RESUMO
A new furostane steroidal saponin was isolated from the leaves of Agave angustifolia var. marginata. On the basis of chemical conversions and spectroscopic analyses, its structure was established as 3-[O-ß-d-glucopyranosyl-(1â3)-O-ß-d-glucopyranosyl-(1â3)-O]-[O-6-deoxy-α-l-mannopyranosyl-(1â4)-ß-d-xylopyranosyl-(1â2)-O-ß-d-glucopyranosyl-(1â4)-ß-d-galactopyranosyl)oxy]-(3ß,5α,22α,25R)-26-(ß-d-glucopyranosyloxy)-22-methoxy-furostane (1). Results of preliminary biological investigations indicated that compound 1 showed significant protective effects against induced gastric ulcers using in vivo experimental models and demonstrated negligible toxicity on membrane integrity in the in vitro assays.
Assuntos
Agave/química , Antiulcerosos/farmacologia , Saponinas/farmacologia , Úlcera Gástrica/tratamento farmacológico , Animais , Antiulcerosos/química , Antiulcerosos/isolamento & purificação , Permeabilidade da Membrana Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Humanos , Masculino , Camundongos , Estrutura Molecular , Folhas de Planta/química , Saponinas/química , Saponinas/isolamento & purificação , Relação Estrutura-AtividadeRESUMO
As part of our search of bioactive saponins from Brazilian plants, phytochemical study of the seeds of Inga laurina led to the isolation of a new complex triterpenoid saponin, named ingasaponin. It is the first saponin isolated from a species of Inga genus. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D-NMR spectroscopic techniques and chemical conversions. Its structure was established as 21-[[(2E,6S)-6-[[6-deoxy-4-O-[(2E,6S)-6-[(ß-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(ß-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(ß-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(ß-D-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]oxy]-16-hydroxy-3-[[O-ß-D-xylopyranosyl-(1 â 2)-O-α-L-arabinopyranosyl-(1 â 6)-2-(acetylamino)-2-deoxy-ß-D-glucopyranosyl]oxy]-(3ß,16α,21ß)-olean-12-en-28-oic acid O-α-L-arabinofuranosyl-(1 â 4)-O-[ß-D-glucopyranosyl-(1 â 3)]-O-6-deoxy-α-L-mannopyranosyl-(1 â 2)-ß-D-glucopyranosyl ester (1). The hemolytic potential of 1 was evaluated using in vitro assays, and its adjuvant activity on the cellular immune response against ovalbumin antigen was investigated using in vivo models.
Assuntos
Adjuvantes Imunológicos/farmacologia , Fabaceae/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Adjuvantes Imunológicos/química , Adjuvantes Imunológicos/isolamento & purificação , Animais , Eritrócitos/citologia , Eritrócitos/efeitos dos fármacos , Masculino , Camundongos , Estrutura Molecular , Ovalbumina/administração & dosagem , Ovalbumina/imunologia , Saponinas/química , Saponinas/farmacologia , Sementes/química , Triterpenos/química , Triterpenos/farmacologiaRESUMO
A new steroidal saponin was isolated from the bulbs of Allium ampeloprasum L. var. porrum. On the basis of chemical evidence, comprehensive spectroscopic analyses, and comparison with known compounds, its structure was established as (3ß,5α,6ß,25R)-3-{(O-ß-D-glucopyranosyl-(1â3)-ß-D-glucopyranosyl-(1â2)-O-[O-ß-D-glucopyranosyl-(1â3)]-O-ß-D-glucopyranosyl-(1â4)-ß-D-galactopyranosyl)oxy}-6-hydroxyspirostan-2-one (1). Results of the present study indicated that 1 exhibited haemolytic activity in the in vitro assays, and immunological adjuvant activity on the cellular immune response against ovalbumin antigen.
