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Metabolism of arachidonic acid in leukocytes: Isolation of a 5,15-dihydroxy-eicosatetraenoic acid

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Lipids

Abstract

A novel metabolite of arachidonic acid was isolated from incubations of peripheral blood leukocytes with the fatty acid and the ionophore A23187. The compound was purified by high performance liquid chromatography and identified by ultraviolet photometry and gas chromatography-mass spectrometry as a 5,15-dihydroxy-6,8,11,13-eicosatetraenoic acid. The compound was also isolated from incubations of human leukocytes with the 15S-hydroperoxy-5,8,11,13(Z,Z,Z,E)-eicosatetraenoic acid, suggesting a double dioxygenation mechanism in the formation of this new metabolite of arachidonic acid. A 5S,15S-dihydroxy-6,8,11,13(E,Z,Z,E)-eicosatetraenoic acid was obtained from incubations of 5S-hydroxy-6,8,11,14(E,Z,Z,Z)-eicosatetraenoic acid with the soybean lipoxygenase and reduction with stannous chloride, and was used as reference compound.

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Abbreviations

GC-MS:

gas chromatography-mass spectrometry

HPLC:

high performance liquid chromatography

Me:

methyl ester

Me3 Si:

trimethylsilyl

PG:

prostaglandin

LTB4 :

leukotriene B4, 5S,12R-dihydroxy-6,8,10,14(Z,E,E,Z)-eicosatetraenoic acid

5S:

12S-diHETE, 5S,12S-dihydroxy-6,8,10,14(E,Z,E,Z)-eicosatetraenoic acid

12-HETE:

12S-hydroxy-5,8,10,14(Z,Z,E,Z)-eicosatetraenoic acid

HHT:

12S-hydroxy-5,8,10 (Z,E,E)-heptadecatrienoic acid

15S-HETE:

15S-hydroxy-5,8,11,13 (Z,Z,Z,E)-eicosatetraenoic acid

15S-HPETE:

15S-hydroperoxy-5,8,11,13(Z,Z,Z,E)-eicosatetraenoic acid

EDTA:

ethylene diamine tetraacetate

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Authors and Affiliations

  1. Laboratoire d'Endocrinologie Moléculaire, Le Centre Hospitalier de l'Université Laval, G1V 4G2, Quebec, Canada

    Pierre Borgeat, Serge Picard, Jean Drapeau & Pierre Vallerand

Authors
  1. Pierre Borgeat
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  2. Serge Picard
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  3. Jean Drapeau
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  4. Pierre Vallerand
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Additional information

See ref. 16 for a preliminary report.

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Borgeat, P., Picard, S., Drapeau, J. et al. Metabolism of arachidonic acid in leukocytes: Isolation of a 5,15-dihydroxy-eicosatetraenoic acid. Lipids 17, 676–681 (1982). https://doi.org/10.1007/BF02534650

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  • DOI: https://doi.org/10.1007/BF02534650

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