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out wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 lecithin 2 function 3 structure and physical properties 4 possible health benefits toggle possible health benefits subsection 4 1 senescence 4 2 lipolysis 4 3 ulcerative colitis 5 biosynthesis 6 gallery 7 see also 8 references 9 external links toggle the table of contents phosphatidylcholine 26 languages العربية беларуская català čeština dansk deutsch español euskara فارسی suomi français galego bahasa indonesia italiano 日本語 한국어 nederlands norsk nynorsk português română русский srpskohrvatski српскохрватски српски srpski türkçe українська 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia class of phospholipids 1 oleoyl 2 palmitoyl phosphatidylcholine phosphatidylcholines pc are a class of glycero phospholipids that incorporate choline within the headgroup they are a major component of biological membranes and can easily be obtained from sources such as egg yolk or soybeans from which they are mechanically or chemically extracted using hexane they are a member of the lecithin group of yellow brownish fatty substances occurring in animal and plant tissues dipalmitoylphosphatidylcholine is a major component of the pulmonary surfactant and is often used in the lecithin sphingomyelin ratio to calculate fetal lung maturity while phosphatidylcholines are found in all plant and animal cells they are absent in the membranes of most bacteria 1 including escherichia coli 2 purified phosphatidylcholine is produced commercially citation needed lecithin edit the name lecithin was derived from greek λέκιθος lekithos egg yolk by theodore nicolas gobley a french chemist and pharmacist of the mid 19th century who applied it to the egg yolk phosphatidylcholine that he identified in 1847 gobley eventually described lecithin from a chemical structural point of view in 1874 phosphatidylcholines are such a major component of lecithin that in some contexts the terms are used as synonyms however lecithin extracts consist of a mixture of phosphatidylcholine and other compounds it is also used along with sodium taurocholate for simulating fed and fasted state biorelevant media in dissolution studies of highly lipophilic drugs function edit phosphatidylcholine is a major constituent of cell membranes and pulmonary surfactant and is more commonly found in the exoplasmic or outer leaflet of a cell membrane it is thought to be transported between membranes within the cell by phosphatidylcholine transfer protein pctp 3 phosphatidylcholine also plays a role in membrane mediated cell signaling and pctp activation of other enzymes 4 structure and physical properties edit palmitoyl oleyl sn phosphatidylcholine a phosphatidylcholine this phospholipid is composed of a choline head group and glycerophosphoric acid with a variety of fatty acids usually one is a saturated fatty acid in the figure this is palmitic acid hexadecanoic acid h 3 c ch 2 14 cooh and the other is an unsaturated fatty acid here oleic acid or 9z octadecenoic acid as in gobley s original egg yolk lecithin they can be found in disaturated species animal lung phosphatidylcholine for example contains a high proportion of dipalmitoylphosphatidylcholine 5 phospholipase d catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid pa releasing the soluble choline headgroup into the cytosol citation needed possible health benefits edit senescence edit a 2009 systematic review of clinical trials in humans found insufficient evidence to support supplementation of lecithin or phosphatidylcholine in dementia the study found that a moderate benefit could not be ruled out without further large scale studies 6 lipolysis edit though phosphatidylcholine has been studied as an alternative to liposuction no peer reviewed study has shown it to have comparable effects 7 8 injection of phosphatidylcholine in lipomas has been studied with mixed results 9 10 ulcerative colitis edit treatment of ulcerative colitis with oral intake of phosphatidylcholine results in decreased disease activity 11 biosynthesis edit although multiple pathways exist for biosynthesis the predominant route in eukaryotes involves condensation between diacylglycerol dag and cytidine 5 diphosphocholine cdp choline or citicoline the conversion is mediated by diacylglycerol cholinephosphotransferase another pathway mainly operative in the liver involves methylation of phosphatidylethanolamine using s adenosyl methionine sam as the methyl group donor 12 gallery edit general structural formula of phosphatidylcholines membrane lipids choline metabolism phosphatidate choline see also edit cdp choline lysophosphatidylcholine phosphatidylserine saturated fatty acid unsaturated fatty acid references edit jackowski s cronan je rock co 1991 chapter 2 