Skip to main content
Biochemical Journal logoLink to Biochemical Journal
. 1989 Apr 15;259(2):315–324. doi: 10.1042/bj2590315

The eicosanoids and their biochemical mechanisms of action.

W L Smith 1
PMCID: PMC1138513  PMID: 2655580

Full text

PDF
315

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Anderson R. J., Berl T., McDonald K. D., Schrier R. W. Evidence for an in vivo antagonism between vasopressin and prostaglandin in the mammalian kidney. J Clin Invest. 1975 Aug;56(2):420–426. doi: 10.1172/JCI108108. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Avdonin P. V., Svitina-Ulitina I. V., Leytin V. L., Tkachuk V. A. Interaction of stable prostaglandin endoperoxide analogs U46619 and U44069 with human platelet membranes: coupling of receptors with high-affinity GTPase and adenylate cyclase. Thromb Res. 1985 Oct 1;40(1):101–112. doi: 10.1016/0049-3848(85)90354-8. [DOI] [PubMed] [Google Scholar]
  3. BERGSTROEM S., DANIELSSON H., SAMUELSSON B. THE ENZYMATIC FORMATION OF PROSTAGLANDIN E2 FROM ARACHIDONIC ACID PROSTAGLANDINS AND RELATED FACTORS 32. Biochim Biophys Acta. 1964 Jul 15;90:207–210. doi: 10.1016/0304-4165(64)90145-x. [DOI] [PubMed] [Google Scholar]
  4. Bailey J. M., Muza B., Hla T., Salata K. Restoration of prostacyclin synthase in vascular smooth muscle cells after aspirin treatment: regulation by epidermal growth factor. J Lipid Res. 1985 Jan;26(1):54–61. [PubMed] [Google Scholar]
  5. Broekman M. J., Ward J. W., Marcus A. J. Fatty acid composition of phosphatidylinositol and phosphatidic acid in stimulated platelets. Persistence of arachidonyl-stearyl structure. J Biol Chem. 1981 Aug 25;256(16):8271–8274. [PubMed] [Google Scholar]
  6. Cairns J. A., Gent M., Singer J., Finnie K. J., Froggatt G. M., Holder D. A., Jablonsky G., Kostuk W. J., Melendez L. J., Myers M. G. Aspirin, sulfinpyrazone, or both in unstable angina. Results of a Canadian multicenter trial. N Engl J Med. 1985 Nov 28;313(22):1369–1375. doi: 10.1056/NEJM198511283132201. [DOI] [PubMed] [Google Scholar]
  7. Capdevila J., Marnett L. J., Chacos N., Prough R. A., Estabrook R. W. Cytochrome P-450-dependent oxygenation of arachidonic acid to hydroxyicosatetraenoic acids. Proc Natl Acad Sci U S A. 1982 Feb;79(3):767–770. doi: 10.1073/pnas.79.3.767. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Christ-Hazelhof E., Nugteren D. H. Isolation of PGH-PGD isomerase from rat spleen. Methods Enzymol. 1982;86:77–84. doi: 10.1016/0076-6879(82)86172-7. [DOI] [PubMed] [Google Scholar]
  9. Christ-Hazelhof E., Nugteren D. H. Prostacyclin is not a circulating hormone. Prostaglandins. 1981 Nov;22(5):739–746. doi: 10.1016/0090-6980(81)90213-6. [DOI] [PubMed] [Google Scholar]
  10. Ciabattoni G., Boss A. H., Daffonchio L., Daugherty J., FitzGerald G. A., Catella F., Dray F., Patrono C. Radioimmunoassay measurement of 2,3-dinor metabolites of prostacyclin and thromboxane in human urine. Adv Prostaglandin Thromboxane Leukot Res. 1987;17B:598–602. [PubMed] [Google Scholar]
  11. Corey E. J., Shih C., Cashman J. R. Docosahexaenoic acid is a strong inhibitor of prostaglandin but not leukotriene biosynthesis. Proc Natl Acad Sci U S A. 1983 Jun;80(12):3581–3584. doi: 10.1073/pnas.80.12.3581. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Culpepper R. M., Andreoli T. E. Interactions among prostaglandin E2, antidiuretic hormone, and cyclic adenosine monophosphate in modulating Cl- absorption in single mouse medullary thick ascending limbs of Henle. J Clin Invest. 1983 Jun;71(6):1588–1601. doi: 10.1172/JCI110915. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Currie M. G., Needleman P. Renal arachidonic acid metabolism. Annu Rev Physiol. 1984;46:327–341. doi: 10.1146/annurev.ph.46.030184.001551. [DOI] [PubMed] [Google Scholar]
  14. Daniel L. W., King L., Waite M. Source of arachidonic acid for prostaglandin synthesis in Madin-Darby canine kidney cells. J Biol Chem. 1981 Dec 25;256(24):12830–12835. [PubMed] [Google Scholar]
