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. 2017 Feb 24;409(11):2967–2980. doi: 10.1007/s00216-017-0243-8

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© The Author(s) 2017

Open Access This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.

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Fig. 1 — Scheme representing the oxylipins (a), and the endocannabinoids, N-acylethanolamines, and fatty acid glycerol esters (b) that were analyzed (in filled squares), with their enzymatic pathways. Detected metabolites in lung lavage fluids are highlighted in bold. Abbreviations: COX—cyclooxygenase, LOX—lipoxygenase, CYP—cytochrome P450, FAAH—fatty acid amide hydrolase, MAGL—monoacylglycerol lipase. Compounds from the COX pathway included prostaglandins (PGD₂, PGE₂, PGF_2α, and 6-ketoPGF_1α) and thromboxane (TXB₂). The LOX pathway metabolites included hydroxyeicosatetraenoic acids (HETEs), hydroxyeicosapentaenoic acids (HEPEs), leukotrienes (LTB₄), oxoeicosatetraenoic acids (oxo-ETEs), hydroxyeicosatrienoic acids (HETrEs), oxooctadecadienoic acid (oxo-ODEs), hydroxyoctadecadienoic acids (HODEs), and trihydroxyoctadecenoic acids (TriHOMEs). The CYP pathway included epoxyeicosatrienoic acids (EETs), epoxyoctadecenoic acids (EpOMEs), dihydroxyoctadecenoic acids (DiHOMEs), and dihydroxyeicosatrienoic acids (DHETs). Endocannabinoids, N-acylethanolamines, and fatty acid glycerol esters included the following: 2-linoleoylglycerol (2-LG), 2-arachidonoylglycerol (2-AG), N-arachidonylglycine (NAGly), stearoyl ethanolamide (SEA), docosatetraenyl ethanolamide (DEA), palmitoleoyl ethanolamide (POEA), palmitoyl ethanolamide (PEA), docosahexaenoyl ethanolamide (DHEA), eicosapentaenoyl ethanolamide (EPEA), oleoyl ethanolamide (OEA), linoleoyl ethanolamide (LEA), arachidonoyl ethanolamide (AEA), prostaglandin F_2α ethanolamide (PGF _2α -EA), and prostaglandin E₂ ethanolamide (PGE ₂ -EA)