RESUMEN
OBJECTIVE: Poncirus trifoliata (P. trifoliata) fruits exert phytotherapeutic effects, depending on their maturity level. However, the mechanism by which these phytotherapeutic effects are exerted remains undefined - especially in cancers. Therefore, in this study, we investigated the effects of the immature fruit extract of P. trifoliata on a B16 melanoma cell line. MATERIALS AND METHODS: The effect of immature P. trifoliata extract on B16 cells was evaluated by MTT assay, cell proliferation, FACScan analysis of cell cycles, confocal imaging analysis, nuclear (Hoechst) staining, apoptosis assay (Annexin V-fluorescein isothiocyanate/propidium iodide staining), and Western blot assay. The capacity of immature P. trifoliata extract to inhibit the invasion and migration of B16 cells was assessed using the scratch-wound assay and Matrigel migration assay. The effect of immature P. trifoliata extract on mitochondrial function was determined via the mitochondrial membrane potential assay, activity, and fraction and cytosol proteins. RESULTS: Treating B16 cells with a methanol extract of immature P. trifoliata (MEPT) significantly inhibited cell viability, migration, and invasiveness in a dose- (p<0.01) and time (p<0.01)- dependent manner. MEPT arrested the cells in the G1 phase of the cell cycle and led to the activation of the PI3K/AKT/p21 pathway. Furthermore, MEPT dose-dependently induced apoptosis in B16 cells by increasing the expression of the pro-apoptotic proteins Bax and Apaf-1, while decreasing the expression of the anti-apoptotic protein, Bcl-2. MEPT treatment also decreased mitochondrial membrane potential. CONCLUSIONS: Immature P. trifoliata extract inhibited the growth of melanoma cells by inducing cell apoptosis through mitochondrial pathways. Therefore, further research into immature P. trifoliata extract as a potential therapeutic compound for melanoma treatment is warranted.
Asunto(s)
Melanoma , Poncirus , Apoptosis , Línea Celular Tumoral , Proliferación Celular , Frutas , Humanos , Melanoma/metabolismo , Mitocondrias/metabolismo , Fosfatidilinositol 3-Quinasas/metabolismo , Extractos Vegetales/farmacología , Poncirus/metabolismoRESUMEN
AIMS: The medicinal fungi Inonotus xeranticus and Phellinus linteus in the family Hymenochaetaceae have been used as traditional medicines for the treatment of various diseases. However, the compound responsible for the antioxidant activity is still unknown. Therefore, this study was conducted to characterize the antioxidant substances present in cultured broths made from these fungi. METHODS AND RESULTS: Antioxidant fractions of the cultured broths obtained from I. xeranticus and P. linteus were analysed using reversed-phase HPLC, which revealed several peaks that exhibited a potent free radical scavenging activity. To identify these antioxidant peaks, an I. xeranticus strain was mass-cultured, and the cultured broth was separated using antioxidant activity-guided fractionation. Four major active substances were purified and identified as hispidin and its dimers, 3,14'-bihispidinyl, hypholomine B, and 1,1-distyrylpyrylethan based on spectroscopic analyses. All compounds exhibited a significant scavenging activity against these radical species in a concentration-dependent manner. CONCLUSIONS: Antioxidant substances found in the cultured broths of the medicinal fungi I. xeranticus and P. linteus were identified as hispidin and its dimers, 3,14'-bihispidinyl, hypholomine B, and 1,1-distyrylpyrylethan. SIGNIFICANCE AND IMPACT OF THE STUDY: Polyphenol antioxidants were isolated from the cultured broth of the medicinal fungi I. xeranticus and P. linteus and identified based on extensive spectroscopic analyses. These compounds exhibited a strong antioxidant activity.
Asunto(s)
Antioxidantes/análisis , Flavonoides/análisis , Hongos/química , Medicina Tradicional , Fenoles/análisis , Polisacáridos/química , Antioxidantes/química , Línea Celular , Cromatografía Líquida de Alta Presión/métodos , Flavonoides/química , Cuerpos Fructíferos de los Hongos/química , Micelio/química , Micología/métodos , Phellinus , Fenoles/química , Extractos Vegetales , Polifenoles , Análisis EspectralRESUMEN
A previously undescribed coumarin and a new coumarino-lignan, together with the known compounds scopoletin and cleomiscosins A, C, and D, have been isolated from the root bark of Hibiscus syriacus, and their structures were assigned on the basis of various spectral studies. The coumarin analogue and scopoletin inhibited monoamine oxidase with moderate IC(50) values. The new coumarino-lignan and cleomiscosin C showed lipid peroxidation inhibitory activity comparable to vitamin E.
