Preparation method and application of a high-antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles

Abstract

The present invention belongs to the field of food technology, and discloses a preparation method and application of a high antioxidant Pickering emulsion stabilized by ternary particles of cyclodextrin-polyphenol-oil molecules self-assembly. The preparation method of the high antioxidant Pickering emulsion comprises the following steps: using an aqueous dispersion of cyclodextrin as an aqueous phase, mixing it with an oil phase and polyphenols at the same time, and stirring and mixing to obtain the high antioxidant Pickering emulsion stabilized by ternary particles of cyclodextrin-polyphenol-oil molecules self-assembly. Stirring and mixing refers to stirring for 1-6 hours at a stirring rate of 250-500rpm and 10-40°C. The high antioxidant Pickering emulsion stabilized by ternary particles of cyclodextrin-polyphenol-oil molecules self-assembly obtained by the method of the present invention has the characteristics of simple preparation, strong oxidative stability, non-toxicity, good biocompatibility, etc., and can be widely used in the fields of food industry, pharmaceutical industry, daily chemicals, etc.

Description

Technical Field

[0001] The invention belongs to the field of food technology, and particularly relates to a preparation method and application of a high-antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles. Background Art

[0002] Emulsion systems play an important role in the food industry. Oxidation of oils and fats in emulsions can cause emulsion foods to deteriorate, affecting the normal consumption of food and even posing potential health risks. Currently, emulsion systems stabilized by small molecule surfactants (such as Tween, Span, etc.) are widely used in the food industry. However, recent authoritative studies have found that small molecule surfactants have cytotoxicity and that small molecule surfactants can pollute the environment when discharged into nature. Therefore, the use of materials derived from natural products to stabilize emulsions and the research and development of safe, non-toxic, environmentally friendly, and highly antioxidant food-grade emulsions have become an urgent need in the food industry.

[0003] Pickering emulsions are a type of emulsion stabilized by the adsorption of solid colloidal particles at the oil-water interface. Their preparation process completely avoids the use of small-molecule surfactants, thereby avoiding the toxicity and environmental pollution associated with these surfactants. Compared to emulsions stabilized by traditional small-molecule surfactants, Pickering emulsions exhibit advantages such as enhanced coagulation stability, Ostwald ripening stability, and oxidative stability. With increasing health awareness and advances in science and technology, the use of green, non-toxic, and biocompatible natural molecules to prepare novel colloidal particles and subsequently stabilize Pickering emulsions has become a research area of ​​increasing interest in the food emulsion industry. Organic particles derived from natural organisms offer advantages such as edibility, biodegradability, and safety to humans and the environment, holding enormous potential for application in the food industry. A growing number of studies have shown that the combination of two or more natural biomaterials with different properties can enhance the interfacial properties of natural molecules. Compared to emulsions stabilized by single-component particles, emulsions stabilized by composite colloidal particles offer significant advantages in physicochemical stability and possess the potential to be multifunctional emulsions, such as high antioxidant activity and the ability to encapsulate and deliver functional active substances.

[0004] Cyclodextrin (CD) is a natural cyclic oligosaccharide derived from starch. Among them, molecules containing 6, 7, and 8 glucose units are of great application value, namely α-, β-, and γ-cyclodextrin, respectively. Cyclodextrin has the structural characteristics of being hydrophilic on the outside, hydrophobic on the inside, and having a special cavity. The cavity inside its molecule can undergo supramolecular interactions with a variety of guest molecules, allowing the guest molecules to fully or partially enter the cyclodextrin cavity to form inclusion complexes, thereby improving the water solubility, stability, and taste of the guest molecules. When in contact with oil components, cyclodextrin can self-assemble with oil molecules at the oil / water interface to form amphiphilic supramolecules. This supramolecule has surface activity and can significantly reduce the oil / water interfacial tension. Studies have shown that the oxidative rancidity of oils in Pickering emulsions often occurs at the oil / water interface. Therefore, it is necessary to provide a green, efficient, and highly antioxidant Pickering emulsion to provide a feasible solution to the problem of oil oxidation in emulsions. Summary of the Invention

