Houpolignols A-C(1-3),unprecedented oligomers of dearomatized obovatol with tetracyclo[9.3.1.0^(2,7).0^(9,14)]pentadecane(1 and 2)and 8,18-dioxapentacyclo[13.3.1.1^(5,9).0^(4,16).0^(13,20)]icosane(3)core structures,to...Houpolignols A-C(1-3),unprecedented oligomers of dearomatized obovatol with tetracyclo[9.3.1.0^(2,7).0^(9,14)]pentadecane(1 and 2)and 8,18-dioxapentacyclo[13.3.1.1^(5,9).0^(4,16).0^(13,20)]icosane(3)core structures,together with their biosynthetic congener houpolignol D(4),were isolated from the cortex of Magnolia officinalis var.biloba.Their structures were determined by spectroscopic analyses,Xray crystallography data,and quantum chemical calculations.Radical cascade cyclizations were proposed as crucial biosynthetic steps of 1-4.(±)-1 showed anti-nonalcoholic steatohepatitis(NASH)effect by promoting fatty acid beta-oxidation.展开更多
A neolignan codonopiloneolignanin A（1） with a novel 2,9：20,9：7,70-tricyclo-8,90-neolignane skeleton was isolated from an aqueous extract of the Codonopsis pilosula roots. Its structure including the absolute confi...A neolignan codonopiloneolignanin A（1） with a novel 2,9：20,9：7,70-tricyclo-8,90-neolignane skeleton was isolated from an aqueous extract of the Codonopsis pilosula roots. Its structure including the absolute configuration was elucidated by extensive spectroscopic analysis, including 2D NMR and electronic circular dichroism calculation. The proposed biosynthetic pathway of compound 1 is also discussed.展开更多
Aim Isolation and structural elucidation of the constituents from the dried flower buds of Magnolia biondii Pamp. Methods Column chromatography and TLC were used to isolate chemical constituents. Spectroscopic methods...Aim Isolation and structural elucidation of the constituents from the dried flower buds of Magnolia biondii Pamp. Methods Column chromatography and TLC were used to isolate chemical constituents. Spectroscopic methods were employed for structural elucidation. Results One benzo furanoid neolignan （licarin B） and two bisepoxy lignans （magnolin, fargesin） were isolated and identified. Conclusion Licarin B is the first reported benzofuranoid lignan from the family Magnoliaceae.展开更多
A pair of neolig nan enan tiomers with an unprecedented carb on skelet on,(+)-/(-)-angeligna nine[(+)-/(-)-1].was isolated as minor components of an aqueous extract of the Angelica sinensis root heads(guitou).Their st...A pair of neolig nan enan tiomers with an unprecedented carb on skelet on,(+)-/(-)-angeligna nine[(+)-/(-)-1].was isolated as minor components of an aqueous extract of the Angelica sinensis root heads(guitou).Their structures were determined by spectroscopic data analysis and the absolute configurations were assigned by the circular dichroism(CD)exciton chirality method as well as electronic CD quantum calculations.The enantiomers represent the first 2,7/-cyclo-8,9z-neolignans,of which biosynthetic pathways originating from precursors ferulic acid and coniferyl alcohol is proposed.In an in vivo test,both the enantiomers showed significant hypnotic effects at a dose of 10 mg/kg(i.g.).展开更多
From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Symplocos cochinchinensis var. philippinensis, 12 compounds were isolated. Spectroscopic analyses of compounds 1 - 3 established their structures to ...From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Symplocos cochinchinensis var. philippinensis, 12 compounds were isolated. Spectroscopic analyses of compounds 1 - 3 established their structures to be megastig-mane glycosides, named symplocosionosides A-C. The absolute structure of 1 was determined by the modified Mosher’s method. Compound 4 was found to be a neolignan glucoside and named symplocosneolignan. The structures of com-pounds 5 and 6, named symplocosins A and B, were elucidated to be the saponins of hederagenin sugar esters. The structures of the remaining known compounds (7 - 12) were identified by comparison of spectroscopic data with those reported in the literature.展开更多
A new 8-O-4′-type neolignan named narynenol （1） was isolated from the roots of Ligularia narynensis. Its structure and the relative configurations were confirmed by spectroscopic data interpretation. 2007 Zhong J...A new 8-O-4′-type neolignan named narynenol （1） was isolated from the roots of Ligularia narynensis. Its structure and the relative configurations were confirmed by spectroscopic data interpretation. 2007 Zhong Jian Jia. Published by Elsevier B.V. on behalf of Chinese Chemical Society, All rights reserved.展开更多
