Bioactive Natural Products - Volume 36 of Studies in Natural Products Chemistry – Elsevier

408 Pages·2016·12.42 MB·English

Elsevier
TheBoulevard,LangfordLane,Kidlington,Oxford,OX51GB,UK
Radarweg29,POBox211,1000AEAmsterdam,TheNetherlands
Firstedition2012
Copyright#2012ElsevierB.V.Allrightsreserved
Nopartofthispublicationmaybereproduced,storedinaretrievalsystem
ortransmittedinanyformorbyanymeanselectronic,mechanical,photocopying,
recordingorotherwisewithoutthepriorwrittenpermissionofthepublisher.
PermissionsmaybesoughtdirectlyfromElsevier’sScience&TechnologyRights
DepartmentinOxford,UK:phone(þ44)(0)1865843830;fax(þ44)(0)1865853333;
email:[e-mail]tyourrequestonlineby
visitingtheElsevierwebsiteathttp://elsevier.com/locate/permissions,andselecting
ObtainingpermissiontouseElseviermaterial
Notice
Noresponsibilityisassumedbythepublisherforanyinjuryand/ordamagetopersonsorproperty
asamatterofproductsliability,negligenceorotherwise,orfromanyuseoroperationofany
methods,products,instructionsorideascontainedinthematerialherein.Becauseofrapid
advancesinthemedicalsciences,inparticular,independentverificationofdiagnosesanddrug
dosagesshouldbemade
BritishLibraryCataloguinginPublicationData
AcataloguerecordforthisbookisavailablefromtheBritishLibrary
LibraryofCongressCataloging-in-PublicationData
AcatalogrecordforthisbookisavailablefromtheLibraryofCongress
ISBN:978-0-444-53836-9
ISSN:1572-5995
ForinformationonallElsevierpublications
visitourwebsiteatstore.elsevier.com
PrintedandboundinGreatBritain
12 13 14 15 10 9 8 7 6 5 4 3 2 1

Atta-ur-Rahman (Ed.) (2012) Bioactive Natural Products –
Volume 36 of Studies in Natural Products Chemistry – Elsevier
Contributors
Awdah Al-Hazmi, College of Medicine, University of Hail, P.O. Box 2440, Hail,
SaudiArabia
Mohammed Al-Karrawi, Department of Environmental Technology, Al Iskan,
Buraida, SaudiArabia
OthmanA.Al-Sagair,CollegeofMedicine,UniversityofHail,P.O.Box2440,Hail,
SaudiArabia
EricAndrianasolo,InstituteofMarineandCoastalSciences,RutgersUniversity,New
Brunswick,New Jersey,USA
JamalM.Arif,CollegeofMedicine,UniversityofHail,P.O.Box2440,Hail,Saudi
Arabia, andDepartmentofBiotechnology,MicrobiologyandBioinformatics,
Integral University,Lucknow,India,
Marcela M. Baracat, Departamento de Ciencias Farmaceuticas, Centro de Ciencias
daSaude,UniversidadeEstadual deLondrina,Londrina,Parana,Brazil
Renato D.R. Cardoso, Departamento de Ciencias Patologicas, Centro de Ciencias
Biologicas, UniversidadeEstadualdeLondrina,Rod.CelsoGarcia Cid,Campus
Universitario, Londrina,Parana,Brazil
RubiaCasagrande,DepartamentodeCienciasFarmaceuticas,CentrodeCienciasda
Saude,UniversidadeEstadualde Londrina,Londrina,Parana,Brazil
Fernando Q. Cunha, Department of Pharmacology, School of Medicine of Ribeirao
Preto,UniversityofSao Paulo,RibeiraoPreto,Sao Paulo,Brazil
Thiago M. Cunha, Department of Pharmacology, School of Medicine of Ribeirao
Preto,UniversityofSao Paulo,RibeiraoPreto,Sao Paulo,Brazil
Salvatore de Rosa, Consiglio Nazionale delle Ricerche Istituto di Chimica Biomole-
colare, Pozzuoli,Naples,Italy
Paul Falkowski, Institute of Marine and Coastal Sciences, Rutgers University, New
Brunswick,New Jersey,USA
Alvina Farooqui, Department of Biotechnology, Microbiology and Bioinformatics,
Integral University,Lucknow,India
Sergio H. Ferreira, Department of Pharmacology, School of Medicine of Ribeirao
Preto,UniversityofSao Paulo,RibeiraoPreto,Sao Paulo,Brazil
Maria J.V. Fonseca, Department of Pharmaceutical Sciences of Ribeirao Preto,
UniversityofSao Paulo,RibeiraoPreto,Sao Paulo,Brazil
SandraR.Georgetti,DepartamentodeCienciasFarmaceuticas,CentrodeCienciasda
Saude,UniversidadeEstadualde Londrina,Londrina,Parana,Brazil
ix
x Contributors
TeppeiKawahara,GraduateSchoolofEnvironmentalScience,HokkaidoUniversity,
Kita-ku,Sapporo,Japan
Yanyan Li, Muse´um National d’Histoire Naturelle, CNRS-UMR 7245, Unite´ Mole´-
culesdeCommunicationetAdaptationdesMicro-organismes,Paris,France
Richard Lutz, Institute of Marine and Coastal Sciences, Rutgers University, New
Brunswick,NewJersey,USA
BastienNay,Muse´umNationald’HistoireNaturelle,CNRS-UMR7245,Unite´ Mole´-
culesdeCommunicationetAdaptationdesMicro-organismes,Paris,France
IfedayoV.Ogungbe,NaturalProductsDrugDiscoveryGroup,DepartmentofChem-
istry,UniversityofAlabamainHuntsville,Huntsville,Alabama,USA
Tatsufumi Okino, Graduate School of Environmental Science, HokkaidoUniversity,
Kita-ku,Sapporo,Japan
MarioSergioPalma,LaboratoryofStructuralBiologyandZoochemistry,CEIS/Dept.
