CN113045555B - Method for extracting silymarin by theoretical calculation assisted screening ternary eutectic solvent - Google Patents
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Abstract
The invention discloses a method for extracting silymarin by using a theoretical calculation-assisted screening ternary eutectic solvent. By quantum chemistry, a single molecule model of 1296 groups of eutectic solvents (Deep Eutectic Solvents, DESs) was established. The silybin is taken as a solute molecular model, the dissolving capacity (SP) of the silybin in different DESs is predicted through theoretical calculation, the three-way DESs with high silymarin extraction rate and low viscosity are obtained through screening, after the DESs are prepared, the defatted silybum marianum seed shell powder is mixed with the silymarin seed shell powder, heating and stirring are carried out, the silymarin extract is obtained through centrifugation, and the content of the silybin in the silymarin extract is measured through high performance liquid chromatography and compared with the traditional organic Solvent extraction. The DESs used for silymarin extraction are screened in an auxiliary mode by adopting a simulation calculation method, manpower and material resources are greatly saved, and the DESs extraction method for silymarin is 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 using a ternary eutectic solvent.
Background
In 2003, abbott et al found for the first time a solvent-eutectic solvent (Deep Eutectic Solvents, DESs) formed from quaternary ammonium salts and amide compounds that was excellent in properties. The solvent has similar properties to ionic liquid, is nontoxic and biodegradable, and is a novel green solvent. At present, eutectic solvents have attracted considerable attention from researchers in various countries around the world, and have shown good application prospects in the fields of separation processes, chemical reactions, functional materials, electrochemistry and the like.
Silybum marianum is a plant of Silybum genus of Compositae, and has been popularized and planted in China in 1972 as a plant for liver protection. The silymarin is a natural active ingredient contained in the silymarin seed shell, mainly silymarin, has the effects of protecting liver, promoting bile flow, reducing blood sugar and blood lipid, resisting cancer, resisting inflammation and resisting coagulation, can prevent ischemic cardiovascular and cerebrovascular diseases and diabetic chronic complications, and has high medical value. Silybin is the component with highest content and highest activity.
At present, the silymarin is mainly extracted by an organic solvent extraction method, and ultrasound and microwave are also tried to strengthen mass transfer so as to shorten the extraction period, and the like (CN 201610763023.7) are used for extracting flavonoid compounds in the stems and leaves of the silybum marianum by ethanol reflux, and water washing and alkali washing are used for adsorption by macroporous resin. Wu Junming et al (CN 201710677923.4) solvent extraction of silybum marianum shells: putting the treated silybum marianum shell strips into an extraction tank, adding ethyl acetate with the amount of 2-4 times, refluxing for 15-24 hours, and recovering the ethyl acetate to obtain the total flavone. Because the traditional solvent extraction has the problems of higher energy consumption, low extraction rate, large damage to active substances, serious toxic substance residues and the like, researchers gradually start to extract natural products such as flavonoid compounds by using green environment-friendly DESs, and the DESs have advantages (CN 201610827959.1) especially for silymarin extraction, but the DESs do not see related documents yet. And because DESs have designability, the combination types are huge, if the DESs are screened one by one through experiments, the labor and material resources and the time input cost are overlarge and the efficiency is low, and the DESs are low in mass transfer rate due to high viscosity, so that the application of the DESs in actual production is greatly limited. In addition to being low-cost and environmentally friendly, water has a good ability to form hydrogen bonds, and recent relevant literature shows that water can participate in the formation of DESs and improve the physicochemical properties thereof, such as viscosity reduction and polarity adjustment. The present invention uses ternary DESs with water as the constituent of the DESs for silymarin extraction.
The fragment activity coefficient type conductor shielding model (COSMO-SAC) is a method for effectively predicting thermodynamic properties of fluid, wherein molecular surface interaction is obtained through quantum chemical computation, and a statistical thermodynamic method is adopted to analyze and analyze local electrostatic action on the molecular surface, and is commonly used for predicting solubility, activity coefficient, liquid-liquid balance, gas-liquid balance and the like of ionic liquid. Therefore, DESs used for extracting silymarin are screened in a quantum chemical calculation assisted mode by combining a COSMO-SAC model, the extraction rate is improved, medicine waste can be avoided, and experimental time is saved.
