Vasson M. Eicosanoids and adipokines in breast cancer: from molecular mechanisms to clinical considerations. Antioxid Redox Signal. 2013;18:323-60 pubmed publisher
    ..Various signaling products of transcription factor, nuclear factor-kappaB, in particular inflammatory eicosanoids, reactive oxygen species (ROS), and cytokines, are thought to be involved in chronic inflammation-induced ..
  16. Sala A, Folco G, Murphy R. Transcellular biosynthesis of eicosanoids. Pharmacol Rep. 2010;62:503-10 pubmed
    ..express all the enzymes necessary for the production of biologically active compounds, it has been shown that eicosanoids are often the result of cell-cell interactions involving the transfer of biosynthetic intermediates, such as ..
  17. Baudry A, Bitard J, Mouillet Richard S, Locker M, Poliard A, Launay J, et al. Serotonergic 5-HT(2B) receptor controls tissue-nonspecific alkaline phosphatase activity in osteoblasts via eicosanoids and phosphatidylinositol-specific phospholipase C. J Biol Chem. 2010;285:26066-73 pubmed publisher
    ..In agreement with the above findings, primary calvarial osteoblasts from 5-HT(2B)R-null mice exhibit defects in TNAP activity. ..
  18. Wang D, DuBois R. Eicosanoids and cancer. Nat Rev Cancer. 2010;10:181-93 pubmed publisher
    b>Eicosanoids, including prostaglandins and leukotrienes, are biologically active lipids that have been implicated in various pathological processes, such as inflammation and cancer...
  19. Lundström S, D Alexandri F, Nithipatikom K, Haeggstrom J, Wheelock A, Wheelock C. HPLC/MS/MS-based approaches for detection and quantification of eicosanoids. Methods Mol Biol. 2009;579:161-87 pubmed publisher
    b>Eicosanoids are oxygenated, endogenous, unsaturated fatty acids derived from arachidonic acid...
  20. Ratnayake W, Galli C. Fat and fatty acid terminology, methods of analysis and fat digestion and metabolism: a background review paper. Ann Nutr Metab. 2009;55:8-43 pubmed publisher
  21. Buczynski M, Dumlao D, Dennis E. Thematic Review Series: Proteomics. An integrated omics analysis of eicosanoid biology. J Lipid Res. 2009;50:1015-38 pubmed publisher
    b>Eicosanoids have been implicated in a vast number of devastating inflammatory conditions, including arthritis, atherosclerosis, pain, and cancer...
  22. Montuschi P. LC/MS/MS analysis of leukotriene B4 and other eicosanoids in exhaled breath condensate for assessing lung inflammation. J Chromatogr B Analyt Technol Biomed Life Sci. 2009;877:1272-80 pubmed publisher
    ..LC/MS/MS for other eicosanoids including 8-isoprostane, a marker of oxidative stress, and cysteinyl-LTs have been developed...
  23. Büyükgüzel E, Hyrsl P, Büyükgüzel K. Eicosanoids mediate hemolymph oxidative and antioxidative response in larvae of Galleria mellonella L. Comp Biochem Physiol A Mol Integr Physiol. 2010;156:176-83 pubmed publisher
    ..We posed the hypothesis that eicosanoids also mediate antioxidant enzymatic defense reactions to pro-oxidant challenge...
  24. Theken K, Schuck R, Edin M, Tran B, Ellis K, Bass A, et al. Evaluation of cytochrome P450-derived eicosanoids in humans with stable atherosclerotic cardiovascular disease. Atherosclerosis. 2012;222:530-6 pubmed publisher
    ..Future studies are necessary to determine the therapeutic utility of modulating these pathways in patients with CAD. ..
  25. Hardwick J, Eckman K, Lee Y, Abdelmegeed M, Esterle A, Chilian W, et al. Eicosanoids in metabolic syndrome. Adv Pharmacol. 2013;66:157-266 pubmed publisher
    ..metabolic derangements trigger a persistent inflammatory cascade, which includes production of lipid autacoids (eicosanoids) that recruit immune cells to the site of injury and subsequent expression of cytokines and chemokines that ..
