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CN118949257B - NHDC/pyruvic acid binary liquid supermolecule self-assembly system and preparation method thereof - Google Patents

NHDC/pyruvic acid binary liquid supermolecule self-assembly system and preparation method thereof Download PDF

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Publication number
CN118949257B
CN118949257B CN202411420755.7A CN202411420755A CN118949257B CN 118949257 B CN118949257 B CN 118949257B CN 202411420755 A CN202411420755 A CN 202411420755A CN 118949257 B CN118949257 B CN 118949257B
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Prior art keywords
pyruvic acid
assembly system
binary liquid
dihydrochalcone
neohesperidin dihydrochalcone
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CN118949257A (en
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王琴
陈淑娴
丁云连
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Wuxi Inspection And Testing Certification Research Institute Wuxi Metrology And Testing Institute Wuxi Fiber Inspection Center
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Wuxi Inspection And Testing Certification Research Institute Wuxi Metrology And Testing Institute Wuxi Fiber Inspection Center
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Abstract

The invention discloses an NHDC/pyruvic acid binary liquid supermolecule self-assembly system and a preparation method thereof, and belongs to the technical field of supermolecules. The method for preparing the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system comprises the steps of mixing pyruvic acid with novel methyl hesperidin dihydrochalcone to prepare the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system. The method of the invention obviously improves the water solubility, oxidation resistance and bacteriostasis of the neohesperidin dihydrochalcone.

Description

NHDC/pyruvic acid binary liquid supermolecule self-assembly system and preparation method thereof
Technical Field
The invention relates to an NHDC/pyruvic acid binary liquid supermolecule self-assembly system and a preparation method thereof, belonging to the technical field of supermolecules.
Background
Neohesperidin dihydrochalcone (NHDC) is a flavonoid derivative obtained by hydrogenation of neohesperidin extracted from Oxytropis myriophyllum. In order to improve the solubility of the neohesperidin dihydrochalcone, the prior art mainly attempts to solve the problem of the solubility of the neohesperidin dihydrochalcone through a series of methods such as wrapping treatment, chemical modification and the like of the neohesperidin dihydrochalcone. However, the processes are too complicated and some organic solvents are used, and the solubility of the obtained novel methyl hesperidin dihydrochalcone is improved but the stability is poor and the novel methyl hesperidin dihydrochalcone cannot be directly used as a raw material.
Specifically:
Patent CN 109730294A discloses a method for increasing the water solubility of neohesperidin dihydrochalcone by using an embedding technology and using glucan-soy isolate protein coupling grafting, but the preparation process is complex, a special reaction device is needed, and the solubility is 4 g/L.
Patent CN 109730295A discloses a process for preparing new methyl hesperidin dihydrochalcone inclusion by using special granulating equipment, the water solubility of the new methyl hesperidin dihydrochalcone is improved to a certain extent, but the equipment cost is additionally increased, and the solubility is 4 g/L.
Patent CN 109836513A discloses a new preparation of octenyl succinic acid alpha-hydroxypropyl-beta-cyclodextrin ester, which is used for embedding with new methyl hesperidin dihydrochalcone, increasing the water solubility of new methyl hesperidin dihydrochalcone, but the preparation of octenyl succinic acid alpha-hydroxypropyl-beta-cyclodextrin ester causes additional cost, and a large amount of organic solvents are needed in the preparation process, so that the environmental protection benefit is poor, and the solubility is 2.52 g/L.
Patent CN 110156852A discloses a chemical method for improving solubility by glycosylation of neohesperidin dihydrochalcone, although the solubility of neohesperidin dihydrochalcone is increased to a certain extent, the process flow adopts a method of synthesizing derivatives by enzyme catalysis, which is relatively complex, and the solubility is 562.7 g/L.
In view of the important application and practical value of the neohesperidin dihydrochalcone, a simpler and green treatment process is needed, and the problems of poor water solubility and instability of the neohesperidin dihydrochalcone are solved more effectively.
