P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome Plant Metabolism and Biotechnology Plant Metabolism and Biotechnology, First Edition. Edited by Hiroshi Ashihara, Alan Crozier, and Atsushi Komamine. © 2011 John Wiley & Sons, Ltd. Published 2011 by John Wiley & Sons, Ltd. ISBN: 978-0-470-74703-2 i sdfsdf P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome Plant Metabolism and Biotechnology Edited by HIROSHI ASHIHARA Department of Biological Sciences, Graduate School of Humanities and Sciences, Ochanomizu University, Tokyo, Japan ALAN CROZIER Plant Products and Human Nutrition Group, School of Medicine, College of Medical, Veterinary and Life Sciences, University of Glasgow, Glasgow, UK ATSUSHI KOMAMINE The Research Institute of Evolutionary Biology, Tokyo, Japan A John Wiley and Sons, Ltd., Publication iii P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome Thiseditionfirstpublished2011 (cid:2)C 2011JohnWiley&Sons,Ltd Registeredoffice JohnWiley&SonsLtd,TheAtrium,SouthernGate,Chichester,WestSussex,PO198SQ,UnitedKingdom Fordetailsofourglobaleditorialoffices,forcustomerservicesandforinformationabouthowtoapplyfor permissiontoreusethecopyrightmaterialinthisbook,pleaseseeourwebsiteatwww.wiley.com. 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PrintedinGreatBritainbyAntonyRoweLtd,Chippenham,Wiltshire iv P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome Contents ListofContributors xiii Preface xv 1 BiosynthesisandMetabolismofStarchandSugars 1 FrederikBo¨rnkeandSophiaSonnewald 1.1 Introduction 1 1.2 CarbonPartitioninginMesophyllCells 2 1.3 SucroseBiosynthesisinSourceLeaves 3 1.3.1 RegulatoryEnzymesofthePathway 4 1.4 StarchMetabolisminSourceLeaves 7 1.4.1 StarchSynthesiswithintheChloroplast 7 1.4.2 StarchBreakdowninLeavesandMetabolismofitsDegradation ProductsintheCytosol 9 1.5 SucrosetoStarchConversioninStorageOrgans 12 1.6 MetabolicEngineeringofCarbohydrateMetabolism 14 1.6.1 IncreasingStarchContent 14 1.6.2 AlteringStarchQuality 15 1.7 EngineeringSolubleSugars 16 1.8 ProductionofNovelCarbohydratesinTransgenicPlants 17 1.9 NetworkAnalysisofCarbohydrateMetabolism 18 Acknowledgements 19 References 19 2 LipidBiosynthesis 27 DavidHildebrand 2.1 Introduction 27 2.2 FattyAcidSynthesis 29 2.3 FattyAcidDesaturases 32 2.3.1 (cid:2)-9Desaturases 32 2.3.2 (cid:2)-12Desaturases 35 2.3.3 (cid:3)-3Desaturases 37 2.4 LipidSignals 38 2.5 Algae 38 2.6 MembraneSynthesis 39 2.7 TAGBiosynthesis 43 v P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome vi Contents 2.8 GeneticEngineeringofOilseedforIndustrialUses 46 2.9 PlantOilsasaRenewableResource 48 Acknowledgements 51 References 52 3 SymbioticNitrogenFixation 67 HiroshiKouchi 3.1 NitrogenFixingOrganismsandtheNitrogenaseSystem 67 3.1.1 NitrogenFixingMicroorganisms 67 3.1.2 TheNitrogenaseComplex 68 3.1.3 NifGenesandRegulation 69 3.2 SymbioticNoduleFormationinLegumePlants 70 3.2.1 InfectionandtheNodulationProcess 70 3.2.2 NodFactors,EarlySymbioticSignallingandtheRhizobial