CN112645994B - 一种红景天苷的提取工艺 - Google Patents
一种红景天苷的提取工艺 Download PDFInfo
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- CN112645994B CN112645994B CN202110049505.7A CN202110049505A CN112645994B CN 112645994 B CN112645994 B CN 112645994B CN 202110049505 A CN202110049505 A CN 202110049505A CN 112645994 B CN112645994 B CN 112645994B
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Abstract
一种红景天苷的提取工艺,包括:步骤一:将红景天提取物与磁性颗粒混合孵化,得到混合液a;步骤二:将混合液a用磁铁或置于磁场中吸引分离,得到吸附磁性颗粒b;步骤三:将吸附磁性颗粒b浸泡于洗脱液A中,然后用磁铁或置于磁场中吸引分离,得到垂钓液c和洗脱磁性颗粒d;步骤四:将垂钓液c乙酰化,然后与五乙酰基葡萄糖混合,加入洗脱磁性颗粒d反应,生成反应物e;步骤五:对反应物e进行脱乙酰基处理,得到红景天苷;其中,磁性颗粒为酪胺将镍或钯络合物固定于磁性二氧化硅材颗粒表面制备得到。本发明利用磁性材料对提取物进行固相吸附,提取率高;而且后续工艺中又使用磁性材料催化非目标物质转化为红景天苷,提高了红景天苷的纯度。
Description
技术领域
本发明属于红景天苷提取技术领域,具体涉及一种红景天苷的提取工艺。
背景技术
红景天(Rhodiola)为景天科红景天属多年生草本或亚灌木植物,是珍稀药用植物之一,被誉为“高原人参”。该属植物在全世界共约90种,在我国分布70多种,主产于华北、东北、西南、西北和华中等地区。其化学成分主要有黄酮类、酪醇、红景天苷(Salidroside)、谷甾醇、有机酸、挥发油、多糖、脂肪、蛋白质等。其中,红景天苷及其苷元酪醇是红景天主要有效成份,也是评价红景天及其提取物的最重要指标。现代药理学研究证实,红景天提取物具有抗衰老、抗肿瘤、抗病毒、抗菌、抗缺氧、抗疲劳、抗辐射、抗氧化、镇痛、对中枢神经及内分泌系统双向调节等多种活性,且具有很小副作用。
天然红景天中红景天苷的提取和分离方法主要有层析法、超滤纯化法、醇沉纯化法、大孔树脂吸附法等。柱层析法可得到较高纯度的红景天苷,但有效成分损失严重,收率太低,只适用于微量标准品的制备;超滤纯化法超滤膜使用过程中,膜污染易造成膜通量锐减,膜清洗过程要用到大量的碱和酸,而且分离选择性较差,产品质量不稳定;乙醇沉淀法在去除杂质的同时,所得干浸膏粘度较大,易吸潮,给后期工艺操作带来不便,此法耗醇量大,成本高,处理时间较长;大孔树脂吸附法使用较为普遍,但仅依靠大孔吸附树脂一种分离方法,得到的红景天苷产品纯度还是偏低。
申请号为CN201610487353.8的文件公开了一种包括如下步骤:(1)将红景天干燥粉碎后,加入PH=3.8-4.5柠檬酸钠/柠檬酸缓冲溶液,然后加入生物酶进行酶解,得酶解液;其中缓冲溶液用量为原料红景天重量的5-10倍;(2)将步骤(1)的酶解液转移至连续逆流提取罐中,并加入重量为红景天原料2-5倍的水,回流提取,过滤,浓缩,得到红景天苷粗提物;(3)将步骤(2)所得红景天苷粗提物加水溶解,用大孔吸附树脂吸附纯化,用35-45%乙醇洗脱,收集洗脱液,减压浓缩得到红景天苷粗品;(4)将步骤(3)所得的红景天苷粗品,用高速逆流色谱法进行分离,收集含有红景天苷的组分,减压蒸干,得到红景天苷纯品。但是该方法应用酶提取,后续的酶的分离回收难度较大,工艺复杂,不利于应用推广。
