Ten novel xanthones,garpedunxanthones A-G(1-5,6a/6b,7a/7b) and nujiangxanthone Q(8),along with sixteen known analogs(9-24),were isolated from Garcinia pedunculata and G.nujiangensis.Their structures were elucidated th...Ten novel xanthones,garpedunxanthones A-G(1-5,6a/6b,7a/7b) and nujiangxanthone Q(8),along with sixteen known analogs(9-24),were isolated from Garcinia pedunculata and G.nujiangensis.Their structures were elucidated through high-resolution electrospray ionization mass spectrometry(HR-ESI-MS) data,comprehensive nuclear magnetic resonance(NMR) spectroscopic analyses,and electronic circular dichroism(ECD) calculations.All compounds without cytotoxicity were assessed for anti-inflammatory properties by measuring the inhibition of nitric oxide(NO) production in lipopolysaccharide(LPS)-induced RAW264.7cells.Structure-activity relationships are also discussed.Compounds 7b,19,and 21 exhibited significant anti-inflammatory activity with IC_(50) values of 16.44±0.69,14.28±0.78,and 10.67±3.28 μmol·L^(-1),respectively.Enzyme-linked immunosorbent assay(ELISA) demonstrated that compounds 7b,19,and 21 inhibited the expression of pro-inflammatory cytokines TNF-α and IL-6 in a dose-dependent manner.The inhibitory effect of compo und 21 on IL-6 at 20 μmol·L^(-1)was comparable to that of the positive control.In network pharmacology studies,potential targets of compounds and inflammation were identified from PharmMapper and GeneCards databases.Gene Ontology(GO) and Kyoto Encyclopedia of Genes and Genomes(KEGG) enrichment analysis revealed that the overlapped targets were intricately associated with major pathogenic processes linked to inflammation,including positive regulation of mitogen-activated protein kinase(MAPK) cascade,protein kinase activity,NO synthase regulator activity,MAPK signaling pathway,and EGFR tyrosine kinase inhibitor resistance.展开更多
Eight known compounds were isolated from the whole plants ofArenaria serpyllifolia L. by solvent fractionation and subsequent separations with silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC chromatography. ...Eight known compounds were isolated from the whole plants ofArenaria serpyllifolia L. by solvent fractionation and subsequent separations with silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC chromatography. Their structures were determined by spectroscopic analysis and identified as quercetin （1）, quercetin 7-O-α-L-rhamnoside （2）, quercetin 3-O-α-L- rhamnoside （3）, 3-O-methyl quercetin （4）, 1,5-dihydroxyxanthone （5）, 1,5-dihydroxyxanthone-6-O-β-D-glucoside （6）, 5-hydroxy- l-methoxyxanthone （7） and 6-deoxyisojacareubin （8）. All these compounds were isolated from this title plant for the first time, and compounds 5-8 were obtained from genus Arenaria for the first time.展开更多
From the CHCl3 part of Swertia decora Franch., a traditional medicinal herb of China, two new xanthones, swertiadecoraxanthone-I and swertiadecoraxanthone-II along with four known compounds have been isolated and iden...From the CHCl3 part of Swertia decora Franch., a traditional medicinal herb of China, two new xanthones, swertiadecoraxanthone-I and swertiadecoraxanthone-II along with four known compounds have been isolated and identified on the basis of spectral analysis and chemical evidence.展开更多
Two novel xanthones, 1,6-dihydroxy-4,5-dimethoxyxanthone （1） and 1,5,6-trihydroxy-7,8-di（3-methyl-2-butenyl）-6＇,6＇-dimethylpyrano（2＇,3＇：3,4）xanthone （2） were isolated from the bark of Garcinia xanthochymu...Two novel xanthones, 1,6-dihydroxy-4,5-dimethoxyxanthone （1） and 1,5,6-trihydroxy-7,8-di（3-methyl-2-butenyl）-6＇,6＇-dimethylpyrano（2＇,3＇：3,4）xanthone （2） were isolated from the bark of Garcinia xanthochymus by normal phase and reverse phase silica gel column chromatography. Their structures were elucidated by spectroscopic methods, especially 2D-NMR techniques.展开更多
Chemical examination of an EtOAc 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...Chemical examination of an EtOAc 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 ICs0 values of 25.97 and 25.60 gmol·L^-1, respectively.展开更多
