RESUMO
In this study, high-performance liquid chromatography was used to determine four components of Shaoyao Gancao Decoction (SGD), and the effect of purification was evaluated using fingerprints, similarity analysis and cell experiments. An effective method for isolation and purification of SGD was established. The adsorption/desorption properties of SGD were evaluated using resin screening, isothermal analysis, adsorption kinetics, and dynamic adsorption-desorption experiments. It was shown that the Langmuir equation fitted the isotherm data well and that a pseudo-second-order model accurately described kinetic adsorption on AB-8 resin. Analysis of thermodynamic parameters showed that the adsorption process was exothermic. Under the optimal process conditions, the concentrations of albiflorin, paeoniflorin, liquiritin and ammonium glycyrrhizinate in the product were 73.05, 134.04, 45.04 and 75.00 mg/g, respectively. The yields of the four components were 71.89 %-86.19 %. Cell experiments showed that the purified SGD retained anti-inflammatory activity. This research lays the foundation for the separation and purification of SGD and subsequent preparation research.
Assuntos
Medicamentos de Ervas Chinesas , Glucosídeos , Monoterpenos , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Glucosídeos/isolamento & purificação , Glucosídeos/química , Monoterpenos/isolamento & purificação , Monoterpenos/química , Adsorção , Flavanonas/isolamento & purificação , Flavanonas/química , Flavanonas/análise , Animais , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/química , Ácido Glicirrízico/análise , Hidrocarbonetos Aromáticos com Pontes/química , Hidrocarbonetos Aromáticos com Pontes/isolamento & purificação , Camundongos , Resinas Sintéticas/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/química , Humanos , Células RAW 264.7RESUMO
The development and exploration of uranium decorporation agents with straightforward synthesis, high removal ability, and low toxicity are crucial guarantees for the safety of workers in the nuclear industry and the public. Herein, we report the use of traditional Chinese medicine licorice for uranium decorporation. Licorice has good adsorption performance and excellent selectivity for uranium in the simulated human environment. Glycyrrhizic acid (GL) has a high affinity for uranium (p(UO2) = 13.67) and will complex with uranium at the carbonyl site. Both licorice and GL exhibit lower cytotoxicity compared to the commercial clinical decorporation agent diethylenetriamine pentaacetate sodium salts (CaNa3-DTPA). Notably, at the cellular level, the uranium removal efficiency of GL is eight times higher than that of CaNa3-DTPA. Administration of GL by prophylactic intraperitoneal injection demonstrates that its uranium removal efficiency from kidneys and bones is 55.2 and 23.9%, while CaNa3-DTPA shows an insignificant effect. The density functional theory calculation of the bonding energy between GL and uranium demonstrates that GL exhibits a higher binding affinity (-2.01 vs -1.15 eV) to uranium compared to DTPA. These findings support the potential of licorice and its active ingredient, GL, as promising candidates for uranium decorporation agents.
Assuntos
Produtos Biológicos , Glycyrrhiza , Ácido Glicirrízico , Urânio , Glycyrrhiza/química , Urânio/química , Urânio/isolamento & purificação , Humanos , Ácido Glicirrízico/química , Ácido Glicirrízico/farmacologia , Ácido Glicirrízico/isolamento & purificação , Produtos Biológicos/química , Produtos Biológicos/farmacologia , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/síntese química , Animais , Teoria da Densidade Funcional , Camundongos , Sobrevivência Celular/efeitos dos fármacosRESUMO
A novel, green and eco-friendly, cost-effective, fast, and reliable high energy ultrasonication (US) extraction with UHPLC-MSMS (Ultrahigh performance liquid chromatography with mass spectrometry) quantification of Glycyrrhizic acid (GZA) is reported herein for the first time. The study provides useful insights regarding the effect of US-factors with statistical analysis and mechanisms, involved in GZA-extraction and analysis. An US-extraction method (US-MD) was developed using three levels of US factors: solvents (AC (acetone), EtOH (ethanol), H2O (water)), time (1, 2, 3 min), amplitudes (30, 40, 50%), pulse (10/0.5, 20/0.5, 30/0.5 sec), particle sizes (0.5, 1, 1.4 mm), and temperatures (20, 30, 40 °C). The US-MD was further validated with high accuracy 98.96 ± 6.82 and r2 = 0.995 whereas, an in-house analytical method (UHPLC-MSMS) was developed and validated to quantify the GZAamount. UHPLCMSMS-MD resulted in a retention time of 0.31 min with MSMS (821.400 > 351.200) in a 1 min run time whereas, UHPLCMSMS-MV showed high accuracy and precision with r2 = 0.998 for GZA. Statistical analysis of K-mean clustering finalized US-set-of-factors showing optimum extract yield (mg/1mg) of 0.48 with sum (2.41 ± 014) and mean (0.27) along with a high GZA-amount (µg/mg) of 8.23 with sum (43.31 ± 2.07) and mean (4.81) for H2O in 3 min at 40 °C using particle size (1.4 mm), amplitude (50%), and pulse (30/0.5). Large scale application of US-UHPLCMSMS confirmed the evaluation power of the method showing the order for GZA amount; Egypt > Pakistan > Syria > India > Palestine > America > Georgia > Morocco. A significant effect for US factors Vs extract yield and GZA amount was observed however, solvent*GZA-amount and extract yield*particle size were more significantly correlated compared to time*temperature*amplitude*pulse analyzed via PCA, GLM-UniANOVA, K-mean, and Pearson's correlation (P ≤ 0.05). A combined mechanism of shear stress, macroturbulence due to acoustic cavitation and implosions, sonochemical, and sonocapillary effect were noted for the US technique producing higher extract yield and GZA amount from licorice.
