A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscop...A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscopie analysis and comparison with related compounds.展开更多
Objective:To investigate the estrogenic effect of(8,9)-furanyl-pterocarpan-3-ol(FPC)on growth of human breast cancer T47D cells and the interactions between the FPC and tamoxifen(TAM),on the growth of estrogen recepto...Objective:To investigate the estrogenic effect of(8,9)-furanyl-pterocarpan-3-ol(FPC)on growth of human breast cancer T47D cells and the interactions between the FPC and tamoxifen(TAM),on the growth of estrogen receptor-dependent breast cancer T47D cells.Methods:The proliferation effect of FPC were conducted on T47D cells in vitro by MTT test.T47D cells were treated with FPC alone(0.01-200μmol/L)or in combination with TAM 20 nmol/L.Furthermore,the expression of ERαor c-Myc were also determined by immunohistochemistry.Results:The results indicated that administration of an anti-estrogen TAM showed growth inhibitory effect on T47D cells,wheraes co-administered with low concentration(less than 1μmol/L)of FPC attenuated to promote cell proliferation.In contrast,the combination of TAM with higher doses(more than 20μmol/L)of FPC showed growth inhibitory.This result was supported by immunocytochemistry studies that the administration of 20 nmol/L TAM down-regulated ER-αand c-Myc,but the combination of 20 nmol/L TAM and 1μmol/L FPC robustly up-regulated expression of ER-α.Thus,the reduced growth inhibition of TAM 20 nmol/L by FPC 1μmol/L on T47D cells may act via the modulation of ER-α.Conclusions:The findings indicate and suggest that FPC had estrogenic activity at low concentrations and anti-estrogenic effect that are likely to be regulated by c-Myc and estrogen receptors.We also confirm that low concentration of FPC attenuated the growth-inhibitory effects of TAM on mammary tumor prevention.Therefore,the present study suggests that caution is warranted regarding the consumption of dietary FPC by breast cancer patients while on TMA therapy.展开更多
A novel phenylpropanoid-substituted catechin glycoside glabraoside A 1 and a new dihydrochalcone 3＇-（7＂-allylphenyl）-2＇,4＇,4＂-trihydroxy-6＇-methoxydihydrochalcone 2 were isolated from the herbs of Sarcandra gl...A novel phenylpropanoid-substituted catechin glycoside glabraoside A 1 and a new dihydrochalcone 3＇-（7＂-allylphenyl）-2＇,4＇,4＂-trihydroxy-6＇-methoxydihydrochalcone 2 were isolated from the herbs of Sarcandra glabra. Their structures were elucidated on the basis of spectroscopic analyses and chiroptical methods.展开更多
Stomach and colorectal cancers are common cancers and leading causes of cancer deaths.Because the alimentary tract can interact directly with dietary components,stomach and colorectal cancer may be closely related to ...Stomach and colorectal cancers are common cancers and leading causes of cancer deaths.Because the alimentary tract can interact directly with dietary components,stomach and colorectal cancer may be closely related to dietary intake.We systematically searched published literature written in English via PubMed by searching for terms related to stomach and colorectal cancer risk and dietary flavonoids up to June 30,2012.Twenty-three studies out of 209 identified articles were finally selected for the analysis.Log point effect estimates and the corresponding standard errors were calculated using covariate-adjusted point effect estimates and 95%CIs from the selected studies.Total dietary flavonoid intake was not associated with a reduced risk of colorectal or stomach cancer [odds ratio(OR)(95%CI) = 1.00(0.90-1.11) and 1.07(0.70-1.61),respectively].Among flavonoid subclasses,the intake of flavonols,flavan-3-ols,anthocyanidins,and proanthocyanidins showed a significant inverse association with colorectal cancer risk [OR(95%CI) = 0.71(0.63-0.81),0.88(0.79-0.97),0.68(0.56-0.82),and 0.72(0.61-0.85),respectively].A significant association was found only between flavonols and stomach cancer risk based on a limited number of selected studies [OR(95%CI) = 0.68(0.46-0.99)].In the summary estimates from casecontrol studies,all flavonoid subclasses except flavones and flavanones were inversely associated with colorectal cancer risk,whereas neither total flavonoids nor any subclasses of flavonoids were associated with colorectal cancer risk in the summary estimates based on the cohort studies.The significant association between flavonoid subclasses and cancer risk might be closely related to bias derived from the case-control design.There was no clear evidence that dietary flavonoids are associated with reduced risk of stomach and colorectal cancer.展开更多
