Phospha tides

The principal lipid constituent of the tubercle bacilli was a wax-like substance. Anderson obtained this by chloroform extraction of fat-free bacilli. The preliminary removal of lipids with alcohol and other solvents served to dissolve the free fatty acids, neutral fat and phospha-tides. The crude wax was fractionated with alcohol or acetone. The purified derivative was a white amorphous powder containing 0.41% nitrogen and 0.77% phosphorus. The substance was very resistant to acid hydrolysis. Continuous treatment with acidified alcohol resulted in very slow hydrolysis. Alkaline hydrolysis proceeded very rapidly, with the formation of ether-soluble components together with a water-soluble polysaccharide. 

Phospholipids. These components are better known to oil processors as phospha-tides and are frequently referred to, together with small quantities of carbohydrates and resins, as gums that have adverse effects on product quality and refined oil yield. Phosphatides are emulsifiers, and so hinder the separation of oil and water phases in the caustic-refining process. The phosphatides are broadly separated into hydratable and nonhydratable types. As the name implies, hydratable phosphatides can be removed by treatment with water, and the nonhydratable compounds, which are salts or coordination compounds of calcium and magnesium primarily... 

Soapstock (free fatty acids, phospha tides)... 

Unlike surfactants, these agents do not appreciably lower surface and interfacial tension thus, they have little tendency to create foam or wet particles. Most deflocculants, however, are not generally considered safe for internal use, and as a result the only acceptable dispersant for internal products is lecithin or a lecithin derivative (naturally occurring mixture of phospha-tides and phospholipids). Because lecithins vary in water solubility and dispersibility characteristics, proper control of product specifications must be maintained to obtain reproducibility. 

It should also be useful to find a definition rendering it possible to include among the lipides a group of compounds that are now usually placed there—the acetal-phospha-tides—formed from two alcoholic groups of glycerol and the aldehydes of the corresponding fatty acids. 

Wittcoff, Harold, The Phospha tides, New York, Reinhold Publishing Corp., 1951. 

Carter and coworkers22 reported the isolation from plant seeds (for example, soya beans) of lipid material that consists of phospha-tides that contain long-chain, aliphatic amino alcohol-sugar conjugates. Purification of the lipid material for degradation studies was performed by solvent extraction, followed by countercurrent distribution.I20-121 The compounds obtained contained122 myo-inositol residues... 

CiaHJ3Oa mol wl 304.46. C 78.89%. H 10.60%, O 10.51%. An essential fatty acid, q.v, and a precursor m the biosynthesis of prostaglandins, thromboxanes, and leukotrienes, q.q. v. Structure Mo wry et al.. J. Biol. Chem. 142, 679 (1942) Arcus, Smedley-Maclean. Biochem- J. 37, 1 (1943). Occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and is a constituent of animal phospha tides. Isolation from Liver lipids Brown, J, Biol. Chem. 80, 455 (1928) from beef... 

It is necessary for export oil requirements that the oil be free of impurities that could settle out during shipment—sludges form when the hygroscopic phospha-tides become hydrated by moisture from the air. 

Thus we may conclude that only the C20- and C22-polyenoic acids of the oleic, linoleic, and linolenic acid types are built into tissue phospha-tides. It cannot yet be decided whether the specificity of the chain elongating and dehydrogenating enzyme system is responsible, or whether a particular selective principle during the formation of the lipid cell structures is active. Possibly both are true. There may also be a relation... 

Lignocaric acid n-tetracosanoic acid, CH3-(CH2)22-C00H, a fatty acid M, 368.6, m.p. 84 °C. La. occurs as an esterified component of glycerides (usually less than 3%) in many seed oils, such as ground nut and rape seed oil. It is an esterified component of certain cerebrosides (e g kerasin), phospha-tides and waxes. 

The close relationship between lipid and carbohydrate metabolism is shown by the interaction of L. and fat tissue. Fatty acids from food or the body s fat depots are degraded by 3-oxidation in the L. Excess fatty acids lead to the formation of ketone bodies. When needed, fatty acids can be synthesized from carbohydrates and transported by the blood as phospha-tides to the fat tissue. Here they are converted to neutral fats. The L. is able to synthesize cholesterol and to export it to other tissues, or convert it into bile acids. 

Metabolism and Functions of Phospha-tides. Specific Fattty Acids Composition of the Red Blood Cell Membranes... 

Wagner, H., Horhammer, L., and Wolff, P. (1961). Thin layer chromatography of phospha-tides and glycolipids. Bloc hem. Z. 334 175-184. 

Cardiolipin (1,3-diphosphatidylglycerol) has been found in soybean lipids (Benson and Strickland, 1960) it is probably the precursor of the 1,3-diglycerophosphoryl glycerol found in com and other vegetable oils (Okubara and Nakajama, 1955) phosphati-dylinositol (V) has been isolated from soybean and peanut phospha-tides (Hawthorne et al., 1960 Lepage et al., 1960 Okubara and Nakajama, 1955). 

As shown on p. 168j, serine can be converted to pyruvate (elimination of water forms the unsaturated amino acid which goes via the imino acid to the a-keto acid) as well as hydroxypyruvate or phosphoserine. The phosphorylated form, which could also come from 3-phosphoglycerate, occurs in a few proteins and phospha-tides (Chapt. XIII). Other bases present in the phosphatides, i.e. ethanolamine and choline, also originate from serine. 

The knowledge of exact turnover figures is of interest when comparing, for example, the amount of fat metabolized with the amount of phospha-tides turned over. In many cases however we can draw conclusions merely by comparing the specific activity of the phosphatides present in an organ under varying conditions. Such a procedure is applied in the study of the effect of ingested fat on the rate of renewal of phosphatides, of the effect of choline, cholesterol, and other substances on the turnover of liver phosphatides, of the site of fonnation of the yolk, embryo, and milk phosphatides, and so on. 

Shortly after administration of labeled phosphate, tagged phospha-tides penetrate from the liver into the circulation. By 40 hours 0.5 to 0.1% of the administered has been incorporated into phosphatides in... 

---