CN118184547A - Method for recycling and preparing arginine from waste water of tetrodotoxin extracted and separated from puffer fish viscera - Google Patents
Method for recycling and preparing arginine from waste water of tetrodotoxin extracted and separated from puffer fish viscera Download PDFInfo
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- CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 title claims abstract description 18
- CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229950010357 tetrodotoxin Drugs 0.000 title claims abstract description 18
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- 238000004064 recycling Methods 0.000 title claims abstract description 7
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 241001627955 Tetraodon lineatus Species 0.000 claims abstract description 10
- 239000003463 adsorbent Substances 0.000 claims abstract description 10
- 239000000284 extract Substances 0.000 claims abstract description 9
- 238000001728 nano-filtration Methods 0.000 claims abstract description 6
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- 239000012043 crude product Substances 0.000 claims abstract description 3
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- 238000004128 high performance liquid chromatography Methods 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
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- 229910002027 silica gel Inorganic materials 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
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- 230000008025 crystallization Effects 0.000 claims description 3
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
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- REFMEZARFCPESH-UHFFFAOYSA-M sodium;heptane-1-sulfonate Chemical compound [Na+].CCCCCCCS([O-])(=O)=O REFMEZARFCPESH-UHFFFAOYSA-M 0.000 claims description 2
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- 235000009697 arginine Nutrition 0.000 abstract description 74
- 239000002699 waste material Substances 0.000 abstract description 8
- 241001465754 Metazoa Species 0.000 abstract description 7
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- 229930064664 L-arginine Natural products 0.000 abstract description 5
- 235000014852 L-arginine Nutrition 0.000 abstract description 5
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- 125000002059 L-arginyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=N[H])N([H])[H] 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for recycling and preparing arginine from waste water of tetrodotoxin extracted and separated from viscera of globefish. The process comprises the following steps: 1) Collecting the waste liquid with high arginine content, concentrating to small volume with nanofiltration concentrator, and concentrating to extract with vacuum concentrator. 2) Extracting arginine in the extract with alcohol water solution, and discarding insoluble impurities. 3) Removing residual pigment in arginine alcohol water solution by using an adsorbent, concentrating under reduced pressure, and recovering an organic solvent to obtain an arginine crude product. 4) Dissolving the crude arginine with water, performing isoelectric precipitation, crystallizing to purify arginine for 1-2 times, and drying and crystallizing to obtain high-purity arginine. The invention can simply recycle the arginine in the animal processing waste liquid to prepare the natural L-arginine with high purity, thereby not only improving the economic value of animal processing, but also reducing the waste of natural biological resources and the pollution of organic wastewater to the environment.
Description
Technical Field
The invention relates to the technical field of recovery and preparation of amino acid from wastes extracted and separated from natural products, in particular to a process for preparing high-purity arginine.
Background
Arginine (Arginine) is a basic amino acid, which is the basic constituent amino acid of various proteins. Natural arginine is L-type and is an essential amino acid for early development of infants. Arginine has a chemical formula of C 6H14N4O2, a molecular weight of 174.2, and an isoelectric point of 10.76. Is soluble in water, insoluble in diethyl ether and slightly soluble in ethanol.
Research shows that arginine has various medicinal functions except as the constituent of protein, including regulating blood sugar, protecting liver, resisting fatigue, enhancing human immunity, delaying senility, promoting wound healing, promoting infant growth, etc. Arginine can also be used as a food flavoring agent and a food flavor. In addition, arginine has also found wide application in the feed industry (Wang Zhe, zhou Yanmin, research progress in physicochemical properties, physiological functions, and production processes of L-arginine, feed research, 2014, 13:80-84).
