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Eicosanoid

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
1Prostaglandin E2 7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid XPR1401EicosanoidShouzo YamamotoPGE2 C20H32O5 352.465Download ChemDraw structure dataProstaglandin E2 exhibits various biological activities such as vasodilatation, uterine contraction, gastrointestinal contraction, bronchodilatation, diuresis, pyrexia, inhibition of gastric secretion, bone resorption and immunosuppression << Ref. 0002>>. Prostaglandin E2 is a ligand to receptors present in the cell membrane, and there are at least 4 subtypes of its receptor. Different tissue distributions and signal transductions of these receptor subtypes explain a variety of biological activities of prostaglandin E2 << Ref. 0003>>. 65-66degC << Ref. 1001>> [a]d-26=-61.0deg(C=1.0, TETRAHYDROFURAN) << Ref. 1001>> ETHYL ACETATE,THF,CHLOROFORM<< Ref. 1002/1006>>. STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions << Ref. 1004/1005>> d,l-mixture ; 3400, 1710, 970cm-1 << Ref. 1003>> 13C-NMR(CDCl3) : 214.71(C9),178.39(C1), 136.62(C14), 131.52(C13), 130.91(C5), 126.69(C6), 73.19(C15), 72.13(C11), 54.55(C12), 53.51(C8), 46.23(C10), 37.00 (C16), 33.56(C2), 31.73(C18), 26.47(C4), 25.20(C7,17), 24.60(C3), 22.64(C19), 14.04. << Ref. 1002>>. 1H-NMR(CDCl3) : d5.67(dd, J=6.6Hz, 15.4, 1H, 14-CH), 5.57(dd, J=8.1, 15.4Hz, 1H, 13-CH), 5.40(m, 2H, 5.6-CH), 4.12(q, J=6.5, 6.7, 6.8Hz, 1H, 15-CH), 4.06(q, J=8.1, 8.2, 8.3Hz, 1H, 11-CH), 2.72(dd, J= << Ref. 1002>> d,l-mixture ; 334(M+-18), 316, 298, 190 << Ref. 1003>> Prostaglandin E2 was found to be accummulating in human semen in an amount of about 13 microgram per ml << Ref. 0001>>. In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin E2. [Table 0001] << Ref. 1001>> Prostaglandin E2 is produced from arachidonic acid via prostaglandins G2 and H2 by the catalyses of prostaglandin endoperoxide synthase (cyclooxygenase) << Ref. 0004>> and prostaglandin E synthase << Ref. 0005>>. Two isoforms of the cyclooxygnease enzyme responsible for prostaglandin H2 synthesis are present. Cyclooxygenase-1 is constitutively found in most mammalian tissues, while cyclooxygnease-2 is induced rapidly and transiently in physiological and pathological events, especially in inflammation << Ref. 0004>>. The biological activities of prostaglandin E2 are lost by oxidation of its 15-hydroxyl group catalyzed by 15-hydroxyprostaglandin dehydrogenase << Ref. 0006>>. cDNAs of the two cyclooxygenase isozymes responsible for prostaglandin H2 synthesis have been cloned, and the primary structures of these enzymes were deduced from the nucleotide seuences << Ref. 0007/0008>>. Their genomic DNA were also cloned, and the genomic structure were eludicated << Ref. 0007>>. cDNAs of four subtypes of prostaglandin E2 receptors (EP1-4) were cloned, and the 7-transmembrane domain structures of the receptors coupled with certain G proteins were reported << Ref. 0003>>. << Ref.0001 >> AUTHOR: Bergstrom, S. TITLE: Prostaglandins: members of a new hormonal system. These physiologically very potent compounds of ubiquitous occurrence are formed from essential fatty acids PubMed ID:4291104 JOURNAL: Science. VOLUME: 157 PAGE: 382-391(1967)
<< Ref.0002 >> AUTHOR: Bergstrom, S., Carlson, L. A., and Weeks, J. R. TITLE: The prostaglandins: a family of biologically active lipids PubMed ID:4873508 JOURNAL: Pharmacol Rev. VOLUME: 20 PAGE: 1-48(1968)
<< Ref.0003 >> AUTHOR: Negishi, M., Sugimoto, Y., and Ichikawa, A. TITLE: Molecular mechanisms of diverse actions of prostanoid receptors PubMed ID:7492609 JOURNAL: Biochim Biophys Acta. VOLUME: 1259 PAGE: 109-119(1995)
<< Ref.0004 >> AUTHOR: Smith, W. L., Garavito, R. M., and DeWitt, D. L. TITLE: Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2 PubMed ID:8969167 JOURNAL: J Biol Chem. VOLUME: 271 PAGE: 33157-33160(1996)
<< Ref.0005 >> AUTHOR: Urade, Y., Watanabe, K., and Hayaishi, O. TITLE: Prostaglandin D, E, and F synthases PubMed ID:8777570 JOURNAL: J Lipid Mediat Cell Signal. VOLUME: 12 PAGE: 257-273(1995)
