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(Received for publication, May 30, 1996, and in revised form, September 30, 1996)
From the Anandamide (arachidonoylethanolamide, AnNH) and
palmitoylethanolamide (PEA) have been proposed as the physiological
ligands, respectively, of central and peripheral cannabinoid receptors. Both of these receptors are expressed in immune cells, including macrophages and mast cells/basophils, where immunomodulatory and/or anti-inflammatory actions of AnNH and PEA have been recently reported. We now provide biochemical grounds to these actions by showing that the
biosynthesis, uptake, and degradation of AnNH and PEA occur in
leukocytes. On stimulation with ionomycin, J774 macrophages and RBL-2H3
basophils produced AnNH and PEA, probably through the hydrolysis of the
corresponding N-acylphosphatidylethanolamines, also found
among endogenous phospholipids. Immunological challenge of RBL-2H3
cells also caused AnNH and PEA release. The chemical structure and the
amounts of AnNH and PEA produced upon ionomycin stimulation were
determined by means of double radiolabeling experiments and isotope
dilution gas chromatography/electron impact mass spectrometry. Both
cell lines rapidly sequestered the two amides from the culture medium
through temperature-dependent, saturable and chemically inactivable mechanisms. Once uptaken by basophils, AnNH and PEA compete
for the same inactivating enzyme which catalyzes their hydrolysis to
ethanolamine. This enzyme was found in both microsomal and 10,000 × g fractions of RBL cell homogenates, and exhibited similar inhibition and temperature/pH dependence profiles but a
significantly higher affinity for PEA with respect to neuronal "anandamide amidohydrolase." The finding of biosynthetic and
inactivating mechanisms for AnNH and PEA in macrophages and basophils
supports the previously proposed role as local modulators of
immune/inflammatory reactions for these two long chain
acylethanolamides.
Volume 272, Number 6,
Issue of February 7, 1997
pp. 3315-3323
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.
,
,
,
Istituto per la Chimica di Molecole di
Interesse Biologico and § Istituto di Cibernetica, CNR,
Viale Toiano 6, 80072, Arco Felice, Napoli, Italy
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