CN102453736A - Method for transforming hyperin into quercetin by enzyme reaction - Google Patents
Method for transforming hyperin into quercetin by enzyme reaction Download PDFInfo
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- CN102453736A CN102453736A CN2010105177955A CN201010517795A CN102453736A CN 102453736 A CN102453736 A CN 102453736A CN 2010105177955 A CN2010105177955 A CN 2010105177955A CN 201010517795 A CN201010517795 A CN 201010517795A CN 102453736 A CN102453736 A CN 102453736A
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Abstract
The invention relates to a method for transforming hyperin into quercetin by using a biological enzyme reaction to improve the biological activity of the hyperin. According to the method, a reaction is performed in an ethanol aqueous solution with the concentration of 30-70% under an effect of naringinase, the reaction temperature is 40-70 DEG C, the reaction time is 1-30 hours, and the glycosyl on the hyperin hydroxyl is cut, such that the hyperin is transformed into the quercetin with the high pharmacological activity. With the present invention, the workability of the hyperin is further improved, and the practical application range of the hyperin is expanded.
Description
Technical field
The present invention relates to utilize Quercetin 3-galactoside to transfer a kind of method of Quercetin to, relate in particular to and utilize enzyme reaction to obtain the method for Quercetin.
Background technology
Quercetin 3-galactoside (Hyperin) molecular formula is C
21H
20O
12, chemical structural formula is suc as formula shown in the I.Faint yellow needle crystal.
(formula I)
Quercetin 3-galactoside derives from natural product.The Quercetin of natural active matter Quercetin 3-galactoside and aglycon thereof has very great development and is worth.Wherein Quercetin 3-galactoside is used for analgesia and spasmolysis more, and the Quercetin purposes is the treatment of clinical cardiovascular disorder more.
Quercetin 3-galactoside has stronger analgesic activity, in vivo with the external spasmolysis that all shows; Damage also has remarkable provide protection to Quercetin 3-galactoside to cerebral ischemia reperfusion.Quercetin 3-galactoside also has sedative effect.
But with regard to pharmacologically active, the medicinal using value of Quercetin of Quercetin 3-galactoside aglycon composition is greater than the using value of Quercetin 3-galactoside.
In medical practice, the molecular structure of natural Quercetin 3-galactoside is not active optimal state, needs after the effect of entero-bacte enzyme system be converted into the Quercetin of aglycon down, just to be absorbed and brings into play drug effect.Many in recent years internal and external test results show that also body can absorb a considerable amount of Quercetins and play pharmacologically active.
In industry, how obtaining high reactivity monomer Quercetin and further improving its output is the field that gets a good eye meaning.Many use acid in the method for existing production Quercetin, alkali etc. have the solvent of certain murder by poisoning to extract to body.And the content of Quercetin is not high in the natural frond, thereby has problems such as yield is low.
If transfer Quercetin 3-galactoside to Quercetin with biological enzyme, can avoid the use of the deleterious solvent extraction process of body, easy to operate, reaction temperature and, can obtain extremely pure aglycon, can be applicable to the industrial mass production of Quercetin.
Transfer Quercetin 3-galactoside to Quercetin through the external biological enzyme process, can obtain the good high reactivity material of tool specificity, its production process is pollution-free again, and has characteristics such as product transformation efficiency height.
Thereby learn and not only improve physiologically active and using value, also can promote suitability for industrialized production if change Quercetin 3-galactoside into Quercetin.
Adding through enzyme is not high or not have the structural transformation of the composition of physiologically active be the high reactivity molecular structure with some physiologically actives, not only improves the physiologically active and the using value of extract, promotes suitability for industrialized production yet.Because Quercetin is easier to absorb with respect to Quercetin 3-galactoside, and the pharmacologically active of aglycon is higher than Quercetin 3-galactoside.
Summary of the invention
The objective of the invention is biological activity and using value, propose a kind of method that Quercetin 3-galactoside is changed into Quercetin with enzyme reaction in order to improve Quercetin 3-galactoside.
