RESUMEN
Seventeen compounds were isolated from the 95% ethanol extract of the stems and leaves of Sapium discolor by using various chromatographic techniques,including silica gel,Sephadex LH-20,MCI,ODS,and semi-preparative HPLC. Their structures were elucidated as sapiumin F( 1),kadsulignan C( 2),ciwujiatone( 3),ethylbrevifolin carboxylate( 4),7-hydroxy-8-methoxycoumarin( 5),fraxetin( 6),fraxidin( 7),isofraxidin( 8),6,7,8-trimethoxycoumarin( 9),5,6,7,8-tetramethoxycoumarin( 10),8-hydroxy-5,6,7-trimethoxycoumarin( 11),3,3'-di-O-methylellagic acid( 12),3,3',4'-tri-O-methylellagic acid( 13),3'-methoxyellagic acid 4'-O-α-rhamnopyranoside( 14),4,5-didehydro-chebulic acid triethyl ester( 15),ent-kaurane-3-oxo-16α,17-diol( 16),and abscisic acid( 17) by spectroscopic data. Compound 1 is a new compound. Except for compounds 4,11,and 13,the remaining compounds were isolated from this plant for the first time. All the isolates were evaluated for their in vitro antineuroinflammatory activities,and the results showed that compounds 6 and 15 significantly inhibited nitric oxide production in lipopolysaccharide-induced BV-2 microglial cells,with IC50 values of 6. 06 and 6. 05 µmol·L-1,respectively.
Asunto(s)
Fitoquímicos/análisis , Hojas de la Planta/química , Tallos de la Planta/química , Sapium/química , Animales , Línea Celular , Cromatografía Líquida de Alta Presión , RatonesRESUMEN
Seventeen compounds, including three new pairs of coumarinolignoid enantiomers, (7' S,8' S)-sapiumins A-C (1a-3a) and (7' R,8' R)-sapiumins A-C (1b-3b), six new taraxerane triterpenoids, sapiumic acids A-F (4-9), and five known taraxerane triterpenoids (10-14), were isolated from an ethanol extract prepared from the stems and leaves of Sapium discolor. The structures of 1-9 and their relative configurations were determined by spectroscopic data analysis, and the absolute configurations of the coumarinolignoids 1a/1b-3a/3b and triterpenoids 6-9 were assigned using experimental and calculated ECD data. Compounds 1a/1b-3a/3b are the first coumarinolignoids to be reported from the genus Sapium. Among all the isolates, compounds 1b, 2a/2b, 3a/3b, and 6-9 inhibited nitric oxide production in lipopolysaccharide-stimulated BV-2 microglial cells, with IC50 values of 1.7-15.3 µM.
Asunto(s)
Cumarinas/aislamiento & purificación , Cumarinas/farmacología , Microglía/metabolismo , Óxido Nítrico/biosíntesis , Ácido Oleanólico/análogos & derivados , Sapium/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Línea Celular , Dicroismo Circular , Humanos , Espectroscopía de Resonancia Magnética , Microglía/efectos de los fármacos , Estructura Molecular , Óxido Nítrico/antagonistas & inhibidores , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Tallos de la Planta/químicaRESUMEN
A new cytisine-type alkaloid, (-)-N-hexanoylcytisine (1), and a new isoflavan, (3S, 4R)-4-hydroxy-7,4'-dimethoxyisoflavan 3'-O-ß-d-glucopyranoside (2), along with 10 known compounds, were isolated from the rhizomes of Sophora tonkinensis. Their structures were determined by spectroscopic methods, chemical evidence, and ECD data analysis. All of the isolates were evaluated for their cytotoxic activities against four human tumor cell lines.
