CN110305925A - Preparation process of enzyme modified rutin mixture - Google Patents
Preparation process of enzyme modified rutin mixture Download PDFInfo
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- CN110305925A CN110305925A CN201910627127.9A CN201910627127A CN110305925A CN 110305925 A CN110305925 A CN 110305925A CN 201910627127 A CN201910627127 A CN 201910627127A CN 110305925 A CN110305925 A CN 110305925A
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- rutin sophorin
- enzyme
- reaction
- rutin
- mixture
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
Abstract
The invention relates to the technical field of enzymology, in particular to a preparation process of an enzyme modified rutin mixture. The method specifically comprises the following steps: reacting rutin and dextrin substances serving as main raw materials under the action of biotransformation enzyme to obtain reaction liquid A after the reaction is finished, refining the reaction liquid A to obtain different enzyme modified rutin mixtures, removing the biological enzyme in the reaction liquid A through ultrafiltration equipment, removing residual sugar in the reaction liquid A through nanofiltration equipment, desalting and decoloring through ion exchange resin and active carbon, concentrating the refined solution in vacuum, and spray drying the concentrated solution to obtain the enzyme modified rutin mixture. The method for preparing the enzyme modified rutin mixture by using the enzyme conversion method has high conversion efficiency and mild reaction, and simultaneously prepares different enzyme modified rutin mixtures by using a plurality of biological enzymes together, thereby greatly improving the flexibility of the preparation process.
Description
Technical field
The present invention relates to technical field of enzymology, in particular to a kind of preparation process of enzyme modification rutin sophorin mixture.
Background technique
Rutin sophorin is also known as rutin, citrin, is that one kind is widely present in the intracorporal flavonols glycocide of plant, two are matched
Sugared body is glucose and rhamnose.Rutin sophorin has extensive pharmacological activity, clinically for preventing and treating cerebral hemorrhage, hypertension, view
Film bleeding, acute hemorrhagic ephritis and treatment chronic bronchitis etc..In addition, rutin sophorin also has ratio in food, cosmetics industry
Wide application.But due to the poorly water-soluble of rutin sophorin, property is also unstable in aqueous solution, application and business valence
Value is restricted.
For the water solubility for improving rutin sophorin, researcher attempts various ways and is modified to it, and common rutin sophorin is modified
Method is mostly chemical method, but the modification process of chemical method is possible to generate potential prestige to the safety that rutin sophorin is applied
The side of body.Carrying out investment to rutin sophorin using cyclodextrin is simple and safe method, but rutin sophorin-cyclodextrin inclusion, dissolution
Degree only improves 10 times than rutin sophorin.Functional components are modified using zymotechnic, is a kind of simple, practical and pacifies
Full method.It is wherein always the hot spot of Recent study using the research that glycosyl point carries out enzyme modification.By functional components
It is modified to amphipathic molecule, wherein hydrophobic region is the skeleton of functional components, and hydrophilic area is grape sugar chain, is greatly improved indissoluble
The dissolubility of property substance.Compared with chemical synthesis, biosynthesis has efficient, stereocpecificity, reacts controllable, is easy to industry
The features such as change, and reaction condition is mild, at low cost, pollution is small, by-product is few.
In view of the above problems, passing through several lifes the invention proposes a kind of preparation process of enzyme modification rutin sophorin mixture
Object enzyme is used in combination, and has prepared different types of enzyme modification rutin sophorin mixture, and every kind of enzyme modification rutin sophorin mixture
Certain functional activity is all had in different field.
Summary of the invention
The present invention provides a kind of preparation process of enzyme modification rutin sophorin mixture, appoint in entire process flow without using
What organic solvent, technical process is environmentally protective, and cost is relatively low.
To achieve the above object, the present invention uses following scheme:
A kind of preparation process of enzyme modification rutin sophorin mixture, including enzymatic conversion, ultrafiltration, nanofiltration, ion exchange resin are pure
The processes such as change, active carbon decoloring, vacuum distillation, spray drying, using dextrin substance as glucosyl group donor, rutin sophorin conduct
Glucosyl group receptor, solvent are purified water, and biological enzyme is added and carries out enzymatic conversion reaction, and the pH for adjusting reaction solution is 5-6,
It is reacted 12-24 hours at 40-60 DEG C, obtains reaction solution A after reaction；Different enzyme modifications is obtained using following two scheme
Rutin sophorin mixture:
Scheme one: being added compounded saccharifying enzyme into reaction solution A, and the reaction was continued at 55 DEG C 5-8 hours, obtains after reaction
To reaction solution B, the residual sugar in the biological enzyme in reaction solution B, then logical nanofiltration equipment removal reaction solution B is removed by ultrafiltration apparatus,
Desalination bleaching processing is carried out finally by ion exchange resin and active carbon, purified solution is concentrated in vacuo, and will
Concentrate is spray-dried, and enzyme modification rutin sophorin mixture 1 is finally obtained.
