CN104817603B - 从莲房中制备槲皮素-3-O-β-D-葡萄糖醛酸苷的方法 - Google Patents
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Abstract
本发明涉及中药技术领域，尤其涉及从莲房中制备槲皮素‑3‑O‑β‑D‑葡萄糖醛酸苷的方法。所述方法是以莲房为原料，经含水乙醇回流提取提取，浓缩液经大孔吸附树脂初步纯化，10%乙醇洗脱部位直接经反相硅胶柱纯化，制得槲皮素‑3‑O‑葡萄糖醛酸苷单体化合物，纯度达90%以上。该方法原料丰富易得，工艺简单易行，操作简便，高效环保，适用于工业应用。
Description
技术领域
本发明涉及中药技术领域，尤其涉及从莲房中制备槲皮素-3-O-β-D-葡萄糖醛酸苷的方法。
背景技术
莲房Nelumbinis Receptaculum是睡莲科植物莲Nelumbo nucifera Gaertn.的干燥花托，味苦，性涩、温，具有化瘀止血的功效，用于崩漏，尿血，痔疮出血，产后瘀阻，恶露不尽。药理研究表明，莲房具有抗氧化、抗辐射、抗肿瘤、抗衰老、抗心肌缺血、保肝和保护心血管等作用。槲皮素-3-O-β-D-葡萄糖醛酸苷是莲房中含量最高的黄酮醇苷类成分，具有抗氧化、抗炎、抗肿瘤等多种生物活性，以往从莲房中分离该化合物的主要步骤为：莲房干燥后粉碎，用75%乙醇回流提取，提取液回收乙醇后加水溶解，依次用石油醚、乙酸乙酯、正丁醇分别萃取。正丁醇部分经硅胶柱反复层析，二氯甲烷-甲醇梯度洗脱后再经过反复硅胶柱色谱、Sephadex LH 20柱色谱后得到槲皮素-3-O-β-D-葡萄糖醛酸苷（Wu YB, Zheng LJ, WuJG, et al. Antioxidant Activities of Extract and Fractions from ReceptaculumNelumbinis and Related Flavonol Glycosides. International Journal ofMolecular Sciences, 2012, 13(6): 7163-7173）；或者新鲜莲房用60%甲醇于50℃浸提，提取液回收溶剂后上AB-8大孔树脂，依次用水洗脱，再用70%乙醇洗脱，70%乙醇洗脱液回收溶剂后加入乙酸酸化后的丙酮，离心后收集沉淀，沉淀溶于水后再经过聚酰胺柱色谱和反相C18柱色谱，以不同浓度的甲醇水混合溶剂洗脱后得到到槲皮素-3-O-β-D-葡萄糖醛酸苷（Xiao JS, Xie BJ, Cao YP, et al. Characterization of Oligomeric Procyanidinsand Identification of Quercetin Glucuronide from Lotus (NelumbonuciferaGaertn.) Seedpod. Journal of Agricultural and Food Chemistry, 2012,60(11): 2825-2829）。
上述的制备方法步骤繁琐、操作费时、产品得率较低、有机溶剂用量较大、成本较高、易造成环境污染，而且产品易残留有机溶剂从而影响产品的安全性，不适合工业化生产。因此，急需一种高效、简便、低成本、安全的提取分离技术来解决现有技术中所存在的这一问题。
发明内容
本发明的目的在于提供从莲房中制备槲皮素-3-O-β-D-葡萄糖醛酸苷的方法。本方法通过乙醇和水混合溶剂来进行提取分离，保证产品的安全性，也简化了分离的流程，适用于工业化生产。
为实现上述目的，本发明采用如下技术方案：以莲房为原料，经含水乙醇回流提取提取，浓缩液经大孔吸附树脂初步纯化，10%乙醇洗脱部位直接经反相硅胶柱纯化，制得槲皮素-3-O-葡萄糖醛酸苷单体化合物。
本发明提供的制备槲皮素-3-O-β-D-葡萄糖醛酸的方法包括以下步骤：
a：将干燥后的莲房粉碎，用30%-75%乙醇回流提取2次，提取液减压浓缩，得到初提取物；
b：步骤a中所得的初提取物加水溶解后过滤，滤液上大孔树脂，依次用10 BV水洗脱，再用15%乙醇洗脱，收集15%乙醇洗脱洗脱液，减压回收溶剂，得到含槲皮素-3-O-葡萄糖醛酸苷的粗提取物；
c：将步骤b中所得的粗提取物过反相C18硅胶柱色谱，以水洗脱4-8倍柱体积，再用15%乙醇洗脱洗，收集15%乙醇洗脱洗脱液，减压回收溶剂，得槲皮素-3-O-β-D-葡萄糖醛酸苷。
所述步骤a中的莲房药材和乙醇水的料液比为1:10-20。
所述步骤a中的提取方法为回流提取、超声提取、和浸渍提取中的任意一种。
