CN114947109A - Preparation and application of octenylsuccinic acid cyclodextrin ester-allicin clathrate compound - Google Patents
Preparation and application of octenylsuccinic acid cyclodextrin ester-allicin clathrate compound Download PDFInfo
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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
- 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
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B4/00—General methods for preserving meat, sausages, fish or fish products
- A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
- A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
- A23B4/20—Organic compounds; Microorganisms; Enzymes
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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
- A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
- A23L13/40—Meat products; Meat meal; Preparation or treatment thereof containing additives
- A23L13/42—Additives other than enzymes or microorganisms in meat products or meat meals
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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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention belongs to the technical field of emulsion preparation, and particularly relates to an octenyl succinic acid cyclodextrin ester-allicin clathrate compound prepared by ultrasonic assistance and application thereof in preparation of high internal phase Pickering emulsion. Under the condition that the pH value is 8.0, octenyl succinic anhydride is added into the beta-cyclodextrin solution, modified OS-beta-CD particles are obtained after ultrasonic treatment, and the obtained particles are embedded by allicin, so that the OS-beta-CD-allicin clathrate compound is obtained. The OS-beta-CD-allicin clathrate compound obtained by the invention has good emulsifying property and antibacterial property, and the prepared high internal phase Pickering emulsion can obviously improve the quality and shelf life of meat products.
Description
Technical Field
The invention belongs to the technical field of emulsion preparation, and particularly relates to an octenyl succinic acid cyclodextrin ester-allicin clathrate (OS-beta-CD-allicin clathrate) prepared by ultrasonic assistance and application thereof in preparation of high internal phase Pickering emulsion.
Background
The meat and meat products are widely loved by consumers, the consumption enthusiasm for meat products with high animal fat content is continuously reduced along with the continuous improvement of the consciousness and consumption level of healthy diet of the consumers, a large amount of cholesterol contained in the fat can induce a plurality of chronic diseases including obesity, and the health of human bodies is seriously influenced. However, when the fat content is reduced, the problems of reduced emulsion stability, poor flavor, reduced product quality and the like of the meat products can be caused. Therefore, low-fat emulsified meat products are the trend in the current food industry, and the high internal phase Pickering emulsion has semisolid characteristics, so that the high internal phase Pickering emulsion is increasingly applied to meat products to replace animal fat due to the unique properties of the high internal phase Pickering emulsion, thereby improving the mouthfeel and the nutritional ingredients of the meat products.
High internal phase Pickering emulsions are a class of ultra-concentrated emulsions with a dispersed phase above 74% and droplets that accumulate and deform into polyhedral geometries, commonly known as ultra-concentrated emulsions or gel emulsions, with potential applications in functional health foods, cosmetics, scaffolds and porous polymer templates. Because of low water content, the emulsion can effectively prevent the breeding of microorganisms, and has longer shelf life compared with other emulsion systems.
Most of the high internal phase Pickering emulsion in the present stage is prepared from protein particles, and the high internal phase Pickering emulsion prepared from the protein particles has good stability, but cannot form stable high internal phase Pickering emulsion when the pH is close to the isoelectric point of protein, and beta-cyclodextrin (beta-CD) cannot be influenced. beta-CD is an oligosaccharide formed by connecting 7 glucose molecules together by alpha-1, 4 glycosidic bonds, is one of the commonly used emulsifiers due to good emulsibility and low production cost, but cannot prepare a stable high internal phase Pickering emulsion. Researches show that the hydrophilic and lipophilic properties of the beta-CD can be effectively improved by introducing the OSA hydrophobic long chain, so that the emulsifying capacity of the beta-CD is improved, and the prepared OS-beta-CD is a high-quality emulsifier for preparing stable high-internal-phase Pickering emulsion. However, the OS- β -CD stabilized high internal phase Pickering emulsions also develop a stratification condition during storage that is affected by microbial growth. Therefore, it is necessary to inhibit the growth and propagation of microorganisms by appropriate means.
Studies have shown that bacteriostatic substances are diverse but generally chemically unstable and susceptible to decomposition, such as allicin.
Therefore, how to further enhance the stability of the high internal phase Pickering emulsion by using bacteriostatic substances is an urgent need to solve the problem at the present stage.
Disclosure of Invention
The invention provides a prepared octenylsuccinic acid cyclodextrin ester-allicin clathrate (OS-beta-CD-allicin clathrate) and a preparation method thereof, which make up the defects of the prior art.
Another object of the present invention is to provide a method for preparing a high internal phase Pickering emulsion with stable OS- β -CD-allicin clathrate.
Another object of the present invention is to provide a use of the high internal phase Pickering emulsion prepared by the above method in low fat meat products, which improves the shelf life of the meat products.
In order to realize the purpose, the invention adopts the technical scheme that:
a preparation method of octenylsuccinic acid cyclodextrin ester-allicin clathrate comprises adding octenylsuccinic anhydride (OSA) into beta-cyclodextrin solution under the condition of pH being 8.0, carrying out ultrasonic treatment to obtain modified OS-beta-CD particles, and embedding the particles with allicin to obtain the OS-beta-CD-allicin clathrate.
