Essential fatty acid - Wikipedia

Only two fatty acids are known to be essential for humans: alpha-linolenic acid (an omega-3 fatty acid) and linoleic acid (an omega-6 fatty acid). Some other ... Essentialfattyacid FromWikipedia,thefreeencyclopedia Jumptonavigation Jumptosearch Fattyacidsrequiredforbiologicalprocessesbutdoesnotincludethefatsthatonlyactasfuel Nottobeconfusedwithessentialoil. Typesoffatsinfood Saturatedfat Unsaturatedfat Monounsaturatedfat ω−7 ω−9 Polyunsaturatedfat ω−3 ω−6 Transfat Interesterifiedfat Seealso Fattyacid Essentialfattyacid Conditionallyessentialfattyacid Triglyceride Cholesterol vte Essentialfattyacids,orEFAs,arefattyacidsthathumansandotheranimalsmustingestbecausethebodyrequiresthemforgoodhealthbutcannotsynthesizethem.[1] Theterm"essentialfattyacid"referstofattyacidsrequiredforbiologicalprocessesbutdoesnotincludethefatsthatonlyactasfuel.Essentialfattyacidsshouldnotbeconfusedwithessentialoils,whichare"essential"inthesenseofbeingaconcentratedessence. Onlytwofattyacidsareknowntobeessentialforhumans:alpha-linolenicacid(anomega-3fattyacid)andlinoleicacid(anomega-6fattyacid).[2]Someotherfattyacidsaresometimesclassifiedas"conditionallyessential",meaningthattheycanbecomeessentialundersomedevelopmentalordiseaseconditions;examplesincludedocosahexaenoicacid(anomega-3fattyacid)andgamma-linolenicacid(anomega-6fattyacid). WhenthetwoEFAswerediscoveredin1923,theyweredesignated"vitaminF",butin1929,researchonratsshowedthatthetwoEFAsarebetterclassifiedasfatsratherthanvitamins.[3] Contents 1Functions 2Nomenclatureandterminology 2.1Examples 3Essentialityinhumandiet 3.1Conditionalessentiality 4Foodsources 5Humanhealth 5.1Referenceintakevalues 5.2Essentialfattyaciddeficiency 6Seealso 7References Functions[edit] Thebiologicaleffectsoftheω-3andω-6fattyacidsaremediatedbytheirmutualinteractions,seeEssentialfattyacidinteractionsfordetail. Inthebody,essentialfattyacidsservemultiplefunctions.Ineachofthese,thebalancebetweendietaryω-3andω-6stronglyaffectsfunction. Theyaremodifiedtomake theclassiceicosanoids(affectinginflammationandmanyothercellularfunctions) theendocannabinoids(affectingmood,behaviorandinflammation) thelipoxinswhichareagroupofeicosanoidderivativesformedviathelipoxygenasepathwayfromω-6EFAsandresolvinsfromω-3(inthepresenceofacetylsalicylicacid,downregulatinginflammation) theisofurans,neurofurans,isoprostanes,hepoxilins,epoxyeicosatrienoicacids(EETs)andneuroprotectinD Theyformlipidrafts(affectingcellularsignaling)[4] TheyactonDNA(activatingorinhibitingtranscriptionfactorssuchasNF-κB,whichislinkedtopro-inflammatorycytokineproduction)[5] Nomenclatureandterminology[edit] Mainarticle:Fattyacid§ Nomenclature