所述步骤b中的大孔树脂优选中极性或弱极性大孔树脂。
本发明的优点是：本提取方法选用安全、无毒的水和乙醇为提取溶剂，既保证了产品的质量又不会污染环境，且生产成本低、制备方法简单，适合用于工业化大生产。另外本产品的研究还可以发掘莲房潜在的医药用途，促进莲房药材的深加工，提高农产品的附加值，增加莲农的收入。
具体实施方式
下面结合具体实施例对本发明作进一步说明，所述的是对本发明的解释而不是限定。
实施例1
莲房药材500g，用10倍30%乙醇回流提取2次，提取液过滤，滤液合并减压浓缩，得到提取物，提取物加水溶解后过滤，滤液上HPD-722大孔树脂，依次用10 BV水洗脱，再用15%乙醇洗脱，收集15%乙醇洗脱液，减压浓缩后用水溶解，上反相C18硅胶柱色谱，以10 BV水洗脱，再用15%乙醇洗脱，收集15%乙醇洗脱液，减压回收溶剂，得槲皮素-3-O-β-D-葡萄糖醛酸苷6.18g，经HPLC法检测，纯度为91.4%。
实施例2
莲房药材500g，用15倍50%乙醇回流提取2次，提取液过滤，滤液合并减压浓缩，得到提取物，提取物加水溶解后过滤，滤液上HPD-400大孔树脂，依次用10 BV水洗脱，再用15%乙醇洗脱，收集15%乙醇洗脱液，减压浓缩后用水溶解，上反相C18硅胶柱色谱，以10 BV水洗脱，再用15%乙醇洗脱，收集15%乙醇洗脱液，减压回收溶剂，得槲皮素-3-O-β-D-葡萄糖醛酸苷6.34g，经HPLC法检测，纯度为92.4%。
实施例3
莲房药材500g，用20倍75%乙醇回流提取2次，提取液过滤，滤液合并减压浓缩，得到提取物，提取物加水溶解后过滤，滤液上AB-8大孔树脂，依次用10 BV水洗脱，再用15%乙醇洗脱，收集15%乙醇洗脱液，减压浓缩后用水溶解，上反相C18硅胶柱色谱，以10 BV水洗脱，再用15%乙醇洗脱，收集15%乙醇洗脱液，减压回收溶剂，得槲皮素-3-O-β-D-葡萄糖醛酸苷5.94g，经HPLC法检测，纯度为93.3%。
以上所述仅为本发明的较佳实施例，凡依本发明申请专利范围所做的均等变化与修饰，皆应属本发明的涵盖范围。
Claims (1)
1.从莲房中制备槲皮素-3-O-β-D-葡萄糖醛酸苷的方法，其特征在于：包括如下步骤：
a：将干燥后的莲房粉碎，用75%乙醇回流提取2次，提取液减压浓缩，得到初提取物；
b：步骤a中所得的初提取物加水溶解后过滤，滤液上大孔树脂，先用水洗脱10个柱体积，再用15%乙醇洗脱，收集15%乙醇洗脱洗脱液，减压回收溶剂，得到含槲皮素-3-O-葡萄糖醛酸苷的粗提取物；
c：将步骤b中所得的粗提取物过反相C18硅胶柱色谱，以水洗脱10倍柱体积，再用15%乙醇洗脱洗，收集15%乙醇洗脱洗脱液，减压回收溶剂，得槲皮素-3-O-β-D-葡萄糖醛酸苷；
所述步骤a中的莲房药材和乙醇水的料液比为1: 20；
步骤b所述大孔树脂为中极性或弱极性大孔树脂。
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| CN116539749A (zh) * | 2023-04-28 | 2023-08-04 | 北京电子科技职业学院 | 一种用于检测监控不同莲中槲皮素-3-O-β-D-葡萄糖醛酸苷含量的系统及方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020187207A1 (en) * | 2001-02-15 | 2002-12-12 | Institut National De La Recherche Agronomique Inra | Method for extracting, fractionating and purifying polyphenolic compounds originating from fresh plant sorting deviations using a high adsorption and elution performance resin |
| CN101851261A (zh) * | 2010-06-10 | 2010-10-06 | 贵州师范大学 | 杠板归药材及其制剂中有效成分的对照品制法及含量测定方法 |
| WO2011140655A1 (en) * | 2010-05-10 | 2011-11-17 | Dalhousie University | Phenolic compositions derived from apple skin and uses thereof |
