Novel Anti-inflammatory and Vasodilatory ω-3 Endocannabinoid Epoxide Regioisomers

Lauren N. Carnevale, Aditi Das

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

Accumulating evidence suggests that diets rich in ω-3 polyunsaturated fatty acids (PUFAs) offer protection against vascular inflammation, neuroinflammation, hypertension, and thrombosis. Recently, biochemical studies have demonstrated that these benefits are partially mediated by their conversion to ω-3 endocannabinoid epoxide metabolites. These lipid metabolites originate from the epoxidation of ω-3 endocannabinoids, docosahexanoyl ethanolamide (DHEA) and eicosapentaenoyl ethanolamide (EPEA) by cytochrome P450 (CYP) epoxygenases to form epoxydocosapentaenoic acid-ethanolamides (EDP-EAs) and epoxyeicosatetraenoic acid-ethanolamides (EEQ-EAs), respectively. The EDP-EAs and EEQ-EAs are endogenously produced in rat brain and peripheral organs. Additionally, EDP-EAs and EEQ-EAs dose-dependently decrease pro-inflammatory IL-6 cytokine and increased anti-inflammatory IL-10 cytokine. Furthermore, the EEQ-EAs and EDP-EAs attenuate angiogenesis and cell migration in cancer cells, induce vasodilation in bovine coronary arteries, and reciprocally regulate platelet aggregation in washed human platelets. Taken together, the ω-3 endocannabinoid epoxides represent a new class of dual acting molecules that display unique pharmacological properties.

Original languageEnglish (US)
Title of host publicationAdvances in Experimental Medicine and Biology
PublisherSpringer New York LLC
Pages219-232
Number of pages14
DOIs
StatePublished - Jan 1 2019

Publication series

NameAdvances in Experimental Medicine and Biology
Volume1161
ISSN (Print)0065-2598
ISSN (Electronic)2214-8019

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Keywords

  • Cannabinoid receptors 1 and 2
  • Cytochrome p450
  • Endocannabinoid
  • Epoxyeicosatrienoic acids
  • Epoxygenase
  • Neuroinflammation
  • Omega-3 fatty acids

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

Carnevale, L. N., & Das, A. (2019). Novel Anti-inflammatory and Vasodilatory ω-3 Endocannabinoid Epoxide Regioisomers. In Advances in Experimental Medicine and Biology (pp. 219-232). (Advances in Experimental Medicine and Biology; Vol. 1161). Springer New York LLC. https://doi.org/10.1007/978-3-030-21735-8_17