Annual Plant Reviews Volume 39: Functions and Biotechnology of Plant Secondary Metabolites, Second edition

429 Pages·2010·2.34 MB·English

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ANNUAL PLANT REVIEWS
VOLUME 39
Functions and Biotechnology of Plant Secondary Metabolites, Second edition Edited by Michael Wink
© 2010 Blackwell Publishing Ltd. ISBN: 978-1-405-18528-8
i
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ANNUAL PLANT REVIEWS
VOLUME 39
Functions and Biotechnology
of Plant Secondary
Metabolites
Second edition
Edited by
Michael Wink
ProfessorofPharmaceuticalBiology
InstituteofPharmacyandMolecularBiotechnology
HeidelbergUniversity
Germany
A John Wiley & Sons, Ltd., Publication
iii
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Thiseditionfirstpublished2010
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LibraryofCongressCataloging-in-PublicationData
Functionsandbiotechnologyofplantsecondarymetabolites/editedby
MichaelWink.–2nded.
p.cm.–(Annualplantreviews;v.39)
Rev.ed.of:Functionsofplantsecondarymetabolitesandtheirexploitationinbiotechnology.
Includesbibliographicalreferencesandindex.
ISBN978-1-4051-8528-8(hardback:alk.paper)
1.Plantmetabolites. 2.Metabolism,Secondary. 3.Plantbiotechnology.
I.Wink,Michael. II.Functionsofplantsecondarymetabolitesandtheirexploitationin
biotechnology. III.Series:Annualplantreviews;v.39.
QK887.F862010
572’.42–dc22
2009031828
AcataloguerecordforthisbookisavailablefromtheBritishLibrary.
(cid:1)
Setin10/12ptPalatinobyAptaraR Inc.,NewDelhi,India
PrintedinSingapore
1 2010
iv
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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
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15. MembraneTransportinPlants
EditedbyM.R.Blatt
16. IntercellularCommunicationinPlants
EditedbyA.J.Fleming
17. PlantArchitectureandItsManipulation
EditedbyCGNTurnbull
18. Plasmodeomata
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
EditedbyDavidC.Logan
32. CellCycleControlandPlantDevelopment
EditedbyD.Inze´
33. IntracellularSignalinginPlants
EditedbyZ.Yang
34. MolecularAspectsofPlantDiseaseResistance
EditedbyJaneParker
35. PlantSystemsBiology
EditedbyGloriaM.CoruzziandRodrigoA.Gutie´rrez
36. TheMossPhyscomitrellapatens
EditedbyC.D.Knight,P.-F.PerroudandD.J.Cove
37. RootDevelopment
EditedbyTomBeeckman
38. FruitDevelopmentandSeedDispersal
EditedbyLarsØstergaard
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CONTENTS
Listofcontributors ix
Preface xi
1 Introduction 1
MichaelWink
1.1 Ecologicalfunctionofsecondarymetabolites 1
1.2 Presenceofdefenceandsignalcompoundsattheright
timeandplace 4
1.3 MolecularmodesofactionofSM 8
1.4 BiotechnologyandutilizationofSM 13
1.5 Conclusions 16
2 MolecularModesofActionofDefensiveSecondaryMetabolites 21
MichaelWinkandOskarSchimmer
2.1 Introduction 21
2.2 Molecularmodesofaction–anoverview 22
2.3 Accumulationofdefenceandsignalcompoundsinplants 128
2.4 Animalresponses:detoxificationmechanismsandadaptations 132
2.5 Concludingremarks 137
3 ChemicalDefenceinMarineEcosystems 162
AnnikaPutzandPeterProksch
3.1 Introduction 162
3.2 Marinenaturalproductsinallelopathicinteractions 165
3.3 Chemicaldefenceagainstfouling 168
3.4 Chemicaldefencesofmarineinvertebratesandalgae
againstconsumers 173
3.5 Favouredallocationofdefensivemetabolitesin
vulnerableandvaluablepartsofmarineinvertebrates
andalgae 182
3.6 Theflexibleresponse:stress-inducedaccumulationof
defencemetabolitesandactivationofprotoxins 186
3.7 Endosymbiontsassourcesforallelochemicalsfoundin
marineinvertebrates 193
3.8 Conclusionsandoutlook 201
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viii (cid:1) Contents
4 Plant–MicrobeInteractionsandSecondaryMetaboliteswith
Antibacterial,AntifungalandAntiviralProperties 214
Ju¨rgenReichling
4.1 Introduction 215
4.2 Phytoalexins 217
4.3 Antibacterialandantifungalagentsofhigherplants 232
4.4 Secondarymetabolitesfromhigherplantswith
antiviralproperties 278
4.5 Conclusions 317
5 NewMedicalApplicationsofPlantSecondaryMetabolites 348
Jo¨rgHeilmann
5.1 Introduction 349
5.2 Compoundswithanticancerandchemopreventiveactivity 349
5.3 Antiviralcompounds 359
5.4 Antimalarialdrugs 360
5.5 Anti-inflammatorydrugs 361
