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1.
J Pharm Pharmacol ; 74(3): 337-350, 2022 Mar 03.
Artigo em Inglês | MEDLINE | ID: mdl-34923582

RESUMO

OBJECTIVES: Plant-derived flavonolignans had been demonstrated to have various biological functions. They are an important class of natural products combined by a flavonoid unit and a phenylpropanoid unit. KEY FINDINGS: From the literature survey, 88 constituents from natural resources were identified. Different derivatives of flavonolignans were listed, fused phenylpropanoid unit with dioxane ring, or cyclic ether, or simple ether side chain, or lactone, and so on. Besides, the pharmacological effects of flavonolignans were summarized as well. It has a wide range of anti-tumour, antioxidant, anti-microorganic and anti-inflammatory effects. SUMMARY: This review had provided a full-scale profile of flavonolignans on its plant sources, phytochemistry and pharmacology, and also proposed some issues and perspectives which may be of concern in the future. It was greatly anticipated that the commercialization of the flavonolignans would lead to uplift the financial abilities of communities attending the growing of the flavonolignans and the relevant and potential production becoming an international herbal and pharmaceutical commodity.


Assuntos
Flavonolignanos/farmacologia , Extratos Vegetais/farmacologia , Plantas Medicinais/química , Animais , Flavonolignanos/isolamento & purificação , Humanos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia
2.
Fitoterapia ; 143: 104541, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-32151639

RESUMO

Four flavanolignans, ceibapentains A (1) and B (2) and cinchonains Ia (3) and Ib (4), were isolated for the first time from an ethyl acetate extract of Ceiba pentandra (L) (Bombacaceae) aerial parts. The ceibapentains A (1) and B (2) are new compounds and their structures, including the absolute configurations, were determined by HRESIMS, 1D and 2D NMR, and electronic circular dichroism analyses, then compared with reported data. Compounds 1-4 were tested for their anti-Alzheimer's activity via an assessment of their inhibitory effect on amyloid ß42 aggregation using a thioflavin T assay. The results revealed that cinchonain Ia (3) showed a higher inhibitory effect (91%) than the standard curcumin (70%). Compounds 1, 2, and 4 exhibited moderate activity, with inhibition ratios of 43%, 47%, and 58%, respectively. A molecular docking study on the binding mode of 3 and curcumin with an amyloid ß1-40 peptide fibril structure indicated a high affinity of cinchonain 1a (3) towards amyloid ß1-40 peptide, in agreement with the experimental results.


Assuntos
Peptídeos beta-Amiloides/antagonistas & inibidores , Ceiba/química , Flavonolignanos/farmacologia , Fragmentos de Peptídeos/antagonistas & inibidores , Dicroísmo Circular , Egito , Flavonolignanos/isolamento & purificação , Humanos , Simulação de Acoplamento Molecular , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Extratos Vegetais/química
3.
Molecules ; 24(6)2019 Mar 14.
Artigo em Inglês | MEDLINE | ID: mdl-30875758

RESUMO

Silybum marianum (L.) is a medicinal plant traditionally used in treatment of liver disorders. In last decades, silymarin (SM), a standardized extract from S. marianum seeds has been studied for its dermatological application, namely for UVB-protective properties. However, information on SM and its polyphenols effect on activity of enzymes participating in the (photo)aging process is limited. Therefore, evaluation of SM and its flavonolignans potential to inhibit collagenase, elastase, and hyaluronidase in tube tests was the goal of this study. The antioxidant and UV screening properties of SM and its flavonolignans silybin, isosilybin, silydianin, silychristin and 2,3-dehydrosilybin (DHSB) were also evaluated by a DPPH assay and spectrophotometrical measurement. DHSB showed the highest ability to scavenge DPPH radical and also revealed the highest UVA protection factor (PF-UVA) that corresponds with its absorption spectrum. SM and studied flavonolignans were found to exhibit anti-collagenase and anti-elastase activity. The most potent flavonolignan was DHSB. None of studied flavonolignans or SM showed anti-hyaluronidase activity. Our results suggest that SM and its flavonolignans may be useful agents for skin protection against the harmful effects of full-spectrum solar radiation including slowing down skin (photo)aging.


