Anti-wrinkle and firming cyclic peptide compounds as well as preparation method and application of anti-wrinkle and firming cyclic peptide compounds

Abstract

The invention provides a structure, a preparation method and an application method of a group of anti-wrinkle compact cyclopeptide compounds. The anti-wrinkle compact cyclic peptide compound comprises an anti-wrinkle cyclic peptide-1 with a sequence of c (CDLARLAMYA), and / or an anti-wrinkle cyclic peptide-2 with a sequence of c (KTFKKTFK). The promotion rates of the anti-wrinkle cyclopeptide-1 to zebra fish collagen gene expression col1a1a, col1a1b and col1a2 under the concentration of 0.001% are respectively 156%, 87% and 103%. The promotion rate of the cyclopeptide on zebra fish elastin Elna gene expression under the test concentration of 0.001% is 132%. Under the concentration of 0.001%, the promotion rates of the anti-wrinkle cyclopeptide-2 on zebra fish collagen gene expression col1a1a, col1a1b and col1a2 are 94%, 84% and 66% respectively. The promotion rate of the cyclopeptide on zebra fish elastin Elna gene expression under the test concentration of 0.001% is 66%.

Description

Technical Field

[0001] The invention relates to a group of cyclic peptides and preparation and use thereof, belonging to the technical field of cosmetics, and in particular to a group of cyclic peptide compounds with anti-wrinkle and firming functions and a preparation method thereof and use thereof in cosmetics. Background Art

[0002] The skin is the largest organ in the human body and plays a role in protecting the internal organs of the body from external damage. Ultraviolet radiation, temperature, air pollution and other factors will accelerate the aging of the skin. However, biological aging of the human body is a heterogeneous process and is not absolutely related to the actual age. Aging intervention strategies such as dietary restrictions, exercise and the effects of effective ingredients can slow down the aging trajectory and improve aging manifestations such as skin wrinkles and dullness.

[0003] As a core ingredient that has won the Nobel Prize many times, peptides have the characteristics of definite structure, clear efficacy mechanism, strong efficacy, and low effective dosage (generally only a few to several hundred ppm are needed to achieve significant effects). Beauty peptides with different functions such as anti-wrinkle, whitening, moisturizing, anti-oxidation, and repair have been widely developed and used.

[0004] However, most of the skin care products on the market that use peptides as active ingredients directly add peptides or peptide concentrates into conventional skin care product matrices. Active peptides will degrade over time in conventional matrix formulas, and after being applied to the skin, the solution is easily broken down by enzymes in the human body, thus affecting its efficacy. Summary of the invention

[0005] The purpose of the present invention is to provide a group of anti-wrinkle and firming cyclic peptide compounds and their preparation methods and uses. The prepared cyclic peptides have significant anti-wrinkle effects and good stability and can be better applied in the field of cosmetics.

[0006] The technical solution adopted by the present invention to achieve the above-mentioned purpose is:

[0007] In the first aspect, the present invention provides a group of cyclic peptide compounds with excellent anti-wrinkle and firming properties, wherein the cyclic peptides are as follows:

[0008] The sequence of anti-wrinkle cyclic peptide-1 is: c(CDLARLAMYA);

[0009] The structural formula of anti-wrinkle cyclic peptide-1 is as shown in Formula Ⅰ:

[0010]

[0011] Anti-wrinkle cyclic peptide-2:

[0012] The sequence of anti-wrinkle cyclic peptide-2 is: c(KTFKKTFK);

[0013] The structural formula of anti-wrinkle cyclic peptide-2 is as shown in Formula II:

[0014]

[0015] In a second aspect, the present invention provides a method for preparing an anti-wrinkle and firming cyclic peptide compound, the preparation steps of which include:

[0016] Step 1: Synthesis of linear peptides:

[0017] 2-Chlorotriphenylmethyl chloride (2-CTC resin, 0.98 mmol / g loading) was weighed in a reaction tube, and dichloromethane (DCM) was added to swell at room temperature for 1 hour. After the solvent was drained, the dichloromethane solution of the first amino acid monomer at the C-terminus (1.5 equiv) and N,N-diisopropylethylamine (DIEA, 5 equiv) was added, and after shaking reaction at room temperature for 1 hour, the resin was washed three times with N,N-dimethylformamide (DMF) and DCM in turn, and then drained.

