Literature Survey

Analysis of Anandamide and other Biologically Active Amides

Anandamide and other biologically active amides are currently attracting great interest because of their important biological functions. The following references were collected as part of our regular literature reviews for our own research purposes, and therefore reflect our personal research interests. We are sure that we have not covered the subject exhaustively, but we have done our best. We hope that this will be a good starting point at least. References are listed alphabetically by the first author of a paper, but not necessarily chronologically by that author. The survey covers the years 1990 onwards, and will be updated at approximately six-monthly intervals.

  • Anagnostopoulos, D., Rakiec,C., Wood,J., Pandarinathan,L., Zvonok,N., Makriyannis,A. and Siafaka-Kapadai,A. Identification of endocannabinoids and related N-acylethanolamines in tetrahymena. A new class of compounds for Tetrahymena. Protist, 161, 452-465 (2010).
  • Arai,Y., Fukushima,T., Shirao,M., Yang,X.J. and Imai,K. Sensitive determination of anandamide in rat brain utilizing a coupled-column HPLC with fluorimetric detection. Biomed. Chromatogr., 14, 118-124 (2000).
  • Astarita, G. and Piomelli,D. Lipidomic analysis of endocannabinoid metabolism in biological samples. J. Chromatogr. B, 877, 2755-2767 (2009).
  • Balvers, M.G.J., Verhoeckx, K.C.M., Meijerink, J., Wortelboer, H.M. and Witkamp, R.F. Measurement of palmitoylethanolamide and other N-acylethanolamines during physiological and pathological conditions. CNS & Neur. Disorders-Drug Targets, 12, 26-33 (2013).
  • Balvers, M.G.J., Verhoeckx,K.C.M. and Witkamp,R.F. 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. J. Chromatogr. B, 877, 1583-1590 (2009).
  • Balvers, M.G.J., Wortelboer, H.M., Witkamp, R.F. and Verhoeckx, K.C.M. Liquid chromatography-tandem mass spectrometry analysis of free and esterified fatty acid N-acyl ethanolamines in plasma and blood cells. Anal. Biochem., 434, 275-283 (2013).
  • Bazinet, R.P., Lee,H.J., Felder,C.C., Porter,A.C., Rapoport,S.I. and Rosenberger,T.A. Rapid high-energy microwave fixation is required to determine the anandamide (N-arachidonoylethanolamine) concentration of rat brain. Neurochem. Res., 30, 597-601 (2005).
  • Bilyk, A., Piazza,G.J., Bistline,R.G. and Haas,M.J. Separation of cholesterol, and fatty acylglycerols, acids and amides by TLC. Lipids, 26, 405-406 (1991).
  • Bisogno, T., Piscitelli,F. and Di Marzo,V. Lipidomic methodologies applicable to the study of endocannabinoids and related compounds: Endocannabinoidomics. Eur. J. Lipid Sci. Technol., 111, 53-63 (2009).
  • Brown, I., Wahle,K.W.J., Cascio,M.G., Smoum-Jaouni,R., Mechoulam,R., Pertwee,R.G. and Heys,S.D. Omega-3 N-acylethanolamines are endogenously synthesised from omega-3 fatty acids in different human prostate and breast cancer cell lines. Prostaglandins Leukotrienes Essential Fatty Acids, 85, 305-310 (2011).
  • Buczynski, M.W., Svensson,C.I., Dumlao,D.S., Fitzsimmons,B.L., Shim,J.H., Scherbart,T.J., Jacobsen,F.E., Hua,X.Y., Yaksh,T.L. and Dennis,E.A. Inflammatory hyperalgesia induces essential bioactive lipid production in the spinal cord. J. Neurochem., 114, 981-993 (2010).
  • Carbonare, M.D., Tonidandel,L., Berto,F., Luise,D., Mardegan,A., Giordano,G., Da Dalt,L., Guiotto,A., Battistin,L., Leon,A. and Traldi,P. Identification of an unusual naturally occurring apolar fatty acid amide in mammalian brain and a method for its quantitative determination. Rapid Commun. Mass Spectrom., 20, 353-360 (2006).
  • Carpenter, T., Poore,D.D., Gee,A.J., Deshpande,P., Merkler,D.J. and Johnson,M.E. Use of reversed phase HP liquid chromatography to assay conversion of N-acylglycines to primary fatty acid amides by peptidylglycine-alpha-amidating monooxygenase. J. Chromatogr. B, 809, 15-21 (2004).