Pyruvic acid is an ionic form of beta-hydroxybutyric acid, one of the important intermediates for ketone body metabolism in vivo. It plays an important role in energy metabolism and ketone body production. The main effects include ketone body energy supply, glycogen metabolism, fat metabolism regulation and ketoacidosis regulation. Pyruvic acid has certain antioxidation effect, can reduce the generation of free radicals and oxidative damage, protects cells from the influence of oxidative stress, and is an intermediate of three nutrient substances of human bodies.
Supramolecular compounds are complex and organized chemical systems formed by non-covalent interactions between a host molecule and several guest molecules. From the chemical point of view, each molecule composing the supermolecule system is not changed, so that the original efficacy can be maintained, but the solubility, bioavailability, stability and the like of each single component in the supermolecule system are greatly improved, namely, the interaction of various molecules of the supermolecule system forms a synergistic effect.
However, no research is currently underway to greatly enhance the solubility of neohesperidin dihydrochalcone by using the supramolecular technique.
Disclosure of Invention
Aiming at the problems, the invention provides a novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system and a preparation method thereof, which improve the water solubility, antibacterial property and oxidation resistance of the novel methyl hesperidin dihydrochalcone.
A first object of the present invention is to provide a method for preparing a novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system, which comprises:
And mixing pyruvic acid with neohesperidin dihydrochalcone to prepare a neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system.
In one embodiment, the molar ratio of pyruvic acid to neohesperidin dihydrochalcone is 0.1-1:0.01;
optionally, the molar ratio of pyruvic acid to neohesperidin dihydrochalcone is 0.1-0.5:0.01.
In one embodiment, the mixing is that pyruvic acid and neohesperidin dihydrochalcone are stirred in air or inert gas at 15-70 ℃ for more than 2 hours, and the stirring speed is 300-500 rpm;
Optionally, stirring for 2 hours at 25-60 ℃.
In one embodiment, the pH of the neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system is 2.5-4.5.
In one embodiment, the mass fraction of the neohesperidin dihydrochalcone in the neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system is 12% -41%.
In one embodiment, mixing a neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system with water to prepare a neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system water solution, wherein the mass fraction of the neohesperidin dihydrochalcone in the water solution is 0.1% -30%;
optionally, the mass fraction is 0.1% -25%.
In one embodiment, the neohesperidin dihydrochalcone is good in stability and cannot be separated out when the mass fraction of the neohesperidin dihydrochalcone in the aqueous solution is 0.1% -30%.
The second purpose of the invention is to provide a novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system prepared by any one of the above methods.
In one embodiment, in the neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system, pyruvic acid can effectively adjust the pH value of the system, and meanwhile, the neohesperidin dihydrochalcone has a synergistic effect, so that the system has multiple effects of resisting bacteria, preserving moisture, resisting oxidation, relieving, repairing and the like.
In one embodiment, in the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system, the water solubility of the novel methyl hesperidin dihydrochalcone is changed by forming intermolecular hydrogen bonds, and the process flow is green, simple and has no environmental pollution problem, thus being suitable for large-scale preparation.
In one embodiment, the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system can be directly applied to the fields of cosmetics, medicines, foods and the like and does not need additional post-treatment such as separation, purification and the like.
In one embodiment, the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system prepared by the invention can be directly diluted by water, and the maximum dilution can still keep the stability of the system and no solid precipitation, thereby being beneficial to formula application.
The third object of the invention is to provide the application of any one of the above methods or the above novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system in the fields of cosmetics, medicines or foods.
In one embodiment, applications in the food field include preparing general foods and specialty foods.
In one embodiment, the general food includes, but is not limited to, a drink, a baked good, a food additive, or a fermented food.
In one embodiment, the specific food product includes, but is not limited to, a health product, a functional food, or a dietary supplement.
In one embodiment, applications in the pharmaceutical arts include, but are not limited to, the preparation of liver protection drugs, hypoglycemic drugs, hypolipidemic drugs, anti-inflammatory or antioxidant drugs, intestinal flora modulating drugs.
In one embodiment, the use in the cosmetic field includes the preparation of a non-functional cosmetic, functional cosmetic or fragrance.