Assuntos
Flavonolignanos/química , Extratos Vegetais/química , Silimarina/química , Pele/efeitos dos fármacos , Antioxidantes/química , Antioxidantes/isolamento & purificação , Flavonolignanos/isolamento & purificação , Humanos , Silybum marianum/química , Sementes/química , Silimarina/isolamento & purificação , Pele/patologia , Pele/efeitos da radiação , Raios Ultravioleta/efeitos adversos
4.
J Chromatogr Sci ; 57(5): 418-425, 2019 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-30753465

RESUMO

Herbal plants are significant for the reason that they have a great potential in discovering drug precursors. However, how to purify compounds with higher purity from them is a question which needs to be discussed. In present study, an offline 2D reversed-phase (RP) preparative liquid chromatography coupled with solid-phase extraction (SPE) method was successfully developed for the separation of flavonolignan diastereoisomers from Arenaria kansuensis. Based on the analysis of results, the major conclusion that we have drawn from it is a RP-SPE was selected for enriching target flavonolignan sample from A. kansuensis. After that, an ODS preparative column was used for 1D preparation, and the target sample (4.6 g) was divided into five fractions with a recovery of 83.9%. Then, a C18HCE preparative column, a polar-modified RP (polar-copolymerized) type, was used for isolating flavonolignan diastereoisomers in the 2D preparation. By establishing optimal 2D chromatography, hydrophilic interaction chromatography (HILIC) columns and normal-phase (NP) columns were tested simultaneously, and the result showed that diastereoisomers are not suitable for HILIC and NP chromatography mode. Our study resulted in a tricin and five analogous derivative flavonolignans with purity >98% were successfully purified from A. kansuensis. This is the initial report of Salcolin C, Salcolin B, Tricin 4'-O-(C-veratroylglycol) ether and 5'-methoxyhydnocarpin D from A. kansuensis. In addition, it tended to be the first time that Tricin 4'-O-(C-veratroylglycol) ether is isolated from natural resource. This method has great potential for efficiently isolating flavonolignan diastereoisomers from A. kansuensis, and it shows a great prospect for the separation of flavonolignans from complex samples.


Assuntos
Arenaria/química , Cromatografia de Fase Reversa/métodos , Flavonolignanos/análise , Flavonolignanos/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/isolamento & purificação , Extração em Fase Sólida/métodos , Estereoisomerismo
5.
Fitoterapia ; 134: 81-87, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30690126

RESUMO

In this study, a new flavonolignan vernicilignan A was isolated from Toxicodendron vernicifluum. The neuroprotective effects of this compound against H2O2 induced cell injury in SH-SY5Y cells were evaluated by MTT assay and LDH release assay. Vernicilignan A dose-dependently attenuated the cell injury and LDH release induced by H2O2 in SH-SY5Y cells. Further study indicated that vernicilignan A reduced cell apoptosis caused by H2O2 treatment via regulation of some apoptotic related proteins including Bax, Bcl-2, caspase 3 and caspase 9. Also, vernicilignan A increase the cell viability of H2O2 treated cells via the activation of Akt and GSK3ß. Base on the findings, vernicilignan A exhibited neuroprotective effects through the activation of PI3K/Akt signaling and inhibition of mitochondria apoptosis pathway. Vernicilignan A might be a promising therapeutic agent for oxidative stress induced neurodegenerative diseases.


Assuntos
Flavonolignanos/farmacologia , Fármacos Neuroprotetores/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Toxicodendron/química , Apoptose , Caspase 3/metabolismo , Caspase 9/metabolismo , Linhagem Celular , Sobrevivência Celular , China , Flavonolignanos/isolamento & purificação , Humanos , Peróxido de Hidrogênio , Mitocôndrias , Estrutura Molecular , Fármacos Neuroprotetores/isolamento & purificação , Fosfatidilinositol 3-Quinases/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Proteínas Proto-Oncogênicas c-akt/metabolismo , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , Transdução de Sinais , Madeira/química , Proteína X Associada a bcl-2/metabolismo
6.
Nat Prod Res ; 31(19): 2233-2238, 2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28287276

RESUMO

Two new compounds a flavanolignan (1), and an alkane (2) along with four known compounds including two fatty acid esters (3-4) and two isocoumarins (5-6) were isolated from the methanolic extract of the stem bark of Newtonia griffoniana. Their structures were elucidated using spectroscopic methods including extensive 1-D and 2-D NMR experiments.


