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

Autor(es):Mostrar menos -

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: Journal of Natural Products; v. 78, n. 5, p. 1101-1112, MAY 2015.
• Citações Web of Science: 29

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). (AU)

• Processo FAPESP: 13/50228-8 - Componentes da biodiversidade, e seus caracteres metabólicos, de ilhas do Brasil - uma abordagem integrada
• Beneficiário: Roberto Gomes de Souza Berlinck
• Linha de fomento: Auxílio à Pesquisa - Programa BIOTA - Temático
• Processo FAPESP: 10/50190-2 - Investigação do potencial biotecnológico e metabólico de organismos marinhos para processos de biorremediação e produção de substâncias com atividades anti-virais, anti-leishmania e anti-inflamatória (Biodiversidade Marinha)
• Beneficiário: Roberto Gomes de Souza Berlinck
• Linha de fomento: Auxílio à Pesquisa - Programa BIOTA - Temático