In one embodiment, the efficacy of the efficacy cosmetic includes, but is not limited to, whitening, soothing, moisturizing, antioxidant, anti-aging, anti-inflammatory, anti-free radical.
The fourth object of the invention is to provide a product containing the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system;
alternatively, the product includes, but is not limited to, a cosmetic, a pharmaceutical or a food product.
The fifth object of the invention is to provide a method for simultaneously improving the solubility, oxidation resistance and antibacterial property of neohesperidin dihydrochalcone, which comprises the steps of mixing pyruvic acid and neohesperidin dihydrochalcone according to a molar ratio of 0.1-1:0.01, stirring in air or inert gas at 25-50 ℃ for 2-6 h, and cooling to normal temperature to prepare a neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system with improved solubility, oxidation resistance and antibacterial property.
The invention has the beneficial effects that:
the neohesperidin dihydrochalcone/pyruvic acid system obtained by supermolecule self-assembly is in a stable liquid state, can be mixed with water in a specific proportion without precipitation, and effectively improves the water solubility and stability of the neohesperidin dihydrochalcone.
Specifically:
(1) The invention prepares a uniform, transparent and stable new methyl hesperidin dihydrochalcone/pyruvic acid binary liquid system by a supermolecule self-assembly technology, wherein the content of the new methyl hesperidin dihydrochalcone in the system can be up to 40 percent, which is far higher than the actual application concentration of the new methyl hesperidin dihydrochalcone, and a sufficient adjusting space is applied to the subsequent formula.
(2) The neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system prepared by the invention obviously enhances the water solubility of the neohesperidin dihydrochalcone, can be mutually dissolved with water, has the mass fraction of the neohesperidin dihydrochalcone up to 30% after mutual dissolution, and does not have any precipitation of solid neohesperidin dihydrochalcone particles.
(3) The novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system prepared by the invention is transparent, has low viscosity, can be directly used as a raw material, and can maintain long-term stability.
(4) The pyruvic acid in the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system prepared by the invention can effectively adjust the pH of the system, and has a synergistic effect with the novel methyl hesperidin dihydrochalcone.
(5) The preparation method of the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system is green and simple, the preparation condition is mild, and the obtained system can be directly put into application without post-treatment such as separation and purification.
In conclusion, the preparation method disclosed by the invention is environment-friendly and simple in flow, and can be used for remarkably improving the water solubility, antibacterial property and stability of the neohesperidin dihydrochalcone, so that the preparation method has an important significance for the application of the neohesperidin dihydrochalcone, and can be widely applied to the fields of cosmetics, foods, biological medicines and the like.
Drawings
FIG. 1 is an infrared spectrogram of a binary liquid supermolecule self-assembly system prepared in example 1;
FIG. 2 shows the DPPH removal rate of the aqueous solution of the binary liquid supermolecule self-assembly system prepared in example 1;
FIG. 3 shows the ABTS clearance of aqueous solutions of binary liquid supramolecular self-assembly systems prepared in example 1;
FIG. 4 shows the appearance of binary liquid supermolecule self-assembled systems prepared in example 1, example 2, comparative example 1 and comparative example 2.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more clear and clear, the present invention will be further described in detail below with reference to the accompanying drawings and examples. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
The invention provides a novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system and provides an embodiment of a preparation method. Traditionally, the novel methyl hesperidin dihydrochalcone has poor water solubility, so that the product is unstable and is not easy to store, thereby reducing the efficacy of the product and affecting the further development and utilization of the product. Thus, measures are needed to increase the solubility of neohesperidin dihydrochalcone and to enhance product stability.
The invention can well solve the problems by utilizing the supermolecule self-assembly technology and changing the water solubility and stability of the novel methyl hesperidin dihydrochalcone through forming intermolecular hydrogen bonds. Meanwhile, the proportion and interaction of the neohesperidin dihydrochalcone and pyruvic acid in the supermolecule self-assembly system are adjusted, so that the applicability of the neohesperidin dihydrochalcone can be obviously improved, the neohesperidin dihydrochalcone can be uniformly dispersed in the water-based skin care product, the stability and the absorbability of the product are improved, the texture, the stability and the efficacy of the related product are improved, and the use experience of a user and the functional effect of the product are improved.
