CN111919991A - Albumen protein-plant polyphenol covalent complex and preparation method thereof - Google Patents
Albumen protein-plant polyphenol covalent complex and preparation method thereof Download PDFInfo
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- CN111919991A CN111919991A CN202010674909.0A CN202010674909A CN111919991A CN 111919991 A CN111919991 A CN 111919991A CN 202010674909 A CN202010674909 A CN 202010674909A CN 111919991 A CN111919991 A CN 111919991A
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- egg white
- plant polyphenol
- white protein
- ultrasonic treatment
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- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 106
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 102
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 238000010668 complexation reaction Methods 0.000 title description 2
- 108010000912 Egg Proteins Proteins 0.000 claims abstract description 127
- 102000002322 Egg Proteins Human genes 0.000 claims abstract description 127
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 65
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 15
- 238000002156 mixing Methods 0.000 claims abstract description 10
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- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 claims description 4
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 claims description 4
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims description 4
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 claims description 4
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000005487 catechin Nutrition 0.000 claims description 4
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 claims description 4
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- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 claims description 4
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- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 13
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- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 13
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- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 13
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- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 8
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3472—Compounds of undetermined constitution obtained from animals or plants
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/045—Organic compounds containing nitrogen as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3526—Organic compounds containing nitrogen
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3544—Organic compounds containing hetero rings
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/30—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation
- A23L5/32—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation using phonon wave energy, e.g. sound or ultrasonic waves
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Life Sciences & Earth Sciences (AREA)
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- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention provides an albumin-plant polyphenol covalent complex and a preparation method thereof, wherein the method comprises the following steps: separating and sterilizing an egg white protein solution; step (2), preparation of the egg white protein-plant polyphenol covalent compound: adjusting the pH of an egg white protein solution, adding hydrogen peroxide and ascorbic acid, mixing, adding plant polyphenol, placing in an ultrasonic reaction system for ultrasonic treatment in cooperation with free radical modification reaction, wherein the ultrasonic treatment is countercurrent ultrasonic treatment or multi-frequency ultrasonic treatment, and obtaining an egg white protein-plant polyphenol covalent compound. The method accelerates the free radical oxidation process of the egg white protein by utilizing the cavitation effect of a countercurrent ultrasonic treatment technology or a multifrequency ultrasonic treatment technology, further accelerates the covalent crosslinking reaction between the egg white protein and the plant polyphenol, and compared with the unmodified egg white protein, the egg white protein-plant polyphenol covalent compound obtained by the method has obvious oxidation stability and high emulsibility.
Description
Technical Field
The invention belongs to the technical field of food processing, and particularly relates to an albumin-plant polyphenol covalent complex and a preparation method thereof.
Background
Egg white protein, as a natural emulsifier, is receiving extensive attention from researchers due to its advantages of good emulsifying properties, high nutritional value, high biocompatibility, etc. However, egg albumin is conditional and relative to the stabilization of the emulsion system. During the storage of the egg white protein emulsion, and the processing operations such as heat treatment and shearing treatment of the emulsion, the egg white protein molecules are easy to lose the protection of a surface hydration layer, so that the oxidative aggregation and precipitation of the egg white protein are caused, and the emulsifying performance of the protein is influenced. The polyphenol compound which is a natural antioxidant with wide source, strong oxidation resistance and edible safety is easy to generate covalent grafting reaction with egg white protein due to the existence of a plurality of reactive groups and active sites in the molecular structure, and researches show that the covalent bonding of polyphenol and protein can irreversibly improve the emulsification property of the protein.
At present, the preparation methods of protein-polyphenol covalent complexes mainly comprise an alkaline method, an enzymatic method and a free radical method. The action mechanisms of the alkaline method and the enzymatic method are similar, the oxidation of polyphenol is mainly induced by alkali or enzyme to form quinone, and the quinone reacts with protein, but the excessive oxidation of polyphenol is easily caused, so that more poor quinone polymers are generated, and the change of the color and luster of the product and the reduction of the nutritional quality are further caused. Compared with an alkaline method and an enzymatic method, the free radical method has mild reaction conditions, can be carried out at room temperature, can prevent the degradation of the antioxidant to a certain extent, and is suitable for producing stable functional protein raw materials. However, in the conventional free radical method, protein and polyphenol are prepared into a solution with a certain concentration, and then the solution is uniformly mixed according to the required mass (or molar ratio) and then placed at 25 ℃ for reaction for 24-48 h, so that the reaction time is long, the energy consumption is high, and the reaction temperature needs to be strictly controlled during the reaction, so that the requirements of shortening the production period and saving the cost in industrial production cannot be met.