AIM:To investigate the growth inhibitory mechanism of four caged xanthones from Garcinia hanburyi in cholangiocarcinoma(CCA) KKU-100 and KKU-M156 cells.METHODS:Four caged xanthones,selected on the basis of their antic...AIM:To investigate the growth inhibitory mechanism of four caged xanthones from Garcinia hanburyi in cholangiocarcinoma(CCA) KKU-100 and KKU-M156 cells.METHODS:Four caged xanthones,selected on the basis of their anticancer potency and chemical structure diversities(i.e.isomorellin,isomorellinol,forbesione and gambogic acid) were used in this study.Growth inhibition of these caged xanthones was determined using the sulforhodamine B assay.Induction of apoptosis was assessed by observing cell morphology,ethidium bromide and acridine orange staining and DNA fragmentation assay.Levels of apoptotic-related gene and protein expressions were determined by a real-time reverse transcriptase polymerase chain reaction and Western blotting analysis,respectively.RESULTS:The compounds were found to inhibit growth of both cell lines in a dose-dependent manner and also showed selective cytotoxicity against the cancer cells when compared with normal peripheral blood mononuclear cells.Growth suppression by these compounds was due to apoptosis,as evidenced by the cell morphological changes,chromatin condensation,nuclear fragmentation,and DNA ladder formation.At the molecular level,these compounds induced down-regulation of Bcl-2 and survivin proteins with up-regulation of Bax and apoptosisinducing factor proteins,leading to the activation of caspase-9 and-3 and DNA fragmentation.The functional group variations did not appear to affect the anticancer activity with regard to the two CCA cell lines;however,at a mechanistic level,isomorellinol exhibited the highest potency in increasing the Bax/Bcl-2 protein expression ratio(120 and 41.4 for KKU-100 and KKU-M156,respectively) and in decreasing survivin protein expression(0.01 fold as compared to control cells in both cell lines).Other activities at the molecular level indicate that functional groups on the prenyl side chain may be important.CONCLUSION:Our findings for the first time demonstrate that four caged xanthones induce apoptosis in CCA cells which is mediated through a mitochondriadependent signaling pathway.展开更多
Three new xanthones, 3, 6-dihydroxy-1, 2, 7-trimethoxyxanthone 1, 1, 3, 6-trihydroxy-2, 7, 8-trimethoxyxanthone 2, and 3, 6-dihydroxy-1, 2, 7, 8-tetramethoxyxanthone 3, were isolated from the roots of Polygala crotala...Three new xanthones, 3, 6-dihydroxy-1, 2, 7-trimethoxyxanthone 1, 1, 3, 6-trihydroxy-2, 7, 8-trimethoxyxanthone 2, and 3, 6-dihydroxy-1, 2, 7, 8-tetramethoxyxanthone 3, were isolated from the roots of Polygala crotalarioides. Their structures were elucidated by spectral and chemical methods.展开更多
A capillary electrophoresis (CE) method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was systematically opt...A capillary electrophoresis (CE) method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was systematically optimized with respect to pH, concentration of running buffers, addition of sulfated b-CD, applied voltage and column temperature. Baseline separation was achieved for the nine xanthones in less than 15 minutes using a background electrolyte consisting of 200 mmol/L borate (pH 9.5) and 10 mmol/L sulfated b-CD.展开更多
The gas phase thermodynamic properties of 135 polychlorinated xanthones(PCXTs)are calculated using a combination of quantum mechanical computations performed with the Gaussian 03 program at the B3LYP/6-311G**level.It ...The gas phase thermodynamic properties of 135 polychlorinated xanthones(PCXTs)are calculated using a combination of quantum mechanical computations performed with the Gaussian 03 program at the B3LYP/6-311G**level.It is found that the chlorine substitution pattern strongly influences the thermodynamic properties of the compounds.The thermodynamic properties of congeners with the same number of chlorines also depend on the chlorine substitution pattern,especially for ortho-substituted congeners.PCXT congeners with one phenyl ring fully chlorinated are found to be the least stable among the analogues.The effect of the chlorine substitution pattern is quantitatively studied by considering the number and position of Cl atom substitution(NPCS).The results show that the NPCS model may be used to predict the thermodynamic properties for all 135 PCXT congeners. In addition,the values of molar heat capacities at constant pressure(cp,m)from 200 to 1000 K for PCXT congeners are calculated,and the temperature dependence relation of this parameter is obtained using the least-squares method.展开更多
