CN115343408A - Synchronous green extraction method of phenolic acids and tanshinone compounds in salvia miltiorrhiza bunge - Google Patents
Synchronous green extraction method of phenolic acids and tanshinone compounds in salvia miltiorrhiza bunge Download PDFInfo
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- CN115343408A CN115343408A CN202211006144.9A CN202211006144A CN115343408A CN 115343408 A CN115343408 A CN 115343408A CN 202211006144 A CN202211006144 A CN 202211006144A CN 115343408 A CN115343408 A CN 115343408A
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- salvia miltiorrhiza
- extraction
- tanshinone
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- 150000007965 phenolic acids Chemical class 0.000 title claims abstract description 18
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Abstract
The invention discloses a synchronous green extraction method of phenolic acids and tanshinone compounds in salvia miltiorrhiza. Pulverizing Saviae Miltiorrhizae radix into Saviae Miltiorrhizae radix powder; adding a biosurfactant sodium chenodeoxycholate into the salvia miltiorrhiza powder to carry out mechanical and chemical grinding treatment to obtain a co-ground product; and taking out the co-ground product, adding deionized water for dissolving, magnetically stirring, centrifuging, and taking an upper layer sample solution. The invention has wide application range, can be used for detecting hydrophilic phenolic acid in various medicinal materials and hydrophobic tanshinone in various medicinal materials, and has wide application potential in extraction of natural medicinal materials. The method can be successfully applied to qualitative and quantitative analysis of hydrophilic phenolic acids (tanshinol, salvianolic acid A, salvianolic acid B, rosmarinic acid and lithospermic acid) and hydrophobic tanshinone (tanshinone I, tanshinone II A, cryptotanshinone and dihydrotanshinone I) in the salvia miltiorrhiza bunge.
Description
Technical Field
The invention belongs to the field of natural medicine extraction and detection, and particularly relates to a synchronous green extraction method of phenolic acids and tanshinone compounds in salvia miltiorrhiza.
Background
The natural products are mainly derived from animals, plants, fungi, microorganisms or metabolites thereof, including flavonoids, alkaloids, polysaccharides, quinones, essential oil and the like, provide primary health care requirements for human beings, and have wide development and application prospects. Extraction is the first step in separating and extracting the target active ingredient from the raw material, and therefore, it is very important to select an appropriate and efficient extraction method according to the properties of the matrix. At present, the common methods for hydrophilic compounds comprise an immersion method, a decoction method and a Soxhlet extraction method, wherein an extraction solvent is generally a mixed solution of water and an organic solvent, so that the extraction of ineffective components (such as polysaccharide, fiber and mucilaginous) is avoided, but the methods have long extraction time, complex steps and low extraction efficiency; the extraction of hydrophobic compounds is generally carried out by ultrasound-assisted extraction and thermal reflux extraction, both of which are considered as common extraction techniques, but neither of which avoids the use of organic solvents. In the existing extraction method, the extraction of the two compounds is mutually split, and few researches consider that hydrophilic compounds and hydrophobic compounds are captured simultaneously. The above disadvantages limit the industrial application of these processes and therefore there is an urgent need to develop a green, simple and promising process to achieve the simultaneous extraction of both classes of compounds in a complex matrix.
Sodium deoxycholate is an inexpensive non-acid tolerant biosurfactant derived from mammalian bile and composed of hydrophilic and hydrophobic groups commonly used to increase the water solubility of organic materials. Biosurfactants have superior properties, such as lower toxicity, higher biodegradability, better environmental compatibility and higher ecological acceptance, compared to chemical surfactants that cause secondary environmental pollution at higher concentrations. Currently, the application of sodium deoxycholate is mainly focused on the utilization of its chemical structure with hydrophilic and hydrophobic groups to achieve cell lysis and the lysis of insoluble proteins (e.g., membrane proteins). However, the performance of sodium deoxycholate as an extractant in the preparation of natural product samples has been rarely studied. Because sodium deoxycholate has the general properties of a surfactant and the capability of forming hydrogen bonds by interaction with a compound, the sodium deoxycholate has potential application prospects as a solid dispersion extracting agent, and can promote the compound to be converted into a water-soluble form after being co-ground with sample powder under the action of high-speed mechanical force.
