Hyaluronic acid peptide composition delivered by modification technology as well as preparation method and application of hyaluronic acid peptide composition

Abstract

The invention discloses a hyaluronic acid peptide composition delivered by a modification technology, which is prepared from the following components in percentage by mass: 1 to 10 percent of polysaccharide modified cyclodextrin, 0.05 to 0.5 percent of hyaluronic acid peptide, 0.01 to 0.5 percent of palmitic acid composite peptide, 0.1 to 0.8 percent of polyhydric alcohol and the balance of deionized water, and the sum of the mass percent of the components is 100 percent. The invention also discloses a preparation method and application of the hyaluronic acid peptide composition. After polysaccharide modified cyclodextrin inclusion treatment, the hyaluronic acid peptide composition freeze-dried powder obtained through a freeze-drying process is good in delivery effect and higher in activity, so that the instantaneity and the long-term tightening effect of the product are more remarkable; and the freeze-dried powder does not easily absorb moisture, is easy to dissolve, is completely transparent after being dissolved, does not shrink, has good stability and does not feel sticky and greasy when being used.

Description

Technical Field

[0001] The present invention belongs to the technical field of cosmetic composition synthesis, and specifically relates to a hyaluronic acid peptide composition delivered via modification technology, and also relates to a preparation method and application of the hyaluronic acid peptide composition. Background Art

[0002] Hyaluronic acid, a glycosaminoglycan, is known as the "ideal natural moisturizer." Decorin and perlecan are two other important proteoglycans in the dermis. Their protein components bind to collagen fibers, while their glycosaminoglycan (GAG) components separate and fill the spaces between them, resulting in finer collagen fibers and improved fiber quality and strength.

[0003] Hyaluronic acid peptide is tetradecylaminobutyrylvalinamidobutyryl urea trifluoroacetate. It is a modified tripeptide that helps combat skin sagging by increasing hyaluronic acid levels in the skin. This tripeptide also increases the expression of decorin and lumican, two important proteoglycans that support the formation of new collagen fibrils, increasing their mass and strength, with a noticeable remodeling effect. It has been shown to promote the renewal of the skin's own hyaluronic acid, resulting in a noticeable remodeling effect and firmer, more hydrated skin. It offers a new, injection-free solution that significantly improves skin firmness, softness, smoothness, and hydration in multiple facial areas. It mimics the body's own mechanism for converting latent TGF-β into its active form. This unique activation leads to an increase in the skin's own synthesis of hyaluronic acid and stimulates the production of lumican and decorin, two important proteoglycans responsible for maintaining a well-structured collagen matrix in the dermis. However, the current application of hyaluronic acid peptide raw materials is mostly in the form of a solution formed by adding solvent water after polyol dispersion as the matrix (such as DSM raw material SYN-HYCAN). This form has the following problems: (1) The degradation rate of hyaluronic acid peptide is high at room temperature, which is not conducive to the release of activity during application and has low bioavailability. In addition, the preservation, storage and transportation conditions are harsh and need to be carried out in the cold chain. There may be corruption problems during storage and transportation; (2) The polyol-dispersed hyaluronic acid peptide aqueous solution has poor solubility, the solution is white, and there is a risk of precipitation; (3) The hyaluronic acid peptide aqueous solution needs to be added with a large amount of polyol in advance. Experiments have shown that at least 5% of 1,2-hexanediol is used to stabilize 0.1% hyaluronic acid peptide in the aqueous solution. The skin feels thick and after adding a large amount of polyol, it is not suitable for freeze-dried powder dosage form. After freeze-drying, the powder shrinks and does not form. Summary of the Invention

[0004] The first objective of the present invention is to provide a hyaluronic acid peptide composition delivered via modification technology, which solves the problem of low stability of hyaluronic acid peptide compositions in the prior art.

[0005] The second object of the present invention is to provide a method for preparing a hyaluronic acid peptide composition delivered via modification technology.

[0006] The third object of the present invention is to provide the use of the hyaluronic acid peptide composition in a cosmetic matrix.

