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Tutorialsandlecturesonlipids

Index

Tutorialseriesonlipids
SetofPowerpointfilescoveringLipidChemistryandLipidMetabolomics

Lipidsdefined
LipidDefinition

Categoriesoflipids
1.FattyAcyls[FA]
2.Glycerolipids[GL]
3.Glycerophospholipids[GP]
4.Sphingolipids[SP]
5.Sterollipids[ST]
6.Prenollipids[PR]
7.Saccharolipids[SL]
8.Polyketides[PK]

Biologicalfunctions
Membranes
Energystorage
Signaling
Otherfunctions

References
Referencesandresources

SeeAlso

AuthorRecommendationsandtools
Classification
Nomenclature
Structuredrawing

TutorialSeriesonLipidChemistryandLipidMetabolomics
PresentedasasetofPowerpointfiles

A:LipidChemistry
Lipidchemistryandclassification

http://www.lipidmaps.org/resources/tutorials/lipid_tutorial.html#L 1/12
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B:LipidMetabolomics
1.FattyAcidBiosynthesis
2.FattyAcidOxidation
3.KetoneBodiesandEssentialFattyAcids
4.ProstaglandinsandOtherEicosanoids
5.GlycerolipidsandGlycerophospholipids
6.Sphingolipids
7.CholesterolandOtherSterols
8.Lipoproteins
9.FatSolubleVitamins

LipidDefinition
Alipidisgenerallyconsideredtobeanymoleculethatisinsolubleinwaterandsolubleinorganicsolvents.Biological
lipidsusuallyrefertoabroadgroupingofnaturallyoccurringmoleculeswhichincludesfattyacids,waxes,
eicosanoids,monoglycerides,diglycerides,triglycerides,phospholipids,sphingolipids,sterols,terpenes,prenols,fat
solublevitamins(suchasvitaminsA,D,EandK)andothers[1,2,3],incontrasttotheothermajorgroupingsof
biologicalmolecules,namelythenucleicacids,aminoacids,andcarbohydrates(sugars).Themainbiological
functionsoflipidsincludetheircentralroleinenergystorage,asstructuralcomponentsofcellmembranes,andas
importantsignalingmolecules.Lipidsmaybebroadlydefinedashydrophobicoramphipathicsmall
moleculesthatoriginateentirelyorinpartbycarbanionbasedcondensationsofthioestersand/orby
carbocationbasedcondensationsofisopreneunits[4].

Lipidbiochemical"buildingblocks"

Usingthisapproach,lipidshavebeendividedintoeightcategories:fattyacyls,glycerolipids,
glycerophospholipids,sphingolipids,saccharolipidsandpolyketides(derivedfromcondensationofketoacyl
subunits)andsterollipidsandprenollipids(derivedfromcondensationofisoprenesubunits)[4,5].

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Mechanismofchainextensionwithketoacylandisoprenegroups

Seeexamplesofstructuresforthe8lipidcatgories.