Asunto(s)
Alcaloides/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Alcaloides/química , Antineoplásicos Fitogénicos/química , Azocinas , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Flavonoides/química , Células Hep G2 , Humanos , Isoflavonas , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Raíces de Plantas/química , Quinolizinas , Rizoma/química , SophoraRESUMEN
Thirteen compounds were isolated from the 95% aqueous EtOH extract of the rhizomes of Sophora tonkinensis by a combination of various chromatographic techniques including column chromatography over silica gel, Sphadex LH-20, MCI, ODS, and semi-preparative HPLC.Their structures were elucidated as 1-(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)ethanone(1), cyclo(Pro-Pro)(2), nicotinic acid(3), p-hydroxybenzonic acid(4), p-methoxybenzonic acid(5), 4-hydroxymethyl-2,6-dimethoxyphenol-1-O-ß-D-glucopyranoside(6), coniferin(7), syringin(8),(-)-secoisolariciresinol-4-O-ß-D-glucopyranoside(9),(-)-syringaresinol-4-O-ß-D-glucopyranoside(10),(-)-syringaresinol-4,4'-di-O-ß-D-glucopyranoside(11),(-)-pinoresinol-4,4'-di-O-ß-D-glucopyranoside(12), and(6S,9R)-roseoside(13) by their physicochemical properties and spectroscopic data.Compound 1 was a new naturalproduct, and compounds 2,5,6,9,10,12 and 13 were obtained from the Sophora genus for the first time.Compound 1 possessed moderate cytotoxic activity against A549 human tumor cell [IC50ï¼23.05 ± 0.46ï¼µmolâ¢L⻹].
Asunto(s)
Medicamentos Herbarios Chinos/química , Rizoma/química , Sophora/química , Cromatografía Líquida de Alta Presión , Medicamentos Herbarios Chinos/aislamiento & purificación , Estructura Molecular , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Three new matrine-type alkaloids, (+)-5α-hydroxyoxysophocarpine (1), (-)-12ß-hydroxyoxysophocarpine (2), and (+)-5α-hydroxylemannine (3), along with 14 known analogues, (-)-sophocarpine (4), (-)-5α-hydroxysophocarpine (5), (-)-9α-hydroxysophocarpine (6), (+)-12α-hydroxysophocarpine (7), (-)-12ß-hydroxysophocarpine (8), (+)-oxysophocarpine (9), (+)-matrine (10), (+)-sophoranol (11), (+)-9α-hydroxymatrine (12), (-)-14ß-hydroxymatrine (13), (+)-oxymatrine (14), (+)-5α-hydroxyoxymatrine (15), (-)-14ß-hydroxyoxymatrine (16), and (+)-sophoramine (17), were isolated from the rhizomes of Sophora tonkinensis. Their structures were elucidated via spectrometric data analyses, and the absolute configurations were established by single-crystal X-ray diffraction and ECD data. Alkaloids 2, 6, 11, and 13 exhibited antiviral activity against the Coxsackie virus B3 (CVB3), with IC50 values of 26.62-252.18 µM, and alkaloids 7, 8, and 17 inhibited influenza virus A/Hanfang/359/95 (H3N2) replication with IC50 values of 63.07-242.46 µM.
Asunto(s)
Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Antivirales/aislamiento & purificación , Antivirales/farmacología , Quinolizinas/aislamiento & purificación , Quinolizinas/farmacología , Rizoma/química , Sophora/química , Alcaloides/química , Antivirales/química , Subtipo H3N2 del Virus de la Influenza A/efectos de los fármacos , Concentración 50 Inhibidora , Estructura Molecular , Quinolizinas/química , Estereoisomerismo , MatrinasRESUMEN
Seven undescribed monoterpenoid indole alkaloids, two N(4)-chloromethylation artifacts, and 10 known alkaloids were isolated from the stems and twigs of Strychnos cathayensis. The corresponding structures were elucidated via spectroscopic data interpretation and electronic circular dichroism. The absolute configuration of (17S)-12-hydroxy-11-methoxydiaboline, the major anomer of 12-hydroxy-11-methoxydiaboline, was characterized by X-ray diffraction analysis for the first time. At an intraperitoneal dose of 30 mg/kg, 12-hydroxy-11-methoxy-N(4)-chloromethyldiaboline and (-)-macusine A exhibited potential analgesic effects with prolongation rates of 99% and 47% for the latency time of hind-paw licking, respectively, compared to the blank control. 12-Hydroxy-11-methoxydiaboline, 12-hydroxy-11-methoxydiaboline N(4)-oxide, retuline N-oxide, and (-)-vincosamide exhibited antiviral activity against Coxsackie virus B3 (CVB3) with IC50 values of 33.33 µM.