Annual Plant Reviews Volume 40: Biochemistry of Plant Secondary Metabolism, Second Edition

477 Pages·2010·12.97 MB·English

fm BLBK250-Wink March3,2010 11:20 CharCount=
ANNUAL PLANT REVIEWS
VOLUME 40
Biochemistry of Plant Secondary Metabolism: Second Edition Edited by Michael Wink
© 2010 Blackwell Publishing Ltd. ISBN: 978-1-405-18397-0
i
fm BLBK250-Wink March3,2010 11:20 CharCount=
ANNUAL PLANT REVIEWS
VOLUME 40
Biochemistry of Plant
Secondary Metabolism
Second Edition
Edited by
Michael Wink
ProfessorofPharmaceuticalBiology
InstituteofPharmacyandMolecularBiotechnology
HeidelbergUniversity
Germany
A John Wiley & Sons, Ltd., Publication
iii
fm BLBK250-Wink March3,2010 11:20 CharCount=
Thiseditionfirstpublished2010
(cid:1)c 2010BlackwellPublishingLtd.
BlackwellPublishingwasacquiredbyJohnWiley&SonsinFebruary2007.Blackwell’s
publishingprogrammehasbeenmergedwithWiley’sglobalScientific,Technical,and
MedicalbusinesstoformWiley-Blackwell.
Registeredoffice
JohnWiley&SonsLtd,TheAtrium,SouthernGate,Chichester,WestSussex,PO198SQ,
UnitedKingdom
Editorialoffices
9600GarsingtonRoad,Oxford,OX42DQ,UnitedKingdom
2121StateAvenue,Ames,Iowa50014-8300,USA
Fordetailsofourglobaleditorialoffices,forcustomerservicesandforinformationabout
howtoapplyforpermissiontoreusethecopyrightmaterialinthisbookpleaseseeour
websiteatwww.wiley.com/wiley-blackwell.
Therightoftheauthortobeidentifiedastheauthorofthisworkhasbeenassertedin
accordancewiththeUKCopyright,DesignsandPatentsAct1988.
Allrightsreserved.Nopartofthispublicationmaybereproduced,storedinaretrieval
system,ortransmitted,inanyformorbyanymeans,electronic,mechanical,
photocopying,recordingorotherwise,exceptaspermittedbytheUKCopyright,Designs
andPatentsAct1988,withoutthepriorpermissionofthepublisher.
Wileyalsopublishesitsbooksinavarietyofelectronicformats.Somecontentthat
appearsinprintmaynotbeavailableinelectronicbooks.
Designationsusedbycompaniestodistinguishtheirproductsareoftenclaimedas
trademarks.Allbrandnamesandproductnamesusedinthisbookaretradenames,
servicemarks,trademarksorregisteredtrademarksoftheirrespectiveowners.The
publisherisnotassociatedwithanyproductorvendormentionedinthisbook.This
publicationisdesignedtoprovideaccurateandauthoritativeinformationinregardtothe
subjectmattercovered.Itissoldontheunderstandingthatthepublisherisnotengaged
inrenderingprofessionalservices.Ifprofessionaladviceorotherexpertassistanceis
required,theservicesofacompetentprofessionalshouldbesought.
LibraryofCongressCataloging-in-PublicationData
Biochemistryofplantsecondarymetabolism/editedbyMichaelWink.–2nded.
p.cm.–(Annualplantreviews;v.40)
Includesbibliographicalreferencesandindex.
ISBN978-1-4051-8397-0(hardback:alk.paper) 1.Plants–Metabolism.
2.Metabolism,Secondary. 3.Botanicalchemistry. I.Wink,Michael.
QK881.B542010
572(cid:1).42–dc22 2009038730
AcataloguerecordforthisbookisavailablefromtheBritishLibrary.
(cid:2)
Setin10/12ptPalatinobyAptaraR Inc.,NewDelhi,India
PrintedinSingapore
1 2010
iv
fm BLBK250-Wink March3,2010 11:20 CharCount=
AnnualPlantReviews
Aseriesforresearchersandpostgraduatesintheplantsciences.Eachvolume
inthisseriesfocusesonathemeoftopicalimportanceandemphasisisplaced
onrapidpublication.
EditorialBoard:
Prof.JeremyA.Roberts(Editor-in-Chief),PlantScienceDivision,Schoolof
Biosciences,UniversityofNottingham,SuttonBoningtonCampus,
Loughborough,Leicestershire,LE125RD,UK;
DrDavidEvans,SchoolofBiologicalandMolecularSciences,Oxford
BrookesUniversity,Headington,Oxford,OX30BP;
Prof.HidemasaImaseki,Obata-Minami2419,Moriyama-ku,Nagoya463,
Japan;
DrMichaelT.McManus,InstituteofMolecularBioSciences,Massey
University,PalmerstonNorth,NewZealand;
DrJocelynK.C.Rose,DepartmentofPlantBiology,CornellUniversity,
Ithaca,NewYork14853,USA.
