Phospholipid - wikipedia Phospholipid Phospholipid The left image shows a phospholipid, and the right image shows the chemical makeup. Phosphatidyl choline is the major component of lecithin. It is also a source for choline in the synthesis of acetylcholine in cholinergic neurons. Cell membranes consist of phospholipid bilayers Phospholipids are a class of lipids that are a major component of all cell membranes. They can form lipid bilayers because of their amphiphilic characteristic. The structure of the phospholipid molecule generally consists of two hydrophobic fatty acid `` tails '' and a hydrophilic `` head '' consisting of a phosphate group. The two components are joined together by a glycerol molecule. The phosphate groups can be modified with simple organic molecules such as choline. The first phospholipid identified in 1847 as such in biological tissues was lecithin, or phosphatidylcholine, in the egg yolk of chickens by the French chemist and pharmacist, Theodore Nicolas Gobley. Biological membranes in eukaryotes also contain another class of lipid, sterol, interspersed among the phospholipids and together they provide membrane fluidity and mechanical strength. Purified phospholipids are produced commercially and have found applications in nanotechnology and materials science. Contents 1 Amphiphilic character 1.1 Diacylglyceride structures 1.2 Phosphosphingolipids 2 Applications 3 Simulations 4 Characterization 4.1 Analysis 5 Phospholipid synthesis 6 Sources 7 In signal transduction 8 Food technology 9 Phospholipid derivatives 10 Abbreviations used and chemical information of glycerophospholipids 11 See also 12 References Amphiphilic character An amphiphile ( from the Greek αμφις, amphis : both and φιλíα, philia : love, friendship ) is a term describing a chemical compound possessing both hydrophilic ( water - loving, polar ) and lipophilic ( fat - loving ) properties. The phospholipid head contains a negatively charged phosphate group and glycerol ; it is hydrophilic ( attracted to water ). The phospholipid tails usually consists of 2 long fatty acid chains ; they are hydrophobic and avoid interactions with water. When placed in aqueous solutions, phospholipids are driven by hydrophobic interactions that result in the fatty acid tails aggregating to minimize interactions with water molecules. These specific properties allow phospholipids to play an important role in the phospholipid bilayer. In biological systems, the phospholipids often occur with other molecules ( e.g., proteins, glycolipids, sterols ) in a bilayer such as a cell membrane. Lipid bilayers occur when hydrophobic tails line up against one another, forming a membrane of hydrophilic heads on both sides facing the water. Such movement can be described by the fluid mosaic model, that describes the membrane as a mosaic of lipid molecules that act as a solvent for all the substances and proteins within it, so proteins and lipid molecules are then free to diffuse laterally through the lipid matrix and migrate over the membrane. Sterols contribute to membrane fluidity by hindering the packing together of phospholipids. However, this model has now been superseded, as through the study of lipid polymorphism it is now known that the behaviour of lipids under physiological ( and other ) conditions is not simple. Diacylglyceride structures See : Glycerophospholipid Phosphatidic acid ( phosphatidate ) ( PA ) Phosphatidylethanolamine ( cephalin ) ( PE ) Phosphatidylcholine ( lecithin ) ( PC ) Phosphatidylserine ( PS ) Phosphoinositides : Phosphatidylinositol ( PI ) Phosphatidylinositol phosphate ( PIP ) Phosphatidylinositol bisphosphate ( PIP2 ) and Phosphatidylinositol trisphosphate ( PIP3 ) Phosphosphingolipids See Sphingolipid Ceramide phosphorylcholine ( Sphingomyelin ) ( SPH ) Ceramide phosphorylethanolamine ( Sphingomyelin ) ( Cer - PE ) Ceramide phosphoryllipid Applications Phospholipids have been widely used to prepare liposomal, ethosomal and other nanoformulations of topical, oral and parenteral drugs for differing reasons like improved bio-availability, reduced toxicity and increased permeability across membranes. Liposomes are often composed of phosphatidylcholine - enriched phospholipids and may also contain mixed Phospholipid chains with surfactant properties. The ethosomal formulation of ketoconazole using phospholipids is a promising option for transdermal delivery in fungal infections. Simulations Computational simulations of phospholipids are often performed using molecular dynamics with force fields such as GROMOS, CHARMM, or AMBER. Characterization Phospholipids are optically highly birefringent, i.e. their refractive index is different along their axis as opposed to perpendicular to it. Measurement of birefringence can be achieved using cross polarisers in a microscope to obtain an image of e.g. vesicle walls or using techniques such as dual polarisation interferometry to quantify lipid order or disruption in supported bilayers. Analysis There are no simple methods available for analysis of phospholipids since the close range of polarity between different phospholipid species makes detection difficult. Oil chemists often use spectroscopy to determine total Phosphorus abundance and then calculate approximate mass of phospholipids based on molecular weight of expected fatty acid species. Modern lipid profiling employs more absolute methods of analysis, with nuclear magnetic resonance spectroscopy ( NMR ), particularly P - NMR, while HPLC - ELSD provides relative values. Phospholipid synthesis Phospholipid synthesis occurs in the cytosole adjacent to ER membrane that is studded with proteins that act in synthesis ( GPAT and LPAAT acyl transferases, phosphatase and choline phosphotransferase ) and allocation ( flippase and floppase ). Eventually a vesicle will bud off from the ER containing phospholipids destined for the cytoplasmic cellular membrane on its exterior leaflet and phospholipids destined for the exoplasmic cellular membrane on its inner leaflet. Sources Common sources of industrially produced phospholipids are soya, rapeseed, sunflower, chicken eggs, bovine milk, fish eggs etc. Each source has a unique profile of individual phospholipid species and consequently differing applications in food, nutrition, pharmaceuticals, cosmetics and drug delivery. In signal transduction Some types of phospholipid can be split to produce products that function as second messengers in signal transduction. Examples include phosphatidylinositol ( 4, 5 ) - bisphosphate ( PIP ), that can be split by the enzyme Phospholipase C into inositol triphosphate ( IP ) and diacylglycerol ( DAG ), which both carry out the functions of the G type of G protein in response to various stimuli and intervene in various processes from long term depression in neurons to leukocyte signal pathways started by chemokine receptors. Phospholipids also intervene in prostaglandin signal pathways as the raw material used by lipase enzymes to produce the prostaglandin precursors. In plants they serve as the raw material to produce Jasmonic acid, a plant hormone similar in structure to prostaglandins that mediates defensive responses against pathogens. Food technology