Phosphatidyl cholines

Phosphatidylcholine is an important component of cell membranes but cell mem branes are more than simply lipid bilayers Although their composition varies with their source a typical membrane contains about equal amounts of lipid and protein and the amount of cholesterol m the lipid fraction can approximate that of phosphatidylcholine The lipid fraction is responsible for the structure of the membrane Phosphatidyl choline provides the bilayer that is the barrier between what is inside the cell and what IS outside Cholesterol intermingles with the phosphatidylcholine to confer an extra measure of rigidity to the membrane... 

Phospholipid (Section 26 4) Adiacylglycerol beanng a choline phosphate head group Also known as phosphatidyl choline... 

Lecithin. Lecithin [8002-43-5] (qv) is a mixture of fat-like compounds that includes phosphatidyl choline, phosphatidyl ethanolamines, inositol phosphatides, and other compounds (37). Commercial lecithin was originally obtained from egg yolks, but is now extracted from soybean oil. Lecithin is used in many products, including margarine, chocolate, ice cream, cake batter, and bread. 

Low concentrations of solubilised jS-albumin inhibit ACh release in slices from rat hippocampus and cortex areas which show degeneration in AzD, but not in slices from the striatum which is unaffected. While not totally specific to ACh, since some inhibition of NA and DA and potentiation of glutamate release have been reported, this effect is achieved at concentrations of A/i below those generally neurotoxic. Since jS-amyloid can inhibit choline uptake it is also possible (see Auld, Kar and Quiron 1998) that in order to obtain sufficient choline for ACh synthesis and the continued function of cholinergic neurons, a breakdown of membrane phosphatidyl choline is required leading to cell death (so-called autocannibalism), /i-amyloid can also reduce the secondary effects of Mi receptor activation such as GTPase activity... 

This requires the provision of the precursor choline which is often given as lecithin (phosphatidyl choline), a natural source of choline found in many foods such as eggs and fish. Large doses (9-10 g) have to be given, probably to overcome the body s... 

DMN oxidative demethylation has been shown to be a liver mi-crosome cytochrome P-450 monooxygenase (10) Lotlikar et al. (11) found that a reconstituted enzyme system, consisting of cytochrome P-450, NADPH-cytochrome P-450 reductase and phosphatidyl choline was effective in catalyzing the demethylation of DMN. The most commonly accepted mechanism for the oxidative demethylation of DMN and, by extension, of other dialkyInltrosamlnes is shown in Scheme 1. 

Soya lecithin is a natural product which contains about 34% glycerides (soya oil), 5% sugars, and 61% phosphatides. The phosphatides in turn are comprised of phosphatidyl choline, i.e., chemical lecithin (20%), phosphatidyl ethanolamine (20%), and phosphatidyl inositol (21%). 

The chromatogram of the commercial soya lecithin as shown in Figure 4 suggests a number of components and all subsequent work was done with the ethanol-soluble fraction, i.e., phosphatidyl choline, or the ethanol-insoluble fraction, comprised primarily of other phosphatides. 

Figure 5. GPC chromatograms of phosphatidyl choline fraction of soya lecithin (conditions same as for Figure 4 except injection volume 50-250 pJL)...

Figure 6. GPC chromatograms of phosphatidyl choline fraction (solvent THF columns 10 A + /O A -f 10 A + 500 A fjJStyragel flow rate 1.81 mL/min injection volume 25-250 fxL)...

Figure 7. Effect of sample size on apparent molecular weight for soya lecithin phosphatide fractions (conditions same as for Figures 5 and 6 (O) ethanol-soluble fraction (phosphatidyl choline), oligomer GPC (%) ethanol-soluble fraction (phosphatidyl choline), "main column (l ) ethanol-insoluble fraction (other phos-p hat ides), "oligomer GPC (A) ethanol-insoluble fraction (other phosphatides),...

In l,2-diacylglycerol-3-phosphate the phosphate group was esterified with choline by means of CDI to give the phosphatidyl choline ... 

