WO2016082059A1 - 一种超声水溶液提取青蒿素的方法 - Google Patents

一种超声水溶液提取青蒿素的方法 Download PDF

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WO2016082059A1
WO2016082059A1 PCT/CN2014/001110 CN2014001110W WO2016082059A1 WO 2016082059 A1 WO2016082059 A1 WO 2016082059A1 CN 2014001110 W CN2014001110 W CN 2014001110W WO 2016082059 A1 WO2016082059 A1 WO 2016082059A1
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artemisinin
aqueous solution
extraction
ultrasonic
artemisia annua
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PCT/CN2014/001110
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English (en)
French (fr)
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肖虎
夏传递
梁克
陶旭丹
王惠芳
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北京罗瑞生物科技有限公司
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Publication of WO2016082059A1 publication Critical patent/WO2016082059A1/zh

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/20—Spiro-condensed systems

Definitions

  • the invention relates to the technical field of extraction and purification of artemisinin, in particular to an aqueous solution ultrasonic extraction of artemisinin and a macroporous resin purification technology.
  • Qinghaosu is a sesquiterpene lactone compound with a peroxy group extracted from the genus Artemisia annua in 1971.
  • the molecular formula is C 15 H 22 O 5 .
  • Pure artemisinin is colorless needle crystal, melting point 156 ⁇ 157 ° C, bitter taste, soluble in ethyl acetate, benzene, chloroform, acetone and glacial acetic acid, soluble in methanol, ethanol, ether and hot petroleum ether, insoluble In the water.
  • Artemisinin has a very good anti-malarial effect and is currently recognized as one of the most effective and safe drugs for the treatment of malaria.
  • artemisinin plays a role in antibacterial, antiparasitic and treatment of immune system diseases, especially in recent years, it has also made outstanding progress in the treatment of tumors.
  • the purification process mainly consists of chromatographic techniques such as macroporous adsorption resin or silica gel column and recrystallization technology. So far, there is no patented technology for separating the artemisinin water extract directly into macroporous resin or silica gel chromatography. At the same time, in the process of water extraction of Artemisia annua L. plant, various kinds of impurities and some components are difficult to remove. We also urgently need new methods to remove impurities from the crude extract of artemisinin.
  • the object of the present invention is to provide a method for extracting green from a yellow plantweed plant quickly, efficiently and safely, in view of the problems of large dosage of organic solvent, low extraction efficiency, environmental pollution caused by solvent use, and low safety of large-scale production.
  • the invention mainly comprises the following steps:
  • Treatment of raw materials The dried Artemisia annua plants are dried and pulverized to obtain a powder of about 20-100 mesh.
  • Ultrasonic water extraction equipment is used to mix the Artemisia annua L. powder and aqueous solution for continuous ultrasonic extraction, and then filtered and centrifuged to obtain artemisinin water extract.
  • the aqueous solution is an acidic solution adjusted to pH 2-7 by an organic acid, and the ratio of the aqueous solution to the raw material of Artemisia annua L. is 1 to 50:1 (V/W), the countercurrent extraction time is 0.5 to 5 hours, and the ultrasonic frequency is 10 ⁇ 50 kHz, ultrasonic power is 5 to 1000 W/cm 2 , and aqueous solution temperature is 20 to 70 °C.
  • the principle of using the aqueous solution ultrasonic extraction technology in the above method is to utilize the mechanical effects, cavitation effects and thermal effects generated during the ultrasonic vibration process, increase the movement speed of water molecules, enhance the penetration of water molecules and promote plant contents.
  • the rapid release; the aqueous solution of the acidic environment on the one hand increases the stability of artemisinin, on the other hand, it has the functions of dissolving and removing impurities.
  • the above method uses an alkyl halide as a dopant, preferably dichloromethane.
