南方红豆杉细胞培养物的化学成分研究

采用硅胶柱色谱、Sephadex LH-20、HPLC等柱色谱技术,从南方红豆杉细胞培养物的80%乙醇(体积分数)提取物中分离得到13个化合物,根据理化性质与波谱数据鉴定化合物的结构分别为:2α,4α,7β,9α,10β-pentaacetoxy-14β-hydroxytax-11-ene(1)、2α,4α,7β,9α,10β-pentaacetoxytax-11-ene(2)、1β-deoxybaccatin VI(3)、2α-acetoxytaxusin(4)、taxuyunnanine C(5)、yunnanxane(6)、2α,5α,10β-triacetoxy-14β-propionyloxy-4(20),11-taxadiene(7)、2α,5α,10β-triacetoxy-14β-isobutyryloxy-4(20),11-taxadiene(8)、2α,5α,10β-triacetoxy-14β-(2’-methyl)butyryloxy-4(20),11-taxadiene(9)、13-dehydroxylbaccatin III(10)、13-dehydroxy-10-deacetylbaccatin III(11)、paclitaxel(12)及β-谷甾醇(13)。其中,化合物1为新化合物,化合物2、4、10和11为首次从南方红豆杉的细胞培养物中分离得到。     

东北红豆杉愈伤组织中紫杉烷类化合物的分离与鉴定(2)

目的进一步明确东北红豆杉(Taxus cuspidata)愈伤组织中的化学成分,为开发可持续利用的红豆杉资源提供物质基础。方法采用硅胶柱色谱、制备型高效液相色谱等手段对愈伤组织的甲醇提取物进行分离和纯化;根据化合物的理化性质和波谱数据并结合相关文献对化合物结构进行鉴定。结果从东北红豆杉愈伤组织甲醇提取物中分离得到7个紫杉烷型二萜类化合物,分别鉴定为taxusin(1)、2α-acetoxytaxusin(2)、14β-hydroxytaxusin(3)、2-deacetyltaxuyunnanine C(4)、10-deacetyltaxuyunnanine C(5)、7-表-紫杉醇(7-epi-taxol,6)、cephalomannine(7)。结论化合物1~5,7为首次从东北红豆杉愈伤组织中分离得到,化合物3~5尚未在东北红豆杉中发现。     

南方红豆杉化学成分的分离与鉴定

目的研究南方红豆杉(Taxus chinensis var.mairei)枝叶的化学成分。方法采用反复硅胶柱色谱、ODS柱色谱、Sephadex LH-20凝胶柱色谱、高效液相制备柱色谱等方法进行分离纯化;运用现代波谱技术确定化合物的结构。结果从南方红豆杉枝叶甲醇提取物的氯仿萃取部分分离得到13个紫杉烷类化合物和1个非紫杉烷类化合物,分别鉴定为三尖杉宁碱(cephalomannine,1)、9α,10β,13α-triacetoxy-5α-cinnamoyoxytaxa-4(20),11-diene(2)、2-deacetoxytaxinine J(3)、13-cinnamoylbaccatin III(4)、7β,9α,10β,13α,20-pentaacetoxy-2α-benzoyloxy-4α,5α-dihydroxytax-11-ene(5)、2-deacetoxydecinnamoyl taxinine J(6)、Taxin B(7)、2α,7β,13α-triacetoxy-5α,10β-dihydroxy-9-keto-2(3-20)abeo-taxane(8)、taxuspine B(9)、taxachitriene A(10)、taxcuspine X(11)、7-epi-10-deacetyl taxol(12)、N-Methyltaxol C(13)、芹菜素(apigenin,14)。结论化合物6、9、12、13、14为首次从南方红豆杉(Taxus chinensis var.mairei)中分离得到,化合物7、8为首次从南方红豆杉枝叶分离得到。     

东北红豆杉化学成分的分离与鉴定(Ⅱ)

目的对东北红豆杉(Taxus cuspidataSieb.et Zucc.)的化学成分进行研究。方法采用硅胶柱色谱等方法进行分离纯化,根据理化性质和NMR波谱数据进行结构鉴定。结果分离得到8个化合物,分别鉴定为柳杉酚(sugiol,1)、20-羟基蜕皮酮(20-hydroxyecdysone,2)、davidioside B(3)、表儿茶素(epicatechin,4)、2-去乙酰氧基-7β,9α-二去乙酰基紫杉宁J(2-deacetoxy-7β,9α-dideacetyl-taxinine J,5)、2-去乙酰氧紫杉宁E(2-deacetoxytaxinine E,6)、7-表-10-去乙酰基巴卡亭III(7-epi-10-deacetyl baccatin III,7)、7-O-β-D-木糖-10-乙酰基巴卡亭III(7-O-β-D-xylose-10-deacetyl baccatin III,8)。结论化合物3为首次从红豆杉属植物中得到,化合物1、5、7、8为首次从东北红豆杉植物中分离得到,并利用二维核磁共振技术首次对化合物6的碳谱数据进行了全归属。     

