RESUMO
One new cycloartane-type triterpenoid, named macrobidoupoic acid A (as an C-24 epimeric mixture, 4a, 4 b), together with three known ones (1-3), were clarified by different chromatography from the M. bidoupensis whole plants. Triterpenoids (1, 3 & 4) were detected for the first time from the Macrosolen genus. Chemical structures of them were illuminated using HR-ESI-MS, and NMR (1 D & 2 D) assessments. The cytotoxic properties of triterpenoids (3 & 4) were examined against two human cancer cell lines (A549, and RD) by MTT assay. As results shown, triterpenoids (3 & 4) possessed moderate cytotoxic activity against A549 and RD cancer cells (IC50 ranged from 5.44 to 39.52 µM).
Assuntos
Triterpenos , Estrutura Molecular , Triterpenos/química , Triterpenos/farmacologiaRESUMO
From the leaves of Schefflera sessiliflora De P. V., two new triterpene saponins including one oleanane-type saponin, named scheffleraside C (1) and one lupane-type saponin scheffleraside D (2), together with six known triterpene saponins (3-8), were isolated by various chromatography methods. Among them, 3 was found for the first time from natural sources, while 6-8 were isolated for the first time from the genus Schefflera. Their structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments, and comparison of their NMR data with previously reported data. Their α-glucosidase inhibition and cytotoxic activity against MCF-7 human breast cancer cell lines were evaluated. The isolates (1, 3-5, 8) showed stronger α-glucosidase inhibitory activity (IC50 = 5.99-76.58 µM) than the standard drug acarbose (IC50 = 214.50 µM). At the concentration of 100 µg/ml, the isolates (1, 2) showed appreciable cytotoxic activity (67.92, 63.83%, respectively).
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Araliaceae/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/farmacologia , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/farmacologia , Saponinas/isolamento & purificação , Saponinas/farmacologia , Triterpenos/isolamento & purificação , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Inibidores de Glicosídeo Hidrolases/química , Humanos , Hipoglicemiantes/química , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Folhas de Planta/química , Saponinas/química , Triterpenos/químicaRESUMO
The phytochemical composition of the Combretum trifoliatum leaves was studied for the first time. Two new triterpenoid saponins, named comtrifoside A (1) and comtrifoside B (2), together with two other saponins (3-4) were purified by variously chromatographic techniques. For the first time, compound 3 was informed from the Combretum genus, as well as all of the isolated compounds (1-4) were reported from C. trifoliatum. The chemical structures of them were clearly characterised using extensive UV-VIS, IR, HRMS-ESI, and NMR experimental data. The in vitro anti-inflammatory activities of 1 & 2 were examined against NO overproduction in LPS activation of RAW264.7.
RESUMO
A new benzofuran derivative, nervione (1), was isolated from Nervilia concolor (Blume) Schltr. (Orchidaceae). Eight previously reported compounds were also isolated: 5,7-dimethoxyflavone (2), 3,5,7-trimethoxyflavone (3), 7-methoxyflavone (4), 3,7-dimethoxy-5-hydroxyflavone (5), tetramethylscutellarein (4',5,6,7-tetramethoxyflavone) (6), 5,7-dimethoxy-4'-hydroxyflavone (7), rhamnetin (8), and 5,7-dihydroxy-3',4'-dimethoxyflavone (9). The structures were elucidated by 1D, 2D NMR, and HRESIMS spectroscopy in addition to the literature. The relative configuration of 1 was defined using DP4+ probability while its absolute configuration was defined by comparison of the ECD spectrum of 1 with those of previously reported compounds. All isolated compounds were evaluated for alpha-glucosidase inhibition, revealing weak or no activity.[Formula: see text].
Assuntos
Benzofuranos , Orchidaceae , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Orchidaceae/química , alfa-GlucosidasesRESUMO
From the Vietnamese plant Macrosolen tricolor (Lecomte) Danser, one new diarylpropanoid, named macrotricolorin A (1) together with three diarylheptanoids including bisdemethoxycurcumin (2), demethoxycurcumin (3) and curcumin (4), were isolated. Their structures were elucidated by intensive analyses of their IR, UV, HR-ESI-MS and NMR (1 D & 2 D) spectra. It is the first time that diarylalkanoids have been reported from the genus Macrosolen. Compound 1 exhibited anti-inflammatory activity against the nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 with an IC50 value of 27.54 ± 1.75 µM.
Assuntos
Loranthaceae , Anti-Inflamatórios/farmacologia , Povo Asiático , Humanos , Lipopolissacarídeos , Óxido NítricoRESUMO
From the leaves of Markhamia stipulata var. canaense V.S. Dang, one new phytosphingolipid, named markhasphingolipid A (6) together with five known compounds, 4',7-O-dimethylapigenin (1), narigenin (2), tectoquinone (3), mollic acid (4), 1-hexadecanoyl-sn-glycerol (5) were classified by various chromatographic methods. Their structures were designated by IR, UV, HR-ESI-MS, HR-ESI-MS/MS and NMR experiments. All compounds were recognized for the first time from this species. The cytotoxicity of all n-hexane fractions and isolated compounds (5 & 6) against three human cancer cell lines (HeLa, HepG2, and MCF-7) were evaluated by SRB assay. All n-hexane fractions expressed cytotoxic effect on three tested cancer cell lines (at the concentration of 100 µg/mL, percent of cytotoxicity ranged from 55.81% to 95.83%) as well as compound 5 (IC50 ranged from 48.51 to 63.30 µM) whereas fraction H.I and compound 6 did not show activity.[Formula: see text].
