CN113583017A - Method for selectively extracting and separating artemisinin/arteannuin by using hydrophilic ionic liquid - Google Patents
Method for selectively extracting and separating artemisinin/arteannuin by using hydrophilic ionic liquid Download PDFInfo
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Abstract
The invention relates to a method for selectively extracting and separating artemisinin/arteannuin by using hydrophilic ionic liquid, which comprises the following specific processes: mixing the ionic liquid aqueous solution and the organic solvent solution of artemisinin/artelene, shaking at constant temperature, standing, respectively taking the ionic liquid phase and the organic solvent phase, diluting to constant volume with methanol, and detecting the concentration of artemisinin and artelene in the raffinate phase (organic solvent phase) and the extract phase (ionic liquid phase) to obtain separation selectivity. The ion liquid aqueous solution can extract the arteannuin from the crude artemisinin product with high selectivity, and then the extraction raffinate is directly cooled and crystallized to obtain the artemisinin product. The method is suitable for removing low-content arteannuin, is simple and green to operate, and can realize high-selectivity separation of artemisinin/arteannuin.
Description
Technical Field
The invention relates to the field of natural product purification and separation, and particularly relates to a method for selectively extracting and separating artemisinin/arteannuin by using a hydrophilic ionic liquid.
Background
Artemisinin is the most effective antimalarial drug recognized by the world health organization, also has the pharmacological activities of resisting parasites, fungi, inflammation and cancers, treating lupus erythematosus and the like, and is mainly derived from artemisia annua. The natural plant contains hundreds of components, including arteannuin, artemether, dihydroartemisinin, deoxyartemisinin, etc. which have a structure similar to artemisinin.
Column chromatography-recrystallization purification is mainly adopted in industry to obtain artemisinin products, but researches show that the prior art is difficult to effectively remove arteannuin. The structures of arteannuin and artemisinin are shown in fig. 1, and the two differ by only one C ═ C bond, and their physicochemical properties are very close. The presence of artemisinine may cause severe side effects such as allergy, reduced drug effectiveness, etc. Therefore, the highly selective separation of arterenes from artemisinin is one of the most challenging problems to obtain high quality artemisinin products.
Patent CN 107746407A discloses a method for reducing arteannuin in, which comprises the steps of firstly preparing petroleum ether extract of artemisia annua, enabling the extract to flow through a silica gel column, then eluting the silica gel column by using mixed liquid of petroleum ether and ethyl acetate, and finally crystallizing and recrystallizing the eluent to achieve the purpose of separating arteannuin and arteannuin, wherein the content of arteannuin can be reduced to 0.93-1.96%, but the process is complex in operation and long in time consumption, so that a new method needs to be developed to obtain high-quality arteannuin. The medium innovation is the key for developing a new process for selectively separating artemisinin and arteannuin, the ionic liquid is a special material with adjustable structure and performance, and the functionalized ionic liquid suitable for a certain requirement can be obtained by changing the structures of anions and/or cations and introducing specific functional groups. The ionic liquid is reported to be capable of identifying and separating homologues with high selectivity through hydrogen bonds and pi-pi action, is widely applied to separation of alkane/olefin, natural active homologues, metal ions and the like, and has separation efficiency superior to that of the traditional medium. For example, the separation selectivity of an ionic liquid system is higher than that of an organic solvent, the separation effect of sulfolane in the organic solvent is the best, the separation selectivity of vitamin D3 and tachysterol 3 is 1.44, and the selectivity of the ionic liquid system can reach 1.77.
The invention uses the ionic liquid aqueous solution as a medium to separate the artemisinin/the arteannuin, can selectively extract the arteannuin (even if the content of the arteannuin is lower than 0.9 percent), to an ionic liquid phase, and then the arteannuin product with high quality can be obtained by cooling and crystallizing the organic solvent phase. Compared with the traditional separation method, the method is simple and efficient, reduces the consumption of organic solvent, reduces the back extraction process, and is an efficient, green and environment-friendly process.
Disclosure of Invention
The invention aims to provide an efficient, green and environment-friendly artemisinin purification method, which utilizes strong interaction between ionic liquid and artemisinin to extract and remove artemisinin from crude artemisinin products in a high selectivity manner so as to obtain high-quality artemisinin products.
In order to achieve the purpose, the invention adopts the following technical scheme:
mixing the ionic liquid aqueous solution with the organic solvent solution of artemisinin/artelene, shaking at constant temperature, standing for layering to obtain two-phase solution, measuring the concentration of artemisinin and artelene in the two phases by high performance liquid chromatography, and calculating to obtain separation selectivity.
