红车轴草和白车轴草化学成分研究
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摘要
本文在综述了豆科(Leguminosae)车轴草属(Trifolium)植物化学成分和药理活性研究的基础上,对车轴草属两种植物红车轴草和白车轴草进行了化学成分的研究,共分离得到26个化合物,其中从红车轴草中分离得到18个化合物,从白车轴草中分离得到8个化合物。综合~1H-NMR、~(13)C-NMR、HR-ESIMS等波谱数据,鉴定了其中的25个化合物的结构。
红车轴草(Trifolium pratense Linn.)为豆科车轴草属多年生草本植物,广泛分布于温带及亚热带地区,我国各地均有栽培或野生。文献报道其具有抗肿瘤,预防胃癌、肠癌、乳腺癌,治疗骨质疏松,改善妇女更年期症状等用途。
利用各种色谱手段,包括常压柱色谱、凝胶色谱、开放ODS柱色谱及制备薄层色谱等从红车轴草的95%乙醇提取物中分离得到18个化合物。通过各种理化常数测定、波谱分析等方法,鉴定了其中17个化合物的结构。它们分别为(6aR,11aR)-山槐素((6aR,11aR)-maackiain,1)、(6aR,11aR)-三叶豆紫檀苷((6aR,11aR)-trifolirhizin,2)、芒柄花素(formononetin,3)、芒柄花苷(ononin,4)、鹰嘴豆芽素A(biochanin A,5)、印度黄檀苷(sissotrin,6)、大豆素(daidzein,7)、大豆苷(daidzin,8)、染料木素(genistein,9)、染料木苷(genistin,10)、德鸢尾素(irilone,11)、红车轴草素(pratensein,12)、毛蕊异黄酮-7-O-β-D-葡萄糖苷(calycosin-7-O-β-D-glucoside,13)、槲皮素(quercetin,14)、pinitol(15)、水杨酸(salicylic acid,16)、β-谷甾醇(β-sitosterol,17)。其中化合物15、16为首次从该植物中分离得到。
白车轴草(Trifolium repens Linn.)为豆科车轴草属多年生草本植物,在全世界广泛分布。文献报道其全草可以入药,具有清热凉血,祛痰止咳,镇静止痛的功效,临床用于治疗癫痫,痔疮出血,硬结肿块等症。
本文对白车轴草的95%乙醇提取物的氯仿萃取物进行了化学成分的分离和鉴定。利于各种色谱手段如硅胶柱色谱、Sephadex LH-20柱色谱、开放ODS柱色谱和中低压柱色谱等手段,从中分离、鉴定了8个化合物。通过各种理化常数测定、波谱分析等方法,分别鉴定为芒柄花素(formononetin,R1)、水杨酸(salicylic acid,R2)、伞形花内酯(umbelliferon,R3)、双白瑞香素(daphnoretin,R4)、trifoliol(R5)、4'-methyoxycoumestrol(R6)、美迪紫檀素(medicarpin,R7)、环阿尔廷-25-烯-3β,24ξ-二醇(cycloart-25-en-3β,24ξ-diol,R8)。其中化合物R2、R3、R4为首次从该植物中分离得到,化合物R8为首次从豆科植物中分离得到。
Based on the review on the chemical constituents and pharmacological research of the genus Trifolium,the chemical constituents of Trifolium pratense Linn.and T.repens Linn.are studied.
Trifolium pratense Linn.,is a herbaceous perennial plant widely distributed in temperate and subtropical regions throughout the world.It has been used as a drug for gastric cancer,bowels cancer,breast cancer,and osteoporosis,and can also improve the condition of women's climacteric symptoms.
By means of many different chromatographic methods such as silica gel,Sephadex LH-20,open ODS column chromatography,and preparative TLC,18 compounds were isolated from Trifolium pratense.By physicochemical data and spectral methods,17 compounds of them were identified as(6aR,11aR)-maackiain(1),(6aR,11 aR)-trifolirhizin(2), formononetin(3),ononin(4),biochanin A(5),sissotrin(6),daldzein(7),daidzin(8),genistein (9),genistin(10),irilone(11),pratensein(12),calycosin-7-O-β-D-glucoside(13),quercetin (14),pinitol(15),salicylic acid(16),andβ-sitosterol(17).Among them,compounds 15 and 16 are reported from this plant for the first time.
Trifolium repens Linn.,is a herbaceous perennial plant which is distributed world-wide. It is used as an important health food for human.It has antispasmodic and expectorant properties,and is used as a drug for epilepsy,haemorrhoids,and lump.
By means of many different chromatographic methods such as silica gel,Sephadex LH-20,ODS column chromatography,and MPLC,8 compounds were isolated from T.repens. By physicochemical data and spectral methods,they were identified as formononetin(R1), salicylic acid(R2),umbelliferon(R3),daphnoretin(R4),trifoliol(R5),4'-methyoxycoumestrol (R6),medicarpin(R7),and cycloart-25-en-3β,24ξ-diol(R8).Among them,compounds 112, R3,and R4 are reported from this plant for the first time,compound R8 is reported from Leguminosae for the first time.
