2-pentadecyl-2-oxazoline: identification in coffee, synthesis and pharmacological activity in a rat model of carrageenan-induced hindpaw inflammation
N-acylethanolamines (NAEs) comprise a family of bioactive lipid molecules present in animal and plant tissues. Among the NAEs, N-palmitoylethamine (PEA) has received much attention owing to its anti-inflammatory, analgesic and neuroprotective activities. 2-Pentadecyl-2-oxazoline (PEA-OXA), the oxazoline of PEA, has been reported to modulate the activity of NAE-hydrolyzing acid amidase (FAAA), the principal catabolic enzyme of PEA. Because PEA is produced on demand and exerts pleiotropic effects on non-neuronal cells implicated in neuroinflammation, modulating the specific amidases for NAEs (FAAA in particular) could be a way to preserve PEA role in maintaining cellular homeostasis through its rapid on-demand synthesis and equally rapid degradation. The present study exploits the LC-MS technique in order to provide the evidence of the natural occurrence of PEA-OXA in coffee beans and Moka infusions extracts and pharmacological approaches to verify its anti-inflammation properties. The method have been optimized and validated in standard solutions by using an Agilent 6460 LC-triple-quadrupole. Sensitivity, linearity and matrix effect were tested and showed appropriate for method purposes.
To the best of our knowledge, the present observations are the first report of PEA-OXA in the plant kingdom.
Pharmacological Research 108 (2016) 23–30
Daniela Impellizzeria, Marika Cordaroa, Giuseppe Bruschettaa, Rosalia Crupia, Jennifer Pascalib, Daniele Alfonsic, Gabriele Marcolongoc, Salvatore Cuzzocreaa
aDepartment of Chemical, Biological, Pharmaceutical and Environmental Sciences, University of Messina, Messina, Italy
bdtoLabs Analytical Excellence Center, Agilent Technologies, Via Fratta 25, Resana (TV), Italy
cEpitech Spa, Via Einaudi 13, Saccolongo (PD), Italy