  15. DeWitt D. L., Day J. S., Sonnenburg W. K., Smith W. L. Concentrations of prostaglandin endoperoxide synthase and prostaglandin I2 synthase in the endothelium and smooth muscle of bovine aorta. J Clin Invest. 1983 Dec;72(6):1882–1888. doi: 10.1172/JCI111151. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. DeWitt D. L., Rollins T. E., Day J. S., Gauger J. A., Smith W. L. Orientation of the active site and antigenic determinants of prostaglandin endoperoxide synthase in the endoplasmic reticulum. J Biol Chem. 1981 Oct 25;256(20):10375–10382. [PubMed] [Google Scholar]
  17. DeWitt D. L., Smith W. L. Primary structure of prostaglandin G/H synthase from sheep vesicular gland determined from the complementary DNA sequence. Proc Natl Acad Sci U S A. 1988 Mar;85(5):1412–1416. doi: 10.1073/pnas.85.5.1412. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. DeWitt D. L., Smith W. L. Purification of prostacyclin synthase from bovine aorta by immunoaffinity chromatography. Evidence that the enzyme is a hemoprotein. J Biol Chem. 1983 Mar 10;258(5):3285–3293. [PubMed] [Google Scholar]
  19. Dyerberg J. Linolenate-derived polyunsaturated fatty acids and prevention of atherosclerosis. Nutr Rev. 1986 Apr;44(4):125–134. doi: 10.1111/j.1753-4887.1986.tb07603.x. [DOI] [PubMed] [Google Scholar]
  20. Erwich J. J., Keirse M. J. Human placental 15-hydroxy-prostaglandin dehydrogenase activity is under fetal genetic control. Prostaglandins. 1988 Jan;35(1):123–131. doi: 10.1016/0090-6980(88)90280-8. [DOI] [PubMed] [Google Scholar]
  21. Farman N., Pradelles P., Bonvalet J. P. Determination of prostaglandin E2 synthesis along rabbit nephron by enzyme immunoassay. Am J Physiol. 1986 Aug;251(2 Pt 2):F238–F244. doi: 10.1152/ajprenal.1986.251.2.F238. [DOI] [PubMed] [Google Scholar]
  22. Fejes-Tóth G., Magyar A., Walter J. Renal response to vasopressin after inhibition of prostaglandin synthesis. Am J Physiol. 1977 May;232(5):F416–F423. doi: 10.1152/ajprenal.1977.232.5.F416. [DOI] [PubMed] [Google Scholar]
  23. Ferreira S. H., Vane J. R. Prostaglandins: their disappearance from and release into the circulation. Nature. 1967 Dec 2;216(5118):868–873. doi: 10.1038/216868a0. [DOI] [PubMed] [Google Scholar]
  24. FitzGerald G. A., Brash A. R., Falardeau P., Oates J. A. Estimated rate of prostacyclin secretion into the circulation of normal man. J Clin Invest. 1981 Nov;68(5):1272–1276. doi: 10.1172/JCI110373. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. FitzGerald G. A. Dipyridamole. N Engl J Med. 1987 May 14;316(20):1247–1257. doi: 10.1056/NEJM198705143162005. [DOI] [PubMed] [Google Scholar]
  26. FitzGerald G. A., Oates J. A., Hawiger J., Maas R. L., Roberts L. J., 2nd, Lawson J. A., Brash A. R. Endogenous biosynthesis of prostacyclin and thromboxane and platelet function during chronic administration of aspirin in man. J Clin Invest. 1983 Mar;71(3):676–688. doi: 10.1172/JCI110814. [DOI] [PMC free article] [PubMed] [Google Scholar]
  27. Fitzpatrick F. A., Ennis M. D., Baze M. E. Novel effects of epoxyeicosatrienoic acid isomers: inhibition of platelet aggregation and cyclooxygenase activity. Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:109–114. [PubMed] [Google Scholar]
  28. Frangos J. A., Eskin S. G., McIntire L. V., Ives C. L. Flow effects on prostacyclin production by cultured human endothelial cells. Science. 1985 Mar 22;227(4693):1477–1479. doi: 10.1126/science.3883488. [DOI] [PubMed] [Google Scholar]
  29. Frielle T., Collins S., Daniel K. W., Caron M. G., Lefkowitz R. J., Kobilka B. K. Cloning of the cDNA for the human beta 1-adrenergic receptor. Proc Natl Acad Sci U S A. 1987 Nov;84(22):7920–7924. doi: 10.1073/pnas.84.22.7920. [DOI] [PMC free article] [PubMed] [Google Scholar]
  30. Funk C. D., Rådmark O., Fu J. Y., Matsumoto T., Jörnvall H., Shimizu T., Samuelsson B. Molecular cloning and amino acid sequence of leukotriene A4 hydrolase. Proc Natl Acad Sci U S A. 1987 Oct;84(19):6677–6681. doi: 10.1073/pnas.84.19.6677. [DOI] [PMC free article] [PubMed] [Google Scholar]