Assuntos
Alcanos/isolamento & purificação , Fabaceae/química , Flavonolignanos/isolamento & purificação , Alcanos/análise , Ácidos Graxos/química , Ácidos Graxos/isolamento & purificação , Flavonolignanos/química , Isocumarinas/química , Isocumarinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Casca de Planta/química , Extratos Vegetais/química
7.
J Agric Food Chem ; 65(7): 1320-1327, 2017 Feb 22.
Artigo em Inglês | MEDLINE | ID: mdl-28135082

RESUMO

Elymus natans, a perennial gramineous grass, plays an important role in animal husbandry and environmental sustenance in the Qinghai-Tibet plateau as a result of its high forage quality and good adaptability to the local environment. A bioassay showed that the extracts of green grasses of E. natans (GG) exhibited stronger phytotoxic activities than withered grasses (WG) against crops and grasses. In view of the secondary metabolites, which may be responsible for the resistance of the plant, the chemical components of GG were investigated. The flavone tricin, E1, and 10 flavonolignans, E2-E11, including three new flavonolignans, E2, E10, and E11, were isolated and identified. As far as we know, this is the first report on the chemical constitutions of the plant until now. The contents of compounds E1 and E4-E7 in GG were significantly higher than those in WG in high-performance liquid chromatography analysis, and they also showed observably phytotoxic activities against lettuce and Festuca arundinacea.


Assuntos
Elymus/química , Flavonolignanos/toxicidade , Extratos Vegetais/toxicidade , Animais , Elymus/toxicidade , Festuca/efeitos dos fármacos , Flavonolignanos/análise , Flavonolignanos/isolamento & purificação , Lactuca/efeitos dos fármacos , Extratos Vegetais/análise , Extratos Vegetais/isolamento & purificação , Poaceae/efeitos dos fármacos
8.
J Pharm Biomed Anal ; 126: 26-33, 2016 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-27136284

RESUMO

Validated methods are needed for the analysis of natural product secondary metabolites. These methods are particularly important to translate in vitro observations to in vivo studies. Herein, a method is reported for the analysis of the key secondary metabolites, a series of flavonolignans and a flavonoid, from an extract prepared from the seeds of milk thistle [Silybum marianum (L.) Gaertn. (Asteraceae)]. This report represents the first UHPLC MS-MS method validated for quantitative analysis of these compounds. The method takes advantage of the excellent resolution achievable with UHPLC to provide a complete analysis in less than 7min. The method is validated using both UV and MS detectors, making it applicable in laboratories with different types of analytical instrumentation available. Lower limits of quantitation achieved with this method range from 0.0400µM to 0.160µM with UV and from 0.0800µM to 0.160µM with MS. The new method is employed to evaluate variability in constituent composition in various commercial S. marianum extracts, and to show that storage of the milk thistle compounds in DMSO leads to degradation.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Flavonolignanos/análise , Silybum marianum/química , Espectrometria de Massas em Tandem/métodos , Dimetil Sulfóxido/química , Flavonoides/análise , Flavonoides/isolamento & purificação , Flavonolignanos/isolamento & purificação , Limite de Detecção , Extratos Vegetais/análise , Extratos Vegetais/química , Sementes , Solventes/química
9.
Curr Pharm Des ; 21(38): 5489-500, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26429716

