CN110229208B - Efficient preparation and separation method of compound 20(R) -ginsenoside Rg3 - Google Patents
Efficient preparation and separation method of compound 20(R) -ginsenoside Rg3 Download PDFInfo
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Abstract
The invention discloses a method for preparing and separating 20(R) -ginsenoside Rg3 (ginsenoside Rg3, C) by efficient direct hydrolysis42H72O13Hereinafter referred to as "Rg 3"), and more particularly to a method for producing a ginseng extract by directly converting a ginseng plant belonging to the genus panax of the family araliaceaeA method for directly preparing a high-purity compound Rg3 by a saponin one-step method. The preparation method comprises the following steps: barium chloride (BaCl ₂) is used as a reaction catalyst, acetic acid aqueous solution is mixed with ginseng total saponins (such as ginseng, American ginseng, pseudo-ginseng, and the like) according to a proportion, and then a high-temperature water bath reaction is utilized to prepare a ginsenoside Rg3 crude product. Dissolving the mixture by using different ethanol concentrations and different water bath temperatures, and further recrystallizing the obtained converted substance by using cooling and ethanol and ethyl acetate solvent methods to prepare the high-purity Rg 3. The method is rapid and efficient, can effectively save the separation and purification time of Rg3, is economic and safe, simple and practical, has high yield, is suitable for industrialized production, and greatly promotes the efficient utilization of the effective components of the panax plants.
Description
Technical Field
The invention belongs to the field of natural compound preparation and separation, and particularly relates to a method for preparing 20(R) -ginsenoside Rg3 by efficiently hydrolyzing total ginsenoside.
Background
Ginsenoside Rg3 (ginsenoside Rg 3) is a tetracyclic triterpene saponin existing in ginseng, and modern pharmacology proves that ginsenoside Rg3 has strong medicinal value, multiple pharmacological activities of resisting cancer and tumor, regulating nervous system, regulating immunologic function, inhibiting aging, protecting liver and kidney functions and the like (see: Choi Y J,et al.Stimulation of DDX3 expression by ginsenoside Rg3 through the Akt/p53 pathwayactivates the innate immune response via TBK1/IKKε/IRF3 signaling,Curr Med Chem2014, royal blue, the anti-tumor effect of the ginsenoside Rg3 and the mechanism research thereof, Heilongjiang medicine 2014, 27, 296-300). Clinical tests show that the ginsenoside Rg3 can effectively inhibit the growth of liver cancer, lung cancer and intestinal cancer, can obviously improve clinical symptoms, and can be prepared into new anti-cancer drugs, such as 'Shenyi capsule', and also can be prepared into anti-tumor oral liquid and injection for clinical application.
However, the ginsenoside Rg3 is a rare saponin, has an extremely low content in natural Panax plants, is about 0.01-0.02% by mass, and can be produced in large quantities after processing; notably, ginsenoside Rg3 naturally occurs in two configurations, 20(S) -Rg3 and 20(R) -Rg 3. A large number of researches show that the pharmacological activity of the R type is obviously stronger than that of the S type, and the pharmacological activity is a key configuration worthy of being deeply explored (see: He Bo, et al. 20(R) -ginsenoside Rg-3 has a protection effect on delayed neuron injury after rat ischemia reperfusion. Shizhen Chinese medicines, 2016, 27, 35-38; Liming crystal, et al. ginsenoside Rg3 research progress. China journal of senior citizen, 2017, 37, 6000-.
Among them, acid hydrolysis is the most common method for preparing ginsenoside Rg3, and it has been found through research that when the strength of acid, hydrolysis temperature and hydrolysis time are not properly controlled, insufficient hydrolysis or excessive hydrolysis is easily caused, and the problem of low yield exists. In addition, at present, acid hydrolysis generally divides ginsenosides into groups to obtain diol group ginsenosides, and then performs acid conversion, but the production technical requirements are too high, so that the application and development of the ginsenosides are often limited, the resource waste is easily caused, the high-purity 20(R) -ginsenoside Rg3 is difficult to obtain, and the research on the pharmacological activity of the ginsenosides is greatly limited.
