CN114410718A - Production method of glucosyl stevioside - Google Patents
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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 discloses a production method of glucosyl stevioside, belonging to the technical field of natural food additives. The method comprises the following steps: (1) CGT enzymatic conversion: the method comprises the following steps of (1) using Cyclodextrin Glucosyltransferase (CGT) as a transglycosylation reaction tool of GSG, using soluble starch, maltodextrin, amylose or amylopectin as glycosyl donors, using any stevioside monomer (such as RA, ST, RD or RM) or a mixture thereof, and also using mother liquor sugar produced in industrial stevioside production and a purified product thereof as an acceptor to produce GSG with higher glycosyl number; (2) and (3) carrying out enzyme digestion by using alpha glucosidase: adding alpha glucosidase into GSG obtained in step (1), and selectively and purposefully regulating and controlling the sugar chain length of glucosyl stevioside by controlling conditions such as reaction time. Finally, a GSG product with high taste quality and rich in 4-7 glucosyl groups is produced by a simpler two-step enzyme reaction process.
Description
Technical Field
The invention relates to a production method of glucosyl stevioside, belonging to the technical field of natural food additives.
Background
The stevioside is a natural high-power sweetener extracted from stevia rebaudiana, the sweet taste is 200-400 times of that of cane sugar, and the calorie is about 1/300 of the cane sugar. Stevia sugar is widely used in Europe, America and Asia countries at present, and can be used for preparing food such as beverage, candy, baked food, etc. The commercial stevioside product is a mixture comprising at least 8 glycoside compounds, the main components of which are Rebaudioside A (RA), stevioside (St), Rebaudioside C (RC), Rebaudioside F (RF), Dulcoside A (DA), and the like. All glycosides have the same steviol aglycone, except for the glycosyl substituents and glycosidic linkages at positions C13 and C19.
Steviol glycosides have both sweet and bitter tastes, and the taste quality of both tastes is related to the number of sugar groups attached to their bulk, as well as the type of glycosidic bond between the sugar groups. For example, RA (one more glucosyl group than ST) is more sweet and the post-bitterness of ST is more pronounced. RD and RM and their isomers (two to three more glucosyl groups than ST) are considered to have better taste quality than RA, and are two kinds of stevioside recognized as the best taste quality in the industry at present. Glucosyl Steviol Glycoside (GSG) is a modified product with improved taste quality and reduced bitterness obtained by covalently bonding one to several glucosyl groups to steviol glycoside through an enzymatic method, and has been approved for use in the united states, china, and other countries. Generally, in the preparation of glucosyl steviol glycoside products, the effect of transglycosidation reaction will produce different GSG products depending on the properties of the enzyme used and the nature of the glycosyl donor, and there is no disclosure or suggestion of a method for effectively regulating the taste quality of GSG. Therefore, the quality of the current commercial GSG products is uneven and unsatisfactory.
Disclosure of Invention
[ problem ] to provide a method for producing a semiconductor device
The invention aims to solve the technical problem that in the preparation process of glucosyl stevioside, a GSG product which is rich in additional 1-3 glucosyl groups and has high quality is finally produced by a simpler process through a method for adjusting the amount of the glucosyl groups.
[ technical solution ] A
According to the invention, alpha-cyclodextrin glucosyltransferase and alpha-glucosidase are adopted to carry out structure modification reaction on stevioside in sequence, and a glucosyl stevioside product can be obtained by controlling reaction conditions, wherein the length of a glucose chain on stevioside which is subjected to enzyme catalysis covalent connection can be adjusted within the range of 1-7 units, and particularly the glucosyl stevioside product with the length of 1-3 units can be obtained.
The first purpose of the invention is to provide a method for producing glucosyl stevioside, wherein a glycosyl donor and stevioside are used as reaction substrates, alpha-cyclodextrin glucosyltransferase is adopted for enzymolysis, and then alpha-glucosidase is adopted for enzymolysis, so that glucosyl stevioside is obtained; glycosyl donors include soluble starch, maltodextrin, amylose or amylopectin.
In one embodiment of the present invention, stevioside refers to a product containing stevioside, and can be any one of stevioside monomers (such as RA, ST, RD or RM, etc.) or a mixture thereof, and can also be mother liquor sugar produced in industrial stevioside production and a purified product thereof.
In one embodiment of the invention, the mass ratio of the glycosyl donor to the stevioside in the substrate is 1-10: 1, the glycosyl donor concentration ranges from 4g/L to 40g/L, and the stevioside concentration ranges from 4g/L to 40 g/L.
In one embodiment of the present invention, the enzymatic conditions for the alpha-cyclodextrin glucosyltransferase are: the addition amount of the enzyme is 0.2-0.5KNU-CP/100mL of substrate, the reaction temperature is 50-70 ℃, the pH value is 7.5, and the reaction time is 10 min-24 h.