Gastradefurphenol（1）,a minor 9.9＇-neolignan with a novel carbon skeleton substituted by two phydroxybenzyls was isolated from an aqueous extract of the Gastrodia elata rhizomes（tian ma）.Its structure was determin...Gastradefurphenol（1）,a minor 9.9＇-neolignan with a novel carbon skeleton substituted by two phydroxybenzyls was isolated from an aqueous extract of the Gastrodia elata rhizomes（tian ma）.Its structure was determined by extensive spectroscopic data analysis.Solvent-dependent free rotational restriction of bonds and equilibrium of two molecular states are discussed by comparison of the NMR spectroscopic data of 1 in acetone-d6 with those in CD3OD.A biogenetic pathway of 1 is postulated to be associated with metabolic processes of L-tyrosine.展开更多
Two new neolignans and one new lignan(1-3)were obtained from the roots of Paeonia lactiflora.Their structures were unambiguously elucidated based on extensive spectroscopic analysis,single-crystal X-ray crystallograph...Two new neolignans and one new lignan(1-3)were obtained from the roots of Paeonia lactiflora.Their structures were unambiguously elucidated based on extensive spectroscopic analysis,single-crystal X-ray crystallography,and the calculated and experimental electronic circular dichroism(ECD)spectra.Compound 1 was a racemic mixture and successfully resolved into the anticipated enantiomers via chiral-phase HPLC.Compound 3 demonstrated moderate inhibitory activity against human carboxylesterase 2A1(hCES2Al)with an IC_(50) value of 7.28±0.94 μmol·L^(-1).展开更多
A new nor-neolignan, named ellisinin A (1), has been isolated from the traditional Tibetan medicinal plants of Cremanthodium ellisii. Its structure has been determined on the basis of spectroscopic evidence, especiall...A new nor-neolignan, named ellisinin A (1), has been isolated from the traditional Tibetan medicinal plants of Cremanthodium ellisii. Its structure has been determined on the basis of spectroscopic evidence, especially by 2DNMR (H-1-(HCOSY)-H-1, HMQC, HMBC).展开更多
A new neolignan glycoside named armaoside (1) was isolated from the whole plant of Pedicularis armata Maxim. Its structure was elucidated by spectroscopic and chemical methods. Antibacterial assay showed that it has m...A new neolignan glycoside named armaoside (1) was isolated from the whole plant of Pedicularis armata Maxim. Its structure was elucidated by spectroscopic and chemical methods. Antibacterial assay showed that it has moderately antibacterial activities against Eschecichia coli, Bacillus subtilis and Staphylococcus aureus.展开更多
A new neolignan glycoside, 4-O-β-d-glucopyranosyl-9-O-β-d-glucopyranosyl-(7R,8S)-dehydrodiconiferyl alcohol was isolated from the fresh roots of Angelica dahurica. The structure of the new compound was elucidated on...A new neolignan glycoside, 4-O-β-d-glucopyranosyl-9-O-β-d-glucopyranosyl-(7R,8S)-dehydrodiconiferyl alcohol was isolated from the fresh roots of Angelica dahurica. The structure of the new compound was elucidated on the basis of spectral analysis.展开更多
A novel neolignan, biondinin A, was isolated from the flower buds of Magnolia biondii Pamp. The structure was established as 3,3',4'- trimethoxy-4,9'-dihydroxy-6.8',9-O-7'-neolignan. It is the firs...A novel neolignan, biondinin A, was isolated from the flower buds of Magnolia biondii Pamp. The structure was established as 3,3',4'- trimethoxy-4,9'-dihydroxy-6.8',9-O-7'-neolignan. It is the first reported neolignan possessing the skeleton of benzo-oxa-cyclooctane.展开更多
Six new oligomeric neolignans including two trimeric neolignans(1 and 2)and four dimeric neolignans(3–6)were isolated from the leaves of Magnolia officinalis var.biloba.Their structures were determined based on HR-ES...Six new oligomeric neolignans including two trimeric neolignans(1 and 2)and four dimeric neolignans(3–6)were isolated from the leaves of Magnolia officinalis var.biloba.Their structures were determined based on HR-ESIMS and NMR data,as well as electronic circular dichroism(ECD)calculations.Compound 1 is formed from two obovatol moieties directly linked to an aromatic ring of the remaining obovatol moiety,which is an unprecedented type of linkage between monomers.All isolates were assessed for their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophage cells.Compounds 1 and 3 showed significantly inhibitory activities with IC50 values of 6.04 and 3.26μmol·L^(−1),respectively.展开更多
Two new biphenyl butyl neolignan derivatives,named gymnothebutyllignans A（1） and B（2）,were isolated from the whole parts of endemic medicinal plant of Gymnotheca involucrata（Saururaceae）.The structures of the ne...Two new biphenyl butyl neolignan derivatives,named gymnothebutyllignans A（1） and B（2）,were isolated from the whole parts of endemic medicinal plant of Gymnotheca involucrata（Saururaceae）.The structures of the new compounds were elucidated by extensive NMR and MS data,and the absolutely configuration of compound 1 was confirmed by X-ray crystal diffraction analysis.展开更多
Four 1,4-benzodioxane neolignans were first synthesized from pyrogallol, in which the Claisen rearrangement was used to afford three important C-6-C-3 units.
