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Methods in Molecular Biology 2306 Fong-Fu Hsu Editor Mass Spectrometry- Based Lipidomics Methods and Protocols M M B ETHODS IN OLECULAR IO LO GY SeriesEditor JohnM.Walker School of Lifeand MedicalSciences University ofHertfordshire Hatfield, Hertfordshire, UK Forfurther volumes: http://www.springer.com/series/7651 For over 35 years, biological scientists have come to rely on the research protocols and methodologiesinthecriticallyacclaimedMethodsinMolecularBiologyseries.Theserieswas thefirsttointroducethestep-by-stepprotocolsapproachthathasbecomethestandardinall biomedical protocol publishing. Each protocol is provided in readily-reproducible step-by step fashion, opening with an introductory overview, a list of the materials and reagents neededtocompletetheexperiment,andfollowedbyadetailedprocedurethatissupported with a helpful notes section offering tips and tricks of the trade as well as troubleshooting advice. These hallmark features were introduced by series editor Dr. John Walker and constitutethekeyingredientineachandeveryvolumeoftheMethodsinMolecularBiology series. Tested and trusted, comprehensive and reliable, all protocols from the series are indexedinPubMed. Mass Spectrometry-Based Lipidomics Methods and Protocols Edited by Fong-Fu Hsu Mass Spectrometry Resource, Division of Endocrinology, Metabolism, and Lipid Research, Department of Medicine, Washington University School of Medicine, St. Louis, MO, USA Editor Fong-FuHsu MassSpectrometryResource DivisionofEndocrinology Metabolism,andLipidResearch DepartmentofMedicine WashingtonUniversitySchoolofMedicine St.Louis,MO,USA ISSN1064-3745 ISSN1940-6029 (electronic) MethodsinMolecularBiology ISBN978-1-0716-1409-9 ISBN978-1-0716-1410-5 (eBook) https://doi.org/10.1007/978-1-0716-1410-5 ©SpringerScience+BusinessMedia,LLC,partofSpringerNature2021 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartofthematerialis concerned,specificallytherightsoftranslation,reprinting,reuseofillustrations,recitation,broadcasting,reproduction onmicrofilmsorinanyotherphysicalway,andtransmissionorinformationstorageandretrieval,electronicadaptation, computersoftware,orbysimilarordissimilarmethodologynowknownorhereafterdeveloped. Theuseofgeneraldescriptivenames,registerednames,trademarks,servicemarks,etc.inthispublicationdoesnotimply, evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevantprotectivelawsandregulations andthereforefreeforgeneraluse. Thepublisher,theauthors,andtheeditorsaresafetoassumethattheadviceandinformationinthisbookarebelievedto betrueandaccurateatthedateofpublication.Neitherthepublishernortheauthorsortheeditorsgiveawarranty, expressedorimplied,withrespecttothematerialcontainedhereinorforanyerrorsoromissionsthatmayhavebeen made.Thepublisherremainsneutralwithregardtojurisdictionalclaimsinpublishedmapsandinstitutionalaffiliations. ThisHumanaimprintispublishedbytheregisteredcompanySpringerScience+BusinessMedia,LLC,partofSpringer Nature. Theregisteredcompanyaddressis:1NewYorkPlaza,NewYork,NY10004,U.S.A. Preface Over the past decade, there have been tremendous advancements in mass spectrometric techniquesinlipididentificationandquantification.Thisbookpresentsanaccountofthese advances.InthisissueoftheMethodsinMolecularBiologyseries,20chaptersareassembled