prostaglandins e


Summary: (11 alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-oic acid (PGE(1)); (5Z,11 alpha,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-oic acid (PGE(2)); and (5Z,11 alpha,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-oic acid (PGE(3)). Three of the six naturally occurring prostaglandins. They are considered primary in that no one is derived from another in living organisms. Originally isolated from sheep seminal fluid and vesicles, they are found in many organs and tissues and play a major role in mediating various physiological activities.

Top Publications

  1. Bridges P, Komar C, Fortune J. Gonadotropin-induced expression of messenger ribonucleic acid for cyclooxygenase-2 and production of prostaglandins E and F2alpha in bovine preovulatory follicles are regulated by the progesterone receptor. Endocrinology. 2006;147:4713-22 pubmed
  2. Boutaud O, Brame C, Salomon R, Roberts L, Oates J. Characterization of the lysyl adducts formed from prostaglandin H2 via the levuglandin pathway. Biochemistry. 1999;38:9389-96 pubmed
    ..These findings provide a basis for investigating protein modification induced by oxygenation of arachidonic acid by the cyclooxygenases. ..
  3. Boutaud O, Brame C, Chaurand P, Li J, Rowlinson S, Crews B, et al. Characterization of the lysyl adducts of prostaglandin H-synthases that are derived from oxygenation of arachidonic acid. Biochemistry. 2001;40:6948-55 pubmed
    ..The reactivity of the PGH-synthase adducts themselves is demonstrated by the formation of intermolecular cross-links. ..
  4. Boutaud O, Andreasson K, Zagol Ikapitte I, Oates J. Cyclooxygenase-dependent lipid-modification of brain proteins. Brain Pathol. 2005;15:139-42 pubmed
    ..In this review, we discuss the cyclooxygenase-dependent lipid-modification of proteins by levuglandins in vitro, in cells in culture and in vivo in transgenic mice over-expressing COX in the brain. ..
  5. Boutaud O, Li J, Zagol I, Shipp E, Davies S, Roberts L, et al. Levuglandinyl adducts of proteins are formed via a prostaglandin H2 synthase-dependent pathway after platelet activation. J Biol Chem. 2003;278:16926-8 pubmed
    ..They also demonstrate that a physiological stimulus is sufficient to lead to the lipid modification of proteins through the levuglandin pathway in human platelets. ..
  6. Zagol Ikapitte I, Masterson T, Amarnath V, Montine T, Andreasson K, Boutaud O, et al. Prostaglandin H(2)-derived adducts of proteins correlate with Alzheimer's disease severity. J Neurochem. 2005;94:1140-5 pubmed
    ..The magnitude of the increase correlates with the pathological evidence of severity. ..
  7. Janett F, Aebi L, Burger D, Imboden I, Hassig M, Kindahl H, et al. Influence of vedaprofen (Quadrisol) on quality and freezability of stallion semen. Theriogenology. 2005;64:1867-77 pubmed
    ..05) effect on motility, normal sperm and sperm with nuclear vacuoles in fresh semen. ..
  8. Mann W, Muttray A, Schaefer D, Klimek L, Faas M, Konietzko J. Exposure to 200 ppm of methanol increases the concentrations of interleukin-1beta and interleukin-8 in nasal secretions of healthy volunteers. Ann Otol Rhinol Laryngol. 2002;111:633-8 pubmed
    ..The German threshold limit of 200 ppm of methanol does not prevent subclinical inflammatory reactions of the nasal respiratory mucosa. ..
  9. Lang P, Kempe D, Myssina S, Tanneur V, Birka C, Laufer S, et al. PGE(2) in the regulation of programmed erythrocyte death. Cell Death Differ. 2005;12:415-28 pubmed
    ..In conclusion, hyperosmotic shock or Cl(-) removal stimulates erythrocyte PS exposure through PGE(2) formation and subsequent activation of Ca(2+)-permeable cation channels. ..

