RESUMO
Lycium barbarum L. berries have a remarkable chemical composition and extensive biological activities, being a valuable component of health and nutraceutical practices. Nevertheless, a deep insight on the intestinal permeation of the pro-healthy bioactive compounds is urgently needed to predict the real effects on human body. This study attempted, for the first time, to optimize the Ultrasound-Assisted Extraction (UAE) of goji berries using a Response Surface Methodology approach and establish the intestinal permeation of the principal pro-healthy compounds. The optimal extraction conditions were a solid:liquid ratio of 8.75 % for 56.21 min, using an intensity of 59.05 W/m2. The optimal extract displayed a remarkable antioxidant capacity, with LC/DAD-ESI-MS analysis unveiled a diverse phytochemical profile, encompassing different compounds (e.g. glu-lycibarbarspermidine F, 2-glu-kukoamine, rutin, 3,5-dicaffeoylquinic acid). The intestinal co-culture model demonstrated that glu-lycibarbarspermidine F (isomer 2) (73.70 %), 3,5-dicaffeoylquinic acid (52.66 %), and isorhamnetin-3-O-rutinoside (49.31 %) traversed the intestinal cell layer, exerting beneficial health-promoting effects.
Assuntos
Antioxidantes , Frutas , Lycium , Extratos Vegetais , Lycium/química , Frutas/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Antioxidantes/farmacologia , Antioxidantes/isolamento & purificação , Humanos , Permeabilidade , Ondas Ultrassônicas , Compostos Fitoquímicos/isolamento & purificação , Mucosa Intestinal/metabolismo , Células CACO-2 , Absorção Intestinal , Rutina/isolamento & purificação , Ultrassom/métodos , Função da Barreira IntestinalRESUMO
With the proposal of the 2030 Agenda for Sustainable Development, the Chinese medicine extraction technology has been innovatively improved to prioritize low energy consumption, sustainability, and minimized organic solvent utilization. Forsythia suspensa (FS) possesses favorable pharmacological properties and is extensively utilized in traditional Chinese medicine. However, due to the limitations of the composition and extraction methods, its potential has not been fully developed. Thus, a combination of ultrasound-assisted extraction (UAE), enzyme-assisted extraction (EAE), and ß-cyclodextrin extraction (ß-CDE) was employed to isolate and purify rutin, phillyrin, and forsythoside A from FS. The results demonstrated that the efficiency of extracting enzymatic and ultrasound assisted ß-cyclodextrin extraction (EUA-ß-CDE) was highly influenced by the temperature and duration of hydrolysis, as well as the duration of the extraction process. According to the results of the single-factor experiment, Box-Behnken design (BBD) in Response surface method (RSM) was used to optimize the experimental parameters to achieve the maximum comprehensive evaluation value (CEV) value. The EUA-ß-CDE compared with other extraction methods, has good extraction effect and low energy consumption by high performance liquid chromatography (HPLC), scanning electron microscopy (SEM), calculation of power consumption and CO2 emission The EUA-ß-CDE compared with other extraction methods, has good extraction effect and low energy consumption by HPLC, SEM, calculation of power consumption and CO2 emission. Then, the structural characteristics of EUA-ß-CDE of FS extract had significant interaction with ß-CD by Fourier infrared spectroscopy (FT-IR) and differential scanning calorimetry (DSC). In addition, EUA-ß-CDE extract has good antioxidant and anti-inflammatory activities. The establishment of EUA-ß-CDE of FS provides a new idea for the development and application of other sustainable extraction methods of traditional Chinese medicine.
Assuntos
Anti-Inflamatórios , Antioxidantes , Forsythia , Ondas Ultrassônicas , beta-Ciclodextrinas , Forsythia/química , beta-Ciclodextrinas/química , Antioxidantes/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Fracionamento Químico/métodos , Enzimas/metabolismo , Temperatura , Glucosídeos/isolamento & purificação , Glucosídeos/química , Glucosídeos/farmacologia , Hidrólise , Rutina/isolamento & purificação , Rutina/química , Rutina/farmacologiaRESUMO
The leaf homogenate of Psychotria insularum is widely used in Samoan traditional medicine to treat inflammation associated with fever, body aches, swellings, wounds, elephantiasis, incontinence, skin infections, vomiting, respiratory infections, and abdominal distress. However, the bioactive components and underlying mechanisms of action are unknown. We used chemical genomic analyses in the model organism Saccharomyces cerevisiae (baker's yeast) to identify and characterize an iron homeostasis mechanism of action in the traditional medicine as an unfractionated entity to emulate its traditional use. Bioactivity-guided fractionation of the homogenate identified two flavonol glycosides, rutin and nicotiflorin, each binding iron in an ion-dependent molecular networking metabolomics analysis. Translating results to mammalian immune cells and traditional application, the iron chelator activity of the P. insularum homogenate or rutin decreased proinflammatory and enhanced anti-inflammatory cytokine responses in immune cells. Together, the synergistic power of combining traditional knowledge with chemical genomics, metabolomics, and bioassay-guided fractionation provided molecular insight into a relatively understudied Samoan traditional medicine and developed methodology to advance ethnobotany.