Phospholipids can act as emulsifiers, enabling oils to form a colloid with water. Phospholipids are one of the components of lecithin which is found in egg - yolks, as well as being extracted from soy beans, and is used as a food additive in many products, and can be purchased as a dietary supplement. Lysolecithins are typically used for water - oil emulsions like margarine, due to their higher HLB ratio. Phospholipid derivatives See table below for an extensive list. Natural phospholipid derivates : egg PC ( Egg lecithin ), egg PG, soy PC, hydrogenated soy PC, sphingomyelin as natural phospholipids. Synthetic phospholipid derivates : Phosphatidic acid ( DMPA, DPPA, DSPA ) Phosphatidylcholine ( DDPC, DLPC, DMPC, DPPC, DSPC, DOPC, POPC, DEPC ) Phosphatidylglycerol ( DMPG, DPPG, DSPG, POPG ) Phosphatidylethanolamine ( DMPE, DPPE, DSPE DOPE ) Phosphatidylserine ( DOPS ) PEG phospholipid ( mPEG - phospholipid, polyglycerin - phospholipid, funcitionalized - phospholipid, terminal activated - phospholipid ) Abbreviations used and chemical information of glycerophospholipids Abbreviation CAS Name Type DDPC 3436 - 44 - 0 1, 2 - Didecanoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DEPA - NA 80724 - 31 - 8 1, 2 - Dierucoyl - sn - glycero - 3 - phosphate ( Sodium Salt ) Phosphatidic acid DEPC 56649 - 39 - 9 1, 2 - Dierucoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DEPE 988 - 07 - 2 1, 2 - Dierucoyl - sn - glycero - 3 - phosphoethanolamine Phosphatidylethanolamine DEPG - NA 1, 2 - Dierucoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Sodium Salt ) Phosphatidylglycerol DLOPC 998 - 06 - 1 1, 2 - Dilinoleoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DLPA - NA 1, 2 - Dilauroyl - sn - glycero - 3 - phosphate ( Sodium Salt ) Phosphatidic acid DLPC 18194 - 25 - 7 1, 2 - Dilauroyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DLPE 1, 2 - Dilauroyl - sn - glycero - 3 - phosphoethanolamine Phosphatidylethanolamine DLPG - NA 1, 2 - Dilauroyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Sodium Salt ) Phosphatidylglycerol DLPG - NH4 1, 2 - Dilauroyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Ammonium Salt ) Phosphatidylglycerol DLPS - NA 1, 2 - Dilauroyl - sn - glycero - 3 - phosphoserine ( Sodium Salt ) Phosphatidylserine DMPA - NA 80724 - 3 1, 2 - Dimyristoyl - sn - glycero - 3 - phosphate ( Sodium Salt ) Phosphatidic acid DMPC 18194 - 24 - 6 1, 2 - Dimyristoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DMPE 988 - 07 - 2 1, 2 - Dimyristoyl - sn - glycero - 3 - phosphoethanolamine Phosphatidylethanolamine DMPG - NA 67232 - 80 - 8 1, 2 - Dimyristoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Sodium Salt ) Phosphatidylglycerol DMPG - NH4 1, 2 - Dimyristoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Ammonium Salt ) Phosphatidylglycerol DMPG - NH4 / NA 1, 2 - Dimyristoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Sodium / Ammonium Salt ) Phosphatidylglycerol DMPS - NA 1, 2 - Dimyristoyl - sn - glycero - 3 - phosphoserine ( Sodium Salt ) Phosphatidylserine DOPA - NA 1, 2 - Dioleoyl - sn - glycero - 3 - phosphate ( Sodium Salt ) Phosphatidic acid DOPC 4235 - 95 - 4 1, 2 - Dioleoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DOPE 4004 - 5 - 1 - 1, 2 - Dioleoyl - sn - glycero - 3 - phosphoethanolamine Phosphatidylethanolamine DOPG - NA 62700 - 69 - 0 1, 2 - Dioleoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Sodium Salt ) Phosphatidylglycerol DOPS - NA 70614 - 14 - 1 1, 2 - Dioleoyl - sn - glycero - 3 - phosphoserine ( Sodium Salt ) Phosphatidylserine DPPA - NA 71065 - 87 - 7 1, 2 - Dipalmitoyl - sn - glycero - 3 - phosphate ( Sodium Salt ) Phosphatidic acid DPPC 63 - 89 - 8 1, 2 - Dipalmitoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DPPE 923 - 61 - 5 1, 2 - Dipalmitoyl - sn - glycero - 3 - phosphoethanolamine Phosphatidylethanolamine DPPG - NA 67232 - 81 - 9 1, 2 - Dipalmitoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Sodium Salt ) Phosphatidylglycerol DPPG - NH4 73548 - 70 - 6 1, 2 - Dipalmitoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Ammonium Salt ) Phosphatidylglycerol DPPS - NA 1, 2 - Dipalmitoyl - sn - glycero - 3 - phosphoserine ( Sodium Salt ) Phosphatidylserine DSPA - NA 108321 - 18 - 2 1, 2 - Distearoyl - sn - glycero - 3 - phosphate ( Sodium Salt ) Phosphatidic acid DSPC 816 - 94 - 4 1, 2 - Distearoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine DSPE 1069 - 79 - 0 1, 2 - Distearoyl - sn - glycero - 3 - phosphoethanolamine Phosphatidylethanolamine DSPG - NA 67232 - 82 - 0 1, 2 - Distearoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Sodium Salt ) Phosphatidylglycerol DSPG - NH4 108347 - 80 - 4 1, 2 - Distearoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol... ) ( Ammonium Salt ) Phosphatidylglycerol DSPS - NA 1, 2 - Distearoyl - sn - glycero - 3 - phosphoserine ( Sodium Salt ) Phosphatidylserine Egg Sphingomyelin empty Liposome EPC Egg - PC Phosphatidylcholine HEPC Hydrogenated Egg PC Phosphatidylcholine HSPC Hydrogenated Soy PC Phosphatidylcholine LYSOPC MYRISTIC 18194 - 24 - 6 1 - Myristoyl - sn - glycero - 3 - phosphocholine Lysophosphatidylcholine LYSOPC PALMITIC 17364 - 16 - 8 1 - Palmitoyl - sn - glycero - 3 - phosphocholine Lysophosphatidylcholine LYSOPC STEARIC 19420 - 57 - 6 1 - Stearoyl - sn - glycero - 3 - phosphocholine Lysophosphatidylcholine Milk Sphingomyelin MPPC 1 - Myristoyl - 2 - palmitoyl - sn - glycero 3 - phosphocholine Phosphatidylcholine MSPC 1 - Myristoyl - 2 - stearoyl - sn - glycero - 3 -- phosphocholine Phosphatidylcholine PMPC 1 - Palmitoyl - 2 - myristoyl - sn - glycero - 3 -- phosphocholine Phosphatidylcholine POPC 26853 - 31 - 6 1 - Palmitoyl - 2 - oleoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine POPE 1 - Palmitoyl - 2 - oleoyl - sn - glycero - 3 - phosphoethanolamine Phosphatidylethanolamine POPG - NA 81490 - 05 - 3 1 - Palmitoyl - 2 - oleoyl - sn - glycero - 3 ( Phospho - rac - ( 1 - glycerol )... ) ( Sodium Salt ) Phosphatidylglycerol PSPC 1 - Palmitoyl - 2 - stearoyl - sn - glycero - 3 -- phosphocholine Phosphatidylcholine SMPC 1 - Stearoyl - 2 - myristoyl - sn - glycero - 3 -- phosphocholine Phosphatidylcholine SOPC 1 - Stearoyl - 2 - oleoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine SPPC 1 - Stearoyl - 2 - palmitoyl - sn - glycero - 3 - phosphocholine Phosphatidylcholine See also Cable theory Galactolipid Sulfolipid References Jump up ^ Mashaghi S. ; Jadidi T. ; Koenderink G. ; Mashaghi A. ( 2013 ). `` Lipid Nanotechnology ''. Int. J. Mol. Sci. 14 : 4242 -- 4282. PMC 3588097. PMID 23429269. doi : 10.3390 / ijms14024242. Jump up ^ Campbell, Neil A. ; Brad Williamson ; Robin J. Heyden ( 2006 ). Biology : Exploring Life. Boston, Massachusetts : Pearson Prentice Hall. ISBN 0 - 13 - 250882 - 6. Jump up ^ Ketoconazole Encapsulated Liposome and Ethosome : GUNJAN TIWARI Jump up ^ N. Culeddu ; M. Bosco ; R. Toffanin & P. Pollesello ( 1998 ). `` High resolution 31P NMR of extracted phospholipids ''. Magnetic Resonance in Chemistry. 36 : 907 -- 912. doi : 10.1002 / ( sici ) 1097 - 458x ( 199812 ) 36 : 12 < 907 : : aid - omr394 > 3.0.co ; 2 - 5. Jump up ^ Furse, Samuel ; Liddell, Susan ; Ortori, Catharine A. ; Williams, Huw ; Neylon, D. Cameron ; Scott, David J. ; Barrett, David A. ; Gray, David A. ( 2013 ). `` The lipidome and proteome of oil bodies from Helianthus annuus ( common sunflower ) ''. Journal of Chemical Biology. 