CategoriesofLipids

Fattyacyls[FA]
Thefattyacyls[FA]areadiversegroupofmoleculessynthesizedbychainelongationofanacetylCoAprimerwith
malonylCoA(ormethylmalonylCoA)groupsthatmaycontainacyclicfunctionalityand/oraresubstitutedwith
heteroatoms.Thefattyacylstructurerepresentsthemajorlipidbuildingblockofcomplexlipidsandthereforeisone
ofthemostfundamentalcategoriesofbiologicallipids.Thefattyacylgroupinthefattyacidsandconjugatesclassis
characterizedbyarepeatingseriesofmethylenegroupsthatimparthydrophobiccharactertothiscategoryoflipids.
Thefirstsubclassincludesthestraightchainsaturatedfattyacidscontainingaterminalcarboxylicacid.Itcouldalso
beconsideredthemostreducedendproductofthepolyketidepathway.Variantsofthisstructurehaveoneormore
methylsubstituentsandencompassquitecomplexbranchedchainfattyacids,suchasthemycolicacids.Thelongest
chaininbranchedchainfattyacidsdefinesthechainlengthofthesecompounds.Aconsiderablenumberofvariations
onthisbasicstructureoccurinallkingdomsoflife,includingfattyacidswithoneormoredoublebondsandeven
acetylenic(triple)bonds.Heteroatomsofoxygen,halogen,nitrogen,andsulfurarealsolinkedtothecarbonchainsin
specificsubclasses.Cyclicfattyacidscontainingthreetosixcarbonatomsaswellasheterocyclicringscontaining
oxygenornitrogenarefoundinnature.Thecyclopentenylfattyacidsareanexampleofthislattersubclass.Thethia
fattyacidsubclasscontainssulfuratom(s)inthefattyacidstructureandisexemplifiedbylipoicacidandbiotin.
Thiolsandthioethersareinthisclass,butthethioestersareplacedintheesterclassbecauseoftheinvolvementof
theseandsimilarestersinfattyacidmetabolismandsynthesis.Separateclassesformorecomplexfattyacidswith
multiplefunctionalgroups(butnonbranched)aredesignatedbythetotalnumberofcarbonatomsfoundinthe
criticalbiosyntheticprecursor.Theseincludeoctadecanoidsandlipidsinthejasmonicacidpathwayofplanthormone
biosynthesis,eventhoughjasmonicacidshavelostsomeoftheircarbonatomsfromthebiochemicalprecursor,12
oxophytodienoicacid.Eicosanoidsderivedfromarachidonicacidincludeprostaglandins,leukotrienes,andother
structuralderivatives.Thedocosanoidscontain22carbonatomsandderivefromacommonprecursor,
docosahexaenoicacid.Manymembersoftheseseparatesubclassesofmorecomplexfattyacidshavedistinct
biologicalactivities.

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Exampleofafattyacid

Othermajorlipidclassesinthefattyacylcategoryincludefattyacidesterssuchaswaxmonoestersanddiestersand
thelactones.Thefattyesterclassalsohassubclassesthatincludeimportantbiochemicalintermediatessuchasfatty
acylthioesterCoAderivatives,fattyacylthioesteracylcarrierprotein(ACP)derivatives,fattyacylcarnitines(estersof
carnitine),andfattyadenylates,whicharemixedanhydrides.Thefattyalcoholsandfattyaldehydesaretypifiedby
terminalhydroxyandoxogroups,respectively.ThefattyamidesarealsoNfattyacylatedaminesandunsubstituted
amides,andmanysimpleamideshaveinterestingbiologicalactivitiesinvariousorganisms.Thefattyamidesinclude
Nacylethanolaminessuchasanandamide.Fattyacylhomoserinelactonesarefattyamidesinvolvedinbacterial
quorumsensingHydrocarbonsareincludedasaclassoffattyacidderivativesbecausetheycorrespondtosixelectron
reductionproductsoffattyacidsthatmayhavebeengeneratedbylossofthecarboxylicacidfromafattyacidorfatty
acylmoietyduringtheprocessofdiagenesisingeologicalsamples.Longchainethersalsohavebeenobservedin
nature.

Examplesofsomeeicosanoids

Viewclassificationoffattyacyls.

Seeexamplesofcorestructuresforprostaglandinsandthromboxanes.

DownloadprostaglandinandthromboxanecorestructuresasaChemdrawfile.

UseonlinedrawingtoolforFAstructures.
DownloadPowerpointTutorials:
Lec.1:FattyAcidBiosynthesis
Lec.2:FattyAcidOxidation
Lec.3:KetoneBodiesandEssentialFattyAcids
Lec.4:ProstaglandinsandOtherEicosanoids

Glycerolipids[GL]
Glycerolipidsarecomposedmainlyofmono,diandtrisubstitutedglycerols,themostwellknownbeingthefatty
acidestersofglycerol(triacylglycerols),alsoknownastriglycerides.Thesecomprisethebulkofstoragefatin
mammaliantissues.Macrocyclicetherlipidsalsooccurasglycerolipidsinthemembranesofarchaebacteria.

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Exampleofaglycerolipid

Glyceroglycolipidsrepresentadditionalsubclasseswhicharecharacterizedbythepresenceofoneormoresugar
residuesattachedtoglycerolviaaglycosidiclinkage.Examplesofstructuresinthiscategoryarethe
digalactosyldiacylglycerolsfoundinplantmembranesandseminolipidfrommammalianspermatazoa.

Viewclassificationofglycerolipids.

Seeexamplesofcorestructuresforsomecommonglycerolipids.

