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1.
Planta Med ; 87(10-11): 879-891, 2021 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-33860477

RESUMEN

Five new compounds, a flavonol glycoside ( 1: ), a megastigmane ( 2: ), 2 cyclohexylethanoids ( 3, 4: ), and a phenylethanoid derivative ( 5: ), together with 15 known compounds ( 6: - 20: ) including flavonoid glycosides, cyclohexylethanoids, and phenolic compounds, have been isolated from Cornus sanguinea drupes. All the structures have been determined by 1D and 2D NMR spectroscopic analysis and mass spectrometry data. The antioxidant capability of the most representative isolated compounds was evaluated in the hydrogen peroxide (H2O2)-induced premature cellular senescence model of human dermal and gingival fibroblasts. Several derivatives counteracted the increase of reactive oxigen species (ROS) production in both cellular models. Among the most promising, compounds 8, 14: , and 20: were able to counteract cell senescence, decreasing the expression of p21 and p53. Furthermore, compound 14: decreased the expression of inflammatory cytokines (IL-6) in both cell models and counteracted the decrease of collagen expression induced by the H2O2 in dermal human fibroblasts. These data highlight the anti-aging properties of several isolated compounds from C. sanguinea drupes, supporting its possible use in the cure of skin or periodontitis lesions.


Asunto(s)
Antioxidantes , Cornus , Antioxidantes/farmacología , Fibroblastos , Frutas , Humanos , Peróxido de Hidrógeno
2.
J Nat Prod ; 83(3): 626-637, 2020 03 27.
Artículo en Inglés | MEDLINE | ID: mdl-32031808

RESUMEN

Four new triterpenoid bidesmosidic saponins (1-4) and a sesquiterpenoid glucoside (5), together with nine known phenolic compounds (6-14), were isolated from the fruits of Elaeagnus umbellata. Their structures were elucidated using 1D and 2D NMR spectroscopy and mass spectrometry data. The antioxidant capability of the isolated compounds was evaluated in human gingival fibroblasts. Compound 6 decreased ROS production and promoted cell proliferation. It also counteracted the cell cycle blockade induced by a low concentration of H2O2 decreasing the expression of p21 and CDKN2A (p16INK4A). Compound 6 decreased the expression of inflammatory cytokines (IL-6 and IL-8) in response to inflammatory stimuli, supporting its possible use in periodontitis lesions.


Asunto(s)
Antioxidantes/farmacología , Puntos de Control del Ciclo Celular/efectos de los fármacos , Elaeagnaceae/química , Fibroblastos/efectos de los fármacos , Antioxidantes/aislamiento & purificación , Células Cultivadas , Frutas/química , Glucósidos/aislamiento & purificación , Glucósidos/farmacología , Humanos , Italia , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Especies Reactivas de Oxígeno , Saponinas/aislamiento & purificación , Saponinas/farmacología , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Triterpenos/aislamiento & purificación , Triterpenos/farmacología
3.
Planta Med ; 85(11-12): 947-956, 2019 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-31163459

RESUMEN

In this paper, the isolation of five new guaianolides (1:  - 5: ) and four (6:  - 9: ) known sesquiterpenes from Ormenis mixta aerial parts is reported. The structural determination of the guaianolides was obtained by NMR spectroscopic data, as well as MS experiments. Their relative configurations were assigned by a combined quantum mechanical/NMR approach, comparing the experimental 13C/1H NMR chemical shift data and 1 J H-H homonuclear coupling constants with the related predicted values. The isolates were assayed for their anti-inflammatory potential evaluating nitric oxide release and cyclooxygenase-2 expression in J774A.1 macrophages treated with lipopolysaccharide from Escherichia coli. Our results indicated that, among the tested compounds, 1:  - 3: , and 7: were able to inhibit nitric oxide release, while all were able to inhibit cyclooxygenase-2 expression with different potencies.