RESUMO

Flavonolignans are plant natural products, composed of a flavonoid moiety and a lignan (phenylpropanoid) part. Current literature focuses on flavonolignans formed from taxifolin and coniferyl alcohol as e.g. silybin and its congeners from fruit extract from the purple variety of the milk thistle (Silybum marianum) denoted as "silymarin". This review describes chemistry and biological activity of so far neglected "non-taxifolin" based flavonolignans, derived from apigenin, luteolin, tricin, chrysoeriol, naringenin and eriodictyol, as the flavonoid part. Up-to-date knowledge on hydnocarpin, hydnocarpin-D, pseudotsuganol, hydnowightin, neohydnocarpin, palstatin, salcolins A and B, anastatins A and B, sinaiticin, silyamandin and silandrin is summarized in the present paper. Most of non-taxifolin derived flavonolignans have been shown to exhibit in vitro and/or in vivo anti-hepatotoxic, anti-oxidant, free radical scavenging, anti-inflammatory, anti-proliferative, anti-cancer, chemotherapy potentiating, anti-melanogenic, anti-bacterial, vasorelaxing, anti-platelet aggregation and/or hypotriglyceridemic activity, often stronger than silybin. Many of these compounds inhibited Staphylococcus aureus multidrug resistance pump NorA and sensitized multidrug resistant cancer cell lines showing a potential as adjuvants. Non-taxifolin derived flavonolignans are a relatively unexplored group of compounds with interesting biological activity and great application potential. Their detailed study could provide a new insight into the biomimetic synthesis in order to obtain new compounds with greater activity and identify new lead structures for the biomedicinal research.


Assuntos
Flavonolignanos/química , Flavonolignanos/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Quercetina/análogos & derivados , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Flavonolignanos/isolamento & purificação , Humanos , Silybum marianum , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Quercetina/química , Quercetina/isolamento & purificação , Quercetina/farmacologia , Staphylococcus aureus/efeitos dos fármacos
10.
Drug Metab Dispos ; 43(11): 1734-43, 2015 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-26316643

RESUMO

Plant-based therapeutics, including herbal products, continue to represent a growing facet of the contemporary health care market. Mechanistic descriptions of the pharmacokinetics and pharmacodynamics of constituents composing these products remain nascent, particularly for metabolites produced following herbal product ingestion. Generation and characterization of authentic metabolite standards are essential to improve the quantitative mechanistic understanding of herbal product disposition in both in vitro and in vivo systems. Using the model herbal product, milk thistle, the objective of this work was to biosynthesize multimilligram quantities of glucuronides of select constituents (flavonolignans) to fill multiple knowledge gaps in the understanding of herbal product disposition and action. A partnership between clinical pharmacology and natural products chemistry expertise was leveraged to optimize reaction conditions for efficient glucuronide formation and evaluate alternate enzyme and reagent sources to improve cost effectiveness. Optimized reaction conditions used at least one-fourth the amount of microsomal protein (from bovine liver) and cofactor (UDP glucuronic acid) compared with typical conditions using human-derived subcellular fractions, providing substantial cost savings. Glucuronidation was flavonolignan-dependent. Silybin A, silybin B, isosilybin A, and isosilybin B generated five, four, four, and three monoglucuronides, respectively. Large-scale synthesis (40 mg of starting material) generated three glucuronides of silybin A: silybin A-7-O-ß-D-glucuronide (15.7 mg), silybin A-5-O-ß-D-glucuronide (1.6 mg), and silybin A-4´´-O-ß-D-glucuronide (11.1 mg). This optimized, cost-efficient method lays the foundation for a systematic approach to synthesize and characterize herbal product constituent glucuronides, enabling an improved understanding of mechanisms underlying herbal product disposition and action.


Assuntos
Flavonolignanos/síntese química , Glucuronídeos/síntese química , Microssomos Hepáticos/enzimologia , Extratos Vegetais/síntese química , Silybum marianum/enzimologia , Animais , Bovinos , Flavonolignanos/isolamento & purificação , Glucuronídeos/isolamento & purificação , Humanos , Extratos Vegetais/isolamento & purificação
11.
Food Chem Toxicol ; 83: 275-82, 2015 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-26172510

