Chemical composition of aspidosperma ulei markgr. and antiplasmodial activity of selected indole alkaloids

• Autor(a) principal: Torres, Zelina Estevam dos Santos
• Data de Publicação: 2013
• Outros Autores: Silveira, Edilberto Rocha, Silva, Luiz Francisco Rocha e, Lima, Emerson Silva, Vasconcellos, Marne Carvalho de, Andrade Uchôa, Daniel Esdras de, Filho, Raimundo Braz, Pohlit, Adrian Martin
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional do INPA
• Texto Completo: https://repositorio.inpa.gov.br/handle/1/16063
• topic: Antimalarial Agent; Indole Alkaloid; Plant Extract; Antimalarial Agent; Indole Alkaloid; 3t3 Cell Line; Animals; Aspidosperma; Chemical Structure; Chemistry; Drug Effects; Drug Sensitivity; Ic 50; Isolation And Purification; Mouse; Plasmodium Falciparum; Toxicity; Aspidosperma; Cell Strain 3t3; Chemistry; Drug Effect; Ic 50; Animal; Antimalarials; Aspidosperma; Indole Alkaloids; Inhibitory Concentration 50; Mice; Molecular Structure; Nih 3t3 Cells; Parasitic Sensitivity Tests; Plant Extracts; Plasmodium Falciparum; Animal; Antimalarials; Aspidosperma; Indole Alkaloids; Inhibitory Concentration 50; Mice; Molecular Structure; Nih 3t3 Cells; Parasitic Sensitivity Tests; Plant Extracts; Plasmodium Falciparum

A new indole alkaloid, 12-hydroxy-N-acetyl-21(N)-dehydroplumeran-18-oic acid (13), and 11 known indole alkaloids: 3,4,5,6-tetradehydro-β-yohimbine (3), 19(E)- hunteracine (4), β-yohimbine (5), yohimbine (6), 19,20-dehydro-17-α-yohimbine (7), uleine (10), 20-epi-dasycarpidone (11), olivacine (8), 20-epi-N-nor-dasycarpidone (14), N-demethyluleine (15) and 20(E)-nor-subincanadine E (12) and a boonein △-lactone 9, ursolic acid (1) and 1D,1O-methyl-chiro-inositol (2) were isolated from the EtOH extracts of different parts of Aspidosperma ulei Markgr. (Apocynaceae). Identification and structural elucidation were based on IR, MS, 1H- and 13C-NMR spectral data and comparison to literature data. The antiplasmodial and antimalarial activity of 1, 5, 6, 8, 10 and 15 has been previously evaluated and 1 and 10 have important in vitro and in vivo antimalarial properties according to patent and/or scientific literature. With the aim of discovering new antiplasmodial indole alkaloids, 3, 4, 11, 12 and 13 were evaluated for in vitro inhibition against the multi-drug resistant K1 strain of the human malaria parasite Plasmodium falciparum. IC50 values of 14.0 (39.9), 4.5 (16.7) and 14.5 (54.3) μg/mL (μM) were determined for 3, 11 and 12, respectively. Inhibitory activity of 3, 4, 11, 12 and 13 was evaluated against NIH3T3 murine fibroblasts. None of these compounds exhibited toxicity to fibroblasts (IC50 > 50 μg/mL). Of the five compounds screened for in vitro antiplasmodial activity, only 11 was active. © 2013 by the authors.