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Journal of Lipid Research, Vol. 44, 742-753, April 2003
Copyright © 2003 by Lipid Research, Inc.

Different modulation of phospholipase A₂ activity by saturated and monounsaturated N-acylethanolamines

Giovanna Zolese^1,*, Michal Wozniak, Paolo Mariani, Letizia Saturni, Enrico Bertoli^* and Annarina Ambrosini^*

^* Istituto di Biochimica, Università di Ancona, 60100 Ancona, Italy
Istituto di Scienze Fisiche and INFM, Università di Ancona, 60100 Ancona, Italy
Department of General Chemistry,, University of Gdansk, Gdansk, Poland

¹ To whom correspondence should be addressed. e-mail zolese{at}popcsi.unian.it

The physiological functions of N-acylethanolamines (NAEs) are poorly understood, although many functions were suggested for these naturally occurring membrane components of plants and animals. The binding with cannabinoid receptors CB1 and CB2 was demonstrated for some NAEs, such as anandamide. However, the chemical nature of these molecules suggests that some of their biological effects on biomembranes could be related, at least partially, to physical interactions with the lipid bilayer. The present work studies the effect of saturated and monounsaturated NAEs on phospholipase A₂ (PLA₂) activity, which is dependent on lipid bilayer features. The present study, performed by 2-dimethylamino-(6-lauroyl)-naphthalene (Laurdan) fluorescence, demonstrates that the acyl chain length and the presence of a single double bond are crucial for the enzymatic activity modulation by NAEs. In fact, saturated NAEs with 10 carbon atoms don't affect the PLA₂ activity, while NAEs with 12 and 16 carbon atoms largely activate the enzyme. On the other hand, an acyl chain length of 18 carbon atoms, with or without the presence of a double bond, only slightly affects the enzymatic activity.

A structural model for NAE-lipid interactions is proposed in order to explain the differences in PLA₂ activity modulation by these fatty acid derivatives.

Abbreviations: DPPC, dipalmitoylphosphatidylcholine; GP, generalized polarization; Laurdan, 2-dimethylamino-(6-lauroyl)-naphthalene; LUV, large unilamellar vesicle; Lyso-PC, lysophosphatidylcholine; MLV, multilamellar vesicle; NAE, N-acylethanolamine; NCEA, N-caprinoylethanolamine; NOEA, N-oleoylethanolamine; NPEA, N-palmitoylethanolamine; NSEA, N-stearoylethanolamine; PL, phospholipid; PLA₂, phospholipase A₂; Prodan, 6-propionyl-2-(dimethylamino)-naphthalene; 3wGP, three-wavelengths GP

Supplementary key words PLA₂ activity • 2-dimethylamino-(6-lauroyl)-naphthalene • 6-propionyl-2-(dimethylamino)-naphthalene • X-rays • dipalmitoylphosphatidylcholine • large unilamellar vesicle

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