Journal
JOURNAL OF LIPID RESEARCH
Volume 49, Issue 1, Pages 48-57Publisher
ELSEVIER
DOI: 10.1194/jlr.M700354-JLR200
Keywords
fatty acid ethanolamine; arachidonoylethanolamide; N-arachidonoyl phosphatidylethanolamines; phosphatidylethanolamine; N-acyl phosphatidylethanolamines; N-acyl transferase; polyunsaturated fatty acids; phospholipids; lipidomic; nervous system
Categories
Funding
- NATIONAL INSTITUTE ON DRUG ABUSE [R21DA022702, R01DA012413] Funding Source: NIH RePORTER
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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 degrees C for 30 min. Furthermore, a targeted lipidomic analysis showed that Ca2+ specifically stimulated the formation of PUFA-containing NArPE species.
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