{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T02:41:28Z","timestamp":1788403288576,"version":"build-2803163510"},"publisher-location":"Cham","reference-count":74,"publisher":"Springer International Publishing","isbn-type":[{"value":"9783030216368","type":"print"},{"value":"9783030217358","type":"electronic"}],"license":[{"start":{"date-parts":[[2019,1,1]],"date-time":"2019-01-01T00:00:00Z","timestamp":1546300800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/www.springer.com\/tdm"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2019]]},"DOI":"10.1007\/978-3-030-21735-8_17","type":"book-chapter","created":{"date-parts":[[2019,9,27]],"date-time":"2019-09-27T17:03:27Z","timestamp":1569603807000},"page":"219-232","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Novel Anti-inflammatory and Vasodilatory \u03c9-3 Endocannabinoid Epoxide Regioisomers"],"prefix":"10.1007","author":[{"given":"Lauren N.","family":"Carnevale","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aditi","family":"Das","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2019,9,28]]},"reference":[{"key":"17_CR1","doi-asserted-by":"publisher","first-page":"561","DOI":"10.1038\/346561a0","volume":"346","author":"LA Matsuda","year":"1990","unstructured":"Matsuda LA, Lolait SJ, Brownstein MJ et al (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346:561\u2013564. https:\/\/doi.org\/10.1038\/346561a0","journal-title":"Nature"},{"key":"17_CR2","first-page":"605","volume":"34","author":"WA Devane","year":"1988","unstructured":"Devane WA, Dysarz FA, Johnson RM et al (1988) Determination rat brain and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol 34:605\u2013613","journal-title":"Mol Pharmacol"},{"key":"17_CR3","doi-asserted-by":"publisher","first-page":"221","DOI":"10.1054\/plef.2001.0360","volume":"66","author":"E Fride","year":"2002","unstructured":"Fride E (2002) Endocannabinoids in the central nervous system\u00a0\u2013 an overview. Prostaglandins Leukot Essent Fat Acids 66:221\u2013233. https:\/\/doi.org\/10.1054\/plef.2001.0360","journal-title":"Prostaglandins Leukot Essent Fat Acids"},{"key":"17_CR4","doi-asserted-by":"publisher","first-page":"1996","DOI":"10.1161\/01.CIR.0000143230.23252.D2","volume":"110","author":"S B\u00e1tkai","year":"2004","unstructured":"B\u00e1tkai S, Pacher P, Osei-Hyiaman D et al (2004) Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Circulation 110:1996\u20132002. https:\/\/doi.org\/10.1161\/01.CIR.0000143230.23252.D2","journal-title":"Circulation"},{"key":"17_CR5","doi-asserted-by":"publisher","first-page":"112","DOI":"10.1016\/j.prostaglandins.2014.11.002","volume":"116\u2013117","author":"S Zelasko","year":"2015","unstructured":"Zelasko S, Arnold WR, Das A (2015) Endocannabinoid metabolism by cytochrome P450 monooxygenases. Prostaglandins Other Lipid Mediat 116\u2013117:112\u2013123. https:\/\/doi.org\/10.1016\/j.prostaglandins.2014.11.002","journal-title":"Prostaglandins Other Lipid Mediat"},{"key":"17_CR6","doi-asserted-by":"publisher","first-page":"54","DOI":"10.1111\/j.1432-1033.1995.tb20780.x","volume":"232","author":"S Galiegue","year":"1995","unstructured":"Galiegue S, Mary S, Marchand J et\u00a0al (1995) Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem 232:54\u201361. https:\/\/doi.org\/10.1111\/j.1432-1033.1995.tb20780.x","journal-title":"Eur J Biochem"},{"key":"17_CR7","doi-asserted-by":"publisher","first-page":"141","DOI":"10.1016\/S0014-2999(00)00211-9","volume":"396","author":"NE Buckley","year":"2000","unstructured":"Buckley NE, McCoy KL, Mezey \u00c9 et al (2000) Immunomodulation by cannabinoids is absent in mice deficient for the cannabinoid CB2receptor. Eur J Pharmacol 396:141\u2013149. https:\/\/doi.org\/10.1016\/S0014-2999(00)00211-9","journal-title":"Eur J Pharmacol"},{"key":"17_CR8","doi-asserted-by":"publisher","first-page":"61","DOI":"10.1038\/365061a0","volume":"365","author":"S Munro","year":"1993","unstructured":"Munro S, Thomas KL, Abu-Shaar M (1993) Molecular characterization of a peripheral receptor for cannabinoids. Nature 365:61\u201365. https:\/\/doi.org\/10.1038\/365061a0","journal-title":"Nature"},{"key":"17_CR9","doi-asserted-by":"publisher","first-page":"430","DOI":"10.1124\/mol.114.094649","volume":"86","author":"A Dhopeshwarkar","year":"2014","unstructured":"Dhopeshwarkar A, Mackie K (2014) CB2 cannabinoid receptors as a therapeutic target\u2013what does the future hold. Mol Pharmacol 86:430\u2013437. https:\/\/doi.org\/10.1124\/mol.114.094649","journal-title":"Mol Pharmacol"},{"key":"17_CR10","doi-asserted-by":"publisher","first-page":"1020","DOI":"10.1124\/jpet.301.3.1020","volume":"301","author":"AC Porter","year":"2002","unstructured":"Porter AC, Sauer J-MM, Knierman MD et al (2002) Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor. J Pharmacol Exp Ther 301:1020\u20131024. https:\/\/doi.org\/10.1124\/jpet.301.3.1020","journal-title":"J Pharmacol Exp Ther"},{"key":"17_CR11","doi-asserted-by":"publisher","first-page":"S163","DOI":"10.1038\/sj.bjp.0706406","volume":"147","author":"RG Pertwee","year":"2006","unstructured":"Pertwee RG (2006) Cannabinoid pharmacology: the first 66 years. Br J Pharmacol 147:S163. https:\/\/doi.org\/10.1038\/sj.bjp.0706406","journal-title":"Br J Pharmacol"},{"key":"17_CR12","doi-asserted-by":"publisher","first-page":"6489","DOI":"10.1021\/acs.biochem.8b00691","volume":"57","author":"L Carnevale","year":"2018","unstructured":"Carnevale L, Arango A, Arnold WR et al (2018) Endocannabinoid virodhamine is an endogenous inhibitor of human cardiovascular CYP2J2 epoxygenase. Biochemistry 57:6489\u20136499. https:\/\/doi.org\/10.1021\/acs.biochem.8b00691","journal-title":"Biochemistry"},{"key":"17_CR13","doi-asserted-by":"publisher","first-page":"E6034","DOI":"10.1073\/pnas.1610325114","volume":"114","author":"DR McDougle","year":"2017","unstructured":"McDougle DR, Watson JE, Abdeen AA et al (2017) Anti-inflammatory \u03c9-3 endocannabinoid epoxides. Proc Natl Acad Sci U S A 114:E6034\u2013E6043. 201610325. https:\/\/doi.org\/10.1073\/pnas.1610325114","journal-title":"Proc Natl Acad Sci U S A"},{"key":"17_CR14","doi-asserted-by":"publisher","first-page":"5319","DOI":"10.1039\/c1sm05141e","volume":"7","author":"SM Sagnella","year":"2011","unstructured":"Sagnella SM, Conn CE, Irena Krodkiewska XM, CJD (2011) Anandamide and analogous endocannabinoids: a lipid self-assembly study. Soft Matter 7:5319\u20135328. https:\/\/doi.org\/10.1039\/c1sm05141e","journal-title":"Soft Matter"},{"key":"17_CR15","doi-asserted-by":"publisher","first-page":"1416","DOI":"10.1194\/jlr.M002436","volume":"51","author":"JT Wood","year":"2010","unstructured":"Wood JT, Williams JS, Pandarinathan L et al (2010) Dietary docosahexaenoic acid supplementation alters select physiological endocannabinoid-system metabolites in brain and plasma. J Lipid Res 51:1416\u20131423. https:\/\/doi.org\/10.1194\/jlr.M002436","journal-title":"J Lipid Res"},{"key":"17_CR16","doi-asserted-by":"publisher","first-page":"856","DOI":"10.1007\/s11481-012-9351-6","volume":"7","author":"H Sharir","year":"2012","unstructured":"Sharir H, Console-Bram L, Mundy C et al (2012) The endocannabinoids anandamide and virodhamine modulate the activity of the candidate cannabinoid receptor GPR55. J Neuroimmune Pharmacol 7:856\u2013865. https:\/\/doi.org\/10.1007\/s11481-012-9351-6","journal-title":"J Neuroimmune Pharmacol"},{"key":"17_CR17","doi-asserted-by":"publisher","first-page":"434","DOI":"10.1038\/nature01807","volume":"424","author":"H Watanabe","year":"2003","unstructured":"Watanabe H, Vriens J, Prenen J et\u00a0al (2003) Anandamide and arachidonic acid use epoxyeicosatrienoic acids to activate TRPV4 channels. Nature 424:434\u2013438. https:\/\/doi.org\/10.1038\/nature01807","journal-title":"Nature"},{"key":"17_CR18","doi-asserted-by":"publisher","first-page":"1226","DOI":"10.1523\/JNEUROSCI.17-04-01226.1997","volume":"17","author":"H Cadas","year":"1997","unstructured":"Cadas H, di Tomaso