The Saviae Miltiorrhizae radix is dried root and rhizome of Salviaminetiriza Bge. Due to its remarkable pharmacological activity, salvia miltiorrhiza is widely used in 1 asian countries for the treatment of cirrhosis, coronary heart disease, diabetes, hypertension and other cardiovascular diseases, and has recently gained popularity worldwide as a health food and nutritional supplement. The bioactive components in salvia miltiorrhiza are mainly divided into two types: hydrophilic phenolic acid (such as tanshinol, salvianolic acid A, salvianolic acid B, rosmarinic acid, tannic acid B, and lithospermic acid) and hydrophobic tanshinone (such as tanshinone I, tanshinone IIA, cryptotanshinone, and dihydrotanshinone I). Currently, sample pretreatment methods such as maceration extraction, ultrasound-assisted extraction, microwave-assisted extraction, and cloud point extraction have been widely used to extract active ingredients from salvia miltiorrhiza. However, the above method involves the use of an organic solvent in the extraction process, and it is difficult to satisfy the requirement of green development; furthermore, these methods are limited to extracting only one of the hydrophilic or hydrophobic compounds, and do not facilitate the capture of both types of analytes simultaneously. Therefore, establishing a simple, efficient and organic solvent-free method to simultaneously capture hydrophilic and hydrophobic compounds in salvia miltiorrhiza is of great significance.
Disclosure of Invention
The invention aims to provide a synchronous green extraction method of phenolic acids and tanshinone compounds in salvia miltiorrhiza in order to overcome the defects of the prior art.
Specifically, the method of the invention is realized by the following technical measures:
a synchronous green extraction method of phenolic acids and tanshinone compounds in Salvia miltiorrhiza Bunge comprises the following steps:
s1, crushing the salvia miltiorrhiza into salvia miltiorrhiza powder by a crusher;
s2, adding a biosurfactant sodium chenodeoxycholate into the salvia miltiorrhiza powder to carry out mechanical and chemical grinding treatment to obtain a co-ground product; the grinding time is 1.0-7.5 minutes; the mass ratio of the salvia miltiorrhiza powder to the biological surfactant sodium chenodeoxycholate is 5:2-5;
s3, taking out the co-ground product, adding deionized water to dissolve the co-ground product, magnetically stirring, centrifuging, and taking an upper-layer sample solution;
s4, performing UHPLC on the upper layer sample solution; the content of the target compound is measured by Agilent 1290-VWD to show the effectiveness of the extraction method.
Preferably, the milling time is 5 minutes;
preferably, the magnetic stirring time is 1.0 to 7.0 minutes, more preferably 5 minutes;
preferably, the mass ratio of the salvia miltiorrhiza bunge powder to the biological surfactant sodium chenodeoxycholate is 5;
preferably, the mass-to-volume ratio of the deionized water to the salvia miltiorrhiza powder in the step S3 is 5 g; more preferably 0.5 mg to 10 ml;
the invention has the advantages that:
1. compared with the traditional method for extracting the compounds in the salvia miltiorrhiza bunge, the method has the advantages of being green and pollution-free, and simultaneously realizing the extraction of hydrophilic and hydrophobic compounds.
2. The method has wide application range, can be used for detecting the hydrophilic phenolic acid in various medicinal materials and detecting the hydrophobic tanshinone in the various medicinal materials, and has wide application potential in the extraction of natural medicinal materials;
the invention takes the mechanical amorphous dispersion extraction assisted by the biosurfactant as a method for quickly determining the hydrophilic and hydrophobic compounds in the traditional Chinese medicine with environmental protection and sensitivity. A series of parameters such as the type of a surfactant, the dosage of the surfactant, the grinding time, the extraction time, the solid-liquid ratio and the like which influence the extraction efficiency are systematically discussed and optimized through a single-factor experiment. Verification experiments of linearity, daily and daytime precision (RSD%), detection Limit (LOD), quantification Limit (LOQ), repeatability, recovery rate and the like are carried out under the optimal conditions. The invention can be successfully applied to qualitative and quantitative analysis of hydrophilic phenolic acids (tanshinol, salvianolic acid A, salvianolic acid B, rosmarinic acid and lithospermic acid) and hydrophobic tanshinone (tanshinone I, tanshinone II A, cryptotanshinone and dihydrotanshinone I) in the salvia miltiorrhiza.
