LBF20207PG22

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Upper classes: LB LBF



Prostaglandin D2
LBF20207PG22.png
Structural Information
Systematic Name 7- [5S -Hydroxy-2R - (3S-hydroxy-trans-1-octenyl) -3-oxocyclopentan-1R -yl] -cis-5-heptenoic acid
Common Name
  • Prostaglandin D2
  • 7- [ 5 (S) -Hydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenyl) -3-oxocyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Symbol PGD2
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
Melting Point 68°C Hayashi_M et al.
Boiling Point
Density
Optical Rotation [ α ]20
D
   =9° (C=2.11,THF) OgawaYet al.
Refractive Index
Solubility ETHYL ACETATE,THF,CHLOROFORM OgawaYet al.
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 Urade_Y et al..
Chemical Synthesis Hayashi_M et al.
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 Urade_Y et al.. Prostaglandin D2 is either reduced to 9 alpha ,11 beta -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 Delta 12-prostaglandin J2 Negishi_M et al..
Biological Activity Biological significance of prostaglandin D2 was unknown except anti-aggregatory and bronchoconstrictive activities Giles_H et al.. Recently prostaglandin D2 has been noted as antineoplastic agent (actually attributed to Delta 12-prostaglandin J2) Fukushima_M Negishi_M et al. and as a sleep-inducing compound Hayaishi_O . Prostaglandin D2 binds to a receptor with 7 transmembrane domains (DP) coupled to a Gs protein Negishi_M et al..
Genetic Information cDNA and genomic DNA of prostaglandin D synthase were cloned Urade_Y et al.. cDNA for DP was isolated Negishi_M et al..
Note
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) : δ 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



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