CN109400673A - A kind of method of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion- - Google Patents
A kind of method of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion- Download PDFInfo
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- CN109400673A CN109400673A CN201811178275.9A CN201811178275A CN109400673A CN 109400673 A CN109400673 A CN 109400673A CN 201811178275 A CN201811178275 A CN 201811178275A CN 109400673 A CN109400673 A CN 109400673A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
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- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention discloses a kind of methods of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-.The method comprising the steps of: 1) extra large rice embryo crushes, low temperature freeze-drying to water content 5-8%, removes extra large rice embryo lipid material using supercritical carbon dioxide extraction method；2) degreasing sea rice embryo hot water extraction takes supernatant to be concentrated to give glutathione crude product；3) glutathione crude product is dissolved in hot water, adds acetic acid to adjust pH value of solution 4-5, is slowly added to zinc acetate, and 100-150rpm is stirred to react, and generates glutathione zinc salts precipitate；PH4-5 is maintained to keep the temperature 30 DEG C of abundant reaction agings of reaction 4h；4) high speed centrifugation removes supernatant, takes precipitating investment 0.5%EDTA solution, dissolution is stirred at room temperature；5) it is slowly added to 10% beta-cyclodextrin aqueous solution, is heated to 45 DEG C, stirring generates precipitating, and centrifugation discards precipitating, the glutathione that supernatant is concentrated under reduced pressure up to purifying.Supercritical extract degreasing avoids organic residue from polluting without using organic solvents such as common petroleum ether n-hexanes, prevents extra large rice embryo lipid material interference separating resulting.
Description
Technical field
The present invention relates to a kind of methods for purifying glutathione, belong to technical field of biochemical industry, more particularly to one kind
The method of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-.
Background technique
Glutathione (glutathione, GSH) is combined by glutamic acid, cysteine and glycine, and sulfydryl is contained
Tripeptides has antioxidation and integrates detoxication.Sulfydryl on cysteine is glutathione active group (event gluathione
Peptide is often abbreviated as G-SH), easily with some drugs (such as paracetamol), toxin (such as free radical, iodoacetic acid, mustard gas, lead, mercury, arsenic
Equal heavy metals) etc. combine, and have and integrate detoxication.Therefore glutathione (glutathione especially in liver cell) can participate in
Biotransformation excretes external so that poisonous substance harmful in body is converted into harmless substance.Glutathione can also be helped
Help the function of keeping normal immune system.
Glutathione is intracellular product, and glutathione must be extracted from cell.Extracting glutathione has following several sides
Method: hot-water extraction, formic acid extracting, ethanolic extraction, sulfuric acid extracting, trichloroacetic acid extracting, organic acid mixing extracting, low temperature extracting
Deng.
A kind of existing common process is separated using cuprous oxide and glutathione reaction precipitating, the tiny hardly possible of post precipitation, and
Mantoquita pollution is difficult to eliminate, and final products contain higher copper ion, are unfavorable for health-oriented products application.
Therefore, a kind of using the extra large rice embryo lipid of supercritical carbon dioxide extraction method removing there is an urgent need to occur
Matter, so that the technique of extraction purification glutathione and those skilled in the art continue the technical problem solved.
Summary of the invention
The purpose of the present invention is to provide a kind of sides of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-
Method, in the process without using organic solvents such as common petroleum ether n-hexanes, has been avoided by supercritical extract degreasing process method
Machine residual contamination, and supercritical temperature is inefficient high, prevents extra large rice embryo lipid material interference separating resulting.