Asunto(s)
Antiinflamatorios/farmacología , Manzanilla/química , Sesquiterpenos de Guayano/farmacología , Animales , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Línea Celular , Ciclooxigenasa 2/metabolismo , Macrófagos/efectos de los fármacos , Macrófagos/metabolismo , Espectroscopía de Resonancia Magnética , Ratones , Óxido Nítrico/metabolismo , Componentes Aéreos de las Plantas/química , Sesquiterpenos de Guayano/química , Sesquiterpenos de Guayano/aislamiento & purificación
4.
Planta Med ; 85(11-12): 1034-1039, 2019 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-30965376

RESUMEN

In this paper, the isolation of one new iridoid glucoside, 6ß-acetoxyipolamiide (1: ), and thirteen (2:  - 14: ) known congeners from two Lamiaceae species, Stachys ocymastrum and Premna resinosa, leaf extracts is reported. The structural determination of the isolated compounds was performed by mono- and bidimensional NMR spectroscopic analysis as well as MS experiments. The isolates were assayed for their antiangiogenic activity by two in vivo models, zebrafish embryos and chick chorioallantoic membrane assays. The compounds with a significant antiangiogenic activity in both assays were ß-hydroxyipolamiide (2: ), ipolamiide (3: ), and buddlejoside A5 (8: ). 6-O-α-l-(3″-O-p-Methoxycinnamoyl-4″-O-acetyl)rhamnopyranosyl catalpol (13: ) and 6-O-α-l-(2″-trans-caffeoyl)rhamnopyranosyl catalpol (6: ) showed the best antiangiogenic response on blood vessel growth in zebrafish embryos, whereas saccatoside (10: ) and 6-O-α-l-(2″-O - : p-methoxycinnamoyl-3″-O-acetyl)rhamnopyranosyl catalpol (14: ) resulted in a strong reduction of capillary formation in the chorioallantoic membrane assay.


Asunto(s)
Inhibidores de la Angiogénesis/farmacología , Iridoides/aislamiento & purificación , Lamiaceae/química , Stachys/química , Animales , Bioensayo , Embrión de Pollo , Relación Dosis-Respuesta a Droga , Iridoides/farmacología , Espectroscopía de Resonancia Magnética , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Hojas de la Planta/química , Pez Cebra
5.
Food Chem ; 360: 129999, 2021 Oct 30.
Artículo en Inglés | MEDLINE | ID: mdl-33989880

RESUMEN

In this study, cherry fruits and petioles from six ancient Italian Prunus avium L. varieties (Ferrovia, Capellina, Morellina, Ciambellana, Napoletana, and Bianca), were compared by chemical and bioinformatic analyses and evaluated for their antiangiogenic activity. The highest levels of total phenols and flavonoids were found in Napoletana petioles, and Morellina and Capellina fruits. HPLC-PDA-MS analyses showed similar phenolic profiles for all fruit extracts, with cyanidin-3-O-rutinoside, flavonols glycosides, and quinic acid derivatives as major components. Flavonoid glycosides were found in all petiole extracts, while proanthocyanidins B type were predominant in Capellina, Napoletana and Bianca. Accordingly to their higher polyphenolic content, petiole extracts exhibited stronger radical scavenging activity compared to the fruits. The best antiangiogenic response was exhibited by Morellina, Ferrovia, and Ciambellana petiole extracts, and by Ferrovia, Morellina, and Capellina fruit extracts; by bioinformatic studies rutin and cyanidin 3-O-rutinoside were recognised as the best candidate bioactive compounds. In conclusion, sweet cherry varietes were confirmed as valuable sources of phenols, showing also potential angiomodulator properties.


Asunto(s)
Inhibidores de la Angiogénesis/análisis , Extractos Vegetales/química , Prunus avium/química , Fosfatasa Alcalina/metabolismo , Inhibidores de la Angiogénesis/farmacología , Animales , Antocianinas/análisis , Antioxidantes/química , Cromatografía Líquida de Alta Presión , Análisis por Conglomerados , Embrión no Mamífero/diagnóstico por imagen , Embrión no Mamífero/metabolismo , Flavonoides/análisis , Frutas/química , Frutas/metabolismo , Italia , Fenoles/análisis , Extractos Vegetales/farmacología , Prunus avium/metabolismo , Espectrometría de Masa por Ionización de Electrospray , Pez Cebra/crecimiento & desarrollo , Pez Cebra/metabolismo
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