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Eicosanoid


DATA No : XPR1801 INFORMANT : Shouzo Yamamoto

NAME : 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

COMMON NAME: PROSTAGLANDIN I2
SYMBOL: PGI2
FORMULA: C20H32O5 MOL.WT (average) : 352.465


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BIOLOGICAL ACTIVITY
Prostaglandin 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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D=78deg(C=0.8820, CHCl3) (Ref. 1014)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:METHYL ESTER ; LIQUID MELT n 3370, 1740, 1695cm-1 (Ref. 1014)

NMR SPECTRA: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)

MASS SPECTRA:11,15-BIS(TRIMETHYLSILYL) ETHER METHYL ESTER ; 495(M+-CH3), 479, 439, 423, 349, 327, 323, 315, 313, 199, 173 (Ref. 1014)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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).
CHEMICAL SYNTHESIS
(Ref. 1014)
[Table 0001]
METABOLISM
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).
GENETIC INFORMATION
cDNA (Ref. 0016) and genomic DNA (Ref. 0018) for prostaglandin I synthase were cloned. cDNA for IP was isolated (Ref. 0003).
NOTE
Stability:unstable in water around neutrality with a half life of about 5 min at 37degC and decomposes to 6-keto-PGF1a(Ref. 0011).
REFERENCES
[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)
[TOP]

[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
VOL:12 PAGE : 443 -448 (1995)
[TOP]

[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.
VOL:30 PAGE : 293-331 (1978)
[TOP]

[0014]
AUTHOR:Whittle, B. J., and Moncada, S.
TITLE:Pharmacological interactions between prostacyclin and thromboxanes PubMed ID:6313114
JOURNAL:Br Med Bull.
VOL:39 PAGE : 232-238 (1983)
[TOP]

[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
VOL:16 PAGE : 543 -603 (1983)
[TOP]

[0016]
AUTHOR:Tanabe, T., and Ullrich, V.
TITLE:Prostacyclin and thromboxane synthases PubMed ID:8777569
JOURNAL:J Lipid Mediat Cell Signal.
VOL:12 PAGE : 243-255 (1995)
[TOP]

[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.
VOL:55 PAGE : 69-102 (1986)
[TOP]

[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.
VOL:36 PAGE : 296-304 (1996)
[TOP]

[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.
VOL:58 PAGE : 974 -983 (1980)
[TOP]

[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.
VOL:100 PAGE : 7690 -7705 (1978)
[TOP]

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