Fundamentals and Applications of Analytical Chemistry

83 Pages·2012·8.92 MB·English

International Journal of Analytical Chemistry
Fundamentals and
Applications of
Analytical Chemistry
in Natural Products
Guest Editors: Norberto P. Lopes, Ernani Pinto,
Michael Niehues, Paul J. Gates, and Ricardo Vessecchi
Fundamentals and Applications of Analytical
Chemistry in Natural Products
International Journal of Analytical Chemistry
Fundamentals and Applications of Analytical
Chemistry in Natural Products
Guest Editors: Norberto P. Lopes, Ernani Pinto, Michael Niehues,
Paul J. Gates, and Ricardo Vessecchi
Copyright©2012HindawiPublishingCorporation.Allrightsreserved.
Thisisaspecialissuepublishedin“InternationalJournalofAnalyticalChemistry.”Allarticlesareopenaccessarticlesdistributedunder
theCreativeCommonsAttributionLicense,whichpermitsunrestricteduse,distribution,andreproductioninanymedium,provided
theoriginalworkisproperlycited.
Editorial Board
MohamedAbdel-Rehim,Sweden JohnP.Hart,UK StigPedersen-Bjergaard,Norway
YoshinobuBaba,Japan JosefHavel,CzechRepublic HansPuxbaum,Austria
GntherK.Bonn,Austria LeiHong,USA M.A.Raggi,Italy
LawrenceA.Bottomley,USA XiaolinHou,Denmark JeanL.Ravanat,France
RichardG.Brereton,UK JanA˚keJo¨nsson,Sweden PeterL.Rinaldi,USA
BogusławBuszewski,Poland TeizoKitagawa,Japan AldoRoda,Italy
YijunChen,China SpasD.Kolev,Australia IsraelSchechter,Israel
AlbertoChisvert,Spain CynthiaK.Larive,USA ThomasJ.Schmidt,Germany
PawelCiborowski,USA RogerM.LeBlanc,USA GiuseppeSpoto,Italy
StephenP.Cramer,USA HianKeeLee,Singapore Shi-GangSun,China
NeilD.Danielson,USA ShaopingLi,China GregM.Swain,USA
IbrahimDarwish,SaudiArabia Jin-MingLin,China K.Tam,Canada
AdilDenizli,Turkey DavidM.Lubman,USA PeterA.Tanner,HongKong
FrancisD’souza,USA JohnH.Luong,Canada JaneThomas-Oates,UK
AntonioFacchetti,USA RolandMarini,Belgium D.Tsikas,Germany
FrantisekForet,CzechRepublic JurisMeija,Canada BeataWalczak,Poland
RuthFreitag,Germany ShojiMotomizu,Japan JosephWang,USA
ChrisD.Geddes,USA EricJ.Munson,USA CharlesL.Wilkins,USA
LoGorton,Sweden BorisF.Myasoedov,Russia PhilipM.Williams,UK
AndrasGuttman,Austria PavelNesterenko,Australia GeorgeS.Wilson,USA
PaulR.Haddad,Australia DimitriosP.Nikolelis,Greece TroyD.Wood,USA
P.Haglund,Sweden FrancescoPalmisano,Italy JyhMyngZen,Taiwan
SteenHonorHansen,Denmark GaborPatonay,USA
Contents
FundamentalsandApplicationsofAnalyticalChemistryinNaturalProducts,NorbertoP.Lopes,
ErnaniPinto,MichaelNiehues,PaulJ.Gates,andRicardoVessecchi
Volume2012,ArticleID156201,2pages
UptakeofSeedsSecondaryMetabolitesbyVirolasurinamensisSeedlings,MassuoJorgeKato,
MassayoshiYoshida,NorbertoPeporineLopes,DeniseBrentandaSilva,andAlbertoJose´ Cavalheiro
Volume2012,ArticleID721494,5pages
MultilayerFilmsElectrodesConsistedofCashewGumandPolyanilineAssembledbytheLayer-by-Layer
Technique:ElectrochemicalCharacterizationandItsUseforDopamineDetermination,
SergioBitencourtArau´joBarros,CleideMariadaSilvaLeite,AnaCristinaFacundodeBrito,
Jose´ RibeiroDosSantosJu´nior,ValtencirZucolotto,andCarlaEiras
Volume2012,ArticleID923208,10pages
SpectrophotometricDeterminationofIron(II)andCobalt(II)byDirect,Derivative,andSimultaneous
