Hydroxyphosphatidylethanolamines via lipoxygenase. J Biol Chem 2007;282: 20151–63. https://doi.org/10.1074/jbc.M611776200.

[81] Morgan C, Nigam Y. Naturally derived factors and their role in the promotion of angiogenesis for the healing of chronic wounds. Angiogenesis 2013;16:493–502. https://doi.org/10.1007/s10456-013-9341-1.

[82] Thomas CP, Morgan LT, Maskrey BH, Murphy RC, Kühn H, Hazen SL, et al. Phospholipid-esterified eicosanoids are generated in agonist-activated human platelets and enhance tissue factor-dependent thrombin generation. J Biol Chem 2010;285:6891–903. https://doi.org/10.1074/jbc.M109.078428.

[83] Aldrovandi M, Hammond VJ, Podmore H, Hornshaw M, Clark SR, Marnett LJ, et al. Human platelets generate phospholipid-esterified prostaglandins via cyclooxygenase-1 that are inhibited by low dose aspirin supplementation. J Lipid Res 2013;54:3085–97. https://doi.org/10.1194/jlr.M041533.

[84] Hutchins PM, Murphy RC. Cholesteryl ester acyl oxidation and remodeling in murine macrophages: formation of oxidized phosphatidylcholine. J Lipid Res 2012;53:1588–97. https://doi.org/10.1194/jlr.M026799.

[85] Liu X, Moon SH, Jenkins CM, Sims HF, Gross RW. Cyclooxygenase-2 mediated oxidation of 2-Arachidonoyl-Lysophospholipids identifies unknown lipid signaling pathways. Cell Chem Biol 2016;23:1217–27. https://doi.org/10.1016/j. chembiol.2016.08.009.

[86] Ha VT, Lainšček D, Gesslbauer B, Jarc-Jovićić E, Hyötyläinen T, Ilic N, et al. Synergy between 15-lipoxygenase and secreted PLA 2 promotes inflammation by formation of TLR4 agonists from extracellular vesicles. Proc Natl Acad Sci 2020; 117:25679–89. https://doi.org/10.1073/pnas.2005111117.

[87] Sagini K, Costanzi E, Emiliani C, Buratta S, Urbanelli L. Extracellular vesicles as conveyors of membrane-derived bioactive lipids in immune system. Int J Mol Sci 2018;19:1227. https://doi.org/10.3390/ijms19041227.

[88] Reinicke M, Shamkeeva S, Hell M, Isermann B, Ceglarek U, Heinemann ML. Targeted Lipidomics for characterization of PUFAs and eicosanoids in extracellular vesicles. Nutrients 2022;14:1319. https://doi.org/10.3390/ nu14071319.

[89] Quehenberger O, Dahlberg-Wright S, Jiang J, Armando AM, Dennis EA. Quantitative determination of esterified eicosanoids and related oxygenated metabolites after base hydrolysis. J Lipid Res 2018;59:2436–45. https://doi.org/ 10.1194/jlr.D089516.

[90] Hammond VJ, O'Donnell VB. Esterified eicosanoids: generation, characterization and function. Hamchem Biophys Acta (BBA) - Biomembran 2012;1818:2403–12. https://doi.org/10.1016/j.bbamem.2011.12.013.

[91] Annevelink CE, Walker RE, Shearer GC. Esterified Oxylipins: do they matter? Metabolites 2022;12:1007. https://doi.org/10.3390/metabo12111007.

[92] Ek-von Mentzer BA, Zhang F, Hamilton JA. Binding of 13-HODE and 15-HETE to phospholipid bilayers, albumin, and intracellular fatty acid binding proteins. J Biol Chem 2001;276:15575–80. https://doi.org/10.1074/jbc.M011623200.

[93] Maclouf J, Kindahl H, Granstrom A, Samuelsson B. Interactions of prostaglandin H2 and thromboxane A2 with human serum albumin. Eur J Biochem 1980;109: 561–6. https://doi.org/10.1111/j.1432-1033.1980.tb04828.x.

[94] Brock TG. Capturing proteins that bind polyunsaturated fatty acids: demonstration using arachidonic acid and eicosanoids. Lipids 2008;43:161–9. https://doi.org/10.1007/s11745-007-3136-3.

[95] Funk CD, FitzGerald GA. COX-2 inhibitors and cardiovascular risk. J Cardiovasc Pharmacol 2007;50:470–9. https://doi.org/10.1097/FJC.0b013e318157f72d.

[96] Record M, Carayon K, Poirot M, Silveste-Poirot S. Exosomes as new vesicular lipid transporters involved in cell–cell communication and various pathophysiologies. Biochim et Biophys Acta (BBA) - Mol Cell Biol Lipids 2014; 1841:108–20. https://doi.org/10.1016/j.bbalip.2013.10.004.

[97] Grapov D, Adams SH, Pedersen TL, Garvey WT, Newman JW. Type 2 diabetes associated changes in the plasma non-esterified fatty acids, Oxylipins and Endocannabinoids. PloS One 2012;7:e48852. https://doi.org/10.1371/journal. pone.0048852.

[98] Guyenet SJ, Carlson SE. Increase in adipose tissue linoleic acid of US adults in the last half century. Adv Nutr 2015;6:660–4. https://doi.org/10.3945/ an.115.009944.

[99] Hodson L, Skeaff CM, Fielding BA. Fatty acid composition of adipose tissue and blood in humans and its use as a biomarker of dietary intake. Prog Lipid Res 2008;47:348–80. https://doi.org/10.1016/j.plipres.2008.03.003.

[100] Gouveia-Figueira S, Späth J, Zivkovic AM, Nording ML. Profiling the Oxylipin and endocannabinoid metabolome by UPLC-ESI-MS/MS in human plasma to monitor postprandial inflammation. PloS One 2015;10:e0132042. https://doi.org/ 10.1371/journal.pone.0132042.

[101] Aukema HM, Ravandi A. Factors affecting variability in free oxylipins in mammalian tissues. Curr Opin Clin Nutr Metab Care 2023;26:91–8. https://doi.org/10.1097/MCO.0000000000000892.

[102] Gladine C, Ostermann AI, Newman JW, Schebb NH. MS-based targeted metabolomics of eicosanoids and other oxylipins: analytical and inter-individual variability. Free Radic Biol Med 2019;144:72–89. https://doi.org/10.1016/j. freeradbiomed.2019.05.012.

[103] Rund KM, Nolte F, Doricic J, Greite R, Schott S, Lichtinghagen R, et al. Clinical blood sampling for oxylipin analysis – effect of storage and pneumatic tube transport of blood on free and total oxylipin profile in human plasma and serum. Analyst 2020;145:2378–88. https://doi.org/10.1039/C9AN01880H.

[104] Mas E, Croft KD, Zahra P, Barden A, Mori TA. Resolvins D1, D2, and other mediators of self-limited resolution of inflammation in human blood following n-3 fatty acid supplementation. Clin Chem 2012;58:1476–84. https://doi.org/ 10.1373/clinchem.2012.190199.