E, Piomelli D (1997) Occurrence and biosynthesis of endogenous cannabinoid precursor, N-arachidonoyl phosphatidylethanolamine, in rat brain. J Neurosci 17:1226\u20131242","journal-title":"J Neurosci"},{"key":"17_CR19","doi-asserted-by":"publisher","first-page":"749","DOI":"10.1042\/BJ20040031","volume":"380","author":"Y-X Sun","year":"2004","unstructured":"Sun Y-X, Tsuboi K, Okamoto Y et al (2004) Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A2 and lysophospholipase D. Biochem J 380:749\u2013756. https:\/\/doi.org\/10.1042\/BJ20040031","journal-title":"Biochem J"},{"key":"17_CR20","doi-asserted-by":"publisher","first-page":"1379","DOI":"10.1111\/bph.12411","volume":"171","author":"N Murataeva","year":"2014","unstructured":"Murataeva N, Straiker A, MacKie K (2014) Parsing the players: 2-arachidonoylglycerol synthesis and degradation in the CNS. Br J Pharmacol 171:1379\u20131391. https:\/\/doi.org\/10.1111\/bph.12411","journal-title":"Br J Pharmacol"},{"key":"17_CR21","doi-asserted-by":"publisher","first-page":"469","DOI":"10.1016\/S1367-5931(03)00079-6","volume":"7","author":"BF Cravatt","year":"2003","unstructured":"Cravatt BF, Lichtman AH (2003) Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system. Curr Opin Chem Biol 7:469\u2013475. https:\/\/doi.org\/10.1016\/S1367-5931(03)00079-6","journal-title":"Curr Opin Chem Biol"},{"key":"17_CR22","doi-asserted-by":"publisher","unstructured":"Ahn K, Johnson DS, Cravatt BF (2010) NIH Public Access 4:763\u2013784. https:\/\/doi.org\/10.1517\/17460440903018857.Fatty","DOI":"10.1517\/17460440903018857.Fatty"},{"key":"17_CR23","doi-asserted-by":"publisher","first-page":"218","DOI":"10.1002\/cbic.200900621","volume":"11","author":"G Labar","year":"2010","unstructured":"Labar G, Bauvois C, Borel F et al (2010) Crystal structure of the human monoacylglycerol lipase, a key actor in endocannabinoid signaling. Chembiochem 11:218\u2013227. https:\/\/doi.org\/10.1002\/cbic.200900621","journal-title":"Chembiochem"},{"key":"17_CR24","doi-asserted-by":"publisher","first-page":"1687","DOI":"10.1021\/cr0782067.Enzymatic","volume":"108","author":"A Kay","year":"2011","unstructured":"Kay A, Michele MK, Benjamin CF (2011) Enzymatic pathways that regulate endocannabinoid signaling in the nervous system. Chem Rev 108:1687\u20131707. https:\/\/doi.org\/10.1021\/cr0782067.Enzymatic","journal-title":"Chem Rev"},{"key":"17_CR25","doi-asserted-by":"publisher","first-page":"1538","DOI":"10.1172\/JCI119677","volume":"100","author":"DG Deutsch","year":"1997","unstructured":"Deutsch DG, Goligorsky MS, Schmid PC et al (1997) Production and physiological actions of anandamide in the vasculature of the rat kidney. J Clin Invest 100:1538\u20131546. https:\/\/doi.org\/10.1172\/JCI119677","journal-title":"J Clin Invest"},{"key":"17_CR26","doi-asserted-by":"publisher","first-page":"435","DOI":"10.2217\/17460875.3.4.435","volume":"3","author":"EA Horne","year":"2008","unstructured":"Horne EA, Stella N (2008) The ins and outs of endocannabinoid signaling in healthy and diseased brain. Futur Lipidol 3:435\u2013452. https:\/\/doi.org\/10.2217\/17460875.3.4.435","journal-title":"Futur Lipidol"},{"key":"17_CR27","doi-asserted-by":"publisher","first-page":"311","DOI":"10.1139\/cjpp-2016-0346","volume":"95","author":"Y Lu","year":"2017","unstructured":"Lu Y, Anderson HD (2017) Cannabinoid signaling in health and disease. Can J Physiol Pharmacol 95:311\u2013327. https:\/\/doi.org\/10.1139\/cjpp-2016-0346","journal-title":"Can J Physiol Pharmacol"},{"key":"17_CR28","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1038\/srep07458","volume":"4","author":"S Chen","year":"2014","unstructured":"Chen S, Zhang H, Pu H et al (2014) Epoxy. Sci Rep 4:1\u20138. https:\/\/doi.org\/10.1038\/srep07458","journal-title":"Sci Rep"},{"key":"17_CR29","doi-asserted-by":"publisher","first-page":"524","DOI":"10.1016\/j.nbd.2011.03.006","volume":"42","author":"S Mievis","year":"2011","unstructured":"Mievis S, Blum D, Ledent C (2011) Worsening