The production method of arginine mainly includes protein hydrolysis method and microbial fermentation method. The protein hydrolysis method mainly takes gelatin, animal hair, pig blood powder and the like which are low in price as raw materials, and the protein raw materials rich in arginine are heated and hydrolyzed by the hydrolysis method to obtain an amino acid mixture containing arginine. The arginine is purified by ion exchange resin separation, active carbon decolorization and other treatments, and the arginine is L-arginine. However, the method has the advantages of complex arginine preparation process, large consumption of water, hydrochloric acid and the like, large production of a large amount of organic wastewater, low yield, high production cost and difficulty in preparing high-purity arginine.
The microbial fermentation method is a method for producing arginine by fermentation using a natural microorganism, a mutant modified microorganism or a genetically engineered microorganism. High arginine yields can be obtained by metabolic engineering to modify the metabolic flux of the microorganism. The method overcomes the problems of complex process, serious environmental pollution and the like existing in the proteolytic method. Meanwhile, the method has the advantages of mild production conditions, high product purity, low production cost and the like, and is suitable for being applied to industrial production of arginine.
Although these methods can produce arginine in large quantities, they all require the arginine to be isolated and purified by relatively complex hydrolysis or fermentation processes. When the tetrodotoxin is extracted from the viscera of the globefish, the waste water for separating the tetrodotoxin by ion exchange column chromatography is found to contain higher arginine. Simple methods and processes for recovering and preparing high purity arginine from these wastewater streams have been developed. The invention can not only prepare high-purity arginine and improve the extraction value of the viscera of the globefish, but also reduce the pollution of waste liquid to the environment.
Disclosure of Invention
When animal extracts such as fish are separated and prepared, a large amount of wastewater is generated. These waste waters have a high arginine content and can be recovered and refined by simple means to high purity arginine products. The invention develops a simple and efficient method for recovering and separating arginine from waste water of tetrodotoxin extracted and separated from the viscera of globefish.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
A method for recycling and preparing arginine from waste water of tetrodotoxin extracted and separated from puffer fish viscera, which is characterized by comprising the following steps:
(1) And detecting the waste water solution in the tetrodotoxin separation and purification process by using HPLC, and collecting the solution with high arginine content.
(2) Concentrating the solution to be abandoned with higher arginine content in the step (1) to a small volume by a nanofiltration concentrator, and then transferring the solution to a vacuum concentrator for concentrating to extract.
(3) Extracting the extract obtained in the step (2) with a lower aliphatic alcohol aqueous solution for several times, extracting arginine therefrom, and centrifuging or filtering to remove impurities insoluble in the alcohol aqueous solution.
(4) Adding a certain amount of adsorbent into the aqueous alcohol solution of arginine obtained in the step (3) to adsorb and remove residual pigment in the solution; or flowing the arginine alcohol water solution through an adsorbent column, and eluting the arginine by using the alcohol water solution. And (3) evaporating the adsorbed arginine alcohol water solution phase under reduced pressure to dryness to obtain an arginine crude product. The recovered organic solvent can be reused.
(5) Dissolving the crude arginine product obtained in the step (4) by using a proper amount of water, centrifuging to remove insoluble substances, adjusting the pH of the solution to an isoelectric point 10.76,4 o C, and crystallizing in a refrigerator overnight. The crystallization was repeated once.
(6) And (3) drying the crystal obtained in the step (5) in vacuum to obtain high-purity arginine powder. HPLC analysis detects arginine.
Specifically, in the step (1), the solution with high arginine content refers to an aqueous solution to be discarded, which is separated by ion exchange resin and has high arginine content (fig. 2). The impurity content in the waste liquid which is not separated by the ion exchange resin is too high, and the arginine is difficult to be separated and purified simply.
Preferably, the nanofiltration concentrator in the step (2) adopts a membrane with the molecular weight cut-off of 100-150 daltons for concentration, and the membrane is transferred into a vacuum concentrator after concentration, and is steamed to paste under 70 o ℃.
Preferably, the aqueous solution of the lower aliphatic alcohol in the step (3) is an aqueous solution of 80-100% of methanol, ethanol, propanol or butanol, etc. The most preferred solvent is 90% ethanol.