Therefore, how to screen 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 to be solved by those skilled in the art.
Disclosure of Invention
The invention aims to provide a method for extracting silymarin by using a theoretical calculation-assisted screening eutectic solvent, which is simple to operate and high in efficiency, and has the advantages of saving experimental cost, high extraction rate and environmental protection.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the method for extracting silymarin by using the ternary eutectic solvent through theoretical calculation assisted screening is characterized by comprising the following steps of:
(1) And (3) constructing a model for optimization: respectively establishing a silymarin model object and a eutectic solvent molecular model by using computer software, and performing structure optimization and energy optimization;
(2) Calculation of dissolution power (SP): further calculating by optimizing the molecular fragment number and hole number of the obtained solute and solvent to obtain the dissolution capacity (SP) of the solute in the eutectic solvent;
(3) Screening and preparing a eutectic solvent: the eutectic solvent with larger dissolution capacity (SP) is screened, the hydrogen bond acceptor, the hydrogen bond donor and water which can be used as the hydrogen bond donor and the hydrogen bond acceptor are mixed, heated and stirred at 60-100 ℃ until a homogeneous, transparent and stable mixed solvent is formed, and the ternary eutectic solvent is obtained after cooling at room temperature;
(4) Extracting silymarin: separating silybum marianum seed shells, crushing by a crusher, sieving, degreasing, 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) Centrifuging the ternary eutectic solvent containing silymarin obtained in the step (4) for 15-30 min at the rotating speed of 5000-12000 r/min, and obtaining supernatant fluid which is silymarin extracting solution.
Preferably, the method for extracting the silymarin by using the ternary eutectic solvent is selected by the aid of theoretical calculation, and the silymarin model in the step (1) is silybin.
Preferably, in the method for extracting silymarin by using the ternary eutectic solvent in the theoretical calculation-assisted screening, the hydrogen bond acceptor in the step (1) includes but is 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 using the ternary eutectic solvent in the theoretical calculation-assisted screening, the molar ratio of the hydrogen bond acceptor to the hydrogen bond donor to the 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 using the ternary eutectic solvent through theoretical calculation-assisted screening, in the step (4), the heating 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 using the ternary eutectic solvent with the aid of theoretical calculation and screening, the silybum marianum seed shell powder in the step (4) is obtained by obtaining seed shells from silybum marianum seeds by adopting a stirring grinding and blowing method, grinding the seed shells into powder by using a grinder, screening the powder by using a 100-mesh screen, degreasing the powder by using petroleum ether in a Soxhlet extraction device, and drying the powder at 105 ℃.
Preferably, in the method for extracting silymarin by using the ternary eutectic solvent in the theoretical calculation-assisted screening, the liquid-material ratio of the silymarin seed shell powder to the volume of the eutectic solvent in the step (4) is 10-50 mL/g, and more preferably 20mL/g.
Preferably, in the method for extracting silymarin by using the ternary eutectic solvent in the theoretical calculation-assisted screening, the heating temperature in the step (4) is 50-100 ℃, the extraction time is 0.5-5 h, more preferably, the heating temperature is 80 ℃, and the extraction time is 4h.
Preferably, in the method for extracting silymarin by using the theoretical calculation-assisted screening ternary eutectic solvent, 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 20min.
The invention introduces the optimal technological conditions for extracting silymarin in silybum marianum by using a eutectic solvent: choline chloride/ethylene glycol/water/is used as an extracting agent (molar ratio is 1:2:1), the liquid-material ratio is 20mL/g, the extracting temperature is 80 ℃, the extracting time is 4h, the extracting is performed for 20min at 8000r/min, the supernatant is taken, and the silymarin extracting solution is obtained, wherein the silymarin extracting rate is 1.44% and is 71.43% higher than that of methanol extraction.