Plants have so much to offer as far as the discovery of new bioactive molecules is concerned.Among the several classes of phytochemicals,xanthones offer greater structural diversity and pharmacological value.They are ...Plants have so much to offer as far as the discovery of new bioactive molecules is concerned.Among the several classes of phytochemicals,xanthones offer greater structural diversity and pharmacological value.They are variable but definitely antioxidant in nature.Thus they are attractive targets for natural product and medicinal chemists.Xanthones and their glycosides possess broad spectrum interesting biological activities,such as cytotoxic,anti-inflammatory,antioxidant,anti-bacterial,neuroprotective,anti-HIV,enzyme inhibition,and hypoglycemic.The radical scavenging ability of these molecules accounts for most of their added therapeutic values.This paper intended to serve as a guide for future endeavors in quest for these molecules.Structure-Activity Relationship(SAR)and mechanism of action is given for better understanding of their role as pharmacological agents.The most recent advances in the isolation of bioactive xanthones and their glycosides were presented here.This paper will assist in directed approaches towards the discovery of analogues of xanthones.展开更多
A microemulsion electrokinetic chromatography method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was syste...A microemulsion electrokinetic chromatography method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was systematically optimized with respect to pH, composition of microemulsion, addition of cyclodextrins, applied voltage and column temperature. Baseline separation was successfully achieved for the nine xanthones, which was also compared with that by micellar electrokinetic chromatography.展开更多
The present study was designed to investigate the chemical constituents of the roots of Cudrania fruticosa Wight. Compounds were isolated by various column chromatographic methods including silica gel, polyamide, seph...The present study was designed to investigate the chemical constituents of the roots of Cudrania fruticosa Wight. Compounds were isolated by various column chromatographic methods including silica gel, polyamide, sephadex LH-20, and semi-preparative HPLC. Their structures were elucidated by a combination of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. Two new xanthones, Cudraxanthone T and U(1-2), along with four known compounds(3-6) were isolated from the roots of Cudrania fruticosa Wight.展开更多
Introduction Xanthones are secondary metabolites commonly occurring in a few higher plant families, fungi and lichen. Their high taxonomic value in such families and their pharmacological properties, including in vitr...Introduction Xanthones are secondary metabolites commonly occurring in a few higher plant families, fungi and lichen. Their high taxonomic value in such families and their pharmacological properties, including in vitro cytotoxicity, in vivo antitumour activity, antifungal, antibacterial, antiinflammatory properties and aldose reductase inhibitory activity have provoked great interest. The discovery of the antidiabetic activity of some axnthones＇ from Swertiaceae has prompted us to undertake a more broadly search for novel xanthones from plants of Polygalaceae. The phytochemical investigation has not been performed on this plant up to now. Herein we report the isolation and structure elucidation of two new xanthones （ compounds 1 and 2 ） and three known xanthones （compound 3, 4 and 5 ）.展开更多
Two new xanthones, 1, 6, 8-trihydroxy-2, 3-methylenedioxyxanthone 1 and 1, 4-di- hydroxy-6, 7-methylenedioxyxanthone 2, were isolated from the roots of Polygala crotalarioides. Their structures were elucidated by spec...Two new xanthones, 1, 6, 8-trihydroxy-2, 3-methylenedioxyxanthone 1 and 1, 4-di- hydroxy-6, 7-methylenedioxyxanthone 2, were isolated from the roots of Polygala crotalarioides. Their structures were elucidated by spectroscopic and chemical methods.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...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 （△fG^θ）. 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·mo1^-1 respectively by comparing the △fG^θ values. Electronic density topology analysis was applied to validate the strength of bond.展开更多
