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{{Short description|Group of chemical compounds}}
{{chembox
[[File:Biosynthesis of phosphatidylglycerol, phosphatidylserine, and phosphatidylethanolamine.svg|thumb|250 px|Biosynthesis of various phospholipids (including phosphatidylethanolamine) in bacteria]]
| verifiedrevid = 400848758
| ImageFile = Phosphatidyl-Ethanolamine.png
| ImageSize =
| IUPACName =
| OtherNames =
| Section1 = {{Chembox Identifiers
| InChIKey = NJGIRBISCGPRPF-KXQOOQHDBR
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NJGIRBISCGPRPF-KXQOOQHDSA-N
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 394115
| PubChem = 446872
| InChI = 1/C40H80NO8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41)36-46-39(42)32-30-28-26-24-22-16-14-12-10-8-6-4-2/h38H,3-37,41H2,1-2H3,(H,44,45)/t38-/m1/s1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C40H80NO8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41)36-46-39(42)32-30-28-26-24-22-16-14-12-10-8-6-4-2/h38H,3-37,41H2,1-2H3,(H,44,45)/t38-/m1/s1
| SMILES = O=C(OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCCCC)COP(=O)(OCCN)O)CCCCCCCCCCCCCC
| MeSHName = phosphatidylethanolamines
}}
| Section2 = {{Chembox Properties
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
}}
| Section3 = {{Chembox Hazards
| Solubility =
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
'''Phosphatidylethanolamine''' (sometimes abbreviated '''PE''') is a [[lipid]] found in [[biological membranes]].<ref>{{cite journal |author=Wellner N, Diep TA, Janfelt C, Hansen HS |title=N-acylation of phosphatidylethanolamine and its biological functions in mammals.|journal=Biochim Biophys Acta |date = 2012 Sep 8. |doi = 10.1016/j.bbalip.2012.08.019 |url=http://www.ncbi.nlm.nih.gov/pubmed/23000428}}</ref> It is synthesized by the addition of [[Cytidine diphosphate|CDP]]-[[ethanolamine]] to [[diglyceride]], releasing [[Cytidine monophosphate|CMP]]. [[S-adenosyl methionine]] can subsequently methylate the amine of phosphatidyl ethanolamine to yield [[phosphatidyl choline]]. It can mainly be found in the inner ([[cytoplasmic]]) leaflet of the [[lipid bilayer]]. <ref>{{cite journal |author=Mishkind, Michael |title=Phosphatidylethanolamine – in a pinch |journal=Trends in Cell Biology |year= 2000 |Month=September |doi =10.1016/S0962-8924(00)01826-2 |url=http://www.sciencedirect.com/science/article/pii/S0962892400018262}}</ref>


'''Phosphatidylethanolamine''' ('''PE''') is a class of [[phospholipid]]s found in [[biological membrane]]s.<ref>{{cite journal |doi=10.1016/j.bbalip.2012.08.019 |title=N-acylation of phosphatidylethanolamine and its biological functions in mammals |year=2012 |last1=Wellner |first1=Niels |last2=Diep |first2=Thi Ai |last3=Janfelt |first3=Christian |last4=Hansen |first4=Harald Severin |journal=Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |pmid=23000428 |volume=1831 |issue=3 |pages=652–62}}</ref> They are synthesized by the addition of [[cytidine diphosphate]]-[[ethanolamine]] to [[diglyceride]]s, releasing [[cytidine monophosphate]]. [[S-Adenosyl methionine|''S''-Adenosyl methionine]] can subsequently [[Methylation|methylate]] the [[amine]] of phosphatidylethanolamines to yield [[phosphatidylcholine]]s.
PE is a [[phospholipid]], which is a lipid derivative. It is not to be confused with the molecule of the same name that is an [[alkaloid]] constituent of [[Ipecac]].


==Function==
==Function==
[[File:Membrane_Lipids.svg|thumb|250 px|The major [[membrane lipids]]:
Phosphatidylethanolamine is found in all living cells, composing 25% of all [[phospholipids]]. In human physiology it is found particularly in nervous tissue such as the [[white matter]] of [[brain]], nerves, neural tissue, and in [[spinal cord]], where it makes up 45% of all phospholipids.<ref name ="Onl">{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S1388198112001874 | title=Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells | author=Vance, Jean E; Tasseva, Guergana | journal=Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |year=2012 | doi=10.1016/j.bbalip.2012.08.016 | Month=August}}</ref> Whereas phosphatidylcholine is the principal phospholipid in animals, PE is the principal one in [[bacterium|bacteria]].