Assuntos
Anti-Inflamatórios/análise , Flavonoides/isolamento & purificação , Quelantes de Ferro/análise , Fenóis/isolamento & purificação , Psychotria/química , Rutina/isolamento & purificação , Animais , Avaliação Pré-Clínica de Medicamentos , Etnobotânica , Feminino , Genômica , Masculino , Medicina Tradicional , Metabolômica , Camundongos Endogâmicos C57BL , Plantas Medicinais/química , Saccharomyces cerevisiae , SamoaRESUMO
BACKGROUND: Caulerpa lentillifera (CL) is a green seaweed, and its edible part represents added value as a functional ingredient. CL was dried and extracted for the determination of its active compounds and the evaluation of its biological activities. The major constituents of CL extract (CLE), including tannic acid, catechin, rutin, and isoquercetin, exhibited beneficial effects, such as antioxidant activity, anti-diabetic activity, immunomodulatory effects, and anti-cancer activities in in vitro and in vivo models. Whether CLE has an anti-inflammatory effect and immune response remains unclear. METHODS: This study examined the effect of CLE on the inflammatory status and immune response of lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and the mechanisms involved therein. RAW264.7 cells were treated with different concentrations of CLE (0.1-1000 µg/mL) with or without LPS (1 µg/mL) for 24 h. Expression and production of the inflammatory cytokines, enzymes, and mediators were evaluated. RESULTS: CLE suppressed expression and production of the pro-inflammatory cytokines IL-6 and TNF-α. Moreover, CLE inhibited expression and secretion of the inflammatory enzyme COX-2 and the mediators PGE2 and NO. CLE also reduced DNA damage. Furthermore, CLE stimulated the immune response by modulating the cell cycle regulators p27, p53, cyclin D2, and cyclin E2. CONCLUSIONS: CLE inhibits inflammatory responses in LPS-activated macrophages by downregulating inflammatory cytokines and mediators. Furthermore, CLE has an immunomodulatory effect by modulating cell cycle regulators.
Assuntos
Anti-Inflamatórios/farmacologia , Catequina/farmacologia , Caulerpa/química , Quercetina/análogos & derivados , Rutina/farmacologia , Taninos/farmacologia , Animais , Catequina/isolamento & purificação , Citocinas/genética , Relação Dose-Resposta a Droga , Regulação da Expressão Gênica/efeitos dos fármacos , Imunidade/efeitos dos fármacos , Lipopolissacarídeos/efeitos adversos , Camundongos , Quercetina/isolamento & purificação , Quercetina/farmacologia , Células RAW 264.7 , Rutina/isolamento & purificação , Taninos/isolamento & purificaçãoRESUMO
In response to the urgent need to control Coronavirus disease 19 (COVID-19), this study aims to explore potential anti-SARS-CoV-2 agents from natural sources. Moreover, cytokine immunological responses to the viral infection could lead to acute respiratory distress which is considered a critical and life-threatening complication associated with the infection. Therefore, the anti-viral and anti-inflammatory agents can be key to the management of patients with COVID-19. Four bioactive compounds, namely ferulic acid 1, rutin 2, gallic acid 3, and chlorogenic acid 4 were isolated from the leaves of Pimenta dioica (L.) Merr (ethyl acetate extract) and identified using spectroscopic evidence. Furthermore, molecular docking and dynamics simulations were performed for the isolated and identified compounds (1-4) against SARS-CoV-2 main protease (Mpro) as a proposed mechanism of action. Furthermore, all compounds were tested for their half-maximal cytotoxicity (CC50) and SARS-CoV-2 inhibitory concentrations (IC50). Additionally, lung toxicity was induced in rats by mercuric chloride and the effects of treatment with P. dioca aqueous extract, ferulic acid 1, rutin 2, gallic acid 3, and chlorogenic acid 4 were recorded through measuring TNF-α, IL-1ß, IL-2, IL-10, G-CSF, and genetic expression of miRNA 21-3P and miRNA-155 levels to assess their anti-inflammatory effects essential for COVID-19 patients. Interestingly, rutin 2, gallic acid 3, and chlorogenic acid 4 showed remarkable anti-SARS-CoV-2 activities with IC50 values of 31 µg/mL, 108 µg/mL, and 360 µg/mL, respectively. Moreover, the anti-inflammatory effects were found to be better in ferulic acid 1 and rutin 2 treatments. Our results could be promising for more advanced preclinical and clinical studies especially on rutin 2 either alone or in combination with other isolates for COVID-19 management.
