CN117224418B - Anti-aging composition and product application thereof - Google Patents
Anti-aging composition and product application thereof Download PDFInfo
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- CN117224418B CN117224418B CN202311502272.7A CN202311502272A CN117224418B CN 117224418 B CN117224418 B CN 117224418B CN 202311502272 A CN202311502272 A CN 202311502272A CN 117224418 B CN117224418 B CN 117224418B
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- galactose
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Abstract
The invention discloses an anti-aging composition and application of a product thereof, and relates to the technical field of polypeptide cosmetics. The anti-aging composition comprises a transdermal absorption enhancer; the percutaneous absorption promoter comprises glycoside derivatives; the glycoside derivative comprises a galactose glycoside derivative, wherein the structure of the galactose glycoside derivative comprises alkyl, ester group and pyrazine; the structure of the galactoside derivative also contains sulfur. The anti-aging composition provided by the invention has an extremely remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, and has remarkable difference compared with the independent use of various functional components.
Description
Technical Field
The invention belongs to the technical field of polypeptide cosmetics, and particularly relates to an anti-aging composition and a product application thereof.
Background
The problem that everyone faces is that aging comes from two aspects, endogenous and exogenous. Endogenous, i.e., human metabolism in the human body with age, can lead to collagen degradation and loss, which is irreversible; exogenous substances, namely substances polluted in life are more and more, oxidized substances are more and more, and generated free radicals can break links of collagen so as to break and lose elasticity.
Polypeptides have a wide variety of biological roles, the most prominent of which is a signaling molecule in a variety of physiological processes including defense, immunity, stress, growth, homeostasis and reproduction. These aspects have been used in the dermatological and cosmetic fields to promote extracellular matrix synthesis, avoid pigmentation, treat innate immunity and inflammation. However, polypeptide actives are sought after by the market due to their remarkable and specific efficacy, without side effects, but also due to their specificity, achieving efficacy against practical complex problems is not as expected.
Although the existing polypeptide composition for resisting aging on the market focuses on exogenous and exogenous aging, the active exogenous and exogenous targets are relatively single, and no clear mechanism and data support exists for the combined synergy. The multiple polypeptide compositions of the invention can achieve the optimal anti-aging effect on the endogenous and exogenous skin by the accurate combination of multiple targets, and meet the demands of consumers.
Disclosure of Invention
The invention aims to provide an anti-aging composition and a product application thereof, wherein the anti-aging composition has an extremely remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, and has remarkable difference compared with single use of various functional components.
The technical scheme adopted by the invention for achieving the purpose is as follows:
a compound for transdermal absorption comprising a glycoside derivative; the glycoside derivative comprises a galactose glycoside derivative, wherein the structure of the galactose glycoside derivative comprises alkyl, ester group and pyrazine;
the structure of the galactoside derivative also contains sulfur. The invention adopts pyrazinyl ethanethiol to chemically modify D-galactose to prepare galactose derivatives, and the galactose derivatives are used by being compounded with water-soluble vitamin E, so that the galactose derivatives have more excellent transdermal absorption promoting capability; the anti-aging composition is used in the preparation process of the anti-aging composition, can effectively improve the action effect of the composition, obviously enhance the action of the composition on promoting the growth of human skin fibroblasts and promote the secretion of type I and type III collagen; further enhancing the effect of the composition on the skin, obviously improving the effect of lightening lines and elasticity, and further improving the compactness and fineness of the skin. The reason for this may be that galactose derivatives are compounded with water-soluble vitamin E, natural chemical groups in the structure of the galactose derivatives can better enter the dermis layer, and chemically modified parts can better open pores, so that substances can be promoted to be absorbed by a human body through the epidermis layer, and the action effect of the composition is enhanced.
Specifically, the galactoside derivative comprises acetic anhydride and pyrazinyl ethanethiol chemically modified D-galactose products.
The preparation method of the galactose derivative comprises the following steps:
mixing D-galactose, acetic anhydride, glacial acetic acid and perchloric acid, and adding acetyl bromide and methanol for reaction to obtain an intermediate O;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, and adding a1, 4-dioxane solution of an intermediate O to react to obtain a galactoside derivative.
