RESUMO
Chemical investigation of the ethanol extract of the whole plant of Megacodon stylophorus led to the isolation and identification of two new seco-hopane triterpenoids, 2,3-seco-22(29)-hopene-2-carboxyl-3-aldehyde (1) and 2,3-seco-4(23),22(29)-hopene-2-carboxyl-3-aldehyde (2), along with 10 known compounds, 3-12. All the isolates were reported from this plant for the first time. The structures of compounds 1 and 2 were determined by detailed analysis of their spectral data including 1D and 2D NMR. In addition, compound 1 was further analyzed by X-ray crystallography. Compounds 1-3 were evaluated for their in vitro anti-proliferative activities on HeLa, MCF-7, and Hep-G2 tumor cell lines. Compound 2 was active against the three cell lines with IC50 values of 3.6, 7.5, and 13.6 µM, respectively, while compound 1 exhibited cytotoxicity on MCF-7 (IC50 14.0 µM) and HeLa (IC50 18.2 µM) cell lines. Antimicrobial activities of compounds 1-2 (minimum inhibitory concentration values in the range of 3.12-12.50 mg/mL) were also observed.
Assuntos
Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Gentianaceae/química , Extratos Vegetais/farmacologia , Triterpenos/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Cristalografia por Raios X , Feminino , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Triterpenos/química , Triterpenos/isolamento & purificaçãoRESUMO
Phytochemical investigation of the EtOH extract obtained from the root of the Euphorbia kansuensis Proch. grown in China resulted in the isolation of two novel norlathyrane diterpenes, named ekanpenoids A and B (1 and 2, resp.). Their structures were established by extensive 1D- and 2D-NMR spectroscopy, as well as other spectra. The isolated diterpenes exhibited potent cytotoxic activities against the HeLa and Hep-G2 cell lines with the IC50 values ranging from 3.6 to 9.7â µg/ml.
Assuntos
Antineoplásicos Fitogênicos/química , Diterpenos/química , Euphorbia/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/toxicidade , Sobrevivência Celular/efeitos dos fármacos , Diterpenos/isolamento & purificação , Diterpenos/toxicidade , Euphorbia/metabolismo , Células HeLa , Células Hep G2 , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Conformação Molecular , Raízes de Plantas/química , Raízes de Plantas/metabolismoRESUMO
Chemical investigation of the ethanolic extracts of the dried leaves of Bergenia purpurascens led to the isolation and identification of a new aromatic glycoside, 1-O-ß-D-glucopyranosyl-2-methoxy-3-hydroxyl-phenylethene (1), along with other 19 known compounds (2-20). The structure of compound 1 was determined by a detailed analysis using various analytical techniques, including 1D and 2D NMR. In vitro anti-proliferative activities of compound 1 on five human cancer cell lines were evaluated. The results showed that compound 1 possessed the most potent effects with the IC50 values of 14.36 ± 1.04 µM against T24 cells. The further bioactivity analysis showed that compound 1 induced apoptosis of T24 cells, and altered anti- and pro-apoptotic proteins, leading to mitochondrial dysfunction and activation of caspase-3 for causing cell apoptosis. The present investigation illustrated compound 1 might be used as a potential antitumour chemotherapy candidate.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Saxifragaceae/química , Antineoplásicos Fitogênicos/química , Apoptose/efeitos dos fármacos , Caspase 3/metabolismo , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Simulação de Acoplamento Molecular , Estrutura Molecular , Extratos Vegetais/química , Folhas de Planta/química , Plantas Medicinais/química , Proteínas Proto-Oncogênicas c-bcl-2/química , Proteínas Proto-Oncogênicas c-bcl-2/metabolismoRESUMO
Chemical constituents of the dried aerial parts of Euphorbia nematocypha were investigated. A new oleanane triterpenoid, trans, trans-2',4'- hexadienedioicacid-1'-ß-amyrin ester (1), together with, ß-amyrin (2), ß-amyrin acetate (3), betulinic acid (4), ellagic acid (5), oleanolic acid (6), ß-sitosterol (7), kaempferol (8), quercetin (9), lupeol (10) and pseudo-taraxasterol (11) were isolated from the methylene chloride extract. Their structures were elucidated on the basis of extensive spectroscopic (1D- & 2D-NMR) and ESI-MS analysis and comparison with data reported in the literature. The new isolated triterpenoid showed moderate cytotoxic activities against HeLa and MCF-7cell lines.
Assuntos
Euphorbia/química , Componentes Aéreos da Planta/química , Triterpenos/química , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Estrutura Molecular , Ácido Oleanólico/análogos & derivadosRESUMO
Two new sesquiterpenes, together with 32 known compounds(3-34), were isolated from Artemisia sieversiana Ehrhart ex willd. and the compounds 3-21 were isolated from this plant for the first time. The new compounds were elucidated as 2α,9α-dihydroxymuurol-3(4)-en-12-oic acid (1) and 13α-methyl-(5αH,6αH,7αH,8αH)-austricin 8-O-ß-D-glucopyranoside (2), respectively. The structural identification of these compounds was mainly achieved by spectroscopic methods including 1D and 2D NMR techniques, and the structure of compound 1 was confirmed by a single crystal X-ray diffraction experiment. Compounds 1-2 were evaluated for cytotoxic activity in vitro against MCF-7, NCI-H460 and Hep-G2 cell lines, respectively.
Assuntos
Artemisia/química , Sesquiterpenos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Células Hep G2 , Humanos , Células MCF-7 , Estrutura Molecular , Sesquiterpenos/químicaRESUMO
A phytochemical study of the ethanolic extract of Chrysosplenium carnosum Hook. f. et Thoms. led to the isolation of two new oleanane-type triterpenoids, 6ß-hydroxy-3-oxoolean-12-en-27-oic acid (1) and 3ß, 21α-dihydroxyolean-12-en-27-oic acid (2), along with fourteen known compounds (3-16), all of which were isolated from this plant for the first time. The structures of these compounds were established on the basis of spectroscopic methods. Compounds 1-4 were evaluated for their in vitro anti-tumor activities on B16F10, SP2/0 and Hep-G2 cells lines. Compounds 1, 3 and 4 exhibited strong inhibitory activity against B16F10 and SP2/0 cells' growth, compared with moderate cytotoxic activity against Hep-G2 cells. However, compound 2 showed to be inactive against these tumor cells.