[[phosphatidylcholine]] (PtdCho);
As a polar head group, phosphatidylethanolamine (PE) creates a more viscous lipid membrane compared to [[phosphatidylcholine]] (PC). For example, the melting temperature of di-oleoyl-PE is -16C while the melting temperature of di-oleoyl-PC is -20C. If the lipids had two palmitoyl chains, PE would melt at 63C while PC would melt already at 41C (See references in Wan et al. Biochemistry 47 2008). Lower melting temperatures correspond, in a simplistic view, to more fluid membranes.


phosphatidylethanolamine (PtdEtn);
PE plays a role in [[membrane fusion]] and in disassembly of the [[contractile ring]] during [[cytokinesis]] in [[cell division]]<ref>{{cite journal | url=http://www.pnas.org/content/93/23/12867 | title=Redistribution of phosphatidylethanolamine at the cleavage furrow of dividing cells during cytokinesis | author=Kazuo Emoto, Toshihide Kobayashi, Akiko Yamaji, et. al. | journal=Proceedings of the National Academy of Sciences | year=1996 | month=November | volume=93 | issue=23 | pages=12867-12872}}</ref>. Additionally, it is thought that PE regulates [[membrane curvature]]. PE acts as an important precursor, [[substrate]], or donor in several biological pathways<ref name ="Onl"></ref>. PE has also shown to be able to propagate infectious [[prions]] without the assistance of any [[proteins]] or [[nucleic acids]], which is a unique characteristic of it.<ref>{{cite journal | url=http://www.pnas.org/content/109/22/8546 | title=Isolation of phosphatidylethanolamine as a solitary cofactor for prion formation in the absence of nucleic acids | author=Nathan R. Deleaulta, Justin R. Piroa, Daniel J. Walsha, Fei Wangb, Jiyan Mab, James C. Geoghegana, and Surachai Supattaponea | journal=Proceedings of the National Academy of Sciences | year=2012 | month=May | volume=109 | issue=22 | pages=8546-8551 | doi=10.1073/pnas.1204498109}}</ref>


[[phosphatidylinositol]] (PtdIns);
In humans, metabolism of PE is thought to be important in the heart. When blood flow to the heart is restricted, the asymmetrical distribution of PE between membrane leaflets is disrupted, and as a result the membrane is disrupted. Additionally, PE plays a role in the secretion of [[lipoproteins]] in the liver. This is because vesicles for secretion of [[VLDL|VLDLs]] coming off of the [[Golgi Apparatus|Golgi]] have a significantly higher PE concentration when compared to other vesicles containing VLDLs.<ref>{{cite journal |url=http://www.jlr.org/content/49/7/1377.full | title=Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids | author=Jean E. Vance | journal=Journal of Lipid Research | year=2008 | month=July | volume=49 |pages=1377-1387 | doi=10.1194/jlr.R700020-JLR200}}</ref>
===Bacteria===
One of the primary roles for PE in bacterial membranes is to spread out the negative charge caused by [[anion|anionic]] membrane [[phospholipid|phospholipids]]. In the bacterium ''E. coli'', PE play a role in supporting [[lactose permease|lactose permease's]] active transport of lactose into the cell, and may play a role in other transport systems as well. PE plays a role in the assembly of lactose permease and other membrane proteins. It acts as a 'chaperone' to help the membrane proteins correctly fold their [[tertiary structures]] so that they can function properly. When PE is not present, the transport proteins have incorrect tertiary structures and do not function correctly. <ref name="AOCS_Lib"> {{cite web | url=http://lipidlibrary.aocs.org/lipids/pe/index.htm | title=Phosphatidylethanolamine and Related Lipids | publisher=The AOCS Lipid Library |date=April 16, 2012 |accessdate=September 03, 2012 | author=Christie, W.W.}}</ref>


[[phosphatidylserine]] (PtdSer).
==Chemistry==

As a [[lecithin]], PE consists of a combination of [[glycerol]] esterified with two [[fatty acids]] and [[phosphoric acid]]. Whereas the phosphate group is combined with [[choline]] in phosphatidylcholine, it is combined with the [[ethanolamine]] in PE. The two fatty acids may be the same, or different, and are usually in the 1,2 positions (though can be in the 1,3 positions).
]]

===In cells===
Phosphatidylethanolamines are found in all living cells, composing 25% of all phospholipids. In human physiology, they are found particularly in nervous tissue such as the [[white matter]] of [[brain]], nerves, neural tissue, and in [[spinal cord]], where they make up 45% of all phospholipids.<ref name ="Onl">{{cite journal |doi=10.1016/j.bbalip.2012.08.016 |title=Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells |year=2012 |last1=Vance |first1=Jean E. |last2=Tasseva |first2=Guergana |journal=Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |pmid=22960354 |volume=1831 |issue=3 |pages=543–54}}</ref>

Phosphatidylethanolamines play a role in [[membrane fusion]] and in disassembly of the [[contractile ring]] during [[cytokinesis]] in [[cell division]].<ref>{{cite journal |doi=10.1073/pnas.93.23.12867 |title=Redistribution of phosphatidylethanolamine at the cleavage furrow of dividing cells during cytokinesis |year=1996 |last1=Emoto |first1=K. |journal=Proceedings of the National Academy of Sciences |volume=93 |issue=23 |pages=12867–72 |bibcode=1996PNAS...9312867E |jstor=40713 |pmid=8917511 |pmc=24012 |last2=Kobayashi |first2=T |last3=Yamaji |first3=A |last4=Aizawa |first4=H |last5=Yahara |first5=I |last6=Inoue |first6=K |last7=Umeda |first7=M|doi-access=free }}</ref> Additionally, it is thought that phosphatidylethanolamine regulates [[membrane curvature]]. Phosphatidylethanolamine is an important precursor, [[substrate (biochemistry)|substrate]], or donor in several biological pathways.<ref name ="Onl" />