Assuntos
Fracionamento Químico/métodos , Cromatografia Líquida de Alta Pressão , Glycyrrhiza/química , Ácido Glicirrízico/análise , Ácido Glicirrízico/isolamento & purificação , Espectrometria de Massas em Tandem , Ondas Ultrassônicas , Química Verde , Fatores de TempoRESUMO
BACKGROUND: The dried roots and rhizomes of medicinal licorices are widely used worldwide as a traditional medicinal herb, which are mainly attributed to a variety of bioactive compounds that can be extracted from licorice root. Endophytes and plants form a symbiotic relationship, which is an important source of host secondary metabolites. RESULTS: In this study, we used high-throughput sequencing technology and high-performance liquid chromatography to explore the composition and structure of the endophytic bacterial community and the content of bioactive compounds (glycyrrhizic acid, liquiritin and total flavonoids) in different species of medicinal licorices (Glycyrrhiza uralensis, Glycyrrhiza glabra, and Glycyrrhiza inflata) and in different planting years (1-3 years). Our results showed that the contents of the bioactive compounds in the roots of medicinal licorices were not affected by the species, but were significantly affected by the main effect growing year (1-3) (P < 0.05), and with a trend of stable increase in the contents observed with each growing year. In 27 samples, a total of 1,979,531 effective sequences were obtained after quality control, and 2432 effective operational taxonomic units (OTUs) were obtained at 97% identity. The phylum Proteobacteria, Actinobacteria, Bacteroidetes and Firmicutes, and the genera unified-Rhizobiaceae, Pseudomonas, Novosphingobium, and Pantoea were significantly dominant in the 27 samples. Distance-based redundancy analysis (db-RDA) showed that the content of total flavonoids explained the differences in composition and distribution of endophytic bacterial communities in roots of cultivated medicinal liquorices to the greatest extent. Total soil salt was the most important factor that significantly affected the endophytic bacterial community in soil factors, followed by ammonium nitrogen and nitrate nitrogen. Among the leaf nutrition factors, leaf water content had the most significant effect on the endophytic bacterial community, followed by total phosphorus and total potassium. CONCLUSIONS: This study not only provides information on the composition and distribution of endophytic bacteria in the roots of medicinal licorices, but also reveals the influence of abiotic factors on the community of endophytic bacteria and bioactive compounds, which provides a reference for improving the quality of licorice.
Assuntos
Flavonoides/biossíntese , Glycyrrhiza uralensis/microbiologia , Glycyrrhiza/microbiologia , Raízes de Plantas/microbiologia , Rizoma/microbiologia , Actinobacteria/classificação , Actinobacteria/genética , Actinobacteria/isolamento & purificação , Amônia/farmacologia , Bacteroidetes/classificação , Bacteroidetes/genética , Bacteroidetes/isolamento & purificação , Código de Barras de DNA Taxonômico , DNA Bacteriano/genética , Endófitos/fisiologia , Firmicutes/classificação , Firmicutes/genética , Firmicutes/isolamento & purificação , Flavanonas/biossíntese , Flavanonas/isolamento & purificação , Flavonoides/classificação , Flavonoides/isolamento & purificação , Glucosídeos/biossíntese , Glucosídeos/isolamento & purificação , Glycyrrhiza/efeitos dos fármacos , Glycyrrhiza/metabolismo , Glycyrrhiza uralensis/efeitos dos fármacos , Glycyrrhiza uralensis/metabolismo , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/metabolismo , Consórcios Microbianos/efeitos dos fármacos , Consórcios Microbianos/genética , Nitratos/farmacologia , Filogenia , Raízes de Plantas/metabolismo , Proteobactérias/classificação , Proteobactérias/genética , Proteobactérias/isolamento & purificação , Rhizobiaceae/classificação , Rhizobiaceae/genética , Rhizobiaceae/isolamento & purificação , Rizoma/metabolismo , Estações do Ano , Metabolismo Secundário , Solo/química , Microbiologia do Solo , SimbioseRESUMO
Glycyrrhizic acid (GL) and its derivants, glycyrrhetinic acid 3-O-mono-ß-d-glucuronide (GAMG) and glycyrrhetinic acid (GA) hydrolyzed in subcritical water, are bioactive substances and edulcorators. In this work, a separation strategy for these three substances was established. The effects of adsorbent and eluent were investigated by static/dynamic adsorption and multi-stage desorption with the mechanism analysis. The adsorption of them onto EXA50 resin was well fitted by the pseudo second-order kinetic model. The optimal dynamic adsorption flow rate was 6 bed volume (BV)/h, and water of pH = 12 was used to elute GL at 4 BV/h, then n-buthanol was used subsequently to elute GA at 1 BV/h, and finally 90% ethanol was applied to elute GAMG at 2 BV/h. As a result, purities of these compounds increased, which demonstrated that this adsorption-desorption technology was simple and efficient, and indicated the potential for large-scale purification and preparation of GL and its derivants in the future.
