stilbenes and physcione

A rapid, efficient, and green sample preparation method has been developed to extract eight active ingredients (gallic acid, catechins, epicatechin, polydatin, 2,3,5,4'-tetrahydroxystilbene-2-O-β-d-glucoside, resveratrol, emodin, and physcion) in radix polygoni multiflori by miniaturized matrix solid-phase dispersion microextraction. Simple and sensitive ultra high performance liquid chromatography combined with ultraviolet detection has been applied to analyze the multiple compounds. The best results were obtained by adding 25 mg sample into 25 mg adsorbent and grinding for 2 min with disorganized silica as adsorbent and 1 mL 150 mM 1-dodecyl-3-methylimidazolium bromide as a green eluting solvent. Good linearity (r

Topics: Catechin; Chromatography, High Pressure Liquid; Emodin; Fallopia multiflora; Gallic Acid; Glucosides; Particle Size; Solid Phase Microextraction; Stilbenes; Surface Properties

Polygoni Multiflori Radix (PMR) has been traditionally used as a tonic and an anti-aging remedy for centuries; however, hepatic lesions linked to PMR have been frequently reported.. This work attempted to investigate the hepatotoxic potential of PMR extract and the toxicokinetics of stilbene glucoside and anthraquinones in PMR extract following repeated administration.. Histopathological and biochemical tests were performed to assess the hepatotoxicity of PMR extract. A rapid and sensitive liquid chromatography-mass spectrometry (LC-MS) assay was developed for toxicokinetic analysis of the main constituents of PMR extract, including 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside (TSG), emodin-8-O-β-D-glucoside and emodin.. The histopathological and biochemical tests indicated that repeated administration of high-dose PMR extract (20 g/kg) for 3 weeks could cause hepatic lesions, while the low-dose treatment (1 g/kg) was safe. Necrosis and steatosis of hepatic cells, inflammatory cell infiltration and mild fibrosis were the main toxicity symptoms caused by high-dose PMR extract in rat liver. The aspartate aminotransferase (AST) levels increased by approximately 17%, from 110.80±0.84 to 129.75±10.83 IU/L, in the high-dose group compared with the control group. The proposed LC-MS method was proven to be suitable for the simultaneous quantification of these three constituents by affording desirable linearity (r(2)>0.998) and satisfactory precision (error less than 10%). The toxicokinetic study showed that emodin could not be detected in the low-dose group, but the AUC and Cmax of emodin displayed a gradual increase with repeated treatments in the high-dose group. The toxicokinetics of TSG in the low- and high-dose groups exhibited similar trends after repeated administration.. Consideration needs to be given to the rational application of PMR in the clinic to balance its benefits and risks. The increased emodin exposure in vivo provided a putative explanation for the observed hepatic lesions induced by PMR extract, although further studies to confirm the potentially causal link between emodin exposure and hepatic lesions are still necessary.

Topics: Animals; Chemical and Drug Induced Liver Injury; Emodin; Glucosides; Liver; Male; Plant Extracts; Plant Roots; Polygonum; Rats, Sprague-Dawley; Stilbenes; Toxicokinetics

