loading

Logout succeed

Logout succeed. See you again!

ebook img

Progress in the Chemistry of Organic Natural Products Vol. 94 PDF

pages269 Pages
release year2011
file size7.174 MB
languageEnglish

Preview Progress in the Chemistry of Organic Natural Products Vol. 94

Progress in the Chemistry of Organic Natural Products Founded by L. Zechmeister Editors: A.D. Kinghorn, Columbus, OH H. Falk, Linz J. Kobayashi, Sapporo Honorary Editor: W. Herz, Tallahassee, FL Editorial Board: V.M. Dirsch, Vienna S. Gibbons, London N.H. Oberlies, Greensboro, NC Y. Ye, Shanghai 94 Progress in the Chemistry of Organic Natural Products Authors: S.S. Ebada, N. Lajkiewicz, J.A. Porco Jr, M. Li-Weber, and P. Proksch M.A.R.C. Bulusu, K. Baumann, and A. Stuetz R.I. Misico, V.E. Nicotra, J.C. Oberti, G. Barboza, R.R. Gil, and G. Burton SpringerWienNewYork Prof.A.DouglasKinghorn,CollegeofPharmacy, OhioStateUniversity,Columbus,OH,USA em.Univ.-Prof.Dr.H.Falk,Institutfu¨rOrganischeChemie, Johannes-Kepler-Universita¨t,Linz,Austria Prof.Dr.J.Kobayashi,GraduateSchoolofPharmaceuticalSciences, HokkaidoUniversity,Sapporo,Japan Thisworkissubjecttocopyright. Allrightsarereserved,whetherthewholeorpartofthematerialisconcerned,specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopyingmachinesorsimilarmeans,andstorageindatabanks. #2011Springer-Verlag/Wien SpringerWienNewYorkisapartof SpringerScienceþBusinessMedia springer.at ProductLiability:Thepublishercangivenoguaranteefortheinformationcontainedinthis book.Thisalsoreferstothatondrugdosageandapplicationthereof.Ineachindividualcase the respective user must check the accuracy of the information given by consulting other pharmaceuticalliterature.Theuseofregisterednames,trademarks,etc.inthispublication does not imply, even in the absence of a specific statement, that such names are exempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. Typesetting:SPI,Chennai Printedonacid-freeandchlorine-freebleachedpaper SPIN:80022757 With45(partlycoloured)Figuresand4colouredPlates ISSN0071-7886 ISBN978-3-7091-0747-8 e-ISBN 978-3-7091-0748-5 DOI10.1007/978-3-7091-0748-5 SpringerWienNewYork Contents Contributors ............................................................... ix ChemistryandBiologyofRocaglamides(¼Flavaglines) andRelatedDerivativesfromAglaiaSpecies(Meliaceae) .............. 1 SherifS.Ebada,NeilLajkiewicz,JohnA.PorcoJr., MinLi-Weber,andPeterProksch 1. Introduction .............................................................. 2 2. StructuralClassificationofRocaglamidesandRelated Compounds ............................................................... 5 2.1. RocaglamideDerivatives ........................................... 5 2.2. AglainDerivatives ................................................. 12 2.3. AglaforbesinDerivatives ........................................... 17 2.4. ForbaglineDerivatives ............................................. 18 3. BiosynthesisofRocaglamidesandRelatedMetabolites ............... 20 4. PharmacologicalSignificanceofRocaglamidesandRelated Compounds .............................................................. 23 4.1. InsecticidalActivity ................................................ 23 4.2. Anti-inflammatoryActivity ........................................ 26 4.3. AnticancerActivity ................................................ 28 5. ChemicalSynthesisofCyclopenta[b]benzofurans ..................... 34 5.1. FirstApproachestotheSynthesisofRocaglamides .............. 34 5.2. TheFirstTotalSynthesisofRocaglamide ......................... 36 5.3. SynthesesofRocaglamideandRelatedNaturalProducts ......... 37 5.4. NewApproachestoRocaglamideandRelated NaturalProducts ................................................... 39 5.5. SynthesesofSilvestrol ............................................. 44 5.6. DevelopmentofRocaglatesandAnaloguesasTherapeutic Agents .............................................................. 47 6. ConcludingRemarks .................................................... 51 References .................................................................. 51 v vi Contents ChemistryoftheImmunomodulatoryMacrolideAscomycin andRelatedAnalogues .................................................... 59 MurtyA.R.C.Bulusu,KarlBaumann,andAntonStuetz 1. Introduction ............................................................. 59 1.1. AscomycinandRelatedNaturalProducts ......................... 60 1.2. AscomycinDerivatives,aNovelClassofAnti-inflammatory Compounds ......................................................... 62 1.3. StructuralFeaturesofAscomycin ................................. 66 2. SynthesisAspects ....................................................... 70 2.1. SynthesisoftheFourDiastereomeric“Furano-Ascomycins” ..... 70 2.2. Synthesisof13CLabelledAscomycin ............................. 72 2.3. ReactivityoftheBindingDomain ................................. 75 2.4. ModificationsintheEffectorandCyclohexylDomains .......... 94 3. Summary ............................................................... 116 References ................................................................. 118 WithanolidesandRelatedSteroids ..................................... 127 RosanaI.Misico,VivianaE.Nicotra,JuanC.Oberti,GloriaBarboza, RobertoR.Gil,andGerardoBurton 1. Introduction ............................................................ 