Eicosanoid

DATA No : XPR3401 INFORMANT : Shouzo Yamamoto

NAME : 5(S)-Hydroxy-6(R)-S-cysteinyleicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid

COMMON NAME	:	LEUKOTRIENE E4
SYMBOL	:	LTE4
FORMULA	:	C₂₃H₃₇O₅N₁S₁ MOL.WT (average) : 439.610

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BIOLOGICAL ACTIVITY

Leukotriene E4 stimulates airway smooth muscles from different animal species, and is less potent than C4 in contracting isolated guinea pig ileum (Ref. 0022).

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	DIMETHYL ESTER ; [a]=+35.2 (Ref. 1063)

DENSITY	:

SOLUBILITY	:	METHANOL (Ref. 1063/1028)

SPECTRAL DATA

UV SPECTRA	:	MONO-POTASSIUM SALT;l = 270(e 40000), 280(e 49400), 291nm( e 40000) (Ref. 1028)

IR SPECTRA	:

NMR SPECTRA	:	DIMETHYL ESTER ; ¹H-NMR(CDCl₃) : d 6.33(dd, J=14.5Hz, 10Hz, 1H, 10CH), 6.0(t, J=10Hz, 1H, 11-CH), 5.62(dd, J=14.4, 9.6Hz, 1H, 7-CH), 5.3(m, J=10,9Hz, 1H, 14-CH), 3.71 and 3.62(2S, 6H, OCH₃), 3.65(m, 1H, 5-CH), 3.4(m, 1H, 6-CH), 2.95(t, J=9Hz, 2H, 13-CH), 2.02(m, 2H, 16-CH), 0.86(t, J=6Hz, 3H, 20-CH) (Ref. 1063)

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

When leukotriene C4 was injected into male subjects, leukotriene E4 was found as a major urinary metabolite (Ref. 0050). Incubation of leukotriene D4 with human polymorphonuclear leukocytes produced leukotriene E4 (Ref. 0051).

CHEMICAL SYNTHESIS

(Ref. 1028)
[Table 0001]

METABOLISM

Leukotriene D4 is converted to E4 by extracellular action of a dipeptidase released from granules of human polymorphonuclear leukocytes (Ref. 0051). Leukotriene E4 is transformed to leukotriene F4 by g-glultamyltransferase in the presence of glutathione, and to N-acetyl leukotriene E4 by incubation with rat liver microsomes (Ref. 0052).

GENETIC INFORMATION

NOTE

REFERENCES

[0022]

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

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[0050]

AUTHOR	:	Orning, L., Kaijser, L., and Hammarstrom, S.
TITLE	:	In vivo metabolism of leukotriene C4 in man: urinary excretion of leukotriene E4 PubMed ID:2992461
JOURNAL	:	Biochem Biophys Res Commun.
VOL	:	130 PAGE : 214-220 (1985)

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[0051]

AUTHOR	:	Lee, C. W., Lewis, R. A., Corey, E. J., and Austen, K. F.
TITLE	:	Conversion of leukotriene D4 to leukotriene E4 by a dipeptidase released from the specific granule of human polymorphonuclear leucocytes PubMed ID:6293969
JOURNAL	:	Immunology.
VOL	:	48 PAGE : 27-35 (1983)

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[0052]

AUTHOR	:	Hammarstrom,S., Oerning,L., and Bernstroem,K.
TITLE	:	Metabolism of leukotrienes. PubMed ID:3001504
JOURNAL	:	Molecular and Cellular Biochemistry
VOL	:	69 PAGE : 7 -16 (1985)

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[1028]

AUTHOR	:	Cohen,N., Banner,B.L., Lopresti,R.J., Wong,F., Rosenberger,M., Liu,Y.-Y., Thom,E., and Liebman,A.A.
TITLE	:	Enantiospecific Syntheses of Leukotrienes C4, D4, and E4 and [14,15³H₂]Leukotriene E4 Dimethyl Ester.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	105 PAGE : 3661 -3672 (1983)

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[1063]

AUTHOR	:	Rosenberger,M., Newkom,C., and Aig,E.R.
TITLE	:	Total Synthesis of Leukotriene E4, a Member of the SRS-A Family.
JOURNAL	:	J. Am. Chem. Soc.
VOL	:	105 PAGE : 3656 -3661 (1983)

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