In one embodiment of the present invention, the enzymatic conditions of the α -glucosidase are: the addition amount of the enzyme is 10-15AGU/100mL of substrate, the reaction temperature is 20-40 ℃, and the reaction time is 2-24 h.
Preferably, the enzymolysis time of the alpha-cyclodextrin glucosyltransferase is 8 hours, and the enzymolysis time of the alpha-glucosidase is 4 hours.
The second purpose of the invention is to provide glucosyl stevioside prepared according to the method.
In one embodiment of the invention, the content of the product with 1-3 additional glucosyl groups in the glucosyl stevioside reaches 80-100%.
A third object of the invention is a product containing glucosyl steviol glycosides as described above.
The fourth purpose of the invention is to provide the application of the glucosyl stevioside in increasing the sweetness of the product.
The invention has the beneficial effects that:
according to the invention, two steps of enzyme reactions are carried out, in the first step, cyclodextrin glucosyltransferase is used as a catalyst, a sugar chain formed by 1-7 glucose units is grafted on any stevioside, the conversion rate of the reaction in the step is more than 70%, and the content of GSG in a product reaches more than 70%; secondly, using alpha-glucosidase as a catalyst, shearing sugar chains on the GSG obtained in the first step of reaction to obtain products with the sugar chain length of 1-3 glucose units, wherein the content of the products with the sugar chain length of 1-3 glucose units reaches 72.6%; after the reaction, the content of GSG in the product reaches more than 60 percent, and the product with the sugar chain length of 1 glucose unit is used as a main component (the content is 48.4 percent), so that the product has obvious taste quality improvement effect in the aspects of aftertaste, afterbitterness and sweetness quality compared with reaction raw materials.
Drawings
FIG. 1 is a comparison of HPLC profiles after conversion of ST starting material to CGT enzyme; (a) HPLC profile of ST sample; (b) HPLC profile of CGT enzyme converted ST.
FIG. 2 shows the results of the conversion of ST by CGTase with time.
FIG. 3 is the results of the reaction of alpha-glucosidase to regulate glucose chain length in GSG.
FIG. 4 is a graph showing the results of ion chromatography of the chain length distribution of example 2.
FIG. 5 shows the results of the PCA analysis of sensory evaluation in example 3.
FIG. 6 is a spider-web plot of sensory evaluation in example 3.
FIG. 7 is an HPLC chromatogram of comparative example 1; (a) HPLC profile of ST standard; (b) HPLC profile of peak amylase in water conversion of ST.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of better illustrating the invention and is not intended to limit the invention thereto.
1. Method for testing purity of glucoside
Refer to high performance liquid chromatography (method two) in GB 8270-2014 food additive stevioside, and adjust X-bridge C18 chromatographic column (4.6X 250mm,5 μm), flow rate of 0.8mL/min, column temperature of 40 deg.C, and mobile phase of 32% (v/v) acetonitrile as appropriate. Each sample was treated with a membrane, and the amount of the sample was 10. mu.L.
In the formula, ASGRepresents the area of the peak corresponding to SG in the sample, AATlThe peak area of the sample as a whole is represented.
2. Method for calculating conversion rate of enzyme-modified SG
The conversion was calculated as follows:
3. method for determining chain length distribution
The chain length distribution was determined using an ICS-5000 high performance anion exchange chromatography system (HPAEC-PAD) equipped with a pulsed amperometric detection system (Thermo Fisher, USA). The column was a CarboPac PA200, 3X 200mm (Thermo Fisher, USA). The mobile phase was 0.25M sodium hydroxide and 1M sodium acetate at a flow rate of 0.5 mL/min.
4. Sensory evaluation method
a. Relative sweetness determination
The relative sweetness of the GSG product was determined according to GB 8270-1999 using 2% (w/v) sucrose as a reference solution, preparing 20mL each of 0.040, 0.050, 0.064, 0.071, 0.080, 0.091, 0.100, 0.111, 0.117, 0.133, 0.154, 0.182, 0.200g/L GSG solutions at room temperature (25 ℃), loading into 30mL disposable tasteless test cups, disordering the order and numbering with a random three digit number. In each test, the sensory panel compares two samples (one is the reference solution) one by one and selects the sample with the sweetness closest to the reference. After each round of testing, the patient had a rest for 3min and was rinsed with clear water. The Relative Sweetness (RSV) of each set of samples was calculated by the following formula:
RSV＝A/B
where A is the concentration of the sucrose reference solution (g/L) and B is the average concentration of the samples selected by the panelists (g/L).
b. Quantitative scoring
Panelists were asked to score sweetness, after bitterness, licorice taste and taste quality on a 15-point scale. Wherein the 'sweet taste and licorice taste' is the sensory attribute tasted when the solution enters the mouth, the 'after sweet taste and after bitter taste' is the aftertaste in the oral cavity after swallowing for 3s, and the taste quality is the overall evaluation of the degree of similarity of the taste quality of the sample and a sucrose standard sample by an evaluator. In order to avoid confusion about the concept of taste attributes and provide a more uniform evaluation criterion in advance, the scores of the reference samples are commonly known after the group discussion by providing 2 reference samples for each attribute, so as to serve as anchor points for scoring in the formal test.
