[Objectives]To study the inhibitory activity of two flavonoid glycosides isolated from Chlorophytum comosum Laxum R.Br on human nasopharyngeal carcinoma(NPC)cell line 5-8F in vitro and its mechanism.[Methods]The flavo...[Objectives]To study the inhibitory activity of two flavonoid glycosides isolated from Chlorophytum comosum Laxum R.Br on human nasopharyngeal carcinoma(NPC)cell line 5-8F in vitro and its mechanism.[Methods]The flavonoid glycosides were isolated and purified from the ethanol alcoholic extract of the roots of Liliaceae plant Chlorophytum comosum by silica gel column chromatography,macroporous resin column chromatography,Sephadex LH-20,and reverse column chromatography(ODS).The inhibitory activity of flavonoid glycosides on human nasopharyngeal carcinoma cells was analyzed by CCK-8 method,and the potential mechanism was preliminarily analyzed by molecular docking.[Results]Two flavonoid glycosides were identified as isovitexin 2″-0-rhamnoside and 7-2″-di-O-β-glucopyranosylisovitexin.Two flavonoid glycosides showed promising inhibitory effect on human nasopharyngeal carcinoma cell line 5-8F,with IC_(50) values of 24.8 and 27.5μmol/L,respectively.Molecular docking results showed that the potential targets of two flavonoid glycosides include CyclinD1,Bcl-2β-Catenin,ILK,TGF-β,in addition,two glycosides showed higher predicted binding affinity towards CyclinD1,which verifies the cytotoxicity of the two compounds on human nasopharyngeal carcinoma cell line 5-8F in vitro.[Conclusions]Two flavonoid glycosides are the active molecules in Chlorophytum comosum that can inhibit the proliferation of human nasopharyngeal carcinoma cells,and have the potential to be used in the research and development of anti nasopharyngeal carcinoma drugs.展开更多
A first total synthesis of isoliquiritin was accomplished starting from p-hydroxy- benzaldehyde and 2,4-dihydroxyacetylphenone. The key step is condensation reaction. In synthetic process need not protect the hydroxy ...A first total synthesis of isoliquiritin was accomplished starting from p-hydroxy- benzaldehyde and 2,4-dihydroxyacetylphenone. The key step is condensation reaction. In synthetic process need not protect the hydroxy group of reacting substance.展开更多
The inhibition of a-glucosidase and glucose-6-phosphatase,two enzymes involved in the carbohydrate metabolism,is an important target to control glycaemia on individuals with type 2 diabetes.In this work we report for ...The inhibition of a-glucosidase and glucose-6-phosphatase,two enzymes involved in the carbohydrate metabolism,is an important target to control glycaemia on individuals with type 2 diabetes.In this work we report for the first time the inhibition of both enzymes by the antihyperglycemic n-butanol extract from Genista tenera(Fabaceae).This extract decreased a-glucosidase and glucose-6-phosphatase activities to 0.97 and 80.25%,respectively,being more effective than acarbose,and phlorizin,the positive controls,which reduced enzymes activities only to 17.39 and 96.06%.Once inflammation and oxidative stress are related to diabetic impairments,the anti-inflammatory activity of the extract was also evaluated,through its inhibitory activity over COX-1 enzyme(47.5%inhibition).Moreover,after induction of oxidative stress by UV radiation,the viability of irradiated rat liver hepatoma cells exposed to the extract was significantly higher(67.82%)than that promoted by ascorbic acid,the positive control(45.05%).In addition,the stability of the extract under gastrointestinal conditions was evaluated by HPLC–DAD-ESI–MS/MS.Flavonoid diglycosides were identified as the main constituents of the extract,and no alterations in the chemical composition nor in the antioxidant activity were observed after in vitro digestion with artificial gastric and pancreatic juices.展开更多
Four prenylated flavonoids compounds 1-4,named sinopodophyllines A-D,and a flavonoid glycoside(compound 13),sinopodophylliside A,together with 19 known compounds(compounds 5-12 and 14-24) were isolated from the fruits...Four prenylated flavonoids compounds 1-4,named sinopodophyllines A-D,and a flavonoid glycoside(compound 13),sinopodophylliside A,together with 19 known compounds(compounds 5-12 and 14-24) were isolated from the fruits of Sinopodophyllum hexandrum.The structures of new compounds were elucidated by extensive spectroscopic analysis,including HRESIMS,1D and 2D NMR.Compounds 1-6,9-11,and 14-17 were tested for their cytotoxicity against human breast-cancer T47 D,MCF-7 and MDA-MB-231 cells in vitro,and compounds 2,5,6,10 and 11 showed significant cytotoxicity(IC50 values < 10 μmol·L^(-1))against T47 D cells.展开更多