研究了民间草药甜草O ldenlandia cantonensisHow的化学成分。从乙醇提取物的乙酸乙酯洗脱部分得到新的五环三萜urs-12-en-29-αoic ac id-3β-ol。该化合物结构通过NMR、IR、MS等波谱数据综合解析确定。研究了urs-12-en-29-αoic ac i...研究了民间草药甜草O ldenlandia cantonensisHow的化学成分。从乙醇提取物的乙酸乙酯洗脱部分得到新的五环三萜urs-12-en-29-αoic ac id-3β-ol。该化合物结构通过NMR、IR、MS等波谱数据综合解析确定。研究了urs-12-en-29-αoic ac id-3β-ol对重组人DNA拓扑异构酶Ⅰ、肝癌细胞BEL-7402和胃腺癌细胞MCG-803的抑制作用,效果显著,IC50值分别为12.0×10-6、6.5×10-6、8.0×10-6g/mL。由V(石油醚)∶V(乙酸乙酯)=20∶1洗脱得到的低极性成分进行了气相色谱-质谱分析,共鉴定60个化合物,其中长链脂肪族化合物,如烷烃、饱和及不饱和羧酸(酯)含量较丰富,占36.16%,萜类和甾体类化合物分别占6.42%和9.28%。展开更多
Objective To study the chemical constituents of Pronephrium triphyllum.Methods The chemical constituents in the plant were isolated and purified with silica gel and Sephadex LH-20.Their structures were identified by a...Objective To study the chemical constituents of Pronephrium triphyllum.Methods The chemical constituents in the plant were isolated and purified with silica gel and Sephadex LH-20.Their structures were identified by analyses of spectral data and physicochemical properties.Results Six compounds were isolated and identified as shelincaoide A(1),n-butyl-β-D-fructopyranoside(2),triphyllin A(3),6,7-di-hydroxycoumarin(4),daucosterol(5),and β-sitosterol(6),respectively.Conclusion Compound 1 is found to be a new compound.Compounds 2 and 4 are firstly isolated from the plants in Pronephrium Presl.and all compounds except 3 are obtained from the species for the first time.展开更多
The synthesis and properties of (Z)-1-(triphenylstannyl)-3-phenyl-1-buten-3-ol (1) are described. Compound 1 crystallizes from alcohol in the monoclinic space group P21/c with unit-cell dimensions a=9.296(2), 6=14.081...The synthesis and properties of (Z)-1-(triphenylstannyl)-3-phenyl-1-buten-3-ol (1) are described. Compound 1 crystallizes from alcohol in the monoclinic space group P21/c with unit-cell dimensions a=9.296(2), 6=14.081(3), c=18.390(5) A,B=97.70(2), V=2385.5(1) A3, Z=4, F(000)=1008, Dc=1.38 g.cm-3,u=10.88 cm-1, final R=0.0359 for 3079 observed reflection [I > 3(I)]. The X-ray diffraction analysis of this compound shows the presence of an intramolecular coordination to the tin atom giving rise to a five-membered ring in which the metal exhibits a distroted trignoal bipyramidal geometry; as a consequence, a phenyl group, probably the apical one, is cleaved more easily by bromine than the vinyl substituent.展开更多
An inexpensive synthesis of 6-ethynylbipyridine has been accomplished using Sonogashira coupling of 2-bromo-6-iodopyridine with 2-methyl-3-butyn-2-ol. Subsequent Stille coupling with 2-(trimethylstannanyl) pyridine an...An inexpensive synthesis of 6-ethynylbipyridine has been accomplished using Sonogashira coupling of 2-bromo-6-iodopyridine with 2-methyl-3-butyn-2-ol. Subsequent Stille coupling with 2-(trimethylstannanyl) pyridine and hydrolysis provided the target compound in an overall high yield.展开更多
Phytochemical investigation of the purified fractions of the active dichloromethane extract of Hysterionica pinifolia (Poir.) Baker led to the identification of five compounds. New acetylenic alcohol (E)-undec-3-en-5,...Phytochemical investigation of the purified fractions of the active dichloromethane extract of Hysterionica pinifolia (Poir.) Baker led to the identification of five compounds. New acetylenic alcohol (E)-undec-3-en-5,7-diyne-1-ol (1) and three other compounds (3), (4), and (5) were reported for the first time in this species. Furthermore, forty-six components from the volatile fraction of H. pinifolia were identified. These compounds were elucidated using 1D and 2D NMR spectroscopy as well as MS-ESI and GC-FID-MS experiments. The dichloromethane extract, its fractions, and the methanolic extract were tested for insecticidal activity against Tribolium castaneum under laboratory conditions. The dichloromethane extract and the fraction F2 were found to be active, showing high larval mortality. The dichloromethane extract was also active against T. castaneum adults. The results have shown that H. pinifolia could be considered, in a near future, as a potential source for the development of a botanical insecticide for pest control.展开更多