Assuntos
Ácido Glicirrízico/isolamento & purificação , Resinas Sintéticas/química , Água/química , Adsorção , Ácido Glicirrízico/análogos & derivados , Concentração de Íons de Hidrogênio , Hidrólise , Cinética , Modelos Teóricos , PorosidadeRESUMO
The technique of high-speed countercurrent chromatography (HSCCC) was applied to the preparative isolation and purification of liquiritin and glycyrrhizic acid from a crude extract of Glycyrrhiza uralensis Fisch for the first time. Using single factor and orthogonal design experiments, the best extraction conditions were 70% ethanol, 1:25 ratio of solid-to-liquid (w/v) and extracted 1.5 h at 80°C. The contents of liquiritin and glycyrrhizic acid in the crude extract were 1.3 and 5.3%, respectively. Using the two-phase solvent system of ethyl acetate-methanol-water (5:2:5, v/v), 6.0 mg liquiritin (the purity was 96.7%, and the recovery was 89.3%), and 20.5 mg glycyrrhizic acid (the purity was 98.9%, and the recovery was 77.1%) were obtained from 500 mg crude extraction by HSCCC, respectively. The retention rate of stationary phase was 51.0%. Their structures were identified by high-performance liquid chromatography, melting points, ultraviolet radiation, Fourier transform infrared (FTIR), Electrospray ionization mass spectrometry (ESI-MS), 1H Nuclear Magnetic Resonance (NMR) and 13C NMR spectra. The scavenging abilities of glycyrrhizic acid to 1,1-diphenyl-2-picrylhydrazyl and hydroxyl free radicals were stronger than those of liquiritin.
Assuntos
Distribuição Contracorrente/métodos , Flavanonas/isolamento & purificação , Glucosídeos/isolamento & purificação , Glycyrrhiza uralensis/química , Ácido Glicirrízico/isolamento & purificação , Antioxidantes/análise , Antioxidantes/química , Antioxidantes/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Flavanonas/análise , Flavanonas/química , Glucosídeos/análise , Glucosídeos/química , Ácido Glicirrízico/análise , Ácido Glicirrízico/química , Extratos Vegetais/química , Análise EspectralRESUMO
In this work, the use of polymeric ultrafiltration and nanofiltration membranes was investigated in order to recover glycyrrhizin and phenolic compounds from licorice wastewaters. Filtration experiments were performed on a laboratory scale using four polyamide thin-film composite membranes (GK, GH, GE, and DK, from GE Osmonics) with different molecular weight cut-offs (from 150 to 3500 Da). The permeate flux and retention values of glycyrrhizin, the total polyphenols, the caffeic acid, the total carbohydrate, and the total antioxidant activity as a function of the transmembrane pressure (TMP) and weight reduction factor (WRF) were evaluated. In selected operating conditions, the membrane productivity decreased in the order of GK > DK > GH > GE, with a similar trend to that of water permeability. Glycyrrhizin was totally rejected by selected membranes, independently of TMP and WRF. For the other antioxidant compounds, the retention values increased by increasing both of the parameters. According to the experimental results, a combination of membranes in a sequential design was proposed as a viable approach to produce concentrated fractions enriched in bioactive compounds and purified water from licorice wastewater.