Further, under the condition that the pH value is 8.0, adding OSA into the beta-cyclodextrin solution, carrying out ultrasonic treatment on a reaction system after fully mixing, and obtaining modified OS-beta-CD particles after washing and drying; embedding allicin with OS-beta-CD to obtain an OS-beta-CD-allicin clathrate; wherein the addition amount of the OSA is 3 percent of the mass of the beta-cyclodextrin; the ultrasonic time is 10-35min, and the power is 150-450W.
The ultrasonic treatment conditions are as follows: the frequency is 30kHz, the temperature is 35 ℃, the work is carried out for 4s, the intermission is 2s, and the ultrasonic treatment is carried out for 10-30 min.
The ultrasonic time is 25-35 min, and the power is 200-300W.
Dissolving the modified OS-beta-CD particles into water to obtain an OS-beta-CD saturated solution, adding the OS-beta-CD saturated solution into the allicin dissolved by absolute ethyl alcohol, and performing ultrasonic mixing embedding to obtain an OS-beta-CD-allicin clathrate compound; wherein the core-wall ratio (W/W) of the allicin and the OS-beta-CD solution is 1: 5-1: 9, the power of the ultrasonic reaction is 150-450W, and the reaction time is 5-25 min. Wherein the mass ratio of the garlic oil to the absolute ethyl alcohol is 1: 1.
The saturated solution of OS-beta-CD contains 1.8% -2.6% of modified OS-beta-CD particles; wherein the saturated solution of OS-beta-CD is prepared by adding modified OS-beta-CD particles into water at 40-50 deg.C, stirring and heating to dissolve completely to obtain saturated solution.
An octenyl succinic acid cyclodextrin ester-allicin clathrate compound is prepared by the method.
The application of the inclusion compound and the application of the inclusion compound in preparing high internal phase Pickering emulsion.
A high internal phase Pickering emulsion comprising said octenyl succinic acid cyclodextrin ester-allicin clathrate.
The emulsion is an oil phase and the cyclodextrin octenyl succinate-allicin clathrate of claim 7, wherein the oil phase comprises 60% to 80% of the emulsion by volume.
Use of a high internal phase Pickering emulsion for the preparation of a lipid substitute.
Preparation of low-fat meat balls
Separating lean pork and backfat of a pig, cutting into small pieces, mincing for 30s by a meat mincer respectively, adding ingredients in proportion, replacing part of fat in meat balls by embedded high internal phase Pickering emulsion stabilized by OS-beta-CD-allicin inclusion compound, uniformly mixing, quickly chopping for 3min, processing into meat balls with the diameter of about 2.5mm, cooking the formed meat balls respectively, cooling and storing in a refrigerator at 4 ℃.
The proportion of the emulsion replacing the back fat of the pig is 25-100%.
The cooking time is 10 min.
The principle of the invention is as follows:
the method utilizes the beta-cyclodextrin with natural hydrophilic property to perform esterification reaction with octenyl succinic anhydride with good hydrophobicity under the alkalescent condition to introduce a hydrophobic group, so that the OS-beta-CD not only contains hydrophobic-C (carbon-carbon) double bonds, but also contains hydrophilic carboxyl groups (-COOH), and the internal structure of the particles of the OS-beta-CD generates certain influence in specific ultrasonic treatment, thereby accelerating the reaction with the octenyl succinic anhydride, improving the hydrophilic and lipophilic properties and further improving the emulsifying capacity of the OS-beta-CD. In stabilizing oil-in-water emulsions, the hydrophilic carboxyl groups penetrate into the water phase and the lipophilic long alkenyl chains penetrate into the oil phase, so that OS- β -CD forms a very dense film at the oil-water interface, thereby preventing emulsion droplets from aggregating with each other to maintain high emulsion stability. When OS-beta-CD forms a physical barrier film on the surface of allicin (fat soluble), it can increase the stability of allicin and bury its odor. In addition, the obtained OS-beta-CD-allicin clathrate compound is also a solid particle with good emulsifying property, and can be used for preparing high internal phase Pickering emulsion and further application.
The preparation method and the obtained product have the following advantages and beneficial effects:
1. the invention uses ultrasonic technology to assist in preparing OS-beta-CD particles, enhances the hydrophobicity of beta-cyclodextrin, belongs to the combination of physical-chemical modification, and has no pollution, and the preparation process is green and environment-friendly.
2. The reaction process assisted by the ultrasonic is simple, rapid and efficient, so that the reaction time is reduced from tens of hours to tens of minutes in the traditional method, the reaction period is greatly shortened, and the efficiency is improved.
3. The invention can provide a high stable environment for the embedded active substance (such as allicin) to carry or protect the active substance; can also improve the bioavailability of the active substance and minimize the influence on the sensory properties of the product.
4. The high internal phase Pickering emulsion prepared by the invention has high stability, can partially replace fat, and has good application prospect in the processing of low-fat emulsified meat emulsion.
Drawings
FIG. 1 is a graph showing the effect of different ultrasonic powers on the degree of substitution of OS- β -CD particles provided in example 1 of the present invention.
Fig. 2 is a graph showing the effect of different ultrasonic powers on the particle size and potential of OS- β -CD particles provided in example 1 of the present invention.
FIG. 3 is a graph showing the effect of different ultrasonic powers on the OS- β -CD particle activation index provided in example 1 of the present invention.
