RESUMEN
The phytochemical investigation of the twig and leaf extracts of Goniothalamus tamirensis led to the isolation and identification of 15 compounds including three rare previously undescribed styryllactones, goniotamirenones A-C, together with 12 known compounds. (Z)-6-Styryl-5,6-dihydro-2-pyranone and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one are reported here for the first time as previously undescribed natural products. Their structures were elucidated by spectroscopic methods. Goniotamirenone A was synthesized via a [2 + 2] cycloaddition reaction of 6-styrrylpyran-2-one in quantitative yield. The absolute configurations of goniotamirenones B and C were identified from experimental and calculated ECD data, while the absolute configurations of (-)-5-acetoxygoniothalamin, (-)-isoaltholactone, parvistone E, and 5-(1-hydroxy-3-phenyl-allyl)-dihydro-furan-2-one were identified by single-crystal X-ray diffraction analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with relevant compounds reported in the literature. (-)-5-Acetoxygoniothalamin exhibited potent cytotoxicity against the colon cancer cell line (HCT116) with an IC50 value of 8.6 µM which was better than the standard control (doxorubicin, IC50 = 9.7 µM), while (Z)-6-styryl-5,6-dihydro-2-pyranone was less active with an IC50 value of 22.1 µM.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Goniothalamus/química , Lactonas/farmacología , Fitoquímicos/farmacología , Extractos Vegetales/farmacología , Estirenos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Cristalografía por Rayos X , Teoría Funcional de la Densidad , Ensayos de Selección de Medicamentos Antitumorales , Células HCT116 , Humanos , Lactonas/química , Lactonas/aislamiento & purificación , Modelos Moleculares , Estructura Molecular , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Estirenos/química , Estirenos/aislamiento & purificaciónRESUMEN
The phytochemical investigation of the leaf extracts of Uvaria hamiltonii (Annonaceae) led to the isolation and identification of ten compounds including a new seco-cyclohexene (1) together with nine known compounds (2-10). Their structures were elucidated by intensive analysis by spectroscopic methods and comparisons of their spectroscopic data with those of compounds reported in the literature. Compounds 2, 8, and 9 showed potent α-glucosidase inhibitory activity with the IC50 values ranging from 2.6-7.1 µM.
Asunto(s)
Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Extractos Vegetales/química , Uvaria/química , Annonaceae/química , Ciclohexenos/aislamiento & purificación , Ciclohexenos/farmacología , Inhibidores de Glicósido Hidrolasas/farmacología , Estructura Molecular , Fitoquímicos/análisis , Fitoquímicos/farmacología , Hojas de la Planta/química , Análisis Espectral , alfa-Glucosidasas/efectos de los fármacosRESUMEN
Four new flavonoids (1-4), a new benzyl benzoate derivative (5), five new oxepinones (6-10), and 14 known compounds (11-24) were isolated from the leaf and twig extracts of Desmos cochinchinensis. Their structures were established by spectroscopic methods. The structure of 1 was also confirmed by X-ray diffraction data. The absolute configurations of 3, 4, and 6-10 were determined from comparisons of their ECD spectra with those of relevant reported compounds. Compounds 1, 2, 6, 8, 10, 12-15, and 17 showed α-glucosidase inhibitory activities with IC50 values ranging from 0.2 to 4.9 µM.
Asunto(s)
Annonaceae/química , Flavonoides/farmacología , Inhibidores de Glicósido Hidrolasas/farmacología , Oxepinas/farmacología , Extractos Vegetales/farmacología , Hojas de la Planta/química , alfa-Glucosidasas/efectos de los fármacos , Flavonoides/química , Inhibidores de Glicósido Hidrolasas/química , Estructura Molecular , Oxepinas/química , Extractos Vegetales/química , Análisis Espectral/métodos , Difracción de Rayos XRESUMEN
The first phytochemical investigation of Casearia graveolens twigs led to the isolation and identification of a new clerodane diterpene, caseariagraveolin (1), together with six known compounds (2-7). Their structures were elucidated by intensive analysis of their spectroscopic data. Compound 1 showed strong cytotoxicity against oral cavity and breast cancer cell lines with IC50 values of 2.48 and 6.63 µM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/química , Casearia/química , Diterpenos de Tipo Clerodano/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Diterpenos de Tipo Clerodano/farmacología , Humanos , Estructura MolecularRESUMEN
Phytochemical investigation of Garcinia propinqua roots led to the isolation and identification of a new xanthone, doitunggarcinone D (1), together with 15 known compounds (2-16). Their structures were elucidated by intensive analysis of spectroscopic data. Compounds 3, 6, 7, 14, 15 and 16 exhibited strong antibacterial activity against Bacillus subtilis TISTR 088 with MIC values in the range of 1-4 µg/mL. Compounds 3, 7, 10 and 14 also showed good antibacterial activity against B. cereus TISTR 688 with MIC values ranging from 4-8 µg/mL.