As a polar head group, phosphatidylethanolamine creates a more viscous lipid membrane compared to [[phosphatidylcholine]]. For example, the melting temperature of di-oleoyl-phosphatidylethanolamine is -16&nbsp;°C while the melting temperature of di-oleoyl-phosphatidylcholine is -20&nbsp;°C. If the lipids had two palmitoyl chains, phosphatidylethanolamine would melt at 63&nbsp;°C while phosphatidylcholine would melt already at 41&nbsp;°C.<ref>See references in Wan et al. Biochemistry 47 2008{{vs|should be to specific references, not the whole list|date=December 2012}}</ref> Lower melting temperatures correspond, in a simplistic view, to more fluid membranes.

===In humans===
In humans, metabolism of phosphatidylethanolamine is thought to be important in the heart. When blood flow to the heart is restricted, the asymmetrical distribution of phosphatidylethanolamine between membrane leaflets is disrupted, and as a result the membrane is disrupted. Additionally, phosphatidylethanolamine plays a role in the secretion of [[lipoproteins]] in the liver. This is because vesicles for secretion of [[very low-density lipoprotein]]s coming off of the [[Golgi apparatus]] have a significantly higher phosphatidylethanolamine concentration when compared to other vesicles containing very low-density lipoproteins.<ref>{{cite journal |doi=10.1194/jlr.R700020-JLR200 |title=Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: Two metabolically related aminophospholipids |year=2008 |last1=Vance |first1=J. E. |journal=The Journal of Lipid Research |volume=49 |issue=7 |pages=1377–87 |pmid=18204094|doi-access=free }}</ref> Phosphatidylethanolamine has also shown to be able to propagate infectious [[prions]] without the assistance of any [[proteins]] or [[nucleic acids]], which is a unique characteristic of it.<ref>{{cite journal |doi=10.1073/pnas.1204498109 |title=Isolation of phosphatidylethanolamine as a solitary cofactor for prion formation in the absence of nucleic acids |year=2012 |last1=Deleault |first1=N. R. |last2=Piro |first2=J. R. |last3=Walsh |first3=D. J. |last4=Wang |first4=F. |last5=Ma |first5=J. |last6=Geoghegan |first6=J. C. |last7=Supattapone |first7=S. |journal=Proceedings of the National Academy of Sciences |volume=109 |issue=22 |pages=8546–51 |bibcode=2012PNAS..109.8546D |pmid=22586108 |pmc=3365173|doi-access=free }}</ref> Phosphatidylethanolamine is also thought to play a role in blood clotting, as it works with [[phosphatidylserine]] to increase the rate of [[thrombin]] formation by promoting binding to [[factor V]] and [[factor X]], two proteins which catalyze the formation of thrombin from [[prothrombin]].<ref>{{cite journal |doi=10.1074/jbc.M111.260141 |title=Modulation of Prothrombinase Assembly and Activity by Phosphatidylethanolamine |year=2011 |last1=Majumder |first1=R. |last2=Liang |first2=X. |last3=Quinn-Allen |first3=M. A. |last4=Kane |first4=W. H. |last5=Lentz |first5=B. R. |journal=Journal of Biological Chemistry |volume=286 |issue=41 |pages=35535–42 |pmid=21859710 |pmc=3195639|doi-access=free }}</ref> The synthesis of endocannabinoid [[anandamide]] is performed from the phosphatidylethanolamine by the successive action of two enzymes, ''N''-[[acetyltransferase]] and [[phospholipase]]-D.<ref>{{cite journal |doi=10.3389/fphar.2014.00037 |title=Cannabinoids for treatment of Alzheimer's disease: moving toward the clinic |year=2014 |last1=Isidro |first1=F. |journal=Frontiers in Pharmacology |volume=5 |pages=37 |pmid=24634659 |pmc=3942876|doi-access=free }}</ref>

===In bacteria===
Where phosphatidylcholine is the principal [[phospholipid]] in animals, phosphatidylethanolamine is the principal one in [[bacterium|bacteria]]. One of the primary roles for phosphatidylethanolamine in bacterial membranes is to spread out the negative charge caused by [[anion]]ic membrane [[phospholipid]]s. In the bacterium ''E. coli'', phosphatidylethanolamine play a role in supporting [[lactose permease]]s active transport of lactose into the cell, and may play a role in other transport systems as well. Phosphatidylethanolamine plays a role in the assembly of lactose permease and other membrane proteins. It acts as a 'chaperone' to help the membrane proteins correctly fold their [[tertiary structures]] so that they can function properly. When phosphatidylethanolamine is not present, the transport proteins have incorrect tertiary structures and do not function correctly.<ref name="AOCS_Lib">{{cite web | url=http://lipidlibrary.aocs.org/lipids/pe/index.htm | title=Phosphatidylethanolamine and Related Lipids | publisher=The AOCS Lipid Library | date=April 16, 2012 | access-date=September 3, 2012 | author=Christie, W.W. | url-status=dead | archive-url=https://web.archive.org/web/20120821202641/http://lipidlibrary.aocs.org/lipids/pe/index.htm | archive-date=August 21, 2012 }}</ref>