Fattyacidsarehydrocarbonspossessingacarboxylgroup(–COOH)groupatoneend,andamethylgroup(–CH3)attheotherend.Theyarealmostalwaysstraight-chained.Thecarbonnexttothecarboxylateisknownasα,thenextcarbonβ,andsoforth.Sincebiologicalfattyacidscanbeofdiverselengths,thelastpositionisoftenlabelledasa"ω",thelastletterintheGreekalphabet.Thus,theω-3indicatesthatthefirstunsaturatedcarbon-carbonbondfromtheterminalend(ω)ofthenchainisthethirdone.Typically,thenumberofcarbonsandthenumberofdoublebondsarealsolistedinshortdescriptionsofunsaturatedfattyacids.Forinstance,ω-318:4,or18:4ω-3,or18:4n−3indicatesstearidonicacid,an18-carbonchainwith4doublebonds,andwithadoublebondbetweenthethirdandfourthcarbonatomsfromtheCH3end.Doublebondsarecisandseparatedbyasinglemethylene(CH2)groupunlessotherwisenoted.Infreefattyacidform,thechemicalstructureofstearidonicacidis: Examples[edit] Polyunsaturatedfattyacidswith16-and18-carbonchainsaresometimesclassifiedasshortchainpolyunsaturatedfattyacids(SC-PUFA),asopposedtolong-chainpolyunsaturatedfattyacids(LC-PUFA),whichhavemorethan18carbonatoms.[6] BoththeessentialfattyacidsareSC-PUFAwithan18-carbonchain: ω-3fattyacid: α-linolenicacidorALA(18:3n-3) ω-6fattyacid: linoleicacidorLA(18:2n-6) Thesetwofattyacidscannotbesynthesizedbyhumansbecausehumanslackthedesaturaseenzymesrequiredfortheirproduction. Theyformthestartingpointforthecreationofmoredesaturatedfattyacids,mostofwhichalsohavealongercarbonchain: ω-3fattyacids: eicosapentaenoicacidorEPA(20:5n-3) docosahexaenoicacidorDHA(22:6n-3) ω-6fattyacids: gamma-linolenicacidorGLA(18:3n-6) dihomo-gamma-linolenicacidorDGLA(20:3n-6) arachidonicacidorAA(20:4n-6) ExceptforGLA,whichhasashort18-carbonchain,thesefattyacidshavemorethan18carbonatomsandaretypicallyclassifiedasLC-PUFA.[6] ω-9fattyacidsarenotessentialinhumansbecausetheycanbesynthesizedfromcarbohydratesorotherfattyacids. Essentialityinhumandiet[edit] Mammalslacktheabilitytointroducedoublebondsinfattyacidsbeyondcarbon9and10,hencetheomega-6linoleicacid(18:2n-6;LA)andtheomega-3linolenicacid(18:3n-3;ALA)areessentialforhumansinthediet.However,humanscanconvertbothLAandALAtofattyacidswithlongercarbonchainsandalargernumberofdoublebonds,byalternativedesaturationandchainelongation. Inhumans,arachidonicacid(20:4n-6;AA)canbesynthesizedfromLA.Inturn,AAcanbeconvertedtoanevenlongerfattyacid,thedocosapentaenoicacid(22:5n-6;DPA).Similarly,ALAcanbeconvertedtodocosahexaenoicacid(22:6n-3;DHA),althoughthelatterconversionislimited,resultinginlowerbloodlevelsofDHAthanthroughdirectingestion.Thisisillustratedbystudiesinvegansandvegetarians.[7]IfthereisrelativelymoreLAthanALAinthedietitfavorstheformationofDPAfromLAratherthanDHAfromALA.ThiseffectcanbealteredbychangingtherelativeratioofLA:ALA,butismoreeffectivewhentotalintakeofpolyunsaturatedfattyacidsislow. Inpreterminfants,thecapacitytoconvertLAtoAAandALAtoDHAislimited,andpreformedAAandDHAmayberequiredtomeettheneedsofthedevelopingbrain.BothAAandDHAarepresentinbreastmilkandcontributealongwiththeparentfattyacidsLAandALAtomeetingtherequirementsofthenewborninfant.ManyinfantformulashaveAAandDHAaddedtothemwithanaimtomakethemmoreequivalenttohumanmilk. Essentialnutrientsaredefinedasthosethatcannotbesynthesizeddenovoinsufficientquantitiesfornormalphysiologicalfunction.ThisdefinitionismetforLAandALAbutnotthelongerchainderivativesinadults.