coveringconventionalMS-based“shotgunlipidomics”bywhichsamplesareintroducedby infusionorloopinjection,aswellasLC-MS-basedlipidomics,whicharebecomingincreas- inglyimportantduetotheever-increasingdemandforacompleteandpreciselipidanalysis of the complex and diversified lipids in nature. This book includes protocols applying chemical reactions, online photochemical reactions combined with various MS methods forcomprehensivecharacterizationofvariouslipidclasses,andquantificationofspecificand rarelipids.Methodologieswithhyphenatedtechniques,suchasionmobility,andtechniques such as offline sample purification with TLC, SPE, and semi-preparative LC for separating lipidsfromvariousbiological specimensarealsoincluded. Ofimportance,pertinentexam- ples that highlight the key role of the state-of-the-art MS methods employing ESI high resolutionMSn(n¼2,3)massspectrometrytoprofilethelipidomeofthemodelorganism from eukaryotic and bacterial systems for biological researches, and the traditional triple quadrupole and MALDI-TOF-TOF mass spectrometry for quantitative and qualitative analysis of specific lipid classes, as well as MALDI-TOF for imaging, are all covered in the book. This book is a collection of the expertise of many contributors in their fields. It is hopedthatthebookisusefulforbiochemistsandmassspectroscopistswhoareinterestedin lipid studies. It is noteworthy that various nomenclature systems have been used, and the abbreviations, nomenclatures, and lipid classification published by LIPID MAPS consor- tium[1]with/withoutmodificationareadoptedinthisbook. St.Louis,MO,USA Fong-FuHsu Reference 1. FahyEetal(2005)Acomprehensiveclassificationsystemforlipids.JLipidRes46(5):839–861 v Contents Preface ..................................................................... v Contributors................................................................. ix 1 MassSpectrometry-BasedLipidomics:AnOverview ........................ 1 Fong-FuHsu 2 HighConfidenceShotgunLipidomicsUsingStructurallySelective IonMobility-MassSpectrometry.......................................... 11 BaileyS.Rose,KatrinaL.Leaptrot,RachelA.Harris, StacyD.Sherrod,JodyC.May,andJohnA.McLean 3 GlobalLipidomicsProfilingbyaHighResolutionLC-MSPlatform .......... 39 ThomasZu¨llig,MartinTrötzmu¨ller,andHaraldC.Köfeler 4 ComprehensiveStructuralCharacterizationofLipids byCouplingPaterno`–Bu¨chiReactionandTandemMassSpectrometry........ 53 QingyuanHu,YuXia,andXiaoxiaoMa 5 ChemicalDerivatization-AidedHighResolutionMassSpectrometry forShotgunLipidomeAnalysis ........................................... 61 VinzenzHofferek,HuaqiSu,andGavinE.Reid 6 QuantitativeAnalysisofPolyphosphoinositide,Bis(monoacylglycero) phosphate,andPhosphatidylglycerolSpeciesbyShotgunLipidomics AfterMethylation....................................................... 77 MeixiaPan,ChaoQin,andXianlinHan 7 MassSpectrometry-BasedShotgunLipidomicsUsingCharge-Switch DerivatizationforAnalysisofComplexLong-ChainFattyAcids .............. 93 CherylFrankfaterandFong-FuHsu 8 One-PotExtractiveTransesterificationofFattyAcidsFollowed byDMOXDerivatizationforLocationofDoubleBonds UsingGC-EI-MS....................................................... 105 CharlesH.Hocart,AbdeljalilElHabti,andGabrielO.James 9 CeramideAnalysisbyMultipleLinked-ScanMassSpectrometry UsingaTandemQuadrupoleInstrument.................................. 