[0005] In order to overcome the shortcomings and deficiencies of the above-mentioned prior art, the primary purpose of the present invention is to prepare food-grade ternary composite particles that stabilize Pickering emulsions in a low-cost, low-energy method, and to improve the oxidative stability of Pickering emulsions, and to provide an environmentally friendly, simple-to-operate method for preparing a highly antioxidant Pickering emulsion that is stabilized by ternary composite particles obtained by self-assembly of organic particles (cyclodextrin, polyphenols, and oil molecules) of natural biological origin. During the emulsification process of the emulsion, cyclodextrin, plant polyphenols, and oil molecules can self-assemble to form supramolecular ternary composite particles, and the composite particles are adsorbed at the oil / water interface to stabilize the Pickering emulsion. The present invention achieves the simultaneous preparation of cyclodextrin-polyphenol-oil molecule ternary colloidal particles and their stabilized Pickering emulsions, and is a green and efficient method for preparing a Pickering emulsion with high antioxidant activity, providing a feasible solution to the oxidation problem of oils in emulsions.

[0006] Another object of the present invention is to provide a high antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles prepared by the above method.

[0007] Another object of the present invention is to provide a cyclodextrin-polyphenol-oil molecule self-assembled ternary particle.

[0008] Another object of the present invention is to provide an application of the highly antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0009] The purpose of the present invention is achieved through the following solutions:

[0010] A method for preparing a high-antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles comprises the following steps:

[0011] The aqueous dispersion of cyclodextrin is used as the aqueous phase, mixed with the oil phase and polyphenols at the same time, and stirred to obtain the high antioxidant Pickering emulsion stabilized by the self-assembled ternary particles of cyclodextrin-polyphenol-oil molecules.

[0012] The cyclodextrin is at least one of α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, and α-cyclodextrin derivatives, β-cyclodextrin derivatives, and γ-cyclodextrin derivatives;

[0013] The concentration of the cyclodextrin aqueous dispersion is 1%-15% (w / w);

[0014] The oil phase includes but is not limited to soybean oil, linseed oil, peanut oil, sunflower oil, corn oil, camellia oil and at least one of peanut oil diglyceride oil, linseed oil diglyceride oil, camellia oil diglyceride oil and corn oil diglyceride oil with different diglyceride contents (15%-80%).

[0015] The volume ratio of the water phase to the oil phase is 6:4-2:8;

[0016] The polyphenols include at least one of flavonoids and non-flavonoids. Flavonoids include but are not limited to at least one of flavonols (such as quercetin and kaempferol), flavanones (such as naringenin and hesperetin), isoflavones (such as daidzein), and corresponding flavonoid derivatives (such as rutin). Non-flavonoids include phenolic acids, which can be specifically divided into p-hydroxybenzoic acids (including but not limited to p-hydroxybenzoic acid, protocatechuic acid, and gallic acid), p-hydroxycinnamic acids (including but not limited to caffeic acid, ferulic acid, and p-coumaric acid), and non-flavonoids include but are not limited to at least one of curcumin, lignin, and resveratrol.

[0017] The molar ratio of the polyphenol to the cyclodextrin is 1:10-2:1.

[0018] The stirring and mixing is preferably carried out at a stirring rate of 250-500 rpm and a temperature of 10-40° C. for 1-6 hours.

[0019] A high-antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles prepared by the method.

[0020] A cyclodextrin-polyphenol-oil molecule self-assembled ternary particle is prepared by the following method: centrifuging a high-antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particle, removing the supernatant, washing the obtained precipitate with a non-polar solvent, and then drying to obtain the cyclodextrin-polyphenol-oil molecule self-assembled ternary particle.

[0021] The centrifugation refers to centrifugation at 15-25°C and 2000-4000 rpm for 15-30 minutes.

[0022] The non-polar solvent is at least one of petroleum ether, cyclohexane, hexane, pentane and the like.

[0023] The drying refers to freeze drying, preferably drying at -60-40°C for 24-72 hours.

[0024] The above-mentioned cyclodextrin-polyphenol-oil molecule self-assembled ternary particles stabilized high antioxidant Pickering emulsion can be widely used in the fields of food industry, functional food, special medical food, daily skin care products, etc.

