藏药鬼箭锦鸡儿化学成分的研究
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摘要
鬼箭锦鸡儿属豆科锦鸡儿属植物,灌木,主产于我国西北部地区。鬼箭锦鸡儿长期以来作为藏医民间用药,又名作毛兴,其根茎具有活血化瘀、降压、消炎散肿等功效,内用治疗高血压、多血症、月经不调,外用治疗跌打损伤等。鬼箭锦鸡儿乙醇提取物进行药理活性筛选试验显示,鬼箭锦鸡儿在抗癌、抗炎、镇痛等多方面具有显著作用。根据活性筛选的指导,本课题对鬼箭锦鸡儿根茎提取物的二氯甲烷和乙酸乙酯萃取部分进行系统分离,运用硅胶、凝胶、反相硅胶、制备液相等方法得到16种单体化合物,通过紫外光谱、红外光谱、质谱、核磁共振等手段对化合物进行结构解析,鉴定结果分别为9个异黄酮:L-高丽槐素(CaJ-1)、阿夫罗摩辛(CaJ-2)、Ψ-赝靛素(CaJ-3)、4’-羟基-6,7,3’-三甲氧基异黄酮(CaJ-4)、7,6’-二羟基-6-甲氧基-3’,4’-亚甲二氧基异黄酮(CaJ-5)、odoratin(CaJ-6)、5,4’-二羟基-7,3’-二甲氧基异黄酮(CaJ-7)、7,4’-二羟基-3’-甲氧基异黄酮(CaJ-8)、7,8,5’-三羟基-3’-甲氧基异黄酮(CaJ-13);3个黄酮:7,3’-二羟基-4’-甲氧基黄酮(CaJ-11)、7,4’-二羟基黄酮(CaJ-12)、7,3’,4’-三羟基黄酮(CaJ-15);1个查尔酮:异甘草素(CaJ-10);2个二苯乙烯单体:白藜芦醇(CaJ-14)、piceatannol(CaJ-16);1个甾醇:胡萝卜苷(CaJ-9)。其中CaJ-5和CaJ-13为新化合物,CaJ-2、CaJ-4、CaJ-7、CaJ-10、CaJ-11、CaJ-12和CaJ-15为锦鸡儿属植物中首次得到的化合物。
Caragana Jubata belongs to the genus Caragana of family Leguminosae. It is a shrub mainly distributed in northwest area of China. C. Jubata, of which Tibetan name is zuomaoxing, has a profound medicinal history in Tibetan traditional medicine. Its rhizome has the efficacy of promoting blood flow, reducing blood pressure and eliminating inflammation, which can be treated with plethora, hypertension, catamenia disorder for internal use while bruises and contused wound for external use. As a result of pharmacological activity screening test, C. Jubata has evident effects on anti-tumor, anti-inflammation and analgesia. Directed by bioactive screening, systematic isolation of dichloromethane and ethyl acetate extract of C. Jubata was carried out. Sixteen compounds were obtained by preparative chromatography methods of silica gel, Sephadex, Toyopearl, RP-gel, HPLC, et al. Based on UV, IR, MS and NMR, those compounds were identified as 9 isoflavones: L-Maackiain (CaJ-1), afrormosin (CaJ-2),Ψ-baptigenin (CaJ-3), 4’-hydroxy-6,7,3’-trimethoxy isoflavone (CaJ-4), 7,6’-dihydroxy-6-methoxy-3’,4’-methylenedioxyisoflavone (CaJ-5), odoratin(CaJ-6), 5,4’-dihydroxy-7,3’-dimethoxyisoflavone (CaJ-7), 7,4’-di- hydroxy-3’-methoxyisoflavone (CaJ-8), 7,8,5’-trihydroxy-3’-methoxyisoflavone (CaJ-13); 3 flavones: 7,3’-dihydroxy-4’-methoxyflavone (CaJ-11), 7,4’-dihydroxy- flavone (CaJ-12), 7,3’,4’-trihydroxyflavone (CaJ-15); 1 chalcone: isoliquiritigenin (CaJ-10); 2 stilbene monomers: resveratrol (CaJ-14), piceatannol (CaJ-16); 1 sterol: daucosterol (CaJ-9). CaJ-5 and CaJ-13 are new compounds, while CaJ-2, CaJ-4, CaJ-7, CaJ-10, CaJ-11, CaJ-12 and CaJ-15 are isolated from genus Caragana for the first time.
Caragana Jubata belongs to the genus Caragana of family Leguminosae. It is a shrub mainly distributed in northwest area of China. C. Jubata, of which Tibetan name is zuomaoxing, has a profound medicinal history in Tibetan traditional medicine. Its rhizome has the efficacy of promoting blood flow, reducing blood pressure and eliminating inflammation, which can be treated with plethora, hypertension, catamenia disorder for internal use while bruises and contused wound for external use. As a result of pharmacological activity screening test, C. Jubata has evident effects on anti-tumor, anti-inflammation and analgesia. Directed by bioactive screening, systematic isolation of dichloromethane and ethyl acetate extract of C. Jubata was carried out. Sixteen compounds were obtained by preparative chromatography methods of silica gel, Sephadex, Toyopearl, RP-gel, HPLC, et al. Based on UV, IR, MS and NMR, those compounds were identified as 9 isoflavones: L-Maackiain (CaJ-1), afrormosin (CaJ-2),Ψ-baptigenin (CaJ-3), 4’-hydroxy-6,7,3’-trimethoxy isoflavone (CaJ-4), 7,6’-dihydroxy-6-methoxy-3’,4’-methylenedioxyisoflavone (CaJ-5), odoratin(CaJ-6), 5,4’-dihydroxy-7,3’-dimethoxyisoflavone (CaJ-7), 7,4’-di- hydroxy-3’-methoxyisoflavone (CaJ-8), 7,8,5’-trihydroxy-3’-methoxyisoflavone (CaJ-13); 3 flavones: 7,3’-dihydroxy-4’-methoxyflavone (CaJ-11), 7,4’-dihydroxy- flavone (CaJ-12), 7,3’,4’-trihydroxyflavone (CaJ-15); 1 chalcone: isoliquiritigenin (CaJ-10); 2 stilbene monomers: resveratrol (CaJ-14), piceatannol (CaJ-16); 1 sterol: daucosterol (CaJ-9). CaJ-5 and CaJ-13 are new compounds, while CaJ-2, CaJ-4, CaJ-7, CaJ-10, CaJ-11, CaJ-12 and CaJ-15 are isolated from genus Caragana for the first time.