Phosphatidylethanolamine also enables bacterial multidrug transporters to function properly and allows the formation of intermediates that are needed for the transporters to properly open and close.<ref>{{cite journal |doi=10.1007/s00018-007-7031-0 |title=Conformational changes in a bacterial multidrug transporter are phosphatidylethanolamine-dependent |year=2007 |last1=Gbaguidi |first1=B. |last2=Hakizimana |first2=P. |last3=Vandenbussche |first3=G. |last4=Ruysschaert |first4=J.-M. |journal=Cellular and Molecular Life Sciences |volume=64 |issue=12 |pages=1571–82 |pmid=17530171|s2cid=2078590 |url=https://dipot.ulb.ac.be/dspace/bitstream/2013/74200/1/Gbaguidi_et_al_2007_Cell_Mol_Life_Sci_64_1571.pdf }}</ref>

==Structure==
[[Image:Ethanolamine.svg|thumb|150 px|[[Ethanolamine]] ]]
As a [[lecithin]], phosphatidylethanolamine consists of a combination of [[glycerol]] esterified with two [[fatty acids]] and [[phosphoric acid]]. Whereas the phosphate group is combined with [[choline]] in phosphatidylcholine, it is combined with [[ethanolamine]] in phosphatidylethanolamine. The two fatty acids may be identical or different, and are usually found in positions 1,2 (less commonly in positions 1,3).


==Synthesis==
==Synthesis==
<!-- Deleted image removed: [[image:Phosphatidylethanolamine Biosynthesis.svg|thumb|Phosphatidylethanolamine Biosynthesis]] -->
[[image:Biosynthesis of phosphatidylglycerol, phosphatidylserine, and phosphatidylethanolamine.svg|thumb|Biosynthesis of Phophatidylethanolamine in Bacteria]]
The [[phosphatidylserine]] [[decarboxylation]] pathway and the [[Serine-phosphoethanolamine synthase|CDP-ethanolamine]] pathways are used to synthesize PE. [[Phosphatidylserine decarboxylase]] (PSD) is the enzyme that is used to decarboxylate phosphatidylserine in the first pathway. The phosphatidylserine decarboxylation pathway is the main source of synthesis for PE in the membranes of the [[mitochondria]]. PE produced in the mitochondrial membrane is also transported throughout the cell to other membranes for use. In a process that mirrors [[phosphatidylcholine]] synthesis, PE is also made via the [[Serine-phosphoethanolamine synthase|CDP-ethanolamine]] pathway, using [[ethanolamine]] as the substrate. Through several steps taking place is both the [[cytosol]] and [[endoplasmic reticulum]], the synthesis pathway yields the end product of PE.<ref>{{cite web |url=http://lipidlibrary.aocs.org/animbio/phospholipids/index.htm#pe | title=Phospholipid Biosynthesis | publisher= The AOCS Lipid Library | date=July 28, 2011 |accessdate=September 03, 2012 | author=Kelly, Karen}}</ref>
The [[phosphatidylserine]] [[decarboxylation]] pathway and the [[Serine-phosphoethanolamine synthase|cytidine diphosphate-ethanolamine]] pathways are used to synthesize phosphatidylethanolamine. [[Phosphatidylserine decarboxylase]] is the enzyme that is used to decarboxylate phosphatidylserine in the first pathway. The phosphatidylserine decarboxylation pathway is the main source of synthesis for phosphatidylethanolamine in the membranes of the [[mitochondria]]. Phosphatidylethanolamine produced in the mitochondrial membrane is also transported throughout the cell to other membranes for use. In a process that mirrors [[phosphatidylcholine]] synthesis, phosphatidylethanolamine is also made via the cytidine diphosphate-ethanolamine pathway, using [[ethanolamine]] as the substrate. Through several steps taking place in both the [[cytosol]] and [[endoplasmic reticulum]], the synthesis pathway yields the end product of phosphatidylethanolamine.<ref>{{cite web |url=http://lipidlibrary.aocs.org/animbio/phospholipids/index.htm#pe | title=Phospholipid Biosynthesis | publisher= The AOCS Lipid Library | date=July 28, 2011 |access-date=September 3, 2012 | author=Kelly, Karen}}</ref> Phosphatidylethanolamine is also found abundantly in soy or egg lecithin and is produced commercially using chromatographic separation.


