New Light on Alkaloid Biosynthesis and Future Prospects PDF
Preview New Light on Alkaloid Biosynthesis and Future Prospects
ADVANCES IN BOTANICAL RESEARCH Series Editors Jean-PierreJacquot Professeur, Membre deL’Institut UniversitairedeFrance, Unite´ Mixte deRecherche INRA,UHP1136“InteractionArbresMicroorganismes”,Universite´ deLorraine,Faculte´ des Sciences, Vandoeuvre, France PierreGadal HonoraryProfesseur,Universite´ Paris-SudXI,InstitutBiologiedesPlantes,Orsay,France AcademicPressisanimprintofElsevier 32JamestownRoad,LondonNW17BY,UK Radarweg29,POBox211,1000AEAmsterdam,TheNetherlands TheBoulevard,LangfordLane,Kidlington,Oxford,OX51GB,UK 225WymanStreet,Waltham,MA02451,USA 525BStreet,Suite1800,SanDiego,CA92101-4495,USA Firstedition2013 Copyright©2013ElsevierLtd.AllRightsReserved. Nopartofthispublicationmaybereproduced,storedinaretrievalsystemortransmittedin anyformorbyanymeanselectronic,mechanical,photocopying,recordingorotherwise withoutthepriorwrittenpermissionofthepublisher. 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ISBN:978-0-12-408061-4 ISSN:0065-2296 ForinformationonallAcademicPresspublications visitourwebsiteatstore.elsevier.com PrintedandboundinUK 13 14 15 16 17 10 9 8 7 6 5 4 3 2 1 CONTRIBUTORS HiroshiAshihara DepartmentofBiologicalSciences,OchanomizuUniversity,Otsuka,Bunkyo-ku,Tokyo, Japan Se´bastienBesseau EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France Fre´de´ricBourgaud Universite´ deLorraine;INRA,LaboratoireAgronomieetEnvironnement,UMR1121, ENSAIA,Vand(cid:1)uvre,andPlantAdvancedTechnologiesSA,Vand(cid:1)uvre,France Yong-EuiChoi DepartmentofForestResources,KangwonNationalUniversity,Chuncheon,Republic ofKorea YoungHaeChoi NaturalProductsLaboratory,InstituteofBiologyLeiden,LeidenUniversity,Leiden, TheNetherlands MarcClastre EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France VincentCourdavault EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France MartineCourtois EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France JoelCre`che EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France AlanCrozier SchoolofMedicine,CollegeofMedical,VeterinaryandLifeSciences,Universityof Glasgow,Glasgow,UnitedKingdom JohnC.D’Auria DepartmentofBiochemistry,MaxPlanckInstituteforChemicalEcology,Jena,Germany RebeccaDauwe PlantBiology&InnovationresearchUnitEA3900-UPJV,Universite´ dePicardieJules Verne,PRESUFECAP,FacultyofSciences,Ilotdespoulies,Amiens,France ix x Contributors ThomasDuge´ deBernonville EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France VincenzoDeLuca DepartmentofBiologicalSciences,BrockUniversity,St.Catharines,Ontario,Canada FranziskaDolke DepartmentofBioorganicChemistry,MaxPlanckInstituteforChemicalEcology,Jena, Germany EricDucos EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France ChristelleDutilleul EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France NathalieGiglioli-Guivarc’h EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France Gae¨lleGle´varec EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France GuiteleDaliaGoldhaber-Pasillas NaturalProductsLaboratory,InstituteofBiologyLeiden,LeidenUniversity,Leiden, TheNetherlands EricGontier PlantBiology&InnovationresearchUnitEA3900-UPJV,Universite´ dePicardieJules Verne,PRESUFECAP,FacultyofSciences,Ilotdespoulies,Amiens,andPlantAdvanced TechnologiesSA,Vand(cid:1)uvre,France NadineImbault EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France JanJirschitzka DepartmentofBiochemistry,MaxPlanckInstituteforChemicalEcology,Jena,Germany Yun-SooKim DepartmentofForestResources,KangwonNationalUniversity,Chuncheon,Republicof Korea ArnaudLanoue EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France EitaroMatsumura ResearchInstituteforBioresourcesandBiotechnology,IshikawaPrefecturalUniversity, Suematsu,Nonoichi,Ishikawa,Japan Contributors xi HiromichiMinami ResearchInstituteforBioresourcesandBiotechnology,IshikawaPrefecturalUniversity, Suematsu,Nonoichi,Ishikawa,Japan AkiraNakagawa ResearchInstituteforBioresourcesandBiotechnology,IshikawaPrefecturalUniversity, Suematsu,Nonoichi,Ishikawa,Japan ThiKhieuOanhNguyen PlantBiology&InnovationresearchUnitEA3900-UPJV,Universite´ dePicardieJules Verne,PRESUFECAP,FacultyofSciences,Ilotdespoulies,Amiens,France AudreyOudin EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France