128 2. WithanolidesinthePlantKingdom ................................... 129 2.1. SolanaceousGeneraContainingWithanolides .................. 129 2.2. Non-SolanaceousGeneraContainingWithanolides ............. 132 3. ClassificationofWithanolides ......................................... 132 3.1. Withanolideswithad-Lactoneord-LactolSideChain ......... 132 3.2. Withanolideswithag-LactoneSideChain ...................... 134 4. WithanolideswithanUnmodifiedSkeleton ........................... 135 4.1. TheWithaniaWithanolides ...................................... 135 4.2. OtherWithanolideswithanUnmodifiedSkeleton .............. 143 5. WithanolideswithModifiedSkeletons ................................ 157 5.1. WithanolideswithAdditionalRingsInvolvingC-21 ........... 157 5.2. PhysalinsandWithaphysalins ................................... 163 5.3. WithanolidesContaininganAromaticRing andRelatedSteroids ............................................. 168 5.4. Withanolideswithag-LactoneSideChain ...................... 172 5.5. 18-Norwithanolides .............................................. 181 5.6. SpiranoidWithanolidesatC-22 ................................. 184 6. ChemicalandBio-transformationsofWithanolides .................. 185 6.1. ChemicalTransformations ....................................... 186 6.2. PhotochemicalTransformations ................................. 188 6.3. Biotransformations ............................................... 189 7. BiologicalActivitiesoftheWithanolides ............................. 192 7.1. InsecticidalActivities ............................................ 193 Contents vii 7.2. PhytotoxicActivities ............................................. 196 7.3. AntiparasiticActivities ........................................... 197 7.4. AntimicrobialActivities ......................................... 199 7.5. Anti-inflammatoryandGlucocorticoidRelatedActivities ...... 200 7.6. Cancer-RelatedActivities ........................................ 203 7.7. CNS-RelatedActivities .......................................... 208 8. ChemotaxonomicConsiderations ...................................... 209 8.1. TribePhysaleae .................................................. 210 8.2. TribesHyoscyameae,Lycieae,andSolaneae ................... 213 8.3. TribeDatureae ................................................... 213 8.4. GenerawithUncertainPositionsintheSolanaceae TaxonomicSystem ............................................... 213 References ................................................................. 216 AuthorIndex ............................................................. 231 SubjectIndex ............................................................. 249 ListedinPubMed . Contributors Gloria Barboza Departamento de Farmacia and IMBIV (CONICET), Facultad de Ciencias Qu´ımicas, Universidad Nacional de Co´rdoba, Ciudad Universitaria, Co´rdoba5000,Argentina,[email protected] Karl Baumann Novartis Institutes for BioMedical Research Vienna, Muthgasse 11/2,A-1190,Vienna,Austria MurtyA.R.C.Bulusu NovartisInstitutesforBioMedicalResearchVienna,Muth- gasse11/2,A-1190,Vienna,Austria Gerardo Burton Departamento de Qu´ımica Orga´nica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabello´n 2, Buenos Aires C1428EGA, Argentina,[email protected] Sherif S. Ebada Institute of Pharmaceutical Biology and Biotechnology, Heinrich-Heine University of Duesseldorf, Universitaetsstrasse 1, D-40225, Duesseldorf, Germany; Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Ain-Shams University, Organization of African Unity 1, 11566Cairo,Egypt,[email protected] RobertoR.Gil DepartmentofChemistry,CarnegieMellonUniversity,4400Fifth AvePittsburgh,PA15213,USA,[email protected] NeilLajkiewicz DepartmentofChemistryandCenterforChemicalMethodology and Library Development (CMLD-BU), Boston University, Commonwealth Avenue590,Boston,MA02215,USA,[email protected] Min Li-Weber Tumor Immunology Program (D030), German Cancer Research Center (DKFZ), Im Neuenheimer Feld 280, D-69120, Heidelberg, Germany, [email protected] ix x Contributors Rosana I. Misico Departamento de Qu´ımica Orga´nica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de BuenosAires,CiudadUniversitaria,Pabello´n2,BuenosAiresC1428EGA,Argentina, [email protected] VivianaE.Nicotra DepartamentodeQu´ımicaOrga´nicaandIMBIV(CONICET), Facultad de Ciencias Qu´ımicas, Universidad Nacional de Co´rdoba, Ciudad Universitaria, Ciencias Qu´ımicas II, Co´rdoba 5000, Argentina, vnicotra@mail. fcq.unc.edu.ar Juan C. Oberti Departamento de Qu´ımica Orga´nica and IMBIV (CONICET), Facultad de Ciencias Qu´ımicas, Universidad Nacional de Co´rdoba, Ciudad Uni- versitaria,CienciasQu´ımicasII,Co´rdoba,Argentina,[email protected] JohnA.PorcoJr. DepartmentofChemistryandCenterforChemicalMethodology andLibraryDevelopment(CMLD-BU),BostonUniversity,CommonwealthAvenue 590,Boston,MA02215,USA,[email protected] PeterProksch InstituteofPharmaceuticalBiologyandBiotechnology,Heinrich- Heine University of Duesseldorf, Universitaetsstrasse 1, D-40225, Duesseldorf, Germany,[email protected] Anton Stuetz Novartis Institutes for BioMedical Research Vienna, Muthgasse 11/2,A-1190,Vienna,Austria,[email protected]

See more

The list of books you might like