Natural Products: Phytochemistry, Botany and Metabolism of Alkaloids, Phenolics and Terpenes

4198 Pages·2013·56.54 MB·English

by  Eitaro Matsumura

Kishan Gopal Ramawat
Jean-Michel Mérillon
Editors
Natural Products
Phytochemistry, Botany and
Metabolism of Alkaloids,
Phenolics and Terpenes
1 3
Reference
Natural Products

Kishan Gopal Ramawat
Jean-Michel Me´rillon
Editors
Natural Products
Phytochemistry, Botany
and Metabolism of Alkaloids,
Phenolics and Terpenes
With1569Figuresand307Tables
Editors-in-Chief:
KishanGopalRamawat
BotanyDepartment,M.L.SukhadiaUniversity
Udaipur313001
India
Jean-MichelMe´rillon
Biological-ActivePlantSubstancesStudyGroup
UniversityofBordeaux
InstituteofVineandWineSciences
Villenaved’Ornon
France
ISBN978-3-642-22143-9 ISBN978-3-642-22144-6(eBook)
ISBN978-3-642-22145-3(Printandelectronicbundle)
DOI10.1007/978-3-642-22144-6
SpringerHeidelbergNewYorkDordrechtLondon
LibraryofCongressControlNumber:2013934974
#Springer-VerlagBerlinHeidelberg2013
Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof
the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations,
recitation,broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,andtransmissionor
informationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar
methodologynowknownorhereafterdeveloped.Exemptedfromthislegalreservationarebriefexcerpts
inconnectionwithreviewsorscholarlyanalysisormaterialsuppliedspecificallyforthepurposeofbeing
enteredandexecutedonacomputersystem,forexclusiveusebythepurchaserofthework.Duplication
ofthispublicationorpartsthereofispermittedonlyundertheprovisionsoftheCopyrightLawofthe
Publisher’s location, in its current version, and permission for use must always be obtained from
Springer.PermissionsforusemaybeobtainedthroughRightsLinkattheCopyrightClearanceCenter.
ViolationsareliabletoprosecutionundertherespectiveCopyrightLaw.
The use of general descriptive names, registered names, trademarks, service marks, etc. in this
publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt
fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse.
While the advice and information in this book are believed to be true and accurate at the date of
publication,neithertheauthorsnortheeditorsnorthepublishercanacceptanylegalresponsibilityfor
anyerrorsoromissionsthatmaybemade.Thepublishermakesnowarranty,expressorimplied,with
respecttothematerialcontainedherein.
Printedonacid-freepaper
SpringerispartofSpringerScience+BusinessMedia(www.springer.com)
Preface
We are pleased to present a five volume treatise on “Natural products:
phytochemistry,botanyandmetabolism”.Naturalproductsareasdiverseasplant
biodiversityanditwasaherculeantasktobringtogether severalhundredleading
scientistsdistributedallovertheworldtocontributeinthisproject.
This five volumes work on Natural Products is reference work providing
state-of-the-art knowledge composed by highly renowned scientists in their field.
The book is intended to serve the needs of graduate students, Ph.D. scholars,
researchersinthefieldofphytochemistry,botany,agriculturalsciences,pharmacy,
nutrition,biotechnology and,industrialscientists andthoseinvolved inmarketing
phytochemicals, plants and their extracts. The present reference work will
encompass the information about well established phytochemicals, biology and
biotechnology of medicinal plants or their products, their biosynthesis, novel
production strategies, demand and uses, metabolism and bioavailability. This
book is a work of tertiary literature containing digested knowledge in an easily
accessibleformat.
Useofmedicinalplantsisasoldashumancivilizationandcontinuouseffortsare
beingmadetoexplorenewandoldmedicinalplantsfornovelbioactivemolecules
ortoproducetheseproductsinhighamountsthroughmoderntechnologies.About
200,000 natural products of plant origin are known and many more are being
identified from higher plants and micro-organisms. Some plants based drugs are
usedsincecenturiesandtherearenotmanyalternativesforsomenaturaldrugsas
cardiac glycosides or morphine. Various facets of bioactive molecules have
developed very rapidly in the last two decades particularly due to newer tools of
isolationandidentificationaswellasrefinedmoleculartechniquestoestablishthe
biologicalpropertiesofisolatedmolecules.Thisendeavouristotimelycompilethis
vastdatageneratedinrecentpast.Thisiswellreflectedin139chaptersrunningin
over 4000 pages of text and vast literature cited in each chapter. The readers will
findcomprehensiveinformationonalmostallbioactivemolecules.Whileplanning
thisbookourendeavourwastoincorporatearticlesthatcover theentire gamutof
bioactive molecules of all the three major classes, viz., alkaloids, phenolics and
terpenes.EachvolumeisfurtherdividedintosectionssuchasGeneralBiologyand
Biotechnology; Classes - Occurrence, Biosynthesis, Structure and Chemistry,
v
vi Preface
Distribution; Methods of Analysis; (para) Pharmacology and Bioavailability; and
NutraceuticalsandFunctionalFoods(inphenolics).
