RESUMO
The use of an HPLC bioactivity profiling/microtiter plate technique in conjunction with capillary probe NMR instrumentation and access to appropriate databases effectively short-circuits conventional dereplication procedures, necessarily based on multimilligram extracts, to a single, more rapid submilligram operation. This approach to dereplication is illustrated using fungal or bacterial extracts that contain known compounds. In each case the dereplication steps were carried out on microgram quantities of extract and demonstrate the discriminating power of (1)H NMR spectroscopy as a definitive dereplication tool.
Assuntos
Produtos Biológicos/química , Técnicas de Química Combinatória/métodos , Extratos Vegetais/química , Cromatografia Líquida de Alta Pressão , Técnicas de Química Combinatória/economia , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
The aerial parts of Carthamus lanatus (Asteraceae) afforded four new oxygenated bisabolane fucosides, 10-hydroperoxy-bisabola-2,11-diene 7-O-beta-D-fucopyranoside, 11-hydro-peroxy-bisabola-2,9-diene 7-O-beta-D-fucopyranoside, 10-hydroxy-bisabola-2,11-diene 7-O-beta-D-fucopyranoside and 11-hydroxy-bisabola-2,9-diene 7-O-beta-D-fucopyranoside together with the known compounds a-bisabolol beta-D-fucopyranoside, asperuloside, sitosterol 3-O-beta-D-glucoside and stigmasterol 3-O-beta-D-glucoside. Asperuloside appears to be the second representative of the iridoid monoterpene group found in the plant family Asteraceae, which until recently was considered to lack iridoids. The main constituent a-bisabolol fucoside exhibited noticeable antibacterial and cytotoxic activities.
Assuntos
Anti-Infecciosos/química , Carthamus/química , Fucose/análogos & derivados , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Sesquiterpenos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Candida/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Fucose/química , Fucose/isolamento & purificação , Fucose/farmacologia , História do Século XVIII , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Modelos Moleculares , Conformação Molecular , Estrutura Molecular , Oxirredução , Extratos Vegetais/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Espectrometria de Massas por Ionização por Electrospray , Staphylococcus aureus/efeitos dos fármacosRESUMO
Sterols, triterpenes, volatiles, polar and other constituents in aerial parts of Carthamus lanatus were analyzed by gas chromatography-mass spectrometry. Over 90 compounds were identified most of them new for the species. Sitosterol and stigmasterol were the most abundant of 10 sterols identified in the sterol fraction. Taraxasterol, alpha- and beta-amyrine prevailed in the triterpene fraction. Volatiles, sterols and a fraction of the dichloromethane extract showed strong cytotoxicity (Artemia salina assay).
Assuntos
Carthamus/química , Componentes Aéreos da Planta/química , Plantas Medicinais/química , Esteróis/química , Esteróis/toxicidade , Triterpenos/química , Triterpenos/toxicidade , Animais , Artemia , Sobrevivência Celular/efeitos dos fármacos , Flores/química , Cromatografia Gasosa-Espectrometria de Massas , Região do Mediterrâneo , Esteróis/isolamento & purificação , Triterpenos/isolamento & purificaçãoRESUMO
Two flavonoid aglycons, eight flavonoid glycosides, chlorogenic acid and syringin were isolated from aerial parts of Carthamus lanatus. Isorhamnetin 3-O-beta-D-glucoside and chlorogenic acid were found for the first time in the genus Carthamus and respectively, quercimeritrin, astragalin, kaempferol 3-O-beta-D-sophoroside and syringin in the species. The ethyl acetate fraction of the methanol extract exhibited a higher antioxidant activity than the butanol fraction measured by the alpha,alpha-diphenyl-beta-picrazylhydrazyl (DPPH) free radical scavenging assay. Cytotoxicity and antioxidant activities of the main constituent, luteolin 7-O-beta-D-glucoside, were evaluated.
Assuntos
Carthamus/química , Flavonoides/química , Fenóis/química , Fenóis/toxicidade , Animais , Artemia , Flavonoides/isolamento & purificação , Flavonoides/toxicidade , Conformação Molecular , Estrutura Molecular , Fenóis/isolamento & purificação , Plantas Medicinais/químicaRESUMO
The anti-inflammatory activity of four total extracts, their fractions and two main constituents (alpha-bisabolol beta-D-fucopyranoside and luteolin 7-O-glucoside) of Carthamus lanatus L. aerial parts, were assessed in vitro by determining the inhibitory effects on induced human neutrophils. The dichloromethane extract and its water-alcoholic part exhibited the most significant inhibitory effects.
Assuntos
Anti-Inflamatórios/química , Carthamus/química , Neutrófilos/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Neutrófilos/fisiologia , Componentes Aéreos da Planta/química , SolventesRESUMO
Total dichloromethane, methanol and water extracts, their fractions as well as volatiles of Carthamus lanatus aerial parts were phytochemically screened and evaluated for antibacterial, antifungal and cytotoxic activity. The H(2)O/MeOH fraction of the CH(2)Cl(2) extract exhibited noticeable antibacterial activity. The same fraction and the volatiles showed significant cytotoxic activity.
Assuntos
Anti-Infecciosos/farmacologia , Artemia/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Carthamus , Escherichia coli/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Animais , Antibacterianos , Anti-Infecciosos/administração & dosagem , Anti-Infecciosos/uso terapêutico , Humanos , Dose Letal Mediana , Testes de Sensibilidade Microbiana , Extratos Vegetais/administração & dosagem , Extratos Vegetais/uso terapêuticoRESUMO
A GC-MS analysis of underivatized alkaloids from leaves of Crinum latifolium was performed. From the identified 15 alkaloids, 9 were found for the first time in this plant. Almost all alkaloids belonged to the crinane type. Substantial changes in the methylation and oxidation pattern of the alkaloids at and after flowering were observed.