Assuntos
Adjuvantes Imunológicos , Eritrócitos/efeitos dos fármacos , Cebolas/química , Saponinas/química , Saponinas/farmacologia , Espirostanos/química , Espirostanos/farmacologia , Adjuvantes Imunológicos/química , Adjuvantes Imunológicos/farmacologia , Animais , Hemólise , Humanos , Espectroscopia de Ressonância Magnética , Masculino , Camundongos , Conformação Molecular , Ovalbumina/imunologia , Saponinas/imunologia , Espirostanos/imunologia , Esteroides/químicaRESUMO
A new steroidal saponin was isolated from the bulbs of Allium ampeloprasum var. porrumL. On the basis of chemical evidence, comprehensive spectroscopic analyses and comparison of known compounds, its structure was established as (3ß,5α,6ß,25R)-6-[(ß-D-glucopyranosyl)oxy]-spirostan-3-yl O-ß-D-glucopyranosyl-(1â2)-O-[ß-D-glucopyranosyl-(1â3)]-ß-D-galactopyranoside. Results of the present study indicated that the steroidal saponin showed haemolytic effects in the in vitro assays and demonstrated antiinflammatory activity and gastroprotective property using in vivo models.
Assuntos
Anti-Inflamatórios/uso terapêutico , Antiulcerosos/uso terapêutico , Hemolíticos/farmacologia , Cebolas/química , Fitoterapia , Extratos Vegetais/uso terapêutico , Saponinas/uso terapêutico , Espirostanos/uso terapêutico , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antiulcerosos/isolamento & purificação , Antiulcerosos/farmacologia , Carragenina , Edema/induzido quimicamente , Edema/tratamento farmacológico , Etanol , Hemolíticos/isolamento & purificação , Masculino , Camundongos , Camundongos Endogâmicos , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas , Saponinas/isolamento & purificação , Saponinas/farmacologia , Espirostanos/isolamento & purificação , Espirostanos/farmacologia , Úlcera Gástrica/induzido quimicamente , Úlcera Gástrica/tratamento farmacológicoRESUMO
The seeds of Clitoria fairchildiana provided a new rotenoid, 6-hydroxy-2,3,9-trimethoxy-[1]benzopyrano[3,4-b][1]benzopyran-12(6H)-one. The structural elucidation was performed using detailed analyses of H- and 13C-NMR spectra including 2DNMR spectroscopic techniques (1H-13CHETCOR) and by comparison with spectrometric data from the literature. The anti-inflammatory activity was investigated using a capillary permeability assay.
Assuntos
Anti-Inflamatórios/química , Clitoria/química , Rotenona/análogos & derivados , Sementes/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Modelos Químicos , Estrutura Molecular , Rotenona/química , Rotenona/isolamento & purificação , Rotenona/farmacologiaRESUMO
A new steroidal saponin was isolated from the leaves of Agave shrevei Gentry. Its structure was established as 26-(beta-D-glucopyranosyloxy)-22-methoxy-3-(O-beta-D-glucopyranosyl-(1-->2)O-[O-beta-D-glucopyranosyl-(1-->4)-O-[O-beta-D-glucopyranosyl-(1-->6)]-O-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranosyl]oxy)-(3beta,5alpha,25R)-furostane. 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 steroidal saponin showed absence of haemolytic effects in the in vitro assay, but demonstrated a significant inhibition of the capillary permeability activity.