Thirteen xanthones were isolated from L.rotatum,which were established as l,8-dihydroxy-3,4,5-trimethoxyxanthone(1);l-hydroxy-3异,8-trimethoxyxanthone(2);8-hydroxy-l,3?5-trimethoxyxaiithone(3);l-hydroxy-3,4,5-trimetho...Thirteen xanthones were isolated from L.rotatum,which were established as l,8-dihydroxy-3,4,5-trimethoxyxanthone(1);l-hydroxy-3异,8-trimethoxyxanthone(2);8-hydroxy-l,3?5-trimethoxyxaiithone(3);l-hydroxy-3,4,5-trimethoxyxanthone(4);l-hydroxy-3,5,8-trimethoxyxanthone(5);l,4,8-trihydroxy-5,6-dimethoxyxanthone(6);l,3,8-trihydroxy-4,7-dimethoxyxanthone(;7)l,8-dihydroxy-3,7-dimethoxyxanthone(8);l-hydroxy-3,5-dimethoxyxanthone(9);l-hydroxy-2,3,4,5-tetramethoxyxanthone(;10)l-hydroxy-2,3,4,7-tetramethoxyxanthone(11);l,7-dihydroxy-3,8-dimethoxyxanthone(12);rel-l,3,5,8-tetrahydroxy-2,4,6,7-tetrahydroxanthen-9-one(13).Compounds 4,6,7,9,10,11,12 and 13 are reported for the first time from Lomatogonium.Furthermore,the activity of xanthones was assessed.展开更多
Metabolism study has been carried out on 1-hydroxy-2,3,5-trimethoxyxanthone （HM-1） and 1-hydroxy-2,3,4,7- tetramethoxyxanthone （HM-2）, which are two biologically active ingredients isolated from the Tibetan herb, ...Metabolism study has been carried out on 1-hydroxy-2,3,5-trimethoxyxanthone （HM-1） and 1-hydroxy-2,3,4,7- tetramethoxyxanthone （HM-2）, which are two biologically active ingredients isolated from the Tibetan herb, Halenia elliptica D. Don., in rat liver microsomes in vitro. A method of high performance liquid chromatography coupled to ion trap time-of-flight mass spectrometry （LCMSn-ESI-IT-TOF） was applied to analyze metabolites of HM-1 and HM-2 on line, and five metabolites were identified containing 1,5-dihydroxy-2,3-dimethoxyxanthone （HM-5）, 1,7-dihydroxy-2,3,4-trimethoxyxanthone （HM-9）, 1,4, 7- trihydroxy-2,3-dimethoxyxanthone （HM-10）, 1,4-dihydroxy-2,3,7-trimethoxyxanthone （HM-11） and 1,2-dilaydroxy-3,4,7- trimethoxyxanthone （HM-12）. Among these metabolites, HM-9, HM-11, and HM-12 were isomers mutually. The results indicated that HM-1 and HM-2 occurred Phase I metabolic reaction of demethylation in rat microsomes in vitro.展开更多
In order to study the relationship between biological and pharmacological activities with their structures, a series of tri- and tetra-oxygenated xanthones including 1-hydroxyl-2,3,4,7- tetramethoxy xanthone 1, 1-hydr...In order to study the relationship between biological and pharmacological activities with their structures, a series of tri- and tetra-oxygenated xanthones including 1-hydroxyl-2,3,4,7- tetramethoxy xanthone 1, 1-hydroxyl-2,3,4,5-tetramethoxyl xanthone 2, 1-hydroxyl-3,5-dimethoxy- xanthone 3, 1,8-dihydroxyl-3,5-dimethoxyl xanthone 4 and 1,5,8-trihydroxyl-3-methoxy xanthone 5 have been isolated from Swertia chirayita. Their structures were established on the basis of spectral and chemical evidences. The crystal structure of 5 was also investigated by single-crystal X-ray diffraction analysis. It crystallizes in the triclinic system, space group P?with a = 7.1540(10), b = 7.520(2), c = 10.671(2) , V = 562.7(2) 3 , α = 86.50(3), β = 80.06(3) , γ = 85.00(3), Z = 2, Dc = 1.618 g/m3, R = 0.0405, wR = 0.1028 and F(000) = 284. The molecular structure of 5 is nearly planar and four substituents are much closer to the plane. Compound 5 contains three intermolecular hydro- gen bonds. A recent study shows that phenolic hydroxyls in xanthones are the main active groups capable of scavenging OH and O2.展开更多
The thermodynamic properties of xanthone（XTH） and 135 polybrominated xanthones（PBXTHs） in the standard state have been calculated at the B3LYP/6-31G＊ level using Gaussian 03 program.The isodesmic reactions were d...The thermodynamic properties of xanthone（XTH） and 135 polybrominated xanthones（PBXTHs） in the standard state have been calculated at the B3LYP/6-31G＊ level using Gaussian 03 program.The isodesmic reactions were designed to calculate the standard enthalpy of formation（△fHθ） and standard free energy of formation（△fGθ） of PBXTH congeners.The relations of these thermodynamic parameters with the number and position of Br atom substitution（NPBS） were discussed,and it was found that there exist high correlation between thermodynamic parameters（entropy（Sθ）,△fHθ and △fGθ） and NPBS.According to the relative magnitude of their △fGθ,the relative stability order of PBXTH congeners was theoretically proposed.The relative rate constants of formation reactions of PBXTH congeners were calculated,Moreover,the values of molar heat capacity at constant pressure（Cp,m） from 200 to 1000 K for PBXTH congeners were also calculated,and the temperature dependence relation of them was obtained,suggesting very good relationships between Cp,m and temperature（T,T^1 and T^2） for almost all PBXTH congeners.展开更多