More Information


  1. Lister A, van der Kraak G. Regulation of prostaglandin synthesis in ovaries of sexually-mature zebrafish (Danio rerio). Mol Reprod Dev. 2009;76:1064-75 pubmed publisher
    ..Collectively, these in vivo results suggest that gonadotropins and steroids are involved in the regulation of the AA pathway in ovarian follicles of zebrafish. ..
  2. Yuan J, Akiyama M, Nakahama K, Sato T, Uematsu H, Morita I. The effects of polyunsaturated fatty acids and their metabolites on osteoclastogenesis in vitro. Prostaglandins Other Lipid Mediat. 2010;92:85-90 pubmed publisher
    ..This study showed a distinct mechanism of the effect of PUFAs on osteoclastogenesis and will provide evidence for therapeutic treatment with DHA in osteoporotic patients. ..
  3. Pillinger M, Dinsell V, Apsel B, Tolani S, Marjanovic N, Chan E, et al. Regulation of metalloproteinases and NF-kappaB activation in rabbit synovial fibroblasts via E prostaglandins and Erk: contrasting effects of nabumetone and 6MNA. Br J Pharmacol. 2004;142:973-82 pubmed
    ..In contrast, nabumetone demonstrates anti-inflammatory and potentially arthroprotective effects that have not been previously appreciated. ..
  4. Ubatuba F. An animal model for the study of arterial thrombosis. Braz J Med Biol Res. 1989;22:993-1000 pubmed
    ..PGI2 was less active in rats than in rabbits (Threshold Protective Dose ratio ca. 4:1). PGE1 and PGD2 showed intermediate activity in both animal models. ..
  5. Ribeiro M, Farina M, Billi S, Perez Martinez S, Brañes M, Villalon M, et al. Effect of in vivo administration of epidermal growth factor on prostaglandin production and NOS activity in term rat placentae. Possible participation of placental EGF receptors. Placenta. 2005;26:758-65 pubmed
    ..Hence, EGF is a very interesting molecule for studying the regulation of placental prostaglandin and nitric oxide production related to the parturition process. ..
  6. Shin H, Kim S, Kang S, Lee D, Choi H. Soluble glucocorticoid-induced tumor necrosis factor receptor stimulates osteoclastogenesis by down-regulation of osteoprotegerin in bone marrow stromal cells. Bone. 2006;39:716-23 pubmed
    ..This suggests that down-regulation of OPG by PGE(2) is involved in sGITR-induced osteoclast (OC) formation in the presence of conditioned medium from mouse bone marrow stromal cells. ..
  7. Sirotkin A, Makarevich A, Corkins M, Kotwica J, Kwon H, Bulla J, et al. Secretory activity of bovine ovarian granulosa cells transfected with sense and antisense insulin-like growth factor (IGF) binding protein-3 and the response to IGF-I, GH, LH, oxytocin and oestradiol. J Mol Endocrinol. 2001;27:329-38 pubmed
    ..IGFBP-3 is a physiological stimulator of IGF-I and prostaglandin release and an inhibitor of steroid and peptide hormone output. ..
  8. Hancock W, Polanski M, Zhang J, Blogg N, Weiner H. Suppression of insulitis in non-obese diabetic (NOD) mice by oral insulin administration is associated with selective expression of interleukin-4 and -10, transforming growth factor-beta, and prostaglandin-E. Am J Pathol. 1995;147:1193-9 pubmed
  9. Casteleijn E, Kuiper J, van Rooij H, Kamps J, Koster J, van Berkel T. Hormonal control of glycogenolysis in parenchymal liver cells by Kupffer and endothelial liver cells. J Biol Chem. 1988;263:2699-703 pubmed
    ..This implies that products of Kupffer and endothelial liver cells may play a role in the regulation of glucose homeostasis by the liver. ..
  10. Huang W, Sun R. [Study on analgesic and accompanying toxic and side effects of euodiae fructus based on clinical efficacy dose]. Zhongguo Zhong Yao Za Zhi. 2013;38:2176-81 pubmed
    ..Its analgesic mechanism is related to the reduction of PGE, content in blood, while its toxic mechanism is related to oxidative injury to some extent. ..