<< Ref.0006 >> AUTHOR: Hansen, H. S. TITLE: 15-hydroxyprostaglandin dehydrogenase. A review PubMed ID:184496 JOURNAL: Prostaglandins. VOLUME: 12 PAGE: 647-679(1976)
<< Ref.0007 >> AUTHOR: Funk, C.D. TITLE: Molecular biology in the eicosanoid field . PubMed ID:8341804 JOURNAL: Progr. Nucleic Acid Res. VOLUME: 45 PAGE: 67 -98 (1993)
<< Ref.0008 >> AUTHOR: Herschman, H.R. TITLE: Prostaglandin synthase 2. PubMed ID:8341804 JOURNAL: Biochim. Biophys. Acta VOLUME: 1299 PAGE: 125 -140 (1996)
<< Ref.1001 >> AUTHOR: Corey, E. J., Schaaf, T. K., Huber, W., Koelliker, U., and Weinshenker, N. M. TITLE: Total synthesis of prostaglandins F2-alpha and E2 as the naturally occurring forms PubMed ID:5411057 JOURNAL: J Am Chem Soc. VOLUME: 92 PAGE: 397-398(1970)
<< Ref.1002 >> AUTHOR: Donaldson,R.E., Saddler,J.C., Byrn,S., McKenzie, A.T., and Fuchs, P.L. TITLE: A Triply Convergent Total Synthesis of L-(-)-Prostaglandin E2. JOURNAL: J. Org. Chem. VOLUME: 48 PAGE: 2167 -2188 (1983)
<< Ref.1003 >> AUTHOR: Chen, S.-M.L., Schaub, R.E., and Grudzinskas,C.V. TITLE: Prostaglandins and Congeners.19. Vinylstannanes:Useful Organometallic Reagents for the Synthesis of Prostaglandins and Prostaglandin Intermediates. JOURNAL: J. Org. Chem. VOLUME: 43 PAGE: 3450 -3454 (1978)
<< Ref.1004 >> AUTHOR: Karim, S. M., Devlin, J., and Hillier, K. TITLE: The stability of dilute solutions of prostaglandins E1, E2, F1-alpha and F2-alpha PubMed ID:5724918 JOURNAL: Eur J Pharmacol. VOLUME: 4 PAGE: 416-420(1968)
<< Ref.1005 >> AUTHOR: Pike, J.E., Lincoln,F.H., and Schneider,W.P. TITLE: Prostanoic Acid Chemistry. JOURNAL: J. Org. Chem. VOLUME: 34 PAGE: 3552 -3557 (1969)
<< Ref.1006 >> AUTHOR: Sih, C. J., Heather, J. B., Sood, R., Price, P., Peruzzotti, G., Lee, L. F., and Lee, S. S. TITLE: Asymmetric total synthesis of (minus)-prostaglandin E1 and (minus)-prostaglandin E2 PubMed ID:1133372 JOURNAL: J Am Chem Soc. VOLUME: 97 PAGE: 865-874(1975)
2PROSTAGLANDIN F2a 7-[3(R),5(S)-Dihydroxy-2(R)-(3(S)-hydroxy-1(E)-octenylcyclopentan-1(R)-yl]-5(Z)-heptenoic acid XPR1501EicosanoidShouzo YamamotoPGF2a C20H34O5 354.481Download ChemDraw structure dataProstaglandin F2a exhibits various biological activities such as uterine contraction, gastrointestinal contraction, bronchoconstriction, luteolysis and vasoconstriction << Ref. 0002>>. Prostaglandin F2a is a ligand to a receptor (FP) present in the cell membrane << Ref. 0003>>. 25-35degC << Ref. 1007>> [a]d-25=23.8 deg(C=1,THF) << Ref. 1001>> ETHYL ACETATE, ACETONE, DIETHYLETHER << Ref. 1005>>. STABILITIES: to be stable under neutral and basic conditions << Ref. 1004>> NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm-1 << Ref. 1005>> 1H-NMR(d6-ACETONE) : d 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) << Ref. 1005>>. 13C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 << Ref. 1008>> 354(M+), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 << Ref. 1009>> Prostaglandin F2a was found to be accummulating in human semen in an amount of about 2 microgram per ml << Ref. 0001>>. In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2a. << Ref. 1001>> [Table 0001] Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2a. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11b-prostaglandin F2 << Ref. 0005>>. cDNA for prostaglandin F synthase was cloned from bovine lung << Ref. 0005>>. cDNA for prostaglandin F2a receptor (FP) was cloned, and its 7ptransmembrane structure was reported << Ref. 0003>>. << Ref.0001 >> AUTHOR: Bergstrom, S. TITLE: Prostaglandins: members of a new hormonal system. These physiologically very potent compounds of ubiquitous occurrence are formed from essential fatty acids PubMed ID:4291104 JOURNAL: Science. VOLUME: 157 PAGE: 382-391(1967)
<< Ref.0002 >> AUTHOR: Bergstrom, S., Carlson, L. A., and Weeks, J. R. TITLE: The prostaglandins: a family of biologically active lipids PubMed ID:4873508 JOURNAL: Pharmacol Rev. VOLUME: 20 PAGE: 1-48(1968)