Assuntos
Glycyrrhiza/química , Ácido Glicirrízico/isolamento & purificação , Membranas Artificiais , Fenóis/isolamento & purificação , Águas Residuárias/química , Ácido Glicirrízico/análise , Fenóis/análise , Ultrafiltração , Fluxo de TrabalhoRESUMO
Licorice-induced pseudoaldosteronism is a common adverse effect in traditional Japanese Kampo medicine, and 3-monoglucuronyl glycyrrhetinic acid (3MGA) was considered as a causative agent of it. Previously, we found 22α-hydroxy-18ß-glycyrrhetyl-3-O-sulfate-30-glucuronide (1), one of the metabolites of glycyrrhizin (GL) in the urine of Eisai hyperbilirubinuria rats (EHBRs) treated with glycyrrhetinic acid (GA), and suggested that it is also a possible causative agent of pseudoaldosteronism. The discovery of 1 also suggested that there might be other metabolites of GA as causal candidates. In this study, we found 22α-hydroxy-18ß-glycyrrhetyl-3-O-sulfate (2) and 18ß-glycyrrhetyl-3-O-sulfate (3) in EHBRs' urine. 2 and 3 more strongly inhibited rat type 2 11ß-hydroxysteroid dehydrogenase than 1 did in vitro. When EHBRs were orally treated with GA, GA and 1-3 in plasma and 1-3 in urine were detected; the levels of 3MGA were quite low. 2 and 3 were shown to be the substrates of organic anion transporter (OAT) 1 and OAT3. In the plasma of a patient suffering from pseudoaldosteronism with rhabdomyolysis due to licorice, we found 8.6 µM of 3, 1.3 µM of GA, and 87 nM of 2, but 1, GL, and 3MGA were not detected. These findings suggest that 18ß-glycyrrhetyl-3-O-sulfate (3) is an alternative causative agent of pseudoaldosteronism, rather than 3MGA and 1.
Assuntos
Glycyrrhiza/efeitos adversos , Ácido Glicirrízico/efeitos adversos , Síndrome de Liddle/etiologia , 11-beta-Hidroxiesteroide Desidrogenase Tipo 2/antagonistas & inibidores , Animais , Relação Dose-Resposta a Droga , Feminino , Glycyrrhiza/química , Ácido Glicirrízico/química , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/urina , Túbulos Renais/efeitos dos fármacos , Túbulos Renais/metabolismo , Síndrome de Liddle/diagnóstico , Espectroscopia de Ressonância Magnética , Estrutura Molecular , RatosRESUMO
Glycyrrhizic acid (GA), a triterpene isolated from the roots and rhizomes of licorice, named Glycyrrhiza glabra, is the principal bioactive ingredient of anti-viral, anti-inflammatory and hepatoprotective effects. GA has been used in the clinical treatment of hepatitis, bronchitis, gastric ulcer, AIDS (acquired immunodeficiency syndrome), certain cancers and skin diseases. It has a direct effect on anti-HBV (hepatitis B virus) via affecting the HBsAg (hepatitis B surface antigen) to extracellular secretion, improving liver dysfunction in patients with chronic hepatitis B, and ultimately improving the immune status of HBV. GA can significantly inhibit the proliferation of HIV, showing an immune activation. The clinical application of GA on the prevention and treatments of various diseases may derive from its numerous pharmacological properties. This review provides the summary of the antiviral effects of GA on research progress and mechanism in recent years.
Assuntos
Antivirais/farmacologia , Ácido Glicirrízico/farmacologia , HIV/efeitos dos fármacos , Hepacivirus/efeitos dos fármacos , Vírus da Hepatite B/efeitos dos fármacos , Antivirais/química , Antivirais/isolamento & purificação , Glycyrrhiza/química , Ácido Glicirrízico/química , Ácido Glicirrízico/isolamento & purificação , Antígenos de Superfície da Hepatite B/metabolismo , HumanosRESUMO
In the last years, consumers are paying much more attention to natural medicines and principles, mainly due to the general sense that natural compounds are safe. On the other hand, there is a growing demand by industry for plants used in traditional medicine that could be incorporated in foods, nutraceuticals, cosmetics, or even pharmaceuticals. Glycyrrhiza glabra Linn. belongs to the Fabaceae family and has been recognized since ancient times for its ethnopharmacological values. This plant contains different phytocompounds, such as glycyrrhizin, 18ß-glycyrrhetinic acid, glabrin A and B, and isoflavones, that have demonstrated various pharmacological activities. Pharmacological experiments have demonstrated that different extracts and pure compounds from this species exhibit a broad range of biological properties, including antibacterial, anti-inflammatory, antiviral, antioxidant, and antidiabetic activities. A few toxicological studies have reported some concerns. This review addresses all those issues and focuses on the pharmacological activities reported for G. glabra. Therefore, an updated, critical, and extensive overview on the current knowledge of G. glabra composition and biological activities is provided here in order to explore its therapeutic potential and future challenges to be utilized for the formulation of new products that will contribute to human well-being.