Further specifically, the preparation method of the galactoside derivative comprises the following steps:
mixing D-galactose, acetic anhydride, glacial acetic acid and perchloric acid, stirring for 0.5-1.5 h at normal temperature, then adding acetyl bromide and methanol, stirring for 1-3 h, pouring into ice water, extracting with dichloromethane, washing an organic phase with saturated sodium bicarbonate solution and saturated sodium chloride solution in sequence, drying with anhydrous sodium sulfate, and concentrating to obtain an intermediate O;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, stirring at normal temperature for 0.5-1.5 h, then adding a1, 4-dioxane solution of an intermediate O, heating to 50-60 ℃ for reaction, monitoring until the reaction is finished by adopting thin layer chromatography, concentrating, extracting by adopting ethyl acetate, drying by adopting anhydrous magnesium sulfate, concentrating, and recrystallizing by adopting a methanol/dichloromethane mixed solution to obtain the galactoside derivative.
Specifically, the molar ratio of D-galactose to acetic anhydride is 1:5-7; the solid-to-liquid ratio of D-galactose to glacial acetic acid was 1g: 8-12 mL; the solid-liquid ratio of D-galactose and perchloric acid is 75-85 g:1mL; the mol ratio of acetyl bromide to D-galactose is 2.5-3:1; the volume ratio of the methanol to the acetyl bromide is 0.6-0.7:1.
Specifically, the molar ratio of pyrazinyl ethanethiol to potassium carbonate is 1:1.3-1.8; the solid-to-liquid ratio of pyrazinyl ethanethiol to 1, 4-dioxane is 0.08-0.1 g:1mL; the volume ratio of water to 1, 4-dioxane is 0.2-0.4:1; the mol ratio of the intermediate O to pyrazinyl ethanethiol is 1.3-1.8:1; the concentration of the 1, 4-dioxane solution of the intermediate O is 1-2 mmol/mL.
A percutaneous absorption enhancer comprising the above compound for percutaneous absorption.
In particular, the transdermal absorption enhancer further comprises water-soluble vitamin E.
Specifically, the mass ratio of the water-soluble vitamin E to the galactoside derivative is 1:5-20.
An anti-aging composition comprises the above percutaneous absorption enhancer.
Specifically, the anti-aging composition comprises any 3-5 of acetyl hexapeptide-8, snake venom peptide, palmitoyl pentapeptide-4, palmitoyl tripeptide-5 and carnosine. The anti-aging composition provided by the invention has an extremely remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, has remarkable difference compared with the independent use of various functional components, and achieves unexpected technical effects.
Wherein, acetyl hexapeptide-8, neurotransmitter inhibitory polypeptide mimics the N-terminal structure of neurotransmitter SNAP-25 protein, thereby reducing the release of acetylcholine (Ach). A snake venom peptide, a neurotransmitter-inhibiting polypeptide that mimics the activity of the snake venom Waglein I, binds to the epsilon subunit of nmAChR to block acetylcholine binding to receptors and to block neuronal excitation transmission. Carnosine blocks free radical reactions and glycosylation reactions, prevents the production of oxidative stress products and glycosylated end (AGE) products, promotes collagen production, and eliminates glycosylated dark yellow proteins. Palmitoyl tripeptide-5, activating transforming growth factor TGF-beta, inhibiting the activity of MMP (matrix metalloproteinase); palmitoyl pentapeptide-4, a hydrolysis product of the procollagen alpha 1 chain-MATRIKINES (messenger peptide) is a precisely mimetic active peptide. Can promote the generation of I and III type collagen and fibronectin. The acetyl tetrapeptide-2 has a certain promotion effect on the collagen COL17A1 formed by DEJ semi-bridged granules, can effectively promote the collagen level and elastic fiber, promote the combination of cells and ECM, and resist adverse effects of skin firmness and adhesion loss. Acetyl dipeptide-1 cetyl ester increases the natural synthesis of endorphins and enkephalins, promptly relieves the red-hot stinging of the skin, is anti-inflammatory and pleasant, and is effective in stimulating the regeneration of elastin.