  • the principle of the method is: on the one hand, due to the high hydrophobicity of the halogen atom and the hydrocarbon group of the halogenated alkane, they are not mutually soluble with water-soluble impurities, but are easily soluble in artemisinin. On the one hand, some haloalkanes (dichloromethane, etc.) have a relatively low boiling point which facilitates the subsequent decompression concentration process.
  • Ethanol is used to dissolve the concentrate of artemisinin, and recrystallized to obtain pure artemisinin.
  • the invention has the beneficial effects that the aqueous solution completely replaces the organic solvent to extract artemisinin, which not only greatly reduces the cost, improves the production safety, but also reduces the solvent environment pollution and the selection of artemisinin extraction.
  • the improvement in properties removes the problem of residual organic solvents that may occur during the extraction process.
  • the application of ultrasonic extraction technology has greatly improved the extraction efficiency of artemisinin in aqueous solution, and realized the technological innovation of artemisinin extraction.
  • the purification process of artemisinin is carried out by directly adsorbing the artemisinin water extract using macroporous adsorption resin and eluting with ethyl acetate.
  • the operation process is simple and the separation effect is obvious.
  • the removal of the impurities of the crude extract of artemisinin is to remove a large amount of water-soluble impurities such as enamel and pigment in the crude extract of artemisinin by the nature of the alkyl halide, and the artemisinin can be easily enriched.
  • the present invention will ultrasonic water extraction
  • the technology and the subsequent separation of macroporous resin, halogenated alkane removal and recrystallization technology have invented a new method of extracting, separating and purifying artemisinin with industrial value, bringing new changes to the industrial production of artemisinin.
  • the aqueous extract of artemisinin was directly adsorbed to saturation by using D101 resin, and the column was eluted with ethyl acetate to obtain an ethyl acetate eluate, which was concentrated under reduced pressure to obtain a crude extract of artemisinin 4.4 g. It is 10.30%.
  • the crude extract of artemisinin was dissolved in dichloromethane, and the resulting precipitate was removed by suction filtration to obtain a crude artemisinin, which was concentrated under reduced pressure to further obtain an artemisinin concentrate. Ethanol was used to dissolve the artemisinin concentrate, and it was allowed to stand at low temperature for 24 hours. After repeated purification, 0.4 g of pure artemisinin was obtained, and the purity was 98.03% (HPLC).
  • the content is 32.91%.
  • the crude extract of artemisinin was dissolved in dichloromethane, and the resulting precipitate was removed by suction filtration to obtain a crude artemisinin, which was concentrated under reduced pressure to further obtain an artemisinin concentrate. Ethanol was used to dissolve the artemisinin concentrate, and it was allowed to stand at low temperature for 24 hours. After repeated purification, 3.7 g of pure artemisinin was obtained with a purity of 98.08% (HPLC).
  • Ultrasonic extraction equipment was used to continuously ultrasonically extract the mixture of Artemisia annua L. and aqueous solution for 2 hours, and then filtered and centrifuged to obtain an artemisinin aqueous extract.
  • the aqueous extract of artemisinin was directly adsorbed to saturation by using HP-20 resin, and the column was eluted with ethyl acetate to obtain an ethyl acetate eluate, which was concentrated under reduced pressure to obtain 65.4 g of crude artemisinin extract. , wherein the artemisinin content is 13.50%.
  • the crude extract of artemisinin was dissolved in dichloromethane, and the resulting precipitate was removed by suction filtration to obtain a crude artemisinin, which was concentrated under reduced pressure to further obtain an artemisinin concentrate. Ethanol was used to dissolve the artemisinin concentrate, and it was allowed to stand at low temperature for 24 hours. After repeated purification, 7.9 g of pure artemisinin was obtained with a purity of 98.20%. (HPLC).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

本发明将黄花蒿经过超声水溶液提取、大孔吸附树脂分离、重结晶纯化得到青蒿素。提取工艺为：1.将黄花蒿枝叶粉末与水溶液混合，经过超声提取过程，获得黄花蒿提取液；2.提取液直接经过大孔树脂分离，乙酸乙酯洗脱、浓缩，获得青蒿素粗品；3.粗品利用卤代烷溶解、固化去除杂质；4.乙醇重结晶，获得青蒿素纯品。本方法把超声与逆流提取技术相结合，仅需要水溶液不使用有机溶剂即可充分提取青蒿素；水提取液直接进行大孔树脂分离，洗脱，提高青蒿素分离效率；增加卤代烷固化粗品中的杂质步骤。