[0007] The first technical solution adopted by the present invention is that the hyaluronic acid peptide composition delivered by modification technology includes the following components by mass percentage: 1-10% modified cyclodextrin modified with polysaccharide, 0.05-0.5% hyaluronic acid peptide, 0.01-0.5% palmitic acid complex peptide, 0.1-0.8% polyol, and the rest is deionized water. The sum of the mass percentages of the above components is 100%.

[0008] The present invention is also characterized in that: The palmitic acid complex peptide is any one or more of palmitoyl tripeptide-1, palmitoyl tripeptide-5, palmitoyl pentapeptide-4, palmitoyl tetrapeptide-7, palmitoyl hexapeptide-12, and palmitoyl tripeptide-8.

[0009] The polyol is any one of 1,2-hexanediol, 1,3-propylene glycol, butanediol, and pentanediol.

[0010] The polysaccharide-modified modified cyclodextrin is any one of oat glucan-modified hydroxypropyl cyclodextrin, dendrobium officinale polysaccharide-modified hydroxypropyl cyclodextrin, and euglena polysaccharide-modified hydroxypropyl cyclodextrin.

[0011] The preparation process of polysaccharide-modified modified cyclodextrin is as follows: dissolve the polysaccharide in water, add sodium hydroxide alkaline solution, mix well, add hydroxypropyl cyclodextrin, ultrasonically vibrate at 40-60°C for 2-10 hours, then slowly drop 1,3-propylene glycol, continue to react at this temperature for 10-24 hours, filter the material and add isopropanol, precipitate the solid and centrifuge, place the centrifuged material in a vacuum drying oven to dry, and obtain polysaccharide-modified modified cyclodextrin; the polysaccharide is any one of oat glucan, dendrobium officinale polysaccharide, and fine algae polysaccharide.

[0012] The second technical solution adopted by the present invention is a method for preparing a hyaluronic acid peptide composition delivered by modification technology, specifically: The polysaccharide-modified modified cyclodextrin powder, hyaluronic acid peptide powder and palmitic acid complex peptide are mixed and stirred evenly, purified water is added, and the solution is slowly stirred until the solution is completely transparent and the inclusion is completed. A polyol is added and filtered to obtain an inclusion composition. The inclusion solution is vacuum freeze-dried to obtain a cake-like freeze-dried powder, which is the hyaluronic acid peptide composition. The vacuum freeze-drying process is as follows: freeze at -50 to -30°C for 2 to 8 hours, then evacuate and heat to -30 to -20°C, maintain for 4 to 15 hours; continue to heat to -20 to -10°C, maintain for 5 to 10 hours; then heat to -10 to 0°C, maintain for 4 to 8 hours; continue to heat to 0 to 20°C, maintain for 3 to 8 hours; finally, heat to 20 to 40°C and maintain for 3 to 20 hours.

[0013] The third technical solution adopted by the present invention is the use of a hyaluronic acid peptide composition delivered by modification technology in a cosmetic matrix. The beneficial effects of the present invention are: (1) The problem of poor solubility of hyaluronic acid peptide and inability to freeze-dry and form it was solved by polysaccharide-modified cyclodextrin inclusion treatment; (2) After the polysaccharide-modified modified cyclodextrin inclusion treatment, the hyaluronic acid peptide composition freeze-dried powder obtained by the freeze-drying process has good delivery efficacy and higher activity, making the product's immediate and long-term firming effect more significant; and the freeze-dried powder is not easy to absorb moisture and is easy to dissolve. After dissolution, it is completely transparent and does not shrink. It has good stability and does not feel sticky on the skin. (3) The combination of hyaluronic acid peptide and palmitoyl peptide has a significant synergistic effect on the anti-aging effect of the skin. The activity of hyaluronic acid peptide and palmitoyl peptide is preserved to the greatest extent after inclusion delivery and freeze-drying. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] Figure 1 This is a picture of a polyol hyaluronic acid peptide aqueous solution; Figure 2 This is a freeze-dried powder of the hyaluronic acid peptide composition prepared by the present invention; Figure 3 This is a diagram showing abnormal freeze-drying phenomenon of freeze-dried powder formed by freeze-drying hyaluronic acid peptide under normal application conditions; Figure 4 This is a freeze-dried state diagram of hyaluronic acid peptide after freeze-drying without modified hydroxypropyl cyclodextrin; Figure 5 This is a diagram of the solution state after the freeze-dried powder of the present invention is completely dissolved in water. DETAILED DESCRIPTION

[0015] The present invention will be described in detail below with reference to specific embodiments and the accompanying drawings.