According to the technical scheme, the invention has the following advantages:
(1) According to the invention, the DES is screened by combining computer simulation and experiments, so that the extraction rate of silymarin is improved, and meanwhile, manpower and material resources are saved;
(2) The ternary eutectic solvent is used, so that the ternary DESs prepared after the water is added have the advantages of simple preparation process, low cost, environmental protection and the like, and the performances of the binary DESs are improved while the viscosity is reduced and the strength of hydrogen bonds is increased;
(3) In addition, the extraction method of the invention has simple operation and high extraction rate of the prepared product, and the extraction rate of the silymarin extracted by the method of the invention is 1.44 percent and 71.43 percent higher than that extracted by methanol.
Drawings
FIG. 1 is a flow chart for modeling the calculation of Solvency (SP).
FIG. 2 is a graph showing the surface charge density of silybin molecules.
Figure 3 is a graph showing the spatial distribution of choline chloride/ethylene glycol/water.
FIG. 4 is a graph showing the dissolution power (SP) heat of silybin in different eutectic solvents.
FIG. 5 is a high performance liquid chromatogram of silybin standard and extractive solution.
FIG. 6 is a graph showing the extraction rate of silybin by typical solvents.
FIG. 7 is a diagram showing the extraction rate of silibinin under different extraction conditions.
Detailed Description
The invention is further described below with reference to examples.
Example 1
(1) Taking a silybin model object as an example, referring to a flow chart shown in fig. 1, a molecular model is built by using Materials Studio software;
(2) The molecular model is subjected to geometric optimization and energy optimization, and a COSMO file is output, 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 built by using Materials Studio software, as shown in figure 3;
(2) Performing geometric optimization and energy optimization on the molecular model, and outputting a COSMO file;
(3) And (2) importing the silybin molecular COSMO file, the COSMO file generated in the step (1) and the data of the number of molecular fragments and the number of holes into a COSMO-VT program, and calculating the dissolving capacity (SP) of the silybin in the choline chloride/1, 2-propanediol/water ternary DES, wherein the SP represents the maximum dissolving capacity 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 the flow chart shown in figure 1, a molecular model is built by using Materials Studio software;
(2) Performing geometric optimization and energy optimization on the molecular model, and outputting a COSMO file;
(3) And (2) importing the silybin molecular COSMO file, the COSMO file generated in the step (1), and the data of the number of molecular fragments and the number of holes into a COSMO-VT program, calculating the dissolving capacity of silybin in choline chloride/ethylene glycol/water DES, and obtaining a heat map of the dissolving capacity of silybin in different DESs in FIG. 4.
TABLE 1 Silybin solvency in superior DESs and conventional Solvents (SP)
The calculated dissolution power (SP) of the choline chloride/ethylene glycol/water system was maximum and the SP of methanol was minimum.
Example 4
Weighing the medicines with different combinations in Table 2 according to the mol ratio shown, placing the medicines into a round bottom flask, heating 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 the eutectic solvent;
at room temperature of 25 ℃, 1mL of the eutectic solvent was sucked up for viscosity measurement by a viscosity meter, and the measurement results are shown in Table 2.
TABLE 2 typical DESs composition and viscosity 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 plant extract silybum marianum extract, the content of the active ingredient in silybum marianum is the highest, and the silybum marianum is the index ingredient of silybum marianum. Therefore, the standard curve is prepared by using the silybin, and the silybin has the maximum absorption peak under the condition of 288nm wavelength;
(1) Standard solution of silybin: accurately weighing 0.05g of silybin reference substance, dissolving in methanol, and fixing volume to 100mL;
(2) The standard solutions were diluted 20-fold, 30-fold, 40-fold, 50-fold and 60-fold, and each concentration 3 group was subjected to HPLC analysis in parallel under the following assay conditions:
chromatographic column: octadecyl bonded silica gel is used as filler, the length is 150mm, and the inner diameter is 4.6mm;
detection wavelength: 288nm;
mobile phase methanol: water=60:40;
flow rate: 0.8mL/min;
sample injection amount: 10 mu L
(3) Drawing a silybin standard curve by taking the concentration (mg/mL) of silybin as an abscissa and the peak area as an ordinate, wherein the standard curve equation is that y=6x10 7 x-63009(R 2 =0.9995), fig. 5a is a typical chromatogram of a silybin standard.