Biology,InstituteofBiosciences,Sa˜oPauloStateUniversity(UNESP),RioClaro,
Sa˜oPaulo,Brazil
SoizicPrado,Muse´umNationald’HistoireNaturelle,CNRS-UMR7245,Unite´ Mole´-
culesdeCommunicationetAdaptationdesMicro-organismes,Paris,France
StephenG.Pyne,SchoolofChemistry,UniversityofWollongong,Wollongong,New
SouthWales,Australia
ThunwadeeRitthiwigrom,DepartmentofChemistry,FacultyofScience,ChiangMai
University,ChiangMai,Thailand
WilliamN.Setzer,Natural ProductsDrugDiscoveryGroup, DepartmentofChemis-
try,UniversityofAlabama inHuntsville,Huntsville,Alabama,USA
MohammadHarisSiddiqui,DepartmentofBiotechnology,MicrobiologyandBioin-
formatics,IntegralUniversity, Lucknow,India
MeenakshiSingh,NaturalProductsDrugDiscoveryGroup,DepartmentofChemistry,
UniversityofAlabama inHuntsville,Huntsville,Alabama,USA
LikTongTan,NaturalSciencesandScienceEducation,NationalInstituteofEduca-
tion,NanyangTechnological University,Singapore,Singapore
GiuseppinaTommonaro,ConsiglioNazionaledelleRicercheIstitutodiChimicaBio-
molecolare,Pozzuoli,Naples,Italy
Waldiceu A. Verri Jr., Departamento de Ciencias Patologicas, Centro de Ciencias
Biologicas,UniversidadeEstadualdeLondrina,Rod. CelsoGarciaCid,Campus
Universitario,Londrina,Parana,Brazil
FabianaT.M.C.Vicentini,DepartmentofPharmaceuticalSciencesofRibeiraoPreto,
UniversityofSao Paulo,RibeiraoPreto,Sao Paulo,Brazil
Preface
This volume of Studies in Natural Products Chemistry is the 36th in the
series. The rapid growth in the natural sciences in the current era has created
an ever-growing need for books and journals which provide state-of-the-art
overviews in specific fields of research. Many aspects of basic research pro-
grams are intimately related to natural products.
With chapters written by leading authorities in their respective fields of
research, Studies in Natural Product Chemistry, Volume 36 presents current
frontiers and future guidelines for research based on important discoveries
made in the field of bioactive natural products. It is a valuable resource for
researchers and engineers working in natural product and medicinal chemis-
try. Elsevier assessed the market needs and launched the Studies in Natural
Product Chemistry series in 1988 and published Volume 35 in 2005. Taking
into consideration the importance of natural product chemistry and the
continuingneedforabookseriesonthistopic,Elsevierhasdecidedtoresume
publishing the series after a break of 6 years.
During the past two decades, the series has published more than 700
in-depth comprehensive review articles covering most of the important
discoveries and advances made in these disciplines. Volume 36 is devoted
to bioactive natural products. The chapters included in these volumes cover
the isolation, biological activities, and synthesis of natural products including
acylpolyamines from spider venoms, hydrothermal vents as new source of
drug discovery, marine cyanobacteria. Also, the readers will find very inter-
esting chapters on chlorosulfolipids, the ecological significance of fungal
endophyte, flavonoids as anti-inflammatory and analgesic drugs, and antil-
eishmanial natural products from plant species.
The current volume is another useful addition to this important series of
volumes on natural product chemistry which now covers more than 25,000
pages and is generallyacknowledged to be the leading book series inNatural
Product Chemistry.