As a preferable technical scheme, the ionic liquid is one or more of trimethylamine hydrochloride, triethylamine hydrochloride, choline chloride, allyl trimethyl ammonium chloride and diallyl dimethyl ammonium chloride, and the artemisinine is selectively extracted and separated into the ionic liquid aqueous solution by virtue of hydrophobic interaction and pi-pi complexation between the ionic liquid and the artemisinine.
As a preferable technical scheme, the content of the arteannuin in the artemisinin crude product is 0.8-7.5%.
According to a preferable technical scheme, the volume ratio of the ionic liquid aqueous solution to the organic solvent solution containing the arteannuin/artemisinin is 0.25: 1-4: 1.
In a preferred embodiment of the present invention, the organic solvent is one or two of cyclohexane and petroleum ether.
As a preferred technical scheme, the oscillation temperature is 30-60 ℃, the time is 0.5-7 hours, the mixture is kept stand for 4 hours at the oscillation temperature for layering to obtain a two-phase solution, 0.5mL of each of an extraction phase (an ionic liquid phase) and a raffinate phase (an organic solvent phase) is respectively taken, the volume is determined to be 5mL by methanol, the concentration of artemisinin and arteannuin in the two phases is measured by high performance liquid chromatography, and the separation selectivity is obtained by calculation.
As a preferred technical scheme, an ionic liquid aqueous solution and an artemisinin crude product organic solvent solution containing 0.8-7.5% of arteannuin are mixed according to a volume ratio of 0.25: 1-4: 1, the mixture is shaken at a constant temperature of 30-60 ℃ for 0.5-7 h, the shaking temperature is kept still for 4h for layering to obtain a two-phase solution, 0.5mL of each of an extraction phase (ionic liquid phase) and a raffinate phase (organic solvent phase) is respectively taken, the volume is fixed to 5mL by methanol, the concentration of the artemisinin and the arteannuin in the two phases is measured by high performance liquid chromatography, and the distribution coefficient and the separation selectivity are calculated.
The invention provides a method for selectively extracting and separating artemisinin/arteannuin by using hydrophilic ionic liquid, the adopted ionic liquid is not easy to volatilize, can be biodegraded, and can identify arteannuin molecules with high selectivity.
Drawings
FIG. 1 shows the structure of artemisinin.
FIG. 2 shows the structure of arterenol.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Comparative example
1) Mixing pure water with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 4.9%) at equal volume, shaking at 50 deg.C for 5 hr, standing at 50 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (water phase) and raffinate phase (organic solvent phase) with 0.5mL respectively by injector, diluting with methanol to 5mL, measuring the concentration of artemisinin and artelene in the two phases respectively by high performance liquid chromatography, and calculating to obtain separation selectivity of 4.53.
Example 1
1) Mixing 5% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 4.9%) at the same volume, shaking at 50 deg.C for 5 hr, standing at 50 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring the concentration of artemisinin and artelene in the two phases respectively by high performance liquid chromatography, and calculating to obtain separation selectivity of 6.45.
Example 2
1) Mixing 5% triethylamine hydrochloride water solution (mole fraction) and cyclohexane solution containing arteannuin/artemisinin (arteannuin content is 4.9%) in equal volume, shaking at 50 deg.C for 5 hr, standing at 50 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 5.97.
Example 3
1) Mixing 5% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 5%) at the same volume, shaking at 50 deg.C for 0.5 hr, standing at 50 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting to 5mL with methanol, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 4.67.
Example 4
1) Mixing 5% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 4.5%) at the same volume, shaking at 50 deg.C for 1 hr, standing at 50 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 6.61.
Example 5
1) Mixing 5% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 5%) at the same volume, shaking at 50 deg.C for 4 hr, standing at 50 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting to 5mL with methanol, measuring artemisinin and artelene concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 4.74.
Example 6
1) Mixing 5% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 5%) at the same volume, shaking at 30 deg.C for 1 hr, standing at 30 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting to 5mL with methanol, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 5.63.
Example 7
1) Mixing 5% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 4.5%) at the same volume, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 5.77.
Example 8
1) Mixing 5% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 5.1%) at the same volume, shaking at 60 deg.C for 1 hr, standing at 60 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 4.16.
Example 9
1) Mixing 10% allyl trimethyl ammonium chloride aqueous solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 4.2%) at the same volume, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 8.49.
