The Identification of N-(2-Hydroxyethyl)-Palmitamide as a Naturally Occurring Anti-Inflammatory Agent

Abstract

a Cells (Pseudon lonas ATCC 11250, E. coli K12) were grown in a special flask designed for this type of experiment6 at 25°for about 20 hours with vigorous mechanical shaking. Basal medium contained 0.15% K2HP04, 0.05% KH2P04, 0.02% MgS04-7H20 and 0.1% Difeo yeast extract. In addition, in exp. 1, 0.1% benzoic acid and 0.1% NH4C1; in exp. 2 and 5, 0.1% L-phenylalanine; in exp. 3 and 6, 0.1% L-tryptophan and in exp. 4 and 7, 0.1% glucose and 0.1% NH4C1 were added as carbon and nitrogen sources. The gas phase was a mixture of nitrogen and oxygen in a ratio of 4:1. Highly enriched 0218 gas was prepared by electrolysis of approximately 33% enriched H2018 purchased from The Weizmann Institute of Science, Israel. Cells were harvested by centrifugation, washed with 0.9% KC1 and distilled water. Pyrolysis was carried out at 500°f or 1 hour with HgCl2 as a catalyst according to D. Rittenberg and L. Ponticorvo (Internat. J. Appl. Radiation and Isotopes, 1, 208 (1956)). The mass spectrometric analyses were carried out in collaboration with Mr. W. E. Comstock of this Institute.tions involving fixation of atmospheric oxygen.6-7 When E. coli, a facultative aerobe, was grown under comparable conditions, 018-enrichment in the cell material was approximately 0.1% or less of that of the atmospheric oxygen. Although the data indicate that E. coli also incorporates atmospheric oxygen, particularly when aromatic compounds are used as carbon sources, oxygenases seem to play a more important role in the metabolism of a strictly aerobic microorganism. Further studies are in progress in order to determine the distribution of oxygenases in various tissues and other microorganisms.(5) O.

Biosynthesis, degradation and pharmacological importance of the fatty acid amides

“…The first non-sphingosine based fatty acid amide isolated from a natural source was N-palmitoylethanolamine from egg yolk in 1957 [3]. Interest in the N-acylethanolamines (NAEs) dramatically increased upon the identification of Narachidonoylethanolamine (anandamide) as the endogenous ligand for the cannabinoid receptors in the mammalian brain [4].…”

Regulation of food intake by oleoylethanolamide

“…The fatty-acid ethanolamides (FAEs) are a family of naturally occurring lipids that are present in both plant and animal tissues [1,2]. Their physiological significance was first recognized nearly 50 years ago, with the discovery of the antiallergic effects of palmitoylethanolamide [1] (PEA, fig.…”

“…Their physiological significance was first recognized nearly 50 years ago, with the discovery of the antiallergic effects of palmitoylethanolamide [1] (PEA, fig. 1), the amide of palmitic acid and ethanolamine.…”

Fatty acid amide hydrolase (FAAH) inhibition enhances memory acquisition through activation of PPAR-α nuclear receptors

“…OEA has primarily been studied as a satiety factor (Rodriguez de Fonseca et al 2001;Fu et al 2003) and PEA as an anti-inflammatory factor (Kuehl et al 1957;Calignano et al 1998;Jaggar et al 1998). OEA and PEA are structurally similar to anandamide but do not bind to or activate cannabinoid CB 1 receptors.…”

“…In addition, anandamide (N-arachidonoylethanolamine), which has primarily been studied as an endogenous ligand for G-proteincoupled cannabinoid CB 1 receptors that mediate the behavioral effects of cannabis and its active constituent D 9 -tetrahydrocannabinol (THC) (Devane et al 1992;Solinas et al 2008), has recently begun to receive attention as a potential endogenous PPAR-a ligand (O'Sullivan 2000; Mackie and Stella 2006;Sun et al 2007). OEA has primarily been studied as a satiety factor (Rodriguez de Fonseca et al 2001;Fu et al 2003) and PEA as an anti-inflammatory factor (Kuehl et al 1957;Calignano et al 1998;Jaggar et al 1998). OEA and PEA are structurally similar to anandamide but do not bind to or activate cannabinoid CB 1 receptors.…”