Drawings
FIG. 1 is a flow chart of the BA-MADE extraction and separation of a target compound;
FIG. 2 is a line graph for examining the extraction effect of different surfactant types; wherein A, B, C, D and E are respectively sodium hyodeoxycholate, sodium chenodeoxycholate, sodium taurocholate, sodium deoxycholate and sodium amniotic fluid cholate;
FIG. 3 is a line graph for examining the extraction effect of different surfactant amounts;
FIG. 4 is a line graph illustrating the extraction effect of different grinding times;
FIG. 5 is a line graph illustrating the extraction effect of different extraction times;
FIG. 6 is a line chart for examining the extraction effect of different solid-liquid ratios.
In fig. 2-6, 1 is danshensu, 2 is rosmarinic acid, 3 is lithospermic acid, 4 is salvianolic acid B,5 is salvianolic acid a,6 is dihydrotanshinone i, 7 is cryptotanshinone, 8 is tanshinone i, and 9 is tanshinone iia.
Detailed Description
As described above, in view of the deficiencies of the prior art, the present inventors have made extensive studies and extensive practices, and propose a technical solution of the present invention, which is mainly based on at least: the salvia miltiorrhiza powder and the sodium chenodeoxycholate are mechanically ground and uniformly dispersed on the surface of the sodium chenodeoxycholate, after the extraction solvent water is added, the target compound attached to the surface of the sodium chenodeoxycholate is rapidly dispersed in the water along with the sodium chenodeoxycholate, and the extraction is realized under the action of magnetic stirring.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and 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. In addition, the technical features involved in the respective embodiments of the present invention described below may be combined with each other as long as they do not conflict with each other.
The invention relates to a synchronous green extraction method of phenolic acids and tanshinone compounds in salvia miltiorrhiza bunge, which comprises the following steps:
s1, crushing the salvia miltiorrhiza into salvia miltiorrhiza powder by a crusher;
s2, adding a biosurfactant sodium chenodeoxycholate into the salvia miltiorrhiza powder to carry out mechanochemical grinding treatment to obtain a co-ground product; the grinding time is 1.0-7.5 minutes; the mass ratio of the salvia miltiorrhiza powder to the biological surfactant sodium chenodeoxycholate is 5:2-5;
s3, taking out the co-ground product, adding deionized water to dissolve the co-ground product, magnetically stirring, centrifuging, and taking an upper-layer sample solution;
preferably, the milling time is 5 minutes;
preferably, the magnetic stirring time is 1.0 to 7.0 minutes, more preferably 5 minutes;
preferably, the mass ratio of the salvia miltiorrhiza powder to the biological surfactant sodium chenodeoxycholate is 5;
preferably, the mass-to-volume ratio of the deionized water to the salvia miltiorrhiza powder in the step S3 is 5 g; more preferably 0.5 mg to 10 ml;
s4, performing UHPLC analysis and extraction effect on the upper layer sample solution;
the UHPLC conditions are specifically as follows:
target analytes were separated by means of an Agilent Zorbax SB-C18 column (5 μm, 4.6X 100 mm) at a column temperature of 25 ℃; the mobile phase was 0.1% formic acid water (solvent a) and acetonitrile (solvent B), and the mobile phase gradient was set as follows: 0-7 minutes, 21-23% by weight B;7-10 minutes, 23-29% by weight of B;10-13 minutes, 29-35% b;13-15 minutes, 35-72% b;15-20 minutes, 72-76% by weight B;20-25 minutes, 76-85% by weight B; the sample volume, flow rate and wavelength were set at 2. Mu.L, 1 ml/min and 280nm, respectively.
The technical solutions of the present invention are further explained below with reference to several preferred embodiments, but the experimental conditions and the setting parameters should not be construed as limitations of the basic technical solutions of the present invention. And the scope of the present invention is not limited to the following examples.
