J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
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A more recent version of this article appeared on January 1, 2008

Papers In Press, published online ahead of print October 23, 2007
J. Lipid Res., doi:10.1194/jlr.M700354-JLR200
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Submitted on August 7, 2007
Revised on September 28, 2007
Accepted on October 18, 2007

Identification of biosynthetic precursors for the endocannabinoid anandamide in the rat brain

Giuseppe Astarita, Faizy Ahmed, and Daniele Piomelli

Pharmacology, University California Irvine, Irvine, CA 92697

Corresponding Author: piomelli{at}uci.edu

Anandamide is an endogenous signaling lipid that binds to and activates cannabinoid receptors in the brain and peripheral tissues. The endogenous precursors of anandamide, N-arachidonoyl phosphotidylethanolamines (NArPEs) are a family of complex glycerophospholipids that derive from the exchange reaction of an arachidonoyl group between the sn-1 position of phosphatidylcholine and the primary amine of phosphatidylethanolamine catalyzed by N-acyl transferase activity. A precise characterization of the molecular composition of NArPE species generating anandamide has not yet been reported. In the present study, using liquid chromatography coupled to electrospray-ionization ion-trap mass-spectrometry (LC/MSn), we identified the major endogenous NArPE species, which mainly contained sn-1 alkenyl groups (C16:0, C18:0, C18:1) and monounsaturated (C18:1) or polyunsaturated acyl groups (C20:4, C22:4, C22:6) in the sn-2 position of the glycerol backbone. Using rat brain particulate fractions, we observed a calcium-dependent increase in both NArPEs and anandamide formation after incubation at 37°C for 30 min. Furthermore, a targeted lipidomic analysis showed that Ca2+ specifically stimulated the formation of PUFA-containing NArPE species. These results reveal a preciously unrecognized preference of brain N-acyl transferase activity for polyunsaturated NArPE and provide new insights on the physiological regulation of anandamide biosynthesis.


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