Specifically, the anti-aging composition is in a dosage form comprising an aqueous solution.
Specifically, the anti-aging composition also comprises an anti-corrosion system, wherein the mass concentration is 0.8-1.2%; the anti-corrosion system comprises p-hydroxyacetophenone and 1,2 hexanediol, wherein the mass ratio of the p-hydroxyacetophenone to the 1,2 hexanediol is 1:0.8-1.2.
Specifically, the mass concentration of the acetyl hexapeptide-8, the snake venom peptide, the palmitoyl pentapeptide-4, the palmitoyl tripeptide-5 or the carnosine in the anti-aging composition is 0.01-0.1%.
Specifically, the mass concentration of the transdermal absorption accelerator in the anti-aging composition is 1.5-4%.
Preferably, the anti-aging composition comprises acetyl hexapeptide-8, a snake venom peptide, palmitoyl pentapeptide-4, and carnosine.
Preferably, the anti-aging composition comprises acetyl hexapeptide-8, a snake venom peptide, palmitoyl tripeptide-5, and carnosine.
Preferably, the anti-aging composition comprises acetyl hexapeptide-8, a snake venom peptide, palmitoyl pentapeptide-4, palmitoyl tripeptide-5, and carnosine.
Further preferably, caffeic acid derivatives are also added into the anti-aging composition, and the mass concentration is 0.05-0.2%; the caffeic acid derivative comprises a product of chemically modified caffeic acid of pyridoxine hydrochloride. The invention adopts the chemical modification of caffeic acid by the pioglitamine hydrochloride to obtain caffeic acid derivatives, and the caffeic acid derivatives show excellent bioactivity. The anti-aging composition can be applied to an anti-aging composition, further enhance the wrinkle removing and wrinkle reducing effects of the composition, remarkably promote proliferation of human skin fibroblasts and promote secretion of I, III type collagen.
Specifically, the preparation method of the caffeic acid derivative comprises the following steps: and mixing caffeic acid with pyridoxine hydrochloride, and carrying out amidation reaction under the condition of a catalytic system to obtain the caffeic acid derivative.
Further specifically, the preparation method of the caffeic acid derivative comprises the following steps:
mixing caffeic acid, triethylamine and tetrahydrofuran, adding pyridoxine hydrochloride at 0-4 ℃, adding DMAP, adding DCC after the reaction liquid is clarified, reacting for 24-26 hours at normal temperature, concentrating under reduced pressure, adding ethyl acetate for extraction, shaking uniformly, placing in a refrigerator overnight, concentrating under reduced pressure, extracting 2-4 times by using ethyl acetate, washing an organic phase by adopting 4-6% sodium bicarbonate concentration and 0.8-1.2 mmol/L hydrochloric acid solution, drying by using anhydrous sodium sulfate, concentrating under reduced pressure, and purifying by column chromatography to obtain caffeic acid derivatives.
Specifically, the solid-to-liquid ratio of caffeic acid to tetrahydrofuran is 0.05-0.08 g:1mL; the molar ratio of the pyrilamine hydrochloride to the caffeic acid is 1-1.5:1; the mol ratio of the triethylamine to the caffeic acid is 1.1-1.3:1; the molar ratio of DMAP to caffeic acid is 0.1-0.2:1; the molar ratio of DCC to caffeic acid is 1.2-1.3:1.
The invention also discloses application of the compound for transdermal absorption in preparing cosmetics or skin care products or medicaments.
The invention also discloses application of the anti-aging composition in preparing cosmetics or skin care products or medicaments.
The invention also discloses application of the caffeic acid derivative in preparing anti-aging cosmetics or skin care products or medicaments.
The invention also discloses application of the galactose derivative in preparing a transdermal absorption promoter.
The invention also discloses application of the galactose derivative in preparing cosmetics or skin care products or medicaments.
