Phospholipid

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Phospholipid




The left image shows a phospholipid, and the right image shows the chemical makeup.





Phosphatidylcholine 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, ethanolamine or serine.


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.[1]




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 Market


  • 8 In signal transduction


  • 9 Food technology


  • 10 Phospholipid derivatives


  • 11 Abbreviations used and chemical information of glycerophospholipids


  • 12 See also


  • 13 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, non-polar) properties. The phospholipid head contains a negatively charged phosphate group and glycerol; it is hydrophilic. The phospholipid tails usually consist 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.[2] 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.[citation needed]



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.[3]



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 spectroscopy), particularly 31P-NMR,[4][5] while HPLC-ELSD[6] 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.[7][8]



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.



Market


The key companies operating in the global Phospholipid market include Avanti Polar Lipids, Lipoid GmbH, VAV Life Sciences Pvt. Ltd.[9] and NOF Corporation.[10]



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 (PIP2), that can be split by the enzyme Phospholipase C into inositol triphosphate (IP3) and diacylglycerol (DAG), which both carry out the functions of the Gq type of G protein in response to various stimuli and intervene in various processes from long term depression in neurons[11] to leukocyte signal pathways started by chemokine receptors.[12]


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
DDPC3436-44-01,2-Didecanoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DEPA-NA80724-31-81,2-Dierucoyl-sn-glycero-3-phosphate (Sodium Salt)
Phosphatidic acid
DEPC56649-39-91,2-Dierucoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DEPE988-07-21,2-Dierucoyl-sn-glycero-3-phosphoethanolamine
Phosphatidylethanolamine
DEPG-NA1,2-Dierucoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Sodium Salt)
Phosphatidylglycerol
DLOPC998-06-11,2-Dilinoleoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DLPA-NA1,2-Dilauroyl-sn-glycero-3-phosphate (Sodium Salt)
Phosphatidic acid
DLPC18194-25-71,2-Dilauroyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DLPE1,2-Dilauroyl-sn-glycero-3-phosphoethanolamine
Phosphatidylethanolamine
DLPG-NA1,2-Dilauroyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Sodium Salt)
Phosphatidylglycerol
DLPG-NH41,2-Dilauroyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Ammonium Salt)
Phosphatidylglycerol
DLPS-NA1,2-Dilauroyl-sn-glycero-3-phosphoserine (Sodium Salt)
Phosphatidylserine
DMPA-NA80724-31,2-Dimyristoyl-sn-glycero-3-phosphate (Sodium Salt)
Phosphatidic acid
DMPC18194-24-61,2-Dimyristoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DMPE988-07-21,2-Dimyristoyl-sn-glycero-3-phosphoethanolamine
Phosphatidylethanolamine
DMPG-NA67232-80-81,2-Dimyristoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Sodium Salt)
Phosphatidylglycerol
DMPG-NH41,2-Dimyristoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Ammonium Salt)
Phosphatidylglycerol
DMPG-NH4/NA1,2-Dimyristoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Sodium/Ammonium Salt)
Phosphatidylglycerol
DMPS-NA1,2-Dimyristoyl-sn-glycero-3-phosphoserine (Sodium Salt)
Phosphatidylserine
DOPA-NA1,2-Dioleoyl-sn-glycero-3-phosphate (Sodium Salt)
Phosphatidic acid
DOPC4235-95-41,2-Dioleoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DOPE4004-5-1-1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine
Phosphatidylethanolamine
DOPG-NA62700-69-01,2-Dioleoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Sodium Salt)
Phosphatidylglycerol
DOPS-NA70614-14-11,2-Dioleoyl-sn-glycero-3-phosphoserine (Sodium Salt)
Phosphatidylserine
DPPA-NA71065-87-71,2-Dipalmitoyl-sn-glycero-3-phosphate (Sodium Salt)
Phosphatidic acid
DPPC63-89-81,2-Dipalmitoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DPPE923-61-51,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine
Phosphatidylethanolamine
DPPG-NA67232-81-91,2-Dipalmitoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Sodium Salt)
Phosphatidylglycerol
DPPG-NH473548-70-61,2-Dipalmitoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Ammonium Salt)
Phosphatidylglycerol
DPPS-NA1,2-Dipalmitoyl-sn-glycero-3-phosphoserine (Sodium Salt)
Phosphatidylserine
DSPA-NA108321-18-21,2-Distearoyl-sn-glycero-3-phosphate (Sodium Salt)
Phosphatidic acid
DSPC816-94-41,2-Distearoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
DSPE1069-79-01,2-Distearoyl-sn-glycero-3-phosphoethanolamine
Phosphatidylethanolamine
DSPG-NA67232-82-01,2-Distearoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Sodium Salt)
Phosphatidylglycerol
DSPG-NH4108347-80-41,2-Distearoyl-sn-glycero-3[Phospho-rac-(1-glycerol...) (Ammonium Salt)
Phosphatidylglycerol
DSPS-NA1,2-Distearoyl-sn-glycero-3-phosphoserine (Sodium Salt)
Phosphatidylserine
EPCEgg-PC
Phosphatidylcholine
HEPCHydrogenated Egg PC
Phosphatidylcholine
HSPCHydrogenated Soy PC
Phosphatidylcholine
LYSOPC MYRISTIC18194-24-61-Myristoyl-sn-glycero-3-phosphocholine
Lysophosphatidylcholine
LYSOPC PALMITIC17364-16-81-Palmitoyl-sn-glycero-3-phosphocholine
Lysophosphatidylcholine
LYSOPC STEARIC19420-57-61-Stearoyl-sn-glycero-3-phosphocholine
Lysophosphatidylcholine