[0018] Then, the Fmoc protection was removed, and 20% piperidine / DMF solution was added for deprotection twice, each time for 10 minutes, and then the resin was washed with DCM and DMF three times in sequence. After drying, the second amino acid was coupled, and the activated second amino acid monomer DMF solution (including 5 equiv of amino acid monomer, 4.75 equiv of condensing agent HBTU and 5 equiv of DIEA) was added. After shaking at room temperature for 1 hour, the resin was washed with DMF and DCM three times in sequence and dried. Repeat the above steps of Fmoc protection removal, washing, coupling, and washing until the last amino acid monomer.

[0019] Prepare the cleavage reagent: hexafluoroisopropanol (HFIP) / DCM (20%) or trifluoroacetic acid (TFA) / DCM (1%), add it to the dry resin, shake and react at room temperature for 0.5 h, repeat once, combine the filtrate and collect it in a centrifuge tube, remove the solvent by rotary evaporation to obtain a crude product.

[0020] Step 2: Cyclization:

[0021] The crude peptide was dissolved in DMF (0.005 M), and HATU (2 equiv) and DIEA (3-6 equiv) were added in sequence after complete dissolution, and the reaction was carried out at room temperature for 2 h. The cyclization process was monitored by LCMS. After the reaction was complete, the solvent was removed by vacuum distillation to obtain a crude cyclopeptide product, which was dissolved in acetonitrile, and the insoluble solid was removed by centrifugation. The filtrate was collected and dried to carry out the next step of deprotection.

[0022] Step 3: Deprotection:

[0023] Prepare a deprotection solution of TFA / triisopropylsilane (TIPS) / DCM = 50:5:45 or TFA / TIPS / 1,2-ethanedithiol (EDT) / DCM = 50:2.5:2.5:45, add it to the crude cyclic peptide product, shake at room temperature for 0.5-2h, and monitor the deprotection process by LCMS. After the deprotection is complete, the solvent is blown dry by an air pump, and the product is purified by a column machine.

[0024] In a third aspect, the present invention provides use of an anti-wrinkle and firming cyclic peptide compound in the preparation of cosmetics.

[0025] Furthermore, the dosage form of the cosmetic includes ointment, cream, emulsion, water, oil, gel, powder, tablet, mud, patch, film, aerosol, spray, freeze-dried preparation or nano preparation.

[0026] Furthermore, the cosmetic has anti-wrinkle and anti-skin aging effects.

[0027] In a fourth aspect, the present invention provides a cosmetic comprising the anti-wrinkle and firming cyclic peptide compound as described above.

[0028] Further, the cosmetic is an anti-wrinkle essence;

[0029] The formula of the anti-wrinkle essence contains the following ingredients in percentage by weight:

[0030] Sclerotium gum 0.5%, p-hydroxyacetophenone 0.3%, phenoxyethanol 0.25%, fragrance 0.02%, PEG-40 hydrogenated castor oil 0.1%, 1,3-butylene glycol 4%, anti-wrinkle firming cyclic peptide compound 0.05, the balance is water;

[0031] The preparation method of the anti-wrinkle essence comprises the following steps:

[0032] 1) Pre-disperse the sclerotium gum with water and stir at 75°C until the solution is transparent and free of precipitation;

[0033] 2) Add p-hydroxyacetophenone and phenoxyethanol, and stir for 5-10 minutes until emulsification is complete;

[0034] 3) Cool down to 40-45°C, pre-disperse the essence with PEG-40 hydrogenated castor oil and add it into the mixed system, then add 1,3-butylene glycol and anti-wrinkle firming cyclic peptide compound.