近年来,由于磁性材料具有超顺磁性、材料整体的制备简单性、应用低毒性等特点,作为一种应用于研发潜能的固相萃取材料,一直受到广泛关注,因此以红景天为研究对象,对红景天提取物进行配体垂钓具有研究价值。而在红景天提取物中的较大比例的红景天苷、苷元酪醇及红景天素均存在可键合的羟基基团,应用现有的磁性材料吸附无法得到纯度高的红景天苷。
发明内容
针对上述存在的问题,本发明的目的是提供一种红景天苷的提取工艺,利用磁性材料对提取物进行固相吸附,提取率高;而且后续工艺中又使用磁性材料催化非目标物质转化为红景天苷,提高了红景天苷的纯度。
为了实现上述目的,本发明的技术方案如下:一种红景天苷的提取工艺,包括以下步骤:
步骤一:将红景天提取物与磁性颗粒混合后孵化,得到混合液a;
步骤二:将所述混合液a用磁铁或置于磁场中吸引分离,得到吸附磁性颗粒b;
步骤三:将所述吸附磁性颗粒b浸泡于洗脱液A中,然后用磁铁或置于磁场中吸引分离,得到垂钓液c和洗脱磁性颗粒d;
步骤四:将所述垂钓液c进行乙酰化,然后与五乙酰基葡萄糖混合,加入所述洗脱磁性颗粒d反应,生成反应物e;
步骤五:对所述反应物e进行脱乙酰基处理,得到红景天苷;
其中,所述磁性颗粒为酪胺将镍或钯络合物固定于磁性二氧化硅材颗粒表面制备得到。
在本方案设计中,磁性颗粒对红景天提取物的处理过程主要包括两部分:第一,聚合于磁性颗粒表面的酪胺上含有的氨基与提取物中主要是红景天苷、苷元酪醇中的酚羟基生成较强的氢键,使得红景天苷、苷元酪醇被吸附于磁性颗粒表面,吸附了活性物质的磁性颗粒在磁场或磁铁作用下可从体系中迅速分离;第二,将吸附了活性物质的磁性颗粒洗脱后即可得到垂钓液,为了使垂钓液中的目标物质红景天苷的收率提高,本发明人对垂钓液进行处理,主要原理为利用磁性颗粒上的催化剂催化垂钓液中乙酰化的苷元酪醇与后来加入的五乙酰基葡萄糖反应合成红景天苷,其反应公式如下:
这样处理不仅使得垂钓液中非目标物质苷元酪醇消除,而且还转化成了目标物质红景天苷,不仅使得红景天苷的收率更高,而且纯度也得到了提升。
作为本发明的进一步优选,所述磁性颗粒的制备方法包括:a.将包覆二氧化硅的磁性材料浸入于Tyr-NXaLb溶液中;得到混合液;b.将所述混合液于30~50摄氏度中反应10~15h;c.过滤、水洗、干燥,得到所述磁性颗粒;其中,所述Tyr代表酪胺;N代表Ni元素或Pd元素;X代表卤素或乙酰氧基;L代表腈基或三苯基膦;a、b均为大于等于1的自然数;在本发明中,L进一步优选为三苯基膦。
在本方案设计中,酪胺能够在溶解氧的作用下发生聚合反应,形成黏附于磁性颗粒表面的聚酪胺层,而催化剂在酪胺聚合过程中能被固定在聚合层处,酪胺固定催化剂的过程如下所示:
上述催化剂固定于磁性颗粒表面的过程可分为两种:一种在酪胺聚合过程中将催化剂包埋于聚酪胺层内,该固定方式不是共价结合的方式,而是借助于酪胺自聚合过程中的黏合作用实现;另一种是催化剂中的三苯基膦与聚酪胺层表面暴露的氨基位点桥联从而将催化剂吸附于聚酪胺层表面,该过程如下所示:
上述两种对催化剂的固定方式可充分保证磁性材料的催化效果,而且如上所示,在催化过程中聚合于磁性材料表面的聚酪胺上的酚羟基发生键合,氨基分布于磁性材料表面,既保证了聚酪胺层不会丧失吸附能力,也保证了聚酪胺本身不会与加入的五乙酰基葡萄糖等物质发生反应。本方案中酪胺的加入量需大于催化剂的加入量,保证磁性颗粒表面具有充分的氨基,以保证磁性颗粒对目标物质的吸附能力。