NicolasPapon EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France OlivierPichon EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France KazukiSaito GraduateSchoolofPharmaceuticalSciences,ChibaUniversity,Chuo-ku,Chiba,and RIKENCenterforSustainableResourceScience,Tsurumi-ku,Yokohama,Japan VonnySalim DepartmentofBiologicalSciences,BrockUniversity,St.Catharines,Ontario,Canada HiroshiSano ResearchandEducationCenterforGeneticInformation,NaraInstituteofScienceand Technology,Nara,Japan,andDepartmentofForestResources,KangwonNational University,Chuncheon,RepublicofKorea FumihikoSato DivisionofIntegratedLifeScience,GraduateSchoolofBiostudies,KyotoUniversity, Oiwake-cho,Kitashirakawa,Sakyo-ku,Kyoto,Japan SupaartSirikantaramas DepartmentofBiochemistry,FacultyofScience,ChulalongkornUniversity,Bangkok, Thailand BenoitSt-Pierre EA2106‘Biomole´culesetBiotechnologiesVe´ge´tales’,Universite´ Franc¸ois-Rabelaisde Tours,Tours,France RobertVerpoorte NaturalProductsLaboratory,InstituteofBiologyLeiden,LeidenUniversity,Leiden, TheNetherlands MamiYamazaki GraduateSchoolofPharmaceuticalSciences,ChibaUniversity,Chuo-ku,Chiba,Japan xii Contributors TakaoYokota DepartmentofBiosciences,TeikyoUniversity,Utsunomiya,Japan SergeyB.Zotchev DepartmentofBiotechnology,NorwegianUniversityofScienceandTechnology, Trondheim,Norway PREFACE Overthepastdecade,applicationsofhigh-throughputtechnologies,suchas expressed sequence tag databases, DNA microarrays, and proteome and metabolome analyses, have considerably accelerated the discovery of new componentsandmechanismsinvolvedintheassemblyofalkaloidsinplants. Combined with an intensive worldwide research programme and using several technical breakthroughs in biochemical, molecular, cellular, and physiological research, they have contributed to impressive advancements in our understanding of alkaloid biosynthesis. In particular, many enzymes actinginalkaloidbiosyntheticpathwayshavebeenidentifiedandcharacter- ized at the molecular level and numerous regulation processes have been also deciphered, highlighting the specific roles of phytohormones in the regulationofalkaloidbiosynthesisaswellasintheirtraffickingandstorage. Differentapproachesbasedonmicroscopyanalysishavealsocontributedto theelucidationofthecomplexandoriginalarchitecturesofalkaloidbiosyn- thetic pathways showing the distribution of the high number of enzymatic steps in different tissues but also in different subcellular compartments. Alkaloids classification, usually based on their chemical structure, is thus reassessedaccordingtoanewvisionoftheirmetabolismandbetterknowl- edgeoftheirbiologicalandecologicalactivities.Thiscomplexorganization canexplain,inpart,thedifficultiesencounteredintheattemptstoimprove alkaloid production in planta as well as the challenges to generate these products via chemical synthesis. Alkaloids have important biological activities, many of which have medicinal properties and are used in the treatment of human ailments, explaining our great interest not only in the identification of new natural molecules but also in the development of alkaloid production processes. Westillbelievethatthesealkaloids,anddrugsdevelopedfromthem,could bepartofourarsenalofmedicinesusedtocureseriousdiseasessuchascancer or AIDS. However, plants contain only low levels of alkaloids. Therefore, improving their production by chemical synthesis or by increasing natural synthesis in plants remains a challenge and motivates research in this field. Oneoftheultimategoalsofcurrentresearchistotransposepartoftherecent discoveries to the development of metabolic engineering strategies to overcometheusuallyverylowyieldofalkaloidproductioninplanta.Inthis context, we have witnessed, over the past 5 years, the emergence of new xiii xiv Preface processes including development of yeast or bacterial platforms for the fermentative production of plant alkaloids. The understanding of alkaloid biosynthetic pathways improves every year and there are now 12,000 natural compounds recognized as alkaloids, according to the discovery and the characterization of new natural mole- cules. Alkaloids present a relatively large prevalence in nature and are rela- tively common chemicals in all kingdoms of living organisms. More than 