InfectionProcess 72 3.3 MutualInteractionsbetweenHostCellsandBacteroidsinLegume Nodules 76 3.3.1 DifferentiationofRhizobiaintoBacteroids 76 3.3.2 ProtectionoftheNitrogenaseSystemfromOxygeninRootNodules 78 3.3.3 MetaboliteExchangebetweenthePlantCellCytosolandBacteroids 79 3.4 MolecularGeneticApproachestotheHostRegulationofNitrogen Fixation 83 3.4.1 TheFix−Mutants:HostLegume-DeterminedIneffectiveNodules 83 3.4.2 MetabolicPartnershipsUnveiledbyFix−Mutants 87 3.4.3 PrematureSenescenceinFix−NodulesandSymbiosome Organisation 90 Acknowledgements 92 References 92 4 SulfurMetabolism 103 HidekiTakahashi 4.1 Introduction 103 4.2 SulfateTransport 104 4.2.1 SulfateTransportMechanisms 104 4.2.2 SulfateUptakeSystem 106 4.2.3 TransportofSulfatefromRootstoShoots 107 4.2.4 SubcellularTransportofSulfate 109 4.2.5 RedistributionofSulfur 109 4.2.6 RegulationofSulfateUptake 110 4.3 SulfateReduction 111 4.3.1 ATPSulfurylase 111 4.3.2 APSReductase 112 4.3.3 APSKinase 112 4.3.4 SulfiteReductase 113 4.3.5 RegulationofSulfateReduction 113 4.4 CysteineBiosynthesis 114 P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome Contents vii 4.4.1 O-Acetylserine(thiol)lyase 114 4.4.2 SerineAcetyltransferase 115 4.4.3 CysteineSynthaseComplex 116 4.5 MethionineBiosynthesis 117 4.5.1 BiosyntheticPathways 117 4.5.2 RegulationofMethionineBiosynthesis 118 4.6 RegulatorsforCoordinationofSulfurMetabolism 118 4.6.1 TranscriptionalRegulators 118 4.6.2 MicroRNA-395 119 4.6.3 OAS-MediatedRegulation 120 4.6.4 OutlookforApplication 120 References 121 5 NucleotideMetabolism 135 RitaZrennerandHiroshiAshihara 5.1 Introduction 135 5.2 PyrimidineMetabolism 136 5.2.1 DeNovoBiosyntheticPathway 136 5.2.2 BiosynthesisofThymidineNucleotides 138 5.2.3 SalvagePathways 139 5.2.4 Catabolism 140 5.2.5 SecondaryMetabolites 142 5.3 PurineMetabolism 142 5.3.1 DeNovoBiosyntheticPathway 142 5.3.2 SalvagePathways 145 5.3.3 Catabolism 146 5.3.4 SecondaryMetabolites 148 5.4 PyridineMetabolism 149 5.4.1 DeNovoBiosyntheticPathway 149 5.4.2 PyridineNucleotideCycle 149 5.4.3 SecondaryMetabolites 152 5.5 BiotechnologicalApproaches 152 5.5.1 NewHerbicideTargets 153 5.5.2 IncreasedGrowthbyIncreasedNucleotidePrecursorAvailability 154 5.5.3 IncreasedPotatoTuberYieldbyModulatingAdenylatePools 155 References 156 6 PurineAlkaloidMetabolism 163 HiroshiAshihara,ShinjiroOgitaandAlanCrozier 6.1 Introduction 163 6.2 ClassificationofPurineAlkaloids 166 6.3 OccurrenceofPurineAlkaloids 166 6.4 BiosynthesisofCaffeine 167 6.4.1 BiosyntheticPathwayfromPurineNucleotides 167 6.4.2 CaffeineBiosynthesisfromXanthosine 168 6.4.3 CellularLocalisationofCaffeineBiosynthesis 170 P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome viii Contents 6.5 CatabolismofCaffeine 171 6.6 PhysiologicalandEcologicalAspectsofPurineAlkaloidMetabolism inPlants 173 6.6.1 TissueAgeandCaffeineMetabolism 173 6.6.2 StressResponseofCaffeineBiosynthesis 173 6.6.3 EcologicalRoleofPurineAlkaloids 176 6.7 