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|LipidBank=DFA8153
|LipidBank=DFA8153
|LipidMaps=LMFA03040001
|LipidMaps=LMFA03040001
|SysName=5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid
|CAS=89663-86-5
|Common Name=&&lipoxin A_4&&5S,6R,15S-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid&&
|SysName=(5S,6R,15S) -Trihydroxy- (trans-7,trans-9,cis-11,trans-13) -eicosatetraenoic acid
|UV Spectra=<FONT FACE="Symbol">l</FONT>max: 302nm <FONT FACE="Symbol">e</FONT>: 50,000
|Common Name=&&Lipoxin A_4&&(5S,6R,15S) -Trihydroxy- (7E,9E,11Z,13E) -eicosatetraenoic acid&&
|Source=LXA4 is formed in vitro by a number of mechanisms from arachidonic acid, 15-HpETE, and leukotriene A4 (LTA4 ) [[Reference:Edenius_C:Stenke_L:Lindgren_JA:,Eur. J. Biochem.,1991,199,401|{{RelationTable/GetFirstAuthor|Reference:Edenius_C:Stenke_L:Lindgren_JA:,Eur. J. Biochem.,1991,199,401}}]][[Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335}}]].
|Solubility=diethyl ether, methanol. [[Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464|{{RelationTable/GetFirstAuthor|Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464}}]]<!--1037-->
|Chemical Synthesis=
|UV Spectra=lambda max: 302nm  epsilon : 50,000, lambda MeOHmax: 287,301 (epsilon 50,000) : 316nm [[Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464|{{RelationTable/GetFirstAuthor|Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464}}]]<!--1037-->, [[Reference:Serhan_CN:Nicolaou_KC:Webber_SE:Veale_CA:Dahlen_SE:Puustinen_TJ:Samuelsson_B:,J._Biol._Chem.,1986,261,16340|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:Nicolaou_KC:Webber_SE:Veale_CA:Dahlen_SE:Puustinen_TJ:Samuelsson_B:,J._Biol._Chem.,1986,261,16340}}]]<!--1038-->
|Metabolism=
|NMR Spectra=^1 H-NMR(250MHz, 5% CD3OD/D2O ) : delta 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). [[Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464|{{RelationTable/GetFirstAuthor|Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464}}]]<!--1037-->
|Mass Spectra=TMS-derivs. ; 582(M^+ ), 492, 482, 379, 289, 203, 173, 171. [[Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Biochem._Biophys._Res._Commun.,1984,118,943|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Biochem._Biophys._Res._Commun.,1984,118,943}}]]<!--1036-->
|Source=LXA4 is formed in vitro by a number of mechanisms from arachidonic acid, 15-HpETE, and leukotriene A4 (LTA4 ) [[Reference:Edenius_C:Stenke_L:Lindgren_JA:,Eur. J. Biochem.,1991,199,401|{{RelationTable/GetFirstAuthor|Reference:Edenius_C:Stenke_L:Lindgren_JA:,Eur. J. Biochem.,1991,199,401}}]][[Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335}}]]. Lipoxin A4 is produced by activated leukocytes [[Reference:Serhan_CN:,Biochim._Biophys._Acta,1994,1212,1|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:,Biochim._Biophys._Acta,1994,1212,1}}]]<!--0035-->, [[Reference:Brady_HR:Serhan_CN:,Curr._Opin._Nephrol._Hypertens.,1996,5,20|{{RelationTable/GetFirstAuthor|Reference:Brady_HR:Serhan_CN:,Curr._Opin._Nephrol._Hypertens.,1996,5,20}}]]<!--0036-->.
|Chemical Synthesis=[http://lipidbank.jp/image/XPR4001FT0001.gif Table0001] [[Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464|{{RelationTable/GetFirstAuthor|Reference:Adams_J:Fitzsimmons_BJ:Girard_Y:Leblanc_Y:Evans_JF:Rokach_J:,J._Am._Chem._Soc.,1985,107,464}}]]<!--1037-->
|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 [[Reference:Serhan_CN:,Biochim._Biophys._Acta,1994,1212,1|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:,Biochim._Biophys._Acta,1994,1212,1}}]]<!--0035-->.
|Genetic Information=cDNA for a receptor specific for lipoxin A4 was cloned out of orphan cDNAs [[Reference:Fiore_S:Maddox_JF:Perez_HD:Serhan_CN:,J._Exp._Med.,1994,180,253|{{RelationTable/GetFirstAuthor|Reference:Fiore_S:Maddox_JF:Perez_HD:Serhan_CN:,J._Exp._Med.,1994,180,253}}]]<!--0037-->.
|Symbol=LXA4
|Biological Activity=LXA is equipotent to LTB in inducing superoxide generation in human neutrophils (0.1 mu M) [[Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335}}]]. LXA4 is associated with several other biological functions including leukocyte activation, chemotaxis promotion, natural killer cell inhibition, and monocyte migration and adhesion [[Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:Hamberg_M:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1984,81,5335}}]][[Reference:Ramstedt_U:Serhan_CN:Nicolaou_KC:Webber_SE:Wigzell_H:Samuelsson_B:,J. Immunol.,1987,138,266|{{RelationTable/GetFirstAuthor|Reference:Ramstedt_U:Serhan_CN:Nicolaou_KC:Webber_SE:Wigzell_H:Samuelsson_B:,J. Immunol.,1987,138,266}}]][[Reference:Maddox_JF:Serhan_CN:,J. Exp. Med.,1996,183,137|{{RelationTable/GetFirstAuthor|Reference:Maddox_JF:Serhan_CN:,J. Exp. Med.,1996,183,137}}]]. 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[[Reference:Serhan_CN:,Biochim._Biophys._Acta,1994,1212,1|{{RelationTable/GetFirstAuthor|Reference:Serhan_CN:,Biochim._Biophys._Acta,1994,1212,1}}]]<!--0035-->.
}}
 
