Eight dibenzocyclooctadiene lignans were isolated from the stems of Schisandra propinqua(Wall.)Hook. f. et Thoms. Their structures were elucidated as acetylgomisin R(1), angeloylgomisin R(2), gomisins A(3), B(4), N(5)...Eight dibenzocyclooctadiene lignans were isolated from the stems of Schisandra propinqua(Wall.)Hook. f. et Thoms. Their structures were elucidated as acetylgomisin R(1), angeloylgomisin R(2), gomisins A(3), B(4), N(5) and O(6), 6 O benzoylgomosin O(7) and schisantherin A(8) by spectral studies. Among them, compound 1 was a new one, compound 2 was discovered in the genus Schisandra for the first time and the others were originally isolated from Schisandra propinqua .展开更多
Seven known dibenzocyclooctadiene lignans,tigloylgomisin P(1), angeloylgomisin P(2),gomisin A(3),Schizandrin(4),angeloylgomisin H(5),gomisin B(6) and R(+)-gomisin M_1(7)were isolated from Kadsura heteroclita.The confo...Seven known dibenzocyclooctadiene lignans,tigloylgomisin P(1), angeloylgomisin P(2),gomisin A(3),Schizandrin(4),angeloylgomisin H(5),gomisin B(6) and R(+)-gomisin M_1(7)were isolated from Kadsura heteroclita.The conformation of tiglolylgomisin P(1)was established by 2D NMR techniques.Using[~3H]platelet activating factor(PAF)binding to human platelet membrane assay,(1),(2)and(7)showed PAF receptor antagonistic activities.展开更多
Phenylpropenes,such as isoeugenol and eugenol,are produced as defend compounds,floral attractants,and flavor constituents by phenylpropene synthases belonging to the PIP reductase family.Moreover,isoeugenol is propose...Phenylpropenes,such as isoeugenol and eugenol,are produced as defend compounds,floral attractants,and flavor constituents by phenylpropene synthases belonging to the PIP reductase family.Moreover,isoeugenol is proposed to be involved in the biosynthesis of dibenzocyclooctadiene lignans,the main active compounds of Schisandra chinensis(Turcz.)Baill.fruits(SCF).S.chinensis,a woody vine plant,is widely used for its medicinal,horticultural,edible,and economic values.In this study,nine ScPIP genes were identified and characterized from the transcriptome datasets of SCF.The expression profiles revealed that ScPIP genes were differentially expressed during different developmental stages of SCF.Three ScPIPs were selected and cloned as candidate genes encoding phenylpropene synthases according to phylogenetic analysis.ScPIP1 was proved to function as isoeugenol synthase(IGS)and designated as ScIGS1 through in vivo functional characterization in Escherichia coli.Subcellular localization analysis demonstrated that ScIGS1 was localized in both the cytoplasm and nucleus.The three-dimensional(3D)model of ScIGS1 was obtained using homology modeling.Site-directed mutagenesis experiments revealed that the substitution of residues at positions 110 and 113 impacted the product specificity of ScIGS1 and the mutation of Lys157 to Ala abolishing catalytic function.Moreover,the kcat values of mutants were lower than that of ScIGS1 using a deep learning approach.In conclusion,this study provides a basis for further research on PIP reductases and the biosynthetic pathway of dibenzocyclooctadiene lignans.展开更多
Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura ...Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura longipedunculata.Their structures were elucidated by spectroscopic analysis,including extensive NM R,MS and ECD(electronic circular dichroism) spectra.Compounds 3 and 4 exhibited potent inhibitory activities against NO(nitric oxide) production of LPS(lipopolysaccharide)-induced murine macrophages with the inhibition rates of 36.3% and 26.9%,respectively.展开更多
The stereochemistry of two 6, 9-oxygen bridge dibenzocyclooctadiene lignans from Kadsura coccinea, are difficult to separate and very unstable. The present study was designed to develop a high-performance liquid chrom...The stereochemistry of two 6, 9-oxygen bridge dibenzocyclooctadiene lignans from Kadsura coccinea, are difficult to separate and very unstable. The present study was designed to develop a high-performance liquid chromatography using circular dichroism detection for the analysis of the stereochemistry. A new 6, 9-oxygen bridge dibenzocyclooctadiene lignans named Kadsulignan Q was firstly found with an S-biphenyl configuration. The other compound was identified as Kadsulignan L with an R- biphenyl configuration. In order to obtain kinetic data on their reversible interconversion, the stability was measured at different deuterated solvents such as deuterated methanol, deuterated chloroform and deuterated dimethylsulfoxide. The lignans were more unstable and converted more easily in deuterated methanol than in deuterated chloroform and deuterated dimethylsulfoxide.展开更多
文摘Eight dibenzocyclooctadiene lignans were isolated from the stems of Schisandra propinqua(Wall.)Hook. f. et Thoms. Their structures were elucidated as acetylgomisin R(1), angeloylgomisin R(2), gomisins A(3), B(4), N(5) and O(6), 6 O benzoylgomosin O(7) and schisantherin A(8) by spectral studies. Among them, compound 1 was a new one, compound 2 was discovered in the genus Schisandra for the first time and the others were originally isolated from Schisandra propinqua .