<< Ref.0003 >> AUTHOR: Negishi, M., Sugimoto, Y., and Ichikawa, A. TITLE: Molecular mechanisms of diverse actions of prostanoid receptors PubMed ID:7492609 JOURNAL: Biochim Biophys Acta. VOLUME: 1259 PAGE: 109-119(1995)
<< Ref.0005 >> AUTHOR: Urade, Y., Watanabe, K., and Hayaishi, O. TITLE: Prostaglandin D, E, and F synthases PubMed ID:8777570 JOURNAL: J Lipid Mediat Cell Signal. VOLUME: 12 PAGE: 257-273(1995)
<< Ref.1001 >> AUTHOR: Corey, E. J., Schaaf, T. K., Huber, W., Koelliker, U., and Weinshenker, N. M. TITLE: Total synthesis of prostaglandins F2-alpha and E2 as the naturally occurring forms PubMed ID:5411057 JOURNAL: J Am Chem Soc. VOLUME: 92 PAGE: 397-398(1970)
<< Ref.1004 >> AUTHOR: Karim, S. M., Devlin, J., and Hillier, K. TITLE: The stability of dilute solutions of prostaglandins E1, E2, F1-alpha and F2-alpha PubMed ID:5724918 JOURNAL: Eur J Pharmacol. VOLUME: 4 PAGE: 416-420(1968)
<< Ref.1005 >> AUTHOR: Pike, J.E., Lincoln,F.H., and Schneider,W.P. TITLE: Prostanoic Acid Chemistry. JOURNAL: J. Org. Chem. VOLUME: 34 PAGE: 3552 -3557 (1969)
<< Ref.1007 >> AUTHOR: Bundy, G. L., Schneider, W. P., Lincoln, F. H., and Pike, J. E. TITLE: The synthesis of prostaglandins E 2 and F 2a from (15R)- and (15S)-PGA 2 PubMed ID:5016033 JOURNAL: J Am Chem Soc. VOLUME: 94 PAGE: 2123-2124(1972)
<< Ref.1008 >> AUTHOR: Lukacs,G., Piriou,F., and Gero,S.D. TITLE: Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Naturally Occurring Substances. Prostaglandins. JOURNAL: Tetrah. Lett. VOLUME: PAGE: 515 -518 (1973)
<< Ref.1009 >> AUTHOR: Horvath, G. TITLE: Mass spectral studies on prostaglandins. IV--Prostaglandin F2alpha PubMed ID:990421 JOURNAL: Biomed Mass Spectrom. VOLUME: 3 PAGE: 127-136(1976)
3PROSTAGLANDIN D2 7-[5(S)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl)-3-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid XPR1301EicosanoidShouzo YamamotoPGD2 C20H32O5 352.465Download ChemDraw structure dataBiological significance of prostaglandin D2 was unknown except anti-aggregatory and bronchoconstrictive activities << Ref. 0009>>. Recently prostaglandin D2 has been noted as antineoplastic agent (actually attributed to D12-prostaglandin J2) << Ref. 0010/0011>> and as a sleep-inducing compound << Ref. 0012>>. Prostaglandin D2 binds to a receptor with 7 transmembrane domains (DP) coupled to a Gs protein << Ref. 0003>>. 68degC << Ref. 1010>> [a]d-20=9deg (C=2.11,THF) << Ref. 1012>> ETHYL ACETATE,THF,CHLOROFORM << Ref. 1012>> KBr : 3400-2500, 1740, 1700, 975cm-1 << Ref. 1010>> 1H-NMR(270MHz, CDCl3) : d 5.63(dd,J=7 & 16Hz,1H,14-CH), 5.43(dd,J=16 & 8.5Hz,1H,13-CH), 4.47(m, 1H, 9-CH), 4.09(bq, J=7Hz, 1H, 15-CH), 2.87(dd, J=12 & 8.5Hz, 1H, 12-CH), 2.45(m, 2H, 10-CH2), 1.95(bm, 1H, 8-CH) << Ref. 1011>> m/e 334, 316, 246, 245, 191, 190, 161, 55 << Ref. 1012>> In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin D2. Prostaglandin D2 is produced in barin, lung, spleen, mast cells and other tissues << Ref. 0005>>. << Ref. 1010>> [Table 0001] Prostaglandin D2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2. There are two isozymes of prostaglandin D synthase (hematopoietic type and lipocalin type) distinguished by glutathione reequirement and effect of inhibitor << Ref. 0005>>. Prostaglandin D2 is either reduced to 9a,11b-prostaglandin F or oxidized to 15-keto-prostaglandin D2 by a specific dehydrogenase << Ref. 0009>>. Non-enzymatic transformation of prostaglandin D2 produces anti-neoplastic D12-prostaglandin J2 << Ref. 0011>>. cDNA and genomic DNA of prostaglandin D synthase were cloned << Ref. 0005>>. cDNA for DP was isolated << Ref. 0011>>. << Ref.0003 >> AUTHOR: Negishi, M., Sugimoto, Y., and Ichikawa, A. TITLE: Molecular mechanisms of diverse actions of prostanoid receptors PubMed ID:7492609 JOURNAL: Biochim Biophys Acta. VOLUME: 1259 PAGE: 109-119(1995)
<< Ref.0005 >> AUTHOR: Urade, Y., Watanabe, K., and Hayaishi, O. TITLE: Prostaglandin D, E, and F synthases PubMed ID:8777570 JOURNAL: J Lipid Mediat Cell Signal. VOLUME: 12 PAGE: 257-273(1995)