===Regulation===
===Regulation===
Synthesis of PE through the [[phosphatidylserine]] [[decarboxylation]] pathway occurs rapidly in the [[inner mitochondrial membrane]]. However, phosphatidylserine is made in the [[endoplasmic reticulum]]. Because of this, the transport of phosphatidylserine from the endoplasmic reticulum to the mitrochondrial membrane and then to the inner mitochondrial membrane limits the rate of synthesis via this pathway. The mechanism for this transport is currently unknown, but may play a role in regulation of the rate of synthesis in this pathway.
Synthesis of phosphatidylethanolamine through the [[phosphatidylserine]] [[decarboxylation]] pathway occurs rapidly in the [[inner mitochondrial membrane]]. However, phosphatidylserine is made in the [[endoplasmic reticulum]]. Because of this, the transport of phosphatidylserine from the endoplasmic reticulum to the mitochondrial membrane and then to the inner mitochondrial membrane limits the rate of synthesis via this pathway. The mechanism for this transport is currently unknown but may play a role in the regulation of the rate of synthesis in this pathway.<ref>{{Cite journal|url=https://www.jstage.jst.go.jp/article/biochemistry1922/133/4/133_4_397/_article/-char/en|title=Biosynthetic Regulation and Intracellular Transport of phosphatidylserine in Mammalian Cells|last1=Kuge|first1=Osamu|last2=Nishijima|first2=Masahiro|journal=The Journal of Biochemistry|volume=133|issue=4|date=1 April 2003|pages=397–403|doi=10.1093/jb/mvg052|pmid=12761285|access-date=30 January 2021|archive-url=https://web.archive.org/web/20210130174316/https://www.jstage.jst.go.jp/article/biochemistry1922/133/4/133_4_397/_article/-char/en|archive-date=30 January 2021|url-access=subscription}}</ref>

==Presence in food, health issues==
Phosphatidylethanolamines in food break down to form phosphatidylethanolamine-linked [[Amadori product]]s as a part of the [[Maillard reaction]].<ref name="JLR">{{cite journal |first1=Jeong-Ho |last1=Oak |first2=Kiyotaka |last2=Nakagawa |first3=Teruo |last3=Miyazawa |title=UV analysis of Amadori-glycated phosphatidylethanolamine in foods and biological samples |journal=The Journal of Lipid Research |pmid=11893788 |url=http://www.jlr.org/cgi/pmidlookup?view=long&pmid=11893788 |year=2002 |volume=43 |issue=3 |pages=523–9|doi=10.1016/S0022-2275(20)30158-9 |doi-access=free }}</ref> These products accelerate [[membrane]] [[lipid]] [[peroxidation]], causing [[oxidative stress]] to cells that come in contact with them.<ref>{{cite journal |doi=10.1016/S0014-5793(00)01966-9 |title=Synthetically prepared Amadori-glycated phosphatidylethanolamine can trigger lipid peroxidation via free radical reactions |year=2000 |last1=Oak |first1=Jeong-Ho |last2=Nakagawa |first2=Kiyotaka |last3=Miyazawa |first3=Teruo |journal=FEBS Letters |volume=481 |pages=26–30 |pmid=10984609 |issue=1|s2cid=23265125 |doi-access=free |bibcode=2000FEBSL.481...26O }}</ref> Oxidative stress is known to cause food deterioration and several diseases. Significant levels of Amadori-phosphatidylethanolamine products have been found in a wide variety of foods such as [[chocolate]], [[soybean milk]], [[infant formula]], and other [[processed foods]]. The levels of Amadori-phosphatidylethanolamine products are higher in foods with high lipid and sugar concentrations that have high temperatures in processing.<ref name="JLR" /> Additional studies have found that Amadori-phosphatidylethanolamine may play a role in [[vascular disease]],<ref>{{cite journal |doi=10.1016/S0014-5793(03)01237-7 |title=Amadori-glycated phosphatidylethanolamine induces angiogenic differentiations in cultured human umbilical vein endothelial cells |year=2003 |last1=Oak |first1=Jeong-Ho |last2=Nakagawa |first2=Kiyotaka |last3=Oikawa |first3=Shinichi |last4=Miyazawa |first4=Teruo |journal=FEBS Letters |volume=555 |issue=2 |pages=419–23 |pmid=14644453|s2cid=33974755 |doi-access= |bibcode=2003FEBSL.555..419O }}</ref> act as the mechanism by which [[diabetes]] can increase the incidence of [[cancer]],<ref>{{cite journal |doi=10.1016/j.febslet.2012.06.027 |title=Amadori-glycated phosphatidylethanolamine up-regulates telomerase activity in PANC-1 human pancreatic carcinoma cells |year=2012 |last1=Eitsuka |first1=Takahiro |last2=Nakagawa |first2=Kiyotaka |last3=Ono |first3=Yuichi |last4=Tatewaki |first4=Naoto |last5=Nishida |first5=Hiroshi |last6=Kurata |first6=Tadao |last7=Shoji |first7=Naoki |last8=Miyazawa |first8=Teruo |journal=FEBS Letters |volume=586 |issue=16 |pages=2542–7 |pmid=22750441|s2cid=5452160 |doi-access=free |bibcode=2012FEBSL.586.2542E }}</ref> and potentially play a role in other diseases as well. Amadori-phosphatidylethanolamine has a higher [[Blood plasma|plasma]] [[concentration]] in diabetes patients than healthy people, indicating it may play a role in the development of the disease or be a product of the disease.<ref>{{cite journal |doi=10.3748/wjg.14.3212 |title=Incidence of reflux esophagitis and H pylori infection in diabetic patients |year=2008 |last1=Ariizumi |first1=Ken |journal=World Journal of Gastroenterology |volume=14 |issue=20 |pages=3212–7 |pmid=18506928 |last2=Koike |first2=T |last3=Ohara |first3=S |last4=Inomata |first4=Y |last5=Abe |first5=Y |last6=Iijima |first6=K |last7=Imatani |first7=A |last8=Oka |first8=T |last9=Shimosegawa |first9=T |pmc=2712855 |doi-access=free }}</ref>