DownloadexamplesofcorestructuresasaChemdrawfile.

UseonlinedrawingtoolforGLstructures.
DownloadPowerpointTutorials:
Lec.5:GlycerolipidsandGlycerophospholipids

Glycerophospholipids[GP]
Glycerophospholipids,alsoreferredtoasphospholipids,areubiquitousinnatureandarekeycomponentsofthelipid
bilayerofcells,aswellasbeinginvolvedinmetabolismandsignaling.Glycerophospholipidsmaybesubdividedinto
distinctclasses,basedonthenatureofthepolarheadgroupatthesn3positionoftheglycerolbackboneineukaryotes
andeubacteriaorthesn1positioninthecaseofarchaebacteria.Examplesofglycerophospholipidsfoundin
biologicalmembranesarephosphatidylcholine(alsoknownasPCorlecithin),phosphatidylethanolamine
(PE),phosphatidylinositol(PI)andphosphatidylserine(PS).Inthecaseoftheglycerophosphoglycerolsand
glycerophosphoglycerophosphates,asecondglycerolunitconstitutespartoftheheadgroup,whereasforthe
glycerophosphoglycerophosphoglycerols(cardiolipins),athirdglycerolunitistypicallyacylatedatthesn1'andsn2'
positionstocreateapseudosymmetricalmolecule.Eachheadgroupclassisfurtherdifferentiatedonthebasisofthe
sn1andsn2substituentsontheglycerolbackbone.Althoughtheglycerolbackboneissymmetrical,thesecond
carbonbecomesachiralcenterwhenthesn1andsn3carbonshavedifferentsubstituents.Alargenumberoftrivial
namesareassociatedwithphospholipids.Inthesystematicnomenclature,mono/diradylglycerophospholipidswith
differentacyloralkylsubstituentsaredesignatedbysimilarconventionsfornamingofclasses(seebelow)andare
groupedaccordingtothecommonpolarmoieties(i.e.,headgroups).Typically,oneortwooftheglycerolhydroxyl
groupsareacylatedwithlongchainfattyacids,buttherearealsoalkyllinkedand1Zalkenyllinked(plasmalogen)
glycerophospholipids,aswellasdialkylethervariantsinprokaryotes.Themainbiosyntheticpathwaysforthe
formationofPCandPEwereelucidatedthroughtheeffortsofEugeneP.Kennedyandcoworkersinthe1950sand
1960s,andmoredetailedinterconversionpathwaystoformadditionalclassesofphospholipidsweredescribedmore
recently.

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Exampleofaglycerophospholipid

Inadditiontoservingasaprimarycomponentofcellularmembranesandbindingsitesforintraandintercellular
proteins,someglycerophospholipidsineukaryoticcells,suchasphosphatidylinositolsandphosphatidicacidsare
eitherprecursorsof,orarethemselves,membranederivedsecondmessengers.

Viewclassificationofglycerophospholipids.

Seeexamplesofcorestructuresforthemajorglycerophospholipidheadgroups.

DownloadexamplesofcorestructuresasaChemdrawfile.

UseonlinedrawingtoolforcreatingGPstructures.
DownloadPowerpointTutorials:
Lec.5:GlycerolipidsandGlycerophospholipids

