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1.
Nat Prod Res ; 35(22): 4388-4393, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31967486

RESUMO

Phytochemical analysis of Thevetia neriifolia seeds resulted in the isolation of one new (1) and 23 known (2-24) 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 1-24 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 , Sementes
2.
J Nat Med ; 73(1): 93-103, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30251034

RESUMO

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 , Humanos
3.
Nat Prod Commun ; 12(2): 255-258, 2017 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30428224

RESUMO

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/química
4.
Carbohydr Res ; 434: 18-26, 2016 Nov 03.
Artigo em Inglês | MEDLINE | ID: mdl-27518204

RESUMO

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/farmacologia
5.
Phytochemistry ; 101: 109-15, 2014 May.
Artigo em Inglês | MEDLINE | ID: mdl-24612536

RESUMO

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.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Glicosídeos/farmacologia , Esteroides/farmacologia , Yucca/química , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/isolamento & purificação , Células HL-60 , Humanos , Estrutura Molecular , Estruturas Vegetais/química , Esteroides/isolamento & purificação
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