[0025] Compared with the prior art, the present invention has the following advantages and beneficial effects:

[0026] 1. The present invention adopts the stirring and emulsifying method to prepare the emulsion. Conventional methods for preparing Pickering emulsions include rotor-stator homogenization and high-pressure homogenization. There is a large friction in the homogenization process, and there is a risk of increasing the temperature of the emulsion, which will lead to instability of temperature-sensitive particles and / or the emulsion; high shear rates will cause fragile particles or aggregates to deform or become unstable, thereby obtaining a wide droplet size distribution. In addition, in industrial production, homogenization requires large-scale homogenizing equipment that can reach the required power, which consumes a lot of energy and has high production costs. It is also difficult to clean and easily causes cross-contamination. The solid particles that stabilize the Pickering emulsion need to overcome a certain adsorption energy before they can be irreversibly adsorbed at the oil-water interface to stabilize the emulsion. Therefore, mechanical energy needs to be provided by high-speed shearing, high-pressure homogenization, etc., and the homogenization process promotes the contact between the particles and the interface, which is beneficial to the adsorption of solid particles at the interface, so that the interfacial tension decreases. The stirring emulsification process has a low rate, generally less than 1000 rpm, which cannot provide sufficient energy for the particles to overcome the adsorption energy and thus stably adsorb at the oil-water interface, thereby reducing the interfacial tension. Therefore, it is generally impossible to form a Pickering emulsion with a small particle size and stability. However, the cyclodextrin in the present invention can self-assemble with polyphenols and oil molecules to form an oil-water amphiphilic complex during the emulsification process, promoting the adsorption of the complex particles at the oil-water interface. Therefore, a Pickering emulsion with a small particle size (10-30 μm) and stability can be obtained without excessive energy input. This is a low-energy emulsion preparation method that forms a composite particle emulsifier through the self-assembly of natural organic molecules, which is easy to achieve large-scale industrial production.

[0027] 2. The present invention realizes the simultaneous preparation of cyclodextrin-polyphenol-oil molecule self-assembled ternary particles and their stable Pickering emulsion. Compared with previous inventions or studies in which a composite colloidal particle dispersion is first prepared or freeze-dried, and then the composite colloidal particles are mixed with an oil phase to prepare a Pickering emulsion, the present invention avoids the loss of polyphenols during the preparation and separation of the composite particles, making the preparation of a highly antioxidant Pickering emulsion more efficient.

[0028] 3. The present invention uses diacylglycerol (DAG) as one of the oil phases. DAG is the most abundant natural component in oils and fats besides triacylglycerol (TAG). Due to differences in metabolic pathways from TAG, DAG is not easily converted into fat for storage in the body, and at the same time avoids various metabolic syndromes caused by long-term intake of high-content TAG. Studies have shown that dietary DAG oil can promote weight loss, reduce body fat, improve serum cholesterol, and can be used as an adjuvant to diet therapy for obesity. The use of DAG to prepare a high-antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles is conducive to expanding the application of Pickering emulsions in new functional foods. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1 This is a diagram showing the appearance of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 1 after standing at room temperature for 24 hours.

[0030] Figure 2 This is a microscope image of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 1 after standing at room temperature for 24 hours.

[0031] Figure 3 This is the appearance of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 2 after storage at room temperature for 30 days.

[0032] Figure 4 This is a microscopic image of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 2 after storage at room temperature for 30 days.

[0033] Figure 5 This is the appearance of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 3 after standing at room temperature for 24 hours.

[0034] Figure 6 Field emission scanning electron microscopy image (A) and a local magnified image (B) of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 3.

[0035] Figure 7 X-ray diffraction pattern of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 4 (A: ternary composite particles, B: ternary physical mixture (the three were mixed uniformly in a mortar without adding water according to the proportions of the ternary complex), C: diglyceride, D: quercetin, E: β-cyclodextrin).

[0036] Figure 8The Fourier transform infrared spectra of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 4 (A: ternary composite particles, B: ternary physical mixture (the three were mixed uniformly in a mortar without adding water according to the proportions of the ternary complex), C: diglyceride, D: quercetin, E: β-cyclodextrin).

