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Plant and Food Carotenoids: Methods and Protocols PDF

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Methods in Molecular Biology 2083 Manuel Rodríguez-Concepción Ralf Welsch Editors Plant and Food Carotenoids 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 biomedicalprotocolpublishing.Eachprotocolisprovidedinreadily-reproduciblestep-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. Plant and Food Carotenoids Methods and Protocols Edited by Manuel Rodríguez-Concepción Centre for Research in Agricultural Genomics (CRAG), CSIC-IRTA-UAB-UB, Barcelona, Spain Ralf Welsch Institute for Biology II, University of Freiburg, Freiburg, Germany Editors ManuelRodr´ıguez-Concepcio´n RalfWelsch CentreforResearchinAgricultural InstituteforBiologyII Genomics(CRAG) UniversityofFreiburg CSIC-IRTA-UAB-UB Freiburg,Germany Barcelona,Spain ISSN1064-3745 ISSN1940-6029 (electronic) MethodsinMolecularBiology ISBN978-1-4939-9951-4 ISBN978-1-4939-9952-1 (eBook) https://doi.org/10.1007/978-1-4939-9952-1 ©SpringerScience+BusinessMedia,LLC,partofSpringerNature2020 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, expressorimplied,withrespecttothematerialcontainedhereinorforanyerrorsoromissionsthatmayhavebeenmade. Thepublisherremainsneutralwithregardtojurisdictionalclaimsinpublishedmapsandinstitutionalaffiliations. ThisHumanaimprintispublishedbytheregisteredcompanySpringerScience+BusinessMedia,LLC,partofSpringer Nature. Theregisteredcompanyaddressis:233SpringStreet,NewYork,NY10013,U.S.A. Preface Carotenoids are a large group of isoprenoid metabolites covering more than 600 com- pounds. A typical carotenoid molecule is a C40 hydrocarbon and forms a chromophore of doublebondsinconjugationwhichabsorbslightinthebluelightspectrum,thusappearing in colorsranging from yellowto orange and red.Although carotenoids areusually synthe- sized by photosynthetic organisms such as plants, animals including humans need to consumecarotenoidswiththeirdiet.Carotenoidspresentinourfoodareanessentialsource ofretinoidssuchasvitaminAandvisualpigments,buttheyarealsousedtoproduceother biologically active molecules that prevent degenerative diseases and promote health. In plants,thefunctionsofcarotenoidscoveralmostallaspectsinbiologicalsystems,including photosynthesis, protection against oxidative stresses, visual attraction, signaling, aroma composition,developmentalregulation,andmembranestabilization. Accordingly,researchoncarotenoidsdevelopedrapidlywithinthelastyears,supported bythedevelopmentofmethodssuitabletoanalyzecarotenoidcleavageproductsandalsoby numerous approaches succeeding in altering carotenoid amounts and patterns in various plant tissues and food sources. Associated with the development of these techniques, knowledge on the functions of carotenoids increased significantly and provided novel insights on how carotenoid biosynthesis is dynamically regulated in coordination with theirstorageanddegradationinplantcellsaswellasthecontributionofcarotenoidcleavage productsinnumerousprocessesinplantsandanimals. Thiscollectionofmethodsisintendedtoenablecarotenoidresearchintotheserecently extendedresearchareasandanswerquestionswhichnowcanbeasked.Themethodsarealso thoughttosupportresearchersapproachingcarotenoidfunctionsfromadifferentresearch area,whoarethusnewinthefieldorhaveonlylittleexperience.Accordingly,themethods are described with additional details of practical relevance usually not included in research publications,whicharethereforesometimesdifficulttotranslateintoreallablife.Wecovera wide spectrum of research aspects, including established protocols for carotenogenic and carotenoid-cleavageenzymecharacterizations,alargechapteronanalytical methodswhich meetstheneedofincreasingknowledgeoncataboliccarotenoidpathways,chaptersonhow both anabolic and catabolic pathways can be considered as well as a chapter on imaging carotenoid storage and carotenogenic metabolon formation in living systems. Finally, we included practical instructions on how carotenoid metabolism can be altered in model organismsandhowcarotenoidfunctioncanbeassessedinanimalsystems. Thismethodcollectionbuildsonthewillingnessofallcontributingauthorstoprovide theirdetailedlabprotocolsandmakethemavailabletoagreateraudiencewhichwehighly appreciate. These