The invention discloses a method for preparing a novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system, which comprises the following steps:
Weighing a certain amount of pyruvic acid and neohesperidin dihydrochalcone, placing the pyruvic acid and the neohesperidin dihydrochalcone into a sealed container, stirring uniformly, then raising the system to a specific temperature, stirring at the temperature for a certain time until the system becomes a uniform and transparent liquid system, cooling the system to room temperature to obtain a target neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembled system, and enabling the obtained system to be mutually soluble with water in a specific proportion, thereby effectively improving the water solubility and stability of the neohesperidin dihydrochalcone.
In the invention, the molar ratio of the raw material n (neohesperidin dihydrochalcone) n (pyruvic acid) is preferably 0.01:0.1-1, more preferably 0.01:0.1-0.8, most preferably 0.01:0.1-0.5, and in particular, in the embodiment of the invention, the molar ratio can be 0.01:0.1, 0.01:0.3 or 0.01:0.5.
In the present invention, the heating atmosphere is inert atmosphere or natural air, preferably helium, nitrogen, argon, carbon dioxide or natural air, and in particular, in the embodiment of the present invention, the heating atmosphere is natural air or nitrogen.
In the present invention, the heating temperature is preferably 20 to 120 ℃, more preferably 20 to 100 ℃, and most preferably 25 to 50 ℃, and in particular, in the embodiment of the present invention, may be 25 ℃, 30 ℃ or 50 ℃.
In the invention, the heating time is preferably 1-24 hours, more preferably 2-12 hours, most preferably 2-6 hours, and in particular, in the embodiment of the invention, 2 h, 4 h or 6h can be adopted.
In the invention, the pH of the binary liquid supermolecule self-assembly system is 2.5-4.5, and in the embodiment of the invention, the pH can be 2.12, 2.87 or 3.56.
In the invention, the mass fraction of the neohesperidin dihydrochalcone in the binary liquid supermolecule self-assembly system can reach 40%, and in the embodiment of the invention, the mass fraction can be 12%, 19% or 41%.
In the invention, the binary liquid supermolecule combination can be dissolved in water with a specific proportion, so that the mass fraction of the neohesperidin dihydrochalcone in the water solution can be kept at 0.1% -30% without precipitation, and in particular, in the embodiment of the invention, the mass fraction can be 0.1%, 15% or 30%.
Specifically, the normal temperature of the present invention means 25 ℃.
In order to further illustrate the invention, the following embodiment is used for describing the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system and the preparation method thereof in detail.
The detection method comprises the following steps:
the fourier infrared spectrum test parameters were:
the machine specification iS Nicolet iS5, the machine manufacturer iS Simer Feier technology company in U.S., the experimental parameters are scanning range of 450-4000 cm -1, and the resolution iS 4 cm -1.
High-low temperature cycle test:
The new methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule combination is frozen at-5 ℃, then placed at 40 ℃ for dissolution, which belongs to 1 cycle, then repeated, and the state after each dissolution is observed to keep stable and uniform liquid without solid precipitation, and the examples are data of 15 cycles.
Example 1
1. A method for preparing a novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system comprises the following steps:
placing 0.1 mol (8.8 g) of pyruvic acid and 0.01 mol (6.12 g) of neohesperidin dihydrochalcone in a closed container, stirring at 400rpm at normal temperature for 2h to obtain a binary liquid supermolecule self-assembled system, wherein the mass fraction of the neohesperidin dihydrochalcone in the system is 41%, and testing the pH value of the system by using a pH meter to be 3.56;
The binary liquid supermolecule self-assembly system is mixed with water in a specific proportion, so that the mass fraction of the neohesperidin dihydrochalcone in the aqueous solution is 30%, namely the solubility is 428.6 mg/g, and the system can keep a stable and uniform liquid state, thus obtaining the binary liquid supermolecule self-assembly system aqueous solution.
