CN101096378B - 白花蛇舌草中环烯醚萜类化合物单体的提取、分离方法 - Google Patents
白花蛇舌草中环烯醚萜类化合物单体的提取、分离方法 Download PDFInfo
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- CN101096378B CN101096378B CN2006100284687A CN200610028468A CN101096378B CN 101096378 B CN101096378 B CN 101096378B CN 2006100284687 A CN2006100284687 A CN 2006100284687A CN 200610028468 A CN200610028468 A CN 200610028468A CN 101096378 B CN101096378 B CN 101096378B
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CN2006100284687A CN101096378B (zh) | 2006-06-30 | 2006-06-30 | 白花蛇舌草中环烯醚萜类化合物单体的提取、分离方法 |
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CN2006100284687A CN101096378B (zh) | 2006-06-30 | 2006-06-30 | 白花蛇舌草中环烯醚萜类化合物单体的提取、分离方法 |
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Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101637475B (zh) * | 2008-07-29 | 2011-06-01 | 上海医药工业研究院 | 鸡矢藤苷酸或含其的植物提取物的应用 |
CN103610798B (zh) * | 2013-11-28 | 2015-11-04 | 中国计量学院 | 一种白花蛇舌草的活性部位及其制备方法、应用 |
CN104547148A (zh) * | 2014-12-15 | 2015-04-29 | 山东省药学科学院 | 一种用于防治老年性痴呆的白花蛇舌草提取物及制备方法 |
CN108503678A (zh) * | 2017-02-24 | 2018-09-07 | 深圳曜曦生命科技有限公司 | 一种环烯醚萜类化合物及其制备方法和应用 |
CN109053831B (zh) * | 2018-09-04 | 2020-04-21 | 山东中医药大学附属医院 | 一种白花蛇舌草中的新型化合物及应用 |
CN109796511B (zh) * | 2019-03-05 | 2021-10-22 | 山东省药学科学院 | 一种新的环烯醚萜类化合物及其制备方法和医药用途 |
WO2021196105A1 (zh) * | 2020-04-02 | 2021-10-07 | 广东新纪元生命科技有限公司 | 白花蛇舌草抗肿瘤有效组分及其制备方法和用途 |
CN112851621B (zh) * | 2021-01-28 | 2023-03-17 | 汕头大学医学院 | 牛白藤总环烯醚萜提取物、提取纯化方法及其应用 |
CN114886907A (zh) * | 2022-06-15 | 2022-08-12 | 山东中医药大学附属医院 | (e)-6-o-对香豆酰鸡屎藤次苷甲酯在制备预防/治疗肝损伤药物中的应用 |
-
2006
- 2006-06-30 CN CN2006100284687A patent/CN101096378B/zh not_active Expired - Fee Related
Non-Patent Citations (4)
Title |
---|
Houming Wu, et al.IFUDOIDS FROM HEDYOTIS DIFFUSA.《Journal of Natural Products》.1991,第54卷(第1期),254-256. * |
Y. Nishihama, et al.Three New iridiod glucosides from hedyotis diffusa.《Planta medica》.1981,第43卷(第1期),28-33. * |
Youngleem Kim, et al.Neuroprotective Constituents from Hedyotis diffusa.《Journal of Natural Products》.2000,第64卷(第1期),75-78. * |
吴孔松等.白花蛇舌草化学成分的研究.《中国药学杂志》.2005,第40卷(第11期),817-819. * |
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