CN113045555A - Method for extracting silymarin by screening ternary eutectic solvent with assistance of theoretical calculation - Google Patents
Method for extracting silymarin by screening ternary eutectic solvent with assistance of theoretical calculation Download PDFInfo
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Abstract
The invention discloses a method for extracting silymarin by screening ternary eutectic solvent with the assistance of theoretical calculation. A single-molecule model of 1296 Eutectic Solvents (Deep European Solvents, DESS) was established by quantum chemical calculations. Using silybin as a solute molecular model, predicting the dissolving capacity (Solvent Power, SP) of the silybin in different DESS through theoretical calculation, screening to obtain ternary DESS with high silybin extraction rate and low viscosity, mixing defatted silybin shell powder with the DESS after preparation, heating and stirring, centrifuging to obtain silybin extract, measuring the content of the silybin in the silybin extract through high performance liquid chromatography, and comparing the silybin extract with the traditional organic Solvent extraction. The invention adopts a simulation calculation method to assist in screening the DESs for extracting the silymarin, greatly saves manpower and material resources, and provides the DESs extraction method for the silymarin, which is green and environment-friendly, simple and convenient to operate and high in extraction rate.
Description
Technical Field
The invention relates to the field of natural product extraction, in particular to a method for extracting a bioactive component silymarin from silybum marianum by a ternary eutectic solvent.
Background
In 2003, Abbott et al first discovered a solvent-Eutectic solvent (Deep European Solvents, DESS) formed from a quaternary ammonium salt and an amide compound with excellent properties. The solvent has similar properties to ionic liquid, is nontoxic and biodegradable, and is a novel green solvent. At present, eutectic solvents attract extensive attention of researchers in various countries in the world, and show good application prospects in the fields of separation processes, chemical reactions, functional materials, electrochemistry and the like.
Silybum marianum is a plant of Silybum of Compositae, and is popularized and planted in China in 1972 as a medicinal plant for protecting liver. The silymarin is a natural active ingredient contained in the silybum marianum seed shell, is mainly silymarin, has the effects of protecting liver and benefiting gallbladder, reducing blood sugar and blood fat, resisting cancer, resisting inflammation and coagulation, can prevent ischemic cardiovascular and cerebrovascular diseases and chronic diabetic complications, and has high medical value. Silibinin is one of the components with highest content and strongest activity.
At present, the silymarin is extracted mainly by an organic solvent extraction method, ultrasonic and microwave are tried to strengthen mass transfer so as to shorten the extraction period, and yangqin (CN201610763023.7) uses ethanol to reflux and extract flavonoid compounds in silymarin stems and leaves, and the flavonoid compounds are repeatedly washed by water and alkali and then absorbed by macroporous resin. Solvent extraction of Silybum marianum shell by Wujunming et al (CN 201710677923.4): putting the treated silybum marianum shell strips into an extraction tank, adding 2-4 times of ethyl acetate, refluxing for 15-24 h, and recovering the ethyl acetate to obtain the total flavonoids. Because the traditional solvent extraction has the problems of high energy consumption, low extraction rate, great damage to active substances, serious toxic substance residue and the like, researchers gradually begin to use green and environment-friendly DESS to extract natural products and the like, and particularly show advantages in the extraction of flavonoids (CN201610827959.1), but the DESs have not seen relevant documents in the extraction of silymarin. And the DESS has designability, so that the combination types are huge, if the DESs are screened one by one through experiments, the investment cost of manpower, material resources and time is overlarge, the efficiency is low, and the DESs have large viscosity and slow mass transfer rate, so that the application of the DESs in actual production is greatly limited. Besides low price and environmental protection, water also has good capability of forming hydrogen bonds, and related documents show that water can participate in forming DESs and improve the physical and chemical properties of the DESs, such as viscosity reduction and polarity adjustment. Therefore, the invention adopts ternary DESs with water as the components of the DESs to extract the silymarin.