[0016] The hyaluronic acid peptide composition delivered by the modification technology of the present invention comprises the following components by mass percentage: 1-10% of polysaccharide-modified modified cyclodextrin, 0.05-0.5% of hyaluronic acid peptide, 0.01-0.5% of palmitic acid complex peptide, 0.1-0.8% of polyol, and the rest is deionized water, and the sum of the mass percentages of the above components is 100%; The palmitic acid complex peptide is any one or more of palmitoyl tripeptide-1, palmitoyl tripeptide-5, palmitoyl pentapeptide-4, palmitoyl tetrapeptide-7, palmitoyl hexapeptide-12, and palmitoyl tripeptide-8; Preferably, the palmitoyl complex peptide is a compound of palmitoyl tripeptide-1, palmitoyl tripeptide-5, and palmitoyl tetrapeptide-7; The polyol is any one of 1,2-hexanediol, 1,3-propylene glycol, butanediol, and pentanediol; The polysaccharide-modified modified cyclodextrin is any one of oat glucan-modified hydroxypropyl cyclodextrin, Dendrobium officinale polysaccharide-modified hydroxypropyl cyclodextrin, and Euglena microcarpa polysaccharide-modified hydroxypropyl cyclodextrin; The polysaccharide-modified modified cyclodextrin is a supramolecular polymer formed by polysaccharide. The specific preparation process is as follows: the polysaccharide is completely dissolved in water, sodium hydroxide alkaline solution is added, and after mixing evenly, hydroxypropyl cyclodextrin is added. The reaction liquid is ultrasonically shaken at 40-60°C for 2-10 hours to form a reaction liquid. 1,3-propylene glycol is then slowly added dropwise as a linker. The reaction is continued at this temperature for 10-24 hours. After filtering the material, isopropyl alcohol is added, the solid is precipitated and further centrifuged. The centrifuged material is placed in a vacuum drying oven to dry to obtain a solid supramolecular polymer, namely the polysaccharide-modified modified cyclodextrin. The mass ratio of polysaccharide to hydroxypropyl cyclodextrin is 1:5-10; the mass ratio of polysaccharide to alkaline solution is 50:1; the mass ratio of linker 1,3-propylene glycol to reaction solution is 1:10; and the mass ratio of isopropyl alcohol to filter material is 5-8:1.

[0017] The polysaccharide is any one of oat glucan, dendrobium officinale polysaccharide, and euglena polysaccharide; The preparation method of the hyaluronic acid peptide composition delivered by modification technology is specifically as follows: polysaccharide-modified modified cyclodextrin powder, hyaluronic acid peptide powder and palmitic acid complex peptide are mixed and stirred evenly, purified water is added in small amounts and multiple times, and slowly stirred until the solution is completely transparent and inclusion is completed, polyol is added, and the inclusion composition is obtained by filtering, and the inclusion solution is vacuum freeze-dried to obtain the resulting cake-like freeze-dried powder, which is the hyaluronic acid peptide composition; The vacuum freeze-drying process is as follows: freezing at -50 to -30°C for 2 to 8 hours, then vacuuming, heating to -30 to -20°C, and maintaining for 4 to 15 hours; continuing to heat to -20 to -10°C, and maintaining for 5 to 10 hours; then heating to -10 to 0°C, and maintaining for 4 to 8 hours; continuing to heat to 0 to 20°C, and maintaining for 3 to 8 hours; and finally heating to 20 to 40°C, and maintaining for 3 to 20 hours to obtain a freeze-dried powder, namely the composition.