[8]Thelongerchainderivativesparticularly,however,havepharmacologicalpropertiesthatcanmodulatediseaseprocesses,butthisshouldnotbeconfusedwithdietaryessentiality. Between1930and1950,arachidonicacidandlinolenicacidweretermed'essential'becauseeachwasmoreorlessabletomeetthegrowthrequirementsofratsgivenfat-freediets.Inthe1950sArildHansenshowedthatinhumans:infantsfedskimmedmilkdevelopedtheessentialfattyaciddeficiency.Itwascharacterizedbyanincreasedfoodintake,poorgrowth,andascalydermatitis,andwascuredbytheadministrationofcornoil. LaterworkbyHansenrandomized426childrentofourtreatments:modifiedcow'smilkformula,skimmedmilkformula,skimmedmilkformulawithcoconutoil,orcow'smilkformulawithcornoil.Theinfantswhoreceivedtheskimmedmilkformulaortheformulawithcoconutoildevelopedessentialfattyaciddeficiencysignsandsymptoms.Thiscouldbecuredbyadministrationofethyllinoleate(theethylesteroflinoleicacid)withabout1%oftheenergyintake.[9] Collinsetal.1970[10]werethefirsttodemonstratelinoleicaciddeficiencyinadults.Theyfoundthatpatientsundergoingintravenousnutritionwithglucosebecameisolatedfromtheirfatsuppliesandrapidlydevelopedbiochemicalsignsofessentialfattyaciddeficiency(anincreasein20:3n-9/20:4n-6ratioinplasma)andskinsymptoms.Thiscouldbetreatedbyinfusinglipids,andlaterstudiesshowedthattopicalapplicationofsunfloweroilwouldalsoresolvethedermalsymptoms.[11]Linoleicacidhasaspecificroleinmaintainingtheskinwater-permeabilitybarrier,probablyasconstituentsofacylglycosylceramides.Thisrolecannotbemetbyanyω-3fattyacidsorbyarachidonicacid. Themainphysiologicalrequirementforω-6fattyacidsisattributedtoarachidonicacid.Arachidonicacidisthemajorprecursorofprostaglandins,leukotrienesthatplayavitalroleincellsignaling,andanendogenouscannabinoidanandamide.[12]Metabolitesfromtheω-3pathway,mainlyfromeicosapentaenoicacid,aremostlyinactive,andthisexplainswhyω-3fattyacidsdonotcorrectthereproductivefailureinratswherearachidonicisneededtomakeactiveprostaglandinsthatcauseuterinecontraction.[13]Tosomeextent,anyω-3orω-6cancontributetothegrowth-promotingeffectsofEFAdeficiency,butonlyω-6fattyacidscanrestorereproductiveperformanceandcorrectthedermatitisinrats.Particularfattyacidsarestillneededatcriticallifestages(e.g.lactation)andinsomediseasestates. Innonscientificwriting,commonusageisthatthetermessentialfattyacidcomprisesalltheω-3or-6fattyacids.Conjugatedfattyacidslikecalendicacidarenotconsideredessential.Authoritativesourcesincludethewholefamilies,butgenerallyonlymakedietaryrecommendationsforLAandALAwiththeexceptionofDHAforinfantsundertheageof6months.RecentreviewsbyWHO/FAOin2009andtheEuropeanFoodSafetyAuthority[14]havereviewedtheevidenceandmaderecommendationsforminimalintakesofLAandALAandhavealsorecommendedintakesoflongerchainω-3fattyacidsbasedontheassociationofoilyfishconsumptionwithalowerriskofcardiovasculardisease.Someearlierreviewlumpedallpolyunsaturatedfattyacidstogetherwithoutqualificationwhethertheywereshortorlong-chainPUFAorwhethertheywereω-3andω-6PUFA.[15][16][17] Conditionalessentiality[edit] Traditionallyspeaking,theLC-PUFAsarenotessentialtohealthyadults.BecausetheLC-PUFAaresometimesrequired,theymaybeconsideredconditionallyessentialfattyacids.