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Neural Plasticity
Volume 2016, Article ID 2426398, 13 pages
http://dx.doi.org/10.1155/2016/2426398
Review Article

Lipidomic Analysis of Endocannabinoid Signaling: Targeted Metabolite Identification and Quantification

1Department of Biological Sciences, Center for Plant Lipid Research, University of North Texas, Denton, TX 76203, USA
2Brookhaven National Laboratory, 50 Bell Avenue, Building 463, P.O. Box 5000, Upton, NY 11973-5000, USA

Received 1 July 2015; Accepted 9 September 2015

Academic Editor: Jean-François Bouchard

Copyright © 2016 Jantana Keereetaweep and Kent D. Chapman. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. W. A. Devane, F. A. Dysarz, M. R. Johnson, L. S. Melvin, and A. C. Howlett, “Determination and characterization of a cannabinoid receptor in rat brain,” Molecular Pharmacology, vol. 34, no. 5, pp. 605–613, 1988. View at Google Scholar · View at Scopus
  2. W. A. Devane, L. Hanus, A. Breuer et al., “Isolation and structure of a brain constituent that binds to the cannabinoid receptor,” Science, vol. 258, no. 5090, pp. 1946–1949, 1992. View at Publisher · View at Google Scholar · View at Scopus
  3. R. Mechoulam, S. Ben-Shabat, L. Hanus et al., “Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors,” Biochemical Pharmacology, vol. 50, no. 1, pp. 83–90, 1995. View at Publisher · View at Google Scholar · View at Scopus
  4. I. Matias, J. W. Wang, A. S. Moriello, A. Nieves, D. F. Woodward, and V. Di Marzo, “Changes in endocannabinoid and palmitoylethanolamide levels in eye tissues of patients with diabetic retinopathy and age-related macular degeneration,” Prostaglandins Leukotrienes and Essential Fatty Acids, vol. 75, no. 6, pp. 413–418, 2006. View at Publisher · View at Google Scholar · View at Scopus
  5. J. Chen, I. Matias, T. Dinh et al., “Finding of endocannabinoids in human eye tissues: implications for glaucoma,” Biochemical and Biophysical Research Communications, vol. 330, no. 4, pp. 1062–1067, 2005. View at Publisher · View at Google Scholar · View at Scopus
  6. C. Muguruza, M. Lehtonen, N. Aaltonen, B. Morentin, J. J. Meana, and L. F. Callado, “Quantification of endocannabinoids in postmortem brain of schizophrenic subjects,” Schizophrenia Research, vol. 148, no. 1–3, pp. 145–150, 2013. View at Publisher · View at Google Scholar · View at Scopus
  7. L. De Petrocellis and V. Di Marzo, “An introduction to the endocannabinoid system: from the early to the latest concepts,” Best Practice and Research: Clinical Endocrinology and Metabolism, vol. 23, no. 1, pp. 1–15, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. P. B. Smith, D. R. Compton, S. P. Welch, R. K. Razdan, R. Mechoulam, and B. R. Martin, “The pharmacological activity of anandamide, a putative endogenous cannabinoid, in mice,” Journal of Pharmacology and Experimental Therapeutics, vol. 270, no. 1, pp. 219–227, 1994. View at Google Scholar · View at Scopus
  9. J. R. Clapper, R. A. Mangieri, and D. Piomelli, “The endocannabinoid system as a target for the treatment of cannabis dependence,” Neuropharmacology, vol. 56, no. 1, pp. 235–243, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. A. Luchicchi and M. Pistis, “Anandamide and 2-arachidonoylglycerol: pharmacological properties, functional features, and emerging specificities of the two major endocannabinoids,” Molecular Neurobiology, vol. 46, no. 2, pp. 374–392, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. Y. Okamoto, J. Morishita, K. Tsuboi, T. Tonai, and N. Ueda, “Molecular characterization of a phospholipase D generating anandamide and its congeners,” The Journal of Biological Chemistry, vol. 279, no. 7, pp. 5298–5305, 2004. View at Publisher · View at Google Scholar · View at Scopus