of Huntington disease phenotype in CB1 receptor knockout mice. Neurobiol Dis 42:524\u2013529. https:\/\/doi.org\/10.1016\/j.nbd.2011.03.006","journal-title":"Neurobiol Dis"},{"key":"17_CR30","doi-asserted-by":"publisher","first-page":"640","DOI":"10.1038\/sj.ijo.0802583","volume":"28","author":"C Ravinet Trillou","year":"2004","unstructured":"Ravinet Trillou C, Delgorge C, Menet C et al (2004) CB1 cannabinoid receptor knockout in mice leads to leanness, resistance to diet-induced obesity and enhanced leptin sensitivity. Int J Obes 28:640\u2013648. https:\/\/doi.org\/10.1038\/sj.ijo.0802583","journal-title":"Int J Obes"},{"key":"17_CR31","doi-asserted-by":"publisher","first-page":"144","DOI":"10.1002\/pbc.23367.The","volume":"58","author":"F Thomas","year":"2013","unstructured":"Thomas F, Gamage AHL (2013) The endocannabinoid system: role in energy regulation. Trends Pharmacol Sci 58:144\u2013148. https:\/\/doi.org\/10.1002\/pbc.23367.The","journal-title":"Trends Pharmacol Sci"},{"key":"17_CR32","doi-asserted-by":"publisher","first-page":"5780","DOI":"10.1073\/pnas.96.10.5780","volume":"96","author":"M Zimmer a","year":"1999","unstructured":"Zimmer a M, Hohmann a G, Herkenham M, Bonner TI (1999) Increased mortality, hypoactivity, and hypoalgesia in cannabinoid CB1 receptor knockout mice. Proc Natl Acad Sci U S A 96:5780\u20135785. https:\/\/doi.org\/10.1073\/pnas.96.10.5780","journal-title":"Proc Natl Acad Sci U S A"},{"key":"17_CR33","doi-asserted-by":"publisher","first-page":"277","DOI":"10.1038\/sj.bjp.0707505","volume":"153","author":"C Benito","year":"2008","unstructured":"Benito C, Tol\u00f3n RM, Pazos MR et al (2008) Cannabinoid CB 2 receptors in human brain inflammation. Br J Pharmacol 153:277\u2013285. https:\/\/doi.org\/10.1038\/sj.bjp.0707505","journal-title":"Br J Pharmacol"},{"key":"17_CR34","doi-asserted-by":"publisher","first-page":"438","DOI":"10.1038\/nrd2553","volume":"7","author":"V Marzo Di","year":"2008","unstructured":"Di Marzo V (2008) Targeting the endocannabinoid system: to enhance or reduce. Nat Rev Drug Discov 7:438\u2013455. https:\/\/doi.org\/10.1038\/nrd2553","journal-title":"Nat Rev Drug Discov"},{"key":"17_CR35","doi-asserted-by":"publisher","first-page":"30","DOI":"10.1038\/nrn3876","volume":"16","author":"V Marzo Di","year":"2014","unstructured":"Di Marzo V, Stella N, Zimmer A (2014) Endocannabinoid signalling and the deteriorating brain. Nat Rev Neurosci 16:30\u201342. https:\/\/doi.org\/10.1038\/nrn3876","journal-title":"Nat Rev Neurosci"},{"key":"17_CR36","doi-asserted-by":"publisher","first-page":"1","DOI":"10.3389\/fnins.2016.00406","volume":"10","author":"G Navarro","year":"2016","unstructured":"Navarro G, Morales P, Rodr\u00edguez-Cueto C et al (2016) Targeting cannabinoid CB2receptors in the central nervous system. Medicinal chemistry approaches with focus on neurodegenerative disorders. Front Neurosci 10:1\u201311. https:\/\/doi.org\/10.3389\/fnins.2016.00406","journal-title":"Front Neurosci"},{"key":"17_CR37","doi-asserted-by":"publisher","first-page":"518","DOI":"10.1016\/j.tins.2006.07.006","volume":"29","author":"F Zipp","year":"2006","unstructured":"Zipp F, Aktas O (2006) The brain as a target of inflammation: common pathways link inflammatory and neurodegenerative diseases. Trends Neurosci 29:518\u2013527. https:\/\/doi.org\/10.1016\/j.tins.2006.07.006","journal-title":"Trends Neurosci"},{"key":"17_CR38","doi-asserted-by":"publisher","first-page":"23278","DOI":"10.1074\/jbc.M201084200","volume":"277","author":"KR Kozak","year":"2002","unstructured":"Kozak KR, Gupta RA, Moody JS et al (2002) 15-lipoxygenase metabolism of 2-arachidonylglycerol: generation of a peroxisome proliferator-activated receptor \u03b1 agonist. J Biol Chem 277:23278\u201323286. https:\/\/doi.org\/10.1074\/jbc.M201084200","journal-title":"J Biol Chem"},{"key":"17_CR39","doi-asserted-by":"publisher","first-page":"576","DOI":"10.1038\/sj.bjp.0707423","volume":"152","author":"SE