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Eicosanoid


DATA No : XPR6003 INFORMANT : Shouzo Yamamoto

NAME : 15(S)-Hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid

COMMON NAME:
SYMBOL: 15(S)-HPETE
FORMULA: C20H32O4 MOL.WT (average) : 336.466


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BIOLOGICAL ACTIVITY
15-Lipoxygenase present in rabbit reticulocytes is presumed to be involved in the breakdown of mitochondrial membrane and the maturation of red cells (Ref. 0062). The enzyme is active with esterified polyunsaturated fatty acids contained in the membrane of subcelluar orgnelles or serum lipoprotein, and its peroxy products may be involved in the pathogenesis of arteriosclerosis (Ref. 0063).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:DIETHYL ETHER (Ref. 1077), ETHYL ACETATE(Ref. 1078), ETHANOL(Ref. 1086), METHANOL(Ref. 1087)
SPECTRAL DATA
UV SPECTRA:lmax = 236nm(e 27000) (Ref. 1086) lmax(ISO-OCTANE) = 236nm(e 30000) (Ref. 1085)

IR SPECTRA:

NMR SPECTRA:METHYL ESTER ; 1H-NMR(360MHz) : d 6.61(dd, J=11, 15.5Hz, 1H, 13-CH), 6.03(dd, J=10.5, 11Hz, 1H, 12-CH), 5.61(J=7.5Hz, 1H, 14-CH), 5.46(dd, J=7.5, 10.5Hz, 1H,11-CH), 5.39(m, 4H, 5,6,8,9-CH), 4.39(m, 1H, 15-CH), 3.67(s, 3H, OCH3), 2.98(2H, 10-CH), 2.81(2H, 7-CH), 2.33(2H, 2-CH), 2.11(2H, 4-CH), 1.72(2H, 3-CH), 1.64(2H, 16-CH), 1.30(6H), 0.88(3H, 20-CH) (Ref. 1087)

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
(Ref. 1086)
[Table 0001]
METABOLISM
When arachidonic acid is allowed to react with 15-lipoxygenase, the predominant product is 15(S)-hydroperoxy-5,8,11,13-(Z,Z,Z,E)-eicosatetraenoic acid (Ref. 0061). The 15-hydroperoxy acid is further transformed to dihydroperoxy acids or 14,15-epoxy acid with a conjugated triene by the catalyses of 12- and 15-lipoxygenases (Ref. 0065), and is a precursor for lipoxin biosynthesis (Ref. 0035).
GENETIC INFORMATION
cDNA and genomic DNA of 15-lipoxygenases were cloned (Ref. 0064).
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]

[0061]
AUTHOR:Bryant, R. W., Bailey, J. M., Schewe, T., and Rapoport, S. M.
TITLE:Positional specificity of a reticulocyte lipoxygenase. Conversion of arachidonic acid to 15-S-hydroperoxy-eicosatetraenoic acid PubMed ID:6804460
JOURNAL:J Biol Chem.
VOL:257 PAGE : 6050-6055 (1982)
[TOP]

[0062]
AUTHOR:Schewe, T., Rapoport, S. M., and Kuhn, H.
TITLE:Enzymology and physiology of reticulocyte lipoxygenase: comparison with other lipoxygenases PubMed ID:3087141
JOURNAL:Adv Enzymol Relat Areas Mol Biol.
VOL:58 PAGE : 191-272 (1986)
[TOP]

[0063]
AUTHOR:Harats,D., Mulkins,M.A., and Sigal,E.
TITLE:A possible role for 15-lipoxygenase in atherogenesis.
JOURNAL:TCM
VOL:5 PAGE : 29 -36 (1995)
[TOP]

[0064]
AUTHOR:Kuehn,H., and Thiele,B.-J.
TITLE:Arachidonate 15-lipoxygenase.
JOURNAL:J. Lipid Mediators Cell Signalling
VOL:12 PAGE : 157 -170 (1995)
[TOP]

[0065]
AUTHOR:Yamamoto, S.
TITLE:Mammalian lipoxygenases: molecular structures and functions PubMed ID:1420284
JOURNAL:Biochim Biophys Acta.
VOL:1128 PAGE : 117-131 (1992)
[TOP]

[1077]
AUTHOR:Porter,N.A., Logan,J. and Kontoyiannidou,V.
TITLE:Preparation and Purification of Arachidonic Acid Hydroperoxides of Biological Importance.
JOURNAL:J. Org. Chem.
VOL:44 PAGE : 3177 -3181 (1979)
[TOP]

[1078]
AUTHOR:Boeynaems, J. M., Brash, A. R., Oates, J. A., and Hubbard, W. C.
TITLE:Preparation and assay of monohydroxy-eicosatetraenoic acids PubMed ID:7004263
JOURNAL:Anal Biochem.
VOL:104 PAGE : 259-267 (1980)
[TOP]

[1085]
AUTHOR:Hamberg,M. and Samuelsson,B.
TITLE:On the Specificity of the Oxygenation of Unsaturated Fatty Acids Catalyzed by Soybean Lipoxidase. PubMed ID:6070850
JOURNAL:J. Biol. Chem.
VOL:242 PAGE : 5329 -5335 (1967)
[TOP]

[1086]
AUTHOR:Baldwin,J.E., Davies,D.I., Hughes,L. and Gutterridge,N.J.A.
TITLE:Synthesis from Arachidonic Acid of Potential Prostaglandin Precursors.
JOURNAL:J. Chem. Soc. Perkin I
VOL: PAGE : 115 -121 (1979)
[TOP]

[1087]
AUTHOR:Van Os, C. P., Rijke-Schilder, G. P., Van Halbeek, H., Verhagen, J., and Vliegenthart, J. F.
TITLE:Double dioxygenation of arachidonic acid by soybean lipoxygenase-1. Kinetics and regio-stereo specificities of the reaction steps PubMed ID:6783108
JOURNAL:Biochim Biophys Acta.
VOL:663 PAGE : 177-193 (1981)
[TOP]

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