RESUMO

The optimal conditions of supercritical carbon dioxide (SC-CO2) (160-220 bars, 40-80 °C) technology combined with co-solvent (ethanol), to recover oil, flavonolignans (silychristin, silydianin and silybinin) and fatty acids from milk thistle seeds, to be used as food additives and/or nutraceuticals, were studied. Moreover, the antioxidant and cytotoxic activities of the SC-CO2 oil seeds extracts were evaluated in Caco-2 carcinoma cells. Pressure and temperature had a significant effect on oil and flavonolignans recovery, although there was not observed a clear trend. SC-CO2 with co-solvent extraction at 220 bars, 40 °C was the optimum treatment to recover oil (30.8%) and flavonolignans from milk thistle seeds. Moreover, linoleic (47.64-66.70%), and oleic (19.68-24.83%) acids were the predominant fatty acids in the oil extracts recovered from milk thistle under SC-CO2. In addition, SC-CO2 extract showed a high antioxidant activity determined by DPPH and ABTS tests. Cytotoxic activities of silychristin, silydianin and silybinin and the obtained SC-CO2 extract (220 bars, 40 °C) were evaluated against Caco-2 cells. The SC-CO2 extract inhibited the proliferation of Caco-2 cells in a dose-responsive manner and induced the highest percentage of mortality of Caco-2 cells (from 43 to 71% for concentrations from 10 up to 100 µg/ml of SC-CO2 oil seeds).


Assuntos
Antineoplásicos Fitogênicos/metabolismo , Antioxidantes/isolamento & purificação , Carcinoma/metabolismo , Flavonolignanos/isolamento & purificação , Óleos de Plantas/isolamento & purificação , Sementes/química , Silybum marianum/química , Anticarcinógenos/análise , Anticarcinógenos/química , Anticarcinógenos/isolamento & purificação , Anticarcinógenos/metabolismo , Antineoplásicos Fitogênicos/análise , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/análise , Antioxidantes/química , Antioxidantes/metabolismo , Células CACO-2 , Carcinoma/patologia , Sobrevivência Celular , Cromatografia com Fluido Supercrítico , Suplementos Nutricionais/análise , Ácidos Graxos/análise , Ácidos Graxos/isolamento & purificação , Flavonolignanos/análise , Flavonolignanos/metabolismo , Aditivos Alimentares/análise , Aditivos Alimentares/química , Aditivos Alimentares/isolamento & purificação , Aditivos Alimentares/metabolismo , Humanos , Óleos de Plantas/química , Óleos de Plantas/metabolismo , Silibina , Silimarina/análise , Silimarina/isolamento & purificação , Silimarina/metabolismo , Tunísia
12.
Molecules ; 20(4): 5616-24, 2015 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-25830790

RESUMO

Two new flavonolignan glycosides, tricin-4'-O-(threo-ß-guaiacylglyceryl) ether 7''-O-ß-D-glucopyranose (4) and tricin-4'-O-(erythro-ß-guaiacylglyceryl) ether 7''-O-ß-D-glucopyranose (5) were isolated from the roots of Zizania latifolia, together with tricin-7-O-ß-D-glucopyranose (1), tricin-4'-O-(threo-ß-guaiacylglyceryl) ether 7-O-ß-D-glucopyranose (2), and tricin-4'-O-(erythro-ß-guaiacylglyceryl) ether 7-O-ß-D-glucopyranose (3). Their structures were identified on the basis of spectroscopic techniques, including HR-ESI/MS, 1D-NMR (1H, 13C, DEPT), 2D-NMR (gCOSY, gHSQC, gHMBC), and IR spectroscopy.


Assuntos
Flavonolignanos/isolamento & purificação , Glicosídeos/isolamento & purificação , Extratos Vegetais/química , Poaceae/química , Flavonolignanos/química , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Componentes Aéreos da Planta/química , Raízes de Plantas/química
13.
Biosci Biotechnol Biochem ; 79(5): 700-6, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25559019

RESUMO

Methanol extract of Zizania latifolia was partitioned with EtOAc, n-BuOH, and H2O. From the EtOAc layers, a new flavonolignan along with a known flavone and three known flavonolignans, tricin (1), salcolin A (2), salcolin B (3), and salcolin C (4), were isolated through repeated silica gel and ODS column chromatography. The chemical structure of the new flavonolignan was determined to be tricin-4'-O-[erythro-ß-guaiacyl-(7″-O-methyl)-glyceryl] ether and was named salcolin D (5) based on physicochemical and spectroscopic data, including FT-NMR and ESI-MS. All compounds were isolated for the first time from this plant. Compounds 2-5, tricin derivatives, all exhibited higher anti-inflammatory and anti-allergy activities than tricin. In particular, salcolin D (5) was shown to have the strongest inhibitory activity against LPS-induced NO production in RAW 264.7 cells as well as ß-hexosaminidase release in IgE-sensitized RBL-2H3 cells. These results suggest that the presence of tricin derivatives conveys allergy and inflammation treatment ability to Z. latifolia.


