OBJECTIVE Senna and rhubarb are classified as stimulative laxatives,and known to have similar effective constituents,the anthraquinones.Being protected by theβ-glucoside bond,the anthraquinones can reach the intestin...OBJECTIVE Senna and rhubarb are classified as stimulative laxatives,and known to have similar effective constituents,the anthraquinones.Being protected by theβ-glucoside bond,the anthraquinones can reach the intestines where they are degraded into complex metabolites by enzymes secreted from the intestinal microbiome.It is these complex metabolites that produce the laxative effects.Then the similarities and differences of action between the anthraquinones require further elucidation.METHODS Here,we studied metabolites of senna anthraquinones(SAQ),rhubarb anthraquinones(RAQ)and their chemical marker,sennoside A(SA),in a rat diarrhea model.In the in vitro biotransformation experiments,SAQ,RAQ and SA were incubated with rat fecal flora solution and the metabolites produced were analyzed using HPLC.In the in vivo studies,the same compounds were investigated for purgation induction,with measurement of histopathology and multiple aquaporins(Aqps)gene expression in six organs.RESULTS SAQ and RAQ had similar principal constituents but could be degraded into different metabolites.A similar profile of Aqps down-regulation for all compounds was seen in the colon,suggesting a similar mechanism of action for purgation.However,in the kidneys and livers of the diarrhea-rats,down-regulation of Aqps was found in the RAQ-rats whereas up-regulation of Aqps was seen in the SAQ-rats.Furthermore,the RAQ-rats showed lower aquaporin 2(Aqp2)protein expression in the kidneys,whilst the SA-rats and SAQ-rats had higher Aqp2 protein expression in the kidneys.This may have implications for side effects of SAQ or RAQ in patients with chronic kidney or liver diseases.CONCLUSION SAQ and RAQ showed similar laxative actions with a similar mechanism,they could display different actions in rat kidneys and livers.We suggest that the clinical usage of senna or rhubarb products should be clarified for patients having chronic kidney or liver diseases.展开更多
[Objectives]To determine the content of five kinds of free anthraquinones in raw rhubarb and stewed rhubarb by HPLC,and compare their content difference,so as to reveal the change rule of material basis before and aft...[Objectives]To determine the content of five kinds of free anthraquinones in raw rhubarb and stewed rhubarb by HPLC,and compare their content difference,so as to reveal the change rule of material basis before and after processing of traditional Chinese medicine.[Methods]The content was determined by HPLC with Thermo BDS HYPERSII C18 column(4.6 mm×250 mm,5μm)as chromatographic column and methanol-0.1%phosphoric acid(85∶15)aqueous solution as mobile phase;the detection wavelength was 256 nm,the flow rate was 1.0 mL/min,the column temperature was 30℃,and the injection volume was 10μL.[Results]Aloe-emodin,rhein,emodin,chrysophanol and emodin methyl ether showed a good linear relationship in the linear range of 0.0207-0.414(R2=0.9999),0.1721-3.442(R2=0.9996),0.0203-0.406(R2=0.9999),0.148-2.96(R2=0.9998)and 0.164-3.28(R2=0.9993),respectively;the content of aloe-emodin decreased by about 8.26%,and rhein decreased by about 9.21%;the content of emodin increased by about 16.44%,chrysophanol increased by about 16.12%,and emodin methyl ether increased by about 20.01%,indicating that the processing technology had different effects on the components of rhubarb.[Conclusions]The content of five free anthraquinones in rhubarb was affected to different degrees after processing,and this method could be used as a quality control method for rhubarb and its different processed products.展开更多
