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FUNDAMENTALS OF PHARMACOGNOSY AND PHYTOTHERAPY CommissioningEditor:PaulineGraham DevelopmentEditor:FionaConn ProjectManager:SruthiViswam DesignDirection:CharlesGray IllustrationManager:MerlynHarvey FUNDAMENTALS OF PHARMACOGNOSY AND PHYTOTHERAPY S E C O N D E D I T I O N Michael Heinrich Dr rer nat habil MA(WSU) Dipl. Biol. FLS ProfessorandHead,CentreforPharmacognosyandPhytotherapy,UCLSchoolofPharmacy, UniversityofLondon,London,UK Joanne Barnes BPharm PhD MRPharmS FLS AssociateProfessorinHerbalMedicines,SchoolofPharmacy,UniversityofAuckland,Auckland,NewZealand Simon Gibbons BSc PhD CChem CSci FRSC FLS ProfessorofPhytochemistry,DepartmentofPharmaceuticalandBiologicalChemistry, UCLSchoolofPharmacy,UniversityofLondon,London,UK Elizabeth M. Williamson BSc(Pharm) PhD MRPharmS FLS ProfessorofPharmacy,SchoolofPharmacy,UniversityofReading,UK Foreword A. Douglas Kinghorn BPharmMSc PhD DScFRPharmS FAAASFAAPS FLS FSP ProfessorandJackL.BealChairofNaturalProductsChemistryandPharmacognosy,CollegeofPharmacy, TheOhioStateUniversity,Columbus,Ohio,USA Epilogue J. David Phillipson DScPhD MSc BSc(Pharm) FRPharmS FLS EmeritusProfessorofPharmacognosy,CentreforPharmacognosyandPhytotherapy,SchoolofPharmacy, UniversityofLondon,London,UK Illustrationsby DebbieMaizels and Simon Gibbons EDINBURGH LONDON NEW YORK OXFORD PHILADELPHIA ST LOUIS SYDNEY TORONTO 2012 © 2012ElsevierLtd.Allrightsreserved. Nopartofthispublicationmaybereproducedortransmittedinanyformorbyanymeans,electronicor mechanical,includingphotocopying,recording,oranyinformationstorageandretrievalsystem, withoutpermissioninwritingfromthepublisher.Detailsonhowtoseekpermission,further informationaboutthePublisher’spermissionspoliciesandourarrangementswithorganizationssuch astheCopyrightClearanceCenterandtheCopyrightLicensingAgency,canbefoundatourwebsite: www.elsevier.com/permissions. Thisbookandtheindividualcontributionscontainedinitareprotectedundercopyrightbythe Publisher(otherthanasmaybenotedherein). Firstedition2004 Secondedition2012 ISBN978-0-7020-3388-9 BritishLibraryCataloguinginPublicationData AcataloguerecordforthisbookisavailablefromtheBritishLibrary LibraryofCongressCataloginginPublicationData AcatalogrecordforthisbookisavailablefromtheLibraryofCongress Notices Knowledgeandbestpracticeinthisfieldareconstantlychanging.Asnewresearchandexperience broadenourunderstanding,changesinresearchmethods,professionalpractices,ormedicaltreatment maybecomenecessary. Practitionersandresearchersmustalwaysrelyontheirownexperienceandknowledgeinevaluating andusinganyinformation,methods,compounds,orexperimentsdescribedherein.Inusingsuch informationormethodstheyshouldbemindfuloftheirownsafetyandthesafetyofothers,including partiesforwhomtheyhaveaprofessionalresponsibility. Withrespecttoanydrugorpharmaceuticalproductsidentified,readersareadvisedtocheckthemost currentinformationprovided(i)onproceduresfeaturedor(ii)bythemanufacturerofeachproductto beadministered,toverifytherecommendeddoseorformula,themethodanddurationof administration,andcontraindications.Itistheresponsibilityofpractitioners,relyingontheirown experienceandknowledgeoftheirpatients,tomakediagnoses,todeterminedosagesandthebest treatmentforeachindividualpatient,andtotakeallappropriatesafetyprecautions. Tothefullestextentofthelaw,neitherthePublishernortheauthors,contributors,oreditors,assume anyliabilityforanyinjuryand/ordamagetopersonsorpropertyasamatterofproductsliability, negligenceorotherwise,orfromanyuseoroperationofanymethods,products,instructions,orideas containedinthematerialherein. The Publisher's policy is to use PrintedinChina paper manufactured from sustainable forests v Contents Foreword vii SECTION 3 NATURAL PRODUCT CHEMISTRY A.DouglasKinghorn Preface ix 6. Natural productchemistry 61 7. Methods innatural product chemistry 106 PART A FUNDAMENTALS OF PHARMACOGNOSY 1 8. Anticancer naturalproducts 129 SECTION 1 PHYTOTHERAPY AND SECTION 4 PHARMACEUTICALS AND PHARMACOGNOSY NUTRACEUTICALS DERIVED FROM PLANT EXTRACTS 1. Importance ofplants inmodernpharmacy and medicine 3 9. Production, standardization and quality control 144 2. Pharmacognosy and its history:people, plantsand naturalproducts 10 10. Toxicity ofherbalconstituents 162 11. What makes phytomedicines unique? 