  26. Imig J, Simpkins A, Renic M, Harder D. Cytochrome P450 eicosanoids and cerebral vascular function. Expert Rev Mol Med. 2011;13:e7 pubmed publisher
    The eicosanoids 20-hydroxyeicosatetraenoic acid (20-HETE) and epoxyeicosatrienoic acids (EETs), which are generated from the metabolism of arachidonic acid by cytochrome P450 (CYP) enzymes, possess a wide array of biological actions, ..
  27. Simanshu D, Kamlekar R, Wijesinghe D, Zou X, Zhai X, Mishra S, et al. Non-vesicular trafficking by a ceramide-1-phosphate transfer protein regulates eicosanoids. Nature. 2013;500:463-7 pubmed publisher
    ..The resulting C1P decrease in plasma membranes and increase in the Golgi complex stimulates cPLA2? release of arachidonic acid, triggering pro-inflammatory eicosanoid generation. ..
  28. Gross G, Gauthier K, Moore J, Campbell W, Falck J, Nithipatikom K. Evidence for role of epoxyeicosatrienoic acids in mediating ischemic preconditioning and postconditioning in dog. Am J Physiol Heart Circ Physiol. 2009;297:H47-52 pubmed publisher
    ..These results suggest a unique role for endogenous EETs in both IPC and POC. ..
  29. Chiang Y, Haddad E, Rajaram S, Shavlik D, Sabate J. The effect of dietary walnuts compared to fatty fish on eicosanoids, cytokines, soluble endothelial adhesion molecules and lymphocyte subsets: a randomized, controlled crossover trial. Prostaglandins Leukot Essent Fatty Acids. 2012;87:111-7 pubmed publisher
    ..5% relative to the control diet. Both walnuts and fish in commonly consumed amounts may have modest albeit distinct effects on circulating adhesion molecules...
  30. Verhoff M, Seitz S, Northoff H, Jauch J, Schaible A, Werz O. A novel C(28)-hydroxylated lupeolic acid suppresses the biosynthesis of eicosanoids through inhibition of cytosolic phospholipase A(2). Biochem Pharmacol. 2012;84:681-91 pubmed publisher
    b>Eicosanoids are potent lipid mediators derived from phospholipase (PL)-released arachidonic acid (AA) coupled to subsequent metabolism by cyclooxygenase (COX)-1/2 or lipoxygenases (LO) which are involved in a variety of homeostatic ..
  31. Camara N, Martins J, Landgraf R, Jancar S. Emerging roles for eicosanoids in renal diseases. Curr Opin Nephrol Hypertens. 2009;18:21-7 pubmed publisher
    b>Eicosanoids are products of arachidonic acid metabolism which have important roles in renal homeostasis and disease...
  32. Young L, Kurzer M, Thomas W, Redmon J, Raatz S. Effect of dietary fat and omega-3 fatty acids on urinary eicosanoids and sex hormone concentrations in postmenopausal women: a randomized controlled feeding trial. Nutr Cancer. 2011;63:930-9 pubmed publisher
    ..effects of dietary fat and n-3 FA intake on breast cancer risk markers, circulating sex hormones and urinary eicosanoids were measured in response to controlled feeding of diets designed to increase plasma concentrations of n-3 FA...
  33. Yazid S, Solito E, Christian H, McArthur S, Goulding N, Flower R. Cromoglycate drugs suppress eicosanoid generation in U937 cells by promoting the release of Anx-A1. Biochem Pharmacol. 2009;77:1814-26 pubmed publisher
    ..1.3.16), which probably forms part of a control loop to limit Anx-A1 release. These experiments provide a basis for a novel mechanism of action for the cromolyns, a group of drugs that have long puzzled investigators. ..