Some examples are sufficient to illustrate the spectrum of chapters in different
sectionssuchas:onalkaloids(Biotechnologyandgeneticengineeringforalkaloid
production, various classes of alkaloids e.g., Purine alkaloids, Ergot alkaloids,
Terpenoid indole alkaloids, Pharmacological effects of ephedrine, Lycopodium
alkaloids, Biological activities of pepper alkaloids, Neurotoxic alkaloids from
cyanobacteria, Prevention of brain disorders by nicotine, Opioids and pain
treatment, Ecological roles of alkaloids); on phenolics (Genetics of flavonoids,
Functional foods: Genetics, metabolome and engineering, phytonutrient levels,
Cocoa cultivation, directed breeding and polyphenolics, classes of phenolics,
Polyphenols and anticancer activity, Tannins and anthocyanins of wine:
phytochemistry and organoleptic properties, Polyphenols and beer quality, Wine
polyphenols and vascular protective effects, Isoflavonoids and phytoestrogenic
activity,Functionalgrapes,Potentialneuroprotectiveactionsofdietaryflavonoids,
Prospects of functional foods / nutraceuticals and markets), and on terpenes (Ter-
penes:Chemistry,biologicalroleandtherapeuticapplications, Biotransformation
of terpenoids and steroids, Production and genetic engineering of terpenoids pro-
ductioninplantcellculturesandorgancultures,Taxol-producingfungi,Metabolic
engineeringofisoprenoidsbiosynthesis,classesofterpenes,Cannabinoids:Chem-
istry and Medicine, Phytosterols: Beneficial effects, Ginsenosides: Biological
activities, Ginkgolides and neuroprotective effects, Quassinoids: Anti-cancer and
antimalarial activities, Phytoecdysteroids: phytochemistry and pharmacological
activity,Brassinosteroidsandtheirbiologicalactivity,andsoon).
These compounds exhibit various ecological functions, provide protection
against attack by herbivores and microbes, and serve as attractants for pollinators
and seed-dispersing agents. Natural products are explored as sources of drugs,
flavouring agents, fragrances and for a wide range of therapies. Rapid progress
has been made inrecent yearsin understanding natural productaccumulationand
synthesis, and regulation and functions. It is timely to bring this information
together with contemporary advances in chemistry, plant biology, ecology, and
pharmacologyandmetabolismofnaturalproductsintheformofacomprehensive
treatiseonnaturalproducts.
Because of the voluminous work for the treatise, this project was spread over
almost two years, from concept to print. We would like to acknowledge
cooperation, patient and support of our contributors who have put their serious
effortstoensurethehighscientificqualityofthisbookwithuptodateinformation.
ThisworkcouldnotbecompletedwithoutactivesupportofSpringerteamwho
took pains in streamlining the production process. We are particularly indebt to
Drs. Marion Hertel, Lydia Muller, Sylvia Blago and Simone Giesler for their
continuoussupportfromveryinceptionoftheproject.
March2013 K.G.Ramawat
J.-M.Me´rillon
About the Editors
Professor (Dr.) K. G. Ramawat, Former Professor & Head Botany Department,
M.L.SukhadiaUniversity,Udaipur,India
Professor K. G. Ramawat did his Ph.D. (1978, Plant Biotechnology) from the
University of Jodhpur, India and joined as faculty member in January 1979.
He joined M.L.Sukhadia University as Associate Professor in 1991 and became
Professor in 2001. He served as Head, Department of Botany (2001-2004,
2010-2012), In charge, Department of Biotechnology (2003-2004), member task
forceonmedicinalandaromaticplants,DepartmentofBiotechnology,Government
of India, New Delhi (2002-2005) and co-ordinator UGC-DRS and DST-FIST
programmes (2002-2012). He did his Post-doctoral at the University of Tours,
France (1983-85) and subsequently worked as visiting professor at University of
Tours(1991)andUniversityofBordeaux2,France(1995,1999,2003,2006,2010).
He visited Poland under INSA-PAN academic exchange programme (2005).
