自胡椒科胡椒属植物樟叶胡椒(Piper polysyphorum C. DC)中分离到六个新木脂素(neolignans)类化合物,经光谱(UV,IR,MS,~1H-NMR,^(13)C-NMR,2D-NMR,CD)分析及衍生物制备,确定Ⅱ为新化合物,即threo-△~7-7-羟基-3,4,5,3′,5′-五甲氧基-8-...自胡椒科胡椒属植物樟叶胡椒(Piper polysyphorum C. DC)中分离到六个新木脂素(neolignans)类化合物,经光谱(UV,IR,MS,~1H-NMR,^(13)C-NMR,2D-NMR,CD)分析及衍生物制备,确定Ⅱ为新化合物,即threo-△~7-7-羟基-3,4,5,3′,5′-五甲氧基-8-O-4′-新木脂素,为一对对映体,命名为樟叶素(polysyphorin),Ⅰ,Ⅲ,Ⅳ为新的对映体,分別为(+)-virolongin,(+)-grandisin及(+)-lancifolin D.化合物Ⅴ为南藤素(wallichinine),Ⅵ为山蒟素D(hancinone D)。血小板活化因子(PAF)受体结合实验及PAF引起的血小板聚集实验证明化合物Ⅰ～Ⅴ具有明显的抑制活性。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.
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
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
以3,4-二羟基苯丙烯酸（咖啡酸）为原料,经酯化和仿生氧化偶联反应得到苯并呋喃类化合物2-（3′,4′-二羟基苯基）-3-甲氧羰基-5-甲氧羰基乙烯基-7-羟基-2,3-二氢苯并呋喃（1）和苯并二氧六环类化合物2-（3′,4′-二羟基苯基）-3-甲氧羰...以3,4-二羟基苯丙烯酸（咖啡酸）为原料,经酯化和仿生氧化偶联反应得到苯并呋喃类化合物2-（3′,4′-二羟基苯基）-3-甲氧羰基-5-甲氧羰基乙烯基-7-羟基-2,3-二氢苯并呋喃（1）和苯并二氧六环类化合物2-（3′,4′-二羟基苯基）-3-甲氧羰基-6-甲氧羰基乙烯基-2,3-二氢-1,4-苯并二氧六环（2）,然后经乙酰化、DDQ氧化脱氢、Pd/C 催化氢化、氢化铝锂还原、碱性条件下脱乙酰基等反应,合成了一系列苯并呋喃新木脂素类化合物3~7和苯并二氧六环新木脂素类化合物8~10.所合成化合物的结构已由核磁共振法（1 H NMR,13 C NMR）、质谱法（MS）进行了表征.其中5~7,9和10是未见文献报道的新化合物,8为天然产物异美商陆醇A.采用MTT法对所合成的苯并呋喃新木脂素类化合物1,3~5进行了生物活性测试.结果表明：化合物1,3,4和5对白血病细胞（HL-60）、肺癌细胞（A-549）、乳腺癌细胞（MCF-7）、结肠癌细胞（SW-480）、肝癌细胞（SMMC-7721）有良好的体外生长抑制活性.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 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
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.
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.
文摘以3,4-二羟基苯丙烯酸（咖啡酸）为原料,经酯化和仿生氧化偶联反应得到苯并呋喃类化合物2-（3′,4′-二羟基苯基）-3-甲氧羰基-5-甲氧羰基乙烯基-7-羟基-2,3-二氢苯并呋喃（1）和苯并二氧六环类化合物2-（3′,4′-二羟基苯基）-3-甲氧羰基-6-甲氧羰基乙烯基-2,3-二氢-1,4-苯并二氧六环（2）,然后经乙酰化、DDQ氧化脱氢、Pd/C 催化氢化、氢化铝锂还原、碱性条件下脱乙酰基等反应,合成了一系列苯并呋喃新木脂素类化合物3~7和苯并二氧六环新木脂素类化合物8~10.所合成化合物的结构已由核磁共振法（1 H NMR,13 C NMR）、质谱法（MS）进行了表征.其中5~7,9和10是未见文献报道的新化合物,8为天然产物异美商陆醇A.采用MTT法对所合成的苯并呋喃新木脂素类化合物1,3~5进行了生物活性测试.结果表明：化合物1,3,4和5对白血病细胞（HL-60）、肺癌细胞（A-549）、乳腺癌细胞（MCF-7）、结肠癌细胞（SW-480）、肝癌细胞（SMMC-7721）有良好的体外生长抑制活性.
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.
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.