  34. Moreno J. Differential effects of arachidonic and eicosapentaenoic Acid-derived eicosanoids on polymorphonuclear transmigration across endothelial cell cultures. J Pharmacol Exp Ther. 2009;331:1111-7 pubmed publisher
    ..EPA is also a substrate for arachidonic acid (AA) cascade enzymes, but it induces the production of alternative eicosanoids such as 3-series prostanoids and 5-series leukotrienes, which are considered to be less proinflammatory than AA ..
  35. Szefel J, Piotrowska M, Kruszewski W, Jankun J, Łysiak Szydłowska W, Skrzypczak Jankun E. Eicosanoids in prevention and management of diseases. Curr Mol Med. 2011;11:13-25 pubmed
    b>Eicosanoids, which originate from polyunsaturated fatty acids (PUFAs), have a major impact on homeostasis maintenance as secondary signal transducers...
  36. Norris P, Reichart D, Dumlao D, Glass C, Dennis E. Specificity of eicosanoid production depends on the TLR-4-stimulated macrophage phenotype. J Leukoc Biol. 2011;90:563-74 pubmed publisher
    ..Using a lipidomic approach, we comprehensively analyzed the eicosanoids made by murine RPMs, TGEMs, BMDM, and the macrophage-like cell line RAW after stimulation with the TLR-4-..
  37. Morgan A, Dioszeghy V, Maskrey B, Thomas C, Clark S, Mathie S, et al. Phosphatidylethanolamine-esterified eicosanoids in the mouse: tissue localization and inflammation-dependent formation in Th-2 disease. J Biol Chem. 2009;284:21185-91 pubmed publisher
    ..The studies suggest a new paradigm for lipids generated by 12/15-LOX in inflammation involving formation of esterified eicosanoids.
  38. Murphy E. Brain fixation for analysis of brain lipid-mediators of signal transduction and brain eicosanoids requires head-focused microwave irradiation: an historical perspective. Prostaglandins Other Lipid Mediat. 2010;91:63-7 pubmed publisher
    ..is essential in reliably assessing brain eicosanoid levels, without such fixation true basal levels of eicosanoids are impossible to determine and the high concentrations seen in some paradigms may be merely an artifact ..
  39. Pratico D, Dogne J. Vascular biology of eicosanoids and atherogenesis. Expert Rev Cardiovasc Ther. 2009;7:1079-89 pubmed publisher
    ..The lipid derivatives eicosanoids have been identified as important mediators that contribute to mechanisms of atherogenesis...
  40. Clark S, Guy C, Scurr M, Taylor P, Kift Morgan A, Hammond V, et al. Esterified eicosanoids are acutely generated by 5-lipoxygenase in primary human neutrophils and in human and murine infection. Blood. 2011;117:2033-43 pubmed publisher
    ..Thus, new molecular species of oxidized PL formed by human neutrophils during bacterial infection are identified and characterized. ..
  41. Fritscher L, Post M, Rodrigues M, Silverman F, Balter M, Chapman K, et al. Profile of eicosanoids in breath condensate in asthma and COPD. J Breath Res. 2012;6:026001 pubmed publisher
    The collection of exhaled breath condensates (EBC) is a noninvasive method for obtaining samples from the lungs. Eicosanoids are lipid mediators implicated in the asthmatic inflammatory response...
  42. Hilberath J, Carlo T, Pfeffer M, Croze R, Hastrup F, Levy B. Resolution of Toll-like receptor 4-mediated acute lung injury is linked to eicosanoids and suppressor of cytokine signaling 3. FASEB J. 2011;25:1827-35 pubmed publisher
    ..Together, these findings indicate pivotal roles for TLR4 in promoting sterile ALI and suggest downstream provocative roles for cysteinyl leukotrienes and protective roles for SOCS3 in the intensity and duration of host responses to ALI. ..
  43. Hyrsl P, Dobes P, Wang Z, Hauling T, Wilhelmsson C, Theopold U. Clotting factors and eicosanoids protect against nematode infections. J Innate Immun. 2011;3:65-70 pubmed publisher
    ..We also provide biochemical and genetic evidence for an involvement of eicosanoids in the same infection model...