[0035] By means of the above technical solution, the beneficial effects of the present invention are:

[0036] 1) The present invention designs and develops a group of anti-wrinkle cyclic peptides with excellent performance: c(CDLARLAMYA), c(KTFKKTFK);

[0037] 2) The present invention provides a method for preparing a group of anti-wrinkle cyclic peptides, wherein the purity of the prepared anti-wrinkle cyclic peptides is greater than 95%;

[0038] 3) The anti-wrinkle cyclic peptide designed and developed by the present invention has a significant anti-wrinkle effect. The promotion rates of anti-wrinkle cyclic peptide-1 on the expression of zebrafish collagen col1a1a, col1a1b and col1a2 genes at a concentration of 0.001% are 156%, 87% and 103% respectively. The promotion rate of the cyclic peptide on the expression of zebrafish elastin Elna gene at a test concentration of 0.001% is 132%. The promotion rates of anti-wrinkle cyclic peptide-2 on the expression of zebrafish collagen col1a1a, col1a1b and col1a2 genes at a concentration of 0.001% are 94%, 84% and 66% respectively. The promotion rate of the cyclic peptide on the expression of zebrafish elastin Elna gene at a test concentration of 0.001% is 66%. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 is the LC-TIC-MS spectrum of anti-wrinkle cyclic peptide-1;

[0040] Figure 2 is the LC-TIC-MS spectrum of anti-wrinkle cyclic peptide-2;

[0041] Figure 3 The bar graph is the relative expression level of zebrafish type I collagen gene of anti-wrinkle cyclic peptide-1;

[0042] Figure 4 The bar graph is the relative expression level of zebrafish type I collagen gene of anti-wrinkle cyclic peptide-2;

[0043] Figure 5 The bar graph is the relative expression level of zebrafish elastin gene of anti-wrinkle cyclic peptide-1;

[0044] Figure 6 This is a bar graph of the relative expression levels of the zebrafish elastin gene of anti-wrinkle cyclic peptide-2. DETAILED DESCRIPTION

[0045] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the specific embodiments of the present invention are described in detail below.

[0046] As used herein, the term "prepared from" is synonymous with "comprising." As used herein, the terms "comprising," "including," "having," "containing," or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises the listed elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.

[0047] When amount, concentration or other value or parameter is expressed as range, preferred range or a series of upper preferred value and lower preferred value limit range, this should be understood as specifically disclosing all ranges formed by any pairing of any range upper limit or preferred value and any range lower limit or preferred value, regardless of whether the range is disclosed separately. For example, when disclosing range "1 to 5", described range should be interpreted as including range "1 to 4", "1 to 3", "1 to 2", "1 to 2 and 4 to 5", "1 to 3 and 5" etc. When numerical range is described in this article, unless otherwise stated, the range is intended to include its end value and all integers and fractions within the range.

[0048] Many specific details are set forth in the following description to facilitate a full understanding of the present invention. However, the present invention can be implemented in many other ways than those described herein, and those skilled in the art can make similar improvements without violating the connotation of the present invention, so the present invention is not limited to the specific embodiments disclosed below.

[0049] Examples 1-3

[0050] The present invention provides a group of anti-wrinkle cyclic peptides with excellent performance, and the anti-wrinkle cyclic peptides include:

[0051] Anti-wrinkle cyclic peptide-1:

[0052] The sequence of anti-wrinkle cyclic peptide-1 is: c(CDLARLAMYA);

[0053] The structural formula of anti-wrinkle cyclic peptide-1 is as shown in Formula Ⅰ:

[0054]

[0055] Anti-wrinkle cyclic peptide-2:

[0056] The sequence of anti-wrinkle cyclic peptide-2 is: c(KTFKKTFK);

[0057] The structural formula of anti-wrinkle cyclic peptide-2 is as shown in Formula II:

[0058]