Preferably, the adsorbent in the step (4) is silica gel, alumina, activated carbon, diatomite or the like. The amount is 1-10% (v/w) of the amount of the adsorbed solution. Or decolorizing with adsorbent column, passing arginine alcohol water solution through adsorption column, and completely eluting arginine with the same solvent. If silica gel is selected for static adsorption, the silica gel with the solvent adding amount of 5% is adsorbed for 2 hours, so that a good decoloring effect can be achieved; if the dynamic adsorption is carried out by using a silica gel adsorption column, the 90% ethanol solution of arginine is passed through the silica gel adsorption column, and is eluted by using 10 times of column volume of 90% ethanol.
Preferably, the crude arginine product of step (5) is dissolved in water. Because arginine has high solubility in water and the solubility changes with temperature, the water consumption cannot be excessive. The water was used until the crude arginine was mostly dissolved, the insoluble material was removed by centrifugation and crystallized in a4 o C refrigerator.
Preferably, the HPLC analysis conditions described in step (6) are: shimadzu LC-20AT HPLC analysis system. Chromatographic column: shim-PACK GIST C-AQ (4.6X250 mm, 5 μm) from Shimadzu corporation. Test 196: 196 nm, mobile phase 1): 25mM monoammonium phosphate-5 mM sodium heptanesulfonate, flow rate: 1 mL/min.
The invention is characterized in that the high-purity arginine is recovered and prepared from the waste liquid of the animal extract industry. The preparation method is simple, the preparation cost is low, and the obtained product is pure natural L-arginine. The invention can not only improve the economic value of the extract production, but also reduce the waste of biological resources and the pollution of organic wastewater to the environment. The method is suitable for recycling arginine in wastewater during various animal extraction processes.
Drawings
FIG. 1 is a flow chart for recovering arginine from an arginine-containing effluent during animal processing.
FIG. 2 is a diagram of HPLC analysis of arginine-containing wastewater solution.
Figure 3 is a graph of HPLC analysis of arginine prepared.
The mass spectrum of arginine prepared in FIG. 4.
Detailed Description
The invention relates to a method for recycling and preparing high-purity arginine from waste water of extracting and separating tetrodotoxin, which comprises the following process flows:
(1) The aqueous solution to be discarded, which has high arginine content and is separated by the ion exchange resin, of tetrodotoxin is detected by HPLC (as shown in figure 2), and 22.8L of eluent with 2596mg arginine content is collected.
(2) Concentrating the eluate with nanofiltration concentrator with molecular weight cut-off of 100-150 daltons to small volume to obtain 1.6L concentrate containing arginine 1756mg, and concentrating the concentrate into extract at 70deg.C with rotary evaporator.
(3) Adding 90% ethanol solution into the extract, wherein the feed liquid ratio is 1: centrifugation was carried out at 50℃for 1h at 30℃at 8000rpm for 10 minutes to remove impurities insoluble in the aqueous alcohol solution, and the remaining solid was repeatedly extracted once with the same 90% ethanol solution, and the supernatants were combined.
(4) Passing the 90% ethanol supernatant through 60-100 mesh silica gel adsorption column, eluting with 90% ethanol with 10 times of column volume, eluting arginine, and evaporating the arginine eluent at 60deg.C under reduced pressure to obtain crude arginine product.
(5) The crude arginine was dissolved in 10mL of water, centrifuged to remove insoluble material, and the pH of the solution was adjusted to isoelectric point 10.76,4 o C and crystallized overnight in a refrigerator. The crystallization was repeated once.
(6) The crystals were dried under vacuum at 60 o C to obtain high purity arginine powder. HPLC analysis shows that the purity of arginine is not less than 99.5% (shown in figure 3). The purified product was identified by mass spectrometry as L-arginine (FIG. 4).
Claims (7)
1. A method for recycling and preparing arginine from waste water of tetrodotoxin extracted and separated from puffer fish viscera, which is characterized by comprising the following steps:
(1) And detecting the waste water solution in the tetrodotoxin separation and purification process by using HPLC, and collecting the solution with high arginine content.
