JPH0453876B2 - - Google Patents

Description

[Detailed description of the invention]

TECHNICAL FIELD OF THE INVENTION The present invention relates to a method for purifying α-glycosylglycyrrhizin, and more particularly to a method for obtaining highly purified α-glycosylglycyrrhizin from a solution containing α-glycosylglycyrrhizin and glycyrrhizin. Technical background of the invention and its problems Conventionally, regarding the purification method of glycyrrhizin contained in licorice extract extracted from licorice,
Various reports have been made (Japanese Unexamined Patent Publication No. 52-139710,
(Japanese Patent Application Laid-Open No. 56-51500, etc.). However, in any of the above methods, it was extremely difficult to remove the bitter and astringent components in the licorice extract. In order to solve these problems,
No. 870 discloses that the bitterness and astringency of glycyrrhizin can be improved by treating an aqueous solution containing glycyrrhizin and starch with cyclodextrin glucanotransferase to obtain a reaction mixture containing α-glycosylglycyrrhizin. A method for removing taste qualities such as and other off-flavors is disclosed, and it is taught that the α-glycosylglycyrrhizin thus obtained can be used in applications such as food and beverages. Furthermore, the above-mentioned Japanese Patent Application Publication No. 58-870 describes the concentration of α-glycosylglycyrrhizin contained in the reaction mixture obtained by reacting cyclodextrin glucanotransferase with an aqueous solution containing glycyrrhizin and starch. As a method for increasing the concentration, the reaction mixture is passed through a column packed with a synthetic adsorbent, and α-glycosylglycyrrhizin and glycyrrhizin are adsorbed onto the synthetic adsorbent, while free saccharides in the reaction mixture are allowed to flow out from the column. , then add methanol water to this column,
A method is disclosed in which an eluate with an increased concentration of α-glycosylglycyrrhizin in the reaction mixture is obtained by performing a treatment such as passing an aqueous ethanol solution or the like through the reaction mixture. However, the eluate with an increased concentration of α-glycosylglycyrrhizin obtained by such a method contains unreacted glycyrrhizin in addition to α-glycosylglycyrrhizin.
Therefore, the solid material obtained from the above eluate contains glycyrrhizin in addition to α-glycosylglycyrrhizin. By the way, the solubility of solid glycyrrhizin in water is extremely low under acidic conditions, and if a large amount of glycyrrhizin is attempted to be dissolved in water, the glycyrrhizin will gel. Therefore, glycyrrhizin and α-
The solubility of a solid material containing glycosylglycyrrhizin is greatly influenced by the content of glycyrrhizin contained together with α-glycosyllythylglytin in this solid material. In this way, when trying to dissolve a solid substance containing glycyrrhizin and α-glycosylglycyrrhizin in water, the glycyrrhizin turns into a gel and cannot be dissolved in large amounts in water. There is a problem in that the use of solid products containing glycosylglycyrrhizin is severely restricted. Purpose of the Invention The present invention aims to solve the problems associated with the prior art as described above, and aims to separate and remove unreacted glycyrrhizin and impurities from the α-glycosylation reaction product of glycyrrhizin to obtain high-purity glycyrrhizin. α- to obtain α-glycosylglycyrrhizin of
An object of the present invention is to provide a method for purifying glycosylglycyrrhizin. Summary of the Invention The method for purifying α-glycosylglycyrrhizin according to the present invention comprises contacting a solution containing α-glycosylglycyrrhizin and glycyrrhizin with an anion exchange resin converted to Cl, SO ₄ or OH type, or - A solution containing glycosylglycyrrhizin and glycyrrhizin and a synthetic resin adsorbent under acidic conditions of PH 1.5 to 6.5 and