FIG. 4 is a graph showing the effect of different sonication times on the degree of OS- β -CD particle substitution provided in example 2 of the present invention.
FIG. 5 is a graph showing the effect of different ultrasonic times on the particle size and potential of OS- β -CD particles provided in example 2 of the present invention.
FIG. 6 is a graph showing the effect of different sonication times on the OS- β -CD particle activation index as provided in example 2 of the present invention.
Fig. 7 is a confocal laser microscope image of the OS- β -CD-allicin clathrate provided in embodiment 3 of the present invention.
FIG. 8 is a graph of the effect of a 2.5% OS- β -CD-allicin clathrate dispersion on storage stability of high internal phase Pickering emulsions at different oil phase ratios provided in example 3 of the present invention.
FIG. 9 is a graph of the effect on storage stability of a 2.5% OS- β -CD-allicin clathrate dispersion, a high internal phase Pickering emulsion having an oil phase volume of 80%, provided in example 3 of the present invention.
FIG. 10 is a confocal microscope showing the high internal phase Pickering emulsion stabilized by OS-beta-CD-allicin clathrate in example 3 of the present invention
Fig. 11 is a graph of the effect of different high internal phase Pickering emulsion replacement amounts on cooking loss of low fat meatballs provided in example 3 of the present invention.
Fig. 12 is a graph of the effect of different high internal phase Pickering emulsion replacement amounts on color difference of low fat meat pellets during different storage periods provided in example 3 of the present invention.
Fig. 13 is a graph of the effect of different high internal phase Pickering emulsion replacement amounts on the texture of low fat meat pellets during different storage periods as provided in example 3 of the present invention.
Fig. 14 is a graph of the effect of different high internal phase Pickering emulsion replacement amounts on the pH of low fat meat pellets during different storage periods as provided in example 3 of the present invention.
Fig. 15 is a graph of the effect of different high internal phase Pickering emulsion replacement amounts on low fat pellets TVB-N during different storage periods as provided in example 3 of the present invention.
Fig. 16 is a graph of the effect of different high internal phase Pickering emulsion replacement amounts on low fat meat ball TBARS during different storage periods as provided in example 3 of the present invention.
FIG. 17 is a graph showing the effect of 2.5% beta-cyclodextrin-allicin clathrate dispersions on the storage stability of Pickering emulsions at different oil phase ratios as provided in comparative example 1 of the present invention.
FIG. 18 is a graph of the effect of 2.5% un-sonicated OS- β -CD-allicin clathrate dispersions on the storage stability of Pickering emulsions at different oil phase ratios as provided in comparative example 2 of the present invention.
Detailed Description
In view of the technical problems in the prior art, the experimental scheme of the invention is provided after a large amount of practices. The following examples are presented to further illustrate embodiments of the present invention, and it should be understood that the embodiments described herein are for purposes of illustration and explanation only and are not intended to limit the invention.
Under the condition that the pH value is 8.0, OSA is added into a beta-cyclodextrin solution, the reaction system is subjected to ultrasonic treatment after the OSA is fully mixed, and the modified OS-beta-CD particles are obtained after washing and drying. Embedding garlicin with OS-beta-CD to obtain an OS-beta-CD-garlicin inclusion compound, mixing the OS-beta-CD-garlicin inclusion compound with corn oil, homogenizing to obtain high internal phase Pickering emulsion, and applying the emulsion to low-fat meat products instead of fat. According to the invention, the allicin molecules are partially or completely embedded into the cavity of the OS-beta-CD, so that the contact between the allicin molecules and the surrounding environment is reduced, the stability of the allicin molecules is increased, the antibacterial effect of the allicin molecules is better exerted, the obtained OS-beta-CD-allicin clathrate compound has good emulsifying property and antibacterial property, and the quality and shelf life of the meat product can be remarkably improved by the prepared high internal phase Pickering emulsion.
Example 1
Weighing 30g of beta-cyclodextrin, dissolving the beta-cyclodextrin in distilled water to prepare a 35% beta-cyclodextrin suspension, stirring for 20min by using a magnetic stirrer, adjusting the beta-cyclodextrin suspension to 8.0 by using a 3% NaOH solution, slowly dripping an OSA ethanol solution with the mass fraction of 16.67% at 35 ℃ according to the condition that octenyl succinic anhydride accounts for 3% of the total amount of the cyclodextrin, continuously stirring by using a constant-temperature magnetic stirrer, and continuously dripping a 3% NaOH solution in the process of dripping the OSA solution to maintain the pH value of a reaction system at 8.0.
Putting the mixed solution added with the OSA solution into an ultrasonic cell disruptor, wherein the ultrasonic treatment conditions are as follows: the frequency is 30kHz, the temperature is 35 ℃, the operation is 4s, the intermission is 2s, the ultrasonic power is 150-450W, and the ultrasonic reaction is carried out for 15 min. After the reaction is finished, adjusting the solution to 6-7 by using 0.1mol/L HCl, centrifuging for 10min at 6000r/min, removing supernatant, washing the precipitate with deionized water for 2 times, then washing with ethanol solution with the volume fraction of 70% for 2 times, drying for 2h at 40 ℃, and crushing and sieving with a 100-mesh sieve.