Assuntos
Glycyrrhiza/química , Extratos Vegetais/farmacologia , Animais , Antibacterianos/farmacologia , Antioxidantes/farmacologia , Antivirais/isolamento & purificação , Antivirais/farmacologia , Inibidores Enzimáticos/farmacologia , Etnofarmacologia , Glycyrrhiza/fisiologia , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/farmacologia , Humanos , Hipoglicemiantes/isolamento & purificação , Hipoglicemiantes/farmacologia , Medicina Tradicional , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/isolamento & purificaçãoRESUMO
PURPOSE: The chemotherapeutic agent irinotecan is hydrolyzed to its active form SN-38 by human carboxyesterases, but SN-38 is converted into the inactive form SN-38G by hepatic UDP-glucuronosyltransferases (UGTs). The aim of the present study was to evaluate the inhibitory effects of two b-glucuronidase-treated Japanese traditional herbal medicines (kampo), Hange-Shashin-To (TJ-14) and Sairei-To (TJ-114) on SN-38 glucuronidation, and the deglycosylation of baicalin (BG) and glycyrrhizic acid (GL) derived from TJ-14 and TJ-114 to form their respective aglycones, baicalein (BA) and glycyrrhetinic acid (GA). METHODS: The inhibitory effects of b-glucuronidase-treated TJ-14 and TJ-114 on SN-38 glucuronidation by human liver microsomes were examined. BA and GA, which were enzymatically converted from BG and GL present in TJ-14 and TJ-114, were examined in the same manner. Furthermore, the enzymatic activities were measured by using recombinant UGT1A1 and UGT1A9 isoforms instead of human liver microsomes. BA, GA, SN-38, and their glycosides/glucuronides were analyzed with an LC-MS system. RESULTS: As regards the linear initial reaction rate, SN-38 glucuronidation by human liver microsomes was significantly inhibited by the addition of b-glucuronidase-untreated TJ-14 and TJ-114, but was more strongly inhibited by the addition of b-glucuronidase-treated TJ-14 and TJ-114. The results of LC-MS analysis and pharmacokinetic studies suggested that BA is the main inhibitor of SN-38 glucuronidation. In the Dixon plot, BA showed competitive inhibition of SN-38 glucuronidation, and the inhibition constant was 8.70 ± 3.24 mM. Previous reports, studies of recombinant UGT isoforms indicated that SN-38 glucuronidation was mainly catalyzed by UGT1A1. CONCLUSIONS: These findings strongly suggested that SN-38 glucuronidation is inhibited by BA. BA could act as a pharmacokinetic regulating factor associated with SN-38 glucuronidation. This article is open to POST-PUBLICATION REVIEW. Registered readers (see "For Readers") may comment by clicking on ABSTRACT on the issue's contents page.
Assuntos
Inibidores Enzimáticos/farmacologia , Flavanonas/farmacologia , Glucuronídeos/antagonistas & inibidores , Irinotecano/antagonistas & inibidores , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Flavanonas/química , Flavanonas/isolamento & purificação , Glucuronidase/antagonistas & inibidores , Glucuronidase/metabolismo , Glucuronídeos/metabolismo , Ácido Glicirrízico/química , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/farmacologia , Medicina Herbária , Humanos , Irinotecano/metabolismo , Japão , Cinética , Microssomos Hepáticos/efeitos dos fármacos , Microssomos Hepáticos/metabolismo , Fatores de TempoRESUMO
Hizikia fusiformis (Harvey) Okamura is a brown seaweed widely used in Korea and Japan, and it contains different therapeutically active constituents. In the present study, we investigated the activities of glycyrrhizin isolated from H. fusiformis, including its metabolites, 18α- and 18ß-glycyrrhetinic acid against Alzheimer's disease (AD) via acetyl and butyrylcholinesterase and ß-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibition. Among these three compounds, 18ß-glycyrrhetinic acid (IC50 = 8.93 ± 0.69 µM) demonstrated two fold potent activity against BACE1 compared to the positive control, quercetin (IC50 = 20.18 ± 0.79 µM). Additionally, glycyrrhizin with an IC50 value of 20.12 ± 1.87 µM showed similarity to quercetin, while 18α-glycyrrhetinic acid showed moderate activity (IC50 = 104.35 ± 2.84 µM). A kinetic study revealed that glycyrrhizin and 18ß-glycyrrhetinic acid were non-competitive and competitive inhibitiors of BACE1, demonstrated via K i values of 16.92 and 10.91 µM, respectively. Molecular docking simulation studies evidently revealed strong binding energy of these compounds for BACE1, indicating their high affinity and capacity for tighter binding to the active site of the enzyme. These data suggest that glycyrrhizin isolated from the edible seaweed, H. fusiformis and its metabolite, 18ß-glycyrrhetinic acid demonstrated selective inhibitory activity against BACE1 to alleviate AD.