  12. G. M. Simon and B. F. Cravatt, “Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain,” Journal of Biological Chemistry, vol. 283, no. 14, pp. 9341–9349, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. J. Liu, L. Wang, J. Harvey-White et al., “A biosynthetic pathway for anandamide,” Proceedings of the National Academy of Sciences of the United States of America, vol. 103, no. 36, pp. 13345–13350, 2006. View at Publisher · View at Google Scholar
  14. J. Liu, L. Wang, J. Harvey-White et al., “Multiple pathways involved in the biosynthesis of anandamide,” Neuropharmacology, vol. 54, no. 1, pp. 1–7, 2008. View at Publisher · View at Google Scholar · View at Scopus
  15. Y.-X. Sun, K. Tsuboi, Y. Okamoto et al., “Biosynthesis of anandamide and N-palmitoylethanolamine by sequential actions of phospholipase A2 and lysophospholipase D,” Biochemical Journal, vol. 380, no. 3, pp. 749–756, 2004. View at Publisher · View at Google Scholar · View at Scopus
  16. T. Bisogno, F. Howell, G. Williams et al., “Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain,” The Journal of Cell Biology, vol. 163, no. 3, pp. 463–468, 2003. View at Publisher · View at Google Scholar · View at Scopus
  17. B. F. Cravatt, D. K. Giang, S. P. Mayfield, D. L. Boger, R. A. Lerner, and N. B. Gilula, “Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides,” Nature, vol. 384, no. 6604, pp. 83–87, 1996. View at Publisher · View at Google Scholar · View at Scopus
  18. T. P. Dinh, D. Carpenter, F. M. Leslie et al., “Brain monoglyceride lipase participating in endocannabinoid inactivation,” Proceedings of the National Academy of Sciences of the United States of America, vol. 99, no. 16, pp. 10819–10824, 2002. View at Google Scholar
  19. G. Astarita and D. Piomelli, “Lipidomic analysis of endocannabinoid metabolism in biological samples,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 877, no. 26, pp. 2755–2767, 2009. View at Publisher · View at Google Scholar · View at Scopus
  20. H. H. O. Schmid, P. C. Schmid, and V. Natarajan, “The N-acylation-phosphodiesterase pathway and cell signalling,” Chemistry and Physics of Lipids, vol. 80, no. 1-2, pp. 133–142, 1996. View at Publisher · View at Google Scholar · View at Scopus
  21. N. R. Bachur, K. Masek, K. L. Melmon, and S. Udenfriend, “Fatty acid amides of ethanolamine in mammalian tissues,” The Journal of Biological Chemistry, vol. 240, pp. 1019–1024, 1965. View at Google Scholar · View at Scopus
  22. R. Mechoulam, E. Fride, and V. Di Marzo, “Endocannabinoids,” European Journal of Pharmacology, vol. 359, no. 1, pp. 1–18, 1998. View at Publisher · View at Google Scholar · View at Scopus
  23. D. E. Epps, P. C. Schmid, V. Natarajan, and H. H. O. Schmid, “N-acylethanolamine accumulation in infarcted myocardium,” Biochemical and Biophysical Research Communications, vol. 90, no. 2, pp. 628–633, 1979. View at Publisher · View at Google Scholar · View at Scopus
  24. A. Dlugos, E. Childs, K. L. Stuhr, C. J. Hillard, and H. De Wit, “Acute stress increases circulating anandamide and other N-acylethanolamines in healthy humans,” Neuropsychopharmacology, vol. 37, no. 11, pp. 2416–2427, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. E. V. Berdyshev, P. C. Schmid, Z. Dong, and H. H. O. Schmid, “Stress-induced generation of N-acylethanolamines in mouse epidermal JB6 P+ cells,” Biochemical Journal, vol. 346, no. 2, pp. 369–374, 2000. View at Publisher · View at Google Scholar · View at Scopus