[105] Matsunobu T, Okuno T, Yokoyama C, Yokomizo T. Thromboxane a synthase-independent production of 12-hydroxyheptadecatrienoic acid, a BLT2 ligand. J Lipid Res 2013;54:2979–87. https://doi.org/10.1194/jlr.M037754.

[106] Yeung J, Apopa PL, Vesci J, Kenyon V, Rai G, Jadhav A, et al. Protein kinase C regulation of 12-lipoxygenase-mediated human platelet activation. Mol Pharmacol 2012;81:420–30. https://doi.org/10.1124/mol.111.075630.

[107] Tuck MK, Chan DW, Chia D, Godwin AK, Grizziwe WE, Krueger KE, et al. Standard operating procedures for serum and plasma collection: early detection research network consensus statement standard operating procedure integration working group. J Proteome Res 2009;8:113–7. https://doi.org/10.1021/pr800545q.

[108] Mazaleuskaya LL, Salamatipour A, Sarantopoulou D, Weng L, FitzGerald GA, Blair IA, et al. Analysis of HETEs in human whole blood by chiral UHPLC-ECAPCI/HRMS. J Lipid Res 2018;59:564–75. https://doi.org/10.1194/jlr. D081414.

[109] Astarita G, Kendall AC, Dennis EA, Nicolaou A. Targeted lipidomic strategies for oxygenated metabolites of polyunsaturated fatty acids. Biochim et Biophys Acta (BBA) - Mol Cell Biol Lipids 2015;1851:456–68. https://doi.org/10.1016/j. bbalip.2014.11.012.

[110] Polinski KJ, Armstrong M, Manke J, Seifert J, Crume T, Yang F, et al. Collection and storage of human plasma for measurement of Oxylipins. Metabolites 2021;11: 137. https://doi.org/10.3390/metabo11030137.

[111] Goodfriend TL, Pedersen TL, Grekin RJ, Hammock BD, Ball DL, Vollmer A. Heparin, lipoproteins, and oxygenated fatty acids in blood: a cautionary note. Prostaglandins Leukot Essent Fatty Acids 2007;77:363–6. https://doi.org/ 10.1016/j.plefa.2007.10.012.

[112] Jonasdottir HS, Brouwers H, Toes REM, Ioan-Facsinia G, Aiera M. Effects of anticoagulants and storage conditions on clinical oxylipid in human plasma. Biochim et Biophys Acta (BBA) - Mol Cell Biol Lipids 2018;1863: 1511–22. https://doi.org/10.1016/j.bbalip.2018.10.003.

[113] Koch E, Mainka M, Dalle C, Ostermann AI, Rund KM, Kutzner L, et al. Stability of oxylipins during plasma generation and long-term storage. Talanta 2020;217: 121074. https://doi.org/10.1016/j.talanta.2020.121074.

[114] Barden AE, Mas E, Croft KD, Phillips M, Mori TA. Minimizing artifactual elevation of lipid peroxidation products (F2-isoprostanes) in plasma during collection and storage. Anal Biochem 2014;449:129–31. https://doi.org/10.1016/j. ab.2013.12.030.

[115] Schebb NH, Ostermann AI, Yang J, Hammock BD, Hahn A, Schuchardt JP. Comparison of the effects of long-chain omega-3 fatty acid supplementation on plasma levels of free and esterified oxylipins. Prostaglandins Other Lipid Mediat 2014;113–115:21–9. https://doi.org/10.1016/j.prostaglandins.2014.05.002.

[116] Massey KA, Nicolaou A. Lipidomics of oxidized polyunsaturated fatty acids. Free Radic Biol Med 2013;59:45–55. https://doi.org/10.1016/j. freeradbiomed.2012.08.565.

[117] Mainka M, Dalle C, Pétraé M, Dalloux-Chiocioli J, Kamptschulte N, Ostermann AI, et al. Harmonized procedures lead to comparable quantification of total oxylipins across laboratories. J Lipid Res 2020;61:4124–36. https://doi.org/ 10.1194/jlr.RA120000991.

[118] Ostermann AI, Koch E, Rund KM, Kutzner L, Mainka M, Schebb NH. Targeting esterified oxylipins by LC-MS - effect of sample preparation on oxylipin pattern. Prostaglandins Other Lipid Mediat 2020;146:106384. https://doi.org/10.1016/j. prostaglandins.2019.106384.

[119] Ostermann AI, Willenberg I, Schebb NH. Comparison of sample preparation methods for the quantitative analysis of eicosanoids and other oxylipins in plasma by means of LC-MS/MS. Anal Bioanal Chem 2015;407:1403–14. https://doi.org/ 10.1007/s00216-014-8377-4.

[120] Song J, Liu X, Rao TS, Chang L, Meehan MJ, Blevitt JM, et al. Phenotyping drug polypharmacology via eicosanoid profiling of blood. J Lipid Res 2015;56: 1492–500. https://doi.org/10.1194/jlr.M058677.

[121] Hennebelle M, Otoki Y, Yang J, Hammock BD, Levitt AJ, Taha AY, et al. Altered soluble epoxide hydrolase-derived oxylipins in patients with seasonal major depression: an exploratory study. Psychiatry Res 2017;252:94–101. https://doi. org/10.1016/j.psychres.2017.02.056.

[122] Mangelsen E, Rothe M, Schulz A, Kourpa A, Panáková D, Kreutz R, et al. Concerted EP2 and EP4 receptor signaling stimulates autocrine prostaglandin E2 activation in human podocytes. Cells 2020;9:1256. https://doi.org/10.3390/ cells9051256.

[123] Harris TR, Griffith JA, Clarke CEC, Garner KL, Bowdridge EC, DeVallance E, et al. Distinct profiles of oxylipid mediators in liver, lung, and placenta after maternal nano-TiO 2 nanoparticle inhalation exposure. Environ Sci: Adv 2023;2:740–8. https://doi.org/10.1039/D2VA00300G.

[124] Deems R, Buczynski MW, Bowers-Gentry R, Harkewicz R, Dennis EA. Detection and Quantitation of Eicosanoids via High Performance Liquid Chromatography- Electrospray Ionization-Mass Spectrometry. 2007. p. 59–82. https://doi.org/ 10.1016/S0076-6879(07)32003-X.

[125] Adigun OA, Pham TH, Grapov D, Nadeem M, Jewell LE, Cheema M, et al. Phyto- oxylipin mediated plant immune response to colonization and infection in the soybean-Phytophthora sojae pathosystem. Front Plant Sci 2023;14. https://doi. org/10.3389/fpls.2023.1141823.

[126] Quaranta A, Zöhrer B, Revol-Cavalier J, Benkestock K, Balas L, Oger C, et al. Development of a Chiral Supercritical Fluid Chromatography–Tandem Mass Spectrometry and Reversed-Phase Liquid Chromatography–Tandem Mass Spectrometry Platform for the Quantitative Metabolic Profiling of Octadecanoid Oxylipins. Anal Chem 2022;94:14618–26. https://doi.org/10.1021/acs. analchem.2c02601.
Hydroxyphosphatidylethanolamines via lipoxygenase. J Biol Chem 2007;282: 20151-63. https://doi.org/10.1074/jbc.M611776200.

