Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can easily be obtained from a variety of readily available sources, such as egg yolk or soybeans, from which they are mechanically or chemically extracted using hexane. They are also a member of the lecithin group of yellow-brownish fatty substances occurring in animal and plant tissues. Dipalmitoylphosphatidylcholine (lecithin) is a major component of the pulmonary surfactant, and is often used in the lecithin–sphingomyelin ratio to calculate fetal lung maturity. While phosphatidylcholines are found in all plant and animal cells, they are absent in the membranes of most bacteria, [1] including Escherichia coli . [2] Purified phosphatidylcholine is produced commercially.[ citation needed ]
The name lecithin was derived from Greek λέκιθος, lekithos 'egg yolk' by Theodore Nicolas Gobley, a French chemist and pharmacist of the mid-19th century, who applied it to the egg yolk phosphatidylcholine that he identified in 1847. Gobley eventually completely described his lecithin from chemical structural point of view, in 1874. Phosphatidylcholines are such a major component of lecithin that in some contexts the terms are sometimes used as synonyms. However, lecithin extracts consist of a mixture of phosphatidylcholine and other compounds. It is also used along with sodium taurocholate for simulating fed- and fasted-state biorelevant media in dissolution studies of highly lipophilic drugs.
Phosphatidylcholine is a major constituent of cell membranes and pulmonary surfactant, and is more commonly found in the exoplasmic or outer leaflet of a cell membrane. It is thought to be transported between membranes within the cell by phosphatidylcholine transfer protein (PCTP). [3]
Phosphatidylcholine also plays a role in membrane-mediated cell signaling and PCTP activation of other enzymes. [4]
This phospholipid is composed of a choline head group and glycerophosphoric acid, with a variety of fatty acids. Usually, one is a saturated fatty acid (in the given figure, this is palmitic acid (hexadecanoic acid, H3C-(CH2)14-COOH); margaric acid (heptadecanoic acid, H3C-(CH2)15-COOH), identified by Gobley in egg yolk, also belong to that class); and the other is an unsaturated fatty acid (here oleic acid, or 9Z-octadecenoic acid, as in Gobley's original egg yolk lecithin). However, there are also examples of disaturated species. Animal lung phosphatidylcholine, for example, contains a high proportion of dipalmitoylphosphatidylcholine. [5]
Phospholipase D catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid (PA), releasing the soluble choline headgroup into the cytosol.[ citation needed ]
A 2009 systematic review of clinical trials in humans found that there was not enough evidence to support supplementation of lecithin or phosphatidylcholine in dementia. The study found that a moderate benefit could not be ruled out until further large scale studies were performed. [6]
Though phosphatidylcholine has been studied as an alternative to liposuction, no peer-reviewed study has shown it to have comparable effects. [7] [8] Injection of phosphatidylcholine in lipomas has been studied, but the results have been mixed. [9] [10]
Treatment of ulcerative colitis with oral intake of phosphatidylcholine has been shown to result in decreased disease activity. [11]
Although multiple pathways exist for the biosynthesis of phosphatidylcholine, the predominant route in eukaryotes involves condensation between diacylglycerol (DAG) and cytidine 5'-diphosphocholine (CDP-choline or citicoline). The conversion is mediated by the enzyme diacylglycerol cholinephosphotransferase. Another pathway, mainly operative in the liver involves methylation of phosphatidylethanolamine with S-adenosyl methionine (SAM) being the methyl group donor. [12]
Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include storing energy, signaling, and acting as structural components of cell membranes. Lipids have applications in the cosmetic and food industries, and in nanotechnology.
Phospholipids are a class of lipids whose molecule has a hydrophilic "head" containing a phosphate group and two hydrophobic "tails" derived from fatty acids, joined by an alcohol residue. Marine phospholipids typically have omega-3 fatty acids EPA and DHA integrated as part of the phospholipid molecule. The phosphate group can be modified with simple organic molecules such as choline, ethanolamine or serine.
Choline is a cation with the chemical formula [(CH3)3NCH2CH2OH]+. Choline forms various salts, such as choline chloride and choline bitartrate. It is an essential nutrient for humans and many other animals, and is a structural part of phospholipids and cell membranes.
Among animals which produce eggs, the yolk is the nutrient-bearing portion of the egg whose primary function is to supply food for the development of the embryo. Some types of egg contain no yolk, for example because they are laid in situations where the food supply is sufficient or because the embryo develops in the parent's body, which supplies the food, usually through a placenta. Reproductive systems in which the mother's body supplies the embryo directly are said to be matrotrophic; those in which the embryo is supplied by yolk are said to be lecithotrophic. In many species, such as all birds, and most reptiles and insects, the yolk takes the form of a special storage organ constructed in the reproductive tract of the mother. In many other animals, especially very small species such as some fish and invertebrates, the yolk material is not in a special organ, but inside the egg cell.
Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances, and are used for smoothing food textures, emulsifying, homogenizing liquid mixtures, and repelling sticking materials.
Deoxycholic acid is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol and acetic acid. When pure, it exists in a white to off-white crystalline powder form.