Example 1 examination of the Effect of biosurfactant species on extraction
The biological surfactant type is an important factor influencing the extraction effect, and the example researches the influence of five biological surfactants, namely sodium hyodeoxycholate, sodium chenodeoxycholate, sodium taurocholate, sodium deoxycholate and sodium amniotic fluid cholate on the extraction effect. Synchronously and greenly extracting phenolic acids and tanshinone compounds in salvia miltiorrhiza bunge, which specifically comprises the following steps:
1.1 taking 5 clean ball milling tanks, numbering 1, 2, 3, 4 and 5, and sequentially adding 0.50 g of salvia miltiorrhiza powder;
1.2 respectively adding 200 mg of sodium hyodeoxycholate, sodium chenodeoxycholate, sodium taurocholate, sodium deoxycholate and sodium amniotic fluid cholate, and then sequentially adding 5 porcelain balls with equal weight;
1.3 symmetrically placing the ball milling tanks, and grinding for 5 minutes;
1.4 taking out the mechanically ground product, pouring the mechanically ground product into 5 clean conical flasks in sequence, adding 10 ml of deionized water, and magnetically stirring for 5 minutes;
1.5 sequentially taking 0.5 ml of sample solution in a centrifuge tube, and centrifuging for 5 minutes at 13000 rpm;
1.6 sucking the intermediate liquid and injecting the liquid phase.
The chromatographic conditions are as follows:
detection wavelength: 280nm; column temperature: 25 deg.C
The results of the experiment are shown in FIG. 2. FIG. 2 is a line graph for examining the extraction effect of different biosurfactant species.
In the present invention, the surfactant acts as a solid dispersing agent, having a large influence on the performance of the established process. The invention requires that the solid dispersing reagent has better extraction capability on hydrophilic and lipophilic compounds in the salvia miltiorrhiza bunge, and has the advantages of environmental protection and good chromatographic performance. Based on the requirements, the effects of various dispersants (sodium hyodeoxycholate, sodium chenodeoxycholate, sodium taurocholate, sodium amniotic fluid cholate and sodium deoxycholate) are examined. The results show that the solubility, viscosity and polarity of the extractant all have an effect on the extraction efficiency of the target compound. As can be seen from FIG. 2, sodium chenodeoxycholate has the best extraction efficiency for all compounds except danshensu. The extraction efficiency of the sodium chenodeoxycholate on the rosmarinic acid is 6 to 20 times higher than that of other extracting solutions. This phenomenon can be explained by the fact that sodium chenodeoxycholate has similar polarity to rosmarinic acid and the electrostatic interaction is stronger. In addition, the alkalinity of a system consisting of the chenodeoxycholic acid and the pure water is stronger than that of other systems, and the system is more favorable for the destruction of the cell wall of the compound, thereby reducing the mass transfer resistance and promoting the dissolution of the compound. Therefore, sodium chenodeoxycholate is selected as the optimal extractant in the invention.
Example 2 examination of the Effect of biosurfactant amount on the extraction
The amount of biosurfactant is an important factor influencing the extraction effect, and the influence of the amounts of the four biosurfactants of 200 mg, 300 mg, 400 mg and 500 mg on the extraction effect is researched in the example. Synchronously and green extracting phenolic acids and tanshinone compounds in salvia miltiorrhiza, which specifically comprises the following steps:
2.1 taking 4 clean ball milling tanks, numbering 1, 2, 3 and 4, and sequentially adding 0.50 g of salvia miltiorrhiza powder;
2.2 adding 200, 300, 400 and 500 mg of sodium chenodeoxycholate respectively, and then sequentially adding 4 ceramic balls with equal weight;
2.3, symmetrically placing the ball milling tanks, and grinding for 5 minutes;
2.4 taking out the mechanically ground product, pouring the mechanically ground product into 4 clean conical flasks in sequence, adding 10 ml of deionized water, and magnetically stirring for 5 minutes;
2.5 taking 0.5 ml of sample solution in turn to be put in a centrifuge tube and centrifuged for 5 minutes at 13000 rpm;
2.6 sucking the intermediate liquid and injecting the liquid phase.
The chromatographic conditions are as follows:
detection wavelength: 280nm; column temperature: at 25 ℃.
The results of the experiment are shown in FIG. 3. FIG. 3 is a line graph for examining the extraction effect of different biosurfactant species.
The selection of the amount of sodium chenodeoxycholate is the key step in the invention to obtain the maximum extraction yield, and therefore the amount of dispersant in the range of 200-500 mg is optimized. As shown in fig. 3, a significant increase in extraction rate was seen by increasing the amount of sodium chenodeoxycholate from 200 mg to 400 mg. This may be due to the fact that during milling, the target compound and the extractant react under high mechanical stress, resulting in the formation of intermolecular hydrogen bonds, which results in the conversion of the analyte to a water-soluble form. It is speculated that after the extraction procedure, purified water is used as the extraction solvent, and forms a "target complex surfactant-water" system with the co-ground product. Biosurfactants with amphiphilic structures facilitate the interpenetration of the system by changing the interfacial state of the system. Therefore, the extraction rate of the objective compound reaches saturation at 400 mg of sodium chenodeoxycholate, and does not increase with the addition amount, and too high dispersant dosage increases the viscosity of the system, resulting in a decrease in efficiency. Therefore, 400 mg was chosen as the dispersant for the present invention.
