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Open AccessArticle

N-Eicosapentaenoyl Dopamine, A Conjugate of Dopamine and Eicosapentaenoic Acid (EPA), Exerts Anti-inflammatory Properties in Mouse and Human Macrophages

1
Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036 Arcavacata di Rende (CS), Italy
2
Division of Human Nutrition and Health, Wageningen University, 6700 AA Wageningen, The Netherlands
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Present address: Department of Functional Genomics and Cancer, Institut de Génétique et de Biologie Moléculaire et Cellulaire, 67404 Illkirch-Graffenstaden, France.
Nutrients 2019, 11(9), 2247; https://doi.org/10.3390/nu11092247
Received: 23 July 2019 / Revised: 4 September 2019 / Accepted: 16 September 2019 / Published: 18 September 2019
(This article belongs to the Special Issue Dietary Lipids and Human Health)
A large body of evidence suggests that dietary n-3 polyunsaturated fatty acids (PUFAs), including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), contribute to a reduced inflammatory tone thereby lowering the risk for several chronic and degenerative diseases. Different mechanisms have been proposed to explain these anti-inflammatory effects, including those involving endocannabinoids and endocannabinoid-like molecules. In this context, fatty acid amides (FAAs), conjugates of fatty acids with amines or amino acids, are an emerging class of compounds. Dopamine conjugates of DHA (N-docosahexaenoyl dopamine, DHDA) and EPA (N-eicosapentaenoyl dopamine, EPDA) have previously been shown to induce autophagy, apoptosis, and cell death in different tumor lines. Additionally, DHDA has displayed anti-inflammatory properties in vitro. Here, we tested the immune-modulatory properties of EPDA in mouse RAW 264.7 and human THP-1 macrophages stimulated with lipopolysaccharide (LPS). EPDA suppressed the production of monocyte chemoattractant protein-1 (MCP-1), and interleukin-6 (IL-6) in both cell lines, and nitric oxide (NO), and macrophage-inflammatory protein-3α (MIP3A) in RAW 264.7 macrophages. At a transcriptional level, EPDA attenuated cyclooxygenase-2 (COX-2) expression in both cell lines and that of MCP-1, IL-6, and interleukin-1β (IL-1β) in THP-1 macrophages. Although further research is needed to reveal whether EPDA is an endogenous metabolite, our data suggest that this EPA-derived conjugate possesses interesting immune-modulating properties. View Full-Text
Keywords: cyclooxygenase-2; cytokines; endocannabinoid; inflammation; N-acyl dopamine; N-eicosapentaenoyl dopamine; polyunsaturated fatty acids (PUFAs) cyclooxygenase-2; cytokines; endocannabinoid; inflammation; N-acyl dopamine; N-eicosapentaenoyl dopamine; polyunsaturated fatty acids (PUFAs)
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Augimeri, G.; Plastina, P.; Gionfriddo, G.; Rovito, D.; Giordano, C.; Fazio, A.; Barone, I.; Catalano, S.; Andò, S.; Bonofiglio, D.; Meijerink, J.; Witkamp, R. N-Eicosapentaenoyl Dopamine, A Conjugate of Dopamine and Eicosapentaenoic Acid (EPA), Exerts Anti-inflammatory Properties in Mouse and Human Macrophages. Nutrients 2019, 11, 2247.

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