lipid metabolism in procaryotes in vance de vance j eds biochemistry of lipids lipoproteins and membranes elsevier pp 80 81 isbn 978 0 444 89321 5 chen f zhao q cai x lv l lin w yu x li c li y xiong m wang xg november 2009 phosphatidylcholine in membrane of escherichia coli changes bacterial antigenicity canadian journal of microbiology 55 11 1328 34 doi 10 1139 w09 082 pmid 19940943 wirtz kw july 1991 phospholipid transfer proteins annual review of biochemistry 60 13 73 99 doi 10 1146 annurev bi 60 070191 000445 pmid 1883207 kanno k wu mk agate ds fanelli bj wagle n scapa ef ukomadu c cohen de october 2007 interacting proteins dictate function of the minimal start domain phosphatidylcholine transfer protein stard2 the journal of biological chemistry 282 42 30728 36 doi 10 1074 jbc m703745200 pmid 17704541 christie ww phosphatidylcholine and related lipids structure occurrence biochemistry and analysis invergowrie dundee dd2 5da scotland james hutton institute archived from the original on 2014 12 11 retrieved 2012 08 06 cite web cs1 maint location link higgins jp flicker l 21 january 2009 higgins jp ed lecithin for dementia and cognitive impairment the cochrane database of systematic reviews 4 3 cd001015 doi 10 1002 14651858 cd001015 pmid 12917896 rotunda am kolodney ms april 2006 mesotherapy and phosphatidylcholine injections historical clarification and review dermatologic surgery 32 4 465 80 citeseerx 10 1 1 506 2372 doi 10 1111 j 1524 4725 2006 32100 x pmid 16681654 s2cid 9994696 recent laboratory investigations17 demonstrate that sodium deoxycholate a bile salt also used as a laboratory detergent 102 103 was just as potent at causing adipocyte lysis and cell death as the complete phosphatidylcholine formula which contains both phosphatidylcholine and deoxycholate figure 3 this bile salt is used to solubilize phosphatidylcholine by forming mixed micelles composed of phosphatidylcholine and deoxycholate 102 104 it is common practice to combine intravenous medications with bile salts to improve their water solubility 105 106 these findings suggest that sodium deoxycholate is the primary active ingredient in the phosphatidylchloline preparations cite journal cite uses deprecated parameter citeseerx help park sh kim dw lee ma yoo sc rhee sc koo sh seol gh cho ey april 2008 effectiveness of mesotherapy on body contouring plastic and reconstructive surgery 121 4 179e 85e doi 10 1097 01 prs 0000304611 71480 0a pmid 18349597 s2cid 22619355 the author when discussing phosphatidylcholine as a part of mesotherapy concludes although there is a preliminary report contradictory to this result there was no body contouring observed in this study there were no statistically significant changes in thigh girth cross sectional area or laboratory values for the lipid profile except for a decrease in the triglyceride level in the blood which might be an indirect effect of the method of aminophylline absorption into the systemic circulation amber kt ovadia s camacho i june 2014 injection therapy for the management of superficial subcutaneous lipomas the journal of clinical and aesthetic dermatology 7 6 46 8 pmc 4086534 pmid 25013540 nanda s may 2011 treatment of lipoma by injection lipolysis journal of cutaneous and aesthetic surgery 4 2 135 7 doi 10 4103 0974 2077 85040 pmc 3183720 pmid 21976907 kokkinidis dg bosdelekidou ee iliopoulou sm tassos ag texakalidis pt economopoulos kp kousoulis aa september 2017 emerging treatments for ulcerative colitis a systematic review scandinavian journal of gastroenterology 52 9 923 931 doi 10 1080 00365521 2017 1326163 pmid 28503977 s2cid 4074211 philip y 2016 02 17 the membranes of cells third ed london pp 61 62 isbn 978 0 12 800486 9 oclc 940961458 cite book cs1 maint location missing publisher link external links edit phosphatidylcholines at the u s national library of medicine medical subject headings mesh v t e lipids phospholipids glycerol backbone glycerophospholipids phosphoglycerides phosphatidyl ethanolamine cephalin pe choline lecithin pc serine ps glycerol pg inositol pi glyco gpi phosphoinositides pip pi 3 p pi 4 p pi 5 p pip 2 pi 3 4 p 2 pi 3 5 p 2 pi 4 5 p 2 pip 3 ether lipids plasmalogen platelet activating factor cardiolipin sphingosine backbone sphingomyelin metabolites inositol phosphate inositol lysophosphatidic acid choline phosphocholine citicoline v t e cell signaling lipid signaling extracellular eicosanoids classic eoxins leukotrienes ltr prostacyclin ipr prostaglandins pgr thromboxane txr nonclassic eets endocannabinoids cbr epi lipoxins fpr2 hepoxilins isoprostanes lipoxins fpr2 oxoeicosanoids oxer resolvins fpr2 lysophospholipids lpa lpar s1p s1pr steroids bile acids gpbar neurosteroids pheromones vnr others paf pafr retinal rho intracellular nuclear receptor steroids sex steroids androgens