  26. M. Degn, K. L. Lambertsen, G. Petersen et al., “Changes in brain levels of N-acylethanolamines and 2-arachidonoylglycerol in focal cerebral ischemia in mice,” Journal of Neurochemistry, vol. 103, no. 5, pp. 1907–1916, 2007. View at Publisher · View at Google Scholar · View at Scopus
  27. L. De Petrocellis, M. G. Cascio, and V. Di Marzo, “The endocannabinoid system: a general view and latest additions,” British Journal of Pharmacology, vol. 141, no. 5, pp. 765–774, 2004. View at Publisher · View at Google Scholar · View at Scopus
  28. P. Urquhart, A. Nicolaou, and D. F. Woodward, “Endocannabinoids and their oxygenation by cyclo-oxygenases, lipoxygenases and other oxygenases,” Biochimica et Biophysica Acta: Molecular and Cell Biology of Lipids, vol. 1851, no. 4, pp. 366–376, 2015. View at Publisher · View at Google Scholar · View at Scopus
  29. K. R. Kozak, B. C. Crews, J. D. Morrow et al., “Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides,” The Journal of Biological Chemistry, vol. 277, no. 47, pp. 44877–44885, 2002. View at Publisher · View at Google Scholar · View at Scopus
  30. K. R. Kozak, J. J. Prusakiewicz, and L. J. Marnett, “Oxidative metabolism of endocannabinoids by COX-2,” Current Pharmaceutical Design, vol. 10, no. 6, pp. 659–667, 2004. View at Publisher · View at Google Scholar · View at Scopus
  31. N. Sang and C. Chen, “Lipid signaling and synaptic plasticity,” Neuroscientist, vol. 12, no. 5, pp. 425–434, 2006. View at Publisher · View at Google Scholar · View at Scopus
  32. M. Yu, D. Ives, and C. S. Ramesha, “Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2,” Journal of Biological Chemistry, vol. 272, no. 34, pp. 21181–21186, 1997. View at Publisher · View at Google Scholar · View at Scopus
  33. R. S. Noecker, M. S. Dirks, N. T. Choplin, P. Bernstein, A. L. Batoosingh, and S. M. Whitcup, “A six-month randomized clinical trial comparing the intraocular pressure-lowering efficacy of bimatoprost and latanoprost in patients with ocular hypertension or glaucoma,” American Journal of Ophthalmology, vol. 135, no. 1, pp. 55–63, 2003. View at Publisher · View at Google Scholar · View at Scopus
  34. R. K. Parrish, P. Palmberg, and W.-P. Sheu, “A comparison of latanoprost, bimatoprost, and travoprost in patients with elevated intraocular pressure: a 12-week, randomized, masked-evaluator multicenter study,” American Journal of Ophthalmology, vol. 135, no. 5, pp. 688–703, 2003. View at Publisher · View at Google Scholar · View at Scopus
  35. D. F. Woodward, R. L. Phelps, A. H.-P. Krauss et al., “Bimatoprost: a novel antiglaucoma agent,” Cardiovascular Drug Reviews, vol. 22, no. 2, pp. 103–120, 2004. View at Google Scholar · View at Scopus
  36. W. S. Edgemond, C. J. Hillard, J. R. Falck, C. S. Kearn, and W. B. Campbell, “Human platelets and polymorphonuclear leukocytes synthesize oxygenated derivatives of arachidonylethanolamide (anandamide): their affinities for cannabinoid receptors and pathways of inactivation,” Molecular Pharmacology, vol. 54, no. 1, pp. 180–188, 1998. View at Google Scholar · View at Scopus
  37. S. J. Craib, H. C. Ellington, R. G. Pertwee, and R. A. Ross, “A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus,” British Journal of Pharmacology, vol. 134, no. 1, pp. 30–37, 2001. View at Publisher · View at Google Scholar · View at Scopus
