Phosphatidylcholine

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1-Oleoyl-2-palmitoyl-phosphatidylcholine 1-Oleoyl-2-almitoyl-phosphatidylcholine Structural Formulae V.1.png
1-Oleoyl-2-palmitoyl-phosphatidylcholine

Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can be easily 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 ]

Contents

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]

Structure and physical properties

Palmitoyl-oleyl-sn-phosphatidylcholine, a phosphatidylcholine 1-palmitoyl-2-oleoylphosphatidylcholine.svg
Palmitoyl-oleyl-sn-phosphatidylcholine, a phosphatidylcholine

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 ]

Possible health benefits

Senescence

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]

Lipolysis

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]

Ulcerative colitis

Treatment of ulcerative colitis with oral intake of phosphatidylcholine has been shown to result in decreased disease activity. [11]

Biosynthesis

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]

Additional images

See also

Related Research Articles

<span class="mw-page-title-main">Lipid</span> Substance of biological origin that is soluble in nonpolar solvents

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.

<span class="mw-page-title-main">Phospholipid</span> Class of lipids

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.

<span class="mw-page-title-main">Choline</span> Chemical compound and essential nutrient

Choline is a cation with the chemical formula [(CH3)3NCH2CH2OH]+. Choline forms various salts, for example choline chloride and choline bitartrate.

<span class="mw-page-title-main">Yolk</span> Part of an egg which feeds the developing embryo

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.

<span class="mw-page-title-main">Lecithin</span> Generic term for amphiphilic substances of plant and animal origin

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.

<span class="mw-page-title-main">Deoxycholic acid</span> Bile acid

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.

<span class="mw-page-title-main">Sphingomyelin</span> Class of chemical compounds

Sphingomyelin is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine head group; therefore, sphingomyelins can also be classified as sphingophospholipids. In humans, SPH represents ~85% of all sphingolipids, and typically make up 10–20 mol % of plasma membrane lipids.

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.

<span class="mw-page-title-main">Glycerophospholipid</span> Class of lipids

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.

<span class="mw-page-title-main">Dipalmitoylphosphatidylcholine</span> Chemical compound

Dipalmitoylphosphatidylcholine (DPPC) is a phospholipid (and a lecithin) consisting of two C16 palmitic acid groups attached to a phosphatidylcholine head-group.

<span class="mw-page-title-main">Phosphatidylserine</span> Chemical compound

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 enzyme of the phospholipase superfamily that catalyses the following reaction

<span class="mw-page-title-main">Phosphatidylethanolamine</span> Group of chemical compounds

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.

<span class="mw-page-title-main">Phosphatidylethanolamine N-methyltransferase</span> Protein-coding gene in the species Homo sapiens

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.

Lipid droplets, also referred to as lipid bodies, oil bodies or adiposomes, are lipid-rich cellular organelles that regulate the storage and hydrolysis of neutral lipids and are found largely in the adipose tissue. They also serve as a reservoir for cholesterol and acyl-glycerols for membrane formation and maintenance. Lipid droplets are found in all eukaryotic organisms and store a large portion of lipids in mammalian adipocytes. Initially, these lipid droplets were considered to merely serve as fat depots, but since the discovery in the 1990s of proteins in the lipid droplet coat that regulate lipid droplet dynamics and lipid metabolism, lipid droplets are seen as highly dynamic organelles that play a very important role in the regulation of intracellular lipid storage and lipid metabolism. The role of lipid droplets outside of lipid and cholesterol storage has recently begun to be elucidated and includes a close association to inflammatory responses through the synthesis and metabolism of eicosanoids and to metabolic disorders such as obesity, cancer, and atherosclerosis. In non-adipocytes, lipid droplets are known to play a role in protection from lipotoxicity by storage of fatty acids in the form of neutral triacylglycerol, which consists of three fatty acids bound to glycerol. Alternatively, fatty acids can be converted to lipid intermediates like diacylglycerol (DAG), ceramides and fatty acyl-CoAs. These lipid intermediates can impair insulin signaling, which is referred to as lipid-induced insulin resistance and lipotoxicity. Lipid droplets also serve as platforms for protein binding and degradation. Finally, lipid droplets are known to be exploited by pathogens such as the hepatitis C virus, the dengue virus and Chlamydia trachomatis among others.

