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SELECTED TOPICS IN THE CHEMISTRY OF NATURAL PRODUCTS 6389tp.indd 2 3/24/08 9:21:15 AM TThhiiss ppaaggee iinntteennttiioonnaallllyy lleefftt bbllaannkk SELECTED TOPICS IN THE CHEMISTRY OF NATURAL PRODUCTS EDITED BY RAPHAEL IKAN Emeritus Professor, Hebrew University of Jerusalem, Israel World Scientific NEW JERSEY • LONDON • SINGAPORE • BEIJING • SHANGHAI • HONG KONG • TAIPEI • CHENNAI 6389tp.indd 1 3/24/08 9:21:15 AM Published by World Scientific Publishing Co. Pte. Ltd. 5 Toh Tuck Link, Singapore 596224 USA office: 27 Warren Street, Suite 401-402, Hackensack, NJ 07601 UK office: 57 Shelton Street, Covent Garden, London WC2H 9HE British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. SELECTED TOPICS IN THE CHEMISTRY OF NATURAL PRODUCTS Copyright © 2008 by World Scientific Publishing Co. Pte. Ltd. All rights reserved. This book, or parts thereof, may not be reproduced in any form or by any means, electronic or mechanical, including photocopying, recording or any information storage and retrieval system now known or to be invented, without written permission from the Publisher. For photocopying of material in this volume, please pay a copying fee through the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, USA. In this case permission to photocopy is not required from the publisher. ISBN-13 978-981-270-569-3 ISBN-10 981-270-569-4 Typeset by Stallion Press Email: [email protected] Printed in Singapore. ChingTing - Selected Topics.pmd 1 2/14/2008, 2:57 PM Dec.11,2007 13:59 SPI-B530 SelectedTopicsintheChemistryofNaturalProducts Contents TomydearwifeYael,ourchildren,Amiram,Ariel,ArnonandEliana, theirspousesandourelevenlovelygrandchildren—allnaturalproducts. Dec.11,2007 13:59 SPI-B530 SelectedTopicsintheChemistryofNaturalProducts Contents TThhiiss ppaaggee iinntteennttiioonnaallllyy lleefftt bbllaannkk Dec.11,2007 13:59 SPI-B530 SelectedTopicsintheChemistryofNaturalProducts Contents Contents Preface ix Acknowledgments xi Contributors xiii Chapter1. TheOriginandtheNatureofNaturalProducts 1 RaphaelIkan Chapter2. Plant-Derived Natural Products in Drug Discovery andDevelopment:AnOverview 11 MarkBahar,YeDeng,JoshuaN.Fletcherand A.DouglasKinghorn Chapter3. Plant and Brain Cannabinoids: The Chemistry of MajorNewPlayersinPhysiology 49 LumirHanušandRaphaelMechoulam Chapter4. NaturalProductsasBiomarker Tracersin EnvironmentalandGeologicalProcesses 77 BerndR.T.Simoneit Chapter5. ToxinsofMarineInvertebratesandMicroorganisms 127 YoelKashmanandYehudaBenayahu Chapter6. Enantiomeric Distribution of Odorous Oxygenated MonoterpenesinAromaticPlants 155 UziRavid Chapter7. Recent Trends of Some Natural Sweet Substances fromPlants 189 BernardCrammer vii Dec.11,2007 13:59 SPI-B530 SelectedTopicsintheChemistryofNaturalProducts Contents viii Contents Chapter8. NaturalProductsforPestManagement 209 StephenO.Duke,AgnesM.Rimando,KevinK.Schrader, CharlesCantrell,KumudiniM.Meepagala, DavidE.Wedge,NurhayatTabanca,and FranckE.Dayan Chapter9. NaturalProductsinMycelialMicroorganisms: ImpactofMorphology 253 SergeiBraun Chapter10. RecentAdvancesintheChemistryof InsectPheromones 285 MangeshJ.GoundalkarandFrancisX.Webster Chapter11. NatureDerivedAntibiotics 351 SrinivasKodaliandJunWang Chapter12. NaturalProductsandRelatedCompoundsof RealizedandPotentialUsein Treating NeurodegenerativeDisease 377 PeterJ.HoughtonandMelanie-JayneHowes Chapter13. PhytotoxicCompoundswithCalmodulin InhibitorPropertiesfromSelectedMexican FungiandPlants 427 RachelMata,Sergio-MartínezLuisand AraceliPérez-Vasques Chapter14. PotentialAnticancerNaturalProductsfrom Plant-AssociatedFungi 471 MarilynT.MarronandA.A.LeslieGunatilaka Chapter15. PlantFungalEndophytes:Interactions,Metabolites andBiosyntheses 503 JohnR.Porter Index 581 Dec.11,2007 13:59 SPI-B530 SelectedTopicsintheChemistryofNaturalProducts Contents Preface Naturalproductscanbethoughtofasoriginatingfrommankind’scuriosity about odor, taste and cures for diseases, both in terrestrial and marine environments. Thestudyofnaturalproductshasalwaysbeenthestartingpointinthe discipline of chemistry worldwide.This observation is due to the impor- tanceoforganiccompoundsinagriculture,medicineandindustry. Nowadays,everystudentandscientistfeeltheneedtoacquirefurther knowledgeinthisfascinatingﬁeldwhichrevealsnatural“secrets.” Thebookcontains15chapterswhichcoverthefollowingtopics:The origin and nature of natural products; plant–derived natural products in drug discovery and development: an overview; plant and brain cannabinoids:thechemistryofmajornewplayersinphysiology;naturalproducts as biomarker tracers for environmental and geological processes; toxins of marine invertebrates and microorganisms; enantiometric composition of odorous oxygenated monoterpenes in aromatic plants; recent trends ofnaturalsweetsubstancesfromplants;naturalproductsforpestmanagement;naturalproductsinmycelialmicroorganisms:impactofmorphology; insects pheromones; natural products and related compounds of realized and potential use in treating neurodegenerative disease; phytotoxic com- poundswithcalmodulininhibitorpropertiesfromselectedMexicanfungi and plants, potential anticancer natural products from plant-anticancer fungi; plant fungal endophytes: interactions, metabolites and biosynthe- ses;antibiotics. The reviews were written by accomplished scientists, with extensive recordsintheirﬁelds.Thisbookisdevotedtomultidisciplinarystudiesof ix

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What is unique about this book? This book is intended for undergraduates, graduates and scientists in general. It introduces certain topics of natural products which are only taught in institutes of higher learning. Despite the fact that there exists a vast literature devoted principally or entirely