Assuntos
Anti-Inflamatórios/farmacologia , Antivirais/farmacologia , Tratamento Farmacológico da COVID-19 , Pimenta , Extratos Vegetais/farmacologia , SARS-CoV-2/efeitos dos fármacos , Animais , Anti-Inflamatórios/química , Antivirais/química , Chlorocebus aethiops , Ácido Clorogênico/isolamento & purificação , Ácido Clorogênico/farmacologia , Ácidos Cumáricos/isolamento & purificação , Ácidos Cumáricos/farmacologia , Ácido Gálico/isolamento & purificação , Ácido Gálico/farmacologia , Humanos , Masculino , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Pimenta/química , Extratos Vegetais/química , Ratos , Rutina/isolamento & purificação , Rutina/farmacologia , Células VeroRESUMO
Although Australia is the largest exporter of faba bean globally, there is limited information available on the levels of bioactive compounds found in current commercial faba bean varieties grown in this country. This study profiled the phenolic acid and flavonoid composition of 10 Australian faba bean varieties, grown at two different locations. Phenolic profiling by HPLC-DAD revealed the most abundant flavonoid to be catechin, followed by rutin. For the phenolic acids, syringic acid was found in high concentrations (72.4-122.5 mg/kg), while protocatechuic, vanillic, p-hydroxybenzoic, chlorogenic, p-coumaric, and trans-ferulic acid were all found in low concentrations. The content of most individual phenolics varied significantly with the variety, while some effect of the growing location was also observed. This information could be used by food processors and plant breeders to maximise the potential health benefits of Australian-grown faba bean.
Assuntos
Antioxidantes/química , Produtos Agrícolas/química , Flavonoides/química , Vicia faba/química , Antioxidantes/classificação , Antioxidantes/isolamento & purificação , Austrália , Catequina/química , Catequina/isolamento & purificação , Ácido Clorogênico/química , Ácido Clorogênico/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Ácidos Cumáricos/química , Ácidos Cumáricos/isolamento & purificação , Produtos Agrícolas/crescimento & desenvolvimento , Produtos Agrícolas/metabolismo , Flavonoides/classificação , Flavonoides/isolamento & purificação , Ácido Gálico/análogos & derivados , Ácido Gálico/química , Ácido Gálico/isolamento & purificação , Humanos , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Parabenos/química , Parabenos/isolamento & purificação , Rutina/química , Rutina/isolamento & purificação , Ácido Vanílico/química , Ácido Vanílico/isolamento & purificação , Vicia faba/crescimento & desenvolvimento , Vicia faba/metabolismoRESUMO
For selective adsorption of main flavonoids from crude Tartary buckwheat extract (rutin, 0.021 mg/mL; quercetin, 0.030 mg/mL; and kaempferol, 0.011 mg/mL), new ionic liquid-based sorbents were successfully prepared by encapsulating [Bmim]Br and [Bmim]Pro in regular spherical non-magnetic and magnetic microcapsules with polysulfone content of 8%, respectively. After appropriate loading process, the microcapsules were comprehensively characterized by infrared spectroscopy, thermogravimetry analysis and scanning electron microscopy. Then the separation strategy was designed to separate rutin and quercetin from kaempferol by combinational use of two kinds of IL-loaded microcapsules (ILLMs). The effects of solid-liquid ratio of ILLMs and extract, pH, time and adsorption temperature were all investigated. The experimental data fit well with the quasi-second-order kinetics model and Langmuir model. After desorption, target flavonoids were well recovered and the ILLMs showed good stability. As the result, a new IL-based separation technology for main flavonoids from food crop was developed for the first time.
Assuntos
Fagopyrum/química , Flavonoides/isolamento & purificação , Tecnologia de Alimentos/métodos , Líquidos Iônicos/química , Misturas Complexas , Flavonoides/análise , Quempferóis/isolamento & purificação , Quercetina/isolamento & purificação , Rutina/isolamento & purificação , VitaminasRESUMO
Rutin (RT), a widely distributed natural flavonoid compound, has been generally utilized as an important active ingredient owing to its considerable biomedical and economic value. Inspired by the structure features of densely-packed bayberry and well-orientated honeycomb, a novel type of magnetic molecularly imprinted polymers (HB-TI-MMIPs) with abundant high-affinity and uniformly-distributed binding sites was rationally constructed for the selective enrichment of RT from Sophora japonica. The polymerization conditions, physicochemical properties, and adsorption performance of the imprinted nanomaterials were systematically investigated. The optimized HB-TI-MMIPs display a high adsorption capacity, fast adsorption rate, and satisfactory selectivity towards RT. Meanwhile, the proposed analytical methodology using HPLC, with HB-TI-MMIPs as adsorbents, successfully applied to enrich and detect RT from Sophora japonica with high recoveries (87.2-94.6%) and good RSDs (lower than 4.3%). Therefore, the fabricated HB-TI-MMIPs with a fast magnetic responsivity and desirable adsorption performance would be attractive in plant active ingredients extraction fields.