红车轴草(Trifolium pratense Linn.)为豆科车轴草属多年生草本植物,广泛分布于温带及亚热带地区,我国各地均有栽培或野生。文献报道其具有抗肿瘤,预防胃癌、肠癌、乳腺癌,治疗骨质疏松,改善妇女更年期症状等用途。
利用各种色谱手段,包括常压柱色谱、凝胶色谱、开放ODS柱色谱及制备薄层色谱等从红车轴草的95%乙醇提取物中分离得到18个化合物。通过各种理化常数测定、波谱分析等方法,鉴定了其中17个化合物的结构。它们分别为(6aR,11aR)-山槐素((6aR,11aR)-maackiain,1)、(6aR,11aR)-三叶豆紫檀苷((6aR,11aR)-trifolirhizin,2)、芒柄花素(formononetin,3)、芒柄花苷(ononin,4)、鹰嘴豆芽素A(biochanin A,5)、印度黄檀苷(sissotrin,6)、大豆素(daidzein,7)、大豆苷(daidzin,8)、染料木素(genistein,9)、染料木苷(genistin,10)、德鸢尾素(irilone,11)、红车轴草素(pratensein,12)、毛蕊异黄酮-7-O-β-D-葡萄糖苷(calycosin-7-O-β-D-glucoside,13)、槲皮素(quercetin,14)、pinitol(15)、水杨酸(salicylic acid,16)、β-谷甾醇(β-sitosterol,17)。其中化合物15、16为首次从该植物中分离得到。
白车轴草(Trifolium repens Linn.)为豆科车轴草属多年生草本植物,在全世界广泛分布。文献报道其全草可以入药,具有清热凉血,祛痰止咳,镇静止痛的功效,临床用于治疗癫痫,痔疮出血,硬结肿块等症。
本文对白车轴草的95%乙醇提取物的氯仿萃取物进行了化学成分的分离和鉴定。利于各种色谱手段如硅胶柱色谱、Sephadex LH-20柱色谱、开放ODS柱色谱和中低压柱色谱等手段,从中分离、鉴定了8个化合物。通过各种理化常数测定、波谱分析等方法,分别鉴定为芒柄花素(formononetin,R1)、水杨酸(salicylic acid,R2)、伞形花内酯(umbelliferon,R3)、双白瑞香素(daphnoretin,R4)、trifoliol(R5)、4'-methyoxycoumestrol(R6)、美迪紫檀素(medicarpin,R7)、环阿尔廷-25-烯-3β,24ξ-二醇(cycloart-25-en-3β,24ξ-diol,R8)。其中化合物R2、R3、R4为首次从该植物中分离得到,化合物R8为首次从豆科植物中分离得到。
Based on the review on the chemical constituents and pharmacological research of the genus Trifolium,the chemical constituents of Trifolium pratense Linn.and T.repens Linn.are studied.
Trifolium pratense Linn.,is a herbaceous perennial plant widely distributed in temperate and subtropical regions throughout the world.It has been used as a drug for gastric cancer,bowels cancer,breast cancer,and osteoporosis,and can also improve the condition of women's climacteric symptoms.
By means of many different chromatographic methods such as silica gel,Sephadex LH-20,open ODS column chromatography,and preparative TLC,18 compounds were isolated from Trifolium pratense.By physicochemical data and spectral methods,17 compounds of them were identified as(6aR,11aR)-maackiain(1),(6aR,11 aR)-trifolirhizin(2), formononetin(3),ononin(4),biochanin A(5),sissotrin(6),daldzein(7),daidzin(8),genistein (9),genistin(10),irilone(11),pratensein(12),calycosin-7-O-β-D-glucoside(13),quercetin (14),pinitol(15),salicylic acid(16),andβ-sitosterol(17).Among them,compounds 15 and 16 are reported from this plant for the first time.
Trifolium repens Linn.,is a herbaceous perennial plant which is distributed world-wide. It is used as an important health food for human.It has antispasmodic and expectorant properties,and is used as a drug for epilepsy,haemorrhoids,and lump.
By means of many different chromatographic methods such as silica gel,Sephadex LH-20,ODS column chromatography,and MPLC,8 compounds were isolated from T.repens. By physicochemical data and spectral methods,they were identified as formononetin(R1), salicylic acid(R2),umbelliferon(R3),daphnoretin(R4),trifoliol(R5),4'-methyoxycoumestrol (R6),medicarpin(R7),and cycloart-25-en-3β,24ξ-diol(R8).Among them,compounds 112, R3,and R4 are reported from this plant for the first time,compound R8 is reported from Leguminosae for the first time.
引文
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