LBF20207PG22: Difference between revisions

No edit summary
No edit summary
Line 14: Line 14:
|IR Spectra=KBr : 3400-2500, 1740, 1700, 975cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115|{{RelationTable/GetFirstAuthor|Reference:Hayashi_M:Tanouchi_T:,J. Org. Chem.,1973,38,2115}}]]
|IR Spectra=KBr : 3400-2500, 1740, 1700, 975cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[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=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(270MHz, CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT> 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}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(270MHz, CDCl<SUB><FONT SIZE=-1>3</FONT></SUB>) : <FONT FACE="Symbol">d</FONT> 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}}]];>.
|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}}
|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<FONT FACE="Symbol">a</FONT>,11<FONT FACE="Symbol">b</FONT>-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 <FONT FACE="Symbol">D</FONT>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}}]];>.
|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<FONT FACE="Symbol">a</FONT>,11<FONT FACE="Symbol">b</FONT>-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 <FONT FACE="Symbol">D</FONT>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}}]].
}}
}}


{{Lipid/Footer}}
{{Lipid/Footer}}

Revision as of 11:55, 25 November 2009

LipidBank Top
(トップ)
Fatty acid
(脂肪酸)
Glycerolipid
(グリセロ脂質)
Sphingolipid
(スフィンゴ脂質)
Journals
(雑誌一覧)
How to edit
(ページの書き方)


Upper classes: LB LBF



PROSTAGLANDIN D2
LBF20207PG22.png
Structural Information
7- [ 5 (S) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -3-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
  • PROSTAGLANDIN D2
  • 7- [ 5 (S) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -3-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Formula C20H32O5
Exact Mass 352.224974134
Average Mass 352.46508
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)C(C[C@@H]1O)=O)CC
Physicochemical Information
68°C Hayashi_M et al.
ETHYL ACETATE,THF,CHLOROFORM OgawaYet al.
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 Urade_Y et al..
Hayashi_M et al.
LBF20207PG22FT0001.gif
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 Urade_Y et al.. Prostaglandin D2 is either reduced to 9a,11b-prostaglandin F or oxidized to 15-keto-prostaglandin D2 by a specific dehydrogenase Giles_H et al.. Non-enzymatic transformation of prostaglandin D2 produces anti-neoplastic D12-prostaglandin J2 Negishi_M et al..
Spectral Information
Mass Spectra m/e 334, 316, 246, 245, 191, 190, 161, 55 OgawaYet al.
UV Spectra
IR Spectra KBr : 3400-2500, 1740, 1700, 975cm-1 HayashiMet al.
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) Jenny_EF et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG22 See above. Fukushima_M 1992
n.a. LBF20207PG22 See above. Giles_H et al. 1988
n.a. LBF20207PG22 See above. Hayaishi_O 1988
n.a. LBF20207PG22 See above. Hayashi_M et al. 1973
n.a. LBF20207PG22 See above. Jenny_EF et al. 1974
n.a. LBF20207PG22 See above. Negishi_M et al. 1995
n.a. LBF20207PG22 See above. Negishi_M et al. 1995
n.a. LBF20207PG22 See above. Ogawa_Y et al. 1986
n.a. LBF20207PG22 See above. Urade_Y et al. 1995