{{MassbankSpectra|
UT000325
UT000326
UT000327
UT000328
UT000329
UT000330
UT000331
UT000332
UT000333
}}
}}


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

Latest revision as of 00:00, 21 January 2014

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Upper classes: LB LBF



IDs and Links
LipidBank DFA8153
LipidMaps LMFA03040001
CAS 89663-86-5
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20407LX01
Lipoxin A4
LBF20407LX01.png
Structural Information
(5S,6R,15S) -Trihydroxy- (trans-7,trans-9,cis-11,trans-13) -eicosatetraenoic acid
  • Lipoxin A4
  • (5S,6R,15S) -Trihydroxy- (7E,9E,11Z,13E) -eicosatetraenoic acid
 LXA4
Formula C20H32O5
Exact Mass 352.224974134
Average Mass 352.46508
SMILES C(CCC(C=CC=CC=CC=CC(O)C(O)CCCC(O)=O)O)CC
Physicochemical Information
diethyl ether, methanol. AdamsJet al.
LXA4 is formed in vitro by a number of mechanisms from arachidonic acid, 15-HpETE, and leukotriene A4 (LTA4 ) Edenius_C et al. Serhan_CN et al.. Lipoxin A4 is produced by activated leukocytes Serhan_CN , Brady_HR et al..
Table0001 Adams_J et al.
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 Serhan_CN .
LXA is equipotent to LTB in inducing superoxide generation in human neutrophils (0.1 mu M) Serhan_CN et al.. LXA4 is associated with several other biological functions including leukocyte activation, chemotaxis promotion, natural killer cell inhibition, and monocyte migration and adhesion Serhan_CN et al. Ramstedt_U et al. Maddox_JF et al.. 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 Serhan_CN .
cDNA for a receptor specific for lipoxin A4 was cloned out of orphan cDNAs Fiore_S et al..
Spectral Information
Mass Spectra TMS-derivs. ; 582(M+), 492, 482, 379, 289, 203, 173, 171. Serhan_CN et al.
UV Spectra λ max: 302nm ε : 50,000, λ MeOHmax: 287,301 (ε 50,000) : 316nm AdamsJet al., Serhan_CN et al.
IR Spectra
NMR Spectra 1H-NMR(250MHz, 5% CD3OD/D2O ) : δ 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). AdamsJet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20407LX01 See above. Adams_J et al. 1985
n.a. LBF20407LX01 See above. Brady_HR et al. 1996
n.a. LBF20407LX01 See above. Edenius_C et al. 1991
n.a. LBF20407LX01 See above. Fiore_S et al. 1994
n.a. LBF20407LX01 See above. Maddox_JF et al. 1996
n.a. LBF20407LX01 See above. Ramstedt_U et al. 1987
n.a. LBF20407LX01 See above. Serhan_CN 1994
n.a. LBF20407LX01 See above. Serhan_CN et al. 1984
n.a. LBF20407LX01 See above. Serhan_CN et al. 1984
n.a. LBF20407LX01 See above. Serhan_CN et al. 1986



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