The structure of trans-[Pd(dtco-3-OH)2] (ClO4)2·2DMSO, in which dtco-3-OH is dithiacyclooctan-3-ol and DMSO is dimethyl sulfoxide, was determined by X-ray crystallographic analysis. The crystal data: space group ...The structure of trans-[Pd(dtco-3-OH)2] (ClO4)2·2DMSO, in which dtco-3-OH is dithiacyclooctan-3-ol and DMSO is dimethyl sulfoxide, was determined by X-ray crystallographic analysis. The crystal data: space group pi, a = 0.7077(2) nm, b = 1.0788(1) nm, c = 1.1111(1) nm, α=67.710(8)°, β = 73. 59(2)°, γ = 85. 39(2)°,R1 = 0 . 0368 and Rw = 0.0998. The palladium (II) is coordinated by four sulfur atoms with a regular square planar configuration. The Pd-S distances are 0.2314(1) and 0.2317(1) nm, respectively. Both dtco-3-OH ligands are in the boat-chair configuration and two hydroxyl groups are on the opposite sites of the PdS4 coordination plane and are towards Pd(II). The Pd-O distance is 0. 285 nm, indicating a weak interaction between them. A typical hydrogen bond between the hydroxyl group of dtco-3-OH ligand and DMSO was observed in the crystal structure. An aqueous solution prepared with the crystals of the complex was used for the investigation of electrospray mass spectrometry ( ESMS ). Besides trans -[ Pd ( dtco-3-OH)2]2+. 2DMSO observed, in the full scan spectrum of ESMS, all relative species of it, which were probably produced during electrospray ionization process, were also detected. From these experiments, it reveals that ESMS is a powerful tool for studying noncovalent interaction present in solution between inorganic complexes and solvents.展开更多
The discovery of novel flavonoids and elucidation of their biosynthesis are fundamental to understanding their roles in plants and their benefits for human and animal health.Here,we report a new pathway for polymeriza...The discovery of novel flavonoids and elucidation of their biosynthesis are fundamental to understanding their roles in plants and their benefits for human and animal health.Here,we report a new pathway for polymerization of a group of novel oligomeric flavonoids in plants.We engineered red cells for discovering genes of interest involved in the flavonoid pathway and identified a gene encoding a novel flavanol polymerase(FP)localized in the central vacuole.FP catalyzes the polymerization of flavanols,such as epicatechin and catechin,to produce yellowish dimers or oligomers.Structural elucidation shows that these compounds feature a novel oligomeric flaven–flavan(FF)skeleton linked by interflavan–flaven and interflaven bonds,distinguishing them from proanthocyanidins and dehydrodicatechins.Detailed chemical and physical characterizations further confirmed the novel FFs as flavonoids.Mechanistic investigations demonstrated that FP polymerizes flavan-3-ols and flav-2-en-3-ol carbocation,forming dimeric or oligomeric flaven-4→8-flavans,which we term“papanridins.”Data from transgenic experiments,mutant analysis,metabolic profiling,and phylogenetic analyses show that the biosynthesis of papanridins is prevalent in cacao,grape,blueberry,corn,rice,Arabidopsis,and other species in the plant kingdom.In summary,our study discoveries a group of novel oligomeric flavonoids,namely papanridins,and reveals that a novel FP-mediated polymerization mechanism for the biosynthesis of papanridins in plants.展开更多
文摘A new flavan-3-ol glucoside, (-)-afzelechin-7-O-β-D-glucopyranoside (1), has been isolated from the stem of Daphniphyllum oldhami. The structure of the new compound was elucidated on the basis of detailed spectroscopie analysis and comparison with related compounds.