Acid-catalytic 1,3-butadiene condensation with para-quinones followed by the obtained product oxidation may be performed in one stage as one-pot process, if assisted by the aqueous solutions of Mo-V-P heteropoly acids...Acid-catalytic 1,3-butadiene condensation with para-quinones followed by the obtained product oxidation may be performed in one stage as one-pot process, if assisted by the aqueous solutions of Mo-V-P heteropoly acids with a composition of HaPzMoyVxOb. 1,4-naphthoquinone (NQ) condensation with 1,3-butadiene in HPA solutions (brutto-composition H15P4Mo18V7O89 and H17P3Mo16V10O89) in the presence of hydrophylic organic solvents (acetone, 1,4-dioxane) provides 70% yield of 9,10-anthraquinone (AQ) containing no less than 90% AQ. In the same conditions reaction NQ with substituted 1,3-butadienes in the presence of the aqueous H17P3Mo16V10O89 (HPA-10) solution allows to prepare substituted AQ with yield up to 90% and purity up to 99%. The catalysts are regenerated by oxygen in separate stage and are reused.展开更多
Natural long-chain alkanol and alkyl carboxylic acid were used to prepare novel hydrophobic deep eutectic solvents(HDESs).These HDESs are liquid at room temperature and have low viscosity(<12.26 mPa·s),low pol...Natural long-chain alkanol and alkyl carboxylic acid were used to prepare novel hydrophobic deep eutectic solvents(HDESs).These HDESs are liquid at room temperature and have low viscosity(<12.26 mPa·s),low polarity(lower than that of methanol,ChCl-based deep eutectic solvents and other reported HDESs),and low density(<0.928 g/mL).A simple one-pot method based on a novel HDES-water two-phase extraction system was constructed for the extraction of weak-polarity bioactive components,anthraquinones,from Rhei Radix et Rhizoma.This HDES-based new extraction method does not consume hazardous organic solvents and can obtain a total anthraquinone yield of 21.52 mg/g,which is close to that obtained by the Chinese pharmacopoeia method(21.22 mg/g)and considerably higher than those by other reported HDESs-based extraction methods(14.20-20.09 mg/g,p<0.01).The high extraction yield can be mainly attributed to the severe destruction of the RRR cell walls by the extraction system and the excellent dissolving ability of novel HDESs for anthraquinones.展开更多
Three new anthraquinones, emodin-8-β-D-(2″-O-coumarate)glucoside 1, emodin-8-β- D-(6′-O-acetyl)glucoside 2 and physicon-8-β-D-(6′-O-acetyl)glucoside 3, were isolated from the roots of Polygonum cillinerve and th...Three new anthraquinones, emodin-8-β-D-(2″-O-coumarate)glucoside 1, emodin-8-β- D-(6′-O-acetyl)glucoside 2 and physicon-8-β-D-(6′-O-acetyl)glucoside 3, were isolated from the roots of Polygonum cillinerve and their structures were established by spectroscopic methods. The biological activity indicated that compound 1 had the scavenging activity on 1,1-diphenyl-2- picrylhydrazyl (DPPH) radicals (the IC50 = 8.5 μmol/L), and compound 1-3 showed no activities against HL-60 and BGC-823 cells by MTT method in vitro.展开更多
The thermodynamic properties of dibenzofurans (DFs), xanthones (XTs) and an- thraquinones (AQs) with one and two positions substituted with hydroxyls in the ideal gas state at 298.15 K and 1.013×10~5 pa were calc...The thermodynamic properties of dibenzofurans (DFs), xanthones (XTs) and an- thraquinones (AQs) with one and two positions substituted with hydroxyls in the ideal gas state at 298.15 K and 1.013×10~5 pa were calculated at the B3LYP/6-311G~* level using Gaussian 03 program. The isodesmic reactions were designed to calculate the standard free energy of formation (Δ_fG^e). Three types of hydrogen bonds exist in the three kinds of chemicals and their bond energies were ascertained as 7-15, 15-23 and 49-58 kJ·mol^(-1) respectively by comparing the Δ_fG^e values. Electronic density topology analysis was applied to validate the strength of bond.展开更多
Chemical examination of an EtO Ac extract of cultured Aspergillus versicolor fungus from deep-sea sediments resulted in the isolation of four xanthones, eight anthraquinones and five alkaloids, including a new xanthon...Chemical examination of an EtO Ac extract of cultured Aspergillus versicolor fungus from deep-sea sediments resulted in the isolation of four xanthones, eight anthraquinones and five alkaloids, including a new xanthone, oxisterigmatocystin D(1) and a new alkaloid, aspergillusine A(13). High resolution electron impact mass spectrometry(HR-EI-MS), FT-IR spectroscopy, and NMR techniques were used to elucidate the structures of these compounds, and the absolute configuration of compound 1 was established by its NMR