Example 3 examination of the Effect of milling time on extraction
The milling time is an important factor affecting the extraction effect, and the present example investigated the effect of four milling times, 1, 2.5, 5, and 7.5 minutes, on the extraction effect. Synchronously and green extracting phenolic acids and tanshinone compounds in salvia miltiorrhiza, which specifically comprises the following steps:
step (1), extracting a target compound;
1-1, crushing the salvia miltiorrhiza into powder by a crusher;
1-2, taking 4 clean ball milling tanks, numbering 1, 2, 3 and 4, and sequentially adding 0.50 g of salvia miltiorrhiza powder;
1-3, respectively adding 400 mg of sodium chenodeoxycholate into the 4 clean ball milling tanks, and then sequentially adding the 4 ball milling tanks;
1-4, respectively grinding the 4 ball milling tanks for 1, 2.5, 5 and 7.5 minutes to obtain four co-grinding products;
1-5, taking out the four co-ground products, pouring the four co-ground products into 4 clean conical flasks in sequence, adding 10 ml of deionized water, and magnetically stirring for 5 minutes;
1-6, sequentially taking 0.5 ml of sample solution in a centrifuge tube, and centrifuging for 5 minutes at 13000 rpm;
and (2) sucking the intermediate liquid and injecting the liquid phase.
The results of the experiment are shown in FIG. 4. Fig. 4 is a line graph of extraction effect for different grinding times.
Grinding time is an important parameter to be optimized in order to obtain maximum efficiency of the present invention with minimum energy consumption. As shown in fig. 4, the extraction rate of the compound gradually increased with the increase of the milling time, and finally reached a plateau. The extraction time depends on the time required for the dissolution diffusion process. This is because after a period of grinding, the cell walls of the sample are disrupted by mechanical force, then the extraction solvent diffuses into the cells, causing the target compound to dissolve into the surrounding extractant, which then diffuses out of the matrix, and then is extracted with water by magnetic stirring. The plateau phase occurs probably because the amount of extractant diffusing into the cells is limited and therefore does not increase indefinitely as the milling time continues to increase. Furthermore, the extraction efficiency of salvianolic acid B is significantly reduced from 5 minutes to 7.5 minutes due to frictional losses, oxidation and instability of the co-milled product caused by over-milling. Thus, the present invention selects 5 minutes as the milling time.
Example 4 examination of the Effect of extraction time on the extraction Effect
The extraction time is an important factor affecting the extraction effect, and the present example investigated the effect of the four extraction times of 1,3,5,7 minutes on the extraction effect. Synchronously and greenly extracting phenolic acids and tanshinone compounds in salvia miltiorrhiza bunge, which specifically comprises the following steps:
step (1), extracting a target compound;
1-1, crushing the salvia miltiorrhiza into powder by a crusher;
1-2, taking 4 clean ball milling tanks, numbering 1, 2, 3 and 4, and sequentially adding 0.50 g of salvia miltiorrhiza powder;
1-3, respectively adding 400 mg of sodium chenodeoxycholate into the 4 clean ball milling tanks, and then sequentially adding the 4 ball milling tanks;
1-4, respectively grinding the 4 ball milling tanks for 5 minutes to obtain four parts of co-ground products;
1-5, taking out the four co-ground products, pouring the four co-ground products into 4 clean conical flasks in sequence, adding 10 ml of deionized water, and respectively carrying out magnetic stirring for 1,3,5,7 minutes;
1-6, sequentially taking 0.5 ml of sample solution in a centrifuge tube, and centrifuging for 5 minutes at 13000 rpm;
and (2) sucking the intermediate liquid and injecting the liquid phase.
The results of the experiment are shown in FIG. 5. Fig. 5 is a line graph for examining the extraction effect of different grinding times.