基金Supported in part by Hibah Competition Grant Research of Faculty of PharmacyGadjah Mada University(Grant No.UGM/FA/851.d/M/05/01)
文摘Objective:To investigate the estrogenic effect of(8,9)-furanyl-pterocarpan-3-ol(FPC)on growth of human breast cancer T47D cells and the interactions between the FPC and tamoxifen(TAM),on the growth of estrogen receptor-dependent breast cancer T47D cells.Methods:The proliferation effect of FPC were conducted on T47D cells in vitro by MTT test.T47D cells were treated with FPC alone(0.01-200μmol/L)or in combination with TAM 20 nmol/L.Furthermore,the expression of ERαor c-Myc were also determined by immunohistochemistry.Results:The results indicated that administration of an anti-estrogen TAM showed growth inhibitory effect on T47D cells,wheraes co-administered with low concentration(less than 1μmol/L)of FPC attenuated to promote cell proliferation.In contrast,the combination of TAM with higher doses(more than 20μmol/L)of FPC showed growth inhibitory.This result was supported by immunocytochemistry studies that the administration of 20 nmol/L TAM down-regulated ER-αand c-Myc,but the combination of 20 nmol/L TAM and 1μmol/L FPC robustly up-regulated expression of ER-α.Thus,the reduced growth inhibition of TAM 20 nmol/L by FPC 1μmol/L on T47D cells may act via the modulation of ER-α.Conclusions:The findings indicate and suggest that FPC had estrogenic activity at low concentrations and anti-estrogenic effect that are likely to be regulated by c-Myc and estrogen receptors.We also confirm that low concentration of FPC attenuated the growth-inhibitory effects of TAM on mammary tumor prevention.Therefore,the present study suggests that caution is warranted regarding the consumption of dietary FPC by breast cancer patients while on TMA therapy.
基金the National Natural Science Foundation of China （No. 20432030） for financial support.
文摘A novel phenylpropanoid-substituted catechin glycoside glabraoside A 1 and a new dihydrochalcone 3＇-（7＂-allylphenyl）-2＇,4＇,4＂-trihydroxy-6＇-methoxydihydrochalcone 2 were isolated from the herbs of Sarcandra glabra. Their structures were elucidated on the basis of spectroscopic analyses and chiroptical methods.