MetabolicEngineeringofCaffeineInPlanta 176 6.7.1 TissueCultureTechnologiesofCoffeePlants 177 6.7.2 SuppressionofCaffeineBiosynthesisinCoffeePlants 177 6.7.3 ProductionofCaffeineinTobaccoPlants 180 6.7.4 ConstructionofTransgenicCaffeine-ProducingTobaccoPlants 180 6.7.5 RepellingEffectsonTobaccoCutworms 181 6.7.6 Perspectives 183 References 184 7 NicotineBiosynthesis 191 TsubasaShojiandTakashiHashimoto 7.1 Introduction 191 7.2 PathwaysandEnzymes 192 7.2.1 PyrrolidineFormation 193 7.2.2 PyridineFormation 195 7.2.3 CouplingofthePyrrolidineandPyridineRings 197 7.2.4 NornicotineFormation 198 7.2.5 AnabasineandAnatabineFormation 199 7.3 CompartmentationandTrafficking 200 7.3.1 Long-DistanceTransportfromRootstoLeaves 200 7.3.2 Cell-SpecificNicotineBiosynthesisinRoots 202 7.3.3 NicotineTransportersInvolvedinVacuolarSequestration 202 7.4 GeneRegulation 203 7.4.1 Jasmonate 203 7.4.2 Ethylene 206 7.4.3 Auxin 206 7.4.4 NICRegulatoryGenes 206 7.5 MetabolicEngineering 207 7.6 RecentDevelopments 208 7.7 Summary 208 References 208 8 TerpenoidBiosynthesis 217 Dae-KyunRo 8.1 Introduction 217 8.2 TerpenoidDiversity 218 8.3 MechanisticAspectsofTerpenoidBiogenesis 222 8.4 TerpeneSynthase–Structure,EvolutionandEngineering 223 8.5 TwoDistinctPathwaysforIsopentenylDiphosphate(IPP)Biosynthesis 225 P1:TIX/OTE/SPH P2:OTE JWST052-FM JWST052-Ashihara February18,2011 17:52 Printer:YettoCome Contents ix 8.5.1 Mevalonate(MVA)Pathway 225 8.5.2 MethylErythritolPhosphate(MEP)Pathway 227 8.6 SubcellularandCellularCompartmentalisationsofTerpenoid Metabolism 228 8.6.1 SubcellularLocalisationandMetabolicCross-Talkbetween MVAandMEPPathways 228 8.6.2 CellularCompartmentalisationofTerpenoidMetabolism 229 8.7 GeneClustersinTerpenoidMetabolism 230 8.8 MetabolicEngineeringofTerpenoidMetabolism 231 8.8.1 MicrobialMetabolicEngineering 232 8.8.2 PlantMetabolicEngineering 233 8.9 ConcludingRemarks 235 References 235 9 BenzylisoquinolineAlkaloidBiosynthesis 241 IsabelDesgagne´-PenixandPeterJFacchini 9.1 Introduction 241 9.2 Biosynthesis 242 9.2.1 (S)-Norcoclaurine 242 9.2.2 (S)-Reticuline 244 9.2.3 MorphinanAlkaloids 245 9.2.4 Sanguinarine 245 9.2.5 AporphineandProtoberberineAlkaloids 247 9.2.6 BisbenzylisoquinolineAlkaloidsandLaudanine 249 9.3 LocalisationandTransportofBenzylisoquinolineAlkaloidsandtheir BiosyntheticEnzymes 249 9.3.1 CellularandSubcellularLocalisation 249 9.3.2 Transport 251 9.4 Regulation 251 9.4.1 GeneRegulation 251 9.4.2 SignalTransduction 251 9.5 ApplicationtoBiotechnology 252 9.5.1 Mutagenesis 252 9.5.2 GeneticTransformationandMetabolicEngineering 252 9.5.3 MetabolicEngineering 254 9.6 Conclusions 254 References 254 10 MonoterpenoidIndoleAlkaloidBiosynthesis 263 VincenzoDeLuca 10.1 Introduction 263 10.2 MonoterpenoidIndoleAlkaloid(MIA)Biosynthesis 265 10.2.1 ContributionsofTwoSeparatePathwaysinMIAAssembly 265 10.2.2 GenesfortheBiosynthesisofSecologanin 266 10.2.3 MIABiosynthesisinCatharanthusRoseus 266
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