Plasmalogens

Literature References: Aldehydogenic lipids characteristic of the animal kingdom; references to their existence in plants and bacteria are rare. Plasmalogens contain an aldehydogenic chain linked to glycerol as an a,b-unsaturated ether. Although most are aldehydogenic phosphatides, nonphosphatide or neutral plasmalogens have been detected in animal tissues. "Native plasmalogens", when deacylated, yield lysoderivatives, lysoplasmalogens, contg the aldehydogenic chain linked to glycerol as an a,b-unsaturated ether. The nomenclature "phosphatidal ethanolamine", "phosphatidal choline", etc. has been proposed for native plasmalogen phosphatides, and "lysophosphatidal ethanolamine", "lysophosphatidal choline", etc. for corresponding deacylated derivatives. This nomenclature minimizes the confusion arising from less precise terms, such as "plasmalogen" or "ethanolamine plasmalogen", "choline plasmalogen", etc. to designate either native compds, lysoderivatives, or other structures which may occur (molecules with two a,b-unsaturated ether chains or with one saturated ether and one a,b-unsaturated ether chain, and true cyclic glyceryl acetal derivatives). First isoln of a pure native plasmalogen (phosphatidal choline): Gottfried, Rapport, Fed. Proc. 20, 278 (1961); eidem, J. Biol. Chem. 237, 329 (1962). Ref: Rapport, Norton, Annu. Rev. Biochem. 31, 103 (1962). Synthesis: Piantadosi et al., J. Org. Chem. 28, 2425 (1963); Chacko et al., ibid. 32, 3698 (1967); Slotboom et al., Chem. Phys. Lipids 1, 192 (1967); Gigg, Gigg, J. Chem. Soc. C 1968, 16, 2030; Vtorov et al., Tetrahedron Lett. 1971, 4605. Reviews: E. Klenk, H. Debuch, "Plasmalogens" in Holman et al., Progr. Chem. Fats Lipids vol. 6, (Macmillan, New York, 1963) pp 1-29; Piantadosi, Snyder, J. Pharm. Sci. 59, 283-297 (1970).