<< Ref.0009 >> AUTHOR: Giles, H., and Leff, P. TITLE: The biology and pharmacology of PGD2 PubMed ID:3283848 JOURNAL: Prostaglandins. VOLUME: 35 PAGE: 277-300(1988)
<< Ref.0010 >> AUTHOR: Fukushima, M. TITLE: Biological activities and mechanisms of action of PGJ2 and related compounds: an update PubMed ID:1438462 JOURNAL: Prostaglandins Leukot Essent Fatty Acids. VOLUME: 47 PAGE: 1-12(1992)
<< Ref.0011 >> AUTHOR: Negishi,M., Koizumi,T., and Ichikawa,A. TITLE: Biological actions of D12-prostaglandin J2. PubMed ID:8777585 JOURNAL: J. Lipid Mediators Cell Signaling VOLUME: 12 PAGE: 443 -448 (1995)
<< Ref.0012 >> AUTHOR: Hayaishi, O. TITLE: Sleep-wake regulation by prostaglandins D2 and E2 PubMed ID:3049580 JOURNAL: J Biol Chem. VOLUME: 263 PAGE: 14593-14596(1988)
<< Ref.1010 >> AUTHOR: Hayashi,M., and Tanouchi,T. TITLE: Syntheses of 11-Dehydro-13,14-dihydro-PGE1 and PGD2. JOURNAL: J. Org. Chem. VOLUME: 38 PAGE: 2115 -2116 (1973)
<< Ref.1011 >> AUTHOR: Jenny,E.F., and Schä$ublin,P. TITLE: Total Synthesis of Prostaglandin D2. JOURNAL: Tetrah. Lett. VOLUME: PAGE: 2235 -2238 (1974)
<< Ref.1012 >> AUTHOR: Ogawa,Y., Nunomoto,M., and Shibasaki,M. TITLE: A Novel Synthsis of Prostaglandin D2. JOURNAL: J. Org. Chm. VOLUME: 51 PAGE: 1625 -1627 (1986)
4PROSTAGLANDIN I2 5(Z)-[7(R)-Hydroxy-6(R)-(3(S)-hydroxyocten-1(E)-yl)-1(S),5(R)-2-oxabicyclo[3.3.0]oct-3-ylidenpentanoic acid XPR1801EicosanoidShouzo YamamotoPGI2 C20H32O5 352.465Download ChemDraw structure dataProstaglandin I2 is a potent anti-aggregatory agent for platelets, relaxes blood vessels, and enhances vascular permeability << Ref. 0014>>. It binds to a receptor with 7 transmembrne domains (IP) coupled to a Gs protein << Ref. 0003>>. [a]D=78deg(C=0.8820, CHCl3) << Ref. 1014>> METHYL ESTER ; LIQUID MELT n 3370, 1740, 1695cm-1 << Ref. 1014>> 1-H-NMR(D2O, GLYCINE BUFFER, pH10.4) : d 5.60(m, 2H, 13,14-CH), 4.66(m, 1H, 9-CH), 4.39(t, 1H, 5-CH), 4.15(q, 1H, 15-CH), 3.97(q, 1H, 11-CH), 2.20(t, 2H, 2-CH2) << Ref. 1013>> 11,15-BIS(TRIMETHYLSILYL) ETHER METHYL ESTER ; 495(M+-CH3), 479, 439, 423, 349, 327, 323, 315, 313, 199, 173 << Ref. 1014>> In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin I2. Prostaglandin I2 is produced in blood vessels, lung and other tissues << Ref. 0013>>. << Ref. 1014>> [Table 0001] Prostaaglandin I2 is produced by isomerization of 9,11-endoperoxide of prostaglandin H2 by the catalysis of prostaglandin I synthaase << Ref. 0015/0016>>. Prostaglandin I2 is unstable and decomposes readily to 6-keto-prostaglandin F2a. Its 2,3-dinor derivative is a major urinary metabolite << Ref. 0017>>. cDNA << Ref. 0016>> and genomic DNA << Ref. 0018>> for prostaglandin I synthase were cloned. cDNA for IP was isolated << Ref. 0003>>. Stability:unstable in water around neutrality with a half life of about 5 min at 37degC and decomposes to 6-keto-PGF1a<< Ref. 0011>>. << Ref.0003 >> AUTHOR: Negishi, M., Sugimoto, Y., and Ichikawa, A. TITLE: Molecular mechanisms of diverse actions of prostanoid receptors PubMed ID:7492609 JOURNAL: Biochim Biophys Acta. VOLUME: 1259 PAGE: 109-119(1995)
<< Ref.0011 >> AUTHOR: Negishi,M., Koizumi,T., and Ichikawa,A. TITLE: Biological actions of D12-prostaglandin J2. PubMed ID:8777585 JOURNAL: J. Lipid Mediators Cell Signaling VOLUME: 12 PAGE: 443 -448 (1995)
<< Ref.0013 >> AUTHOR: Moncada, S., and Vane, J. R. TITLE: Pharmacology and endogenous roles of prostaglandin endoperoxides, thromboxane A2, and prostacyclin PubMed ID:116251 JOURNAL: Pharmacol Rev. VOLUME: 30 PAGE: 293-331(1978)
<< Ref.0014 >> AUTHOR: Whittle, B. J., and Moncada, S. TITLE: Pharmacological interactions between prostacyclin and thromboxanes PubMed ID:6313114 JOURNAL: Br Med Bull. VOLUME: 39 PAGE: 232-238(1983)
<< Ref.0015 >> AUTHOR: Pace-Asciak,C.R., and Smith,W.L. TITLE: Enzymes in the biosynthesis and catabolism of the eicosanoids: prostaglandins, thromboxanes, leukotrienes and hydroxy fatty acids. JOURNAL: The Enzymes VOLUME: 16 PAGE: 543 -603 (1983)