Scheme two:, rhamnosidase is continuously added into reaction solution B, the reaction was continued at 55 DEG C 12-18 hours, reaction
After obtain reaction liquid C, reaction liquid C is also carried out identical ultrafiltration, nanofiltration, desalination bleaching, concentration and spray drying engineering,
Finally obtain enzyme modification rutin sophorin mixture 2.
Further, enzymatic conversion reaction refers in the presence of biology enzyme, on the hydroxyl of water-insoluble receptor, access one
A or multiple glucosyl groups to be changed into water solubility, while not influencing its bioactivity.
Further, glucosyl group donor is dextrin substance, including beta-cyclodextrin, alpha-cyclodextrin, maltodextrin etc.；It is raw
Object enzyme includes alpha-glucosaccharase transferase, cyclodextrin glycosyltransferase etc.；
Further, rutin sophorin and the mass ratio that feeds intake of dextrin substance are 1: 1~1: 6.
Further, reaction solution A, major solute are to include: glucosyl group rutin sophorin, rutin sophorin, residual sugar and other impurity,
Wherein glucosyl group rutin sophorin refers to by single glucosyl group rutin sophorin, double glucosyl group rutin sophorins, tri-glucose base rutin sophorin, four
The mixture of the glucosans base rutin sophorin such as glucosyl group rutin sophorin composition；Reaction solution B, major solute are as follows: single glucosyl group
Rutin sophorin, rutin sophorin, residual sugar and other impurity；Reaction liquid C, major solute are as follows: single glucosyl group rutin sophorin, isoquercitin,
Residual sugar and other impurity.
Further, compounded saccharifying enzyme includes amylase, Pullulanase etc., and effect is by glucosan Ji Yunxiangganshui
Xie Weidan glucosyl group rutin sophorin.
Further, enzyme modification rutin sophorin mixture 1 be buff powder, component include: single glucosyl group rutin sophorin,
Rutin sophorin, and single glucosyl group rutin sophorin content is 70%~80%, rutin sophorin content is 10%~20%；Enzyme modification rutin sophorin
Mixture 2 is buff powder, and component includes: single glucosyl group rutin sophorin, isoquercitin, and single glucosyl group rutin sophorin contains
Amount is 70%~80%, and isoquercitin content is 10%~20%；Rhamnosidase, effect is that rutin sophorin is hydrolyzed to different Mongolian oak
Pi Su.
Further, ultrafiltration apparatus is rolling ultrafiltration membrane, and the molecular cut off of film can make the removal of the enzyme in reaction solution
Rate is 95% or more；Nanofiltration equipment is rolling nanofiltration membrane, and the molecular cut off of film can make the removal rate of residual sugar in reaction solution exist
90% or more.
Further, its concentration of the concentrate after vacuum concentration is 20%~40%；Spray drying, inlet temperature control
At 150 DEG C~180 DEG C.
Innovative point and advantage of the invention is:
This technique prepares enzyme modification rutin sophorin mixture using bioenzymatic conversion method, and high production efficiency, specificity is strong, and
With greatly developing for biological enzyme technology in recent years, more efficient functionality enzymes are put into large-scale production, so that enzyme turns
The production efficiency of change method has caught up with and surpassed chemical synthesis；Simultaneously without using any organic solvent, wastewater discharge in this technique
Far smaller than chemical synthesis, and heavy metal and other noxious materials are free of in waste water；This technique is enzyme-linked by a variety of biologies simultaneously
It closes and uses, obtained different products, so that this technique has higher flexibility, production can be adjusted according to the variation in market
The purpose product of technique；The method that this technique selects wound membrane filtration to combine with ion exchange resin on purifying process, is removed
Miscellaneous high-efficient, discharge of wastewater is few；This production efficiency is high on the whole, and process is more easy, and environment friendly is higher.
Specific embodiment
Below with reference to embodiment, the present invention is described further, embodiment be in order to better illustrate the present invention, and
It does not limit the invention.