==See also==
==See also==
* [[N-acylphosphatidylethanolamine|''N''-Acylphosphatidylethanolamine]]
* [[N-acylphosphatidylethanolamine|''N''-Acylphosphatidylethanolamine]]
* [[Phosphatidyl ethanolamine methyltransferase]]
* [[Phosphatidyl ethanolamine methyltransferase]]

==References==
{{Reflist}}


==External links==
==External links==
* {{MeshName|Phosphatidylethanolamines}}
* {{MeshName|Phosphatidylethanolamines}}
* [http://lipidlibrary.aocs.org/lipids/pe/index.htm Phosphatidylethanolamine] at the The AOCS Lipid Library.
* [https://web.archive.org/web/20120821202641/http://lipidlibrary.aocs.org/lipids/pe/index.htm Phosphatidylethanolamine] at the AOCS Lipid Library.

==Additional images==
<gallery>
Image:Membrane lipids.png|[[membrane lipids]]
Image:Ethanolamine.png|[[ethanolamine]]
</gallery>

==References==
{{reflist}}


{{Phospholipids}}
{{Phospholipids}}
{{Acetylcholine receptor modulators}}
{{Cholinergics}}


[[Category:Cholinergics]]
[[Category:Phospholipids]]
[[Category:Phospholipids]]
[[Category:Membrane biology]]
[[Category:Membrane biology]]
[[Category:Phosphatidylethanolamines]]


{{biochemistry-stub}}

[[cs:Fosfatidylethanolamin]]
[[de:Phosphatidylethanolamine]]
[[es:Fosfatidiletanolamina]]
[[fr:Phosphatidyléthanolamine]]
[[gl:Fosfatidiletanolamina]]
[[it:Fosfatidiletanolammina]]
[[sr:Fosfatidiletanolamin]]

Latest revision as of 21:08, 19 May 2024

Biosynthesis of various phospholipids (including phosphatidylethanolamine) in bacteria

Phosphatidylethanolamine (PE) is a class of phospholipids found in biological membranes.[1] They are synthesized by the addition of cytidine diphosphate-ethanolamine to diglycerides, releasing cytidine monophosphate. S-Adenosyl methionine can subsequently methylate the amine of phosphatidylethanolamines to yield phosphatidylcholines.

Function

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The major membrane lipids: phosphatidylcholine (PtdCho); phosphatidylethanolamine (PtdEtn); phosphatidylinositol (PtdIns); phosphatidylserine (PtdSer).

In cells

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Phosphatidylethanolamines are found in all living cells, composing 25% of all phospholipids. In human physiology, they are found particularly in nervous tissue such as the white matter of brain, nerves, neural tissue, and in spinal cord, where they make up 45% of all phospholipids.[2]

Phosphatidylethanolamines play a role in membrane fusion and in disassembly of the contractile ring during cytokinesis in cell division.[3] Additionally, it is thought that phosphatidylethanolamine regulates membrane curvature. Phosphatidylethanolamine is an important precursor, substrate, or donor in several biological pathways.[2]

As a polar head group, phosphatidylethanolamine creates a more viscous lipid membrane compared to phosphatidylcholine. For example, the melting temperature of di-oleoyl-phosphatidylethanolamine is -16 °C while the melting temperature of di-oleoyl-phosphatidylcholine is -20 °C. If the lipids had two palmitoyl chains, phosphatidylethanolamine would melt at 63 °C while phosphatidylcholine would melt already at 41 °C.[4] Lower melting temperatures correspond, in a simplistic view, to more fluid membranes.