Sphingolipids[SP]
Sphingolipidsareacomplexfamilyofcompoundsthatshareacommonstructuralfeature,asphingoidbasebackbone
thatissynthesizeddenovofromserineandalongchainfattyacylCoA,thenconvertedintoceramides,
phosphosphingolipids,glycosphingolipids,andotherspecies,includingproteinadducts.Anumberoforganismsalso
producesphingoidbaseanalogsthathavemanyofthesamefeaturesassphingolipids(suchaslongchainalkyland
vicinalaminoandhydroxylgroups)butdifferinotherfeatures.Thesehavebeenincludedinthiscategorybecause
someareknowntofunctionasinhibitorsorantagonistsofsphingolipids,andinsomeorganisms,thesetypesof
compoundsmayserveassurrogatesforsphingolipids.Sphingolipidscanbedividedintoseveralmajorclasses:the
sphingoidbasesandtheirsimplederivatives(suchasthe1phosphate),thesphingoidbaseswithanamidelinked
fattyacid(e.g.,ceramides),andmorecomplexsphingolipidswithheadgroupsthatareattachedviaphosphodiester
linkages(thephosphosphingolipids),viaglycosidicbonds(thesimpleandcomplexglycosphingolipidssuchas
cerebrosidesandgangliosides),andothergroups(suchasphosphonoandarsenosphingolipids).Themajor
sphingoidbaseofmammalsiscommonlyreferredtoas"sphingosine,"becausethatnamewasaffixedbythefirst
scientisttoisolatethiscompound.Sphingosineis(2S,3R,4E)2aminooctadec4ene1,3diol(itisalsocalledD
erythrosphingosineandsphing4enine).Thisisonlyoneofmanysphingoidbasesfoundinnature,whichvaryin
alkylchainlengthandbranching,thenumberandpositionsofdoublebonds,thepresenceofadditionalhydroxyl
groups,andotherfeatures.Thestructuralvariationhasfunctionalsignificanceforexample,sphingoidbasesinthe
dermishaveadditionalhydroxylsatposition4(phytoceramides)and/or6thatcaninteractwithneighboring
molecules,therebystrengtheningthepermeabilitybarrierofskin.Sphingoidbasesarefoundinavarietyof
derivatives,includingthe1phosphates,lysosphingolipids(suchassphingosine1phosphocholineaswellas
sphingosine1glycosides),andNmethylderivatives(Nmethyl,N,Ndimethyl,andN,N,Ntrimethyl).Inaddition,a
largenumberoforganisms,suchasfungiandsponges,producecompoundswithstructuralsimilaritytosphingoid
bases,someofwhich(suchasmyriocinandthefumonisins)arepotentinhibitorsofenzymesofsphingolipid
metabolism.Ceramides(Nacylsphingoidbases)areamajorsubclassofsphingoidbasederivativeswithanamide
linkedfattyacid.Thefattyacidsaretypicallysaturatedormonounsaturatedwithchainlengthsfrom14to26carbon
atomsthepresenceofahydroxylgrouponcarbon2isfairlycommon.Ceramidessometimeshavespecializedfatty
acidswhichhasa30carbonfattyacidwithahydroxylgroupontheterminalcarbon.Ceramidesaregenerally
precursorsofmorecomplexsphingolipids.Themajorphosphosphingolipidsofmammalsaresphingomyelins
(ceramidephosphocholines),whereasinsectscontainmainlyceramidephosphoethanolaminesandfungihave
phytoceramidephosphoinositolsandmannosecontainingheadgroups.

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Exampleofasphingolipid(ceramide)

Glycosphingolipidsareclassifiedonthebasisofcarbohydratecomposition:1)neutralglycosphingolipidscontainone
ormoreunchargedsugarssuchasglucose(Glu),galactose(Gal),Nacetylglucosamine(GlcNAc),N
acetylgalactosamine(GalNAc),andfucose(Fuc),whicharegroupedintofamiliesbasedonthenatureoftheglyco
substituentsasshowninthelisting2)acidicglycosphingolipidscontainionizedfunctionalgroups(phosphateor
sulfate)attachedtoneutralsugarsorchargedsugarresiduessuchassialicacid(NacetylorNglycoloylneuraminic
acid).Thelatterarecalledgangliosides,andthenumberofsialicacidresiduesisusuallydenotedwithasubscript
letter(i.e.,mono,diortri)plusanumberreflectingthesubspecieswithinthatcategory3)basic
glycosphingolipids4)amphotericglycosphingolipids.Forafewglycosphingolipids,historicallyassignednamesas
antigensandbloodgroupstructuresarestillincommonuse(e.g.,LewisxandsialylLewisx).Someaquaticorganisms
containsphingolipidsinwhichthephosphateisreplacedbyaphosphonoorarsenategroup.Theothercategory
includessphingolipidsthatarecovalentlyattachedtoproteinsforexample,hydroxyceramidesand
glucosylceramidesareattachedtosurfaceproteinsofskin,andinositolphosphoceramidesareusedasmembrane
anchorsforsomefungalproteinsinamanneranalogoustotheglycosylphosphatidylinositolanchorsthatareattached
toproteinsinothereukaryotes.
Viewclassificationofsphingolipids.

Seeexamplesofstructuresforthemajorsphingolipidsandthesugarresiduesfoundinglycosphingolipids.

