Showing chemical card for PE(20:4(6Z,8E,10E,14Z)-2OH(5S,12R)/18:2(9Z,12Z)) (CFc000240955)
Record Information
Version
1.0
Creation Date
2022-08-28 10:25:12 UTC
Update Date
2022-09-14 02:17:16 UTC
Chemfont ID
CFc000240955
Molecule Identification
Common Name
PE(20:4(6Z,8E,10E,14Z)-2OH(5S,12R)/18:2(9Z,12Z))
Definition
PE(20:4(6Z,8E,10E,14Z)-2OH(5S,12R)/18:2(9Z,12Z)) is an oxidized phosphatidylethanolamine (PE). Oxidized phosphatidylethanolamines are glycerophospholipids in which a phosphorylethanolamine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylethanolamines belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphatidylethanolamines can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PE(20:4(6Z,8E,10E,14Z)-2OH(5S,12R)/18:2(9Z,12Z)), in particular, consists of one chain of one Leukotriene B4 at the C-1 position and one chain of 9Z,12Z-octadecadienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PEs can be synthesized via three different routes. In one route, the oxidized PE is synthetized de novo following the same mechanisms as for PEs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PE backbone, mainly through the action of LOX (PMID: 33329396 ).
