Handbook of Marine Natural Products PDF
Preview Handbook of Marine Natural Products
Handbook of Marine Natural Products Ernesto Fattorusso William H. Gerwick Orazio Taglialatela-Scafati Editors Handbook of Marine Natural Products With691Figuresand45Tables Editors ErnestoFattorusso DipartimentodiChimicadelleSostanzeNaturali Universita`diNapoliFedericoII ViaMontesano49 80131Naples Italy WilliamH.Gerwick ScrippsInstitutionofOceanography SkaggsSchoolofPharmacyandPharmaceuticalSciences UniversityofCalifornia SanDiego,CA92093 USA OrazioTaglialatela-Scafati DipartimentodiChimicadelleSostanzeNaturali Universita`diNapoliFedericoII ViaMontesano49 80131Naples Italy ISBN:978-90-481-3833-3 Thispublicationisavailablealsoas: ElectronicpublicationunderISBN978-90-481-3834-0and PrintandelectronicbundleunderISBN978-90-481-3856-2 DOI:10.1007/978-90-481-3834-0 SpringerDordrecht,Heidelberg,NewYork,London LibraryofCongressControlNumber:2012934368 #SpringerScienceþBusinessMediaB.V.2012 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. Theuseofgeneraldescriptivenames,registerednames,trademarks,servicemarks,etc.inthispublication doesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevant protectivelawsandregulationsandthereforefreeforgeneraluse.Whiletheadviceandinformationinthis bookarebelievedtobetrueandaccurateatthedateofpublication,neithertheauthorsnortheeditorsnor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publishermakesnowarranty,expressorimplied,withrespecttothematerialcontainedherein. Printedonacid-freepaper SpringerispartofSpringerScienceþBusinessMedia(www.springer.com) Preface Thefieldofmarinenaturalproductsisnearingthe50yearmarksinceitsoriginin the1960swithpioneeringstudiesinJapanbyToshiIrieandintheUnitedStates by Paul Scheuer. Since that time and their early studies to describe the funda- mental organic chemistry of marine organisms, it has grown and evolved to be highly multidisciplinary, integrating methods development in organic structure analysis, pharmacology, synthetic and medicinal chemistry, toxicology, biosyn- thesis and mechanistic bioorganic chemistry, and genomics. Indeed, the field is reaching a maturity in approach and societal significance that could only be guessed at in the early days, and several marine-derived or marine-inspired drugs are now on the market (7) or in various stages of clinical trial (13). Of equal significance, more than 120 marine natural products are articles of com- merce for their utility as reference standards and pharmacologicalprobesof cell biology. However, with this maturity comes a responsibility on the part of students and researchers in the marine natural products sciences to know the history and origins of the field, and so enabled, to keep vital and current the subjectthroughinnovationandcreativenewscience. Anumberofreviewsandmulti-authormonographshaveappearedinthisfield with the primary objective of providing a scholarly perspective on some dimen- sionofmarinenaturalproductsaswellasanentrypointtotherelevantliterature. Most notably, the book series championed by Paul Scheuer and the yearly scholarly reviews by Faulkner and subsequently by the Munro and Blunt team haveservedourcommunitywellintheseregards.However,exceptforearlytexts by Scheuer and Pietra, and various specialty volumes such as that of Valerie Paul on Marine Chemical Ecology, comprehensive textbooks covering this field have not appeared which are suitable as an introduction to the field or a companion to an advanced undergraduate/graduate university course on the topic.Thishasbeenashortcomingwhichhasbothmadeteachingofthissubject difficultintheclassroomandcomplextoarticulatethescopeandnaturetothose outsideofthefield. Itiswiththisgoalandvisioninmindthattheeditorsfirstcametogetherin2008 ataMarineNaturalProductsGordonResearchConferenceinVentura,California, tobeginorganizing a textbook in thisfield of marine natural products science. At that time we outlined a volume of considerable scope, divided into six sections, which would provide a comprehensive overview of this highly diverse field. v vi Preface We next identified potential leaders in the field to provide chapters on specific topics within each of these sections. We were highly gratified that almost all contactedauthorswereabletoacceptourinvitationtocontributetothishandbook, and, subsequently, to receive their inspiring and scholarly chapters. Without the efforts and dedication of these many authors, this volume clearly would not have been possible, and we thank them all most sincerely. We believe that it was the shared vision of all of the authors that provided the motivation to contribute to atextbookthatwouldhelpdefinethefieldaswellasprovideacontemporaryguide tothoseenteringthisexcitingbranchofscience. A unique feature of this volume is the inclusion of a series of thought- provoking study questions at the end of each chapter. Some of these will aid in understanding the principles and concepts presented in each chapter, whereas others