methods are intended to be used as reference methods to unify research methods and to allow carotenoid research to be extended into other fields of plant and animal research. We would like to thank John M. Walker for the invitation to create this volume of Methods in Molecular Biology and for his careful instructions on the way to finalizeit. Barcelona,Spain ManuelRodrı´guez-Concepci(cid:1)on Freiburg,Germany RalfWelsch v Contents Preface ..................................................................... v Contributors................................................................. xi PART I INTRODUCTION 1 PathwaysforCarotenoidBiosynthesis,Degradation,andStorage............. 3 TianhuSun,YaakovTadmor,andLiLi PART II ACTIVITIES 2 ASimpleInVitroAssaytoMeasuretheActivityofGeranylgeranyl DiphosphateSynthaseandOtherShort-ChainPrenyltransferases ............. 27 M.VictoriaBarjaandManuelRodrı´guez-Concepci(cid:1)on 3 Expression,Purification,andEnzymeActivityAssayofPhytoene SynthaseInVitro ....................................................... 39 MaurizioCamagnaandRalfWelsch 4 ImprovedExpressionandPurificationoftheCarotenoidBiosynthetic EnzymeZ-ISO ......................................................... 53 EleanoreT.WurtzelandJesu´sBeltra´n 5 DeterminationofInVitroandInVivoActivitiesofPlant CarotenoidCleavageOxygenases ......................................... 63 LourdesG(cid:1)omez-G(cid:1)omez,GianfrancoDiretto,OussamaAhrazem, andSalimAl-Babili 6 ExpressionandCharacterizationofMammalianCarotenoid CleavageDioxygenases .................................................. 75 LindaDoraThomas,SrinivasaganRamkumar, andJohannesvonLintig 7 Transportomicsfor theCharacterizationofPlantApocarotenoid TransmembraneTransporters............................................. 89 OliviaCostantinaDemurtas,RitadeBritoFrancisco, EnricoMartinoia,andGiovanniGiuliano PART III ANALYTICS 8 ApplicationsofVisibleSpectroscopyandColorMeasurementsin theAssessmentsofCarotenoidLevelsinFoods............................. 103 PaulaMapelli-Brahm,FranciscoJ.Rodrı´guez-Pulido,CarlaM.Stinco, FranciscoJ.Heredia,andAntonioJ.Mele´ndez-Martı´nez 9 ARoutineMethodfor theExtractionandHPLC-DADProfiling ofMajorPlantandFoodCarotenoids ..................................... 117 Da´masoHornero-Me´ndez vii viii Contents 10 AcquisitionofMassSpectrometryDataofCarotenoids:AFocus onBigDataManagement................................................ 135 AntonioPe´rez-Ga´lvez,IsabelViera,andMarı´aRoca 11 cis/transCarotenoidExtraction,Purification,Detection, Quantification,andProfilinginPlantTissues............................... 145 YagizAlagoz,NamrajDhami,ChrisMitchell, andChristopherI.Cazzonelli 12 DeterminationofPlantVolatileApocarotenoids............................ 165 Jose´L.RamblaandAntonioGranell 13 AMethodforExtractionandLC-MS-BasedIdentification ofCarotenoid-DerivedDialdehydesinPlants............................... 177 JianingMi,Kun-PengJia,AparnaBalakrishna, andSalimAl-Babili 14 FractionationofTomatoFruitChromoplasts............................... 189 Karel DePourcqandAlbertBoronat 15 QuantificationofStrigolactones .......................................... 199 CarlosRial,RosaM.Varela,Jose´M.G.Molinillo, AlexandraG.Dura´n,andFranciscoA.Macı´as 16 CarotenoidandApocarotenoidAnalysisbySFE-SFC-QqQ/MS.............. 209 DanieleGiuffrida,MariosimoneZoccali,andLuigiMondello PART IV IMAGING 17 ElucidatingCarotenoidBiosyntheticEnzymeLocalization andInteractionsUsingFluorescentMicroscopy ............................ 223 MariaShumskaya,RenaF.Quinlan,andEleanoreT.Wurtzel 18 VisualizationofCarotenoid-StorageStructuresinFruits byTransmissionElectronMicroscopy ..................................... 235 JoannaLado,JaimeZacarias,Marı´aJesu´sRodrigo, andLorenzoZacarı´as 19 LightMicroscopyandRamanImagingofCarotenoidsin PlantCellsInSituandinReleasedCaroteneCrystals ....................... 245 TomaszOleszkiewicz,MartaZ.Pacia,EwaGrzebelus, andRafalBaranski PART V DYNAMICS 20 CarotenoidIsotopologProfilingin13C-LabeledLeafExtracts byLC-MSandLC-FTICR-MS........................................... 263 Bj¨ornThieleandShizueMatsubara 21 QuantificationofCarotenoidPathwayFluxinGreenand NongreenSystems...................................................... 