The object of the invention to solve the technical problems adopts the following technical solutions to realize.It proposes according to the present invention
A kind of cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-method, comprising steps of
1) extra large rice embryo embryo crushes, low temperature freeze-drying to water content 5-8%, de- using supercritical carbon dioxide extraction method
Except extra large rice embryo lipid material；
2) degreasing sea rice embryo embryo hot water extraction, takes supernatant to be concentrated to give glutathione crude product；
3) glutathione crude product is dissolved in hot water, and acetic acid is added to adjust solution PH 4-5, is slowly added to zinc acetate, generates gluathione
Peptide zinc salts precipitate；It maintains PH4-5 to keep the temperature 30 DEG C, reacts the abundant reaction aging of 4h；
4) high speed centrifugation removes supernatant, takes precipitating investment 0.5%EDTA solution, dissolution 2h is stirred at room temperature；
5) it is slowly added to 10% beta-cyclodextrin aqueous solution, is heated to 45 DEG C, stirring generates precipitating, and centrifugation discards precipitating, on
The glutathione that clear liquid is concentrated under reduced pressure up to purifying.
The method of the above-mentioned cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, in step 1), extra large rice embryo embryo
Crushing is coarse powder；Using the extracting pressure 30-35MPa of supercritical carbon dioxide extraction method, 35-40 DEG C of temperature, CO2Add
5% ethyl alcohol proposes completely as entrainer cycling extraction to lipid.
The method of the above-mentioned cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, in step 2), 100-150rpm
It is stirred to react, generates glutathione zinc salts precipitate, be in sposh shape.
The method of the above-mentioned cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, in step 4), 12000rpm from
Heart 15min, removes supernatant, takes precipitating；Precipitating investment 0.5%EDTA solution, precipitation solution ratio are 1:20.
By above-mentioned technical proposal, the invention has the advantages that and advantageous effects:
1) present invention has without using common petroleum ether n-hexane etc. in the process by supercritical extract degreasing process method
Solvent avoids organic residue from polluting, and supercritical temperature is inefficient high, prevents extra large rice embryo lipid material interference separation knot
Fruit.
2) non-toxic using metal ion such as zinc salt, and precipitate particle great Yi removal；Beta-cyclodextrin molecule is cylindrical in shape, and can be wrapped
Metal ion forms inclusion compound precipitating, easily removes to obtain high-purity glutathione.
Specific embodiment
The invention discloses a kind of methods of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, specific to wrap
Include following processing step:
1) it is 2-3mm coarse powder, low temperature freeze-drying to water content 5-8% that extra large rice embryo, which crushes,；Using stream of supercritical carbon dioxide
The extra large rice embryo lipid material of body extraction removing, extracting pressure 30-35MPa, 35-40 DEG C of temperature, CO2Add 5% ethyl alcohol as folder
Band agent cycling extraction proposes completely to lipid.60 DEG C of hot water extraction 30min of degreasing sea rice embryo, take supernatant to be concentrated to give glutathione
Crude product；
2) glutathione crude product is dissolved in hot water, adds acetic acid to adjust solution PH 4-5, is slowly added to zinc acetate, 100-150rpm
It is stirred to react, generates glutathione zinc salts precipitate, be in sposh shape；
3) PH4-5 is maintained to keep the temperature 30 DEG C of abundant reaction agings of reaction 4h；
4) high speed centrifugation 12000rpm is centrifuged 15min, removes supernatant, takes precipitating；
5) precipitating investment 0.5%EDTA solution, precipitation solution ratio are 1:20, and dissolution 2h is stirred at room temperature；
6) it is slowly added to 10% beta-cyclodextrin aqueous solution, is heated to 45 DEG C, stirring generates precipitating；
7) centrifugation discards precipitating, the glutathione that supernatant is concentrated under reduced pressure up to purifying.
The method of extraction purification glutathione of the invention, technological principle are as follows:
Glutathione and divalent metal zinc ion are combined and generate other impurities in glutathione zinc salts precipitate and coarse body fluid
Separation；Precipitating plus EDTA aqueous dissolution, divalent metal discharge glutathione by EDTA Separation by Complexation；Cyclodextrin solution is added,
Since cyclodextrin molecular is cylindrical in shape, the impurity such as inclusion bivalent metal ion form inclusion compound macromolecular precipitating, are centrifuged decontamination, pure
The glutathione solution of change is obtained, and concentrated crystallization obtains high-purity glutathione.