O\u2019Sullivan","year":"2007","unstructured":"O\u2019Sullivan SE (2007) Cannabinoids go nuclear: evidence for activation of peroxisome proliferator-activated receptors. Br J Pharmacol 152:576\u2013582. https:\/\/doi.org\/10.1038\/sj.bjp.0707423","journal-title":"Br J Pharmacol"},{"key":"17_CR40","doi-asserted-by":"publisher","first-page":"452","DOI":"10.1038\/22761","volume":"400","author":"PM Zygmunt","year":"1999","unstructured":"Zygmunt PM, Petersson J, Andersson DA et al (1999) Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 400:452\u2013457","journal-title":"Nature"},{"key":"17_CR41","doi-asserted-by":"publisher","first-page":"5899","DOI":"10.1021\/cr2002799","volume":"111","author":"CA Rouzer","year":"2011","unstructured":"Rouzer CA, Marnett LJ (2011) Endocannabinoid oxygenation by cyclooxygenases, lipoxygenases, and cytochromes P450: cross-talk between the eicosanoid and endocannabinoid signaling pathways. Chem Rev 111:5899\u20135921. https:\/\/doi.org\/10.1021\/cr2002799","journal-title":"Chem Rev"},{"key":"17_CR42","doi-asserted-by":"publisher","first-page":"31532","DOI":"10.1074\/jbc.M111.237990","volume":"286","author":"R Yang","year":"2011","unstructured":"Yang R, Fredman G, Krishnamoorthy S et al (2011) Decoding functional metabolomics with docosahexaenoyl ethanolamide (DHEA) identifies novel bioactive signals\u2217. J Biol Chem 286:31532\u201331541. https:\/\/doi.org\/10.1074\/jbc.M111.237990","journal-title":"J Biol Chem"},{"key":"17_CR43","doi-asserted-by":"publisher","first-page":"163","DOI":"10.1016\/j.bioelechem.2018.11.014","volume":"126","author":"M Aoki","year":"2019","unstructured":"Aoki M, Matsumoto NM, Okubo Y, Ogawa R (2019) Bioelectrochemistry cytochrome P450 genes play central roles in transcriptional response by keratinocytes to a high-voltage alternating current electric fi eld. Bioelectrochemistry 126:163\u2013171. https:\/\/doi.org\/10.1016\/j.bioelechem.2018.11.014","journal-title":"Bioelectrochemistry"},{"key":"17_CR44","doi-asserted-by":"publisher","first-page":"965","DOI":"10.1124\/mol.108.053439","volume":"75","author":"NT Snider","year":"2009","unstructured":"Snider NT, Nast JA, Tesmer LA, Hollenberg PF (2009) A cytochrome P450-derived epoxygenated metabolite of anandamide is a potent cannabinoid receptor 2-selective agonist. Mol Pharmacol 75:965\u2013972. https:\/\/doi.org\/10.1124\/mol.108.053439","journal-title":"Mol Pharmacol"},{"key":"17_CR45","doi-asserted-by":"publisher","first-page":"136","DOI":"10.1124\/pr.109.001081","volume":"62","author":"NT Snider","year":"2010","unstructured":"Snider NT, Walker VJ, Hollenberg PF (2010) Oxidation of the endogenous cannabinoid arachidonoyl ethanolamide by the cytochrome P450 monooxygenases: physiological and pharmacological implications. Pharmacol Rev 62:136\u2013154. https:\/\/doi.org\/10.1124\/pr.109.001081","journal-title":"Pharmacol Rev"},{"key":"17_CR46","doi-asserted-by":"publisher","first-page":"537","DOI":"10.1124\/jpet.116.232553","volume":"357","author":"VJ Walker","year":"2016","unstructured":"Walker VJ, Griffin AP, Hammar DK, Hollenberg PF (2016) Metabolism of anandamide by human cytochrome P450 2J2 in the reconstituted system and human intestinal microsomes. J Pharmacol Exp Ther 357:537\u2013544. https:\/\/doi.org\/10.1124\/jpet.116.232553","journal-title":"J Pharmacol Exp Ther"},{"key":"17_CR47","doi-asserted-by":"publisher","first-page":"130","DOI":"10.1016\/j.prostaglandins.2013.05.002","volume":"104\u2013105","author":"BT Kalish","year":"2013","unstructured":"Kalish BT, Kieran MW, Puder M, Panigrahy D (2013) The growing role of eicosanoids in tissue regeneration, repair, and wound healing. Prostaglandins Other Lipid Mediat 104\u2013105:130\u2013138. https:\/\/doi.org\/10.1016\/j.prostaglandins.2013.05.002","journal-title":"Prostaglandins Other Lipid Mediat"},{"issue":"80","key":"17_CR48","doi-asserted-by":"publisher","first-page":"1276","DOI":"10.1126\/science.285.5431.1276","volume":"285","author":"K Node","year":"1999","unstructured":"Node K, Huo