CN116144722A - Preparation method of low-glycosylation glucosyl stevioside - Google Patents
Preparation method of low-glycosylation glucosyl stevioside Download PDFInfo
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/56—Preparation of O-glycosides, e.g. glucosides having an oxygen atom of the saccharide radical directly bound to a condensed ring system having three or more carbocyclic rings, e.g. daunomycin, adriamycin
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- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
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- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
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Abstract
The invention relates to the technical field of sweetener production, in particular to a preparation method of low-glycosylated glucosyl stevioside, which comprises the following steps: (1) Adding purified water into stevioside and beta-cyclodextrin to dissolve, moderate pH, adding glucosyltransferase, reacting and heating to obtain reaction product feed liquid; (2) Taking a reaction product feed liquid, cooling, adding glucose-based amylase, reacting for a period of time after heat preservation, and heating to obtain the reaction product feed liquid for later use; (3) Taking a reaction product feed liquid to enter a resin column, flushing the resin column by purified water and ethanol, and collecting a desorption liquid for later use; (4) And (3) taking desorption liquid, concentrating until the solid content is 40-60 wt%, and spray drying to obtain the low-glycosylation glucosyl stevioside product. The preparation method can improve the yield of the low-glycosylated glucosyl stevioside.
Description
Technical Field
The invention relates to the technical field of sweetener production, in particular to a preparation method of low-glycosylation glucosyl stevioside.
Background
Steviol glycosides are a collective term for about 40 glycoside molecules in stevia extract, and consist of hydrophilic glycosyl groups with sweet taste and steviol aglycones with hydrophobic taste. Wherein rebaudiosides D and M have a good taste, rebaudioside A (RA) has a good taste but a slightly lasting sweetness, while Stevioside (Stevioside, st), rebaudioside C and other low molecular weight steviosides have a slightly bitter or licorice aftertaste, which reduces its quality as a natural sweetener. In addition to the effect of the bitter impurities on the mouthfeel and taste properties of steviol glycoside products, the steviol aglycone molecular structure of the steviol glycoside itself is also a factor in producing bitter aftertaste and post-sweetness (i.e., sweetness lingering). From the biological point of view of taste, the difference in binding energy of different steviol glycosides to sweet taste receptors and bitter taste receptors is an important factor. In order to improve the taste of stevioside, glycosyl is introduced through enzymatic glycosylation so as to obtain a sweetener with proper taste, but the existing preparation method is not easy to control the reaction, and the prepared low-glycosylated glucosyl stevioside has lower yield. Thus, a method for preparing a low-glycosylated glucosyl stevioside was explored and studied to solve the above problems.
Disclosure of Invention
The technical problems to be solved by the invention are as follows: aiming at the defects existing in the prior art, the preparation method of the low-glycosylated glucosyl stevioside is provided, and the yield of the low-glycosylated glucosyl stevioside can be improved by using the preparation method.
In order to solve the technical problems, the technical scheme of the invention is as follows:
a method of preparing a low glycosylated glucosyl stevioside, the method comprising the steps of:
(1) Mixing raw materials of stevioside and beta-cyclodextrin according to the mass ratio of 1:1-5, adding purified water, stirring and dissolving, controlling the reaction temperature and pH, adding glucosyltransferase, reacting for a period of time after heat preservation, and heating to obtain a reaction product feed liquid for standby;
(2) Taking the reaction product feed liquid in the step (1), cooling, adding glucose-based amylase, reacting for a period of time after heat preservation, and heating to obtain the reaction product feed liquid for later use;
(3) Taking the reaction product feed liquid prepared in the step (2), positively flowing into a resin column, washing the macroporous resin column by purified water, washing the resin column by 10-30% v/v ethanol, washing the resin column by 60-80% v/v ethanol, and collecting the desorption liquid for later use;
(4) And (3) concentrating the desorption solution obtained in the step (3) until the solid content is 40-60 wt%, and spray-drying to obtain the low-glycosylation glucosyl stevioside product.
As an improved technical scheme, the purified water and the steviol glycoside in the step (1) are added according to the mass ratio of 3-5:1.
As an improved technical scheme, the reaction temperature is controlled to be 50-60 ℃ and the pH is controlled to be 5.5-6.2 in the step (1).
As an improved technical scheme, the reaction time in the step (1) is 12-24h, and the temperature is raised to 95-100 ℃.