[0018] The application of the hyaluronic acid peptide composition delivered by the modification technology of the present invention is to mix the hyaluronic acid peptide composition with water and add it to a cosmetic matrix to form a cosmetic with anti-aging effect; the addition amount of the composition is 1% to 10% of the total mass of the cosmetic; the cosmetic matrix is ​​an aqueous solution, a facial mask, an essence, etc. The inclusion rate test results of hyaluronic acid peptide after polysaccharide-modified modified cyclodextrin inclusion and ordinary modified cyclodextrin inclusion hyaluronic acid peptide are as follows (UV spectrophotometry): Table 1 Inclusion rate test results

[0019] from Figure 1 、 Figure 5 It can be seen from the table that the water solubility of the hyaluronic acid peptide composition is significantly enhanced after inclusion of the freeze-dried polysaccharide-modified modified cyclodextrin. It can be seen from Table 1 that the inclusion capacity of the modified cyclodextrin modified by polysaccharide is also significantly improved. Figure 5 It can also be seen that after the freeze-dried powder is completely dissolved in water, the solution becomes clear and transparent.

[0020] Comparison of freeze-dried ordinary hyaluronic acid peptide aqueous solution, freeze-dried hyaluronic acid peptide composition after polysaccharide modified cyclodextrin inclusion, and freeze-dried hyaluronic acid peptide composition after unmodified modified cyclodextrin inclusion, as shown in the figure. Figure 2 、 Figure 3 、 Figure 4 As shown, it can be seen that the freeze-dried composition of the present invention is in good condition, in the form of a complete cake, without cracks or shrinkage.

[0021] Example 1 The hyaluronic acid peptide composition delivered by the modification technology includes the following components by mass percentage: 1.0% hydroxypropyl cyclodextrin modified with oat glucan, 0.05% hyaluronic acid peptide, 0.01% palmitic acid complex peptide, 0.1% polyol, and the rest is deionized water. The sum of the mass percentages of the above components is 100%; The palmitic acid complex peptide is a combination of palmitoyl tripeptide-1, palmitoyl tripeptide-5, and palmitoyl tetrapeptide-7, with a mass ratio of 1:1:1; the polyol is 1,2-hexanediol; The preparation process of oat glucan-modified hydroxypropyl cyclodextrin is as follows: 1g of oat β-glucan is completely dissolved in 100g of water, 20mg of sodium hydroxide is added to completely dissolve the alkaline solution, and after mixing evenly, 5g of hydroxypropyl cyclodextrin is added, and ultrasonic vibration is performed at 40°C for 2h. 1,3-propylene glycol (with a ratio of 1:10 to the feed liquid) is slowly added dropwise as a linker, and the reaction is carried out for 10h. After filtering the material, isopropanol (with a ratio of 5:1 to the feed liquid) is added, the solid is precipitated and further centrifuged. The centrifuged material is placed in a vacuum drying oven and dried to obtain a solid supramolecular polymer, namely, the polysaccharide-modified modified cyclodextrin. Oat glucan-modified hydroxypropyl cyclodextrin powder, hyaluronic acid peptide powder, and palmitic acid peptide were mixed and stirred evenly. Purified water was added in small amounts and stirred slowly until the solution became completely transparent. After inclusion, polyol was added and filtered to obtain an inclusion complex. The inclusion complex solution was vacuum freeze-dried to obtain a freeze-dried powder. The vacuum freeze-drying process is as follows: freezing at -50°C for 2 hours, then evacuating the temperature, heating to -30°C, and maintaining for 4 hours; continuing to heat to -20°C, and maintaining for 5 hours; then heating to -10°C, and maintaining for 4 hours; continuing to heat to 0°C, and maintaining for 3 hours; and finally heating to 20°C, and maintaining for 3 hours to obtain a freeze-dried powder, namely the composition.

[0022] The composition obtained in the above step is mixed with water and then added to the cosmetic base toner, and mixed to obtain a cosmetic with anti-aging effect. The addition amount is 1%, as shown in Table 2; Table 2 Toner formula

[0023] The treated hyaluronic acid peptide freeze-dried powder composition can be directly added to the cosmetic matrix after being dissolved in water, which solves the problem that palmitoyl polypeptide and hyaluronic acid peptide cannot be added to aqueous products due to their solubility problems, or the transparency is affected after addition, and they are easy to precipitate after addition.

[0024] Example 2 The hyaluronic acid peptide composition delivered by modification technology includes the following components by mass percentage: 10% hydroxypropyl cyclodextrin modified with oat glucan, 0.5% hyaluronic acid peptide, 0.5% palmitic acid complex peptide, 0.8% polyol, and the rest is deionized water, the total being 100%.