20%ofidentifiedplantsareabletoproducealkaloidsofoneformoranother. Thesealkaloidsshowaverylargedegreeofdiversitythatisatleastequivalent tothatobservedbetweentheplantspeciesthemselves.Thisstructuraldiver- sity is probably the result of specific biochemical differentiation over the course of evolutionary time which reflects changing interactions of mole- cules with biological targets leading to adaption of plants to their changing environment. Thus, in our quest to identify new bioactive molecules after havinglargelyexploredtheplantkingdom,wearenowgreatlyinterestedin marineorganisms.Indeed,ifseveralplant-derivedalkaloidsarenowclassed asleadingdrugsinthetreatmentofdifferenttypesofcancer,marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities suggesting exciting perspectives. Alkaloids have already been the subject of many books and academic works from various scientific fields. New Light on Alkaloid Biosynthesis and Future Prospects is intended to present different alkaloid families displaying the best characterized biosynthetic pathways and ecological role and the most advanced biotechnological developments. The book is divided into eleven chapters. Chapters 1 to 6 focus on plant alkaloid biosynthesis with aparticularemphasisonmonotepernoidindolealkaloids,tropanealkaloids, purine alkaloids and isoquinoline alkaloids. This presentation is completed bythechapter9whichaimsatpresentingthetechnologicaladvancesleading totheidentificationandthecharacterizationofnewalkaloidsandthechap- ter 10 which illustratesa distinctecological roleof alkaloids.Moreover the finalchapter11givesanoverviewofmarinealkaloidssinceveryinteresting discoveries have been recently made. Four chapters from 5 to 8 are more dedicated to the presentation of recent biotechnological developments leading to improvement in alkaloids production. Two of them present example(s) of the biotechnological production of camptothecin and the development of plant systems adapted to the production of specialized metabolites.Thetwoothersdescribethewaysusedtoimprovetheproduc- tionofisoquinolinealkaloidsbymetabolicengineeringintransgenicplants Preface xv or by usingan emerging concept of fermentative production of plant alka- loids by heterologous microbial systems. Inconclusion,Iwantedheretoacknowledgealltheauthorswhoagreed tosharetheirknowledgeonalkaloidsandtocontributetothisbookandalso thecolleaguesofmylaboratoryfortheirassistanceinthepreparationofthis book.Ihopeitwillbeofinterestnotonlyforresearchersbutalsoforstudents or anyone who is interested in the field of specialized metabolite research. NATHALIE GIGLIOLI-GUIVARC’H March 2013 CHAPTER ONE Towards Complete Elucidation of Monoterpene Indole Alkaloid Biosynthesis Pathway: Catharanthus roseus as a Pioneer System Vonny Salim, Vincenzo De Luca1 DepartmentofBiologicalSciences,BrockUniversity,St.Catharines,Ontario,Canada 1Correspondingauthor:e-mailaddress:[email protected] Contents 1. Introduction 2 2. DivisionofMIABiosynthesisPathway 5 2.1 Earlymonoterpenebiosynthesis 5 2.2 Iridoidbiosynthesis 10 2.3 EarlyMIAbiosynthesis 12 2.4 ThelateMIAbiosynthesispathway 16 3. OrganisationandSpatialSeparationofMIABiosynthesis 18 3.1 EpidermisasanimportantbiosyntheticsiteofMIAsandtheirprecursors 19 3.2 Theuseofepidermis-enrichedtranscriptomicresourcesforgenediscovery 20 4. Large-ScaleGenomicApproachesinFunctionalCharacterisationofGenesInvolved inMIABiosynthesis 21 4.1 ThesharedpathwaysamongApocynaceaefamily 21 4.2 Toolsforscreeningthecandidategenes 22 5. MetabolicEngineeringoftheMIABiosynthesisPathway 24 6. ConclusionsandPerspectives 27 Acknowledgements 29 References 29 Abstract The development of various plant-based engineering efforts has been facilitated by recentlarge-scaletranscriptomicresources.Inconsiderationoftheprogressinthestudy ofmonoterpeneindolealkaloid(MIA)metabolismachievedinthelastdecade,some strategieshavebeendevelopedformetabolicengineeringefforts.However,unidentified biosyntheticgenesinthepathwaylimitthispotential.Catharanthusroseusisthemost well-studiedmedicinalplantowingtoitsproductionofvaluableanticancerdimericMIAs such as vinblastine. This chapter highlights the cell-, organ-, development- and AdvancesinBotanicalResearch,Volume68 #2013ElsevierLtd 1 ISSN0065-2296 Allrightsreserved. http://dx.doi.org/10.1016/B978-0-12-408061-4.00001-8
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