Below by way of specific preferred embodiment combination effete test embodiment, invention is further described in detail, but the present invention
It is not limited in embodiment below.
Embodiment 1
A kind of method of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, specifically:
1) sea 20kg rice embryo is crushed as coarse powder, low temperature freeze-drying to water content 5-8%；Using stream of supercritical carbon dioxide
The extra large rice embryo lipid material of body extraction removing, extracting pressure 30-35MPa, 35-40 DEG C of temperature, CO2Add 5% ethyl alcohol as folder
Band agent cycling extraction proposes completely to lipid；
2) 60 DEG C of hot water extraction 30min of degreasing sea rice embryo take supernatant to be concentrated to give glutathione crude product 230g；Glutathione
Crude product is dissolved in hot water, and acetic acid 20% is added to adjust pH value of solution 4-5, it is slowly added to 12% (g/100ml of zinc acetate?), 100-150rpm
It is stirred to react, generates glutathione zinc salts precipitate, be in sposh shape；
3) pH4-5 is maintained to keep the temperature 30 DEG C of abundant reaction agings of reaction 4h；High speed centrifugation 12000rpm is centrifuged 15min, goes
Clearly, precipitating is taken；Precipitating investment 0.5%EDTA solution, precipitation solution w/v are 1:20, and dissolution 2h is stirred at room temperature；
It is slowly added to 10% beta-cyclodextrin aqueous solution, is heated to 45 DEG C, stirring generates precipitating；Centrifugation discards precipitating, and supernatant decompression is dense
It contracts up to the glutathione 32g of purifying.
The white crystalline solid of the glutathione of purifying, glutathione purity are 96%.
Embodiment 2
A kind of method of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, specifically:
1) sea 2kg rice embryo is crushed as coarse powder, low temperature freeze-drying to water content 5-8%；Using stream of supercritical carbon dioxide
The extra large rice embryo lipid material of body extraction removing, extracting pressure 30-35MPa, 35-40 DEG C of temperature, CO2Add 5% ethyl alcohol as folder
Band agent cycling extraction proposes completely to lipid；
2) 60 DEG C of hot water extraction 30min of degreasing sea rice embryo, take supernatant to be concentrated to give glutathione crude product；Glutathione crude product
It is dissolved in hot water, adds acetic acid to adjust pH value of solution 4-5, is slowly added to zinc acetate, 100-150rpm is stirred to react, and generates glutathione zinc
Salt precipitating is in sposh shape；
3) pH4-5 is maintained to keep the temperature 30 DEG C of abundant reaction agings of reaction 4h；High speed centrifugation 12000rpm is centrifuged 15min, goes
Clearly, precipitating is taken；Precipitating investment 0.5%EDTA solution, precipitation solution ratio are 1:20, and dissolution 2h is stirred at room temperature；It is slowly added to
10% beta-cyclodextrin aqueous solution is heated to 45 DEG C, and stirring generates precipitating；Centrifugation discards precipitating, and supernatant is concentrated under reduced pressure up to pure
The glutathione 2.6g of change, white crystalline solid, purity 98%.
Embodiment 3
A kind of method of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, specifically:
1) sea 100kg rice embryo is crushed as coarse powder, low temperature freeze-drying to water content 5-8%；Using supercritical carbon dioxide
The extra large rice embryo lipid material of fluids extraction removing, extracting pressure 30-35MPa, 35-40 DEG C of temperature, CO2Add 5% ethyl alcohol conduct
Entrainer cycling extraction proposes completely to lipid；
2) 60 DEG C of hot water extraction 30min of degreasing sea rice embryo, take supernatant to be concentrated to give glutathione crude product；Glutathione crude product
It is dissolved in hot water, adds acetic acid to adjust pH value of solution 4-5, is slowly added to zinc acetate, 100-150rpm is stirred to react, and generates glutathione zinc
Salt precipitating is in sposh shape；
3) pH4-5 is maintained to keep the temperature 30 DEG C of abundant reaction agings of reaction 4h；High speed centrifugation 12000rpm is centrifuged 15min, goes
Clearly, precipitating is taken；Precipitating investment 0.5%EDTA solution, precipitation solution ratio are 1:20, and dissolution 2h is stirred at room temperature；It is slowly added to
10% beta-cyclodextrin aqueous solution is heated to 45 DEG C, and stirring generates precipitating；Centrifugation discards precipitating, and supernatant is concentrated under reduced pressure up to pure
The glutathione 186g of change, white crystalline solid, purity 96%.