And respectively carrying out high-low temperature cycle test (15 times of cycle storage at-5 ℃ and 40 ℃) on the binary liquid supermolecule self-assembly system and the binary liquid supermolecule self-assembly system aqueous solution, and finally keeping stable and uniform liquid state of the two systems without solid precipitation.
And (3) placing the prepared uniform transparent stable binary liquid supermolecule self-assembly system at normal temperature for 24h, and performing data characterization by using an infrared spectrometer for sampling.
The infrared spectrogram of the binary liquid supermolecule self-assembly system is shown in fig. 1, and the result shows that the absorption peak of the binary liquid supermolecule self-assembly system prepared in the embodiment 1 corresponds to the absorption peak of hydroxyl (hydrogen bond) in the range of 3500-3200 cm -1, compared with pyruvic acid, the binary liquid supermolecule self-assembly system has obvious peak, compared with neohesperidin dihydrochalcone, the peak position obviously moves to low wave number, and the peak position is influenced by interaction of a large number of hydrogen bonds generated in the system. In addition, the carbonyl peak at 1636 cm -1 moves to 1734 at cm -1 in the high wavenumber direction relative to neomethyl hesperidin dihydrochalcone, which is due to the change in carbonyl electron cloud density caused by the generation of numerous hydrogen bonds within the system. The above results all confirm that pyruvic acid and neomethyl hesperidin dihydrochalcone form a supermolecule self-assembly system through intermolecular hydrogen bonds.
2. Performance detection
Adding triple distilled water into the binary liquid supermolecule self-assembly system obtained in the example 1 to prepare binary liquid supermolecule self-assembly system aqueous solutions with the concentration of the neohesperidin dihydrochalcone of 0.1 mg/mL, 0.2 mg/mL, 0.4 mg/mL, 0.6 mg/mL, 0.8 mg/mL and 1 mg/mL, and performing an antioxidation test by taking a neohesperidin dihydrochalcone standard solution with an equal concentration and a pyruvic acid solution with an equal concentration as a control.
(1) DPPH radical scavenging method for determining oxidation resistance.
The DPPH free radical has stronger absorption peak at 517nm wavelength visible light and shows purple color, when the neohesperidin dihydrochalcone free radical is combined with electrons provided by an oxidation resistance sample in a pairing way, the purple color disappears and becomes colorless or faint yellow, and the absorbance before and after the reaction is measured by an ultraviolet-visible spectrophotometer to show the color change.
Weighing DPPH 5.0 mg, dissolving with proper amount of absolute ethyl alcohol, fully dissolving with light-shielding ultrasonic, and then preparing into DPPH solution with concentration of 50 mug/mL by using absolute ethyl alcohol to fix volume to 100 mL.
Solutions were prepared in 96-well plates according to table 1:
TABLE 1
After the sample solutions were mixed uniformly, the reaction was conducted at 25℃in the absence of light for 30 min, and the absorbance was measured at a wavelength of 517: 517 nm.
Radical scavenging was calculated according to the following formula:
P is the clearance, A a、Ab、Ac、Ad, and corresponds to the absorbance value of each well in the table.
The results are shown in Table 2 and FIG. 2, and the results show that the DPPH clearance rate of the aqueous solution of the binary liquid supermolecule self-assembly system is superior to that of the single-component neohesperidin dihydrochalcone and pyruvic acid.
TABLE 2 DPPH detection results
(2) ABTS radical scavenging method measures oxidation resistance.
The ABTS is oxidized to generate more stable ABTS free radical, which shows blue-green color and has maximum absorption peak at 734 nm wavelength visible light. The sample is discolored after being reacted with ABTS free radical, and the absorbance value after the reaction is measured to compare the free radical clearance. The oxidation resistance a 0 value of the sample was determined by comparing the clearance with the clearance of neohesperidin dihydrochalcone, using the relative half clearance.
An aqueous ABTS solution of 7 mmol/L and an aqueous potassium persulfate solution of 2.45 mmol/L were provided. The above solutions were mixed uniformly in equal volumes, left in a dark environment for 12 h times, and diluted with deionized water to an absorbance value a 734 nm =0.70±0.02 as a measurement solution (ABTS solution).