DownloadsphingolipidandsugarstructuresasaChemdrawfile.

UseonlinedrawingtoolforSPstructures.
DownloadPowerpointTutorials:
Lec.6:Sphingolipids

Sterollipids[ST]
Sterollipids,suchascholesterolanditsderivativesareanimportantcomponentofmembranelipids,[8]alongwith
theglycerophospholipidsandsphingomyelins.Thesteroids,whichalsocontainthesamefusedfourringcore
structure,havedifferentbiologicalrolesashormonesandsignalingmolecules.TheC18steroidsincludetheestrogen
familywhereastheC19steroidscomprisetheandrogenssuchastestosteroneandandrosterone.TheC21subclass
includestheprogestogensaswellastheglucocorticoidsandmineralocorticoids.

Cholesterolstructureandnumbering

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Thesecosteroids,comprisingvariousformsofvitaminD,arecharacterizedbycleavageoftheBringofthecore
structure.Otherexamplesofsterolsarethebileacidsandtheirconjugates,[9]whichinmammalsareoxidized
derivativesofcholesterolandaresynthesizedintheliver.

Viewclassificationofsterollipids.

Seeexamplesofcorestructuresforthesterols.

DownloadexamplesofcorestructuresasaChemdrawfile.

UseonlinedrawingtoolforSTstructures.
DownloadPowerpointTutorials:
Lec.7:CholesterolandOtherSterols
Lec.8:Lipoproteins

PrenolLipids[PR]
Prenollipidsaresynthesizedfromthe5carbonprecursorsisopentenyldiphosphateanddimethylallyldiphosphate
thatareproducedmainlyviathemevalonicacid(MVA)pathway.[10]Thesimpleisoprenoids(linearalcohols,
diphosphates,etc.)areformedbythesuccessiveadditionofC5units,andareclassifiedaccordingtothenumberof
theseterpeneunits.Structurescontaininggreaterthan40carbonsareknownaspolyterpenes.

Examplesofisoprenoidstructures

CarotenoidsareimportantsimpleisoprenoidsthatfunctionasantioxidantsandasprecursorsofvitaminA.Another
biologicallyimportantclassofmoleculesisexemplifiedbythequinonesandhydroquinones,whichcontainan
isoprenoidtailattachedtoaquinonoidcoreofnonisoprenoidorigin.VitaminEandvitaminK,aswellasthe
ubiquinones,areexamplesofthisclass.Bacteriasynthesizepolyprenols(calledbactoprenols)inwhichtheterminal
isoprenoidunitattachedtooxygenremainsunsaturated,whereasinmammalianpolyprenols(dolichols)theterminal
isoprenoidisreduced.

Viewclassificationofprenollipids.
Seeexamplesofcorestructuresforthemonoterpenes,diterpenes,triterpenesand
Quinones/hydroquinones.
Downloadexamplesofcorestructuresforthemonoterpenes,diterpenes,triterpenesand
Quinones/hydroquinonesasaChemdrawfile.
DownloadPowerpointTutorials:
Lec.9:FatSolubleVitamins

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Saccharolipids[SL]
Saccharolipidsdescribecompoundsinwhichfattyacidsarelinkeddirectlytoasugarbackbone,formingstructures
thatarecompatiblewithmembranebilayers.Inthesaccharolipids,asugarsubstitutesfortheglycerolbackbonethat
ispresentinglycerolipidsandglycerophospholipids.Themostfamiliarsaccharolipidsaretheacylatedglucosamine
precursorsoftheLipidAcomponentofthelipopolysaccharidesinGramnegativebacteria.

StructureofKdo2LipidA.Glucosamineresiduesinblue,Kdoresiduesinred,
acylchainsinblackandphosphategroupsingreen

TypicallipidAmoleculesaredisaccharidesofglucosamine,whicharederivatizedwithasmanyassevenfattyacyl
chains.TheminimallipopolysacchariderequiredforgrowthinE.coliisKdo2LipidA,ahexaacylateddisaccharideof
glucosaminethatisglycosylatedwithtwo3deoxyDmannooctulosonicacid(Kdo)residues.

Viewclassificationofsaccharolipids.