Assuntos
Antialérgicos/farmacologia , Anti-Inflamatórios não Esteroides/farmacologia , Flavonoides/química , Poaceae/química , Animais , Antialérgicos/química , Anti-Inflamatórios não Esteroides/química , Linhagem Celular/efeitos dos fármacos , Avaliação Pré-Clínica de Medicamentos/métodos , Flavonas/química , Flavonas/farmacologia , Flavonoides/farmacologia , Flavonolignanos/química , Flavonolignanos/isolamento & purificação , Flavonolignanos/farmacologia , Imunoglobulina E/farmacologia , Lignanas/química , Lignanas/farmacologia , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Ratos , beta-N-Acetil-Hexosaminidases/antagonistas & inibidores , beta-N-Acetil-Hexosaminidases/metabolismo
14.
J Sep Sci ; 37(17): 2300-6, 2014 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-24923482

RESUMO

Silymarin extracted from Silybum marianum (L.) Gaertn consists of a large number of flavonolignans, of which diastereoisomeric flavonolignans including silybin A and silybin B, and isosilybin A and isosilybin B are the main bioactive components, whose preparation from the crude extracts is still a difficult task. In this work, binary-column recycling preparative high-performance liquid chromatography systems without sample loop trapping, where two columns were switched alternately via one or two six-port switching valves, were established and successfully applied to the isolation and purification of the four diastereoisomeric flavonolignans from silymarin. The proposed system showed significant advantages over conventional preparative high-performance liquid chromatography with a single column in increasing efficiency and reducing the cost. To obtain the same amounts of products, the proposed system spends only one tenth of the time that the conventional system spends, and needs only one eleventh of the solvent that the conventional system consumes. Using the proposed system, the four diastereoisomers were successfully isolated from silymarin with purities over 98%.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Medicamentos de Ervas Chinesas/isolamento & purificação , Flavonolignanos/isolamento & purificação , Silybum marianum/química , Cromatografia Líquida de Alta Pressão/instrumentação , Medicamentos de Ervas Chinesas/química , Flavonolignanos/química , Estereoisomerismo
15.
Plant Foods Hum Nutr ; 66(1): 91-6, 2011 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-21373805

RESUMO

Njavara is an important medicinal rice variety of Kerala, India, widely used in Ayurveda as a 'health food' and in the treatment of rheumatoid arthritis, paralysis, neurodegenerative diseases and in rejuvenation therapy. Phytochemical investigations and spectroscopic studies of the diethyl ether fraction of methanolic extract of Njavara Black (NB) rice bran gave three important compounds namely, tricin and two rare flavonolignans- tricin 4'-O-(erythro-ß-guaiacylglyceryl) ether and tricin 4'-O-(threo-ß-guaiacylglyceryl) ether. The EC(50) values of these compounds in DPPH system were 90.39, 352.04 and 208.1 µg/ml, respectively. Quantification of the compounds by HPLC in NB and staple, non-medicinal rice varieties Sujatha (SJ) and Palakkadan Matta (PM) showed that tricin is present 39.64 and 16.12 fold higher in NB, compared to SJ and PM, respectively. This is the first report on the occurrence of tricin at significantly higher levels in Njavara and occurrence of the two flavonolignans in Oryza sativa species. Of the three compounds, tricin and the threo- form of flavonolignan showed anti-inflammatory effect of >65% after 5 h, at 2 mg/kg, in carrageenan-induced, paw edema experiments in rats. The results of the study corroborate with the preferential use of Njavara in indigenous medicine, over staple varieties.


