Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/31391
Title: Alkaloids from leaves of Guatteria pogonopus (Annonaceae) and their Cytotoxicities
Authors: Santos, Maria de Fátima Costa
Fontes, José Eraldo do Nascimento
Dutra, Lívia Macedo
Bomfim, Larissa M.
Costa, Cinara Oliveira D'Sousa
Moraes, Valéria Regina de Souza
Barison, Andersson
Soares, Milena Botelho Pereira
Silva, Felipe Moura Araujo da
Almeida, Jackson Roberto Guedes da Silva
Koolen, Héctor Henrique Ferreira
Bezerra, Daniel Pereira
Costa, Emmanoel Vilaça
Affilliation: Universidade Federal de Sergipe. Departamento de Química. São Cristóvão, SE, Brasil / Universidade Federal do Paraná. Centro de Ressonância Magnética Nuclear. Curitiba, PR, Brasil.
Universidade Federal de Sergipe. Departamento de Química. São Cristóvão, SE, Brasil.
Universidade Federal do Paraná. Centro de Ressonância Magnética Nuclear. Curitiba, PR, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.
Universidade Federal de Sergipe. Departamento de Química. São Cristóvão, SE, Brasil.
Universidade Federal do Paraná. Centro de Ressonância Magnética Nuclear. Curitiba, PR, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, Brasil.
Universidade Federal do Amazonas. Departamento de Química. Manaus, AM, Brasil.
Universidade Federal do Vale do São Francisco. Núcleo de Estudos e Pesquisas de Plantas Medicinais. Petrolina, PE, Brasil.
Universidade do Estado do Amazonas. Escola Superior de Ciências da Saúde. Manaus, AM, Brasil.
Universidade Federal do Paraná. Centro de Ressonância Magnética Nuclear. Curitiba, PR, Brasil.
Universidade Federal do Amazonas. Departamento de Química. Manaus, AM, Brasil.
Abstract: The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (−)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC50 of 9.60 μmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC50 values of 3.41 an 8.50 μmol L-1, respectively.
Keywords: Alkaloids
Guatteria pogonopus
Leaves
Annonaceae
NMR
Cytotoxicity
keywords: Alcalóides
Guatteria pogonopus
Annonaceae
RMN
Citotoxicidade
Issue Date: 2018
Publisher: Sociedade Brasileira de Química
Citation: SANTOS, M. F. C. et al. Alkaloids from leaves of Guatteria pogonopus (Annonaceae) and their Cytotoxicities. Quimica Nova, v. 41, n. 8, p. 884-890, 2018.
DOI: 10.21577/0100-4042.20170258
ISSN: 0100-4042
Copyright: open access
Appears in Collections:BA - IGM - Artigos de Periódicos

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