<span class="mw-page-title-main">Sec14</span>

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.

<span class="mw-page-title-main">Phosphatidylcholine transfer protein</span> Intracellular phospholipid binding protein

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.

<span class="mw-page-title-main">1-Lysophosphatidylcholine</span>

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.

<span class="mw-page-title-main">Egg lecithin</span>

Egg lecithin is a type of lecithin, a group of compounds primarily containing phospholipids, that is derived from eggs.

<span class="mw-page-title-main">CDP-choline pathway</span>

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).

References

  1. Jackowski S, Cronan JE, Rock CO (1991). "Chapter 2: Lipid metabolism in procaryotes" . In Vance DE, Vance J (eds.). Biochemistry of Lipids, Lipoproteins and Membranes. Elsevier. pp.  80–81. ISBN   978-0-444-89321-5.
  2. Chen F, Zhao Q, Cai X, Lv L, Lin W, Yu X, Li C, Li Y, Xiong M, Wang XG (November 2009). "Phosphatidylcholine in membrane of Escherichia coli changes bacterial antigenicity". Canadian Journal of Microbiology. 55 (11): 1328–34. doi:10.1139/w09-082. PMID   19940943.
  3. Wirtz KW (July 1991). "Phospholipid transfer proteins". Annual Review of Biochemistry. 60 (13): 73–99. doi:10.1146/annurev.bi.60.070191.000445. PMID   1883207.
  4. Kanno K, Wu MK, Agate DS, Fanelli BJ, Wagle N, Scapa EF, Ukomadu C, Cohen DE (October 2007). "Interacting proteins dictate function of the minimal START domain phosphatidylcholine transfer protein/StarD2". The Journal of Biological Chemistry. 282 (42): 30728–36. doi: 10.1074/jbc.M703745200 . PMID   17704541.
  5. Christie WW. "Phosphatidylcholine and Related Lipids: Structure, Occurrence, Biochemistry and Analysis". Invergowrie, Dundee (DD2 5DA), Scotland.: James Hutton Institute. Archived from the original on 2014-12-11. Retrieved 2012-08-06.{{cite web}}: CS1 maint: location (link)
  6. Higgins JP, Flicker L (21 January 2009). Higgins JP (ed.). "Lecithin for dementia and cognitive impairment". The Cochrane Database of Systematic Reviews. 4 (3): CD001015. doi:10.1002/14651858.CD001015. PMID   12917896.
  7. Rotunda AM, Kolodney MS (April 2006). "Mesotherapy and phosphatidylcholine injections: historical clarification and review". Dermatologic Surgery. 32 (4): 465–80. CiteSeerX   10.1.1.506.2372 . doi:10.1111/j.1524-4725.2006.32100.x. PMID   16681654. S2CID   9994696. 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.
  8. Park SH, Kim DW, Lee MA, Yoo SC, Rhee SC, Koo SH, Seol GH, Cho EY (April 2008). "Effectiveness of mesotherapy on body contouring". Plastic and Reconstructive Surgery. 121 (4): 179e–85e. doi:10.1097/01.prs.0000304611.71480.0a. PMID   18349597. S2CID   22619355. 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.'
  9. Amber KT, Ovadia S, Camacho I (June 2014). "Injection therapy for the management of superficial subcutaneous lipomas". The Journal of Clinical and Aesthetic Dermatology. 7 (6): 46–8. PMC   4086534 . PMID   25013540.
  10. Nanda S (May 2011). "Treatment of lipoma by injection lipolysis". Journal of Cutaneous and Aesthetic Surgery. 4 (2): 135–7. doi: 10.4103/0974-2077.85040 . PMC   3183720 . PMID   21976907.
  11. Kokkinidis DG, Bosdelekidou EE, Iliopoulou SM, Tassos AG, Texakalidis PT, Economopoulos KP, Kousoulis AA (September 2017). "Emerging treatments for ulcerative colitis: a systematic review". Scandinavian Journal of Gastroenterology. 52 (9): 923–931. doi:10.1080/00365521.2017.1326163. PMID   28503977. S2CID   4074211.
  12. Philip Y (2016-02-17). The membranes of cells (Third ed.). London. pp. 61–62. ISBN   9780128004869. OCLC   940961458.{{cite book}}: CS1 maint: location missing publisher (link)