Then, the substitution degree, the particle size, the potential and the activation index of the OS-beta-CD particles obtained by the modification treatment are tested (see FIGS. 1-3), and as can be seen from FIG. 1, the influence on the substitution degree of the OS-beta-CD increases firstly and then decreases with the increase of the ultrasonic power; when the ultrasonic power reaches 225W, the OS-beta-CD substitution degree reaches the maximum value; as the ultrasonic power continues to increase, the degree of substitution continues to decrease. As can be seen from FIG. 2, the influence of the ultrasonic power on the grain size of OS- β -CD also shows a tendency of rising first and then falling, and the absolute value of the potential is maximum at 225W. As can be seen from fig. 3, the particle activation index exhibits a maximum at 225W, while a higher activation index indicates a higher hydrophobicity.
From the above data, it can be seen that an ultrasonic power of 225W is the optimum power.
Example 2
Weighing 30g of beta-cyclodextrin, dissolving in distilled water to prepare a beta-cyclodextrin suspension with the concentration of 35%, stirring for 20min by using a magnetic stirrer, adjusting the beta-cyclodextrin suspension to 8.0 by using a 3% NaOH solution, slowly dripping an OSA ethanol solution with the mass fraction of 16.67% at 35 ℃ according to the condition that the addition amount of octenyl succinic anhydride is 3% of the total amount of the beta-cyclodextrin, continuously stirring by using a constant-temperature magnetic stirrer, and continuously dripping the 3% NaOH solution in the process of dripping the OSA solution to maintain the pH of a reaction system at 8.0.
Placing the mixed solution added with the OSA solution in a cell disruptor, and carrying out ultrasonic treatment under the following conditions: the frequency is 30kHz, the temperature is 35 ℃, the work is 4s, the intermission is 2s, the ultrasonic power is 225W, and the ultrasonic reaction is carried out for 0-35 min. After the reaction is finished, adjusting the solution to 6-7 by using 0.1mol/L HCl, centrifuging for 10min at 6000r/min, removing supernatant, washing the precipitate for 2 times by using ethanol solution with the volume fraction of 70%, washing for 2 times by using deionized water, drying for 2h at 40 ℃, and crushing and sieving by using a 100-mesh sieve.
The degree of substitution, particle size, potential and activation index of the OS- β -CD particles obtained by the above modification treatment were then tested (see fig. 4 to 6),
as can be seen from FIG. 4, when the ultrasonic reaction is between 0-15 min, the degree of substitution of OS- β -CD increases with the increase of the reaction time; when the ultrasound reaches 20min, the degree of substitution is reduced; then, along with the increase of the reaction, the substitution degree is increased, the substitution degree reaches the maximum value when the ultrasonic reaction is carried out for 30min, and the substitution degree is slightly reduced when the ultrasonic reaction is carried out continuously, namely the ultrasonic reaction is carried out for 35 min. As can be seen from fig. 5, the maximum value of the ultrasonic time to the particle size of OS- β -CD occurred at 30min, and the absolute value of the potential was also the maximum, which corresponds to the degree of particle substitution. As can be seen from fig. 6, the activation index also corresponds to the degree of substitution, reaching a maximum at 30min, indicating that the hydrophobicity of β -CD increases with increasing degree of substitution after OSA modification.
From the above data, it can be seen that the ultrasound time of 30min is optimal. Namely, when the ultrasonic power is 225W and the ultrasonic reaction is carried out for 30min, the prepared octenyl succinic acid cyclodextrin anhydride has the maximum degree of substitution and the best hydrophobicity.
Example 3
Weighing 2.4g of the modified OS-beta-CD particles obtained under the conditions of ultrasonic power of 225W and ultrasonic reaction for 30min, dissolving in distilled water, weighing allicin according to the core-wall ratio of 1:8(W/W), slowly adding 50% by mass of allicin ethanol solution into 2.4% OS-beta-CD saturated solution, fully and uniformly stirring, and embedding for 5min under the ultrasonic condition of 225W. And after the embedding reaction is finished, centrifuging, washing out the non-embedded allicin on the surfaces of the particles by using ethanol, and drying to obtain the OS-beta-CD-allicin clathrate compound.
Dissolving the obtained OS-beta-CD-allicin clathrate compound in distilled water to form 2.5% saturated solution, mixing the saturated solution with oil phase, wherein the volume fraction of the vegetable oil is 60% -80%, and homogenizing the mixed solution 13000rmp/min for 2min by using a high-speed homogenizing dispersion machine to obtain high internal phase Pickering emulsion with stable OS-beta-CD-allicin clathrate compound.
FIG. 7 is a confocal laser microscopy of the OS- β -CD-allicin clathrate. As can be seen, the color of OS- β -CD appears red when excited at 633nm after staining with Nile blue (FIG. a), the color of allicin appears green when excited at 488nm after staining with Nile red (FIG. b), and the green allicin in the field is wrapped by the red OS- β -CD (FIG. c), which indicates that the complexation reaction of OS- β -CD and allicin occurs and the allicin enters the cavity of OS- β -CD.