东北红豆杉愈伤组织中松香烷型二萜类成分的分离与鉴定

目的明确东北红豆杉(Taxus cuspidata)愈伤组织中的化学成分,为开发可持续利用的红豆杉资源提供物质基础。方法采用硅胶柱色谱、制备型HPLC等手段对愈伤组织的乙酸乙酯和甲醇提取物进行分离和纯化,根据化合物的理化性质和波谱数据并结合相关文献对化合物结构进行鉴定。结果从东北红豆杉愈伤组织中共分离得到7个松香烷型二萜化合物,分别鉴定为hinokiol(1)、美丽红豆杉素A(taxamairin A,2)、美丽红豆杉素C(taxamairin C,3)、taxayunnin(4)、margoci-lin(5)、3,20-epoxy-12-methoxy-8,11,13-abietatriene-3,7,11-triol(6)和brevitaxin(7)。结论化合物1~7均为首次从东北红豆杉植物中分离得到。     

曼地亚红豆杉中一个新3,11-环紫杉烷型二萜(英文)

研究曼地亚红豆杉针叶的化学成分,应用硅胶、SephadexLH-20、MCI和反相HPLC等多种色谱手段进行分离和纯化,通过1D,2DNMR和MS方法确定化合物的结构。分离得到一个新化合物,命名为1β,2α,9α,10β-tetrahydroxy-5α-cinnamoyloxy-3,11-cyclotaxa-4(20)-en-13-one(1)。另外鉴定了6个已知紫杉烷型二萜类化合物,分别为2α,7β,9α,10β,13α-pentaacetoxytaxa-4(20),11-dien-5α-ol(2),2-deacetoxy-5-decinnamoyltaxinineJ(3),taxuspineF(4),taxuspinananeK(5),taxchinA(6),baccatinIV(7),其中化合物2,5,6,7为首次在曼地亚红豆杉中得到。     

云南红豆杉抗肿瘤活性成分的研究

云南红豆杉(Taxus yunnanensis Cheng et L.K.Fu)树皮的乙醇提取物显示较强的抗肿瘤活性,从中分离得到8个紫杉烷类二萜及其生物碱。经光谱分析和化学反应鉴定7个已知物为taxinine E(1),taxinine J(2),1-acetoxy-5-deacetvl baccatin Ⅰ(4),baccatin Ⅲ(5),taxol(6),cephalomannine(7)和7-xylosyl-10-deacetyl taxol(8)。化合物3命名为云南红豆杉甲素(ymlnanxane),为一新的紫杉烷二萜化合物,其结构为taxa-4(20),11-diene-2α,5α,10β,14β-tetraol-2α,5α,10β-triacetate-14β-αmethyl-β-hydroxyl butyrate,并通过X-射线单晶衍射予以证实.经体外筛迭化合物3具有抗肿瘤活性。     

东北红豆杉愈伤组织培养物中具有抗多药耐药性的新的紫杉烷类化合物

作者建立了一种使东北红豆杉Taxus cuspidata Sieb.et Zucc.愈伤组织稳定而快速生长的方法,并通过对在多种不同培养条件下愈伤组织中次生代谢产物的研究,发现紫杉宁NN-11(2)具有显著的抗多药耐药性(MDR)。继之作者对该愈伤组织做进一步分析,得到了一个新的紫杉烷类化合物(1)。将冻干的愈伤组织依次用正己烷、醋酸乙酯和甲醇提取。醋酸乙酯部位经硅胶柱色谱分离,正己烷-丙酮梯度洗脱,得7个部位F1~F7。F5用正相HPLC分离,己烷-醋酸乙酯(2∶1)洗脱,得到化合物1和2。化合物1为白色无定型粉末,[α]D20+105.2°(c,0.08,CHCl3),分子式C33H…     

东北红豆杉化学成分的分离与鉴定

目的对东北红豆杉(Taxus cuspidtaSibe.et Zucc.)的化学成分进行研究。方法采用硅胶柱色谱等方法进行分离纯化,根据理化性质和NMR波谱数据进行结构鉴定。结果分离得到8个化合物,分别鉴定为大黄素甲醚(physcion,1)、油酸甲酯(methyl oleate,2)、紫杉宁(taxinine,3)、5α-羟基-9α,10β,13α-三乙酰氧紫杉烷-4(20),11-二烯(5α-hydroxy-9α,10β,13α-triacetoxytaxa-4(20),11-diene,4)、云南紫杉宁C(taxuyunnanine C,5)、2-去乙酰氧-5α-羟基紫杉宁J(2-deacetoxydecin-namoyl taxinine J,6)、2-去乙酰氧紫杉宁J(2-deacetoxytaxinine J,7)、11-羟基-12-甲氧基松香烷-8,11,13-三烯-3,7-二酮(11-hydroxy-12-methoxyabieta-8,11,13-triene-3,7-dione,8)。结论化合物1、2为首次从红豆杉属植物中分离得到,化合物4、8为首次从该种植物中分离得到。     