[81] Morgan C, Nigam Y. Naturally derived factors and their role in the promotion of angiogenesis for the healing of chronic wounds. Angiogenesis 2013;16:493-502. https://doi.org/10.1007/s10456-013-9341-1.

[82] Thomas CP, Morgan LT, Maskrey BH, Murphy RC, Kühn H, Hazen SL, et al. Phospholipid-esterified eicosanoids are generated in agonist-activated human platelets and enhance tissue factor-dependent thrombin generation. J Biol Chem 2010;285:6891-903. https://doi.org/10.1074/jbc.M109.078428.

[83] Aldrovandi M, Hammond VJ, Podmore H, Hornshaw M, Clark SR, Marnett LJ, et al. Human platelets generate phospholipid-esterified prostaglandins via cyclooxygenase-1 that are inhibited by low dose aspirin supplementation. J Lipid Res 2013;54:3085-97. https://doi.org/10.1194/jlr.M041533.

[84] Hutchins PM, Murphy RC. Cholesteryl ester acyl oxidation and remodeling in murine macrophages: formation of oxidized phosphatidylcholine. J Lipid Res 2012;53:1588-97. https://doi.org/10.1194/jlr.M026799.

[85] Liu X, Moon SH, Jenkins CM, Sims HF, Gross RW. Cyclooxygenase-2 mediated oxidation of 2-Arachidonoyl-Lysophospholipids identifies unknown lipid signaling pathways. Cell Chem Biol 2016;23:1217-27. https://doi.org/10.1016/j.chembiol.2016.08.009.

[86] Ha VT, Lainšček D, Gesslbauer B, Jarc-Jovićić E, Hyötyläinen T, Ilic N, et al. Synergy between 15-lipoxygenase and secreted PLA 2 promotes inflammation by formation of TLR4 agonists from extracellular vesicles. Proc Natl Acad Sci 2020; 117:25679-89. https://doi.org/10.1073/pnas.2005111117.

[87] Sagini K, Costanzi E, Emiliani C, Buratta S, Urbanelli L. Extracellular vesicles as conveyors of membrane-derived bioactive lipids in immune system. Int J Mol Sci 2018;19:1227. https://doi.org/10.3390/ijms19041227.

[88] Reinicke M, Shamkeeva S, Hell M, Isermann B, Ceglarek U, Heinemann ML. Targeted Lipidomics for characterization of PUFAs and eicosanoids in extracellular vesicles. Nutrients 2022;14:1319. https://doi.org/10.3390/nu14071319.

[89] Quehenberger O, Dahlberg-Wright S, Jiang J, Armando AM, Dennis EA. Quantitative determination of esterified eicosanoids and related oxygenated metabolites after base hydrolysis. J Lipid Res 2018;59:2436-45. https://doi.org/10.1194/jlr.D089516.

[90] Hammond VJ, O'Donnell VB. Esterified eicosanoids: generation, characterization and function. Hamchim Biophys Acta (BBA) - Biomembran 2012;1818:2403-12. https://doi.org/10.1016/j.bbamem.2011.12.013.

[91] Annevelink CE, Walker RE, Shearer GC. Esterified Oxylipins: do they matter? Metabolites 2022;12:1007. https://doi.org/10.3390/metabo12111007.

[92] Ek-von Mentzer BA, Zhang F, Hamilton JA. Binding of 13-HODE and 15-HETE to phospholipid bilayers, albumin, and intracellular fatty acid binding proteins. J Biol Chem 2001;276:15575-80. https://doi.org/10.1074/jbc.M011623200.

[93] Maclouf J, Kindahl H, Granstrom A, Samuelsson B. Interactions of prostaglandin H2 and thromboxane A2 with human serum albumin. Eur J Biochem 1980;109: 561-6. https://doi.org/10.1111/j.1432-1033.1980.tb04828.x.

[94] Brock TG. Capturing proteins that bind polyunsaturated fatty acids: demonstration using arachidonic acid and eicosanoids. Lipids 2008;43:161-9. https://doi.org/10.1007/s11745-007-3136-3.

[95] Funk CD, FitzGerald GA. COX-2 inhibitors and cardiovascular risk. J Cardiovasc Pharmacol 2007;50:470-9. https://doi.org/10.1097/FJC.0b013e318157f72d.

[96] Record M, Carayon K, Poirot M, Silveste-Poirot S. Exosomes as new vesicular lipid transporters involved in cell-cell communication and various pathophysiologies. Biochim et Biophys Acta (BBA) - Mol Cell Biol Lipids 2014; 1841:108-20. https://doi.org/10.1016/j.bbalip.2013.10.004.

[97] Grapov D, Adams SH, Pedersen TL, Garvey WT, Newman JW. Type 2 diabetes associated changes in the plasma non-esterified fatty acids, Oxylipins and Endocannabinoids. PloS One 2012;7:e48852. https://doi.org/10.1371/journal.pone.0048852.

[98] Guyenet SJ, Carlson SE. Increase in adipose tissue linoleic acid of US adults in the last half century. Adv Nutr 2015;6:660-4. https://doi.org/10.3945/an.115.009944.

[99] Hodson L, Skeaff CM, Fielding BA. Fatty acid composition of adipose tissue and blood in humans and its use as a biomarker of dietary intake. Prog Lipid Res 2008;47:348-80. https://doi.org/10.1016/j.plipres.2008.03.003.

[100] Gouveia-Figueira S, Späth J, Zivkovic AM, Nording ML. Profiling the Oxylipin and endocannabinoid metabolome by UPLC-ESI-MS/MS in human plasma to monitor postprandial inflammation. PloS One 2015;10:e0132042. https://doi.org/10.1371/journal.pone.0132042.

[101] Aukema HM, Ravandi A. Factors affecting variability in free oxylipins in mammalian tissues. Curr Opin Clin Nutr Metab Care 2023;26:91-8. https://doi.org/10.1097/MCO.0000000000000892.

[102] Gladine C, Ostermann AI, Newman JW, Schebb NH. MS-based targeted metabolomics of eicosanoids and other oxylipins: analytical and inter-individual variability. Free Radic Biol Med 2019;144:72-89. https://doi.org/10.1016/j.freeradbiomed.2019.05.012.

[103] Rund KM, Nolte F, Doricic J, Greite R, Schott S, Lichtinghagen R, et al. Clinical blood sampling for oxylipin analysis – effect of storage and pneumatic tube transport of blood on free and total oxylipin profile in human plasma and serum. Analyst 2020;145:2378-88. https://doi.org/10.1039/C9AN01880H.

[104] Mas E, Croft KD, Zahra P, Barden A, Mori TA. Resolvins D1, D2, and other mediators of self-limited resolution of inflammation in human blood following n-3 fatty acid supplementation. Clin Chem 2012;58:1476-84. https://doi.org/10.1373/clinchem.2012.190199.

[105] Matsunobu T, Okuno T, Yokoyama C, Yokomizo T. Thromboxane a synthase-independent production of 12-hydroxyheptadecatrienoic acid, a BLT2 ligand. J Lipid Res 2013;54:2979-87. https://doi.org/10.1194/jlr.M037754.