文摘Stomach and colorectal cancers are common cancers and leading causes of cancer deaths.Because the alimentary tract can interact directly with dietary components,stomach and colorectal cancer may be closely related to dietary intake.We systematically searched published literature written in English via PubMed by searching for terms related to stomach and colorectal cancer risk and dietary flavonoids up to June 30,2012.Twenty-three studies out of 209 identified articles were finally selected for the analysis.Log point effect estimates and the corresponding standard errors were calculated using covariate-adjusted point effect estimates and 95%CIs from the selected studies.Total dietary flavonoid intake was not associated with a reduced risk of colorectal or stomach cancer [odds ratio(OR)(95%CI) = 1.00(0.90-1.11) and 1.07(0.70-1.61),respectively].Among flavonoid subclasses,the intake of flavonols,flavan-3-ols,anthocyanidins,and proanthocyanidins showed a significant inverse association with colorectal cancer risk [OR(95%CI) = 0.71(0.63-0.81),0.88(0.79-0.97),0.68(0.56-0.82),and 0.72(0.61-0.85),respectively].A significant association was found only between flavonols and stomach cancer risk based on a limited number of selected studies [OR(95%CI) = 0.68(0.46-0.99)].In the summary estimates from casecontrol studies,all flavonoid subclasses except flavones and flavanones were inversely associated with colorectal cancer risk,whereas neither total flavonoids nor any subclasses of flavonoids were associated with colorectal cancer risk in the summary estimates based on the cohort studies.The significant association between flavonoid subclasses and cancer risk might be closely related to bias derived from the case-control design.There was no clear evidence that dietary flavonoids are associated with reduced risk of stomach and colorectal cancer.
文摘研究了民间草药甜草O ldenlandia cantonensisHow的化学成分。从乙醇提取物的乙酸乙酯洗脱部分得到新的五环三萜urs-12-en-29-αoic ac id-3β-ol。该化合物结构通过NMR、IR、MS等波谱数据综合解析确定。研究了urs-12-en-29-αoic ac id-3β-ol对重组人DNA拓扑异构酶Ⅰ、肝癌细胞BEL-7402和胃腺癌细胞MCG-803的抑制作用,效果显著,IC50值分别为12.0×10-6、6.5×10-6、8.0×10-6g/mL。由V(石油醚)∶V(乙酸乙酯)=20∶1洗脱得到的低极性成分进行了气相色谱-质谱分析,共鉴定60个化合物,其中长链脂肪族化合物,如烷烃、饱和及不饱和羧酸(酯)含量较丰富,占36.16%,萜类和甾体类化合物分别占6.42%和9.28%。
基金Science and Technology Project of Zhongshan,China (20071A036)
文摘Objective To study the chemical constituents of Pronephrium triphyllum.Methods The chemical constituents in the plant were isolated and purified with silica gel and Sephadex LH-20.Their structures were identified by analyses of spectral data and physicochemical properties.Results Six compounds were isolated and identified as shelincaoide A(1),n-butyl-β-D-fructopyranoside(2),triphyllin A(3),6,7-di-hydroxycoumarin(4),daucosterol(5),and β-sitosterol(6),respectively.Conclusion Compound 1 is found to be a new compound.Compounds 2 and 4 are firstly isolated from the plants in Pronephrium Presl.and all compounds except 3 are obtained from the species for the first time.
基金Project supported by the National Natural Sciences Foundation of China.
文摘The synthesis and properties of (Z)-1-(triphenylstannyl)-3-phenyl-1-buten-3-ol (1) are described. Compound 1 crystallizes from alcohol in the monoclinic space group P21/c with unit-cell dimensions a=9.296(2), 6=14.081(3), c=18.390(5) A,B=97.70(2), V=2385.5(1) A3, Z=4, F(000)=1008, Dc=1.38 g.cm-3,u=10.88 cm-1, final R=0.0359 for 3079 observed reflection [I > 3(I)]. The X-ray diffraction analysis of this compound shows the presence of an intramolecular coordination to the tin atom giving rise to a five-membered ring in which the metal exhibits a distroted trignoal bipyramidal geometry; as a consequence, a phenyl group, probably the apical one, is cleaved more easily by bromine than the vinyl substituent.
文摘An inexpensive synthesis of 6-ethynylbipyridine has been accomplished using Sonogashira coupling of 2-bromo-6-iodopyridine with 2-methyl-3-butyn-2-ol. Subsequent Stille coupling with 2-(trimethylstannanyl) pyridine and hydrolysis provided the target compound in an overall high yield.
