RESUMO
From the underground parts of Thalictrum orientale Boiss., a new phenolic compound 1 was isolated in addition to one known cyanoglycoside, lithospermoside (2). For the structure elucidation of all compounds, 1D- and 2D-NMR techniques (DEPT, COSY, HMBC, HSQC) and MS (HR-MALDI) were used. The structure of the new compound was established as 2-(4'-hydroxyphenyl)-nitroethane-4'-O-[beta-xylopyranosyl-(1 --> 6)-beta-glucopyranoside] (1).
Assuntos
Dissacarídeos/química , Nitrocompostos/química , Fenóis/química , Ranunculaceae/química , Dissacarídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Conformação Molecular , Estrutura Molecular , Nitrocompostos/isolamento & purificação , Rotação Ocular , Fenóis/isolamento & purificação , Extratos Vegetais/química , Ranunculaceae/classificação , TurquiaRESUMO
A new phenylethanoid tetraglycoside, physocalycoside (2), was isolated from the aerial parts of Phlomis physocalyx. Its structure was identified as 3-hydroxy-4-methoxy-beta-phenylethoxy-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-rhamnopyranosyl-(1-->3)]-4-O-feruloyl-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside, on the basis of spectroscopic evidence. In addition, one known iridoid glucoside, lamiide (1) and five known phenylethanoid glycosides, wiedemannioside C (3), verbascoside (= acteoside) (4), leucosceptoside A (5), martynoside (6), and forsythoside B (7) were also characterized. Compounds 2-7 demonstrated radical scavenging properties towards the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.
Assuntos
Cinamatos/química , Glicosídeos/química , Lamiaceae/química , Oligossacarídeos/química , Componentes Aéreos da Planta/química , Trissacarídeos/química , Sequência de Carboidratos , Cinamatos/isolamento & purificação , Glicosídeos/isolamento & purificação , Modelos Moleculares , Conformação Molecular , Dados de Sequência Molecular , Oligossacarídeos/isolamento & purificação , Álcool Feniletílico/química , Álcool Feniletílico/isolamento & purificação , Trissacarídeos/isolamento & purificaçãoRESUMO
From the methanolic extract of the underground parts of Globularia cordifolia, a new iridoid glycoside, 5-hydroxydavisioside (1) and a new bisiridoid glycoside, globuloside C (2) were isolated along with six known iridoid glycosides, aucubin, melampyroside, monomelittoside, globularifolin, alpinoside and asperuloside. The structures of the isolates were established by 1D and 2D NMR spectroscopy in combination with IR, UV and MS analyses.
Assuntos
Iridoides/química , Extratos Vegetais/química , Scrophulariaceae/química , Iridoides/isolamento & purificação , Espectroscopia de Ressonância Magnética/métodos , Modelos Moleculares , Conformação Molecular , Rotação Ocular , Raízes de Plantas/química , Rizoma/químicaRESUMO
A new sterol, ajugasalicigenin (1), and three new sterol glycosides, ajugasaliciosides F-H (2-4), were isolated and characterized from the aerial parts of Ajuga salicifolia. Compounds 1-4 are further representatives of the stigmastane type of sterols. Their cytotoxicity against KB (HeLa) and Jurkat T cancer cells was evaluated.
Assuntos
Ajuga/química , Antineoplásicos Fitogênicos/isolamento & purificação , Glicosídeos/isolamento & purificação , Plantas Medicinais/química , Esteróis/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Concentração Inibidora 50 , Células Jurkat/efeitos dos fármacos , Células KB/efeitos dos fármacos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo , Esteróis/química , Esteróis/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacos , TurquiaRESUMO
From the aerial parts of Ajuga salicifolia (L.) Schreber, a new ionone glycoside (3beta-hydroxy-7,8-dihydro-4-oxo-beta-ionol-9-O-beta-D-glucopyranoside) was isolated, along with the known compounds, corchoionoside C, 8-O-acetylmioporoside, ajugol, harpagide, 8-O-acetylharpagide, lavandulifolioside and leonosides A and B. This is the first report of the occurrence of ionone glycosides and 8-O-acetylmioporoside in Ajuga species. Ajugol, lavandulifolioside, leonoside A and B were isolated for the first time from Ajuga salicifolia. The structures were elucidated by means of 1D-, 2D-NMR spectroscopy, and HR-MALDI mass spectrometry.
Assuntos
Ajuga/química , Glicosídeos/química , Iridoides/química , Glicosídeos/isolamento & purificação , Iridoides/isolamento & purificação , Conformação Molecular , Estrutura MolecularRESUMO
Two new iridoids, 10-O-benzoylglobularigenin (1) and dumuloside (2) were isolated from the aerial parts of Globularia dumulosa together with seven known iridoid glucosides, davisioside (3), aucubin (4), melampyroside (5), catalpol (6), 10-O-benzoylcatalpol (7), alpinoside (8) and deacetylalpinoside (9). Three phenylethanoid glycosides, verbascoside, decaffeoyl-verbascoside, leucosceptoside A and three flavone glucosides, pectolinarigenin 7-O-beta-D-glucopyranoside, nepetin 7-O-B-D-glucopyranoside, demethoxycentaureidin 7-O-beta-D-glucopyranoside were also isolated and characterized. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, HR-MALDIMS, 1D- and 2D NMR) methods.
Assuntos
Iridoides/química , Scrophulariaceae/química , Glicosídeos/química , Glicosídeos/isolamento & purificação , Indicadores e Reagentes , Iridoides/isolamento & purificação , Modelos Moleculares , Conformação Molecular , Rotação Ocular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Espectrofotometria , TurquiaRESUMO
The major compounds isolated from the methanolic extract of the aerial parts of Urtica dioica L. were determined as quercetin-3-O-rutinoside (1). kaempherol-3-O-rutinoside (2). and isorhamnetin-3-O-glucoside (3). by chromatographic, chemical (acidic hydrolysis) and spectral (UV, IR, (1)H-NMR, (13)C-NMR) methods. Their immunomodulatory activities were studied in vitro by chemotaxis (Boyden Migration Chamber) and intracellular killing activity (NBT reduction) tests. Compounds 1, 2, 3 and the total flavonoid fraction were determined to have significant chemotactic effects in 4, 8, 16 microg doses. According to the results of the NBT reduction test, all flavonoid glycosides showed high intracellular killing activity. The results of both assays confirmed the immunostimulatory activity of the flavonoid fraction and the isolated flavonoid glycosides on neutrophils suggesting that they could possibly be useful for treating patients suffering from neutrophil function deficiency and chronic granulomatous diseases.
Assuntos
Adjuvantes Imunológicos/farmacologia , Neutrófilos/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/farmacologia , Urtica dioica , Adjuvantes Imunológicos/química , Quimiotaxia/efeitos dos fármacos , Flavonoides/farmacologia , Glicosídeos/farmacologia , Humanos , Extratos Vegetais/química , Caules de PlantaRESUMO
Nepeta ucrainica L. is used as a herbal tea in Kazakhistan. Phytochemical investigations of the aerial parts of the plant resulted in the isolation of verbascoside (1) and 1,5,9-epi-deoxyloganic acid (2). The structures of the compounds were elucidated by spectral (UV, IR, (1)H-NMR and (13)C-NMR) methods and HPLC analysis. The in vitro immunomodulatory activity of verbascoside was investigated by assessing neutrophil function; chemotaxis and intracellular killing activity. Verbascoside showed an increased chemotactic activity in all doses applied compared with the medium used as a negative control and had a positive effect on respiratory burst of neutrophils, but there was an opposite effect with increasing doses, pointing to a possible suppression of neutrophil intracellular killing activity.