MethodsUsing2-Hydroxy-1-Naphthaldehyde-p-Hydroxybenzoichydrazone,V.S.AnusuyaDeviand
V.KrishnaReddy
Volume2012,ArticleID981758,12pages
ChemicalConstituentsofEssentialOilfromLippiasidoidesCham.(Verbenaceae)LeavesCultivatedin
Hidrolaˆndia,Goia´s,Brazil,SandraRibeirodeMorais,ThiagoLeviSilvaOliveira,MariaTeresaFreitasBara,
EdemilsonCardosodaConceic¸a˜o,MariaHelenaRezende,PedroHenriqueFerri,andJose´ RealinodePaula
Volume2012,ArticleID363919,4pages
CharacterisationofFlavonoidAglyconesbyNegativeIonChip-BasedNanosprayTandemMass
Spectrometry,PaulJ.GatesandNorbertoP.Lopes
Volume2012,ArticleID259217,7pages
ApplicationofMonoclonalAntibodiesagainstBioactiveNaturalProducts:EasternBlottingand
PreparationofKnockoutExtract,HiroyukiTanaka,OsamuMorinaga,TakuhiroUto,ShunsukeFuji,
FrederickAsareAboagye,NguyenHuuTung,XiaoWeiLi,WarapornPutalun,andYukihiroShoyama
Volume2012,ArticleID260425,10pages
ConcentrationofInorganicElementsContentinBenthicSeaweedsofFernandodeNoronhaArchipelago
bySynchrotronRadiationTotalReflectionX-RayFluorescenceAnalysis(SRTXRF),
LeandroDeSantisFerreira,RosanaPeporineLopes,MabelNormaCostasUlbrich,ThaisGuaratini,
PioColepicolo,NorbertoPeporineLopes,RicardoClapisGarla,EuricoCabralOliveiraFilho,
AdrianMartinPohlit,andOrgheˆdaLuizaArau´joDominguesZucchi
Volume2012,ArticleID407274,8pages
DevelopmentofaNovelBiosensorUsingCationicAntimicrobialPeptideandNickelPhthalocyanine
UltrathinFilmsforElectrochemicalDetectionofDopamine,MaysaF.Zampa,IneˆsMariadeS.Arau´jo,
Jose´ RibeirodosSantosJu´nior,ValtencirZucolotto,Jose´ RobertodeS.A.Leite,andCarlaEiras
Volume2012,ArticleID850969,7pages
PreliminaryAssessmentoftheChemicalStabilityofDriedExtractsfromGuazumaulmifoliaLam.
(Sterculiaceae),GiselyC.Lopes,RenataLonghini,PauloVictorP.dosSantos,AdrianoA.S.Arau´jo,
MarcosLucianoBruschi,andJoa˜oCarlosP.deMello
Volume2012,ArticleID508945,7pages
ApolarCompoundsinSeaweedsfromFernandodeNoronhaArchipelago(NortheasternCoastofBrazil),
LeandroDeSantisFerreira,IzabelCristinaCasanovaTuratti,NorbertoPeporineLopes,ThaisGuaratini,
PioColepicolo,EuricoCabralOliveiraFilho,andRicardoClapisGarla
Volume2012,ArticleID431954,5pages
HindawiPublishingCorporation
InternationalJournalofAnalyticalChemistry
Volume2012,ArticleID156201,2pages
doi:10.1155/2012/156201
Editorial
Fundamentals and Applications of Analytical Chemistry in
Natural Products
NorbertoP.Lopes,1ErnaniPinto,2MichaelNiehues,1PaulJ.Gates,3andRicardoVessecchi1
1Nu´cleodePesquisaemProdutosNaturaiseSint´etico,FaculdadedeCiˆenciasFarmacˆeuticasdeRibeira˜oPreto,
UniversidadedeSa˜oPaulo,14040-901Ribeira˜oPreto,SP,Brazil
2DepartamentodeAna´lisesCl´ınicaseToxicolo´gicas,FaculdadedeCiˆenciasFarmacˆeuticas,UniversidadedeSa˜oPaulo,
05508-900Sa˜oPaulo,SP,Brazil
3SchoolofChemistry,UniversityofBristol,Cantock’sClose,BristolBS81TS,UK
CorrespondenceshouldbeaddressedtoNorbertoP.Lopes,[email protected]
Received15March2012;Accepted15March2012
Copyright©2012NorbertoP.Lopesetal.ThisisanopenaccessarticledistributedundertheCreativeCommonsAttribution
License,whichpermitsunrestricteduse,distribution,andreproductioninanymedium,providedtheoriginalworkisproperly
cited.