The segment activity coefficient conductor shielding model (COSMO-SAC) is a method for effectively predicting the thermodynamic properties of fluids, wherein molecular surface interaction is obtained through quantum chemical calculation, and the molecular surface local electrostatic interaction is analyzed by adopting a statistical thermodynamic method, so that the method is commonly used for predicting the solubility, activity coefficient, liquid-liquid balance, gas-liquid balance and the like of ionic liquids. Therefore, the DESS used for extracting silymarin is screened in an auxiliary manner by quantum chemical computation by combining with a COSMO-SAC model, so that the extraction rate is improved, meanwhile, the waste of medicines can be avoided, and the experimental time can be saved.
Therefore, how to screen the DESs through computer simulation calculation and combine theoretical calculation results with experimental verification to obtain a simple, efficient, green and environment-friendly silymarin extraction scheme is a problem that needs to be solved by technical personnel in the field.
Disclosure of Invention
The invention aims to provide the method for extracting the silymarin by screening the eutectic solvent with the assistance of the theoretical calculation, which is simple to operate and high in efficiency, and has the advantages of experiment cost saving, high extraction rate and environmental friendliness.
In order to achieve the purpose, the invention adopts the following technical scheme:
the method for extracting silymarin by screening ternary eutectic solvent with the assistance of theoretical calculation is characterized by comprising the following steps:
(1) constructing a model for optimization: respectively establishing a silymarin model substance and a eutectic solvent molecular model by using computer software, and performing structure optimization and energy optimization;
(2) calculated dissolution capacity (SP): further calculating by utilizing the optimized molecular fragment number and cavity number of the solute and the solvent to obtain the dissolving capacity (SP) of the solute in the eutectic solvent;
(3) screening and preparing a eutectic solvent: screening a eutectic solvent with larger dissolving capacity (SP), mixing a hydrogen bond acceptor, a hydrogen bond donor and water which can be used as both the hydrogen bond donor and the hydrogen bond acceptor, heating and stirring at 60-100 ℃ until a homogeneous, transparent and stable mixed solvent is formed, and cooling at room temperature to obtain a ternary eutectic solvent;
(4) extracting silymarin: separating silybum marianum seed shells, crushing by a crusher, sieving, degreasing and drying to obtain silybum marianum seed shell powder, mixing the silybum marianum seed shell powder with the eutectic solvent obtained in the step (3) according to the liquid-material ratio of 10-50 mL/g, and heating and stirring at 50-100 ℃ for 0.5-5 h to extract silymarin;
(5) and (4) centrifuging the silymarin-containing ternary eutectic solvent obtained in the step (4) at the rotating speed of 5000-12000 r/min for 15-30 min to obtain centrifugal supernatant, namely the silymarin extracting solution.
Preferably, in the method for extracting silymarin by using the ternary eutectic solvent, which is assisted by the theoretical calculation, the silymarin model substance in the step (1) is silybin.
Preferably, in the method for extracting silymarin by using ternary eutectic solvent assisted screening by theoretical calculation, the hydrogen bond receptors in the step (1) include but are not limited to choline chloride, betaine and tetraethylammonium bromide; hydrogen bond donors include, but are not limited to, 1, 2-propanediol, glycerol, ethylene glycol. Preferably, in the method for extracting silymarin by screening the ternary eutectic solvent with the assistance of theoretical calculation, the molar ratio of the hydrogen bond acceptor, the hydrogen bond donor and water in the step (3) is 1:2: 0-1: 2:2, and more preferably 1:2:1 or 1:1: 1.
Preferably, in the method for extracting silymarin by screening the ternary eutectic solvent with the assistance of the theoretical calculation, the heating in the step (4) is performed in a water bath kettle at 60-100 ℃, and more preferably, the heating temperature of the water bath kettle is 80 ℃.
Preferably, in the method for extracting silymarin by screening the ternary eutectic solvent with the assistance of the theoretical calculation, the silybum marianum seed shell powder in the step (4) is obtained by obtaining shell shells from silybum marianum seeds by stirring, polishing and blowing, grinding into powder by a grinder, sieving by a 100-mesh sieve, degreasing by petroleum ether in a Soxhlet extraction device, and drying at 105 ℃.