  31. Garcia-Perez A., Smith W. L. Apical-basolateral membrane asymmetry in canine cortical collecting tubule cells. Bradykinin, arginine vasopressin, prostaglandin E2 interrelationships. J Clin Invest. 1984 Jul;74(1):63–74. doi: 10.1172/JCI111419. [DOI] [PMC free article] [PubMed] [Google Scholar]
  32. Gerber J. G., Payne N. A., Murphy R. C., Nies A. S. Prostacyclin produced by the pregnant uterus in the dog may act as a circulating vasodepressor substance. J Clin Invest. 1981 Mar;67(3):632–636. doi: 10.1172/JCI110077. [DOI] [PMC free article] [PubMed] [Google Scholar]
  33. Glomset J. A. Fish, fatty acids, and human health. N Engl J Med. 1985 May 9;312(19):1253–1254. doi: 10.1056/NEJM198505093121909. [DOI] [PubMed] [Google Scholar]
  34. Goerig M., Habenicht A. J., Heitz R., Zeh W., Katus H., Kommerell B., Ziegler R., Glomset J. A. sn-1,2-Diacylglycerols and phorbol diesters stimulate thromboxane synthesis by de novo synthesis of prostaglandin H synthase in human promyelocytic leukemia cells. J Clin Invest. 1987 Mar;79(3):903–911. doi: 10.1172/JCI112900. [DOI] [PMC free article] [PubMed] [Google Scholar]
  35. Gorman R. R., Fitzpatrick F. A., Miller O. V. Reciprocal regulation of human platelet cAMP levels by thromboxane A2 and prostacyclin. Adv Cyclic Nucleotide Res. 1978;9:597–609. [PubMed] [Google Scholar]
  36. Grandt R., Aktories K., Jakobs K. H. Guanine nucleotides and monovalent cations increase agonist affinity of prostaglandin E2 receptors in hamster adipocytes. Mol Pharmacol. 1982 Sep;22(2):320–326. [PubMed] [Google Scholar]
  37. Grantham J. J., Orloff J. Effect of prostaglandin E1 on the permeability response of the isolated collecting tubule to vasopressin, adenosine 3',5'-monophosphate, and theophylline. J Clin Invest. 1968 May;47(5):1154–1161. doi: 10.1172/JCI105804. [DOI] [PMC free article] [PubMed] [Google Scholar]
  38. Habenicht A. J., Goerig M., Grulich J., Rothe D., Gronwald R., Loth U., Schettler G., Kommerell B., Ross R. Human platelet-derived growth factor stimulates prostaglandin synthesis by activation and by rapid de novo synthesis of cyclooxygenase. J Clin Invest. 1985 Apr;75(4):1381–1387. doi: 10.1172/JCI111839. [DOI] [PMC free article] [PubMed] [Google Scholar]
  39. Hamberg M., Samuelsson B. Prostaglandin endoperoxides. Novel transformations of arachidonic acid in human platelets. Proc Natl Acad Sci U S A. 1974 Sep;71(9):3400–3404. doi: 10.1073/pnas.71.9.3400. [DOI] [PMC free article] [PubMed] [Google Scholar]
  40. Hamberg M., Svensson J., Samuelsson B. Thromboxanes: a new group of biologically active compounds derived from prostaglandin endoperoxides. Proc Natl Acad Sci U S A. 1975 Aug;72(8):2994–2998. doi: 10.1073/pnas.72.8.2994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  41. Hammarström S. Conversion of 5,8,11-eicosatrienoic acid to leukotrienes C3 and D3. J Biol Chem. 1981 Mar 10;256(5):2275–2279. [PubMed] [Google Scholar]
  42. Hammarström S., Orning L., Bernström K., Gustafsson B., Norin E., Kaijser L. Metabolism of leukotriene C4 in rats and humans. Adv Prostaglandin Thromboxane Leukot Res. 1985;15:185–188. [PubMed] [Google Scholar]
  43. Handler J. S., Orloff J. Antidiuretic hormone. Annu Rev Physiol. 1981;43:611–624. doi: 10.1146/annurev.ph.43.030181.003143. [DOI] [PubMed] [Google Scholar]
  44. Hansen H. S. Essential fatty acid supplemented diet increases renal excretion of prostaglandin E2 and water in essential fatty acid deficient rats. Lipids. 1981 Nov;16(11):849–854. doi: 10.1007/BF02535041. [DOI] [PubMed] [Google Scholar]
  45. Hebert S. C., Andreoli T. E. Control of NaCl transport in the thick ascending limb. Am J Physiol. 1984 Jun;246(6 Pt 2):F745–F756. doi: 10.1152/ajprenal.1984.246.6.F745. [DOI] [PubMed] [Google Scholar]
  46. Hedin L., Gaddy-Kurten D., Kurten R., DeWitt D. L., Smith W. L., Richards J. S. Prostaglandin endoperoxide synthase in rat ovarian follicles: content, cellular distribution, and evidence for hormonal induction preceding ovulation. Endocrinology. 1987 Aug;121(2):722–731. doi: 10.1210/endo-121-2-722. [DOI] [PubMed] [Google Scholar]
