Analysis of ECs and related compounds in plasma: Artifactual isomerization and ex vivo enzymatic generation of 2-MGs

Journal of Lipid Research

Volumn 55, Issue 5, 2014, Pages 966-977

  Pastor, Antoni ^a,b   Farré, Magí ^a,b   Fitó, Montserrat ^c,d   Fernandez Aranda, Fernando ^c,e   De La Torre, Rafael ^a,c,f  

^a Human Pharmacology and Clinical Neurosciences Research Group Neuroscience Research Program Cardiovascular Risk and Nutrition Research Group   (Spain)

^b HOSPITAL DEL MAR   (Spain)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^d Instituto de Salud Carlos III   (Spain)

^e HOSPITAL UNIVERSITARI DE BELLVITGE   (Spain)

^f UNIVERSITAT POMPEU FABRA   (Spain)

Author keywords

2 arachidonoylglycerol; 2 monoacylglycerol; 2 oleoylglycerol; Endocannabinoids; Human; Orlistat; Validation

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 2 OLEOYLGLYCEROL; ENDOCANNABINOID; MONOACYLGLYCEROL; TETRAHYDROLIPSTATIN; UNCLASSIFIED DRUG; 2-ARACHIDONYLGLYCEROL; 2-OLEOYLGLYCEROL; ACYLGLYCEROL; ARACHIDONIC ACID DERIVATIVE; LACTONE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BLOOD ANALYSIS; COLD; CONTROLLED STUDY; EX VIVO STUDY; HUMAN; ISOMER; ISOMERIZATION; MALE; NORMAL HUMAN; PH; PRIORITY JOURNAL; ANTAGONISTS AND INHIBITORS; ARTIFACT; BLOOD; CHEMISTRY; DRUG STABILITY; FEMALE; ISOMERISM; METABOLISM; PROCEDURES; REPRODUCIBILITY;

ARACHIDONIC ACIDS; ARTIFACTS; BLOOD CHEMICAL ANALYSIS; DRUG STABILITY; ENDOCANNABINOIDS; FEMALE; GLYCERIDES; HUMANS; ISOMERISM; LACTONES; LIPASE; MALE; REPRODUCIBILITY OF RESULTS;

EID: 84899558014     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.D043794     Document Type: Article

References (31)