Four new phenolic glycosides,including two flavonoid glycosides(1 and 2) and two lignan glycosides(3 and 4),were isolated from the traditional Chinese medicine formula,Baoyuan decoction.Their structures were establish...Four new phenolic glycosides,including two flavonoid glycosides(1 and 2) and two lignan glycosides(3 and 4),were isolated from the traditional Chinese medicine formula,Baoyuan decoction.Their structures were established by detailed analysis of the NMR and HR-ESI-MS spectroscopic data and their absolute configurations were determined by the experimental electronic circular dichroism data as well as chemical methods.Furthermore,the sources of the four new compounds were determined by the UPLC-Qtrap-MS method,which proved that 1 and 2 are originated from Glycyrrhiza uralensis,and 3 and4 are from Cinnamomum cassia.展开更多
Objective To explore the investigation method of complicated and profound traditional Chinese herbal medicine,the potential action mechanisms of flavonoids from Scutellaria baicalensis were studied by docking calculat...Objective To explore the investigation method of complicated and profound traditional Chinese herbal medicine,the potential action mechanisms of flavonoids from Scutellaria baicalensis were studied by docking calculation.Methods In total,eight flavonoids(aglycones and their glicosides) from S.baicalensis were selected as ligands.The crystalline structures of targets related to common diseases were used as the receptors for calculation.The calculations were conducted with Schrdinger software package.The grading standard of selectivity was developed according to G-score between ligands and receptors.Results Twenty-six pharmacologic actions have been reported.Among all effects in literature,nine of them can be deduced from the docking calculation of aglycone.From glycosides with grade ++,25 reported effects can be estimated by calculation.Apparently,the target selectivity of aglycones and their glycosides are different form the virtual evaluation.The virtual evaluation results of glycosides were closer to the reported effects.Conclusion Our proposed virtual evaluation method seems an effective way to investigate the complicated system of traditional Chinese herbal medicine.It suggests that aglycones may be effective as the form of glucoside in vivo,and metabolism is a very important factor for virtual evaluation.展开更多
基金Supported by Youth Fund Project of Zhaoqing University(QZ202235)Zhaoqing Science and Technology Plan Project(2022040311011).
文摘[Objectives]To study the inhibitory activity of two flavonoid glycosides isolated from Chlorophytum comosum Laxum R.Br on human nasopharyngeal carcinoma(NPC)cell line 5-8F in vitro and its mechanism.[Methods]The flavonoid glycosides were isolated and purified from the ethanol alcoholic extract of the roots of Liliaceae plant Chlorophytum comosum by silica gel column chromatography,macroporous resin column chromatography,Sephadex LH-20,and reverse column chromatography(ODS).The inhibitory activity of flavonoid glycosides on human nasopharyngeal carcinoma cells was analyzed by CCK-8 method,and the potential mechanism was preliminarily analyzed by molecular docking.[Results]Two flavonoid glycosides were identified as isovitexin 2″-0-rhamnoside and 7-2″-di-O-β-glucopyranosylisovitexin.Two flavonoid glycosides showed promising inhibitory effect on human nasopharyngeal carcinoma cell line 5-8F,with IC_(50) values of 24.8 and 27.5μmol/L,respectively.Molecular docking results showed that the potential targets of two flavonoid glycosides include CyclinD1,Bcl-2β-Catenin,ILK,TGF-β,in addition,two glycosides showed higher predicted binding affinity towards CyclinD1,which verifies the cytotoxicity of the two compounds on human nasopharyngeal carcinoma cell line 5-8F in vitro.[Conclusions]Two flavonoid glycosides are the active molecules in Chlorophytum comosum that can inhibit the proliferation of human nasopharyngeal carcinoma cells,and have the potential to be used in the research and development of anti nasopharyngeal carcinoma drugs.
文摘A first total synthesis of isoliquiritin was accomplished starting from p-hydroxy- benzaldehyde and 2,4-dihydroxyacetylphenone. The key step is condensation reaction. In synthetic process need not protect the hydroxy group of reacting substance.