Preferably, in the method for extracting silymarin by screening ternary eutectic solvent assisted by theoretical calculation, the volume of the ternary eutectic solvent and the liquid-to-material ratio of the silybum marianum seed shell powder in the step (4) are 10-50 mL/g, and more preferably 20 mL/g.
Preferably, in the method for extracting silymarin by screening the ternary eutectic solvent with the assistance of the theoretical calculation, the heating temperature in the step (4) is 50-100 ℃, the extraction time is 0.5-5 h, and more preferably, the heating temperature is 80 ℃, and the extraction time is 4 h.
Preferably, in the method for extracting silymarin by screening the ternary eutectic solvent with the assistance of theoretical calculation, the rotation speed of centrifugation in the step (5) is 5000-12000 r/min, the centrifugation time is 15-30 min, and more preferably, the rotation speed of centrifugation is 8000r/min and the centrifugation time is 20 min.
The invention introduces the optimal process conditions for extracting silymarin from silybum marianum by using a eutectic solvent: taking choline chloride/ethylene glycol/water/as an extracting agent (the molar ratio is 1:2:1), the liquid-material ratio is 20mL/g, the extraction temperature is 80 ℃, the extraction time is 4h, the centrifugation is carried out for 20min at 8000r/min, and the supernatant is taken to obtain the silymarin extracting solution, wherein the extraction rate of the silymarin is 1.44 percent, and is 71.43 percent higher than that of the methanol extraction.
According to the technical scheme, the invention has the following advantages:
(1) the method adopts the combination of computer simulation and experiment to screen DES, thereby improving the silymarin extraction rate and saving manpower and material resources;
(2) the ternary eutectic solvent is used, so that the preparation method has the advantages of simple preparation process, low cost, environmental friendliness and the like, and the ternary DESS prepared by adding water improves the performance of the binary DESS while reducing the viscosity and increasing the strength of hydrogen bonds;
(3) in addition, the extraction method is simple to operate, the extraction rate of the prepared product is high, and the extraction rate of silymarin extracted by the method is 1.44 percent and is 71.43 percent higher than that of the silymarin extracted by methanol.
Drawings
FIG. 1 is a flow chart of simulated calculated capacity (SP).
FIG. 2 is a chart of surface charge density of silybin molecules.
Figure 3 is a spatial distribution diagram of choline chloride/ethylene glycol/water.
FIG. 4 is a chart showing the Solubility (SP) of silibinin in different eutectic solvents as a thermal map.
FIG. 5 is a high performance liquid chromatogram of standard silybin and extractive solution.
FIG. 6 is a diagram showing the extraction rate of silybin by a typical solvent.
FIG. 7 is a graph showing the extraction rate of silybin under different extraction conditions.
Detailed Description
The present invention is further described below with reference to examples.
Example 1
(1) Taking a silibinin model as an example, and referring to a flow chart shown in the attached figure 1, a molecular model is established by using Materials Studio software;
(2) and performing geometric optimization and energy optimization on the molecular model, and outputting a COSMO file as shown in FIG. 2.
Example 2
(1) Taking choline chloride/1, 2-propylene glycol/water ternary DES as an example, referring to the flow chart shown in figure 1, a molecular model is established by using Materials Studio software, as shown in figure 3;
(2) carrying out geometric optimization and energy optimization on the molecular model, and outputting a COSMO file;
(3) and (2) importing the silybin molecule COSMO file, the COSMO file generated in the step (1) and the data of the number of the molecular fragments and the number of the holes into a COSMO-VT program, and calculating the dissolving capacity (SP) of the silybin in the choline chloride/1, 2-propylene glycol/water ternary DES, wherein the SP represents the maximum dissolving amount of the silybin in the solvent, and the larger the SP is, the stronger the dissolving capacity of the silybin in the solvent is.
Example 3
(1) Taking choline chloride/ethylene glycol/water ternary DES as an example, referring to a flow chart shown in figure 1, and establishing a molecular model by using Materials Studio software;
(2) carrying out geometric optimization and energy optimization on the molecular model, and outputting a COSMO file;
(3) introducing the silybin molecule COSMO file, the COSMO file generated in the step (1) and the data of the number of the molecule fragments and the number of the holes into a COSMO-VT program, and calculating the dissolving capacity of the silybin in choline chloride/ethylene glycol/water DES, wherein FIG. 4 is a heat map of the dissolving capacity of the silybin in different DESs.