represent actual topics for further research. A careful consideration of these questions by interested students will certainly enhance the level of under- standingofthematerialpresentedaswellasstimulatenewideassuitableasactual researchprojects. Upon receipt of the various chapters the editors undertook the multistage process of editing, improving consistency between chapters, and identifying index terms. We thank the multitude of people at our respective institutions for their contributions to various aspects of this lengthy process. We also thank the several key people at Springer who have helped this volume become a reality. Andfinally,wethankourfamiliesfortheirunderstandingduringthemanyearly mornings and late evenings that we were engaged in the writing and editorial process.However,ifwereachourvisiontohaveprovidedatrulyusefultextfor thoseenteringthefieldofmarinenaturalproductsscience,then,indeed,itwillall havebeenworthwhile.Tothereadersofthisvolume,wesincerelywishthatyou willfindknowledge,perspective,andinspirationinyourscholarlypursuitofthe marinenaturalproductssciences.Wehopethatthisvolumewillassistyouasyou continuethetraditionofinnovationandcreativitythathascharacterizedthisfield overitsfirst50years. ErnestoFattorusso WilliamH.Gerwick OrazioTaglialatela-Scafati February2012 About the Editors ErnestoFattorusso DipartimentodiChimicadelleSostanze Naturali Universita` diNapoliFedericoII ViaMontesano49 80131Naples Italy Ernesto Fattorusso graduated in Chemistry in 1960 and got Libera Docenza in NaturalProductsChemistryin1967.HewasassistantprofessorattheUniversityof Naples(1963–1975);in1975,hebecamefullProfessorofOrganicChemistryatthe Faculty ofScience. In1980, hemoved tothe Faculty ofPharmacy, where he was electedDeantwice.Since2011,heisProfessorEmeritusofOrganicChemistryof the University of Naples Federico II. He has published more than 400 scientific papersandon2008editedthebookModernAlkaloids.Hisresearchactivitystarted bystudyingthestructureandbiogenesisofmelanins,and,sincetheendof1960s, hehaspioneeredthechemicalinvestigationofmarinemetabolites.Hehaswonthe A. Quilico Award (2002) of Italian Chemical Society, the P. Scheuer Award (2004) of Akademie of Erfurt, and the P. Scheuer Award (2010) of University of HonoluluFoundation.Since2005,heisEditorofSteroids. vii viii AbouttheEditors WilliamH.Gerwick ScrippsInstitutionofOceanography SkaggsSchoolofPharmacyand PharmaceuticalSciences UniversityofCalifornia SanDiego,CA92093 USA William Gerwick holds a Ph.D. from Scripps Institution of Oceanography, UniversityofCaliforniaSanDiego(1981)wherehedescribedtheuniqueorganic secondary metabolites of several marine macroalgae. His postdoctoral research focused on the biosynthesis of microbial natural products at the University of Connecticut. He was an assistant professor of Chemistry at the University of Puerto Rico in 1982–1983, and then professor of Pharmaceutical Sciences at the Oregon State University College of Pharmacy for over 20 years. In 2005, he returned as Full Professor to Scripps and the newly formed Skaggs School of Pharmacy and Pharmaceutical Sciences, UCSD, and in 2011 was named Distin- guished Professor of Oceanography and Pharmaceutical Sciences. He has served as president of the American Society of Pharmacognosy, a member for the NIH scientific review committee on natural products chemistry, and holds affiliate positions at several other universities and institutions around the world. In 2011, hewasawardedtheUCSanDiegoChancellor’sAssociatesAwardforExcellence in Engineering and Scientific Research. He has served on several scientific and reviewpanelsintheUSAandabroad,includinghiscurrentroleontheOceansand Human Health National Advisory Committee. His research fuses marine natural productsdrugdiscoveryresearchwithbiosyntheticinvestigationsatthechemical, biochemical, and genetic levels, and he has pioneered the integrated use of advancedanalyticalinstrumentationinthisareaofscientificresearch. AbouttheEditors ix OrazioTaglialatela-Scafati DipartimentodiChimicadelleSostanze Naturali Universita` diNapoliFedericoII ViaMontesano49 80131Naples Italy Orazio Taglialatela-Scafati holds a Ph.D. in Bioactive Natural Products (1997) from the University of Naples Federico II. He was appointed as Assistant ProfessorofOrganicChemistryin1999and,since2004,heisAssociateProfessor inOrganicChemistryatFacultyofPharmacy,UniversityofNaplesFedericoII. He has served on several scientific and review panels and he is member of the EditorialBoardofthescientificjournalsSteroidsandMarineDrugs.Hisresearch activityfocusesonisolation,stereostructuralelucidation,andsemi-synthetictrans- formation of bioactive secondary metabolites (especially with antitumor, antima- larial, and anti-inflammatory activities) from marine invertebrates and terrestrial plants. He is the author of about 100 research papers and the editor of the books FlavourandFragranceChemistryandModernAlkaloids.
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