Progress in the Chemistry of Organic Natural Products Vol. 94

269 Pages·2011·7.174 MB·English

by  Sherif S. Ebada, Neil Lajkiewicz (auth.), A. Douglas Kinghorn, Heinz Falk, Junichi Kobayashi (eds.)

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
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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]