166 SECTION 2 BASIC PLANT BIOLOGY SECTION 5 MEDICINAL PLANTS IN SELECTED 3. General principles ofbotany: morphology HEALTHCARE SYSTEMS and systematics 25 4. Families yielding important 12. Traditionalsystems ofherbal medicine 175 phytopharmaceuticals 33 13. Complementary and Alternative medicine 189 5. Ethnobotany and ethnopharmacy 49 vi Contents 21. The musculoskeletalsystem 277 PART B IMPORTANT NATURAL PRODUCTS AND PHYTOMEDICINES USED IN PHARMACY AND MEDICINE 201 22. The skin 285 23. The eye 291 14. The gastrointestinal and biliary system 203 24. Ear,nose and orthopharynx 293 15. The cardiovascular system 219 25. Miscellaneous supportive therapies for stress, 16. The respiratorysystem 227 ageing, cancerand debility 296 17. The central nervoussystem 241 Epilogue – apersonal view 304 18. Infectiousdiseases 252 J.DavidPhillipson 19. The endocrinesystem 266 Index 311 20. The reproductive tract 274 vii Foreword Worldwide,drugsderivedfromorganismscontinue consumed ‘nonvitamin, nonmineral natural pro- tobeimportantforthetreatmentandpreventionof ducts’,amountingtothesumof$14.8billion.There- manydiseases.Pharmacognosy,whichisdefinedin fore, societal interest in pharmacognosy is likely to thisbookas‘thescienceofbiogenicornature-derived increaseinthefutureasthebiochemicalroleofphy- pharmaceuticals and poisons’, has been an estab- tomedicines, nutraceuticals and natural drugs in lished basic pharmaceutical science that has been generalbecomesmoreclearlydefined. taught in institutions of pharmacy education for Thissecondeditionofthisvolume,Fundamentalsof about two centuries. This subject area has changed PharmacognosyandPhytotherapy,byMichaelHeinrich, considerably since its initiation, having metamor- Joanne Barnes, Simon Gibbons and Elizabeth phosed from a largely descriptive botanical and Williamson, aims to provide a contemporary and mycologicalfieldinthelate19thandearly20thcentu- in-depthperspectiveofnaturalproduct drugsused ries,tohavingmoreofachemicalandbiologicalfocus in the practice of pharmacy. The book is organized withinthelast50yearsorso.Today,pharmacognosy intotwomajorparts,entitled‘Fundamentalsofphar- embraces the scientific study of compounds from macognosy’(PartA)and‘Importantnaturalproducts plants,animalsandmicrobes,ofbothterrestrialand andphytomedicinesusedinpharmacyandmedicine’ marineorigin,andhasevolvedrelativelyrecentlyto (PartB).PartAisdividedintofivesections,dealing,in also include phytotherapy and nutraceuticals. The turn,with:thehistoryandimportanceofpharmacog- teaching of pharmacognosy has become even more nosyand phytotherapyinpharmacyand medicine; relevant than previously over the last decade, as a relevant principles of botany and ethnobotany; the resultoftheincreasinguseofherbalremedies(phyto- chemistryofsecondarymetabolitesoforganismsper- medicines)bythepublicinEurope,NorthAmerica tinenttodrugtherapy;thecharacterizationandstan- and Australasia. When entering a pharmacy today dardization of phytomedicines and nutraceuticals; itbecomesapparentthatconsiderableshelfspaceis andtheuseofmedicinalplantsinOrientalandSouth devoted to a selection of ‘herbs’, to a degree which Asiansystemsof traditionalmedicine,aswellasin wouldhavebeenquiteunimaginableeven20years Western complementary and alternative medicine. ago.IftheUnitedStatesistakenasanexample,com- PartBprovidescoverageoftheuseofphytomedicines munity pharmacists nowadays have to deal with a in various therapeutic categories, affecting, respec- ratherbewilderingarrayofbotanical‘dietarysupple- tively: the gastrointestinal and biliary systems; the ments’,manyofwhichwereintroducedsoonafterthe cardiovascular system; the respiratory system; the passageoftheDietarySupplementHealthandEdu- centralnervoussystem;infectiousdiseases;theendo- cationActof1994.InamajorNationalHealthInter- crine system; the reproductive and urinary tracts; view Survey, commissioned by the Centers for the musculoskeletal system; the skin; the eyes; the DiseaseControlandPrevention(CDC),itwasfound ear,noseandpharynx;andmiscellaneoussupportive