Description

一种超声水溶液提取青蒿素的方法 技术领域
本发明涉及青蒿素的提取、纯化技术领域，尤其涉及青蒿素的水溶液超声提取和大孔树脂纯化技术。
背景技术
青蒿素(Qinghaosu，Artemisinin)是我国科学家在1971年首次从菊科植物黄花蒿(Artemisia annua)中提取出的具有过氧基团的倍半萜内酯化合物，分子式为C15H22O5。纯青蒿素为无色针状结晶，熔点156～157℃，味苦，易溶于乙酸乙酯、苯、氯仿、丙酮和冰醋酸，能溶于甲醇、乙醇、乙醚和热石油醚，不溶于水。青蒿素具有十分优良的抗疟疾作用，是当前公认的治疗疟疾最有效、最安全的药物之一。除此之外，青蒿素在抗菌、抗寄生虫和治疗免疫系统疾病方面发挥一定的作用，特别是近年来其在治疗肿瘤方面也取得了突出进展。
从提取方法上来讲，目前从黄花蒿提取青蒿素的方法基本上有两大类，它们分别是有机溶剂提取法、超临界流体萃取法。国内主要使用的是有机溶剂提取法，其采用乙醇、丙酮、汽油等对黄花蒿进行提取，再经过大孔树脂或硅胶柱分离、结晶得到青蒿素纯品。国内绝大多数青蒿素生产企业都沿用这种经典的提取方法，例如CN101899055A“快速提制青蒿素的方法”、CN102718774A“一种制备青蒿素的方法”、CN103408566A“一种青蒿素提取新工艺”等都采用这种策略。其主要的缺点是使用有机溶剂作为溶媒，提取成本高、环境污染严重、规模化生产操作安全风险增大等。超临界流体萃取法，利用了二氧化碳等物质在超临界条件下的特殊状态实现提取，不存在溶剂残留、产品能保持固有成分特性。据报道在我国青蒿素的超临界流体萃取也有研究、应用，例如CN1931860A“从青蒿植物中提取分离纯化青蒿素的方法”、CN1869037A“一种提取青蒿素的方法”等。此法控制溶剂进入超临界状态需要提供高压和低温条件，故存在设备投入大、规模生产能力低、运行成本高，进行大规模工业生产设备安全性低等问题。
从分离纯化上来讲，由于黄花蒿中的青蒿素含量较低，提取过程中也会随之带来大量的杂质，因而需要进行纯化。现阶段纯化工艺主要以大孔吸附树脂或硅胶柱等层析技术和重结晶技术为主。到目前为止，未见将青蒿素水提取液直接进行大孔树脂或硅胶层析分离的专利技术，与此同时面对黄花蒿植物水提取过程中杂质种类多样，部分组分不易去除等问题，我们也迫切需要新的方法去除青蒿素粗提物中的杂质。
鉴于上述青蒿素提取、分离、纯化方法存在的问题，我们在寻找一整套提取效率高、青 蒿素产量大、溶剂成本低、安全环保且利于大规模工业生产的青蒿素提取、分离方法，这也是本发明解决以上问题的优势。
发明内容
本发明目的是针对现有提取方法有机溶剂用量大、提取效率低、溶剂使用造成环境污染，大规模生产安全性低等问题，提供了一种从黄花蒿植物中快速、高效、安全地提取青蒿素的全新方法。
本发明主要包括以下几个步骤：
1.原料的处理：将干燥的黄花蒿植物经过干燥粉碎获得20-100目左右的粉末。
2.青蒿素的提取：利用超声水提取设备，将黄花蒿粉末和水溶液混合进行连续超声提取，再经过过滤、离心，获得青蒿素水提取液。其中水溶液为经过有机酸调节pH值为2～7的酸性溶液，提取时水溶液与青蒿原料比为1～50∶1(V/W)，逆流提取时间为0.5～5小时，超声频率为10～50kHz，超声功率为5～1000W/cm2，水溶液温度为20～70℃。
上述方法中使用水溶液超声提取技术的原理为：利用超声振动过程中产生的机械效应，空化效应和热效应，增大水分子的运动速度、加强了水分子的穿透力并有促进植物内容物的快速释放；酸性环境的水溶液一方面增加青蒿素的稳定性，另一方面具有助溶、除杂作用。
3.青蒿素的分离：青蒿素的水提取液直接使用非极性或弱极性大孔吸附树脂分离，再用乙酸乙酯对吸附柱进行洗脱，获得乙酸乙酯提取液，减压浓缩，获得青蒿素粗提物。
4.青蒿素粗提物杂质的去除：青蒿素粗提物用卤代烷(优选二氯甲烷)溶解，将鞣质和色素等成分形成的沉淀去除，得到青蒿素粗品，减压浓缩，进一步获得青蒿素浓缩液。
