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
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
Two new neolignans, Kadsuranin G and Kadsuranin H, were isolated from Piper Kadsura (Choisy) Ohwi. Baaed on the spectroscopic analysis (UV, IR, MS, NNR, and X-ray) and chemical reactions, their structures were establi...Two new neolignans, Kadsuranin G and Kadsuranin H, were isolated from Piper Kadsura (Choisy) Ohwi. Baaed on the spectroscopic analysis (UV, IR, MS, NNR, and X-ray) and chemical reactions, their structures were established as 7R,BR,1'S,2'R,3'5-△^(8')-3,4,5'-trimethoxy-2'-hydroxy-1',2',3',4'-tetrahydro-4'-oxo-7,3',8,1'-neolignan and 7R,8R,1'S,2'R,3'S-△^(8')-3,4,5'-trimethoxy-2'-acetyloxy-1',2',3',4'-tetrahydro-4'-oxo-7,3',8,1'-neolignan.展开更多
Two new bicyclo[3,2,1]octanoid neolignans,named as kadsurenin I and kadsurenin J were isolated from Piper kadsura(Choiey)Ohwi.Based on the spectros- copic analysis(UV,IR,MS and NMR)and chemical derivatization,their st...Two new bicyclo[3,2,1]octanoid neolignans,named as kadsurenin I and kadsurenin J were isolated from Piper kadsura(Choiey)Ohwi.Based on the spectros- copic analysis(UV,IR,MS and NMR)and chemical derivatization,their structures were established as 7R,8R,1'R,2'S,3'R-Δ~s'-3,4,5'-trimethoxy-2'-hydroxy-1',2',3',4'- tetrahydro-4'-oxo-7.3',8.1'-neolignan and 7R,8R,1'R,2'S,3'R-Δ~s'-3,4,5'-trimethoxy -2'-acetoxy-1',2',3',4'-tetrabydro-4'-oxo-7.3',8.1'-neolignan respectively.展开更多
Two new neolignans,manneoinsigins A(1)and B(2),together with four known lignans,were isolated from the leaves and stems of Manglietia insignis.The new compounds were established on the basis of extensive spectroscopic...Two new neolignans,manneoinsigins A(1)and B(2),together with four known lignans,were isolated from the leaves and stems of Manglietia insignis.The new compounds were established on the basis of extensive spectroscopic analyses.All compounds except 2 were tested for their cytotoxic activity.Compound 3 showed weak cytotoxic activity against the HL-60 human tumor cell line with the IC50 value of 23.5μM.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 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
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
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 series of 2-aryl-5-alkyl-7-methoxylbenzo[b]furan derivatives have been synthesized by utilizing the coupling of methyl 3- methoxy-4hydroxy-5-bromocinnamate with cuprous phenylacetylide as the key step. The structure...A series of 2-aryl-5-alkyl-7-methoxylbenzo[b]furan derivatives have been synthesized by utilizing the coupling of methyl 3- methoxy-4hydroxy-5-bromocinnamate with cuprous phenylacetylide as the key step. The structures of the new compounds were confirmed by 1H NMR, IR and MS. The structure of compound 14 was further confirmed by single crystal X-ray. Compound 17 showed cytotoxic activity against human lung carcinoma A549.展开更多
Three neolignans, （±）-demethylnitidanin（1）, herpetol（2） and salvinal（3） were synthesized from methyl 4,5-dihydroxy-3-methoxy cinnamate or methyl 4-hydroxy-3-methoxy cinnamate with Ag2O-catalyzed biomimeti...Three neolignans, （±）-demethylnitidanin（1）, herpetol（2） and salvinal（3） were synthesized from methyl 4,5-dihydroxy-3-methoxy cinnamate or methyl 4-hydroxy-3-methoxy cinnamate with Ag2O-catalyzed biomimetic oxidative coupling as the key step of the synthetic route. Five novel benzofuran neolignan-4＇-O-β-D-glycosides（4―8） were achieved by the glycosylation reactions of benzofuran neolignans 2, 3 and 15. The structures of all the compounds synthesized were determined by MS, 1H NMR and IR spectra. （±）-Demethylnitidanin（1） and herpetol（2） were the first synthesized and the synthesis of salvinal（3） was efficiently improved by the new synthetic routes.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
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 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 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
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
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.