Assuntos
Secretases da Proteína Precursora do Amiloide/antagonistas & inibidores , Anti-Inflamatórios/farmacologia , Ácido Aspártico Endopeptidases/antagonistas & inibidores , Simulação por Computador , Ácido Glicirretínico/análogos & derivados , Ácido Glicirrízico/farmacologia , Simulação de Acoplamento Molecular/métodos , Alga Marinha , Secretases da Proteína Precursora do Amiloide/metabolismo , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/metabolismo , Ácido Aspártico Endopeptidases/metabolismo , Relação Dose-Resposta a Droga , Electrophorus , Ácido Glicirretínico/isolamento & purificação , Ácido Glicirretínico/metabolismo , Ácido Glicirretínico/farmacologia , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/metabolismo , Cavalos , HumanosRESUMO
Molecularly imprinted polymers of glycyrrhizic acid were prepared by solution polymerization using glycyrrhizic acid as the template molecule, N-vinypyrrolidone as functional monomer, N,N-methylene bisacrylamide as cross-linker and ascorbic acid and hydrogen peroxide as initiators. Focused on the adsorption capacity and separation degree of the polymer to glycyrrhizic acid, the effects of the monomers, crosslinker and initiators were investigated and optimized. Finally, the structure of the polymer was characterized by using Fourier transform infrared spectroscopy and scanning electron microscopy. To obtain objective results, non-imprinted molecular polymers prepared under the same conditions were also characterized. The adsorption quantity of the polymer was measured by high-performance liquid chromatography. Under the optimum conditions, the maximum adsorption capacity of glycyrrhizic acid approached 15 mg/g, and the separation degree was as high as 2.5. The adsorption kinetics could be well described by a pseudo-first-order model, while the thermodynamics of the adsorption process could be described by the Langmuir model.
Assuntos
Ácido Glicirrízico/isolamento & purificação , Impressão Molecular , Adsorção , Polimerização , PolímerosRESUMO
There have been numerous case reports of severe adverse events including deaths following chronic licorice ingestion. The aim of the present study was to evaluate the effect of chronic ingestion of licorice on blood pressure, plasma potassium, plasma renin activity and plasma aldosterone. A search of MEDLINE, PubMed, EMBASE, CENTRAL, DARE, CINAHL and Current Contents Connect was performed from inception through to 26 April 2017. Trials that included a treatment group ingesting a product containing at least 100 mg of glycyrrhizic acid daily were selected. Pooled mean changes from baseline with 95% confidence intervals were calculated for diastolic blood pressure, systolic blood pressure, plasma potassium, plasma renin activity and plasma aldosterone using a random effects model. An assessment of dose-response was also undertaken. A total of 18 studies (n=337) were included in the meta-analysis. There was a statistically significant increase in mean systolic blood pressure (5.45 mm Hg, 95% CI 3.51-7.39) and diastolic blood pressure (3.19 mm Hg, 95% CI 0.10-6.29) after chronic ingestion of a product containing glycyrrhizic acid. Plasma potassium (-0.33 mmol l-1, 95% CI -0.42 to 0.23), plasma renin activity (-0.82 ngml-1 per hour, 95% CI -1.27 to -0.37) and plasma aldosterone (-173.24 pmol l-1, 95% CI -231.65 to -114.83) were all significantly decreased. A significant correlation was noted between daily dose of glycyrrhizic acid and systolic blood pressure (r2=0.55) and diastolic blood pressure (r2=0.65), but not for the other outcome measures. Hence, chronic licorice ingestion is associated with an increase in blood pressure and a drop in plasma potassium, even at modest doses. This is of particular relevance for individuals with existing cardiovascular disease.
Assuntos
Pressão Sanguínea/efeitos dos fármacos , Glycyrrhiza/efeitos adversos , Ácido Glicirrízico/efeitos adversos , Hipertensão/induzido quimicamente , Hipopotassemia/induzido quimicamente , Extratos Vegetais/efeitos adversos , Potássio/sangue , Adulto , Aldosterona/sangue , Biomarcadores/sangue , Feminino , Glycyrrhiza/química , Ácido Glicirrízico/isolamento & purificação , Humanos , Hipertensão/diagnóstico , Hipertensão/fisiopatologia , Hipopotassemia/sangue , Hipopotassemia/diagnóstico , Masculino , Pessoa de Meia-Idade , Extratos Vegetais/isolamento & purificação , Renina/sangue , Sistema Renina-Angiotensina/efeitos dos fármacos , Fatores de Risco , Adulto JovemRESUMO
In this work, a new molecularly imprinted solid phase extraction protocol was developed for the selective extraction and purification of glycyrrhizic acid from liquorice roots in aqueous media. The molecularly imprinted polymers (MIPs) for glycyrrhizic acid were prepared by using bismethacryloyl-ß-cyclodextrin and methacrylic acid as double functional monomers and characterized by Fourier transform infrared spectroscopy, scanning electron microscope, thermo gravimetric analysis, nitrogen adsorption and elemental analysis. In aqueous media, the adsorption properties of MIPs including adsorption kinetics, adsorption isotherms and selectivity adsorption were investigated. The characterization of imprinted polymers indicated that the prepared MIPs had good stability and many cavity structures. The results of adsorption experiments illustrated the MIPs had high adsorption capacity of glycyrrhizic acid (69.3 mg g-1) with the imprinting factor 3.77, and it took ~5 min to get adsorption equilibrium. The MIPs could be used as an solid phase extraction sorbent absorbent for enrichment and purification of glycyrrhizic acid from the crude extraction of licorice roots, and the results showed promising practical value.
