Literature DB >> 24780080

Inhibition of COX-2-mediated eicosanoid production plays a major role in the anti-inflammatory effects of the endocannabinoid N-docosahexaenoylethanolamine (DHEA) in macrophages.

Jocelijn Meijerink1, Mieke Poland, Michiel G J Balvers, Pierluigi Plastina, Carolien Lute, Jvalini Dwarkasing, Klaske van Norren, Renger F Witkamp.   

Abstract

BACKGROUND AND
PURPOSE: N-docosahexaenoylethanolamine (DHEA) is the ethanolamine conjugate of the long-chain polyunsaturated n-3 fatty acid docosahexaenoic (DHA; 22: 6n-3). Its concentration in animal tissues and human plasma increases when diets rich in fish or krill oil are consumed. DHEA displays anti-inflammatory properties in vitro and was found to be released during an inflammatory response in mice. Here, we further examine possible targets involved in the immune-modulating effects of DHEA. EXPERIMENTAL APPROACH: Antagonists for cannabinoid (CB)1 and CB2 receptors and PPARγ were used to explore effects of DHEA on NO release by LPS-stimulated RAW264.7 cells. The possible involvement of CB2 receptors was studied by comparing effects in LPS-stimulated peritoneal macrophages obtained from CB2 (-/-) and CB2 (+/+) mice. Effects on NF-κB activation were determined using a reporter cell line. To study DHEA effects on COX-2 and lipoxygenase activity, 21 different eicosanoids produced by LPS-stimulated RAW264.7 cells were quantified by LC-MS/MS. Finally, effects on mRNA expression profiles were analysed using gene arrays followed by Ingenuity(®) Pathways Analysis. KEY
RESULTS: CB1 and CB2 receptors or PPARs were not involved in the effects of DHEA on NO release. NF-κB and IFN-β, key elements of the myeloid differentiation primary response protein D88 (MyD88)-dependent and MyD88-independent pathways were not decreased. By contrast, DHEA significantly reduced levels of several COX-2-derived eicosanoids. Gene expression analysis provided support for an effect on COX-2-mediated pathways. CONCLUSIONS AND IMPLICATIONS: Our findings suggest that the anti-inflammatory effects of DHEA in macrophages predominantly take place via inhibition of eicosanoids produced through COX-2. LINKED ARTICLES: This article is part of a themed section on Cannabinoids 2013 published in volume 171 issue 6. To view the other articles in this section visit http://onlinelibrary.wiley.com/doi/10.1111/bph.2014.171.issue-6/issuetoc.
© 2014 The British Pharmacological Society.

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Year:  2014        PMID: 24780080      PMCID: PMC4280965          DOI: 10.1111/bph.12747

Source DB:  PubMed          Journal:  Br J Pharmacol        ISSN: 0007-1188            Impact factor:   8.739


  59 in total

Review 1.  The role of pattern-recognition receptors in innate immunity: update on Toll-like receptors.

Authors:  Taro Kawai; Shizuo Akira
Journal:  Nat Immunol       Date:  2010-04-20       Impact factor: 25.606

Review 2.  n-3 fatty acids in cardiovascular disease.

Authors:  Raffaele De Caterina
Journal:  N Engl J Med       Date:  2011-06-23       Impact factor: 91.245

3.  Biosynthesis and inactivation of N-arachidonoylethanolamine (anandamide) and N-docosahexaenoylethanolamine in bovine retina.

Authors:  T Bisogno; I Delton-Vandenbroucke; A Milone; M Lagarde; V Di Marzo
Journal:  Arch Biochem Biophys       Date:  1999-10-15       Impact factor: 4.013

4.  Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.

Authors:  T Sheskin; L Hanus; J Slager; Z Vogel; R Mechoulam
Journal:  J Med Chem       Date:  1997-02-28       Impact factor: 7.446

5.  Dietary docosahexaenoic acid supplementation alters select physiological endocannabinoid-system metabolites in brain and plasma.

Authors:  Jodianne T Wood; John S Williams; Lakshmipathi Pandarinathan; David R Janero; Carol J Lammi-Keefe; Alexandros Makriyannis
Journal:  J Lipid Res       Date:  2010-01-13       Impact factor: 5.922

6.  Postprandial dietary lipid-specific effects on human peripheral blood mononuclear cell gene expression profiles.

Authors:  Mark Bouwens; Mechteld Grootte Bromhaar; Jenny Jansen; Michael Müller; Lydia A Afman
Journal:  Am J Clin Nutr       Date:  2009-11-18       Impact factor: 7.045

Review 7.  The peripheral cannabinoid receptor knockout mice: an update.