Example 10
1) Mixing 40% allyl trimethyl ammonium chloride aqueous solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 4.3%) at the same volume, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 11.41.
Example 11
1) Mixing 35% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 4.4%) at the same volume, shaking at 40 deg.C for 0.5 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 10.70.
Example 12
1) Mixing 25% allyl trimethyl ammonium chloride water solution (mole fraction) with petroleum ether solution containing arteannuin/artemisinin (arteannuin content 1.7%) at the same volume, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 10.18.
Example 13
1) Mixing 25% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 3.5%) at the same volume, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 9.11.
Example 14
1) Mixing 25% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content is 2.9%) at volume ratio of 0.25:1, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 7.29.
Example 15
3) Mixing 25% diallyl dimethyl ammonium chloride aqueous solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content is 3.7%) at a volume ratio of 1:1, shaking at 40 deg.C for 1h, standing at 40 deg.C for 4h, and layering to obtain two-phase solution.
4) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting with methanol to 5mL, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 6.87.
Example 16
1) Mixing 25% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 0.8%) at a volume ratio of 1:1, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting to 5mL with methanol, measuring artemisinin and arteannuin concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 12.23.
Example 17
1) Mixing 25% allyl trimethyl ammonium chloride water solution (mole fraction) with cyclohexane solution containing arteannuin/artemisinin (arteannuin content 7.5%) at a volume ratio of 1:1, shaking at 40 deg.C for 1 hr, standing at 40 deg.C for 4 hr, and layering to obtain two-phase solution.
2) Extracting extract phase (ionic liquid phase) and raffinate phase (organic solvent phase) with 0.5mL respectively, diluting to 5mL with methanol, measuring artemisinin and artelene concentration in two phases with high performance liquid chromatography, and calculating to obtain separation selectivity of 10.03.
The artemisinin/artelene concentration in the extract phase (e)/raffinate phase (r) was determined by High Performance Liquid Chromatography (HPLC), and the distribution coefficient (D) and separation selectivity (S) of artemisinin and artelene were calculated according to the following formula.
The above description is only for the specific implementation steps of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are included in the scope of the present invention.
Claims (7)
1. A method for selectively extracting and separating artemisinin/arteannuin by hydrophilic ionic liquid is characterized in that firstly, crude artemisinin products containing low-content arteannuin and organic solvent are mixed according to a certain proportion to obtain a uniform organic phase, then ionic liquid aqueous solution is added according to a certain proportion, constant temperature oscillation is carried out, finally standing and layering are carried out to obtain two-phase solution, the ionic liquid aqueous solution can extract arteannuin from the crude artemisinin products with high selectivity, and then the extraction residual phase is directly cooled and crystallized, thus obtaining artemisinin products.
2. The method according to claim 1, wherein the ionic liquid is one or a mixture of two or more of trimethylamine hydrochloride, triethylamine hydrochloride, choline chloride, allyl trimethyl ammonium chloride and diallyl dimethyl ammonium chloride.
3. The method according to claim 1, wherein the organic solvent is one or a mixture of cyclohexane and petroleum ether.
4. The method according to claim 1, characterized in that the amount fraction of ionic liquid species in the ionic liquid aqueous solution is between 5% and 40%.
5. The method according to claim 1, wherein the volume ratio of the ionic liquid aqueous solution to the organic solution is 0.25:1 to 4: 1.
6. The method according to claim 1, wherein the constant temperature shaking is performed at 30-60 ℃ for 0.5-7 hours.
7. The method of claim 1, wherein the artemisinin crude product has a content of artemisinin ranging from 0.8% to 7.5%.
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| EP0908460A1 (en) * | 1997-10-06 | 1999-04-14 | Council of Scientific and Industrial Research | A process for the simultaneous production of artemisinin and essential oil from the plant artemisia annua |
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| CN107312015A (en) * | 2017-06-21 | 2017-11-03 | 禹州市天源生物科技有限公司 | A kind of technique of efficiently extracting and producing artemisinin by ionic liquid |
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| EP0908460A1 (en) * | 1997-10-06 | 1999-04-14 | Council of Scientific and Industrial Research | A process for the simultaneous production of artemisinin and essential oil from the plant artemisia annua |
| CN101597296A (en) * | 2008-06-02 | 2009-12-09 | 中国科学院过程工程研究所 | A kind of novel method of efficiently extracting and producing artemisinin by ionic liquid |
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