Raw and processed Polygoni Multiflori Radix (PMR and PMRP) are used in the prevention and treatment of non-alcoholic fatty liver disease (NAFLD), hyperlipidemia or related diseases. In our previous research, 2, 3, 5, 4'-tetrahydroxy-stilbene-2-O-β-D-glucoside (TSG) displayed the most important role in the total cholesterol (TC) lowering effect among all the chemical constituents of Polygonum multiflorum. Emodin and physcion displayed more favorable triglyceride (TG) reducing effects than TSG. However, there are few researches focus on the approach and mechanism of how do Polygonum multiflorum exhibit good lipid regulation activity. The targeted sites of active substances of Polygonum multiflorum are still not clearly elucidated. This research pays close attention to how major chemical components of Polygonum multiflorum affect the TC and TG contents in liver cells.. In this research, a sensitive, accurate and rapid in vitro model, steatosis hepatic L02 cell, was used to explore target sites of active chemical substances of Polygonum multiflorum for 48h. Steatosis hepatic L02 cell was exposed to emodin, physcion and TSG, respectively. The contents of four key enzymes in the pathway of synthesis and decomposition of TC and TG were investigated after exposure. Meanwhile, the contents of lipid transfer protein were also tested. The diacylgycerol acyltransferase 1 (DGAT1) controlled the biosynthesis of TG from free fatty acids while 3-hydroxy-3-methyl-glutaryl-CoA reductase (HMG-CoA reductase) limited the biosynthesis of TC. Hepatic triglyceride lipase (HTGL) and cholesterol 7α-hydroxylase (CYP7A) played the key role in the lipolysis procedure of TG and TC.. The synthesis of TC and TG in steatosis L02 cells were apparently increased in the model group compared to the control group. Intracellular contents of HMG-CoA reductase and DGAT1 increased 32.33% and 56.52%, while contents of CYP7A and HTGL decreased 21.61% and 47.37%. Emodin, physcion and TSG all showed down-regulation effects on HMG-CoA reductase, while up-regulation effects on CYP7A. The most remarkable effect on HMG-CoA reductase was found on emodin. Emodin could reduce the DGAT1 content from 438.44 ± 4.51 pg/mL in model group to 192.55 ± 9.85 pg/mL (100 μm). The content of HTGL in 300 μm physcion group was 3.15 ± 0.15 U/mL, which was more significantly effective than the control, lovastatin and fenofibrate group.. TSG could raise the content of CYP7A and then promote the lipolysis of cholesterol. Moreover, TSG also showed the best LDL-reducing effect. Emodin could inhibit HMG-CoA reductase and DGAT1, which were key enzymes in the synthesis of TC and TG. Physcion increased the content of HTGL, and then could boost the lipolysis of triglyceride. At the same time, physcion showed the best VLDL-reducing effect. In view of the above conclusions, we contributed the lipid regulation activity to an overall synergy of TSG, emodin and physcion.

Topics: Cell Line; Cholesterol; Cholesterol 7-alpha-Hydroxylase; Diacylglycerol O-Acyltransferase; Emodin; Fatty Liver; Glucosides; Humans; Hydroxymethylglutaryl CoA Reductases; Plant Roots; Polygonum; Stilbenes; Triglycerides

Japanese knotweed (Fallopia japonica , also known as Polygonum cuspidatum) is a common invasive plant species on Prince Edward Island (PEI), Canada, whereas it has been used in Chinese medicine and more recently as a raw material for extracting resveratrol. This paper reports on the quantification of resveratrol, polydatin, emodin, and physcion in roots, stems, and leaves of Japanese knotweed samples from PEI and British Columbia (BC), Canada, and nine provinces of China, by ultraperformance liquid chromatography (UPLC). The results showed that the root contains a much higher level of resveratrol than the stem and leaf, and it is accumulated in its highest level in October. PEI-grown knotweed contains similar levels of resveratrol and polydatin compared to Chinese samples collected in the month of October, but the contents of the other anthraquinones (emodin and physcion) are different. As such, Japanese knotweed grown in PEI could be a commercially viable source of raw material for resveratrol production; however, caution has to be taken in harvesting the right plant species.

Topics: Antioxidants; Emodin; Fallopia japonica; Glucosides; Plant Leaves; Plant Roots; Plant Stems; Plant Weeds; Prince Edward Island; Quality Control; Resveratrol; Stilbenes

Polygonum cuspidatum is a plant with spreading rhizomes and numerous reddish-brown stems that has been used in Korean folk medicine to improve oral hygiene. Nevertheless, there are no reports related to its possible effect on the virulence of dental biofilms. In this study, the ability of a fraction (F1) separated from P. cuspidatum, alone or in combination with fluoride, to disrupt virulence factors and the composition of Streptococcus mutans biofilms was examined. F1 was mainly composed of resveratrol, emodin and physcion (approximately 16.2%, 18.9% and 2.07% of the weight of F1, respectively). F1 showed inhibitory effects on acid production and F-ATPase activity of S. mutans in biofilms, and could enhance fluoride activity against acid production and acid tolerance of S. mutans in biofilms. When S. mutans biofilms were briefly treated with F1 (10 min, a total of five times), the biomass accumulation, water-insoluble polysaccharides and intracellular iodophilic polysaccharides were reduced. Furthermore, the fluoride activity against biomass accumulation was enhanced by F1. These results suggest that F1 may be useful in the control of dental biofilms and in improving the cariostatic properties of fluoride without increasing its exposure.

