ArticleThe Journal of biological chemistry2008
Identification of novel endogenous cytochrome p450 arachidonate metabolites with high affinity for cannabinoid receptors.
Article in The Journal of biological chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 39 papers.
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Who cites it
39 citing papers in PubMed, 78 citations in OpenAlex.
- Novel Tetraolefinic Chain Phenyl Substituted Endocannabinoid Probes.Journal of medicinal chemistry · 2025Article
- The Hunt for the Putative Epoxyeicosatrienoic Acid Receptor.ACS chemical biology · 2025Review
- The gut microbiome in patients with Cushing's disease affects depression- and anxiety-like behavior in mice.Microbiome · 2024Article
- Cannabinoid receptor type 1 activation causes a water diuresis by inducing an acute central diabetes insipidus in mice.American journal of physiology. Renal physiology · 2024Article
- Endocannabinoid signaling pathways: beyond CB1R and CB2R.Journal of cell communication and signaling · 2021Review
- Cannabidiol and Neurodevelopmental Disorders in Children.Frontiers in psychiatry · 2021Review
- Molecular Mechanism and Cannabinoid Pharmacology.Handbook of experimental pharmacology · 2020Article
- The Interplay between the Endocannabinoid System, Epilepsy and Cannabinoids.International journal of molecular sciences · 2019Review
- Endocannabinoid Virodhamine Is an Endogenous Inhibitor of Human Cardiovascular CYP2J2 Epoxygenase.Biochemistry · 2018Article
- The arachidonic acid monooxygenase: from biochemical curiosity to physiological/pathophysiological significance.Journal of lipid research · 2018Article
- Anti-inflammatory ω-3 endocannabinoid epoxides.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- Epoxyeicosatrienoic Acids and 20-Hydroxyeicosatetraenoic Acid on Endothelial and Vascular Function.Advances in pharmacology (San Diego, Calif.) · 2016Review
- Cytochrome P450 and Lipoxygenase Metabolites on Renal Function.Comprehensive Physiology · 2015Review
- Endocannabinoid Signaling in Autism.Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics · 2015Review
- Arachidonic acid monooxygenase: Genetic and biochemical approaches to physiological/pathophysiological relevance.Prostaglandins & other lipid mediators · 2015Review
- Peripheral FAAH and soluble epoxide hydrolase inhibitors are synergistically antinociceptive.Pharmacological research · 2015Article
- Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism.Biochimica et biophysica acta · 2015Review
- Endocannabinoids anandamide and 2-arachidonoylglycerol are substrates for human CYP2J2 epoxygenase.The Journal of pharmacology and experimental therapeutics · 2014Article
- Parsing the players: 2-arachidonoylglycerol synthesis and degradation in the CNS.British journal of pharmacology · 2014Review
- Multiple functions of endocannabinoid signaling in the brain.Annual review of neuroscience · 2012Review
Corrections and comments
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Authors and funding
9 authors at 3 institutions in 1 country.
Funding
Abstract
Arachidonic acid is an essential constituent of cell membranes that is esterified to the sn-2-position of glycerophospholipids and is released from selected lipid pools by phospholipase cleavage. The released arachidonic acid can be metabolized by three enzymatic pathways: the cyclooxygenase pathway forming prostaglandins and thromboxanes, the lipoxygenase pathway generating leukotrienes and lipoxins, and the cytochrome P450 (cP450) pathway producing epoxyeicosatrienoic acids and hydroxyeicosatetraenoic acids. The present study describes a novel group of cP450 epoxygenase-dependent metabolites of arachidonic acid, termed 2-epoxyeicosatrienoylglycerols (2-EG), including two regioisomers, 2-(11,12-epoxyeicosatrienoyl)glycerol (2-11,12-EG) and 2-(14,15-epoxyeicosatrienoyl)glycerol (2-14,15-EG), which are both produced in the kidney and spleen, whereas 2-11,12-EG is also detected in the brain. Both 2-11,12-EG and 2-14,15-EG activated the two cannabinoid (CB) receptor subtypes, CB1 and CB2, with high affinity and elicited biological responses in cultured cells expressing CB receptors and in intact animals. In contrast, the parental arachidonic acid and epoxyeicosatrienoic acids failed to activate CB1 or CB2 receptors. Thus, these cP450 epoxygenase-dependent metabolites are a novel class of endogenously produced, biologically active lipid mediators with the characteristics of endocannabinoids. This is the first evidence of a cytochrome P450-dependent arachidonate metabolite that can activate G-protein-coupled cell membrane receptors and suggests a functional link between the cytochrome P450 enzyme system and the endocannabinoid system.
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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.