α-glycosylglycyrrhizin and glycyrrhizin are separated by contacting them under heating conditions of ~90°C, adsorbing glycyrrhizin on an anion exchange resin or synthetic resin adsorbent, and letting α-glycosylglycyrrhizin flow out. It is a feature. Since the present invention has the above characteristics, unreacted glycyrrhizin and impurities can be separated and removed from the α-glycosylation reaction product of glycyrrhizin to obtain highly pure α-glycosylglycyrrhizin. Furthermore, since the α-glycosylglycyrrhizin purified by the present invention does not substantially contain unreacted glycyrrhizin, it exhibits high solubility in water even under acidic conditions, and therefore hardly causes gelation. There is no bitterness or astringency. DETAILED DESCRIPTION OF THE INVENTION The method for purifying α-glycosylglycyrrhizin according to the present invention will be specifically described below. α by anion exchange resin or synthetic resin adsorbent
- Main treatment of glycosylglycyrrhizin and glycyrrhizin-containing solution The solution containing α-glycosylglycyrrhizin and glycyrrhizin used in the present invention is obtained by treating the solution containing glycyrrhizin and starch with cyclodextrin glucanotransferase. A solution obtained by inactivating the reaction solution by heating as necessary is used. As the anion exchange resin used in the present invention, a weak base resin or a strong base resin can be used. As the weak basic resin, specifically, Diaion WA-20, 30, etc., commercially available from Mitsubishi Kasei Corporation, are used. Specifically, as the strong basic resin, Diaion PA408, PA412, etc. commercially available from Mitsubishi Kasei Corporation are used. Such an anion exchange resin is pre-treated with Cl,
It is preferable to use SO ₄ , OH type, etc. by substitution. The synthetic resin adsorbent used in the present invention is composed of a porous polymer resin that has a large network structure and exhibits intermediate polarity or non-polarity, and has a wide range of surface area, porosity, and pore size distribution. Examples include resin adsorbents. Examples of non-polar synthetic resin adsorbents include styrene-divinylbenzene polymers,
It has a specific surface area of 800 m ² /g, an average pore diameter of 40 to 100 angstroms, and a porosity of 30 to 55% by volume. Such a synthetic resin adsorbent is, for example, available from Organo Co., Ltd. under the trade name Amberlite Adsorbent XAD-
2. Commercially available as XAD-4 or HP-20 from Mitsubishi Kasei Corporation. Examples of synthetic resin adsorbents with intermediate polarity include acrylic ester polymers, which have a specific surface area of 100 to 500 m ² /g, an average pore diameter of 70 to 250 angstroms, and an average pore diameter of 50 to 250 angstroms.
It has a porosity of 60% by volume. Such synthetic resin adsorbents are commercially available, for example, from Organo Co., Ltd. under the trade names Amberlite Adsorbent XAD-7 and XAD-8. In the present invention, a solution containing α-glycosylglycyrrhizin and glycyrrhizin described above is brought into contact with the anion exchange resin or synthetic resin adsorbent described above, and glycyrrhizin is adsorbed onto the anion exchange resin or synthetic resin adsorbent. ,α
- By draining glycosylglycyrrhizin, α-glycosylglycyrrhizin and glycyrrhizin are separated, and α-glycosylglycyrrhizin is purified. When adsorbing glycyrrhizin onto a synthetic resin adsorbent, a solution containing α-glycosylglycyrrhizin and glycyrrhizin is heated under acidic conditions at 30 to 90°C, preferably using an acid as described below.
It is desirable to heat it to 40-60°C. The reason why it is preferable to contact the solution containing α-glycosylglycyrrhizin and glycyrrhizin with the synthetic resin adsorbent under such acidic conditions is that under acidic conditions, the glycyrrhizin contained in the solution is strongly adsorbed by the adsorbent. This is because glycyrrhizin can be efficiently separated from the above solution. This acidic condition has a PH value of 1.5 to
6.5, preferably 3.0 to 6.0.