  • Chapman, K.D., Venables,B.J., Diana,E.E. and Gross,G.W. Identification and quantification of neuroactive acylethanolamines in cottonseed processing fractions. J. Am. Oil Chem. Soc., 80, 223-229 (2003).
  • Chen, J., Paudel,K.S., Derbenev,A.V., Smith,B.N. and Stinchcomb,A.L. Simultaneous quantification of anandamide and other endocannabinoids in dorsal vagal complex of rat brainstem by LC-MS. Chromatographia, 69, 1-7 (2009).
  • Chou, H.J. Determination of diethanolamine and N-nitrosodiethanolamine in fatty acid diethanolamides. J. Ass. Off. Anal. Chem. Int., 81, 943-947 (1998).
  • Cravatt, B.F., Lerner,R.A. and Boger,D.L. Structure determination of an endogenous sleep-inducing lipid, cis-9-octadecenamide (oleamide): a synthetic approach to the chemical analysis of trace quantities of a natural product. J. Am. Chem. Soc., 118, 580-590 (1996).
  • Divito, E.B., Davic, A.P., Johnson, M.E. and Cascio, M. Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides. Anal. Chem., 84, 2388-2394 (2012).
  • Dumlao, D.S., Buczynski,M.W., Norris,P.C., Harkewicz,R. and Dennis,E.A. High-throughput lipidomic analysis of fatty acid derived eicosanoids and N-acylethanolamines. Biochim. Biophys. Acta, 1811, 724-736 (2011)
  • Fanelli, F., Di Lallo, V.D., Belluomo, I., De Iasio, R., Baccini, M., Casadio, E., Gasparini, D.I., Colavita, M., Gambineri, A., Grossi, G., Vicennati, V., Pasquali, R. and Pagotto, U. 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 (2012).
  • Fontana, A., Dimarzo,V., Cadas,H. and Piomelli,D. Analysis of anandamide, an endogenous cannabinoid substance, and of other natural N-acylethanolamines. Prostaglandins Leukotrienes Essential Fatty Acids, 53, 301-308 (1995).
  • Gee, A.J., Groen,L.A. and Johnson,M.E. Ion trap mass spectrometry of trimethylsilylamides following gas chromatography. J. Mass Spectrom., 35, 305-310 (2000).
  • Gee, A.J., Groen,L.A. and Johnson,M.E. Determination of fatty acid amides as trimethylsilyl derivatives by gas chromatography with mass spectrometric detection. J. Chromatogr. A, 849, 541-552 (1999).
  • Giuffrida, A. and Piomelli,D. Isotope dilution GC/MS determination of anandamide and other fatty acylethanolamides in rat blood plasma. FEBS Letts, 422, 373-376 (1998).
  • Giuffrida, A., de Fonseca,F.R. and Piomelli,D. Quantification of bioactive acylethanolamides in rat plasma by electrospray mass spectrometry. Anal. Biochem., 280, 87-93 (2000).
  • Glass, M., Hong,J.W., Sato,T.A. and Mitchell,M.D. Misidentification of prostamides as prostaglandins. J. Lipid Res., 46, 1364-1368 (2005).
  • Gonthier, M.-P., Hoareau,L., Festy,F., Matias,I., Valenti,M., Bes-Houtmann,S., Rouch,C., Silva,C.R.-D., Chesne,S., d'Hellencourt,C.L.), Cesari,M., Di Marzo,V. and Roche,R. Identification of endocannabinoids and related compounds in human fat cells. Obesity, 15, 837-845 (2007).
  • Gryff-Keller, A., Kraska-Dziadecka, A. and Kubica, D. Detection of acylglycines in urine by H-1 and C-13 NMR for the diagnosis of inborn metabolic diseases. Acta Biochim. Pol., 59, 613-617 (2012).
  • Gunstone, F.D. High-resolution 13C NMR spectra of long-chain acids, methyl esters, glycerol esters, nitriles, amides, alcohols and acetates. Chem. Phys. Lipids, 66, 189-193 (1993).
  • Hamberger, A. and Stenhagen,G. Erucamide as a modulator of water balance: New function of a fatty acid amide. Neurochem. Res., 28, 177-185 (2003).