  38. N. Ueda, K. Yamamoto, S. Yamamoto et al., “Lipoxygenase-catalyzed oxygenation of arachidonylethanolamide, a cannabinoid receptor agonist,” Biochimica et Biophysica Acta—Lipids and Lipid Metabolism, vol. 1254, no. 2, pp. 127–134, 1995. View at Publisher · View at Google Scholar · View at Scopus
  39. N. T. Snider, V. J. Walker, and P. F. Hollenberg, “Oxidation of the endogenous cannabinoid arachidonoyl ethanolamide by the cytochrome P450 monooxygenases: physiological and pharmacological implications,” Pharmacological Reviews, vol. 62, no. 1, pp. 136–154, 2010. View at Publisher · View at Google Scholar · View at Scopus
  40. M. Connor, C. W. Vaughan, and R. J. Vandenberg, “N-Acyl amino acids and N-acyl neurotransmitter conjugates: neuromodulators and probes for new drug targets,” British Journal of Pharmacology, vol. 160, no. 8, pp. 1857–1871, 2010. View at Publisher · View at Google Scholar · View at Scopus
  41. S. M. Huang, T. Bisogno, M. Trevisani et al., “An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors,” Proceedings of the National Academy of Sciences of the United States of America, vol. 99, no. 12, pp. 8400–8405, 2002. View at Publisher · View at Google Scholar · View at Scopus
  42. S. M. Huang, T. Bisogno, T. J. Petros et al., “Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain,” The Journal of Biological Chemistry, vol. 276, no. 46, pp. 42639–42644, 2001. View at Publisher · View at Google Scholar · View at Scopus
  43. S. Maione, L. de Petrocellis, V. de Novellis et al., “Analgesic actions of N-arachidonoyl-serotonin, a fatty acid amide hydrolase inhibitor with antagonistic activity at vanilloid TRPV1 receptors,” British Journal of Pharmacology, vol. 150, no. 6, pp. 766–781, 2007. View at Publisher · View at Google Scholar · View at Scopus
  44. B. F. Cravatt, O. Prospero-Garcia, G. Siuzdak et al., “Chemical characterization of a family of brain lipids that induce sleep,” Science, vol. 268, no. 5216, pp. 1506–1509, 1995. View at Publisher · View at Google Scholar · View at Scopus
  45. M. W. Buczynski and L. H. Parsons, “Quantification of brain endocannabinoid levels: methods, interpretations and pitfalls,” British Journal of Pharmacology, vol. 160, no. 3, pp. 423–442, 2010. View at Publisher · View at Google Scholar · View at Scopus
  46. D. Richardson, C. A. Ortori, V. Chapman, D. A. Kendall, and D. A. Barrett, “Quantitative profiling of endocannabinoids and related compounds in rat brain using liquid chromatography-tandem electrospray ionization mass spectrometry,” Analytical Biochemistry, vol. 360, no. 2, pp. 216–226, 2007. View at Publisher · View at Google Scholar · View at Scopus
  47. S. Hardison, S. T. Weintraub, and A. Giuffrida, “Quantification of endocannabinoids in rat biological samples by GC/MS: technical and theoretical considerations,” Prostaglandins and Other Lipid Mediators, vol. 81, no. 3-4, pp. 106–112, 2006. View at Publisher · View at Google Scholar · View at Scopus
  48. M. Lehtonen, M. Storvik, H. Malinen et al., “Determination of endocannabinoids in nematodes and human brain tissue by liquid chromatography electrospray ionization tandem mass spectrometry,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 879, no. 11-12, pp. 677–694, 2011. View at Publisher · View at Google Scholar · View at Scopus