基金The authors gratefully acknowledge Fundacāo para a Ciência e a Tecnologia for financial support of the projects PTDC/QUI/67165/2006 and PEst-OE/QUI/UI0612/2013The authors also thank the European Commission for approval of the INOVAFUNAGEING commitment and the support of the project“PERsonalised ICT supported Service for Independent Living and Active Ageing”,FP7-ICT-2013-10,Project Nr.610359,2013-2016The collaboration of the staff from the Herbarium of Jardim Botanico da Madeira,for providing plant material,is also acknowledged.
文摘The inhibition of a-glucosidase and glucose-6-phosphatase,two enzymes involved in the carbohydrate metabolism,is an important target to control glycaemia on individuals with type 2 diabetes.In this work we report for the first time the inhibition of both enzymes by the antihyperglycemic n-butanol extract from Genista tenera(Fabaceae).This extract decreased a-glucosidase and glucose-6-phosphatase activities to 0.97 and 80.25%,respectively,being more effective than acarbose,and phlorizin,the positive controls,which reduced enzymes activities only to 17.39 and 96.06%.Once inflammation and oxidative stress are related to diabetic impairments,the anti-inflammatory activity of the extract was also evaluated,through its inhibitory activity over COX-1 enzyme(47.5%inhibition).Moreover,after induction of oxidative stress by UV radiation,the viability of irradiated rat liver hepatoma cells exposed to the extract was significantly higher(67.82%)than that promoted by ascorbic acid,the positive control(45.05%).In addition,the stability of the extract under gastrointestinal conditions was evaluated by HPLC–DAD-ESI–MS/MS.Flavonoid diglycosides were identified as the main constituents of the extract,and no alterations in the chemical composition nor in the antioxidant activity were observed after in vitro digestion with artificial gastric and pancreatic juices.
基金supported by Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine(No.2010JZ-W-01)Ministry of Education,PRC,and National Key Technology R&D Program“New Drug Innovation”of China(Nos.2009ZX09308-004,2013ZX09103002-006)
文摘Four prenylated flavonoids compounds 1-4,named sinopodophyllines A-D,and a flavonoid glycoside(compound 13),sinopodophylliside A,together with 19 known compounds(compounds 5-12 and 14-24) were isolated from the fruits of Sinopodophyllum hexandrum.The structures of new compounds were elucidated by extensive spectroscopic analysis,including HRESIMS,1D and 2D NMR.Compounds 1-6,9-11,and 14-17 were tested for their cytotoxicity against human breast-cancer T47 D,MCF-7 and MDA-MB-231 cells in vitro,and compounds 2,5,6,10 and 11 showed significant cytotoxicity(IC50 values < 10 μmol·L^(-1))against T47 D cells.
基金financially supported by the National Natural Sciences Foundation of China(Nos.81222051 and 81530097)the National Key Technology R&D Program“New Drug Innovation”of China(No.2012ZX09301002-002-002)
文摘Four new phenolic glycosides,including two flavonoid glycosides(1 and 2) and two lignan glycosides(3 and 4),were isolated from the traditional Chinese medicine formula,Baoyuan decoction.Their structures were established by detailed analysis of the NMR and HR-ESI-MS spectroscopic data and their absolute configurations were determined by the experimental electronic circular dichroism data as well as chemical methods.Furthermore,the sources of the four new compounds were determined by the UPLC-Qtrap-MS method,which proved that 1 and 2 are originated from Glycyrrhiza uralensis,and 3 and4 are from Cinnamomum cassia.
基金Ministry of Science and Technology of the PR China (No:2007BAI41B01)Tianjin Municipal Science and Technology Commission (No:07TCZDJC05300)
文摘Objective To explore the investigation method of complicated and profound traditional Chinese herbal medicine,the potential action mechanisms of flavonoids from Scutellaria baicalensis were studied by docking calculation.Methods In total,eight flavonoids(aglycones and their glicosides) from S.baicalensis were selected as ligands.The crystalline structures of targets related to common diseases were used as the receptors for calculation.The calculations were conducted with Schrdinger software package.The grading standard of selectivity was developed according to G-score between ligands and receptors.Results Twenty-six pharmacologic actions have been reported.Among all effects in literature,nine of them can be deduced from the docking calculation of aglycone.From glycosides with grade ++,25 reported effects can be estimated by calculation.Apparently,the target selectivity of aglycones and their glycosides are different form the virtual evaluation.The virtual evaluation results of glycosides were closer to the reported effects.Conclusion Our proposed virtual evaluation method seems an effective way to investigate the complicated system of traditional Chinese herbal medicine.It suggests that aglycones may be effective as the form of glucoside in vivo,and metabolism is a very important factor for virtual evaluation.