  47. Homma S., Gapstur S. M., Yusufi A. N., Dousa T. P. In situ phosphorylation of proteins in MCTs microdissected from rat kidney: effect of AVP. Am J Physiol. 1988 Apr;254(4 Pt 2):F512–F520. doi: 10.1152/ajprenal.1988.254.4.F512. [DOI] [PubMed] [Google Scholar]
  48. Houslay M. D., Bojanic D., Wilson A. Platelet activating factor and U44069 stimulate a GTPase activity in human platelets which is distinct from the guanine nucleotide regulatory proteins, Ns and Ni. Biochem J. 1986 Mar 15;234(3):737–740. doi: 10.1042/bj2340737. [DOI] [PMC free article] [PubMed] [Google Scholar]
  49. Huslig R. L., Fogwell R. L., Smith W. L. The prostaglandin forming cyclooxygenase of ovine uterus: relationship to luteal function. Biol Reprod. 1979 Oct;21(3):589–600. doi: 10.1095/biolreprod21.3.589. [DOI] [PubMed] [Google Scholar]
  50. Ingerman-Wojenski C., Silver M. J., Smith J. B., Macarak E. Bovine endothelial cells in culture produce thromboxane as well as prostacyclin. J Clin Invest. 1981 May;67(5):1292–1296. doi: 10.1172/JCI110157. [DOI] [PMC free article] [PubMed] [Google Scholar]
  51. Jarabak J. Inhibition of the human placental NAD- and NADP-linked 15-hydroxyprostaglandin dehydrogenases by nonsteroidal anti-inflammatory drugs. Prostaglandins. 1988 Mar;35(3):403–411. doi: 10.1016/0090-6980(88)90131-1. [DOI] [PubMed] [Google Scholar]
  52. Jouvenaz G. H., Nugteren D. H., Beerthuis R. K., van Dorp D. A. A sensitive method for the determination of prostaglandins by gas chromatography with electron-capture detection. Biochim Biophys Acta. 1970 Feb 10;202(1):231–234. doi: 10.1016/0005-2760(70)90246-8. [DOI] [PubMed] [Google Scholar]
  53. Karthein R., Nastainczyk W., Ruf H. H. EPR study of ferric native prostaglandin H synthase and its ferrous NO derivative. Eur J Biochem. 1987 Jul 1;166(1):173–180. doi: 10.1111/j.1432-1033.1987.tb13499.x. [DOI] [PubMed] [Google Scholar]
  54. Kirschenbaum M. A., Lowe A. G., Trizna W., Fine L. G. Regulation of vasopressin action by prostaglandins. Evidence for prostaglandin synthesis in the rabbit cortical collecting tubule. J Clin Invest. 1982 Dec;70(6):1193–1204. doi: 10.1172/JCI110718. [DOI] [PMC free article] [PubMed] [Google Scholar]
  55. Kobilka B. K., MacGregor C., Daniel K., Kobilka T. S., Caron M. G., Lefkowitz R. J. Functional activity and regulation of human beta 2-adrenergic receptors expressed in Xenopus oocytes. J Biol Chem. 1987 Nov 15;262(32):15796–15802. [PubMed] [Google Scholar]
  56. Kobilka B. K., Matsui H., Kobilka T. S., Yang-Feng T. L., Francke U., Caron M. G., Lefkowitz R. J., Regan J. W. Cloning, sequencing, and expression of the gene coding for the human platelet alpha 2-adrenergic receptor. Science. 1987 Oct 30;238(4827):650–656. doi: 10.1126/science.2823383. [DOI] [PubMed] [Google Scholar]
  57. Kulmacz R. J., Lands W. E. Prostaglandin H synthase. Stoichiometry of heme cofactor. J Biol Chem. 1984 May 25;259(10):6358–6363. [PubMed] [Google Scholar]
  58. Lands W. E., Samuelsson B. Phospholipid precursors of prostaglandins. Biochim Biophys Acta. 1968 Oct 22;164(2):426–429. doi: 10.1016/0005-2760(68)90168-9. [DOI] [PubMed] [Google Scholar]
  59. Laniado-Schwartzman M., Davis K. L., McGiff J. C., Levere R. D., Abraham N. G. Purification and characterization of cytochrome P-450-dependent arachidonic acid epoxygenase from human liver. J Biol Chem. 1988 Feb 15;263(5):2536–2542. [PubMed] [Google Scholar]
  60. Lapetina E. G., Billah M. M., Cuatrecasas P. The initial action of thrombin on platelets. Conversion of phosphatidylinositol to phosphatidic acid preceding the production of arachidonic acid. J Biol Chem. 1981 May 25;256(10):5037–5040. [PubMed] [Google Scholar]
  61. Lee T. H., Hoover R. L., Williams J. D., Sperling R. I., Ravalese J., 3rd, Spur B. W., Robinson D. R., Corey E. J., Lewis R. A., Austen K. F. Effect of dietary enrichment with eicosapentaenoic and docosahexaenoic acids on in vitro neutrophil and monocyte leukotriene generation and neutrophil function. N Engl J Med. 1985 May 9;312(19):1217–1224. doi: 10.1056/NEJM198505093121903. [DOI] [PubMed] [Google Scholar]
