Enzymatic formation of anandamide

Vitam Horm. 2009:81:1-24. doi: 10.1016/S0083-6729(09)81001-7.

Abstract

In animal tissues anandamide and other bioactive N-acylethanolamines are principally produced from glycerophospholipids through the transacylation-phosphodiesterase pathway consisting of two enzymatic reactions. The first reaction is the generation of N-acylphosphatidylethanolamine (NAPE) by transferring an acyl group esterified at sn-1 position of glycerophospholipid to the amino group of phosphatidylethanolamine. This reaction is catalyzed by Ca(2+)-dependent N-acyltransferase. The discovery of Ca(2+)-independent N-acyltransferase revealed the existence of plural enzymes which are capable of catalyzing this reaction. The second reaction is the release of N-acylethanolamine from NAPE catalyzed by NAPE-hydrolyzing phospholipase D (NAPE-PLD). The enzyme belongs to the metallo-beta-lactamase family and specifically hydrolyzes NAPEs. Recent studies, including analysis of NAPE-PLD-deficient mice, led to the discovery of NAPE-PLD-independent pathways for the anandamide biosynthesis.

Publication types

  • Review

MeSH terms

  • Acyltransferases / chemistry
  • Acyltransferases / metabolism*
  • Amino Acid Sequence
  • Animals
  • Arachidonic Acids / biosynthesis*
  • Calcium / pharmacology
  • Cannabinoid Receptor Modulators / biosynthesis*
  • Endocannabinoids
  • Humans
  • Mice
  • Molecular Sequence Data
  • Organ Specificity
  • Phosphatidylethanolamines / metabolism
  • Phospholipase D / chemistry
  • Phospholipase D / deficiency
  • Phospholipase D / metabolism
  • Phospholipases / metabolism*
  • Polyunsaturated Alkamides
  • Sequence Alignment

Substances

  • Arachidonic Acids
  • Cannabinoid Receptor Modulators
  • Endocannabinoids
  • Phosphatidylethanolamines
  • Polyunsaturated Alkamides
  • phosphatidylethanolamine
  • Acyltransferases
  • Phospholipases
  • N-acylphosphatidylethanolamine phospholipase D, mouse
  • Phospholipase D
  • Calcium
  • anandamide