Identification of endocannabinoids and related N-acylethanolamines in tetrahymena. A new class of compounds for Tetrahymena.
The endocannabinoid system is a lipid signaling system in mammalian cells. We reported that major components of the endocannabinoid system such as fatty acid amide hydrolase and monoacylglycerol lipase, are present in the protist Tetrahymena, with characteristics similar to those in mammals. Tetrahymena is a model organism for molecular and cellular biology studies as its genome sequence is available. Here we report the presence of N-acylethanolamines (AcEs) and their respective 2-acylglycerols (2-AcGs) in Tetrahymena thermophila for the first time; the former is a new lipid class for the protist. Using LC-MS/MS we identified, N y-linolenoyl, N-eicosenoyl, N-linoleoyl, N-palmitoyl, N-stearoyl and N-oleoylethanolamines as well as the corresponding monoacylglycerols. The levels of 2-acylglycerols were much higher than the corresponding N-acylethanolamines, as reported for mammals. To our knowledge, N-gamma-linolenoylethanolamine (GLEA) was found for the first time in nature. Anandamide and 2-AG were present in trace amounts. These results demonstrate the existence of a new lipid class in Tetrahymena, strengthen the conviction that the endocannabinoid system is present in this protist, verifying its importance throughout evolution. Tetrahymena could be used as a model for metabolic studies on the endocannabinoids, as well as for the study of drugs targeted towards biosynthetic and catabolic enzymes of AcEs and 2-AcGs.
Anagnostopoulos
Dimitris
D
Department of Chemistry, University of Athens, Panepistimioupolis, 15771 Athens, Greece.
Rakiec
Carmelina
C
Wood
Jodi
J
Pandarinathan
Lakshmipathi
L
Zvonok
Nikolai
N
Makriyannis
Alexandros
A
Siafaka-Kapadai
Athanasia
A
D063385:Cannabinoid Receptor Modulators / Q000032:analysis* / Q000302:isolation & purification; D002853:Chromatography, Liquid; D063388:Endocannabinoids; D004983:Ethanolamines / Q000032:analysis* / Q000302:isolation & purification; D053719:Tandem Mass Spectrometry; D016808:Tetrahymena thermophila / Q000737:chemistry*
D063385:Cannabinoid Receptor Modulators; D063388:Endocannabinoids; D004983:Ethanolamines; C022203:N-acylethanolamines