Titlesintheseries:
1. Arabidopsis
EditedbyM.AndersonandJ.A.Roberts
2. BiochemistryofPlantSecondaryMetabolism
EditedbyM.Wink
3. FunctionsofPlantSecondaryMetabolitesandTheirExploitationin
Biotechnology
EditedbyM.Wink
4. MolecularPlantPathology
EditedbyM.DickinsonandJ.Beynon
5. VacuolarCompartments
EditedbyD.G.RobinsonandJ.C.Rogers
6. PlantReproduction
EditedbyS.D.O’NeillandJ.A.Roberts
7. Protein–ProteinInteractionsinPlantBiology
EditedbyM.T.McManus,W.A.LaingandA.C.Allan
8. ThePlantCellWall
EditedbyJ.K.C.Rose
9. TheGolgiApparatusandthePlantSecretoryPathway
EditedbyD.G.Robinson
10. ThePlantCytoskeletoninCellDifferentiationandDevelopment
EditedbyP.J.Hussey
11. Plant–PathogenInteractions
EditedbyN.J.Talbot
12. PolarityinPlants
EditedbyK.Lindsey
13. Plastids
EditedbyS.G.Moller
14. PlantPigmentsandTheirManipulation
EditedbyK.M.Davies
15. MembraneTransportinPlants
EditedbyM.R.Blatt
v
fm BLBK250-Wink March3,2010 11:20 CharCount=
16. IntercellularCommunicationinPlants
EditedbyA.J.Fleming
17. PlantArchitectureandItsManipulation
EditedbyC.G.N.Turnbull
18. Plasmodesmata
EditedbyK.J.Oparka
19. PlantEpigenetics
EditedbyP.Meyer
20. FloweringandItsManipulation
EditedbyC.Ainsworth
21. EndogenousPlantRhythms
EditedbyA.HallandH.McWatters
22. ControlofPrimaryMetabolisminPlants
EditedbyW.C.PlaxtonandM.T.McManus
23. BiologyofthePlantCuticle
EditedbyM.Riederer
24. PlantHormoneSignaling
EditedbyP.HaddenandS.G.Thomas
25. PlantCellSeparationandAdhesion
EditedbyJ.R.RobertsandZ.Gonzalez-Carranza
26. SenescenceProcessesinPlants
EditedbyS.Gan
27. SeedDevelopment,DormancyandGermination
EditedbyK.J.BradfordandH.Nonogaki
28. PlantProteomics
EditedbyC.Finnie
29. RegulationofTranscriptioninPlants
EditedbyK.Grasser
30. LightandPlantDevelopment
EditedbyG.Whitelam
31. PlantMitochondria
EditedbyD.C.Logan
32. CellCycleControlandPlantDevelopment
EditedbyD.Inz’e
33. IntracellularSignalinginPlants
EditedbyZ.Yang
34. MolecularAspectsofPlantDiseaseResistance
EditedbyJaneParker
35. PlantSystemsBiology
EditedbyG.CoruzziandR.Guti’errez
36. TheMossPhyscomitrellaPatens
EditedbyC.D.Knight,P.-F.PerroudandD.J.Cove
37. RootDevelopment
EditedbyTomBeeckman
38. FruitDevelopmentandSeedDispersal
EditedbyLarsØstergaard
39. FunctionandBiotechnologyofPlantSecondaryMetabolites
EditedbyM.Wink
40. BiochemistryofPlantSecondaryMetabolism
EditedbyM.Wink
vi
fm BLBK250-Wink March3,2010 11:20 CharCount=
CONTENTS
Contributors x
Preface xiii
1 Introduction:biochemistry,physiologyandecological
functionsofsecondarymetabolites 1
MichaelWink
1.1 Introduction 1
1.2 Biosynthesis 2
1.3 Transport,storageandturnover 9
1.4 Costsofsecondarymetabolism 13
1.5 Ecologicalroleofsecondarymetabolites 14
References 17
2 Biosynthesisofalkaloidsandbetalains 20
MargaretF.Roberts,DieterStrackandMichaelWink
2.1 Introduction 20
2.2 Nicotineandtropanealkaloids 23
2.3 Pyrrolizidinealkaloids(PAs) 33
2.4 Benzylisoquinolinealkaloids 35
2.5 Monoterpeneindolealkaloids(MIA) 46
2.6 Ergotalkaloids 56
2.7 Acridonealkaloidbiosynthesis 60
2.8 Purinealkaloids 61
2.9 Taxol 62
2.10 Betalains 66
2.11 Conclusions 75
References 75