FIG. 8 is an appearance diagram of Pickering emulsions with different oil-water ratios, which are stabilized based on OS-beta-CD-allicin clathrate, placed for 1d, 7d and 41 d. The emulsion with the particle concentration of 2.5 percent and the oil phase proportion of 60 percent to 80 percent can form stable emulsion when being prepared, and the emulsion has the phenomenon of elutriation in different degrees after being stored for 7 days; the added oil phase volume is 60-70%, the layering phenomenon of the emulsion is obvious, and the emulsion with the oil phase volume of 75-80% is stable and does not have the layering phenomenon. After 41 days of storage, emulsions with oil phase volumes of 75% to 80% remained stable and did not separate.
FIG. 9 is an appearance plot of 2.5% OS- β -CD-allicin clathrate dispersion, high internal phase Pickering emulsions at 80% oil phase volume at 1d, 30d, 60d, 90d, 120d, and 147 d. The high internal phase Pickering emulsion has good stability within 1-120d, and the delamination phenomenon is not generated all the time; at 147d, the emulsion delaminated. This shows that the OS-beta-CD-allicin clathrate compound prepared by ultrasonic modification has good stability, and the storage time of the stable emulsion is 3.5 times of that of the OS-beta-CD-allicin clathrate compound stable emulsion without ultrasonic modification.
FIG. 10 is a confocal laser microscopy of high internal phase Pickering emulsion stabilized by OS- β -CD-allicin clathrate. As can be seen from the graph (a), corn oil is excited to green at 488nm after nile red staining, while the OS- β -CD-allicin clathrate is excited to red at 633nm after nile blue staining in graph (b), and the bright green areas and red color dispersed around them in the field graph (c) indicate that the OS- β -CD-allicin clathrate stabilized high internal phase Pickering emulsion is a typical O/W type emulsion. Furthermore, it can be seen from the figure that the oil droplets are evenly and tightly distributed into the continuous phase containing the OS- β -CD-allicin clathrate, resulting in a high internal phase Pickering emulsion with good stability.
Example 4
A low fat preparation was prepared using the high internal phase Pickering emulsion from the above example to obtain 80% oil phase:
removing visible fascia, separating lean pork and backfat, cutting into small pieces, mincing and beating respectively for 30s by a meat mincer, adding the ingredients according to the proportion recorded in the following table, respectively replacing backfat with high internal phase Pickering emulsion stabilized by OS-beta-CD-allicin inclusion compound according to different proportions, quickly chopping and stirring for 3min after uniformly mixing, processing into meat balls with the diameter of about 2.5mm, respectively cooking the formed meat balls, fishing out the meat balls, cooling to room temperature, and storing at 4 ℃.
The formulation of low fat meat pellets prepared from different experimental groups using high internal phase Pickering emulsion instead of pig backfat is shown in table 1, while low fat meat pellets without high internal phase Pickering emulsion were used as control.
TABLE 1 Low fat meat ball formula using high internal phase Pickering emulsion instead of pig backfat
Optimal high internal phase Pickering emulsion replacement was obtained for the different low fat meatballs obtained above through cooking loss, texture, sensory evaluation, and later storage.
1) The cooking loss rate is an important index for evaluating the quality reduction degree of the meat product in the cooking process, and the cooking loss rate of the low-fat meat balls is calculated by measuring the weight change of the meat balls before and after cooking. The effect of different fat replacement amounts on the loss rate of cooked low fat meatballs is shown in fig. 11. As can be seen from the graph, the cooking loss rate of the low-fat meatballs decreases as the amount of fat replacement increases. The reason for this is probably that after the high internal phase Pickering emulsion is added, the interaction between the emulsion OS-beta-CD-allicin clathrate and the protein in the meat emulsion is enhanced, a more stable and elastic network structure is formed, the binding ability to water is enhanced, the water holding capacity is improved, and the process quality is improved, so that the cooking loss rate of the low-fat meat balls is reduced.
2) Sensory evaluation has a key influence on the determination of food quality, and according to the requirements specified in GB/T2210-2008, sensory evaluators should grade the tissue state, taste, color and the like of the meatballs. As can be seen from table 2, compared to the control group (meat balls without fat replaced with emulsion), the sensory scores of the texture and mouthfeel of the low-fat meat balls are increased with the increase of the fat replacement amount, but the scores of the low-fat meat balls are decreased with the increase of the fat replacement amount, the color of the low-fat meat balls is not greatly affected by the addition amount of the emulsion, but the meat balls have light garlic flavor when the addition amount of the emulsion exceeds 75%. When the addition amount of the high internal phase Pickering emulsion is 50%, each sensory score of the meat balls is very high, the acceptability of the meat balls is highest, the interaction among meat paste proteins is enhanced, a more stable and elastic network structure is formed compared with a control group, and the taste is improved.
TABLE 2 sensory evaluation results of different emulsion substitution ratios
3) The color of the product is an important index for evaluating the meat product, the proper color of the meat product can increase the product preference of consumers and stimulate the consumers to consume, and the L value, the a value and the b value of the low-fat meat balls are measured by using a color difference meter. FIG. 12 is a graph showing the effect of different fat replacement amounts on the color difference of low-fat meat balls, and it can be seen that as the fat replacement amount of the emulsion is increased, the L values of the meat balls are increased and are larger than those of the control group, while the a values and the b values are decreased with the fat replacement amount. During storage, the L values for the different fat substitutes increased with increasing storage time, and the a and b values decreased with increasing storage time.
