RESUMO
Fractionation of the chloroform extract from the aerial part of Argemone mexicana led to the isolation of two benzophenanthridine-type alkaloids, N-demethyloxysanguinarine and pancorine; three benzylisoquinoline-type alkaloids, (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxyisoquinoline, (+)-higenamine and (+)-reticuline. Among them, N-demethyloxysanguinarine is a new compound, and (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxy-isoquinoline was isolated form a natural source for the first time, to which was assigned a trivial name, (+)-argenaxine. In addition, six known non-alkaloidal compounds were also isolated and identified. All compounds were characterized on the basis of their spectral data and chemical evidences. Some isolated alkaloids from this species were evaluated for their cytotoxicity to human nasopharyngeal carcinoma (HONE-1) and human gastric cancer (NUGC) cell lines. Chelerythrine was found to exhibit significant activity against NUGC cell line, while angoline inhibited both types. (+)-Argenaxine showed moderate activity against the NUGC cell line.
Assuntos
Alcaloides/toxicidade , Argemone/química , Sobrevivência Celular/efeitos dos fármacos , Isoquinolinas/toxicidade , Fenantridinas/isolamento & purificação , Fenantridinas/toxicidade , Componentes Aéreos da Planta/química , Alcaloides/química , Alcaloides/isolamento & purificação , Humanos , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Modelos Moleculares , Estrutura Molecular , Neoplasias Nasofaríngeas , Fenantridinas/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Neoplasias Gástricas , Células Tumorais CultivadasRESUMO
Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argemone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[ c]phenanthridine (+/-)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 microg/mL and 14.6, respectively.
Assuntos
Alcaloides/farmacologia , Fármacos Anti-HIV/farmacologia , Argemone , Alcaloides de Berberina , HIV-1/efeitos dos fármacos , Fenantrenos/farmacologia , Fitoterapia , Extratos Vegetais/farmacologia , Alcaloides/administração & dosagem , Alcaloides/química , Alcaloides/uso terapêutico , Fármacos Anti-HIV/administração & dosagem , Fármacos Anti-HIV/química , Fármacos Anti-HIV/uso terapêutico , Benzofenantridinas , Infecções por HIV/tratamento farmacológico , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Fenantrenos/administração & dosagem , Fenantrenos/uso terapêutico , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Relação Estrutura-AtividadeRESUMO
Three new eudesmanolide sesquiterpenes, neolitacumone A-C (1-3), and one new benzylisoquinoline alkaloid, neolitacumonine (5), along with 27 known compounds were isolated from the stem bark of Neolitsea acuminatissima. The structures of compounds 1-3 and 5 were established on the basis of spectral and chemical evidence. Compounds 2, 3, and 20 were selectively inhibitory to Hep 2,2,15 cells with IC50 values in the range 0.24-0.04 microg/mL. Compound 20 was marginally cytotoxic to Hep G2 cells.