279 JulianKoschmiederandRalfWelsch 22 HistochemicalandMolecularQuantificationofArbuscular Mycorrhiza Symbiosis ................................................... 293 JuanM.Garcı´a,Marı´aJ.Pozo,andJuanA.L(cid:1)opez-Ra´ez Contents ix PART VI BIOTECHNOLOGY 23 UseofPotyvirusVectorstoProduceCarotenoidsinPlants .................. 303 Jose´-AntonioDaro`s 24 Agrobacteriumtumefaciens-MediatedStableTransformation ofDaucuscarota........................................................ 313 ChristianGonzalez-CalquinandClaudiaStange 25 CRISPR-Cas-MediatedGeneKnockoutinTomato ......................... 321 GwenSwinnen,ThomasJacobs,LaurensPauwels,andAlainGoossens 26 ModulationofActivityofaCarotenoidPathwayThroughthe UseoftheTeT-onRegulatorySystem:ApplicationintheFungus Fusariumfujikuroi...................................................... 343 JuliaMarente,PedroOrtega,JavierPardo-Medina,JavierAvalos, andM.CarmenLim(cid:1)on PART VII NUTRITION AND HEALTH 27 InterventionStudiesinHumans.......................................... 363 Begon˜aOlmedilla-Alonso 28 InVitroDigestionforControlandMonitoringofFoodEffects inRelationtoMicellarizationIndexofCarotenoids......................... 375 AntonioPe´rez-Ga´lvezandJavierFontecha 29 EvaluationofCarotenoidsProtectionAgainstOxidativeStress intheAnimalModelCaenorhabditiselegans................................ 387 PatriciaMartorell,SilviaLlopis,Jose´VicenteGil,SalvadorGenove´s, DanielRam(cid:1)on,LorenzoZacarı´as,andMarı´aJesu´sRodrigo 30 MouseModelstoStudyAntiobesogenicEffectsofCarotenoids .............. 403 JoanRibot,BojanStojnic,AndreuPalou,andM.LuisaBonet Index ...................................................................... 419 Contributors OUSSAMA AHRAZEM • DepartamentodeCienciayTecnologı´aAgroforestalyGene´tica, InstitutoBota´nico,UniversidaddeCastilla-LaMancha,Albacete,Spain YAGIZALAGOZ • HawkesburyInstitutefor theEnvironment,WesternSydneyUniversity, Penrith,NSW,Australia SALIMAL-BABILI • TheBioActivesLab,BiologicalandEnvironmentalSciencesand EngineeringDivision,KingAbdullahUniversityofScienceandTechnology(KAUST), Thuwal,KingdomofSaudiArabia JAVIERAVALOS • DepartamentodeGene´tica,FacultaddeBiologı´a,UniversidaddeSevilla, Seville,Spain APARNA BALAKRISHNA • TheBioActivesLab,BiologicalandEnvironmentalSciencesand EngineeringDivision,KingAbdullahUniversityofScienceandTechnology(KAUST), Thuwal,KingdomofSaudiArabia RAFALBARANSKI • FacultyofBiotechnologyandHorticulture,DepartmentofPlantBiology andBiotechnology,UniversityofAgricultureinKrakow,Krakow,Poland M.VICTORIABARJA • CentreforResearchinAgriculturalGenomics(CRAG),CSIC-IRTA- UAB-UB,Barcelona,Spain JESU´SBELTRA´N • DepartmentofBiologicalSciences,LehmanCollege,TheCityUniversityof NewYork,Bronx,NY,USA;TheGraduateSchoolandUniversityCenter-CUNY,New York,NY,USA;DepartmentofBotanyandPlantSciences,UniversityofCalifornia, Riverside,CA,USA M.LUISABONET • GrupdeRecercaNutrigeno`micaiObesitat,LaboratorideBiologia Molecular,Nutrici(cid:1)oiBiotecnologia(LBNB)oftheUniversitatdelesIllesBalears,CIBER deFisiopatologı´adelaObesidadyNutrici(cid:1)on(CIBERobn)andInstitutd’Investigaci(cid:1)o Sanit`ariaIllesBalears(IdISBa),PalmadeMallorca,Spain ALBERTBORONAT • CenterforResearchinAgriculturalGenomics(CSIC-IRTA-UAB-UB), Barcelona,Spain;DepartmentofBiochemistryandMolecularBiomedicine,Facultyof Biology,UniversityofBarcelona,Barcelona,Spain MAURIZIOCAMAGNA • GraduateSchoolofBioagriculturalSciences,NagoyaUniversity, Nagoya,Japan;FacultyofBiology,UniversityofFreiburg,Freiburg,Germany CHRISTOPHERI.CAZZONELLI • HawkesburyInstitutefor theEnvironment,WesternSydney University,Penrith,NSW,Australia JOSE´-ANTONIO DARO`S • InstitutodeBiologı´aMolecular yCelulardePlantas(Consejo SuperiordeInvestigacionesCientı´ficas-UniversitatPolite`cnicadeVale`ncia),Valencia, Spain RITADEBRITOFRANCISCO • DepartmentofPlantandMicrobialBiology,Universityof Zurich,Zurich,Switzerland OLIVIACOSTANTINADEMURTAS • ENEA,ItalianNationalAgencyforNewTechnologies, EnergyandSustainableEconomicDevelopment,C.R.Casaccia,Rome,Italy KARELDEPOURCQ • Center forResearchinAgriculturalGenomics(CSIC-IRTA-UAB- UB),Barcelona,Spain;DepartmentofBiochemistryandMolecularBiomedicine,Faculty ofBiology,UniversityofBarcelona,Barcelona,Spain NAMRAJDHAMI • HawkesburyInstitutefor theEnvironment,WesternSydneyUniversity, Penrith,NSW,Australia xi

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