基金This project was supported by National Natural Science Foundation of China.
文摘Seven known dibenzocyclooctadiene lignans,tigloylgomisin P(1), angeloylgomisin P(2),gomisin A(3),Schizandrin(4),angeloylgomisin H(5),gomisin B(6) and R(+)-gomisin M_1(7)were isolated from Kadsura heteroclita.The conformation of tiglolylgomisin P(1)was established by 2D NMR techniques.Using[~3H]platelet activating factor(PAF)binding to human platelet membrane assay,(1),(2)and(7)showed PAF receptor antagonistic activities.
基金supported by grants from the National Natural Science Foundation of China(No.82204576)the CAMS Innovation Fund for Medical Sciences(CIFMS)(No.2022-I2M-JB-009).
文摘Phenylpropenes,such as isoeugenol and eugenol,are produced as defend compounds,floral attractants,and flavor constituents by phenylpropene synthases belonging to the PIP reductase family.Moreover,isoeugenol is proposed to be involved in the biosynthesis of dibenzocyclooctadiene lignans,the main active compounds of Schisandra chinensis(Turcz.)Baill.fruits(SCF).S.chinensis,a woody vine plant,is widely used for its medicinal,horticultural,edible,and economic values.In this study,nine ScPIP genes were identified and characterized from the transcriptome datasets of SCF.The expression profiles revealed that ScPIP genes were differentially expressed during different developmental stages of SCF.Three ScPIPs were selected and cloned as candidate genes encoding phenylpropene synthases according to phylogenetic analysis.ScPIP1 was proved to function as isoeugenol synthase(IGS)and designated as ScIGS1 through in vivo functional characterization in Escherichia coli.Subcellular localization analysis demonstrated that ScIGS1 was localized in both the cytoplasm and nucleus.The three-dimensional(3D)model of ScIGS1 was obtained using homology modeling.Site-directed mutagenesis experiments revealed that the substitution of residues at positions 110 and 113 impacted the product specificity of ScIGS1 and the mutation of Lys157 to Ala abolishing catalytic function.Moreover,the kcat values of mutants were lower than that of ScIGS1 using a deep learning approach.In conclusion,this study provides a basis for further research on PIP reductases and the biosynthetic pathway of dibenzocyclooctadiene lignans.
基金supported by the NSFC (Nos. 30830115 and 20802082)the Major State Basic Research Development Program of China (Nos. 2009CB522300 and 2009CB940900)+2 种基金the Young Academic and Technical Leader Rising Foundation of Yunnan Province (2006PY01-47)the Drug Development from Five Medicinal Plants in West China and their Sustainable Uses (KZCX2-XB2-15)fund from CAS (KSCX2-EW-Q-10)~~
基金financially supported by CAMS Initiative for Innovative Medicine(No.CAMS-2016-I2M-1-010)the Drug Innovation Major Project(No.2018ZX09711001-001-003)。
文摘Four new seco-dibenzocyclooctadiene lignans,kadlongilignans A-D(1-4),consisting of a rare 6,7-seco-(1),two 15,16-seco-(2 and 3) and a 9,10-seco-dibenzocyclooctadiene(4) lignans,were isolated from the roots of Kadsura longipedunculata.Their structures were elucidated by spectroscopic analysis,including extensive NM R,MS and ECD(electronic circular dichroism) spectra.Compounds 3 and 4 exhibited potent inhibitory activities against NO(nitric oxide) production of LPS(lipopolysaccharide)-induced murine macrophages with the inhibition rates of 36.3% and 26.9%,respectively.
基金supported by the PAPD(Priority Academic Program Development)of Jiangsu Higher Education Institutions,University Science Research Project of Jiangsu Province(No.09KJB350002)National Key Technology R&D Program(No.2012BAI30B02),National Natural Science Foundation of China(No.30901853)Hepatic Fibrosis Innovative Medicine-Research and Development of Fructus Schisandrae capsule(No.F12-157-9-00)
文摘The stereochemistry of two 6, 9-oxygen bridge dibenzocyclooctadiene lignans from Kadsura coccinea, are difficult to separate and very unstable. The present study was designed to develop a high-performance liquid chromatography using circular dichroism detection for the analysis of the stereochemistry. A new 6, 9-oxygen bridge dibenzocyclooctadiene lignans named Kadsulignan Q was firstly found with an S-biphenyl configuration. The other compound was identified as Kadsulignan L with an R- biphenyl configuration. In order to obtain kinetic data on their reversible interconversion, the stability was measured at different deuterated solvents such as deuterated methanol, deuterated chloroform and deuterated dimethylsulfoxide. The lignans were more unstable and converted more easily in deuterated methanol than in deuterated chloroform and deuterated dimethylsulfoxide.
