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Anti-inflammatory ω-3 endocannabinoid epoxides.

Daniel R McDougle1,2, Josephine E Watson3, Amr A Abdeen4

  • 1Department of Comparative Biosciences, University of Illinois at Urbana-Champaign, Champaign, IL 61801.

Proceedings of the National Academy of Sciences of the United States of America
|July 9, 2017
PubMed
Summary

Researchers discovered novel ω-3 endocannabinoid epoxides, derived from docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). These compounds exhibit anti-inflammatory and anti-angiogenic effects, potentially aiding in treating neuroinflammatory diseases.

Keywords:
cytochrome P450endocannabinoidepoxyeicosatrienoic acidsepoxygenaseneuroinflammation

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Area of Science:

  • Lipidomics
  • Biochemistry
  • Pharmacology

Background:

  • Diets rich in ω-3 polyunsaturated fatty acids (PUFAs) offer anti-inflammatory benefits.
  • Bioactive metabolites derived from PUFAs contribute to these effects.
  • Endocannabinoid and cytochrome P450 (CYP) epoxygenase pathways are key metabolic routes.

Purpose of the Study:

  • To identify and characterize a new class of ω-3 PUFA-derived lipid metabolites.
  • To investigate the endogenous production and physiological roles of these novel compounds.
  • To explore their therapeutic potential for inflammatory and cerebrovascular diseases.

Main Methods:

  • Targeted lipidomics to detect ω-3 endocannabinoid epoxides (EEQ-EA and EDP-EA).
  • In vitro studies using activated BV-2 microglial cells and human CYP2J2 for metabolite production.
  • Neuroinflammation assays measuring IL-6 and IL-10 cytokine levels.
  • Functional assays assessing antiangiogenic, vasodilatory, and platelet aggregation effects.

Main Results:

  • Discovery of ω-3 endocannabinoid epoxides: epoxyeicosatetraenoic acid-ethanolamide (EEQ-EA) and epoxydocosapentaenoic acid-ethanolamide (EDP-EA).
  • These metabolites are endogenously present in rat tissues and produced via epoxygenation of ω-3 endocannabinoids (DHEA, EPEA).
  • EEQ-EA and EDP-EA demonstrated dose-dependent reduction of IL-6 and increase of IL-10, mediated partly by cannabinoid receptor-2.
  • They exhibited antiangiogenic effects, vasodilation, and reciprocal regulation of platelet aggregation.

Conclusions:

  • ω-3 endocannabinoid epoxides are a novel class of bioactive lipids with significant physiological functions.
  • Their effects are mediated through both endocannabinoid and epoxyeicosanoid signaling pathways.
  • These findings suggest potential therapeutic applications for neuroinflammatory and cerebrovascular conditions.