Cited by 393Cannabis and Cannabinoid ResearchInflammatory mediators and NSAID effectsEicosanoids and Hypertension Pharmacology

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Oxygenation of the Endocannabinoid, 2-Arachidonylglycerol, to Glyceryl Prostaglandins by Cyclooxygenase-2

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Kozak, Kevin R., Rowlinson, Scott W., Marnett, Lawrence J.·2000·Journal of Biological Chemistry

DOI 10.1074/jbc.m007088200

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Abstract

Cyclooxygenases (COX) play an important role in lipid signaling by oxygenating arachidonic acid to endoperoxide precursors of prostaglandins and thromboxane. Two cyclooxygenases exist which differ in tissue distribution and regulation but otherwise carry out identical chemical functions. The neutral arachidonate derivative, 2-arachidonylglycerol (2-AG), is one of two described endocannabinoids and appears to be a ligand for both the central (CB1) and peripheral (CB2) cannabinoid receptors. Here we report that 2-AG is a substrate for COX-2 and that it is metabolized as effectively as arachidonic acid. COX-2-mediated 2-AG oxygenation provides the novel lipid, prostaglandin H(2) glycerol ester (PGH(2)-G), in vitro and in cultured macrophages. PGH(2)-G produced by macrophages is a substrate for cellular PGD synthase, affording PGD(2)-G. Pharmacological studies reveal that macrophage production of PGD(2)-G from endogenous sources of 2-AG is calcium-dependent and mediated by diacylglycerol lipase and COX-2. These results identify a distinct function for COX-2 in endocannabinoid metabolism and in the generation of a new family of prostaglandins derived from diacylglycerol and 2-AG.

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Authors: Kozak, K. R., Rowlinson, S. W., & Marnett, L. J.
Affiliations: Vanderbilt University (US)
Corresponding author: Marnett, Lawrence J.
ORCID: Kozak, Kevin R.
Marnett, Lawrence J.
Venue: Journal of Biological Chemistry
Publisher: Elsevier BV
Published: 2000-10
Volume: 275
Issue: 43
Pages: 33744-33749
ISSN: 0021-9258 (ISSN-L)
DOI: 10.1074/jbc.m007088200
OpenAlex: W2086458197
Cited by: 390
References: 44
Citations by year: 2026: 2 · 2025: 5 · 2024: 4 · 2023: 8 · 2022: 18 · 2021: 13 · 2020: 16 · 2019: 14 · 2018: 10 · 2017: 17 · 2016: 18 · 2015: 15 · 2014: 16 · 2013: 19 · 2012: 18
FWCI: 8.84
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
creativecommons.org/licenses/by/4.0/ (vor, 7306 d)
Locations: Journal of Biological Chemistry (publishedVersion, cc-by)
PubMed (publishedVersion)
Funders: National Institutes of Health (5r35ca047479-10)
National Cancer Institute (CA-47479, CA 68484, P01CA068484)
National Institute of Environmental Health Sciences (ES00267)
Topics: Health Sciences › Medicine › Pharmacology (medical) › Cannabis and Cannabinoid Research
Health Sciences › Medicine › Pharmacology (medical) › Inflammatory mediators and NSAID effects
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
Keywords: 2-arachidonoylglycerol, endocannabinoids, cyclooxygenase-2, endocannabinoid metabolism, macrophages, diacylglycerol lipase, lipid signaling, arachidonic acid oxygenation
MeSH terms: Animals, Arachidonic Acids, Binding Sites, Cell Line, Glycerides, Humans, Isoenzymes, Male, Membrane Proteins, Prostaglandin-Endoperoxide Synthases, Sheep, Prostaglandin D2, Mice, Cyclooxygenase 1, Cyclooxygenase 2, Cannabinoid Receptor Modulators, Endocannabinoids

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Oxygenation of the Endocannabinoid, 2-Arachidonylglycerol, to Glyceryl Prostaglandins by Cyclooxygenase-2

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