Phosphatidic acid as the biosynthetic precursor of the endocannabinoid 2-arachidonoylglycerol in intact mouse neuroblastoma cells stimulated with ionomycin

J Neurochem. 1999 May;72(5):2113-9. doi: 10.1046/j.1471-4159.1999.0722113.x.

Abstract

In mouse neuroblastoma N18TG2 cells prelabeled with [3H]arachidonic acid ([3H]AA) the biosynthesis of 2-arachidonoylglycerol (2-AG) is induced by ionomycin in a fashion sensitive to an inhibitor of diacylglycerol (DAG) lipase, RHC 80267, but not to four different phospholipase C (PLC) blockers. Pulse experiments with [3H]AA showed that ionomycin stimulation leads to the sequential formation of [3H]phosphatidic acid ([3H]PA), [3H]DAG, and [3H]2-AG. [3H]2-AG biosynthesis in N18TG2 cells prelabeled with [3H]AA was counteracted by propranolol and N-ethylmaleimide, two inhibitors of the Mg2+/Ca2(+)-dependent brain PA phosphohydrolase. Pretreatment of cells with exogenous phospholipase D (PLD) led to a strong potentiation of ionomycin-induced [3H]2-AG formation. These data indicate that DAG precursors for 2-AG in intact N18TG2 cells are obtained from the hydrolysis of PA and not through the activation of PLC. The presence of 2% ethanol during ionomycin stimulation failed to elicit the synthesis of [3H]phosphatidylethanol and did not counteract the formation of [3H]PA, thus arguing against the activation of PLD by the Ca2+ ionophore. Selective inhibitors of secretory phospholipase A2 and the acyl-CoA acylase inhibitor thimerosal significantly reduced [3H]2-AG biosynthesis. The implications of these latter findings, and of the PA-dependent pathways of 2-AG formation described here, are discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arachidonic Acids*
  • Cannabinoid Receptor Modulators
  • Cyclohexanones / pharmacology
  • Diglycerides / antagonists & inhibitors
  • Diglycerides / metabolism
  • Endocannabinoids
  • Enzyme Inhibitors / pharmacology
  • Glycerides / antagonists & inhibitors
  • Glycerides / biosynthesis*
  • Hydrolysis
  • Ionomycin / pharmacology*
  • Ionophores / pharmacology*
  • Lipoprotein Lipase / antagonists & inhibitors
  • Mice
  • Neuroblastoma / metabolism*
  • Neuroblastoma / pathology
  • Phosphatidic Acids / metabolism*
  • Phospholipase D / pharmacology
  • Phosphoric Monoester Hydrolases / antagonists & inhibitors
  • Prodrugs / metabolism*
  • Protease Inhibitors / pharmacology
  • Tumor Cells, Cultured / drug effects
  • Tumor Cells, Cultured / metabolism
  • Type C Phospholipases / antagonists & inhibitors

Substances

  • Arachidonic Acids
  • Cannabinoid Receptor Modulators
  • Cyclohexanones
  • Diglycerides
  • Endocannabinoids
  • Enzyme Inhibitors
  • Glycerides
  • Ionophores
  • Phosphatidic Acids
  • Prodrugs
  • Protease Inhibitors
  • Ionomycin
  • 1,6-bis(cyclohexyloximinocarbonyl)hexane
  • glyceryl 2-arachidonate
  • Lipoprotein Lipase
  • Phosphoric Monoester Hydrolases
  • Type C Phospholipases
  • Phospholipase D