This special issue is aimed at collecting together recent of seaweed from the Fernando de Noronha archipelago. In
developments in the field of natural product analysis. This addition, a second paper has used SRTXRF analysis as a
issue covers methodologies and applications as diverse as techniquetodetermineseveralinorganicspecieswithinthe
secondary metabolite identification to the detection of same archipelago. Both papers contribute to an increased
metalsinfoodstuffs.Thechemistryofnaturalproductshas understanding of adsorption and accumulation of such
gainedprominencenotonlyduetotheon-goingsearchfor naturalelementsbyalgaeinthatspecificarea.
new bioactive substances but also in related areas such as V. S. A. Devi and V. K. Reddy’s paper presents
foodchemistryandchemicalecology. a methodology for spectrophotometric determination of
Wefeelthatthisspecialissuerepresentssomeofthewide iron(II)andcobalt(II)using2-hydroxi-1-naphthaldehyde-p-
rangingresearchcurrentlyperformedinthisdiverseareaand hydroxybenzoichydrazonewhichcanthenbeappliedforthe
this is exemplified by the affiliations of the authors of the analyses of biological and water samples that contain these
papersincludedwhichismadeupofchemists,biochemists, metals.
biologists, physicists, toxicologists, physiologists, pharma- The paper by G. C. Lopes et al. reports the preliminary
ceutists,andgeochemists.Whatalloftheseresearchershave estimationofthestabilityofthedriedextractfromthebark
in common, despite their wide ranging backgrounds, is the ofGuazumaulmifoliaLam.(“Mutamba”).Thermogravime-
need to make use of the powerful techniques of analytical try analysis along with HPLC were used in the study. The
chemistrytoanalyzenaturalcompoundsincomplexmatri- resultscanbeusedasachemicalmarkerinthequalitycontrol
ces.Thus,thisspecialissueisdedicatedtoallthereadersthat ofdriedextractsofG.ulmifolia.
wouldliketoapplyanalyticalchemistryfornaturalproducts The study by M. F. Zampa et al. is the first report
analysis. of the antimicrobial peptide from the skin of the Phyl-
This issue presents ten papers, which describe either lomedusa hypochondrialis frog and its incorporation into
a specific analytical method for specific types of natural nanostructured layered films in conjunction with nickel-
products, the use of natural compounds to aid analytical tetrasulfonated phthalocyanines. The film was used as a
developments, or modern techniques for the analysis of biosensortodetectdopamine,aneurotransmitterassociated
metalsinfoodstuffsandfoodqualitycontrol(agrowingarea withdiseasessuchasAlzheimer’sandParkinson’s.
ofinterest). S. B. A. Barros et al. demonstrate the exploitation
ThearticlebyL.deS.Ferreiraetal.describestheuseof of the polyelectrolytic behavior of natural cashew gum
hyphenatedtechniquestodeterminefattyacidsinaspecies (Anacardium occidentale L.), found in northeast Brazil, as a
2 InternationalJournalofAnalyticalChemistry
componentofananocompositeelectrode.Theperformance
of the electrodes was evaluated by the determination of
dopamine.
The paper by H. Tanaka et al. presents matrix-assisted
laserdesorption/ionization(MALDI)massspectrometryfor
theconfirmationofthehaptennumberinsynthesizedanti-
gens.TwouniqueapplicationsusingMAb,Easternblotting,
andknockoutextracthavebeenintroducedinthispaper.The
Easternblottingmethodhasgreatpotentialapplicationsfor
thewiderangeofnaturalproducts.
The article of S. R. de Moraes et al. highlights the use
of Lippia sidoides Cham. (also known as alecrim pimenta),
nativetonortheasternBrazilandnorthernMinasGerais,and
theiressentialoils.Theoxygenatedmonoterpene1,8-cineole
wasthemajorconstituent,followedbyisoborneolandbornyl
acetate.Thechemicalcompositionofessentialoilsdescribed
inthispaperdiffersfromthatdescribedintheliteraturefor
L.sidoidesfoundinitsnativeenvironment.
The paper of M. J. Kato et al. demonstrates the GC-
MS monitoring of the major secondary metabolites and
fatty acids occurring in the seeds of Virola surinamensis,
duringgerminationandseedlingdevelopment.Theauthors
conclude that the germination of V. surinamensis seeds and
the seedling development are processes in which both fatty
acidsandsecondarymetabolites(lignans,isoflavonoidsand
juruenolides) are equally consumed in the seeds indicating
their potential physiological role as energy and carbon
sources.