The present invention can achieve higher efficiency by increasing the mass transfer rate of the target compound and reducing the time required for equilibrium partitioning, thus studying the effect of stirring time on extraction efficiency in the range of 1-7 minutes. The results in fig. 5 show that the extraction efficiency for most analytes increases significantly when the stirring time is increased from 1 minute to 5 minutes, and then reaches equilibrium or drops slightly. This is possible because appropriate stirring times allow better contact between the co-mulled product and the solvent, thereby enhancing diffusion of the analyte into the aqueous phase; however, too long stirring time results in structural destruction of the compound, partial loss of the solvent, generation of bubbles, and dissolution of the non-target compound of salvia miltiorrhiza, all of which negatively affect the extraction efficiency. Considering that increasing the magnetic stirring time did not significantly improve the extraction yield of the target analyte and adversely affected the integrity of the sample extract, the present invention selected 5 minutes as the extraction time.
Example 5 examination of the influence of solid-liquid ratio on the extraction Effect
The solid-liquid ratio is an important factor influencing the extraction effect, and the influence of the addition of four solid-liquid ratios of 7.5 ml, 10.0 ml, 12.5 ml and 15.0 ml of deionized water on the extraction effect is studied in the example. Synchronously and greenly extracting phenolic acids and tanshinone compounds in salvia miltiorrhiza bunge, which specifically comprises the following steps:
step (1), extracting a target compound;
1-1, crushing the salvia miltiorrhiza into powder by a crusher;
1-2, taking 4 clean ball milling tanks, numbering 1, 2, 3 and 4, and sequentially adding 0.50 g of salvia miltiorrhiza powder;
1-3, respectively adding 400 mg of sodium chenodeoxycholate into the 4 clean ball milling tanks, and then sequentially adding the 4 ball milling tanks;
1-4, respectively grinding the 4 ball milling tanks for 5 minutes to obtain four parts of co-ground products;
1-5, taking out the four co-ground products, pouring the four co-ground products into 4 clean conical flasks in sequence, adding 7.5 ml, 10.0 ml, 12.5 ml and 15.0 ml of deionized water respectively, and magnetically stirring for 5 minutes;
1-6, sequentially taking 0.5 ml of sample solution in a centrifuge tube, and centrifuging for 5 minutes at 13000 rpm;
and (2) sucking the intermediate liquid and injecting the liquid phase.
The extraction efficiency of the present invention also depends on the appropriate solid-to-liquid ratio, and therefore the effect of a series of solid-to-liquid ratios (0.5, 0.5. FIG. 6 shows that the extraction yield peaks at a solid-to-liquid ratio of 0.5. At sufficient extraction time, reducing the volume of solvent can concentrate the broken cells in contact with the solvent, thereby promoting the formation of more hydrogen bonds, and thus increasing water solubility. Furthermore, dissolution of the drug substance is a physical process, and thus, as the volume of waste is reduced, the chance of the target analyte contacting purified water is increased, resulting in a higher leaching rate. Although the results show that the extraction efficiency can be continuously improved without changing the amount of the sample powder by reducing the volume of water in a certain range, the solution is slightly viscous at a solid-to-liquid ratio of 0.5. Continuing to reduce the volume of solvent will result in an impaired sensitivity of the instrument and affect the reproducibility of the experiment. Therefore, the present invention selects 0.5.
To further validate the feasibility of the method, methodological investigations were performed including intra-day precision, inter-day precision, reproducibility, and sample recovery.
Precision within a day
Step (1), taking 3 clean 1.5 mL centrifuge tubes, numbering 1, 2 and 3, and respectively preparing standard solutions of three target analytes of 20 mu g/mL;
step (2), centrifuging the standard solution of the three target analytes for 5 minutes at 13000 rpm;
step (3), sucking the centrifuged intermediate liquid, and injecting the liquid phase;
and (4) carrying out sample injection analysis, wherein sample injection is carried out for 6 times in different time periods in the same day.
Precision of day
Step (1), taking 3 clean 1.5 mL centrifuge tubes, numbering 1, 2 and 3, and respectively preparing standard solutions of three target analytes of 20 mu g/mL;
step (2), centrifuging the standard solution of the three target analytes for 5 minutes at 13000 rpm;
step (3), sucking the intermediate liquid and injecting the liquid phase;
and (4) injecting samples for analysis, wherein the samples are injected at the same time point within three days and are injected for 2 times every day.
