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https://observatorio.fm.usp.br/handle/OPI/12032
Title: | Anti-parasitic Guanidine and Pyrimidine Alkaloids from the Marine Sponge Monanchora arbuscula |
Authors: | SANTOS, Mario F. C.; HARPER, Philip M.; WILLIAMS, David E.; MESQUITA, Juliana T.; PINTO, Erika G.; COSTA-SILVA, Thais A. da; HAJDU, Eduardo; FERREIRA, Antonio G.; SANTOS, Raquel A.; MURPHY, Patrick J.; ANDERSEN, Raymond J.; TEMPONE, Andre G.; BERLINCK, Roberto G. S. |
Citation: | JOURNAL OF NATURAL PRODUCTS, v.78, n.5, p.1101-1112, 2015 |
Abstract: | 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). |
Appears in Collections: | Artigos e Materiais de Revistas Científicas - IMT |
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