<< Ref.0016 >> AUTHOR: Tanabe, T., and Ullrich, V. TITLE: Prostacyclin and thromboxane synthases PubMed ID:8777569 JOURNAL: J Lipid Mediat Cell Signal. VOLUME: 12 PAGE: 243-255(1995)
<< Ref.0017 >> AUTHOR: Needleman, P., Turk, J., Jakschik, B. A., Morrison, A. R., and Lefkowith, J. B. TITLE: Arachidonic acid metabolism PubMed ID:3017195 JOURNAL: Annu Rev Biochem. VOLUME: 55 PAGE: 69-102(1986)
<< Ref.0018 >> AUTHOR: Yokoyama, C., Yabuki, T., Inoue, H., Tone, Y., Hara, S., Hatae, T., Nagata, M., Takahashi, E. I., and Tanabe, T. TITLE: Human gene encoding prostacyclin synthase (PTGIS): genomic organization, chromosomal localization, and promoter activity PubMed ID:8812456 JOURNAL: Genomics. VOLUME: 36 PAGE: 296-304(1996)
<< Ref.1013 >> AUTHOR: Kotovych,G., Aarts,G.H.M., Takashima,T.T., and Bigam,G. TITLE: The Solution Conformation of Prostacyclin as Determined by High Field Proton Magnetic Resonance Techniques. JOURNAL: Can. J. Chem. VOLUME: 58 PAGE: 974 -983 (1980)
<< Ref.1014 >> AUTHOR: Johnson,R.A., Lincoln,F.H., Nidy,E.G., Schneider,W.P., Thompson,J.L., and Axen,U. TITLE: Synthesis and Characterization of Prostacyclin, 6-Ketoprostaglandin F1a, Prostaglandin I1, and Prostaglandin I3. JOURNAL: J. Am. Chem. Soc. VOLUME: 100 PAGE: 7690 -7705 (1978)
5PROSTAGLANDIN G2 7-[2(R)-(3(S)-Hydroperoxy-1(E)-octenyl)-1(R),4(S)-5,6-dioxabicyclo[2.2.1]-heptan-3(R)-yl]-5(Z)-heptenoic acid XPR1601EicosanoidShouzo YamamotoPGG2 C20H32O6 368.464Download ChemDraw structure dataProstaglandin G2 is a metabolic intermediate, but the compound as such has biological activities of bronchoconstriction and vasoconstriction << Ref. 0013/0020>>. 13C-NMR : d 84.6(C15) << Ref. 1016>> Prostaglandin G2 is produced by bis-dioxygenation and cyclization of arachidonic acid as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues << Ref. 0015/0019>>. << Ref. 1016>> [Table 0001] Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 << Ref. 0019>>. The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds << Ref. 0004/0008>>. cDNA and genomic DNA each for cyclooxygenas-1 and 2 were cloned << Ref. 0007>>. Stability:unstable in water around neutrality with a half life of about 5 min at 37degC and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid<< Ref. 0068>>. << Ref.0004 >> AUTHOR: Smith, W. L., Garavito, R. M., and DeWitt, D. L. TITLE: Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2 PubMed ID:8969167 JOURNAL: J Biol Chem. VOLUME: 271 PAGE: 33157-33160(1996)
<< Ref.0007 >> AUTHOR: Funk, C.D. TITLE: Molecular biology in the eicosanoid field . PubMed ID:8341804 JOURNAL: Progr. Nucleic Acid Res. VOLUME: 45 PAGE: 67 -98 (1993)
<< Ref.0008 >> AUTHOR: Herschman, H.R. TITLE: Prostaglandin synthase 2. PubMed ID:8341804 JOURNAL: Biochim. Biophys. Acta VOLUME: 1299 PAGE: 125 -140 (1996)
<< Ref.0013 >> AUTHOR: Moncada, S., and Vane, J. R. TITLE: Pharmacology and endogenous roles of prostaglandin endoperoxides, thromboxane A2, and prostacyclin PubMed ID:116251 JOURNAL: Pharmacol Rev. VOLUME: 30 PAGE: 293-331(1978)
<< Ref.0015 >> AUTHOR: Pace-Asciak,C.R., and Smith,W.L. TITLE: Enzymes in the biosynthesis and catabolism of the eicosanoids: prostaglandins, thromboxanes, leukotrienes and hydroxy fatty acids. JOURNAL: The Enzymes VOLUME: 16 PAGE: 543 -603 (1983)
<< Ref.0019 >> AUTHOR: Yamamoto,S. (1983) Enzymes in the arachidonic acid cascade. in Prostaglandins and related substances (Pace-Asciak,C.R. and Granstroem,E., eds), pp171-202, Elsevier, Amsterdam TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0020 >> AUTHOR: Chijimatsu, Y., Nguyen, T. V., and Said, S. I. TITLE: Effects of prostaglandin endoperoxide analogs on contractile elements in lung and gastrointestinal tract PubMed ID:866698 JOURNAL: Prostaglandins. VOLUME: 13 PAGE: 909-916(1977)
<< Ref.0068 >> AUTHOR: Nugteren, D. H., and Hazelhof, E. TITLE: Isolation and properties of intermediates in prostaglandin biosynthesis PubMed ID:4776443 JOURNAL: Biochim Biophys Acta. VOLUME: 326 PAGE: 448-461(1973)
<< Ref.1016 >> AUTHOR: Porter,N.A., Byers,J.D., Ali,A.E., and Eling,T.E. TITLE: Prostaglandin G2. JOURNAL: J. Am. Chem. Soc. VOLUME: 102 PAGE: 1183 -1184 (1980)
