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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
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Santos, Mario F. C. [1] ; Harper, Philip M. [2] ; Williams, David E. [3, 4] ; Mesquita, Juliana T. [5] ; Pinto, Erika G. [5, 6] ; da Costa-Silva, Thais A. [5] ; Hajdu, Eduardo [7] ; Ferreira, Antonio G. [8] ; Santos, Raquel A. [9] ; Murphy, Patrick J. [2] ; Andersen, Raymond J. [3, 4] ; Tempone, Andre G. [5, 6] ; Berlinck, Roberto G. S. [1]
Total Authors: 13
Affiliation:
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
[2] Bangor Univ, Sch Chem, Bangor LL57 2UW, Gwynedd - Wales
[3] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1 - Canada
[4] Univ British Columbia, Dept Earth Ocean & Atmospher Sci, Vancouver, BC V6T 1Z1 - Canada
[5] Adolfo Lutz Inst, Ctr Parasitol & Micol, BR-01246000 Sao Paulo, SP - Brazil
[6] Univ Sao Paulo, Inst Med Trop Sao Paulo, BR-05403000 Sao Paulo, SP - Brazil
[7] Univ Fed Rio de Janeiro, Museu Nacl, BR-20940040 Rio De Janeiro, RJ - Brazil
[8] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[9] Univ Franca, Programa Posgrad Ciencias, Lab Genet & Biol Mol, BR-14404600 Franca, SP - Brazil
Total Affiliations: 9
Document type: Journal article
Source: Journal of Natural Products; v. 78, n. 5, p. 1101-1112, MAY 2015.
Web of Science Citations: 29
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). (AU)

FAPESP's process: 13/50228-8 - Biodiversity components, and its metabolic characters, of Brazilian Islands
Grantee:Roberto Gomes de Souza Berlinck
Support type: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 10/50190-2 - Investigation of metabolic and biotechnological potential of marine organisms in bioremediation processes and for the production of substances with anti-viral, anti-inflammatory and anti-Leishmania activities (Marine Biodiversity)
Grantee:Roberto Gomes de Souza Berlinck
Support type: BIOTA-FAPESP Program - Thematic Grants