Assuntos
Biomimética , Imãs/química , Polímeros Molecularmente Impressos/química , Myrica , Rutina/química , Sophora/química , Adsorção , Rutina/isolamento & purificação , Propriedades de SuperfícieRESUMO
Ruta chalepensis L. (Rutaceae), a perennial herb with wild and cultivated habitats, is well known for its traditional uses as an anti-inflammatory, analgesic, antipyretic agent, and in the treatment of rheumatism, nerve diseases, neuralgia, dropsy, convulsions and mental disorders. The antimicrobial activities of the crude extracts from the fruits, leaves, stem and roots of R. chalepensis were initially evaluated against two Gram-positive and two Gram-negative bacterial strains and a strain of the fungus Candida albicans. Phytochemical investigation afforded 19 compounds, including alkaloids, coumarins, flavonoid glycosides, a cinnamic acid derivative and a long-chain alkane. These compounds were tested against a panel of methicillin-resistant Staphylococcus aureus (MRSA) strains, i.e., ATCC 25923, SA-1199B, XU212, MRSA-274819 and EMRSA-15. The MIC values of the active compounds, chalepin (9), chalepensin (10), rutamarin (11), rutin 3'-methyl ether (14), rutin 7,4'-dimethyl ether (15), 6-hydroxy-rutin 3',7-dimethyl ether (16) and arborinine (18) were in the range of 32-128 µg/mL against the tested MRSA strains. Compounds 10 and 16 were the most active compounds from R. chalepensis, and were active against four out of six tested MRSA strains, and in silico studies were performed on these compounds. The anti-MRSA activity of compound 16 was comparable to that of the positive control norfloxacin (MICs 32 vs 16 µg/mL, respectively) against the MRSA strain XU212, which is a Kuwaiti hospital isolate that possesses the TetK tetracycline efflux pump. This is the first report on the anti-MRSA property of compounds isolated from R. chalepensis and relevant in silico studies on the most active compounds.
Assuntos
Simulação por Computador , Furocumarinas/farmacologia , Staphylococcus aureus Resistente à Meticilina/efeitos dos fármacos , Ruta/química , Ruta/crescimento & desenvolvimento , Rutina/farmacologia , Antibacterianos/química , Antibacterianos/farmacologia , Furocumarinas/química , Furocumarinas/isolamento & purificação , Ligação de Hidrogênio , Iraque , Ligantes , Testes de Sensibilidade Microbiana , Simulação de Acoplamento Molecular , Rutina/química , Rutina/isolamento & purificaçãoRESUMO
A green, novel and efficacious method for the simultaneous extraction and enrichment of rutin and narcissoside from the compound Anoectochilus roxburghii (Wall.) Lindl. oral liquid (CAROL) and Anoectochilus roxburghii (Wall.) Lindl. was developed. Ionic liquid-surfactant synergic cloud-point extraction (IL-CPE) was used to enrich two analytes, which were determined by high-performance liquid chromatography (HPLC). Some parameters affecting IL-CPE were optimized, such as ratio and volume of 1-butyl-3-methyl-imidazolium hexafluorophosphate and Triton X-114, pH of the sample, NaCl concentration, total extraction volume, incubation temperature and time, centrifuge rate and time. The corresponding linearity range for two analytes exhibited good linearity (r2ï¼0.9997), with the average added recoveries ranging from 92.1% to 98.9%. The limits of detection of rutin and narcissoside were 0.26 and 0.30 ng/mL, respectively. The method was successfully applied for the determination of two flavonoids in the complex-matrix sample, i.e. CAROL and the water extract of A. roxburghii. The mass spectrum data showed that the sample contained rutin and narcissoside. Compared with conventional extraction methods, IL-CPE exhibited higher extraction efficiency and better extraction selectivity. This method may provide a novel platform for the determination of active ingredients in compound Chinese medicine oral liquid and herb.
