LBF20406LT14: Difference between revisions

(New page: {{Lipid/Header}} {{Hierarchy|{{PAGENAME}}}} {{Metabolite |LipidBank=XPR3201 |LipidMaps=LMFA03020003 |SysName=5S-Hydroxy-6R-S-gamma-glutamylcysteinylglycinyl- (trans-7,trans-9,cis-11,cis-...)
 
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|Biological Activity=Leukotriene C4 is a potent stimulator of airway smooth muscles and causes bronchoconstriction as demonstrated in vitro and in vivo experiments, and gastrointestinal smooth muscles are also contracted. Vascular permeability is enhanced by leukotriene C4 at concentrations lower by 3-4 orders of magnitude than histamine [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]]. Gasstrointestinal smooth muscles are contracted [[Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1}}]][[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]]. Leukotriene C4 binds to a receptor with 7 transmembrane domains coupled to Gi α /o protein (CysLT1) with an affinity lower by two orders of magnitude than that of leukotriene D4 [[Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789|{{RelationTable/GetFirstAuthor|Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789}}]].
|Biological Activity=Leukotriene C4 is a potent stimulator of airway smooth muscles and causes bronchoconstriction as demonstrated in vitro and in vivo experiments, and gastrointestinal smooth muscles are also contracted. Vascular permeability is enhanced by leukotriene C4 at concentrations lower by 3-4 orders of magnitude than histamine [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]]. Gasstrointestinal smooth muscles are contracted [[Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1}}]][[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]]. Leukotriene C4 binds to a receptor with 7 transmembrane domains coupled to Gi α /o protein (CysLT1) with an affinity lower by two orders of magnitude than that of leukotriene D4 [[Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789|{{RelationTable/GetFirstAuthor|Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789}}]].
|Genetic Information=cDNA and genomic DNA of 5-lipoxygenase [[Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67|{{RelationTable/GetFirstAuthor|Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67}}]] and those for leukotriene C synthase [[Reference:Lam_BK:Penrose_JF:Freeman_GJ:Austen_KF:,Proc. Natl. Acad. Sci. U. S. A.,1994,91,7663|{{RelationTable/GetFirstAuthor|Reference:Lam_BK:Penrose_JF:Freeman_GJ:Austen_KF:,Proc. Natl. Acad. Sci. U. S. A.,1994,91,7663}}]][[Reference:Penrose_JF:Spector_J:Baldasaro_M:Xu_K:Boyce_J:Arm_JP:Austen_KF:Lam_BK:,J. Biol. Chem.,1996,271,11356|{{RelationTable/GetFirstAuthor|Reference:Penrose_JF:Spector_J:Baldasaro_M:Xu_K:Boyce_J:Arm_JP:Austen_KF:Lam_BK:,J. Biol. Chem.,1996,271,11356}}]] were cloned. cDNA for CysLT1 was cloned [[Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789|{{RelationTable/GetFirstAuthor|Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789}}]].
|Genetic Information=cDNA and genomic DNA of 5-lipoxygenase [[Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67|{{RelationTable/GetFirstAuthor|Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67}}]] and those for leukotriene C synthase [[Reference:Lam_BK:Penrose_JF:Freeman_GJ:Austen_KF:,Proc. Natl. Acad. Sci. U. S. A.,1994,91,7663|{{RelationTable/GetFirstAuthor|Reference:Lam_BK:Penrose_JF:Freeman_GJ:Austen_KF:,Proc. Natl. Acad. Sci. U. S. A.,1994,91,7663}}]][[Reference:Penrose_JF:Spector_J:Baldasaro_M:Xu_K:Boyce_J:Arm_JP:Austen_KF:Lam_BK:,J. Biol. Chem.,1996,271,11356|{{RelationTable/GetFirstAuthor|Reference:Penrose_JF:Spector_J:Baldasaro_M:Xu_K:Boyce_J:Arm_JP:Austen_KF:Lam_BK:,J. Biol. Chem.,1996,271,11356}}]] were cloned. cDNA for CysLT1 was cloned [[Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789|{{RelationTable/GetFirstAuthor|Reference:Lynch_KR:ONeill_GP:Liu_Q:Im_DS:Sawyer_N:Metters_KM:Coulombe_N:Abramovitz_M:Figueroa_DJ:Zeng_Z_et_al:,Nature,1999,399,789}}]].
}}
{{MassbankSpectra|
UT000307
UT000308
UT000309
UT000310
UT000311
UT000312
UT000313
UT000314
UT000315
}}
}}


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

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



Leukotriene C4
LBF20406LT14.png
Structural Information
5S-Hydroxy-6R-S-γ-glutamylcysteinylglycinyl- (trans-7,trans-9,cis-11,cis-14) -eicosatetraenoic acid
  • Leukotriene C4
  • 5S-Hydroxy-6R-S-γ-glutamylcysteinylglycinyl- (7E,9E,11Z,14Z) -eicosatetraenoic acid
  • 5 (S) -Hydoxy-6 (R) -S-γ-glutamylcysteinylglycinyleicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid
LTC4
Formula C30H47N3O9S
Exact Mass 625.303300807
Average Mass 625.7750000000001
SMILES C(O)(=O)[C@H](CCC(=O)N[C@@H](C(=O)NCC(O)=O)CS[C@H](C=CC=CC=CCC=CCCCCC)[C@H](O)CCCC(O)=O)N
Physicochemical Information
METHANOL Corey_EJ et al.
Leukotriene C4 is produced by polymorphonuclear leukocytes, mast cells and macrophages of various animal species upon various stimulations on the cells Samuelsson_B et al. Hammarstrom_S .
Corey_EJ et al.
LBF20406SF01FT0001.gif
Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee C4 incorporating glutathione by the catalysis of leukotriene C synthase Samuelsson_B et al..
Leukotriene C4 is a potent stimulator of airway smooth muscles and causes bronchoconstriction as demonstrated in vitro and in vivo experiments, and gastrointestinal smooth muscles are also contracted. Vascular permeability is enhanced by leukotriene C4 at concentrations lower by 3-4 orders of magnitude than histamine Hammarstrom_S . Gasstrointestinal smooth muscles are contracted Samuelsson_B et al. Hammarstrom_S . Leukotriene C4 binds to a receptor with 7 transmembrane domains coupled to Gi α /o protein (CysLT1) with an affinity lower by two orders of magnitude than that of leukotriene D4 Lynch_KR et al..
cDNA and genomic DNA of 5-lipoxygenase Funk_CD and those for leukotriene C synthase Lam_BK et al. Penrose_JF et al. were cloned. cDNA for CysLT1 was cloned Lynch_KR et al..
Spectral Information
Mass Spectra the Chart Pace-Asciak_CR
UV Spectra λ MeOH
max
     = 270( ε 32,000), 280( ε 40,000), 290( ε 31,000)nm Corey_EJ et al.
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406LT14 See above. Corey_EJ et al. 1980
n.a. LBF20406LT14 See above. Funk_CD 1993
n.a. LBF20406LT14 See above. Hammarstrom_S 1983
n.a. LBF20406LT14 See above. Lam_BK et al. 1994
n.a. LBF20406LT14 See above. Lynch_KR et al. 1999
n.a. LBF20406LT14 See above. Pace-Asciak_CR 1989
n.a. LBF20406LT14 See above. Penrose_JF et al. 1996
n.a. LBF20406LT14 See above. Samuelsson_B et al. 1982