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Eicosanoid


DATA No : XPR4101 INFORMANT : Shouzo Yamamoto

NAME : 5(S),14(R),15(S)-Trihydroxyeicosa-6(E),8(Z),10(E),12(E)-tetraenoic acid

COMMON NAME: LIPOXIN B4
SYMBOL: LXB4
FORMULA: C20H32O5 MOL.WT (average) : 352.465


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BIOLOGICAL ACTIVITY
Lipoxin B4 is either vasoconstrictive or vasodilatory, and blocks the cytotoxic action of NK cell (Ref. 0035).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:METHYL ESTER ; [a]d-20=19.2deg(C=1.16, CHLOROFORM) (Ref. 1041)

DENSITY:

SOLUBILITY:METHANOL (Ref. 1039)
SPECTRAL DATA
UV SPECTRA:l MeOHmax = 288, 300(e 50,000), 315nm (Ref. 1040)

IR SPECTRA:METHYL ESTER ; CHCl3 solution, n 3610, 3470, 3030, 3015, 2960, 2935, 2860, 1735, 1605, 1440, 1230, 1000, 980cm-1 (Ref. 1041)

NMR SPECTRA:1H-NMR(250MHz, CDCl3) : d 6.68(m, 2H), 6.36(dd, J=14.8 and 10.5Hz, 1H), 6.23(dd, J=14.1 and 10.7Hz, 1H), 6.0(m, 2H), 5.75(m, 2H), 4.17(m, 2H), 3.70(m, 1H), 3.65(s, 3H), 2.34(t, J=7.1Hz, 2H), 1.78-1.21(m, 12H), 0.86(t, J=6.4Hz, 3H) (Ref. 1041)

MASS SPECTRA:TRIMETHYLSILYL ETHER METHYL ESTER ; 582(M+), 492, 482, 409, 402, 379, 329, 319, 307, 289, 203, 173 (Ref. 1040)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Lipoxin B4 is produced by activated leukocytes (Ref. 0035/0036).
CHEMICAL SYNTHESIS
(Ref. 1041)
[Table 0001]
METABOLISM
Dual lipoxygenation pathways are considered for lipoxin B4 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

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]

[1039]
AUTHOR:Serhan,C.N., Hamberg,M., and Samuelsson,B.
TITLE:Lipoxins: Novel Series of Biologically Active Compounds Formed from Arachidonic Acid in Human Leukocytes. PubMed ID:6089195
JOURNAL:Proc. Nat. Acad. Sci. USA
VOL:81 PAGE : 5335 -5339 (1984)
[TOP]

[1040]
AUTHOR:Serhan, C. N., Hamberg, M., Samuelsson, B., Morris, J., and Wishka, D. G.
TITLE:On the stereochemistry and biosynthesis of lipoxin B PubMed ID:3083410
JOURNAL:Proc Natl Acad Sci U S A.
VOL:83 PAGE : 1983-1987 (1986)
[TOP]

[1041]
AUTHOR:Nicolaou,K.C., and Webber,S.E.
TITLE:Stereocontrolled Total Synthesis of Lipoxin B.
JOURNAL:Synthesis
VOL: PAGE : 453 -461 (1986)
[TOP]

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