TABLE 1 sensory evaluation scoring criteria
In the quantitative evaluation, the concentration of SG samples was 0.04% (w/v). All samples were contained in 30mL disposable tasteless test cups with a random 3-digit digital label. The sensory panel then compares the samples, sample by sample, attribute by attribute, to the corresponding reference, and marks the corresponding scores for the samples on a 15-point linear scale. Between each set of tests, participants were asked to rest for 5min and rinse with clear water.
5. Biological material
The alpha-cyclodextrin glucosyltransferase used in the examples was purchased from Novozyme, and the enzyme activity was 3 KNU-CP/g; alpha-glucosidase is purchased from Novozyme, and the enzyme activity is 300 AGU/mL; peak amylase was purchased from Sigma and had an enzyme activity of 126U/mg.
Example 1:
a50 mL reaction system is prepared: st concentration is 4g/L, starch concentration is 10g/L, alpha-CGTase addition amount is 0.1 mu L/mL, reaction temperature is 60 ℃, pH is not adjusted (pH is 7.5). Respectively reacting for 10min, 0.5h, 1h, 2h, 4h, 8h, 12h and 24h, and inactivating enzyme in boiling water bath for 10min after the reaction is finished. The samples were subjected to HPLC analysis and the GSG conversion was calculated according to equation (1).
The conversion is shown in figure 2, under which conditions 64.6% conversion is achieved in 10 minutes, with 8 hours up to 73.2% and 24 hours up to 84.3%.
Example 2:
a50 mL reaction system is prepared: st concentration is 4g/L, starch concentration is 10g/L, CGT enzyme addition amount is 0.1 muL/mL, reaction temperature is 60 ℃, and enzyme deactivation is carried out in boiling water bath for 10min after 8h of reaction. After the system is cooled to room temperature, alpha glucosidase is added in an amount of 0.04 mu L/mL, and the temperature is controlled at 25 ℃. Respectively reacting for 2h, 4h, 8h, 12h and 24h, and inactivating enzyme in boiling water bath for 10min after the reaction is finished. The samples were subjected to HPLC analysis and the GSG conversion was calculated according to equation (1).
Samples with reaction times of 0h, 4h and 24h were taken, diluted to 1.0mg/mL and pretreated by filtration through a 0.22 μm membrane to determine the chain length distribution.
The GSG conversion is shown in FIG. 3, where the GSG content gradually decreases with reaction time, decreasing to about 60% at 24 h.
FIG. 4 is a graph of the results of ion chromatography of the chain length distribution of example 2, in which the signal at 28min is ST, and the signals on the time axis are, in order, GSG products having 1 to 6 glucosyl groups attached to ST. After 4h and 24h of glucosidase treatment, the GSG component is converted to mainly products with ST-linked sugar chain length of 1-3 glucose units, and the content of the products with ST-linked sugar chain length of 1-3 glucose units reaches 70.4% and 72.6%, respectively.
Example 3
Preparing 3 parts of 200mL reaction system: the concentration of mother liquor sugar crystallization purified glucoside (RSG) is 4g/L, the concentration of starch is 10g/L, the addition amount of CGT enzyme is 0.1 muL/mL, the reaction temperature is 60 ℃, and after 8 hours of reaction, enzyme deactivation is carried out in boiling water bath for 10 min. Wherein 1 part of the sample is reserved and marked as GSG 8-0. And after the rest two parts of the system are cooled to room temperature, adding alpha glucosidase in an adding amount of 0.04 mu L/mL, controlling the temperature to be 25 ℃, reacting for 4h and 24h respectively, and inactivating the enzyme in a boiling water bath for 10min after the reaction is finished, wherein the reaction time is marked as GSG8-4 and GSG8-24 respectively.
A sensory panel comprising 12 members was evaluated for relative sweetness according to the method described above for RSG, GSG8-0 (transglycosylation for 8 hours) and GSG8-24 (hydrolysis for 4 hours after transglycosylation for 8 hours). The relative sweetness of RSG is 251.40 + -3.65, GSG8-0 is 216.87 + -0.33, and GSG8-24 is 233.82 + -1.01 by taking 2% of sucrose as reference.
