CN101602768B - 一种芝麻素和芝麻林素的提纯方法 - Google Patents
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Abstract
本发明涉及一种芝麻油中的芝麻素和芝麻林素的提纯方法。先从芝麻油中分离得到不含脂肪类成分的木脂素类化合物，之后加入乙醚析出芝麻素；过滤，所得滤液减压浓缩后用氯仿溶解，然后加入石油醚至有白色浑浊出现，加热溶解后静置析出芝麻林素。本发明芝麻素和芝麻林素的纯化方法，具有操作简单、安全经济、工艺稳定性强等优点，特别适宜工业化应用，该方法可同时得到高纯度的芝麻素和芝麻林素，达到综合利用的目的。
Description
(一)技术领域
本发明涉及一种芝麻油中的芝麻素和芝麻林素的提纯方法。
(二)背景技术
芝麻素是一种主要存在于芝麻中的木酚素类化合物，分子式为C20H18O6，熔点121-123℃，其含量约占芝麻的0.2％-0.5％，在非焙烤和未经精炼工艺处理的芝麻油中含量为0.5-1％，是芝麻中重要的生物活性成分之一。大量的体外实验、动物实验和临床实验证明芝麻素具有广泛的生物活性，它不仅可以保护及强化肝功能、调节血压、降低胆固醇，更可以直接作用于组织器官，发挥其优异的抗氧化能力。除了研究其生理学活性及其对机体健康的有益效应外，也有人对芝麻素的杀菌效果和对其它食用植物油品成分的稳定作用进行了研究。研究结果显示，芝麻素这一天然植物成分，不仅可以作为保持食品风味的防腐剂，也能够作为增强机体健康的保健品添加剂，还可开发成防病治病的天然药物。
芝麻林素也是存在于芝麻及芝麻油中的主要木脂素类成分之一，分子式为C20H18O7，熔点93-94℃，是芝麻中重要的生物活性成分之一，其含量仅次于芝麻素，约占芝麻的0.1-0.3％，在非焙烤和未经精炼工艺处理的芝麻油中含量为0.2-0.5％，是芝麻中重要的生物活性成分之一。研究表明芝麻林素具有消除体内自由基、降低血清中的胆固醇、增强机体免疫力、抗高血压、抗血栓、缓解动脉粥样硬化，并有促进酒精代谢、加强解毒活性、抗肝中毒、抑制乳腺癌等众多功效。除了其本身具有抗氧化活性外，还可在一定条件下转化为抗氧化能力更强的芝麻酚和芝麻素酚，应用前景十分广阔。
芝麻及芝麻油中含有相对较多的芝麻素和芝麻林素，但现有的成熟的制备技术只能得到单一的芝麻素，而同时制备得到芝麻林素的技术仍不成熟；能够同时纯化出芝麻素和芝麻林素的方法工艺繁琐复杂，特别是制备高纯度的芝麻林素需要多次柱层析操作，且最后的纯化阶段大都用制备高效液相色谱法纯化，显然不适于工业化生产应用，这也限制了芝麻林素相关产品的开发。
(三)发明内容
本发明的目的在于提供一种芝麻素和芝麻林素的提纯方法，克服现有方法只能得到单一有效成分或纯化方法复杂不适于工业应用的缺陷。
本发明采用的技术方案如下：
一种芝麻素和芝麻林素的提纯方法，先从芝麻油中分离得到不含脂肪类成分的木脂素类化合物，之后加入乙醚析出芝麻素；过滤，所得滤液减压浓缩后用氯仿溶解，然后加入石油醚至有白色浑浊出现，加热溶解后静置析出芝麻林素。
所述乙醚的用量为每克木脂素类化合物加入5-15mL。
加入乙醚静置析出芝麻素，所述的静置的时间为0.5-24h，静置温度为-10-20℃。
氯仿的加入量为每克木脂素类化合物加入3-10mL。
加热溶解后所述的静置的时间为12-48h，静置温度为-20-5℃。
从芝麻油中分离得到不合脂肪类成分的木脂素类化合物的方法为溶剂低温沉淀法、皂化法、柱层析法、减压蒸馏法中的一种或两种以上方法的结合。
所述的芝麻油为非焙炒芝麻粗油或焙炒芝麻油或从饼粕中提取的残油。
本发明的纯化芝麻素和芝麻林素的方法，首先是从芝麻油中分离出不合脂肪类成分的木脂素类化合物，再采用特定溶剂析晶的方法从木脂素类化合物中纯化出高纯度的芝麻素和芝麻林素。析出的芝麻素固体和芝麻林素固体分别经乙醇重结晶，纯度可达95％以上。
具体的，得到主要成分为芝麻素和芝麻林素的木脂素类混合物后，先将混合物中加入一定量的乙醚，静置一段时间使混合物中的芝麻素析出，过滤，滤饼为白色粉末状固体即芝麻素；滤液减压蒸除溶剂后再用少量氯仿溶解，然后加入石油醚至有白色浑浊出现为止，稍加热溶解后，静置一段时间后即有白色芝麻林素固体析出。
本发明在纯化芝麻林素的过程中，根据该混合物中芝麻素含量相对较高及芝麻素不溶于乙醚而芝麻林素微溶于乙醚这一特性，用乙醚溶剂法析晶先分离出大部分的芝麻素；分离出大部分芝麻素后，混合物中的主要成分仍为芝麻素和芝麻林素及其他不皂化物，但芝麻素的含量大大降低，芝麻林素的含量增大。因此采用氯仿和石油醚的混合溶剂析晶又可使芝麻林素析出；相对于往常精制芝麻林素一般采用的工艺稳定性差、处理量小、对操作者要求高、填料成本高的色谱法，该方法具有操作简单、安全经济、工艺稳定性强等优点，特别适宜工业化生产，该方法同时还能得到高纯度的芝麻素产品，达到综合利用的目的。