Repeatability of
Refer to the following experimental procedure, run 3 groups in parallel as a survey
Step (1), taking 3 clean 1.5 mL centrifuge tubes, numbering 1, 2 and 3, and respectively preparing sample extracting solutions under optimal conditions (400 mg sodium chenodeoxycholate, 5-minute grinding time, 5-minute extraction time and 0.5:10g/mL solid-to-liquid ratio);
step (2), centrifuging the standard solution of the three target analytes for 5 minutes at 13000 rpm;
and (3) sucking the intermediate liquid, injecting the liquid phase, and analyzing the result.
Sample recovery rate
With reference to the following experimental procedure, 3 groups were run in parallel for each concentration
Step (1), weighing 0.50 g of salvia miltiorrhiza powder (80 meshes), grinding the powder and 400 mg of sodium chenodeoxycholate for 5 minutes, adding 10 ml of purified water, magnetically stirring for 5 minutes, centrifuging at 13000rpm for 5 minutes, and taking out an intermediate liquid (100 microliters);
step (2), adding a standard (a mixed standard with the content of 1 mu g/mg and 10 mu g/mg), and standing at room temperature for 2 hours to ensure that the mixed standard and a sample uniformly react;
step (3), centrifuging the mixed standard and the sample 13000 for 5 minutes after the uniform reaction;
and (4) sucking the intermediate liquid and injecting the liquid phase.
The results are summarized in tables 1-2 below:
TABLE 1
TABLE 2
The above embodiments are not intended to limit the present invention, and the present invention is not limited to the above embodiments, and all embodiments are within the scope of the present invention as long as the requirements of the present invention are met.
Claims (7)
1. A synchronous green extraction method of phenolic acids and tanshinone compounds in salvia miltiorrhiza is characterized by comprising the following steps:
s1, crushing the salvia miltiorrhiza into salvia miltiorrhiza powder by a crusher;
s2, adding a biosurfactant sodium chenodeoxycholate into the salvia miltiorrhiza powder to carry out mechanochemical grinding treatment to obtain a co-ground product; the grinding time is 1.0-7.5 minutes; the mass ratio of the salvia miltiorrhiza powder to the biological surfactant sodium chenodeoxycholate is 5:2-5;
and S3, taking out the co-ground product, adding deionized water to dissolve the co-ground product, magnetically stirring, centrifuging, and taking an upper layer sample solution.
2. The method of claim 1, wherein the milling time of step S2 is 5 minutes.
3. The method according to claim 1, wherein the mass ratio of the salvia miltiorrhiza powder to the biosurfactant sodium chenodeoxycholate in the step S2 is 5.
4. The method of claim 1, wherein the magnetic stirring time of step S3 is 1.0-7.0 minutes.
5. The method of claim 4, wherein the magnetic stirring time of step S3 is 5 minutes.
6. The method of claim 1, wherein the mass-to-volume ratio of the deionized water to the red sage root powder in step S3 is 5 g.
7. The method of claim 6, wherein the mass to volume ratio of the deionized water to the Danshen powder in step S3 is 0.5 mg to 10 ml.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110240580A (en) * | 2019-05-16 | 2019-09-17 | 浙江中医药大学 | A method of Salvia root P.E is prepared using eutectic solvent |
| CN110763793A (en) * | 2019-11-05 | 2020-02-07 | 云南楚雄天利药业有限公司 | Method for detecting active ingredients of salvia miltiorrhiza and products |
| CN114527214A (en) * | 2022-02-22 | 2022-05-24 | 杭州师范大学 | Green extraction method of hydrophobic components in traditional Chinese medicine |
-
2022
- 2022-08-22 CN CN202211006144.9A patent/CN115343408A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110240580A (en) * | 2019-05-16 | 2019-09-17 | 浙江中医药大学 | A method of Salvia root P.E is prepared using eutectic solvent |
| CN110763793A (en) * | 2019-11-05 | 2020-02-07 | 云南楚雄天利药业有限公司 | Method for detecting active ingredients of salvia miltiorrhiza and products |
| CN114527214A (en) * | 2022-02-22 | 2022-05-24 | 杭州师范大学 | Green extraction method of hydrophobic components in traditional Chinese medicine |
Non-Patent Citations (1)
| Title |
|---|
| SI-CHEN ZHU 等: "Simultaneous capture of hydrophilic and hydrophobic compounds from complex plants by biosurfactant-assisted mechanical amorphous dispersion extraction", JOURNAL OF CHROMATOGRAPHY A, vol. 1678, pages 1 - 14 * |
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Application publication date: 20221115 |