Disclosure of Invention
The egg white protein is taken as a raw material, the plant polyphenol is taken as a chemical modification reagent, ascorbic acid/hydrogen peroxide is taken as a free radical initiator, and the cavitation effect of a countercurrent ultrasonic treatment technology or a multifrequency ultrasonic treatment technology is utilized to accelerate the free radical oxidation process of the egg white protein, so that the covalent crosslinking reaction between the egg white protein and the plant polyphenol is accelerated. Compared with unmodified egg white protein, the egg white protein-plant polyphenol covalent compound has obvious oxidation stability and high emulsibility, and the novel bifunctional egg powder product is prepared by the method.
The technical scheme of the invention is as follows: a preparation method of albumin-plant polyphenol covalent complex comprises the following steps:
separating and sterilizing an egg white protein solution;
step (2), preparation of the egg white protein-plant polyphenol covalent compound: adjusting the pH of the egg white protein solution obtained by the step (1), adding hydrogen peroxide and ascorbic acid, mixing, adding plant polyphenol, placing in an ultrasonic reaction system for ultrasonic treatment in cooperation with free radical modification reaction, wherein the ultrasonic treatment is countercurrent ultrasonic treatment or multi-frequency ultrasonic treatment, and obtaining the egg white protein-plant polyphenol covalent compound.
In the scheme, the separation and sterilization of the egg white protein solution in the step (1) comprises the following steps:
soaking fresh eggs in warm water, cleaning the eggshells with chlorine water, finally washing residual chlorine on the surfaces of the eggshells with clear water, beating the eggs after drying, separating egg white and yolk, removing frenulum in egg white liquid, stirring at a low temperature until the egg white protein solution is uniform, performing pasteurization treatment on the uniformly dispersed egg white protein solution at the temperature of 55-57 ℃ for 3-4 min, and drying for later use.
In the scheme, the weight ratio of the egg white protein to the plant polyphenol in the step (2) is 10: 1.
In the scheme, the preparation of the egg white protein-plant polyphenol covalent compound in the step (2) specifically comprises the following steps:
preparing 100mL of the egg white protein solution with the concentration of 1% obtained in the step (1), adjusting the pH value to 3.0, adding 1mL of 5mol/L hydrogen peroxide and 0.25g of ascorbic acid powder, fully mixing, adding 0.1g of plant polyphenol solution, placing the mixture in an ultrasonic reaction system, performing ultrasonic treatment and free radical modification reaction for 20-60 min, wherein the ultrasonic treatment is a countercurrent ultrasonic treatment or multi-frequency ultrasonic treatment mode, and obtaining the egg white protein-plant polyphenol covalent compound.
Further, the reaction time in the step (2) is 50-60 min.
In the above scheme, the plant polyphenol is tea polyphenol, catechin, chlorogenic acid or epigallocatechin gallate.
In the above scheme, the ultrasonic treatment is a countercurrent ultrasonic treatment;
the parameters of the countercurrent ultrasonic treatment are as follows: pulse width 5s, ultrasonic interval time 3s, ultrasonic frequency 40kHz, and ultrasonic power density 100W/L, wherein the feed liquid passes through the ultrasonic probe in a countercurrent circulation mode.
In the above scheme, the ultrasonic treatment is a multi-frequency ultrasonic treatment mode;
the multi-frequency ultrasonic treatment mode is three-frequency synchronous ultrasonic treatment, or dual-frequency synchronous ultrasonic treatment, or single-frequency ultrasonic treatment, and the multi-frequency ultrasonic treatment parameters are as follows: the ultrasonic power density is 100W/L, the ultrasonic pulse working time is 10s, the pulse interval time is 5s, and the ultrasonic time is 60 min.