1-(4-hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxyphenoxy)-propane-1,3-diol. A 8-O-4' neolignan, has been stereoselectively synthesized in eight steps from ferulic acid, and the directly cis opening of epoxide in...1-(4-hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxyphenoxy)-propane-1,3-diol. A 8-O-4' neolignan, has been stereoselectively synthesized in eight steps from ferulic acid, and the directly cis opening of epoxide in eposidation and Mitsunobu reaction were used ingeniously as two key steps with high stereoselectively.展开更多
Two new 8-O-4＇ neolignan glycosides, named matteustruthiosides A（1） and B（2） were isolated from the aerial parts of Matteuccia struthiopteris. Their chemical structures were characterized on the basis of various ...Two new 8-O-4＇ neolignan glycosides, named matteustruthiosides A（1） and B（2） were isolated from the aerial parts of Matteuccia struthiopteris. Their chemical structures were characterized on the basis of various spectroscopic techniques. The absolute configurations of them were determined by experimental circular dichroism（CD） spectra. Compounds 1 and 2 were inactive against influenza A（H1N1） virus in vitro.展开更多
Three new bicyclooctanoid neolignans, kadsurenin A, kadsurenin B and kadsurenin C were isolated from Piper kadsura (Choisy) Ohwi. Based on the spectroscopic analysis (UV, JR, MS, NMR, and X-ray), their structures were...Three new bicyclooctanoid neolignans, kadsurenin A, kadsurenin B and kadsurenin C were isolated from Piper kadsura (Choisy) Ohwi. Based on the spectroscopic analysis (UV, JR, MS, NMR, and X-ray), their structures were established as 7R, 8R, 3'S, 4'R, 5'R-△^(s')-3,4-methyienedioxy-5'-methoxy-4'-acetyloxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan; 7R, 8R, 3'S, 4'R, 5'R-△^(s')-3, 4-methylenedioxy-5'-methoxy-4'-hydroxy-2',3',4',5'-tetrahydro-2'-oxo-7. 3', 8. 5'-neolignan and 7R, 8R. 3'S, 4'R, 5'R-△^(s')-3, 4, 5'-trimethoxy-4'-hydroxy- 2', 3', 4', 5'-tetrahydro-2'-oxo-7. 3', 8. 5'-neolignan respectively.展开更多
基金Financial support for this study is from the National Natural Science Foundation of China(No.32170406)the Social Development Special Projects-Key Research and Development Plan of Science and Technology Department of Yunnan Province(No.202303AC100025)the 111 Project from Ministry of Education of China and the State Administration of Foreign Export Affairs of China(No.B18056).
文摘Houpolignols A-C(1-3),unprecedented oligomers of dearomatized obovatol with tetracyclo[9.3.1.0^(2,7).0^(9,14)]pentadecane(1 and 2)and 8,18-dioxapentacyclo[13.3.1.1^(5,9).0^(4,16).0^(13,20)]icosane(3)core structures,together with their biosynthetic congener houpolignol D(4),were isolated from the cortex of Magnolia officinalis var.biloba.Their structures were determined by spectroscopic analyses,Xray crystallography data,and quantum chemical calculations.Radical cascade cyclizations were proposed as crucial biosynthetic steps of 1-4.(±)-1 showed anti-nonalcoholic steatohepatitis(NASH)effect by promoting fatty acid beta-oxidation.