[0059] The preparation method of the anti-wrinkle cyclic peptide comprises the following steps:

[0060] Step 1: Synthesis of linear peptides:

[0061] 2-Chlorotriphenylmethyl chloride (2-CTC resin, 0.98mmol / g loading) was weighed in a reaction tube, and dichloromethane (DCM) was added to swell at room temperature for 1 hour. After the solvent was drained, the first amino acid monomer at the C-terminus (1.5equiv) and N,N-diisopropylethylamine (DIEA, 5equiv) in dichloromethane solution were added. After shaking at room temperature for 1 hour, the resin was washed 3 times with N,N-dimethylformamide (DMF) and DCM in turn, and then drained. Subsequently, Fmoc protection was removed, and 20% piperidine / DMF solution was added for deprotection twice, each time for 10 minutes, and then the resin was washed 3 times with DCM and DMF in turn. After drying, the second amino acid was coupled, and the activated second amino acid monomer DMF solution (including 5equiv of amino acid monomer, 4.75equiv of condensing agent HBTU and 5equiv of DIEA) was added. After shaking at room temperature for 1 hour, the resin was washed 3 times with DMF and DCM in turn, and then drained. Repeat the above steps of removing Fmoc protection, washing, coupling, and washing until the last amino acid monomer. Prepare the cleavage reagent: hexafluoroisopropanol (HFIP) / DCM (20%) or trifluoroacetic acid (TFA) / DCM (1%), add it to the dry resin, shake and react at room temperature for 0.5h, repeat once, collect the combined filtrate in a centrifuge tube, and remove the solvent by rotary evaporation to obtain a crude product.

[0062] Step 2: Cyclization:

[0063] The crude peptide was dissolved in DMF (0.005 M), and HATU (2 equiv) and DIEA (3-6 equiv) were added in sequence after complete dissolution, and the reaction was carried out at room temperature for 2 h. The cyclization process was monitored by LCMS. After the reaction was complete, the solvent was removed by vacuum distillation to obtain a crude cyclopeptide product, which was dissolved in acetonitrile, and the insoluble solid was removed by centrifugation. The filtrate was collected and dried to carry out the next step of deprotection.

[0064] Step 3: Deprotection:

[0065] Prepare a deprotection solution of TFA / triisopropylsilane (TIPS) / DCM = 50:5:45 or TFA / TIPS / 1,2-ethanedithiol (EDT) / DCM = 50:2.5:2.5:45, add it to the crude cyclic peptide product, shake at room temperature for 1 hour, and monitor the deprotection process by LCMS. After the deprotection is complete, blow dry the solvent with an air pump, and purify the product using a column machine.

[0066] Efficacy Test Example 1

[0067] LCMS identification method of anti-wrinkle cyclic peptides:

[0068] LCMS test conditions: Shimadzu LCMS2050; chromatographic column Shimazu shim-pack GISTC18 (2μm, 100mmx2.1mm); flow rate 0.3mL / min; mobile phase A (H2O); mobile phase B (acetonitrile, containing 0.01% HCOOH);

[0069] Test method: Wavelength 204nm. Elution gradient: 0-0.5min, maintain 5% B; 0.5-5min, the proportion of B increases to 95%; 5-8min, the proportion of B remains at 95%; then, decrease to 5% within 0.5min and maintain for 1.5min to equilibrate the column.

[0070] The LC-TIC-MS spectrum of anti-wrinkle cyclic peptide-1 is shown in Figure 1 As shown; the LC-TIC-MS spectrum of anti-wrinkle cyclic peptide-2 is as shown Figure 2 shown.

[0071] Efficacy Test Example 2

[0072] Zebrafish type I collagen gene expression promotion test:

[0073] The zebrafish type I collagen gene expression promotion test method was tested using the "zebrafish type I collagen gene expression promotion test method".