In humans

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In humans, metabolism of phosphatidylethanolamine is thought to be important in the heart. When blood flow to the heart is restricted, the asymmetrical distribution of phosphatidylethanolamine between membrane leaflets is disrupted, and as a result the membrane is disrupted. Additionally, phosphatidylethanolamine plays a role in the secretion of lipoproteins in the liver. This is because vesicles for secretion of very low-density lipoproteins coming off of the Golgi apparatus have a significantly higher phosphatidylethanolamine concentration when compared to other vesicles containing very low-density lipoproteins.[5] Phosphatidylethanolamine has also shown to be able to propagate infectious prions without the assistance of any proteins or nucleic acids, which is a unique characteristic of it.[6] Phosphatidylethanolamine is also thought to play a role in blood clotting, as it works with phosphatidylserine to increase the rate of thrombin formation by promoting binding to factor V and factor X, two proteins which catalyze the formation of thrombin from prothrombin.[7] The synthesis of endocannabinoid anandamide is performed from the phosphatidylethanolamine by the successive action of two enzymes, N-acetyltransferase and phospholipase-D.[8]

In bacteria

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Where phosphatidylcholine is the principal phospholipid in animals, phosphatidylethanolamine is the principal one in bacteria. One of the primary roles for phosphatidylethanolamine in bacterial membranes is to spread out the negative charge caused by anionic membrane phospholipids. In the bacterium E. coli, phosphatidylethanolamine play a role in supporting lactose permeases active transport of lactose into the cell, and may play a role in other transport systems as well. Phosphatidylethanolamine plays a role in the assembly of lactose permease and other membrane proteins. It acts as a 'chaperone' to help the membrane proteins correctly fold their tertiary structures so that they can function properly. When phosphatidylethanolamine is not present, the transport proteins have incorrect tertiary structures and do not function correctly.[9]

Phosphatidylethanolamine also enables bacterial multidrug transporters to function properly and allows the formation of intermediates that are needed for the transporters to properly open and close.[10]

Structure

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Ethanolamine

As a lecithin, phosphatidylethanolamine consists of a combination of glycerol esterified with two fatty acids and phosphoric acid. Whereas the phosphate group is combined with choline in phosphatidylcholine, it is combined with ethanolamine in phosphatidylethanolamine. The two fatty acids may be identical or different, and are usually found in positions 1,2 (less commonly in positions 1,3).

Synthesis

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The phosphatidylserine decarboxylation pathway and the cytidine diphosphate-ethanolamine pathways are used to synthesize phosphatidylethanolamine. Phosphatidylserine decarboxylase is the enzyme that is used to decarboxylate phosphatidylserine in the first pathway. The phosphatidylserine decarboxylation pathway is the main source of synthesis for phosphatidylethanolamine in the membranes of the mitochondria. Phosphatidylethanolamine produced in the mitochondrial membrane is also transported throughout the cell to other membranes for use. In a process that mirrors phosphatidylcholine synthesis, phosphatidylethanolamine is also made via the cytidine diphosphate-ethanolamine pathway, using ethanolamine as the substrate. Through several steps taking place in both the cytosol and endoplasmic reticulum, the synthesis pathway yields the end product of phosphatidylethanolamine.[11] Phosphatidylethanolamine is also found abundantly in soy or egg lecithin and is produced commercially using chromatographic separation.

Regulation

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Synthesis of phosphatidylethanolamine through the phosphatidylserine decarboxylation pathway occurs rapidly in the inner mitochondrial membrane. However, phosphatidylserine is made in the endoplasmic reticulum. Because of this, the transport of phosphatidylserine from the endoplasmic reticulum to the mitochondrial membrane and then to the inner mitochondrial membrane limits the rate of synthesis via this pathway. The mechanism for this transport is currently unknown but may play a role in the regulation of the rate of synthesis in this pathway.[12]

Presence in food, health issues

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Phosphatidylethanolamines in food break down to form phosphatidylethanolamine-linked Amadori products as a part of the Maillard reaction.[13] These products accelerate membrane lipid peroxidation, causing oxidative stress to cells that come in contact with them.[14] Oxidative stress is known to cause food deterioration and several diseases. Significant levels of Amadori-phosphatidylethanolamine products have been found in a wide variety of foods such as chocolate, soybean milk, infant formula, and other processed foods. The levels of Amadori-phosphatidylethanolamine products are higher in foods with high lipid and sugar concentrations that have high temperatures in processing.[13] Additional studies have found that Amadori-phosphatidylethanolamine may play a role in vascular disease,[15] act as the mechanism by which diabetes can increase the incidence of cancer,[16] and potentially play a role in other diseases as well. Amadori-phosphatidylethanolamine has a higher plasma concentration in diabetes patients than healthy people, indicating it may play a role in the development of the disease or be a product of the disease.[17]