123 Fong-FuHsu 10 ComprehensiveMouseSkinCeramideAnalysisonaSolid-Phase andTLCSeparationwithHigh-ResolutionMassSpectrometryPlatform ...... 139 Meei-HuaLin,JeffreyH.Miner,andFong-FuHsu 11 MassSpectrometricAnalysisofMeibomianGlandLipids .................... 157 JianzhongChen 12 QuantificationofPlasmaOxylipinsUsingSolid-PhaseExtraction andReversed-PhaseLiquidChromatography-TripleQuadrupole MassSpectrometry...................................................... 171 Guan-yuanChenandQibinZhang 13 TargetedLipidomicsofDrosophilamelanogasterDuringDevelopment ........ 187 EstherXueYiGohandXueLiGuan vii viii Contents 14 ShotgunLipidomicAnalysisofLeishmaniaCells............................ 215 KaiZhangandFong-FuHsu 15 CharacterizationoftheUncommonLipidFamilies inCorynebacteriumglutamicumbyMassSpectrometry...................... 227 RajuV.V.TatituriandFong-FuHsu 16 MassSpectrometricAnalysisofBioactiveSphingolipidsinFungi.............. 239 AshutoshSinghandMaurizioDelPoeta 17 AnalyticalMethodologiesforLipidomicsinHempPlant .................... 257 AndreaCerrato,AnnaLauraCapriotti,CarmelaMariaMontone, SaraElsaAita,GiuseppeCannazza,CinziaCitti, SusyPiovesana,andLaganàAldo 18 ShotgunBacterialLipidAAnalysisUsingRoutineMALDI-TOF MassSpectrometry...................................................... 275 Ge´raldLarrouy-Maumus 19 ImagingofPolarandNonpolarLipidsUsingDesorption ElectrosprayIonization/Post-photoionizationMassSpectrometry............ 285 ChengyuanLiu,FeiQi,andYangPan 20 Matrix-AssistedLaserDesorption/Ionization-MassSpectrometry ImagingofLipidsintheIschemicRatBrainSection:APracticalApproach .... 299 Hay-YanJ.Wang Index ...................................................................... 313 Contributors SARAELSAAITA • DepartmentofChemistry,UniversitàdiRoma“LaSapienza”,Rome,Italy LAGANA` ALDO • DepartmentofChemistry,UniversitàdiRoma“LaSapienza”,Rome,Italy; CNRNANOTEC,CampusEcotekne,UniversityofSalento,Lecce,Italy GIUSEPPE CANNAZZA • DepartmentofLifeSciences,UniversityofModenaandReggio Emilia,Modena,Italy;CNRNANOTEC,CampusEcotekne,UniversityofSalento, Lecce,Italy ANNALAURACAPRIOTTI • DepartmentofChemistry,UniversitàdiRoma“LaSapienza”, Rome,Italy ANDREA CERRATO • DepartmentofChemistry,UniversitàdiRoma“LaSapienza”, Rome,Italy GUAN-YUANCHEN • Center forTranslationalBiomedicalResearch,UniversityofNorth CarolinaatGreensboro,Kannapolis,NC,USA;GraduateInstituteofForensicMedicine, NationalTaiwanUniversity,Taipei,Taiwan JIANZHONGCHEN • DepartmentofOptometryandVisionScience,TheUniversityof AlabamaatBirmingham,Birmingham,AL,USA CINZIACITTI • DepartmentofLifeSciences,UniversityofModenaandReggioEmilia, Modena,Italy;CNRNANOTEC,CampusEcotekne,UniversityofSalento,Lecce,Italy MAURIZIODELPOETA • DepartmentofMicrobiologyandImmunology,StonyBrook University,StonyBrook,NY,USA;DivisionofInfectiousDiseases,StonyBrookUniversity, StonyBrook,NY,USA;VeteransAffairsMedicalCenter,Northport,NY,USA ABDELJALILELHABTI • ResearchSchoolofBiology,AustralianNationalUniversity, Canberra,ACT,Australia CHERYLFRANKFATER • DivisionofEndocrinology,Metabolism,andLipidResearch, DepartmentofMedicine,WashingtonUniversitySchoolofMedicine,St.Louis,MO,USA ESTHERXUEYIGOH • LeeKongChianSchoolofMedicine,NanyangTechnological University,Singapore,Singapore XUELIGUAN • LeeKongChianSchoolofMedicine,NanyangTechnologicalUniversity, Singapore,Singapore XIANLINHAN • BarshopInstituteforLongevityandAgingStudies,UniversityofTexas HealthScienceCenteratSanAntonio,SanAntonio,TX,USA;DepartmentofMedicine— Diabetes,UniversityofTexasHealthScienceCenteratSanAntonio,SanAntonio, TX,USA RACHELA.HARRIS • CenterforInnovativeTechnology,DepartmentofChemistry,Vanderbilt InstituteofChemicalBiology,VanderbiltInstituteforIntegrativeBiosystemsResearchand Education,Vanderbilt-IngramCancerCenter,VanderbiltUniversity,Nashville, TN,USA CHARLESH.HOCART • ResearchSchoolofBiology,AustralianNationalUniversity, Canberra,ACT,Australia;IsotopomicsinChemicalBiologyGroup,SchoolofChemistry andChemicalEngineering,ShaanxiUniversityofScienceandTechnology,Xi’an,China ix x Contributors VINZENZHOFFEREK • SchoolofChemistry,TheUniversityofMelbourne,Parkville, VIC,Australia FONG-FUHSU • MassSpectrometryResource,DivisionofEndocrinology,Metabolism,and LipidResearch,DepartmentofMedicine,WashingtonUniversitySchoolofMedicine,St. Louis,MO,USA QINGYUANHU • StateKeyLaboratoryofPrecisionMeasurementTechnologyand Instruments,DepartmentofPrecisionInstrument,TsinghuaUniversity,Beijing,China GABRIEL O.JAMES • ResearchSchoolofBiology,AustralianNationalUniversity,Canberra, ACT,Australia HARALD C.KO¨FELER • CoreFacilityMassSpectrometry,MedicalUniversityofGraz, Graz,Austria GE´RALD LARROUY-MAUMUS • MRCCentreforMolecularBacteriologyandInfection, DepartmentofLifeSciences,FacultyofNaturalSciences,ImperialCollegeLondon, London,UK KATRINAL.LEAPTROT • Center forInnovativeTechnology,DepartmentofChemistry, VanderbiltInstituteofChemicalBiology,VanderbiltInstituteforIntegrativeBiosystems ResearchandEducation,Vanderbilt-IngramCancerCenter,VanderbiltUniversity, Nashville,TN,USA MEEI-HUALIN • DivisionofNephrology,DepartmentofMedicine,WashingtonUniversity SchoolofMedicine,St.Louis,MO,USA CHENGYUANLIU • NationalSynchrotronRadiationLaboratory,UniversityofScienceand TechnologyofChina,Hefei,China XIAOXIAOMA • StateKeyLaboratoryofPrecisionMeasurementTechnologyandInstruments, DepartmentofPrecisionInstrument,TsinghuaUniversity,Beijing,China JODY C.MAY • Center forInnovativeTechnology,DepartmentofChemistry,Vanderbilt InstituteofChemicalBiology,VanderbiltInstituteforIntegrativeBiosystemsResearchand Education,Vanderbilt-IngramCancerCenter,VanderbiltUniversity,Nashville, TN,USA JOHNA.MCLEAN • CenterforInnovativeTechnology,DepartmentofChemistry,Vanderbilt InstituteofChemicalBiology,VanderbiltInstituteforIntegrativeBiosystemsResearchand Education,Vanderbilt-IngramCancerCenter,VanderbiltUniversity,Nashville, TN,USA JEFFREYH.MINER • DivisionofNephrology,DepartmentofMedicine,Washington UniversitySchoolofMedicine,St.Louis,MO,USA;DepartmentofCellBiologyand Physiology,WashingtonUniversitySchoolofMedicine,St.Louis,MO,USA CARMELAMARIAMONTONE • DepartmentofChemistry,UniversitàdiRoma“LaSapienza”, Rome,Italy MEIXIAPAN • BarshopInstituteforLongevityandAgingStudies,UniversityofTexasHealth ScienceCenteratSanAntonio,SanAntonio,TX,USA YANGPAN • NationalSynchrotronRadiationLaboratory,UniversityofScienceand TechnologyofChina,Hefei,China SUSY PIOVESANA • DepartmentofChemistry,UniversitàdiRoma“LaSapienza”, Rome,Italy FEIQI • KeyLaboratoryforPowerMachineryandEngineeringofMinistryofEducation, ShanghaiJiaoTongUniversity,Shanghai,China CHAOQIN • BarshopInstituteforLongevityandAgingStudies,UniversityofTexasHealth ScienceCenteratSanAntonio,SanAntonio,TX,USA