[106] Yeung J, Apopa PL, Vesci J, Kenyon V, Rai G, Jadhav A, et al. Protein kinase C regulation of 12-lipoxygenase-mediated human platelet activation. Mol Pharmacol 2012;81:420-30. https://doi.org/10.1124/mol.111.075630.

[107] Tuck MK, Chan DW, Chia D, Godwin AK, Grizziwe WE, Krueger KE, et al. Standard operating procedures for serum and plasma collection: early detection research network consensus statement standard operating procedure integration working group. J Proteome Res 2009;8:113-7. https://doi.org/10.1021/pr800545q.

[108] Mazaleuskaya LL, Salamatipour A, Sarantopoulou D, Weng L, FitzGerald GA, Blair IA, et al. Analysis of HETEs in human whole blood by chiral UHPLC-ECAPCI/HRMS. J Lipid Res 2018;59:564-75. https://doi.org/10.1194/jlr.D081414.

[109] Astarita G, Kendall AC, Dennis EA, Nicolaou A. Targeted lipidomic strategies for oxygenated metabolites of polyunsaturated fatty acids. Biochim et Biophys Acta (BBA) - Mol Cell Biol Lipids 2015;1851:456-68. https://doi.org/10.1016/j.bbalip.2014.11.012.

[110] Polinski KJ, Armstrong M, Manke J, Seifert J, Crume T, Yang F, et al. Collection and storage of human plasma for measurement of Oxylipins. Metabolites 2021;11: 137. https://doi.org/10.3390/metabo11030137.

[111] Goodfriend TL, Pedersen TL, Grekin RJ, Hammock BD, Ball DL, Vollmer A. Heparin, lipoproteins, and oxygenated fatty acids in blood: a cautionary note. Prostaglandins Leukot Essent Fatty Acids 2007;77:363-6. https://doi.org/10.1016/j.plefa.2007.10.012.

[112] Jonasdottir HS, Brouwers H, Toes REM, Ioan-Facsinia G, Aiera M. Effects of anticoagulants and storage conditions on clinical oxylipid in human plasma. Biochim et Biophys Acta (BBA) - Mol Cell Biol Lipids 2018;1863: 1511-22. https://doi.org/10.1016/j.bbalip.2018.10.003.

[113] Koch E, Mainka M, Dalle C, Ostermann AI, Rund KM, Kutzner L, et al. Stability of oxylipins during plasma generation and long-term storage. Talanta 2020;217: 121074. https://doi.org/10.1016/j.talanta.2020.121074.

[114] Barden AE, Mas E, Croft KD, Phillips M, Mori TA. Minimizing artifactual elevation of lipid peroxidation products (F2-isoprostanes) in plasma during collection and storage. Anal Biochem 2014;449:129-31. https://doi.org/10.1016/j.ab.2013.12.030.

[115] Schebb NH, Ostermann AI, Yang J, Hammock BD, Hahn A, Schuchardt JP. Comparison of the effects of long-chain omega-3 fatty acid supplementation on plasma levels of free and esterified oxylipins. Prostaglandins Other Lipid Mediat 2014;113-115:21-9. https://doi.org/10.1016/j.prostaglandins.2014.05.002.

[116] Massey KA, Nicolaou A. Lipidomics of oxidized polyunsaturated fatty acids. Free Radic Biol Med 2013;59:45-55. https://doi.org/10.1016/j.freeradbiomed.2012.08.565.

[117] Mainka M, Dalle C, Pétraé M, Dalloux-Chiocioli J, Kampschulte N, Ostermann AI, et al. Harmonized procedures lead to comparable quantification of total oxylipins across laboratories. J Lipid Res 2020;61:4124-36. https://doi.org/10.1194/jlr.RA120000991.

[118] Ostermann AI, Koch E, Rund KM, Kutzner L, Mainka M, Schebb NH. Targeting esterified oxylipins by LC-MS - effect of sample preparation on oxylipin pattern. Prostaglandins Other Lipid Mediat 2020;146:106384. https://doi.org/10.1016/j.prostaglandins.2019.106384.

[119] Ostermann AI, Willenberg I, Schebb NH. Comparison of sample preparation methods for the quantitative analysis of eicosanoids and other oxylipins in plasma by means of LC-MS/MS. Anal Bioanal Chem 2015;407:1403-14. https://doi.org/10.1007/s00216-014-8377-4.

[120] Song J, Liu X, Rao TS, Chang L, Meehan MJ, Blevitt JM, et al. Phenotyping drug polypharmacology via eicosanoid profiling of blood. J Lipid Res 2015;56: 1492-500. https://doi.org/10.1194/jlr.M058677.

[121] Hennebelle M, Otoki Y, Yang J, Hammock BD, Levitt AJ, Taha AY, et al. Altered soluble epoxide hydrolase-derived oxylipins in patients with seasonal major depression: an exploratory study. Psychiatry Res 2017;252:94-101. https://doi.org/10.1016/j.psychres.2017.02.056.

[122] Mangelsen E, Rothe M, Schulz A, Kourpa A, Panáková D, Kreutz R, et al. Concerted EP2 and EP4 receptor signaling stimulates autocrine prostaglandin E2 activation in human podocytes. Cells 2020;9:1256. https://doi.org/10.3390/cells9051256.

[123] Harris TR, Griffith JA, Clarke CEC, Garner KL, Bowdridge EC, DeVallance E, et al. Distinct profiles of oxylipid mediators in liver, lung, and placenta after maternal nano-TiO 2 nanoparticle inhalation exposure. Environ Sci: Adv 2023;2:740-8. https://doi.org/10.1039/D2VA00300G.

[124] Deems R, Buczynski MW, Bowers-Gentry R, Harkewicz R, Dennis EA. Detection and Quantitation of Eicosanoids via High Performance Liquid Chromatography-Electrospray Ionization-Mass Spectrometry. 2007. p. 59-82. https://doi.org/10.1016/S0076-6879(07)32003-X.

[125] Adigun OA, Pham TH, Grapov D, Nadeem M, Jewell LE, Cheema M, et al. Phyto-oxylipin mediated plant immune response to colonization and infection in the soybean-Phytophthora sojae pathosystem. Front Plant Sci 2023;14. https://doi.org/10.3389/fpls.2023.1141823.

[126] Quaranta A, Zöhrer B, Revol-Cavalier J, Benkestock K, Balas L, Oger C, et al. Development of a Chiral Supercritical Fluid Chromatography-Tandem Mass Spectrometry and Reversed-Phase Liquid Chromatography-Tandem Mass Spectrometry Platform for the Quantitative Metabolic Profiling of Octadecanoid Oxylipins. Anal Chem 2022;94:14618-26. https://doi.org/10.1021/acs.analchem.2c02601.
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[128] Diskin C, Zotta A, Corcoran SE, Tyrrell VJ, Zaslona Z, O'Donnell VB, et al. 4-Octyl-Itaconate and dimethyl fumarate inhibit COX2 expression and prostaglandin production in macrophages. J Immunol 2021;207:2561-9. https://doi.org/10.4049/jimmunol.20100488.