3 Biosynthesisofcyanogenicglycosides,glucosinolatesand
non-proteinaminoacids 92
DirkSelmar
3.1 Introduction 93
3.2 Cyanogenicglycosides 94
3.3 Glucosinolates 128
3.4 Non-proteinaminoacids 146
Acknowledgements 157
References 157
vii
fm BLBK250-Wink March3,2010 11:20 CharCount=
viii (cid:1) Contents
4 Biosynthesisofphenylpropanoidsandrelatedcompounds 182
MaikePetersen,JoachimHansandUlrichMatern
4.1 Introduction 182
4.2 Generalphenylpropanoidpathwayandformationof
hydroxycinnamateconjugates 183
4.3 Coumarins 197
4.4 Lignans 209
4.5 Gallotanninsandellagitannins 223
4.6 Conclusion 229
References 230
5 Biochemistryofterpenoids:monoterpenes,sesquiterpenes
andditerpenes 258
MohamedAshour,MichaelWinkandJonathanGershenzon
5.1 Introduction 259
5.2 Function 260
5.3 Biosynthesis 263
5.4 Conclusions 285
References 286
6 Biochemistryofsterols,cardiacglycosides,brassinosteroids,
phytoecdysteroidsandsteroidsaponins 304
WolfgangKreisandFriederMu¨ller-Uri
6.1 Introduction 305
6.2 Sterols 308
6.3 Cardiacglycosides 319
6.4 Brassinosteroids 336
6.5 Phytoecdysteroids 341
6.6 Steroidsaponinsandsteroidalkaloids 343
6.7 Conclusions 347
References 348
7 Chemotaxonomyseenfromaphylogeneticperspectiveand
evolutionofsecondarymetabolism 364
MichaelWink,FlaviaBotschen,ChristinaGosmann,HolgerScha¨fer
andPeterG.Waterman
7.1 Introduction 365
7.2 Establishmentofchemotaxonomyasaresearchdiscipline 365
7.3 Developmentsinsmallmoleculechemotaxonomyover
thepast35years 380
7.4 Molecularbiologyandplanttaxonomy 382
7.5 Comparisonbetweenpatternsofsecondarymetabolites
andmolecularphylogeny 383
fm BLBK250-Wink March3,2010 11:20 CharCount=
Contents (cid:1) ix
7.6 Evolutionofplantsecondarymetabolism 406
Acknowledgements 426
References 426
Index 434
Colorplatecanbefoundbetweenpages368and369.
fm BLBK250-Wink March3,2010 11:20 CharCount=
CONTRIBUTORS
MohamedAshour
InstituteofPharmacyandMolecularBiotechnology
HeidelbergUniversity
Heidelberg
Germany
FlaviaBotschen
InstituteofPharmacyandMolecularBiotechnology
HeidelbergUniversity
Heidelberg
Germany
JonathanGershenzon
Max-Planck-InstituteofChemicalEcology
Jena
Germany
ChristinaGosmann
InstituteofPharmacyandMolecularBiotechnology
HeidelbergUniversity
Heidelberg
Germany
JoachimHans
InstituteofPharmaceuticalBiology
Philips-UniversityMarburg
Marburg
Germany
WolfgangKreis
InstituteofBotanyandPharmaceuticalBiology
UniversityErlangen-Nu¨rnberg
Erlangen
Germany
x
fm BLBK250-Wink March3,2010 11:20 CharCount=
Contributors (cid:1) xi
UlrichMatern
InstituteofPharmaceuticalBiology
Philips-UniversityMarburg
Marburg
Germany
MaikePetersen
InstituteofPharmaceuticalBiology
Philips-UniversityMarburg
Marburg
Germany
MargaretF.Roberts
RetiredfromTheSchoolofPharmacy
UniversityofLondon
London
UnitedKingdom
HolgerScha¨fer
InstituteofPharmacyandMolecularBiotechnology
HeidelbergUniversity
Heidelberg
Germany
DirkSelmar
InstituteofPlantBiology
TechnicalUniversityBraunschweig
Braunschweig
Germany
DieterStrack
DepartmentofSecondaryMetabolism
InstituteofPlantBiochemistry
Halle
Germany
FriederMu¨ller-Uri
InstituteofBotanyandPharmaceuticalBiology
UniversityErlangen-Nu¨rnberg
Erlangen
Germany