过山蕨乙醇提取物化学成分的分离鉴定
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摘要
目的:研究过山蕨Camptosorus sibiricus全草95%乙醇提取物的化学成分,并测定其抗氧化活性。方法:采用正相硅胶,小孔树脂(MCI),LH-20型羟丙基葡聚糖凝胶(Sephadex LH-20),制备薄层色谱和反相HPLC等多种色谱技术进行分离纯化,通过波谱数据分析,结合文献鉴定了化合物的结构。结果:共分离得到11个化合物,分别鉴定为香豆酸(1),香豆酸4-O-β-D-吡喃葡萄糖苷(2),顺式对香豆酸4-O-β-D-吡喃葡萄糖苷(3),阿魏酸4-O-β-D-吡喃葡萄糖苷(4),咖啡酸甲酯(5),阿魏酸甲酯(6),丁香酸(7),丁香酸-4-O-β-D-吡喃葡萄糖苷(8),原儿茶醛(9),香草醛(10),丁香醛(11)。结论:化合物3～11均为首次从过山蕨属中分离得到。对从过山蕨乙醇提取物中分离的11个化合物采用类超氧化物歧化酶(SOD-like)活性测试法进行了抗氧化活性研究,结果显示化合物7,9～11均有一定活性,四者的半抑制浓度(IC50)分别为16. 70,11. 70,12. 23,13. 52μmol·L~(-1);在浓度1. 0×10~(-4)mol·L~(-1)下,其他化合物均未表现出活性。
Objective: To study the chemical constituents in 95% ethanol extract of the whole plant of Camptosorus sibiricus and determine its antioxidant activity. Method: Compounds were isolated by a combination of various chromato-graphic techniques,including column chromatography over silica gel and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified on the basis of physicochemical properties and spectral data reported in the literature. Result: Eleven compounds were identified as trans-p-coumaric acid( 1), trans-pcoumaric acid 4-O-β-D-glucoside( 2),cis-p-coumaric acid 4-O-β-D-glucoside( 3),( E)-ferulic acid-4-O-β-Dglucoside( 4),caffeic acid methyl ester( 5),ferulic acid methyl ester( 6),syringic acid( 7),syringic acid-4-O-β-D-glucopyranoside( 8),protocatechualdehyde( 9),vanillain( 10) and syringaldehyde( 11),respectively.Conclusion: Compounds 3-11 are isolated from the genus Camptosorus for the first time. In the in vitro SOD-like activity assays,compounds 7,9-11 show an antioxidant activity with half maximal inhibitory concentration( IC50)values of 16. 70,11. 70,12. 23 and 13. 52 μmol·L~(-1),respectively.
Objective: To study the chemical constituents in 95% ethanol extract of the whole plant of Camptosorus sibiricus and determine its antioxidant activity. Method: Compounds were isolated by a combination of various chromato-graphic techniques,including column chromatography over silica gel and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified on the basis of physicochemical properties and spectral data reported in the literature. Result: Eleven compounds were identified as trans-p-coumaric acid( 1), trans-pcoumaric acid 4-O-β-D-glucoside( 2),cis-p-coumaric acid 4-O-β-D-glucoside( 3),( E)-ferulic acid-4-O-β-Dglucoside( 4),caffeic acid methyl ester( 5),ferulic acid methyl ester( 6),syringic acid( 7),syringic acid-4-O-β-D-glucopyranoside( 8),protocatechualdehyde( 9),vanillain( 10) and syringaldehyde( 11),respectively.Conclusion: Compounds 3-11 are isolated from the genus Camptosorus for the first time. In the in vitro SOD-like activity assays,compounds 7,9-11 show an antioxidant activity with half maximal inhibitory concentration( IC50)values of 16. 70,11. 70,12. 23 and 13. 52 μmol·L~(-1),respectively.
引文
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[21]王业玲.石见穿化学成分及其生物活性研究[D].沈阳:沈阳药科大学,2008.
[22]王新玲,王晓梅,胡君萍,等.新疆鼠尾草不同部位不同极性提取物抗氧化活性[J].中国实验方剂学杂志,2017,23(23):62-65.
