ABSTRACT
Diabetes mellitus is a serious threat to human life and health. The α-glucosidase and protein tyrosine phosphatase 1B (PTP1B) were important targets for the treatment of type 2 diabetes mellitus. In this paper, euparin, a natural product from Eupatorium chinense possessed extensive pharmacological activities, was selected as the lead compound. It was derived into chalcone compounds with high efficiency, and the inhibitory activities of these 30 products on α-glucosidase and PTP1B were tested. The results showed that compounds 12 and 15 had good inhibitory activities against both enzymes. The IC50 value of 12 to inhibit α-glucosidase and PTP1B was 39.77 and 39.31 µM, and the IC50 value of 15 to inhibit α-glucosidase and PTP1B was 9.02 and 3.47 µM, respectively. In addition, molecular docking results showed that compounds 12 and 15 exhibited good binding affinities toward both α -glucosidase and PTP1B with negative binding energies. The results of the present study demonstrate that compounds 12 and 15 might be beneficial in the treatment of type 2 diabetes.
Subject(s)
Diabetes Mellitus, Type 2 , Glycoside Hydrolase Inhibitors , Humans , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/chemistry , Diabetes Mellitus, Type 2/drug therapy , alpha-Glucosidases/metabolism , Molecular Structure , Protein Tyrosine Phosphatase, Non-Receptor Type 1 , Molecular Docking SimulationABSTRACT
Depression is the most significant risk factor for suicide, yet the causes are complex and disease mechanism remains unclear. The incidence and disability rate of depression are very high and the efficacy of some traditional antidepressants is not completely satisfactory. Recently, some studies have found that benzofurans have anti-oxidation and anti-monoamine oxidase properties, which are related to depression. Euparin is a monomer compound of benzofuran, previous work by our team found that it improves the behavior of depressed mice. However, additional antidepressant effects and mechanisms of Euparin have not been reported. In this study, the Chronic Unpredictable Mild Stress (CUMS) model of mice was used to further investigate the effect and mechanism of Euparin on depression. Results showed that Euparin (8, 16 and 32 mg/kg) reduced depression-like behavior in mice compared with the model group. Meanwhile, all doses of Euparin were found to increase the contents of monoamine neurotransmitter and decrease monoamine oxidase and reactive oxygen species (ROS) levels in brain of depression mice. Additionally, Euparin restored CUMS-induced decrease of Spermidine/Spermine N1-Acetyltransferase 1 (SAT1), N-methyl-D-aspartate receptor subtype 2B (NMDAR2B) and brain derived neurotrophic factor (BDNF) expression. These findings demonstrate that Euparin has antidepressant properties, and its mechanism involves the SAT1/NMDAR2B/BDNF signaling pathway.
Subject(s)
Benzofurans/pharmacology , Depression/drug therapy , Signal Transduction/drug effects , Stress, Psychological/complications , Acetyltransferases/metabolism , Animals , Behavior Observation Techniques , Behavior, Animal/drug effects , Benzofurans/therapeutic use , Brain-Derived Neurotrophic Factor/metabolism , Depression/diagnosis , Depression/pathology , Depression/psychology , Disease Models, Animal , Dopamine , Dose-Response Relationship, Drug , Drug Evaluation, Preclinical , Frontal Lobe/drug effects , Frontal Lobe/metabolism , Frontal Lobe/pathology , Hippocampus/drug effects , Hippocampus/metabolism , Hippocampus/pathology , Humans , Male , Mice , Neurotransmitter Agents/metabolism , Norepinephrine/metabolism , Receptors, N-Methyl-D-Aspartate/metabolism , Serotonin/metabolism , Specific Pathogen-Free Organisms , Stress, Psychological/psychologyABSTRACT
An efficient procedure for the synthesis of benzochromene derivatives employing 1-(6-hydroxy-2-isopropenyl-1-benzofuran-yl)-1-ethanone (euparin), aldehydes, alkyl bromides, dialkyl acetylenedicarboxylate and triphenylphosphine in the presence of KF/CP NPs as a heterogeneous base nano-catalyst in water at 80 °C is investigated. Also, the antioxidant activity of some synthesized compounds was studied. The workup of mixture of reaction is simple, and the products can be separated easily by filtration. KF/CP NPs showed a good improvement in the yield of the product and displayed significant reusable activity.
Subject(s)
Antioxidants/chemical synthesis , Chemistry Techniques, Synthetic , Chromans/chemical synthesis , Green Chemistry Technology , Nanoparticles , Zeolites/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Catalysis , Chromans/chemistry , Chromans/pharmacology , Iron/chemistryABSTRACT
A novel class of benzofuran derivatives is prepared from the isocyanide-based MCR, euparin and aldehydes in the presence of ZnO-nanorods as a catalyst in excellent yields at room temperature under solvent-free conditions as a green reaction medium. Also, the antioxidant activities of some synthesised compounds such as 4a, 4b, 10a and 10b were evaluated by DPPH radical scavenging and ferric reduction activity potential (FRAP) assays. Compound 10b, was shown moderate radical scavenging activity and very good reducing activity compared to standards (BHT and TBHQ).