  11. Lagerstrand L, Hedenstierna G. Gas-exchange impairment: its correlation to lung mechanics in acute airway obstruction (studies on a rabbit asthma model). Clin Physiol. 1990;10:363-80 pubmed
    ..These factors might be alveolar oedema, or mucus and oedema in the smallest airways. ..
  12. Seguineau C, Racotta I, Palacios E, Delaporte M, Moal J, Soudant P. The influence of dietary supplementation of arachidonic acid on prostaglandin production and oxidative stress in the Pacific oyster Crassostrea gigas. Comp Biochem Physiol A Mol Integr Physiol. 2011;160:87-93 pubmed publisher
    ..To further confirm the involvement of PG in the changes of haemocyte count, phagocytosis and ROS production upon ARA supplementation, it would be interesting to test cyclooxygenase and lipooxygenase inhibitors in similar experiments. ..
  13. Barr R, Black A, Dowd P, Koro O, Mistry K, Isaacs J, et al. The in vitro 5-lipoxygenase and cyclo-oxygenase inhibitor L-652,343 does not inhibit 5-lipoxygenase in vivo in human skin. Br J Clin Pharmacol. 1988;25:23-6 pubmed
    ..This shows the importance of confirming that the action of 5-lipoxygenase inhibiting drugs in vitro occurs in vivo. ..
  14. Sirotkin A, Makarevich A, Kwon H, Kotwica J, Bulla J, Hetenyi L. Do GH, IGF-I and oxytocin interact by regulating the secretory activity of porcine ovarian cells?. J Endocrinol. 2001;171:475-80 pubmed
  15. Aid S, Parikh N, Palumbo S, Bosetti F. Neuronal overexpression of cyclooxygenase-2 does not alter the neuroinflammatory response during brain innate immune activation. Neurosci Lett. 2010;478:113-8 pubmed publisher
    ..This is likely due to the direct effect of LPS on glial rather than neuronal cells. ..
  16. Karhumäki E. Effect of leukocyte and other tissue dialysates on NBT reduction and prostaglandin production in mice. Acta Pathol Microbiol Immunol Scand C. 1987;95:251-6 pubmed
    ..These results may indicate that all dialysates can be a source of a non-specifically-acting immunomodulatory preparation and that the infection-resistance-increasing substances seem to operate via the monocyte/macrophage activation. ..
  17. Lawrence R, Jones R, Wilson N. Characterization of receptors involved in the direct and indirect actions of prostaglandins E and I on the guinea-pig ileum. Br J Pharmacol. 1992;105:271-8 pubmed
    ..7. In view of the complexity of prostanoid action on the guinea-pig ileum we feel that the preparation must be used with caution to ascertain the EPl agonist or antagonist potencies of novel compounds. ..
  18. Fekkes D, Bode W, Zijlstra F, Pepplinkhuizen L. Eicosanoid and amino acid metabolism in transient acute psychoses with psychedelic symptoms. Prostaglandins Leukot Essent Fatty Acids. 1996;54:261-4 pubmed
    ..These results are consistent with the hypothesis that the metabolism of GSH is impaired in transient psychotic states. ..
  19. Shibata Y, Volkman A. The effect of hemopoietic microenvironment on splenic suppressor macrophages in congenitally anemic mice of genotype Sl/Sld. J Immunol. 1985;135:3905-10 pubmed
    ..In aggregate, these findings delineate three functionally definable populations of mononuclear phagocytes that appear to be independently regulated. ..
  20. Hidaka T, Nakano M, Inokuchi T, Sugiyama M, Nishi J, Ogura R. Arachidonate metabolism in bovine gallbladder mucosa. Kurume Med J. 1991;38:129-33 pubmed
    ..These results indicate that bovine gallbladder mucosa contains higher levels of fatty acid cyclooxygenase, and PGE2 isomerase and PGI2 synthetase in a proportion different from that in the muscle. ..