6PROSTAGALANDIN H2 7-[2(R)-(3(S)-Hydroxy-1(E)-octenyl)-1(R),4(S)-5,6-dioxabicyclo[2.2.1]heptan-3(R)-yl]-5(Z)-heptenoic acid XPR1701EicosanoidShouzo YamamotoPGH2 C20H32O5 352.465Download ChemDraw structure dataProstaglandin H2 is a metabolic intermediate, but the compound as such is bioactive to aggregate platelets and to contract artery << Ref. 0013/0020>>. CHLOROFORM, METHYLENE CHLORIDE, ETHYL ACETATE << Ref. 1018/1019>> METHYL ESTER:to be cited the Chart<< Ref. 1018>> 1H-NMR :to be cited the Chart<< Ref. 1018>>. 13C-NMR(CD2Cl2) : 178.5(C1), 133.5, 130.4, 130,0, 128.4, 82.1, 79.6(C9 & C11), 72.7(C15), 50.4, 48.2, 42.4, 37.0, 33.1, 31.7, 26.9, 26.3, 25.1, 24.5, 22.7, 14.0 << Ref. 1019>> 15-TRIMETHYLSILYL ETHER METHYL ETHER :to be cited the Chart<< Ref. 1020>> Prostaglandin H2 is produced by 15-hydroperoxide reduction of prostaglandin G2 as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues << Ref. 0015/0019>>. << Ref. 1019>> [Table 0001] Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 << Ref. 0019>>. The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds << Ref. 0004/0008>>. cDNA and genomic DNA each for cyclooxygenase-1 and 2 were cloned << Ref. 0007>>. Stability:unstable in water around neutrality with a half life of about 5 min at 37degC and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid<< Ref. 0068>>. << Ref.0004 >> AUTHOR: Smith, W. L., Garavito, R. M., and DeWitt, D. L. TITLE: Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2 PubMed ID:8969167 JOURNAL: J Biol Chem. VOLUME: 271 PAGE: 33157-33160(1996)
<< Ref.0007 >> AUTHOR: Funk, C.D. TITLE: Molecular biology in the eicosanoid field . PubMed ID:8341804 JOURNAL: Progr. Nucleic Acid Res. VOLUME: 45 PAGE: 67 -98 (1993)
<< Ref.0008 >> AUTHOR: Herschman, H.R. TITLE: Prostaglandin synthase 2. PubMed ID:8341804 JOURNAL: Biochim. Biophys. Acta VOLUME: 1299 PAGE: 125 -140 (1996)
<< Ref.0013 >> AUTHOR: Moncada, S., and Vane, J. R. TITLE: Pharmacology and endogenous roles of prostaglandin endoperoxides, thromboxane A2, and prostacyclin PubMed ID:116251 JOURNAL: Pharmacol Rev. VOLUME: 30 PAGE: 293-331(1978)
<< Ref.0015 >> AUTHOR: Pace-Asciak,C.R., and Smith,W.L. TITLE: Enzymes in the biosynthesis and catabolism of the eicosanoids: prostaglandins, thromboxanes, leukotrienes and hydroxy fatty acids. JOURNAL: The Enzymes VOLUME: 16 PAGE: 543 -603 (1983)
<< Ref.0019 >> AUTHOR: Yamamoto,S. (1983) Enzymes in the arachidonic acid cascade. in Prostaglandins and related substances (Pace-Asciak,C.R. and Granstroem,E., eds), pp171-202, Elsevier, Amsterdam TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.0020 >> AUTHOR: Chijimatsu, Y., Nguyen, T. V., and Said, S. I. TITLE: Effects of prostaglandin endoperoxide analogs on contractile elements in lung and gastrointestinal tract PubMed ID:866698 JOURNAL: Prostaglandins. VOLUME: 13 PAGE: 909-916(1977)
<< Ref.0068 >> AUTHOR: Nugteren, D. H., and Hazelhof, E. TITLE: Isolation and properties of intermediates in prostaglandin biosynthesis PubMed ID:4776443 JOURNAL: Biochim Biophys Acta. VOLUME: 326 PAGE: 448-461(1973)
<< Ref.1018 >> AUTHOR: Gorman, R. R., Sun, F. F., Miller, O. V., and Johnson, R. A. TITLE: Prostaglandins H1 and H2. Convenient biochemical synthesis and isolation. Further biological and spectroscopic characterization PubMed ID:887795 JOURNAL: Prostaglandins. VOLUME: 13 PAGE: 1043-1053(1977)
<< Ref.1019 >> AUTHOR: Porter,N.A., Byers,J.D., Holden,K.M. and Menzel,D.B. TITLE: Synthesis of Prostaglandin H2. JOURNAL: J. Am. Chem. Soc. VOLUME: 101 PAGE: 4319 -4322 (1979)
<< Ref.1020 >> AUTHOR: Johnson, R. A., Nidy, E. G., Baczynskyj, L., and Gorman, R. R. TITLE: Synthesis of prostaglandin H2 methyl ester PubMed ID:915166 JOURNAL: J Am Chem Soc. VOLUME: 99 PAGE: 7738-7740(1977)
7Prostaglandin A3 9-oxo-15S-hydroxy-prosta-5Z,10,13E,17Z-tetraen-1-oic acid XPR1702EicosanoidTakehiko Yokomizo C20H28O4 332.434Download ChemDraw structure data PGA3 is non-enzymatic dehydration product of PGE3.