Topics: Biofilms; Drug Synergism; Emodin; Fallopia japonica; Fluorides; Humans; Hydrogen-Ion Concentration; Plant Extracts; Resveratrol; Stilbenes; Streptococcus mutans; Virulence Factors

Radix Polygoni Multiflori (RPM) and Radix Polygoni Multiflori Praeparata (RPMP) were traditionally widely used as Chinese herbal medicine. However, liver adverse reactions caused by RPM or RPMP were frequently reported all around the world recent years. The aim of this study was to study the cytotoxicities of RPM, RPMP and their major constituents on human liver cell L-02 simultaneously.. Multi-assays, including MTT assay, neutral red uptake (NRU) assay, LDH leakage percentage and liver enzyme secretion (AST, ALT and ALP) were used. Cytotoxicities of major chemical constituents of RPM, 2, 3, 5, 4'-tetrahydroxy-stilbene-2-O-β-D-glucoside (TSG), physcion and emodin, were tested. The cytotoxicities of water, 50% ethanol and 95% ethanol extractions of RPM and RPMP were tested. HPLC-DAD analysis was carried to reveal the content change of TSG, physcion and emodin after the processing procedure.. The TD(50) of TSG, physcion and emodin in MTT assay were >10,000 μM, 2853.61 μM and 520.37 μM. In the NRU assay, the TD(50) of TSG, physcion and emodin were much smaller (1401.53 μM, 1140.00 μM, and 3.80 μM). Emodin induced much severe liver enzyme secretion than TSG and physcion. Cell proliferation and LDH leakage rate showed no difference between RPM and RPMP extractions, but ALP, AST and ALT secretions in RPMP extractions were significant lower than that of PMR groups. Water extractions of RPM and RPMP were less toxic than any other solvent in most of the assays. Positive correlation was found between the TSG/emodin ratio and MTT survival rate. The emodin/physcion ratio also showed positive correlation with the LDH leakage percentage.. In conclusion, Radix Polygonum multiflorum and Radix Polygonum multiflorum Praeparata were not liver injure inducing in our in vitro assays. However, the processing produce of RPM could reduce its effect on both cell proliferation and enzyme secretion of liver cell. Judging from cell proliferation, integrity of cell membrane and enzyme secretion, three major chemical constituents of RPM: TSG, physcion and emodin showed no, moderate and severe cytotoxicity against human liver cell line L-02 respectively. Chemical constituents-cytotoxicity relationship investigation revealed that TSG and physcion probably had attenuating effect to emodin. The attenuating mechanisms were still under investigation.

Topics: Alanine Transaminase; Alkaline Phosphatase; Aspartate Aminotransferases; Cell Line; Cell Proliferation; Chemical and Drug Induced Liver Injury; Dose-Response Relationship, Drug; Drugs, Chinese Herbal; Emodin; Glucosides; Humans; L-Lactate Dehydrogenase; Liver; Plant Roots; Plants, Medicinal; Polygonaceae; Solvents; Stilbenes

The aim of this study was to separate the anti-acidogenic substances against Streptococcus mutans UA 159 from Polygonum cuspidatum.. The anti-acidogenic substances were separated by a series of liquid-liquid fractionations followed by normal-phase silica gel liquid chromatography, based on high-performance liquid chromatography and glycolytic pH-drop assay. The effectiveness of the separated substances on the acidogenicity of Streptococcus mutans UA 159 was examined using sodium fluoride as a positive control. The chemical composition and quantities of the components of the substances was also assessed by qualitative-quantitative chromatographic analysis.. Among the substances separated from P. cuspidatum, F3 showed the strongest inhibitory effect on the acidogenicity of S. mutans UA 159 in a dose-dependent manner without displaying any bactericidal activity. F3 decreased the acidogenicity of S. mutans even at 12.5 microg ml(-1) (P < 0.05). F3 consisted mainly of resveratrol and emodin (C(14)H(12)O(3) and C(14)H(4)O(2)(OH)(3)CH(3), respectively), which made up approximately 60% of the weight of F3.. F3 can be considered as a promising agent for controlling the acidogenicity of S. mutans and subsequent dental caries formation.