Phosphatidylinositol or inositol phospholipid is a biomolecule. It was initially called "inosite" when it was discovered by Léon Maquenne and Johann Joseph von Scherer in the late 19th century. It was discovered in bacteria but later also found in eukaryotes, and was found to be a signaling molecule.
Phosphatidic acids are anionic phospholipids important to cell signaling and direct activation of lipid-gated ion channels. Hydrolysis of phosphatidic acid gives rise to one molecule each of glycerol and phosphoric acid and two molecules of fatty acids. They constitute about 0.25% of phospholipids in the bilayer.
Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes in eukaryotic cells. They are a type of lipid, of which its composition affects membrane structure and properties. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea.
Théodore (Nicolas) Gobley (French:[ɡɔblɛ]; 11 May 1811, in Paris – 1 September 1876, in Bagnères-de-Luchon, was the first to isolate and ultimately determine the chemical structure of lecithin, the first identified and characterized member of the phospholipids class. He was also a pioneer researcher in the study and analysis of the chemical components of brain tissues.
Dipalmitoylphosphatidylcholine (DPPC) is a phospholipid (and a lecithin) consisting of two C16 palmitic acid groups attached to a phosphatidylcholine head-group.
Phosphatidylserine is a phospholipid and is a component of the cell membrane. It plays a key role in cell cycle signaling, specifically in relation to apoptosis. It is a key pathway for viruses to enter cells via apoptotic mimicry. Its exposure on the outer surface of a membrane marks the cell for destruction via apoptosis.
Phospholipase D (EC 3.1.4.4, lipophosphodiesterase II, lecithinase D, choline phosphatase, PLD; systematic name phosphatidylcholine phosphatidohydrolase) is an anesthetic sensitive and mechanosensitive enzyme of the phospholipase superfamily that catalyses the following reaction
Phosphatidylethanolamine (PE) is a class of phospholipids found in biological membranes. They are synthesized by the addition of cytidine diphosphate-ethanolamine to diglycerides, releasing cytidine monophosphate. S-Adenosyl methionine can subsequently methylate the amine of phosphatidylethanolamines to yield phosphatidylcholines.
Phosphatidylethanolamine N-methyltransferase is a transferase enzyme which converts phosphatidylethanolamine (PE) to phosphatidylcholine (PC) in the liver. In humans it is encoded by the PEMT gene within the Smith–Magenis syndrome region on chromosome 17.
Sec14 is a cytosolic protein found in yeast which plays a role in the regulation of several cellular functions, specifically those related to intracellular transport. Encoded by the Sec14 gene, Sec14p may transport phosphatidylinositol and phosphatidylcholine produced in the endoplasmic reticulum and the Golgi body to other cellular membranes. Additionally, Sec14p potentially plays a role in the localization of lipid raft proteins. Sec14p is an essential gene in yeast, and is homologous in function to phosphatidylinositol transfer protein in mammals. A conditional mutant with non-functional Sec14p presents with Berkeley bodies and deficiencies in protein secretion.
Phosphatidylcholine transfer protein (PCTP), also known as StAR-related lipid transfer domain protein 2 (STARD2), is a specific intracellular phospholipid binding protein that can transfer phosphatidylcholine between different membranes in the cytosol.
1-Lysophosphatidylcholines are a class of phospholipids that are intermediates in the metabolism of lipids. They result from the hydrolysis of an acyl group from the sn-1 position of phosphatidylcholine. They are also called 2-acyl-sn-glycero-3-phosphocholines. The synthesis of phosphatidylcholines with specific fatty acids occurs through the synthesis of 1-lysoPC. The formation of various other lipids generates 1-lysoPC as a by-product.
Egg lecithin is a type of lecithin, a group of compounds primarily containing phospholipids, that is derived from eggs.
The CDP-choline pathway, first identified by Eugene P. Kennedy in 1956, is the predominant mechanism by which mammalian cells synthesize phosphatidylcholine (PC) for incorporation into membranes or lipid-derived signalling molecules. The CDP-choline pathway represents one half of what is known as the Kennedy pathway. The other half is the CDP-ethanolamine pathway which is responsible for the biosynthesis of the phospholipid phosphatidylethanolamine (PE).
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: CS1 maint: location (link)Recent laboratory investigations17 demonstrate that sodium deoxycholate, a bile salt also used as a laboratory detergent,102,103 was just as potent at causing adipocyte lysis and cell death as the complete phosphatidylcholine formula, which contains both phosphatidylcholine and deoxycholate (Figure 3). This bile salt is used to solubilize phosphatidylcholine by forming mixed micelles composed of phosphatidylcholine and deoxycholate.102,104 It is common practice to combine intravenous medications with bile salts to improve their water solubility.105,106 These findings suggest that sodium deoxycholate is the primary active ingredient in the phosphatidylchloline preparations.
The author, when discussing phosphatidylcholine as a part of mesotherapy concludes: 'Although there is a preliminary report contradictory to this result, there was no body contouring observed in this study. There were no statistically significant changes in thigh girth, cross-sectional area, or laboratory values for the lipid profile except for a decrease in the triglyceride level in the blood, which might be an indirect effect of the method of aminophylline absorption into the systemic circulation.'
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