引文
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[2] 牛西午,中国锦鸡儿属的资源研究——分布及分种描述,西北植物学报,1999,15(9):107~133
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[12] 张甦,中间锦鸡儿的化学成分研究(Ⅳ):[硕士学位论文],复旦大学,2005
[13] 孙智华,中间锦鸡儿倍半萜类化合物的分离及活性研究:[博士学位论文],复旦大学,2004
[14] 刘红霞,狭叶锦鸡儿化学成分的研究:[博士学位论文],中国协和医科大学,2004
[15] 杨敬芝,李建北,张万隆等,鬼箭锦鸡儿化学成分的研究,中草药,2003,34(5):405~406
[16] Umarov A., Batyuk V. S., Khaletskii A. M. Myricetin glycosides from Caragana jubata. Mater Yubileinoi Resp Nauchn Konf Farm. 1972: 99~101
[17] Umarov, A., Batyuk, V.S., Khaletskii, A.M., et al. Flavonols from Caragana jubata. Khimiya Prirodnykh Soedinenii. 1971, 7(4): 522~523
[18] 王玉兰,陈未名,李广义,藏药鬼箭锦鸡儿的化学成分,中草药,1986,17(8):8~10
[19] 贾世山,周桂坤,中间锦鸡儿根异黄酮的分离鉴定,中药通报,1988,13(12):738~739
[20] 张礼萍,鞠美华,胡昌奇,金雀根中的异黄酮类成分,中草药,1996,27(3):134~136
[21] Yuldashev, M. P., Batirov, E. Kh., Butayarov, A. V., et al. Flavonoids from the aerial parts of Caragana alaica Pojark. Rastitel'nye Resursy. 2000, 36(4): 53~55
[22] Ma C. W., Ham I., Whang W. K. The flavonoids from Caragana Chamlagu leaves. Yakhak Hoechi. 1999, 43(2): 143~149
[23] Polovinko A. E., Yakovlev G. P. Flavonoids of Caragana pygmaea. Khimiya Prirodnykh Soedinenii. 1985, (2): 268
[24] Shpekina G. A. Flavonoids of Caragana spinosa. Khimiya Prirodnykh Soedinenii. 1990, (1): 117~118
[25] Jin G. Z., Li J. D., Ahn B. Z. Isoflavones from the root of Caragana microphylla Lam. Yakhak Hoechi. 1992, 36(5): 481~485
[26] Polovinko A. E., Shostakovskaya N. G. Flavonoids of Caragana aurantiaca. Khimiya Prirodnykh Soedinenii. 1987, (3): 450~451
[27] Xiang T., Uno T., Ogino F., et al. Antioxidant constituents of Caragana Tibetica. Chem. Pharm. Bull. 2005, 53(9): 1204~1206
[28] Kitanaka S., Takido M., Mizoue K., et al. Oligomeric stilbenes from Caragana chamlagu Lamark root. Chem. Pharm. Bull. 1996, 44(3): 565~567
[29] Cho Y. K., Lee M. W., Kang H. M., et al. Acylglucosyl sterols from the roots of Caragana chamlagu. Saengyak Hakhoechi. 1992, 23(1): 14~19
[30] Lee Y. B., Yoo S. J., Kim J. S., et al. Saponins from the roots of Caragana chamlagu. Saengyak Hakhoechi. 1990, 21(2): 193~194
[31] Sung H. K., Kim I. H. Studies on the sterols of Caragana chamlagu Lamarck. Yakhak Hoechi. 1978, 22(4): 219~225
[32] Boinik V. V., Kovalev V. N., Komissarenko N. F., et al. Coumarins from the aboveground part of Caragana frutex. Khimiya Prirodnykh Soedinenii. 1983, (6): 780-781
[33] Lin W. H., Fu H. Z., Zhang L. H. Ywo new triterpenoids from the roots of Caragana intermedia K.. J. Chin. Pharm. Sci. 1998, 7(1): 1~5
[34] Boinik V. V., Kovalev V. N., Komissarenko N. F., et al. Coumarins from the aboveground part of Caragana frutex. Khimiya Prirodnykh Soedinenii. 1983, (6): 780~781
[35] 朴惠顺,金光洙,李迎军等,小叶锦鸡儿醋酸乙酯提取物抗炎作用的研究,时珍国医国药,2006,17(8):1453~1454
[36] 金景姬,方文龙,金正男等,小叶锦鸡儿的抗炎作用,中国中药杂志,1993,18(5):306~308
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