RESUMO
Eight new amide alkaloids (1-8) and 19 known ones were isolated from the whole plant of Piper boehmeriaefolium. Their structures were determined through spectroscopic data analyses. Cytotoxic activity of these amides against human cervical carcinoma HeLa cells was evaluated, and 1-[(9E)-10-(3,4-methylenedioxyphenyl)-9-decenoyl]pyrrolidine (9) exhibited significant inhibitory activity with an IC(50) value of 2.7 µg/mL.
Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Amidas/isolamento & purificação , Amidas/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Piper/química , Pirrolidinas/isolamento & purificação , Pirrolidinas/farmacologia , Alcaloides/química , Amidas/química , Antineoplásicos Fitogênicos/química , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Feminino , Células HeLa , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Pirrolidinas/química , EstereoisomerismoRESUMO
A new piperidine alkaloid and three known tetranortriterpenoids were isolated from the methanol extracts of the rhizomes of Arisaema decipiens Schott (Araceae) and their chemical structures were identified as (-)-(2R*,3S*,6S*)-N,2-dimethyl-3-hydroxy-6-(9-phenylnonyl) piperidine (1), 6-deacetylnimbin (2), 28-deoxonimbolide (3) and nimbin (4). The N-methylated derivative (1a) of 1 was synthesized. Compound 1 exhibited weak inhibitory activity against the MCF-7 cell line, while compound 1a showed potential inhibitory activity against the MCF-7 cell line with an IC50 value of 4.6 µM and weak inhibitory activity against K562 and SK-OV-3 cells. This plant in genus Arisaema is firstly reported as the source of limonoids that are considered a natural antitumor herbal medicine.
Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Arisaema/química , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Limoninas/análise , Limoninas/química , Piperidinas/síntese química , Piperidinas/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/isolamento & purificação , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/patologia , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Etnicidade , Feminino , Humanos , Limoninas/síntese química , Limoninas/isolamento & purificação , Limoninas/farmacologia , Imageamento por Ressonância Magnética , Neoplasias Ovarianas/tratamento farmacológico , Neoplasias Ovarianas/patologia , Piperidinas/química , Piperidinas/isolamento & purificação , Rizoma/químicaRESUMO
Palhinine A, a novel C(16)N-type Lycopodium alkaloid with a unique 5/6/6/9 tetracyclic ring system, was isolated from the whole plant of Palhinhaea cernua L. (Lycopodiaceae). Its structure was elucidated by spectroscopic methods, and the absolute configuration was determined by single-crystal X-ray diffraction analysis using the Flack parameter. Palhinine A is reported as the first example of Lycopodium alkaloids of which C-16 is fused to a new ring through a C-16-C-4 lingkage.