N-acyl ethanolamine

Gray, G.M. Phosphatidyl-(N-acyl)-ethanolamine a lipid component of mammalian epidermis. Biochim. Biophys. Acta 1976 431 1-8. 

Fowler CJ (2003) Plant-derived, synthetic and endogenous cannabinoids as neuroprotective agents non-psychoactive cannabinoids, entourage compounds and inhibitors of N-acyl ethanolamine breakdown as therapeutic strategies to avoid psychotropic effects. Brain Res Rev 41 26-43... 

Smart, D., Jonsson, K.O., Vandevoorde, S., Lambert, D.M., and Fowler, C.J. (2002) Entourage effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism, Br. J. Pharmacol, 136 452-8. 

Moesgaard, B., Petersen, G., Jaroszewski, J.W., and Hansen, H.S. (2000) Age dependent accumulation of N-acyl-ethanolamine phospholipids in ischemic rat brain. A P NMR and enzyme activity study. Journal of Lipid Research 41 985-990. 

Markey, S.P., Dudding, T., and Wang, T.C. (2000) Base- and acid-catalyzed interconversions of O-acyl- and N-acyl-ethanolamines a cautionary note for lipid analyses. J Lipid Res. 41 657-662. 

Hill, M.N., MiUer, G.E., Carrier, E.J., GorzaUca, B.B. and HiUard, C.J. (2009) Circulating endocannabinoids and N-acyl ethanolamines are differentially regulated in major depression and following exposure to social stress. Psychoneuroendocrinology 34,1257-1262. 

Natarajan V, Schmid PC, Reddy PV, Schmid HHO. Catabolism of N-acyl-ethanolamine phospholipids by dog brain preparations. J Neurochem 1984 42 1613-1619. 

Burstein and Hunter (1995) observed that THC stimulated the biosynthesis of anandamide in neuroblastoma cells employing either ethanolamine or arachidonic acid as the label. Anandamide bios5mthesis has also been shown to occur in primary cultures of rat brain neurons labelled with [H]-ethanolamine when stimulated with ionomycin, a Ca ionophore (Di Marzo et al. 1994). These authors proposed an alternate model for the biosynthesis of anandamide in which N-arachidonoyl phosphatidyl ethanolamine is cleaved by a phospholipase D activity to yield phosphatidic acid and ararchidonoylethanolamide. This model is based upon extensive studies undertaken by Schmid and collaborators (1990), who have shown that fatty acid ethanolamide formation results from the N-acylation of phosphatidyl ethanolamine by a transacylase to form N-acyl phosphatidylethanolamine. Possibly resulting from postmortem changes, this compound is subsequently hydrolyzed to the fatty acid ethanolamide and the corresponding phosphatide by a phosphodiesterase, phospholipase D. 

FIGURE 7.3 Comparison of theiV-acyl moieties of iV-acylethanolamines (A), N-acyl moieties of N-acyl PEs (B), fatty acids esterified at the 1-position of phosphatidylcholine (C) and free fatty acids (D) in rat brain. Values are the means of four to six determinations. (From Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., Ishima, Y, and Waku, K. (1996) Transacylase-mediated and phosphodiesterase-mediated synthesis of iV-arachidonoylethanolamine, an endogenous cannabinoid receptor ligand, in rat brain microsomes. Comparison with synthesis from free arachidonic acid and ethanolamine, European Journal of Biochemistry 240 53-62. With permission.)... 

The fatty acid analyses of Dawson et al. (1969) and Aneja et al. (1969) showed the N-acyl group to be much more saturated than the O-acyl group. Wilson and Rinne (1978) have reported that APE has approximately 70% 18 2 at all stages of development of the seed, but they did not measure O-acyl and A -acyl separately. MacMurray and Morrison (1970) have reported that wheat flour lipids also are rich in the Al-acyl derivatives of ethanolamine containing phospholipids. 

Tlie polar head group of the molecule regulates the overall charge and hydrophilicity of the membrane. The major polar groups in biomembranes may be choline, ethanolamine, serine, inositol, galactose or in some cases n-acetylneuraminic acid. The non-polar acyl-chains influence greatly the fluidity and the packing of the membrane. Saturated fatty acid residues while decrease the fluidity and produce more compact membranes, unsatiirated acyi-chains increase the fluidity and minimize the lipid orientation of the membrane. 

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