that in 2007 about 20% of the US adult population therapies. viii Foreword This comprehensive pharmacognosy textbook foruseincontinuingeducationcoursesbypharma- integrates effectively the traditional elements of cists, dentists, nurses and physicians. In addition, pharmacognosyandphytotherapy.Thefourtalented all those with a scientific interest in herbalism co-authors have been successful in this endeavour and complementary and alternative medicine will in large part because they have contributed their also find the content of value. The book will also collectivetechnicalexpertiseinseveraldiverseareas, serve as a reliable source of information on natural including ethnobotany and ethnopharmacology, product drugs for the informed lay reader. It is classical botanical pharmacognosy, natural product predicted that Fundamentals of Pharmacognosy and chemistry, phytochemistry, phytotherapy and clini- Phytotherapy will soon become a classic in its field. calpharmacy. This volume will be especially warmly welcomed This book may be confidently recommended for by educators of future pharmacists and of other purchase by undergraduate and professional doc- healthcare professionals. toral students in pharmacy, as well as beginning graduate students in programmes in the pharma- ProfessorA.DouglasKinghorn, ceutical sciences. It will also be of great interest Columbus,Ohio ix Preface In the last few decades pharmacognosy as an aca- accounts of alternative medicine systems such as demicdiscipline,anditsapplicationinhealthcare, medicalherbalism,traditionalChineseandAyurve- has changed almost beyond recognition. With the dicmedicine,aromatherapyandothers,andacom- revival of interest in natural drugs, phytotherapy prehensive section on plant drugs arranged into and herbal remedies, new courses are springing therapeuticcategories.Ourpurposeistoequipthe up to educate students of pharmacy, medicine, studentwiththeknowledgetoevaluatethesethera- medicalherbalism,nursingandrelatedprofessions. pies,usethemwhenlookingtodevelopdrugsand Knowledge about plant-derived products is essen- herbalproducts,andwhenadvisingthepatientwho tialinallareasofhealthcare,notonlybecausethese wishestotrythem. forms of treatment are a popular and widely used Natural product-derived drugs also include healthcare choice (often as over-the-counter pro- thoseproducedbybiotechnologyandfromanimal ducts), but also because of the importance of them and microbial sources, but we considered that, as inmanymedicaltraditions.Here,weaimtoprovide vast and important subjects in their own right, no a modern, therapy-oriented perspective, as well as comprehensivecoveragewaspossibleinthistext. an overview which any reader or educated lay- Chemical structures are included whenever person will find interesting and useful. This book necessary andappropriate, and wehope to encou- isnotaguidetotreatment,butatextbookpresenting rage students to appreciate the relevance of the the scientific principles and the evidence, where information they impart. In this new edition, we applicable, underpinning the use of herbal- and have increased the references and further reading otherplant-derivedmedicines. material in each section, so the reader can delve The content arose in part from the new lecture further into the subject, and consult the original courses developed by the authors, and is intended workfromwhichourinformationwastaken. tocoverallfundamentalaspectsofpharmacognosy Wethankallthosewhohavecontributedadvice, (thestudyofdrugsofnaturalorigin)aswellasadd- suggestionsandsupport,includingourcolleagues, ing topics on the therapeutic use of such drugs, andnotforgettingourfamiliesofcourse. which is phytotherapy. There is no other book which covers the subject of medicinal plants as an important element of contemporary health care in MichaelHeinrich,Lismore(Australia)and quitethiswayandwhichreflectsthecurrentpublic London(UK) interest in natural health care. We have combined JoanneBarnes,Auckland(NewZealand) sections on the scientific study of plant drugs – SimonGibbons,London(UK) phytochemistry,ethnopharmacyandbotany–with ElizabethM.Williamson,Reading(UK)