Format

Send to

Choose Destination
Prostaglandins Other Lipid Mediat. 2019 Aug;143:106337. doi: 10.1016/j.prostaglandins.2019.106337. Epub 2019 May 11.

Emerging class of omega-3 fatty acid endocannabinoids & their derivatives.

Author information

1
Department of Biochemistry, Urbana, IL 61801, United States.
2
Division of Nutritional Sciences, Urbana, IL 61801, United States.
3
Department of Comparative Biosciences, Urbana, IL 61802, United States; Department of Biochemistry, Urbana, IL 61801, United States; Division of Nutritional Sciences, Urbana, IL 61801, United States; Beckman Institute for Advanced Science, Neuroscience Program, Center for Biophysics and Quantitative Biology, Department of Bioengineering, University of Illinois at Urbana-Champaign, Urbana, IL 61801, United States. Electronic address: aditidas@illinois.edu.

Abstract

Cannabinoid receptor activation is involved in homeostatic regulation of the body. These receptors are activated by cannabinoids, that include the active constituents of Cannabis sativa, as well as endocannabinoids (eCBs). The eCBs are endogenously synthesized from the omega-6 and omega-3 polyunsaturated fatty acids (PUFAs). The consumption of omega-3 fatty acids shifts the balance towards a higher proportion of omega-3 eCBs, whose physiological functions warrants further investigation. Herein, we review the discovery of omega-3 fatty acid derived eCBs that are generated from long chain omega-3 PUFAs - docosahexaenoyl ethanolamide (DHA-EA or synaptamide), docosahexanoyl-glycerol (DHG), eicosapentaenoyl ethanolamide (EPA-EA) and eicosapentanoylglycerol (EPG). Furthermore, we outline the lesser known omega-3 eCB-like molecules that arise from the conjugation of omega-3 fatty acids with neurotransmitters serotonin and dopamine - DHA-serotonin (DHA-5HT), DHA-dopamine (DHA-DA), EPA-serotonin (EPA-5HT) and EPA-dopamine (EPA-DA). Additionally, we describe the role of omega-3 eCBs and their derivatives in different disease states, such as pain, inflammation and cancer. Moreover, we detail the formation and potential physiological roles of the oxidative metabolites that arise from the metabolism of omega-3 eCBs by eicosanoid synthesizing enzymes - cyclooxygenase (COX), lipoxygenase (LOX) and cytochrome P450 epoxygenase (CYP450). In summary, we outline the novel findings regarding a growing class of signaling molecules that can control the physiological and pathophysiological processes in the body.

KEYWORDS:

Cancer; Endocannabinoids; Inflammation; Metabolism; Omega-3 fatty acids

Supplemental Content

Full text links

Icon for Elsevier Science Icon for PubMed Central
Loading ...
Support Center