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Eicosanoid


DATA No : XPR1301 INFORMANT : Shouzo Yamamoto

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

COMMON NAME: PROSTAGLANDIN D2
SYMBOL: PGD2
FORMULA: C20H32O5 MOL.WT (average) : 352.465


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BIOLOGICAL ACTIVITY
Biological 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).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:68degC (Ref. 1010)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-20=9deg (C=2.11,THF) (Ref. 1012)

DENSITY:

SOLUBILITY:ETHYL ACETATE,THF,CHLOROFORM (Ref. 1012)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:KBr : 3400-2500, 1740, 1700, 975cm-1 (Ref. 1010)

NMR SPECTRA: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)

MASS SPECTRA:m/e 334, 316, 246, 245, 191, 190, 161, 55 (Ref. 1012)

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 D2. Prostaglandin D2 is produced in barin, lung, spleen, mast cells and other tissues (Ref. 0005).
CHEMICAL SYNTHESIS
(Ref. 1010)
[Table 0001]
METABOLISM
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).
GENETIC INFORMATION
cDNA and genomic DNA of prostaglandin D synthase were cloned (Ref. 0005). cDNA for DP was isolated (Ref. 0011).
NOTE

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]

[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]

[0009]
AUTHOR:Giles, H., and Leff, P.
TITLE:The biology and pharmacology of PGD2 PubMed ID:3283848
JOURNAL:Prostaglandins.
VOL:35 PAGE : 277-300 (1988)
[TOP]

[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.
VOL:47 PAGE : 1-12 (1992)
[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]

[0012]
AUTHOR:Hayaishi, O.
TITLE:Sleep-wake regulation by prostaglandins D2 and E2 PubMed ID:3049580
JOURNAL:J Biol Chem.
VOL:263 PAGE : 14593-14596 (1988)
[TOP]

[1010]
AUTHOR:Hayashi,M., and Tanouchi,T.
TITLE:Syntheses of 11-Dehydro-13,14-dihydro-PGE1 and PGD2.
JOURNAL:J. Org. Chem.
VOL:38 PAGE : 2115 -2116 (1973)
[TOP]

[1011]
AUTHOR:Jenny,E.F., and Schä$ublin,P.
TITLE:Total Synthesis of Prostaglandin D2.
JOURNAL:Tetrah. Lett.
VOL: PAGE : 2235 -2238 (1974)
[TOP]

[1012]
AUTHOR:Ogawa,Y., Nunomoto,M., and Shibasaki,M.
TITLE:A Novel Synthsis of Prostaglandin D2.
JOURNAL:J. Org. Chm.
VOL:51 PAGE : 1625 -1627 (1986)
[TOP]

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