RESUMEN
One novel compound, (R)-3, 6-diethoxy-4-hydroxycyclohex-3-en-1-one (1) and thirteen known compounds were isolated from the waste tobacco leaves. The structures of two compounds (1-2) were confirmed and attributed firstly by the extensive spectroscopic data, including 1D/2D NMR, IR, HR-ESI-MS, CD, and ECD spectra. Notably, seven compounds (2, 3, 9, 10, 11, 12, and 13) exhibited better tyrosinase inhibitory activity than the positive control kojic acid. The binding modes of these compounds revealed that their structure formed strong hydrogen bonds and van der Waals forces with the active sites of tyrosinase. These results indicated that waste tobacco leaves are good resources for developing tyrosinase inhibitors.
Asunto(s)
Inhibidores Enzimáticos , Monofenol Monooxigenasa , Nicotiana , Hojas de la Planta , Monofenol Monooxigenasa/antagonistas & inhibidores , Monofenol Monooxigenasa/metabolismo , Hojas de la Planta/química , Nicotiana/química , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/aislamiento & purificación , Estructura Molecular , Relación Estructura-Actividad , Simulación del Acoplamiento MolecularRESUMEN
Three new compounds, including two new sesquiterpenes (1-2), named Annuumine E-F, and one new natural product, 3-hydroxy-2,6-dimethylbenzenemethanol (3), together with seventeen known compounds (4-20) were isolated from the ethanol extract of the roots of Capsicum annuum L. Among them, five compounds (4, 5, 9, 10 and 20) were isolated from this plant for the first time. The structures of new compounds (1-3) were determined via detailed analysis of the IR, HR-ESI-MS and 1D and 2D NMR spectra. The anti-inflammatory activities of the isolated compounds were evaluated by their ability to reduce NO release by LPS-induced RAW 264.7 cells. Notably, compound 11 exhibited moderate anti-inflammatory activity (IC50 =21.11â µM). Moreover, the antibacterial activities of the isolated compounds were also evaluated.
Asunto(s)
Capsicum , Animales , Ratones , Capsicum/química , Estructura Molecular , Células RAW 264.7 , Antiinflamatorios/química , Antibacterianos/farmacologíaRESUMEN
To identify the active constituents with α-glucosidase inhibitory activities in Sabia parviflora, three new compounds, namely, sabiaparviflora A-C (1, 2 and 8), and seven known compounds were isolated from the plant by repeated column chromatography. The structures of the new compounds were identified by extensive application of spectroscopic methods, including 1H NMR, 13C NMR, IR and HR-ESI-MS. All compounds, except for compounds 3-5, 9 and 10 were isolated for the first time from S. parviflora. Their α-glucosidase inhibitory activities were evaluated for the first time by the PNPG method. Three compounds (1, 7 and 10) exhibited marked activities, with IC50 values ranging from 104 to 324 µM, and their structure-activity relationship is preliminarily discussed herein.
Asunto(s)
Inhibidores de Glicósido Hidrolasas , alfa-Glucosidasas , Estructura Molecular , Inhibidores de Glicósido Hidrolasas/farmacología , Inhibidores de Glicósido Hidrolasas/química , alfa-Glucosidasas/metabolismo , Relación Estructura-Actividad , Extractos Vegetales/químicaRESUMEN
Four new pentacyclic triterpenoids named Sabiadiscolor A-D (1 and 7-9) together with eleven known ones were isolated by repeated column chromatography. Their structures were identified and characterized by NMR and MS spectral data as 6 oleanane-type pentacyclic triterpenoids (1-6), 7 ursane-type ones (7-13), and 2 lupanane-type ones (14-15). Except for compound 15, all other compounds were isolated from Sabia discolor Dunn for the first time. Their α-glycosidase inhibitory activities were evaluated, which showed that compounds 1, 3, 8, 9, 13, and 15 implied remarkable activities with IC50 values ranging from 0.09 to 0.27 µM, and the preliminary structure-activity relationship was discussed.
Asunto(s)
Triterpenos , Glicósido Hidrolasas , Estructura Molecular , Semillas , Relación Estructura-Actividad , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
To scientifically clarify the hepatoprotective constituents of Fructus Schizandrae chinensis, eleven batches samples of total dibenzocyclooctadiene lignans (TDL) from Schisandra chinensis were prepared by using the optimum extraction technique. Characteristic high-performance liquid chromatography (HPLC) chromatograms were obtained through HPLC analysis technology, and the hepatoprotective effects of the eleven batches of TDL were evaluated by MTT assay. Based on the chemical and biological activity results, the spectrum-effect relationship between the characteristic HPLC fingerprints and the hepatoprotective effect of TDL was established using Minitab 16.0 data analysis software. On the basis of the spectrum-effect relationship, thirteen compounds (1-13) were obtained from the TDL by chemical natural product chemical separation and purification technology, and their structures were identified on the basis of the spectral data and the literature. Based on these compounds, thirteen common peaks among the thirty-three chromatographic peaks in the above HPLC fingerprints were identified. Our findings showed that some components, including, schisandrin B (2), schisandrin A (3), and schisandrol B (7) had significant roles in promoting hepatoprotective activity. Preliminary verification of the spectrum-effect relationship of TDL from S. chinensis was carried out, and the results confirmed that the activity of a composite of these three key components in optimal ratios was better than that of any individual compound, which potentially confirmed the reliability of the spectrum-effect relationship and the synergistic effects of traditional Chinese medicine.