[129] Diskin C, Corcoran SE, Tyrrell VJ, McGettrick AF, Zaslona Z, O'Donnell VB, et al. The trypanosome-derived metabolite Indole-3-pyruvate inhibits prostaglandin production in macrophages by targeting COX2. J Immunol 2021;207:2551-60. https://doi.org/10.4049/jimmunol.2100402.

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[131] Rund KM, Peng S, Greite R, Claaßen C, Nolte F, Oger C, et al. Dietary omega-3 PUFA improved tubular function after ischemia induced acute kidney injury in mice but did not attenuate impairment of renal function. Prostaglandins Other Lipid Mediat 2020;146:106386. https://doi.org/10.1016/j.prostaglandins.2019.106386.

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[138] Hasanally D, Chaudhary R, Ravandi A. Role of Phospholipases and Oxidized Phospholipids in Inflammation. Phospholipids in Health and Disease. New York, NY: Springer New York; 2014. p. 55-72. https://doi.org/10.1007/978-1-4939-0464-8_3.

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[146] Af Forselles KJ, Root J, Clarke T, Davey D, Aughton K, Dack K, et al. In vitro and in vivo characterization of PF-04418948, a novel, potent and selective prostaglandin EP2 receptor antagonist. Br J Pharmacol 2011;164:1847-56. https://doi.org/10.1111/j.1476-5381.2011.01495.x.

[147] Gray SJ, Heptinstall S. The effects of PGE2 and CL 115,347, an antihypertensive PGE2 analogue, on human blood platelet behaviour and vascular contractility. Eur J Pharmac 1985;114:129-37. https://doi.org/10.1016/0014-2999(85)90620-x.

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[152] Smith JP, Haddad EV, Downey JD, Breyer RM, Boutaud O. PGE2 decreases reactivity of human platelets by activating EP2 and EP4. Thromb Res 2010;126: e23-9. https://doi.org/10.1016/j.thromres.2010.04.003.

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[155] Bauer J, Ripperger A, Frantz S, Ergün S, Schwedhelm E, Benndorf RA. Pathophysiology of isoprostanes in the cardiovascular system: implications of isoprostane-mediated thromboxane a 2 receptor activation. Br J Pharmacol 2014; 171:3115-31. https://doi.org/10.1111/bph.12677.

[156] Green D, Ruparel S, Gao X, Ruparel N, Patil M, Akopian A, et al. Central activation of TRPV1 and TRPA1 by novel endogenous agonists contributes to mechanical allodynia and thermal hyperalgesia after burn injury. Mol Pain 2016:12. https://doi.org/10.1177/1744806916661725.

[157] Patwardhan AM, Akopian AN, Ruparel NB, Diogenes A, Weintraub ST, Uhlson C, et al. Heat generates oxidized linoleic acid metabolites that activate TRPV1 and produce pain in rodents. J Clin Investig 2010;120:1617-26. https://doi.org/10.1172/JCI14678.

[158] Campbell WB, Fleming I. Epoxyeicosatrienoic acids and endothelial-dependent responses. Pflugers Arch 2010;459:881-95. https://doi.org/10.1007/s00424-010-0804-6.

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[160] Ostermann AI, Schebb NH. Effects of omega-3 fatty acid supplementation on the pattern of oxylipins: a short review about the modulation of hydroxy-, dihydroxy-, and epoxy-fatty acids. Food Funct 2017;8:2355-67. https://doi.org/10.1039/C7FO00403F.

[161] Camacho-Muñoz D, Kiezel-Tsugunova M, Kiss O, Uddin M, Sundén M, Ryaboshkina M, et al. Omega-3 carboxylic acids and fenofibrate differentially alter plasma lipid mediators in patients with non-alcoholic fatty liver disease. FASEB J 2021:35. https://doi.org/10.1096/fj.202100380RR.

[162] Dasilva G, Pazos M, García-Egido E, Gallardo JM, Ramos-Romero S, Torres JL, et al. A lipidomic study on the regulation of inflammation and oxidative stress targeted by marine ω-3 PUFA and polyphenols in high-fat high-sucrose diets. J Nutr Biochem 2017;43:53-67. https://doi.org/10.1016/j.jnutbio.2017.02.007.

[163] Fischer R, Konkel A, Mehling H, Blossey K, Gapelyuk A, Wessel N, et al. Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway. J Lipid Res 2014;55:1150-64. https://doi.org/10.1194/jlr.M047357.

[164] Gottschall H, Schmöcker C, Hartmann D, Rohwer N, Rund K, Kutzner L, et al. Aspirin alone and combined with a statin suppresses eicosanoid formation in human colon tissue. J Lipid Res 2018;59:864-71. https://doi.org/10.1194/jlr.M078725.

[165] Welch BM, Keil AP, Bommarito PA, Vant' Erve TJ, Deterding LJ, Williams JG, et al. Longitudinal exposure to consumer product chemicals and changes in plasma oxylipins in pregnant women. Environ Int 2021;157:106787. https://doi.org/10.1016/j.envint.2021.106787.

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[167] Warner DR, Liu H, Ghosh Dastidar S, Warner JB, Prodhan MAI, Yin X, et al. Ethanol and unsaturated dietary fat induce unique patterns of hepatic ω-6 and ω-3 PUFA oxylipins in a mouse model of alcoholic liver disease. PloS One 2018;13: e0204119. https://doi.org/10.1371/journal.pone.0204119.

[168] Caligiuri SPB, Pierce GN, Ravandi A, Aukema HM. The plasma Oxylipidome links smoking status to peripheral artery disease. Metabolites 2022;12:627. https://doi.org/10.3390/metabo12070627.

[169] Martinez JA, Skiba MB, Chow H-HS, Chew WM, Saboda K, Lance P, et al. A protective role for arachidonic acid metabolites against advanced colorectal adenoma in a phase III trial of selenium. Nutrients 2021;13:3877. https://doi.org/10.3390/nu13113877.

[170] Schramm DD, Wang JF, Holt RR, Ensunsa JL, Gonsalves JL, Lazarus SA, et al. Chocolate procyanidins decrease the leukotriene-prostacyclin ratio in humans and human aortic endothelial cells. Am J Clin Nutr 2001;73:36-40. https://doi.org/10.1093/ajcn/73.1.36.

[171] Miyamoto J, Igarashi M, Watanabe K, Karaki S, Mukouyama H, Kishino S, et al. Gut microbiota confers host resistance to obesity by metabolizing dietary polyunsaturated fatty acids. Nat Commun 2019;10:4007. https://doi.org/10.1038/s41467-019-11978-0.

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[174] Ávila-Román J, Arreaza-Gil V, Cortés-Espárin A, Soliz-Rueda JR, Mulero M, Muguerza B, et al. Impact of gut microbiota on plasma oxylipins profile under healthy and obesogenic conditions. Clin Nutr 2021;40:1475-86. https://doi.org/10.1016/j.clnu.2021.02.035.

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[131] Rund KM, Peng S, Greite R, Claaßen C, Nolte F, Oger C, et al. Dietary omega-3 PUFA improved tubular function after ischemia induced acute kidney injury in mice but did not attenuate impairment of renal function. Prostaglandins Other Lipid Mediat 2020;146:106386. https://doi.org/10.1016/j.prostaglandins.2019.106386.