(2) Concentrating the solution with high arginine content in the step (1) to a small volume by a nanofiltration concentrator, and then transferring the solution into a vacuum concentrator to concentrate into extract.
(3) Extracting the extract obtained in the step (2) with a lower aliphatic alcohol aqueous solution for several times, extracting arginine therefrom, and centrifuging or filtering to remove impurities insoluble in the alcohol aqueous solution.
(4) Adding a certain amount of adsorbent into the arginine alcohol water solution obtained in the step (3) to adsorb and remove residual pigment in the solution; or flowing the arginine alcohol water solution through an adsorbent column, and eluting the arginine by using the alcohol water solution. And (3) evaporating the adsorbed arginine alcohol water solution phase under reduced pressure to dryness to obtain an arginine crude product. The recovered organic solvent can be reused.
(5) Dissolving the crude arginine product obtained in the step (4) by using a proper amount of water, centrifuging to remove insoluble substances, adjusting the pH of the solution to an isoelectric point 10.76,4 o C, and crystallizing in a refrigerator overnight. The crystallization was repeated once.
(6) And (3) drying the crystal obtained in the step (5) in vacuum to obtain high-purity arginine powder. HPLC analysis detects arginine.
2. The method for recovering and separating and preparing arginine from the waste water of the extraction and separation of tetrodotoxin from the viscera of globefish according to claim 1, wherein the method comprises the following steps: the solution with high arginine content in the step (1) refers to an aqueous solution to be discarded, which is separated by ion exchange resin and has high arginine content (figure 2).
3. The method for recovering and separating and preparing arginine from the waste water of the extraction and separation of tetrodotoxin from the viscera of globefish according to claim 1, wherein the method comprises the following steps: the nanofiltration concentrator in the step (2) adopts a membrane with the molecular weight cut-off of 100-150 daltons for concentration, and the membrane is transferred into a vacuum concentrator after concentration, and is steamed to paste under 70 o ℃.
4. The method for recovering and separating and preparing arginine from the waste water of the extraction and separation of tetrodotoxin from the viscera of globefish according to claim 1, wherein the method comprises the following steps: the lower aliphatic alcohol aqueous solution referred to in the step (3) is an aqueous solution of 80-100% methanol, ethanol, propanol or butanol, etc., such as 90% ethanol.
5. The method for recovering and separating and preparing arginine from the waste water of the extraction and separation of tetrodotoxin from the viscera of globefish according to claim 1, wherein the method comprises the following steps: the adsorbent referred to in the step (4) is silica gel, alumina, activated carbon, diatomite and other adsorbents. The amount is 1-10% (v/w, preferably 5%) of the amount of the adsorbed solution. Or decolorizing with adsorbent column (such as silica gel adsorption column), passing arginine alcohol water solution through adsorption column, and eluting arginine with the same solvent.
6. The method for recovering and separating and preparing arginine from the waste water of the extraction and separation of tetrodotoxin from the viscera of globefish according to claim 1, wherein the method comprises the following steps: and (5) dissolving the crude arginine product in the step (5) with water. Because arginine has high solubility in water and the solubility changes with temperature, the water consumption cannot be excessive. The water was used until the crude arginine was mostly dissolved, the insoluble material was removed by centrifugation and crystallized in a 4 o C refrigerator.
7. The method for recovering and separating and preparing arginine from the waste water of the extraction and separation of tetrodotoxin from the viscera of globefish according to claim 1, wherein the method comprises the following steps: the HPLC analysis conditions described in the step (1) and the step (6) are as follows: shimadzu LC-20AT HPLC analysis system. Chromatographic column: shim-PACK GIST C-AQ (4.6X250 mm, 5 μm) from Shimadzu corporation. Test 196: 196 nm, mobile phase 1): 25mM monoammonium phosphate-5 mM sodium heptanesulfonate, flow rate: 1 mL/min.
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