Comparative example 1 (does not use supercritical carbon dioxide extraction method to remove)
A kind of method of extraction purification glutathione, specifically:
1) extra large rice embryo is crushed as 2-3mm coarse powder, low temperature freeze-drying to water content 5-8%；It is mixed and is extracted using organic acid
Remove extra large rice embryo lipid material；In organic acid skimming processes, glutathione causes later period metal salt heavy with dissolution, loss
It forms sediment unobvious, yield is relatively low.
2) 60 DEG C of hot water extraction 30min of degreasing sea rice embryo, take supernatant to be concentrated to give glutathione crude product；Glutathione crude product
It is dissolved in hot water, adds acetic acid to adjust pH value of solution 4-5, is slowly added to zinc acetate, 100-150rpm is stirred to react, and generates glutathione zinc
Salt precipitating is in sposh shape；
3) pH4-5 is maintained to keep the temperature 30 DEG C of abundant reaction agings of reaction 4h；High speed centrifugation 12000rpm is centrifuged 15min, goes
Clearly, precipitating is taken；Precipitating investment 0.5%EDTA solution, precipitation solution ratio are 1:20, and dissolution 2h is stirred at room temperature；It is slowly added to
10% beta-cyclodextrin aqueous solution is heated to 45 DEG C, and stirring generates precipitating；Centrifugation discards precipitating, and supernatant is concentrated under reduced pressure up to pure
The glutathione of change is in canescence blocks of solid, purity 56%.
Comparative example 2 (does not use metal ion and β-ring paste reaction precipitating)
A kind of method of extraction purification glutathione, specifically:
1) extra large rice embryo is crushed as 2-3mm coarse powder, low temperature freeze-drying to water content 5-8%；Using supercritical carbon dioxide
The extra large rice embryo lipid material of fluids extraction extracting removing, extracting pressure 30-35MPa, 35-40 DEG C of temperature, CO2Add 5% ethyl alcohol
It is proposed completely as entrainer cycling extraction to lipid；
2) 60 DEG C of hot water extraction 30min of degreasing sea rice embryo, take supernatant to be concentrated to give glutathione crude product；Glutathione crude product
It is dissolved in hot water, adds acetic acid to adjust pH value of solution 4-5, is slowly added to cuprous oxide, 100-150rpm is stirred to react, and generates glutathione
Mantoquita precipitating is in sposh shape；
3) pH4-5 is maintained to keep the temperature 30 DEG C of abundant reaction agings of reaction 4h；High speed centrifugation 12000rpm is centrifuged 15min, goes
Clearly, precipitating is taken；Precipitating investment 0.5%EDTA solution, precipitation solution ratio are 1:20, and dissolution 2h is stirred at room temperature；It is slowly added to
10% beta-cyclodextrin aqueous solution is heated to 45 DEG C, and stirring generates precipitating；Centrifugation discards precipitating, and supernatant is concentrated under reduced pressure up to pure
The glutathione of change is in brown bulk shape solid, purity 60%, content of copper ion height.
Copper oxidule precipitation glutathione produces glutathione mantoquita precipitating, will precipitate in water in suspension after filtering, and add vulcanization
The copper ion of sodium reaction, vulcanized sodium and glutathione mantoquita, which combines, generates copper sulfide precipitation, releases glutathione.Disadvantage is
Copper ion is extremely difficult in later-period purification to be completely removed, and copper ion is toxic；The smell is awful for the vulcanized sodium of introducing, micro- in later product
The sulfide of amount influences the quality of glutathione finished product.