Example 6: investigation of typical solvent species
The method for extracting silymarin by using the ternary eutectic solvent through theoretical calculation assisted screening is characterized by comprising the following steps of:
(1) Mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent uniform stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) Obtaining seed shells from silybum marianum seeds by adopting a stirring grinding and air blowing method, grinding the seed shells into powder by using a grinder, sieving by using a 100-mesh screen, degreasing by using petroleum ether in a Soxhlet extraction device, drying in an oven at 105 ℃, accurately weighing 0.5g of the seed shell powder of silybum marianum, mixing with 10mL of choline chloride/glycol/water eutectic solvent obtained in the step (1) according to a liquid-material ratio of 20mL/g, heating and stirring at 80 ℃, and extracting for 4 hours to obtain silymarin crude extract;
(3) Centrifuging the extracting solution obtained in the step (2) for 20min at 8000r/min, wherein the obtained supernatant is silymarin extracting solution;
(4) Carrying out HPLC analysis on the filtrate obtained in the step (3) after a proper amount of dilution, wherein fig. 5b is a typical chromatogram of the silymarin extracting solution, comparing the peak areas of the chromatogram determined by the silymarin extracting solution with a standard curve to obtain the extracting solution concentration c, and calculating to obtain the silybin extracting rate:
in the above formula:
c is the concentration of the extract in mg/mL
V is the volume of the extracting solution, and the unit is mL
m is the mass of silybum marianum seed shell powder, and the unit is g
As shown in fig. 6, the highest extraction rate of the choline chloride/ethylene glycol/water system was obtained. Therefore, in the investigation of the typical solvent type, the extraction effect of a choline chloride/ethylene glycol/water system is optimal, and the calculation result is consistent.
Example 7: optimizing extraction time
The method for extracting silymarin by using the ternary eutectic solvent through theoretical calculation assisted screening is characterized by comprising the following steps of:
(1) Mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent uniform stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) Grinding the silybum marianum seed shells into powder by adopting a stirring grinding and air blowing method, sieving the powder by using a grinder, degreasing the powder by using petroleum ether in a Soxhlet extraction device, drying the powder in a baking oven at 105 ℃, accurately weighing 0.25g of the silybum marianum seed shells, mixing the powder with 10mL of choline chloride/glycol/water eutectic solvent obtained in the step (1) according to the liquid-material ratio of 40mL/g, and extracting for 2h,3h,4h,5h and 6h respectively, and heating and stirring at 70 ℃ to obtain silymarin crude extract;
(3) Centrifuging the extracting solution obtained in the step (2) for 20min at 8000r/min, wherein the obtained supernatant is silymarin extracting solution;
(4) And respectively taking silymarin extract, diluting with a proper amount, and performing HPLC analysis. And (5) comparing the standard curves to obtain the concentration of the extracting solution, and calculating to obtain the silybin extraction rate. As shown in FIG. 7a, the extraction time was 4 hours, and the extraction rate was 1.31% at maximum.
Example 8: optimizing extraction temperature
The method for extracting silymarin by using the ternary eutectic solvent through theoretical calculation assisted screening is characterized by comprising the following steps of:
(1) Mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent uniform stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) Grinding the silybum marianum seed shells into powder by adopting a stirring grinding and air blowing method, sieving the powder by using a grinder, degreasing the powder by using petroleum ether in a Soxhlet extraction device, drying the powder in a baking oven at 105 ℃, accurately weighing 0.5g of the silybum marianum seed shells, mixing the powder with 10mL of choline chloride/glycol/water eutectic solvent obtained in the step (1) according to the liquid-material ratio of 20mL/g, extracting the mixture for 3 hours, and heating and stirring the mixture at 50 ℃,60 ℃,70 ℃,80 ℃ and 90 ℃ respectively to obtain silymarin crude extract;
(3) Centrifuging the extracting solution obtained in the step (2) for 20min at 8000r/min, wherein the obtained supernatant is silymarin extracting solution;
(4) And respectively taking silymarin extract, diluting with a proper amount, and performing HPLC analysis. And (5) comparing the standard curves to obtain the concentration of the extracting solution, and calculating to obtain the silybin extraction rate. 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 using the ternary eutectic solvent through theoretical calculation assisted screening is characterized by comprising the following steps of:
(1) Mixing choline chloride, ethylene glycol and water according to a molar ratio of 1:2:1, heating to form a transparent uniform stable mixed solution system, and cooling at room temperature to obtain a eutectic solvent;
(2) Obtaining seed shells from silybum marianum seeds by adopting a stirring grinding and air blowing method, grinding the seed shells of silybum marianum into powder by using a grinder, sieving by using a 100-mesh screen, degreasing by using petroleum ether in a Soxhlet extraction device, drying in an oven at 105 ℃, mixing the seed shell powder of silybum marianum with the choline chloride/ethylene glycol/water eutectic solvent obtained in the step (1) in a liquid-material ratio of 10,20,30,40 and 50mL/g, extracting for 4 hours, heating and stirring at 70 ℃ to obtain silymarin crude extract;
(3) Centrifuging the extracting solution obtained in the step (2) for 20min at 8000r/min, wherein the obtained supernatant is silymarin extracting solution;
(4) And respectively taking silymarin extract, diluting with a proper amount, and performing HPLC analysis. And (5) comparing the standard curves to obtain the concentration of the extracting solution, and calculating to obtain the silybin extraction rate. As shown in FIG. 7c, the maximum extraction rate was 1.35% when the liquid-to-material ratio was 20mL/g.