Further, the ultrasonic wave of the three-frequency synchronous ultrasonic treatment is 20/28/40 kHz; the ultrasonic wave of the double-frequency synchronous ultrasonic treatment is 20/40kHz, and the ultrasonic wave of the single-frequency treatment is 40 kHz.
In the scheme, the method also comprises the step (3) of purifying and drying the egg white protein-plant polyphenol covalent compound;
the purification and drying of the egg white protein-plant polyphenol covalent compound specifically comprise the following steps: dialyzing the egg white protein-plant polyphenol covalent compound solution reacted in the step (2), removing unreacted free plant polyphenol, collecting dialysate and drying.
The invention also provides the egg white protein-plant polyphenol covalent compound prepared by the preparation method.
Compared with the prior art, the invention has the beneficial effects that:
1. compared with the traditional free radical method, the method adopts the green pollution-free countercurrent ultrasonic technology and the multi-mode ultrasonic technology to prepare the egg white protein-plant polyphenol covalent compound with oxidation resistance and high emulsibility by cooperating with the traditional free radical method, and has the advantages of simple operation, mild conditions and no generation of toxic and harmful byproducts.
2. The cavitation effect based on the countercurrent ultrasonic wave or the multi-mode ultrasonic wave technology accelerates the free radical oxidation process of the egg white protein, accelerates the covalent crosslinking of the egg white protein and the polyphenol compound, and further shortens the reaction time.
3. Compared with unmodified egg white protein, the egg white-polyphenol covalent compound prepared by the method has obviously improved oxidation resistance and emulsibility.
Detailed Description
The terms used in the present invention are generally understood by those of ordinary skill in the art unless otherwise indicated. The present invention is described in further detail below with reference to specific examples and with reference to the data. The examples are described herein for the purpose of illustrating the invention and are not to be construed as limiting the scope of the invention.
According to the invention, a countercurrent ultrasonic treatment technology or a multi-frequency ultrasonic treatment technology is introduced to cooperate with a traditional free radical method, the cavitation effect, the thermal effect, the mechanical effect and the chemical effect of ultrasonic waves are utilized to improve the grafting efficiency of egg white protein and plant polyphenol, the reaction time is shortened, and simultaneously, an egg white protein-plant polyphenol covalent compound with obviously improved oxidation resistance and emulsibility is obtained.
The preparation method of the egg white protein-plant polyphenol covalent compound comprises the following steps: (1) separating and sterilizing an egg white protein solution; (2) preparing an egg white protein-plant polyphenol covalent compound; (3) purifying and drying the egg white protein-plant polyphenol covalent compound; (4) measuring the oxidation resistance of the egg white protein-plant polyphenol covalent compound; (5) preparing beta-carotene emulsion by taking an egg white protein-plant polyphenol covalent compound as an emulsifier.
(1) The separation and sterilization of the egg white protein solution specifically comprises the following steps: soaking a fresh egg which is inspected and has a complete and undamaged eggshell in warm water at about 30 ℃ for cleaning, then cleaning the eggshell with 50mg/L of chlorine water, finally washing residual chlorine on the surface of the eggshell with clear water, airing at room temperature, beating the egg and separating egg white and egg yolk, removing frenulum in egg white liquid, then stirring at low temperature for 20min until the egg white liquid is uniform, then carrying out traditional pasteurization treatment on the uniformly dispersed egg white solution at 55-57 ℃ for 3-4 min, and then drying for later use.
The drying is freeze drying, vacuum drying or spray drying.
(2) The preparation method of the egg white protein-plant polyphenol covalent compound comprises the following steps: preparing 100mL of 1% egg white protein solution, and adjusting the pH value to 3.0; then adding 1mL of 5mol/L hydrogen peroxide and 0.25g of ascorbic acid powder, and fully mixing; and then adding a plant polyphenol solution in a certain proportion into the solution, placing the solution into an ultrasonic reaction system for synergistic reaction for 20-60 min to obtain an egg white protein-plant polyphenol covalent compound, wherein the ultrasonic treatment is a countercurrent ultrasonic treatment or multi-frequency ultrasonic treatment mode.
The polyphenol can be tea polyphenol, catechin, chlorogenic acid, and epigallocatechin gallate.