Compared with the prior art, the invention has the following beneficial effects:
the composition provided by the invention is used for obtaining one or more peptide skin anti-aging compositions by screening combination collocations and single components in different proportions, and combining researches aiming at application characteristics of respective raw materials, for example, the unprecedented effects of single substances are invented through a composition form, so that innovative application of new effects of combining new targets is obtained. The invention adopts pyrazinyl ethanethiol to chemically modify D-galactose to prepare galactose derivatives, and the galactose derivatives are used by being compounded with water-soluble vitamin E, so that better transdermal absorption promoting capability is shown; the anti-aging composition is used in the preparation process of the anti-aging composition, can effectively improve the action effect of the composition, obviously enhance the action of the composition on promoting the growth of human skin fibroblasts and promote the secretion of type I and type III collagen; further enhances the effect of the composition on the skin, obviously improves the effect of improving the wrinkle and elasticity, and obviously improves the compactness and fineness of the skin. Meanwhile, the caffeic acid derivative is obtained by adopting the chemical modification of the pisiform hydrochloride, and is applied to an anti-aging composition, so that the wrinkle removing and wrinkle reducing effects of the composition can be further enhanced, the proliferation of human skin fibroblasts is obviously promoted, and the secretion of I, III type collagen is promoted.
Therefore, the invention provides an anti-aging composition and the application of the product thereof, wherein the anti-aging composition has very remarkable effect of removing wrinkles, remarkably promotes proliferation of human skin fibroblasts, promotes secretion of I, III type collagen, and has remarkable difference compared with the independent use of various functional components.
Drawings
FIG. 1 is an infrared test result of galactose derivatives in the examples of the present invention;
FIG. 2 shows the results of an infrared test of caffeic acid derivatives in an example of the invention.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the following describes in detail various embodiments of the present invention with reference to the embodiments. However, those of ordinary skill in the art will understand that in various embodiments of the present invention, numerous technical details have been set forth in order to provide a better understanding of the present application. However, the technical solutions claimed in the present application can be implemented without these technical details and with various changes and modifications based on the following embodiments.
Example 1:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, acetyl hexapeptide-8,0.05% in a mass concentration of snake venom peptide in a mass concentration of 0.05%, palmitoyl pentapeptide-4,0.05% in a mass concentration of palmitoyl tripeptide-5 in a mass concentration of 0.05% and carnosine in a mass concentration of 0.05%.
Example 2:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the raw material components comprise a preservative system with the mass concentration of 1% (comprising p-hydroxyacetophenone and 1, 2-hexanediol, the mass ratio of the p-hydroxyacetophenone to the 1:1), a transdermal absorption enhancer with the mass concentration of 2.5% (comprising water-soluble vitamin E and D-galactose, the mass ratio of the water-soluble vitamin E to the D-galactose being 1:12), acetyl hexapeptide with the mass concentration of 0.05-8,0.05% snake venom peptide with the mass concentration, palmitoyl pentapeptide with the mass concentration of 0.05-4,0.05% carnosine.
Example 3:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the raw material components comprise a preservative system (comprising p-hydroxyacetophenone and 1, 2-hexanediol in a mass ratio of 1:1) with a mass concentration of 1%, a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) with a mass concentration of 2.5%, acetyl hexapeptide with a mass concentration of 0.05-8,0.05% of snake venom peptide and palmitoyl tripeptide with a mass concentration of 0.05-5,0.05% of carnosine.
Example 4:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and galactose derivatives in a mass ratio of 1:12) in a mass concentration of 2.5%, acetyl hexapeptide-8,0.05% of snake venom peptide in a mass concentration of 0.05%, palmitoyl pentapeptide-4,0.05% of palmitoyl tripeptide-5,0.05% of carnosine in a mass concentration of 0.05%.