5.6 Antidepressantdrugs 363
5.7 Anti-ischaemicdrugs 364
5.8 Immunostimulatorydrugs 365
5.9 Conclusions 366
6 ProductionofNaturalProductsbyPlantCellandOrganCultures 381
August-WilhelmAlfermann
6.1 Introduction 381
6.2 Productionofnaturalproductsbycellandorgancultures 383
6.3 Elicitation 383
6.4 Increase/decreaseofproductyieldsbygeneticmanipulation 384
6.5 BiosyntheticpathwaysdelineationusingRNA-interference 385
6.6 Masscultivationofplantcellcultures 386
6.7 Productionofrecombinantproteinsbyplantsandplant
cellcultures 388
6.8 Productionofplantnaturalproductsinmicrobes 389
6.9 Perspectives 390
Index 399
Colourplate(betweenpages50and51)
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CONTRIBUTORS
August-WilhelmAlfermann
UniversityofDu¨sseldorf
InstituteofMolecularBiologyofPlants
Universita¨tsstr.1
40225Du¨sseldorf
Germany
Jo¨rgHeilmann
UniversityofRegensburg
FacultyofNaturalSciences
PharmaceuticalBiology
93040Regensburg
Germany
PeterProksch
UniversityofDu¨sseldorf
InstituteofPharmaceuticalBiologyandBiotechnology
Universita¨tsstr.1
40225Du¨sseldorf
Germany
AnnikaPutz
UniversityofDu¨sseldorf
InstituteofPharmaceuticalBiologyandBiotechnology
Universita¨tsstr.1
40225Du¨sseldorf
Germany
Ju¨rgenReichling
Ruprecht-Karls-UniversityHeidelberg
InstituteofPharmacyandMolecularBiotechnology
Div.Biology
ImNeuenheimerFeld364
69120Heidelberg
Germany
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x (cid:1) Listofcontributors
OskarSchimmer
Retiredfrom
UniversityErlangen-Nu¨rnberg
InstituteofBotanyandPharmaceuticalBiology
Erlangen
Germany
MichaelWink
Ruprecht-Karls-UniversityHeidelberg
InstituteofPharmacyandMolecularBiotechnology
Div.Biology
ImNeuenheimerFeld364
69120Heidelberg
Germany
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PREFACE
A characteristic feature of plants is their capacity to synthesize and store a
wide variety of low-molecular-weight compounds, the so-called secondary
metabolites (SM) or natural products. The number of described structures
exceeds100000;therealnumberinnatureiscertainlymuchhigherbecause
only 20–30% of plants have been investigated in phytochemistry so far. In
contrast to primary metabolites, which are essential for the life of every
plant,theindividualtypesofSMusuallyoccurinalimitednumberofplants,
indicatingthattheyarenotessentialforprimarymetabolism,i.e.anabolism
orcatabolism.
WhereasSMhadbeenconsideredtobewasteproductsorotherwiseuse-
less compounds for many years, it has become evident over the last three
decades that SM have important roles for the plants producing them: they
may function as signal compounds within the plant, or between the plant,
producing them and other plants, microbes, herbivores, predators of herbi-
vores, pollinating or seed-dispersing animals. More often SM serve as de-
fence chemicals against herbivorous animals (insects, molluscs, mammals),
microbes (bacteria, fungi), viruses or plants competing for light, water and
nutrients.Therefore,SMareultimatelyimportantforthefitnessoftheplant
producingthem.PlantsusuallyproducecomplexmixturesofSM,oftenrepre-
sentingdifferentclasses,suchasalkaloids,phenolicsorterpenoids.Itislikely
thattheindividualcomponentsofamixturecanexertnotonlyadditivebut
certainly also synergistic effects by attacking more than a single molecular
target.BecausethestructuresofSMhavebeenshapedandoptimisedduring
morethan500millionyearsofevolution,manyofthemexertinterestingbio-
logicalandpharmacologicalpropertieswhichmakethemusefulformedicine
orasbiorationalpesticides.
InthisvolumeofAnnualPlantReviews,wehavetriedtoprovideanup-
to-datesurveyofthefunctionofplantSM,theirmodesofactionandtheiruse
inpharmacologyasmolecularprobes,inmedicineastherapeuticagents,and
inagricultureasbiorationalpesticides.Acompanionvolume–Biochemistry
ofPlantSecondaryMetabolismeditedbyM.Wink–publishedsimultaneously
provides overviews of the biosynthetic pathways (enzymes, genes) leading
to the formation of alkaloids, glucosinolates, cyanogenic glucosides, non-
protein amino acids, flavonoids and other phenolics and terpenoids. The
mechanismsoftransportandstoragewerealsodiscussedaswellasageneral
outlineoftheevolutionofsecondarymetabolism.
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