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Eicosanoid


DATA No : XPR3101 INFORMANT : Shouzo Yamamoto

NAME : 5(S),12(R)-Dihydroxyeicosa-6(Z),8(E),10(E),14(Z)-tetraenoic acid

COMMON NAME: LEUKOTRIENE B4
SYMBOL: LTB4
FORMULA: C20H32O4 MOL.WT (average) : 336.466


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BIOLOGICAL ACTIVITY
Leukotriene B4 causes adhesion of leukocytes to endothelial cells, stimulates chemotaxis and chemokinesis of leukocytes(Ref. 0022), and enhances superoxide anion production by human polymorphonuclear leukocytes (Ref. 0023). Leukotriene B4 binds to a specific receptor with 7 transmembrane domains coupled to Gi/Go or Gq protein (Ref. 0024).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:METHANOL (Ref. 1021)
SPECTRAL DATA
UV SPECTRA:METHANOL : 260(e 38,000), 270.5(e 50,000), 281(e 39,000)nm (Ref. 1021)

IR SPECTRA:

NMR SPECTRA:1H-NMR(250MHz, D2O) : d 6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) (Ref. 1022)

MASS SPECTRA:m/e 336, 319, 301 (Ref. 1023)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Leukotriene B4 is produced by polymorphonuclear leukocytes and macrophages of various animal species upon various stimulations on the cells (Ref. 0021/0022).
CHEMICAL SYNTHESIS
(Ref. 1021)
[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 B4 by leukotriene A hydrolase (Ref. 0025). Leukotriene B4 is metabolized to lose its bioactivities either by w-oxidation (Ref. 0022) or by leukotriene B4 12-hydroxydehydrogenase (Ref. 0026).
GENETIC INFORMATION
cDNA and genomic DNA of 5-lipoxygenase (Ref. 0007) and cDNA for Leukotriene A hydrolase (Ref. 0007) were cloned. cDNA for leukotriene B 12-hydroxydehydrogenase was cloned (Ref. 0027).
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)
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[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]

[0023]
AUTHOR:Sumimoto, H., Takeshige, K., and Minakami, S.
TITLE:Superoxide production of human polymorphonuclear leukocytes stimulated by leukotriene B4 PubMed ID:6322859
JOURNAL:Biochim Biophys Acta.
VOL:803 PAGE : 271-277 (1984)
[TOP]

[0024]
AUTHOR:Yokomizo, T., Izumi, T., Chang, K., Takuwa, Y., and Shimizu, T.
TITLE:A G-protein-coupled receptor for leukotriene B4 that mediates chemotaxis PubMed ID:9177352
JOURNAL:Nature.
VOL:387 PAGE : 620-624 (1997)
[TOP]

[0025]
AUTHOR:Ford-Hutchinson, A. W., Gresser, M., and Young, R. N.
TITLE:5-Lipoxygenase PubMed ID:7979243
JOURNAL:Annu Rev Biochem.
VOL:63 PAGE : 383-417 (1994)
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[0026]
AUTHOR:Yokomizo,T., Izumi,T., Takahashi,T., Kazama,T., Kobayashi,Y., Sato,F., Taketani,Y., and Shimizu,T.
TITLE:Enzymatic inactivation of leukotrieneB4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase. PubMed ID:8394361
JOURNAL:J. Biol. Chem.
VOL:268 PAGE : 18128 -18135 (1993)
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[0027]
AUTHOR:Yokomizo,T., Ogawa,Y., Uozumi,N., Kume,K., Izumi,T., Shimizu,T.
TITLE:cDNA cloning, expression, and mutagenesis study of leukotriene B4 12-hydroxydehydrogenase. PubMed ID:8576264
JOURNAL:J. Biol. Chem.
VOL:271 PAGE : 2844 -2850 (1996)
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[1021]
AUTHOR:Corey,E.J., Marfat,A., Goto,G., and Brion F.
TITLE:Leukotriene B. Total Synthesis and Assignment of Stereochemistry.
JOURNAL:J. Am. Chem. Soc.
VOL:102 PAGE : 7984 -7985 (1980)
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[1022]
AUTHOR:Merrer,Y.L., Gravier-Pelletier,C., Micas-Languin,D., Mestre,F., Durö$ault,A., and Depezay,J.-C.
TITLE:Total Synthesis of Leukotriene B4 [(+)-LTB4] and Homo-LTB4 from D-Mannitol.
JOURNAL:J. Org. Chem.
VOL:54 PAGE : 2409 -2416 (1989)
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[1023]
AUTHOR:Yergey, J. A., Kim, H. Y., and Salem, N., Jr.
TITLE:High-performance liquid chromatography/thermospray mass spectrometry of eicosanoids and novel oxygenated metabolites of docosahexaenoic acid PubMed ID:2942056
JOURNAL:Anal Chem.
VOL:58 PAGE : 1344-1348 (1986)
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