[132] Vesper HW, Myers GL, Miller WG. Current practices and challenges in the standardization and harmonization of clinical laboratory tests. Am J Clin Nutr 2016;104:907S-12S. https://doi.org/10.3945/ajcn.115.110387.

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[134] Biringer RG. A review of non-prostanoid, eicosanoid receptors: expression, characterization, regulation, and mechanism of action. J Cell Commun Signal 2022;16:5-46. https://doi.org/10.1007/s12079-021-00630-6.

[135] Biringer RG. A review of Prostanoid receptors: expression, characterization, regulation, and mechanism of action. J Cell Commun Signal 2021;15:155-84. https://doi.org/10.1007/s12079-020-00585-0.

[136] Marion-Letellier R, Savoye G, Ghosh S. Fatty acids, eicosanoids and PPAR gamma. Eur J Pharmacol 2016;785:44-9. https://doi.org/10.1016/j.ejphar.2015.11.004.

[137] Milne GL, Yin H, Hardy KD, Davies SS, Roberts LJ. Isoprostane generation and function. Chem Rev 2011;111:5973-96. https://doi.org/10.1021/cr200160h.

[138] Hasanally D, Chaudhary R, Ravandi A. Role of Phospholipases and Oxidized Phospholipids in Inflammation. Phospholipids in Health and Disease. New York, NY: Springer New York; 2014. p. 55-72. https://doi.org/10.1007/978-1-4939-0464-8_3.

[139] Paramjit S, Tappia NSD. Phospholipases in health and disease. In: Paramjit S, Tappia NSD, editors. Advances in biochemistry in health and disease. vol. 10. Springer; 2014.

[140] Lauder SN, Allen-Redpath K, Slatter DA, Aldrovandi M, O'Connor A, Farewell D, et al. Networks of enzymatically oxidized membrane lipids support calcium-dependent coagulation factor binding to maintain hemostasis. Sci Signal 2017;10. https://doi.org/10.1126/scisignal.aan2787.

[141] Slatter DA, Percy CL, Allen-Redpath K, Gajsiewicz JM, Brooks NJ, Clayton A, et al. Enzymatically oxidized phospholipids restore thrombin generation in coagulation factor deficiencies. JCI Insight 2018:3. https://doi.org/10.1172/jci.insight.98459.

[142] Uderhardt S, Ackermann JA, Filleter T, Hammond VJ, Willeit J, Santer P, et al. Enzymatic lipid oxidation by eosinophils propagates coagulation, hemostasis, and thrombotic disease. J Exp Med 2017;214:2121-38. https://doi.org/10.1084/jem.20161070.

[143] Petrich K, Ludwig P, Kühn H, Schewe T. The suppression of 5-lipoxygenation of arachidonic acid in human polymorphonuclear leucocytes by the 15-lipoxygenase product (15 S)-hydroxy-(5, 8 Z, 11 Z, 13 E)-eicosatetraenoic acid: structure-activity relationship and mechanism of action. Biochem J 1996;314:911-6. https://doi.org/10.1042/bj3140911.

[144] Willenberg I, Ostermann AI, Schebb NH. Targeted metabolomics of the arachidonic acid cascade: current state and challenges of LC-MS analysis of oxylipins. Anal Bioanal Chem 2015;407:2675-83. https://doi.org/10.1007/s00216-014-8369-4.

[145] Braune S, Küpper J-H, Jung F. Effect of Prostanoids on human platelet function: an overview. Int J Mol Sci 2020;21:9020. https://doi.org/10.3390/ijms21239020.

[146] Af Forselles KJ, Root J, Clarke T, Davey D, Aughton K, Dack K, et al. In vitro and in vivo characterization of PF-04418948, a novel, potent and selective prostaglandin EP2 receptor antagonist. Br J Pharmacol 2011;164:1847-56. https://doi.org/10.1111/j.1476-5381.2011.01495.x.

[147] Gray SJ, Heptinstall S. The effects of PGE2 and CL 115,347, an antihypertensive PGE2 analogue, on human blood platelet behaviour and vascular contractility. Eur J Pharmac 1985;114:129-37. https://doi.org/10.1016/0014-2999(85)90620-x.

[148] Norel X, Sugimoto Y, Ozen G, Abdelazeem H, Amgoud Y, Bouhadoun A, et al. International Union of Basic and Clinical Pharmacology. CIX. Differences and similarities between human and rodent prostaglandin E 2 receptors (EP1-4) and prostacyclin receptor (IP): specific roles in pathophysiologic conditions. Pharmacol Rev 2020;72:910-68. https://doi.org/10.1124/pr.120.019331.

[149] Kida T, Sawada K, Kobayashi K, Hori M, Ozaki H, Murata T. Diverse effects of prostaglandin E2 on vascular contractility. Heart Vessels 2014;29:390-5. https://doi.org/10.1007/s00380-013-0374-6.

[152] Smith JP, Haddad EV, Downey JD, Breyer RM, Boutaud O. PGE2 decreases reactivity of human platelets by activating EP2 and EP4. Thromb Res 2010;126: e23-9. https://doi.org/10.1016/j.thromres.2010.04.003.

[153] Attie AD, Raines RT. Analysis of receptor-ligand interactions. J Chem Educ 1995; 72:119-24. https://doi.org/10.1021/ed072p119.

[154] Rittchen S, Rohrer K, Platzer W, Knuplez E, Bärnthaler T, Marsh LM, et al. Prostaglandin D2 strengthens human endothelial barrier by activation of E-type receptor 4. Biochem Pharmacol 2020;182:114277. https://doi.org/10.1016/j.bcp.2020.114277.

[155] Bauer J, Ripperger A, Frantz S, Ergün S, Schwedhelm E, Benndorf RA. Pathophysiology of isoprostanes in the cardiovascular system: implications of isoprostane-mediated thromboxane a 2 receptor activation. Br J Pharmacol 2014; 171:3115-31. https://doi.org/10.1111/bph.12677.

[156] Green D, Ruparel S, Gao X, Ruparel N, Patil M, Akopian A, et al. Central activation of TRPV1 and TRPA1 by novel endogenous agonists contributes to mechanical allodynia and thermal hyperalgesia after burn injury. Mol Pain 2016:12. https://doi.org/10.1177/1744806916661725.

[157] Patwardhan AM, Akopian AN, Ruparel NB, Diogenes A, Weintraub ST, Uhlson C, et al. Heat generates oxidized linoleic acid metabolites that activate TRPV1 and produce pain in rodents. J Clin Investig 2010;120:1617-26. https://doi.org/10.1172/JCI14678.

[158] Campbell WB, Fleming I. Epoxyeicosatrienoic acids and endothelial-dependent responses. Pflugers Arch 2010;459:881-95. https://doi.org/10.1007/s00424-010-0804-6.

[159] Bäck M, Brink C, Chiang N, Dahlén S-E, Dent G, Drazen J, et al. Leukotriene receptors in GtoPdb v.2023.1. In: IUPHAR/BPS Guide to Pharmacology CITE. 2023; 2023. https://doi.org/10.2218/gtopdb/F35/2023.1.

