RESUMEN
Nine geranylated flavanones isolated from the fruits of Paulownia tomentosa (4-12) and two from the roots of Morus alba (13 and 14) were examined for cytotoxicity to selected human cancer cell lines and normal human fibroblasts. Cytotoxicity was determined in vitro using a calcein AM cytotoxicity assay. Cytotoxicity for the THP-1 monocytic leukemia cell line was tested using erythrosin B cell staining. The geranylated compounds tested were compared with the known simple flavanone standards taxifolin (1), naringenin (2), and hesperetin (3) and with the standard anticancer drugs olomoucine II, diaziquone, and oxaliplatin and the antineoplastic compound camptothecin, and showed different levels of cytotoxicity. The effects of structural changes on cytotoxic activity, including geranyl substitution of the flavanone skeleton and the oxidation pattern of ring B of the flavanones, are discussed.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Flavanonas/aislamiento & purificación , Flavanonas/farmacología , Magnoliopsida/química , Plantas Medicinales/química , Antineoplásicos Fitogénicos/química , Apoptosis/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Fibroblastos/efectos de los fármacos , Flavanonas/química , Frutas/química , Humanos , Estructura Molecular , Morus/química , Resonancia Magnética Nuclear Biomolecular , Raíces de Plantas/química , Relación Estructura-Actividad , TurquíaRESUMEN
Using exhaustive chromatographic separation we have isolated (-)-tigloyl-deangeloyl-gomisin F as a novel dibenzocyclooctadiene lignan from schisandra chinensis. With the help of HPLC, we further isolated (+)-schisandrin, (+)-deoxyschisandrin, (+)-γ-schisandrin, (-)-gomisin J, (+)-gomisin A, (-)-gomisin N, (-)-tigloyl-gomisin P, (-)-wuweizisu C, (-)-gomisin D, rubrisandrin A, (-)-gomisin G, (+)-gomisin K (3) and (-)-schisantherin C. A full NMR description of (-)-schisantherin C was carried out with the aim to confirm previous reports of its structure. Compounds isolated were identified on the basis of UV, IR, (1)H- and (13)C-NMR and MS. The cytotoxicity of lignans was tested for the BY-2 cell line alone and as a synergistic effect with the cytotoxic agent camptothecin. Lignans showed various toxicity and synergistic and antagonistic effects on camptothecin-induced cytotoxicity. Cytotoxicity against colon cancer cell line LoVo was also tested.
Asunto(s)
Apoptosis/efectos de los fármacos , Citotoxinas/toxicidad , Lignanos/toxicidad , Schisandra/química , Línea Celular , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Fraccionamiento Químico , Cromatografía Líquida de Alta Presión , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Humanos , Lignanos/química , Lignanos/aislamiento & purificación , Resonancia Magnética Nuclear Biomolecular , Extractos Vegetales/química , Nicotiana/efectos de los fármacosRESUMEN
The in vitro antiradical activity of Schisandra chinensis lignans was investigated using DPPH, ABTS+, Fenton reaction inhibition and tyrosine-nitration inhibition assays, as were the in vivo antidiabetic activities of selected lignans in an animal model of alloxan-induced diabetes. Different degrees of antiradical activity were found, depending upon the structural parameters of the tested compounds. Unfortunately, the compounds showed no antidiabetic activity in concentration range tested.
Asunto(s)
Antioxidantes/farmacología , Depuradores de Radicales Libres/farmacología , Lignanos/farmacología , Modelos Animales , Extractos Vegetales/farmacología , Schisandra/química , Animales , Cromatografía Líquida de Alta Presión , Femenino , Ratones , Ratones Endogámicos ICRRESUMEN
A different behavior of the two dibenzocyclooctadiene lignans (+)-deoxyschisandrin (1) and (-)-gomisin N (2), from Schisandra chinensis fruits, was observed against two human tumour cell lines, (2008 and LoVo). These lignans inhibited cell growth in a dose-dependent manner on both cell lines, but inducing different types of cell death. In particular, (+)-deoxyschisandrin (1) caused apoptosis in colon adenocarcinoma cells (LoVo) but not in ovarian adenocarcinoma cells (2008), while (-)-gomisin N (2) induced apoptosis on both the cell lines used. Mitochondrial-mediated pathway was not involved in apoptotic stimuli. Both compounds caused G2/M phase cell growth arrest correlated with tubulin polymerization.