Solutions were prepared in 96-well plates according to table 3:
TABLE 3 Table 3
After the sample solutions were mixed uniformly, the reaction was conducted at 25℃in the absence of light for 5 min, and the absorbance was measured at a wavelength of 734 nm.
Radical scavenging was calculated according to the following formula:
P is the clearance, A a、Ab、Ac、Ad, and corresponds to the absorbance value of each well in the table.
The results are shown in Table 4 and FIG. 3, and the results show that the ABTS clearance of the aqueous solution of the binary liquid supermolecule self-assembly system is superior to that of the single-component neohesperidin dihydrochalcone and pyruvic acid.
TABLE 4 ABTS detection results
The comprehensive results show that the binary liquid supermolecule self-assembly system aqueous solution has excellent antioxidant capacity, and compared with the neohesperidin dihydrochalcone standard substance and pyruvic acid, the antioxidant capacity of the sample is improved, and supermolecule synergistic effect is shown.
(3) Antibacterial property
Adding triple distilled water into the binary liquid supermolecule self-assembly system obtained in the example 1 to prepare binary liquid supermolecule self-assembly system aqueous solutions with different neohesperidin dihydrochalcone concentrations. An antibacterial test was performed with triple distilled water as a control.
The streptococcus bacteria liquid cultured overnight for recovery is inoculated into 5mL THB liquid culture medium according to the inoculum size of 1% v/v, and is subjected to static culture for 24h in an incubator with 37 ℃ and 5% CO 2. And taking out the bacteria for standby when the bacterial load reaches 10 9 CFU/mL after the bacteria grow to the logarithmic growth medium stage.
Sterile operation is carried out in a biosafety cabinet, aqueous solutions of binary liquid supermolecule self-assembly systems with different concentrations are respectively added into sterile 96-well culture plates, liquid medicine is added into 1 st to 9 th wells, 100 mu L of each well is added, and 100 mu L of triple distilled water is added into 10 th wells to serve as a control.
Ten times of the culture inoculum solution is diluted by a culture medium, diluted and added into a corresponding 96-well culture plate according to 100 mu L/well, the culture inoculum solution is placed in an incubator with 37 ℃ and 5% CO 2 for standing and incubation for 24 hours after being sealed, and the antibacterial effect of the binary liquid supermolecule self-assembly system aqueous solution is observed.
After 24h incubation of drug and bacteria, 100 μl of THB-coated plates were taken from each well and incubated in an incubator at 37 ℃ with 5% co 2 for 24h at the lowest drug concentration for complete sterile growth, designated MIC. The significant growth test of bacteria in the positive control wells (i.e., without drug) is only significant.
The minimum complete inhibitory concentration plate experiment proves that the binary liquid supermolecule self-assembly system has obvious inhibitory effects on streptococcus mutans, streptococcus suis serotype 2 and streptococcus group A, and the results are shown in table 5, and the minimum inhibitory concentration of the binary liquid supermolecule self-assembly system is at the mg/mL level. Namely, the binary liquid supermolecule self-assembly system has good efficacy in the aspect of antibacterial performance.
TABLE 5 antibacterial effect
Example 2
The preparation method of the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system comprises the following steps:
placing 0.3 mol (26.4 g) of pyruvic acid and 0.01 mol (6.12 g) of neohesperidin dihydrochalcone in a closed container, ensuring that the container is slowly heated up in a natural air atmosphere, continuously heating and stirring for 4h after the temperature is raised to 30 ℃, cooling the container to normal temperature to obtain a binary liquid supermolecule self-assembly system, wherein the mass fraction of the neohesperidin dihydrochalcone in the system is 19%, and testing the pH value of the system by using a pH meter to be 2.87;
The binary liquid supermolecule self-assembly system is mixed with water in a specific proportion, so that the mass fraction of the neohesperidin dihydrochalcone in the aqueous solution is 15%, namely the solubility is 176.5 mg/g. The system can keep stable and uniform liquid state to obtain a binary liquid supermolecule self-assembly system aqueous solution;
And respectively carrying out high-low temperature cycle test (15 times of cycle storage at-5 ℃ and 40 ℃) on the binary liquid supermolecule self-assembly system and the binary liquid supermolecule self-assembly system aqueous solution, and finally keeping stable and uniform liquid state of the two systems without solid precipitation.