When the countercurrent ultrasonic treatment is adopted, the preferable parameters of the countercurrent ultrasonic treatment are as follows: pulse width 5s, ultrasonic interval time 3s, ultrasonic frequency 40kHz, and ultrasonic power density 100W/L, wherein the feed liquid passes through the ultrasonic probe in a countercurrent circulation mode.
When a multi-frequency ultrasonic treatment mode is adopted, the multi-frequency ultrasonic treatment mode can be three-frequency synchronous ultrasonic treatment, dual-frequency synchronous ultrasonic treatment or single-frequency ultrasonic treatment, and the parameters are preferably as follows: the ultrasonic power density is 100W/L, the ultrasonic pulse working time is 10s, the pulse interval time is 5s, and the ultrasonic time is 60 min.
(3) The purification and drying of albumin-plant polyphenol covalent complex specifically comprises the following steps: dialyzing the reacted egg white protein-plant polyphenol covalent compound solution, removing unreacted free plant polyphenol, collecting dialysate and drying. The drying is freeze drying, vacuum drying or spray drying.
(4) The determination of the oxidation resistance DPPH of the egg albumin-plant polyphenol covalent complex is as follows:
preparing a 1mg/mL egg albumin-plant polyphenol covalent complex sample stock solution, diluting into 2mL sample solutions with concentrations of 0, 0.02, 0.04, 0.08 and 0.2mg/mL respectively, adding 2mL of 0.125mmol/mL DPPH ethanol solution (0.0049g DPPH is dissolved in 100mL 95% ethanol, dissolving by ultrasonic for 5min, storing in dark place), shaking uniformly, standing at room temperature for 30min, and measuring the absorbance A at 517nmSample (I). Taking 2mL of each of the above concentration samples, adding 2mL of 95% ethanol as a control, and measuring the absorbance value A at 517nmControlCalibration blank was 2mL deionized water and 2mL 95% ethanol. Determination of the absorbance A at 517nm for 2mL of DPPH and 2mL of distilled waterBlank spaceThe DPPH clearance (%) is calculated as follows:
(5) the preparation method of the beta-carotene emulsion taking the egg white protein-plant polyphenol covalent complex as the emulsifier comprises the following steps:
and (4) preparing an oil-in-water type beta-carotene emulsion by taking the egg white protein-tea polyphenol covalent compound prepared in the step (3) as an emulsifier. Dissolving the egg white protein-plant polyphenol covalent complex freeze-dried powder in 10mmol/L phosphate buffer solution with pH of 7.0, stirring overnight to ensure complete dispersion and dissolution, obtaining an egg white protein-plant polyphenol covalent complex solution with the concentration of 1% (w/w) as a water phase, and simultaneously adding 0.02% (w/w) of an antibacterial agent. Dispersing beta-carotene (0.1%, w/w) into soybean oil, and performing ultrasonic treatment at 50 deg.C for 20min to completely dissolve to obtain oil phase. Then, the water phase and the oil phase are mixed according to the mass ratio of 9:1, stirred for 2min by a high-speed disperser at the speed of 15000r/min to form a coarse emulsion, further homogenized (60MPa) by a high-pressure homogenizer for 3 times, then immediately cooled to room temperature, and stored at 4 ℃ in a dark place for subsequent measurement. The beta-carotene is easy to be oxidized and degraded by light, and the light-proof treatment is well carried out by using tin foil paper in the experimental process.
The plant polyphenol in the present invention may be tea polyphenol, catechin, chlorogenic acid, epigallocatechin gallate, and the present invention will be described in detail below by taking tea polyphenol as an example.
