RESUMO
Phytochemical analysis of Thevetia neriifolia seeds resulted in the isolation of one new (1) and 23 known (2ï¼24) cardenolide glycosides. The structure of 1 was determined based on one- and two-dimensional NMR spectroscopic analysis and acid hydrolytic cleavage reaction. The effect of the cytotoxic activity of 1ï¼24 on three human oral carcinoma cell lines was assessed. The cell lines included Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, HSC-4 human tongue carcinoma cells, and HGF human gingival fibroblast cells. The isolated compounds had a cytotoxic effect on the carcinoma cells with IC50 values ranging from 0.004 µM to 64.9 µM. The structure-activity relationship is also discussed.
Assuntos
Antineoplásicos Fitogênicos , Carcinoma , Thevetia , Antineoplásicos Fitogênicos/farmacologia , Cardenolídeos/farmacologia , Linhagem Celular , Glicosídeos/farmacologia , Humanos , SementesRESUMO
Seven new pregnane glycosides (1-7) and eight known compounds (8-15) were isolated from the bark of Marsdenia cundurango (Asclepiadaceae). The structures of 1-7 were determined by spectroscopic analysis, including two-dimension NMR spectroscopy, chemical transformations, and chromatographic analysis of the hydrolyzed products. The isolated compounds 1-15 were evaluated for their cytotoxic activity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and TIG-3 normal human lung cells, including apoptosis-inducing activity of a representative pregnane glycoside in HL-60 cells.
Assuntos
Citotoxinas/uso terapêutico , Glicosídeos/química , Células HL-60/metabolismo , Marsdenia/química , Casca de Planta/química , Pregnanos/química , Citotoxinas/farmacologia , HumanosRESUMO
Phytochemical investigation of the MeOH extract of the roots and rhizomes of Saposhnikovia divaricata (Umbelliferae) resulted in the isolation of six chromons (1-6)-and five polyacetylene derivatives (7-11). Compounds 9 and 11 were isolated from S. divaricate for the first time. The chromon derivatives -(1-6) were evaluated for their cytotoxic activity against HL-60 human promyclocytic leukemia cells. Compound 1 (3'-O-angeloylhamaudol) showed the most potent cytotoxic activity with an IC50 value of 4.41 µM and was found to induce apoptotic cell death in HL-60 cells. The loss of mitochondrial membrane potential, release of cytochrome c into the cytoplasm, and activation of caspase-9 in the 1-treated HL-60 cells suggests that I induces apoptosis through the mitochondial-dependent apoptotic pathway.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Apiaceae/química , Extratos Vegetais/farmacologia , Apoptose/efeitos dos fármacos , Células HL-60 , Humanos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Extratos Vegetais/análise , Raízes de Plantas/química , Rizoma/químicaRESUMO
Ten new triterpene glycosides, stryphnosides G-P (1-10), were isolated from the pericarps of Stryphnodendron fissuratum (Legminosae). The structures of 1-10 were determined based on spectroscopic analyses, including various two-dimensional NMR spectroscopic techniques, and the results of hydrolytic cleavage. The sugar moiety attached to C-3 of the aglycone of 4, 5, and 7-10 is composed of five or six monosaccharides, of which the terminal α-l-arabinosyl unit has a 1C4 conformation. Compounds 2 and 5 differ from the other isolates in having an α-l-rhamnosyl unit at the C-21 hydroxy group. The cytotoxic activity of 1-10, stryphnosides A-F (11-16), and their aglycones (1a, 11a, 14a, and 16a) against HL-60 cells was also examined.
Assuntos
Fabaceae/química , Glicosídeos/química , Triterpenos/química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células HL-60 , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Triterpenos/isolamento & purificação , Triterpenos/farmacologiaRESUMO
Six steroidal glycosides and 14 known compounds were isolated from the underground parts of Yucca glauca (Agavaceae). Their structures were determined from extensive spectroscopic analysis, including analysis of two-dimensional NMR data, and from chemical transformations. The compounds were also evaluated for cytotoxic activities against HL-60 human leukemia cells and A549 human lung adenocarcinoma cells. Four spirostanol glycosides and three furostanol glycosides exhibited cytotoxic activities against both HL-60 and A549 cells. Two of the compounds induced apoptosis in HL-60 cells.