For example:
CN 201210547486.1 discloses a method for producing ginsenoside Rg3 by hydrolyzing total ginsenoside, which comprises the steps of dissolving the total ginsenoside in an aqueous solution containing 65-70% of ethanol by volume and 6-8% of acetic acid by volume to prepare a solution containing 6-7% of the total ginsenoside by mass and volume, and hydrolyzing the solution in a hydrolysis tank at 80-85 ℃ for 90-100 minutes. And desalting and drying by combining with macroporous resin, wherein the content of the obtained dried ginsenoside Rg3 is 20-30 times of the mass ratio.
CN 201310654074.2 discloses a method for rapidly and non-thermally preparing rare ginsenoside Rg3(S), and relates to a high-voltage pulse electric field technology coupled acid hydrolysis preparation method, wherein acidic solutions of ginsenoside Rb1 are uniformly mixed at normal temperature, the acidity is 0.1-2%, the electric field intensity is 5-25 kV/cm, the pulse number is 1-15, and an organic solvent is centrifuged to obtain ginsenoside (S) -Rg 3.
CN 201410385464.9 discloses a method for preparing ginsenoside Rg3, which utilizes panaxadiol group ginsenoside to carry out hydrolysis with weak acid, and ginsenosides Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rc, Rd, notogenside R4 and the like have similar structures and are substituted by acidolysis on a C-20 substituent by carrying out selective hydrolysis under the protection of a protective agent at a C-20 substituent, thereby obtaining the ginsenoside Rg 3.
CN 201510726006.1 discloses a method for preparing Rg3 and Rh2 from panax notoginseng leaf total saponins, wherein the panax notoginseng saponins are panaxadiol saponins, and the ginsenosides are prepared by performing microwave hydrolysis and purification, hydrolyzing in a microwave reactor at 50-103 ℃ for 5-60 min by using an inorganic acid aqueous solution (hydrochloric acid and acetic acid) with the concentration of 0.2-4M, deacidifying by using a macroporous resin layer, eluting and concentrating to obtain the ginsenosides Rg3 and Rh 2. The invention enhances the selective hydrolysis by jointly using the microwave, so that the time for complete hydrolysis is greatly shortened, and the dosage of the acid catalyst is obviously reduced.
CN 201610599632.3 discloses a preparation method and application of a high-purity compound ginsenoside Rg3 (20 (R) -ginsenosideRg 3). The method comprises the steps of selecting panaxadiol saponins, dissolving the panaxadiol saponins by using 10-30% acetic acid aqueous solution, placing the panaxadiol saponins in a low-temperature environment at 0-4 ℃, reacting the panaxadiol saponins in water bath at 80-90 ℃ for 2-4 hours, dissolving a crude product by using hot ethanol containing ethyl acetate at 30-90 ℃, cooling and recrystallizing the crude product, so that the high-purity 20(R) -ginsenosideRg3 is obtained.
As can be seen from the prior art for preparing Rg3 by acid conversion, the characteristics and the main disadvantages of the prior acid conversion are shown in the table:
TABLE 1 comparison of the prior art processes for preparing and separating Rg3
| Acid conversion process | Raw materials | Transformation method | Purifying the fraction | Disadvantages of |
| CN201210547486.1 | Total saponins of Ginseng radix | Hydrolyzing the aqueous solution containing ethanol and acetic acid, and purifying by macroporous resin | Rg3 | The purification time is long, and the single component is difficult to obtain |
| CN201310654074.2 | Rb1 | High-voltage pulse electric field technology coupling acid hydrolysis | Rg3(S) | The safety is poor, the cost is high, the waste is serious, and R configuration products cannot be generated |
| CN201410385464.9 | Panaxadiol saponins | Hydrolysis with weak acid | Rg3 | High requirements on raw materials, high cost, complex process and difficulty in obtaining single component |
| CN201510726006.1 | Notoginseng radix total saponin | Hydrolyzing with inorganic acid, microwave hydrolyzing, and purifying with macroporous resin | Rg3、Rh2 | Poor safety, complex process, long purification time, waste of resources and no pollutionSingle component, presence of impurities |
| CN201610599632.3 | Panaxadiol saponins | Weak acid hydrolysis, recrystallization of pyridine-containing ethanol at different concentrations | Rg3(R) | High requirement on raw materials, complex process, high cost and resource waste |
The comparison shows that the separation and purification of the ginsenoside Rg3 at present usually have the following problems: (1) most methods combine acid conversion and macroporous resin purification, and the method has long separation time, needs desalination treatment, easily causes resource waste and is environment-friendly; (2) the method mainly obtains the whole Rg3 through ginsenoside conversion, contains impurities, and mostly adopts column chromatography separation such as silica gel and the like for the single configuration (R) -Rg3 separation, so that the separation cost is high, and the environment is not friendly; (3) the panaxadiol saponins are required to be separated into diol group and triol group and then converted and prepared by using the panaxadiol saponins, although the conversion efficiency is high, the obtaining of the diol group usually requires more time and cost, the complexity of the process is increased to a certain extent, and the resource waste is caused.