基金Financial support from the National Natural Science Foundation of China (Nos. 30825044, 21132009)the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT, No. IRT1007)the National Science and Technology Project of China (Nos. 2012ZX09301002-002, 2011ZX0 9307-002-01) are acknowledged
文摘A neolignan codonopiloneolignanin A（1） with a novel 2,9：20,9：7,70-tricyclo-8,90-neolignane skeleton was isolated from an aqueous extract of the Codonopsis pilosula roots. Its structure including the absolute configuration was elucidated by extensive spectroscopic analysis, including 2D NMR and electronic circular dichroism calculation. The proposed biosynthetic pathway of compound 1 is also discussed.
文摘Aim Isolation and structural elucidation of the constituents from the dried flower buds of Magnolia biondii Pamp. Methods Column chromatography and TLC were used to isolate chemical constituents. Spectroscopic methods were employed for structural elucidation. Results One benzo furanoid neolignan （licarin B） and two bisepoxy lignans （magnolin, fargesin） were isolated and identified. Conclusion Licarin B is the first reported benzofuranoid lignan from the family Magnoliaceae.
基金Financial support from the National Natural Sciences Foundation of China(No.81630094)CAMS Innovation Fund for Medical Science(No.2017-I2M-3-010)The Drug Innovation Major Project(No.2018ZX09711001-001)is acknowledged.
文摘A pair of neolig nan enan tiomers with an unprecedented carb on skelet on,(+)-/(-)-angeligna nine[(+)-/(-)-1].was isolated as minor components of an aqueous extract of the Angelica sinensis root heads(guitou).Their structures were determined by spectroscopic data analysis and the absolute configurations were assigned by the circular dichroism(CD)exciton chirality method as well as electronic CD quantum calculations.The enantiomers represent the first 2,7/-cyclo-8,9z-neolignans,of which biosynthetic pathways originating from precursors ferulic acid and coniferyl alcohol is proposed.In an in vivo test,both the enantiomers showed significant hypnotic effects at a dose of 10 mg/kg(i.g.).
文摘From the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Symplocos cochinchinensis var. philippinensis, 12 compounds were isolated. Spectroscopic analyses of compounds 1 - 3 established their structures to be megastig-mane glycosides, named symplocosionosides A-C. The absolute structure of 1 was determined by the modified Mosher’s method. Compound 4 was found to be a neolignan glucoside and named symplocosneolignan. The structures of com-pounds 5 and 6, named symplocosins A and B, were elucidated to be the saponins of hederagenin sugar esters. The structures of the remaining known compounds (7 - 12) were identified by comparison of spectroscopic data with those reported in the literature.
文摘A new 8-O-4′-type neolignan named narynenol （1） was isolated from the roots of Ligularia narynensis. Its structure and the relative configurations were confirmed by spectroscopic data interpretation. 2007 Zhong Jian Jia. Published by Elsevier B.V. on behalf of Chinese Chemical Society, All rights reserved.
基金Financial support from the National Natural Science Foundation of China(Nos.81502942 and 81630094)
文摘Gastradefurphenol（1）,a minor 9.9＇-neolignan with a novel carbon skeleton substituted by two phydroxybenzyls was isolated from an aqueous extract of the Gastrodia elata rhizomes（tian ma）.Its structure was determined by extensive spectroscopic data analysis.Solvent-dependent free rotational restriction of bonds and equilibrium of two molecular states are discussed by comparison of the NMR spectroscopic data of 1 in acetone-d6 with those in CD3OD.A biogenetic pathway of 1 is postulated to be associated with metabolic processes of L-tyrosine.
基金supported by the National Natural Science Foundation of China(Nos.81773589 and 82073978)Beijing Natural Science Foundation(No.JQ18026)the Innovation Platform for the Development and Construction of Special Project of Key Laboratory for Tibet Plateau Phytochemistry of Qinghai Province(No.2020-ZJ-Y20).
文摘Two new neolignans and one new lignan(1-3)were obtained from the roots of Paeonia lactiflora.Their structures were unambiguously elucidated based on extensive spectroscopic analysis,single-crystal X-ray crystallography,and the calculated and experimental electronic circular dichroism(ECD)spectra.Compound 1 was a racemic mixture and successfully resolved into the anticipated enantiomers via chiral-phase HPLC.Compound 3 demonstrated moderate inhibitory activity against human carboxylesterase 2A1(hCES2Al)with an IC_(50) value of 7.28±0.94 μmol·L^(-1).
文摘A new nor-neolignan, named ellisinin A (1), has been isolated from the traditional Tibetan medicinal plants of Cremanthodium ellisii. Its structure has been determined on the basis of spectroscopic evidence, especially by 2DNMR (H-1-(HCOSY)-H-1, HMQC, HMBC).
