Mass-Spectrometric Identification of Anandamide and 2-Arachidonoylglycerol in Nematodes
Marko Lehtonen
Department of Pharmaceutical Chemistry, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorKaja Reisner
Department of Neurobiology, A. I. Virtanen Institute for Molecular Sciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio (fax: +358 17 162 456)
Institute of Molecular and Cell Biology, University of Tartu, Riia 23, Tartu 51010, Estonia
Search for more papers by this authorSeppo Auriola
Department of Pharmaceutical Chemistry, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorGarry Wong
Department of Neurobiology, A. I. Virtanen Institute for Molecular Sciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio (fax: +358 17 162 456)
Department of Biosciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorJames C. Callaway
Department of Neurobiology, A. I. Virtanen Institute for Molecular Sciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio (fax: +358 17 162 456)
Department of Biosciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorMarko Lehtonen
Department of Pharmaceutical Chemistry, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorKaja Reisner
Department of Neurobiology, A. I. Virtanen Institute for Molecular Sciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio (fax: +358 17 162 456)
Institute of Molecular and Cell Biology, University of Tartu, Riia 23, Tartu 51010, Estonia
Search for more papers by this authorSeppo Auriola
Department of Pharmaceutical Chemistry, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorGarry Wong
Department of Neurobiology, A. I. Virtanen Institute for Molecular Sciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio (fax: +358 17 162 456)
Department of Biosciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorJames C. Callaway
Department of Neurobiology, A. I. Virtanen Institute for Molecular Sciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio (fax: +358 17 162 456)
Department of Biosciences, University of Kuopio, P. O. Box 1627, FI-70211 Kuopio
Search for more papers by this authorAbstract
The purpose of the study was to see if nematodes (Caenorhabditis elegans, Caenorhabditis briggsae, and Pelodera strongyloides) produce endocannabinoids; i.e., anandamide (AEA) and 2-arachidonoylglycerol (2-AG). In this study, AEA and 2-AG were identified as endogenous products from nematodes by using electrospray-ionization ion-trap MS/MS (ESI-IT-MS) experiments operated in the positive-ionization mode. Endocannabinoids were identified by product ion scan and concentrations were measured by triple quadrupole mass spectrometry in the multiple reaction monitoring mode (MRM). Both AEA and 2-AG were identified in all of the nematode samples, even though these species lack known cannabinoid receptors. Neither AEA nor 2-AG were detected in the fat-3 mutant of C. elegans, which lacks the necessary enzyme to produce arachidonic acid, the fatty acid precursor of these endocannabinoids.
References
- 1 W. A. Devane, L. Hanus, A. Breuer, R. G. Pertwee, L. A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, R. Mechoulam, Science 1992, 258, 1946.
- 2 R. Mechoulam, S. Ben-Shabat, L. Hanus, M. Ligumsky, N. E. Kaminski, A. R. Schatz, A. Gopher, S. Almog, B. R. Martin, D. R. Compton, R. G. Pertwee, G. Griffin, M. Bayewitch, J. Barg, Z. Vogel, Biochem. Pharmacol. 1995, 50, 83.
- 3 T. Bisogno, A. Ligresti, V. Di Marzo, Pharmacol., Biochem. Behav. 2005, 81, 224.
- 4 V. Di Marzo, L. De Petrocellis, F. Fezza, A. Ligresti, T. Bisogno, Prostaglandins, Leukotrienes Essent. Fatty Acids 2002, 66, 377.
- 5 V. Di Marzo, C. S. Breivogel, Q. Tao, D. T. Bridgen, R. K. Razdan, A. M. Zimmer, A. Zimmer, B. R. Martin, J. Neurochem. 2000, 75, 2434.
- 6 P. M. Zygmunt, J. Petersson, D. A. Andersson, H. Chuang, M. Sørgård, V. Di Marzo, D. Julius & E. D. Högestätt, Nature 1999, 400, 452.
- 7
J. M. McPartland, P. L. Pruitt, J. Cannabis Ther. 2002, 1, 73.
10.1300/J175v02n01_04 Google Scholar
- 8 J. E. Lauckner, J. B. Jensen, H.-Y. Chen, H.-C. Lu, B. Hille, K. Mackie, Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 2699.
- 9 J. M. McPartland, Brain Res. Rev. 2004, 45, 18.