Assuntos
Bignoniaceae/química , Folhas de Planta/química , Esfingolipídeos/isolamento & purificação , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Células HeLa , Humanos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Análise Espectral , Esfingolipídeos/química , Esfingolipídeos/farmacologiaRESUMO
One new cycloartane triterpenoid, named markhacanasin C (1), together with three known triterpenoids, oleanolic acid (2), ursolic acid (3) and 6ß,19α-dihydroxyursolic acid (4) were isolated by various chromatographic methods from the most cytotoxic fraction of the ethyl acetate extract of Markhamia stipulata var. canaense V.S. Dang leaves. Among them, 4 was reported for the first time from the genus Markhamia, while 2 and 3 were found for the first time from this species. Their structures were elucidated by IR, UV, HR-ESI-MS and NMR experiments. The cytotoxicity of isolated compounds (3 and 4) against three human cancer cell lines (HeLa, HepG2, and MCF-7) were evaluated. At the concentration of 100 µg/mL, 3 exhibited significant cytotoxic activity (86.36 ± 3.69%).
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Bignoniaceae/química , Triterpenos/química , Triterpenos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Células Hep G2 , Humanos , Células MCF-7 , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Extratos Vegetais/química , Folhas de Planta/química , Espectrometria de Massas por Ionização por Electrospray , Triterpenos/isolamento & purificação , Ácido UrsólicoRESUMO
One new flavonol glycoside named visconoside C (1), together with seven known flavonol glycosides, quercetin 3-O-ß-d-glucopyranoside 7-O-α-l-rhamnopyranoside (2), quercetin 7-O-α-l-rhamnopyranoside (3), astragalin (4), kaempferol 3-O-(4-O-acetyl)-α-l-rhamnopyranoside (5), kaempferol 7-O-α-l-rhamnopyranoside (6), kaempferitrin (7) and kaempferol 3-O-ß-d-glucopyranoside 7-O-α-l-rhamnopyranoside (8) were isolated by various chromatography methods from the leaves of Cleome viscosa L. Their structures were elucidated by IR, UV, HR-ESI-MS and NMR (1D & 2D) experiments. The cytotoxicity and hepatoprotective activities using HepG2 human hepatoma cell line of 1 were measured by MTT assay. At the concentration of 25 µM and 50 µM, 1 showed cytotoxic activity against HepG2 cells (cell viability was decreased to 22.2 and 23.0%, respectively, compared with doxorubicin control), while at the concentration of 100 µM, 1 showed hepatoprotective activity against CCl4-induced hepatotoxicity on HepG2 cells (34.3%, compared with quercetin control).
Assuntos
Cleome/química , Flavonoides/farmacologia , Substâncias Protetoras/química , Substâncias Protetoras/farmacologia , Avaliação Pré-Clínica de Medicamentos/métodos , Flavonoides/química , Glicosídeos/química , Glicosídeos/farmacologia , Células Hep G2 , Humanos , Quempferóis/química , Quempferóis/isolamento & purificação , Quempferóis/farmacologia , Fígado/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Folhas de Planta/química , Espectrometria de Massas por Ionização por Electrospray , VietnãRESUMO
From the fruit of Pandanus tectorius Parkinson ex Du Roi, one new (1) and six known aldehyde compounds (2-7) were isolated by various chromatography methods. Based on their spectroscopic data, these compounds were identified as (Z)-4-hydroxy-3-(4-hydroxy-3-methylbut-2-en-1-yl) benzaldehyde (1), p-hydroxybenzaldehyde (2), syringaldehyde (3), (E)-ferulaldehyde (4), (E)-sinapinaldehyde (5), vanillin (6) and 5-hydroxymethylfurfual (7). The α-glucosidase inhibitory activity of all compounds was measured. The isolated compounds (1-6) showed better α-glucosidase inhibitory activity (IC50 values ranging from 36.5 to 192.4 µM) than the standard drug acarbose (IC50 = 214.5 µM).
Assuntos
Aldeídos/química , Benzaldeídos/química , Frutas/química , Pandanaceae/química , Aldeídos/isolamento & purificação , Benzaldeídos/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , VietnãRESUMO
From the leaves of Schefflera sessiliflora De P. V., one new C20-gibberellin diterpene 2ß,12ß-dihydroxygibberellin (12ß-hydroxy-GA110 or 2ß-hydroxy-GA112) (1), together with three known compounds, trans-tiliroside (2), kaempferol 3-O-ß-D-glucuronopyranoside (3), 5-p-trans-coumaroylquinic acid (4), was isolated for the first time from the genus Schefflera by various chromatography methods. Their structures were elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and comparison with previous reported data. The α-glucosidase inhibitory activity of all compounds was measured. The isolates (2, 3) showed better α-glucosidase inhibitory activity (IC50 = 134.60, 147.10 µM, respectively) than the standard drug acarbose (IC50 = 214.50 µM).