During last 38 years of his career, he has published more than 170 peer reviewed
papers and articles. He has edited books on Biotechnology of medicinal plants,
secondary metabolites, Bioactive molecules, Herbal drugs, Plant defence:
biological control, Desert plants; published by Science Publishers Inc, Enfield,
USA and Springer Verlag, Germany. His research on recalcitrant woody legume
treesofdesert(Prosopis,Zizyphus,Commiphora),productionofusefulmetabolites
vii
viii AbouttheEditors
fromwoodyplants(Comiphora,Pueraria)wasfundedbyUGC,CSIR,ICAR,DBT
andDST,NewDelhi.Worksrelatedtouseofnovelgrowthmodulatorsandelicitors
on the production of guggulsterones, stibenes and isoflvonoids are well cited.
Hehassuperviseddoctoralthesisof25students.Heismemberofseveralacademic
bodies,associationsandeditorialboardsofjournals.
Professeur Jean-Michel Me´rillon, Directeur de l’EA 3675 (Groupe d’Etude des
Substances Ve´ge´tales a` Activite´ Biologique + Polyphe´nols Biotech), Faculte´ de
Pharmacie, Universite´ de Bordeaux, Institut des Sciences de la Vigne et du Vin,
Villenaved’Ornon,France
Professor J.M. Me´rillon received his M.Pharma. (1979) and Ph.D. (1984) from the
UniversityofToursinFrance.HejoinedtheUniversityofToursasassistantprofessor
in1981,becameassociateprofessorin1987,andafullprofessorin1993atthefaculty
ofPharmacy,UniversityofBordeaux,France.Heiscurrentlygroupleaderofa“study
group on biologically active plant substances” at the Institute of Vine and Wine
Sciences,whichcomprises25scientistsandresearchstudents.Hisgrouphasworked
for many years on phenolic compounds from vine and wine, mainly complex
stilbenes and their involvement in health. He has supervised the doctoral theses of
18 students. He has published more than 125 research papers in internationally
recognizedjournals.HehasanHindexof29accordingtotheanalysisofdocuments
publishedbetween1996and2013.Hehasco-editedfourbooksonsecondarymetab-
olites and biotechnology (Science Publishers, USA; Springer, Germany). He is
involvedindevelopingteachingonplantbiology,naturalbioactivecompoundsand
biotechnology.Hehastraveledwidelyasaseniorprofessor.Scientistsfromseveral
countriesareworkinginhislaboratoryandhisresearchissupportedbyfundingfrom
theAquitaineRegionalGovernment,theMinistryofHigherEducationandResearch,
and various private companies. He founded a technology transfer unit in 2004,
Polyphenols Biotech, providing support for R&D programs for SMEs and major
groupsfromthecosmetic,pharmaceutical,agriculturalandhealth-nutritionsectors.
Contents
Volume 1
PartI Alkaloids:GeneralBiologyandBiotechnology ........... 1
1 MicrobialProductionofPlantBenzylisoquinolineAlkaloids ... 3
EitaroMatsumura,MotokiMatsuda,FumihikoSato,and
HiromichiMinami
2 AlkaloidsofMarineMacroalgae ......................... 25
KasımCemalG€uven,BurakCoban,EkremSezik,
H€useyinErdugan,andFerdaKaleag˘asıog˘lu
3 NeurotoxicAlkaloidsfromCyanobacteria .................. 39
RalfKellmann,OlivierPloux,andBrettA.Neilan
4 BioproductionofTerpenoidIndoleAlkaloidsfromCatharanthus
roseusCellCultures ................................... 85
LorenaAlmagro,MarianaSottomayor,andMariaAngelesPedren˜o
5 BioactiveAlkaloidsfromSouthAmericanPsychotriaandRelated
Rubiaceae ........................................... 119
He´lioNittaMatsuura,DiogoDenardiPorto,andArthurGermano
Fett-Neto
6 EcologicalRoleofAlkaloids ............................. 149
ShailyGoyal
7 PlantInVitroSystemsasSourcesofTropaneAlkaloids ...... 173
VasilGeorgiev,AndreyMarchev,StrahilBerkov,and
AtanasPavlov
8 BiotechnologyandGeneticEngineeringfor
AlkaloidProduction ................................... 213
SmitaSrivastavaandAshokKumarSrivastava
9 MarinePyrroloiminoquinoneAlkaloids,Makaluvaminesand
Discorhabdins,andMarinePyrrole-ImidazoleAlkaloids ...... 251
HiromichiFujiokaandYasuyukiKita
ix