[18] Foodsources[edit] Someofthefoodsourcesofω-3andω-6fattyacidsarefishandshellfish,seaweedoil,flaxseed(linseed)andflaxseedoil,hempseed,oliveoil,soyaoil,canola(rapeseed)oil,chiaseeds,pumpkinseeds,sunflowerseeds,leafyvegetables,andwalnuts. Essentialfattyacidsplayapartinmanymetabolicprocesses,andthereisevidencetosuggestthatlowlevelsofessentialfattyacids,orthewrongbalanceoftypesamongtheessentialfattyacids,maybeafactorinanumberofillnesses,includingosteoporosis.[19] Fishisthemainsourceofthelongeromega-3fats;eicosapentaenoicacid(EPA)anddocosahexaenoicacid(DHA),thoughtheyinitiallyacquirethesefatsthroughtheconsumptionofalgaeandseaweed.Someplant-basedfoodscontainomega-3intheformofalpha-linolenicacid(ALA),whichappearstohaveamodestbenefitforcardiovascularhealth.[20]Thehumanbodycan(andincaseofapurelyvegetariandietoftenmustunlesscertainalgaeorsupplementsderivedfromthemareconsumed)convertALAtoEPAandsubsequentlyDHA.ThiselongationofALAisinefficient.ConversiontoDHAishigherinwomenthaninmen;thisisthoughttoreflecttheneedtoprovideDHAtothefetusandinfantduringpregnancyandbreastfeeding.[21] TheIUPACLipidHandbookprovidesaverylargeanddetailedlistingoffatcontentsofanimalandvegetablefats,includingω-3and-6oils.[22]TheNationalInstitutesofHealth'sEFAEducationgrouppublishesEssentialFatsinFoodOils.[23]Thislists40commonoils,moretightlyfocusedonEFAsandsortedbyn-6:3ratio.VegetableLipidsasComponentsofFunctionalFoodlistsnotablevegetablesourcesofEFAsaswellascommentaryandanoverviewofthebiosyntheticpathwaysinvolved.[24]Carefulreaderswillnotethatthesesourcesarenotinexcellentagreement.EFAcontentofvegetablesourcesvarieswithcultivationconditions.Animalsourcesvarywidely,bothwiththeanimal'sfeedandthattheEFAmakeupvariesmarkedlywithfatsfromdifferentbodyparts. Humanhealth[edit] Mainarticle:Dietandheartdisease Essentialfattyacidsplayanimportantroleinthelifeanddeathofcardiaccells.[25][26][27][28]Additionally,essentialfattyacidsarecrucialforthedevelopmentofseveralendocannabinoidswithamultitudeoffunctionsinthebody,suchasDocosahexaenoylethanolamide(DHA-EA/synaptamide).Manyomega-3andomega-6derivedessentialfattyacidsactsimilarlytoendocannabinoidssuchasanandamideand2-AG,possessingactivityattheCB1andCB2receptors,amongothers.29 Referenceintakevalues[edit] ReferenceintakevaluesforaspublishedbythePanelonDieteticProducts,NutritionandAllergiesoftheEuropeanFoodSafetyAuthority(EFSA).[29] Commonname Type Referenceintakevalues alpha-Linolenicacid(ALA) Omega-3 2g Linoleicacid(LA) Omega-6 10g IntheUnitedStates,theAdequateIntake(AI)foromega-3fattyacidsisforALA.Itisbasedonthemedianintake,andforadultsthevaluesare1.6g/dayformenand1.1g/dayforwomen.EPAandDHAcontributeabout10percentoftotalomega-3intake.TheAIforomega-6fattyacidsisforlinoleicacidandisalsobasedonthemedianintake:17g/dayforyoungermen,droppingto14g/dayformenover50yearsold;foryoungerwomen12g/d,and11g/dayforwomenover50.Studieshaveshownthatsmallerintakesreversethesymptomsofdeficiency,butthereisinadequateinformationtosetanEstimatedAverageRequirement(EAR)foreither.