[160] Ostermann AI, Schebb NH. Effects of omega-3 fatty acid supplementation on the pattern of oxylipins: a short review about the modulation of hydroxy-, dihydroxy-, and epoxy-fatty acids. Food Funct 2017;8:2355-67. https://doi.org/10.1039/C7FO00403F.

[161] Camacho-Muñoz D, Kiezel-Tsugunova M, Kiss O, Uddin M, Sundén M, Ryaboshkina M, et al. Omega-3 carboxylic acids and fenofibrate differentially alter plasma lipid mediators in patients with non-alcoholic fatty liver disease. FASEB J 2021:35. https://doi.org/10.1096/fj.202100380RR.

[162] Dasilva G, Pazos M, García-Egido E, Gallardo JM, Ramos-Romero S, Torres JL, et al. A lipidomic study on the regulation of inflammation and oxidative stress targeted by marine ω-3 PUFA and polyphenols in high-fat high-sucrose diets. J Nutr Biochem 2017;43:53-67. https://doi.org/10.1016/j.jnutbio.2017.02.007.

[163] Fischer R, Konkel A, Mehling H, Blossey K, Gapelyuk A, Wessel N, et al. Dietary omega-3 fatty acids modulate the eicosanoid profile in man primarily via the CYP-epoxygenase pathway. J Lipid Res 2014;55:1150-64. https://doi.org/10.1194/jlr.M047357.

[164] Gottschall H, Schmöcker C, Hartmann D, Rohwer N, Rund K, Kutzner L, et al. Aspirin alone and combined with a statin suppresses eicosanoid formation in human colon tissue. J Lipid Res 2018;59:864-71. https://doi.org/10.1194/jlr.M078725.

[165] Welch BM, Keil AP, Bommarito PA, Vant' Erve TJ, Deterding LJ, Williams JG, et al. Longitudinal exposure to consumer product chemicals and changes in plasma oxylipins in pregnant women. Environ Int 2021;157:106787. https://doi.org/10.1016/j.envint.2021.106787.

[166] Wang T, Han Y, Li H, Wang Y, Xue T, Chen X, et al. Changes in bioactive lipid mediators in response to short-term exposure to ambient air particulate matter: a targeted lipidomic analysis of oxylipin signaling pathways. Environ Int 2021;147: 106314. https://doi.org/10.1016/j.envint.2020.106314.

[167] Warner DR, Liu H, Ghosh Dastidar S, Warner JB, Prodhan MAI, Yin X, et al. Ethanol and unsaturated dietary fat induce unique patterns of hepatic ω-6 and ω-3 PUFA oxylipins in a mouse model of alcoholic liver disease. PloS One 2018;13: e0204119. https://doi.org/10.1371/journal.pone.0204119.

[168] Caligiuri SPB, Pierce GN, Ravandi A, Aukema HM. The plasma Oxylipidome links smoking status to peripheral artery disease. Metabolites 2022;12:627. https://doi.org/10.3390/metabo12070627.

[169] Martinez JA, Skiba MB, Chow H-HS, Chew WM, Saboda K, Lance P, et al. A protective role for arachidonic acid metabolites against advanced colorectal adenoma in a phase III trial of selenium. Nutrients 2021;13:3877. https://doi.org/10.3390/nu13113877.

[170] Schramm DD, Wang JF, Holt RR, Ensunsa JL, Gonsalves JL, Lazarus SA, et al. Chocolate procyanidins decrease the leukotriene-prostacyclin ratio in humans and human aortic endothelial cells. Am J Clin Nutr 2001;73:36-40. https://doi.org/10.1093/ajcn/73.1.36.

[171] Miyamoto J, Igarashi M, Watanabe K, Karaki S, Mukouyama H, Kishino S, et al. Gut microbiota confers host resistance to obesity by metabolizing dietary polyunsaturated fatty acids. Nat Commun 2019;10:4007. https://doi.org/10.1038/s41467-019-11978-0.

[172] Nieman DC, Pence BD. Exercise immunology: Future directions. J Sport Health Sci 2020;9:432-45. https://doi.org/10.1016/j.jshs.2019.12.003.

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[188] Schuchardt JP, Schmidt S, Kressel G, Dong H, Willenberg I, Hammock BD, et al. Comparison of free serum oxylipin concentrations in hyper- vs. normolipidemic men. Prostaglandins Leukot Essent Fatty Acids 2013;89:19–29. https://doi.org/ 10.1016/j.plefa.2013.04.001.

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[199] Chistyakov DV, Azbukina NV, Lopachev AV, Goriainov SV, Astakhova AA, Pititsyna EV, et al. Plasma oxylipin profiles reflect Parkinson's disease stage. Prostaglandins Other Lipid Mediat 2024;171:106788. https://doi.org/10.1016/j.prostaglandins.2023.106788.

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[205] Ren J, Ren A, Huang Z, Deng X, Jiang Z, Xue Y, et al. Metabolomic profiling of Long-chain polyunsaturated fatty acid oxidation in adults with retinal vein occlusion: a case-control study. Am J Clin Nutr 2023;118:579–90. https://doi.org/10.1016/j.ajcnut.2023.07.006.

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[183] Caligiuri SPB, Aukema HM, Ravandi A, Lavallée R, Guzman R, Pierce GN. Specific plasma oxylipins increase the odds of cardiovascular and cerebrovascular events in patients with peripheral artery disease. Can J Physiol Pharmacol 2017;95: 961–8. https://doi.org/10.1139/cjpp-2016-0615.

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[187] Dalle C, Tournayre J, Mainka M, Basiak-Rasaa A, Pétraë M, Lefevre-Arbogast S, et al. The plasma Oxylipin signature provides a deep phenotyping of metabolic syndrome complementary to the clinical criteria. Int J Mol Sci 2022;23:11688. https://doi.org/10.3390/ijms231911688.

[188] Schuchardt JP, Schmidt S, Kressel G, Dong H, Willenberg I, Hammock BD, et al. Comparison of free serum oxylipin concentrations in hyper- vs. normolipidemic men. Prostaglandins Leukot Essent Fatty Acids 2013;89:19–29. https://doi.org/ 10.1016/j.plefa.2013.04.001.

[189] Jiménez-Franco A, Castané H, Martínez-Navidad C, Placed-Gallego C, Hernández-Aguilera A, Fernández-Arroyo S, et al. Metabolic adaptations in severe obesity: insights from circulating oxylipins before and after weight loss. Clin Nutr 2024; 43:246–58. https://doi.org/10.1016/j.clnu.2023.12.002.

[190] Grapov D, Fiehn O, Campbell C, Chandler CJ, Burnett DJ, Souza EC, et al. Impact of a weight loss and fitness intervention on exercise-associated plasma oxylipin patterns in obese, insulin-resistant, sedentary women. Physiol Rep 2020;8. https://doi.org/10.14814/phy2.14547.

[191] Hernandez-Carretero A, Weber N, La Frano MR, Ying W, Lantero Rodriguez J, Sears DD, et al. Obesity-induced changes in lipid mediators persist after weight loss. Int J Obes (Lond) 2018;42:728–36. https://doi.org/10.1038/ijo.2017.266.