If this PH value is less than 1.5, the glycyrrhizin in the solution tends to precipitate or gel, making it difficult to contact the solution with the synthetic resin adsorbent containing this glycyrrhizin, which is not preferable. If the pH value exceeds 6.5, the effect of adding the acid will not be sufficiently exhibited, which is not preferable. Examples of the acid used to acidify the solution containing α-glycosylglycyrrhizin and glycyrrhizin include inorganic acids and organic acids. Inorganic acids include hydrochloric acid, sulfuric acid,
Phosphoric acid and the like can be used. Further, as the organic acid, acetic acid, citric acid, tartaric acid, lactic acid, succinic acid, etc. can be used. These inorganic or organic acids are used as an aqueous solution. The reason why it is desirable to bring the solution containing α-glycosylglycyrrhizin and glycyrrhizin into contact with the synthetic resin adsorbent under the above-mentioned heating conditions is that the solution and the adsorbent should not come into contact under acidic conditions. This is to prevent the precipitation or gelation of unreacted glycyrrhizin in the solution, which occurs as the pH value of the solution is lowered, and to increase the adsorption of glycyrrhizin to the adsorbent. When using an anion exchange resin as an adsorbent, when adsorbing α-glycosylglycyrrhizin onto the anion exchange resin, using the above-mentioned acid,
A solution containing α-glycosylglycyrrhizin and glycyrrhizin may be heated to 30 to 90°C under acidic conditions. In this way, when a solution containing α-glycosylglycyrrhizin and glycyrrhizin is brought into contact with an anion exchange resin or a synthetic resin adsorbent, α-glycosylglycyrrhizin and glycyrrhizin are adsorbed on the anion exchange resin or synthetic resin. It is thought that because of the difference in adsorption power to the agent, only glycyrrhizin is adsorbed to the anion exchange resin or synthetic resin adsorbent, while α-glycosylglycyrrhizin is eluted, making it possible to separate the two. Specifically, when a solution containing α-glycosylglycyrrhizin and glycyrrhizin is brought into contact with an anion exchange resin or a synthetic resin adsorbent (hereinafter both may be collectively referred to as resin), glycyrrhizin strongly binds to the resin. α, which has a weaker adsorption power to resin than glycyrrhizin.
- It is thought that glycosylglycyrrhizin flows out from the resin as it is without being adsorbed to the resin. Furthermore, even if α-glycosylglycyrrhizin is once adsorbed to the resin, when α-glycosylglycyrrhizin is adsorbed and glycyrrhizin approaches the adsorption site of the anionic resin or synthetic resin adsorbent, the adsorption of α-glycosylglycyrrhizin and glycyrrhizin to the resin. Due to the difference in power,
At the adsorption site, α-glycosylglycyrrhizin and glycyrrhizin are exchanged, glycyrrhizin is adsorbed to the resin, and α-glycosylglycyrrhizin is desorbed from the resin in return.
It is believed that glycosylglycyrrhizin and glycyrrhizin are separated using an anion exchange resin or a synthetic resin adsorbent. Therefore, when a solution containing α-glycosylglycyrrhizin and glycyrrhizin is brought into contact with an anion exchange resin or a synthetic resin adsorbent, and glycyrrhizin is adsorbed onto the anion exchange resin or synthetic resin adsorbent, some Even if α-glycosylglycyrrhizin is adsorbed on an anion exchange resin or synthetic resin adsorbent, glycyrrhizin and a solution containing glycyrrhizin and an anion exchange resin or synthetic resin adsorbent on which α-glycosylglycyrrhizin has been adsorbed are further adsorbed. By contacting, α-glycosylglycyrrhizin and glycyrrhizin are exchanged at the adsorption site where α-glycosylglycyrrhizin is adsorbed,
α-glycosylglycyrrhizin can be desorbed. Even if the solution containing α-glycosylglycyrrhizin and glycyrrhizin contains impurities such as monosaccharides, oligosaccharides, or unreacted dextrins, these impurities will not be adsorbed by the anion exchange resin or synthetic resin adsorbent. . Therefore, these impurities adhering to the resin upon contact of the anion exchange resin or synthetic resin adsorbent with the solution can be easily removed from the resin by washing the resin with water or hot water. As described above, an α-glycosylglycyrrhizin solution from which glycyrrhizin has been separated is obtained. In the present invention, the above-mentioned solution containing α-glycosylglycyrrhizin and glycyrrhizin is brought into contact with an anion exchange resin or a synthetic resin adsorbent. Although it can be carried out by a batch method in which an adsorbent is added, it is usually preferable to carry out a column method in which a column is filled with an anion exchange resin or a synthetic resin adsorbent. When a solution containing α-glycosylglycyrrhizin and glycyrrhizin is brought into contact with an anion exchange resin or a synthetic resin adsorbent by the column method, the flow of the solution containing α-glycosylglycyrrhizin and glycyrrhizin in the column is It is preferable that the speed is about 0.1 to 3 per hour in space velocity (SV). The α-glycosylglycyrrhizin solution obtained by flowing out and desorbing from the anion exchange resin or synthetic resin adsorbent in this way is treated with H
Although it is possible to further desalt and purify using a type ion exchange resin, the α-glycosylglycyrrhizin solution obtained as described above can also be consumed as is, or it may be concentrated or
It can also be dried and powdered for consumption. After outflowing and desorbing α-glycosylglycyrrhizin using an anion exchange resin or a synthetic resin adsorbent as described above, as described later,
An anion exchange resin or a synthetic resin agent is used to desorb α-glycosylglycyrrhizin and/or glycyrrhizin in “pre-treatment” or “post-treatment” using a synthetic resin adsorbent. Remaining adsorbed glycyrrhizin and some α
-Desorbs and recovers glycosylglycyrrhizin, etc.