Analogues of phosphatidyl ethanolamine, phosphatidyl choline, and phosphatidic acid with pantoic acid skeleton were prepared by phosphorylation with the respective phosphoric mono-, bis-, and tristriazolide [17]... 

Normal lungs, however, produce a chemical substance referred to as pulmonary surfactant. Made by alveolar type II cells within the alveoli, surfactant is a complex mixture of proteins (10 to 15%) and phospholipids (85 to 90%), including dipalmitoyl phosphatidyl choline, the predominant constituent. By interspersing throughout the fluid lining the alveoli, surfactant disrupts the cohesive forces between the water molecules. As a result, pulmonary surfactant has three major functions ... 

The nomenclature for associating individual fatty acid groups with particular phosphodig-lyceride derivatives is straightforward. For instance, a phosphatidic acid (PA) derivative which contains two myristic acid chains is commonly called dimyristoyl phosphatidic acid (DMPA). Likewise, a PC derivative containing two palmitate chains is called dipalmitoyl phosphatidyl choline (DPPC). Other phosphodiglyceride derivatives are similarly named. 

Fig. 5 Surface pressure/area isotherm for the compression cycle of dipalmitoylphos-phatidyl choline (dashed line) and l-palmitoyl-2-(l2-hydroxystearoyl)phosphatidyl choline (solid line) on a pure water subphase at 25°C. Reprinted with permission from Arnett et al., 1989. Copyright 1989 American Chemical Society.

Shorter chain analogs of DPPC were also investigated in order to determine if the lack of stereo-differentiation in monolayer properties could be due to DPPC s higher gel point or complicating steric effects. Figure 15 shows the compression/expansion isotherms of DPPC as compared with racemic and enantiomeric dimyristoylphosphatidyl choline (DMPC) and dilauroyl phosphatidyl choline (DLPC). Again no stereodifferentiation in monolayer properties was observed as reflected by 11/A isotherms or dynamic surface tension. 

Table 1. comparison of Mal3(Phyt)2 and egg york phosphatidyl choline EPC... 

Talsma [1.34] showed with phospholipon 100 H, a hydrated phosphatidyl-choline of soya beans, (Nattermann, Cologne) and dicetylphosphate (DCP) (molar ratio 10 1) from which bilayer liposomes have been produced, the influence of one CPA (I), of several CPAs (II), of the vesicle size (III), and the cooling rate (IV). In all of the following tests Tris buffer of pH 7.4 is used. 

Crowe and Crowe [3.39] proved that it is sufficient for certain liposomes, e. g. egg phosphatidyl-choline (DPPC), to be vitrified by trehalose or dextran during freezing and freeze drying. In trehalose the retention rate was almost 100 %, and in dextran more than 80 %. This did not apply to egg PC-liposomes Dextran as CPA alone led to an almost total loss of the CF-indicator, but addition of dextran into a trehalose solution (Fig. 3.20) also reduced the retention rate of CF substantially, e. g. from 90 % in a pure trehalose to approx. 45 % if trehalose and dextran were in equal amounts in the solution. Since T of dextran is approx. -10 °C and Tg- of trehalose is -30 to -32 °C, dextran should form a glass phase at much higher temperatures than trehalose. Therefore the stabilization of egg- PC with trehalose cannot be related with the vitrification. Crowe showd with IR spectroscopy that egg-PC freeze dried with 2 g trehalose/g lipid had almost the identical spectrographic characteristics as the hydrous lipid Trehalose molecules replaced the water molecules, and hydrogen... 

Hauser, H., Pascher, I., Pearson, R. H. and Sundell, S. (1981). Preferred conformation and molecular packing of phophatidylethanolamine and phosphatidyl choline, Biochim. Biophys. Acta, 650, 21-51. 

The pA a shift can be directly measured by the solvatochromic shift of the ultraviolet absorption spectra. For PCP, the p%lir is 5.97 in phosphatidyl choline membranes, and increases up to 6.78 in the negatively charged phosphatidyl glycerol membranes [123], The addition of cholesterol decreases the pATam again slightly in both types of membranes. 

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