  62. Lee T. H., Mencia-Huerta J. M., Shih C., Corey E. J., Lewis R. A., Austen K. F. Effects of exogenous arachidonic, eicosapentaenoic, and docosahexaenoic acids on the generation of 5-lipoxygenase pathway products by ionophore-activated human neutrophils. J Clin Invest. 1984 Dec;74(6):1922–1933. doi: 10.1172/JCI111612. [DOI] [PMC free article] [PubMed] [Google Scholar]
  63. Lefkowitz R. J., Mullikin D., Wood C. L., Gore T. B., Mukherjee C. Regulation of prostaglandin receptors by prostaglandins and guanine nucleotides in frog erythrocytes. J Biol Chem. 1977 Aug 10;252(15):5295–5303. [PubMed] [Google Scholar]
  64. Lester H. A., Steer M. L., Levitzki A. Prostaglandin-stimulated GTP hydrolysis associated with activation of adenylate cyclase in human platelet membranes. Proc Natl Acad Sci U S A. 1982 Feb;79(3):719–723. doi: 10.1073/pnas.79.3.719. [DOI] [PMC free article] [PubMed] [Google Scholar]
  65. Lewis H. D., Jr, Davis J. W., Archibald D. G., Steinke W. E., Smitherman T. C., Doherty J. E., 3rd, Schnaper H. W., LeWinter M. M., Linares E., Pouget J. M. Protective effects of aspirin against acute myocardial infarction and death in men with unstable angina. Results of a Veterans Administration Cooperative Study. N Engl J Med. 1983 Aug 18;309(7):396–403. doi: 10.1056/NEJM198308183090703. [DOI] [PubMed] [Google Scholar]
  66. Lister M. D., Deems R. A., Watanabe Y., Ulevitch R. J., Dennis E. A. Kinetic analysis of the Ca2+-dependent, membrane-bound, macrophage phospholipase A2 and the effects of arachidonic acid. J Biol Chem. 1988 Jun 5;263(16):7506–7513. [PubMed] [Google Scholar]
  67. Ludwig P., Holzhütter H. G., Colosimo A., Silvestrini M. C., Schewe T., Rapoport S. M. A kinetic model for lipoxygenases based on experimental data with the lipoxygenase of reticulocytes. Eur J Biochem. 1987 Oct 15;168(2):325–337. doi: 10.1111/j.1432-1033.1987.tb13424.x. [DOI] [PubMed] [Google Scholar]
  68. Marcus A. J., Safier L. B., Ullman H. L., Islam N., Broekman M. J., Falck J. R., Fischer S., von Schacky C. Platelet-neutrophil interactions. (12S)-hydroxyeicosatetraen-1,20-dioic acid: a new eicosanoid synthesized by unstimulated neutrophils from (12S)-20-dihydroxyeicosatetraenoic acid. J Biol Chem. 1988 Feb 15;263(5):2223–2229. [PubMed] [Google Scholar]
  69. Marshall P. J., Boatman D. E., Hokin L. E. Direct demonstration of the formation of prostaglandin E2 due to phosphatidylinositol breakdown associated with stimulation of enzyme secretion in the pancreas. J Biol Chem. 1981 Jan 25;256(2):844–847. [PubMed] [Google Scholar]
  70. Matsumoto T., Funk C. D., Rådmark O., Hög J. O., Jörnvall H., Samuelsson B. Molecular cloning and amino acid sequence of human 5-lipoxygenase. Proc Natl Acad Sci U S A. 1988 Jan;85(1):26–30. doi: 10.1073/pnas.85.1.26. [DOI] [PMC free article] [PubMed] [Google Scholar]
  71. Mauco G., Chap H., Douste-Blazy L. Characterization and properties of a phosphatidylinositol phosphodiesterase (phospholipase C) from platelet cytosol. FEBS Lett. 1979 Apr 15;100(2):367–370. doi: 10.1016/0014-5793(79)80371-3. [DOI] [PubMed] [Google Scholar]
  72. Minami M., Ohno S., Kawasaki H., Rådmark O., Samuelsson B., Jörnvall H., Shimizu T., Seyama Y., Suzuki K. Molecular cloning of a cDNA coding for human leukotriene A4 hydrolase. Complete primary structure of an enzyme involved in eicosanoid synthesis. J Biol Chem. 1987 Oct 15;262(29):13873–13876. [PubMed] [Google Scholar]
  73. Mizuno K., Yamamoto S., Lands W. E. Effects of non-steroidal anti-inflammatory drugs on fatty acid cyclooxygenase and prostaglandin hydroperoxidase activities. Prostaglandins. 1982 May;23(5):743–757. [PubMed] [Google Scholar]
  74. Moonen P., Buytenhek M., Nugteren D. H. Purification of PGH-PGE isomerase from sheep vesicular glands. Methods Enzymol. 1982;86:84–91. doi: 10.1016/0076-6879(82)86173-9. [DOI] [PubMed] [Google Scholar]
  75. Narumiya S., Salmon J. A. Arachidonic acid-15-lipoxygenase from rabbit peritoneal polymorphonuclear leukocytes. Methods Enzymol. 1982;86:45–48. doi: 10.1016/0076-6879(82)86166-1. [DOI] [PubMed] [Google Scholar]