  49. C. Nucci, V. Gasperi, R. Tartaglione et al., “Involvement of the endocannabinoid system in retinal damage after high intraocular pressure-induced ischemia in rats,” Investigative Ophthalmology & Visual Science, vol. 48, no. 7, pp. 2997–3004, 2007. View at Publisher · View at Google Scholar · View at Scopus
  50. A. Kilaru, G. Isaac, P. Tamura et al., “Lipid profiling reveals tissue-specific differences for ethanolamide lipids in mice lacking fatty acid amide hydrolase,” Lipids, vol. 45, no. 9, pp. 863–875, 2010. View at Publisher · View at Google Scholar · View at Scopus
  51. B. Yagen and S. Burstein, “Novel and sensitive method for the detection of anandamide by the use of its dansyl derivative,” Journal of Chromatography B: Biomedical Sciences and Applications, vol. 740, no. 1, pp. 93–99, 2000. View at Publisher · View at Google Scholar · View at Scopus
  52. A. A. Zoerner, F.-M. Gutzki, S. Batkai et al., “Quantification of endocannabinoids in biological systems by chromatography and mass spectrometry: a comprehensive review from an analytical and biological perspective,” Biochimica et Biophysica Acta, vol. 1811, no. 11, pp. 706–723, 2011. View at Publisher · View at Google Scholar · View at Scopus
  53. D. Schreiber, S. Harlfinger, B. M. Nolden et al., “Determination of anandamide and other fatty acyl ethanolamides in human serum by electrospray tandem mass spectrometry,” Analytical Biochemistry, vol. 361, no. 2, pp. 162–168, 2007. View at Publisher · View at Google Scholar · View at Scopus
  54. P. M. W. Lam, T. H. Marczylo, M. El-Talatini et al., “Ultra performance liquid chromatography tandem mass spectrometry method for the measurement of anandamide in human plasma,” Analytical Biochemistry, vol. 380, no. 2, pp. 195–201, 2008. View at Publisher · View at Google Scholar · View at Scopus
  55. J. T. Wood, J. S. Williams, L. Pandarinathan et al., “Comprehensive profiling of the human circulating endocannabinoid metabolome: clinical sampling and sample storage parameters,” Clinical Chemistry and Laboratory Medicine, vol. 46, no. 9, pp. 1289–1295, 2008. View at Publisher · View at Google Scholar · View at Scopus
  56. J. Palandra, J. Prusakiewicz, J. S. Ozer, Y. Zhang, and T. G. Heath, “Endogenous ethanolamide analysis in human plasma using HPLC tandem MS with electrospray ionization,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 877, no. 22, pp. 2052–2060, 2009. View at Publisher · View at Google Scholar · View at Scopus
  57. M. G. J. Balvers, K. C. M. Verhoeckx, and R. F. Witkamp, “Development and validation of a quantitative method for the determination of 12 endocannabinoids and related compounds in human plasma using liquid chromatography-tandem mass spectrometry,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 877, no. 14-15, pp. 1583–1590, 2009. View at Publisher · View at Google Scholar · View at Scopus
  58. C. A. Opitz, N. Rimmerman, Y. Zhang et al., “Production of the endocannabinoids anandamide and 2-arachidonoylglycerol by endothelial progenitor cells,” FEBS Letters, vol. 581, no. 25, pp. 4927–4931, 2007. View at Publisher · View at Google Scholar · View at Scopus
  59. J. Folch, M. Lees, and G. H. Sloane Stanley, “A simple method for the isolation and purification of total lipides from animal tissues,” Journal of Biological Chemistry, vol. 226, no. 1, pp. 497–509, 1957. View at Google Scholar · View at Scopus
  60. E. G. Bligh and W. J. Dyer, “A rapid method of total lipid extraction and purification,” Canadian Journal of Biochemistry and Physiology, vol. 37, no. 8, pp. 911–917, 1959. View at Publisher · View at Google Scholar · View at Scopus