The invention can fully make up the defects of the prior art, and has the main technical advantages that: (1) the cheap and easily obtained panax total saponins are utilized to carry out direct hydrolysis, the acidity and the conversion time are strictly controlled, the complete conversion of the panax total saponins is ensured to the maximum extent, and the yield of the ginsenoside Rg3 is improved. Meanwhile, (2) barium chloride is added as a catalyst, so that the acid consumption and concentration are effectively reduced, and the reaction efficiency and yield are greatly improved; (3) the method has the main advantages that the diol type saponin and the triol type saponin do not need to be separated in advance, the interference of the triol type saponin is effectively avoided, and the target product Rg3 is directly separated from the conversion solution. Finally, (4) the invention fully utilizes the solubility difference of S-type and R-type ginsenoside Rg3 under the conditions of different ethanol concentrations and different temperatures to further purify R-Rg3, thereby obtaining the high-purity 20(R) -ginsenoside Rg 3. The invention adopts the ginseng total saponins with wide sources as raw materials, saves the separation process of grouping the ginseng saponins, and can obtain the 20(R) -ginsenoside Rg3 only by one-step hydrolysis, one-step centrifugation and recrystallization.
It is worth mentioning that the above reaction substrates can be obtained industrially, can be purchased from the market, and can be completely used for obtaining the rare saponin Rg 3.
Disclosure of Invention
The invention belongs to the field of natural compound preparation, mainly aims to make up for the existing process method for preparing ginsenoside Rg3 by acid hydrolysis, and provides a method for efficiently hydrolyzing total ginsenoside to obtain high-purity 20(R) -ginsenoside Rg 3.
The method for preparing 20(R) -ginsenoside Rg3 by using the total ginsenoside comprises the following steps: barium chloride is used as a catalyst, 6-15% acetic acid water solution is selected as a reaction solution with the addition amount controlled between 0.5-5%, and the ginseng total saponins are added in proportion while stirring; and then, placing the reaction solution in a water bath at 75-85 ℃ for reaction for 2-3 h, standing, cooling, taking out the precipitate to obtain a ginsenoside Rg3 crude product, dissolving the crude product with 50-90% of ethanol, simultaneously adding a certain amount of ethyl acetate, controlling the temperature to be 30-80 ℃, controlling the amount of ethyl acetate to be 0.5-1%, and cooling and recrystallizing to obtain the 20(R) -ginsenoside Rg3 with the purity of 95-99.99%.
In the above method, the total saponins of Ginseng radix comprise total saponins of caulis Et folium Ginseng, total saponins of fructus Ginseng, total saponins of caulis Et folium Panacis Quinquefolii, total saponins of fructus Panacis Quinquefolii, and other total saponins of Panax.
In the method, the Rg3 crude product is added with 0.5-1% ethyl acetate in 50-90% ethanol, the temperature is controlled at 30-80 ℃, the two configurations of the ginsenoside Rg3 are fully utilized, the solubility is different under the conditions of different ethanol concentrations and temperatures, the purification time can be fully reduced by adding a certain amount of ethyl acetate, and the high-purity 20(R) -ginsenoside Rg3 is obtained after cooling and recrystallization. The method is simple and efficient, reduces the process of separating and purifying by using macroporous resin and silica gel, reduces the production cost, has strong practical value, and simultaneously avoids the problem of component loss caused by the phenomena of saponin grouping, adsorption and the like.