  21. Ruzicka T, Ring J. Enhanced releasability of prostaglandin E2 and leukotrienes B4 and C4 from leukocytes of patients with atopic eczema. Acta Derm Venereol. 1987;67:469-75 pubmed
    ..Thus, our data support the hypothesis of enhanced releasability of inflammatory mediators in atopic eczema. ..
  22. Aussel C, Fehlmann M. Effect of alpha-fetoprotein and indomethacin on arachidonic acid metabolism in P388D1 macrophages: role of leukotrienes. Prostaglandins Leukot Med. 1987;28:325-36 pubmed
    ..In addition, it is shown that the effects of AFP and AFP+Indomethacin on cyclooxygenase activity might be explained by the endogenous synthesis of leukotrienes. ..
  23. Trachte G, Hook P, Kemp J, Acosta E, Ziegler R. Thromboxane synthesis and actions in isolated adrenergic nerve (pheochromocytoma-12) cells. J Pharmacol Exp Ther. 1988;247:43-6 pubmed
    ..These results are indicative of PGE, PGF and thromboxane production by isolated adrenergic neuronal tissue. A thromboxane receptor agonist also was observed to potentiate norepinephrine release. ..
  24. Palombo J, DeMichele S, Boyce P, Lydon E, Liu J, Huang Y, et al. Effect of short-term enteral feeding with eicosapentaenoic and gamma-linolenic acids on alveolar macrophage eicosanoid synthesis and bactericidal function in rats. Crit Care Med. 1999;27:1908-15 pubmed
  25. Tsujikawa T, Ohta N, Nakamura T, Satoh J, Uda K, Ihara T, et al. Medium-chain triglycerides modulate ileitis induced by trinitrobenzene sulfonic acid. J Gastroenterol Hepatol. 1999;14:1166-72 pubmed
    ..These results suggested that TNBS enteritis might be useful as an IBD animal model and that MCT modulates intestinal inflammation and is less damaging than LCT. ..
  26. Neuwirth R, Singhal P, Diamond B, Hays R, Lobmeyer L, Clay K, et al. Evidence for immunoglobulin Fc receptor-mediated prostaglandin2 and platelet-activating factor formation by cultured rat mesangial cells. J Clin Invest. 1988;82:936-44 pubmed
    ..These observations may be of significance for immune-mediated glomerular diseases...
  27. Wright K, Weaver S, Patel K, Coopman K, Feeney M, Kolios G, et al. Differential regulation of prostaglandin E biosynthesis by interferon-gamma in colonic epithelial cells. Br J Pharmacol. 2004;141:1091-7 pubmed
    ..This may have important implications for the clinical use of IFN gamma in inflammatory diseases. ..
  28. Alvarez J, Porwollik S, Laconcha I, Gisakis V, Vivanco A, Gonzalez I, et al. Detection of a Salmonella enterica serovar California strain spreading in spanish feed mills and genetic characterization with DNA microarrays. Appl Environ Microbiol. 2003;69:7531-4 pubmed
    ..enterica serovar Typhimurium LT2 gene clusters that are absent from serovar California. ..
  29. Tendo M, Yashiro M, Nakazawa K, Yamada N, Hirakawa K. Inhibitory effect of a selective cyclooxygenase inhibitor on the invasion-stimulating activity of orthotopic fibroblasts for scirrhous gastric cancer cells. Cancer Sci. 2005;96:451-5 pubmed
  30. Jung T. Prostaglandins, leukotrienes, and other arachidonic acid metabolites in the pathogenesis of otitis media. Laryngoscope. 1988;98:980-93 pubmed
    ..It is clear from these studies that arachidonic acid metabolites are important inflammatory mediators in the pathogenesis of otitis media. ..
  31. Miller V, Vanhoutte P. Prostaglandins but not nitric oxide are endothelium-derived relaxing factors in the trout aorta. Acta Pharmacol Sin. 2000;21:871-6 pubmed
    ..A phylogenetic appearance of nitric-oxide sensitive mechanism for vasodilatation, perhaps is associated with the transition from water to air respiration. ..