作为本发明的进一步优选,所述包覆二氧化硅的磁性材料的制备方法包括:所述包覆二氧化硅的磁性材料的制备方法包括:(1)将Fe3O4颗粒活化,然后加入硅源反应,得到反应颗粒;(2)将所述反应颗粒分别用蒸馏水、无水乙醇洗涤,干燥,即得包覆二氧化硅的磁性材料。
作为本发明的进一步优选,所述步骤五中反应物e的脱乙酰基处理包括:将所述反应物e加入到甲醇钠-甲醇溶液中反应或经强酸性阳离子交换树脂处理,得到红景天苷。
在本方案设计中,乙酰化处理是用于避免苷元酪醇中的酚羟基没有被保护,在与五乙酰基葡萄糖反应时形成酚羟基上的O-糖苷键副产物,该副产物与红景天苷为同分异构体,难以与红景天苷分离;同时乙酰化处理也可保护垂钓液中的红景天苷上的酚羟基不发生反应;而脱乙酰基处理则是对反应后的产物,主要是五乙酰红景天苷、四乙酰红景天苷进行脱酰化处理,得到目标物质红景天苷。在本发明中,考虑到后续的分离回收,强酸性阳离子交换树脂为较优选择,但若考虑成本,则可选择使用甲醇钠-甲醇溶液。
作为本发明的进一步优选,所述硅源包括硅酸钠、正硅酸甲酯、正硅酸乙酯中的一种。本发明进一步优选为正硅酸乙酯。
作为本发明的进一步优选,所述甲醇钠-甲醇溶液中甲醇钠的摩尔浓度为0.1-0.5M。
作为本发明的进一步优选,所述洗脱液A为乙酸钠-乙酸-乙醇溶液。
作为本发明的进一步优选,所述步骤四中乙酰化处理采用乙酸酐-四氢呋喃溶液。
综上所述,本发明具有以下有益效果:
本发明应用的磁性颗粒可对红景天提取物进行固相吸附,不仅吸附效率高,而且后续处理步骤简单,溶剂方便回收,具有良好的应用前景。
本发明还对磁性颗粒表面固接了催化剂,使磁性颗粒同时具有催化剂的催化效果,进而催化提取物中非目标物质苷元酪醇反应转化为目标物质红景天苷,该转化方式简单易实施,催化剂可重复利用,不仅可提高红景天苷的收率,还可提高红景天苷的纯度。
本发明制备的磁性颗粒可重复利用,极大地节约了使用的生产成本,具有广阔的应用前景。
本发明制备的磁性颗粒具有快速磁响应,在外部磁场存在的情况下能快速磁分离,具有很广的应用前景。
附图说明
附图1为本发明磁性颗粒的重复利用性能结果图。
具体实施方式
实施例1
本实施例提取红景天苷的工艺具体如下:
一、制备磁性颗粒
(1)称取3.46g的六水合氯化铁置于含有70ml乙二醇中,缓慢加入7.66g无水乙酸钠,在室温下剧烈搅拌30min直至完全溶解,得到均匀的黄色溶液,然后将溶液转移至Teflon-lined不锈钢高压反应釜中,200摄氏度下反应12h后,得到黑色沉淀,用无水乙醇洗涤3次再用去离子水洗涤3次,60摄氏度真空干燥12h,得到四氧化三铁颗粒;
(2)称取已制备的200mg四氧化三铁颗粒加入到含有100ml乙醇/水(4/1,v/v)和2ml氨水(质量浓度28%)的溶液中,超声30min,加入2mlTEOS(正硅酸乙酯),室温下搅拌12h,得到黑色颗粒,然后用蒸馏水和无水乙醇各洗涤3次,60摄氏度真空干燥12h,得到包覆二氧化硅的四氧化三铁颗粒;
(3)将100ml酪胺-氢氧化钠溶液(酪胺浓度0.1mol/L,氢氧化钠浓度0.2mol/L)和5mlpdI2(Ph3P)3-THF溶液(pdI2(Ph3P)3浓度0.1mol%)混合,称取200mg包覆二氧化硅的四氧化三铁颗粒加入到混合液中,40摄氏度搅拌反应12h,转速200rpm,过滤得到棕黑色颗粒,用蒸馏水、乙醇各清洗3次,60摄氏度真空干燥12h,得到磁性颗粒。