Topics: Acids; Anthracenes; Cariostatic Agents; Chelating Agents; Chemical Fractionation; Chromatography, Gel; Chromatography, High Pressure Liquid; Chromatography, Liquid; Dose-Response Relationship, Drug; Drugs, Chinese Herbal; Emodin; Fallopia japonica; Glucosides; Glycolysis; Glycosides; Humans; Hydrogen-Ion Concentration; Materials Testing; Phenols; Plant Extracts; Resveratrol; Sodium Fluoride; Stilbenes; Streptococcus mutans

To study the chemical constituents from Radix Boehmeriae.. Compounds were isolated by various column chromatographies with silica gel, their structures were elucidated by spectral analysis and chemical evidence.. Eight compounds were isolated and their structures were identified as emodin (1), emodin-8-O-beta-glucopyranoside (2), physcion (3), polydatin (4), catechin (5), epicatechin (6), potassium nitrate (7), sitosterol (8).. Among these compounds, 3 -7 are isolated from Radix Boehmeriae for the first time.

Topics: Boehmeria; Catechin; Chromatography; Emodin; Glucosides; Magnetic Resonance Spectroscopy; Nitrates; Plant Roots; Potassium Compounds; Stilbenes

A reverse-phase HPLC method was developed for simultaneous quantification of six bioactive compounds in Rhizoma et Radix Polygoni Cuspidati. These compounds--polydatin (1), resveratrol (2), rhein (3), emodin (4), chrysophanol (5) and physcion (6)--were analysed from 24 authentic samples of the herb using UV HPLC. Based on the UV absorption characteristics of the six compounds, absorption wavelengths of 306 nm were chosen to quantify compounds 1 and 2, and 290 nm for compounds 3-6. A reliable and reproducible quantitative HPLC method for analysing authentic samples of Rhizoma et Radix Polygoni Cuspidati from different cultivation regions was developed. The results showed that the concentration of compound 1 in samples from Sichuan was almost 2 fold higher than that of samples acquired in Guangxi. Furthermore, compounds 3 and 5 were not found in all the samples tested. Thus, instead of using polydatin (1) and emodin (4) as markers for quality assessment, as in conventional practice, these findings show that compounds 2 and 6 are more suited to act as marker compounds for a more specific assessment of the quality of this herb.

Topics: Anthraquinones; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Emodin; Fallopia japonica; Glucosides; Molecular Structure; Reproducibility of Results; Resveratrol; Rhizome; Stilbenes; Technology, Pharmaceutical

To study the technological parameters of the purification process for effective part from Polygonum cuspidatum.. Using adsorption capacities and desorption rates of polydatin, resveratrol,emodin,physcion and total anthraquinone as the primary screening indexes, six resins were surveyed,and the optimized conditions of adsorption and desorption of the effective ingredients were studied.. Resin D101 gave good separation performance and was selected to purify the effective part in Polygonum cuspidatum. The optimum parameters were established as the following: 1 BV (bed volume) sample extract was passed through the column with a flow rate of 2.4 BV x h(-1), 30 min later,the column was washed with 2 BV water, 2 BV 20% ethanol, 5 BV 50% ethanol, 2 BV 70% ethanol and 5 BV 95% ethanol, respectively. The combined 50% and 95% ethanolic elutes were concentrated to yield the purified effctive part.. The purity of the total effective ingredients in the product was up to 36. 87%. Macroporous resin D101 could be well used in separating and purifying the effective part from Polygonum cuspidatum.

Topics: Adsorption; Anthraquinones; Drugs, Chinese Herbal; Emodin; Fallopia japonica; Glucosides; Plants, Medicinal; Resins, Synthetic; Resveratrol; Stilbenes; Technology, Pharmaceutical; Temperature

To provide scientific basis for the selection of agrotype and property fertilization for Rumex gmelini cultivated in compliance with good agricultural practice (GAP).. HPLC method was applied to determinate the content of seven active constituents (resveratrol, polydatin, chrysophanol 1-glucoside, nepodin, emodin, chrysophanol and physcion) of annual R. gmelini. And the correlation between soil nutrients and content of active constituents in the root of R. gmelini were analyzed by stepwise regression analysis.. Seven regression equation were established. The statistic significance was found in three of them.. The soil with high total K level is not suitable for R. gmelini cultivation. But the higher available N, available P, available K level of soil is suitable.

Topics: Anthraquinones; Ecosystem; Emodin; Fertilizers; Glucosides; Nitrogen; Phosphorus; Plant Roots; Plants, Medicinal; Potassium; Regression Analysis; Resveratrol; Rumex; Soil; Stilbenes

To establish a HPLC method for simultaneous determination of resveratrol, emodin, chrysophanol, physcion in root of Polygonum cuspidatum and its extract.. The separation was performed in a Hypersil ODS C18 column with a mobile phase of Acetonitrile-1%HAc. The flow rate was 1.0 mL x min(-1) and detection wavelength was at 287 nm.. The mean recovery and RSD of resveratrol, emodin, chrysophanol, physcion was 101.8%, RSD 1.7%; 96.2%, RSD 1.4%; 99.7%, RSD 1.0%; 98.60%, RSD 0.97% respectively.. The method is accurate, simple and reliable. It can be used for quality control of P. cuspidatum and its extract.