4) The addition amount of the fat content can obviously influence the texture and mouthfeel of the meat product, and the hardness, elasticity and chewiness of the low-fat meat balls are measured by a texture analyzer. As can be seen from fig. 13, compared with the control group, the hardness and chewiness of the meat balls are obviously increased along with the increasing of the fat substitution amount, but the elasticity of the meat balls is not obviously changed, which is probably because the interaction among meat emulsion proteins is enhanced along with the increasing of the fat substitution amount, and a network structure which is more stable and elastic than the control group is formed, so that the partial texture quality index of the meat balls is enhanced. Throughout storage, the hardness and chewiness of the meatballs increase with storage time, and the elasticity, just the opposite, decreases with storage time. The change in hardness may be due to the relatively good water holding capacity of the meat pellets at the initial stage of storage and the relatively low hardness of the meat pellets, with the moisture loss of the meat pellets over time and the increase in hardness.
5) Microbial contamination is one of the major factors responsible for spoilage of food products, and it reflects the degree to which meat products are spoiled. The total number of colonies of the low-fat meat balls is determined by referring to GB 4789.2-2016 (national food safety Standard food microbiological inspection colony number determination). Table 3 shows the ratio of different fat replacements to the total number of colonies of low fat meat pellets during storage, as seen at 0d, the different fats were replacedThe colony number of the generation amount is not different from that of the control group, the colony number of the samples with different fat substitution amounts is obviously less than that of the control group (P < 0.05) along with the prolonging of the storage time, and the larger the fat substitution ratio is, the less the meat balls are polluted. The total number of colonies on 9d of the meat balls of the control group reaches 9.67 multiplied by 10 5 Spoilage begins, and the meatballs with 100% fat replacement begin to spoil at 15 d. This is probably due to the inclusion of unstable allicin in the high internal phase Pickering emulsion used to replace fat, which has a very good microbial inhibitory effect, and the slow release of allicin over storage time inhibits the growth and proliferation of microorganisms in the meatballs to some extent.
TABLE 3 Total colony count results for different fat replacement ratios
6) The pH value can be used as an important index for inspecting the freshness of meat products, and the pH value of the low-fat meat balls is measured by referring to GB51009.237-2016 (food pH value measurement). As can be seen from fig. 14, the pH values of the samples in each group tended to decrease and then increase with increasing storage period, with the control group reaching the lowest pH value on day 3 and the experimental group (25% to 100%) reaching the lowest pH value on day 6. At the 0d, the pH value difference between the control group and the experimental group is not obvious, because the meat product is used as a good buffer system, has good buffer effect on the added emulsion and can well maintain the pH value stability of the meat balls; the first drop in pH exhibited as the shelf life increased may be due to the breakdown of myoglycogen and adenosine triphosphate in the meat pellets to produce lactic acid and phosphoric acid, respectively, resulting in a decrease in the pH of the meat pellets; the reason why the pH value gradually rises is that the number of microorganisms is increased, and the pH value of the meat balls is increased due to the fact that alkaline substances such as ammonia, amine and the like are generated by protein decomposition under the action of the microorganisms. And the fat-replacement group showed mostly a lower pH value compared to the control group throughout the storage period. The low-fat meat balls with different fat substitute ratios have different pH value change ranges, the pH value of the control group is reduced most quickly, and the pH value with 100 percent of substitution degree is changed most slowly. This is probably because the lower the fat content of the low-fat meat ball, the slower the deterioration speed of the low-fat meat ball is, and the allicin has inhibition effect on the microorganism, and from the result that the total number of the bacterial colonies is obviously reduced along with the increase of the fat substitution amount according to the result of replacing the total number of the bacterial colonies by different emulsions, the emulsion has inhibition effect on the growth and the reproduction of the microorganism, thereby delaying the increase speed of the pH value.
7) Volatile basic nitrogen (TVB-N) is also an important evaluation index of the freshness of meat products, the change of the TVB-N is related to the utilization of protein by microorganisms and enzymes in the meat products, and the lower the TVB-N value is, the higher the freshness of the meat products is. The TVB-N of the low-fat meat balls is determined by referring to GB5009.228-2016 (determination method for volatile basic nitrogen). FIG. 15 is a graph showing the TVB-N values of low fat meat pellets with different fat replacement amounts during storage, at 0d, the TVB-N values of 25%, 50% fat replacement amounts of low fat meat pellets did not differ much from the TVB-N values of the control group, with the TVB-N values of the meat pellets decreasing significantly (P < 0.05) with increasing fat replacement, and the TVB-N values of the experimental group with different fat replacement amounts being substantially less (P < 0.05) than the TVB-N values of the control group with increasing storage time. This is probably because the high internal phase Pickering emulsion is embedded with allicin, and the larger the fat replacement ratio is, the better the bacteriostatic effect of allicin is, and the more the growth of TVB-N in the meat ball can be inhibited, which is consistent with the trend of the pH of the meat ball and the change of the total number of bacterial colonies.
