title: Different modulation of phospholipase A2 activity by saturated and monounsaturated N-acylethanolamines.
abstract: 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.
authors.affiliation: Istituto di Biochimica, Università di Ancona, Italy. zolese@popcsi.unian.it
authors.forename: Giovanna
authors.initials: G
authors.lastname: Zolese
authors.forename: Michal
authors.initials: M
authors.lastname: Wozniak
authors.forename: Paolo
authors.initials: P
authors.lastname: Mariani
authors.forename: Letizia
authors.initials: L
authors.lastname: Saturni
authors.forename: Enrico
authors.initials: E
authors.lastname: Bertoli
authors.forename: Annarina
authors.initials: A
authors.lastname: Ambrosini
mesh_terms: D000818:Animals; D004983:Ethanolamines / Q000494:pharmacology*; D005227:Fatty Acids / Q000494:pharmacology; D005231:Fatty Acids, Unsaturated / Q000494:pharmacology; D005456:Fluorescent Dyes; D006868:Hydrolysis; D008051:Lipid Bilayers / Q000737:chemistry; D008081:Liposomes / Q000737:chemistry; D008560:Membrane Fluidity; D044367:Phase Transition; D010741:Phospholipases A / Q000378:metabolism*; D054467:Phospholipases A2; D013552:Swine; D013696:Temperature; D014961:X-Ray Diffraction
chemical_list: D004983:Ethanolamines; D005227:Fatty Acids; D005231:Fatty Acids, Unsaturated; D005456:Fluorescent Dyes; D008051:Lipid Bilayers; D008081:Liposomes; C022203:N-acylethanolamines; D010741:Phospholipases A; D054467:Phospholipases A2