Biological phosphatidylcholine

Koryta et al. [48] first stressed the relevance of adsorbed phospholipid monolayers at the ITIES for clarification of biological membrane phenomena. Girault and Schiffrin [49] first attempted to characterize quantitatively the monolayers of phosphatidylcholine and phos-phatidylethanolamine at the ideally polarized water-1,2-dichloroethane interface with electrocapillary measurements. The results obtained indicate the importance of the surface pH in the ionization of the amino group of phosphatidylethanolamine. Kakiuchi et al. [50] used the video-image method to study the conditions for obtaining electrocapillary curves of the dilauroylphosphatidylcholine monolayer formed on the ideally polarized water-nitrobenzene interface. This phospholipid was found to lower markedly the surface tension by forming a stable monolayer when the interface was polarized so that the aqueous phase had a negative potential with respect to the nitrobenzene phase [50,51] (cf. Fig. 5). 

The majority of CYP enzymes are located in a hydrophobic environment in the endoplasmic reticulum of cells, although cytosolic enzymes also exist, such as CYP101. In order to mimic the physiological environment of CYP enzymes, a number of groups have used phospholipids to construct biosensors such as DDAB, dimeristoyl-L-a-phosphatidylcholine (DMPC), dilauroylphosphatidylethanolamine (DLPE) and distearoylphosphatidylethanolamine (DSPE). Phospholipid layers form stable vesicular dispersions that bear structural relationship with the phospholipid components of biologically important membranes. By this way a membranous environment is created that facilitates electron transfer between the enzyme s redox center and the electrode. 

An important characteristic of mammalian 15-LOX is its capacity to oxidize the esters of unsaturated acid in biological membranes and plasma lipoproteins without their hydrolysis to free acids. Jung et al. [19] found that human leukocyte 15-LOX oxidized phosphatidylcholine at carbon-15 of the AA moiety. Soybean and rabbit reticulocyte 15-LOXs were also active while human leukocyte 5-LOX, rat basophilic leukemia cell 5-LOX, and rabbit platelet 12-LOX were inactive. It was suggested that the oxygenation of phospholipid is a unique property of 15-LOX. However, Murray and Brash [20] showed that rabbit reticulocyte... 

As mentioned above, PAF and PAF-like molecules are rapidly synthesized by keratinocytes following UV exposure. We suggest that two mechanisms are involved. UV-induced free radical formation leads to membrane oxidation and the formation of oxidized phosphatidylcholine. The PAF-like molecules bind to PAF receptors in either a paracrine or autocrine fashion. This induces the release of arachidonic acid from the membrane, activates PI.A2 and promotes the synthesis of bona fide PAF.55 The newly synthesized PAF then binds to PAF receptors, which upregulates the production of more PAF and downstream biological modifiers such as eicosanoids and cytokines. Ultimately this activates the cascade of events that leads to immune suppression. 

The biological membrane is composed of lipid bilayers and proteins, and it is generally agreed that the lipid bilayer (layer width, 50-70 A) is the basic structural unit (e.g. Brockerhoff, 1977). The most abundant bilayer-forming lipids are the phosphatidylcholines (lecithins). These compounds have a... 

Lipid-protein interactions are of major importance in the structural and dynamic properties of biological membranes. Fluorescent probes can provide much information on these interactions. For example, van Paridon et al.a) used a synthetic derivative of phosphatidylinositol (PI) with a ris-parinaric acid (see formula in Figure 8.4) covalently linked on the sn-2 position for probing phospholipid vesicles and biological membranes. The emission anisotropy decays of this 2-parinaroyl-phosphatidylinositol (PPI) probe incorporated into vesicles consisting of phosphatidylcholine (PC) (with a fraction of 5 mol % of PI) and into acetylcholine receptor rich membranes from Torpedo marmorata are shown in Figure B8.3.1. 

LEH is primarily composed of a combination of saturated high-carbon phospholipids and cholesterol. Synthetic phospholipids replaced hydrogenated soy lecithin when the latter was found to induce several untoward biological responses (40). Current choice of a saturated high-carbon phospholipid is mostly between distearoyl phosphatidylcholine (DSPC, 55°C) and... 

Phosphatidylcholines are the most prominent components of biological membranes and therefore often serve as model biomembrane systems in biophysical studies.Due to their amphiphathic character, phospholipids have a strong tendency to spontaneously form bilayer structures when... 

Our present ideas about the nature of biological membranes, which are so fundamental to all biochemical processes, are based on the Singer-Nicholson mosaic model. This model of the membrane is based on a phospholipid bilayer that is, however, asymmetrical. In the outside monolayer, phosphatidylcholine (lecithin) predominates, whereas the inner monolayer on the cytoplasmic side is rich in a mixture of phos-phatidylethanolamine, phosphatidylserine, and phosphatidylinositol. Cholesterol molecules are also inserted into the bilayer, with their 3-hydroxyl group pointed toward the aqueous side. The hydrophobic fatty acid tails and the steran skeleton of cholesterol... 

Plasma membrane lipids are asymmetrically distributed between the two monolayers of the bilayer, although the asymmetry, unlike that of membrane proteins, is not absolute. In the plasma membrane of the erythrocyte, for example, choline-containing lipids (phosphatidylcholine and sphingomyelin) are typically found in the outer (extracellular or exoplasmic) leaflet (Fig. 11-5), whereas phosphatidylserine, phosphatidyl-ethanolamine, and the phosphatidylinositols are much more common in the inner (cytoplasmic) leaflet. Changes in the distribution of lipids between plasma membrane leaflets have biological consequences. For example, only when the phosphatidylserine in the plasma membrane moves into the outer leaflet is a platelet able to play its role in formation of a blood clot. For many other cells types, phosphatidylserine exposure on the outer surface marks a cell for destruction by programmed cell death. 

Hay and Morrison (1971) later presented additional data on the fatty acid composition and structure of milk phosphatidylethanolamine and -choline. Additionally, phytanic acid was found only in the 1-position of the two phospholipids. The steric hindrance presented by the four methyl branches apparently prevents acylation at the 2-position. The fairly even distribution of monoenoic acids between the two positions is altered when the trans isomers are considered, as a marked asymmetry appears with 18 1 between the 1- and 2-positions of phosphatidylethanolamine, but not of phosphatidylcholine. Biologically, the trans isomers are apparently handled the same as the equivalent saturates because the latter have almost the same distribution. There are no appreciable differences in distribution of cis or trans positional isomers between positions 1 and 2 in either phospholipid. Another structural asymmetry observed is where cis, cis nonconjugated 18 2s are located mostly in the 2-position in both phospholipids. It appears that one or more trans double bonds in the 18 2s hinders the acylation of these acids to the 2-position. 

A Cantafora, R Masella. Improved determination of individual molecular species of phosphatidylcholine in biological samples by high performance liquid chromatography with internal standards. J Chromatogr 593 139-146, 1992. 

Two main types of lipids occur in biological membranes phospholipids and sterols. The predominant phospholipids in most membranes are phosphoglycerides, which are phosphate esters of the three-carbon alcohol, glycerol. A typical structure is that of phosphatidylcholine (lecithin) ... 

MacDonald RC, Ashley GW, Shida MM et al (1999) Physical and biological properties of cationic triesters of phosphatidylcholine. Biophys J 77 2612-2629... 

At present the number of steroid 13C NMR studies on molecules of biological interest is very small. The spectra of cholesteryl linoleate alone and in aqueous codispersions of egg phosphatidylcholine have been reported. (37) Line width considerations are used to draw conclusions of steroid organization and molecular motion. These results have been compared with the changes in the spectra of human serum... 

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