  76. Narumiya S., Salmon J. A., Cottee F. H., Weatherley B. C., Flower R. J. Arachidonic acid 15-lipoxygenase from rabbit peritoneal polymorphonuclear leukocytes. Partial purification and properties. J Biol Chem. 1981 Sep 25;256(18):9583–9592. [PubMed] [Google Scholar]
  77. Needleman P., Raz A., Minkes M. S., Ferrendelli J. A., Sprecher H. Triene prostaglandins: prostacyclin and thromboxane biosynthesis and unique biological properties. Proc Natl Acad Sci U S A. 1979 Feb;76(2):944–948. doi: 10.1073/pnas.76.2.944. [DOI] [PMC free article] [PubMed] [Google Scholar]
  78. Negishi M., Ito S., Yokohama H., Hayashi H., Katada T., Ui M., Hayaishi O. Functional reconstitution of prostaglandin E receptor from bovine adrenal medulla with guanine nucleotide binding proteins. J Biol Chem. 1988 May 15;263(14):6893–6900. [PubMed] [Google Scholar]
  79. Neufeld E. J., Majerus P. W. Arachidonate release and phosphatidic acid turnover in stimulated human platelets. J Biol Chem. 1983 Feb 25;258(4):2461–2467. [PubMed] [Google Scholar]
  80. Nugteren D. H. Arachidonic acid-12-lipoxygenase from bovine platelets. Methods Enzymol. 1982;86:49–54. doi: 10.1016/0076-6879(82)86167-3. [DOI] [PubMed] [Google Scholar]
  81. Ohki S., Ogino N., Yamamoto S., Hayaishi O. Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular gland microsomes. J Biol Chem. 1979 Feb 10;254(3):829–836. [PubMed] [Google Scholar]
  82. Pagels W. R., Sachs R. J., Marnett L. J., Dewitt D. L., Day J. S., Smith W. L. Immunochemical evidence for the involvement of prostaglandin H synthase in hydroperoxide-dependent oxidations by ram seminal vesicle microsomes. J Biol Chem. 1983 May 25;258(10):6517–6523. [PubMed] [Google Scholar]
  83. Pong S. S., DeHaven R. N. Characterization of a leukotriene D4 receptor in guinea pig lung. Proc Natl Acad Sci U S A. 1983 Dec;80(24):7415–7419. doi: 10.1073/pnas.80.24.7415. [DOI] [PMC free article] [PubMed] [Google Scholar]
  84. Relman A. S. Aspirin for the primary prevention of myocardial infarction. N Engl J Med. 1988 Jan 28;318(4):245–246. doi: 10.1056/NEJM198801283180410. [DOI] [PubMed] [Google Scholar]
  85. Rittenhouse-Simmons S. Differential activation of platelet phospholipases by thrombin and ionophore A23187. J Biol Chem. 1981 May 10;256(9):4153–4155. [PubMed] [Google Scholar]
  86. Roberts L. J., 2nd, Sweetman B. J., Lewis R. A., Austen K. F., Oates J. A. Increased production of prostaglandin D2 in patients with systemic mastocytosis. N Engl J Med. 1980 Dec 11;303(24):1400–1404. doi: 10.1056/NEJM198012113032405. [DOI] [PubMed] [Google Scholar]
  87. Rollins T. E., Smith W. L. Subcellular localization of prostaglandin-forming cyclooxygenase in Swiss mouse 3T3 fibroblasts by electron microscopic immunocytochemistry. J Biol Chem. 1980 May 25;255(10):4872–4875. [PubMed] [Google Scholar]
  88. Rome L. H., Lands W. E. Structural requirements for time-dependent inhibition of prostaglandin biosynthesis by anti-inflammatory drugs. Proc Natl Acad Sci U S A. 1975 Dec;72(12):4863–4865. doi: 10.1073/pnas.72.12.4863. [DOI] [PMC free article] [PubMed] [Google Scholar]
  89. Roth G. J., Machuga E. T., Ozols J. Isolation and covalent structure of the aspirin-modified, active-site region of prostaglandin synthetase. Biochemistry. 1983 Sep 27;22(20):4672–4675. doi: 10.1021/bi00289a010. [DOI] [PubMed] [Google Scholar]
  90. Roth G. J., Machuga E. T., Strittmatter P. The heme-binding properties of prostaglandin synthetase from sheep vesicular gland. J Biol Chem. 1981 Oct 10;256(19):10018–10022. [PubMed] [Google Scholar]
  91. Roth G. J., Siok C. J., Ozols J. Structural characteristics of prostaglandin synthetase from sheep vesicular gland. J Biol Chem. 1980 Feb 25;255(4):1301–1304. [PubMed] [Google Scholar]
  92. Samuelsson B., Dahlén S. E., Lindgren J. A., Rouzer C. A., Serhan C. N. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science. 1987 Sep 4;237(4819):1171–1176. doi: 10.1126/science.2820055. [DOI] [PubMed] [Google Scholar]