Y, Ruan X et al (1999) Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 285(80):1276\u20131279. https:\/\/doi.org\/10.1126\/science.285.5431.1276","journal-title":"Science"},{"key":"17_CR49","doi-asserted-by":"publisher","first-page":"782","DOI":"10.1038\/labinvest.2017.21","volume":"97","author":"H Zhao","year":"2017","unstructured":"Zhao H, Chen J, Chai J et\u00a0al (2017) Cytochrome P450 (CYP) epoxygenases as potential targets in the management of impaired diabetic wound healing. Lab Investig 97:782\u2013791. https:\/\/doi.org\/10.1038\/labinvest.2017.21","journal-title":"Lab Investig"},{"key":"17_CR50","doi-asserted-by":"publisher","first-page":"616","DOI":"10.1124\/jpet.114.216598","volume":"351","author":"DR McDougle","year":"2014","unstructured":"McDougle DR, Kambalyal A, Meling DD, Das A (2014) Endocannabinoids anandamide and 2-Arachidonoylglycerol are substrates for human CYP2J2 Epoxygenase. J Pharmacol Exp Ther 351:616\u2013627. https:\/\/doi.org\/10.1124\/jpet.114.216598","journal-title":"J Pharmacol Exp Ther"},{"key":"17_CR51","doi-asserted-by":"publisher","first-page":"590","DOI":"10.1124\/jpet.107.119321.hydrolysis","volume":"321","author":"NT Snider","year":"2007","unstructured":"Snider NT, Kornilov AM, Kent UM, Hollenberg PF (2007) Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. J Pharmacol Exp Ther 321:590\u2013597. https:\/\/doi.org\/10.1124\/jpet.107.119321.hydrolysis","journal-title":"J Pharmacol Exp Ther"},{"key":"17_CR52","doi-asserted-by":"publisher","first-page":"3947","DOI":"10.1021\/cr020443g","volume":"104","author":"B Meunier","year":"2004","unstructured":"Meunier B, de Visser SP, Shaik S (2004) Mechanism of oxidation reactions catalyzed by cytochrome P450 enzymes. Chem Rev 104:3947\u20133980. https:\/\/doi.org\/10.1021\/cr020443g","journal-title":"Chem Rev"},{"key":"17_CR53","doi-asserted-by":"publisher","first-page":"6402","DOI":"10.1073\/pnas.101119098","volume":"98","author":"A Berger","year":"2001","unstructured":"Berger A, Crozier G, Bisogno T et al (2001) Anandamide and diet: inclusion of dietary arachidonate and docosahexaenoate leads to increased brain levels of the corresponding N-acylethanolamines in piglets. Proc Natl Acad Sci 98:6402\u20136406. https:\/\/doi.org\/10.1073\/pnas.101119098","journal-title":"Proc Natl Acad Sci"},{"key":"17_CR54","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1111\/j.1471-4159.2010.06815.x","volume":"114","author":"M Dennis","year":"2010","unstructured":"Dennis M (2010) Inflammatory hyperalgesia induces essential bioactive lipid production in the spinal cord. J Neurochem 114:981\u2013993","journal-title":"J Neurochem"},{"key":"17_CR55","doi-asserted-by":"publisher","first-page":"300","DOI":"10.1006\/abbi.1999.1410","volume":"370","author":"T Bisogno","year":"1999","unstructured":"Bisogno T, Delton-Vandenbroucke I, Milone A, Lagarde MDMV (1999) Biosynthesis and inactivation of N-arachidonoylethanolamine (anandamide) and N-docosahexaenoylethanolamine in bovine retina. Arch Biochem Biophys 370:300\u2013307","journal-title":"Arch Biochem Biophys"},{"key":"17_CR56","doi-asserted-by":"publisher","first-page":"772","DOI":"10.1111\/bph.12030","volume":"169","author":"J Meijerink","year":"2013","unstructured":"Meijerink J, Balvers M, Witkamp R (2013) N-acyl amines of docosahexaenoic acid and other n-3 polyunsatured fatty acids\u00a0\u2013 from fishy endocannabinoids to potential leads. Br J Pharmacol 169:772\u2013783. https:\/\/doi.org\/10.1111\/bph.12030","journal-title":"Br J Pharmacol"},{"key":"17_CR57","first-page":"542","volume":"296","author":"X Cui","year":"2001","unstructured":"Cui X, Kawashima H, Barclay TB et al (2001) Molecular cloning and regulation of expression of two novel mouse CYP4F genes: expression in peroxisome proliferator-activated receptor alpha-deficient mice upon lipopolysaccharide and clofibrate challenges. J Pharmacol Exp Ther 296:542\u2013550","journal-title":"J Pharmacol Exp