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Originally published In Press as doi:10.1194/jlr.M700354-JLR200 on October 23, 2007

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Journal of Lipid Research, Vol. 49, 48-57, January 2008
Copyright © 2008 by American Society for Biochemistry and Molecular Biology

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

Giuseppe Astarita*, Faizy Ahmed{dagger} and Daniele Piomelli1,*

* Department of Pharmacology and Center for Drug Discovery, University of California, Irvine, CA 92967
{dagger} Agilent Technologies, University of California, Irvine/Agilent Analytical Discovery Facility, University of California, Irvine, CA 92967

Published, JLR Papers in Press, October 23, 2007.

1 To whom correspondence should be addressed. e-mail: 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 phosphatidylethanolamines (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, 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 (C20:4, C22:4, C22:6) acyl groups at 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 previously unrecognized preference of brain N-acyl transferase activity for polyunsaturated NArPE and provide new insights on the physiological regulation of anandamide biosynthesis.

Supplementary key words fatty acid ethanolamine • arachidonoylethanolamide • N-arachidonoyl phosphatidylethanolamines • phosphatidylethanolamine • N-acyl phosphatidylethanolamines • N-acyl transferase • polyunsaturated fatty acids • phospholipids • lipidomic • nervous system


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