Control group: conventional free radical process (without introduction of ultrasound)
The preparation method of the egg albumin-plant polyphenol covalent complex comprises the following steps:
(1) soaking a fresh egg which is inspected and has a complete and undamaged eggshell in warm water at about 30 ℃ for cleaning, then cleaning the eggshell with 50mg/L of chlorine water, finally washing residual chlorine on the surface of the eggshell with clear water, airing at room temperature, beating the egg and separating egg white and egg yolk, removing frenulum in egg white liquid, and then stirring at low temperature for 20min until the egg white liquid is uniform to obtain a uniformly dispersed egg white solution;
(2) carrying out pasteurization on the egg white solution obtained by the treatment in the step (1) at 55-57 ℃ for 3-4 min;
(3) carrying out spray drying treatment on the egg white solution subjected to pasteurization treatment in the step (2), wherein the specific conditions are as follows: the air inlet temperature is 150 ℃, the air outlet temperature is 75 ℃, the mixture is naturally cooled after spray drying, then the mixture is sieved by a 30-mesh sieve to remove coarse particles, and finally the mixture is subjected to vacuum packaging to obtain a finished product of egg white powder;
(4) and (3) preparing the dried egg white protein powder in the step (3) into an egg white protein solution with the concentration of 1% w/v and the pH value of 3.0, adding 1.0mL of hydrogen peroxide solution and 0.25g of ascorbic acid into 100mL of the egg white protein solution, fully mixing the solution at room temperature, adding 0.1g of tea polyphenol powder, and continuing to react for 24 hours at the temperature of 25 ℃. Dialyzing the reacted solution, spray-drying the dialyzate to obtain the egg albumin-tea polyphenol covalent compound, and measuring the oxidation resistance and the emulsification property of the compound.
(5) Preparing and characterizing the beta-carotene emulsion with the egg white protein-tea polyphenol covalent complex prepared in the step (4) as an emulsifier:
and (4) preparing oil-in-water type beta-carotene emulsion by taking the egg white protein-tea polyphenol covalent compound prepared in the step (4) as an emulsifier. Dissolving the egg white protein-tea polyphenol covalent compound freeze-dried powder in 10mmol/L phosphate buffer solution with pH of 7.0, stirring overnight to ensure complete dispersion and dissolution, obtaining an egg white protein-tea polyphenol covalent compound solution with the concentration of 1% w/w as a water phase, and simultaneously adding 0.02% w/w of an antibacterial agent. Dispersing 0.1% w/w beta-carotene into soybean oil, and performing ultrasonic treatment at 50 deg.C for 20min to completely dissolve to obtain oil phase. Then, mixing the water phase and the oil phase according to the mass ratio of 9:1, stirring for 2min by a high-speed disperser at the speed of 15000r/min to form a coarse emulsion, further homogenizing by a high-pressure homogenizer at 60MPa, repeatedly homogenizing for 3 times, immediately cooling to room temperature, and storing at 4 ℃ in a dark place for subsequent measurement. The beta-carotene is easy to be oxidized and degraded by light, and the light-proof treatment is well carried out by using tin foil paper in the experimental process.
Zeta potential and particle size determination of the beta-carotene emulsion: the emulsion was diluted with distilled water to a protein concentration of 0.1%, and the potential change of the emulsion was measured using a Zeta potential particle size analyzer. The emulsion was diluted with distilled water at a volume ratio of 20:1 and the particle size of the emulsion was measured by a laser particle sizer.
Examples 1-5 counter-current ultrasonic technique in conjunction with conventional free radical process
The preparation method of the egg white protein-tea polyphenol covalent compound comprises the following steps:
(1) soaking a fresh egg which is inspected and has a complete and undamaged eggshell in warm water at about 30 ℃ for cleaning, then cleaning the eggshell with 50mg/L of chlorine water, finally washing residual chlorine on the surface of the eggshell with clear water, airing at room temperature, beating the egg and separating egg white and egg yolk, removing frenulum in egg white liquid, and then stirring at low temperature for 20min until the egg white liquid is uniform to obtain a uniformly dispersed egg white solution;
(2) and (2) carrying out pasteurization on the egg white solution obtained by the treatment in the step (1) at 55-57 ℃ for 3-4 min.
(3) And (3) carrying out freeze drying treatment on the egg white solution subjected to pasteurization treatment in the step (2) at the temperature of-20 ℃ for 48h, and finally carrying out vacuum packaging on the egg white solution to obtain the finished egg white powder.
(4) Preparing the dried egg white protein powder in the step (3) into an egg white protein solution with 1% (w/v) and pH of 3.0, adding 1.0mL of hydrogen peroxide solution and 0.25g of ascorbic acid into 100mL of the egg white protein solution, fully mixing at room temperature, then adding 0.1g of tea polyphenol powder, and treating the mixed solution of the egg white protein and the polyphenol with 40kHz ultrasonic waves, wherein the ultrasonic treatment conditions are as follows: the power is 100W, the temperature is 25 ℃, the time is 20-60 min, and the pulse width is 5s, and the ultrasonic interval time is 3s in table 1. Dialyzing the reacted solution, and spray-drying the dialyzate to obtain the egg white protein-tea polyphenol covalent compound.
