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Published on July 25, 2002; 10.1104/pp.001974

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Received January 4, 2002
Returned for revision March 6, 2002
Accepted April 8, 2002

Inhibition of Phospholipase D{alpha} by N-Acylethanolamines

Shea L. Austin-Brown and Kent D. Chapman *

Department of Biological Sciences, Division of Biochemistry and Molecular Biology, University of North Texas, Denton, Texas 76203--5220

* Corresponding author; email: chapman{at}unt.edu.

N-Acylethanolamines (NAEs) are endogenous lipids in plants produced from the phospholipid precursor, N-acylphosphatidylethanolamine, by phospholipase D (PLD). Here, we show that seven types of plant NAEs differing in acyl chain length and degree of unsaturation were potent inhibitors of the well-characterized, plant-specific isoform of PLD—PLD{alpha}. It is notable that PLD{alpha}, unlike other PLD isoforms, has been shown not to catalyze the formation of NAEs from N-acylphosphatidylethanolamine. In general, inhibition of PLD{alpha} activity by NAEs increased with decreasing acyl chain length and decreasing degree of unsaturation, such that N-lauroylethanolamine and N-myristoylethanolamine were most potent with IC50s at submicromolar concentrations for the recombinant castor bean (Ricinus communis) PLD{alpha} expressed in Escherichia coli and for partially purified cabbage (Brassica oleracea) PLD{alpha}. NAEs did not inhibit PLD from Streptomyces chromofuscus, and exhibited only moderate, mixed effects for two other recombinant plant PLD isoforms. Consistent with the inhibitory biochemical effects on PLD{alpha} in vitro, N-lauroylethanolamine, but not lauric acid, selectively inhibited abscisic acid-induced closure of stomata in epidermal peels of tobacco (Nicotiana tabacum cv Xanthi) and Commelina communis at low micromolar concentrations. Together, these results provide a new class of biochemical inhibitors to assist in the evaluation of PLD{alpha} physiological function(s), and they suggest a novel, lipid mediator role for endogenously produced NAEs in plant cells.




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