As an improved technical scheme, the glucosyl transferase in the step (1) is added according to the dosage of 1ml to 5ml in each 100g steviol glycoside, and the activity of the glucosyl transferase is 100U/g.
As an improved technical scheme, the glucosyl amylase in the step (2) is added according to the dosage of 0.1ml-0.5ml in each 100g steviol glycoside, and the activity of the glucosyl amylase is 100000u/ml.
As an improved technical scheme, the temperature of the reaction product liquid in the step (2) is reduced to 40-60 ℃, the reaction time is 24-48h, and the temperature is increased to 95-100 ℃.
As an improved technical scheme, the resin filled in the resin column in the step (3) is macroporous adsorption resin, and the reactant liquid positively flows into the resin column according to the flow rate of 0.5/h-1.5 BV/h; the purified water washes the resin column at a flow rate of 1BV/h-3BV/h in an amount of 1-2BV of the resin column volume.
As an improved technical scheme, 10% -30% v/v of ethanol in the step (3) positively washes the resin column at a flow rate of 1BV-3 BV/h; 60% -80% v/v ethanol was forward flushed through the resin column at a flow rate of 1BV/h-3 BV/h.
After the technical scheme is adopted, the invention has the beneficial effects that:
the preparation method of the invention takes stevioside and beta-cyclodextrin as raw materials, after adding water for dissolution, controlling the reaction temperature and pH, adding glucosyltransferase, heating for inactivating enzyme after reacting for 12-24 hours, cooling the obtained reactant liquid, adding glucosyltransferase, heating for inactivating enzyme after reacting for 24-48 hours, and the obtained reactant liquid enters a resin column, the resin column is washed by purified water, and unreacted dextrin flows out along with the washing of the purified water; and then, washing out impurities by adopting 10-30% v/v of ethanol, and finally, washing out a resin column by adopting 60-80% v/v of ethanol, concentrating and drying the collected desorption solution to obtain the low-grafting low-glycosylation glucosyl stevioside product. The preparation method greatly improves the yield of the low-glycosylated glucosyl stevioside.
Detailed Description
The present invention will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
Example 1
A method for preparing a low glycosylated glucosyl stevioside comprising the steps of:
(1) Mixing raw materials of stevioside (100 g) and beta-cyclodextrin according to the mass ratio of 1:1, adding purified water with the mass 3 times of that of the stevioside, stirring and dissolving, controlling the reaction temperature at 50 ℃, controlling the pH at 5.5, adding 1ml of glucosyltransferase with the activity of 100U/g, reacting for 12 hours, and heating to 95 ℃ to inactivate the enzyme, thus obtaining a reaction product feed liquid for later use;
(2) Taking the reaction product feed liquid in the step (1), cooling to 40 ℃, adding 0.1ml of glucosyl amylase with the enzyme activity of 100000u/ml, reacting for 24 hours, and heating to 95 ℃ to inactivate the enzyme to obtain the reaction product feed liquid for later use;
(3) Taking the reaction product feed liquid prepared in the step (2), positively flowing into a resin column (the type of macroporous resin is T81) according to the flow rate of 0.5BV/h, positively flushing the macroporous resin column with purified water with the volume of 1BV of the resin column according to the flow rate of 1BV/h, positively flushing the resin column with 10% v/v ethanol according to the flow rate of 1BV/h, positively flushing the resin column with 60% v/v ethanol according to the flow rate of 1BV/h, and collecting the desorption liquid for later use;
(4) And (3) concentrating the desorption solution obtained in the step (3) until the content of solid content is 40wt%, and spray-drying to obtain the low-glycosylated glucosyl stevioside product.
