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 as they can form lipid bilayers. Most phospholipids contain a diglyceride, a phosphate group, and a simple organic molecule such as choline; one exception to this rule is sphingomyelin, which is derived from sphingosine instead of glycerol. The first phospholipid identified as such in biological tissues was lecithin, or phosphatidylcholine, in the egg yolk, by Theodore Nicolas Gobley, a French chemist and pharmacist, in 1847. The structure of the phospholipid molecule generally consists of hydrophobic tails and a hydrophilic head. 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]
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Contents
- 1 Amphipathic character
- 2 Types of phospholipid
- 2.1 Diacylglyceride structures
- 2.2 Phosphosphingolipids
- 3 Simulations
- 4 Characterization
- 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
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Amphipathic character[edit]
The 'head' is hydrophilic (attracted to water), while the hydrophobic 'tails' are repelled by water and are forced to aggregate. The hydrophilic head contains the negatively charged phosphate group, and may contain other polar groups. The hydrophobic tail usually consists of long fatty acid hydrocarbon chains. When placed in water, phospholipids form a variety of structures depending on the specific properties of the phospholipid. 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 contributes 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.
Types of phospholipid[edit]
Diacylglyceride structures[edit]
- 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 triphosphate (PIP3).
Phosphosphingolipids[edit]
- Ceramide phosphorylcholine (Sphingomyelin) (SPH)
- Ceramide phosphorylethanolamine (Sphingomyelin) (Cer-PE)
- Ceramide phosphoryllipid
Simulations[edit]
Computational simulations of phospholipids are often performed using molecular dynamics with force fields such as GROMOS, CHARMM, or AMBER.
Characterization[edit]
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[edit]
There are no simple methods available for analysis of Phospholipids since the close range of polarity between different phospholipid species makes detection difficult.[3] Oil chemists often use spectroscopy to determine total Phosphorus content and then calculate content of Phospholipids based on molecular weight of expected fatty acid species. The absolute method of analysis of Phospholipids in 31P-NMR [4] while HPLC-ELSD[5] provides relative values.
Phospholipid synthesis[edit]
Phospholipid synthesis occurs in the cytosol 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.[6]
Sources[edit]
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[edit]
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[7] to leukocyte signal pathways started by chemokine receptors.[8]
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[edit]
Phospholipids can act as an emulsifier, 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.
Phospholipid derivatives[edit]
- See table below for an extensive list.
- Natural phospholipid derivates:
- egg PC, 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[edit]
| 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[edit]
- Cable theory
- Galactolipid
- Sulfolipid
References[edit]
- ^ Mashaghi S., Jadidi T., Koenderink G., Mashaghi A. (2013). "Lipid Nanotechnology". Int. J. Mol. Sci. 2013 (14): 4242–4282. doi:10.3390/ijms14024242.
- ^ Campbell, Neil A.; Brad Williamson; Robin J. Heyden (2006). Biology: Exploring Life. Boston, Massachusetts: Pearson Prentice Hall. ISBN 0-13-250882-6. [page needed]
- ^ HPLC SEPARATION of PHOSPHOLIPIDS - W.W. Christie
- ^ High resolution 31P NMR of extracted phospholipids - P. Meneses and T. Glonek
- ^ HPLC analysis of phospholipids in crude oil for evaluation of soybean deterioration - T.L. Mounts, A.M. Nash
- ^ Lodish, Harvey; Berk, Krieger, Kaiser, Scott, Bretsher, Ploegh, Matsuaira (2008). Molecular Cell Biology. W.H. Freeman and Company. ISBN 0-7167-7601-4. [page needed]
- ^ Choi, S.-Y.; Chang, J; Jiang, B; Seol, GH; Min, SS; Han, JS; Shin, HS; Gallagher, M et al. (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.
- ^ 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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Structures of the cell membrane
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| Membrane lipids |
- Lipid bilayer
- Phospholipids
- Proteolipids
- Sphingolipids
- Sterols
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| Membrane proteins |
- Membrane glycoproteins
- Integral membrane proteins/transmembrane protein
- Peripheral membrane protein/Lipid-anchored protein
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| Other |
- Caveolae/Coated pits
- Cell junctions
- Glycocalyx
- Lipid raft/microdomains
- Membrane contact sites
- Membrane nanotubes
- Myelin sheath
- Nodes of Ranvier
- Nuclear envelope
- Phycobilisomes
- Porosomes
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B memb: cead, trns (1A, 1C, 1F, 2A, 3A1, 3A2-3, 3D), othr
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Lipids: phospholipids
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Glycerol backbone
(Glycerophospholipids/
Phosphoglycerides) |
Phosphatidyl-: -ethanolamine/cephalin (PE) · -choline/lechithin (PC) · -serine (PS) · -glycerol (PG) · -inositol (PI) (glyco- (GPI))
Phosphoinositides: PIP (PI(3)P, PI(4)P, PI(5)P) · PIP2 (PI(3,4)P2, PI(3,5)P2, PI(4,5)P2) · PIP3
Cardiolipin
Ether lipids: Plasmalogen (Platelet-activating factor)
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| Sphingosine backbone |
Sphingomyelin
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| Metabolites |
Inositol phosphate · Inositol
Lysophosphatidic acid
Choline · Phosphocholine · Citicoline
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mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m
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k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon
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m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)
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- biochemical families: carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- amino acids / intermediates
- tetrapyrroles / intermediates
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