[30] Essentialfattyaciddeficiency[edit] Essentialfattyaciddeficiencyresultsinadermatitissimilartothatseeninzincorbiotindeficiency.[31] Seealso[edit] Eicosanoid Hydroxyeicosatetraenoicacid Leukotriene Prostaglandin Thromboxane Specializedproresolvingmediators Essentialaminoacid Essentialfattyacidinteractions Fattyacidmetabolism Fattyacidsynthase Krilloil Nonclassiceicosanoid Oilyfish Omega-3fattyacid Omega-6fattyacid Polyunsaturatedfat References[edit] 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^Maccarrone,M;Finazzi-Agró,A(22August2003)."Theendocannabinoidsystem,anandamideandtheregulationofmammaliancellapoptosis".CellDeath&Differentiation.10(9):946–955.doi:10.1038/sj.cdd.4401284.PMID 12934069. ^Sanders,Tom;Emery,Peter(2003).MolecularBasisofHumanNutrition.London:TaylorFrances.ISBN 9780367806323. ^Jones,A(2010)."EFSAScientificOpiniononDietaryReferenceValuesforfats,includingsaturatedfattyacids,polyunsaturatedfattyacids,monounsaturatedfattyacids,transfattyacidsandcholesterol".EFSAJournal.8(3):1461.doi:10.2903/j.efsa.2010.1461. ^HeatherHutchins,MS,RD(2005-10-19)."SymposiumHighlights--Omega-3FattyAcids:RecommendationsforTherapeuticsandPrevention".Omega-3fattyacidsandtheircounterparts,n-6fattyacids,areessentialpolyunsaturatedfattyacids(PUFA)becausetheycannotbesynthesizeddenovointhebody.{{citeweb}}:CS1maint:multiplenames:authorslist(link) ^NugentKP,SpigelmanAD,PhillipsRK(June1996)."Tissueprostaglandinlevelsinfamilialadenomatouspolyposispatientstreatedwithsulindac".DiseasesoftheColonandRectum.39(6):659–62.doi:10.1007/BF02056946.PMID 8646953.S2CID 25642190.Arachidonicacidisanessentialfattyacid… ^Carlstedt-DukeJ,BrönnegårdM,StrandvikB(December1986)."Pathologicalregulationofarachidonicacidreleaseincysticfibrosis:theputativebasicdefect".ProceedingsoftheNationalAcademyofSciencesoftheUnitedStatesofAmerica.83(23):9202–6.Bibcode:1986PNAS...83.9202C.doi:10.1073/pnas.83.23.9202.PMC 387103.PMID 3097647.[T]heturnoverofessentialfattyacidsisincreased(7).Arachidonicacidisoneoftheessentialfattyacidsaffected. ^CunnaneSC(November2003)."Problemswithessentialfattyacids:timeforanewparadigm?".ProgressinLipidResearch.42(6):544–68.doi:10.1016/S0163-7827(03)00038-9.PMID 14559071. ^KrugerMC,HorrobinDF(September1997)."Calciummetabolism,osteoporosisandessentialfattyacids:areview".ProgressinLipidResearch.36(2–3):131–51.doi:10.1016/S0163-7827(97)00007-6.PMID 9624425. ^PanA,ChenM,ChowdhuryR,et al.(December2012)."α-Linolenicacidandriskofcardiovasculardisease:asystematicreviewandmeta-analysis".Am.J.Clin.Nutr.(Systematicreview).96(6):1262–73.doi:10.3945/ajcn.112.044040.PMC 3497923.PMID 23076616. ^BurdgeGC,CalderPC(September2005)."Conversionofalpha-linolenicacidtolonger-chainpolyunsaturatedfattyacidsinhumanadults"(PDF).Reprod.Nutr.Dev.45(5):581–97.doi:10.1051/rnd:2005047.PMID 16188209.Archived(PDF)fromtheoriginalon2017-08-15. ^"IUPACLipidHandbook"(PDF).iupac.org.Archived(PDF)fromtheoriginalon2006-02-12. ^"EssentialFatsinFoodOils"(PDF).efaeducation.org.Archived(PDF)fromtheoriginalon2014-12-10. ^VegetableLipidsasComponentsofFunctionalFoodArchived2006-03-20attheWaybackMachine,StuchlikandZak ^HonoréE,BarhaninJ,AttaliB,LesageF,LazdunskiM(March1994)."Externalblockadeofthemajorcardiacdelayed-rectifierK+channel(Kv1.5)bypolyunsaturatedfattyacids".ProceedingsoftheNationalAcademyofSciencesoftheUnitedStatesofAmerica.91(5):1937–41.Bibcode:1994PNAS...91.1937H.doi:10.1073/pnas.91.5.1937.PMC 43279.PMID 8127910. ^ReiffelJA,McDonaldA(August2006)."Antiarrhythmiceffectsofomega-3fattyacids".TheAmericanJournalofCardiology.98(4A):50i–60i.doi:10.1016/j.amjcard.2005.12.027.PMID 16919517. ^LandmarkK,AlmCS(November2006)."[Alpha-linolenicacid,cardiovasculardiseaseandsuddendeath]".TidsskriftfordenNorskeLægeforening(inNorwegian).126(21):2792–4.PMID 17086218. ^HerbautC(September2006)."[Omega-3andhealth]".RevueMédicaledeBruxelles(inFrench).27(4):S355–60.PMID 17091903. ^EuropeanFoodSafetyAuthority(EFSA)(2009-07-01)."Labellingreferenceintakevaluesforn-3andn-6polyunsaturatedfattyacids".EFSAJournal.7(7):1176.doi:10.2903/j.efsa.2009.1176.ISSN 1831-4732. ^FoodandNutritionBoard(2004)."DIETARYREFERENCEINTAKESFOREnergy,Carbohydrate,Fiber,Fat,FattyAcids,Cholesterol,Protein,andAminoAcids"(PDF).pp. 464,471. ^James,WilliamD.;Elston,Dirk;Treat,JamesR.;Rosenbach,MishaA.;Neuhaus,Isaac(2019-01-18).Andrews'DiseasesoftheSkin:ClinicalDermatology.p. 482.ISBN 9780323551885. vteFoodchemistry Additives Carbohydrates Coloring Enzymes Essentialfattyacids Flavors Fortification Lipids "Minerals"(Chemicalelements) Proteins Vitamins Water vteTypesoflipidsGeneral Saturation:Saturatedfat Unsaturatedfat Monounsaturatedfat Polyunsaturatedfat Essentialfattyacid Other:Fat Oil Geometry Transfat Omega-3fattyacid Omega-6fattyacid Omega-9fattyacid Eicosanoids Arachidonicacid Prostaglandins Prostacyclin Thromboxane Leukotrienes Fattyacids Caprylicacid Capricacid Lauricacid Myristicacid Palmiticacid Stearicacid Arachidicacid Behenicacid Lignocericacid Glycerides Monoglyceride Diglyceride Triglyceride Triheptanoin Trimyristin Tripalmitin Tristearin Trilinolein Triolein Phospholipids Phosphatidylserine Phosphatidylinositol Phosphatidylethanolamine Cardiolipin Dipalmitoylphosphatidylcholine Sphingolipids Ceramide Steroids Cholesterol Corticosteroids Sexsteroids Secosteroids Retrievedfrom"https://en.wikipedia.org/w/index.php?title=Essential_fatty_acid&oldid=1082549389" Categories:EssentialfattyacidsHiddencategories:CS1maint:multiplenames:authorslistWebarchivetemplatewaybacklinksCS1Norwegian-languagesources(no)CS1French-languagesources(fr)ArticleswithshortdescriptionShortdescriptionisdifferentfromWikidata Navigationmenu Personaltools NotloggedinTalkContributionsCreateaccountLogin Namespaces ArticleTalk English Views ReadEditViewhistory More Search Navigation MainpageContentsCurrenteventsRandomarticleAboutWikipediaContactusDonate Contribute HelpLearntoeditCommunityportalRecentchangesUploadfile Tools WhatlinkshereRelatedchangesUploadfileSpecialpagesPermanentlinkPageinformationCitethispageWikidataitem Print/export DownloadasPDFPrintableversion Languages 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