(5) And (4) preparing oil-in-water type beta-carotene emulsion by taking the egg white protein-tea polyphenol covalent compound prepared in the step (4) as an emulsifier. Dissolving the egg white protein-tea polyphenol covalent complex freeze-dried powder in 10mmol/L phosphate buffer solution with pH of 7.0, stirring overnight to ensure complete dispersion and dissolution, obtaining an egg white protein-tea polyphenol covalent complex solution with the concentration of 1% (w/w) as a water phase, and simultaneously adding 0.02% (w/w) of an antibacterial agent. Dispersing 0.1% w/w beta-carotene into soybean oil, and performing ultrasonic treatment at 50 deg.C for 20min to completely dissolve to obtain oil phase. Then, mixing the water phase and the oil phase according to the mass ratio of 9:1, stirring for 2min by a high-speed disperser at the speed of 15000r/min to form a coarse emulsion, further homogenizing by a high-pressure homogenizer for 3 times, immediately cooling to room temperature, and storing at 4 ℃ in a dark place for subsequent measurement. The beta-carotene is easy to be oxidized and degraded by light, and in the experimental process, the tinfoil paper is well used for shading treatment, and then the potential and the polydispersity index (PDI) of the emulsion are measured.
TABLE 1 Effect of different countercurrent ultrasonic (40kHz) treatment times on the antioxidant and emulsion Properties of ovalbumin-tea Polyphenol covalent complexes
Note: in the table, DPPH.removing ability was measured at a concentration of 0.2mg/mL of the albumin-tea polyphenol covalent complex.
As can be seen from Table 1, the DPPH removing capacity of the egg white protein is increased from 11.8% to 46.3% -87.3% after the egg white protein is subjected to covalent modification by tea polyphenol, the oxidation resistance is remarkably improved, and the effect improvement is most remarkable after the egg white protein is subjected to synergistic reaction for 50-60 min by ultrasonic waves. Furthermore, the higher the absolute value of the Zeta potential of the emulsion, the greater the interfacial film strength of the droplets, the more stable such an emulsion; the smaller the PDI, the narrower the particle size distribution of the emulsion, and the higher the Zeta potential and the narrower particle size distribution of the emulsion after the egg white protein is covalently modified by the tea polyphenol, which shows that the stability of the emulsion is also obviously improved.
Compared with the traditional free radical modification method for 24 hours in water bath, the countercurrent ultrasonic technology can accelerate the covalent crosslinking of the egg white protein and the polyphenol compound, the reaction time is 20-60 min, and the covalent modification time of the egg white protein and the tea polyphenol is obviously reduced. The method is simple to operate, the conditions are mild, and unreacted free radical initiating reagents are removed by a dialysis method after the reaction is finished, so that toxic and harmful byproducts are not generated.
Examples 6-10 Multi-mode ultrasonic technique in conjunction with conventional free radical Process
Examples 6-10 were prepared in the same manner as examples 1-5, except that the sonication equipment and sonication parameters were varied. Table 2 is the effect of different ultrasound modes on the oxidation resistance, emulsion potential and PDI of the albumin-tea polyphenol covalent complex.
TABLE 2 Effect of ultrasound mode on Oxidation resistance and emulsion Properties of egg white protein-tea Polyphenol covalent complexes
Note: in the table, DPPH.removing ability was measured at a concentration of 0.2mg/mL of the albumin-tea polyphenol covalent complex.
As can be seen from Table 2, the DPPH removing capability of egg white protein can be remarkably improved by adopting the ultrasonic modes in cooperation with the tea polyphenol free radical covalent modification, so that the oxidation resistance of the egg white protein is further improved, wherein the improvement effect of ultrasonic single-frequency treatment of 40kHz and ultrasonic 20/28/40kHz is the most remarkable.
In addition, except 20/28kHz double-frequency synchronous ultrasonic treatment, the stability of the emulsion is also obviously improved as the higher Zeta potential and narrower particle size distribution of the emulsion are obtained after covalent modification of the ultrasonic wave and the tea polyphenol.