  • Han, B.N., McPhail,K.L., Ligresti,A., Di Marzo,V. and Gerwick,W.H. Semiplenamides A-G, fatty acid amides from a Papua New Guinea collection of the marine cyanobacterium Lyngbya semiplena. J. Nat. Prod., 66, 1364-1368 (2003).
  • Han, B.N., Wright, R., Kirchhoff, A.M., Chester, J.A., Cooper, B.R., Davisson, V.J. and Barker, E. Quantitative LC-MS/MS analysis of arachidonoyl amino acids in mouse brain with treatment of FAAH inhibitor. Anal. Biochem., 432, 74-81 (2013).
  • Hanus, L.O., Fales,H.M., Spande,T.F. and Basile,A.S. A gas chromatographic-mass spectral assay for the quantitative determination of oleamide in biological fluids. Anal. Biochem., 270, 159-166 (1999).
  • Hardison, S., Weintraub,S.T. and Giuffrida,A. Quantification of endocannabinoids in rat biological samples by GC/MS: Technical and theoretical considerations. Prostaglandins Other Lipid Mediators, 81, 106-112 (2006).
  • Jian, W.Y., Edom,R., Weng,N.D., Zannikos,P., Zhang,Z.M. and Wang,H. 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, 878, 1687-1699 (2010).
  • Jung, H.J., Lee,W.Y., Yoo,Y.S., Chung,B.C. and Choi,M.H. Database-dependent metabolite profiling focused on steroid and fatty acid derivatives using high-temperature gas chromatography-mass spectrometry. Clin. Chim. Acta, 411, 818-824 (2010).
  • Kaphalia, B.S.and Ansari,G.A.S. Single step thin-layer chromatographic method for quantitation of enzymatic formation of fatty acid anilides. J. Chromatogr. B, 705, 269-275 (1998).
  • Kasai, H.F., Tsubuki,M. and Honda,T. Studies on high-energy collision-induced dissociation of endogenous cannabinoids: 2-arachidonoylglycerol and N-arachidonoylethanolamide in FAB-mass spectrometry. Anal. Sci., 22, 921-930 (2006).
  • Kasai, H.F., Tsubuki,M., Takahashi,K., Honda,T. and Ueda,H. 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. Anal. Sci., 19, 1593-1598 (2003).
  • Kilaru, A., Isaac,G., Tamura,P., Baxter,D., Duncan,S.R., Venables,B.J., Welti, R., Koulen,P. and Chapman,K.D. Lipid profiling reveals tissue-specific differences for ethanolamide lipids in mice lacking fatty acid amide hydrolase. Lipids, 45, 863-875 (2010).
  • Kingsley, P.J. and Marnett,L.J. Analysis of endocannabinoids by Ag+ coordination tandem mass spectrometry. Anal. Biochem., 314, 8-15 (2003).
  • Kingsley, P.J. and Marnett,L.J. LC-MS-MS analysis of neutral eicosanoids. Methods Enzymol., 433, 91-112 (2007).
  • Kingsley, P.J. and Marnett,L.J. Analysis of endocannabinoids, their congeners and COX-2 metabolites. J. Chromatogr. B, 877, 2746-2754 (2009).
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  • Lam, P.M.W., Marczylo,T.H. and Konje,J.C. Simultaneous measurement of three N-acylethanolamides in human bio-matrices using ultra performance liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem., 398, 2089-2097 (2010).
  • Lam, P.M.W., Marczylo,T.H., El-Talatini,M., Finney,M., Nallendran,V., Taylor,A.H. and Konje,J.C. Ultra performance liquid chromatography tandem mass spectrometry method for the measurement of anandamide in human plasma. Anal. Biochem., 380, 195-201 (2008).
  • Lehtonen, M., Reisner,K., Auriola,S., Wong,G. and Callaway,J.C. Mass-spectrometric identification of anandamide and 2-arachidonoylglycerol in nematodes. Chem. Biodiversity, 5, 2431-2441 (2008).
  • Lehtonen, M., Storvik,M., Malinen,H., Hyytia,P., Lakso,M., Auriola,S., Wong,G. and Callaway,J.C. Determination of endocannabinoids in nematodes and human brain tissue by liquid chromatography electrospray ionization tandem mass spectrometry. J. Chromatogr. B, 879, 677-694 (2011).
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February 5, 2014