Phospholipid
Phospholipids
Phospholipids are a key component of all
The first phospholipid identified in 1847 as such in biological tissues was
Phospholipids in biological membranes
Arrangement
The phospholipids are
In aqueous solutions, phospholipids are driven by
In biological membranes, the phospholipids often occur with other molecules (e.g., proteins, glycolipids, sterols) in a bilayer such as a cell membrane.[5] Lipid bilayers occur when hydrophobic tails line up against one another, forming a membrane of hydrophilic heads on both sides facing the water.[citation needed]
Dynamics
These specific properties allow phospholipids to play an important role in the cell membrane. Their movement can be described by the fluid mosaic model, which 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 However, this model has now been superseded, as through the study of lipid polymorphism it is now known that the behaviour of lipids under physiological (and other) conditions is not simple.[citation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]
Main phospholipids
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.[6] Advances in phospholipid research lead to exploring these biomolecules and their conformations using lipidomics.[citation needed]
Simulations
Computational simulations of phospholipids are often performed using molecular dynamics with force fields such as GROMOS, CHARMM, or AMBER.[citation needed]
Characterization
Phospholipids are optically highly
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
provides relative values.Phospholipid synthesis
Phospholipid synthesis occurs in the cytosolic side of ER membrane [10] 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.[11][12]
Sources
Common sources of industrially produced phospholipids are soya, rapeseed, sunflower, chicken eggs, bovine milk, fish eggs etc. Phospholipids for gene delivery such as distearoylphosphatidylcholine, dioleoyl-3-trimethylammonium propane etc. are produced synthetically. Each source has a unique profile of individual phospholipid species, as well as fatty acids, and consequently differing applications in food, nutrition, pharmaceuticals, cosmetics and drug delivery.[citation needed]
In signal transduction
Some types of phospholipid can be split to produce products that function as
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.[citation needed]
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 soybeans, 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.[citation needed]
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, functionalized-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 | |
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
References
- ^ "Phospholipid". Encyclopedia Britannica. Retrieved 2020-12-22.
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- ^ Alberts, Bruce; Johnson, Alexander; Lewis, Julian; Raff, Martin; Roberts, Keith; Walter, Peter (2002), "The Lipid Bilayer", Molecular Biology of the Cell. 4th edition, Garland Science, retrieved 2023-05-25
- ]
- ^ Ketoconazole Encapsulated Liposome and Ethosome: GUNJAN TIWARI.
- S2CID 85602251.
- PMID 23532185.
- S2CID 84380025.
- PMID 28119445.
- ISBN 978-0-7167-7601-7.
- PMID 27956138.
- PMID 16339037.
- PMID 16614259.