Ther"},{"key":"17_CR58","doi-asserted-by":"publisher","first-page":"437","DOI":"10.1111\/j.1471-4159.2005.03380.x","volume":"95","author":"K Maresz","year":"2005","unstructured":"Maresz K, Carrier EJ, Ponomarev ED et al (2005) Modulation of the cannabinoid CB2 receptor in microglial cells in response to inflammatory stimuli. J Neurochem 95:437\u2013445. https:\/\/doi.org\/10.1111\/j.1471-4159.2005.03380.x","journal-title":"J Neurochem"},{"key":"17_CR59","doi-asserted-by":"publisher","first-page":"6530","DOI":"10.1073\/pnas.1304321110","volume":"110","author":"G Zhang","year":"2013","unstructured":"Zhang G, Panigrahy D, Mahakian LM et al (2013) Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis. Proc Natl Acad Sci 110:6530\u20136535. https:\/\/doi.org\/10.1073\/pnas.1304321110","journal-title":"Proc Natl Acad Sci"},{"key":"17_CR60","doi-asserted-by":"publisher","first-page":"3032","DOI":"10.1021\/jm00072a026","volume":"36","author":"L Hanu\u0161","year":"1993","unstructured":"Hanu\u0161 L, Gopher A, Almog S, Mechoulam R (1993) Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J Med Chem 36:3032\u20133034. https:\/\/doi.org\/10.1021\/jm00072a026","journal-title":"J Med Chem"},{"key":"17_CR61","doi-asserted-by":"publisher","first-page":"471","DOI":"10.1021\/jm9505167","volume":"39","author":"BF Thomas","year":"1996","unstructured":"Thomas BF, Adams IB, Mascarella SW et al (1996) Structure-activity analysis of anandamide analogs: relationship to a cannabinoid pharmacophore. J Med Chem 39:471\u2013479. https:\/\/doi.org\/10.1021\/jm9505167","journal-title":"J Med Chem"},{"key":"17_CR62","doi-asserted-by":"publisher","first-page":"3481","DOI":"10.1194\/jlr.M006007","volume":"51","author":"C Morisseau","year":"2010","unstructured":"Morisseau C, Inceoglu B, Schmelzer K et al (2010) Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids. J Lipid Res 51:3481\u20133490. https:\/\/doi.org\/10.1194\/jlr.M006007","journal-title":"J Lipid Res"},{"key":"17_CR63","doi-asserted-by":"publisher","unstructured":"Coussens LM, Werb Z (2002) Inflammation and cancer. Pharmaceut Biotechnol 420(6917)860. Nature 420:860\u2013867. https:\/\/doi.org\/10.1038\/nature01322.Inflammation","DOI":"10.1038\/nature01322.Inflammation"},{"key":"17_CR64","doi-asserted-by":"publisher","first-page":"923","DOI":"10.1194\/jlr.P031260","volume":"54","author":"A Jaudszus","year":"2013","unstructured":"Jaudszus A, Gruen M, Watzl B et al (2013) Evaluation of suppressive and pro-resolving effects of EPA and DHA in human primary monocytes and T-helper cells. J Lipid Res 54:923\u2013935. https:\/\/doi.org\/10.1194\/jlr.P031260","journal-title":"J Lipid Res"},{"key":"17_CR65","doi-asserted-by":"publisher","first-page":"156","DOI":"10.1097\/MCO.0b013e32835d2d99","volume":"16","author":"A Laviano","year":"2013","unstructured":"Laviano A, Rianda S, Molfino A, Fanelli FR (2013) Omega-3 fatty acids in cancer. Curr Opin Clin Nutr Metab Care 16:156\u2013161. https:\/\/doi.org\/10.1097\/MCO.0b013e32835d2d99","journal-title":"Curr Opin Clin Nutr Metab Care"},{"key":"17_CR66","doi-asserted-by":"publisher","first-page":"1143","DOI":"10.1111\/j.1476-5381.2010.01113.x","volume":"162","author":"PH Cui","year":"2011","unstructured":"Cui PH, Petrovic N, Murray M (2011) The \u03c9-3 epoxide of eicosapentaenoic acid inhibits endothelial cell proliferation by p38 MAP kinase activation and cyclin D1\/CDK4 down-regulation. Br J Pharmacol 162:1143\u20131155. https:\/\/doi.org\/10.1111\/j.1476-5381.2010.01113.x","journal-title":"Br J Pharmacol"},{"key":"17_CR67","doi-asserted-by":"publisher","first-page":"6530","DOI":"10.1073\/pnas.1304321110\/-\/DCSupplemental","volume":"110","author":"Z Guodong","year":"2013","unstructured":"Guodong Z, Dipak P, Lisa MM et al (2013) Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis. Proc Natl Acad Sci 110:6530\u20136535. https:\/\/doi.org\/10.1073\/pnas.1304321110\/-\/DCSupplemental . www.pnas.org\/cgi\/doi\/10.1073\/pnas.1304321110","journal-title":"Proc Natl Acad