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Eicosanoid


DATA No : XPR3201 INFORMANT : Shouzo Yamamoto

NAME : 5(S)-Hydoxy-6(R)-S-g-glutamylcysteinylglycinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid

COMMON NAME: LEUKOTRIENE C4
SYMBOL: LTC4
FORMULA: C30H47O9N3S1 MOL.WT (average) : 625.775


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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 (Ref. 0022). Gasstrointestinal smooth muscles are contracted (Ref. 0021/0022). Leukotriene C4 binds to a receptor with 7 transmembrane domains coupled to Gia/o protein (CysLT1) with an affinity lower by two orders of magnitude than that of leukotriene D4 (Ref. 0030).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:METHANOL (Ref. 1024)
SPECTRAL DATA
UV SPECTRA:l MeOHmax = 270(e 32,000), 280(e 40,000), 290(e 31,000)nm (Ref. 1024)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:the Chart(Ref. 1025)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Leukotriene C4 is produced by polymorphonuclear leukocytes, mast cells and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).
CHEMICAL SYNTHESIS
(Ref. 1024)
[Table 0001]
METABOLISM
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 (Ref. 0021).
GENETIC INFORMATION
cDNA and genomic DNA of 5-lipoxygenase (Ref. 0007) and those for leukotriene C synthase (Ref. 0028/0029) were cloned. cDNA for CysLT1 was cloned (Ref. 0030).
NOTE

REFERENCES
[0007]
AUTHOR:Funk, C.D.
TITLE:Molecular biology in the eicosanoid field . PubMed ID:8341804
JOURNAL:Progr. Nucleic Acid Res.
VOL:45 PAGE : 67 -98 (1993)
[TOP]

[0021]
AUTHOR:Samuelsson, B., and Hammarstrom, S.
TITLE:Leukotrienes: a novel group of biologically active compounds PubMed ID:6293196
JOURNAL:Vitam Horm.
VOL:39 PAGE : 1-30 (1982)
[TOP]

[0022]
AUTHOR:Hammarstrom, S.
TITLE:Leukotrienes PubMed ID:6311078
JOURNAL:Annu Rev Biochem.
VOL:52 PAGE : 355-377 (1983)
[TOP]

[0028]
AUTHOR:Lam, B. K., Penrose, J. F., Freeman, G. J., and Austen, K. F.
TITLE:Expression cloning of a cDNA for human leukotriene C4 synthase, an integral membrane protein conjugating reduced glutathione to leukotriene A4 PubMed ID:8052639
JOURNAL:Proc Natl Acad Sci U S A.
VOL:91 PAGE : 7663-7667 (1994)
[TOP]

[0029]
AUTHOR:Penrose, J. F., Spector, J., Baldasaro, M., Xu, K., Boyce, J., Arm, J. P., Austen, K. F., and Lam, B. K.
TITLE:Molecular cloning of the gene for human leukotriene C4 synthase. Organization, nucleotide sequence, and chromosomal localization to 5q35 PubMed ID:8626689
JOURNAL:J Biol Chem.
VOL:271 PAGE : 11356-11361 (1996)
[TOP]

[0030]
AUTHOR:Lynch, K. R., O'Neill, G. P., Liu, Q., Im, D. S., Sawyer, N., Metters, K. M., Coulombe, N., Abramovitz, M., Figueroa, D. J., Zeng, Z., et al.
TITLE:Characterization of the human cysteinyl leukotriene CysLT1 receptor PubMed ID:10391245
JOURNAL:Nature.
VOL:399 PAGE : 789-793 (1999)
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[1024]
AUTHOR:Corey,E.J., Clark,D.A., Goto,G., Marfat,A., Mioskowski,C., Samuelsson,B., and Hammarströ$m,S.
TITLE:Stereospecific Total Synthesis of a 'Slow Reacting Substance' of Anaphylaxis, Leucotriene C-1.
JOURNAL:J. Am. Chem. Soc.
VOL:102 PAGE : 1436 -1439 (1980)
[TOP]

[1025]
AUTHOR:Pace-Asciak, C. R.
TITLE:Mass spectra of prostaglandins and related products PubMed ID:2521759
JOURNAL:Adv Prostaglandin Thromboxane Leukot Res.
VOL:18 PAGE : 1-565 (1989)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.