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Eicosanoid


DATA No : XPR1401 INFORMANT : Shouzo Yamamoto

NAME : 7-[3(R)-Hydroxy-2(R)-(3(S)-hydroxy-1(E)-octenyl-5-oxocyclopentan-1(R)-yl]-5(Z)-heptenoic acid

COMMON NAME: Prostaglandin E2
SYMBOL: PGE2
FORMULA: C20H32O5 MOL.WT (average) : 352.465


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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 (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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:65-66degC (Ref. 1001)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-26=-61.0deg(C=1.0, TETRAHYDROFURAN) (Ref. 1001)

DENSITY:

SOLUBILITY: 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)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:d,l-mixture ; 3400, 1710, 970cm-1 (Ref. 1003)

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. (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)

MASS SPECTRA:d,l-mixture ; 334(M+-18), 316, 298, 190 (Ref. 1003)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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.
CHEMICAL SYNTHESIS

[Table 0001] (Ref. 1001)
METABOLISM
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).
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 (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).
NOTE

REFERENCES
[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.
VOL:157 PAGE : 382-391 (1967)
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[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.
VOL:20 PAGE : 1-48 (1968)
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[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.
VOL:1259 PAGE : 109-119 (1995)
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[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.
VOL:271 PAGE : 33157-33160 (1996)
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[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.
VOL:12 PAGE : 257-273 (1995)
[TOP]

[0006]
AUTHOR:Hansen, H. S.
TITLE:15-hydroxyprostaglandin dehydrogenase. A review PubMed ID:184496
JOURNAL:Prostaglandins.
VOL:12 PAGE : 647-679 (1976)
[TOP]

[0007]
AUTHOR:Funk, C.D.
TITLE:Molecular biology in the eicosanoid field . PubMed ID:8341804
JOURNAL:Progr. Nucleic Acid Res.
VOL:45 PAGE : 67 -98 (1993)
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[0008]
AUTHOR:Herschman, H.R.
TITLE:Prostaglandin synthase 2. PubMed ID:8341804
JOURNAL:Biochim. Biophys. Acta
VOL:1299 PAGE : 125 -140 (1996)
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[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.
VOL:92 PAGE : 397-398 (1970)
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[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.
VOL:48 PAGE : 2167 -2188 (1983)
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[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.
VOL:43 PAGE : 3450 -3454 (1978)
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[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.
VOL:4 PAGE : 416-420 (1968)
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[1005]
AUTHOR:Pike, J.E., Lincoln,F.H., and Schneider,W.P.
TITLE:Prostanoic Acid Chemistry.
JOURNAL:J. Org. Chem.
VOL:34 PAGE : 3552 -3557 (1969)
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[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.
VOL:97 PAGE : 865-874 (1975)
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