I would like to express thanks to Miss Taqdees Malik and Mr. Wasim
Ahmadfortheirassistanceinthepreparationofthevolume.Iamalsograteful
to Mr. Mahmood Alam for his editorial assistance.
Prof. Atta-ur-Rahman, FRS
Patron-in-Chief
International Centre for Chemical & Biological Sciences
University of Karachi
Karachi, Pakistan
xi
Studies in Natural
Products Chemistry
edited by Atta-ur-Rahman
VOL. 1 Stereoselective Synthesis (Part A)
VOL. 2 Structure Elucidation (Part A)
VOL. 3 Stereoselective Synthesis (Part B)
VOL. 4 Stereoselective Synthesis (Part C)
VOL. 5 Structure Elucidation (Part B)
VOL. 6 Stereoselective Synthesis (Part D)
VOL. 7 Structure and Chemistry (Part A)
VOL. 8 Stereoselective Synthesis (Part E)
VOL. 9 Structure and Chemistry (Part B)
VOL. 10 Stereoselective Synthesis (Part F)
VOL. 11 Stereoselective Synthesis (Part G)
VOL. 12 Stereoselective Synthesis (Part H)
VOL. 13 Bioactive Natural Products (Part A)
VOL. 14 Stereoselective Synthesis (Part I)
VOL. 15 Structure and Chemistry (Part C)
VOL. 16 Stereoselective Synthesis (Part J)
VOL. 17 Structure and Chemistry (Part D)
VOL. 18 Stereoselective Synthesis (Part K)
VOL. 19 Structure and Chemistry (Part E)
VOL. 20 Structure and Chemistry (Part F)
VOL. 21 Bioactive Natural Products (Part B)
VOL. 22 Bioactive Natural Products (Part C)
VOL. 23 Bioactive Natural Products (Part D)
xiii
xiv StudiesinNaturalProductsChemistry
VOL. 24 Bioactive Natural Products (Part E)
VOL. 25 Bioactive Natural Products (Part F)
VOL. 26 Bioactive Natural Products (Part G)
VOL. 27 Bioactive Natural Products (Part H)
VOL. 28 Bioactive Natural Products (Part I)
VOL. 29 Bioactive Natural Products (Part J)
VOL. 30 Bioactive Natural Products (Part K)
VOL. 31 Studies in Natural Products Chemistry: Cumulative Indices
Vol. 1–30
VOL. 32 Bioactive Natural Products (Part L)
VOL. 33 Bioactive Natural Products (Part M)
VOL. 34 Bioactive Natural Products (Part N)
VOL. 35 Bioactive Natural Products (Part O)
VOL. 36 Bioactive Natural Products
Chapter 1
Isolation, Biological Activities,
and Synthesis of the Natural
Casuarines
Thunwadee Ritthiwigrom* and Stephen G. Pyne{
*DepartmentofChemistry,FacultyofScience,ChiangMaiUniversity,ChiangMai,Thailand
{SchoolofChemistry,UniversityofWollongong,Wollongong,NewSouthWales,Australia
INTRODUCTION
Casuarine 1 [1], casuarine-6-O-a-glucoside 2 [2], 6-epi-casuarine 3 (uniflor-
ine A) [3–5], and 3-epi-casuarine 4 [6] are members of the expanding group
of polyhydroxylated 3-hydroxymethylpyrrolizidine natural products (Fig. 1)
[7]. This group also includes australine [8], alexine [9] (7a-epi-australine),
several other epi-australines (1-epi-australine, 3-epi-australine [10], 2,3-di-
epi-australine, 2,3,7-tri-epi-australine) [11], 1-epi-australine-2-O-a-glucoside,
and the more recently isolated hyacinthacine alkaloids of which 19 novel
compounds have been identified [12]. This group, along with the polyhy-
droxylated pyrrolidine, piperidine, indolizidine, and nortropane alkaloids,
has glycosidase inhibitory activities and thus has potential utility as antiviral,
anticancer, antidiabetic, and antiobesity drugs [7]. Three structurally related
synthetic compounds have been marketed as antidiabetic drugs to treat type-
II diabetes based on their potent a-glucosidase inhibitory activities, while
others have been identified as candidates for therapeutics to treat type-1
Gaucher disease [7]. These potentially useful biological activities, along with
the stereochemical richness of these alkaloids (uniflorine A and casuarine
havesixcontiguousstereogeniccarbons),havemadethesecompoundsattrac-
tive and important synthetic targets [13]. This chapter describes the isolation,
structureelucidation,glycosidaseinhibitoryactivities,andthesynthesisofthe
four naturally occurring casuarines.
BioactiveNaturalProducts,Vol.36.DOI:10.1016/B978-0-444-53836-9.00018-9
1
#2012ElsevierB.V.Allrightsreserved.