[192] Tuomisto K, Palmu J, Long T, Watrous JD, Mercader K, Lagerborg KA, et al. A plasma metabolite score of three eicosanoids predicts incident type 2 diabetes: a prospective study in three independent cohorts. BMJ Open Diabetes Res Care 2022;10:e002519. https://doi.org/10.1136/bmjdc2021-002519.

[193] Tans R, Bande R, van Rooij A, Molloy BJ, Stienstra R, Tack CJ, et al. Evaluation of cyclooxygenase oxylipins as potential biomarker for obesity-associated adipose tissue inflammation and type 2 diabetes using targeted multiple reaction monitoring mass spectrometry. Prostaglandins Leukot Essent Fatty Acids 2020; 160:102157. https://doi.org/10.1016/j.plefa.2020.102157.

[194] Grapov D, Adams SH, Pedersen TL, Garvey WT, Newman JW. Type 2 diabetes associated changes in the plasma non-esterified fatty acids, oxylipins and endocannabinoids. PloS One 2012;7:e48852. https://doi.org/10.1371/journal.pone.0048852.

[195] Buckner T, Vanderlinden LA, DeFelice BC, Carry PM, Kechris K, Dong F, et al. The oxylipin profile is associated with development of type 1 diabetes: the diabetes

autoimmunity study in the young (DAISY). Diabetologia 2021;64:1785–94. https://doi.org/10.1007/s00125-021-05457-9.

[196] Li Q, Rempel JD, Ball TB, Aukema H, Minuk GY. Plasma Oxylipins levels in nonalcoholic fatty liver disease. Dig Dis Sci 2020;65:3605–13. https://doi.org/ 10.1007/s10620-020-06095-8.

[197] Chocholoušková M, Jirásko R, Vrátna D, Gátek J, Melichar B, Holcapek M. Reversed phase UHPLC/ESI-MS determination of oxylipins in human plasma: a case study of female breast cancer. Anal Bioanal Chem 2019;411:1239–51. https://doi.org/10.1007/s00216-018-1556-y.

[198] Martinez JA, Skiba MB, Chow H-HS, Chew WM, Saboda K, Lance P, et al. A protective role for arachidonic acid metabolites against advanced colorectal adenoma in a phase III trial of selenium. Nutrients 2021;13:3877. https://doi. org/10.3390/nu13113877.

[199] Chistyakov DV, Azbukina NV, Lopachev AV, Goriainov SV, Astakhova AA, Pititsyna EV, et al. Plasma oxylipin profiles reflect Parkinson's disease stage. Prostaglandins Other Lipid Mediat 2024;171:106788. https://doi.org/10.1016/j. prostaglandins.2023.106788.

[200] Gouveia-Figueira S, Goldin K, Hashemian SA, Lindberg A, Persson M, Nording ML, et al. Plasma levels of the endocannabinoid anandamide, related N- acylethanolamines and linoleic acid-derived oxylipins in patients with migraine. Prostaglandins Leukot Essent Fatty Acids 2017;120:15–24. https://doi.org/ 10.1016/j.plefa.2017.04.005.

[201] Borkowski K, Pedersen TL, Seyfried NT, Lah JJ, Levey AI, Hales CM, et al. Association of plasma and CSF cytochrome P450, soluble epoxide hydrolase, and ethanolamide metabolism with Alzheimer's disease. Alzheimers Res Ther 2021; 13:149. https://doi.org/10.1186/s13195-021-00893-6.

[202] Hennebelle M, Otoki Y, Yang J, Hammock BD, Levitt AJ, Taha AY, et al. Altered soluble epoxide hydrolase-derived oxylipins in patients with seasonal major depression: an exploratory study. Psychiatry Res 2017;252:94–101. https://doi. org/10.1016/j.psychres.2017.02.056.

[203] Rhee SY, Jung ES, Suh DH, Jeong SJ, Kim K, Chon S, et al. Plasma amino acids and oxylipins as potential multi-biomarkers for predicting diabetic macular edema. Sci Rep 2021;11:9727. https://doi.org/10.1038/s41598-021-88104-y.

[204] Xu J, Fu C, Sun Y, Wen X, Chen C-B, Huang C, et al. Untargeted and Oxylipin- targeted metabolomics study on the plasma samples of primary open-angle Glaucoma patients. Biomolecules 2024;14:307. https://doi.org/10.3390/ biom14030307.

[205] Ren J, Ren A, Huang Z, Deng X, Jiang Z, Xue Y, et al. Metabolomic profiling of Long-chain polyunsaturated fatty acid oxidation in adults with retinal vein occlusion: a case-control study. Am J Clin Nutr 2023;118:579–90. https://doi. org/10.1016/j.ajcnut.2023.07.006.

[206] Biagini D, Oliveri P, Baj A, Gasperina DD, Ferrante FD, Lomonaco T, et al. The effect of SARS-CoV-2 variants on the plasma oxylipins and PUFAs of COVID-19 patients. Prostaglandins Other Lipid Mediat 2023;169:106770. https://doi.org/ 10.1016/j.prostaglandins.2023.106770.

[207] Deme P, Moniruzzaman M, Moore D, Heaton R, Ellis R, Letendre S, et al. Association of Plasma Eicosanoid Levels with Immune, viral, and cognitive outcomes in people with HIV. Neurology 2022;99. https://doi.org/10.1212/ WNL.00000000000200945.

[208] Surowiec I, Gouveia-Figueira S, Orikiriza J, Lindquist E, Bonde M, Magambo J, et al. The oxylipin and endocannabinoid responses in acute phase plasmodium falciparum malaria in children. Malar J 2017;16:358. https://doi.org/10.1186/ s12936-017-2001-y.

[209] Ben-Mustapha Y, Ben-Fradj MK, Hadj-Taieb S, Serghini M, Ben Ahmed M, Boubaker J, et al. Altered mucosal and plasma polyunsaturated fatty acids, oxylipins, and endocannabinoids profiles in Crohn's disease. Prostaglandins Other Lipid Mediat 2023;168:106741. https://doi.org/10.1016/j. prostaglandins.2023.106741.

[210] Svensk M, Raffetseder J, Brudin L, Lindberg R, Blomberg M, Axelsson D, et al. Plasma oxylipin levels associated with preterm birth in preterm labor. https://doi.org/ 10.1016/j.plefa.2021.102251.

[211] Deng B-Q, Li M-Y, Fu X, Luo Y, Qiao Q, Liu J-Y. Targeted metabolomics study of human plasma revealed activation of the cytochrome P450 Epoxygenase/epoxide hydrolase Axis in patients with IgA nephropathy. J Proteome Res 2022;21: 2969–78. https://doi.org/10.1021/acs.jproteome.2c00471.

[212] Dalle C, Ostermann AI, Konrad T, Coudy-Gandilhon C, Decourt A, Barthélémy J-C, et al. Muscle loss associated changes of Oxylipin signatures during biological aging: an exploratory study from the PROOF cohort. J Gerontol: Series A 2019;74: 608–15. https://doi.org/10.1093/gerona/gly187.