It can be reused in place of the solution containing α-glycosylglycyrrhizin and glycyrrhizin used in the present invention. Glycyrrhizin and α from anion exchange resin
- When desorbing glycosylglycyrrhizin, use a desorbent containing an alkali or organic solvent,
If salts such as NaCl, CaCl ₂ , Na ₂ SO ₄ are added and used as a desorbent, the desorption of glycyrrhizin and the partially adsorbed α-glycosylglycyrrhizin becomes easier. In addition, glycyrrhizin and some α-
The desorption and recovery operation of glycosylglycyrrhizin has the advantage that it also serves as a regeneration treatment for the anion exchange resin or synthetic resin adsorbent at the same time. By performing this operation, it becomes possible to reuse the anion exchange resin or synthetic resin adsorbent used for purifying α-glycosylglycyrrhizin. Not only glycyrrhizin was isolated, but also α-
In order to obtain glycosylglycyrrhizin and highly purified α-glycosylglycyrrhizin from which impurities such as monosaccharides, oligosaccharides, or unreacted dextrins present in the glycyrrhizin-containing solution have been separated, the above-mentioned anion exchange resin or Prior to the treatment of α-glycosylglycyrrhizin and a solution containing glycyrrhizin (main treatment) with a synthetic resin adsorbent, or after this "main treatment", treatment with a synthetic resin adsorbent such as that used in the "main treatment" above. It is preferable to perform the following treatment on the solution. Below, we will discuss cases in which a solution containing α-glycosylglycyrrhizin and glycyl is treated with a synthetic resin adsorbent (pretreatment) prior to treatment with an anion exchange resin or synthetic resin adsorbent, and an anion exchange resin or synthetic resin adsorbent. The explanation will be made separately for the case where the treatment with a synthetic resin adsorbent is performed after the treatment of α-glycosylglycyrrhizin and a solution containing glycyrrhizin with an adsorbent (post-treatment). Pretreatment with a synthetic resin adsorbent A case in which a solution containing α-glycosylglycyrrhizin and glycyrrhizin is treated with a synthetic resin adsorbent prior to treatment with an anion exchange resin or a synthetic resin adsorbent (main treatment) will be explained. do. A solution containing α-glycosylglycyrrhizin and glycyrrhizin and a synthetic resin adsorbent similar to that used in the above-mentioned "main treatment" are used. are brought into contact with each other to adsorb α-glycosylglycyrrhizin and glycyrrhizin onto the synthetic resin adsorbent. When adsorbing α-glycosylglycyrrhizin and glycyrrhizin onto a synthetic adsorbent, a solution containing α-glycosylglycyrrhizin and glycyrrhizin is added to the synthetic resin under acidic conditions using the acid described above under the heating conditions described above. It is desirable to pass the liquid through the adsorbent. As described above, after adsorbing α-glycosylglycyrrhizin and glycyrrhizin in a solution containing α-glycosylglycyrrhizin and glycyrrhizin to a synthetic resin adsorbent, alkaline water, an alkaline organic solvent, an alkali water-containing organic solvent, Desorption of α-glycosylglycyrrhizin and glycyrrhizin from a synthetic resin adsorbent is performed using a water-containing organic solvent or an organic solvent. Even if a solution containing α-glycosylglycyrrhizin and glycyrrhizin contains impurities such as monosaccharides, oligosaccharides, or unreacted dextrins, these impurities are not adsorbed by the synthetic resin adsorbent. Therefore, even if such impurities adhere to the synthetic resin adsorbent, the impurities can be removed from the synthetic resin adsorbent by washing with water. When desorbing α-glycosylglycyrrhizin and glycyrrhizin from a synthetic resin adsorbent, alkaline water, alkaline organic solvents, alkaline hydrous organic solvents, hydrous organic solvents, or organic solvents are used as desorbents. Specifically, the following are used. Specific examples of alkaline water include carbonated soda water, ammonia water, caustic soda water, and caustic potash water. The alkali concentration of such alkaline water is preferably 0.1 to 2.0 normal concentration. The alkaline water-containing organic solvent is a mixed solvent of alkaline water and an organic solvent, and specifically includes a mixed solvent of an aqueous sodium hydroxide solution and methanol. In this alkaline water-containing organic solvent, the alkali has a normal concentration of 0.01 to 2.0, and the water has a normal concentration of 5 to 2.0.