The invention adopts a simulation calculation method to assist in screening DESs used for silymarin extraction, and provides the DESs extraction method of silymarin with high extraction rate, environmental protection and simple operation while greatly saving manpower and material resources, thereby obtaining the optimal technological conditions for extracting silymarin: taking choline chloride/glycol/water as an extracting agent (molar ratio of 1:2:1), wherein the liquid-material ratio is 20mL/g, the extracting temperature is 80 ℃, the extracting time is 4h, the extracting time is 8000r/min, centrifuging for 20min, and taking the supernatant to obtain the silymarin extracting solution. The method of the invention is used for extracting silymarin which is far higher than common organic solvent (methanol).
It should be understood by those skilled in the art that the above embodiments are exemplary embodiments only and that various changes, substitutions and alterations can be made hereto without departing from the spirit and scope of the invention.
Claims (3)
1. The method for extracting the silybin by using the ternary eutectic solvent through theoretical calculation assisted screening is characterized by comprising the following steps of:
(1) And (3) constructing a model for optimization: respectively establishing a silybin molecular model and a eutectic solvent molecular model by using computer software, and performing structure optimization and energy optimization;
(2) Calculation of dissolution power (SP): further calculating by optimizing the molecular fragment number and hole number of the obtained solute and solvent to obtain the dissolution capacity (SP) of the solute in the eutectic solvent;
(3) Screening and preparing a eutectic solvent: the eutectic solvent with larger dissolution capacity (SP) is screened, a hydrogen bond acceptor, a hydrogen bond donor and water which can be used as the hydrogen bond donor and the hydrogen bond acceptor are mixed, heated and stirred at 60-100 ℃ until a homogeneous, transparent and stable mixed solvent is formed, and the ternary eutectic solvent is obtained by cooling at room temperature;
the hydrogen bond acceptor is one of choline chloride and betaine; the hydrogen bond donor is one of 1, 2-propylene glycol, glycerol and ethylene glycol;
(4) Extracting silybin: separating silybum marianum seed shells, crushing by a crusher, sieving, degreasing, 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-to-material ratio of 10-50 mL/g, and heating and stirring at 50-100 ℃ for 0.5-5 h to extract silybin;
(5) Centrifuging the ternary eutectic solvent containing the silybin obtained in the step (4) for 15-30 min at the rotating speed of 5000-12000 r/min, and obtaining a supernatant fluid which is the silybin extracting solution.
2. The method for extracting silybin 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 the step (3) is 1:2:1.
3. The method for extracting silybin by using the ternary eutectic solvent with the aid of theoretical calculation and screening according to claim 1, wherein the silybum marianum seed shell powder in the step (4) is obtained by obtaining seed shells from silybum marianum seeds by adopting a stirring grinding and wind blowing method, grinding the seed shells into powder by using a grinder, sieving the powder by using a 80-120-mesh sieve, degreasing the powder by using petroleum ether in a Soxhlet extraction device for 0.5-1.5 h, and drying the powder at 105 ℃.
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