上述方法中使用卤代烷作为除杂剂，优选二氯甲烷，其方法原理是：一方面由于卤代烷的卤原子和烃基的高度疏水性导致他们与水溶性杂质不能互溶，却易溶解青蒿素，另一方面有些卤代烷(二氯甲烷等)具有比较低的沸点利于后续减压浓缩过程。
5.青蒿素的重结晶：选用乙醇溶解青蒿素浓缩液，重结晶获得青蒿素纯品。
与现有技术相比，本发明的有益效果是：实现了水溶液完全代替有机溶剂提取青蒿素，不但成本大幅度下降、提高生产安全性，而且减少了溶剂环境污染、青蒿素提取的选择性提高，去除了提取过程中可能产生的有机溶剂残留问题。与此同时，超声提取技术的应用大幅度的提高了水溶液对青蒿素的提取效率，实现了青蒿素提取的技术革新。青蒿素的纯化过程是将青蒿素水提取液直接使用大孔吸附树脂吸附，并用乙酸乙酯洗脱，操作过程简单，分离效果明显。青蒿素粗提物杂质的去除，是利用卤代烷的性质除去青蒿素粗提物中的鞣质、色素等大量水溶性杂质成分，可以对青蒿素进行简便的富集。综上所述，本发明将超声水提取 技术及后续的大孔树脂分离、卤代烷除杂、重结晶技术相结合，发明了一种具有产业价值的青蒿素提取、分离、纯化新方法，为青蒿素的工业生产带来新变革。
具体实施方式
在下面的具体实施方案中进一步说明了本发明，这并不限制本发明的范围。在不脱离本发明上述技术思想情况下，根据本领域普通技术知识和惯用手段，做出各种替换和变更，均应包括在本发明的范围内。
实例1
取黄花蒿枝叶90.0克(青蒿素含量0.56％)粉碎至50目，加入0.05％苹果酸水溶液(pH＝3)4L浸泡，水温控制在45℃。利用超声提取设备，将黄花蒿与水混合物进行连续超声提取2小时，再经过过滤、离心，获得青蒿素水提取液。青蒿素的水提取液直接使用D101树脂吸附至饱和，再用乙酸乙酯对吸附柱进行洗脱，获得乙酸乙酯洗脱液，减压浓缩，获得青蒿素粗提物4.4克，含量为10.30％。青蒿素粗提物用二氯甲烷溶解，抽滤去除产生的沉淀，得到青蒿素粗品，减压浓缩，进一步获得青蒿素浓缩液。选用乙醇溶解青蒿素浓缩液，低温静置24小时，经反复纯化后，获得青蒿素纯品0.4克，纯度为98.03％(HPLC)。
实例2
取黄花蒿枝叶1.0千克(青蒿素含量0.47％)粉碎至20目，加入自来水(pH＝6.5)30L浸泡，水温控制在45℃。利用超声提取设备，将黄花蒿与水混合物进行连续超声提取3小时，再经过过滤、离心，获得青蒿素水提取液。青蒿素的水提取液直接使用HP-20树脂吸附至饱和，再用乙酸乙酯对吸附柱进行洗脱，获得乙酸乙酯洗脱液，减压浓缩，获得青蒿素粗提物13.0克，含量为32.91％。青蒿素粗提物用二氯甲烷溶解，抽滤去除产生的沉淀，得到青蒿素粗品，减压浓缩，进一步获得青蒿素浓缩液。选用乙醇溶解青蒿素浓缩液，低温静置24小时，经反复纯化后，获得青蒿素纯品3.7克，纯度为98.08％(HPLC)。
实例3
取黄花蒿枝叶1.6千克(青蒿素含量0.60％)粉碎至50目，加入含有0.1％柠檬酸的水溶液(pH＝3)50L浸泡，水温控制在50℃。利用超声提取设备，将黄花蒿与水溶液混合物进行连续超声提取2小时，再经过过滤、离心，获得青蒿素水提取液。青蒿素的水提取液直接使用HP-20树脂吸附至饱和，再用乙酸乙酯对吸附柱进行洗脱，获得乙酸乙酯洗脱液，减压浓缩，获得青蒿素粗提物65.4克，其中青蒿素含量为13.50％。青蒿素粗提物用二氯甲烷溶解，抽滤去除产生的沉淀，得到青蒿素粗品，减压浓缩，进一步获得青蒿素浓缩液。选用乙醇溶解青蒿素浓缩液，低温静置24小时，经反复纯化后，获得青蒿素纯品7.9克，纯度为98.20％ (HPLC)。
实例4
取黄花蒿枝叶1吨(青蒿素含量0.42％)粉碎至20目，加入自来水(pH＝6.5)35吨浸泡，水温控制为50℃。利用超声提取设备，将黄花蒿和水混合物进行连续超声提取4小时，再经过过滤、离心，获得青蒿素水提取液。青蒿素的水提取液直接使用AB-8树脂吸附，再用乙酸乙酯对吸附柱进行洗脱，获得乙酸乙酯洗脱液，减压浓缩，获得青蒿素粗提物13.5千克，含量为28.21％。青蒿素粗提物用二氯甲烷溶解，抽滤去除产生的沉淀，得到青蒿素粗品，减压浓缩，进一步获得青蒿素浓缩液。选用乙醇溶解青蒿素浓缩液，低温静置24小时，经反复纯化后，获得青蒿素纯品3.57千克，纯度为98.13％(HPLC)。