In an amount of 60% by weight, the organic solvent is preferably present in an amount of 40-95% by weight. Specifically, the organic solvent includes methanol,
Examples include alcohols such as ethanol and isopropanol, ketones such as acetone, and ethers such as ethyl ether. Among these, ethanol is preferably used. The water-containing organic solvent is a mixed solvent of water and the above-mentioned organic solvent, and specifically, a mixed solvent of ethanol and water is used. In such water-containing organic solvents, water is preferably present in an amount of 5 to 60% by weight. As mentioned above, if a solution containing α-glycosylglycyrrhizin and glycyrrhizin is “pretreated” with a synthetic resin adsorbent, impurities are removed from the solution, resulting in a solution containing substantially only α-glycosylglycyrrhizin and glycyrrhizin. is obtained. This solution containing only α-glycosylglycyrrhizin and glycyrrhizin is used in place of the solution containing α-glycosylglycyrrhizin and glycyrrhizin, and the “main treatment” is performed using an anion exchange resin or a synthetic resin adsorbent as described above.
This not only removes glycyrrhizin, but also substantially removes impurities such as monosaccharides, oligosaccharides, or unreacted dextrin present in solutions containing α-glycosylglycyrrhizin and glycyrrhizin. Purity α-glycosylglycyrrhizin is obtained. Post-treatment with a synthetic resin adsorbent A solution containing α-glycosylglycyrrhizin and glycyrrhizin is subjected to "main treatment" using an anion exchange resin or a synthetic resin adsorbent as described above.
Then, glycyrrhizin is separated and a solution containing α-glycosylglycyrrhizin is obtained.
This solution contains impurities such as monosaccharides, oligosaccharides, and unreacted dextrins. In order to separate such impurities and α-glycosylglycyrrhizin, a solution containing them is brought into contact with a synthetic resin adsorbent as described above in the same way as the "pretreatment" with the synthetic resin adsorbent as described above. After adsorbing α-glycosylglycyrrhizin on a synthetic resin adsorbent and removing monosaccharides, oligosaccharides, unreacted dextrins, etc. with water, α-glycosylglycyrrhizin can be desorbed using a desorbent as described above. . At this time, it is not necessarily necessary to heat the solution. The α-glycosylglycyrrhizin purified as described above has high solubility in water even under acidic conditions, hardly gels, and has no bitter or astringent taste. Therefore,
α-Glycyrrhizin-free α-glycosylglycyrrhizin obtained by the present invention can be extremely easily prepared into foods, drinks, medicines, etc. compared to α-glycosylglycyrrhizin containing glycyrrhizin. Furthermore, since highly purified α-glycosylglycyrrhizin itself is tasteless and odorless, it is extremely easy to ingest foods, drinks, medicines, etc. containing α-glycosylglycyrrhizin. Effects of the Invention In the present invention, when purifying α-glycosylglycyrrhizin, a solution containing α-glycosylglycyrrhizin and glycyrrhizin is brought into contact with an anion exchange resin or a synthetic resin adsorbent, and glycyrrhizin is purified using an anion exchange resin or a synthetic resin adsorbent. Since α-glycosylglycyrrhizin and glycyrrhizin are separated by adsorbing them onto a synthetic resin adsorbent and letting α-glycosylglycyrrhizin flow out, unreacted glycyrrhizin and impurities can be separated from the α-glycosylation reaction product of glycyrrhizin. By removing it, highly purified α-glycosylglycyrrhizin can be obtained. Further, the α-glycosylglycyrrhizin purified according to the present invention does not substantially contain glycyrrhizin, so it exhibits