人工栽培的南方红豆杉化学成分研究（Ⅲ）

从人工栽培的南方红豆杉全株乙醇提取物的氯仿萃取部位通过反复硅胶和凝胶柱层析分离得到4个化合物,采用波谱解析(IR,ESI-MS,1HNMR和13C NMR)等方法确定了其结构,4个化合物分别鉴定为taxamairin K(1),2α,4α-dideacetoxy-7β-benzoyloxy-5β,20-epoxy-9α,10β,13α,15-tetrahydroxy-11(15→1)abeotaxa-11-ene(2),7β-xylosyl-taxol(3),10-deacetoxy-7-xylosyl-taxol(4),其中化合物1为新化合物。     

Isolation of taxoids from cell suspension cultures of Taxus wallichiana

Cell suspension cultures of stem-derived callus of Taxus wallichiana in MS-F culture media were found to produce three C-14 oxygenated taxoids and one regular taxoid. The taxoids were identified as yunnanxane (1), 2 alpha, 5 alpha, 10 beta, 14 beta-tetraacetoxy-4(20),11-taxadiene (2), 2 alpha, 5 alpha, 10 beta-triacetoxy-14 beta-(2-methyl)-butyryloxy-4(20),11-taxadiene (3) and 1 beta-hydroxybaccatin I (4).     

Biotransformation of 2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene by cell suspension cultures of Catharanthus roseus

Catharanthus roseus cell suspension cultures were employed for the biotransformation of 2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene ( 1), and four metabolites were obtained. Based on their physical and chemical data, the structures of the four metabolites were respectively elucidated as 10beta-hydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (2), 5alpha-hydroxy-2alpha,10beta, 14beta-triacetoxy-4(20),11-taxadiene (3), 6alpha,10beta-dihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (4), and 6alpha,9alpha,10beta-trihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (5), among which 3 and 5 were characterized as new taxoids. The effects of the stages of substrate addition on the biotransformation were also investigated. The results revealed that the biotransformation rate for 1 reached 85.3 % and the yield of 2 70 % when 1 was administered during the mid-linear phase (9 - 12 th day) of the cell growth cycle. On the other hand, the yield for 4 reached the highest level of 11.8 % when 1 was added in the early linear phase (6 th day).     

Biotransformation of 4(20),11-taxadienes by cell suspension cultures of Platycodon grandiflorum

Platycodon grandiflorum cell suspension cultures were employed to biotransform the taxane diterpenoids 2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene (1) and 9alpha-hydroxy-2alpha,5alpha,10beta,14beta-tetraacetoxy-4(20),11-taxadiene (2). One product, 10beta-hydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (3) was obtained from 1 and two products, 9alpha,10beta-dihydroxy-2alpha,5alpha,14beta-triacetoxy-4(20),11-taxadiene (4) and 10beta-hydroxy-2alpha,5alpha,9alpha,14beta-tetraacetoxy-4(20),11-taxadiene (5) were obtained from 2 incubated with Platycodon cultured cells respectively, among which 5 is characterized as a new taxoid compound. The effects of the addition stage for 1 and 2 on the biotransformation were investigated and the results revealed that: (1) the optimal addition stage for 1 was in the early logarithmic phase (6th day) of the cell growth period, in which 78% of 1 was converted and the yield for 3 reached 75%; (2) the optimal addition stage for 2 was on the mid-logarithmic phase (12th day) of the cell growth period, in which 25.3% of 2 was converted and the yields for 4 and 5 reached 18.9 and 14.5%, respectively.     

Biotransformation of 4(20),11-taxadienes by cell suspension cultures of Platycodon grandiflorum

Platycodon grandiflorum cell suspension cultures were employed to biotransform the taxane diterpenoids 2 f ,5 f , 10 g ,14 g -tetraacetoxy-4(20),11-taxadiene ( 1 ) and 9 f -hydroxy-2 f , 5 f ,10 g ,14 g -tetraacetoxy-4(20),11-taxadiene ( 2 ). One product, 10 g -hydroxy-2 f ,5 f ,14 g -triacetoxy-4(20),11-taxadiene ( 3 ) was obtained from 1 and two products, 9 f ,10 g -dihydroxy-2 f ,5 f ,14 g -triacetoxy-4(20),11-taxadiene ( 4 ) and 10 g -hydroxy-2 f ,5 f ,9 f ,14 g -tetraacetoxy-4(20),11-taxadiene ( 5 ) were obtained from 2 incubated with Platycodon cultured cells respectively, among which 5 is characterized as a new taxoid compound. The effects of the addition stage for 1 and 2 on the biotransformation were investigated and the results revealed that: (1) the optimal addition stage for 1 was in the early logarithmic phase (6th day) of the cell growth period, in which 78% of 1 was converted and the yield for 3 reached 75%; (2) the optimal addition stage for 2 was on the mid-logarithmic phase (12th day) of the cell growth period, in which 25.3% of 2 was converted and the yields for 4 and 5 reached 18.9 and 14.5%, respectively.