本发明相对于现有技术，有以下优点：
本发明芝麻素和芝麻林素的纯化方法，具有操作简单、安全经济、工艺稳定性强等优点，特别适宜工业化应用，该方法可同时得到高纯度的芝麻素和芝麻林素，达到综合利用的目的；析出的芝麻素和芝麻林素分别经乙醇重结晶处理可得到纯度达95％以上的产品。
(四)具体实施方式：
以下以具体实施例来说明本发明的技术方案，但本发明的保护范围不限于此：
实施例1
取石油醚萃取的芝麻油100g，加入甲醇500mL，90℃回流萃取20min，待冷至室温后，置-30℃下冷冻8h，甘油三酯凝固，在-20℃下抽滤，得木脂素类化合物的混合物的萃取液，减压脱除甲醇，得浅黄色膏状物。
向该膏状物中加入20mL质量浓度为5％的氢氧化钾的乙醇溶液，90℃皂化10min，冷却后加水100mL并转移至500mL分液漏斗中用乙醚萃取，再经水洗、无水硫酸钠干燥、抽滤及减压脱除溶剂操作得浅黄色半固体膏状物。
向浅黄色半固体膏状物中加入20mL乙醚，充分振荡后密封于5℃条件下放置6h，析出白色粉末状芝麻素固体，抽滤得滤液及白色粉末状固体，该固体用8mL乙醇重结晶析出白色针状结晶，经分离、洗涤及真空干燥得纯度达95％以上的芝麻素0.41g。滤液蒸除溶剂后，加3mL氯仿稍加热溶解，然后加入石油醚直至有白色浑浊出现，稍加热使浑浊消失后，0℃静置12h，析出白色固体，该白色固体经5mL乙醇重结晶析出白色羽毛状晶体，经分离、洗涤及真空干燥得纯度达95％以上的芝麻林素0.24g。
实施例2
取市售焙炒芝麻油200mL，加入到氧化铝柱(40cm×4cm i.d.，氧化铝150g)中，并用石油醚洗脱，采用2mL洗脱液加1mL含2％(wt％)蔗糖的浓盐酸加热反应5min进行监测，至反应出现微红色时洗脱剂更换为乙酸乙酯进行洗脱，直至不出现颜色反应为止。乙酸乙酯洗脱液经减压蒸除溶剂后得黄色半固状膏体。
该膏体先后用乙醚、氯仿、石油醚及乙醇等进行析晶和重结晶处理，得到纯度达95％以上的芝麻素和芝麻林素分别为0.68g和0.33g。所用乙醚为25mL，氯仿为4mL，芝麻素和芝麻林素重结晶所用乙醇分别为10mL和6mL，其他同实施例1。
Claims (4)
1.一种芝麻素和芝麻林素的提纯方法，其特征在于，先从芝麻油中分离得到不含脂肪类成分的木脂素类化合物，之后加入乙醚析出芝麻素；过滤，所得滤液减压浓缩后用氯仿溶解，然后加入石油醚至有白色浑浊出现，加热溶解后静置析出芝麻林素；所述乙醚的用量为每克木脂素类化合物加入5-15mL；氯仿的加入量为每克木脂素类化合物加入3-10mL；从芝麻油中分离得到不含脂肪类成分的木脂素类化合物的方法为溶剂低温沉淀法、皂化法、柱层析法、减压蒸馏法中的一种或两种以上方法的结合。
2.如权利要求1所述的芝麻素和芝麻林素的提纯方法，其特征在于，加入乙醚静置析出芝麻素，所述的静置的时间为0.5-24h，静置温度为-10-20℃。
3.如权利要求1所述的芝麻素和芝麻林素的提纯方法，其特征在于，所述的静置的时间为12-48h，静置温度为-20-5℃。
4.如权利要求1-3之一所述的芝麻素和芝麻林素的提纯方法，其特征在于，所述的芝麻油为非焙炒芝麻粗油、焙炒芝麻油或从饼粕中提取的残油。
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101254187A (zh) * | 2008-02-22 | 2008-09-03 | 朱萧俊 | 一种治疗代谢综合症的组合物 |
-
2009
- 2009-07-17 CN CN2009100654601A patent/CN101602768B/zh not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101254187A (zh) * | 2008-02-22 | 2008-09-03 | 朱萧俊 | 一种治疗代谢综合症的组合物 |
Non-Patent Citations (1)
| Title |
|---|
| 张燕飞等.芝麻中芝麻素提取工艺研究进展.《粮食与油脂》.2008,(第11期),全文. * |
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