Example 2
A method for preparing a low glycosylated glucosyl stevioside comprising the steps of:
(1) Mixing raw materials of stevioside (100 g) and beta-cyclodextrin according to the mass ratio of 1:2, adding purified water with the mass 3.5 times of that of the stevioside, stirring and dissolving, controlling the reaction temperature at 52 ℃, controlling the pH at 5.8, adding 2ml of glucosyltransferase with the activity of 100U/g, reacting for 15 hours, and heating to 96 ℃ to inactivate the enzyme to obtain a reaction product feed liquid for later use;
(2) Taking the reaction product feed liquid in the step (1), cooling to 48 ℃, adding glucosyl amylase with the enzyme activity of 100000u/ml, reacting for 28 hours, and heating to 96 ℃ to inactivate the enzyme to obtain the reaction product feed liquid for later use;
(3) Taking the reaction product feed liquid prepared in the step (2), positively flowing into a resin column (the type of macroporous resin is T81) according to the flow rate of 0.8BV/h, positively flushing the macroporous resin column with purified water with the volume of 1.5BV of the resin column according to the flow rate of 1.5BV/h, positively flushing the resin column with 20% v/v ethanol according to the flow rate of 1.5BV/h, positively flushing the resin column with 70% v/v ethanol according to the flow rate of 1.5BV/h, and collecting the desorption liquid for later use;
(4) And (3) concentrating the desorption solution obtained in the step (3) until the solid content is 48%, and spray-drying to obtain the low-glycosylation glucosyl stevioside product.
Example 3
A method for preparing a low glycosylated glucosyl stevioside comprising the steps of:
(1) Mixing raw materials of stevioside (100 g) and beta-cyclodextrin according to the mass ratio of 1:3.5, adding purified water with the mass 4.5 times of that of the stevioside, stirring and dissolving, controlling the reaction temperature at 55 ℃, controlling the pH at 6.0, adding 3.5ml of glucosyltransferase with the activity of 100U/g, reacting for 20 hours, and heating to 97 ℃ to inactivate the enzyme, thus obtaining a reaction product feed liquid for later use;
(2) Taking the reaction product feed liquid in the step (1), cooling to 55 ℃, adding 0.35ml of glucosyl amylase with the enzyme activity of 100000u/ml, reacting for 32 hours, and heating to 98 ℃ to inactivate the enzyme to obtain the reaction product feed liquid for later use;
(3) Taking the reaction product feed liquid prepared in the step (2), positively flowing into a resin column (the type of macroporous resin is T81) according to the flow rate of 1.2BV/h, positively flushing the macroporous resin column with purified water with the volume of 1.8BV of the resin column according to the flow rate of 2.5BV/h, positively flushing the resin column with 25% v/v ethanol according to the flow rate of 2.5BV/h, positively flushing the resin column with 75% v/v ethanol according to the flow rate of 1.5BV/h, and collecting the desorption liquid for later use;
(4) And (3) concentrating the desorption solution obtained in the step (3) until the solid content is 55wt%, and spray-drying to obtain the low-glycosylated glucosyl stevioside product.
Example 4
A method for preparing a low glycosylated glucosyl stevioside comprising the steps of:
(1) Mixing raw materials of stevioside (100 g) and beta-cyclodextrin according to the mass ratio of 1:5, adding purified water with the mass 5 times of that of the stevioside, stirring and dissolving, controlling the reaction temperature at 60 ℃, controlling the pH at 6.2, adding 5ml of glucosyltransferase with the activity of 100U/g, reacting for 24 hours, and heating to 100 ℃ to inactivate the enzyme to obtain a reaction product feed liquid for later use;
(2) Taking the reaction product feed liquid in the step (1), cooling to 60 ℃, adding 0.5ml of glucosyl amylase with the enzyme activity of 100000u/ml, reacting for 36 hours, and heating to 100 ℃ to inactivate the enzyme to obtain the reaction product feed liquid for later use;
(3) Taking the reaction product feed liquid prepared in the step (2), positively flowing into a resin column (the type of macroporous resin is T81) according to the flow rate of 1.5BV/h, positively flushing the macroporous resin column with purified water with the volume of 2BV of the resin column according to the flow rate of 3BV/h, positively flushing the resin column with 30% v/v ethanol according to the flow rate of 3BV/h, positively flushing the resin column with 80% v/v ethanol according to the flow rate of 3BV/h, and collecting the desorption liquid for later use;
(4) And (3) concentrating the desorption solution obtained in the step (3) until the solid content is 60wt%, and spray-drying to obtain the low-glycosylated glucosyl stevioside product.
Example 5
Unlike the operation of example 3, the reaction time of step (1) was 16h; the reaction time of the step (2) is 40h; the rest of the operations are the same.
Example 6
Unlike the operation of example 3, the reaction time of step (1) was 14h; the reaction time of the step (2) is 45h; the rest of the operations are the same;
example 7
Unlike the operation of example 3, the reaction time of step (1) was 12h; the reaction time of the step (2) is 48 hours; the rest of the operations are the same;
in order to better demonstrate that the yield of the low glycosylated glucosyl stevioside can be improved with the preparation method of the present invention, 5 comparative examples are given with reference to example 3, and specific experimental data are detailed in table 1.
