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Hepoxilins: A review on their enzymatic formation, metabolism and chemical synthesis

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Lipids

Abstract

This article reviews published evidence describing the enzymatic and nonenzymatic formation and the routes of metabolism of the hepoxilins. Also treated are the major approaches used for the chemical synthesis of these compounds and for some of their analogs.

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Abbreviations

GST:

glutathione S-transferase

hepoxilin A3 :

HxA3, 8(S/R)-hydroxy-11(S),12(S)-trans-epoxy-eicosa-5Z,9E,14Z-trienoic acid

hepoxilin A3-C:

HxA3-C, 8(S/R),12(S)-dihydroxy-11(R)-glutathionyl-cicosa-5Z,9E,14Z-trienoic acid

hepoxilin B3 :

HxB3, 10(S/R)-hydroxy-11(S),12(S)-trans-epoxy-eicosa-5Z,8Z,14Z-trienoic acid

12-HETE:

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

12(S)-HPETE:

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

HPLC:

high-performance liquid chromatography

TCPO:

trichloropropene oxide

trioxilin A3 :

TrXA3, 8(S/R),11(R),12(S)-trihydroxy-eicosa-5Z,9E,14Z-trienoic acid

trioxilin B3 :

TrXB3, 10(S/R),11(R),12(R)-trihydroxy-eicosa-5Z,8Z-trienoic acid

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Authors and Affiliations

  1. Research Institute, Hospital for Sick Children, 555 University Ave., M5G 1X8, Toronto, Ontario, Canada

    C. R. Pace-Asciak, Denis Reynaud & Peter M. Demin

  2. Department of Pharmacology, Faculty of Medicine, University of Toronto, M5S 1A8, Toronto, Ontario, Canada

    C. R. Pace-Asciak

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  1. C. R. Pace-Asciak
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Pace-Asciak, C.R., Reynaud, D. & Demin, P.M. Hepoxilins: A review on their enzymatic formation, metabolism and chemical synthesis. Lipids 30, 107–114 (1995). https://doi.org/10.1007/BF02538262

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