Assuntos
Fracionamento Químico/métodos , Imidazóis/química , Octoxinol/química , Orchidaceae/química , Rutina , Cromatografia Líquida de Alta Pressão/métodos , Flavonoides/análise , Flavonoides/química , Flavonoides/isolamento & purificação , Limite de Detecção , Modelos Lineares , Reprodutibilidade dos Testes , Rutina/análise , Rutina/química , Rutina/isolamento & purificaçãoRESUMO
This study aimed to evaluate the antidiabetic potential of the rind of Punica granatum var. nana. Acute oral toxicity test revealed the safety profile of its ethanolic extract. The extract was administered at 200 mg/kg b.wt to streptozotocin-induced diabetic rats. Serum diagnostic markers of diabetes (insulin, glucose and glycated hemoglobin), inflammatory mediators (tumor necrosis factor-α, interleukin-6, and nitric oxide), and oxidative stress (total antioxidant capacity and reduced glutathione and malondialdehyde) were assayed. The ethanolic extract was further fractionated and assessed for the aforementioned bioactivities at two different doses (100 and 200 mg/kg b.wt). The results revealed that the ethyl acetate fraction of rind exhibited the highest activities. Using different chromatographic techniques, four compounds were isolated and identified as rutin, gallic acid, nictoflorin, and tulipanin. In conclusion: The ethyl acetate fraction of the rind of Punica granatum var. nana may provide a potential therapeutic approach for hyperglycemia.
Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Extratos Vegetais/farmacologia , Punica granatum/química , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Antioxidantes/análise , Antioxidantes/química , Antioxidantes/farmacologia , Fracionamento Químico , Diabetes Mellitus Experimental/metabolismo , Relação Dose-Resposta a Droga , Ácido Gálico/isolamento & purificação , Hipoglicemiantes/administração & dosagem , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Ratos , Rutina/isolamento & purificação , Testes de Toxicidade AgudaRESUMO
Flavonol glucosides was extracted from red onion solid waste (ROSW) and multi-functional properties were determined to develop alternative strategy for therapeutic beneficiation and utilisation as functional food. The major flavonol glucosides extracted from ROSW were confirmed as quercetin-3, 4'-O-diglucoside (QDG), quercetin-3-O-glucoside (isoquercetin), quercetin-4'-O-glucoside (spiraeoside), isorhamnetin- 4'-glucoside (IMG), quercetin glycoside (QG), and quercetin (Q) using a combination of chromatographic, spectroscopic and scientific literature data. The ROSW solvent fractions and extracted flavonol glucosides showed significant antioxidant effect with DPPH, ABTS, FRAP, and ORAC radical scavenging assays. The in vitro and in silico study revealed that the QG, QDG, isoquercetin, and spiraeoside from ROSW exhibited potent α-glucosidase, tyrosinase and xanthine oxidase enzyme inhibitory activity. In addition, QG, QDG, isoquercetin, and spiraeoside showed potent anticancer effect on HeLa cancer lines. Considering these results, the utilization of ROSW and their flavonol glucosides might be helpful for developing potential antioxidant, anticancer and enzyme inhibitory agents.
Assuntos
Flavonóis/análise , Glucosídeos/análise , Cebolas/química , Extratos Vegetais/análise , Resíduos/análise , Antioxidantes/análise , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Linhagem Celular , Simulação por Computador , Flavonóis/isolamento & purificação , Flavonóis/farmacologia , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Humanos , Oxirredução , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Rutina/análise , Rutina/isolamento & purificaçãoRESUMO
Context: There are numerous pharmacological activities for Ruta graveolens and its bioactive constituent, rutin, on learning and memory.Objective: This study aimed to examine the effect of R. graveolens and rutin on memory in rats.Materials and methods: In this study animals were treated with the hydroalcholic extract of R. graveolens and rutin by IP injection for 10 days. Behavioural and biochemical tests as well as HPLC analysis and antioxidant activity of extract have been evaluated.Results: R. graveolens extract and rutin significantly increased learning and improved spatial memory, as well as secondary latency; moreover, there were significant increases in the serum and brain antioxidant capacity as well as the level of TBARS in serum and brain tissues. Results also showed that R. graveolens has significant DPPH radical scavenging effect (IC50: 159.17 ± 1.56 µg/mL). The HPLC analysis of extract showed that caffeic acid (19.92 ± 0.01), rutin (40.15 ± 0.01), and apigenin (0.84 ± 0.01) mg/g of dry extract are the main components of the extract.Discussion and conclusion: Regarding the effects of R. graveolens extract and rutin on animal brain cells, memory function, and learning, additional studies, including clinical trials, might be beneficial in producing natural supplementary drugs from this herb.