high solubility in water even under acidic conditions, almost never gels, and is tasteless and odorless. Therefore, the highly purified α-glycosylglycyrrhizin obtained by the present invention can be easily prepared into foods, drinks, medicines, etc., and the foods, drinks, and medicines containing α-glycosylglycyrrhizin are extremely easy to ingest. Become. EXAMPLES The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples. First, sample solutions used in the following examples were prepared prior to implementation of the examples. The method for preparing this sample solution is shown below. Preparation of sample solution Glycyrrhizin (purity 98% or higher, Tokiwa Plant Chemical Research Institute product, GAS-E) (sample A) at 160%
g and 480 g of dextrin (DE6),
Hot water was added, and the pH value was adjusted to 5.8 using 2N NaOH and dissolved to obtain a solution of 2.0 (pre-reaction solution). Add 7000 units of Bacillus stayathermofueras enzyme to the pre-reaction solution obtained in this way, and heat the mixture at 60℃.
The α-glycosylation reaction of glycyrrhizin was carried out at a temperature of 40 hours. The liquid obtained by this reaction (liquid after reaction) was heated at 95°C.
The enzyme was inactivated by heating at a temperature of , and a sample solution was obtained. 50 ml of this sample liquid was taken out and vacuum concentrated and dried to obtain 15.5 g of a dry sample (sample B). Glycyrrhin α obtained as described above
- In order to investigate the reaction rate of the glycosylation reaction, the amount of glycyrrhizin in the pre-reaction solution and the post-reaction solution was measured using high performance liquid chromatography (HPLC).
The measurement conditions were UV 254 nm, ODS column, water/acetonitrile/acetic acid = 60/40/1, and flow rate 1 ml/M. As a result of the measurement, the post-reaction solution contains the pre-reaction solution.
24% of glycyrrhizin remains unreacted, and the α-glucosylation reaction rate of glycyrrhizin is
It turned out to be 76%. Example 1 A column was filled with 0.50% of porous strong basic resin, and the porous strong basic resin was replaced with OH type with 1N NaOH. Next, before the sample solution was allowed to flow through the resin, the column packing material was thoroughly washed with hot water. A sample solution of 1.0 was allowed to flow down the column that had been washed with warm water at a space velocity (SV) of 2.0 (per hour), and then warm water was allowed to flow down to thoroughly wash the column, resulting in an effluent containing 270.6 g of solids. Got 2.4. When this effluent was analyzed by HPLC, no glycyrrhizin peak was observed. Next, fill another column with non-polar porous resin adsorbent 2.0, and add a mixture of ethanol/water = 60/40.
4.0 to activate the adsorbent, the column packing was thoroughly washed with warm water. Then,
The pH value of the above effluent 2.4 was adjusted to 4.0 using 2N HCl, and it was allowed to flow down the column at a space velocity (SV) of 2.0 (per hour) to adsorb α-glycosylglycyrrhizin. Next, the column was thoroughly washed with warm water to remove impurities such as monosaccharides, oligosaccharides, or dextrins that were not adsorbed to the column packing material. Next, a mixed solution of water/ethanol = 1/1 (4.0) was allowed to flow down the column to desorb α-glycosylglycyrrhizin, thereby obtaining a desorption solution (4.0).
This desorption liquid contained 80.2 g of solid content. Example 2 A column was filled with 1.6 parts of a non-polar porous resin adsorbent and washed with 3.2 parts of a mixture of ethanol/water = 60/40 to activate the adsorbent, and then thoroughly washed with warm water. Then, 0.60 of the sample solution was added using 2N HCl.