Topics: Anthraquinones; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Emodin; Fallopia japonica; Plant Roots; Plants, Medicinal; Quality Control; Resveratrol; Stilbenes

To establish the HPLC fingerprint of Rhizoma Polygoni Cuspidati (Polygonum cuspidatum).. The HPLC separation was carried with Diamonsil C18 column and eluted with a gradient from methanol and 0.1% phosphoric acid, the detection wavelength was at 230 nm and recording 70 min. The similarity of chromatograms was compared by mean of the software from Zhongnan University.. The constituents of P. cuspidatum were well separated by HPLC, and the similarity was above 0.80.. The method can be used for the study of fingerprints of Rhizoma Polygoni Cuspidati.

Topics: Chromatography, High Pressure Liquid; Emodin; Fallopia japonica; Glucosides; Plants, Medicinal; Quality Control; Reproducibility of Results; Resveratrol; Rhizome; Stilbenes; Technology, Pharmaceutical

Different methods of processing Radix Polygoni Multiflori and the change of chemical components including emodin, physcion, 2,3,5,4'-stilbene glucoside, and tannin were investigated. The dried roots of polygoni were processed in different ways, such as, steamed with black bean sauce, steamed with water, stewed with black bean sauce, and stewed with black bean sauce at high pressure, for h and 36 h, respectively. The process stewing with black bean sauce was also investigated for 12, 24, 36 h, and 48 h, respectively. The results indicated that 2,3,5,4'-stilbene glucoside and total free anthraquinones varied in different processes. In the process of black bean sauce stewing, the content of 2,3,5,4'-stilbene glucoside decreased with processing time, reached 17% of original at 48 h. The content of tannin and combined and free anthraquinones also decreased with processing time. It was concluded, therefore, that the processing of Radix Polygoni Multiflori should be standardized to avoid significant variation of chemical contents.

Topics: Emodin; Glucosides; Hot Temperature; Plant Roots; Plants, Medicinal; Polygonum; Stilbenes; Tannins; Technology, Pharmaceutical

To establish a method used for optimization of harvesting time and determine the best time for harvesting Rumex gmelini.. An HPLC method was applied to determinate the contents of seven active constituents(resveratrol, polydatin, chrysophanol 1-glucoside, nepodin, emodin, chrysophanol and physcion)of R. gmelini at different development stage. The result was analyzed by principal component analysis.. The accumulation of active constituents showed a regular pattern.. The best harvesting time of R. gmelini is early July.

Topics: Anthraquinones; Emodin; Glucosides; Plant Roots; Plants, Medicinal; Principal Component Analysis; Quality Control; Resveratrol; Rumex; Seasons; Stilbenes

High-speed counter-current chromatography (HSCCC) was applied to the separation and purification of five compounds from the Chinese medicinal herb Polygonum cuspidatum Sieb. et Zucc. The crude extracts from P. cuspidatum Sieb. et Zucc were treated with light petroleum-ethyl acetate-methanol-water (2:5:4:6, v/v). Sample 1 was obtained from the lower phase and sample 2 from the upper phase. The sample 1 was separated with light petroleum-ethyl acetate-water (1:5:5, v/v) and yielded 19.3mg of piceid, 17.6 mg of anthraglycoside B from 200mg of sample 1. The sample 2 was separated with light petroleum-ethyl acetate-methanol-water (3:5:4:6, v/v) and light petroleum-ethyl acetate-methanol-water (3:5:7:3, v/v) in a gradient elution and yielded 18.5mg of resveratrol, 35.3mg of emodin and 8.2mg of physcion from 220 mg of sample 2. The purity of each compound is over 95% as determined by HPLC. The chemical structures of these components were identified by (1)H NMR and (13)C NMR.

Topics: Anthracenes; Chromatography, High Pressure Liquid; Countercurrent Distribution; Emodin; Fallopia japonica; Glucosides; Glycosides; Molecular Structure; Plant Preparations; Reproducibility of Results; Resveratrol; Stilbenes