The invention has the beneficial effects that: the method can fully make up the process defects of the existing acid hydrolysis, adopts the ginseng total saponins with wide sources and low price as the raw material, fully ensures the high-efficiency hydrolysis of the ginseng saponins by the catalysis of barium chloride and the hydrolysis of low-concentration acetic acid and strictly controls factors such as the concentration of the acetic acid, the hydrolysis temperature and the hydrolysis time, and the like, further purifies the 20(R) -ginseng saponin Rg3 by different concentrations and temperatures of ethanol, can effectively solve the technical problems of more impurities generated in the hydrolysis process and difficult separation, saves the purification time, and is suitable for industrial production. The method is economical and safe, does not pollute the environment, adopts cheap and easily available total ginsenoside as raw material, and promotes the development and utilization of the ginseng plant; and the purification process is simple and efficient, and has strong practical significance.
The invention is further illustrated by the following specific examples.
Detailed Description
Example 1:
weighing 100g of total saponins of ginseng stem and leaf, analyzing by HPLC to mainly contain Rg1, Re, Rb1, Rc, Rd and other components, the total content is about 85% (UV method), taking 6% acetic acid water solution 2L as reaction liquid, adding 2% barium chloride, then adding the total saponins of ginseng stem and leaf according to the proportion of 1:20, stirring while adding, placing the reaction liquid in water bath at 80 ℃ for reaction for 2h, standing, cooling, centrifuging, taking out precipitate to obtain a crude product of the ginsenoside Rg3 (comprising R and S configuration Rg3, the total sum of which is more than 90%, and containing a small amount of Rg5 and Rk 1) which is about 8.6g, and the yield is 8.6%.
Dissolving the obtained Rg3 crude product in 50-90% ethanol, controlling the temperature at 90 ℃, adding 0.5% ethyl acetate, uniformly stirring, cooling, and recrystallizing to obtain 20(R) -ginsenoside Rg3, wherein the recovery rate of R-Rg3 is 85% from the crude product to the purified product.
And (3) subjecting the three batches of R-shaped Rg3 obtained after recrystallization to HPLC analysis, wherein the purity is 97.5-98.3%.
Example 2:
weighing 100g of ginseng fruit total saponins, analyzing by HPLC to mainly contain Rg1, Re, Rb1, Rc, Rd and other components, wherein the total content is about 85% (UV method), taking 8% acetic acid water solution 2L as reaction liquid, adding 1.5% barium chloride as catalyst, then adding ginseng stem leaf total saponins according to the proportion of 1:20, stirring while adding, placing the reaction liquid in water bath at 85 ℃ for reaction for 2.5h, standing, cooling, centrifuging, taking out precipitates, obtaining a crude product of the ginsenoside Rg3 (comprising R and S configuration Rg3, the total amount of which is more than 90%, and containing a small amount of Rg5 and Rk 1) which is about 7.8g, and the yield is 7.8%.
Dissolving the obtained Rg3 crude product in 50-90% ethanol, controlling the temperature at 90 ℃, adding 0.5% ethyl acetate, stirring uniformly, cooling, recrystallizing to obtain 20(R) -ginsenoside Rg3, wherein the recovery rate of R-Rg3 is 84.5% from the crude product to the purified product.
And (3) carrying out HPLC analysis on the three batches of R-shaped Rg3 obtained after recrystallization, wherein the purity is 97.1-98.2%.
Example 3:
weighing 100g of American ginseng stem and leaf total saponin, analyzing by HPLC to mainly contain Rg1, Re, Rb1, Rb3, Rc, Rd and other components, wherein the total content is about 85% (UV method), taking 15% acetic acid water solution 2L as reaction liquid, adding 2% barium chloride as catalyst, then adding the ginseng stem and leaf total saponin according to the proportion of 1:20, stirring while adding, placing the reaction liquid in 80 ℃ water bath for reaction for 2.5h, standing, cooling, centrifuging, taking out precipitate to obtain a crude product of the ginsenoside Rg3 (comprising R and S configuration Rg3, the sum of which is more than 90%, and containing a small amount of Rg5 and Rk 1) which is about 12.5g, and the yield is 12.5%.
