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Phytochemistry ; 223: 114139, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38750707

RESUMO

Eleven undescribed isoquinoline alkaloids (1-8, 14, 15, and 24), along with 19 analogues (9-13, 16-23, and 25-30) were isolated from the barks of Alangium salviifolium. The structures of the undescribed compounds were elucidated through the analysis of their HR-ESI-MS, 1D and 2D NMR, IR, UV, and X-ray diffraction. The absolute configuration of 8 was established via the ECD calculation. Notably, compounds 1/2 and 3/4 were two pairs of C-14 epimers. The isolated alkaloids were evaluated for their cytotoxicity against various cancer cell lines, including SGC-7901, HeLa, K562, A549, BEL-7402, HepG2, and B16, ß-carboline-benzoquinolizidine (14-22) and cepheline-type (24-28) alkaloids exhibited remarkable cytotoxicity, with IC50 values ranging from 0.01 to 48.12 µM. Remarkably, compounds 17 and 21 demonstrated greater cytotoxicity than the positive control doxorubicin hydrochloride. Furthermore, a significant proportion of these bioactive alkaloids possess a C-1' epimer configuration. The exploration of their structure-activity relationship holds promise for directing future investigations into alkaloids derived from Alangium, potentially leading to novel insights and therapeutic advancements.


Assuntos
Alcaloides , Antineoplásicos Fitogênicos , Ensaios de Seleção de Medicamentos Antitumorais , Isoquinolinas , Casca de Planta , Humanos , Alcaloides/química , Alcaloides/farmacologia , Alcaloides/isolamento & purificação , Casca de Planta/química , Isoquinolinas/química , Isoquinolinas/farmacologia , Isoquinolinas/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Estrutura Molecular , Relação Estrutura-Atividade , Linhagem Celular Tumoral , Alangiaceae/química , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga
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