Polyketides[PK]
Polyketidesaresynthesizedbypolymerizationofacetylandpropionylsubunitsbyclassicenzymesaswellasiterative
andmultimodularenzymesthatsharemechanisticfeatureswiththefattyacidsynthases.Theycompriseaverylarge
numberofsecondarymetabolitesandnaturalproductsfromanimal,plant,bacterial,fungalandmarinesources,and
havegreatstructuraldiversity.Manypolyketidesarecyclicmoleculeswhosebackbonesareoftenfurthermodifiedby
glycosylation,methylation,hydroxylation,oxidation,and/orotherprocesses.Manycommonlyusedantimicrobial,
antiparasitic,andanticanceragentsarepolyketidesorpolyketidederivatives,suchaserythromycins,tetracylines,
avermectins,andantitumorepothilones.

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Examplesofpolyketidestructures

Viewclassificationofpolyketides.

BiologicalFunctionsofLipids

Membranes
Eukaryoticcellsarecompartmentalizedintomembranesurroundedorganelleswhichcarryoutavarietyofbiological
functions.Theglycerophospholipidsarethemainstructuralcomponentofbiologicalmembranes,suchastheplasma
membraneofcellsandtheintracellularmembranesoforganellesinmamaliancellstheplasmamembranephysically
separatestheintracellularcomponentsfromtheextracellularenvironment.Theglycerophospholipidsare
amphipathicmolecules(containingbothhydrophobicandhydrophilicregions)thatcontainaglycerolcorelinkedto
twofattyacidderived"tails"byesterlinkagesandtoone"head"groupbyaphosphateesterlinkage.While
glycerophospholipidsarethemajorcomponentofbiologicalmembranes,othernonglyceridelipidcomponentssuch
assphingomyelinandsterols(mainlycholesterolinmamaliancellmembranes)arealsofoundinbiological
membranes.Inplantsandalgae,thegalactosyldiacylglycerols,andsulfoquinovosyldiacylglycerol,whichlacka
phosphategroup,areimportantcomponentsofmembranesofchloroplastsandrelatedorganellesandarethemost
abundantlipidsinphotosynthetictissues,includingthoseofhigherplants,algaeandcertainbacteria.Cardiolipinsare
asubclassofglycerophospholipidscontainingfouracylchainsandthreeglycerolgroupsthatareparticularly
abundantintheinnermitochondrialmembranewhereinadditiontofunctioningasacomponentofmembranes,they
activateenzymesinvolvedwithoxidativephosphorylation.
Biologicalmembranesarecomposedoflipidbilayers.Theformationoflipidbilayersisanenergeticallypreferred
processwhentheglycerophospholipidsdescribedaboveareinanaqueousenvironment.Inanaqueoussystem,the
polarheadsoflipidsaligntowardsthepolar,aqueousenvironment,whilethehydrophobictailsminimizetheir
contactwithwaterandtendtoclustertogether,formingavesicledependingontheconcentrationofthelipid,this
biophysicalinteractionmayresultintheformationofmicelles,liposomes,orlipidbilayers.Otheraggregationstates
arealsoobservedandformpartofthepolymorphismofamphiphile(lipid)behavior.Phasebehaviorisanareaof
studythatreflectsthebiophysicalpropertiesoflipids.Micellesandbilayersforminthepolarmediumasaresultof
thehydrophobiceffect.Whendissolvingalipophilicoramphiphilicsubstanceinapolarenvironment,thepolar
molecules(i.e.,waterinanaqueoussolution)becomemoreorderedaroundthedissolvedlipophilicsubstance,since
thepolarmoleculescannotformhydrogenbondstothelipophilicareasoftheamphiphile.Thus,inanaqueous
environment,thewatermoleculesformanordered"clathrate"cagearoundthedissolvedlipophilicmolecule.

Energystorage
Triacylglycerols,storedinvariouscells,butespeciallyinadipose(fat)tissue,areamajorformofenergystoragein
mammals.Theadipocyte,orfatcell,isdesignedforcontinuoussynthesisandbreakdownoftriacylglycerols,with
breakdowncontrolledmainlybytheactivationoftheenzymeknownashormonesensitivelipase.Thecomplete
oxidationoffattyacidsprovideshighcaloriccontent,about9kcal/g,comparedwith4kcal/gforthebreakdownof
carbohydratesandproteins.Sinceagramofcarbohydrateorproteinhasconsiderablewaterofhydrationassociated
withit,itoccupiesmorevolumethanagramoffat,sothatfatisanevenmoreefficientstorageformofenergy.
Migratorybirdsthatmustflylongdistanceswithouteatingusestoredenergyoftriacylglycerolstofueltheirflights.

