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

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art_SANTOS_Antiparasitic_Guanidine_and_Pyrimidine_Alkaloids_from_the_Marine_2015.PDF (2.25 MB)
Citações na Scopus
61
Tipo de produção
article
Data de publicação
2015
DOI
Scopus
Web of Science
PubMed
Título da Revista
ISSN da Revista
Título do Volume
Editora
AMER CHEMICAL SOC
Autores
SANTOS, Mario F. C.
HARPER, Philip M.
WILLIAMS, David E.
MESQUITA, Juliana T.
COSTA-SILVA, Thais A. da
HAJDU, Eduardo
FERREIRA, Antonio G.
SANTOS, Raquel A.
MURPHY, Patrick J.
Citação
JOURNAL OF NATURAL PRODUCTS, v.78, n.5, p.1101-1112, 2015
Projetos de Pesquisa
Unidades Organizacionais
Fascículo
Resumo
HPLC-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).
Palavras-chave
URI
https://observatorio.fm.usp.br/handle/OPI/12032
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Coleções
Artigos e Materiais de Revistas Científicas - IMT