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Eicosanoid


DATA No : XPR1001 INFORMANT : Shouzo Yamamoto

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

COMMON NAME: PROSTAGLANDIN A2
SYMBOL: PGA2
FORMULA: C20H30O4 MOL.WT (average) : 334.450


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BIOLOGICAL ACTIVITY
Antitumor activity of prostaglandin A2 is known (Ref. 0038), and prostaglandin A2 rduces blood pressure (Ref. 0002).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20=+140deg(C=1.15, CHLOROFORM) (Ref. 1042)

DENSITY:

SOLUBILITY:ETHANOL, CHLOROFORM, METHANOL, DIETHYLETHER (Ref. 1005)
SPECTRAL DATA
UV SPECTRA:EtOH: 217 nm (e 9900) (Ref. 1005)

IR SPECTRA:NUJOL : n 3400, 1705, 1580, 1255, 1115, 1070, 1015 cm-1 (Ref. 1005)

NMR SPECTRA:1H-NMR(CDCl3) : d 7.57(dd, 1H, 10-CH), 6.2(dd, 1H, 11-CH), 5.6(m, 2H, 13,14-CH), 5.4 (m, 2H, 5,6-CH), 4.12(1H, m, 12-CH), 3.23(m, 1H), 0.89(t, 3H, 0-CH3) (Ref. 1043). METHYL ESTER : 13C-NMR(CDCl3) 210.3, 174.0, 165.0, 135.2, 133.3, 131.0, 130.2, 126.7, 72.4, 52.1, 51.5, 49.6, 37.3, 33.5, 31.8, 27.4, 26.7, 25.1, 24.8, 22.6, 14.0 (Ref. 1044)

MASS SPECTRA:m/e 334(M+), 316, 190 (Ref. 1005)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Prostaglandin A2 was found in human semen in an amount of about 50 micrograms per ml as measured in combination with prostaglandins A1, B1 and B2 (Ref. 0001).
CHEMICAL SYNTHESIS
(Ref. 1042)
[Table 0001]
METABOLISM
Prostaglandin A2 is produced by non-enzymatic degradation of prostaglandin E2 (Ref. 0039), and human serum has an enzymatic activity to convert prostaglandin E2 to A2 (Ref. 0040).
GENETIC INFORMATION

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)
[TOP]

[0038]
AUTHOR:Fukushima,M.
TITLE:Prostaglandin J2-anti-tumor and anti-viral activities and the mechanisms involved. PubMed ID:2073399
JOURNAL:Eicosanoids
VOL:3 PAGE : 189 -199 (1990)
[TOP]

[0039]
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)
[TOP]

[0040]
AUTHOR:Polet, H., and Levine, L.
TITLE:Metabolism of prostaglandins E, A, and C in serum PubMed ID:234423
JOURNAL:J Biol Chem.
VOL:250 PAGE : 351-357 (1975)
[TOP]

[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)
[TOP]

[1042]
AUTHOR:Corey, E. J., and Moinet, G.
TITLE:Direct, stereocontrolled synthesis of a prostaglandins using the bicyclo[2.2.1]heptene approach PubMed ID:4746271
JOURNAL:J Am Chem Soc.
VOL:95 PAGE : 6331-6332 (1973)
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[1043]
AUTHOR:Schneider, W. P., Bundy, G. L., Lincoln, F. H., Daniels, E. G., and Pike, J. E.
TITLE:Isolation and chemical conversions of prostaglandins from Plexaura homomalla: Preparation of prostaglandin E2, prostaglandin F2alpha, and their 5,6-trans isomers PubMed ID:13095
JOURNAL:J Am Chem Soc.
VOL:99 PAGE : 1222-1232 (1977)
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[1044]
AUTHOR:Cooper, G. F., and Fried, J.
TITLE:Carbon-13 nuclear magnetic resonance spectra of prostaglandins and some prostaglandin analogs PubMed ID:4514326
JOURNAL:Proc Natl Acad Sci U S A.
VOL:70 PAGE : 1579-1584 (1973)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.