TABLE 1 Silibinin solubility in the preferred DESs and conventional Solvents (SP)
The resulting choline chloride/ethylene glycol/water system was calculated to have the greatest Solvency (SP) and the methanol to have the least SP.
Example 4
Weighing the medicines with different combinations in the table 2 according to the molar ratios shown, placing the medicines into a round-bottom flask, heating the medicines in a water bath at 80 ℃ in a magnetic stirrer, magnetically stirring the medicines until the medicines are colorless, transparent and uniform, taking out the flask, and cooling the flask at room temperature to obtain a eutectic solvent;
at room temperature of 25 ℃, 1mL of the eutectic solvent was aspirated and used for viscosity measurement by a viscometer, and the measurement results are shown in table 2.
TABLE 2 typical DESS compositions and viscosities thereof
The addition of water may reduce the viscosity of the DESs.
Example 5: establishment of a Standard Curve
According to the national standard SW/T7-2013, the silybum marianum extract is a plant extract, the highest content of active ingredients in silymarin is silybin, and the silybin is a silymarin index ingredient. Therefore, a standard curve is prepared by using silybin, and the silybin has a maximum absorption peak under the condition of 288nm of wavelength;
(1) standard solution of silybin: accurately weighing 0.05g of silybin reference substance, dissolving with methanol, and metering to 100 mL;
(2) the standard solutions were diluted 20-fold, 30-fold, 40-fold, 50-fold and 60-fold, and HPLC analysis was performed in parallel for each concentration group of 3, with the following analytical detection conditions:
a chromatographic column: octadecyl bonding silica gel is used as a filling agent, the length is 150mm, and the inner diameter is 4.6 mm;
detection wavelength: 288 nm;
the mobile phase is methanol and water, 60: 40;
flow rate: 0.8 mL/min;
sample introduction amount: 10 μ L
(3) Using silibinin concentration (mg/mL) as abscissa and peak area as ordinate to draw silibinin standard curve, wherein the standard curve equation is that y is 6 × 107x-63009(R20.9995), fig. 5a is a typical chromatogram of the silibinin standard.
Example 6: examination of typical solvent classes
The method for extracting silymarin by screening ternary eutectic solvent with the assistance of theoretical calculation is characterized by comprising the following steps:
(1) mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent, uniform and stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) stirring and polishing and blowing to obtain seed shells from silybum marianum seeds, grinding the silybum marianum seed shells into powder by using a grinder, sieving by using a 100-mesh sieve, degreasing by using petroleum ether in a Soxhlet extraction device, drying in a 105-DEG C oven, accurately weighing 0.5g of silybum marianum seed shell powder, mixing with 10mL of choline chloride/ethylene glycol/water eutectic solvent obtained in the step (1) according to the liquid-material ratio of 20mL/g, heating and stirring at 80 ℃, and extracting for 4 hours to obtain a silymarin crude extracting solution;
(3) centrifuging the extracting solution obtained in the step (2) at 8000r/min for 20min to obtain centrifugal supernatant, namely silymarin extracting solution;
(4) diluting the filtrate obtained in the step (3) by a proper amount, and performing HPLC analysis, wherein a graph 5b is a typical chromatogram of the silymarin extracting solution, comparing a spectrogram peak area measured by the silymarin extracting solution with a standard curve to obtain an extracting solution concentration c, and calculating to obtain the silybin extraction rate:
in the above formula:
c is the concentration of the extract in mg/mL
V is the volume of the extract in mL
m is the mass of the milk thistle seed shell powder, and the unit is g
As shown in fig. 6, the highest extraction rate was obtained for the choline chloride/ethylene glycol/water system. Therefore, in the investigation of typical solvent types, the extraction effect of the choline chloride/ethylene glycol/water system is the best and is consistent with the calculation result.