8Prostaglandin B3 9-oxo-15S-hydroxy-prosta-5Z,8(12),13E,17Z-tetraen-1-oic acid XPR1703EicosanoidTakehiko Yokomizo C20H28O4 332.434Download ChemDraw structure data PGB3 is a non-enzymatic dehydration product resulting from the treatment of PGE3 with strong base.
913,14-dihydro-15keto Prostaglandin D2 9a-hydroxy-11,15-dioxo-prost-5Z-en-1-oic acid XPR1704EicosanoidTakehiko Yokomizo C20H32O5 352.465Download ChemDraw structure data 13,14-dihydro-15keto PGD2 is a metabolite of PGD2 which is formed through the PG 15-dehydrogenase pathway.<< Ref. 2003>> << Ref.2003 >> AUTHOR: Hirata, Y., Hayashi, H., Ito, S., Kikawa, Y., Ishibashi, M., Sudo, M., Miyazaki, H., Fukushima, M., Narumiya, S., and Hayaishi, O. TITLE: Occurrence of 9-deoxy-delta 9,delta 12-13,14-dihydroprostaglandin D2 in human urine PubMed ID:3053696 JOURNAL: J Biol Chem. VOLUME: 263 PAGE: 16619-16625(1988)
10Prostaglandin D3 9a,15S-dihydroxy-11-oxo-prosta-5Z,13E,17Z-trien-1-oic acid XPR1705EicosanoidTakehiko Yokomizo C20H30O5 350.449Download ChemDraw structure dataPGD3 has almost same ability to decrease systemic blood pressure in rats and to decrease intraocular pressure in rabbits.<< Ref. 2005/2006/2007>> However, it is 3 to 5 times more potent than PGD2 in the inhibition of ADP-induced human platelet aggregation.<< PGD3 is produced by the metabolism of EPA via the cyclooxygenase pathway.<< Ref. 2004>> << Ref.0004 >> AUTHOR: Smith, W. L., Garavito, R. M., and DeWitt, D. L. TITLE: Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2 PubMed ID:8969167 JOURNAL: J Biol Chem. VOLUME: 271 PAGE: 33157-33160(1996)
<< Ref.0008 >> AUTHOR: Herschman, H.R. TITLE: Prostaglandin synthase 2. PubMed ID:8341804 JOURNAL: Biochim. Biophys. Acta VOLUME: 1299 PAGE: 125 -140 (1996)
<< Ref.0019 >> AUTHOR: Yamamoto,S. (1983) Enzymes in the arachidonic acid cascade. in Prostaglandins and related substances (Pace-Asciak,C.R. and Granstroem,E., eds), pp171-202, Elsevier, Amsterdam TITLE: JOURNAL: VOLUME: PAGE: - ()
<< Ref.2004 >> AUTHOR: Kulkarni,P.S.,Kaufman,P.L.,Srinivasan,B.D. TITLE: Eicosapentaenoic acid metabolism in cynomolgus and rhesus conjunctiva and eyelid. PubMed ID:2846724 JOURNAL: J.Ocul.Pharmacol. VOLUME: 3 PAGE: 349 -356 (1987)
<< Ref.2005 >> AUTHOR: Bundy,G.L.,Morton,D.R.,Peterson,D.C. TITLE: Synthesis and platelet aggregation inhibiting activity of prostaglandin D analogues. PubMed ID:6854581 JOURNAL: J.Med.Chem. VOLUME: 26 PAGE: 790 -799 (1983)
<< Ref.2006 >> AUTHOR: Goh, Y., Nakajima, M., Azuma, I., and Hayaishi, O. TITLE: Effects of prostaglandin D2 and its analogues on intraocular pressure in rabbits PubMed ID:3236567 JOURNAL: Jpn J Ophthalmol. VOLUME: 32 PAGE: 471-480(1988)
<< Ref.2007 >> AUTHOR: Kulkarni, P. S., and Srinivasan, B. D. TITLE: Prostaglandins E3 and D3 lower intraocular pressure PubMed ID:4019112 JOURNAL: Invest Ophthalmol Vis Sci. VOLUME: 26 PAGE: 1178-1182(1985)
11D17-Prostaglandin E1 9-oxo-11a,15S-dihydroxy-prosta-13E,17Z-dien-1-oic acid XPR1706EicosanoidTakehiko Yokomizo C20H32O5 352.465Download ChemDraw structure dataD17-PGE1 is about half as potent as PGE1 as an inhibitor of ADP-induced aggregation of rabbbit PRP.<< Ref. 2008>> In humanPRP, D17-PGE1 is a more potent antiplatelet agonist than PGE1. D17-PGE1 is produced by the cyclooxigenase metabolism of w-3 arachidonic acid. << Ref.2008 >> AUTHOR: Kobzar, G., Mardla, V., Jarving, I., Lohmus, M., Vahemets, A., Samel, N., and Lille, U. TITLE: Comparison of the inhibitory effect of E-prostaglandins in human and rabbit platelet-rich plasma and washed platelets PubMed ID:7904921 JOURNAL: Comp Biochem Physiol C. VOLUME: 106 PAGE: 489-494(1993)