  93. Schlondorff D., Satriano J. A., Schwartz G. J. Synthesis of prostaglandin E2 in different segments of isolated collecting tubules from adult and neonatal rabbits. Am J Physiol. 1985 Jan;248(1 Pt 2):F134–F144. doi: 10.1152/ajprenal.1985.248.1.F134. [DOI] [PubMed] [Google Scholar]
  94. Schwartzman M. L., Abraham N. G., Masferrer J., Dunn M. W., McGiff J. C. Cytochrome P450-dependent arachidonate metabolism in corneal epithelium: formation of biologically active compounds. Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:78–83. [PubMed] [Google Scholar]
  95. Schwartzman M., Liberman E., Raz A. Bradykinin and angiotensin II activation of arachidonic acid deacylation and prostaglandin E2 formation in rabbit kidney. Hormone-sensitive versus hormone-insensitive lipid pools of arachidonic acid. J Biol Chem. 1981 Mar 10;256(5):2329–2333. [PubMed] [Google Scholar]
  96. Shak S., Goldstein I. M. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. J Biol Chem. 1984 Aug 25;259(16):10181–10187. [PubMed] [Google Scholar]
  97. Shen R. F., Tai H. H. Immunoaffinity purification and characterization of thromboxane synthase from porcine lung. J Biol Chem. 1986 Sep 5;261(25):11592–11599. [PubMed] [Google Scholar]
  98. Shibata D., Steczko J., Dixon J. E., Hermodson M., Yazdanparast R., Axelrod B. Primary structure of soybean lipoxygenase-1. J Biol Chem. 1987 Jul 25;262(21):10080–10085. [PubMed] [Google Scholar]
  99. Shimizu T., Yamamoto S., Hayaishi O. Purification of PGH-PGD isomerase from rat brain. Methods Enzymol. 1982;86:73–77. doi: 10.1016/0076-6879(82)86171-5. [DOI] [PubMed] [Google Scholar]
  100. Sibley D. R., Lefkowitz R. J. Molecular mechanisms of receptor desensitization using the beta-adrenergic receptor-coupled adenylate cyclase system as a model. Nature. 1985 Sep 12;317(6033):124–129. doi: 10.1038/317124a0. [DOI] [PubMed] [Google Scholar]
  101. Smith W. L., Bell T. G. Immunohistochemical localization of the prostaglandin-forming cyclooxygenase in renal cortex. Am J Physiol. 1978 Nov;235(5):F451–F457. doi: 10.1152/ajprenal.1978.235.5.F451. [DOI] [PubMed] [Google Scholar]
  102. Smith W. L., Lands W. E. Stimulation and blockade of prostaglandin biosynthesis. J Biol Chem. 1971 Nov;246(21):6700–6702. [PubMed] [Google Scholar]
  103. Smith W. L. Prostaglandin biosynthesis and its compartmentation in vascular smooth muscle and endothelial cells. Annu Rev Physiol. 1986;48:251–262. doi: 10.1146/annurev.ph.48.030186.001343. [DOI] [PubMed] [Google Scholar]
  104. Soberman R. J., Harper T. W., Murphy R. C., Austen K. F. Identification and functional characterization of leukotriene B4 20-hydroxylase of human polymorphonuclear leukocytes. Proc Natl Acad Sci U S A. 1985 Apr;82(8):2292–2295. doi: 10.1073/pnas.82.8.2292. [DOI] [PMC free article] [PubMed] [Google Scholar]
  105. Sonnenburg W. K., Smith W. L. Regulation of cyclic AMP metabolism in rabbit cortical collecting tubule cells by prostaglandins. J Biol Chem. 1988 May 5;263(13):6155–6160. [PubMed] [Google Scholar]
  106. Sprecher H., VanRollins M., Sun F., Wyche A., Needleman P. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized in the kidney. J Biol Chem. 1982 Apr 10;257(7):3912–3918. [PubMed] [Google Scholar]
  107. Stanford N., Roth G. J., Shen T. Y., Majerus P. W. Lack of covalent modification of prostaglandin synthetase (cyclo-oxygenase) by indomethacin. Prostaglandins. 1977 Apr;13(4):669–675. doi: 10.1016/0090-6980(77)90237-4. [DOI] [PubMed] [Google Scholar]
  108. Tachibana M., Fex J., Urade Y., Hayaishi O. Brain-type prostaglandin D synthetase occurs in the rat cochlea. Proc Natl Acad Sci U S A. 1987 Nov;84(21):7677–7680. doi: 10.1073/pnas.84.21.7677. [DOI] [PMC free article] [PubMed] [Google Scholar]
  109. Tanaka Y., Ward S. L., Smith W. L. Immunochemical and kinetic evidence for two different prostaglandin H-prostaglandin E isomerases in sheep vesicular gland microsomes. J Biol Chem. 1987 Jan 25;262(3):1374–1381. [PubMed] [Google Scholar]