[0025] The palmitic acid complex peptide is a combination of palmitoyl tripeptide-1, palmitoyl tripeptide-5, and palmitoyl tetrapeptide-7, with a mass ratio of 1:1:1; the polyol is 1,3-propylene glycol; The preparation process of wheat glucan-modified hydroxypropyl cyclodextrin is as follows: 0.5g of oat β-glucan is completely dissolved in 100g of water, 10mg of sodium hydroxide is added to completely dissolve the alkaline solution, and after mixing evenly, 5g of hydroxypropyl cyclodextrin is added. The mixture is ultrasonically shaken at 60°C for 10 hours, and 1,3-propylene glycol (with a ratio of 1:10 to the liquid) is slowly added dropwise as a linker. The reaction is carried out for 24 hours. After filtering the material, isopropanol (with a ratio of 8:1 to the liquid) is added. The solid is precipitated and further centrifuged. The centrifuged material is placed in a vacuum drying oven and dried to obtain a solid supramolecular polymer, which is the polysaccharide-modified modified cyclodextrin. Oat glucan-modified hydroxypropyl cyclodextrin powder, hyaluronic acid peptide powder, and palmitic acid peptide complex were mixed and stirred uniformly. Purified water was added in small amounts and stirred slowly until the solution became completely transparent. The inclusion complex was then added with a polyol and filtered to obtain the inclusion complex. The inclusion complex solution was vacuum freeze-dried to obtain a freeze-dried powder cake.

[0026] The freeze-drying process is as follows: freezing at -30°C for 8 hours, then vacuuming, heating to -20°C, and maintaining for 15 hours; continuing to heat to -10°C, and maintaining for 10 hours; then heating to 0°C, and maintaining for 8 hours; continuing to heat to 20°C, and maintaining for 8 hours; and finally heating to 40°C, and maintaining for 20 hours to obtain a freeze-dried powder, namely the composition.

[0027] The composition obtained in the above steps was mixed with water and then added to the cosmetic base toner, and mixed to obtain a cosmetic with anti-aging effect. The addition amount was 10%, as shown in Table 3; Table 3 Toner formula

[0028] Example 3 The hyaluronic acid peptide composition delivered by modification technology includes the following components by mass percentage: 5% hydroxypropyl cyclodextrin modified with oat glucan, 0.225% hyaluronic acid peptide, 0.245% palmitic acid complex peptide, 0.35% polyol, and the rest is deionized water, the total being 100%.

[0029] The palmitic acid complex peptide is a combination of palmitoyl tripeptide-1, palmitoyl tripeptide-5, and palmitoyl tetrapeptide-7, with a mass ratio of 1:1:1; the polyol is 1,2-hexanediol; The preparation process of glucan-modified hydroxypropyl cyclodextrin is as follows: 0.8 g of oat β-glucan is completely dissolved in 100 g of water, 16 mg of sodium hydroxide is added to completely dissolve the alkaline solution, and after mixing evenly, 8 g of hydroxypropyl cyclodextrin is added. The mixture is ultrasonically shaken at 50°C for 6 hours, 1,3-propylene glycol (1:10 to the feed liquid) is slowly added dropwise as a linker, and the reaction is carried out for 16 hours. After filtering the material, isopropanol (6.5:1 to the feed liquid) is added, the solid is precipitated and further centrifuged. The centrifuged material is placed in a vacuum drying oven and dried to obtain a solid supramolecular polymer, namely, the polysaccharide-modified modified cyclodextrin. Oat glucan-modified hydroxypropyl cyclodextrin powder, hyaluronic acid peptide powder, and palmitic acid peptide were mixed and stirred evenly. Purified water was added in small amounts and stirred slowly until the solution became completely transparent. After inclusion, polyol was added and filtered to obtain an inclusion complex. The inclusion complex solution was vacuum freeze-dried to obtain a freeze-dried powder. The freeze-drying process is as follows: freezing at -40°C for 5 hours, then vacuuming, heating to -25°C, and maintaining for 9.5 hours; continuing to heat to -15°C, and maintaining for 7.5 hours; then heating to -5°C, and maintaining for 6 hours; continuing to heat to 10°C, and maintaining for 5.5 hours; and finally heating to 30°C, and maintaining for 11.5 hours to obtain a freeze-dried powder, namely the composition.