| WO2012048119A2 (en) * | 2010-10-06 | 2012-04-12 | The Board Of Trustees Of The University Of Arkansas | Anti-biofilm compositions and methods for using |
| CN102827221A (zh) * | 2012-08-25 | 2012-12-19 | 浙江大学 | 荷叶中具α-葡萄糖苷酶抑制活性的化合物及用途 |
| CN102824756A (zh) * | 2012-09-07 | 2012-12-19 | 浙江大学 | 一种从植物提取物中筛选甘油三酯酶抑制剂的方法 |
| US20130323372A1 (en) * | 2010-11-19 | 2013-12-05 | Laboratoires Expanscience | Method for extracting molelcules of interest from all or part of a plant matrix |
-
2015
- 2015-04-11 CN CN201510168190.2A patent/CN104817603B/zh not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020187207A1 (en) * | 2001-02-15 | 2002-12-12 | Institut National De La Recherche Agronomique Inra | Method for extracting, fractionating and purifying polyphenolic compounds originating from fresh plant sorting deviations using a high adsorption and elution performance resin |
| WO2011140655A1 (en) * | 2010-05-10 | 2011-11-17 | Dalhousie University | Phenolic compositions derived from apple skin and uses thereof |
| CN101851261A (zh) * | 2010-06-10 | 2010-10-06 | 贵州师范大学 | 杠板归药材及其制剂中有效成分的对照品制法及含量测定方法 |
| WO2012048119A2 (en) * | 2010-10-06 | 2012-04-12 | The Board Of Trustees Of The University Of Arkansas | Anti-biofilm compositions and methods for using |
| US20130323372A1 (en) * | 2010-11-19 | 2013-12-05 | Laboratoires Expanscience | Method for extracting molelcules of interest from all or part of a plant matrix |
| CN102827221A (zh) * | 2012-08-25 | 2012-12-19 | 浙江大学 | 荷叶中具α-葡萄糖苷酶抑制活性的化合物及用途 |
| CN102824756A (zh) * | 2012-09-07 | 2012-12-19 | 浙江大学 | 一种从植物提取物中筛选甘油三酯酶抑制剂的方法 |
Non-Patent Citations (1)
| Title |
|---|
| Characterization of Oligomeric Procyanidins and Identification of Quercetin Glucuronide from Lotus (Nelumbo nucifera Gaertn.) Seedpod;Jun-Song Xiao，等;《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》;20120228;第60卷;第2825页右栏最后一段至2826页右栏第1段，2828页右栏第一段 * |
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