See also

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References

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  1. ^ Wellner, Niels; Diep, Thi Ai; Janfelt, Christian; Hansen, Harald Severin (2012). "N-acylation of phosphatidylethanolamine and its biological functions in mammals". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1831 (3): 652–62. doi:10.1016/j.bbalip.2012.08.019. PMID 23000428.
  2. ^ a b Vance, Jean E.; Tasseva, Guergana (2012). "Formation and function of phosphatidylserine and phosphatidylethanolamine in mammalian cells". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1831 (3): 543–54. doi:10.1016/j.bbalip.2012.08.016. PMID 22960354.
  3. ^ Emoto, K.; Kobayashi, T; Yamaji, A; Aizawa, H; Yahara, I; Inoue, K; Umeda, M (1996). "Redistribution of phosphatidylethanolamine at the cleavage furrow of dividing cells during cytokinesis". Proceedings of the National Academy of Sciences. 93 (23): 12867–72. Bibcode:1996PNAS...9312867E. doi:10.1073/pnas.93.23.12867. JSTOR 40713. PMC 24012. PMID 8917511.
  4. ^ See references in Wan et al. Biochemistry 47 2008[verification needed]
  5. ^ Vance, J. E. (2008). "Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: Two metabolically related aminophospholipids". The Journal of Lipid Research. 49 (7): 1377–87. doi:10.1194/jlr.R700020-JLR200. PMID 18204094.
  6. ^ Deleault, N. R.; Piro, J. R.; Walsh, D. J.; Wang, F.; Ma, J.; Geoghegan, J. C.; Supattapone, S. (2012). "Isolation of phosphatidylethanolamine as a solitary cofactor for prion formation in the absence of nucleic acids". Proceedings of the National Academy of Sciences. 109 (22): 8546–51. Bibcode:2012PNAS..109.8546D. doi:10.1073/pnas.1204498109. PMC 3365173. PMID 22586108.
  7. ^ Majumder, R.; Liang, X.; Quinn-Allen, M. A.; Kane, W. H.; Lentz, B. R. (2011). "Modulation of Prothrombinase Assembly and Activity by Phosphatidylethanolamine". Journal of Biological Chemistry. 286 (41): 35535–42. doi:10.1074/jbc.M111.260141. PMC 3195639. PMID 21859710.
  8. ^ Isidro, F. (2014). "Cannabinoids for treatment of Alzheimer's disease: moving toward the clinic". Frontiers in Pharmacology. 5: 37. doi:10.3389/fphar.2014.00037. PMC 3942876. PMID 24634659.
  9. ^ Christie, W.W. (April 16, 2012). "Phosphatidylethanolamine and Related Lipids". The AOCS Lipid Library. Archived from the original on August 21, 2012. Retrieved September 3, 2012.
  10. ^ Gbaguidi, B.; Hakizimana, P.; Vandenbussche, G.; Ruysschaert, J.-M. (2007). "Conformational changes in a bacterial multidrug transporter are phosphatidylethanolamine-dependent" (PDF). Cellular and Molecular Life Sciences. 64 (12): 1571–82. doi:10.1007/s00018-007-7031-0. PMID 17530171. S2CID 2078590.
  11. ^ Kelly, Karen (July 28, 2011). "Phospholipid Biosynthesis". The AOCS Lipid Library. Retrieved September 3, 2012.
  12. ^ Kuge, Osamu; Nishijima, Masahiro (1 April 2003). "Biosynthetic Regulation and Intracellular Transport of phosphatidylserine in Mammalian Cells". The Journal of Biochemistry. 133 (4): 397–403. doi:10.1093/jb/mvg052. PMID 12761285. Archived from the original on 30 January 2021. Retrieved 30 January 2021.
  13. ^ a b Oak, Jeong-Ho; Nakagawa, Kiyotaka; Miyazawa, Teruo (2002). "UV analysis of Amadori-glycated phosphatidylethanolamine in foods and biological samples". The Journal of Lipid Research. 43 (3): 523–9. doi:10.1016/S0022-2275(20)30158-9. PMID 11893788.
  14. ^ Oak, Jeong-Ho; Nakagawa, Kiyotaka; Miyazawa, Teruo (2000). "Synthetically prepared Amadori-glycated phosphatidylethanolamine can trigger lipid peroxidation via free radical reactions". FEBS Letters. 481 (1): 26–30. Bibcode:2000FEBSL.481...26O. doi:10.1016/S0014-5793(00)01966-9. PMID 10984609. S2CID 23265125.
  15. ^ Oak, Jeong-Ho; Nakagawa, Kiyotaka; Oikawa, Shinichi; Miyazawa, Teruo (2003). "Amadori-glycated phosphatidylethanolamine induces angiogenic differentiations in cultured human umbilical vein endothelial cells". FEBS Letters. 555 (2): 419–23. Bibcode:2003FEBSL.555..419O. doi:10.1016/S0014-5793(03)01237-7. PMID 14644453. S2CID 33974755.
  16. ^ Eitsuka, Takahiro; Nakagawa, Kiyotaka; Ono, Yuichi; Tatewaki, Naoto; Nishida, Hiroshi; Kurata, Tadao; Shoji, Naoki; Miyazawa, Teruo (2012). "Amadori-glycated phosphatidylethanolamine up-regulates telomerase activity in PANC-1 human pancreatic carcinoma cells". FEBS Letters. 586 (16): 2542–7. Bibcode:2012FEBSL.586.2542E. doi:10.1016/j.febslet.2012.06.027. PMID 22750441. S2CID 5452160.
  17. ^ Ariizumi, Ken; Koike, T; Ohara, S; Inomata, Y; Abe, Y; Iijima, K; Imatani, A; Oka, T; Shimosegawa, T (2008). "Incidence of reflux esophagitis and H pylori infection in diabetic patients". World Journal of Gastroenterology. 14 (20): 3212–7. doi:10.3748/wjg.14.3212. PMC 2712855. PMID 18506928.
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