RESUMEN
AIM: To isolate and identify the active constituents of Erigeron brevisapus (Vant.) Hand.-Mazz. METHODS: The chemical constituents were isolated by silica gel column chromatography and two new compounds were obtained. Their structures were elucidated by IR, MS, 1HNMR, 13CNMR, DEPT and 2DNMR. The injury of BCMEC (bovine cerebral microvascular endothelial cell) was determined by lactic dehydrogenase (LDH), the ability of the drugs anti-oxidation and scavenging oxidation of free radical was measured by colorimetric method. RESULTS: Two new compounds have been identified as 1-O-methyl-3, 5-O-dicaffeoyl quinic acid methyl ester (III) and 5-O-caffeoyl quinic acid butyl ester (IV). CONCLUSION: Compounds III and IV are new compounds. Compound III can protect BCMEC injury by LPC.
Asunto(s)
Asteraceae/química , Ácidos Cafeicos/aislamiento & purificación , Endotelio Vascular/efectos de los fármacos , Plantas Medicinales/química , Ácido Quínico/aislamiento & purificación , Animales , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Ácidos Cafeicos/química , Ácidos Cafeicos/farmacología , Bovinos , Separación Celular , Endotelio Vascular/metabolismo , L-Lactato Deshidrogenasa/metabolismo , Microcirculación/citología , Estructura Molecular , Sustancias Protectoras/aislamiento & purificación , Sustancias Protectoras/farmacología , Ácido Quínico/análogos & derivados , Ácido Quínico/química , Ácido Quínico/farmacologíaRESUMEN
OBJECTIVE: To study the chemical constituents from the upground part of Erigeron breviscapus. METHOD: The compounds were separated and purified by column chromatography with silica gel, and identified by IR, MS, NMR and 2D-NMR. RESULT: Two new compounds were isolated and identified as 5,4'-dihydroxy flavonod-7-O-beta-D-pyranglycuronate buthyl ester(VI) and 3,5-dimethoxy benzene carbonic acid-4-O-beta-D-pyranglucose(VII). CONCLUSION: Compounds VI and VII were new compounds.
Asunto(s)
Asteraceae/química , Benzoatos/aislamiento & purificación , Flavonoides/aislamiento & purificación , Glucósidos/aislamiento & purificación , Glucuronatos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Plantas Medicinales/química , Benzoatos/química , Flavonoides/química , Glucósidos/química , Glucuronatos/química , Glicósidos/química , Estructura Molecular , Éteres FenílicosRESUMEN
OBJECTIVE: To study the chemical constituents of Erigeron breviscapus. METHOD: The constituents were separated and purified by column chromatography with silica gel, and identified by IR, MS, NMR and physical data. RESULT: Five compounds were isolated and identified as 3, 5, 6, 4'-tetrahydroxy-7-methoxy flavonoid(I); 5, 7, 4'-trihydroxy flavonoid(II); 3, 5, 6, 7, 4'-pentahydroxy flavonoid(III); scutellarein (IV) and 5, 7, 4'-trihydroxy flavanone(V). CONCLUSION: Compounds I, III and V were isolated from this plant for the first time.
Asunto(s)
Apigenina , Asteraceae/química , Flavonoides/aislamiento & purificación , Glucuronatos , Plantas Medicinales/química , Flavonoides/químicaRESUMEN
Two new constituents with a novel basic skeleton were isolated from Erigeron breviscapus. On the basis of chemical and spectroscopic evidences, the structures of the new compounds were elucidated as 1R,3R-dihydroxy-4S,5R-dicaffeoyloxy cyclohexane carboxylic acid methyl ester (V), 1,4-dihydroxy-3R,5R-dicaffeoyloxy cyclohexane carboxylic acid methyl ester (VI).
Asunto(s)
Ácidos Cafeicos/química , Ciclohexanos/química , Plantas Medicinales/química , Ácidos Cafeicos/aislamiento & purificación , China , Ciclohexanos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Conformación Molecular , Extractos Vegetales/análisis , Espectrometría de Masa Bombardeada por Átomos Veloces , Espectrofotometría InfrarrojaRESUMEN
From the ethanol extract of Viscum coloratum (Kom.) Nakai, a glucoside of aliphatic diol and three other glucosides were isolated. Based on chemical and spectroscopic analysis, the structures have been elucidated as 2-beta-D-glucosyl-3-methylpropanol (VIII), syringin (IX), eleatheroside E (X) and syringenin-4'-O-D-apiosylglucoside (XI). VIII is a new glucoside of aliphatic diol and named 3-beta-D-glucopyranosyloxy-butanol-2. Three other compounds (IX-XI) were found for the first time in this plant.
Asunto(s)
Muérdago/química , Plantas Medicinales , Butanoles/química , Butanoles/aislamiento & purificación , Glucósidos/química , Glucósidos/aislamiento & purificación , Estructura MolecularRESUMEN
From the ethanol extract of Viscum coloratum (Kom.) Nakai, a new flavonoid has been isolated. Based on chemical and spectroscopic analysis, the structure of VII has been elucidated as rhamnazin-3-0-beta-D-apisoyl-(1----2)-[6"-O-(3-hydroxy-3- methylglutarate)]- glucoside and named Viscumneoside VII.
Asunto(s)
Medicamentos Herbarios Chinos/química , Flavonoides/aislamiento & purificación , Glicósidos/aislamiento & purificación , Flavonoides/química , Glicósidos/químicaRESUMEN
In order to determine the absolute configuration of the chiral center of viscumneoside IV, which was isolated from Viscum coloratum (Kom) Nakai, (R, S)-mevalonolactone was synthesized as shown in scheme 1. Then treatment with (S) (-)-1-phenylethylamine in THF gave two diasteromeric amides, which were transformed into the monoacetates and separated by HPLC. The first eluted peak (tR10.07 min.) had the (R)-configuration and the second one the (S)-configuration (tR11.20 min). Viscumneoside IV was treated with borane and hydrolyzed to give mevalonolactone which was treated with (S)-(-)-1-phenylethylamine in THF as mentioned above. The monoacetates of the resulting amides were subjected to HPLC. By comparison with the reference peaks, the absolute configuration at the acyl moiety of viscumneoside IV was shown to have the (R)-configuration.