Asunto(s)
Apoptosis/efectos de los fármacos , Puntos de Control del Ciclo Celular/efectos de los fármacos , Ciclooctanos/farmacología , Lignanos/farmacología , Compuestos Policíclicos/farmacología , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Frutas/química , Humanos , Estructura Molecular , Schisandra/químicaRESUMEN
Three new nervogenic acid glycosides, 1-O-alpha-L-rhamnopyranosyl 3,5-bis(3-methyl-but-2-enyl)-4-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-benzoate, 3,5-bis(3-methyl-but-2-enyl)-4-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-benzoic acid, and bis{3,5-bis(3-methyl-but-2-enyl)-4-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]-benzoyl} 1,2-O-beta-d-glucopyranose, which we named condobulbosides A-C, were isolated from a methanol extract of the leaves of Liparis condylobulbon together with an apigenin C-glycoside, schaftoside. Their structures were established on the basis of spectral techniques, namely, UV, IR, HR-MS spectroscopy, both 1D and 2D NMR experiments, and chemical reactions.
Asunto(s)
Glicósidos/química , Orchidaceae/química , Hojas de la Planta/química , Glicósidos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Monosacáridos/química , Monosacáridos/aislamiento & purificación , Espectrofotometría Infrarroja , Espectrofotometría UltravioletaRESUMEN
The newly discovered 5,7-dihydroxy-6-geranylchromone ( 1) was isolated from PAULOWNIA TOMENTOSA fruit and subsequently characterized. The structure of the isolated compound was elucidated on the basis of extensive NMR experiments including HMQC, HMBC, COSY, and NOESY, as well as HR-MS, IR, and UV. The cytotoxicity of 1 was evaluated using a plant cell model represented by tobacco BY-2 cells. The other phytoconstituents ( 2 - 8) previously isolated from P. TOMENTOSA were similarly evaluated together with the known flavanones 10 and 11. The cytotoxicity (human erythro-leukaemia cell line K562) and activity on erythroid differentiation of compounds 2 - 9 and 12 and 13 have also been evaluated. Acteoside ( 2) was determined to be the most toxic of the compounds tested on BY-2 cells, diplacone ( 6) on the K562 cell line. Some aspects of the relationship between the flavanone skeleton substitution and the metabolic activation necessary for a toxic effect are discussed.
Asunto(s)
Cromonas/toxicidad , Frutas/química , Magnoliopsida/química , Fenoles/toxicidad , Diferenciación Celular/efectos de los fármacos , Cromonas/química , Cromonas/aislamiento & purificación , Células Eritroides/efectos de los fármacos , Flavanonas/química , Flavanonas/aislamiento & purificación , Flavanonas/toxicidad , Humanos , Células K562 , Dosificación Letal Mediana , Resonancia Magnética Nuclear Biomolecular , Fenoles/química , Fenoles/aislamiento & purificación , Nicotiana/citología , Nicotiana/efectos de los fármacosRESUMEN
Eight C-6-geranylflavonoids ( 1- 8) were isolated from an ethanol extract of Paulownia tomentosa fruits. Tomentodiplacone ( 1), 3'- O-methyl-5'-hydroxydiplacone ( 2), 3'- O-methyl-5'- O-methyldiplacone ( 3), and tomentodiplacone B ( 4) were obtained as new compounds, and 3'- O-methyldiplacol ( 5) was isolated for the first time from a natural source. The structures of these new compounds were determined by using mass spectrometry (including HRMS) and 1D and 2D NMR spectroscopy, and the absolute configurations of the compounds were determined by circular dichroism. The antibacterial activities of 1- 8 against seven bacteria and yeast were evaluated.