Claims (6)

  1. 连续超声水提取青蒿素的新方法，将黄花蒿(Artemisia annua)枝叶与水溶液混合，经过连续超声水溶液提取，获得黄花蒿提取液；水溶液提取物离心去除沉淀、直接经过大孔树脂吸附，乙酸乙酯洗脱，减压浓缩，获得青蒿素粗品；青蒿素粗品利用卤代烷纯化；再经过重结晶获得纯品。
  2. 根据权利要求1所述的连续超声水提取青蒿素的新方法，其特征在于提取原料为菊科(Compositae)，蒿属(Artemisia)中含有青蒿素成分的植物茎叶，其中优选黄花蒿(Artemisia annua)枝叶。
  3. 根据权利要求1所述的连续超声水提取青蒿素的新方法，其特征在于水溶液含有柠檬酸、乙酸、苹果酸、抗坏血酸(Vc)等一种或几种有机酸，其中有机酸含量为0％～1％，优选0.05％～0.4％，水溶液pH值为2～7.5。
  4. 根据权利要求1所述的连续超声水提取青蒿素的新方法，其特征在于黄花蒿枝叶粉碎为10～200目，优选20～100目；黄花蒿粉末与水溶液的质量体积比为1∶1～50；连续超声的参数为：浸泡液超声时间为0.5～5h，超声功率5～50kW，超声频率为10～50kHz对青蒿素浸泡液进行连续超声提取，超声提取温度为20～70℃。
  5. 根据权利要求1所述的连续超声水提取青蒿素的新方法，其特征在于大孔树脂类型为非极性或弱极性大孔分离树脂，优选型号为D101、HP20树脂，洗脱溶液为乙酸乙酯。
  6. 根据权利要求1所述的连续超声水提取青蒿素的新方法，其特征在于青蒿素粗品的纯化采用卤代烷，优选二氯甲烷。
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