The above-listed detailed description is only a specific description of a possible embodiment of the present invention, and they are not intended to limit the scope of the present invention, and equivalent embodiments or modifications made without departing from the technical spirit of the present invention should be included in the scope of the present invention.
Claims (10)
1. A preparation method of an albumin-plant polyphenol covalent complex is characterized by comprising the following steps:
separating and sterilizing an egg white protein solution;
step (2), preparation of the egg white protein-plant polyphenol covalent compound: adjusting the pH of the egg white protein solution obtained by the step (1), adding hydrogen peroxide and ascorbic acid, mixing, adding plant polyphenol, placing in an ultrasonic reaction system for ultrasonic treatment in cooperation with free radical modification reaction, wherein the ultrasonic treatment is countercurrent ultrasonic treatment or multi-frequency ultrasonic treatment, and obtaining the egg white protein-plant polyphenol covalent compound.
2. The method for preparing the covalent complex of egg white protein and plant polyphenol as claimed in claim 1, wherein the weight ratio of the egg white protein to the plant polyphenol in the step (2) is 10: 1.
3. The method for preparing the covalent complex of egg white protein and plant polyphenol as claimed in claim 1, wherein the preparation of the covalent complex of egg white protein and plant polyphenol in the step (2) is specifically as follows:
preparing 100mL of the egg white protein solution with the concentration of 1% obtained in the step (1), adjusting the pH value to 3.0, adding 1mL of 5mol/L hydrogen peroxide and 0.25g of ascorbic acid powder, fully mixing, adding 0.1g of plant polyphenol solution, placing the mixture in an ultrasonic reaction system for ultrasonic treatment and free radical modification reaction, wherein the ultrasonic treatment is a countercurrent ultrasonic treatment or multi-frequency ultrasonic treatment mode, and the reaction time is 20-60 min, so as to obtain the egg white protein-plant polyphenol covalent compound.
4. The method for preparing the covalent complex of egg white protein and plant polyphenol as claimed in claim 3, wherein the reaction time in the step (2) is 50-60 min.
5. The method for preparing the covalent complex of egg white protein and plant polyphenol as claimed in claim 1, wherein the plant polyphenol is tea polyphenol, catechin, chlorogenic acid or epigallocatechin gallate.
6. The method for preparing an ovalbumin-plant polyphenol covalent complex according to claim 3, wherein the ultrasonic treatment is a counter current ultrasonic treatment;
the parameters of the countercurrent ultrasonic treatment are as follows: pulse width 5s, ultrasonic interval time 3s, ultrasonic frequency 40kHz, and ultrasonic power density 100W/L, wherein the feed liquid passes through the ultrasonic probe in a countercurrent circulation mode.
7. The method for preparing an ovalbumin-plant polyphenol covalent complex according to claim 3, wherein the ultrasonic treatment is a multi-frequency ultrasonic treatment mode;
the multi-frequency ultrasonic treatment mode is three-frequency synchronous ultrasonic treatment, or dual-frequency synchronous ultrasonic treatment, or single-frequency ultrasonic treatment, and the multi-frequency ultrasonic treatment parameters are as follows: the ultrasonic power density is 100W/L, the ultrasonic pulse working time is 10s, the pulse interval time is 5s, and the ultrasonic time is 60 min.
8. The method for preparing the covalent complex of egg white protein and plant polyphenol as claimed in claim 7, wherein the ultrasonic wave of the tri-frequency synchronous ultrasonic treatment is 20/28/40 kHz; the ultrasonic wave of the double-frequency synchronous ultrasonic treatment is 20/40kHz, and the ultrasonic wave of the single-frequency treatment is 40 kHz.
9. The method for preparing the covalent complex of egg albumin and plant polyphenol as claimed in claim 1, further comprising the steps of (3) purifying and drying the covalent complex of egg albumin and plant polyphenol;
the purification and drying of the egg white protein-plant polyphenol covalent compound specifically comprise the following steps: dialyzing the egg white protein-plant polyphenol covalent compound solution reacted in the step (2), removing unreacted free plant polyphenol, collecting dialysate and drying.
10. An albumin-plant polyphenol covalent complex, characterized in that it is prepared by the method according to any one of claims 1 to 9.
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