[0037] Figure 9 DPPH radical scavenging rate of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 5 (from left to right are blank control, ternary particles with concentrations of 0.25, 0.50, 0.75, and 1.00 mg / mL).

[0038] Figure 10 Figure 5 shows the oxidative stability of the Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 5 and a control (Tween 80 emulsion, a Tween 80 emulsion containing the same amount of ferulic acid as the Pickering emulsion, and a pure oil phase) during storage at 25°C for 15 days. Figure A shows the hydroperoxide value, and Figure B shows the thiobarbituric acid reactive substances (TBARS) value.

[0039] Figure 11 This is the appearance of the product formed in Comparative Example 1.

[0040] Figure 12 This is the appearance of the product formed in Comparative Example 2.

[0041] Figure 13 This is a microscope image of the product formed in Comparative Example 3.

[0042] Figure 14 This is a microscope image of the product formed in Comparative Example 4.

[0043] Figure 15 This is a microscope image of the product formed in Comparative Example 5. DETAILED DESCRIPTION

[0044] The present invention will be described in further detail below with reference to the Examples and accompanying drawings, but the embodiments of the present invention are not limited thereto. Where specific conditions are not specified in the Examples, conventional conditions or conditions recommended by the manufacturer were followed. Reagents or instruments used, where the manufacturer is not specified, are commercially available conventional products.

[0045] Unless otherwise specified, all reagents used in the examples can be purchased from the market.

[0046] Example 1

[0047] (1) α-cyclodextrin was dispersed in water at a concentration of 1% (w / w);

[0048] (2) The cyclodextrin dispersion obtained in step (1) was mixed with peanut oil diglyceride containing 15% DAG at a volume ratio of 6:4, and rutin was added so that the molar ratio of rutin to α-cyclodextrin was 1:10. The mixture was stirred at a stirring rate of 500 rpm and 40° C. for 1 hour using a magnetic stirrer to obtain a highly antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0049] Figure 1 This is a diagram showing the appearance of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 1 after standing at room temperature for 24 hours. Figure 2 This is a microscopic image of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 1 after standing at room temperature for 24 hours. Figure 1 and Figure 2 It can be seen that the Pickering emulsion formed under these conditions is uniform and stable.

[0050] Example 2

[0051] (1) β-cyclodextrin was dispersed in water at a concentration of 15% (w / w);

[0052] (2) The cyclodextrin dispersion obtained in step (1) was mixed with linseed oil diglyceride having an 80% DAG content at a volume ratio of 2:8, and p-hydroxybenzoic acid was added so that the molar ratio of p-hydroxybenzoic acid to β-cyclodextrin was 2:1. The mixture was stirred for 6 hours using a magnetic stirrer at a stirring rate of 250 rpm and a temperature of 10° C. to obtain a highly antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0053] Figure 3 This is the appearance of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 2 after storage at room temperature for 30 days. Figure 4 This is a microscopic image of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 2 after storage at room temperature for 30 days. Figure 3 and Figure 4 It can be seen that the Pickering emulsion formed under these conditions remains uniform and stable after storage at room temperature for 30 days.

[0054] Example 3

[0055] (1) Dispersing γ-cyclodextrin in water at a concentration of 3% (w / w);

[0056] (2) The cyclodextrin dispersion obtained in step (1) was mixed with camellia seed oil diglyceride having a DAG content of 40% in a volume ratio of 1:1, and caffeic acid was added so that the molar ratio of caffeic acid to γ-cyclodextrin was 1:4. The mixture was stirred for 5 h using a magnetic stirrer at a stirring rate of 300 rpm and 25° C. to obtain a highly antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0057] Figure 5 This is the appearance of the high antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 3 after standing at room temperature for 24 hours. Figure 5 It can be seen that a uniform and stable Pickering emulsion can be formed under these conditions. Figure 6 The field emission scanning electron microscope image (A) and the local magnified image (B) of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 3. Figure 6 It can be seen that the particles of the ternary complex formed under this condition have a compact structure and are irregular in shape.