1213,14-dihydro Prostaglandin E1 9-oxo-11a,15S-dihydroxy-prostan-1-oic acid XPR1707EicosanoidTakehiko Yokomizo C20H36O5 356.497Download ChemDraw structure data13,14-dihydro PGE1 is an inhibitor of ADP-induced platelet aggregation in human PRP.
1313,14-dihydro-15keto Prostaglandin E1 9,15-dioxo-11a-hydroxy-prostan-1-oic acid XPR1708EicosanoidTakehiko Yokomizo C20H34O5 354.481Download ChemDraw structure data13,14-dihydro-15keto PGE1 is a week inhibitor of ADP-induced platelet aggregation in human PRP. 13,14-dihydro-15keto PGE1 is a metabolite of PGE1.<< Ref. 2010/2011>> << Ref.2010 >> AUTHOR: Hamberg,M. and Samuelsson,B. TITLE: On the metabolism of prostaglandins E1 and E2 in man. PubMed ID:5126221 JOURNAL: J.Biol.Chem. VOLUME: 246 PAGE: 6713 -6721 (1971)
<< Ref.2011 >> AUTHOR: Leonhardt, A., Krauss, M., Gieler, U., Schweer, H., Happle, R., and Seyberth, H. W. TITLE: In vivo formation of prostaglandin E1 and prostaglandin E2 in atopic dermatitis PubMed ID:9115911 JOURNAL: Br J Dermatol. VOLUME: 136 PAGE: 337-340(1997)
1415-keto Prostaglandin E1 9,15-dioxo-11a-hydroxy-prost-13E-en-1-oic acid XPR1709EicosanoidTakehiko Yokomizo C20H32O5 352.465Download ChemDraw structure data15-keto PGE1 has very slight biological activity compared to PGE1.<< Ref. 2013>> 15-keto PGE1 is the inactive metabolite of PGE1 via PG15-dehydrogenase << Ref.2013 >> AUTHOR: Westwick, J. TITLE: The effect of pulmonary metabolites of prostaglandins E1, E2 and F2alpha on ADP-induced aggregation of human and rabbit platelets [proceedings] PubMed ID:974413 JOURNAL: Br J Pharmacol. VOLUME: 58 PAGE: 297P-298P(1976)
1519(R)-hydroxy Prostaglandin E1 9-oxo-11a,15S,19R-trihydroxy-prost-13E-en-1-oic acid XPR1710EicosanoidTakehiko Yokomizo C20H34O6 370.480Download ChemDraw structure data 19(R)-hydroxy PGE1 has contractile activity on smooth muscle preparations.<< Ref. 2014/2015>> 19(R)-hydroxy PGE1 is the major prostaglandin found in the semen of primates. << Ref.2014 >> AUTHOR: Kelly, R. W., Taylor, P. L., Hearn, J. P., Short, R. V., Martin, D. E., and Marston, J. H. TITLE: 19-Hydroxyprostaglandin E1 as a major component of the semen of primates PubMed ID:817207 JOURNAL: Nature. VOLUME: 260 PAGE: 544-545(1976)
<< Ref.2015 >> AUTHOR: Woodward, D. F., Protzman, C. E., Krauss, A. H., and Williams, L. S. TITLE: Identification of 19 (R)-OH prostaglandin E2 as a selective prostanoid EP2-receptor agonist PubMed ID:8248550 JOURNAL: Prostaglandins. VOLUME: 46 PAGE: 371-383(1993)
165-trans Prostaglandin E2 9-oxo-11a,15S-dihydroxy-prosta-5E,13E-dien-1-oic acid XPR1711EicosanoidTakehiko Yokomizo C20H32O5 352.465Download ChemDraw structure data5-trans PGE2 has 18 times potency in activating adenylate cyclase compared to PGE2.<< Ref. 2017>> 5-trans PGE2 accelerates fibrinolysis by enhancing plasminogen activation mediated dby tissue-type plasminogen activator.<< Ref. 2018>> And it also inhibits platelet