Assuntos
Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Flavonolignanos/isolamento & purificação , Flavonolignanos/farmacologia , Oryza/química , Plantas Medicinais/química , Animais , Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Cromatografia Líquida de Alta Pressão/métodos , Suplementos Nutricionais/análise , Extratos Vegetais/farmacologia , Ratos
16.
J Asian Nat Prod Res ; 13(1): 80-3, 2011 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-21253954

RESUMO

A new flavonolignan, anthelminthicol A (1), together with four known compounds, was isolated from the EtOAc extracts of the seeds of Hydnocarpus anthelminthica. Their structures were elucidated using extensive spectroscopic techniques. Bioassay showed that compounds 3-5 could inhibit nitric oxide production in LPS-stimulated RAW 264.7 macrophage cell lines, with IC(50) values of 7.81, 9.38, and 10.55 µM, respectively.


Assuntos
Anti-Inflamatórios não Esteroides/isolamento & purificação , Anti-Inflamatórios não Esteroides/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Flavonolignanos/isolamento & purificação , Flavonolignanos/farmacologia , Salicaceae/química , Animais , Anti-Inflamatórios não Esteroides/química , Dinoprostona/farmacologia , Medicamentos de Ervas Chinesas/química , Flavonolignanos/química , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Óxido Nítrico/farmacologia , Ressonância Magnética Nuclear Biomolecular , Sementes/química
17.
J Asian Nat Prod Res ; 12(9): 765-9, 2010 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-20839123

RESUMO

Two new phenolic glycosides, syringic acid-4-O-α-L-rhamnoside (1) and (-)-hydnocarpin-7-O-ß-D-glucoside (2), were isolated from the traditional Chinese medicinal herb Inula cappa. The structures of the new compounds were elucidated by means of spectroscopic methods such as 1D, 2D NMR, and HR-ESI-MS.


Assuntos
Asteraceae/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Flavonolignanos/isolamento & purificação , Ácido Gálico/análogos & derivados , Glucosídeos/isolamento & purificação , Glicosídeos/isolamento & purificação , Inula/química , Medicamentos de Ervas Chinesas/química , Flavonolignanos/química , Ácido Gálico/química , Ácido Gálico/isolamento & purificação , Glucosídeos/química , Glicosídeos/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Fenóis/química , Estereoisomerismo
18.
Proc Natl Acad Sci U S A ; 107(13): 5995-9, 2010 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-20231449

RESUMO

Silymarin, also known as milk thistle extract, inhibits hepatitis C virus (HCV) infection and also displays antioxidant, anti-inflammatory, and immunomodulatory actions that contribute to its hepatoprotective effects. In the current study, we evaluated the hepatoprotective actions of the seven major flavonolignans and one flavonoid that comprise silymarin. Activities tested included inhibition of: HCV cell culture infection, NS5B polymerase activity, TNF-alpha-induced NF-kappaB transcription, virus-induced oxidative stress, and T-cell proliferation. All compounds were well tolerated by Huh7 human hepatoma cells up to 80 muM, except for isosilybin B, which was toxic to cells above 10 muM. Select compounds had stronger hepatoprotective functions than silymarin in all assays tested except in T cell proliferation. Pure compounds inhibited JFH-1 NS5B polymerase but only at concentrations above 300 muM. Silymarin suppressed TNF-alpha activation of NF-kappaB dependent transcription, which involved partial inhibition of IkappaB and RelA/p65 serine phosphorylation, and p50 and p65 nuclear translocation, without affecting binding of p50 and p65 to DNA. All compounds blocked JFH-1 virus-induced oxidative stress, including compounds that lacked antiviral activity. The most potent compounds across multiple assays were taxifolin, isosilybin A, silybin A, silybin B, and silibinin, a mixture of silybin A and silybin B. The data suggest that silymarin- and silymarin-derived compounds may influence HCV disease course in some patients. Studies where standardized silymarin is dosed to identify specific clinical endpoints are urgently needed.


