Lauroylethanolamide is a potent competitive inhibitor of lipoxygenase activity

FEBS Lett. 2010 Jul 16;584(14):3215-22. doi: 10.1016/j.febslet.2010.06.008. Epub 2010 Jun 10.

Abstract

The lipoxygenase (LOX) pathway was proposed to compete with hydrolysis and be partly responsible for the metabolism of polyunsaturated N-acylethanolamines (PU-NAEs). Treatment of Arabidopsis seedlings with lauroylethanolamide (NAE 12:0) resulted in elevated levels of PU-NAE species, and this was most pronounced in plants with reduced NAE hydrolase activity. Enzyme activity assays revealed that NAE 12:0 inhibited LOX-mediated oxidation of PU lipid substrates in a dose-dependent and competitive manner. NAE 12:0 was 10-20 times more potent an inhibitor of LOX activities than lauric acid (FFA 12:0). Furthermore, treatment of intact Arabidopsis seedlings with NAE 12:0 (but not FFA 12:0) substantially blocked the wound-induced formation of jasmonic acid (JA), suggesting that NAE 12:0 may be used in planta to manipulate oxylipin metabolism.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Arabidopsis / enzymology
  • Arabidopsis / metabolism
  • Cyclopentanes
  • Enzyme Assays
  • Ethanolamines
  • Hydrolysis
  • Lauric Acids
  • Lipids
  • Lipoxygenase / metabolism*
  • Oxylipins
  • Plants / enzymology
  • Plants / metabolism
  • Seedlings / enzymology
  • Seedlings / metabolism

Substances

  • Cyclopentanes
  • Ethanolamines
  • Lauric Acids
  • Lipids
  • N-acylethanolamines
  • Oxylipins
  • lauric acid
  • jasmonic acid
  • Lipoxygenase