[0074] Table 1 shows the test results of 0.001% anti-wrinkle cyclic peptide zebrafish collagen gene expression. Figure 3 As shown, compared with the blank control group, 0.001% anti-wrinkle cyclic peptide-1 of the present invention promoted the expression of Col1a1a by 156%, Col1a1b by 87%, and Col1a2 by 103%. Figure 4 As shown, compared with the blank control group, the expression promotion rate of Col1a1a by 0.001% anti-wrinkle cyclic peptide-2 of the present invention is as high as 94%, the expression promotion rate of Col1a1b is as high as 84%, and the expression promotion rate of Col1a2 is as high as 66%.

[0075] It can be seen from Table 1 that 0.001% anti-wrinkle cyclic peptide-1 and anti-wrinkle cyclic peptide-1 of the present invention have a significant promoting effect on the expression of zebrafish collagen gene compared with hexapeptide-11 in comparative example 1.

[0076] Table 1 Collagen gene expression promotion rate

[0077]

[0078] Zebrafish elastin gene expression promotion test:

[0079] The zebrafish elastin gene expression promotion test method was tested using the "Zebrafish elastin gene expression promotion test method".

[0080] Table 2 shows the test results of promoting zebrafish elastin gene expression with 0.001% anti-wrinkle cyclic peptide. Figure 5 As shown, compared with the blank control group, the expression promotion rate of 0.001% anti-wrinkle cyclic peptide-1 of the present invention on elastin gene Elna is as high as 132%; Figure 6 As shown, compared with the blank control group, the expression promotion rate of 0.001% anti-wrinkle cyclic peptide-2 of the present invention on elastin gene Elna is as high as 44%.

[0081] It can be seen from Table 2 that 0.001% anti-wrinkle cyclic peptide-1 and anti-wrinkle cyclic peptide-2 of the present invention have a significant promoting effect on the expression of zebrafish elastin gene compared with the application of hexapeptide-11 in comparative example 1.

[0082] Table 2 Promotion rate of elastin gene expression

[0083] category Compound Elna expression promotion rate Example 1 Anti-wrinkle cyclic peptide-1 132％ Example 2 Anti-wrinkle cyclic peptide-2 44％ Comparative Example 1 Hexapeptide-11 ＜3％

[0084] Application Test Example 1-2

[0085] Anti-wrinkle serum formula:

[0086] Table 3 Anti-wrinkle essence formula of Application Example 1, Application Example 2, and Comparative Example 1

[0087]

[0088]

[0089] The preparation method of the above anti-wrinkle essence is:

[0090] 1) Pre-disperse the sclerotium gum in phase A with water and stir at 75°C until the solution is transparent and free of precipitation;

[0091] 2) Add the ingredients of phase B to phase A according to Table 3 and stir for 8 minutes until emulsification is complete;

[0092] 3) Cool down to 42°C, pre-disperse the essence in phase C with PEG-40 hydrogenated castor oil and add it to the mixed system, add phase D according to Table 3, and stir evenly.

[0093] Efficacy Test Example 3

[0094] Anti-aging effect test method of anti-wrinkle essence

[0095] 1) Recruit 60 volunteers aged 18 to 40 (30 males and 30 females). The volunteers were evaluated to have no obvious skin damage and skin problems. They were randomly divided into 6 groups, with 10 people in each group (5 males and 5 females);

[0096] 2) Clean the subject's face with the same neutral cleanser in a constant temperature and humidity environment;

[0097] 3) In groups 1 to 4, a blank control sample was applied on the left side of the face and forehead, and samples of application examples 1 to 2 were evenly applied on the right side of the face and forehead, respectively. Application example 1 was applied to groups 1 to 2, and application example 2 was applied to groups 3 to 4, with a total sample amount of 2±0.2 g;

[0098] 4) Apply the blank control sample on the face and the left side of the forehead of Groups 5 to 6, and evenly apply the sample of Comparative Example 1 on the right side of the face and forehead, respectively, with a total sample amount of 2±0.2 g;

[0099] 5) Use VISA facial tester to measure facial wrinkles for 12 hours and 24 hours, measure three sets of data at each symmetrical part and calculate the average value;

[0100] 6) Based on the percentile score given by the VISA facial tester (the percentile score describes the skin feature score of the tester compared with other people of the same age, gender, and skin type, the higher the score, the better) improvement value (post-improvement score - pre-improvement score) is used as calculation, and the anti-aging effect of the essence is evaluated according to the number of people with different improvement situations.