[0030] The composition obtained in the above steps was mixed with water and then added to the cosmetic base toner, and mixed to obtain a cosmetic with anti-aging effect. The addition amount was 5.5%, as shown in Table 4; Table 4 Toner formula

[0031] Comparative Example 1 This comparative example provides a method for preparing a freeze-dried composition for delivering hyaluronic acid peptides. The specific implementation method is the same as that of Example 1, except that oat glucan-modified hydroxypropyl cyclodextrin is not added.

[0032] Comparative Example 2 This comparative example provides a method for preparing a freeze-dried composition for delivering hyaluronic acid peptides. The specific implementation method is the same as that of Example 1, except that no palmitic acid complex peptide is added.

[0033] Comparative Example 3 This comparative example provides a method for preparing a freeze-dried composition for delivering hyaluronic acid peptides. The specific implementation method is the same as that of Example 1, except that no polyol is added before freeze-drying. By comparing Comparative Example 1 with Example 1, it can be found that the inclusion rate of the hyaluronic acid peptide after inclusion in the modified cyclodextrin modified with polysaccharide is higher, the inclusion process is simple, the permeability is higher, the absorbability is better, and the solubility is stronger; By comparing Comparative Example 2 with Example 1, it can be found that the anti-aging effect of the modified cyclodextrin inclusion compound of hyaluronic acid peptide modified by polysaccharide is more obvious than the inclusion compound of hyaluronic acid peptide not complexed with palmitoyl polypeptide; By comparing Comparative Example 3 with Example 1, it can be found that adding a small amount of polyol can improve the freeze-drying effect of the inclusion composition and no cracks appear.

[0034] Example 4 In order to determine the type of the composite palmitoyl polypeptide in the present invention, a large number of research experiments were conducted, and the specific experiments are as follows: 1. Hyaluronic acid peptide + 9% 1,2-hexanediol aqueous solution; 2. The solution of hyaluronic acid peptide after inclusion in modified cyclodextrin modified with polysaccharide; 3. The solution of hyaluronic acid peptide + palmitoyl tripeptide-1 after inclusion in polysaccharide-modified modified cyclodextrin; 4. The solution of hyaluronic acid peptide + palmitoyl tripeptide-1 + palmitoyl pentapeptide-4 after inclusion in polysaccharide-modified modified cyclodextrin; 5. The solution of hyaluronic acid peptide + palmitoyl tripeptide-1 + palmitoyl tripeptide-5 after inclusion in polysaccharide-modified modified cyclodextrin; 6. A solution of hyaluronic acid peptide + palmitoyl tripeptide-1 + palmitoyl tripeptide-5 + palmitoyl hexapeptide-12 after inclusion in polysaccharide-modified modified cyclodextrin; 7. The solution of hyaluronic acid peptide + palmitoyl tripeptide-1 + palmitoyl tripeptide-5 + palmitoyl tetrapeptide-7 after inclusion in polysaccharide-modified modified cyclodextrin; 8. A solution of hyaluronic acid peptide + palmitoyl tripeptide-1 + palmitoyl tripeptide-5 + palmitoyl tripeptide-8 after inclusion in polysaccharide-modified modified cyclodextrin; 9. A solution of hyaluronic acid peptide + palmitoyl tripeptide-1 + palmitoyl tripeptide-5 + palmitoyl pentapeptide-4 + palmitoyl hexapeptide-12 + palmitoyl tripeptide-8 after inclusion in polysaccharide-modified modified cyclodextrin; The above samples were subjected to in vitro anti-wrinkle and firming tests (elastase inhibition test); Principle of the test: Elastase acts on N-succinyl-alanine-alanine-alanine-p-nitroaniline (AAAPAN) to produce p-nitroaniline, which absorbs at 410 nm and appears yellow. The activity of elastase is examined by detecting the release of p-nitroaniline at 410 nm. The elastase inhibition rate of a single sample is determined by UV spectrophotometry using AAAPAN as a substrate.

