Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula

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dc.contributorSistema FMUSP-HC: Faculdade de Medicina da Universidade de São Paulo (FMUSP) e Hospital das Clínicas da FMUSP
dc.contributor.authorSANTOS, Mario F. C.
dc.contributor.authorHARPER, Philip M.
dc.contributor.authorWILLIAMS, David E.
dc.contributor.authorMESQUITA, Juliana T.
dc.contributor.authorPINTO, Erika G.
dc.contributor.authorCOSTA-SILVA, Thais A. da
dc.contributor.authorHAJDU, Eduardo
dc.contributor.authorFERREIRA, Antonio G.
dc.contributor.authorSANTOS, Raquel A.
dc.contributor.authorMURPHY, Patrick J.
dc.contributor.authorANDERSEN, Raymond J.
dc.contributor.authorTEMPONE, Andre G.
dc.contributor.authorBERLINCK, Roberto G. S.
dc.date.accessioned2015-10-26T16:53:12Z
dc.date.available2015-10-26T16:53:12Z
dc.date.issued2015
dc.description.abstractHPLC-UV-ELSD-MS-guided fractionation of the anti-parasitic extract obtained from the marine sponge Monanchora arbuscula, collected off the southeastern coast of Brazil, led to the isolation of a series of guanidine and pyrimidine alkaloids. The pyrimidines monalidine A (1) and arbusculidine A (7), as well as the guanidine alkaloids batzellamide A (8) and hemibatzelladines 9-11, represent new minor constituents that were identified by analysis of spectroscopic data. The total synthesis of monalidine A confirmed its structure. Arbusculidine A (7), related to the ptilocaulin/mirabilin/netamine family of tricyclic guanidine alkaloids, is the first in this family to possess a benzene ring. Batzellamide A (8) and hemibatzelladines 9-11 represent new carbon skeletons that are related to the batzelladines. Evaluation of the anti-parasitic activity of the major known metabolites, batzelladines D (12), F (13), L (14), and nor-L (15), as well as of synthetic monalidine A (1), against Trypanosoma cruzi and Leishmania infantum is also reported, along with a detailed investigation of parasite cell-death pathways promoted by batzelladine L (14) and norbatzelladine L (15).
dc.description.indexMEDLINE
dc.description.sponsorshipSao Paulo State Funding Agency (FAPESP) BIOTA/BIOprospecTA grants [2010/50190-2, 2013/50228-8]
dc.description.sponsorshipNSERC (Canada)
dc.description.sponsorshipERDF BEACON project
dc.description.sponsorshipKESS program (European Social Fund)
dc.description.sponsorshipMorvus Technology Ltd.
dc.description.sponsorshipFAPESP
dc.description.sponsorshipCNPq
dc.identifier.citationJOURNAL OF NATURAL PRODUCTS, v.78, n.5, p.1101-1112, 2015
dc.identifier.doi10.1021/acs.jnatprod.5b00070
dc.identifier.eissn1520-6025
dc.identifier.issn0163-3864
dc.identifier.urihttps://observatorio.fm.usp.br/handle/OPI/12032
dc.language.isoeng
dc.publisherAMER CHEMICAL SOC
dc.relation.ispartofJournal of Natural Products
dc.rightsrestrictedAccess
dc.rights.holderCopyright AMER CHEMICAL SOC
dc.subject.othercrambe-crambe
dc.subject.otherptilomycalin-a
dc.subject.otherantimalarial activity
dc.subject.othernatural-products
dc.subject.otherbiemna-laboutei
dc.subject.otherbatzelladine-f
dc.subject.otherrevision
dc.subject.otherpulchra
dc.subject.otherstereochemistry
dc.subject.otherunguifera
dc.subject.wosPlant Sciences
dc.subject.wosChemistry, Medicinal
dc.subject.wosPharmacology & Pharmacy
dc.titleAnti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula
dc.typearticle
dc.type.categoryoriginal article
dc.type.versionpublishedVersion
dspace.entity.typePublication
hcfmusp.affiliation.countryCanadá
hcfmusp.affiliation.countryPaís de Gales
hcfmusp.affiliation.countryisogb
hcfmusp.affiliation.countryisoca
hcfmusp.author.externalSANTOS, Mario F. C.:Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil
hcfmusp.author.externalHARPER, Philip M.:Bangor Univ, Sch Chem, Bangor LL57 2UW, Gwynedd, Wales
hcfmusp.author.externalWILLIAMS, David E.:Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada; Univ British Columbia, Dept Earth Ocean & Atmospher Sci, Vancouver, BC V6T 1Z1, Canada
hcfmusp.author.externalMESQUITA, Juliana T.:Adolfo Lutz Inst, Ctr Parasitol & Micol, BR-01246000 Sao Paulo, SP, Brazil
hcfmusp.author.externalCOSTA-SILVA, Thais A. da:Adolfo Lutz Inst, Ctr Parasitol & Micol, BR-01246000 Sao Paulo, SP, Brazil
hcfmusp.author.externalHAJDU, Eduardo:Univ Fed Rio de Janeiro, Museu Nacl, BR-20940040 Rio De Janeiro, RJ, Brazil
hcfmusp.author.externalFERREIRA, Antonio G.:Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil
hcfmusp.author.externalSANTOS, Raquel A.:Univ Franca, Programa Posgrad Ciencias, Lab Genet & Biol Mol, BR-14404600 Franca, SP, Brazil
hcfmusp.author.externalMURPHY, Patrick J.:Bangor Univ, Sch Chem, Bangor LL57 2UW, Gwynedd, Wales
hcfmusp.author.externalANDERSEN, Raymond J.:Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada; Univ British Columbia, Dept Earth Ocean & Atmospher Sci, Vancouver, BC V6T 1Z1, Canada
hcfmusp.author.externalBERLINCK, Roberto G. S.:Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP, Brazil
hcfmusp.citation.scopus62
hcfmusp.contributor.author-fmusphcERIKA GRACIELLE PINTO
hcfmusp.contributor.author-fmusphcANDRE GUSTAVO TEMPONE CARDOSO
hcfmusp.description.beginpage1101
hcfmusp.description.endpage1112
hcfmusp.description.issue5
hcfmusp.description.volume78
hcfmusp.origemWOS
hcfmusp.origem.pubmed25924111
hcfmusp.origem.scopus2-s2.0-84930209248
hcfmusp.origem.wosWOS:000355158300015
hcfmusp.publisher.cityWASHINGTON
hcfmusp.publisher.countryUSA
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