Preparation of galactose derivatives:
mixing D-galactose, acetic anhydride, glacial acetic acid and perchloric acid, stirring for 1h at normal temperature, then adding acetyl bromide and methanol, stirring for 2h, then pouring into ice water, extracting with dichloromethane, washing an organic phase with saturated sodium bicarbonate solution and saturated sodium chloride solution in sequence, drying with anhydrous sodium sulfate, and concentrating to obtain an intermediate O; in the preparation process, the molar ratio of D-galactose to acetic anhydride is 1:6.2; the solid-to-liquid ratio of D-galactose to glacial acetic acid was 1g:10mL; the solid-to-liquid ratio of D-galactose to perchloric acid was 81g:1mL; the molar ratio of acetyl bromide to D-galactose is 2.8:1; the volume ratio of the methanol to the acetyl bromide is 0.66:1;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, stirring for 1h at normal temperature, then adding a1, 4-dioxane solution of an intermediate O, heating to 50 ℃ for reaction, monitoring until the reaction is finished by adopting thin layer chromatography, concentrating, extracting by adopting ethyl acetate, drying by using anhydrous magnesium sulfate, concentrating, and recrystallizing by using a methanol/dichloromethane mixed solution to obtain a galactose derivative; in the preparation process, the molar ratio of pyrazinyl ethanethiol to potassium carbonate is 1:1.5; the solid-to-liquid ratio of pyrazinyl ethanethiol to 1, 4-dioxane was 0.09g:1mL; the molar ratio of the intermediate O to the pyrazinyl ethanethiol is 1.5:1; the concentration of the 1, 4-dioxane solution of intermediate O was 1.6mmol/mL.
Example 5:
an anti-aging composition in the form of an aqueous formulation, which differs from example 4 in that: the raw material component also comprises caffeic acid derivative with the mass concentration of 0.1 percent.
Preparation of caffeic acid derivatives:
mixing caffeic acid, triethylamine and tetrahydrofuran, adding pyridoxine hydrochloride at 0 ℃, adding DMAP, adding DCC after the reaction liquid is clarified, reacting for 24 hours at normal temperature, concentrating under reduced pressure, adding ethyl acetate for extraction, shaking uniformly, placing in a refrigerator overnight, concentrating under reduced pressure, extracting with ethyl acetate for 3 times, washing the organic phase sequentially with 5% sodium bicarbonate concentration and 1mmol/L hydrochloric acid solution, drying with anhydrous sodium sulfate, concentrating under reduced pressure, and purifying by column chromatography to obtain caffeic acid derivatives; in the specific preparation process, the solid-to-liquid ratio of the caffeic acid to the tetrahydrofuran is 0.065g:1mL; the molar ratio of the pyrilamine hydrochloride to the caffeic acid is 1.3:1; the molar ratio of triethylamine to caffeic acid is 1.2:1; the molar ratio of DMAP to caffeic acid is 0.15:1; the molar ratio of DCC to caffeic acid was 1.25:1.
Example 6:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the raw material components also comprise caffeic acid derivatives with mass concentration of 0.05-0.2%.
The caffeic acid derivative was prepared in the same manner as in example 5.
Example 7:
an anti-aging composition in the form of an aqueous formulation, which differs from example 1 in that: the galactose derivatives in the raw material components were prepared in this example.
The galactose derivatives are prepared differently from example 4 in that: an equimolar amount of 2,2' - (1, 2-ethanediylbisoxo) diethyl mercaptan was used in place of pyrazinyl ethanethiol.
Comparative example 1:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1) with a mass concentration of 1%, a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) with a mass concentration of 2.5%, and acetyl hexapeptide-8 with a mass concentration of 0.35%.
Comparative example 2:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and a snake venom peptide in a mass concentration of 0.35%.
Comparative example 3:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1) with a mass concentration of 1%, a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) with a mass concentration of 2.5%, and palmitoyl pentapeptide-4 with a mass concentration of 0.35%.
Comparative example 4:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and palmitoyl tripeptide-5 in a mass concentration of 0.35%.
Comparative example 5:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and carnosine in a mass concentration of 0.35%.
Comparative example 6:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and acetyl hexapeptide-8 in a mass concentration of 0.3%.
Comparative example 7:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and a snake venom peptide in a mass concentration of 0.3%.
Comparative example 8:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and palmitoyl pentapeptide-4 in a mass concentration of 0.3%.