Asunto(s)
Ciclooctanos/farmacología , Lignanos/farmacología , Hígado/efectos de los fármacos , Sustancias Protectoras/farmacología , Schisandra/química , Animales , Tetracloruro de Carbono , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Análisis por Conglomerados , Ciclooctanos/química , Ciclooctanos/aislamiento & purificación , Análisis de los Mínimos Cuadrados , Lignanos/química , Lignanos/aislamiento & purificación , Ratones , Estructura Molecular , Sustancias Protectoras/química , Sustancias Protectoras/aislamiento & purificaciónRESUMEN
We integrate the genomics, proteomics, and phosphoproteomics of 480 clinical tissues from 146 patients in a Chinese colorectal cancer (CRC) cohort, among which 70 had metastatic CRC (mCRC). Proteomic profiling differentiates three CRC subtypes characterized by distinct clinical prognosis and molecular signatures. Proteomic and phosphoproteomic profiling of primary tumors alone successfully distinguishes cases with metastasis. Metastatic tissues exhibit high similarities with primary tumors at the genetic but not the proteomic level, and kinase network analysis reveals significant heterogeneity between primary colorectal tumors and their liver metastases. In vivo xenograft-based drug tests using 31 primary and metastatic tumors show personalized responses, which could also be predicted by kinase-substrate network analysis no matter whether tumors carry mutations in the drug-targeted genes. Our study provides a valuable resource for better understanding of mCRC and has potential for clinical application.
Asunto(s)
Antineoplásicos/uso terapéutico , Neoplasias Colorrectales/tratamiento farmacológico , Genómica/métodos , Metástasis de la Neoplasia/tratamiento farmacológico , Proteínas Quinasas/genética , Proteínas Quinasas/metabolismo , Proteómica/métodos , Animales , Antineoplásicos/farmacología , China , Estudios de Cohortes , Neoplasias Colorrectales/genética , Neoplasias Colorrectales/metabolismo , Perfilación de la Expresión Génica , Regulación Neoplásica de la Expresión Génica/efectos de los fármacos , Humanos , Ratones , Terapia Molecular Dirigida , Metástasis de la Neoplasia/genética , Fosforilación , Medicina de Precisión , Pronóstico , Proteínas Quinasas/farmacología , Ensayos Antitumor por Modelo de XenoinjertoRESUMEN
The regioselective demethoxylation and dehalogenation of dihalogenated dibenzocyclooctadiene lignans derivatives were realized in a one-step reaction with excellent yields in the sodium and t-butanol reaction system.
RESUMEN
Schisanhenol (Sol) was isolated from Schisandra rubriflora, and a series of derivatives (1-16, 15a-16a, and 15b-16b) were designed and prepared by chemical modification. The curative and protective effects of these dibenzocyclooctadiene lignan analogues against tobacco mosaic virus (TMV) were evaluated. Most analogues exhibited stronger protective effects than the positive control ningnanmycin. Dibromoschisanhenol (6) at 0.25mM exhibited the strongest protective activity (83.5±1.8% at 0.25mM), and 14-(3, 5-dibenzyloxy)-benzoyloxyschisanhenol (16) showed a significant curative effect (78.0±3.8% at 0.15mM) that was much stronger than that of the commercial virucide ningnanmycin. This study is the first to demonstrate that natural dibenzocyclooctadiene lignans and analogues are active against plant viruses.
Asunto(s)
Antivirales/farmacología , Ciclooctanos/farmacología , Lignanos/farmacología , Compuestos Policíclicos/farmacología , Virus del Mosaico del Tabaco/efectos de los fármacos , Antivirales/química , Ciclooctanos/química , Lignanos/química , Estructura Molecular , Compuestos Policíclicos/química , Relación Estructura-ActividadRESUMEN
AIM: To study the bufadienolides in the Chinese traditional drug "Ch'an Su" and their cytotoxic activity. METHOD: Various chromatographic techniques were used to isolate the constituents, and their structures were elucidated through physical and spectroscopic data. RESULTS: Twenty compounds were isolated, and eighteen were evaluated in vitro for their cytotoxic activity against A-549 and K-562 cells. CONCLUSION: Compound 1 (bufalin 3ß-acrylic ester) was a new bufadienolide and exhibited the most potent activity against the two tumor cell lines with IC50 values of 7.16 and 6.83 nmol · L(-1). The relationships between structure and activity are discussed.
Asunto(s)
Venenos de Anfibios/uso terapéutico , Antineoplásicos/uso terapéutico , Productos Biológicos/uso terapéutico , Bufanólidos/uso terapéutico , Neoplasias/tratamiento farmacológico , Venenos de Anfibios/química , Venenos de Anfibios/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Productos Biológicos/química , Productos Biológicos/farmacología , Bufanólidos/química , Bufanólidos/aislamiento & purificación , Bufanólidos/farmacología , Humanos , Concentración 50 Inhibidora , Células K562 , Medicina Tradicional China , Estructura Molecular , Relación Estructura-ActividadRESUMEN
A new hasubanan alkaloid, hernsubanine E (1), as well as two known compounds p-hydroxybenzaldehyde (2) and (-)-syringaresinol (3) have been isolated from the whole plants of Stephania hernandifolia by various column chromatographic methods. Their structures were identified by physicochemical properties and spectral analyses. Compounds 2 and 3 were isolated from the genus of Stephania for the first time.