Assuntos
Ácido Glicirrízico/análise , Metacrilatos/química , Impressão Molecular/métodos , Extração em Fase Sólida/métodos , beta-Ciclodextrinas/química , Ácido Glicirrízico/química , Ácido Glicirrízico/isolamento & purificação , Limite de Detecção , Modelos Lineares , Reprodutibilidade dos TestesRESUMO
Glycyrrhizin (GA), a major bioactive compound in licorice, has been extensively used throughout the world as a medicine to treat chronic viral hepatitis and allergic dermatitis. In this study, a new method based on hydrophilic interaction solid phase extraction (HILIC-SPE) and preparative reversed-phase liquid chromatography (prep-RPLC) was developed to purify GA with high purity from the complex licorice extract. Via evaluation of retention behavior of GA and flavonoids in different commercially available columns, a hydrophilic column--Click XIon was finally chosen for the purification due to its excellent resolution toward GA and flavonoids under HILIC mode. To optimize the SPE elution conditions, relative factors including water content, pH and ionic strength had been investigated in chromatographic condition. The result indicated that the most appropriate water content was 30% and pH at 4.00, as well as salt concentration should be controlled at 5mM. In addition, the optimization revealed that GA experiences both hydrophilic interaction and ion-exchange interaction on the Click XIon material. According to the chromatographic evaluation, the optimized conditions were applied to HILIC-SPE to enrich GA from licorice, which leads to an increased content of GA from 13.67% to 64.22%. Finally, prep-RPLC was performed to obtain GA with purity higher than 99.00%ï¼which demonstrating great prospect in large-scale preparation of GA.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Antivirais/isolamento & purificação , Cromatografia de Fase Reversa/métodos , Glycyrrhiza/química , Ácido Glicirrízico/isolamento & purificação , Extração em Fase Sólida/métodos , Anti-Inflamatórios/análise , Antivirais/análise , Ácido Glicirrízico/análise , Interações Hidrofóbicas e HidrofílicasRESUMO
OBJECTIVE: To develop a simple and sensitive high performance liquid chromatographic method for simultaneous determination of catechin hydrate, epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate, dihydromyricetin, glycyrrhizic acid and glycyrrhetinic acid in healthy food for anti-hangover and hepatoprotection, and compare with the capillary electrophoresis method established by our laboratory. METHODS: The samples were ultrasonically extracted by using methanol-water( 4ⶠ1, V/V) for 30 minutes and then centrifuged at 10 000 r/min for 10 minutes. The supernatant was filtered and injected into the HPLC system and then separated on a C_(18) column( 5 µm × 250 mm × 4. 6 mm) at 30â with gradient elution at a flow rate of 0. 8mL/min. Catechins and dihydromyricetin were detected at the wavelength of 210 nm, glycyrrhizic acid and glycyrrhetinic acid were detected at 250 nm. RESULTS: Under the optimal analytical conditions, the peak area of each analyte and its concentration had agood correlation within the linear range( r ≥ 0. 9996). The limits of detection and quantification of the method were 0. 07-1. 25 µg/g( S/N = 3) and 0. 22-4. 18 µg/g( S/N = 10), respectively. The intra-and inter-day relative standard deviations( RSDs)of the mixed standard solution were 0. 26%-1. 95% and 1. 17%-3. 89%, respectively. The spiked recoveries of the analytes were 86. 15%-98. 61%. CONCLUSION: The established method is sensitive and reliable, and could be used for quality control of the healthy food for anti-hangover and hepatoprotection.