Assuntos
Agave/química , Hemólise/efeitos dos fármacos , Extratos Vegetais/química , Folhas de Planta/química , Saponinas/química , Esteroides/química , Animais , Sequência de Carboidratos , Espectroscopia de Ressonância Magnética , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Conformação Molecular , Dados de Sequência Molecular , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Saponinas/isolamento & purificação , Saponinas/farmacologia , Esteroides/isolamento & purificação , Esteroides/farmacologiaRESUMO
A novel triterpenoidal saponin, called pulcherrimasaponin (CP05), isolated from the leaves of Calliandra pulcherrima Benth. shows remarkable similarities to the previously described potent adjuvant, QS21 saponin (Quillaja saponaria Molina). On the basis of chemical and physicochemical evidence, its structure was established as [3beta,16alpha,28[2E,6S[2E,6S(2E,6S)]]]-olean-12-en-28-oic acid 3-[[O-alpha-l-arabinopyranosyl-(1-->2)-O-alpha-l-arabinopyranosyl-(1-->6)-2-(acetylamino)-2-deoxy-beta-d-glucopyranosyl]oxy]-16-hydroxy-O-beta-d-glucopyranosyl-(1-->3)-O-[O-beta-d-xylopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-O-6-deoxy-alpha-l-mannopyranosyl-(1-->2)-6-O-[6-[[2-O-2,6-dimethyl-1-oxo-6-(beta-d-xylopyranosyloxy)-2,7-octadienyl]-[(6-deoxy-beta-d-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-beta-d-xylopyranosyl]oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-beta-d-glucopyranosyl ester. In vivo toxicity assays disclosed similar and transitory local swelling and loss of hair but no lethality for mice. The haemolytic index was higher for QS21 (5 microg/ml) than for CP05 (13 microg/ml). Mouse vaccination with either CP05 or QS21 in combination with the fucose-mannose ligand (FML) antigen of Leishmania donovani showed anti-FML responses, significantly enhanced over the saponin and saline controls, in IgM, IgG, IgG1, IgG2a, IgG2b and IgG3. Antibody levels were similar for both vaccines in most subtypes. However, QS21-FML vaccine showed a 1.5 to 2.1 proportional increase over the CP05-FML vaccine in IgG, IgG2a and IgG3 responses. The delayed type of hypersensitivity against leishmanial antigen was impressively increased for CP05-FML and for QS21-FML-treated animals over controls (p<0.005). Enhancement was similar for both vaccines (p<0.05). The safety analysis and the effect on humoral and cellular immune responses demonstrated that the novel Calliandra pulcherrima Benth. CP05 saponin is a potential candidate for a vaccine adjuvant.
Assuntos
Adjuvantes Imunológicos/uso terapêutico , Fabaceae/imunologia , Imunização/métodos , Leishmaniose Visceral/prevenção & controle , Vacinas Protozoárias/imunologia , Saponinas/química , Adjuvantes Imunológicos/isolamento & purificação , Animais , Anticorpos Antiprotozoários/biossíntese , Cricetinae , Modelos Animais de Doenças , Fabaceae/química , Feminino , Humanos , Leishmaniose Visceral/imunologia , Leishmaniose Visceral/parasitologia , Camundongos , Camundongos Endogâmicos BALB C , Extratos Vegetais/imunologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/uso terapêutico , Folhas de Planta , Vacinas Protozoárias/administração & dosagem , Quillaja/imunologia , Saponinas/imunologiaRESUMO
A new steroidal saponin was isolated from the leaves of Agave attenuata. Its structure was established as (3beta,beta,25S)-spirostan-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 hemolytic activity of the steroidal saponin was evaluated using an in vitro assay.
Assuntos
Agave/química , Saponinas/química , Saponinas/isolamento & purificação , Bioensaio , Técnicas de Cultura de Células , Eritrócitos , Hemólise , Humanos , Espectroscopia de Ressonância Magnética , Folhas de Planta/química , Saponinas/farmacologiaRESUMO
Costus spicatus, used in Brazilian traditional medicine to expel kidney stones, contains steroidal saponins with different chemical characteristics. In spite of its popular utilization as potent diuretic, no scientific reports correlate this activity with the chemical constituents of the extract. Therefore, two steroidal saponins (3 beta,22 alpha,25R)-26-(beta-D-glucopyranosyloxy)-2-methoxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside (1) and (3 beta,22 alpha,25R)-spirostan-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside (1a), were isolated from the rhizomes of this plant and their effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated. It was observed that 1 and 1a inhibit specifically the Na+-ATPase activity.
Assuntos
Saponinas/farmacologia , ATPase Trocadora de Sódio-Potássio/efeitos dos fármacos , ATPase Trocadora de Sódio-Potássio/metabolismo , Esteroides/farmacologia , Animais , Terapias Complementares , Costus , Cães , Rim/efeitos dos fármacos , Rim/enzimologia , Rim/fisiologia , Cinética , Fitoterapia , SuínosRESUMO
A new steroidal saponin was isolated from the leaves of Sansevieria cylindrica. Its structure was established as (3beta,12beta,15alpha,25S)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl 12-O- (6-deoxy-alpha-L-mannopyranosyl)-15-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside. The structural identification was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, HMBC and HMQC) and chemical conversions. The steroidal saponin showed no haemolytic effects in the in vitro assays and demonstrated inhibition of the capillary permeability activity.