  61. A. Giuffrida, F. Rodríguez de Fonseca, and D. Piomelli, “Quantification of bioactive acylethanolamides in rat plasma by electrospray mass spectrometry,” Analytical Biochemistry, vol. 280, no. 1, pp. 87–93, 2000. View at Publisher · View at Google Scholar · View at Scopus
  62. M. Lehtonen, M. Storvik, E. Tupala, P. Hyytiä, J. Tiihonen, and J. C. Callaway, “Endogenous cannabinoids in post-mortem brains of Cloninger type 1 and 2 alcoholics,” European Neuropsychopharmacology, vol. 20, no. 4, pp. 245–252, 2010. View at Publisher · View at Google Scholar · View at Scopus
  63. G. G. Muccioli and N. Stella, “An optimized GC-MS method detects nanomolar amounts of anandamide in mouse brain,” Analytical Biochemistry, vol. 373, no. 2, pp. 220–228, 2008. View at Publisher · View at Google Scholar · View at Scopus
  64. B. Tan, Y. W. Yu, M. F. Monn, H. V. Hughes, D. K. O'Dell, and J. M. Walker, “Targeted lipidomics approach for endogenous N-acyl amino acids in rat brain tissue,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 877, no. 26, pp. 2890–2894, 2009. View at Publisher · View at Google Scholar · View at Scopus
  65. S. Patel, D. J. Rademacher, and C. J. Hillard, “Differential regulation of the endocannabinoids anandamide and 2-arachidonylglycerol within the limbic forebrain by dopamine receptor activity,” Journal of Pharmacology and Experimental Therapeutics, vol. 306, no. 3, pp. 880–888, 2003. View at Publisher · View at Google Scholar · View at Scopus
  66. S. Patel, E. J. Carrier, V. Ho et al., “The postmortal accumulation of brain N-arachidonylethanolamine (anandamide) is dependent upon fatty acid amide hydrolase activity,” Journal of Lipid Research, vol. 46, no. 2, pp. 342–349, 2005. View at Publisher · View at Google Scholar · View at Scopus
  67. A. Fontana, V. Di Marzo, H. Cadas, and D. Piomelli, “Analysis of anandamide, an endogenous cannabinoid substance, and of other natural N-acylethanolamines,” Prostaglandins, Leukotrienes and Essential Fatty Acids, vol. 53, no. 4, pp. 301–308, 1995. View at Publisher · View at Google Scholar · View at Scopus
  68. F. Fezza, T. Bisogno, A. Minassi, G. Appendino, R. Mechoulam, and V. Di Marzo, “Noladin ether, a putative novel endocannabinoid: inactivation mechanisms and a sensitive method for its quantification in rat tissues,” FEBS Letters, vol. 513, no. 2-3, pp. 294–298, 2002. View at Publisher · View at Google Scholar · View at Scopus
  69. S. Oka, A. Tsuchie, A. Tokumura et al., “Ether-linked analogue of 2-arachidonoylglycerol (noladin ether) was not detected in the brains of various mammalian species,” Journal of Neurochemistry, vol. 85, no. 6, pp. 1374–1381, 2003. View at Publisher · View at Google Scholar · View at Scopus
  70. F. Fanelli, V. D. Di Lallo, I. Belluomo et al., “Estimation of reference intervals of five endocannabinoids and endocannabinoid related compounds in human plasma by two dimensional-LC/MS/MS,” Journal of Lipid Research, vol. 53, no. 3, pp. 481–493, 2012. View at Publisher · View at Google Scholar · View at Scopus
  71. D. S. Dumlao, M. W. Buczynski, P. C. Norris, R. Harkewicz, and E. A. Dennis, “High-throughput lipidomic analysis of fatty acid derived eicosanoids and N-acylethanolamines,” Biochimica et Biophysica Acta, vol. 1811, no. 11, pp. 724–736, 2011. View at Publisher · View at Google Scholar · View at Scopus