Assuntos
Aprendizagem da Esquiva/efeitos dos fármacos , Encéfalo/efeitos dos fármacos , Ruta , Rutina/farmacologia , Memória Espacial/efeitos dos fármacos , Animais , Aprendizagem da Esquiva/fisiologia , Encéfalo/metabolismo , Masculino , Distribuição Aleatória , Ratos , Ratos Sprague-Dawley , Traumatismo por Reperfusão/tratamento farmacológico , Traumatismo por Reperfusão/metabolismo , Rutina/isolamento & purificação , Rutina/uso terapêutico , Memória Espacial/fisiologiaRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: Cecropia Loefl. species (Urticaceae) are widely spread across the rainforest in tropical and subtropical regions of Central and South America. Inhabitants of different regions of Brazil employ leaves, fruits and sprouts of Cecropia hololeuca Miq. mainly as anti-inflammatory, anti-asthmatic, expectorant, fever suppressant, and against cough. AIM OF THE STUDY: To evaluate the antinociceptive and anti-inflammatory activities of an aqueous leaf extract of C. hololeuca in a murine model of zymosan-induced arthritis (ZIA) and characterize compounds contributing to these effects. MATERIALS AND METHODS: The crude aqueous extract of C. hololeuca (CAE) was obtained by infusion, screened for antinociceptive and anti-inflammatory activities, and fractionated (solvent partition; RP-2 and Sephadex G-25 column chromatography), yielding fractions that were chemically and pharmacologically investigated. TLC, HPLC-DAD, HPLC-DAD-ESI-MS/MS and NMR analyses were peformed. The antinociceptive activity was assessed by means of acetic acid-induced writhing, hot-plate and rota-rod tests. ZIA was used to evaluate the anti-arthritic activity of oral treatment with CAE, butanolic (BF) and aqueous fraction (AF), as well as the fractions obtained from BF (F2, F2-A and F2-B). Rutin, a flavonoid found in C. hololeuca, was also tested. Mechanical hypernociception, joint edema, local neutrophil recruitment and articular TNF-α quantification were performed to measure the severity of arthritis and identify the anti-inflammatory potential of C. hololeuca. RESULTS: CAE (0.03-1 g/kg, p.o.) showed a dose-related inhibitory effect on acetic acid-induced writhing test, but did not change the pain latency in the hotplate test, nor the first fall time on the rota-rod test. In addition, CAE (1 g/kg, p.o.) inhibited by 65% the mechanical hypernociception, 46% the joint edema, 54% the neutrophil recruitment and 53% the articular TNF-α concentration levels in ZIA. BF (0.4 g/kg, p.o.), AF (0.6 g/kg), F2 (0.1 g/kg) and F2-A (0.045 g/kg), but not F2-B (0.055 g/kg), inhibited the mechanical hypernociception, joint edema and neutrophil recruitment in ZIA. Rutin (0.001-0.03 g/kg, p.o.) produced dose-related inhibitory effects in the mechanical hypernociception, joint edema and neutrophil recruitment, and at 0.03 g/kg also inhibited articular TNF-α synthesis after intra-articular zymosan injection. Isoorientin, isovitexin, rutin and isoquercitrin were identified in the most active fraction (F2-A), along with luteolin and apigenin derivatives, tentatively identified as isoorientin-2â³-O-glucoside and isovitexin-2â³-O-glucoside. CONCLUSION: This study corroborates the popular use by oral route of aqueous preparations of C. hololeuca against joint inflammatory disorders, such as rheumatoid arthritis. Our results demonstrated for the first time that oral administration of rutin shows antinociceptive and anti-inflammatory effects in ZIA, indicating that this flavonoid is one of the immunomodulatory compounds involved in the anti-arthritic activity of C. hololeuca.
Assuntos
Analgésicos/administração & dosagem , Anti-Inflamatórios/administração & dosagem , Artralgia/prevenção & controle , Artrite Experimental/prevenção & controle , Cecropia , Flavonoides/administração & dosagem , Articulações/efeitos dos fármacos , Dor Nociceptiva/prevenção & controle , Extratos Vegetais/administração & dosagem , Rutina/administração & dosagem , Administração Oral , Analgésicos/isolamento & purificação , Animais , Anti-Inflamatórios/isolamento & purificação , Artralgia/induzido quimicamente , Artralgia/metabolismo , Artralgia/fisiopatologia , Artrite Experimental/induzido quimicamente , Artrite Experimental/metabolismo , Artrite Experimental/fisiopatologia , Cecropia/química , Citocinas/metabolismo , Precursores Enzimáticos , Flavonoides/isolamento & purificação , Mediadores da Inflamação/metabolismo , Articulações/metabolismo , Articulações/fisiopatologia , Masculino , Camundongos , Infiltração de Neutrófilos/efeitos dos fármacos , Dor Nociceptiva/induzido quimicamente , Dor Nociceptiva/metabolismo , Dor Nociceptiva/fisiopatologia , Limiar da Dor/efeitos dos fármacos , Extratos Vegetais/isolamento & purificação , Rutina/isolamento & purificaçãoRESUMO
Enantiomer separation and the isolation of natural products from plants pose challenging separation problems resulting from the similarity of molecules and the number of compounds present in synthesis or extract mixtures. Furthermore, limited theory is available to predict productivities for possible alternative separation techniques. The application and performance of chromatography- and crystallization-based processes are demonstrated for various case studies devoted to isolating valuable target compounds from complex initial mixtures. In all cases, the first emphasis is set to determine the process-specific phase equilibria to identify feasible process options. For all examples considered, yields and productivities are evaluated and compared for different scenarios. Guidelines to approach and solve similar separation tasks are given.