文摘A new neolignan glycoside named armaoside (1) was isolated from the whole plant of Pedicularis armata Maxim. Its structure was elucidated by spectroscopic and chemical methods. Antibacterial assay showed that it has moderately antibacterial activities against Eschecichia coli, Bacillus subtilis and Staphylococcus aureus.
文摘A new neolignan glycoside, 4-O-β-d-glucopyranosyl-9-O-β-d-glucopyranosyl-(7R,8S)-dehydrodiconiferyl alcohol was isolated from the fresh roots of Angelica dahurica. The structure of the new compound was elucidated on the basis of spectral analysis.
文摘A novel neolignan, biondinin A, was isolated from the flower buds of Magnolia biondii Pamp. The structure was established as 3,3',4'- trimethoxy-4,9'-dihydroxy-6.8',9-O-7'-neolignan. It is the first reported neolignan possessing the skeleton of benzo-oxa-cyclooctane.
基金supported by the Program for Changjiang Scholars and Innovative Research Team in University(No.IRT_15R63)the Drug Innovation Major Project(No.2018ZX09711-001-007)the 111 Project from Ministry of Education of China,and the State Administration of Foreign Export Affairs of China(No.B18056).
文摘Six new oligomeric neolignans including two trimeric neolignans(1 and 2)and four dimeric neolignans(3–6)were isolated from the leaves of Magnolia officinalis var.biloba.Their structures were determined based on HR-ESIMS and NMR data,as well as electronic circular dichroism(ECD)calculations.Compound 1 is formed from two obovatol moieties directly linked to an aromatic ring of the remaining obovatol moiety,which is an unprecedented type of linkage between monomers.All isolates were assessed for their inhibitory effects on NO production in LPS-stimulated RAW 264.7 macrophage cells.Compounds 1 and 3 showed significantly inhibitory activities with IC50 values of 6.04 and 3.26μmol·L^(−1),respectively.
基金financially supported by grants from the National Natural Sciences Foundation of China(No.31560102)
文摘Two new biphenyl butyl neolignan derivatives,named gymnothebutyllignans A（1） and B（2）,were isolated from the whole parts of endemic medicinal plant of Gymnotheca involucrata（Saururaceae）.The structures of the new compounds were elucidated by extensive NMR and MS data,and the absolutely configuration of compound 1 was confirmed by X-ray crystal diffraction analysis.
基金the National Natural Science Foundation of China (No. 29772012)
文摘Four 1,4-benzodioxane neolignans were first synthesized from pyrogallol, in which the Claisen rearrangement was used to afford three important C-6-C-3 units.
基金the National Natural Science Foundation of China (No.29972015).
文摘1-(4-hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxyphenoxy)-propane-1,3-diol. A 8-O-4' neolignan, has been stereoselectively synthesized in eight steps from ferulic acid, and the directly cis opening of epoxide in eposidation and Mitsunobu reaction were used ingeniously as two key steps with high stereoselectively.
基金financially supported by State Key Laboratory of Bioactive Substance and Function of Natural Medicines (No. GTZK201304)the Key Projects of the National Science and Technology Pillar Program (No. 2012BAI30B02)
文摘Two new 8-O-4＇ neolignan glycosides, named matteustruthiosides A（1） and B（2） were isolated from the aerial parts of Matteuccia struthiopteris. Their chemical structures were characterized on the basis of various spectroscopic techniques. The absolute configurations of them were determined by experimental circular dichroism（CD） spectra. Compounds 1 and 2 were inactive against influenza A（H1N1） virus in vitro.
基金The project was supported by National Natural Science Foundation of China
文摘Three new bicyclooctanoid neolignans, kadsurenin A, kadsurenin B and kadsurenin C were isolated from Piper kadsura (Choisy) Ohwi. Based on the spectroscopic analysis (UV, JR, MS, NMR, and X-ray), their structures were established as 7R, 8R, 3'S, 4'R, 5'R-△^(s')-3,4-methyienedioxy-5'-methoxy-4'-acetyloxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan; 7R, 8R, 3'S, 4'R, 5'R-△^(s')-3, 4-methylenedioxy-5'-methoxy-4'-hydroxy-2',3',4',5'-tetrahydro-2'-oxo-7. 3', 8. 5'-neolignan and 7R, 8R. 3'S, 4'R, 5'R-△^(s')-3, 4, 5'-trimethoxy-4'-hydroxy- 2', 3', 4', 5'-tetrahydro-2'-oxo-7. 3', 8. 5'-neolignan respectively.