Nine prenylated and geranylated xanthones were synthesized in two steps with total yields ranging from 11%to 36%.All of the compounds were first reported.Then,the antitumor,anti-tyrosinase,anti-pancreatic lipase,antif...Nine prenylated and geranylated xanthones were synthesized in two steps with total yields ranging from 11%to 36%.All of the compounds were first reported.Then,the antitumor,anti-tyrosinase,anti-pancreatic lipase,antifungal and antibacterial activities of all or part of compounds 1–9 were evaluated.Compound 9 exhibited clear antitumor activity,and its cytotoxicity against MCF-7 and MDA-MB-231 cells was stronger compared with cisplatin.Compounds 1–4 and 6–7 also exhibited certain activity other than the antitumor activity described above.These results demonstrated that compounds 1–4,6–7 and 9 were very promising leads for further structural modification.展开更多
文摘Ten novel xanthones,garpedunxanthones A-G(1-5,6a/6b,7a/7b) and nujiangxanthone Q(8),along with sixteen known analogs(9-24),were isolated from Garcinia pedunculata and G.nujiangensis.Their structures were elucidated through high-resolution electrospray ionization mass spectrometry(HR-ESI-MS) data,comprehensive nuclear magnetic resonance(NMR) spectroscopic analyses,and electronic circular dichroism(ECD) calculations.All compounds without cytotoxicity were assessed for anti-inflammatory properties by measuring the inhibition of nitric oxide(NO) production in lipopolysaccharide(LPS)-induced RAW264.7cells.Structure-activity relationships are also discussed.Compounds 7b,19,and 21 exhibited significant anti-inflammatory activity with IC_(50) values of 16.44±0.69,14.28±0.78,and 10.67±3.28 μmol·L^(-1),respectively.Enzyme-linked immunosorbent assay(ELISA) demonstrated that compounds 7b,19,and 21 inhibited the expression of pro-inflammatory cytokines TNF-α and IL-6 in a dose-dependent manner.The inhibitory effect of compo und 21 on IL-6 at 20 μmol·L^(-1)was comparable to that of the positive control.In network pharmacology studies,potential targets of compounds and inflammation were identified from PharmMapper and GeneCards databases.Gene Ontology(GO) and Kyoto Encyclopedia of Genes and Genomes(KEGG) enrichment analysis revealed that the overlapped targets were intricately associated with major pathogenic processes linked to inflammation,including positive regulation of mitogen-activated protein kinase(MAPK) cascade,protein kinase activity,NO synthase regulator activity,MAPK signaling pathway,and EGFR tyrosine kinase inhibitor resistance.
基金National Key Technology R&D Program"New Drug Innovation"of China(Grant No.2012ZX09301002-002-002,2012ZX09304-005)
文摘Eight known compounds were isolated from the whole plants ofArenaria serpyllifolia L. by solvent fractionation and subsequent separations with silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC chromatography. Their structures were determined by spectroscopic analysis and identified as quercetin （1）, quercetin 7-O-α-L-rhamnoside （2）, quercetin 3-O-α-L- rhamnoside （3）, 3-O-methyl quercetin （4）, 1,5-dihydroxyxanthone （5）, 1,5-dihydroxyxanthone-6-O-β-D-glucoside （6）, 5-hydroxy- l-methoxyxanthone （7） and 6-deoxyisojacareubin （8）. All these compounds were isolated from this title plant for the first time, and compounds 5-8 were obtained from genus Arenaria for the first time.
基金This work was supported in part by Shanghai Municipal Educational Committee (grants S970204).
文摘From the CHCl3 part of Swertia decora Franch., a traditional medicinal herb of China, two new xanthones, swertiadecoraxanthone-I and swertiadecoraxanthone-II along with four known compounds have been isolated and identified on the basis of spectral analysis and chemical evidence.
基金the National Natural Science Foundation of China （No. 30670215）
文摘Two novel xanthones, 1,6-dihydroxy-4,5-dimethoxyxanthone （1） and 1,5,6-trihydroxy-7,8-di（3-methyl-2-butenyl）-6＇,6＇-dimethylpyrano（2＇,3＇：3,4）xanthone （2） were isolated from the bark of Garcinia xanthochymus by normal phase and reverse phase silica gel column chromatography. Their structures were elucidated by spectroscopic methods, especially 2D-NMR techniques.
基金supported by the Knowledge Innovation Program of Shenzhen(JCYJ20160428181415376 andJCYJ20150529153646078)
文摘Chemical examination of an EtOAc 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 ICs0 values of 25.97 and 25.60 gmol·L^-1, respectively.