The present invention combines precipitating glutathione using zinc salt, avoids mantoquita heavy metal toxicity；It is molten that EDTA is suspended in after precipitating
In liquid, EDTA is chelate divalent metal agent, and glutathione can be released in conjunction with zinc salt, cyclodextrin solution is added, due to cyclodextrin
The tubular structure of molecule can include metal ion, generate precipitating, and the metal ion then chelated includes in cyclodextrin under precipitating
Come, filtering or centrifuge separation, supernatant is exactly the glutathione solution of high-purity, condensing crystallizing.EDTA and cyclodextrin are normal
With pharmaceutic adjuvant, have no irritating odor nontoxicity, avoids the adverse effect for introducing sulfide.
In summary, the present invention is due to organic molten without using common petroleum ether n-hexane etc. using supercritical extract degreasing
Agent avoids organic residue from polluting, and prevents extra large rice embryo lipid material interference separating resulting.In addition, comprehensive use metal ion such as
Zinc salt is non-toxic, and precipitates particle great Yi removal；Beta-cyclodextrin molecule is cylindrical in shape, and it is heavy to include metal ion formation inclusion compound
It forms sediment, easily removes to obtain high-purity glutathione.
The above described is only a preferred embodiment of the present invention, be not intended to limit the present invention in any form, therefore
Without departing from the technical solutions of the present invention, to the above embodiments according to the technical essence of the invention any simply to repair
Change, equivalent variations and modification, all of which are still within the scope of the technical scheme of the invention.
Claims (5)
1. a kind of method of the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-, which is characterized in that this method includes
Step:
1) extra large rice embryo crushes, low temperature freeze-drying to water content 5-8%, removes extra large rice using supercritical carbon dioxide extraction method
Rice embryo lipid material；
2) degreasing sea rice embryo hot water extraction takes supernatant to be concentrated to give glutathione crude product；
3) glutathione crude product is dissolved in hot water, and acetic acid is added to adjust pH value of solution 4-5, is slowly added to zinc acetate, generates glutathione zinc
Salt precipitating；It maintains pH4-5 to keep the temperature 30 DEG C, reacts the abundant reaction aging of 4h；
4) high speed centrifugation removes supernatant, takes precipitating investment 0.5%EDTA solution, dissolution 2h is stirred at room temperature；
5) it is slowly added to 10% beta-cyclodextrin aqueous solution, is heated to 45 DEG C, stirring generates precipitating, and centrifugation discards precipitating, supernatant
The glutathione up to purifying is concentrated under reduced pressure.
2. the method for the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-according to claim 1, feature
Be: in step 1), it is 2-3mm coarse powder that extra large rice embryo, which crushes,；Using the extracting pressure of supercritical carbon dioxide extraction method
30-35MPa, 35-40 DEG C of temperature, CO25% ethyl alcohol is added to propose completely as entrainer cycling extraction to lipid.
3. the method for the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-according to claim 1, feature
Be: in step 2), 100-150rpm is stirred to react, and generates glutathione zinc salts precipitate, is in sposh shape.
4. the method for the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-according to claim 1, feature
Be: in step 4), 12000rpm is centrifuged 15min, removes supernatant, takes precipitating；Precipitating investment 0.5%EDTA solution, precipitation solution
Than for 1:20.
5. the method for the cyclodextrin encapsulated extraction purification glutathione of precipitation by metallic ion-according to claim 1, feature
Be: in step 5), the white crystalline solid of the glutathione of purifying, glutathione purity is 96-98%.
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| CN101134773A (en) * | 2007-07-25 | 2008-03-05 | 吉林农业大学 | Method for extracting corn free radical scavenger |
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| CN106957717A (en) * | 2016-01-11 | 2017-07-18 | 徐蕴山 | A kind of meter of dregs of rice supercritical extract method for producing oil and its rice dregs of rice of manufacture oil and the degreasing rice dregs of rice |
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