  72. P. C. Schmid, K. D. Schwartz, C. N. Smith, R. J. Krebsbach, E. V. Berdyshev, and H. H. O. Schmid, “A sensitive endocannabinoid assay. The simultaneous analysis of N-acylethanolamines and 2-monoacylglycerols,” Chemistry and Physics of Lipids, vol. 104, no. 2, pp. 185–191, 2000. View at Publisher · View at Google Scholar · View at Scopus
  73. T. Obata, Y. Sakurai, Y. Kase, Y. Tanifuji, and T. Horiguchi, “Simultaneous determination of endocannabinoids (arachidonylethanolamide and 2-arachidonylglycerol) and isoprostane (8-epiprostaglandin F2α) by gas chromatography-mass spectrometry-selected ion monitoring for medical samples,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 792, no. 1, pp. 131–140, 2003. View at Publisher · View at Google Scholar · View at Scopus
  74. B. J. Venables, C. A. Waggoner, and K. D. Chapman, “N-acylethanolamines in seeds of selected legumes,” Phytochemistry, vol. 66, no. 16, pp. 1913–1918, 2005. View at Publisher · View at Google Scholar · View at Scopus
  75. J. Keereetaweep, E. B. Blancaflor, E. Hornung, I. Feussner, and K. D. Chapman, “Ethanolamide oxylipins of linolenic acid can negatively regulate Arabidopsis seedling development,” Plant Cell, vol. 25, no. 10, pp. 3824–3840, 2013. View at Publisher · View at Google Scholar · View at Scopus
  76. L. Walter, A. Franklin, A. Witting, T. Möller, and N. Stella, “Astrocytes in culture produce anandamide and other acylethanolamides,” The Journal of Biological Chemistry, vol. 277, no. 23, pp. 20869–20876, 2002. View at Publisher · View at Google Scholar · View at Scopus
  77. A. Giuffrida and D. Piomelli, “Isotope dilution GC/MS determination of anandamide and other fatty acylethanolamides in rat blood plasma,” FEBS Letters, vol. 422, no. 3, pp. 373–376, 1998. View at Publisher · View at Google Scholar · View at Scopus
  78. K. Kempe, F.-F. Hsu, A. Bohrer, and J. Turk, “Isotope dilution mass spectrometric measurements indicate that arachidonylethanolamide, the proposed endogenous ligand of the cannabinoid receptor, accumulates in rat brain tissue post mortem but is contained at low levels in or is absent from fresh tissue,” Journal of Biological Chemistry, vol. 271, no. 29, pp. 17287–17295, 1996. View at Publisher · View at Google Scholar · View at Scopus
  79. A. A. Zoerner, F. M. Gutzki, M. T. Suchy et al., “Targeted stable-isotope dilution GC-MS/MS analysis of the endocannabinoid anandamide and other fatty acid ethanol amides in human plasma,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 877, no. 26, pp. 2909–2923, 2009. View at Publisher · View at Google Scholar · View at Scopus
  80. M. Maccarrone, M. Attinà, A. Cartoni, M. Bari, and A. Finazzi-Agrò, “Gas chromatography-mass spectrometry analysis of endogenous cannabinoids in healthy and tumoral human brain and human cells in culture,” Journal of Neurochemistry, vol. 76, no. 2, pp. 594–601, 2001. View at Publisher · View at Google Scholar · View at Scopus
  81. H. F. Kasai, M. Tsubuki, K. Takahashi, T. Honda, and H. Ueda, “Analyses of anandamide and endocannabinoid-like compounds using collision-induced dissociation in fast atom bombardment ionization-mass spectrometry and gas chromatography/chemical ionization-mass spectrometry,” Analytical Sciences, vol. 19, no. 12, pp. 1593–1598, 2003. View at Publisher · View at Google Scholar · View at Scopus
  82. T. C. Kirkham, C. M. Williams, F. Fezza, and V. Di Marzo, “Endocannabinoid levels in rat limbic forebrain and hypothalamus in relation to fasting, feeding and satiation: stimulation of eating by 2-arachidonoyl glycerol,” British Journal of Pharmacology, vol. 136, no. 4, pp. 550–557, 2002. View at Publisher · View at Google Scholar · View at Scopus
