Phosphatidyl-(N-acyl)-ethanolamine. A lipid component of mammalian epidermis.
A lipid present in the granular cells of mammalian epidermis was identified as phosphatidyl-(N-acyl)-ethanolamine. The structure was deduced from the ratio of phosphorus : nitrogen : glycerol : fatty acid esters : total fatty acid (1 : 0.94 : 0.97 : 2.1 : 2.9), from analyses of the products of alkaline and acid hydrolyses and from its infrared spectrum. Conclusive evidence was obtained by a direct comparison of the chromatographic properties, degradation products and infrared spectrum of the isolated lipid with those of synthetic 1,2-dipalmitoyl-sn-glycero-3-phospho-(N-palmitoyl)-ethanolamine. The fatty acids attached to the ethanolamine were predominantly saturated (69% of total) and hexadecanoic acid was the major component (41% of total). Phosphatidyl-(N-acyl)-ethanolamine was hydrolysed by a phospholipase C (Bacillus cereus) to diacylglycerol, inorganic phosphorus and N-acylethanolamine. Evidence for the presence of N-acylethanolamine in granular cells and in stratum corneum suggested that an epidermal phospholipase C may be involved in the catabolism of phosphatidyl-(N-acyl)-ethanolamine.
D000818:Animals; D002855:Chromatography, Thin Layer; D004423:Ear; D005227:Fatty Acids / Q000032:analysis; D010714:Phosphatidylethanolamines / Q000032:analysis*; D010740:Phospholipases; D012867:Skin / Q000032:analysis*; D013055:Spectrophotometry, Infrared; D013552:Swine; D013623:Tail
D005227:Fatty Acids; D010714:Phosphatidylethanolamines; D010740:Phospholipases