8) The thiobarbituric acid value (TBARS value) is an important index for measuring the degree of oxidation of fat in meat products, and is a result of the reaction of 2-thiobarbituric acid (TBA) with derivatives produced by oxidative decomposition in meat products, and the higher the TBARS value is, the higher the degree of oxidation is. TBARS values were calculated for the low fat meatballs by measuring absorbance at 532 nm. Figure 16 is a graph of the change in TBARS values during storage for low fat pellets with different fat replacement levels at day 0, which was significantly less than the TBARS value for the control (P < 0.05), probably because the control added fat was not well encapsulated, the fat oxidation was high during the run, and the decrease in fat addition to the pellets also resulted in a decrease in TBARS value. The TBARS values of the experimental group are obviously lower than those of the control group (P is less than 0.05) in different fat substitution amounts along with the prolonging of the storage time, and the larger the fat substitution ratio is, the lighter the meat balls are subjected to the oxidation degree of the fat. This is probably because the emulsion solid particles have an insulating effect, when preparing the high internal phase Pickering emulsion, the OS- β -CD-allicin inclusion compound wraps the corn germ oil inside, and as the addition amount of the high internal phase Pickering emulsion increases, the meat emulsion forms a more dense gel network structure, which reduces the contact of the corn germ oil and fat with oxygen, thereby inhibiting the oxidation of the fat. In addition, a reduction in the added fat level of the meatballs also leads to a reduction in the TBARS value.
Comparative example 1
Weighing 2.4g of unmodified beta-cyclodextrin particles, dissolving the particles in distilled water to form 2.4% of particle dispersion liquid, weighing allicin according to a core-wall ratio of 1:8(W/W), mixing an allicin ethanol solution with the mass fraction of 50% and an OS-beta-CD solution, fully and uniformly stirring, and embedding for 5min under the ultrasonic condition of 225W. After the embedding reaction is finished, centrifuging, washing out the non-embedded allicin on the particle surface by using ethanol, and drying to obtain the beta-cyclodextrin-allicin clathrate compound.
Dissolving the obtained beta-cyclodextrin-allicin clathrate compound in distilled water to form 2.5% saturated solution, mixing with corn oil, wherein the volume fraction of the corn oil is 60% -80%, and homogenizing the mixed solution 13000rmp/min for 2min by using a high-speed homogenizing dispersion machine to obtain emulsion with stable beta-cyclodextrin-allicin clathrate compound.
The storage stability of the emulsions obtained above was tested and is shown in fig. 17, which is an appearance diagram of Pickering emulsions with different oil-water ratios for 1d, 7d and 41d based on the stability of the inclusion compound of beta-cyclodextrin-allicin. The emulsion with the particle concentration of 2.5 percent and the oil phase proportion of 60 percent to 70 percent can form stable emulsion when being prepared, and the stable emulsion can not be formed when the oil phase proportion is 75 percent to 80 percent; after 7 days of storage, the emulsion has creaming phenomena of different degrees, the volume of the added oil phase is 60-70%, the creaming phenomenon of the emulsion is obvious, and the oil phase and the water phase of the emulsion are separated at 75-80%, so that the beta-cyclodextrin-allicin clathrate compound which is not modified can not prepare stable high-internal-phase Pickering emulsion.
Comparative example 2
Weighing 30g of beta-cyclodextrin, dissolving in distilled water to prepare 35% cyclodextrin suspension, stirring for 20min by using a magnetic stirrer, adjusting the cyclodextrin suspension to 8.0 by using 3% NaOH solution, slowly dropwise adding 16.67% OSA ethanol solution at 35 ℃, and continuously dropwise adding 3% NaOH solution in the process of dropwise adding the OSA solution to maintain the pH of a reaction system. Continuously stirring for 4h by using a constant-temperature magnetic stirrer, adjusting the solution to 6-7 by using 0.1mol/L HCl after the reaction is finished, centrifuging for 10min at 6000r/min, removing supernatant, washing precipitate for 2 times by using ethanol solution with volume fraction of 70%, washing for 2 times by using deionized water, drying for 2h at 40 ℃, and crushing and sieving by using a 100-mesh sieve.
Weighing 2.4g of the modified OS-beta-CD obtained after magnetic stirring, dissolving the modified OS-beta-CD in distilled water to form 2.4% of particle dispersion liquid, weighing allicin according to the core-wall ratio of 1:8(W/W), fully and uniformly mixing an allicin ethanol solution with the mass fraction of 50% and the OS-beta-CD solution, and embedding the mixture for 5min under the ultrasonic condition of 225W. And after the embedding reaction is finished, centrifuging, washing out the non-embedded allicin on the surfaces of the particles by using ethanol, and drying to obtain the OS-beta-CD-allicin clathrate compound.
Dissolving the OS-beta-CD-allicin clathrate compound in distilled water to form 2.5% of saturated solution, mixing the saturated solution with oil phase, wherein the volume fraction of the vegetable oil is 60% -80%, and homogenizing the mixed solution 13000rmp/min for 2min by using a high-speed homogenizing dispersion machine to obtain high internal phase Pickering emulsion with stable OS-beta-CD-allicin clathrate compound.