  83. D. Koga, T. Santa, T. Fukushima, H. Homma, and K. Imai, “Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric determination of anandamide and its analogs in rat brain and peripheral tissues,” Journal of Chromatography B: Biomedical Applications, vol. 690, no. 1-2, pp. 7–13, 1997. View at Publisher · View at Google Scholar · View at Scopus
  84. D. J. Liput, E. Tsakalozou, D. C. Hammell, K. S. Paudel, K. Nixon, and A. L. Stinchcomb, “Quantification of anandamide, oleoylethanolamide and palmitoylethanolamide in rodent brain tissue using high performance liquid chromatography-electrospray mass spectroscopy,” Journal of Pharmaceutical Analysis, vol. 4, no. 4, pp. 234–241, 2014. View at Publisher · View at Google Scholar · View at Scopus
  85. W. Jian, R. Edom, N. Weng, P. Zannikos, Z. Zhang, and H. Wang, “Validation and application of an LC-MS/MS method for quantitation of three fatty acid ethanolamides as biomarkers for fatty acid hydrolase inhibition in human plasma,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 878, no. 20, pp. 1687–1699, 2010. View at Publisher · View at Google Scholar · View at Scopus
  86. Y. Wang, Y. Liu, Y. Ito et al., “Simultaneous measurement of anandamide and 2-arachidonoylglycerol by polymyxin B-selective adsorption and subsequent high-performance liquid chromatography analysis: increase in endogenous cannabinoids in the sera of patients with endotoxic shock,” Analytical Biochemistry, vol. 294, no. 1, pp. 73–82, 2001. View at Publisher · View at Google Scholar · View at Scopus
  87. J. Williams, J. Wood, L. Pandarinathan et al., “Quantitative method for the profiling of the endocannabinoid metabolome by LC-atmospheric pressure chemical ionization-MS,” Analytical Chemistry, vol. 79, no. 15, pp. 5582–5593, 2007. View at Publisher · View at Google Scholar · View at Scopus
  88. A. A. Zoerner, S. Batkai, M.-T. Suchy et al., “Simultaneous UPLC-MS/MS quantification of the endocannabinoids 2-arachidonoyl glycerol (2AG), 1-arachidonoyl glycerol (1AG), and anandamide in human plasma: minimization of matrix-effects, 2AG/1AG isomerization and degradation by toluene solvent extraction,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 883-884, pp. 161–171, 2012. View at Publisher · View at Google Scholar · View at Scopus
  89. A. A. Amoako, T. H. Marczylo, P. M. W. Lam et al., “Quantitative analysis of anandamide and related acylethanolamides in human seminal plasma by ultra performance liquid chromatography tandem mass spectrometry,” Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, vol. 878, no. 31, pp. 3231–3237, 2010. View at Publisher · View at Google Scholar · View at Scopus
  90. P. J. Kingsley and L. J. Marnett, “Analysis of endocannabinoids by Ag+ coordination tandem mass spectrometry,” Analytical Biochemistry, vol. 314, no. 1, pp. 8–15, 2003. View at Publisher · View at Google Scholar · View at Scopus
  91. H. B. Bradshaw, N. Rimmerman, J. F. Krey, and J. M. Walker, “Sex and hormonal cycle differences in rat brain levels of pain-related cannabimimetic lipid mediators,” American Journal of Physiology—Regulatory Integrative and Comparative Physiology, vol. 291, no. 2, pp. R349–R358, 2006. View at Publisher · View at Google Scholar · View at Scopus
  92. N. Stella, P. Schweitzer, and D. Plomelli, “A second endogenous cannabinoid that modulates long-term potentiation,” Nature, vol. 388, no. 6644, pp. 773–778, 1997. View at Publisher · View at Google Scholar · View at Scopus