[0101] The test results of anti-aging essence are shown in Table 4:

[0102] Table 4 Test results of anti-aging essence (people)

[0103]

[0104] In Table 4, in the 12-hour test, 80% of the facial improvement values ​​of Group 1 and Group 2 (i.e., Application Example 1) were above 10, and 55% of the forehead wrinkles were improved; in the 12-hour test, 70% of the facial improvement values ​​of Group 3 and Group 4 (i.e., Application Example 2) were above 10, and 45% of the forehead wrinkles were improved. In the 12-hour test, the anti-wrinkle essences of Application Examples 1 and 2 had a better improvement effect, and the degree of improvement on facial texture was higher.

[0105] In Table 4, in the 24-hour test, 95% of the facial improvement values ​​of Group 1 and Group 2 (i.e., Application Example 1) were above 10, and 60% of the forehead wrinkles were improved; in the 24-hour test, 75% of the facial improvement values ​​of Group 3 and Group 4 (i.e., Application Example 2) were above 10, and 60% of the forehead wrinkles were improved. It can be seen that in the 24-hour test, the anti-wrinkle essences of Application Examples 1 and 2 maintained a good improvement effect under the long-term essence effect. In the 24-hour test, the anti-wrinkle essences of Application Examples 1 and 2 had a good improvement effect on facial texture and forehead wrinkles.

[0106] In Table 4, in the 12-hour test, 25% of the facial improvement values ​​of Group 5 and Group 6 (i.e., Comparative Example 1) were above 10, and the forehead wrinkles were improved by 35%; in the 24-hour test, 30% of the facial improvement values ​​were above 10, and the forehead wrinkles were improved by 25%. The comparative example has a certain effect of improving facial texture and forehead wrinkles, but it is weaker than that of Examples 1 and 2.

[0107] The above description is only a preferred embodiment of the present invention and does not limit the present invention in any form. Therefore, any simple modification, equivalent change and modification made to the above embodiment according to the technical essence of the present invention without departing from the technical solution of the present invention still fall within the scope of the technical solution of the present invention.

Claims

1. A group of anti-wrinkle and firming cyclic peptide compounds, characterized in that: The anti-wrinkle and firming cyclic peptide compound is anti-wrinkle cyclic peptide-1 and / or anti-wrinkle cyclic peptide-2: Anti-wrinkle cyclic peptide-1: The sequence of anti-wrinkle cyclic peptide-1 is: c(CDLARLAMYA); The structural formula of anti-wrinkle cyclic peptide-1 is as shown in Formula Ⅰ: Anti-wrinkle cyclic peptide-2: The sequence of anti-wrinkle cyclic peptide-2 is: c(KTFKKTFK); The structural formula of anti-wrinkle cyclic peptide-2 is as shown in Formula II:

