Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S]
Beneficial physiological effects of long-chain n-3 polyunsaturated fatty acids are widely accepted but the mechanism(s) by which these fatty acids act remains unclear. Herein, we report the presence, distribution, and regulation of the levels of n-3 epoxy-fatty acids by soluble epoxide hydrolase (sE...
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doaj-0cc550e168cb4fa5b115950cc1c7a34e2021-04-28T05:57:33ZengElsevierJournal of Lipid Research0022-22752010-12-01511234813490Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S]Christophe Morisseau0Bora Inceoglu1Kara Schmelzer2Hsing-Ju Tsai3Steven L. Jinks4Christine M. Hegedus5Bruce D. Hammock6Department of Entomology and Cancer Center, and Anesthesiology and Pain Medicine, Davis, CA 95616Department of Entomology and Cancer Center, and Anesthesiology and Pain Medicine, Davis, CA 95616Department of Entomology and Cancer Center, and Anesthesiology and Pain Medicine, Davis, CA 95616Department of Entomology and Cancer Center, and Anesthesiology and Pain Medicine, Davis, CA 95616School of Medicine, University of California, Davis, CA 95616Department of Entomology and Cancer Center, and Anesthesiology and Pain Medicine, Davis, CA 95616To whom correspondence should be addressed. bdhammock@ucdavis.edu; Department of Entomology and Cancer Center, and Anesthesiology and Pain Medicine, Davis, CA 95616Beneficial physiological effects of long-chain n-3 polyunsaturated fatty acids are widely accepted but the mechanism(s) by which these fatty acids act remains unclear. Herein, we report the presence, distribution, and regulation of the levels of n-3 epoxy-fatty acids by soluble epoxide hydrolase (sEH) and a direct antinociceptive role of n-3 epoxy-fatty acids, specifically those originating from docosahexaenoic acid (DHA). The monoepoxides of the C18:1 to C22:6 fatty acids in both the n-6 and n-3 series were prepared and the individual regioisomers purified. The kinetic constants of the hydrolysis of the pure regioisomers by sEH were measured. Surprisingly, the best substrates are the mid-chain DHA epoxides. We also demonstrate that the DHA epoxides are present in considerable amounts in the rat central nervous system. Furthermore, using an animal model of pain associated with inflammation, we show that DHA epoxides, but neither the parent fatty acid nor the corresponding diols, selectively modulate nociceptive pathophysiology. Our findings support an important function of epoxy-fatty acids in the n-3 series in modulating nociceptive signaling. Consequently, the DHA and eicosapentaenoic acid epoxides may be responsible for some of the beneficial effects associated with dietary n-3 fatty acid intake.http://www.sciencedirect.com/science/article/pii/S0022227520313596soluble epoxide hydrolasecentral nervous systempain |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Christophe Morisseau Bora Inceoglu Kara Schmelzer Hsing-Ju Tsai Steven L. Jinks Christine M. Hegedus Bruce D. Hammock |
spellingShingle |
Christophe Morisseau Bora Inceoglu Kara Schmelzer Hsing-Ju Tsai Steven L. Jinks Christine M. Hegedus Bruce D. Hammock Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S] Journal of Lipid Research soluble epoxide hydrolase central nervous system pain |
author_facet |
Christophe Morisseau Bora Inceoglu Kara Schmelzer Hsing-Ju Tsai Steven L. Jinks Christine M. Hegedus Bruce D. Hammock |
author_sort |
Christophe Morisseau |
title |
Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S] |
title_short |
Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S] |
title_full |
Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S] |
title_fullStr |
Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S] |
title_full_unstemmed |
Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[S] |
title_sort |
naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids[s] |
publisher |
Elsevier |
series |
Journal of Lipid Research |
issn |
0022-2275 |
publishDate |
2010-12-01 |
description |
Beneficial physiological effects of long-chain n-3 polyunsaturated fatty acids are widely accepted but the mechanism(s) by which these fatty acids act remains unclear. Herein, we report the presence, distribution, and regulation of the levels of n-3 epoxy-fatty acids by soluble epoxide hydrolase (sEH) and a direct antinociceptive role of n-3 epoxy-fatty acids, specifically those originating from docosahexaenoic acid (DHA). The monoepoxides of the C18:1 to C22:6 fatty acids in both the n-6 and n-3 series were prepared and the individual regioisomers purified. The kinetic constants of the hydrolysis of the pure regioisomers by sEH were measured. Surprisingly, the best substrates are the mid-chain DHA epoxides. We also demonstrate that the DHA epoxides are present in considerable amounts in the rat central nervous system. Furthermore, using an animal model of pain associated with inflammation, we show that DHA epoxides, but neither the parent fatty acid nor the corresponding diols, selectively modulate nociceptive pathophysiology. Our findings support an important function of epoxy-fatty acids in the n-3 series in modulating nociceptive signaling. Consequently, the DHA and eicosapentaenoic acid epoxides may be responsible for some of the beneficial effects associated with dietary n-3 fatty acid intake. |
topic |
soluble epoxide hydrolase central nervous system pain |
url |
http://www.sciencedirect.com/science/article/pii/S0022227520313596 |
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