文摘Two new neolignans, Kadsuranin G and Kadsuranin H, were isolated from Piper Kadsura (Choisy) Ohwi. Baaed on the spectroscopic analysis (UV, IR, MS, NNR, and X-ray) and chemical reactions, their structures were established as 7R,BR,1'S,2'R,3'5-△^(8')-3,4,5'-trimethoxy-2'-hydroxy-1',2',3',4'-tetrahydro-4'-oxo-7,3',8,1'-neolignan and 7R,8R,1'S,2'R,3'S-△^(8')-3,4,5'-trimethoxy-2'-acetyloxy-1',2',3',4'-tetrahydro-4'-oxo-7,3',8,1'-neolignan.
文摘Two new bicyclo[3,2,1]octanoid neolignans,named as kadsurenin I and kadsurenin J were isolated from Piper kadsura(Choiey)Ohwi.Based on the spectros- copic analysis(UV,IR,MS and NMR)and chemical derivatization,their structures were established as 7R,8R,1'R,2'S,3'R-Δ~s'-3,4,5'-trimethoxy-2'-hydroxy-1',2',3',4'- tetrahydro-4'-oxo-7.3',8.1'-neolignan and 7R,8R,1'R,2'S,3'R-Δ~s'-3,4,5'-trimethoxy -2'-acetoxy-1',2',3',4'-tetrabydro-4'-oxo-7.3',8.1'-neolignan respectively.
基金This project was supported financially by the NSFC(No.20802082 and 30830115)the projects from the Chinese Academy of Sciences(KSCX2-EW-Q-10 and KSCX1-YW-R-24)+2 种基金the Major State Basic Research Development Program of China(No.2009CB522300 and 2009CB940900)the Natural Science Foundation of Yunnan Province(2012FB178 and 20080A007)the project of recruited top talent of sciences and technology of Yunnan Province(2009C1120).
文摘Two new neolignans,manneoinsigins A(1)and B(2),together with four known lignans,were isolated from the leaves and stems of Manglietia insignis.The new compounds were established on the basis of extensive spectroscopic analyses.All compounds except 2 were tested for their cytotoxic activity.Compound 3 showed weak cytotoxic activity against the HL-60 human tumor cell line with the IC50 value of 23.5μM.
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).
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.
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.
文摘A series of 2-aryl-5-alkyl-7-methoxylbenzo[b]furan derivatives have been synthesized by utilizing the coupling of methyl 3- methoxy-4hydroxy-5-bromocinnamate with cuprous phenylacetylide as the key step. The structures of the new compounds were confirmed by 1H NMR, IR and MS. The structure of compound 14 was further confirmed by single crystal X-ray. Compound 17 showed cytotoxic activity against human lung carcinoma A549.
基金Supported by the Personal Training Funds in National Basic Science of China(No.J0830415)
文摘Three neolignans, （±）-demethylnitidanin（1）, herpetol（2） and salvinal（3） were synthesized from methyl 4,5-dihydroxy-3-methoxy cinnamate or methyl 4-hydroxy-3-methoxy cinnamate with Ag2O-catalyzed biomimetic oxidative coupling as the key step of the synthetic route. Five novel benzofuran neolignan-4＇-O-β-D-glycosides（4―8） were achieved by the glycosylation reactions of benzofuran neolignans 2, 3 and 15. The structures of all the compounds synthesized were determined by MS, 1H NMR and IR spectra. （±）-Demethylnitidanin（1） and herpetol（2） were the first synthesized and the synthesis of salvinal（3） was efficiently improved by the new synthetic routes.
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.
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 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 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.
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.