Technical scheme of the present invention is following: a kind of Quercetin 3-galactoside is changed into the method for Quercetin, it is characterized in that this method comprises the steps:
1) Quercetin 3-galactoside is joined in the 30%-70% ethanol system, regulate pH (4-8), system reaches certain temperature (40-70 ℃), stirs temperature control reaction down 30 hours;
2) 2) in above-mentioned reaction system, add naringinase, (standard vigor 475AGUPg),
For containing a kind of enzyme of beta-glucosidase.
Enzyme according to the invention is preferably naringinase.
On the basis of technique scheme, technical program of the present invention also lies in: said concentration of ethanol is 30%.
The invention provides a kind of applying biological enzyme reaction makes Quercetin 3-galactoside change Quercetin into to improve its bioactive method.Under the effect of enzyme, the glycosyl on the Quercetin 3-galactoside hydroxyl is scaled off becomes the Quercetin that has more using value.The present invention can significantly improve the pharmacologically active of Quercetin 3-galactoside, makes it in the medical practice process, be easy to effective use; And in experimental study, improve the transformation efficiency that Quercetin 3-galactoside is converted into aglycon, the production Quercetin is provided, or reduces the difficulty of its extraction; Can enlarge simultaneously processibility and the practical ranges of Quercetin 3-galactoside.
Description of drawings
Figure one uses the acetic acid ethyl acetate extract analytical results for Quercetin 3-galactoside changes the glycosides product.Among the figure: 1 is the Quercetin 3-galactoside standard substance; 2 is Quercetin; 3 is the Quercetin standard substance.
Embodiment
Instance 1: in the 1000mL triangular flask; Add 10mg Quercetin 3-galactoside standard substance and 400ml30% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 6.0, system reaches 50 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 50 ℃, 200rpm, stirring reaction 30 hours.With under the same terms, not adding enzyme is control group again.After reaction finishes; Use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume; Extraction liquid is with G silica-gel plate (100mm * 25mm); With ETHYLE ACETATE: formic acid=25: 1 is that moving phase is launched, sight and carry out qualitative analysis, result (1.R as shown in Figure 1 with the TLC method under the 365nm uv lamp
F Quercetin 3-galactoside standard substance=0.36 2.R
The f reaction product=0.90 3.R
The f control group=0.36), reaction product R
fValue 0.90 is much larger than standard substance R
fValue 0.36 shows through enzyme reaction and has produced the Quercetin of polarity less than Quercetin 3-galactoside that reaction mechanism can be represented with following chemical equation:
Reaction mechanism can be represented with following chemical equation:
Instance 2: in the 1000ml triangular flask; Add 10mg Quercetin 3-galactoside standard substance and 400ml40% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 5.0, system reaches 40 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 40 ℃, 200rpm, stirring reaction 30 hours.With under the same terms, not adding enzyme is control group again.After reaction finishes; Use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume; Extraction liquid is with G silica-gel plate (100mm * 25mm); ETHYLE ACETATE: formic acid: water=30: 2: 3 is that moving phase is launched, observation and carry out qualitative analysis, result (1.R as shown in Figure 2 with the TLC method under the 365nm UV-light
F Quercetin 3-galactoside standard substance=0.44 2.R
The f reaction product=0.923.R
The f control group=0.44).Reaction product R
fValue 0.92 is much larger than standard substance R
fValue 0.44 shows through enzyme reaction and has produced the Quercetin of polarity less than Quercetin 3-galactoside that reaction mechanism is identical with instance 1.
Instance 3: in the 1000ml triangular flask; Add 10mg Quercetin 3-galactoside standard substance and 400ml 50% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 6.0, system reaches 60 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 60 ℃, 200rpm, stirring reaction 30 hours.With under the same terms, not adding enzyme is control group again.After reaction finishes, use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume, extraction liquid is with ETHYLE ACETATE: formic acid=25: 1 be the moving phase expansion, sight and carry out qualitative analysis, result (1.R as shown in Figure 1 with the TLC method under the 365nm uv lamp
F Quercetin 3-galactoside standard substance=0.36 2.R
The f reaction product=0.90 3.R
The f control group=0.36), reaction product R
fValue 0.90 is much larger than standard substance R
fValue 0.36 shows through enzyme reaction and has produced the Quercetin of polarity less than Quercetin 3-galactoside that reaction mechanism is identical with instance 1.