In the evaluation and analysis of the mouthfeel quality of SG samples, PCA analysis (fig. 5) showed that an increase in the amount of sugar groups reduced bitterness and increased sweetness. Through the glycosylation treatment of CGT enzyme, the bitterness and the licorice flavor of RSG are effectively reduced. GSG8-0, a transglycosylation product of RSG, was slightly less sweet than RA, but significantly less bitter and less aftersweet. The alpha-glucosidase modified products GSG8-4 and GSG-8-24 showed similar mouthfeel in sensory evaluation. GSG products exhibit unique taste attributes that differ from other elemental SG. The acceptance of the GSG product by the panel was close to that of RM.
The specific score of SG samples is in the spider-web plot (fig. 6). RSG purified from MLS crystals exhibits a more pronounced licorice flavor because it contains small amounts of polyphenols. The sweet, after-bitter and licorice flavor attributes of GSG8-0, obtained by modifying the elongation of the glucosyl chain with CGTase, were all reduced, while its taste quality was closer to RA (FIG. 6). After 4 hours of treatment with alpha-glucosidase, GSG8-4 showed a stronger sweet taste, whereas the bitterness remained low. Although licorice flavor was slightly increased, the overall acceptance of GSG8-4 was close to RM. After 24 hours of alpha-glucosidase treatment, GSG8-24 is composed mainly of short glucosyl chain components, and its taste quality evaluation is slightly reduced compared to GSG 0-4. Therefore, preferably, the enzymolysis condition of the alpha-cyclodextrin glucosyltransferase is the addition amount of 0.3KNU-CP/100mL, the reaction temperature is 60 ℃, and the reaction time is 8h, and the enzymolysis condition of the alpha-glucosidase is the addition amount of 12AGU/100mL, the reaction temperature is 25 ℃, and the reaction time is 4 h.
Comparative example 1
The reaction parameters are the same as example 1, but the peak amylase is used to replace alpha-cyclodextrin glucosyltransferase, the addition amount is 1260U/100mL, the reaction temperature is 25 ℃, and the reaction time is 8 h. The samples were subjected to HPLC analysis and the GSG conversion was calculated according to equation (1). The sample profile is shown in fig. 7(b), and the GSG conversion rate is about 14.4%, which is significantly lower than that of cgtase.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (10)
1. The production method of the glucosyl stevioside is characterized in that a glycosyl donor and the stevioside are used as reaction substrates, alpha-cyclodextrin glucosyltransferase is firstly adopted for enzymolysis, and then alpha-glucosidase is adopted for enzymolysis, so that the glucosyl stevioside is obtained.
2. The method of claim 1, wherein the glycosyl donor comprises soluble starch, maltodextrin, amylose or amylopectin.
3. The method according to claim 1 or 2, wherein the stevioside refers to a stevioside-containing product, and is any one of stevioside monomers or a mixture thereof, or a mother liquor sugar produced in industrial stevioside production and a purified product thereof.
4. The method according to any one of claims 1 to 3, wherein the mass ratio of the glycosyl donor to the steviol glycoside in the substrate is 1-10: 1, the glycosyl donor concentration is 4-40 g/L, and the steviol glycoside concentration is 4-40 g/L.
5. The method of any one of claims 1-4, wherein the alpha-cyclodextrin glycosyltransferase is enzymatically hydrolyzed under conditions selected from the group consisting of: the addition amount of the enzyme is 0.2-0.5KNU-CP/100mL of substrate, the reaction temperature is 50-70 ℃, the pH value is 7-8, and the reaction time is 10 min-24 h.
6. The method according to any one of claims 1 to 5, wherein the enzymatic conditions of the α -glucosidase are: the addition amount of the enzyme is 10-15AGU/100mL of substrate, the reaction temperature is 20-40 ℃, and the reaction time is 2-24 h.
7. A glucosyl steviol glycoside prepared according to the method of any one of claims 1 to 6.
8. The glucosyl steviol glycoside according to claim 7, wherein the content of the product with 1-3 additional glucosyl groups in the glucosyl steviol glycoside is 80-100%.
9. A product comprising the glucosyl steviol glycoside of claim 7.
10. Use of the glucosyl steviol glycoside according to claim 7 for increasing the sweetness of a product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116462777A (en) * | 2023-04-14 | 2023-07-21 | 桂林莱茵合成生物技术有限公司 | Novel glucosyl stevioside RMM and application and synthesis method thereof |
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| CN116462777A (en) * | 2023-04-14 | 2023-07-21 | 桂林莱茵合成生物技术有限公司 | Novel glucosyl stevioside RMM and application and synthesis method thereof |
| CN116462777B (en) * | 2023-04-14 | 2023-11-17 | 桂林莱茵合成生物技术有限公司 | Novel glucosyl stevioside RMM and application and synthesis method thereof |
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