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Eicosanoid


DATA No : XPR4001 INFORMANT : Shouzo Yamamoto

NAME : 5(S),6(R),15(S)-Trihydroxyeicosa-7(E),9(E),11(Z),13(E)-tetraenoic acid

COMMON NAME: LIPOXIN A4
SYMBOL: LXA4
FORMULA: C20H32O5 MOL.WT (average) : 352.465


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BIOLOGICAL ACTIVITY
Lipoxin A4 is either vasoconstrictive or vasodilatory, and has immunoregulatory activities blocking the cytotoxic action of NK cell, inhibiting adherence and chemotaxis of leukocytes induced by FMLP, PAF or leukotriene B4 (Ref. 0035).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:DIETHYL ETHER, METHANOL (Ref. 1037)
SPECTRAL DATA
UV SPECTRA:l MeOHmax = 287, 301(e 50,000), 316nm (Ref. 1037/1038)

IR SPECTRA:

NMR SPECTRA:1H-NMR(250MHz, 5% CD3OD/D2O ) : d 0.8-0.9(brt, 3H), 1.2-1.8(m, 14H), 2.1-2.3(m, 2H), 3.4-3.6(m, 1H), 3.95-4.05(t, J=6.8Hz, 1H), 4.1-4.2(q, J=7.1Hz, 1H), 5.6-5.85(seven lines, 2H), 5.9-6.1(m, 2H), 6.2-6.45(m, 2H), 6.6-6.8(m, 2H) (Ref. 1037)

MASS SPECTRA:TMS-derivs. ; 582(M+), 492, 482, 379, 289, 203, 173, 171 (Ref. 1036)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Lipoxin A4 is produced by activated leukocytes (Ref. 0035/0036).
CHEMICAL SYNTHESIS
(Ref. 1037)
[Table 0001]
METABOLISM
Dual lipoxygenation pathways are considered for lipoxin A4 synthesis from arachidonic acid; either 15-lipoxygenase and 5-lipoxygenase in leukocytes or 5-lipoxygenase in leukocytes and 12-lipoxygenase in platelets (Ref. 0035).
GENETIC INFORMATION
cDNA for a receptor specific for lipoxin A4 was cloned out of orphan cDNAs (Ref. 0037).
NOTE

REFERENCES
[0035]
AUTHOR:Serhan, C. N.
TITLE:Lipoxin biosynthesis and its impact in inflammatory and vascular events PubMed ID:8155718
JOURNAL:Biochim Biophys Acta.
VOL:1212 PAGE : 1-25 (1994)
[TOP]

[0036]
AUTHOR:Brady,H.R., and Serhan,C.N.
TITLE:Lipoxins: putative braking signals in host defense, inflammation and hypersensitivity. PubMed ID:8834158
JOURNAL:Curr. Opinion Hephrol.Hypertension
VOL:5 PAGE : 20 -27 (1996)
[TOP]

[0037]
AUTHOR:Fiore,S., Maddox,J.F., Perez,H.D., and Serhan,C.N.
TITLE:Identification of a human cDNA encoding a functional high affinity lipoxin A4 receptor. PubMed ID:8834158
JOURNAL:J. Exp. Med.
VOL:180 PAGE : 253 -260 (1994)
[TOP]

[1036]
AUTHOR:Serhan, C. N., Hamberg, M., and Samuelsson, B.
TITLE:Trihydroxytetraenes: a novel series of compounds formed from arachidonic acid in human leukocytes PubMed ID:6422933
JOURNAL:Biochem Biophys Res Commun.
VOL:118 PAGE : 943-949 (1984)
[TOP]

[1037]
AUTHOR:Adams,J., Fitzsimmons,B.J., Girard,Y., Leblanc,Y, Evans,J.F., and Rokach,J.
TITLE:Enantiospecific and Stereospecific Synthesis of Lipoxin A. Stereochemical Assignment of the Natural Lipoxin A and Its Possible Biosynthesis.
JOURNAL:J. Am. Chem. Soc.
VOL:107 PAGE : 464 -469 (1985)
[TOP]

[1038]
AUTHOR:Serhan, C. N., Nicolaou, K. C., Webber, S. E., Veale, C. A., Dahlen, S. E., Puustinen, T. J., and Samuelsson, B.
TITLE:Lipoxin A. Stereochemistry and biosynthesis PubMed ID:3097008
JOURNAL:J Biol Chem.
VOL:261 PAGE : 16340-16345 (1986)
[TOP]

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