  32. Jawerbaum A, Gonzalez E, Novaro V, Faletti A, Gimeno M. Nitric oxide mediates increased prostaglandin E production by oocyte-cumulus complexes in the non-insulin-dependent diabetic rat. Reprod Fertil Dev. 1998;10:185-90 pubmed
    ..NO synthase activity was higher in diabetic ovaries than in controls. The present results suggest that NO mediates the increased PGE production by diabetic OVA, probably a result of overproduction of NO. ..
  33. Fringes B, Klein P, Lorenz D, Oehlert W. Light microscopic quantitative investigation on the effects of prostaglandin E2 (PGE2) on the lectin binding pattern in rat gastric mucosa injured by ethanol or sodium taurocholate. Acta Histochem Suppl. 1988;36:263-72 pubmed
  34. Woods R, Thien F. Polyunsaturated fats and asthma. Thorax. 2002;57:94 pubmed
  35. Miles E, Allen E, Calder P. In vitro effects of eicosanoids derived from different 20-carbon Fatty acids on production of monocyte-derived cytokines in human whole blood cultures. Cytokine. 2002;20:215-23 pubmed
    ..PGE(1), PGE(2) and PGE(3) show a similar pattern and magnitude of effect. This suggests that the anti-inflammatory effects of dietary fish oil may not be mediated through a simple substitution of one family of eicosanoids for another. ..
  36. Rao T, Seth S, Manchanda S, Nayar U. The involvement of the sympathetic nervous system in the centrogenic pressor and tachycardiac effects of prostaglandins E2 and F2 alpha in anaesthetised cats. Brain Res. 1987;435:7-14 pubmed
    ..c.v. PGE2 and PGF2 alpha. The results suggest that the centrally administered PGE2 and PGF2 alpha augment sympathetic outflow to the heart and vascular system and thereby cause excitatory cardiovascular responses in anaesthetised cats. ..
  37. Tawfik O, Sagrillo C, Johnson D, Dey S. Decidualization in the rat: role of leukotrienes and prostaglandins. Prostaglandins Leukot Med. 1987;29:221-7 pubmed
    ..These results are interpreted to indicate that there is an interaction between LTs and PGs in the induction of the uterine decidual response. ..
  38. Vitiello R, Giordano C, Macchieraldo A, Pecorari G, Sartoris A. [Prostaglandins, suppressive action cells and carcinoma of the larynx: preliminary data]. Acta Otorhinolaryngol Ital. 1990;10:73-8 pubmed
    ..On the basis of these results, while awaiting further data, it can be suggested that future therapy be based on the administration of indomethacin in patients suffering from this disease. ..
  39. Campbell P, Tolson T. Modulation of human monocyte leukotactic responsiveness by thromboxane A2 and 12-hydroxyheptadecatrienoic acid (12-HHT). J Leukoc Biol. 1988;43:117-24 pubmed
    ..These data suggest a major regulatory role for thromboxane synthetase products in human monocyte leukotaxis. ..
  40. DeChiara T, Young D, Semionow R, Stern A, Batula Bernardo C, Fiedler Nagy C, et al. Structure-function analysis of murine interleukin 1: biologically active polypeptides are at least 127 amino acids long and are derived from the carboxyl terminus of a 270-amino acid precursor. Proc Natl Acad Sci U S A. 1986;83:8303-7 pubmed
    ..This amino-terminal end flexibility supports a processing model for IL-1 maturation that partially explains IL-1 polypeptide heterogeneity. ..
  41. Mackey J, Anbar R. High-dose ibuprofen therapy associated with esophageal ulceration after pneumonectomy in a patient with cystic fibrosis: a case report. BMC Pediatr. 2004;4:19 pubmed
    ..This report demonstrates that gastrointestinal tract anatomical abnormalities or dysmotility may be contraindications for therapy with high-dose ibuprofen in patients with cystic fibrosis. ..