Asunto(s)
Antioxidantes/aislamiento & purificación , Cumarinas/aislamiento & purificación , Dioxanos/aislamiento & purificación , Lignanos/aislamiento & purificación , Malvaceae/química , Inhibidores de la Monoaminooxidasa/aislamiento & purificación , Animales , Antioxidantes/química , Antioxidantes/farmacología , Encéfalo/efectos de los fármacos , Encéfalo/metabolismo , Cromatografía Líquida de Alta Presión , Cumarinas/química , Cumarinas/farmacología , Dioxanos/química , Dioxanos/farmacología , Técnicas In Vitro , Concentración 50 Inhibidora , Corea (Geográfico) , Lignanos/química , Lignanos/farmacología , Peroxidación de Lípido/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Ratones , Microsomas Hepáticos/efectos de los fármacos , Estructura Molecular , Inhibidores de la Monoaminooxidasa/química , Inhibidores de la Monoaminooxidasa/farmacología , Raíces de Plantas/química , Plantas Medicinales/química , Ratas , Escopoletina/farmacología , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Relación Estructura-Actividad , Vitamina E/farmacologíaRESUMEN
Four ellagic acid rhamnosides were isolated from the stem bark of Eucalyptus globulus. Their structures have been established on the basis of the analysis of their 1H NMR, 13C NMR, HMBC, IR and MS spectral data. The HMBC data of these compounds were most useful for their structure determinations, with these bring determined to be 3-O-methylellagic acid 3'-O-alpha-rhamnopyranoside, 3-O-methylellagic acid 3'-O-alpha-3''-O-acetylrhamnopyranoside, 3-O-methylellagic acid 3'-O-alpha-2''-O-acetylrhamnopyranoside, 3-O-methylellagic acid 3'-O-alpha-4''-O-acetylrhamnopyranoside, respectively. Their antioxidant activities were evaluated by measuring the inhibition of lipid peroxidation using rat liver microsomes, with IC50 values of 10.0-14.0 microg/ml.
Asunto(s)
Antioxidantes/química , Antioxidantes/aislamiento & purificación , Ácido Elágico/química , Ácido Elágico/aislamiento & purificación , Eucalyptus/química , Plantas Medicinales , Animales , Antioxidantes/farmacología , Factores Biológicos/química , Factores Biológicos/aislamiento & purificación , Factores Biológicos/farmacología , Ácido Elágico/farmacología , Concentración 50 Inhibidora , Peroxidación de Lípido/efectos de los fármacos , Peroxidación de Lípido/fisiología , Microsomas Hepáticos/metabolismo , Extractos Vegetales , Tallos de la Planta/química , Ratas , Ramnosa/químicaRESUMEN
Twelve compounds with lipid peroxidation inhibitory activity were isolated from the stem bark of E. globulus. Their structures were assigned as a new aromatic monoterpene (1) and eleven known compounds, pinoresinol (2), vomifoliol (3), 3,4,5-trimethoxyphenol 1-O-beta-D-(6'-O-galloyl)glucopyranoside (4), methyl gallate (5), rhamnazin (6), rhamnetin (7), eriodictyol (8), quercetin (9), taxifolin (10), engelitin (11), and catechin (12) on the basis of UV, mass, and NMR spectroscopic analyses. These compounds except vomifoliol significantly inhibited lipid peroxidation in rat liver microsome.
Asunto(s)
Eucalyptus/química , Peroxidación de Lípido/efectos de los fármacos , Plantas Medicinales , Animales , Técnicas In Vitro , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Microsomas Hepáticos/efectos de los fármacos , Microsomas Hepáticos/metabolismo , Epidermis de la Planta/química , Tallos de la Planta/química , Ratas , Espectrometría de Masa Bombardeada por Átomos Veloces , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Espectroscopía Infrarroja por Transformada de FourierRESUMEN
A new lignan named as hibiscuside, (+)-pinoresinol 4-O-[beta-glucopyranosyl (1--->2)-alpha-rhamnoside] (1), and a known lignan, syringaresinol (2) were isolated from the root bark of Hibiscus syriacus together with two feruloyltyramines (3,4) and three known isoflavonoids (5,6,7). The structures of these compounds have been established on the basis of their NMR, mass UV spectra. Among these phenolic compounds, 6"-O-acetyldaidzin (5), 6"-O-acetylgenistin (6), and 3-hydroxydaidzein (7) with IC(50) values of 8.2, 10.6, and 4.1 microM, respectively, significantly inhibited lipid peroxidation in rat liver microsomes. Hibiscuside (1), E- and Z-N-feruloyl tyramines (3,4) exhibited moderate antioxidant activity.
Asunto(s)
Antioxidantes/química , Compuestos Bicíclicos Heterocíclicos con Puentes/química , Disacáridos/química , Lignanos/química , Malvaceae/química , Animales , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Compuestos Bicíclicos Heterocíclicos con Puentes/aislamiento & purificación , Compuestos Bicíclicos Heterocíclicos con Puentes/farmacología , Disacáridos/aislamiento & purificación , Disacáridos/farmacología , Furanos/química , Furanos/aislamiento & purificación , Glicósidos , Técnicas In Vitro , Lignanos/aislamiento & purificación , Lignanos/farmacología , Peroxidación de Lípido/efectos de los fármacos , Microsomas Hepáticos/efectos de los fármacos , Microsomas Hepáticos/metabolismo , RatasRESUMEN
Three new naphthalenes, designated as syriacusins A-C, were isolated from the root bark of Hibiscus syriacus. These compounds were identified as 2,7-dihydroxy-6-methyl-8-methoxy-1-naphthalenecarbaldehyde, 2-hydroxy-6-hydroxymethyl-7,8-dimethoxy-1-naphthalenecarbaldehyde, 1-carboxy-2,8-dihydroxy-6-methyl-7-methoxynaphthalenecarbolactone (1-->8), respectively, on the basis of various spectral studies. The compounds inhibited lipid peroxidation with IC50s of 0.54, 5.90 and 1.02 micrograms ml-1, respectively. The first compound also showed cytotoxicity against some human cancer cell lines with an ED50 of 1.5-2.4 micrograms ml-1.