Embodiment 1:
120kg maltodextrin is added in 300kg purified water, heat and adds 60kg rutin sophorin after mixing evenly, is used
The pH that dilute hydrochloric acid adjusts reaction solution is 5, and the alpha-glucosaccharase transferase (4000U/ml) of 1500ml, the normal pressure at 50 DEG C is added
React 15h；1000ml compounded saccharifying enzyme (5000U/ml) is added into reaction solution after reaction, the reaction was continued at 55 DEG C 8
Hour, the reaction solution containing single glucosyl group rutin sophorin and rutin sophorin is obtained after reaction, reaction solution is diluted 1 times, then
It is filtered to remove alpha-glucosaccharase transferase and compounded saccharifying enzyme by rolling ultrafiltration membrane (molecular cut off 10000), using volume
Formula nanofiltration membrane (molecular cut off 200) removes residual sugar.Then it is 10% that reaction solution is diluted to concentration again, then is handed over by ion
It changes resin and carries out desalting processing, then decolourize according to 0.5% addition active carbon of amount of liquid, active carbon is removed by filters pressing
Afterwards, filtrate is concentrated in vacuo (70 DEG C of -0.1Mpa) to concentration is 30%, is then spray-dried to concentrate, spraying
Inlet temperature is 160 DEG C, obtains light yellow enzyme modification rutin sophorin mixture 71kg, wherein the content of single glucosyl group rutin sophorin is
73.6%, rutin sophorin content 17.1%.
Embodiment 2:
180kg alpha-cyclodextrin is added in 400kg purified water, heat and adds 60kg rutin sophorin after mixing evenly, is used
The pH that dilute hydrochloric acid adjusts reaction solution is 5, and the alpha-glucosaccharase transferase (4000U/ml) of 1800ml, the normal pressure at 50 DEG C is added
React 15h；1200ml compounded saccharifying enzyme (5000U/ml) is added into reaction solution after reaction, the reaction was continued at 55 DEG C 8
Hour, 400g rhamnosidase (20000U/g) is continuously added into reaction solution after reaction, the reaction was continued at 55 DEG C 15
Hour, the reaction solution containing single glucosyl group rutin sophorin and isoquercitin is obtained after reaction, reaction solution is diluted 1 times, so
Three kinds of reaction enzymes are filtered to remove by rolling ultrafiltration membrane (molecular cut off 15000) afterwards, using rolling nanofiltration membrane (retention molecule
200) amount removes residual sugar.Then it is 10% that reaction solution is diluted to concentration again, then is carried out at desalination by ion exchange resin
Then reason is decolourized according to 0.5% addition active carbon of amount of liquid, after removing active carbon by filters pressing, filtrate is carried out true
Sky concentration (80 DEG C of -0.1Mpa) to concentration is 30%, is then spray-dried to concentrate, spray inlet temperature 170
DEG C, light yellow enzyme modification rutin sophorin mixture 80kg is obtained, wherein the content of single glucosyl group rutin sophorin is 75.2%, isoquercitrin
Cellulose content 16.3%.
Embodiment 3:
180kg alpha-cyclodextrin is added in 400kg purified water, heat and adds 80kg rutin sophorin after mixing evenly, is used
The pH that dilute hydrochloric acid adjusts reaction solution is 5, and the alpha-glucosaccharase transferase (4000U/ml) of 1800ml, the normal pressure at 50 DEG C is added
React 20h；1200ml compounded saccharifying enzyme (5000U/ml) is added into reaction solution after reaction, the reaction was continued at 55 DEG C 8
Hour, 400g rhamnosidase (20000U/g) is continuously added into reaction solution after reaction, the reaction was continued at 55 DEG C 18
Hour, the reaction solution containing single glucosyl group rutin sophorin and isoquercitin is obtained after reaction, reaction solution is diluted 1 times, so
Three kinds of reaction enzymes are filtered to remove by rolling ultrafiltration membrane (molecular cut off 15000) afterwards, using rolling nanofiltration membrane (retention molecule
200) amount removes residual sugar.Then it is 10% that reaction solution is diluted to concentration again, then is carried out at desalination by ion exchange resin
Then reason is decolourized according to 0.5% addition active carbon of amount of liquid, after removing active carbon by filters pressing, filtrate is carried out true
Sky concentration (80 DEG C of -0.1Mpa) to concentration is 30%, is then spray-dried to concentrate, spray inlet temperature 170
DEG C, light yellow enzyme modification rutin sophorin mixture 95kg is obtained, wherein the content of single glucosyl group rutin sophorin is 72.5%, isoquercitrin
Cellulose content 18.7%.
Including the above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto,
Anyone skilled in the art in the technical scope disclosed by the present invention, can easily think of the change or the replacement, all
It is covered by the protection scope of the present invention.Therefore, protection scope of the present invention should be with the scope of protection of the claims
Subject to.