[0035] This method is an in vitro test method, which mainly characterizes whether the sample has anti-wrinkle and firming effects by evaluating the inhibition rate of the sample on elastase activity; Main reagents: Tris-HCL (tris(hydroxymethyl)aminomethane hydrochloride): reagent grade, ≥99%, Ron; Elastase: sourced from porcine pancreas, brand Sigma, type IV, protein 50-90%, lyophilized powder, ≥30 units / mg protein (Biuret); (-)-epigallocatechin gallate (EGCG): R003353, 98%, Ron; Dimethyl sulfoxide (DMSO): AR, R012316, Ron; N-succinyl-alanine-alanine-alanine-p-nitroaniline (AAAPAN), ≥98% (HPLC), Sigma main instruments: UV spectrophotometer, Genesys 180, ThermoFisher; Test method: Draw the inhibition rate reference curve of the positive control Taking EGCG as the system reference, it was diluted with pure water to the concentration shown in Table 5. The test and calculation were carried out according to the experimental method. The reference curve was drawn with the reference concentration as the X-axis and the elastase activity inhibition rate as the Y-axis.

[0036] Table 5 (-)-epigallocatechin gallate dilution concentration

[0037] Elastase inhibition test Pretreatment: Water-soluble test substances were diluted with water to form multi-level concentration samples, and oil-soluble cosmetics were diluted with 50% DMSO-water solution to form multi-level concentration samples.

[0038] Prepare the test reaction system according to Table 6, and measure the absorbance of each reaction tube at a wavelength of 410 nm using an ultraviolet spectrophotometer.

[0039] Table 6 Elastase activity inhibition test reaction system

[0040] The inhibition rate of the sample on elastase activity was calculated according to the following formula.

[0041] Inhibition rate = ((AB) - (CD)) * 100 / (AB) 5. Test results The results and reference curve of the inhibition rate of elastase activity by the positive control substance EGCG are shown in Table 7; Table 7 EGCG inhibition rate on elastase activity

[0042] The test results showed that the positive control EGCG had a good inhibitory effect on elastase activity, and the concentration and inhibition rate had a strong correlation and linearity. This showed that the designed test system was effective and the test samples had consistent experimental results on elastase activity. Table 8 Original results of elastase activity inhibition test

[0043] From the above experiments 1 and 2, it can be seen that the aqueous solution of the modified cyclodextrin containing hyaluronic acid peptide modified by polysaccharide has a higher inhibition rate of elastase and better firming and anti-wrinkle effect compared with its alcohol solution; Through experiments 2, 3, 5, and 7, it can be seen that the aqueous solution of hyaluronic acid peptide compounded with palmitoyl tripeptide-1, palmitoyl tripeptide-5, and palmitoyl tetrapeptide-7, after being included in the modified cyclodextrin modified with polysaccharide, has a higher inhibition rate of elastase, better firming and anti-wrinkle effects, and more significant synergistic effect. Through experiments 3 and 4, 5 and 6, 7 and 8, 8 and 9, and 6 and 9, it can be seen that the inhibition rate of elastase in the aqueous solution of hyaluronic acid peptide compounded with three palmitoyl peptides, palmitoyl pentapeptide-4, palmitoyl hexapeptide-12, and palmitoyl tripeptide-8, after being included in the modified cyclodextrin modified with polysaccharide will be improved.

[0044] In summary, by optimizing the types of complex palmitoyl peptides and pairing them with hyaluronic acid peptides, the peptides with significant synergistic effects are: palmitoyl tripeptide-1, palmitoyl tripeptide-5, and palmitoyl tetrapeptide-7.

[0045] Example 5 The results of the in vitro transdermal test of Example 1 showed that the apparent transdermal coefficient of the composition of Example 1 was 18 times that of the hyaluronic acid peptide alcohol solution with the same proportion, and 5 times that of the ordinary inclusion solution.

[0046] Example 6 The stability of the freeze-dried powders of Examples 1, 2, and 3 was tested. After 3 months of the experiment, there was no abnormal phenomenon such as shrinkage, moisture absorption, and discoloration.

[0047] The lyophilized powder prepared in Example 1, the lyophilized powder in Comparative Example 1, and a 5.5% solution of hyaluronic acid peptide + 9% 1,2-hexanediol were added to anti-aging toners for efficacy testing (moisturizing, firming, elasticity, roughness improvement, and wrinkle reduction). These were designated as Toner No. 1, Toner No. 2, and Toner No. 3, respectively. The test parameters and instruments are shown in Table 9. The data and indicators obtained from 30 subjects after using each sample for 14 and 28 days are shown in Table 10.