The article of P. J. Gates and N. P. Lopes describes the
application of negative ion chip-based nanospray tandem
mass spectrometry for the analysis of flavonoid aglycones.
The methodology is tested by the analysis of a crude green
tea extract, where the expected flavonoids were readily
identified.
NorbertoP.Lopes
ErnaniPinto
MichaelNiehues
PaulJ.Gates
RicardoVessecchi
HindawiPublishingCorporation
InternationalJournalofAnalyticalChemistry
Volume2012,ArticleID721494,5pages
doi:10.1155/2012/721494
Research Article
Uptake of Seeds Secondary Metabolites by
VirolasurinamensisSeedlings
MassuoJorgeKato,1MassayoshiYoshida,1NorbertoPeporineLopes,2
DeniseBrentandaSilva,3andAlbertoJose´ Cavalheiro4
1InstitutodeQu´ımica,UniversidadedeSa˜oPaulo,CP26077,05599-970Sa˜oPaulo,SP,Brazil
2Nu´cleodePesquisaemProdutosNaturaiseSint´eticos(NPPNS),FaculdadedeCiˆenciasFarmacˆeuticasdeRibeira˜oPreto,
UniversidadedeSa˜oPaulo,14040-903Ribeira˜oPreto,SP,Brazil
3LychnofloraPesquisaeDesenvolvimentoemProdutosNaturaisLTDA,IncubadoraSupera,CampusdaUSP,
14040-900Ribeira˜oPreto,SP,Brazil
4Nu´cleodeBioensaio,Bioss´ınteseeEcofisiologiadeProdutosNaturais(NuBBE),InstitutodeQu´ımica,UniversidadeEstadualPaulista,
CP355,14800-900Araraquara,SP,Brazil
CorrespondenceshouldbeaddressedtoMassuoJorgeKato,[email protected]
Received2September2011;Accepted19December2011
AcademicEditor:ErnaniPinto
Copyright©2012MassuoJorgeKatoetal. This is an open access article distributed under the Creative Commons Attribution
License,whichpermitsunrestricteduse,distribution,andreproductioninanymedium,providedtheoriginalworkisproperly
cited.
ThemajorsecondarymetabolitesandfattyacidsoccurringintheseedsofVirolasurinamensisweremonitoredbyGC-MSduring
germinationandseedlingdevelopment.Theroleascarbonsourceforseedlingdevelopmentwasindicatedconsideringthatboth
classesofcompoundsweresimilarlyconsumedintheseedsandthatnoselectiveconsumptionofcompoundscouldbedetected.
1.Introduction ofhydroxytetralonelignansandapreferentialaccumulation
of a lignan hydroxy-otobain was observed in the whole
Several neotropical trees produce fruits with large and
seedlings[7].
heavyseeds[1].Virolasurinamensisisamyristicaceoustree
Inviewofthelackofsystematicinvestigationregarding
growingintheAmazonianfloodedplainsandproducesseeds
this important event in the reproduction of tropical trees,
duringtherainyseason[2,3].Seedsareviableshortlyafter
thetranslocationofsecondarymetabolitesoccurringinlarge
ripeningandareadaptedtobedispersedbywaterorbylarge
seeds to be used as a defensive compounds in the seedlings
birds such as toucans and ara¸caris. The seedling formation
remainsasahypothesis[8,9].
can be divided in two distinct phases: seed germination
and seedling development [4]. The cotyledons are hidden Virola surinamensis seeds contain 15.4% of soluble
in the seed coat (cryptocotylar) and are storage organs of tannins as a dry mass and the highest concentration of
fattymaterialandpolysaccharidesthatarerecruitedforthe compoundswithaprobabledefensivefunctionyetrecorded
maintenanceofseedlingduringitsgrowthanddevelopment [10]. Their cotyledons are rich in triacylglycerols and free
[5].AstudycarriedoutonV.venosarevealedthatthemajor fatty acids. Phytochemical analysis of V. surinamensis seeds
lignanscubebinanddihydrokusunokininaccumulatedinthe collected at Combu Island demonstrated the occurrence of
seeds were not detected in its seedlings which accumulated lignoids, propiophenone, and γ-lactones in these organs
a polyketide instead [6]. The major constituent identified [11].AnalysisofseedlingleavesofV.surinamensisgrowingin
in the seedling roots was shown to be the lignan sesamin, thefield,ingreenhouseconditionsandinmicropropagated
a minor constituent in the seeds. A different result were plantlets revealed the absence of lignans and the exclusive
observed with V. sebifera in which a possible translocation occurrenceofjuruenolideC(8a)(Figure1)[12].Herein,we