ar estrogens er progestogens pr corticosteroids glucocorticoids gr mineralocorticoids mr others bile acids fxr calcitriol vdr others eicosanoids ppar free fatty acids ppar retinoic acid rar rxr second messenger general arachidonic acid dag pkc trpc ip 3 ip 3 r ryr phosphatidic acid phosphoinositides pip 2 irks pip 3 pkb akt btk pdpk1 ptdins 3 4 p 2 pkb akt pdpk1 sphingolipids c1p ceramide capps ksr1 pkcζ ctsd glucosylceramides s1p sphingosine sdk1 pkh ypk precursors general fatty acids ω 3 ω 6 steroids squalene lanosterol cholesterol v t e dietary supplements types bodybuilding supplement energy drink energy bar fatty acids herbal supplements minerals prebiotics probiotics lactobacillus bifidobacterium protein supplements vitamins vitamins and chemical elements minerals retinol vitamin a b vitamins thiamine b 1 riboflavin b 2 niacin b 3 pantothenic acid b 5 pyridoxine b 6 biotin b 7 folic acid b 9 cobalamin b 12 ascorbic acid vitamin c ergocalciferol and cholecalciferol vitamin d tocopherol vitamin e naphthoquinone vitamin k calcium choline chromium cobalt copper fluorine iodine iron magnesium manganese molybdenum phosphorus potassium selenium sodium sulfur zinc other common ingredients aakg β hydroxy β methylbutyrate carnitine chondroitin sulfate cod liver oil copper gluconate creatine dietary fiber echinacea ephedra fish oil folic acid ginseng glucosamine glutamine grape seed extract guarana iron supplements japanese honeysuckle krill oil lingzhi linseed oil lipoic acid milk thistle melatonin red yeast rice royal jelly saw palmetto spirulina st john s wort taurine wheatgrass wolfberry yohimbine zinc gluconate related articles codex alimentarius enzyte hadacol herbal tea nutraceutical multivitamin nutrition category acetylcholine receptor modulators v t e muscarinic acetylcholine receptor modulators machrs tooltip muscarinic acetylcholine receptors agonists 77 lh 28 1 ac 42 ac 260 584 aceclidine acetylcholine af30 af150 s af267b alvameline aqra 741 arecoline bethanechol butyrylcholine carbachol cdd 0034 cdd 0078 cdd 0097 cdd 0098 cdd 0102 cevimeline choline cis dioxolane desmethylclozapine norclozapine ethoxysebacylcholine guvacoline gxv 813 ex a8078 itameline ly 593 039 l 689 660 ly 2 033 298 mcna343 methacholine milameline muscarine ngx 267 ocvimeline oxotremorine pd 151 832 pilocarpine rs86 sabcomeline sdz 210 086 sebacylcholine suberyldicholine talsaclidine tazomeline thiopilocarpine vedaclidine vu 0029767 vu 0090157 vu 0152099 vu 0152100 vu 0238429 way 132 983 xanomeline ym 796 positive allosteric modulators anavex 3 71 af710b antagonists 3 quinuclidinyl benzilate 4 damp aclidinium bromide formoterol abediterol af dx 250 af dx 384 ambutonium bromide anisodamine anisodine antihistamines first generation e g brompheniramine buclizine captodiame chlorphenamine chlorpheniramine cinnarizine clemastine cyproheptadine dimenhydrinate dimetindene diphenhydramine doxylamine meclizine mequitazine perlapine phenindamine pheniramine phenyltoloxamine promethazine propiomazine triprolidine aq ra 741 atropine atropine methonitrate atypical antipsychotics e g clozapine fluperlapine olanzapine fluoxetine rilapine quetiapine tenilapine zotepine benactyzine benzatropine benztropine benzilone benzilylcholine mustard benzydamine bevonium bibn 99 biperiden bornaprine camylofin car 226 086 car 301 060 car 302 196 car 302 282 car 302 368 car 302 537 car 302 668 caramiphen cimetropium bromide clidinium bromide cloperastine cs 27349 cyclobenzaprine cyclopentolate darifenacin dau 5884 desfesoterodine dexetimide dibd dicycloverine dicyclomine dihexyverine difemerine diphemanil metilsulfate ditran drofenine ea 3167 ea 3443 ea 3580 ea 3834 emepronium bromide etanautine etybenzatropine ethybenztropine fenpiverinium fentonium bromide fesoterodine flavoxate glycopyrronium bromide beclometasone formoterol indacaterol neostigmine hexahydrodifenidol hexahydrosiladifenidol hexbutinol hexocyclium himbacine hl 031 120 homatropine imidafenacin ipratropium bromide salbutamol isopropamide j 104 129 hyoscyamine mamba toxin 3 mamba toxin 7 mazaticol mebeverine meladrazine mepenzolate methantheline methoctramine methylatropine methylhomatropine methylscopolamine metixene muscarinic toxin 7 n ethyl 3 piperidyl benzilate n methyl 3 piperidyl benzilate nefopam octatropine methylbromide anisotropine methylbromide orphenadrine otenzepad af dx 116 otilonium bromide oxapium iodide oxitropium bromide oxybutynin oxyphencyclimine oxyphenonium bromide pbid pd 102 807 pd 0298029 penthienate pethidine pfhhsid phenglutarimide phenyltoloxamine pipenzolate bromide piperidolate pirenzepine piroheptine pizotifen poldine pridinol prifinium bromide procyclidine profenamine ethopropazine propantheline bromide propiverine quinidine 3 quinuclidinyl thiochromane 4 carboxylate revefenacin rociverine...