TABLE 4 different indices of beta-cyclodextrin, non-sonicated OS-beta-CD, optimal conditions OS-beta-CD
As is clear from table 4, after OSA modification, the β -cyclodextrin particle size decreased, the absolute potential value increased, and the hydrophobicity was also enhanced. The degree of substitution of OS-beta-CD prepared at an ultrasonic power of 225W and an ultrasonic time of 30min was 0.0296, which is 2.1 times that of the sample not subjected to ultrasonic treatment. Under the optimal condition, the prepared OS-beta-CD has the particle size of 1111.83nm, the potential of-17.83 mV and the activation index of 93.22 percent, so that the hydrophobicity of the OS-beta-CD is enhanced, and the emulsifying capacity is improved.
FIG. 18 is an appearance diagram of Pickering emulsions with different oil-water ratios, which are stabilized based on OS-beta-CD-allicin clathrate, placed for 1d, 7d and 41 d. When the concentration of the OS-beta-CD-allicin clathrate compound which is not subjected to ultrasonic modification is 2.5%, emulsion with an oil phase proportion of 60% -75% can form stable emulsion when being prepared, and 80% of the emulsion can form stable emulsion, but a small amount of oil is separated out immediately; after 7 days of storage, the emulsion has the phenomenon of elutriation to different degrees; the volume of the added oil phase is 60-70%, the layering phenomenon of the emulsion is obvious, and the emulsion with the oil phase proportion of 75-80% is not layered; after being stored for 41 days, the emulsion with the oil phase proportion of 75-80% begins to be layered, and the high internal phase Pickering emulsion prepared by the OS-beta-CD-allicin clathrate compound modified by ultrasonic waves is not layered at 41 days and is layered at 147 days.
In conclusion, the OS-beta-CD assisted by the ultrasonic wave has better surface hydrophobicity and improves the emulsifying capacity of the beta-cyclodextrin compared with the unmodified beta-cyclodextrin and the OS-beta-CD not modified by the ultrasonic wave. Moreover, high internal phase Pickering emulsions prepared with ultrasonically modified OS- β -CD-allicin clathrates have excellent storage stability relative to unmodified β -cyclodextrin-allicin clathrates and non-ultrasonically modified OS- β -CD-allicin clathrates. And the high internal phase Pickering emulsion can be used for replacing fat in the meat product, so that the quality of the meat product can be improved, and the shelf life of the meat product can be prolonged.
Claims (10)
1. A preparation method of an octenyl succinic acid cyclodextrin ester-allicin clathrate compound is characterized by comprising the following steps: under the condition that the pH value is 8.0, Octenyl Succinic Anhydride (OSA) is added into the beta-cyclodextrin solution, modified OS-beta-CD particles are obtained after ultrasonic treatment, and the obtained particles are embedded by allicin, so that the OS-beta-CD-allicin clathrate compound is obtained.
2. A process for preparing an octenylsuccinate cyclodextrin ester-allicin clathrate according to claim 1, comprising: adding OSA into the beta-cyclodextrin solution under the condition that the pH value is 8.0, fully mixing, carrying out ultrasonic treatment on a reaction system, washing and drying to obtain modified OS-beta-CD particles; embedding allicin with OS-beta-CD to obtain an OS-beta-CD-allicin clathrate; wherein the addition amount of the OSA is 3 percent of the mass of the beta-cyclodextrin; the ultrasonic time is 10-35min, and the power is 150-450W.
3. A process for preparing an octenylsuccinate cyclodextrin ester-allicin clathrate according to claim 2, comprising: the ultrasonic treatment conditions are as follows: the frequency is 30kHz, the temperature is 35 ℃, the work is carried out for 4s, the pause is 2s, and then the ultrasonic treatment is carried out for 10-30 min.
4. A process for preparing an octenylsuccinate cyclodextrin ester-allicin clathrate according to claim 2, comprising: dissolving the modified OS-beta-CD particles into water to obtain an OS-beta-CD saturated solution, adding the OS-beta-CD saturated solution into the allicin dissolved by absolute ethyl alcohol, and performing ultrasonic mixing embedding to obtain an OS-beta-CD-allicin clathrate compound; wherein the core-wall ratio (W/W) of the allicin and the OS-beta-CD solution is 1: 5-1: 9, the power of the ultrasonic reaction is 150-450W, and the reaction time is 5-25 min.
5. A process for preparing an octenylsuccinate cyclodextrin ester-allicin clathrate according to claim 4, comprising: the saturated solution of OS-beta-CD contains 1.8% -2.6% of modified OS-beta-CD particles; wherein the saturated solution of OS-beta-CD is prepared by adding modified OS-beta-CD particles into water at 40-50 deg.C, stirring and heating to dissolve completely to obtain saturated solution.
6. An octenylsuccinate-allicin clathrate made by the process of claim 1, wherein: the cyclodextrin ester of octenyl succinic acid-allicin clathrate is prepared by the method of claim 1.
7. Use of the clathrate according to claim 1, characterized in that: the inclusion compound is applied to preparation of high internal phase Pickering emulsion.
8. A high internal phase Pickering emulsion characterized by: a clathrate compound comprising the cyclodextrin ester of octenyl succinate-allicin of claim 1.
9. The high internal phase Pickering emulsion of claim 8, wherein: the emulsion is an oil phase and the cyclodextrin octenyl succinate-allicin clathrate of claim 6, wherein the oil phase comprises 60% to 80% of the emulsion by volume.
10. Use of a high internal phase Pickering emulsion according to claim 8, wherein: the use of said emulsion in the preparation of a lipid substitute.
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