Authors:  N E Buckley
Journal:  Br J Pharmacol       Date:  2007-10-29       Impact factor: 8.739

8.  The Concise Guide to PHARMACOLOGY 2013/14: enzymes.

Authors:  Stephen P H Alexander; Helen E Benson; Elena Faccenda; Adam J Pawson; Joanna L Sharman; Michael Spedding; John A Peters; Anthony J Harmar
Journal:  Br J Pharmacol       Date:  2013-12       Impact factor: 8.739

9.  The Concise Guide to PHARMACOLOGY 2013/14: ion channels.

Authors:  Stephen P H Alexander; Helen E Benson; Elena Faccenda; Adam J Pawson; Joanna L Sharman; William A Catterall; Michael Spedding; John A Peters; Anthony J Harmar
Journal:  Br J Pharmacol       Date:  2013-12       Impact factor: 8.739

10.  Inducible nitric oxide synthase induction underlies lipid-induced hepatic insulin resistance in mice: potential role of tyrosine nitration of insulin signaling proteins.

Authors:  Alexandre Charbonneau; André Marette
Journal:  Diabetes       Date:  2010-01-26       Impact factor: 9.461

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  14 in total

1.  Anti-inflammatory ω-3 endocannabinoid epoxides.

Authors:  Daniel R McDougle; Josephine E Watson; Amr A Abdeen; Reheman Adili; Megan P Caputo; John E Krapf; Rodney W Johnson; Kristopher A Kilian; Michael Holinstat; Aditi Das
Journal:  Proc Natl Acad Sci U S A       Date:  2017-07-07       Impact factor: 11.205

2.  Effects of Cannabidiol Chewing Gum on Perceived Pain and Well-Being of Irritable Bowel Syndrome Patients: A Placebo-Controlled Crossover Exploratory Intervention Study with Symptom-Driven Dosing.

Authors:  Anne-Claire B van Orten-Luiten; Nicole M de Roos; Soumia Majait; Ben J M Witteman; Renger F Witkamp
Journal:  Cannabis Cannabinoid Res       Date:  2021-02-11

3.  Docosahexaenoic acid-containing choline phospholipid modulates LPS-induced neuroinflammation in vivo and in microglia in vitro.

Authors:  Célia Fourrier; Julie Remus-Borel; Andrew D Greenhalgh; Michel Guichardant; Nathalie Bernoud-Hubac; Michel Lagarde; Corinne Joffre; Sophie Layé
Journal:  J Neuroinflammation       Date:  2017-08-24       Impact factor: 8.322

4.  The anti-inflammatory compound palmitoylethanolamide inhibits prostaglandin and hydroxyeicosatetraenoic acid production by a macrophage cell line.

Authors:  Linda Gabrielsson; Sandra Gouveia-Figueira; Jenny Häggström; Mireille Alhouayek; Christopher J Fowler
Journal:  Pharmacol Res Perspect       Date:  2017-02-27

5.  In Vitro Anti-Inflammatory and Radical Scavenging Properties of Chinotto (Citrus myrtifolia Raf.) Essential Oils.

Authors:  Pierluigi Plastina; Astari Apriantini; Jocelijn Meijerink; Renger Witkamp; Bartolo Gabriele; Alessia Fazio
Journal:  Nutrients       Date:  2018-06-18       Impact factor: 5.717

6.  Plasma fatty acid ethanolamides are associated with postprandial triglycerides, ApoCIII, and ApoE in humans consuming a high-fructose corn syrup-sweetened beverage.

Authors:  Candice Allister Price; Donovan A Argueta; Valentina Medici; Andrew A Bremer; Vivien Lee; Marinelle V Nunez; Guoxia X Chen; Nancy L Keim; Peter J Havel; Kimber L Stanhope; Nicholas V DiPatrizio
Journal:  Am J Physiol Endocrinol Metab       Date:  2018-04-10       Impact factor: 4.310

7.  Transcriptome Profiling and Molecular Pathway Analysis of Genes in Association with Salinity Adaptation in Nile Tilapia Oreochromis niloticus.

Authors:  Zhixin Xu; Lei Gan; Tongyu Li; Chang Xu; Ke Chen; Xiaodan Wang; Jian G Qin; Liqiao Chen; Erchao Li
Journal:  PLoS One       Date:  2015-08-25       Impact factor: 3.240

8.  Effects and mechanisms of docosahexaenoic acid on the generation of angiopoietin-2 by rat brain microvascular endothelial cells under an oxygen- and glucose-deprivation environment.

Authors:  Xiaobo Chen; Qiang Wang; Leyun Zhan; Aihua Shu
Journal:  Springerplus       Date:  2016-09-09

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

Authors:  Giuseppina Augimeri; Pierluigi Plastina; Giulia Gionfriddo; Daniela Rovito; Cinzia Giordano; Alessia Fazio; Ines Barone; Stefania Catalano; Sebastiano Andò; Daniela Bonofiglio; Jocelijn Meijerink; Renger Witkamp
Journal:  Nutrients       Date:  2019-09-18       Impact factor: 5.717

Review 10.  n-3 Polyunsaturated Fatty Acid Amides: New Avenues in the Prevention and Treatment of Breast Cancer.

Authors:  Cinzia Giordano; Pierluigi Plastina; Ines Barone; Stefania Catalano; Daniela Bonofiglio
Journal:  Int J Mol Sci       Date:  2020-03-26       Impact factor: 5.923

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