Subject(s)
Antioxidants/pharmacology , Benzofurans/chemical synthesis , Benzofurans/pharmacology , Petasites/chemistry , Antioxidants/chemical synthesis , Benzofurans/chemistry , Drug Evaluation, Preclinical/methods , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Green Chemistry Technology , Iron/chemistry , Zinc Oxide/chemistryABSTRACT
Objective To study chemical constituents of the roots of Eupatorium chinense. Methods The chemical constituents were separated and purified by the normal phase silica gel column chromatography, preparative thin-layer chromatography, and preparative HPLC. Their structures were determined by various spectral data. Results Nineteen compounds were isolated from the acetic ether extract of E. chinense and the structures were identified as euparin (1), 1-[2-(1-acetoxymethyl-vinyl)-6-hydroxy-benzofuran-5-yl]- ethanone (2), 6-hydroxy-3β-methoxytrematone (3), euparone (4), 8-methoxy-9-hydroxythymol (5), dehydroespeleton (6), 8-methoxy-9-hydroxythymol 3-O-angelate (7), 9-hydroxythymol (8), 4-hydroxy cinnamic acid methyl ester (9), p-hydroxy benzaldehyde (10), 8,9-dehydro-10-hydroxythymol (11), diisobutyl phthalate (12), dibutyl phthalate (13), p-coumaric acid (14), dihydrocoumarin (15), methylcaffeate (16), 2,5-dimethylphenol (17), 1H-indazole (18), and (Z)-3-(hydroxymethyl)-7-methylocta- 2,6-dienly1 acetate (19). Conclusion The chemical constituents are investigated and identified from the roots of E. chinense for the first time. Among them, compounds 2, 3, 5-11 are isolated from E. chinense for the first time, and compounds 6, 9, 12, 14-19 are isolated from the genus of Eupatorium for the first time. Compounds 1-4 are benzofurans, which are the characteristic constituents in Eupatorium genus.
ABSTRACT
A reversed phase high performance liquid chromatography (HPLC) method was established for the simultaneous determination of 12,13-dihydroxyeuparin and glycyrrhizic acid in Yanyanfang mixture.A Grace Apollo C18 column (250 mm× 4.6 mm,5 μm) was used as the stationary phase and the mobile phase was composed of acetonitrile and aqueous phosphoric acid (0.2％,v/v).Gradient elution was carried out at the flow rate of 1.0 mL/min and the column temperature was 30 ℃.An ultraviolet (UV) detector was used with a selected wavelength of 240 nm.Calibration curves were linear within the concentration range of 4.6-45.75 μg/mL for 12,13-dihydroxyeuparin (r＞0.9999) and 106.9-1068.9μg/mL for glycyrrhizic acid (r＞0.9999),respectively.Recoveries were 102.18 ％ for 12,13-dihydroxyeuparin and 101.17％ for glycyrrhizic acid.The method developed could be applied to the simultaneous determination of 12,13-dihydroxyeuparin and glycyrrhizic acid in Yanyanfang mixture.
ABSTRACT
A reversed phase high performance liquid chromatography （HPLC） method was established for the simultaneous determination of 12, 13-dihydroxyeuparin and glycyrrhizic acid in Yanyanfang mixture. A Grace Apollo Cl8 column （250 mm × 4.6 mm, 5 μm） was used as the stationary phase and the mobile phase was composed of acetonitrile and aqueous phosphoric acid （0.2%, v/v）. Gradient elution was carried out at the flow rate of 1.0 mL/min and the column temperature was 30 ℃. An ultraviolet （UV） detector was used with a selected wavelength of 240 nm. Calibration curves were linear within the concentration range of 4.6-45.75 μg/mL for 12, 13-dihydroxyeuparin （r〉0.9999） and 106.9-1068.9μg/mL for glycyrrhizic acid （r〉0.9999）, respectively. Recoveries were 102.18% for 12, 13-dihydroxyeuparin and 101.17% for glycyrrhizic acid. The method developed could be applied to the simultaneous determination of 12, 13- dihydroxyeuparin and glycyrrhizic acid in Yanyanfang mixture.
ABSTRACT
Objective To establish the HPLC fingerprint of Eupatorium chinense.Methods The ana-lysis was performed on a Kromasil C18 column(250 mm?4.6 mm,5 ?m) with acetonitrile-water as mobile phase in a gradient mode.The flow rate was 1.0 mL/min.The column temperature was 25 ℃ and the detection wavelength was 230 nm.Results The fingerprint of E.chinense with common 13 peaks was established.The relative retention time and the ranges of relative area of the common peaks were determined.Conclusion The established fingerprint could be used for the quality control of E.chinense.