6 ( 2 ) : 63 -- 76. PMC 3606697. PMID 23532185. doi : 10.1007 / s12154 - 012 - 0090 - 1. Jump up ^ T.L. Mounts ; A.M. Nash ( 1990 ). `` HPLC analysis of phospholipids in crude oil for evaluation of soybean deterioration ''. Journal of the American Oil Chemists ' Society. 67 ( 11 ) : 757 -- 760. doi : 10.1007 / BF02540486. Jump up ^ Lodish H, Berk A, et al. ( 2007 ). Molecular Cell Biology ( 6th ed. ). W.H. Freeman. ISBN 0 - 7167 - 7601 - 4. Jump up ^ Zheng, Lei ( 2016 ). `` Biogenesis, transport and remodeling of lysophospholipids in Gram - negative bacteria ''. Biochimica et Biophysica Acta. doi : 10.1016 / j. bbalip. 2016.11. 015. Jump up ^ Choi, S. - Y. ; Chang, J ; Jiang, B ; Seol, GH ; Min, SS ; Han, JS ; Shin, HS ; Gallagher, M ; Kirkwood, A ( 2005 ). `` Multiple Receptors Coupled to Phospholipase C Gate Long - Term Depression in Visual Cortex ''. Journal of Neuroscience. 25 ( 49 ) : 11433 -- 43. PMID 16339037. doi : 10.1523 / JNEUROSCI. 4084 - 05.2005. Jump up ^ Cronshaw, D.G. ; Kouroumalis, A ; Parry, R ; Webb, A ; Brown, Z ; Ward, SG ( 2006 ). `` Evidence that phospholipase C - dependent, calcium - independent mechanisms are required for directional migration of T lymphocytes in response to the CCR4 ligands CCL17 and CCL22 ''. Journal of Leukocyte Biology. 79 ( 6 ) : 1369 -- 80. PMID 16614259. doi : 10.1189 / jlb. 0106035. Structures of the cell membrane Membrane lipids Lipid bilayer Phospholipids Proteolipids Sphingolipids Sterols Membrane proteins Membrane glycoproteins Integral membrane proteins / transmembrane protein Peripheral membrane protein / Lipid - anchored protein Other Caveolae / Coated pits Cell junctions Glycocalyx Lipid raft / microdomains Membrane contact sites Membrane nanotubes Myelin sheath Nodes of Ranvier Nuclear envelope Phycobilisomes Porosomes Lipids : phospholipids Glycerol backbone ( Glycerophospholipids / Phosphoglycerides ) Phosphatidyl - : - ethanolamine / cephalin ( PE ) - choline / lecithin ( PC ) - serine ( PS ) - glycerol ( PG ) - inositol ( PI ) glyco - ( GPI ) Phosphoinositides : PIP PI ( 3 ) P PI ( 4 ) P PI ( 5 ) P PIP PI ( 3, 4 ) P PI ( 3, 5 ) P PI ( 4, 5 ) P PIP Ether lipids : Plasmalogen Platelet - activating factor Cardiolipin Sphingosine backbone Sphingomyelin Metabolites Inositol phosphate Inositol Lysophosphatidic acid Choline Phosphocholine Citicoline GND : 4131432 - 3 NDL : 00569532 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Phospholipid&oldid=805908215 '' Categories : Phospholipids Anionic surfactants Hidden categories : Wikipedia articles needing page number citations from October 2012 All articles with unsourced statements Articles with unsourced statements from December 2014 Wikipedia articles with GND identifiers Talk Contents About Wikipedia Български Bosanski Català Čeština Dansk Deutsch Eesti Ελληνικά Español Euskara فارسی Français Gaeilge Galego 한국어 Hrvatski Bahasa Indonesia Íslenska Italiano עברית Basa Jawa ქართული Latviešu Lëtzebuergesch Lietuvių Македонски Nederlands 日本 語 Norsk Norsk nynorsk Polski Português Română Русский Shqip Simple English Slovenčina Slovenščina Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska தமிழ் ไทย Türkçe Українська 中文 Edit links This page was last edited on 18 October 2017, at 11 : 53. 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Question: what is the hydrophilic portion of a phospholipid molecule
Answer: a hydrophilic "head" consisting of a phosphate group