[0048] Table 9 Instrument measurement parameter description and related equipment

[0049] Table 10 Efficacy test data

[0050] The above efficacy test results show that the composition of Example 1 has significant improvements in every aspect of anti-aging compared to Comparative Example 1 and the hyaluronic acid peptide solution, and has significant immediate firming and wrinkle-removing effects in the firming and wrinkle-removing tests.

Claims

1. A hyaluronic acid peptide composition delivered via modification technology, characterized in that: The composition includes the following components by mass percentage: polysaccharide-modified modified cyclodextrin 1-10%, hyaluronic acid peptide 0.05-0.5%, palmitic acid complex peptide 0.01-0.5%, polyol 0.1-0.8%, and the rest is deionized water. The sum of the mass percentages of the above components is 100%.

2. The hyaluronic acid peptide composition delivered by modification technology according to claim 1, characterized in that: The palmitic acid complex peptide is any one or more of palmitoyl tripeptide-1, palmitoyl tripeptide-5, palmitoyl pentapeptide-4, palmitoyl tetrapeptide-7, palmitoyl hexapeptide-12, and palmitoyl tripeptide-8.

3. The hyaluronic acid peptide composition delivered by modification technology according to claim 2, characterized in that: The palmitoyl complex peptide is a compound of palmitoyl tripeptide-1, palmitoyl tripeptide-5, and palmitoyl tetrapeptide-7.

4. The hyaluronic acid peptide composition delivered by modification technology according to claim 1, characterized in that: The polyol is any one of 1,2-hexanediol, 1,3-propylene glycol, butanediol, and pentanediol.

5. The hyaluronic acid peptide composition delivered by modification technology according to claim 1, characterized in that: The polysaccharide-modified modified cyclodextrin is any one of oat glucan-modified hydroxypropyl cyclodextrin, dendrobium officinale polysaccharide-modified hydroxypropyl cyclodextrin, and euglena polysaccharide-modified hydroxypropyl cyclodextrin.

6. The hyaluronic acid peptide composition delivered by modification technology according to claim 5, characterized in that: The preparation process of the polysaccharide-modified modified cyclodextrin is as follows: dissolving the polysaccharide in water, adding sodium hydroxide alkaline solution, mixing evenly, adding hydroxypropyl cyclodextrin, ultrasonically shaking at 40-60°C for 2-10 hours, then slowly dripping 1,3-propylene glycol, continuing to react at this temperature for 10-24 hours, filtering the material body, adding isopropanol, precipitating the solid and centrifuging, and placing the centrifuged material body in a vacuum drying oven to obtain the polysaccharide-modified modified cyclodextrin; the polysaccharide is any one of oat glucan, Dendrobium officinale polysaccharide, and fine algae polysaccharide.

7. The method for preparing the hyaluronic acid peptide composition delivered by modification technology according to any one of claims 1 to 6, characterized in that: Specifically: The polysaccharide-modified modified cyclodextrin powder, hyaluronic acid peptide powder and palmitic acid complex peptide are mixed and stirred evenly, purified water is added, and the mixture is slowly stirred until the solution is completely transparent and the inclusion is completed. Polyol is added and the inclusion composition is filtered to obtain the inclusion composition. The inclusion solution is vacuum freeze-dried to obtain the resulting cake-like freeze-dried powder, which is the hyaluronic acid peptide composition.

8. The method for preparing the hyaluronic acid peptide composition delivered via modification technology according to claim 7, wherein: The vacuum freeze-drying process is as follows: freezing at -50 to -30°C for 2 to 8 hours, then vacuuming, heating to -30 to -20°C, and maintaining for 4 to 15 hours; continuing to heat to -20 to -10°C, and maintaining for 5 to 10 hours; then heating to -10 to 0°C, and maintaining for 4 to 8 hours; continuing to heat to 0 to 20°C, and maintaining for 3 to 8 hours; and finally heating to 20 to 40°C, and maintaining for 3 to 20 hours.

9. Use of the hyaluronic acid peptide composition delivered by the modification technology according to any one of claims 1 to 6 in a cosmetic matrix.

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