features and coupling constant. Furthermore, the biosynthesis pathway of these xanthones and anthraquinones were deduced, and their antioxidant activity and cytotoxicity in human cancer cell lines(HTC-8, Bel-7420, BGC-823, A549, and A2780) were evaluated. The trolox equivalent antioxidant capacity(TEAC) assay indicated most of the xanthones and anthraquinones possessing moderate antioxidant activities. The Nrf2-dependent luciferase reporter gene assay revealed that compounds 6, 7, 9, and 12 potentially activated the expression of Nrf2-regulated gene. In addition, compounds 5 and 11 showed weak cytotoxicity on A549 with the IC50 values of 25.97 and 25.60 μmol×L^(–1), respectively.展开更多
OBJECTIVE: To examine changes in the morphology and physiological functions of human proximal tubular epithelial cells (HK-2 cells) caused by total Dahuang (Radix Et Rhizoma Rhei Palmati) anthraquinones (TDA) and emod...OBJECTIVE: To examine changes in the morphology and physiological functions of human proximal tubular epithelial cells (HK-2 cells) caused by total Dahuang (Radix Et Rhizoma Rhei Palmati) anthraquinones (TDA) and emodin. METHODS: HK-2 cells were cultured on polycarbonate (PCF) membranes to form a complete monolayer of cells. A fluorescein isothiocyanate- dextran (FITC) permeability assay was conducted and secretion of γ-glutamyltranspeptidase (GGT), lactate dehydrogenase (LDH), N-acetyl-β-D-glucosaminidase (NAG) and kidney injury molecule 1 (KIM-1) was examined. The reabsorption of glucose and the excretion of para-aminohippuric acid (PAH) by HK-2 cells were also examined. The morphology of HK-2 cells was observed using optical microscopy and scanning electron microscopy. The cytoskeleton of HK-2 cells was observed under a fluorescence microscope. RESULTS: Compared with the results for the dimethyl sulfoxide group, treatment of cells with TDA and emodin showed statistically significant differences in the FITC leakage rate, the apical / basolateral ratio of LDH and GGT, and the secretion of GGT, LDH, NAG and KIM-1. At 64 μg/mL, TDA markedly inhibited blood glucose reabsorption and remarkably suppressed PAH excretion by HK-2 cells. Both TDA and emodin caused various degrees of damage to the morphology and cytoskeleton of HK-2 cells with the degree of damage correlating positively with the dosage of the tested substances.CONCLUSION: Both TDA and emodin caused damage to human renal proximal tubular epithelial cells at certain dosages. At the same dosage, TDA caused more severe damage than emodin to the HK-2 cells.展开更多
Objective To develop a quantitative method for simultaneously determining multi-components in Rhei Radix et Rhizoma using one chemical reference substance.Methods The contents of multi-components were calculated by th...Objective To develop a quantitative method for simultaneously determining multi-components in Rhei Radix et Rhizoma using one chemical reference substance.Methods The contents of multi-components were calculated by the UV relative correction factors(RCFs)of chrysophanol,physcion,and rhein to emodin.Results The values of RCFs at 274 nm for rhein,chrysophanol,and physcion to emodin were 0.712,0.674,and 1.051.The calibration curves were linear over the ranges of 0.02-4.08,0.02-4.12,0.07-12.92,and 0.02-3.68μg/mL for rhein,emodin, chrysophanol,and physcion,respectively.The contents of emodin in 18 samples were determined by the external standard method,and the contents of the other three anthraquinone aglycones were calculated according to their RCFs. Conclusion No significant difference is found in comparison with the classical method,indicating that the RCFs have high reliability within their linear ranges and could be used in quality control of Rhei Radix et Rhizoma.The quantitative analysis of multi-component with a single marker is especially suitable for herbal medicines containing unstable or hard to be purified components as quality control markers.展开更多