Example 7: optimizing extraction time
The method for extracting silymarin by screening ternary eutectic solvent with the assistance of theoretical calculation is characterized by comprising the following steps:
(1) mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent, uniform and stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) stirring, grinding and blowing to obtain seed shells from silybum marianum seeds, grinding the silybum marianum seed shells into powder by using a grinder, sieving by using a 100-mesh sieve, degreasing by using petroleum ether in a Soxhlet extraction device, drying in a 105-DEG C oven, accurately weighing 0.25g of silybum marianum seed shell powder, mixing with 10mL of choline chloride/ethylene glycol/water eutectic solvent obtained in the step (1) according to the liquid-material ratio of 40mL/g for 2h,3h,4h,5h and 6h respectively, and heating and stirring at 70 ℃ to obtain a silymarin crude extracting solution;
(3) centrifuging the extracting solution obtained in the step (2) at 8000r/min for 20min to obtain centrifugal supernatant, namely silymarin extracting solution;
(4) and (4) respectively taking the silymarin extracting solution, diluting the silymarin extracting solution by a proper amount, and then carrying out HPLC analysis. The concentration of the extract is obtained by comparing with a standard curve, and the extraction rate of the silibinin is calculated. As shown in FIG. 7a, the extraction time was 4 hours, and the extraction yield was 1.31% at the maximum.
Example 8: optimizing extraction temperature
The method for extracting silymarin by screening ternary eutectic solvent with the assistance of theoretical calculation is characterized by comprising the following steps:
(1) mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent, uniform and stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) stirring, grinding and blowing to obtain seed shells from silybum marianum seeds, grinding the silybum marianum seed shells into powder by using a grinder, sieving by using a 100-mesh sieve, degreasing by using petroleum ether in a Soxhlet extraction device, drying in a 105-DEG C oven, accurately weighing 0.5g of silybum marianum seed shell powder, mixing with 10mL of choline chloride/ethylene glycol/water eutectic solvent obtained in the step (1) according to the liquid-material ratio of 20mL/g, extracting for 3h, and heating and stirring at 50 ℃,60 ℃,70 ℃,80 ℃ and 90 ℃ respectively to obtain a silymarin crude extract;
(3) centrifuging the extracting solution obtained in the step (2) at 8000r/min for 20min to obtain centrifugal supernatant, namely silymarin extracting solution;
(4) and (4) respectively taking the silymarin extracting solution, diluting the silymarin extracting solution by a proper amount, and then carrying out HPLC analysis. The concentration of the extract is obtained by comparing with a standard curve, and the extraction rate of the silibinin is calculated. As shown in FIG. 7b, the extraction rate was 1.23% at 80 ℃.
Example 9: optimizing liquid-to-material ratio
The method for extracting silymarin by screening ternary eutectic solvent with the assistance of theoretical calculation is characterized by comprising the following steps:
(1) mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent, uniform and stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) stirring, grinding and blowing to obtain seed shells from silybum marianum seeds, grinding the silybum marianum seed shells into powder by using a grinder, sieving by using a 100-mesh sieve, degreasing by using petroleum ether in a Soxhlet extraction device, drying in a 105-DEG C oven, mixing the silybum marianum seed shell powder with the choline chloride/ethylene glycol/water eutectic solvent obtained in the step (1) according to the liquid-material ratio of 10,20,30,40 and 50mL/g, extracting for 4 hours, and heating and stirring at 70 ℃ to obtain a silymarin crude extract;
(3) centrifuging the extracting solution obtained in the step (2) at 8000r/min for 20min to obtain centrifugal supernatant, namely silymarin extracting solution;
(4) and (4) respectively taking the silymarin extracting solution, diluting the silymarin extracting solution by a proper amount, and then carrying out HPLC analysis. The concentration of the extract is obtained by comparing with a standard curve, and the extraction rate of the silibinin is calculated. As shown in FIG. 7c, the extraction yield was 1.35% at a liquid-to-feed ratio of 20 mL/g.
