Identification of N-acylphosphatidylserine molecules in eukaryotic cells

Biochemistry. 2007 Dec 18;46(50):14500-13. doi: 10.1021/bi701907g. Epub 2007 Nov 22.

Abstract

While profiling the lipidome of the mouse brain by mass spectrometry, we discovered a novel family of N-acylphosphatidylserine (N-acyl-PS) molecules. These N-acyl-PS species were enriched by DEAE-cellulose column chromatography, and they were then characterized by accurate mass measurements, tandem mass spectrometry, liquid chromatography/mass spectrometry, and comparison to an authentic standard. Mouse brain N-acyl-PS molecules are heterogeneous and constitute about 0.1% of the total lipid. In addition to various ester-linked fatty acyl chains on their glycerol backbones, the complexity of the N-acyl-PS series is further increased by the presence of diverse amide-linked N-acyl chains, which include saturated, monounsaturated, and polyunsaturated species. N-Acyl-PS molecular species were also detected in the lipids of pig brain, mouse RAW264.7 macrophage tumor cells, and yeast, but not Escherichia coli. N-Acyl-PSs may be biosynthetic precursors of N-acylserine molecules, such as the recently reported signaling lipid N-arachidonoylserine from bovine brain. We suggest that a phospholipase D might cleave N-acyl-PS to generate N-acylserine, in analogy to the biosynthesis of the endocannabinoid N-arachidonoylethanolamine (anadamide) from N-arachidonoylphosphatidylethanolamine.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Brain / metabolism
  • Chromatography, Ion Exchange
  • Chromatography, Liquid
  • Eukaryotic Cells / metabolism*
  • Fatty Acids / analysis
  • Lipids / chemistry
  • Lipids / isolation & purification
  • Mass Spectrometry
  • Mice
  • Molecular Structure
  • Phosphatidylserines / chemistry*
  • Phosphatidylserines / metabolism*
  • Phospholipase D / metabolism
  • Spectrometry, Mass, Electrospray Ionization
  • Swine
  • Tandem Mass Spectrometry

Substances

  • Fatty Acids
  • Lipids
  • Phosphatidylserines
  • Phospholipase D