Assuntos
Produtos Biológicos/química , Plantas/metabolismo , Anilidas/química , Anilidas/isolamento & purificação , Produtos Biológicos/isolamento & purificação , Catálise , Cromatografia Líquida , Cristalização , Nitrilas/química , Nitrilas/isolamento & purificação , Rutina/química , Rutina/isolamento & purificação , Estereoisomerismo , Compostos de Tosil/química , Compostos de Tosil/isolamento & purificaçãoRESUMO
In this study, the phenolic profiles and bioactivities of five representative cultivars of okra collected in China were investigated. Noticeable variations of phenolic compounds and their bioactivities were observed among these different cultivars of okra. The contents of total flavonoids (TFC) in "Shuiguo", "Kalong 8", "Kalong 3", "Wufu", and "Royal red" ranged from 1.75 to 3.39 mg RE/g DW, of which "Shuiguo" showed the highest TFC. Moreover, five individual phenolic compounds were found in okra by high performance liquid chromatography analysis, including isoquercitrin, protocatechuic acid, quercetin-3-O-gentiobioside, quercetin, and rutin, while isoquercitrin and quercetin-3-O-gentiobioside were detected as the main phenolic compounds in okra. Moreover, all tested okra exhibited significant antioxidant activities (2,2-diphenyl-1-picrylhydrazyl radical scavenging capacity, 2,2'-azino-bis (3-ethylenzthiazoline-6-sulphonic acid) radical scavenging capacity, and ferric reducing antioxidant power) and inhibitory effects on digestive enzymes (lipase, α-glucosidase, and α-amylase). Indeed, "Shuiguo" exhibited much better antioxidant activities and inhibitory activities on digestive enzymes, which might be attributed to its high TFC. Results suggested that okra, especially "Shuiguo", could be developed as natural antioxidants and inhibitors against hyperlipidemia and hyperglycemia in the fields of functional foods and pharmaceuticals, which could meet the increasing demand for high-quality okra with health-promoting properties in China.
Assuntos
Abelmoschus/química , Frutas/química , Lipase/antagonistas & inibidores , alfa-Amilases/antagonistas & inibidores , alfa-Glucosidases/química , Animais , Antioxidantes/química , Antioxidantes/classificação , Antioxidantes/isolamento & purificação , Benzotiazóis/antagonistas & inibidores , Benzotiazóis/química , Compostos de Bifenilo/antagonistas & inibidores , Compostos de Bifenilo/química , Dissacarídeos/química , Dissacarídeos/isolamento & purificação , Flavonoides/química , Flavonoides/classificação , Flavonoides/isolamento & purificação , Hidroxibenzoatos/química , Hidroxibenzoatos/isolamento & purificação , Lipase/química , Fenóis/química , Fenóis/classificação , Fenóis/isolamento & purificação , Picratos/antagonistas & inibidores , Picratos/química , Extratos Vegetais/química , Quercetina/análogos & derivados , Quercetina/química , Quercetina/isolamento & purificação , Rutina/química , Rutina/isolamento & purificação , Ácidos Sulfônicos/antagonistas & inibidores , Ácidos Sulfônicos/química , Ácidos Sulfônicos/isolamento & purificação , Suínos , Tiazóis/química , Tiazóis/isolamento & purificação , alfa-Amilases/químicaRESUMO
To correlate the beneficial effects of cherry consumption with their phenolic composition, a full and precise characterization is required. However, there is not a specific method to fully extract all phenolic compounds from sweet cherries. Thus, this study aimed to optimize the extraction of sweet cherry phenolics by response surface methodology and fully characterize the phenolic profile of Royal Dawn sweet cherries by HPLC-ESI-MS/MS. Extraction conditions were evaluated and optimized to 55 °C, MeOH 72%, 12 mL/g in two extraction steps. Royal Dawn sweet cherries presented rutin as the predominant phenolic compound, unlike most sweet cherry varieties. Additionally, ethanol was evaluated as a replacement solvent, obtaining lower extraction rates, especially for anthocyanins. However, in terms of total amounts, non-anthocyanin compounds were similarly extracted. The developed methodology was fast and can be routinely used in the evaluation of the phenolic profile of sweet cherries and to produce phenolic-rich extracts for the food industry.