  110. Teitelbaum I., Mansour J. N., Berl T. Effect of cAMP on prostaglandin E2 production in cultured rat inner medullary collecting tubule cells. Am J Physiol. 1986 Oct;251(4 Pt 2):F671–F677. doi: 10.1152/ajprenal.1986.251.4.F671. [DOI] [PubMed] [Google Scholar]
  111. Torikai S., Kurokawa K. Effect of PGE2 on vasopressin-dependent cell cAMP in isolated single nephron segments. Am J Physiol. 1983 Jul;245(1):F58–F66. doi: 10.1152/ajprenal.1983.245.1.F58. [DOI] [PubMed] [Google Scholar]
  112. 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 Aug 1;264(2):428–437. doi: 10.1016/0003-9861(88)90308-6. [DOI] [PubMed] [Google Scholar]
  113. Ulevitch R. J., Watanabe Y., Sano M., Lister M. D., Deems R. A., Dennis E. A. Solubilization, purification, and characterization of a membrane-bound phospholipase A2 from the P388D1 macrophage-like cell line. J Biol Chem. 1988 Mar 5;263(7):3079–3085. [PubMed] [Google Scholar]
  114. Ullrich V., Haurand M. Thromboxane synthase as a cytochrome P450 enzyme. Adv Prostaglandin Thromboxane Leukot Res. 1983;11:105–110. [PubMed] [Google Scholar]
  115. VAN DORPD, BEERTHUIS R. K., NUGTEREN D. H., VONKEMAN H. THE BIOSYNTHESIS OF PROSTAGLANDINS. Biochim Biophys Acta. 1964 Jul 15;90:204–207. doi: 10.1016/0304-4165(64)90144-8. [DOI] [PubMed] [Google Scholar]
  116. Van Der Ouderaa F. J., Buytenhek M., Nugteren D. H., Van Dorp D. A. Acetylation of prostaglandin endoperoxide synthetase with acetylsalicylic acid. Eur J Biochem. 1980 Aug;109(1):1–8. doi: 10.1111/j.1432-1033.1980.tb04760.x. [DOI] [PubMed] [Google Scholar]
  117. Van der Ouderaa F. J., Buytenhek M., Nugteren D. H., Van Dorp D. A. Purification and characterisation of prostaglandin endoperoxide synthetase from sheep vesicular glands. Biochim Biophys Acta. 1977 May 25;487(2):315–331. doi: 10.1016/0005-2760(77)90008-x. [DOI] [PubMed] [Google Scholar]
  118. Watanabe K., Iguchi Y., Iguchi S., Arai Y., Hayaishi O., Roberts L. J., 2nd Stereospecific conversion of prostaglandin D2 to 9 alpha, 11 beta-prostaglandin F2 and prostaglandin H2 to prostaglandin F2 alpha by PGF synthetase. Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:44–46. [PubMed] [Google Scholar]
  119. Watanabe T., Umegaki K., Smith W. L. Association of a solubilized prostaglandin E2 receptor from renal medulla with a pertussis toxin-reactive guanine nucleotide regulatory protein. J Biol Chem. 1986 Oct 15;261(29):13430–13437. [PubMed] [Google Scholar]
  120. Weksler B. B., Kent J. L., Rudolph D., Scherer P. B., Levy D. E. Effects of low dose aspirin on platelet function in patients with recent cerebral ischemia. Stroke. 1985 Jan-Feb;16(1):5–9. doi: 10.1161/01.str.16.1.5. [DOI] [PubMed] [Google Scholar]
  121. Weksler B. B., Ley C. W., Jaffe E. A. Stimulation of endothelial cell prostacyclin production by thrombin, trypsin, and the ionophore A 23187. J Clin Invest. 1978 Nov;62(5):923–930. doi: 10.1172/JCI109220. [DOI] [PMC free article] [PubMed] [Google Scholar]
  122. Weksler B. B. Regulation of cyclooxygenase activity in human vascular tissue. Adv Prostaglandin Thromboxane Leukot Res. 1987;17A:238–243. [PubMed] [Google Scholar]
  123. Whiteley P. J., Needleman P. Mechanism of enhanced fibroblast arachidonic acid metabolism by mononuclear cell factor. J Clin Invest. 1984 Dec;74(6):2249–2253. doi: 10.1172/JCI111651. [DOI] [PMC free article] [PubMed] [Google Scholar]
  124. Whorton A. R., Young S. L., Data J. L., Barchowsky A., Kent R. S. Mechanism of bradykinin-stimulated prostacyclin synthesis in porcine aortic endothelial cells. Biochim Biophys Acta. 1982 Jul 20;712(1):79–87. doi: 10.1016/0005-2760(82)90087-x. [DOI] [PubMed] [Google Scholar]
  125. Yokoyama C., Shinjo F., Yoshimoto T., Yamamoto S., Oates J. A., Brash A. R. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. J Biol Chem. 1986 Dec 15;261(35):16714–16721. [PubMed] [Google Scholar]
  126. Yumoto N., Hatanaka M., Watanabe Y., Hayaishi O. Involvement of GTP-regulatory protein in brain prostaglandin E2 receptor and separation of the two components. Biochem Biophys Res Commun. 1986 Feb 26;135(1):282–289. doi: 10.1016/0006-291x(86)90974-5. [DOI] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES