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Eicosanoid


DATA No : XPR5001 INFORMANT : Shouzo Yamamoto

NAME : 8-Hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z,Z),9(E)-trienoic acid

COMMON NAME: HEPOXILIN A3
SYMBOL: HxA3
FORMULA: C20H32O4 MOL.WT (average) : 336.466


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BIOLOGICAL ACTIVITY
As the biological activities of hepoxilin A3, insulin secretion from pancreas is stimulated, the enhanced vascular permeability by bradykinin is potentiated, hyperpolarization in hippocampal CA1 neurons is caused, and platelet aggregation is inhibited. At the molecular level hepoxilin A3 releases intracellular calcium, and opens potassium channel. Hepoxilin-specific binding proteins are present in human neutrophils (Ref. 0055).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:DIETHYL ETHER (Ref. 1071)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:METHYL ESTER TRIS-TMS ETHER ; m/e 422(M+), 407, 391, 332, 311, 282, 269(base peak) (Ref. 1070)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Hepoxilin A3 together with hepoxilin B3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin (Ref. 0055).
CHEMICAL SYNTHESIS
(Ref. 1072)
[Table 0001]
METABOLISM
The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production (Ref. 0056).
GENETIC INFORMATION

NOTE

REFERENCES
[0055]
AUTHOR:Pace-Asciak, C. R.
TITLE:Hepoxilins: a review on their cellular actions PubMed ID:7947989
JOURNAL:Biochim Biophys Acta.
VOL:1215 PAGE : 1-8 (1994)
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[0056]
AUTHOR:Pace-Asciak, C. R., Reynaud, D., and Demin, P. M.
TITLE:Hepoxilins: a review on their enzymatic formation, metabolism and chemical synthesis PubMed ID:7769965
JOURNAL:Lipids.
VOL:30 PAGE : 107-114 (1995)
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[1070]
AUTHOR:Walker, I. C., Jones, R. L., and Wilson, N. H.
TITLE:The identification of an epoxy-hydroxy acid as a product from the incubation of arachidonic acid with washed blood platelets PubMed ID:523677
JOURNAL:Prostaglandins.
VOL:18 PAGE : 173-178 (1979)
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[1071]
AUTHOR:Pace-Asciak, C. R., Mizuno, K., and Yamamoto, S.
TITLE:Resolution by DEAE-cellulose chromatography of the enzymatic steps in the transformation of arachidonic acid into 8, 11, 12- and 10, 11, 12-trihydroxy-eicosatrienoic acid by the rat lung PubMed ID:6405454
JOURNAL:Prostaglandins.
VOL:25 PAGE : 79-84 (1983)
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[1072]
AUTHOR:Corey,E.J. and Su,W.
TITLE:Total Synthesis of Biologically Active Metabolites of Arachidonic Acid. The Two 8-Hydroxy-11,12(S,S)-epoxyeicosa-5,14(Z),9(E)-trienoic Acids.
JOURNAL:Tetrah. Lett.
VOL:25 PAGE : 5119 -5122 (1984)
[TOP]

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