Comparative example 1
The procedure was as in example 3, except that the reaction temperature in step (1) was 45℃and the rest was the same.
Comparative example 2
The procedure was as in example 3, except that the reaction temperature in step (1) was 65℃and the rest was the same.
Comparative example 3
Unlike example 3, after the purified water rinse in step (3), the remainder was the same with a 35% -45% v/v ethanol rinse;
comparative example 4
Unlike the procedure of example 3, the final 55% v/v ethanol rinse in step (3) was used, the remainder of the procedure being the same;
comparative example 5
Unlike the procedure of example 3, the final rinse of step (3) with 85% v/v ethanol was performed identically;
TABLE 1
The glycosylation degree is less than or equal to 4 glucosyl groups (mainly comprising 1 substituent, 2 substituent and 3 substituent) are regarded as low-glycosylation glucosyl stevioside. As can be seen from the data in Table 1, the process of the present invention increases the yield of steviol glycosides for the extraction of glycosylated glucosyl groups.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, and alternatives falling within the spirit and principles of the invention.
Claims (9)
1. A process for the preparation of a low glycosylated glucosyl steviol glycoside, characterized in that the process comprises the steps of:
(1) Mixing raw materials of stevioside and beta-cyclodextrin according to the mass ratio of 1:1-5, adding purified water, stirring and dissolving, controlling the reaction temperature and pH, adding glucosyltransferase, reacting for a period of time after heat preservation, and heating to obtain a reaction product feed liquid for standby;
(2) Taking the reaction product feed liquid in the step (1), cooling, adding glucose-based amylase, reacting for a period of time after heat preservation, and heating to obtain the reaction product feed liquid for later use;
(3) Taking the reaction product feed liquid prepared in the step (2), positively flowing into a resin column, washing the macroporous resin column by purified water, washing the resin column by 10-30% v/v ethanol, washing the resin column by 60-80% v/v ethanol, and collecting the desorption liquid for later use;
(4) And (3) concentrating the desorption solution obtained in the step (3) until the solid content is 40-60 wt%, and spray-drying to obtain the low-glycosylation glucosyl stevioside product.
2. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: the purified water and the steviol glycoside in the step (1) are added according to the mass ratio of 3-5:1.
3. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: in the step (1), the reaction temperature is controlled to be 50-60 ℃ and the pH is controlled to be 5.5-6.2.
4. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: the reaction time in the step (1) is 12-24h, and the temperature is raised to 95-100 ℃.
5. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: the glycosyltransferase in the step (1) is added according to the amount of 1ml to 5ml in each 100g steviol glycoside, and the activity of the glycosyltransferase is 100U/g.
6. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: the glucosyl amylase in the step (2) is added according to the dosage of 0.1ml-0.5ml of steviol glycoside per 100g, and the activity of the glucosyl amylase is 100000u/ml.
7. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: in the step (2), the temperature of the reaction product feed liquid is reduced to 40-60 ℃, the reaction time is 24-48h, and the temperature is increased to 95-100 ℃.
8. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: the resin filled in the resin column in the step (3) is macroporous adsorption resin, and the reactant liquid positively flows into the resin column according to the flow rate of 0.5/h-1.5 BV/h; the purified water washes the resin column at a flow rate of 1BV/h-3BV/h in an amount of 1-2BV of the resin column volume.
9. A method for preparing a low glycosylated glucosyl stevioside according to claim 1, wherein: in the step (3), 10% -30% v/v of ethanol positively washes the resin column according to the flow rate of 1BV-3 BV/h; 60% -80% v/v ethanol was forward flushed through the resin column at a flow rate of 1BV/h-3 BV/h.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116769857A (en) * | 2023-08-23 | 2023-09-19 | 诸城市浩天药业有限公司 | Preparation, separation and purification process of glycosylated inositol |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116769857A (en) * | 2023-08-23 | 2023-09-19 | 诸城市浩天药业有限公司 | Preparation, separation and purification process of glycosylated inositol |
| CN116769857B (en) * | 2023-08-23 | 2023-11-07 | 诸城市浩天药业有限公司 | Preparation, separation and purification process of glycosylated inositol |
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