RESUMEN
Fifteen previously undescribed 2-(2-phenylethyl)chromone dimers, along with two known analogues were isolated from Chinese agarwood (Aquilaria sinensis) by a LC-MS-guided fractionation procedure. Their structures were elucidated on the basis of spectroscopic and spectrometric data (1D and 2D NMR, IR, and HRESIMS). The isolated compounds exhibited significant inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW264.7â¯cells with IC50 values in the range 0.6-37.1⯵M.
Asunto(s)
Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , Cromonas/química , Thymelaeaceae/química , Animales , Antiinflamatorios no Esteroideos/aislamiento & purificación , Cromatografía Liquida , Cromonas/aislamiento & purificación , Dimerización , Evaluación Preclínica de Medicamentos/métodos , Concentración 50 Inhibidora , Lipopolisacáridos/farmacología , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Óxido Nítrico/antagonistas & inhibidores , Óxido Nítrico/metabolismo , Plantas Medicinales/química , Células RAW 264.7 , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Five new 2-(2-phenylethyl)chromone derivatives (1-5), along with eleven known compounds (6-16) were isolated from Chinese agarwood. Their structures were elucidated by spectroscopic data (NMR, UV, IR, and MS) analyses and comparison of their spectroscopic and physical data with the literature values. The absolute configurations of 2-4 were determined by electronic circular dichroism (ECD) calculations. Compounds 2-4, 11, 12, and 15 exhibited significant inhibition of nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 cells with IC50 values in the range 1.6-7.3µM.
Asunto(s)
Antiinflamatorios/química , Flavonoides/química , Thymelaeaceae/química , Animales , Antiinflamatorios/aislamiento & purificación , Flavonoides/aislamiento & purificación , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7 , Madera/químicaRESUMEN
A quantitative HPLC-DAD method was developed for simultaneous determination of N-trans-p-coumaroyloctopamine and N-trans-p-coumaroyltyramine in Solani Melongenae Radix from different cultivation regions in China The separation was performed on an Agilent Eclipse XDB C18 column (4.6 mm x 250 mm, 5 microm) at 30 degrees C with a gradient elution of methanol and 0.1% formic acid in water as mobile phase. The flow rate was set at 1.0 mL x min(-1) and the detection wavelength was 300 nm. The calibration curves of N-trans-p-coumaroyloctopamine and N-trans-p-coumaroyltyramine were linear over the ranges of 2.84-68.16, 3.10-74.40 mg x L(-1), and the average recoveries (n = 9) were 99.30% and 102.8%, respectively. The developed method was successfully applied for the analysis of sixteen samples from different cultivation regions in China, which indicated that the method is simple, rapid, accurate, and reliable for quality evaluation of Solani Melongenae Radix.
Asunto(s)
Amidas/análisis , Cromatografía Líquida de Alta Presión/métodos , Medicamentos Herbarios Chinos/análisis , Raíces de Plantas/química , Solanaceae/química , China , Solanaceae/clasificaciónRESUMEN
Six new polyoxygenated triterpenoids, cannabifolins A-F (1-6), and eight known triterpenoids, 7-14, were isolated from the leaves of Vitex negundo var. cannabifolia. The absolute configuration of cannabifolin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 1 and 2 represent a class of rare natural pentacyclic triterpenoids bearing cis-fused C/D rings and are the first examples of 12,19-epoxy ursane- and oleanane-type triterpenoids. Compounds 3, 7, 8, and 14 exhibited inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values in the range 24.9-40.5 µM.
Asunto(s)
Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Ácido Oleanólico/análogos & derivados , Vitex/química , Animales , Antiinflamatorios/química , Cristalografía por Rayos X , Medicamentos Herbarios Chinos/química , Lipopolisacáridos/farmacología , Macrófagos/efectos de los fármacos , Ratones , Conformación Molecular , Estructura Molecular , Óxido Nítrico/biosíntesis , Ácido Oleanólico/química , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/farmacología , Hojas de la Planta/químicaRESUMEN
Four new lignanamides, melongenamides A-D (1-4), together with six known ones (5-10), were isolated from the roots of Solanum melongena L. Their structures were elucidated on the basis of 1D and 2D NMR experiments and by comparison of their spectroscopic and physical data with the literature values. Compounds 2-8 exhibited inhibitions of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values ranging from 16.2 to 58.5 µM.
Asunto(s)
Amidas/química , Antiinflamatorios/farmacología , Lignanos/química , Macrófagos/efectos de los fármacos , Solanum melongena/química , Amidas/aislamiento & purificación , Amidas/farmacología , Animales , Antiinflamatorios/aislamiento & purificación , Concentración 50 Inhibidora , Lignanos/aislamiento & purificación , Lignanos/farmacología , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Raíces de Plantas/químicaRESUMEN
Ten new labdane diterpenoids, lagopsins A-H (1-3, 5, 7-10) and 15-epi-lagopsins C and D (4, 6), together with five known labdane diterpenoids (11-15), were isolated from the whole plants of Lagopsis supina. The absolute configuration of lagopsin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 7, 9, 13, and 15 exhibited moderate inhibition of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells with IC50 values in the range 14.9-34.9 µM.