Assuntos
Fenóis/isolamento & purificação , Prunus avium/química , Antocianinas/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Etanol , Frutas/química , Metanol , Extratos Vegetais/química , Rutina/isolamento & purificação , Solventes , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em TandemRESUMO
Tartary buckwheat (Fagopyrum tataricum (L.) Gaertn) is rich in functional compounds such as rutin, quercetin, d-chiro-inositol, dietary fiber, and essential amino acids. Electric field (EF) treatment before sprout germination results in physiological and chemical changes, and some alterations might lead to positive applications in plant seeds. MTT assay showed that the effect of total flavonoids on human gastric cancer cell line MGC80-3 was significantly changed after EF treatment for different germination days (3-7 days). Among them, the total flavonoids of tartary buckwheat (BWTF) on the third day had the most obvious inhibitory effect on MGC80-3 (p < 0.01). In addition, flow cytometry evidenced that different ratios of quercetin and rutin had effects on the proliferation of MGC80-3. The same content of quercetin and rutin had the best effect, reaching 6.18 ± 0.82%. The anti-cancer mechanism was mainly promoted by promoting the expression of apoptotic proteins. The expression of Bax/Bcl-2 and caspase-8 in MGC80-3 cells was mediated by BWTFs. This study has good research value for improving the biological and economic value of tartary buckwheat.
Assuntos
Fagopyrum/fisiologia , Quercetina/farmacologia , Rutina/farmacologia , Neoplasias Gástricas/metabolismo , Caspase 8/metabolismo , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cromatografia Líquida de Alta Pressão , Fagopyrum/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Germinação , Humanos , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , Quercetina/isolamento & purificação , Rutina/isolamento & purificação , Neoplasias Gástricas/tratamento farmacológico , Proteína X Associada a bcl-2/metabolismoRESUMO
In order to improve the permeation and adsorption properties of graphene oxide, heteroatoms and deep eutectic solvent were introduced in this study. After being modified, the structural properties of graphene oxide were improved and the materials were applied to the determination of myricetin and rutin in tea sample by pipette-tip solid-phase extraction method. The materials were characterized by scanning electron microscopy, Fourier transform infrared spectroscopy, X-Ray diffractomer, energy dispersive spectroscopy, atomic force microscope, and specific surface area by Brunauer-Emmett-Teller N2 adsorption desorption analysis. Meanwhile, they were tested by static and dynamic adsorption. The result showed that the materials after modifying had better adsorption amount for myricetin and rutin than graphene oxide. The calibration graphs of myricetin and rutin in MeOH were linear over 0.10-500.00 µg/mL, and the limits of detection and quantification were in the range of 0.00546-0.0182 µg/mL and 0.00741-0.0247 µg/mL, respectively. A reliable analytical method was developed for recognition targets in tea sample by DES modified nitrogen-doped graphene oxide with satisfactory extraction recoveries (myricetin 99.77%, rutin 98.14%). It was potential for the rapid purification of myricetin and rutin in tea sample combined with the pipette-tip solid-phase extraction.
Assuntos
Flavonoides/isolamento & purificação , Grafite/química , Rutina/isolamento & purificação , Extração em Fase Sólida , Flavonoides/química , Tamanho da Partícula , Rutina/química , Solventes/química , Propriedades de SuperfícieRESUMO
Dimorphandra gardneriana Tulasne é conhecida como fava danta, é uma árvore brasileira, naturalmente do Cerrado e Caatinga, têm uma importância ecológica e funcional, seus frutos são ricos em flavonoides (rutina, quercetina, isoquercitrina). O objetivo deste trabalho foi estudar a estabilidade térmica da fava danta e da rutina purifica através da termogravimetria. As amostras foram analisadas no Termogravimétrico Shimadzu, TGA-51, no Laboratório de Materiais do IFPI, onde foram acondicionadas em porta-amostras de platina, com atmosfera de nitrogênio e com fluxo de 50 mL/min. A temperatura foi elevada a 600°C, com taxa de aquecimento de 2 °C/min. Obteve-se sucesso com a purificação da fava danta, pois a rutina obtida teve maior uniformidade nos eventos térmicos e maior estabilidade térmica em relação a fava.