RESUMO
As part of the ongoing efforts in discovering potentially bioactive natural products from medicinal plants, the present study was conducted to isolate a new complex triterpenoid saponin from the barks of Albizia lebbeck. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of 1H and 13C NMR spectra including 2D-NMR (COSY, TOCSY, HSQC and HMBC) spectroscopic techniques, high-resolution electrospray ionization mass spectrometry (HRESIMS) analysis and chemical conversions. Its structure was established as 21-[[(2E,6S)-6-[6-deoxy-4-O-[(2E,6S)-6-hydroxy-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]-[(ß-d-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]-[(ß-d-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]oxy]-16-hydroxy-3-[[O-ß-d-xylopyranosyl-(1â¯ââ¯2)-O-α-l-arabinopyranosyl-(1â¯ââ¯6)-2-(acetylamino)-2-deoxy-ß-d-glucopyranosyl]oxy]-(3ß,16α,21ß)-olean-12-en-28-oic acid O-α-l-arabinofuranosyl-(1â¯ââ¯4)-O-[ß-d-glucopyranosyl-(1â¯ââ¯3)]-O-6-deoxy-α-l-mannopyranosyl-(1â¯ââ¯2)-ß-d-glucopyranosyl ester (1). Additionally, this study aimed to investigate the permeability property of 1, its activity on membrane integrity and supramolecular interactions with cellular constituents using in vitro experimental models.
Assuntos
Albizzia/química , Membrana Celular/efeitos dos fármacos , Saponinas/química , Triterpenos/química , Animais , Eritrócitos/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Masculino , Camundongos , Estrutura Molecular , Permeabilidade , Saponinas/farmacocinética , Espectrometria de Massas por Ionização por Electrospray , Triterpenos/farmacocinéticaRESUMO
Many classes of phytochemical products are finding therapeutic use, for example, complex triterpenoid saponins containing in their structures monoterpene moieties. Some of these compounds possess cytotoxic, anti-HIV and adjuvant activities. This review aims to give an overview of these complex triterpenoid saponins with biological activity from the Leguminosae.
Assuntos
Fabaceae/química , Saponinas/química , Saponinas/farmacologia , Triterpenos/química , Triterpenos/farmacologia , Estrutura MolecularRESUMO
A new steroidal saponin, 3-{(O-6-deoxy-a-L-mannopyranosyl-(1 --> 4)-O-beta-D-glucopyranosyl-(1 --> 3)-O-[O-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 2)]-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranosyl)oxy}-6-hydroxy-(3beta,5alpha,6alpha,25R)-spirostan-12-one, was isolated from Agave brittoniana Trel. The structure was determined by extensive NMR spectroscopy studies and chemical conversions. Its effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated. It was observed that this steroidal saponin exerts a biphasic effect on the Na+-ATPase activity. It is concluded that the effect of the aqueous extract as a diuretic is due, at least in part, to the action of saponin on the ouabain-insensitive Na+-ATPase.
Assuntos
Agave/química , Saponinas/química , Saponinas/farmacologia , ATPase Trocadora de Sódio-Potássio/metabolismo , Esteroides/química , Esteroides/farmacologia , Animais , Configuração de Carboidratos , Sequência de Carboidratos , Membrana Celular/enzimologia , Túbulos Renais/enzimologia , Cinética , Metilação , Modelos Moleculares , Dados de Sequência Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química , Saponinas/isolamento & purificação , Sódio/farmacologia , ATPase Trocadora de Sódio-Potássio/efeitos dos fármacos , Esteroides/isolamento & purificação , SuínosRESUMO
A polysaccharide, an alpha-D-glucan with an apparent molecular weight of 6.85 x 10(4), called PSa glucan, was isolated from fresh seeds of Sorghum arundinaceum by fractionation on Sephacryl S-300 HR and Sephadex G-25. Chemical and spectroscopic studies indicated that it has a highly branched glucan type structure composed of alpha-(1-->4) linked D-glucopyranose residues with (1-->3), (1-->6) branching points, and a significant amount of alpha-(1-->6) branching to alpha-(1-->3) linked D-glucopyranose residues. The anti-inflammatory activity of the polysaccharide was performed using the capillary permeability assay.
Assuntos
Anti-Inflamatórios/química , Grão Comestível/química , Polissacarídeos/química , Sementes/química , Animais , Anti-Inflamatórios/farmacologia , Configuração de Carboidratos , Sequência de Carboidratos , Cromatografia Gasosa-Espectrometria de Massas , Masculino , Metilação , Camundongos , Camundongos Endogâmicos BALB C , Dados de Sequência Molecular , Oligossacarídeos/química , Oligossacarídeos/isolamento & purificação , Extratos Vegetais/química , Polissacarídeos/isolamento & purificação , Polissacarídeos/farmacologia , EsteroidesRESUMO
A new steroidal saponin was isolated from the leaves of Agave attenuata Salm-Dyck. Its structure was established as (3beta,5beta,22alpha,25S)-26-(beta-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside. The structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR and COLOC) and chemical conversions. The haemolytic potential of the steroidal saponin was evaluated and the anti-inflammatory activity was performed using the capillary permeability assay.
Assuntos
Agave/química , Fitosteróis/química , Extratos Vegetais/química , Saponinas/química , Configuração de Carboidratos , Sequência de Carboidratos , Dados de Sequência Molecular , Estrutura Molecular , Oligossacarídeos/química , Oligossacarídeos/isolamento & purificação , Fitosteróis/isolamento & purificação , Folhas de Planta/química , Saponinas/isolamento & purificaçãoRESUMO
An arabinogalactan with mean Mr of 6.85 x 10(4), was isolated from the pulps of Melocactus depressus Hook by fractionation on Sephacryl S-300 HR. Chemical and spectroscopic studies indicated that it has a branched arabinogalactan type structure composed of beta-(1-->4) linked D-galactopyranose residues with beta-(1-->3) and beta-(1-->6) branching points. Its structural features include also alpha-(1-->2), alpha-(1-->3) and alpha-(1-->5) linked L-arabinofuranose residues. The polysaccharide demonstrated a phagocytosis stimulating property.