Claims (9)
1. a kind of preparation process of enzyme modification rutin sophorin mixture, which is characterized in that handed over including enzymatic conversion, ultrafiltration, nanofiltration, ion
The processes such as purifying resin, active carbon decoloring, vacuum distillation, spray drying are changed, using dextrin substance as glucosyl group donor, rue
For fragrant glycosides as glucosyl group receptor, solvent is purified water, and biological enzyme is added and carries out enzymatic conversion reaction, the pH for adjusting reaction solution is
5-6 reacts 12-24 hours at 40-60 DEG C, obtains reaction solution A after reaction；It is obtained using following two scheme different
Enzyme modification rutin sophorin mixture:
Compounded saccharifying enzyme is added in one: Xiang Suoshu reaction solution A of scheme, the reaction was continued at 55 DEG C 5-8 hours, obtains after reaction
To reaction solution B, the residual sugar in the biological enzyme in reaction solution B, then logical nanofiltration equipment removal reaction solution B is removed by ultrafiltration apparatus,
Desalination bleaching processing is carried out finally by ion exchange resin and active carbon, purified solution is concentrated in vacuo, and will
Concentrate is spray-dried, and enzyme modification rutin sophorin mixture 1 is finally obtained.
Scheme two: continuously adding rhamnosidase into reaction solution B, the reaction was continued at 55 DEG C 12-18 hours, after reaction
Reaction liquid C is obtained, identical ultrafiltration, nanofiltration, desalination bleaching, concentration and spray drying engineering are carried out to reaction liquid C, finally obtained
Enzyme modification rutin sophorin mixture 2.
2. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: the enzyme
Conversion reaction refers in the presence of biology enzyme, on the hydroxyl of water-insoluble receptor, accesses one or more glucosyl groups, from
And it is changed into water solubility, while not influencing its bioactivity.
3. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: the Portugal
Grape glycosyl donor is dextrin substance, including beta-cyclodextrin, alpha-cyclodextrin, maltodextrin etc.；The biological enzyme includes α-Portugal
Polyglycoside transferase, cyclodextrin glycosyltransferase etc..
4. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: the rue
Fragrant glycosides and the mass ratio that feeds intake of dextrin substance are 1: 1~1: 6.
5. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: described is anti-
Answer liquid A, major solute are as follows: glucosyl group rutin sophorin, rutin sophorin, residual sugar and other impurity, wherein glucosyl group rutin sophorin be
Refer to by single glucosyl group rutin sophorin, double glucosyl group rutin sophorins, tri-glucose base rutin sophorin, four Portugals glucosyl group rutin sophorin Deng Duo
The mixture of grape glycosyl rutin composition；The reaction solution B, major solute are as follows: single glucosyl group rutin sophorin, rutin sophorin,
Residual sugar and other impurity；The reaction liquid C, major solute are as follows: single glucosyl group rutin sophorin, isoquercitin, residual sugar and its
Its impurity.
6. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: described answers
Closing carbohydrase includes amylase, Pullulanase etc., and effect is that glucosan base rutin sophorin is hydrolyzed to single glucosyl group rue
Glycosides.
7. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: the enzyme changes
Property rutin sophorin mixture 1 be buff powder, component includes: single glucosyl group rutin sophorin, rutin sophorin, and single glucosyl group rue
Fragrant glycosides content is 70%~80%, and rutin sophorin content is 10%~20%；The enzyme modification rutin sophorin mixture 2 is yellow powder
End, component includes: single glucosyl group rutin sophorin, isoquercitin, and single glucosyl group rutin sophorin content is 70%~80%, different
Quercetin content is 10%~20%；The rhamnosidase, effect is that rutin sophorin is hydrolyzed to isoquercitin.
8. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: described is super
Filter equipment is rolling ultrafiltration membrane, and the molecular cut off of film can make the removal rate of the enzyme in reaction solution 95% or more；It is described to receive
Filter equipment is rolling nanofiltration membrane, and the molecular cut off of film can make the removal rate of residual sugar in reaction solution 90% or more.
9. a kind of preparation process of enzyme modification rutin sophorin mixture according to claim 1, it is characterised in that: the vacuum
Its concentration of concentrate after concentration is 20%~40%；The spray drying, inlet temperature are controlled at 150 DEG C~180 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111560407A (en) * | 2020-05-25 | 2020-08-21 | 江苏恒正合生命科学有限公司 | Preparation process of water-soluble rutin derivative |
| CN115976140A (en) * | 2022-12-27 | 2023-04-18 | 南京安佰思生物科技有限公司 | Production and preparation process of enzyme-modified isoquercitrin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111560407A (en) * | 2020-05-25 | 2020-08-21 | 江苏恒正合生命科学有限公司 | Preparation process of water-soluble rutin derivative |
| CN115976140A (en) * | 2022-12-27 | 2023-04-18 | 南京安佰思生物科技有限公司 | Production and preparation process of enzyme-modified isoquercitrin |
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