[0058] Example 4

[0059] (1) β-cyclodextrin was dispersed in water at a concentration of 5% (w / w);

[0060] (2) The cyclodextrin dispersion obtained in step (1) was mixed with corn oil diglyceride having a DAG content of 60% at a volume ratio of 4:6, and quercetin was added so that the molar ratio of quercetin to β-cyclodextrin was 1:2. A magnetic stirrer was used to stir at a stirring rate of 400 rpm and 30° C. for 4 h to obtain a highly antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0061] The Pickering emulsion was centrifuged (10,000 × g, 10 min) and the supernatant was discarded. The resulting precipitate was washed three times with petroleum ether and finally freeze-dried (-40°C, 48 h) to obtain cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0062] Figure 7 This is the X-ray diffraction pattern of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 4. Figure 8 This is the Fourier transform infrared spectrum of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 4. Figure 7 and Figure 8 It can be seen that ternary composite particles can be formed under this condition rather than a simple physical mixture.

[0063] Example 5

[0064] (1) α-cyclodextrin was dispersed in water at a concentration of 10% (w / w);

[0065] (2) The cyclodextrin dispersion obtained in step (1) was mixed with peanut oil diglyceride having a DAG content of 70% at a volume ratio of 3:7, and ferulic acid was added so that the molar ratio of ferulic acid to α-cyclodextrin was 1:1. The mixture was stirred for 3 h using a magnetic stirrer at a stirring rate of 450 rpm and 35° C. to obtain a highly antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0066] The Pickering emulsion was centrifuged (10,000 × g, 10 min) and the supernatant was discarded. The resulting precipitate was washed three times with petroleum ether and finally freeze-dried (-40°C, 48 h) to obtain cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

[0067] Figure 9 The DPPH radical scavenging rate of the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles obtained in Example 5 (from left to right are blank control, ternary particles with concentrations of 0.25, 0.50, 0.75, and 1.00 mg / mL). The specific experimental method is as follows: the freshly prepared ternary particles are mixed with 1.4 mL of DPPH radical solution (10 -4 The mixture was then incubated in the dark for 30 minutes. The absorbance was measured at 517 nm relative to the blank. The absorbance of the sample and control group was compared to determine the DPPH radical scavenging rate of the sample. Figure 10 The oxidative stability of the Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in Example 5 and the control group (the Tween 80 emulsion prepared by high-speed shearing at 10,000 rpm for 3 min with an aqueous solution containing 2% (w / w) Tween 80 as the aqueous phase, peanut oil diglyceride oil with 70% DAG content as the oil phase, a water-oil volume ratio of 3:7, and a Tween 80 emulsion containing the same amount of ferulic acid as the Pickering emulsion prepared by high-speed shearing at 10,000 rpm for 3 min with an aqueous solution containing 2% (w / w) Tween 80 as the aqueous phase, peanut oil diglyceride oil with 70% DAG content containing 1.99% (w / w) ferulic acid as the oil phase, a water-oil volume ratio of 3:7, and a pure oil phase) during storage at 25°C for 15 days: Figure A shows the hydroperoxide value, and Figure B shows the thiobarbituric acid reactant (TBARS) value. Figure 9 and Figure 10 It can be seen that the ternary complex particles formed under this condition have high antioxidant activity, and the Pickering emulsion stabilized by them has good oxidative stability.

[0068] Comparative Example 1

[0069] The steps and conditions of Example 1 were compared, except that the concentration of α-cyclodextrin in the aqueous dispersion in step (1) was 0.5% (w / w). Under the conditions of this comparative example, a Pickering emulsion could not be formed.

[0070] Figure 11 This is the appearance of the product formed in Comparative Example 1. Under these conditions, oil-water separation occurs and the emulsion cannot be stabilized.

[0071] Comparative Example 2

[0072] The steps and conditions of Reference Example 2 were the same, except that the stirring time in step (2) was 0.5 h. Under the conditions of this comparative example, no Pickering emulsion could be formed.

[0073] Figure 12 This is the appearance of the product formed in Comparative Example 2. Under these conditions, oil-water separation occurred and the emulsion could not be stabilized.