Assuntos
Catequina/análise , Cromatografia Líquida de Alta Pressão/métodos , Flavonóis/análise , Ácido Glicirretínico/análise , Ácido Glicirrízico/análise , Catequina/análogos & derivados , Catequina/isolamento & purificação , Eletroforese Capilar , Flavonóis/isolamento & purificação , Ácido Glicirretínico/isolamento & purificação , Ácido Glicirrízico/isolamento & purificação , Humanos , Sensibilidade e EspecificidadeRESUMO
The multi-drug resistance offered by Pseudomonas aeruginosa to antibiotics can be attributed towards its propensity to develop biofilm, modification in cell membrane and to efflux antibacterial drugs. The present study explored the activity of Glycyrrhiza glabra and one of its pure compounds, glycyrrhizic acid against P. aeruginosa and their mechanism of action in terms of the effect on membrane permeability, efflux activity, and biofilm formation were determined. Minimum inhibitory concentrations were determined by using broth dilution technique. The minimum bactericidal concentrations were assessed on agar plate. The MIC of the extract and glycyrrhizic acid was found to be 200 and 100 µg ml(-1), respectively. The MBC was found to be 800 and 400 µg ml(-1) in the case of extract and glycyrrhizic acid, respectively. Time -dependent killing efficacy was also estimated. Flowcytometric analysis with staining methods was used to determine the effect of extract and glycyrrhizic acid at 2 × MIC on different physiological parameters and compared it with the standard (antibiotic). The growth of P. aeruginosa was significantly inhibited by extract and the pure compound. The herbal extract and the glycyrrhic acid were also found to effective in targeting the physiological parameters of the bacteria that involve cell membrane permeabilization, efflux activity, and biofilm formation. This study reports the antipseudomonal action of Glycyrrhiza glabra and one of its compound and provides insight into their mode of action.
Assuntos
Antibacterianos/farmacologia , Biofilmes/efeitos dos fármacos , Membrana Celular/efeitos dos fármacos , Glycyrrhiza/química , Ácido Glicirrízico/farmacologia , Permeabilidade/efeitos dos fármacos , Pseudomonas aeruginosa/efeitos dos fármacos , Antibacterianos/isolamento & purificação , Transporte Biológico Ativo/efeitos dos fármacos , Membrana Celular/fisiologia , Ácido Glicirrízico/isolamento & purificação , Testes de Sensibilidade Microbiana , Viabilidade Microbiana/efeitos dos fármacos , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Pseudomonas aeruginosa/fisiologiaRESUMO
AIM: Study the composition of plant extracts using high-performance liquid chromatography. (HPLC) and evaluation of their antimicrobial effect against Vibrio cholerae El Tor. MATERIALS AND METHODS: Qualitative and quantitative composition of plant extracts was studied using HPLC. Determination of sensitivity of microorganisms to plant extracts was carried out by diffusion into agar method and serial dilutions method. RESULTS: Antibacterial effect of water, water-alcohol and acetone extracts of roots of Limonium gmelinii L., Berberis vulgaris L. and Glycyrrhiza glabra L. was studied. The most effective methods of extraction of biologically active substances, possessing antimicrobial effect against various strains of V. cholerae El Tor, were determined. CONCLUSION: The use of HPLC allowed to establish the presence of catechines, alkaloids protoberberines and glycyrrhizic acid in xtracts, possessing antimicrobial effect against V. cholera El Tor strains.
Assuntos
Antibacterianos/química , Alcaloides de Berberina/química , Catecóis/química , Ácido Glicirrízico/química , Extratos Vegetais/química , Vibrio cholerae/efeitos dos fármacos , Acetona/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Alcaloides de Berberina/isolamento & purificação , Alcaloides de Berberina/farmacologia , Berberis/química , Catecóis/isolamento & purificação , Catecóis/farmacologia , Cromatografia Líquida de Alta Pressão , Etanol/química , Glycyrrhiza/química , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/farmacologia , Testes de Sensibilidade Microbiana , Plumbaginaceae/química , Solventes/química , Vibrio cholerae/crescimento & desenvolvimento , Água/químicaRESUMO
This paper is to investigate the optimization conditions of ultrasonic technique for extraction process of Xiaoqinglong granules in medium scale. First of all, single factor experiment was used to determine the overall impact tendency and range of each factorï¼ secondly, Box-Behnken method was used for optimization and detecting the content of paeoniflorin, ephedrine hydrochloride, glycyrrhizic acid of the liquid medicine. Their respective extraction rate was calculated and the comprehensive evaluation was carried out. The results were used as the evaluation basis for the efficacy of Xiaoqinglong granules ultrasonic extraction. The test results showed that the optimum extraction process of Xiaoqinglong granules by ultrasonic extraction was under the following conditions: ultrasonic power 600 W, liquid-solid ratio 10â¶1, extraction for 31 min. Under this condition, the predicted value of extraction rate for Xiaoqinglong granules was 85.90%, and the test value was 85.87%. The mathematical model(P<0.01) established in this paper was significant, and can be used for the analysis and prediction of the ultrasonic extraction process of Xiaoqinglong granules.