Dissolving the obtained Rg3 crude product in 50-90% ethanol, controlling the temperature at 90 ℃, adding 0.5% ethyl acetate, stirring uniformly, cooling, recrystallizing to obtain 20(R) -ginsenoside Rg3, wherein the recovery rate of R-Rg3 is 86.2% from the crude product to the purified product.
And (3) carrying out HPLC analysis on the three batches of R-shaped Rg3 obtained after recrystallization, wherein the purity is 97.1-97.9%.
Example 4:
weighing 100g of American ginseng fruit total saponins, analyzing by HPLC (high performance liquid chromatography) to mainly contain Rg1, Re, Rb1, Rb3, Rc, Rd and other components, wherein the total content is about 85% (UV method), taking 12% acetic acid water solution 2L as reaction liquid, adding 1% barium chloride as a catalyst, then adding ginseng stem leaf total saponins according to the proportion of 1:15, stirring while adding, placing the reaction liquid in water bath at 85 ℃ for reaction for 2.5h, standing, cooling, centrifuging, taking out precipitates to obtain a crude product of the ginsenoside Rg3 (comprising R and S configuration Rg3, the sum of which is more than 90%, and containing a small amount of Rg5 and Rk 1) of about 13.6g, and the yield is 13.6%.
Dissolving the obtained Rg3 crude product in 50-90% ethanol, controlling the temperature at 90 ℃, adding 0.5% ethyl acetate, stirring uniformly, cooling, recrystallizing to obtain 20(R) -ginsenoside Rg3, wherein the recovery rate of R-Rg3 from the crude product to the purified product is 87.4%.
And performing HPLC analysis on the three batches of R-shaped Rg3 obtained after recrystallization, wherein the purity is 97.5-98.2%.
Example 5:
confirming the importance of the catalyst barium chloride, the influence of the added barium chloride on the conversion rate of R-Rg3 is determined by recrystallization experiments of the conversion crude product described in example 1, and is shown in Table 2: the addition of barium chloride has great influence on the recovery rate of crude products, and the combined effect of the barium chloride and the crude products is obviously superior to that of acetic acid used alone.
TABLE 2 influence of different catalyst additions on the recovery and purity of R-Rg3 crude product
| Catalyst and process for preparing same | Crude recovery (%) | Detection method |
| 0.0 percent of barium chloride | 34.2 | Gravimetric method |
| 0.5 percent of barium chloride | 68.5 | Gravimetric method |
| Barium chloride 1.0% | 71.1 | Gravimetric method |
| Barium chloride 1.5% | 78.3 | Gravimetric method |
| 2.0 percent of barium chloride | 86.2 | Gravimetric method |
Example 6:
confirming the importance of the catalyst barium salt, the influence of different barium salts added to the conversion crude product described in example 1 on the preparation yield of R-Rg3 was confirmed by recrystallization experiments, and is shown in Table 3: the addition of different barium salts has great influence on the recovery rate of crude products, the following results show that the results are only shown by the same addition amount of 2.0 percent, and other optimization experiments are not listed. The results show that: through optimization experiments, barium chloride is preferably used as a catalyst in the invention.
TABLE 3 influence of different catalyst additions on the recovery and purity of R-Rg3 crude product
| Catalyst and process for preparing same | Crude productRecovery (%) | Detection method |
| 2.0 percent of barium sulfate is added | 51.4 | Gravimetric method |
| 2.0 percent of barium nitrate is added | 65.2 | Gravimetric method |
| 2.0 percent of barium chloride | 86.2 | Gravimetric method |
| 2.0 percent of barium carbonate | 75.1 | Gravimetric method |
Example 7:
confirming the importance of the crystallization solvent ethyl acetate, the influence of the presence or absence of ethyl acetate addition on the purity of R-Rg3 was determined by recrystallization experiments of the crude product of the transformation as described in example 1, as shown in Table 4: the addition of ethyl acetate has great influence on the recovery rate of the crude product, and the combined effect of the ethyl acetate and the ethanol is obviously superior to that of the ethyl acetate or the ethanol which is used independently.
In addition, although pyridine is used as a crystallization solvent additive, it is not completely suitable for product crystallization due to its toxicity, and is not environment-friendly.