基金Supported by Grants from the Center of Excellence for Innovation in Chemistry,Commission on Higher Education,No 48-03-3-00-144Faculty of Medicine,No 51-03-2-00-008 and Khon Kaen University,No 50-03-1-01-005,Research Funds,Khon Kaen University,Thailand
文摘AIM:To investigate the growth inhibitory mechanism of four caged xanthones from Garcinia hanburyi in cholangiocarcinoma(CCA) KKU-100 and KKU-M156 cells.METHODS:Four caged xanthones,selected on the basis of their anticancer potency and chemical structure diversities(i.e.isomorellin,isomorellinol,forbesione and gambogic acid) were used in this study.Growth inhibition of these caged xanthones was determined using the sulforhodamine B assay.Induction of apoptosis was assessed by observing cell morphology,ethidium bromide and acridine orange staining and DNA fragmentation assay.Levels of apoptotic-related gene and protein expressions were determined by a real-time reverse transcriptase polymerase chain reaction and Western blotting analysis,respectively.RESULTS:The compounds were found to inhibit growth of both cell lines in a dose-dependent manner and also showed selective cytotoxicity against the cancer cells when compared with normal peripheral blood mononuclear cells.Growth suppression by these compounds was due to apoptosis,as evidenced by the cell morphological changes,chromatin condensation,nuclear fragmentation,and DNA ladder formation.At the molecular level,these compounds induced down-regulation of Bcl-2 and survivin proteins with up-regulation of Bax and apoptosisinducing factor proteins,leading to the activation of caspase-9 and-3 and DNA fragmentation.The functional group variations did not appear to affect the anticancer activity with regard to the two CCA cell lines;however,at a mechanistic level,isomorellinol exhibited the highest potency in increasing the Bax/Bcl-2 protein expression ratio(120 and 41.4 for KKU-100 and KKU-M156,respectively) and in decreasing survivin protein expression(0.01 fold as compared to control cells in both cell lines).Other activities at the molecular level indicate that functional groups on the prenyl side chain may be important.CONCLUSION:Our findings for the first time demonstrate that four caged xanthones induce apoptosis in CCA cells which is mediated through a mitochondriadependent signaling pathway.
文摘Three new xanthones, 3, 6-dihydroxy-1, 2, 7-trimethoxyxanthone 1, 1, 3, 6-trihydroxy-2, 7, 8-trimethoxyxanthone 2, and 3, 6-dihydroxy-1, 2, 7, 8-tetramethoxyxanthone 3, were isolated from the roots of Polygala crotalarioides. Their structures were elucidated by spectral and chemical methods.
基金The authors would like to acknowledge Agilent Technologies for providing the capillary electrophoresis system and Bioanalytical System for present of sulfated b-CD. The study is supported by NSFC Grant No. 29875001.
文摘A capillary electrophoresis (CE) method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was systematically optimized with respect to pH, concentration of running buffers, addition of sulfated b-CD, applied voltage and column temperature. Baseline separation was achieved for the nine xanthones in less than 15 minutes using a background electrolyte consisting of 200 mmol/L borate (pH 9.5) and 10 mmol/L sulfated b-CD.
基金Supported by the National Natural Science Foundation of China （20977046, 20737001）.
文摘The gas phase thermodynamic properties of 135 polychlorinated xanthones(PCXTs)are calculated using a combination of quantum mechanical computations performed with the Gaussian 03 program at the B3LYP/6-311G**level.It is found that the chlorine substitution pattern strongly influences the thermodynamic properties of the compounds.The thermodynamic properties of congeners with the same number of chlorines also depend on the chlorine substitution pattern,especially for ortho-substituted congeners.PCXT congeners with one phenyl ring fully chlorinated are found to be the least stable among the analogues.The effect of the chlorine substitution pattern is quantitatively studied by considering the number and position of Cl atom substitution(NPCS).The results show that the NPCS model may be used to predict the thermodynamic properties for all 135 PCXT congeners. In addition,the values of molar heat capacities at constant pressure(cp,m)from 200 to 1000 K for PCXT congeners are calculated,and the temperature dependence relation of this parameter is obtained using the least-squares method.