Assuntos
Flavonolignanos/isolamento & purificação , Flavonolignanos/farmacologia , Fígado/efeitos dos fármacos , Substâncias Protetoras/isolamento & purificação , Substâncias Protetoras/farmacologia , Silimarina/química , Silimarina/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Antivirais/química , Antivirais/isolamento & purificação , Antivirais/farmacologia , Linhagem Celular Tumoral , Avaliação Pré-Clínica de Medicamentos , Flavonolignanos/química , Hepatite C/tratamento farmacológico , Hepatite C/prevenção & controle , Humanos , Fatores Imunológicos/química , Fatores Imunológicos/isolamento & purificação , Fatores Imunológicos/farmacologia , Fígado/citologia , Fígado/metabolismo , NF-kappa B/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Substâncias Protetoras/química , Linfócitos T/efeitos dos fármacos , Linfócitos T/imunologia
19.
Phytochemistry ; 71(2-3): 271-9, 2010 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-20006366

RESUMO

Tricin-type flavonolignans, (2S)-dihydrotricin 4'-O-(erythro-beta-guaiacylglyceryl) ether, (2S)-dihydrotricin 4'-O-(threo-beta-guaiacylglyceryl) ether, (2S)-dihydrotricin 4'-O-(threo-beta-4-hydroxyphenylglyceryl) ether, tricin 4'-O-(erythro-beta-4-hydroxyphenylglyceryl) ether, tricin 4'-O-(threo-beta-4-hydroxylphenylglyceryl) ether, and (2S)-dihydrotricin 4'-O-(beta-6''-methoxy-4''-oxo-chroman-3''-yloxy) ether namely calquiquelignan A-F, respectively, were isolated and characterized from the EtOAc extract of Calamus quiquesetinervius. Additionally, six known phenolic compounds, including dihydrotricin, tricin, salcolin A, p-hydroxybenzoic acid, (2S, 3S)-trans-dihydrokapempferol and (2S)-naringenin, were also obtained and identified from the extract. Structures of the flavonolignans were assigned based on spectroscopic analyses that included 1D and 2D NMR spectroscopic techniques, such as HMQC, HMBC, and NOESY. Bioassay results showed that calquiquelignan A, dihydrotricin and (2S)-naringenin exhibited significant vasodilatory potencies, as indicated by 60.3%, 80.3% and 60.9% relaxations, respectively, at 100 microM. Salcolin A showed potent platelet aggregation inhibition, compared with aspirin. Most of the tricin-type derivatives (calquiquelignan A-B, dihydrotricin and tricin) also exhibited more potent hydroxyl radical ((.)OH) scavenging activity than trolox as characterized by the ultraweak chemiluminescence assay.


Assuntos
Antioxidantes/farmacologia , Calamus/química , Flavonolignanos/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Vasoconstrição/efeitos dos fármacos , Vasodilatadores/farmacologia , Animais , Antioxidantes/isolamento & purificação , Flavonolignanos/isolamento & purificação , Masculino , Estrutura Molecular , Fenóis/isolamento & purificação , Extratos Vegetais/química , Caules de Planta , Ratos , Ratos Sprague-Dawley , Vasodilatadores/isolamento & purificação
20.
Zhongguo Zhong Yao Za Zhi ; 31(4): 269-79, 2006 Feb.
Artigo em Chinês | MEDLINE | ID: mdl-16706012

RESUMO

In this article, the research of chemical constituents and bioactivities in recent ten years has been reviewed of plants from the 12 genera in Flacourtiaceae related to the medicinal resources in China. The research in China about the plants from Flacourtiaceae was done very little, but many literatures have been reported abroad. The plants from Flacourtiaceae mostly contain the constituents such as aromatic glucosides, lignanoid glucosides, diterpenoids and cyclopentenoid cyanohydrin glucosides et al. These compounds or plant extracts mainly show antibacterial, antiviral, antitumor, hypolipidemic and hypoglycemic activities. The research of plants from Carrierea, Itoa and Bennettiodendron of Flacourtiaceae in China is still blank. The systemic research about chemical constituents and bioactivities of plants from these genera will play important roles in the discovery of novel natural products and active constituents, and provide valuable reference for the classifying of plants from these genera.


Assuntos
Extratos Vegetais/farmacologia , Plantas Medicinais/química , Salicaceae/química , Animais , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antineoplásicos Fitogênicos , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Flavonolignanos/química , Flavonolignanos/isolamento & purificação , Flavonolignanos/farmacologia , Glucosídeos/química , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Humanos , Hipolipemiantes/isolamento & purificação , Hipolipemiantes/farmacologia , Estrutura Molecular , Extratos Vegetais/isolamento & purificação , Plantas Medicinais/classificação , Salicaceae/classificação
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