Eight new 9,10-anthraquinones(1-8)including three acetonide derivatives of 3-hydroxy-2-hydroxymethyl-9,10-anthraquinones(68)were isolated from an ethanol extract of the roots of Knoxia valeriamoides.On the basis of ch...Eight new 9,10-anthraquinones(1-8)including three acetonide derivatives of 3-hydroxy-2-hydroxymethyl-9,10-anthraquinones(68)were isolated from an ethanol extract of the roots of Knoxia valeriamoides.On the basis of chemical transformation reactions of the co-occurring 14 and 15 combined with HPLC-DAD-ESI-MS analysis of the extracts,the previously and newly isolated 2-methoxymethy-and 2-ethoxymethyl-9,10-anthraquinones(4,5,and 9-13),as well as the 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone acetonide derivatives(68),were shown to be solvolytic artifacts.In the in vitro assays,compound 4 was active to protect hepatocyte(WB-F344)damage.展开更多
文摘OBJECTIVE Senna and rhubarb are classified as stimulative laxatives,and known to have similar effective constituents,the anthraquinones.Being protected by theβ-glucoside bond,the anthraquinones can reach the intestines where they are degraded into complex metabolites by enzymes secreted from the intestinal microbiome.It is these complex metabolites that produce the laxative effects.Then the similarities and differences of action between the anthraquinones require further elucidation.METHODS Here,we studied metabolites of senna anthraquinones(SAQ),rhubarb anthraquinones(RAQ)and their chemical marker,sennoside A(SA),in a rat diarrhea model.In the in vitro biotransformation experiments,SAQ,RAQ and SA were incubated with rat fecal flora solution and the metabolites produced were analyzed using HPLC.In the in vivo studies,the same compounds were investigated for purgation induction,with measurement of histopathology and multiple aquaporins(Aqps)gene expression in six organs.RESULTS SAQ and RAQ had similar principal constituents but could be degraded into different metabolites.A similar profile of Aqps down-regulation for all compounds was seen in the colon,suggesting a similar mechanism of action for purgation.However,in the kidneys and livers of the diarrhea-rats,down-regulation of Aqps was found in the RAQ-rats whereas up-regulation of Aqps was seen in the SAQ-rats.Furthermore,the RAQ-rats showed lower aquaporin 2(Aqp2)protein expression in the kidneys,whilst the SA-rats and SAQ-rats had higher Aqp2 protein expression in the kidneys.This may have implications for side effects of SAQ or RAQ in patients with chronic kidney or liver diseases.CONCLUSION SAQ and RAQ showed similar laxative actions with a similar mechanism,they could display different actions in rat kidneys and livers.We suggest that the clinical usage of senna or rhubarb products should be clarified for patients having chronic kidney or liver diseases.
基金National Natural Science Foundation(81360524,81660701)Youth Fund of Guangxi University of Chinese Medicine(2019QN036)Project for Improving Basic Scientific Research Ability of Young and Middle-aged Teachers in Colleges and Universities of Guangxi(2019KY0341).
文摘[Objectives]To determine the content of five kinds of free anthraquinones in raw rhubarb and stewed rhubarb by HPLC,and compare their content difference,so as to reveal the change rule of material basis before and after processing of traditional Chinese medicine.[Methods]The content was determined by HPLC with Thermo BDS HYPERSII C18 column(4.6 mm×250 mm,5μm)as chromatographic column and methanol-0.1%phosphoric acid(85∶15)aqueous solution as mobile phase;the detection wavelength was 256 nm,the flow rate was 1.0 mL/min,the column temperature was 30℃,and the injection volume was 10μL.[Results]Aloe-emodin,rhein,emodin,chrysophanol and emodin methyl ether showed a good linear relationship in the linear range of 0.0207-0.414(R2=0.9999),0.1721-3.442(R2=0.9996),0.0203-0.406(R2=0.9999),0.148-2.96(R2=0.9998)and 0.164-3.28(R2=0.9993),respectively;the content of aloe-emodin decreased by about 8.26%,and rhein decreased by about 9.21%;the content of emodin increased by about 16.44%,chrysophanol increased by about 16.12%,and emodin methyl ether increased by about 20.01%,indicating that the processing technology had different effects on the components of rhubarb.[Conclusions]The content of five free anthraquinones in rhubarb was affected to different degrees after processing,and this method could be used as a quality control method for rhubarb and its different processed products.