Comparative example 9:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and palmitoyl tripeptide-5 in a mass concentration of 0.3%.
Comparative example 10:
an anti-aging composition is in the form of water, and comprises a preservative system (comprising p-hydroxyacetophenone and 1,2 hexanediol in a mass ratio of 1:1), a transdermal absorption enhancer (comprising water-soluble vitamin E and D-galactose in a mass ratio of 1:12) in a mass concentration of 2.5%, and carnosine in a mass concentration of 0.3%.
Test example 1:
infrared sign
The testing is carried out by adopting a Fourier infrared spectrometer, and the testing range is 500-4000 cm -1 。
The galactose derivatives prepared in example 4 were subjected to the above-described test, and the results are shown in fig. 1. From the analysis of the figure, 1758cm of infrared spectrum -1 Characteristic absorption peak of acetyl C=O on sugar ring appears nearby and is 1600-1400 cm -1 The characteristic absorption peaks of the pyrazine ring exist within the range, and the above results indicate that galactose derivatives in example 4 were successfully prepared.
The caffeic acid derivative prepared in example 5 was subjected to the above test, and the results are shown in fig. 2. From the figureAs can be seen from the analysis in the middle, 1670cm of the infrared spectrum -1 、1545cm -1 The characteristic absorption peaks of the amide groups occurring nearby indicate successful preparation of the caffeic acid derivative in example 5.
Test example 2:
determination of transdermal absorption Property
3 diffusion cells are simultaneously arranged in a transdermal diffusion tester, and the area of each cell opening is 3cm 2 The volume is 8mL, the receiving solution is 0.9% physiological saline, the penetrating skin is the abdominal skin of the mice, and the specific preparation method comprises the following steps: taking 3 mice of the same kind with close weight, scraping abdominal hair, feeding for 24 hours, removing peeled fat, removing foreign hair, cleaning with normal saline, respectively smearing the same amount of anti-aging composition test samples, smearing for 20 minutes, and transferring to a diffusion cell for transmittance detection.
The anti-aging compositions prepared in example 1, example 4, and example 7 were subjected to the above test, and the results are shown in table 1:
TABLE 1 results of percutaneous absorption test
From the data analysis in table 1, the carnosine transmittance of the anti-aging composition prepared in example 4 is obviously higher than that of examples 1 and 7, and the effect of example 7 is better than that of example 1, which shows that the prepared galactose derivative of the invention is compounded with water-soluble vitamin E to obtain a transdermal absorption enhancer which shows better transdermal promoting effect; and the galactose derivative is obtained by adopting pyrazinyl ethanethiol to chemically modify galactose, and the galactose derivative is compounded with other components, so that the transdermal absorption promoting effect of the transdermal absorption promoter can be further enhanced.
Test example 3:
investigation of proliferation effect of human skin fibroblast
Human skin fibroblasts were inoculated into MEM medium containing 5% fetal bovine serum by volume fraction, as 5% CO 2 Culturing in incubator at 37deg.C, changing liquid 1 time every 3d, culturing for 7d, and sucking out originalThe cells were washed 3 times with PBS buffer, 0.5mL of 0.25% Trypsin-1mM EDTA 4Na solution was added, followed by 10mL of MEM medium, the cells were suspended by suction, transferred to a centrifuge tube, centrifuged at 2000rpm for 5min, the supernatant removed, and an appropriate amount of MEM medium containing 5% fetal bovine serum by volume was added, and the cells were suspended by suction. Taking a 96-well plate, adding 100 [ mu ] L of cell suspension (containing 1000 cells) into each well, adding 20 [ mu ] L of a test sample, setting an equal volume of PBS buffer solution as a blank control group, culturing in an incubator for 72 hours, taking out, adding 15 [ mu ] L of WST-8 solution into each well, incubating in the incubator for 4 hours, taking out, and measuring an OD value at 450 nm.
