ArticleProceedings of the National Academy of Sciences of the United States of America2017
Anti-inflammatory ω-3 endocannabinoid epoxides.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. It is linked to trial NCT05386862 (Wayne Warrior CAnnabis Research and Education), which is not on this map. Cited by 98 papers, 1 of them a synthesis that pooled it.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Wayne Warrior CAnnabis Research and Education: Naturalistic Observation and Harm Reduction
Who cites it
98 citing papers in PubMed, 1 synthesis or guideline pooled it, 165 citations in OpenAlex.
- A large-scale genome-wide association study meta-analysis of cannabis use disorder.The lancet. Psychiatry · 2020Pooled it
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- Hemodialysis and erythrocyte epoxy fatty acids.Physiological reports · 2020Trial
- Combination of arginine, glutamine, and omega-3 fatty acid supplements for perioperative enteral nutrition in surgical patients with gastric adenocarcinoma or gastrointestinal stromal tumor (GIST): A prospective, randomized, double-blind study.Journal of postgraduate medicineTrial
- Regioselective epoxidation of a polyunsaturated fatty acid by a vanadyl complex with redox-active ligands.Chemical communications (Cambridge, England) · 2026Article
- Adolescent Dietary Supplementation of Omega-3 Polyunsaturated Fatty Acids Alleviates PTSD-Like Fear Memory and Affective Dysregulation in Rats.Smart medicine · 2026Article
- DICER-driven regulation of lipid metabolism and macrophage-adipocyte crosstalk in partial lipodystrophy.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2026Article
- Polynitrogen-containing compounds as multi-target sEH/FAAH inhibitors: Structure-activity relationship and pharmacological studies.Bioorganic & medicinal chemistry · 2026Article
- Altered Plasma Endocannabinoids and Oxylipins in Adolescents with Major Depressive Disorders: A Case-Control Study.Nutrients · 2026Article
- Integrated multi-omics reveals dysbiosis in hemodialysis patients: A multi-center study.PloS one · 2026Observational
- Omega-3 polyunsaturated fatty acids and mortality risk in depression: immune-inflammatory mediation in NHANES 1999-2018.Nutrition journal · 2025Article
- Adipogenicity-induced human mesenchymal stem cells treated with hemp seed oil stimulate brown-like adipocytes and decrease adipokine levels through the activation of cannabinoid receptor 2 (CB2).Journal of cannabis research · 2025Article
- C-reactive protein modulates lipid mediators in a pro-inflammatory direction.Journal of inflammation (London, England) · 2025Article
- The Hunt for the Putative Epoxyeicosatrienoic Acid Receptor.ACS chemical biology · 2025Review
- Persistent immune dysregulation and metabolic alterations following SARS-CoV-2 infection.medRxiv : the preprint server for health sciences · 2025Article
- Immune Dysregulation in Depression and Anxiety: A Review of the Immune Response in Disease and Treatment.Cells · 2025Review
- Brain Cytochrome P450: Navigating Neurological Health and Metabolic Regulation.Journal of xenobiotics · 2025Review
- Differences in total and differential white blood cell counts and in inflammatory parameters between psychiatric inpatients with and without recent consumption of cannabinoids, opioids, or cocaine: A retrospective single-center study.Brain, behavior, & immunity - health · 2024Article
- Relationship between sex, APOE genotype, endocannabinoids and cognitive change in older adults with metabolic syndrome during a 3-year Mediterranean diet intervention.Nutrition journal · 2024Article
- Comparative Study of Gas and Liquid Chromatography Methods for the Determination of Underivatised Neutral and Acidic Cannabinoids and Cholesterol.Molecules (Basel, Switzerland) · 2024Article
38 more citing papers are in PubMed but not listed here.
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
10 authors at 3 institutions in 1 country.
Funding
Abstract
Clinical studies suggest that diets rich in ω-3 polyunsaturated fatty acids (PUFAs) provide beneficial anti-inflammatory effects, in part through their conversion to bioactive metabolites. Here we report on the endogenous production of a previously unknown class of ω-3 PUFA-derived lipid metabolites that originate from the crosstalk between endocannabinoid and cytochrome P450 (CYP) epoxygenase metabolic pathways. The ω-3 endocannabinoid epoxides are derived from docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) to form epoxyeicosatetraenoic acid-ethanolamide (EEQ-EA) and epoxydocosapentaenoic acid-ethanolamide (EDP-EA), respectively. Both EEQ-EAs and EDP-EAs are endogenously present in rat brain and peripheral organs as determined via targeted lipidomics methods. These metabolites were directly produced by direct epoxygenation of the ω-3 endocannabinoids, docosahexanoyl ethanolamide (DHEA) and eicosapentaenoyl ethanolamide (EPEA) by activated BV-2 microglial cells, and by human CYP2J2. Neuroinflammation studies revealed that the terminal epoxides 17,18-EEQ-EA and 19,20-EDP-EA dose-dependently abated proinflammatory IL-6 cytokines while increasing anti-inflammatory IL-10 cytokines, in part through cannabinoid receptor-2 activation. Furthermore the ω-3 endocannabinoid epoxides 17,18-EEQ-EA and 19,20-EDP-EA exerted antiangiogenic effects in human microvascular endothelial cells (HMVEC) and vasodilatory actions on bovine coronary arteries and reciprocally regulated platelet aggregation in washed human platelets. Taken together, the ω-3 endocannabinoid epoxides' physiological effects are mediated through both endocannabinoid and epoxyeicosanoid signaling pathways. In summary, the ω-3 endocannabinoid epoxides are found at concentrations comparable to those of other endocannabinoids and are expected to play critical roles during inflammation in vivo; thus their identification may aid in the development of therapeutics for neuroinflammatory and cerebrovascular diseases.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.