基金funding support from the National Natural Science Foundation of China (No. 81673579)Hunan Province Universities 2011 Collaborative Innovation Center of Protection and Utilization of Hu-Xiang Chinese Medicine ResourcesHunan Provincial Key Laboratory of Diagnostics in Chinese Medicine
文摘Plants have so much to offer as far as the discovery of new bioactive molecules is concerned.Among the several classes of phytochemicals,xanthones offer greater structural diversity and pharmacological value.They are variable but definitely antioxidant in nature.Thus they are attractive targets for natural product and medicinal chemists.Xanthones and their glycosides possess broad spectrum interesting biological activities,such as cytotoxic,anti-inflammatory,antioxidant,anti-bacterial,neuroprotective,anti-HIV,enzyme inhibition,and hypoglycemic.The radical scavenging ability of these molecules accounts for most of their added therapeutic values.This paper intended to serve as a guide for future endeavors in quest for these molecules.Structure-Activity Relationship(SAR)and mechanism of action is given for better understanding of their role as pharmacological agents.The most recent advances in the isolation of bioactive xanthones and their glycosides were presented here.This paper will assist in directed approaches towards the discovery of analogues of xanthones.
文摘A microemulsion electrokinetic chromatography method has been firstly used for the separation of the therapeutically important xanthones from Securidaca inappendiculata. The separation of the nine xanthones was systematically optimized with respect to pH, composition of microemulsion, addition of cyclodextrins, applied voltage and column temperature. Baseline separation was successfully achieved for the nine xanthones, which was also compared with that by micellar electrokinetic chromatography.
基金supported by the National Natural Science Foundation of China(No.81172949)the Program for Excellent Talents of Liaoning Province of China(No.LR2013058)
文摘The present study was designed to investigate the chemical constituents of the roots of Cudrania fruticosa Wight. Compounds were isolated by various column chromatographic methods including silica gel, polyamide, sephadex LH-20, and semi-preparative HPLC. Their structures were elucidated by a combination of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. Two new xanthones, Cudraxanthone T and U(1-2), along with four known compounds(3-6) were isolated from the roots of Cudrania fruticosa Wight.
文摘Introduction Xanthones are secondary metabolites commonly occurring in a few higher plant families, fungi and lichen. Their high taxonomic value in such families and their pharmacological properties, including in vitro cytotoxicity, in vivo antitumour activity, antifungal, antibacterial, antiinflammatory properties and aldose reductase inhibitory activity have provoked great interest. The discovery of the antidiabetic activity of some axnthones＇ from Swertiaceae has prompted us to undertake a more broadly search for novel xanthones from plants of Polygalaceae. The phytochemical investigation has not been performed on this plant up to now. Herein we report the isolation and structure elucidation of two new xanthones （ compounds 1 and 2 ） and three known xanthones （compound 3, 4 and 5 ）.
文摘Two new xanthones, 1, 6, 8-trihydroxy-2, 3-methylenedioxyxanthone 1 and 1, 4-di- hydroxy-6, 7-methylenedioxyxanthone 2, were isolated from the roots of Polygala crotalarioides. Their structures were elucidated by spectroscopic and chemical methods.
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 （△fG^θ）. 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·mo1^-1 respectively by comparing the △fG^θ values. Electronic density topology analysis was applied to validate the strength of bond.
基金We thank the fourth national survey of traditional Chinese medicine resources(2018016)for funding this research.
文摘Thirteen xanthones were isolated from L.rotatum,which were established as l,8-dihydroxy-3,4,5-trimethoxyxanthone(1);l-hydroxy-3异,8-trimethoxyxanthone(2);8-hydroxy-l,3?5-trimethoxyxaiithone(3);l-hydroxy-3,4,5-trimethoxyxanthone(4);l-hydroxy-3,5,8-trimethoxyxanthone(5);l,4,8-trihydroxy-5,6-dimethoxyxanthone(6);l,3,8-trihydroxy-4,7-dimethoxyxanthone(;7)l,8-dihydroxy-3,7-dimethoxyxanthone(8);l-hydroxy-3,5-dimethoxyxanthone(9);l-hydroxy-2,3,4,5-tetramethoxyxanthone(;10)l-hydroxy-2,3,4,7-tetramethoxyxanthone(11);l,7-dihydroxy-3,8-dimethoxyxanthone(12);rel-l,3,5,8-tetrahydroxy-2,4,6,7-tetrahydroxanthen-9-one(13).Compounds 4,6,7,9,10,11,12 and 13 are reported for the first time from Lomatogonium.Furthermore,the activity of xanthones was assessed.