TABLE 4 influence of different crystallization solvents on the recovery and purity of R-Rg3 crude product
| Selection of crystallization solvent | Crude recovery (%) | Purity (%) | Detection method |
| Ethyl acetate (0.5%) + ethanol (90%) | 86.2 | ≥98.3 | HPLC |
| Ethanol (90%) | 78.4 | ≥97.2 | HPLC |
| Ethyl acetate (0.5%) | 55.3 | ≥91.2 | HPLC |
Example 8:
hydrolyzing the above 4 kinds of common Panax saponins, purifying the converted precipitate to obtain (R) -Rg3, comparing hydrolysis and purification time, and analyzing the purity by HPLC, as shown in Table 5:
TABLE 5.4 comparison of precipitation yield and purification time after hydrolysis of Panax total saponins
| Group of | Recovery (%) | Purifying the fraction | Crude product yield (%) | Application time (h) | Purity (%) | Detection method |
| Example 1 | 86.0% | (R)-Rg3 | 8.6% | 4h | ≥97.0 | HPLC |
| Example 2 | 84.5% | (R)-Rg3 | 7.8% | 4h | ≥97.0 | HPLC |
| Example 3 | 86.2% | (R)-Rg3 | 12.5% | 4h | ≥97.0 | HPLC |
| Example 4 | 87.4% | (R)-Rg3 | 13.6% | 4h | ≥97.0 | HPLC |
Through the hydrolysis and purification processes of the four panax total saponins in the embodiment and the comprehensive comparison of the prior acid hydrolysis process, the invention adopts the direct hydrolysis of the panax total saponins, thereby effectively reducing the cost increase and the resource waste caused by the grouping of the saponins; the barium chloride is creatively added as a catalyst, so that the acid concentration is effectively reduced, and the environmental pollution and the energy consumption are reduced; the high-purity (R) -Rg3 is obtained by using the solubility difference for precipitation and purification and adding ethyl acetate through recrystallization, the process of further separating by adopting macroporous resin and silica gel is reduced, and the purification time is obviously saved; in addition, the method is economic and safe, the purification process is simple and efficient, and impurities generated in the hydrolysis and purification processes are effectively avoided.
The above examples are merely to describe and illustrate the method of obtaining high purity 20(R) -ginsenoside Rg3 by efficiently hydrolyzing four common panax total saponins, and to briefly illustrate. However, the present invention is not limited to the above embodiment. Changes in detail and alternative forms of the technical solution of the present invention may be made and the present invention may be implemented in various forms without departing from the scope of the core gist of the present invention, but these changes and alternatives are within the scope of the present invention and will not be described herein.
Claims (3)
1. A method for preparing high purity 20(R) -ginsenoside Rg3 from total saponins of Panax of Araliaceae comprises the following steps: selecting 6-15% acetic acid water solution as reaction solution, and adding barium chloride (BaCl)2) As a catalyst, the addition amount of barium chloride is within the range of 0.5-2%, and ginseng is added according to the proportionThe ratio of the total ginsenoside to acetic acid aqueous solution is 1: 15-1: 20, stirring is carried out while adding, the reaction solution is placed in a water bath at the temperature of 75-85 ℃ for reaction for 2-3 h, and the mixture is kept stand and cooled to be taken out for precipitation, so as to obtain a crude product of ginsenoside Rg 3; dissolving with 50-90% ethanol, adding a certain amount of ethyl acetate, controlling the addition amount of the ethyl acetate to be 0.5-1% and the temperature to be 30-80 ℃, and cooling and recrystallizing to obtain the high-purity 20(R) -ginsenoside Rg 3.
2. The process according to claim 1, wherein: the total saponin of Panax of Araliaceae is selected from one of total saponins of Ginseng radix, total saponins of caulis Et folium Ginseng, total saponins of fructus Ginseng, total saponins of caulis Et folium Panacis Quinquefolii, total saponins of fructus Panacis Quinquefolii or total saponins of caulis Et folium Notoginseng.
3. A recrystallization process as claimed in claim 1, wherein: the purity of the obtained 20(R) -ginsenoside Rg3 is 97.0-99.99%.
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