The anti-aging compositions prepared in examples 1 to 7 and comparative examples 1 to 10 were subjected to the above test, and the results are shown in Table 2:
TABLE 2 results of human skin fibroblast proliferation effect test
From the analysis of the data in Table 2, it is clear that the OD values of the anti-aging compositions prepared using example 1 of the present invention are significantly better than those of comparative examples 1 to 5, and the effects are better than those of examples 2 and 3; meanwhile, the effects of the embodiment 2 and the embodiment 3 are obviously better than those of the comparative examples 6-10, and the composition provided by the invention has a synergistic effect when being compounded, and the combined use of 4 or 5 functional components has the effect of obviously promoting the growth of human skin fibroblasts, and has the effect of obviously promoting the growth of human skin fibroblasts compared with the independent use of the components. Example 4 has better effect than example 1 and example 7, and example 7 has better effect than example 1, which shows that the galactose derivative prepared by the invention is compounded with water-soluble vitamin E, and can be used as a transdermal absorption promoter in an anti-aging composition to further enhance the growth effect of the composition on human skin fibroblasts; and the pyrazinyl ethanethiol is adopted to chemically modify galactose to obtain galactose derivatives, and the galactose derivatives are compounded with other components, so that the enhancement effect is further improved. Example 5 is better than example 4 and example 6 is better than example 1, indicating that the caffeic acid derivative obtained by chemically modifying caffeic acid with pyridoxine hydrochloride can effectively promote the growth of human skin fibroblasts when applied in anti-aging compositions.
Type I and type III collagen secretion influence test
Adding 1000 human skin fibroblasts into each hole in a 96-hole plate, keeping the liquid change for 3 days, adding 20 mu L of test sample into each hole, and setting an equal volume of PBS buffer solution as a blank comparison group; then culturing for 7d, then measuring the content of the type I collagen and the type III collagen by adopting an ELASA method, and calculating the content improvement rate (unifying treatment is carried out on the basis of a blank control group).
The anti-aging compositions prepared in examples 1 to 7 and comparative examples 1 to 10 were subjected to the above test, and the results are shown in Table 3:
TABLE 3 results of human skin fibroblast proliferation effect test
From the data analysis in Table 3, it is clear that the anti-aging composition prepared in example 1 of the present invention has a significantly better type I and type III collagen content than comparative examples 1 to 5 and a significantly better effect than examples 2 and 3; meanwhile, the effects of the embodiment 2 and the embodiment 3 are obviously better than those of the comparative examples 6-10, which shows that the composition provided by the invention has a synergistic enhancement effect when being compounded, and the combination of 4 or 5 functional components has the effect of obviously promoting the secretion of the type I collagen and the type III collagen. Example 4 has better effect than example 1 and example 7, and example 7 has better effect than example 1, which shows that the galactose derivative prepared by the invention is compounded with water-soluble vitamin E, and can be used as a transdermal absorption promoter in an anti-aging composition to further enhance the secretion promotion effect of the composition on type I and type III collagen; and the pyrazinyl ethanethiol is adopted to chemically modify galactose to obtain galactose derivatives, and the galactose derivatives are compounded with other components, so that the enhancement effect is further improved. Example 5 is better than example 4 and example 6 is better than example 1, indicating that chemical modification of caffeic acid with pyridoxine hydrochloride to obtain caffeic acid derivatives can effectively promote the secretion of type I and type III collagen.
Test example 4:
human trial evaluation
Randomly extracting 140 healthy volunteers (the ages of 25-55 years old, women, skin photo-biological types are II-IV skin, and the facial skin has the problems of fine wrinkles, poor elasticity, darkness and the like), wherein each 10 persons are one group, the inner face of the tested person is used for 2 times within 1 day, 1mL each time is uniformly coated on the face, and the skin is cleaned by clear water after 10 minutes and continuously used for 4 weeks; can maintain the regularity of life and avoid solar ultraviolet irradiation during the study. Wherein skin elasticity is measured using a skin elasticity tester MPA580 from CK, germany, and using a Revisclometer RV600 probe; the wrinkles, the tightness and the fineness are all measured by a skin detector, and a Visia skin detector is specifically adopted.