[0074] Comparative Example 3

[0075] The steps and conditions of Reference Example 3 were used, except that the volume ratio of the aqueous phase to the oil phase in step (2) was 7:3. Under the conditions of this comparative example, a Pickering emulsion could not be formed.

[0076] Figure 13 This is a microscope image of the product formed in Comparative Example 3. Under this condition, the emulsion demulsification phenomenon is serious and the emulsion cannot be stabilized.

[0077] Comparative Example 4

[0078] The steps and conditions of Example 1 were compared, except that the polyphenol added in step (2) was epigallocatechin gallate. Under the conditions of this comparative example, ternary composite particles that stabilized the Pickering emulsion could not be formed.

[0079] Figure 14 This is a microscope image of the product formed in Comparative Example 4. Under this condition, the emulsion demulsification phenomenon is serious and the emulsion cannot be stabilized.

[0080] Comparative Example 5

[0081] Refer to the steps and conditions of Example 1, except that in step (2), peanut diglyceride oil and α-cyclodextrin were first mixed and stirred at 40°C and 500 rpm for 0.5 h, and then rutin was added and stirred for a further 0.5 h. Under the conditions of this comparative example, no ternary complex-stabilized Pickering emulsion or ternary composite particles could be formed.

[0082] Figure 15 This is a microscopic image of the product formed in Comparative Example 5. Under these conditions, the emulsion demulsifies severely and cannot be stabilized. No rutin particles are observed outside the emulsion droplets, and no ternary composite particles can be formed.

[0083] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be considered as equivalent replacement methods and are included in the scope of protection of the present invention.

Claims

1. A method for preparing a high antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles, characterized in that The following steps are involved: The aqueous dispersion of cyclodextrin is used as the aqueous phase, mixed with the oil phase and polyphenols at the same time, and stirred to obtain the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles stabilized by high antioxidant Pickering emulsion; The concentration of the cyclodextrin aqueous dispersion is 1%-15%; The volume ratio of the water phase to the oil phase is 6:4-2:8; The molar ratio of the polyphenols to the cyclodextrin is 1:10-2:1; The polyphenols include at least one of rutin, p-hydroxybenzoic acid, caffeic acid, quercetin, and ferulic acid; The stirring and mixing refers to stirring at a stirring rate of 250-500 rpm and a temperature of 10-40° C. for 1-6 hours.

2. The method for preparing the highly antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles according to claim 1, characterized in that: The cyclodextrin is at least one of α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin.

3. The method for preparing the highly antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles according to claim 1, characterized in that: The oil phase is at least one of soybean oil, linseed oil, peanut oil, sunflower oil, corn oil, camellia oil, and peanut oil diglyceride oil with a diglyceride content of 15%-80%, linseed oil diglyceride oil with a diglyceride content of 15%-80%, camellia oil diglyceride oil with a diglyceride content of 15%-80%, and corn oil diglyceride oil with a diglyceride content of 15%-80%.

4. A high antioxidant Pickering emulsion stabilized by cyclodextrin-polyphenol-oil molecule self-assembled ternary particles prepared by the method according to any one of claims 1 to 3.

5. A cyclodextrin-polyphenol-oil molecule self-assembled ternary particle, characterized in that The cyclodextrin-polyphenol-oil molecule self-assembled ternary particles are prepared by the following method: centrifuging the highly antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles in claim 4, removing the supernatant, washing the obtained precipitate with a non-polar solvent, and then drying to obtain the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles.

6. The cyclodextrin-polyphenol-oil molecule self-assembled ternary particles according to claim 5, characterized in that: The centrifugation refers to centrifugation at 15-25 ℃, 2000-4000 rpm, for 15-30 minutes; The non-polar solvent is at least one of petroleum ether, cyclohexane, hexane, and pentane; The drying refers to freeze drying.

7. Use of the highly antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles according to claim 4 or the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles according to claim 5 in the food industry and daily skin care products.

8. Use of the highly antioxidant Pickering emulsion stabilized by the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles according to claim 4 or the cyclodextrin-polyphenol-oil molecule self-assembled ternary particles according to claim 5 in functional foods and special medical foods.

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