文摘Acid-catalytic 1,3-butadiene condensation with para-quinones followed by the obtained product oxidation may be performed in one stage as one-pot process, if assisted by the aqueous solutions of Mo-V-P heteropoly acids with a composition of HaPzMoyVxOb. 1,4-naphthoquinone (NQ) condensation with 1,3-butadiene in HPA solutions (brutto-composition H15P4Mo18V7O89 and H17P3Mo16V10O89) in the presence of hydrophylic organic solvents (acetone, 1,4-dioxane) provides 70% yield of 9,10-anthraquinone (AQ) containing no less than 90% AQ. In the same conditions reaction NQ with substituted 1,3-butadienes in the presence of the aqueous H17P3Mo16V10O89 (HPA-10) solution allows to prepare substituted AQ with yield up to 90% and purity up to 99%. The catalysts are regenerated by oxygen in separate stage and are reused.
基金the National Natural Science Foundation of China (Grant Nos.: 81673394 and 82073811)the Fundamental Research Funds for the Central Universities (Grant No.: 2042020kf1010)the Large-scale Instrument and Equipment Sharing Foundation of Wuhan University (Grant No.: LF20170838)
文摘Natural long-chain alkanol and alkyl carboxylic acid were used to prepare novel hydrophobic deep eutectic solvents(HDESs).These HDESs are liquid at room temperature and have low viscosity(<12.26 mPa·s),low polarity(lower than that of methanol,ChCl-based deep eutectic solvents and other reported HDESs),and low density(<0.928 g/mL).A simple one-pot method based on a novel HDES-water two-phase extraction system was constructed for the extraction of weak-polarity bioactive components,anthraquinones,from Rhei Radix et Rhizoma.This HDES-based new extraction method does not consume hazardous organic solvents and can obtain a total anthraquinone yield of 21.52 mg/g,which is close to that obtained by the Chinese pharmacopoeia method(21.22 mg/g)and considerably higher than those by other reported HDESs-based extraction methods(14.20-20.09 mg/g,p<0.01).The high extraction yield can be mainly attributed to the severe destruction of the RRR cell walls by the extraction system and the excellent dissolving ability of novel HDESs for anthraquinones.
文摘Three new anthraquinones, emodin-8-β-D-(2″-O-coumarate)glucoside 1, emodin-8-β- D-(6′-O-acetyl)glucoside 2 and physicon-8-β-D-(6′-O-acetyl)glucoside 3, were isolated from the roots of Polygonum cillinerve and their structures were established by spectroscopic methods. The biological activity indicated that compound 1 had the scavenging activity on 1,1-diphenyl-2- picrylhydrazyl (DPPH) radicals (the IC50 = 8.5 μmol/L), and compound 1-3 showed no activities against HL-60 and BGC-823 cells by MTT method in vitro.
文摘The thermodynamic properties of dibenzofurans (DFs), xanthones (XTs) and an- thraquinones (AQs) with one and two positions substituted with hydroxyls in the ideal gas state at 298.15 K and 1.013×10~5 pa were calculated at the B3LYP/6-311G~* level using Gaussian 03 program. The isodesmic reactions were designed to calculate the standard free energy of formation (Δ_fG^e). Three types of hydrogen bonds exist in the three kinds of chemicals and their bond energies were ascertained as 7-15, 15-23 and 49-58 kJ·mol^(-1) respectively by comparing the Δ_fG^e values. Electronic density topology analysis was applied to validate the strength of bond.
基金supported by the Knowledge Innovation Program of Shenzhen(JCYJ20160428181415376 andJCYJ20150529153646078)
文摘Chemical examination of an EtO Ac extract of cultured Aspergillus versicolor fungus from deep-sea sediments resulted in the isolation of four xanthones, eight anthraquinones and five alkaloids, including a new xanthone, oxisterigmatocystin D(1) and a new alkaloid, aspergillusine A(13). High resolution electron impact mass spectrometry(HR-EI-MS), FT-IR spectroscopy, and NMR techniques were used to elucidate the structures of these compounds, and the absolute configuration of compound 1 was established by its NMR features and coupling constant. Furthermore, the biosynthesis pathway of these xanthones and anthraquinones were deduced, and their antioxidant activity and cytotoxicity in human cancer cell lines(HTC-8, Bel-7420, BGC-823, A549, and A2780) were evaluated. The trolox equivalent antioxidant capacity(TEAC) assay indicated most of the xanthones and anthraquinones possessing moderate antioxidant activities. The Nrf2-dependent luciferase reporter gene assay revealed that compounds 6, 7, 9, and 12 potentially activated the expression of Nrf2-regulated gene. In addition, compounds 5 and 11 showed weak cytotoxicity on A549 with the IC50 values of 25.97 and 25.60 μmol×L^(–1), respectively.
