张姣,德吉,付爱玲,陈道峰,卢燕.密枝圆柏的化学成分及其抗补体、抗氧化活性[J].中草药,2019,(13):3008-3016
密枝圆柏的化学成分及其抗补体、抗氧化活性
Anticomplementary and anti-oxidant activities of constituents from Juniperus convallium
投稿时间:2019-04-26  
DOI:10.7501/j.issn.0253-2670.2019.13.003
中文关键词:  密枝圆柏  抗补体  抗氧化  穗花杉双黄酮  柏木双黄酮  芹菜素  槲皮素-3-O-β-D-葡萄糖苷
英文关键词:Juniperus convallium Rehder et E. H. Wilson  anticomplementary activity  anti-oxidant activity  amentoflavone  cupressu-flavone  apigenin  quercetin 3-O-β-D-glucoside
基金项目:国家自然科学基金面上项目(81673690);西藏自治区科技计划重大科技项目(XZ201801-GH-13)
作者单位E-mail
张姣 复旦大学药学院, 上海 201203
西南大学药学院, 重庆 400715 
 
德吉 西藏大学理学院, 西藏 拉萨 850000  
付爱玲 西南大学药学院, 重庆 400715  
陈道峰 复旦大学药学院, 上海 201203  
卢燕 复旦大学药学院, 上海 201203 luyan@fudan.edu.cn 
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中文摘要:
      目的 对密枝圆柏Juniperus convallium进行化学成分和抗补体、抗氧化活性研究。方法 采用正相硅胶、ODS-C18、Sephadex LH-20以及制备型HPLC等方法进行分离纯化,结合理化性质和波谱数据鉴定化合物结构,采用细胞溶血法测定经典、旁路途径的抗补体活性及作用靶点,DPPH、ABTS、FRAP法研究抗氧化活性。结果 从密枝圆柏醋酸乙酯部位分离鉴定了17个化合物,包括黄酮类化合物9个:穗花杉双黄酮(1)、柏木双黄酮(2)、柏木双黄酮葡萄糖苷(3)、柚皮素-7-O-葡萄糖苷(4)、芹菜素(5)、山柰酚-3-O-(6″-O-E-肉桂酰基)-β-D-吡喃葡萄糖苷(6)、槲皮素-3-O-β-D-葡萄糖苷(7)、槲皮素吡喃鼠李糖苷(8)和海波拉亭-7-O-β-D-吡喃葡萄糖苷(9);木脂素类化合物3个:异马尾松脂苷B(10)、异落叶松脂素-2a-O-β-D-葡萄糖苷(11)和异落叶松脂素-3a-O-β-D-葡萄糖苷(12);萜类化合物3个:柳叶二醇(13)、3β-羟基山达海松酸(14)和(1R,3R,4aR,4bS,7R,10aR)-7-乙烯基-1,2,3,4,4a,4b,5,6,7,9,10,10a-十二氢-3-羟基-1,4a,7-三甲基-1-菲甲醇(15);以及大丁苷元(16)和β-谷甾醇(17)。除16外,不同类型化合物对补体系统都显示了一定程度的抑制活性,经典途径50%抑制溶血所需浓度(CH50)为0.05~3.99 mmol/L,旁路途径50%抑制溶血所需浓度(AP50)为0.58~19.13 mmol/L,其中,黄酮类化合物尤其是双黄酮类,是密枝圆柏中重要的抗补体活性成分,并且酚羟基和糖苷基团是影响其抗补体活性的重要因素。仅羟基基团较多的黄酮类(1359)和木脂素类(1012)化合物显示不同程度的抗氧化活性。结论 所有化合物均为首次从密枝圆柏中分离得到,黄酮及木脂素类是其抗补体和抗氧化的主要活性成分,且显示出一定的构效关系,为密枝圆柏药效物质基础及质量控制研究提供了依据。
英文摘要:
      Objective To investigate the chemical constituents from Juniperus convallium, as well as their anticomplementary and antioxidant activities. Methods The constituents were isolated and purified by column chromatography over silica gel, Sephadex LH-20, ODS-C18, and preparative HPLC. Their structures were identified by spectra analysis. The cell hemolysis assay was used to evaluate the anticomplementary activities and the targets through classical and alternative pathways. Also the anti-oxidant activities were tested by DPPH, ABTS and FRAP methods. Results A total of 17 compounds were obtained from the ethyl acetate extract of J. convallium and identified as amentoflavone (1), cupressuflavone (2), cupressuflavone-4″'-O-β-D-glucosides (3), naringenin-7-O-glycoside (4), apigenin (5), tiliroside (6), quercetin 3-O-β-D-glucoside (7), quercetin-3-O-rhamnoside (8), hypolaetin-7-O-β-D-glucopyranoside (9), isomassonianoside B (10), (+)-isolariciresinol 2a-O-β-D-glucoside (11), (+)-isolarisiresinol 3a-O-β-D-glucopyranoside 12), cryptomeridiol (13), 3β-hydroxysandaracopimeric acid (14), (1R,3R,4aR,4bS,7R,10aR)-7-ethenyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydro-3-hydroxy-1,4a,7-trimethyl-1-phenanthrene methanol (15), 4-hydroxy-5-methyl-coumarin (16) and β-sitosterol (17). Compounds 1-15 and 17 showed anticomplementary activities in different degrees (CH50:0.05-3.99 mmol/L, AP50:0.58-19.13 mmol/L). The flavonoids, especially the biflavonoids, are the important anticomplementary constituents in J. convallium. Further analysis of structure-activity relationship showed that phenolic hydroxyl and glycosidic groups influenced their anticomplementary activity. Only the flavonoids (1-3, 5-9) and lignans (10-12) showed different degrees of antioxidant activities due to their hydroxyl groups. Conclusion All the 17 compounds are isolated from J. convallium for the first time. The flavonoids and lignans are the important anticomplementary and antioxidant constituents in J. convallium with a certain structure-acticity relationship. This study provides a good reference for further research on the pharmacological substance and quality control of J. convallium.
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