- 10 J. M. McPartland, I. Matias, V. Di Marzo, M. Glass, Gene 2006, 370, 64.
- 11 J. M. McPartland, J. Agraval, D. Gleeson, K. Heasman, M. Glass, J. Evol. Biol. 2006, 19, 366.
- 12 M. Salzet, G. B. Stefano, Prostaglandins, Leukotrienes Essent. Fatty Acids 2002, 66, 353.
- 13 L. De Petrocellis, D. Melck, T. Bisogno, A. Milone, V. Di Marzo, Neuroscience 1999, 92, 377.
- 14 I. Matias, J. M. McPartland, V. Di Marzo, J. Neurochem. 2005, 93, 1141.
- 15 F. Fezza, J. W. Dillwith, T. Bisogno, J. S. Tucker, V. Di Marzo, J. R. Sauer, Biochim. Biophys. Acta 2003, 1633, 61.
- 16 L. De Petrocellis, D. Melck, T. Bisogno, V. Di Marzo, Chem. Phys. Lipid 2000, 108, 191.
- 17 J. M. McPartland, V. Di Marzo, L. De Petrocellis, A. Mercer, M. Glass, J. Comp. Neurol. 2001, 436, 423.
- 18 R. Wilson, R. Ainscough, K. Anderson, C. Baynes, M. Berks, J. Bonfield, J. Burton, M. Connell, T. Copsey, J. Cooper, A. Coulson, M. Craxton, S. Dear, Z. Du, R. Durbin, A. Favello, A. Fraser, L. Fulton, A. Gardner, P. Green, T. Hawkins, L. Hillier, M. Jier, L. Johnston, M. Jones, J. Kershaw, J. Kirsten, N. Laisster, P. Latreille, J. Lightning, C. Lloyd, B. Mortimore, M. O'Callaghan, J. Parsons, C. Percy, L. Rifken, A. Roopra, D. Saunders, R. Shownkeen, M. Sims, N. Smaldon, A. Smith, M. Smith, E. Sonnhammer, R. Staden, J. Sulston, J. Thierry-Mieg, K. Thomas, M. Vaudin, K. Vaughan, R. Waterston, A. Watson, L. Weinstock, J. Wilkinson-Sproat & P. Wohldman, Nature 1994, 368, 32.
- 19 J. M. McPartland, M. Glass, Gene 2003, 312, 297.
- 20 M. R. Elphick, M. Egertova, Philos. Trans. R. Soc. London, Ser. B 2001, 356, 381.
- 21 J. G. Wallis, J. L. Watts, J. Browse, Trends Biochem. Sci. 2002, 27, 467.
- 22 J. Watts, J. Browse, Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5854.
- 23 N. G. Bazan, J. Lipid Res. 2003, 44, 2221.
- 24 P. Benatti, G. Peluso, R. Nicolai, M. Calvani, J. Am. Coll. Nutr. 2004, 23, 281.
- 25 D. W. Ma, J. Seo, K. C. Switzer, Y. Y. Fan, D. N. McMurray, J. R. Lupton, R. S. Chapkin, J. Nutr. Biochem. 2004, 15, 700.
- 26 M. L. Blaxter, J. Biol. Chem. 1993, 268, 6600.
- 27 D. Schwudke, J. Oegema, L. Burton, E. Entchev, J. T. Hannich, C. S. Ejsing, T. Kurzchalia, A. Shevchenko, Anal. Chem. 2006, 78, 585.
- 28 J. Folch, M. Lees, G. H. Sloane Stanley, J. Biol. Chem. 1957, 226, 497.
- 29 O. Schaaf, K. Dettner, Lipids 2000, 35, 543.
- 30 J. L. Watts, J. Browse, Arch. Biochem. Biophys. 1999, 362, 175.
- 31 R. R. Brenner, in ‘Essential Fatty Acids and Prostaglandins’, Ed. R. T. Holman, Pergamon Press, 1981, Vol. 20, pp. 41–47.
- 32 J. L. Watts, E. Phillips, K. R. Griffing, J. Browse, Genetics 2003, 163, 581.
- 33 T. Tanaka, K. Ikita, T. Ashida, Y. Motoyama, Y. Yamaguchi, K. Satouchi, Lipids 1996, 31, 1173.
- 34 S. Brenner, Genetics 1974, 77, 71.
- 35 ‘The Nematode Caenorhabditis elegans’, Ed. W. B. Wood, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, 1988.