View source for LBF20207PG22

{{Lipid/Header}}

{{Hierarchy|{{PAGENAME}}}}

{{Metabolite
|LipidBank=XPR1301
|LipidMaps=LMFA03010004
|SysName=7- [5S -Hydroxy-2R - (3S-hydroxy-trans-1-octenyl) -3-oxocyclopentan-1R -yl] -cis-5-heptenoic acid
|Common Name=&&Prostaglandin D_2&&7- [ 5 (S) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -3-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid&&
|Melting Point=68°C [[Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115|{{RelationTable/GetFirstAuthor|Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115}}]]
|Optical=[ alpha ]^{20}_D =9° (C=2.11,THF) [[Reference:Ogawa_Y:Nunomoto_M:Shibasaki_M:,J. Org. Chem.,1986,51,1625|{{RelationTable/GetFirstAuthor|Reference:Ogawa_Y:Nunomoto_M:Shibasaki_M:,J. Org. Chem.,1986,51,1625}}]]
|Solubility=ETHYL ACETATE,THF,CHLOROFORM [[Reference:Ogawa_Y:Nunomoto_M:Shibasaki_M:,J. Org. Chem.,1986,51,1625|{{RelationTable/GetFirstAuthor|Reference:Ogawa_Y:Nunomoto_M:Shibasaki_M:,J. Org. Chem.,1986,51,1625}}]]
|Mass Spectra=m/e 334, 316, 246, 245, 191, 190, 161, 55 [[Reference:Ogawa_Y:Nunomoto_M:Shibasaki_M:,J. Org. Chem.,1986,51,1625|{{RelationTable/GetFirstAuthor|Reference:Ogawa_Y:Nunomoto_M:Shibasaki_M:,J. Org. Chem.,1986,51,1625}}]]
|IR Spectra=KBr : 3400-2500, 1740, 1700, 975cm^{-1} [[Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115|{{RelationTable/GetFirstAuthor|Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115}}]]
|NMR Spectra=^1 H-NMR(270MHz, CDCl_3 ) :  delta  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) [[Reference:Jenny_EF:Schaeublin_P:,Tetrah. Lett.,1974,,2235|{{RelationTable/GetFirstAuthor|Reference:Jenny_EF:Schaeublin_P:,Tetrah. Lett.,1974,,2235}}]]
|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 [[Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257|{{RelationTable/GetFirstAuthor|Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257}}]].
|Chemical Synthesis=[[Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115|{{RelationTable/GetFirstAuthor|Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115}}]] {{Image200|LBF20207PG22FT0001.gif}}
|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 [[Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257|{{RelationTable/GetFirstAuthor|Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257}}]]. Prostaglandin D2 is either reduced to 9 alpha ,11 beta -prostaglandin F or oxidized to 15-keto-prostaglandin D2 by a specific dehydrogenase [[Reference:Giles_H:Leff_P:,Prostaglandins,1988,35,277|{{RelationTable/GetFirstAuthor|Reference:Giles_H:Leff_P:,Prostaglandins,1988,35,277}}]]. Non-enzymatic transformation of prostaglandin D2 produces anti-neoplastic  Delta 12-prostaglandin J2 [[Reference:Negishi_M:Koizumi_T:Ichikawa_A:,J. Lipid Mediat. Cell Signal.,1995,12,443|{{RelationTable/GetFirstAuthor|Reference:Negishi_M:Koizumi_T:Ichikawa_A:,J. Lipid Mediat. Cell Signal.,1995,12,443}}]].
|Symbol=PGD2
|Biological Activity=Biological significance of prostaglandin D2 was unknown except anti-aggregatory and bronchoconstrictive activities [[Reference:Giles_H:Leff_P:,Prostaglandins,1988,35,277|{{RelationTable/GetFirstAuthor|Reference:Giles_H:Leff_P:,Prostaglandins,1988,35,277}}]]. Recently prostaglandin D2 has been noted as antineoplastic agent (actually attributed to  Delta 12-prostaglandin J2) [[Reference:Fukushima_M:,Prostaglandins Leukot. Essent. Fatty Acids,1992,47,1|{{RelationTable/GetFirstAuthor|Reference:Fukushima_M:,Prostaglandins Leukot. Essent. Fatty Acids,1992,47,1}}]][[Reference:Negishi_M:Koizumi_T:Ichikawa_A:,J. Lipid Mediat. Cell Signal.,1995,12,443|{{RelationTable/GetFirstAuthor|Reference:Negishi_M:Koizumi_T:Ichikawa_A:,J. Lipid Mediat. Cell Signal.,1995,12,443}}]] and as a sleep-inducing compound [[Reference:Hayaishi_O:,J. Biol. Chem.,1988,263,14593|{{RelationTable/GetFirstAuthor|Reference:Hayaishi_O:,J. Biol. Chem.,1988,263,14593}}]]. Prostaglandin D2 binds to a receptor with 7 transmembrane domains (DP) coupled to a Gs protein [[Reference:Negishi_M:Sugimoto_Y:Ichikawa_A:,Biochim. Biophys. Acta,1995,1259,109|{{RelationTable/GetFirstAuthor|Reference:Negishi_M:Sugimoto_Y:Ichikawa_A:,Biochim. Biophys. Acta,1995,1259,109}}]].
|Genetic Information=cDNA and genomic DNA of prostaglandin D synthase were cloned [[Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257|{{RelationTable/GetFirstAuthor|Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257}}]]. cDNA for DP was isolated [[Reference:Negishi_M:Koizumi_T:Ichikawa_A:,J. Lipid Mediat. Cell Signal.,1995,12,443|{{RelationTable/GetFirstAuthor|Reference:Negishi_M:Koizumi_T:Ichikawa_A:,J. Lipid Mediat. Cell Signal.,1995,12,443}}]].
}}

{{MassbankSpectra|
UT000334
UT000335
UT000336
UT000337
UT000338
UT000339
UT000340
UT000341
UT000342
}}

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