Signaling
Inrecentyears,considerableevidencehasemergeddemonstratingthatlipidsignalingisavitalcomponentofcell
signaling.Lipidsignalingmayoccurviaactivationofavarietyofreceptors,includingGproteincoupledandnuclear
receptors,andmembersofseveraldifferentlipidcategorieshavebeenidentifiedassignalingmoleculesandcellular

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messengers.Therearemanyexamplesofimportantsignalinglipidsincludingsphingosine1phosphate,a
sphingolipidderivedfromceramidethatisapotentmessengermoleculeinvolvedinregulatingcalciummobilization,
cellgrowth,andapoptosisdiacylglycerol(DAG)andtheinositolphosphatesdervivedfromthe
phosphatidylinositolphosphates(PIPs),involvedincalciummediatedactivationofproteinkinaseCthe
prostaglandins,whichareonetypeoffattyacidderivedeicosanoidinvolvedininflammationandimmunitythe
steroidhormonessuchasestrogen,testosteroneandcortisol,whichmodulateahostoffunctionssuchas
reproduction,metabolismandbloodpressureandtheoxysterolssuchas25hydroxycholesterolthatareliverX
receptoragonists.

Otherfunctions
The"fatsoluble"vitamins(A,D,EandK),whichareisoprenebasedlipids,areessentialnutrientsstoredintheliver
andfattytissueswithadiverserangeoffunctions.Acylcarnitinesareinvolvedinthetransportandmetabolismof
fattyacidsinandoutofmitochondria,wheretheyundergobetaoxidation.Polyprenolsandtheirphosphorylated
derivativesalsoplayimportanttransportroles,inthiscasethetransportofoligosaccharidesacrossmembranes.
Polyprenolphosphatesugarsandpolyprenoldiphosphatesugarsfunctioninextracytoplasmicglycosylation
reactions,inextracellularpolysaccharidebiosynthesis(forexample,peptidoglycanpolymerizationinbacteria),andin
eukaryoticproteinNglycosylation.

Recommendationsandtools:classification,nomenclatureandstructuredrawing
Viewauthorrecommendationsfor:ClassificationNomenclatureStructuredrawing

ReferencesandResources
[1]Vance,D.E.andVance,J.E.editors.BiochemistryofLipids,LipoproteinsandMembranes5thedition.Elsevier
Science,NewYork.(2008).

[2]Dennis,E.A.Lipidomicsjoinstheomicsevolution.Proc.Natl.Acad.Sci.U.S.A.106:20892090(2009).

[3]Brown,H.A.editorMethodsinEnzymologyAcademicPress,SanDiego,vol.432,400pp(2007).

[4]FahyE.,SubramaniamS.,MurphyR.,NishijimaM.,RaetzC.,ShimizuT.,SpenerF.,vanMeerG.,WakelamM.
andDennisE.A.UpdateoftheLIPIDMAPScomprehensiveclassificationsystemforlipids.J.LipidRes.50:S9S14,
(2009).PubMedID:19098281.

[5]FahyE.,SubramaniamS.,BrownH.,GlassC.,MerrillJ.A.,MurphyR.,RaetzC.,RussellD.,SeyamaY.,ShawW.,
ShimizuT.,SpenerF.,vanMeerG.,VannieuwenhzeM.,WhiteS.,WitztumJ.andDennisE.A.Acomprehensive
classificationsystemforlipids.J.LipidRes.46:839861(2005).PubMedID:15722563.

[6]Murphy,R.C.andSmith,W.L.Theeicosanoids:cyclooxygenase,lipoxygenase,andepoxygenasepathways.In
BiochemistryofLipids,LipoproteinsandMembranes4thedition.Vance,D.E.,andVance,J.E.editors.Elsevier
Science,NewYork.341371,(2002).

[7]Stam,H.,Schoonderwoerd,K.andHulsmann,W.C.Synthesis,storageanddegradationofmyocardial
triglycerides.BasicRes.Cardiol.82(Suppl.1):1928,(1987).

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