The anti-aging compositions prepared in examples 1 to 7 and comparative examples 1 to 5 were subjected to the above test, and the results are shown in Table 4:
TABLE 4 results of human body test
From the data analysis in table 4, it is known that the skin striae-lightening rate, elasticity-improving rate, firmness-improving rate and fineness-improving rate of the subject are significantly better than those of comparative examples 1 to 5 and are better than those of examples 2 and 3 after the anti-aging composition prepared in example 1 is used; meanwhile, the effects of the embodiment 2 and the embodiment 3 are obviously better than those of the comparative examples 8-14, which shows that the composition provided by the invention has a synergistic enhancement effect when being compounded, and the combination of 4 or 5 functional components shows better action effects, especially in the aspects of improving skin elasticity, improving wrinkles and the like. The effect of example 4 is better than that of examples 1 and 7, and the effect of example 7 is better than that of example 1, which shows that the galactose derivative prepared by the invention is compounded with water-soluble vitamin E, and the galactose derivative is used as a transdermal absorption promoter in an anti-aging composition, so that the effect of the composition on skin can be further enhanced, the effect of improving the light lines and the elasticity is obviously improved, and the compactness and the fineness of the skin are further improved; and the pyrazinyl ethanethiol is adopted to chemically modify galactose to obtain galactose derivatives, and the galactose derivatives are compounded with other components, so that the enhancement effect is further improved. Example 5 is better than example 4 and example 6 is better than example 1, indicating that chemical modification of caffeic acid with pyridoxine hydrochloride to obtain caffeic acid derivatives, applied in anti-aging compositions, can effectively improve the skin wrinkling and elasticity effects of the composition.
The conventional technology in the above embodiments is known to those skilled in the art, and thus is not described in detail herein.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (5)
1. A percutaneous absorption promoter comprises glycoside derivatives and water-soluble vitamin E; the glycoside derivative comprises a galactoside derivative, wherein the structure of the galactoside derivative comprises alkyl, ester group and pyrazine; the structure of the galactoside derivative also comprises sulfur; the galactoside derivative comprises acetic anhydride and pyrazinyl ethanethiol chemically modified D-galactose products;
in the preparation of the galactoside derivative, D-galactose, acetic anhydride, glacial acetic acid and perchloric acid are taken and mixed, acetyl bromide and methanol are added for reaction to obtain an intermediate O, and the molar ratio of the D-galactose to the acetic anhydride is 1:5-7; the solid-to-liquid ratio of D-galactose to glacial acetic acid was 1g: 8-12 mL; the solid-liquid ratio of D-galactose and perchloric acid is 75-85 g:1mL; the mol ratio of acetyl bromide to D-galactose is 2.5-3:1; the volume ratio of the methanol to the acetyl bromide is 0.6-0.7:1;
mixing pyrazinyl ethanethiol, potassium carbonate, 1, 4-dioxane and water, and adding a1, 4-dioxane solution of an intermediate O to react to obtain a galactoside derivative; the molar ratio of pyrazinyl ethanethiol to potassium carbonate is 1:1.3-1.8; the solid-to-liquid ratio of pyrazinyl ethanethiol to 1, 4-dioxane is 0.08-0.1 g:1mL; the volume ratio of water to 1, 4-dioxane is 0.2-0.4:1; the mol ratio of the intermediate O to pyrazinyl ethanethiol is 1.3-1.8:1; the concentration of the 1, 4-dioxane solution of the intermediate O is 1-2 mmol/mL.
2. The percutaneous absorption enhancer according to claim 1, wherein: the mass ratio of the water-soluble vitamin E to the galactoside derivative is 1:5-20.
3. An anti-aging composition comprising the transdermal absorption enhancer of claim 1.
4. An anti-aging composition according to claim 3, wherein: the anti-aging composition comprises any 3-5 of acetyl hexapeptide-8, snake venom peptide, palmitoyl pentapeptide-4, palmitoyl tripeptide-5 and carnosine.
5. Use of the anti-aging composition of claim 3 in the preparation of a cosmetic or skin care product or medicament.
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