基金the supports of the National Natural Science Foundation of China(No.30873115)National Science and Technology Special Projects(Nos.2009zx09301-003-5-1 and 2009zx09301-003-7-1)supported by the analytical center of the Peking branch of Japanese Shimadzu Corporation to provide the LCMS~n-IT-TOF system
文摘Metabolism study has been carried out on 1-hydroxy-2,3,5-trimethoxyxanthone （HM-1） and 1-hydroxy-2,3,4,7- tetramethoxyxanthone （HM-2）, which are two biologically active ingredients isolated from the Tibetan herb, Halenia elliptica D. Don., in rat liver microsomes in vitro. A method of high performance liquid chromatography coupled to ion trap time-of-flight mass spectrometry （LCMSn-ESI-IT-TOF） was applied to analyze metabolites of HM-1 and HM-2 on line, and five metabolites were identified containing 1,5-dihydroxy-2,3-dimethoxyxanthone （HM-5）, 1,7-dihydroxy-2,3,4-trimethoxyxanthone （HM-9）, 1,4, 7- trihydroxy-2,3-dimethoxyxanthone （HM-10）, 1,4-dihydroxy-2,3,7-trimethoxyxanthone （HM-11） and 1,2-dilaydroxy-3,4,7- trimethoxyxanthone （HM-12）. Among these metabolites, HM-9, HM-11, and HM-12 were isomers mutually. The results indicated that HM-1 and HM-2 occurred Phase I metabolic reaction of demethylation in rat microsomes in vitro.
基金The project was supported by the Key Laboratory for Natural Medicine of Gansu Province and Foundation of Lanzhou University of Technology
文摘In order to study the relationship between biological and pharmacological activities with their structures, a series of tri- and tetra-oxygenated xanthones including 1-hydroxyl-2,3,4,7- tetramethoxy xanthone 1, 1-hydroxyl-2,3,4,5-tetramethoxyl xanthone 2, 1-hydroxyl-3,5-dimethoxy- xanthone 3, 1,8-dihydroxyl-3,5-dimethoxyl xanthone 4 and 1,5,8-trihydroxyl-3-methoxy xanthone 5 have been isolated from Swertia chirayita. Their structures were established on the basis of spectral and chemical evidences. The crystal structure of 5 was also investigated by single-crystal X-ray diffraction analysis. It crystallizes in the triclinic system, space group P?with a = 7.1540(10), b = 7.520(2), c = 10.671(2) , V = 562.7(2) 3 , α = 86.50(3), β = 80.06(3) , γ = 85.00(3), Z = 2, Dc = 1.618 g/m3, R = 0.0405, wR = 0.1028 and F(000) = 284. The molecular structure of 5 is nearly planar and four substituents are much closer to the plane. Compound 5 contains three intermolecular hydro- gen bonds. A recent study shows that phenolic hydroxyls in xanthones are the main active groups capable of scavenging OH and O2.
基金Supported by the NNSFC (20737001, 20977046)NSF of Zhejiang Province (2008Y507280)
文摘The thermodynamic properties of xanthone（XTH） and 135 polybrominated xanthones（PBXTHs） in the standard state have been calculated at the B3LYP/6-31G＊ level using Gaussian 03 program.The isodesmic reactions were designed to calculate the standard enthalpy of formation（△fHθ） and standard free energy of formation（△fGθ） of PBXTH congeners.The relations of these thermodynamic parameters with the number and position of Br atom substitution（NPBS） were discussed,and it was found that there exist high correlation between thermodynamic parameters（entropy（Sθ）,△fHθ and △fGθ） and NPBS.According to the relative magnitude of their △fGθ,the relative stability order of PBXTH congeners was theoretically proposed.The relative rate constants of formation reactions of PBXTH congeners were calculated,Moreover,the values of molar heat capacity at constant pressure（Cp,m） from 200 to 1000 K for PBXTH congeners were also calculated,and the temperature dependence relation of them was obtained,suggesting very good relationships between Cp,m and temperature（T,T^1 and T^2） for almost all PBXTH congeners.
基金Leading Project of Fujian Provincial Department of Science and Technology(Grant No.2018Y0072)。
文摘Nine prenylated and geranylated xanthones were synthesized in two steps with total yields ranging from 11%to 36%.All of the compounds were first reported.Then,the antitumor,anti-tyrosinase,anti-pancreatic lipase,antifungal and antibacterial activities of all or part of compounds 1–9 were evaluated.Compound 9 exhibited clear antitumor activity,and its cytotoxicity against MCF-7 and MDA-MB-231 cells was stronger compared with cisplatin.Compounds 1–4 and 6–7 also exhibited certain activity other than the antitumor activity described above.These results demonstrated that compounds 1–4,6–7 and 9 were very promising leads for further structural modification.