Sci"},{"key":"17_CR68","doi-asserted-by":"publisher","first-page":"5569","DOI":"10.1021\/acs.jmedchem.8b00243","volume":"61","author":"J Roy","year":"2018","unstructured":"Roy J, Watson JE, Hong IS et al (2018) Antitumorigenic properties of omega-3 endocannabinoid epoxides. J Med Chem 61:5569\u20135579. https:\/\/doi.org\/10.1021\/acs.jmedchem.8b00243","journal-title":"J Med Chem"},{"key":"17_CR69","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1097\/FJC.0b013e3181506445","volume":"50","author":"BD Hammock","year":"2011","unstructured":"Hammock BD, Wagner Karen IB (2011) The soluble epoxide hydrolase as a pharmaceutical target for pain management. Pain Manag 50:383\u2013386. https:\/\/doi.org\/10.1097\/FJC.0b013e3181506445","journal-title":"Pain Manag"},{"key":"17_CR70","doi-asserted-by":"publisher","first-page":"7","DOI":"10.1016\/j.phrs.2015.04.001","volume":"97","author":"O Sasso","year":"2015","unstructured":"Sasso O, Wagner K, Morisseau C et al (2015) Peripheral FAAH and soluble epoxide hydrolase inhibitors are synergistically antinociceptive. Pharmacol Res 97:7\u201315. https:\/\/doi.org\/10.1016\/j.phrs.2015.04.001","journal-title":"Pharmacol Res"},{"key":"17_CR71","doi-asserted-by":"publisher","first-page":"24514","DOI":"10.1074\/jbc.M709873200","volume":"283","author":"JK Chen","year":"2008","unstructured":"Chen JK, Chen JK, Imig JD et al (2008) Identification of novel endogenous cytochrome P450 arachidonate metabolites with high affinity for cannabinoid receptors. J Biol Chem 283:24514\u201324524. https:\/\/doi.org\/10.1074\/jbc.M709873200","journal-title":"J Biol Chem"},{"key":"17_CR72","doi-asserted-by":"publisher","first-page":"817","DOI":"10.1042\/bj3510817","volume":"351","author":"T Bisogno","year":"2000","unstructured":"Bisogno T, Melck D, Bobrov M et al (2000) N-acyl-dopamines: novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem J 351:817. https:\/\/doi.org\/10.1042\/bj3510817","journal-title":"Biochem J"},{"key":"17_CR73","doi-asserted-by":"publisher","first-page":"225","DOI":"10.1080\/1475636031000080216","volume":"18","author":"CJ Fowler","year":"2003","unstructured":"Fowler CJ, Tiger G, L\u00f3pez-Rodr\u00edguez ML et al (2003) Inhibition of fatty acid amidohydrolase, the enzyme responsible for the metabolism of the endocannabinoid anandamide, by analogues of arachidonoyl-serotonin. J Enzyme Inhib Med Chem 18:225\u2013231. https:\/\/doi.org\/10.1080\/1475636031000080216","journal-title":"J Enzyme Inhib Med Chem"},{"key":"17_CR74","doi-asserted-by":"publisher","first-page":"823","DOI":"10.1016\/j.bbalip.2017.05.008","volume":"1862","author":"Y Wang","year":"2017","unstructured":"Wang Y, Balvers MGJ, Hendriks HFJ et al (2017) Docosahexaenoyl serotonin emerges as most potent inhibitor of IL-17 and CCL-20 released by blood mononuclear cells from a series of N-acyl serotonins identified in human intestinal tissue. Biochim Biophys Acta Mol Cell Biol Lipids 1862:823\u2013831. https:\/\/doi.org\/10.1016\/j.bbalip.2017.05.008","journal-title":"Biochim Biophys Acta Mol Cell Biol Lipids"}],"container-title":["Advances in Experimental Medicine and Biology","The Role of Bioactive Lipids in Cancer, Inflammation and Related Diseases"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1007\/978-3-030-21735-8_17","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,7,24]],"date-time":"2024-07-24T05:07:33Z","timestamp":1721797653000},"score":1,"resource":{"primary":{"URL":"http:\/\/link.springer.com\/10.1007\/978-3-030-21735-8_17"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019]]},"ISBN":["9783030216368","9783030217358"],"references-count":74,"URL":"https:\/\/doi.org\/10.1007\/978-3-030-21735-8_17","relation":{},"ISSN":["0065-2598","2214-8019"],"issn-type":[{"value":"0065-2598","type":"print"},{"value":"2214-8019","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019]]},"assertion":[{"value":"28 September 2019","order":1,"name":"first_online","label":"First Online","group":{"name":"ChapterHistory","label":"Chapter History"}}]}}