Milk Sphingomyelin MPPC
1-Myristoyl-2-palmitoyl-sn-glycero 3-phosphocholine
Phosphatidylcholine
MSPC1-Myristoyl-2-stearoyl-sn-glycero-3–phosphocholine
Phosphatidylcholine
PMPC1-Palmitoyl-2-myristoyl-sn-glycero-3–phosphocholine
Phosphatidylcholine
POPC26853-31-61-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
POPE1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine
Phosphatidylethanolamine
POPG-NA81490-05-31-Palmitoyl-2-oleoyl-sn-glycero-3[Phospho-rac-(1-glycerol)...] (Sodium Salt)
Phosphatidylglycerol
PSPC1-Palmitoyl-2-stearoyl-sn-glycero-3–phosphocholine
Phosphatidylcholine
SMPC1-Stearoyl-2-myristoyl-sn-glycero-3–phosphocholine
Phosphatidylcholine
SOPC1-Stearoyl-2-oleoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine
SPPC1-Stearoyl-2-palmitoyl-sn-glycero-3-phosphocholine
Phosphatidylcholine


See also


  • Cable theory

  • Galactolipid

  • Sulfolipid


References




  1. ^ Mashaghi S.; Jadidi T.; Koenderink G.; Mashaghi A. (2013). "Lipid Nanotechnology". Int. J. Mol. Sci. 14 (2): 4242–4282. doi:10.3390/ijms14024242. PMC 3588097. PMID 23429269..mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em


  2. ^ Campbell, Neil A.; Brad Williamson; Robin J. Heyden (2006). Biology: Exploring Life. Boston, Massachusetts: Pearson Prentice Hall. ISBN 978-0-13-250882-7.
    [page needed]



  3. ^ Ketoconazole Encapsulated Liposome and Ethosome: GUNJAN TIWARI


  4. ^ N. Culeddu; M. Bosco; R. Toffanin & P. Pollesello (1998). "High resolution 31P NMR of extracted phospholipids". Magnetic Resonance in Chemistry. 36 (12): 907–912. doi:10.1002/(sici)1097-458x(199812)36:12<907::aid-omr394>3.0.co;2-5.


  5. ^ 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. doi:10.1007/s12154-012-0090-1. PMC 3606697. PMID 23532185.


  6. ^ 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.


  7. ^ Lodish H, Berk A, et al. (2007). Molecular Cell Biology (6th ed.). W. H. Freeman. ISBN 978-0-7167-7601-7.


  8. ^ Zheng L, Lin Y, Lu S, Zhang J, Bogdanov M (November 2017). "Biogenesis, transport and remodeling of lysophospholipids in Gram-negative bacteria". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1862 (11): 1404–1413. doi:10.1016/j.bbalip.2016.11.015. PMC 6162059. PMID 27956138.


  9. ^ "VAV Life Sciences launches India's first phospholipid manufacturing plant". Express Pharma. Retrieved January 31, 2017.


  10. ^ "2017 Global Soybean Phospholipid Market:- Avanti Polar Lipids, VAV Life Sciences, Lipoid GmbH, Cargill, Danisco and ADM". PostObserver. PRNewswire. Retrieved April 21, 2018.


  11. ^ 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. doi:10.1523/JNEUROSCI.4084-05.2005. PMID 16339037.


  12. ^ 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. doi:10.1189/jlb.0106035. PMID 16614259.











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