文摘Phytochemical investigation of the purified fractions of the active dichloromethane extract of Hysterionica pinifolia (Poir.) Baker led to the identification of five compounds. New acetylenic alcohol (E)-undec-3-en-5,7-diyne-1-ol (1) and three other compounds (3), (4), and (5) were reported for the first time in this species. Furthermore, forty-six components from the volatile fraction of H. pinifolia were identified. These compounds were elucidated using 1D and 2D NMR spectroscopy as well as MS-ESI and GC-FID-MS experiments. The dichloromethane extract, its fractions, and the methanolic extract were tested for insecticidal activity against Tribolium castaneum under laboratory conditions. The dichloromethane extract and the fraction F2 were found to be active, showing high larval mortality. The dichloromethane extract was also active against T. castaneum adults. The results have shown that H. pinifolia could be considered, in a near future, as a potential source for the development of a botanical insecticide for pest control.
基金Project supported by the National Natural Science Foundation of China (Nos. 29871017, 29823001) and the Natural Science Foundation of Jiangsu Province (No. BK97015).
文摘The structure of trans-[Pd(dtco-3-OH)2] (ClO4)2·2DMSO, in which dtco-3-OH is dithiacyclooctan-3-ol and DMSO is dimethyl sulfoxide, was determined by X-ray crystallographic analysis. The crystal data: space group pi, a = 0.7077(2) nm, b = 1.0788(1) nm, c = 1.1111(1) nm, α=67.710(8)°, β = 73. 59(2)°, γ = 85. 39(2)°,R1 = 0 . 0368 and Rw = 0.0998. The palladium (II) is coordinated by four sulfur atoms with a regular square planar configuration. The Pd-S distances are 0.2314(1) and 0.2317(1) nm, respectively. Both dtco-3-OH ligands are in the boat-chair configuration and two hydroxyl groups are on the opposite sites of the PdS4 coordination plane and are towards Pd(II). The Pd-O distance is 0. 285 nm, indicating a weak interaction between them. A typical hydrogen bond between the hydroxyl group of dtco-3-OH ligand and DMSO was observed in the crystal structure. An aqueous solution prepared with the crystals of the complex was used for the investigation of electrospray mass spectrometry ( ESMS ). Besides trans -[ Pd ( dtco-3-OH)2]2+. 2DMSO observed, in the full scan spectrum of ESMS, all relative species of it, which were probably produced during electrospray ionization process, were also detected. From these experiments, it reveals that ESMS is a powerful tool for studying noncovalent interaction present in solution between inorganic complexes and solvents.
基金funded by the US Department of Agriculture 526614-09725(D.-Y.X.)in 2006.
文摘The discovery of novel flavonoids and elucidation of their biosynthesis are fundamental to understanding their roles in plants and their benefits for human and animal health.Here,we report a new pathway for polymerization of a group of novel oligomeric flavonoids in plants.We engineered red cells for discovering genes of interest involved in the flavonoid pathway and identified a gene encoding a novel flavanol polymerase(FP)localized in the central vacuole.FP catalyzes the polymerization of flavanols,such as epicatechin and catechin,to produce yellowish dimers or oligomers.Structural elucidation shows that these compounds feature a novel oligomeric flaven–flavan(FF)skeleton linked by interflavan–flaven and interflaven bonds,distinguishing them from proanthocyanidins and dehydrodicatechins.Detailed chemical and physical characterizations further confirmed the novel FFs as flavonoids.Mechanistic investigations demonstrated that FP polymerizes flavan-3-ols and flav-2-en-3-ol carbocation,forming dimeric or oligomeric flaven-4→8-flavans,which we term“papanridins.”Data from transgenic experiments,mutant analysis,metabolic profiling,and phylogenetic analyses show that the biosynthesis of papanridins is prevalent in cacao,grape,blueberry,corn,rice,Arabidopsis,and other species in the plant kingdom.In summary,our study discoveries a group of novel oligomeric flavonoids,namely papanridins,and reveals that a novel FP-mediated polymerization mechanism for the biosynthesis of papanridins in plants.
