LBF20207PG23

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Upper classes: LB LBF



Prostaglandin E2
LBF20207PG23.png
Structural Information
Systematic Name 7- [3R -Hydroxy-2R - (3S -hydroxy-trans-1-octenyl-5-oxocyclopentan-1R -yl] -cis-5-heptenoic acid
Common Name
  • Prostaglandin E2
  • 7- [ 3 (R) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl-5-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Symbol PGE2
Formula C20H32O5
Exact Mass 352.224974134
Average Mass 352.46508
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)[C@@H](CC1=O)O)CC
Physicochemical Information
Melting Point 65-66°C Corey_EJ et al.
Boiling Point
Density
Optical Rotation [ α ]26
D
   =-61.0°(C=1.0, TETRAHYDROFURAN) Corey_EJ et al.
Refractive Index
Solubility ETHYL ACETATE,THF,CHLOROFORM Donaldson_RE et al. Sih_CJ et al.. STABILITIES: to be stable under neutral condition. to decompose to PGA2 under acidic and to PGB2 under basic conditions Karim_SM et al. Pike_JE et al.
Source Prostaglandin E2 was found to be accummulating in human semen in an amount of about 13 microgram per ml Bergstrom_S . In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin E2.
Chemical Synthesis
LBF20207PG23FT0001.gif
Corey_EJ et al.
Metabolism Prostaglandin E2 is produced from arachidonic acid via prostaglandins G2 and H2 by the catalyses of prostaglandin endoperoxide synthase (cyclooxygenase) Smith_WL et al. and prostaglandin E synthase Urade_Y et al.. 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 Smith_WL et al.. The biological activities of prostaglandin E2 are lost by oxidation of its 15-hydroxyl group catalyzed by 15-hydroxyprostaglandin dehydrogenase Hansen_HS .
Biological Activity Prostaglandin E2 exhibits various biological activities such as vasodilatation, uterine contraction, gastrointestinal contraction, bronchodilatation, diuresis, pyrexia, inhibition of gastric secretion, bone resorption and immunosuppression Bergstrom_S et al.. 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 Negishi_M et al..
Genetic Information 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 Funk_CD Herschman_HR Their genomic DNA were also cloned, and the genomic structure were eludicated Funk_CD . 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 Negishi_M et al..
Note
Spectral Information
Mass Spectra d,l-mixture ; 334(M+-18), 316, 298, 190 Chen_SML et al.
UV Spectra
IR Spectra d,l-mixture ; 3400, 1710, 970cm-1 Chen_SML et al.
NMR Spectra 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. Donaldson_RE et al.. 1H-NMR(CDCl3) : δ 5.67(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= Donaldson_RE et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG23 See above. Bergstrom_S 1967
n.a. LBF20207PG23 See above. Bergstrom_S et al. 1968
n.a. LBF20207PG23 See above. Chen_SML et al. 1978
n.a. LBF20207PG23 See above. Corey_EJ et al. 1970
n.a. LBF20207PG23 See above. Donaldson_RE et al. 1983
n.a. LBF20207PG23 See above. Funk_CD 1993
n.a. LBF20207PG23 See above. Hansen_HS 1976
n.a. LBF20207PG23 See above. Herschman_HR 1996
n.a. LBF20207PG23 See above. Karim_SM et al. 1968
n.a. LBF20207PG23 See above. Negishi_M et al. 1995
n.a. LBF20207PG23 See above. Pike_JE et al. 1969
n.a. LBF20207PG23 See above. Sih_CJ et al. 1975
n.a. LBF20207PG23 See above. Smith_WL et al. 1996
n.a. LBF20207PG23 See above. Urade_Y et al. 1995



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