基金Supported by the Central Public Welfare Research Institutes Foundation-funded Project:A new research of renal toxicity early detection of Chinese medicine(ZZ0908035)Establishment of HK-2 cell monolayer model of human proximal renal tubular epithelial cells(ZXKT15022)+1 种基金Bioactivity based quality control for Chinese herbal medicine using Rhubarb as model system(GH2017-01-02)Natural Science Foundation-funded Project:Study on the bacterial endotoxin detection method of traditional Chinese medicine injections(90709043)
文摘OBJECTIVE: To examine changes in the morphology and physiological functions of human proximal tubular epithelial cells (HK-2 cells) caused by total Dahuang (Radix Et Rhizoma Rhei Palmati) anthraquinones (TDA) and emodin. METHODS: HK-2 cells were cultured on polycarbonate (PCF) membranes to form a complete monolayer of cells. A fluorescein isothiocyanate- dextran (FITC) permeability assay was conducted and secretion of γ-glutamyltranspeptidase (GGT), lactate dehydrogenase (LDH), N-acetyl-β-D-glucosaminidase (NAG) and kidney injury molecule 1 (KIM-1) was examined. The reabsorption of glucose and the excretion of para-aminohippuric acid (PAH) by HK-2 cells were also examined. The morphology of HK-2 cells was observed using optical microscopy and scanning electron microscopy. The cytoskeleton of HK-2 cells was observed under a fluorescence microscope. RESULTS: Compared with the results for the dimethyl sulfoxide group, treatment of cells with TDA and emodin showed statistically significant differences in the FITC leakage rate, the apical / basolateral ratio of LDH and GGT, and the secretion of GGT, LDH, NAG and KIM-1. At 64 μg/mL, TDA markedly inhibited blood glucose reabsorption and remarkably suppressed PAH excretion by HK-2 cells. Both TDA and emodin caused various degrees of damage to the morphology and cytoskeleton of HK-2 cells with the degree of damage correlating positively with the dosage of the tested substances.CONCLUSION: Both TDA and emodin caused damage to human renal proximal tubular epithelial cells at certain dosages. At the same dosage, TDA caused more severe damage than emodin to the HK-2 cells.
文摘Objective To develop a quantitative method for simultaneously determining multi-components in Rhei Radix et Rhizoma using one chemical reference substance.Methods The contents of multi-components were calculated by the UV relative correction factors(RCFs)of chrysophanol,physcion,and rhein to emodin.Results The values of RCFs at 274 nm for rhein,chrysophanol,and physcion to emodin were 0.712,0.674,and 1.051.The calibration curves were linear over the ranges of 0.02-4.08,0.02-4.12,0.07-12.92,and 0.02-3.68μg/mL for rhein,emodin, chrysophanol,and physcion,respectively.The contents of emodin in 18 samples were determined by the external standard method,and the contents of the other three anthraquinone aglycones were calculated according to their RCFs. Conclusion No significant difference is found in comparison with the classical method,indicating that the RCFs have high reliability within their linear ranges and could be used in quality control of Rhei Radix et Rhizoma.The quantitative analysis of multi-component with a single marker is especially suitable for herbal medicines containing unstable or hard to be purified components as quality control markers.
基金Financial support from the National Natural Sciences Foundation of China(NNSFC,grant Nos.30825044 and 20932007)the National Science and Technology Project of China(No.2009ZX09311-004)is acknowledged.
文摘Eight new 9,10-anthraquinones(1-8)including three acetonide derivatives of 3-hydroxy-2-hydroxymethyl-9,10-anthraquinones(68)were isolated from an ethanol extract of the roots of Knoxia valeriamoides.On the basis of chemical transformation reactions of the co-occurring 14 and 15 combined with HPLC-DAD-ESI-MS analysis of the extracts,the previously and newly isolated 2-methoxymethy-and 2-ethoxymethyl-9,10-anthraquinones(4,5,and 9-13),as well as the 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone acetonide derivatives(68),were shown to be solvolytic artifacts.In the in vitro assays,compound 4 was active to protect hepatocyte(WB-F344)damage.