1. Montecucco, F., and V. Di Marzo. 2012. At the heart of the matter: the endocannabinoid system in cardiovascular function and dysfunction. Trends Pharmacol. Sci. 33 : 331-340.
2. Bilkei-Gorzo, A. 2012. The endocannabinoid system in normal and pathological brain ageing. Philos. Trans. R. Soc. Lond. B Biol. Sci. 367 : 3326-3341.
3. Giuffrida, A., and A. Seillier. 2012. New insights on endocannabinoid transmission in psychomotor disorders. Prog. Neuropsychopharmacol. Biol. Psychiatry. 38 : 51-58.
4. Ashton, C. H., and P. B. Moore. 2011. Endocannabinoid system dysfunction in mood and related disorders. Acta Psychiatr. Scand. 124 : 250-261.
5. Monteleone, P. 2011. New frontiers in endocrinology of eating disorders. Curr. Top. Behav. Neurosci. 6 : 189-208.
6. Ben-Shabat, S., E. Fride, T. Sheskin, T. Tamiri, M. H. Rhee, Z. Vogel, T. Bisogno, L. De Petrocellis, V. Di Marzo, and R. Mechoulam. 1998. An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity. Eur. J. Pharmacol. 353 : 23-31.
7. Hansen, K. B., M. M. Rosenkilde, F. K. Knop, N. Wellner, T. A. Diep, J. F. Rehfeld, U. B. Andersen, J. J. Holst, and H. S. Hansen. 2011. 2-Oleoyl glycerol is a GPR119 agonist and signals GLP-1 release in humans. J. Clin. Endocrinol. Metab. 96 : E1409-E1417.
8. Syed, S. K., H. H. Bui, L. S. Beavers, T. B. Farb, J. Ficorilli, A. K. Chesterfield, M-S. Kuo, K. Bokvist, D. G. Barrett, and A. M. Efanov. 2012. Regulation of GPR119 receptor activity with endocannabinoidlike lipids. Am. J. Physiol. Endocrinol. Metab. 303 : E1469-E1478.
9. Borrelli, F., and A. Izzo. 2009. Role of acylethanolamides in the gastrointestinal tract with special reference to food intake and energy balance. Best Pract. Res. Clin. Endocrinol. Metab. 23 : 33-49.
10. Brown, I., M. G. Cascio, K. W. J. Wahle, R. Smoum, R. Mechoulam, R. A. Ross, R. G. Pertwee, and S. D. Heys. 2010. Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis. 31 : 1584-1591.
11. Yang, R., G. Fredman, S. Krishnamoorthy, N. Agrawal, D. Irimia, D. Piomelli, and C. N. Serhan. 2011. Decoding functional metabolomics with docosahexaenoyl ethanolamide (DHEA) identifies novel bioactive signals. J. Biol. Chem. 286 : 31532-31541.
12. Fanelli, F., V. D. Di Lallo, I. Belluomo, and R. De Iasio. 2012. Estimation of reference intervals of five endocannabinoids and endocannabinoid related compounds in human plasma by two dimensional-LC/MS/MS. J. Lipid Res. 53 : 481-493.
13. Zoerner, A. A., F. M. Gutzki, S. Batkai, M. May, C. Rakers, S. Engeli, J. Jordan, and D. Tsikas. 2011. Quantification of endocannabinoids in biological systems by chromatography and mass spectrometry: a comprehensive review from an analytical and biological perspective. Biochim. Biophys. Acta. 1811 : 706-723.
14. Zoerner, A. A., S. Batkai, M. T. Suchy, F. M. Gutzki, S. Engeli, J. Jordan, and D. Tsikas. 2012. 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. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 883-884 : 161-171.
15. Di Marzo, V. 2011. Endocannabinoid signaling in the brain: biosynthetic mechanisms in the limelight. Nat. Neurosci. 14 : 9-15.
16. Bisogno, T., F. Howell, G. Williams, A. Minassi, M. G. Cascio, A. Ligresti, I. Matias, A. Schiano-Moriello, P. Paul, E-J. Williams, et al. 2003. Cloning of the first sn1-DAG lipases points to the spatial and temporal regulation of endocannabinoid signaling in the brain. J. Cell Biol. 163 : 463-468.
17. Rouzer, C. A., K. Ghebreselasie, and L. J. Marnett. 2002. Chemical stability of 2-arachidonylglycerol under biological conditions. Chem. Phys. Lipids. 119 : 69-82.
18. Jian, W., R. Edom, N. Weng, P. Zannikos, Z. Zhang, and H. Wang. 2010. 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. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 878 : 1687-1699.
19. Iannotti, F. A., F. Piscitelli, A. Martella, E. Mazzarella, M. Allarà, V. Palmieri, C. Parrella, R. Capasso, and V. Di Marzo. 2013. Analysis of the "endocannabinoidome" in peripheral tissues of obese Zucker rats. Prostaglandins Leukot. Essent. Fatty Acids. 89 : 127-135.
20. Zoerner, A. A., F. M. Gutzki, M. T. Suchy, B. Beckmann, S. Engeli, J. Jordan, and D. Tsikas. 2009. Targeted stable-isotope dilution GC-MS/MS analysis of the endocannabinoid anandamide and other fatty acid ethanol amides in human plasma. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 877 : 2909-2923.
21. Skonberg, C., A. Artmann, C. Cornett, S. H. Hansen, and H. S. Hansen. 2010. Pitfalls in the sample preparation and analysis of N-acylethanolamines. J. Lipid Res. 51 : 3062-3073.
22. Sternby, B., D. Hartmann, B. Borgström, and A. Nilsson. 2002. Degree of in vivo inhibition of human gastric and pancreatic lipases by Orlistat (tetrahydrolipstatin, THL) in the stomach and small intestine. Clin. Nutr. 21 : 395-402.
23. Hoover, H. S., J. L. Blankman, S. Niessen, and B. F. Cravatt. 2008. Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling. Bioorg. Med. Chem. Lett. 18 : 5838-5841.
24. Hsu, K. L., K. Tsuboi, A. Adibekian, H. Pugh, K. Masuda, and B. F. Cravatt. 2012. DAGL β inhibition perturbs a lipid network involved in macrophage inflammatory responses. Nat. Chem. Biol. 8 : 999-1007.
25. Mattson, F. H., and R. A. Volpenhein. 1964. The digestion and absorption of triglycerides. J. Biol. Chem. 239 : 2772-2777.
26. Mu, H., and C. E. Høy. 2004. The digestion of dietary triacylglycerols. Prog. Lipid Res. 43 : 105-133.
27. Kindel, T., D. M. Lee, and P. Tso. 2010. The mechanism of the formation and secretion of chylomicrons. Atheroscler. Suppl. 11 : 11-16.
28. Karpe, F., T. Olivecrona, G. Walldius, and A. Hamsten. 1992. Lipoprotein lipase in plasma after an oral fat load: relation to free fatty acids. J. Lipid Res. 33 : 975-984.
29. Goodman, K. B., M. J. Bury, M. Cheung, M. A. Cichy-Knight, S. E. Dowdell, A. K. Dunn, D. Lee, J. A. Lieby, M. L. Moore, D. A. Scherzer, et al. 2009. Discovery of potent, selective sulfonylfuran urea endothelial lipase inhibitors. Bioorg. Med. Chem. Lett. 19 : 27-30.
30. Hofmann, A. F., and B. Borgstrom. 1963. Hydrolysis of long-chain monoglycerides in micellar solution by pancreatic lipase. Biochim. Biophys. Acta. 70 : 317-331.
31. Buczynski, M. W., and L. H. Parsons. 2010. Quantification of brain endocannabinoid levels: methods, interpretations and pitfalls. Br. J. Pharmacol. 160 : 423-442.