RESUMO
Ten cardiac glycosides (1-10) including six 20,22-dihydrodigitoxigenin and four gitoxigenin glycosides were isolated from the stems of Vallaris glabra together with six known triterpenoid cinnamates. Spectroscopic data of these previously undescribed compounds are reported. All isolates were evaluated for their growth inhibitory activities against three cancer cell lines, and compound 2 was the most active against KB cells with an IC50 value of 0.03 ± 0.001 µM. Also, compounds 1, 3, 5, and 6 and the triterpenoid cinnamates 11-13 showed inhibitory activity (IC50 < 10 µM) for one or more of the cell lines used.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Digitoxigenina/análogos & derivados , Glicosídeos/química , Caules de Planta/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Digitoxigenina/química , Digitoxigenina/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Análise Espectral/métodosRESUMO
Five 12,20-epoxypregnane glycosides (1-3, 5, and 6) and two 11,12-seco-pregnane glycosides (4 and 7) with spirodilactone motifs, as well as spirodilactone cleavage products 8 and 9, were isolated from the stems of Hoya kerrii. The relative configurations of the three related skeletons were supported by ROESY experiments and X-ray crystallographic analyses. The isolates were evaluated for their anti-inflammatory activity based on the inhibition of NO production in RAW264.7 cells, and some showed IC50 values ranging from 12.6 to 96.5 µM. The most potent compound, 9a, was also examined for its anti-inflammatory mechanism against mRNA expression and was found to down-regulate mRNA expression of iNOS and COX-2 in a dose-dependent manner.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Apocynaceae/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Pregnanos/isolamento & purificação , Pregnanos/farmacologia , Animais , Anti-Inflamatórios/química , Cristalografia por Raios X , Ciclo-Oxigenase 2/efeitos dos fármacos , Ciclo-Oxigenase 2/metabolismo , Relação Dose-Resposta a Droga , Glicosídeos/química , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/metabolismo , Camundongos , Conformação Molecular , Estrutura Molecular , Óxido Nítrico/biossíntese , Óxido Nítrico Sintase Tipo II/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Caules de Planta/química , Pregnanos/química , TailândiaRESUMO
Thirteen cardenolide glycosides (1-13) were isolated from the CH2Cl2 and MeOH extracts of Vallaris glabra leaves. The structures of the new compounds (2-13) were identified by spectroscopic methods, with the absolute configurations of the sugar moieties determined by acid hydrolysis. All compounds were evaluated for their cytotoxic activity against human cervix adenocarcinoma, lung carcinoma, and colorectal adenocarcinoma cell lines. The two most potent compounds [2'-O-acetylacoschimperoside P (1) and oleandrigenin-3-O-α-l-2'-O-acetylvallaropyranoside (2)] exhibited IC50 values in the range of 0.03-0.07 µM.
Assuntos
Glicosídeos Cardíacos/isolamento & purificação , Glicosídeos Cardíacos/farmacologia , Antineoplásicos Fitogênicos/química , Apocynaceae/química , Cardenolídeos , Glicosídeos Cardíacos/química , Feminino , Glicosídeos/química , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta , Tailândia , Neoplasias do Colo do Útero/tratamento farmacológicoRESUMO
Two 15beta-hydroxycardenolides (1,2) and a 16alpha-hydroxycalactinic acid methyl ester (3) along with eleven known compounds including 16alpha-hydroxycalotropagenin, coroglaucigenin, 16alpha-hydroxycalotropin, calactinic acid, calotoxin, 6'-O-(E-4-hydroxycinnamoyl)desglucouzarin, 12beta-hydroxycoroglaucigenin, frugoside, calotropagenin, 9,12,13-trihydroxyoctadeca-10(E),15(Z)-dienoic acid and R-(-)-mevalonolactone were isolated from the polar fraction of the CH(2)Cl(2) extract, and n-BuOH extract of the leaves of this plant. The isolated compounds were evaluated for their inhibitory activities against a panel of cell lines.
Assuntos
Antineoplásicos/química , Calotropis/química , Cardenolídeos/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Cardenolídeos/química , Cardenolídeos/isolamento & purificação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Concentração Inibidora 50 , Células KB , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Extratos Vegetais/químicaRESUMO
Sixteen compounds including dihydroxy prenylfuranocoumarins/3-hydroxy-3-methylglutaric acid conjugates and dihydroxy prenylfuranocoumarins/3-hydroxy-3-methylglutaric acid/1-O-flavonyl-ß-d-glucopyranoside conjugates, together with other dihydroxyprenylfuranocoumarins conjugates, were isolated from the ethyl acetate extract of the fruit peels of Citrus hystrix. Some of the isolates were evaluated for their cholinesterase inhibitory activity, but only one compound possessing a 3-O-ß-d-glucopyranosyl-3,5,7,4'-tetrahydroxy-6,8,3'-trimethoxyflavonol nucleus in the prenylfuranocoumarin-HMGA conjugate showed strong activity.