[23]肖凯,冯大伟,杨金丽,等.盔状黄芩中的苯乙醇苷及黄酮苷类化合物分析[J].中国实验方剂学杂志,2017,23(20):36-41.
[2]李宁.过山蕨和山茶种子的化学成分和药理活性研究[D].沈阳:沈阳药科大学,2006.
[3] ZHANG P,CHENG Y Y,MA Z J,et al. New cycloartane glycosides from Camptosorus sibiricus Rupr.[J]. J Asian Nat Prod Res,2008,10(11):1069-1074.
[4]沈阳药学院药学四十一期队.过山蕨的扩张血管作用和毒性[J].沈阳药学院学报,1977,7(7):34-37.
[5]沈阳药学院药学四十一期队.过山蕨治疗脉管炎有效部位的实验研究[J].沈阳药学院学报,1977,7(38):38-43.
[6]徐绥绪.过山蕨治疗心血管病的研究. 5.过山蕨治疗脉管炎有效成分的研究[J].沈阳药学院学报,1979,36(11):36-46.
[7]梁大连,程艳玲,董世波,等.过山蕨总黄酮对大鼠血栓闭塞性脉管炎的改善作用[J].现代药物与临床,2011,26(6):481-484.
[8]张宝凤,周荣汉,董淑华,等.过山蕨治疗心血管病的研究[J].沈阳药学院学报,1979,11(29):29-35.
[9]梁大连,于亮,李宁,等.过山蕨水提物的化学成分[J].沈阳药科大学学报,2017,34(7):541-545,552.
[10]郭娟丽,张培成,张智武.油菜花粉的化学成分研究[J].中国中药杂志,2009,34(10):1235-1237.
[11]吴慧星,李晓帆,李荣,等.番石榴叶中抗氧化活性成分的研究[J].中草药,2010,41(10):1593-1597.
[12]徐璐,李艳茸,李春,等.藏药甘青乌头化学成分研究[J].中国中药杂志,2013,38(17):2818-2825.
[13]马双成,毕培曦,黄荣春,等.金银花药材中抗呼吸道病毒感染的咖啡酰奎宁酸类成分的定量研究[J].药物分析杂志,2005,25(7):751-755.
[14] Pieters L,Dyck S V,Gao M,et al. Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization[J]. J Med Chem,1999,42:5475-5481.
[15] CHANG Y C,CHANG R F,WU Y C. The constituents of Lindera glauea[J]. J Chin Chem Soc,2000,47:373-380.
[16] Kashiwada Y,Nonaka G I,Nishioka I. Tannins and related compounds. XLV. Rhubarb.(5):isolation and characterization of flavan-3-ol and procyanidin glucosides[J]. Chem Pharm Bull,1986,34(8):3208-3222.
[17]赵爱华,赵勤实,李蓉涛,等.肾茶的化学成分研究[J].云南植物研究,2004,26(5):563-568.
[18]羊晓东,梅双喜,杨蓉,等.云南兔耳草的化学化学成分研究[J].天然产物研究与开发,2002,14(6):1-3.
[19] Schwartz A. Efficient synthesis of 3, 4, 5-trimethoxybenzaldehyde via reissert aldehyde synthesis[J]. J Org Chem,1982,47(11):2213-2214.
[20] LI N,LI X,ZHANG Y,et al. Free radical scavengers,antioxidants and aldose reductase inhibitors from Camptosorus sibiricus Rupr[J]. Z Naturforsch C,2008,63(1/2):66-68.
[21]王业玲.石见穿化学成分及其生物活性研究[D].沈阳:沈阳药科大学,2008.
[22]王新玲,王晓梅,胡君萍,等.新疆鼠尾草不同部位不同极性提取物抗氧化活性[J].中国实验方剂学杂志,2017,23(23):62-65.
[23]肖凯,冯大伟,杨金丽,等.盔状黄芩中的苯乙醇苷及黄酮苷类化合物分析[J].中国实验方剂学杂志,2017,23(20):36-41.