  44. Suram S, Gangelhoff T, Taylor P, Rosas M, Brown G, Bonventre J, et al. Pathways regulating cytosolic phospholipase A2 activation and eicosanoid production in macrophages by Candida albicans. J Biol Chem. 2010;285:30676-85 pubmed publisher
    Resident tissue macrophages are activated by the fungal pathogen Candida albicans to release eicosanoids, which are important modulators of inflammation and immune responses...
  45. Gilroy D. Eicosanoids and the endogenous control of acute inflammatory resolution. Int J Biochem Cell Biol. 2010;42:524-8 pubmed publisher
    ..In this setting, the biochemical synthesis of key pro-resolution eicosanoids as well as their mode of action in self-limiting inflammation will be discussed.
  46. Maddipati K, Zhou S. Stability and analysis of eicosanoids and docosanoids in tissue culture media. Prostaglandins Other Lipid Mediat. 2011;94:59-72 pubmed publisher
    ..Other than the few clinically used eicosanoids such as prostaglandin F(2)?, prostacyclin, and prostaglandin E(2), little is known about the stability of a ..
  47. Srikanth K, Park J, Stanley D, Kim Y. Plasmatocyte-spreading peptide influences hemocyte behavior via eicosanoids. Arch Insect Biochem Physiol. 2011;78:145-60 pubmed publisher
    ..Prostaglandins (PGs), one group of eicosanoids formed from arachidonic acid (AA), also mediate plasmatocyte spreading (PS), although the potential ..
  48. Iliff J, Fairbanks S, Balkowiec A, Alkayed N. Epoxyeicosatrienoic acids are endogenous regulators of vasoactive neuropeptide release from trigeminal ganglion neurons. J Neurochem. 2010;115:1530-42 pubmed publisher
    Epoxyeicosatrienoic acids (EETs) are bioactive eicosanoids produced from arachidonic acid by cytochrome P450 epoxygenases...
  49. Piotrowska V, Piotrowski W, Kurmanowska Z, Marczak J, Górski P, Antczak A. Rhinosinusitis in COPD: symptoms, mucosal changes, nasal lavage cells and eicosanoids. Int J Chron Obstruct Pulmon Dis. 2010;5:107-17 pubmed
    ..Nasal lavages were collected for cytological examination and eicosanoids (cysteinyl leukotrienes, leukotriene B4, 8-isoprostane)...
  50. Petho G, Reeh P. Sensory and signaling mechanisms of bradykinin, eicosanoids, platelet-activating factor, and nitric oxide in peripheral nociceptors. Physiol Rev. 2012;92:1699-775 pubmed publisher
    ..Identified molecular elements of these signaling pathways may serve as validated targets for development of novel types of analgesic drugs. ..
  51. Ferrer R, Moreno J. Role of eicosanoids on intestinal epithelial homeostasis. Biochem Pharmacol. 2010;80:431-8 pubmed publisher
    ..For example, eicosanoids derived from arachidonic acid are proposed as mediators involved in the regulation of epithelial structure/..
  52. Pelikan Z. Delayed asthmatic response to bronchial challenge with allergen-mediators, eicosanoids, eosinophil and neutrophil constituents in the blood and urine. Respiration. 2011;82:225-36 pubmed publisher
    ..05). These results would indicate an active and prominent involvement of neutrophils, in addition to the previously demonstrated role of the Th1 lymphocytes, in the clinical DYAR. ..
  53. Novgorodtseva T, Karaman Y, Zhukova N, Lobanova E, Antonyuk M, Kantur T. Composition of fatty acids in plasma and erythrocytes and eicosanoids level in patients with metabolic syndrome. Lipids Health Dis. 2011;10:82 pubmed publisher
    ..b>Eicosanoids level in MS patients blood serum was studied by enzyme immunoassay...