二、红景天提取物的制备
(1)称取2kg红景天,粉碎后加入12L水在40摄氏度下浸泡2h,然后升温至60摄氏度超声提取2h,过滤后得到提取液;(2)将提取液经浓缩至蒸干,得到干燥物约30g,再用300ml无水乙醇加工干燥物溶解,得到红景天提取物。
三、红景天苷的提取
(1)取50mg磁性颗粒加入至5ml红景天提取物中混合孵化,在漩涡振荡器上振荡10min,然后放置于强磁磁场中吸引,移出清液,取出磁性颗粒;
(2)将步骤(1)取出的磁性颗粒用5ml无水乙醇浸洗,在漩涡振荡器上振荡10min,放置于强磁磁场中吸引,移出清液,取出磁性颗粒,重复2次;
(3)将步骤(2)取出的磁性颗粒浸泡在5mlpH=3.6的乙酸钠-乙酸-乙醇溶液中,超声振荡20min,然后再加入5ml70%乙醇溶液,超声振荡30min,然后放置于强磁磁场中吸引,得到的清液即为垂钓液,得到的磁性颗粒即为洗脱后的磁性颗粒。
(4)向垂钓液中加入0.1mlAc2O-THF溶液和25mg洗脱后的磁性颗粒,搅拌反应60min后,加入0.2mol五乙酰基葡萄糖,回流反应3h,放置于强磁磁场中吸引,回收溶液,然后加入100ml水搅拌,再加入100ml乙酸乙酯萃取3次,合并有机层,无水硫酸钠干燥,回收乙酸乙酯,得到提取液;
(5)向提取液中加入5ml甲醇钠-甲醇溶液(1/3,v/v)搅拌反应60min,然后加入50ml水搅拌,再加入50ml乙酸乙酯萃取3次,合并有机层,无水硫酸钠干燥,回收乙酸乙酯,乙酸乙酯/石油醚结晶得到白色固体。
在本实施例中,pdI2(Ph3P)3中pd可替换为Ni,I可替代为Cl、Br、OAc中的一种,制备以pdI2(Ph3P)3为例,制备方法一:取PdI2和配体三苯基膦(摩尔比1:3)混合均匀后,在干燥箱中200摄氏度干燥24h,冷却备用。制备方法二:取100gPdI2和配体三苯基膦(摩尔比1:3)混合均匀后,加入DMF250ml和1molDBU,130摄氏度回流12h后,减压蒸馏蒸出溶剂,剩余物加入200ml无水乙醇,室温搅拌60min后,过滤,无水乙醇洗涤,150摄氏度干燥3h,冷却备用。
在本实施例中,所用试剂均可从常规途径购买得到,故不再赘述。
实施例2
本实施例与实施例1的不同之处在于,pdI2(Ph3P)3-THF溶液替换为pdCl2(Ph3P)2-DMSO溶液;红景天苷的提取步骤为:
(1)取50mg磁性颗粒加入至5ml红景天提取物中混合孵化,在漩涡振荡器上振荡10min,然后放置于强磁磁场中吸引,移出清液,取出磁性颗粒;
(2)将步骤(1)取出的磁性颗粒用5ml无水乙醇浸洗,在漩涡振荡器上振荡10min,放置于强磁磁场中吸引,移出清液,取出磁性颗粒,重复2次;
(3)将步骤(2)取出的磁性颗粒浸泡在5ml pH=3.6的乙酸钠-乙酸-乙醇溶液中,超声振荡20min,然后再加入5ml70%乙醇溶液,超声振荡30min,在得到的体系中,清液即为垂钓液,磁性颗粒即为洗脱磁性颗粒。
(4)向步骤(3)的体系中加入0.1mlAc2O-THF溶液,搅拌反应60min后,加入0.2mol五乙酰基葡萄糖,回流反应3h,放置于强磁磁场中吸引,回收溶剂,然后加入100ml水搅拌,再加入100ml乙酸乙酯萃取3次,合并有机层,无水硫酸钠干燥,回收乙酸乙酯,得到提取液;
(5)将提取液与5g732型强酸性阳离子交换树脂加入至100ml95%乙醇中回流过夜,过滤,回收乙醇,乙酸乙酯/石油醚结晶得到白色固体。
实施例3
本实施例与实施例1的不同之处在于,pdI2(Ph3P)3-THF溶液替换为NiCl2(Ph3P)2-DMF溶液。