Instance 4: in the 1000ml triangular flask; Add 10mg Quercetin 3-galactoside standard substance and 400ml60% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 7.0, system reaches 50 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 50 ℃, 200rpm, stirring reaction 30 hours.With under the same terms, not adding enzyme is control group again.After reaction finishes; Use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume; Extraction liquid is with G silica-gel plate (100mm * 25mm); ETHYLE ACETATE: formic acid: water=30: 2: 3 is that moving phase is launched, observation and carry out qualitative analysis, result (1.R as shown in Figure 2 with the TLC method under the 365nm UV-light
F Quercetin 3-galactoside standard substance=0.44 2.R
The f reaction product=0.923.R
The f control group=0.44).Reaction product R
fValue 0.92 is much larger than standard substance R
fValue 0.44 shows through enzyme reaction and has produced the Quercetin of polarity less than Quercetin 3-galactoside that reaction mechanism is identical with instance 1.
Instance 5: in the 1000ml triangular flask; Add 10mg Quercetin 3-galactoside standard substance and 400ml 40% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 4.0, system reaches 70 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 50 ℃, 200rpm, stirring reaction 30 hours.With under the same terms, not adding enzyme is control group again.After reaction finishes, use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume, extraction liquid is with ETHYLE ACETATE: formic acid=25: 1 be the moving phase expansion, sight and carry out qualitative analysis, result (1.R as shown in Figure 1 with the TLC method under the 365nm uv lamp
F Quercetin 3-galactoside standard substance=0.36 2.R
The f reaction product=0.90 3.R
The f control group=0.36), reaction product R
fValue 0.90 is much larger than standard substance R
fValue 0.36 shows through enzyme reaction and has produced the Quercetin of polarity less than Quercetin 3-galactoside that reaction mechanism is identical with instance 1.
Claims (4)
1. a method that generates Quercetin is characterized in that this method comprises the steps:
1) the Quercetin 3-galactoside standard substance are joined in the 30%-70% ethanol, the pH value is 4-8, and system temperature is 40 ℃ to 70 ℃;
2) in above-mentioned system, add naringinase, the reaction times is 30 o'clock hours.
2. according to the described method of claim 1, it is characterized in that naringinase is made up of β-rhamnosidase and beta-glucosidase.Naringinase (standard vigor 475AGUPg).
3. according to the described method of claim 1, it is characterized in that: temperature is 50 ℃.
4. according to claim 1,2,3 described methods, it is characterized in that: said pH value is 6.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2010105177955A CN102453736A (en) | 2010-10-15 | 2010-10-15 | Method for transforming hyperin into quercetin by enzyme reaction |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103589702A (en) * | 2013-11-19 | 2014-02-19 | 南京市第一医院 | Application of heat-resistant beta-glucosidase and mutants thereof |
| CN104561165A (en) * | 2014-06-19 | 2015-04-29 | 山东大学（威海） | Method for converting hyperoside to quercetin by enzyme reaction |
| CN111333602A (en) * | 2020-04-16 | 2020-06-26 | 四川迪菲特药业有限公司 | Recovery and conversion process of waste mother liquor in troxerutin production |
-
2010
- 2010-10-15 CN CN2010105177955A patent/CN102453736A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103589702A (en) * | 2013-11-19 | 2014-02-19 | 南京市第一医院 | Application of heat-resistant beta-glucosidase and mutants thereof |
| CN103589702B (en) * | 2013-11-19 | 2014-09-10 | 南京市第一医院 | Application of heat-resistant beta-glucosidase and mutants thereof |
| CN104561165A (en) * | 2014-06-19 | 2015-04-29 | 山东大学（威海） | Method for converting hyperoside to quercetin by enzyme reaction |
| CN111333602A (en) * | 2020-04-16 | 2020-06-26 | 四川迪菲特药业有限公司 | Recovery and conversion process of waste mother liquor in troxerutin production |
| CN111333602B (en) * | 2020-04-16 | 2022-12-16 | 四川协力制药股份有限公司 | Recovery and conversion process of waste mother liquor in troxerutin production |
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Application publication date: 20120516 |