  42. Bishai I, Dinarello C, Coceani F. Prostaglandin formation in feline cerebral microvessels: effect of endotoxin and interleukin-1. Can J Physiol Pharmacol. 1987;65:2225-30 pubmed
    ..We conclude that the cerebral microvasculature does not lend itself to an active role in the genesis of fever by being the site at which blood-borne interleukin-1 promotes prostaglandin E2 synthesis.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  43. Green A, Johnson J. Evidence for impaired coupling of receptors to Gi protein in adipocytes from streptozocin-induced diabetic rats. Diabetes. 1991;40:88-94 pubmed
    ..This revealed that the amounts of each of these G proteins were normal in membranes from the diabetic rats.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  44. Tran Thi T, Gyufko K, Haussinger D, Decker K. Net prostaglandin release by perfused rat liver after stimulation with phorbol 12-myristate 13-acetate. J Hepatol. 1988;6:151-7 pubmed
    ..e., from the vena cava to the portal vein, phorbol myristate acetate or PGE2 exerted only minor effects. These observations suggest a topological heterogeneity of producer and responder cells, respectively, in the liver sinusoid. ..
  45. Li Y, Ji D, Zhong S, Zhu J, Chen S, Hu G. Anti-tumor effects of proteoglycan from Phellinus linteus by immunomodulating and inhibiting Reg IV/EGFR/Akt signaling pathway in colorectal carcinoma. Int J Biol Macromol. 2011;48:511-7 pubmed publisher
  46. Norel X, Walch L, Labat C, Gascard J, Dulmet E, Brink C. Prostanoid receptors involved in the relaxation of human bronchial preparations. Br J Pharmacol. 1999;126:867-72 pubmed
    ..1 microM; n=3). 5. These data suggest that the relaxation of human isolated bronchial preparations induced by prostanoids involved IP-, EP2- and to a lesser extent DP-receptors but not EP4-receptor. ..
  47. Goh Y, Nakajima M, Azuma I, Hayaishi O. Prostaglandin D2 reduces intraocular pressure. Br J Ophthalmol. 1988;72:461-4 pubmed
    ..These results suggest that PGD2 or its analogues may be useful for treating glaucoma. ..
  48. Cannon J, Clark B, Wingfield P, Schmeissner U, Losberger C, Dinarello C, et al. Rabbit IL-1. Cloning, expression, biologic properties, and transcription during endotoxemia. J Immunol. 1989;142:2299-306 pubmed
    ..Liver tissue removed 4 h after endotoxin infusion produced lymphocyte-activating factors which were neutralized by more than 90% with a combination of goat anti-rabbit IL-1 alpha and anti-IL-1 beta. ..
  49. Venkatesh B, Tan C, Lam T. Prostaglandins and teleost neurohypophyseal hormones induce premature parturition in the guppy, Poecilia reticulata. Gen Comp Endocrinol. 1992;87:28-32 pubmed
    ..It may be that in the guppy, in which ovulation occurs at the end of gestation just prior to parturition, gonadotropin is not involved in the induction of ovulation and parturition. ..
  50. Zhao G, Raines A, Wieland M, Schwartz Z, Boyan B. Requirement for both micron- and submicron scale structure for synergistic responses of osteoblasts to substrate surface energy and topography. Biomaterials. 2007;28:2821-9 pubmed
    ..The results demonstrate a synergistic effect between high surface energy and topography of Ti substrates and show that both micron-scale and submicron scale structural features are necessary. ..
  51. Watson D, Kelly R, Miller W. Prostaglandins and prognosis in human breast cancer. Br J Cancer. 1987;56:367-70 pubmed
    ..It therefore seems unlikely that the level of these particular prostaglandins within breast carcinomas plays a fundamental role in the prognosis of the disease. ..
  52. Ujihara M, Tsuchida S, Satoh K, Sato K, Urade Y. Biochemical and immunological demonstration of prostaglandin D2, E2, and F2 alpha formation from prostaglandin H2 by various rat glutathione S-transferase isozymes. Arch Biochem Biophys. 1988;264:428-37 pubmed
    ..The F-reductase activity (3.3) was mostly catalyzed by the 1-2 group (75%). In the testis, the E-isomerase activity (3.9) was catalyzed by the 1-2 group (20-30%), the 3-4 group, and Yn1Yn2 (30-60%). ..