实施例4
本实施例与实施例2的不同之处在于,pdI2(Ph3P)3-THF溶液替换为NiBrCN-DMSO溶液。
对比例1
与实施例1的不同之处在于,红景天苷的提取步骤为:(1)取50mg磁性颗粒加入至5ml红景天提取物中混合孵化,在漩涡振荡器上振荡10min,然后放置于强磁磁场中吸引,移出清液,取出磁性颗粒;(2)将步骤(1)取出的磁性颗粒用5ml无水乙醇浸洗,在漩涡振荡器上振荡10min,放置于强磁磁场中吸引,移出清液,取出磁性颗粒,重复2次;(3)将步骤(2)取出的磁性颗粒浸泡在5mlpH=3.6的乙酸钠-乙酸-乙醇溶液中,超声振荡20min,然后再加入5ml70%乙醇溶液,超声振荡30min,然后放置于强磁磁场中吸引,得到的清液即为垂钓液;(4)从垂钓液中回收乙醇,然后酸乙酯/石油醚结晶得到白色固体。
分别计算实施例1~4及对比例1的纯度和收率,结果如下表所示:
如上表数据所得,对比例1的纯度和收率明显下降,其原因可能是磁性颗粒同样吸附提取了提取物中的含羟基的其他组分,造成了收率和纯度都不高的结果。
本发明还对实施例1中制备的磁性材料进行重复性试验,结果如附图1所示,该材料经过6次的吸附-解析-催化过程后,吸附量仍能达到初始吸附量的85%左右,第7次开始保持不变,由此可得,经过多次吸附-解析-催化过程,材料的吸附能力没有发生太大的变化,具有重复利用的特点。
本文中所描述的具体实施例仅仅是对本发明精神作举例说明。本发明所属技术领域的技术人员可以对所描述的具体实施例做各种各样的修改或补充或采用类似的方式替代,但并不会偏离本发明的精神或者超越所附权利要求书所定义的范围。
Claims (4)
1.一种红景天苷的提取工艺,其特征在于,包括以下步骤:
步骤一:将红景天提取物与磁性颗粒混合后孵化,得到混合液a;
步骤二:将所述混合液a用磁铁或置于磁场中吸引分离,得到吸附磁性颗粒b;
步骤三:将所述吸附磁性颗粒b浸泡于洗脱液A中,然后用磁铁或置于磁场中吸引分离,得到垂钓液c和洗脱磁性颗粒d;
步骤四:将所述垂钓液c进行乙酰化,然后与五乙酰基葡萄糖混合,加入所述洗脱磁性颗粒d反应,生成反应物e;
步骤五:对所述反应物e进行脱乙酰基处理,得到红景天苷;
其中,
所述洗脱液A为乙酸钠-乙酸-乙醇溶液;
步骤一中所述磁性颗粒的制备方法包括:a.将包覆二氧化硅的磁性材料浸入于Tyr-NXaLb溶液中;得到混合液;b.将所述混合液于30~50摄氏度中反应10~15h;c.过滤、水洗、干燥,得到所述磁性颗粒;其中,所述Tyr代表酪胺;N代表Ni元素或Pd元素;X代表卤素或乙酰氧基;L代表腈基或三苯基膦;a、b均为大于等于1的自然数;
步骤a中所述包覆二氧化硅的磁性材料的制备方法包括:(1)将Fe3O4颗粒活化,然后加入硅源反应,得到反应颗粒;(2)将所述反应颗粒分别用蒸馏水、无水乙醇洗涤,干燥,即得包覆二氧化硅的磁性材料;所述硅源为硅酸钠、正硅酸甲酯、正硅酸乙酯中的一种。
2.根据权利要求1所述的一种红景天苷的提取工艺,其特征在于,所述步骤五中反应物e的脱乙酰基处理包括:将所述反应物e加入到甲醇钠-甲醇溶液中反应或经强酸性阳离子交换树脂处理,得到红景天苷。
3.根据权利要求2所述的一种红景天苷的提取工艺,其特征在于,所述甲醇钠-甲醇溶液中甲醇钠的摩尔浓度为0.1-0.5M。
4.根据权利要求1所述的一种红景天苷的提取工艺,其特征在于,所述步骤四中乙酰化处理采用乙酸酐-四氢呋喃溶液。
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