The invention adopts a simulation calculation method to assist in screening the DESs for extracting the silymarin, greatly saves manpower and material resources, provides the DESs extraction method for the silymarin with high extraction rate, environmental protection and simple and convenient operation, and obtains the optimal process conditions for extracting the silymarin: taking choline chloride/ethylene glycol/water as an extracting agent (the molar ratio is 1:2:1), the liquid-material ratio is 20mL/g, the extraction temperature is 80 ℃, the extraction time is 4h, 8000r/min is centrifuged for 20min, and the supernate is taken to obtain the silymarin extracting solution. The method for extracting silymarin is far higher than that of a common organic solvent (methanol).
Those skilled in the art will appreciate that the above embodiments are merely exemplary embodiments and that various changes, substitutions, and alterations can be made without departing from the spirit and scope of the invention.
Claims (5)
1. The method for extracting silymarin by screening ternary eutectic solvent with the assistance of theoretical calculation is characterized by comprising the following steps:
(1) constructing a model for optimization: respectively establishing a silymarin model substance and a eutectic solvent molecular model by using computer software, and performing structure optimization and energy optimization;
(2) calculated dissolution capacity (SP): further calculating by utilizing the optimized molecular fragment number and cavity number of the solute and the solvent to obtain the dissolving capacity (SP) of the solute in the eutectic solvent;
(3) screening and preparing a eutectic solvent: screening a eutectic solvent with high dissolving capacity (SP), mixing a hydrogen bond acceptor, a hydrogen bond donor and water which can be used as both the hydrogen bond donor and the hydrogen bond acceptor, heating and stirring at 60-100 ℃ until a homogeneous, transparent and stable mixed solvent is formed, and cooling at room temperature to obtain a ternary eutectic solvent;
(4) extracting silymarin: separating silybum marianum seed shells, crushing by a crusher, sieving, degreasing and drying to obtain silybum marianum seed shell powder, mixing the silybum marianum seed shell powder with the eutectic solvent obtained in the step (3) according to the liquid-material ratio of 10-50 mL/g, and heating and stirring at 50-100 ℃ for 0.5-5 h to extract silymarin;
(5) and (4) centrifuging the silymarin-containing ternary eutectic solvent obtained in the step (4) at the rotating speed of 5000-12000 r/min for 15-30 min, and obtaining centrifugal supernatant, namely the silymarin extracting solution.
2. The method for extracting silymarin by using the ternary eutectic solvent as the auxiliary screening agent in the theoretical calculation manner as claimed in claim 1, wherein the silymarin model compound in the step (1) is silybin.
3. The method for extracting silymarin by using ternary eutectic solvent with auxiliary screening of theoretical calculation as claimed in claim 1, wherein the eutectic solvent hydrogen bond receptor in step (1) includes but is not limited to choline chloride, betaine, tetraethylammonium bromide; hydrogen bond donors include, but are not limited to, 1, 2-propanediol, glycerol, ethylene glycol.
4. The method for extracting silymarin by theoretical calculation assisted screening of ternary eutectic solvents according to claim 1, wherein the molar ratio of the hydrogen bond acceptor, the hydrogen bond donor and water in step (3) is 1:2: 0-1: 2: 2.
5. The method for extracting silymarin by aid of the ternary eutectic solvent for theoretical calculation and screening as claimed in claim 1, wherein in step (4), the silybum marianum seed shell powder is obtained by stirring, grinding and blowing the silybum marianum seed shell by a wind blowing method, grinding the silybum marianum seed shell powder by a grinder, sieving the silybum marianum seed shell powder by a 80-120-mesh sieve, degreasing the silybum marianum seed shell powder by a Soxhlet extraction device for 0.5-1.5 h by petroleum ether, and drying the silybum marianum seed.
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| CN117476126A (en) * | 2023-12-28 | 2024-01-30 | 中国农业科学院蜜蜂研究所 | Propolis flavone extraction method for targeted preparation of uric acid-reducing activity and application |
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| CN117476126A (en) * | 2023-12-28 | 2024-01-30 | 中国农业科学院蜜蜂研究所 | Propolis flavone extraction method for targeted preparation of uric acid-reducing activity and application |
| CN117476126B (en) * | 2023-12-28 | 2024-03-19 | 中国农业科学院蜜蜂研究所 | Propolis flavone extraction method for targeted preparation of uric acid-reducing activity and application |
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