2. The method for preparing the anti-wrinkle and firming cyclic peptide compound according to claim 1, characterized in that: The preparation steps include: Step 1: Synthesis of linear peptides: 2-CTC resin was weighed in a reaction tube, and DCM was added to swell at room temperature for 1 hour. After the solvent was drained, the DCM solution of the first amino acid monomer at the C-terminus and DIEA was added, and after shaking reaction at room temperature for 1 hour, the resin was washed with DMF and DCM three times in sequence, and then drained. Then, the Fmoc protection was removed, and 20% piperidine / DMF solution was added for deprotection twice, each time for 10 minutes, and then the resin was washed with DCM and DMF three times in sequence; after being drained, the second amino acid was coupled, and the activated second amino acid monomer DMF solution was added. After shaking at room temperature for 1 hour, the resin was washed with DMF and DCM three times in sequence and drained; the above steps of Fmoc protection removal, washing, coupling, and washing were repeated until the last amino acid monomer; cutting; Step 2: Cyclization: The crude peptide product was dissolved in DMF, and HATU and DIEA were added in sequence after complete dissolution, and the reaction was carried out at room temperature for 2 hours; LCMS monitored the cyclization process, and after the reaction was complete, the solvent was removed by vacuum distillation to obtain a crude cyclopeptide product, which was dissolved in acetonitrile, and the insoluble solid was removed by centrifugation, and the filtrate was collected and spin-dried to carry out the next step of deprotection; Step 3: Deprotection: Prepare a deprotection solution of TFA / TIPS / DCM or TFA / TIPS / EDT / DCM, add it to the crude cyclic peptide product, shake at room temperature for 0.5-2h, and monitor the deprotection progress by LCMS; after the deprotection is complete, blow dry the solvent with an air pump, and purify the product using a column machine.

3. The method for preparing the anti-wrinkle and firming cyclic peptide compound according to claim 2, characterized in that: In the step 1, the concentration of the 2-CTC resin is 0.98 mmol / gloading; The first amino acid monomer at the C-terminus is 1.5 equiv; the DIEA is 5 equiv; The second amino acid monomer DMF solution includes 5 equiv of amino acid monomer, 4.75 equiv of condensing agent HBTU and 5 equiv of DIEA; The cleavage reagent: hexafluoroisopropanol (HFIP) / DCM (20%) or trifluoroacetic acid (TFA) / DCM (1%).

4. The method for preparing the anti-wrinkle and firming cyclic peptide compound according to claim 2, characterized in that: In the step 2, the DMF is 0.005M; The HATU is 2 equiv; the DIEA is 3-6 equiv.

5. The method for preparing the anti-wrinkle and firming cyclic peptide compound according to claim 2, characterized in that: In the step 3, the deprotection solution is TFA / TIPS / DCM=50:5:45 or TFA / TIPS / EDT / DCM=50:2.5:2.5:

45.

6. Use of the anti-wrinkle and firming cyclic peptide compound according to any one of claims 1 to 5 in the preparation of cosmetics.

7. The use according to claim 6, characterized in that The dosage form of the cosmetics includes ointments, creams, emulsions, aqueous solutions, oils, gels, powders, tablets, muds, patches, films, aerosols, sprays, freeze-dried preparations or nano preparations.

8. The use according to claim 6, characterized in that The cosmetic has the effects of anti-wrinkle and anti-skin aging.

9. A cosmetic, characterized in that: The invention comprises the anti-wrinkle and firming cyclic peptide compound according to any one of claims 1 to 5; the dosage form of the cosmetic comprises ointment, cream, emulsion, water, oil, gel, powder, tablet, mud, patch, film, aerosol, spray, freeze-dried preparation or nano preparation.

10. The cosmetic according to claim 9, characterized in that The cosmetic is an anti-wrinkle essence; The formula of the anti-wrinkle essence contains the following ingredients in percentage by weight: Sclerotium gum 0.5%, p-hydroxyacetophenone 0.3%, phenoxyethanol 0.25%, fragrance 0.02%, PEG-40 hydrogenated castor oil 0.1%, 1,3-butylene glycol 4%, anti-wrinkle firming cyclic peptide compound 0.05, the balance is water; The preparation method of the anti-wrinkle essence comprises the following steps: 1) Pre-disperse the sclerotium gum with water and stir at 75°C until the solution is transparent and free of precipitation; 2) Add p-hydroxyacetophenone and phenoxyethanol, and stir for 5-10 minutes until emulsification is complete; 3) Cool down to 40-45°C, pre-disperse the essence with PEG-40 hydrogenated castor oil and add it into the mixed system, then add 1,3-butylene glycol and anti-wrinkle firming cyclic peptide compound.

Images