Example 3
The preparation method of the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system comprises the following steps:
Placing 0.5 mol (44 g) of pyruvic acid and 0.01 mol (6.12 g) of neohesperidin dihydrochalcone in a closed container, ensuring that the container is slowly heated up in a natural air atmosphere, continuously heating and stirring for 6h after the temperature is raised to 50 ℃, cooling the container to normal temperature to obtain a binary liquid supermolecule self-assembly system, wherein the mass fraction of the neohesperidin dihydrochalcone in the system is 12%, and testing the pH value of the system by using a pH meter to be 2.12;
The binary liquid supermolecule self-assembly system is mixed with water in a specific proportion, so that the mass fraction of the neohesperidin dihydrochalcone in the aqueous solution is 0.1%, namely the solubility is 1 mg/g. The system can keep stable and uniform liquid state to obtain a binary liquid supermolecule self-assembly system aqueous solution;
And respectively carrying out high-low temperature cycle test (15 times of cycle storage at-5 ℃ and 40 ℃) on the binary liquid supermolecule self-assembly system and the binary liquid supermolecule self-assembly system aqueous solution, and finally keeping stable and uniform liquid state of the two systems without solid precipitation.
Comparative example 1
The method is characterized in that 0.1 mol pyruvic acid and 0.01 mol neomethyl hesperidin dihydrochalcone are placed in a closed container, the container is guaranteed to be slowly heated in a natural air atmosphere, heating is carried out to 80 ℃ and then continuous heating and stirring are carried out for 2h, the system is changed into a uniform transparent liquid state along with the time.
As a result, as shown in FIG. 4, the heating temperature was increased only as compared with example 1, but the color of the system was deepened, and it was presumed that a chemical reaction might occur during the reaction.
Comparative example 2
The solution was prepared by placing 0.1 mol pyruvic acid and 0.01 mol neomethyl hesperidin dihydrochalcone in a closed container, stirring at 400rpm at room temperature for 1h, and the system state was a solid-liquid mixture over time.
As a result, as shown in FIG. 4, compared with example 1, the stirring time was shortened, a uniform and stable transparent liquid system could not be obtained, the system was kept in a solid-liquid mixed state, and this system was mixed with water in a specific ratio so that the mass fraction of neohesperidin dihydrochalcone was 30%, i.e., the solubility was 428.6 mg/g, but the system could not be kept in a stable and uniform liquid state, and solid insoluble matters were present.
Comparative example 3
The new methyl hesperidin dihydrochalcone of 0.02 mol and the pyruvic acid of 0.2 mol are placed in a closed container and stirred for 2 hours at 400rpm at normal temperature, and the system state is a solid-liquid mixture along with the time.
Compared with the example 1, only the feeding amount of the neohesperidin dihydrochalcone is increased, a uniform and stable transparent liquid system cannot be obtained, the system is kept in a solid-liquid mixed state, and the system is mixed with water in a specific proportion, so that the mass fraction of the neohesperidin dihydrochalcone is 30%, namely, the solubility is 428.6 mg/g, but the system cannot keep a stable and uniform liquid state, and solid insoluble matters exist.
Comparative example 4
The new methyl hesperidin dihydrochalcone of 0.02 mol and lactic acid of 0.2 mol are placed in a closed container and stirred for 2 hours at 400rpm at normal temperature, and the system state is a solid-liquid mixture along with the time.
Compared with the embodiment 1, lactic acid is selected to replace pyruvic acid, a uniform and stable transparent liquid system cannot be obtained, the system is kept in a solid-liquid mixed state, and the system is mixed with water in a specific proportion, so that the mass fraction of the neohesperidin dihydrochalcone is 30%, namely the solubility is 428.6 mg/g, but the system cannot keep a stable and uniform liquid state, and solid insoluble matters exist.
Comparative example 5
0.02 Mol glycyrrhizic acid and 0.2 mol pyruvic acid are placed in a closed container, stirred at 400rpm for 2 hours at normal temperature, and the system state is a solid-liquid mixture with the time.