The pH value was adjusted to 4.0, heated to 55°C, and flowed down the column at a space velocity (SV) = 2.0 (hourly). The column was then thoroughly washed with warm water to wash away impurities such as monosaccharides, oligosaccharides, or dextrins from the column. After that, water/
The adsorbed matter of this column packing material was desorbed using ethanol = 1/1 mixed solution 3.2, and the desorption solution 3.6
I got it. This desorption liquid contained 74.4 g of solid content. When this desorption solution was analyzed by HPLC, it was found that the desorption solution contained 23% glycyrrhizin in terms of area ratio. Next, 0.3 of the porous strong base resin was placed in another column, and the porous strong base resin was replaced with the OH type using 1N NaOH. After replacing the column with the OH type, the column was thoroughly washed with water. Next, the above desorption liquid 3.6 was added to the space velocity (SV) = 3.0.
(hourly) down the column. The column on which the desorption solution was allowed to flow was washed with water to obtain an output solution of 5.0.
The liquid contained 46.0g of solids. HPLC
When this effluent was analyzed, no glycyrrhizin peak was observed. Example 3 A column was filled with 0.25 g of a non-polar porous resin adsorbent and washed with 0.5 g of a 60/40 mixture of ethanol/water to activate the adsorbent, followed by thorough washing with warm water. Then, 0.30% of the sample solution was added using 2N HCl.
The pH value was adjusted to 4.0, heated to 55°C, and flowed down the column at a space velocity (SV) = 2.0 (hourly). Next, warm water was allowed to flow down to thoroughly wash the column, yielding effluent 0.7 containing 71.0 g of solid content.
When this effluent was analyzed by HPLC, no peak of clityrrhizin was observed. Next, the column was regenerated and activated with 0.5 of a 60/40 mixture of ethanol/water, and then thoroughly washed with warm water. Next, the above effluent 0.7 is SV=2.0
(hourly) to adsorb α-glycosylglycyrrhizin through the column. Next, the column was thoroughly washed with warm water to remove unadsorbed impurities such as monosaccharides, oligosaccharides, or dextrins from the column. Then, 0.5 of a mixed solution of ethanol/water = 1/1 was allowed to flow down the column to desorb α-glycoglycyrrhizin, thereby obtaining a desorption solution of 0.5.
This desorption solution contained 9.1 g of solid content. The desorption liquid sample of Example 1, the effluent sample of Example 2, and the desorption liquid sample of Example 3 were vacuum concentrated, dried, and powdered to obtain sample C. , A, and B were subjected to the following measurements. Comparative Solubility Test The solubility of Samples C, A, and B was measured (pH4.5 buffer solution, 25°C). The results are shown in Table 1.

【table】

[Table] Taste Comparison Test Samples C, A, and B were subjected to a taste comparison test by 10 panelists at room temperature of 25°C. The results are shown in Table 2. (Sample A, B: water
(based on the maximum dissolution amount per 100g)

[Table] Gelation concentration The gelation concentration (ie, the concentration at which fluidity is lost) of Samples C, A, and B was measured. (PH3.5, 5℃, 12
time) The results are shown in Table 3.

【table】

【table】

Claims (1)

[Claims] 1. A solution containing α-glycosylglycyrrhizin and glycyrrhizin, and Cl, SO ₄ or
The method is characterized in that α-glycosylglycyrrhizin and glycyrrhizin are separated by contacting an anion exchange resin substituted with OH type, adsorbing glycyrrhizin to the anion exchange resin, and causing α-glycosylglycyrrhizin to flow out. α to do
- A method for purifying glycosylglycyrrhizin. 2. A solution containing α-glycosylglycyrrhizin and glycyrrhizin and a synthetic resin adsorbent.
By contacting under acidic conditions of PH1.5 to 6.5 and heating conditions of 30 to 90°C, glycyrrhizin is adsorbed to a synthetic resin adsorbent, and α-glycosylglycyrrhizin flows out, α-glycosylglycyrrhizin and glycyrrhizin are separated. A method for purifying α-glycosylglycyrrhizin, the method comprising separating α-glycosylglycyrrhizin.