J. Lipid Res.
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A more recent version of this article appeared on September 1, 2005

Papers In Press, published online ahead of print June 16, 2005
J. Lipid Res., doi:10.1194/jlr.M500121-JLR200
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Submitted on March 31, 2005
Revised on May 31, 2005
Accepted on June 3, 2005

On the importance of anandamide structural features for its interactions with dipalmitoylphosphatidylcholine bilayesr: Effects on PLA2 activity

Simona Ambrosi, Letizia Ragni, Annarina Ambrosini, Lydia Paccamiccio, Paolo Mariani, Rosamaria Fiorini, Enrico Bertoli, and Giovanna Zolese

Istituto di Biochimica, Università Politecnica delle Marche, Ancona 60131

Corresponding Author: g.zolese{at}univpm.it

The acylethanolamide anandamide (AEA) occurs in a variety of mammalian tissues and, as a result of its action on cannabinoid receptors, exhibits several cannabimimetic activities. Moreover, some of its effects are mediated through interaction with an ion-channel-type vanilloid receptor (VR1 receptor). However, the chemical features of AEA could suggest that some of its biological effects could be related to physical interactions with the lipidic part of the membrane. The present work studies the effect of AEA-induced structural modifications of Dipalmitoylphosphatidylcholine (DPPC) bilayer on phospholipase A2 (PLA2) activity, that is strictly dependent on lipid bilayer features. The present study, performed by 2-dimethylamino-(6-lauroyl)-naphtalene (Laurdan) fluorescence, demonstrates that the effect of AEA on PLA2 activity is concentration dependent. In fact, at low AEA/DPPC molar ratios (from R=0.001 to R=0.04) there is an increase of the enzymatic activity, which is completely inhibited for R=0.1. X-ray diffraction data indicate that the AEA affects DPPC membrane structural properties in a concentration dependent way. Since the biphasic effect of increasing AEA concentrations on PLA2 activity is to be related to the induced modifications of membrane bilayer structural properties, it is suggested that AEA-phospholipid interactions may be important to produce, at least in part, some of the similarly biphasic responses of some physiological activities to AEA increasing concentrations.


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