Compared with the embodiment 1, glycyrrhizic acid is selected to replace neohesperidin dihydrochalcone, a uniform and stable transparent liquid system cannot be obtained, the system is kept in a solid-liquid mixed state, and the system is mixed with water in a specific proportion, so that the mass fraction of the glycyrrhizic acid is 30%, namely the solubility is 428.6 mg/g, but the system cannot keep a stable and uniform liquid state, and solid insoluble matters exist.
Comparative example 6
The solution was stirred at 400rpm for 2 hours at room temperature in a closed container with 0.02 mol glycyrrhetinic acid and 0.2. 0.2 mol pyruvic acid, and the system was a solid-liquid mixture over time.
Compared with the embodiment 1, the glycyrrhetinic acid is selected to replace the neohesperidin dihydrochalcone, a uniform and stable transparent liquid system cannot be obtained, the system is kept in a solid-liquid mixed state, and the system is mixed with water in a specific proportion, so that the mass fraction of the glycyrrhetinic acid is 30%, namely the solubility is 428.6 mg/g, but the system cannot keep a stable and uniform liquid state, and solid insoluble matters exist.
Comparative example 7
The cis-3-hexenyl ester of 0.1 mol pyruvic acid and the neomethyl hesperidin dihydrochalcone of 0.01 mol are placed in a closed container, and stirred at normal temperature for 2h, and the system is changed into a uniform transparent liquid state along with the time.
Compared with the example 1, the cis-3-hexenyl pyruvate is selected to replace pyruvic acid to obtain a uniform and stable transparent liquid system, the system is kept in a liquid state, and the system is mixed with water in a specific proportion, so that the mass fraction of neohesperidin dihydrochalcone is 30%, namely the solubility is 428.6 mg/g, but the system cannot keep a stable and uniform liquid state, and solid insoluble matters exist.
As can be seen from comparative examples 4-7, the prepared binary system is unstable and has the problem of poor solubility due to the replacement of one of pyruvic acid and neohesperidin dihydrochalcone. It can be seen that neohesperidin dihydrochalcone cannot form a binary liquid supermolecule self-assembly system with conventional acid, whereas pyruvic acid cannot form a binary liquid supermolecule self-assembly system with other insoluble compounds, and that the combination of pyruvic acid or neohesperidin dihydrochalcone has the specificity of raw materials.
While the invention has been described with reference to the preferred embodiments, it is not limited thereto, and various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.

Claims (10)

1. A method for preparing a neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system is characterized by comprising the steps of mixing pyruvic acid and neohesperidin dihydrochalcone according to a molar ratio of 0.1-1:0.01, stirring in air or inert gas at 25-50 ℃ for 2-6 h, and cooling to normal temperature to obtain the neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system.
2. The novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system prepared by the method of claim 1.
3. Use of the novel methyl hesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system according to claim 2 in the fields of cosmetics, pharmaceuticals or food preparation.
4. Use according to claim 3, characterized in that the use in the field of preparing food products comprises preparing drinks, bakery products, food additives, fermented food products.
5. The use according to claim 3, wherein the use in the field of preparing medicaments comprises preparing liver protection medicaments, hypoglycemic medicaments, hypolipidemic medicaments, anti-inflammatory medicaments, antioxidant medicaments, intestinal flora modulating medicaments.
6. Use according to claim 3, characterized in that the use in the cosmetic field comprises the preparation of non-functional cosmetics, functional cosmetics.
7. Use according to claim 3, characterized in that the use in the cosmetic field is the preparation of fragrances.
8. A cosmetic product characterized in that it comprises a neohesperidin dihydrochalcone/pyruvic acid binary liquid supermolecule self-assembly system according to claim 2.
9. A medicament comprising the neohesperidin dihydrochalcone/pyruvic acid binary liquid supramolecular self-assembly system according to claim 2.
10. A food product comprising the neohesperidin dihydrochalcone/pyruvic acid binary liquid supramolecular self-assembly system according to claim 2.
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