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CN118791560B - A peptide capable of regulating sebum secretion and its synthesis method and application - Google Patents

A peptide capable of regulating sebum secretion and its synthesis method and application Download PDF

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Publication number
CN118791560B
CN118791560B CN202410775766.0A CN202410775766A CN118791560B CN 118791560 B CN118791560 B CN 118791560B CN 202410775766 A CN202410775766 A CN 202410775766A CN 118791560 B CN118791560 B CN 118791560B
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oil control
polypeptide
phase
stirring
oil
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CN118791560A (en
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李桃
邵炳豪
丁明宁
曾双
马洁婷
黎文祥
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Guangzhou Muke Biotechnology Co ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K7/00Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04Linear peptides containing only normal peptide links
    • C07K7/06Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/008Preparations for oily skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/008Preparations for oily hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Chemical & Material Sciences (AREA)
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  • Birds (AREA)
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  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

The invention provides a structure, a preparation method and an application method of a group of oil control polypeptides. The sequences of the oil control polypeptides are Pal-Tyr-Gly-Gly-Phe-Leu-OH, pal-Tyr- (D) Ala-Gly-Phe-Leu-OH and Pal-Leu-Lys-Thr-Arg-Asn-OH respectively. The inhibition rates of 5 alpha-reductase of the three polypeptides at 0.1% concentration are 39.00%, 30.94% and 40.31% respectively. The application form comprises, but is not limited to, application in daily chemicals, wherein the daily chemicals are selected from oil control essence, oil control cream, oil control facial mask, oil control scalp essence, oil control shampoo and acne removal essence, and the application method in daily chemical products is to disperse oil control polypeptide into solvents such as glycerin, propylene glycol and butanediol and then add the oil control polypeptide into daily chemical products. The prepared oil control polypeptide has excellent oil control effect when applied to oil control essence or oil control hair washing products.

Description

Peptide capable of regulating sebum secretion and synthesis method and application thereof
Technical Field
The invention relates to synthesis and application of a group of peptides, belongs to the technical field of cosmetics, and particularly relates to peptides capable of regulating sebum secretion, and a synthesis method and application thereof.
Background
Sebaceous glands are a type of multi-acinar holoak secretory tissue distributed throughout the skin except the palms and soles, with the highest density on the scalp and face. The normal lipid on the skin surface can play a role of barrier, and can moisten the skin, resist infection and maintain the bacterial balance on the skin surface of a human body. Excessive sebum secretion from sebaceous glands can lead to excessive oil production from the skin, affecting the aesthetics of the face and hair, and may promote the development of acne or other diseases.
Chinese patent 2020110294878 discloses a plant extract composition with multi-target scalp oil control and dandruff removal effects, a preparation method thereof and a scalp care composition, wherein the composition consists of 20-40% of camellia seed extract, 15-25% of tea bran polysaccharide, 10-30% of citrus peel extract, 10-30% of eucalyptus extract and 1-20% of radix sophorae flavescentis extract, and the multi-target oil control and dandruff removal purposes are realized through four different ways (inhibiting microbial lipase, inhibiting malassezia B-carbonic anhydrase, inhibiting 5 a-reductase in scalp cells and inhibiting propionibacterium acnes).
The polypeptide is a core component for repeatedly giving the Nobel prize, and has the characteristics of definite structure, clear efficacy mechanism, strong efficacy, low onset of action (the remarkable effect can be achieved by adding only a few to hundreds of ppm), and the like, and the cosmetic peptide with different effects of resisting wrinkle, whitening, moisturizing, resisting oxidation, repairing, and the like is widely developed and applied. Chinese patent CN 107325157B discloses decapeptides and nonapeptides with sebum secretion regulating effect, the amino acid sequences of the two polypeptides being distributed Ser-Val-Ala-Lys-Arg-Glu-Cys-Arg-Asp-gin and Glu-His-Gly-Pro-Phe-Asp-Ala-gin-Pro.
The prior art has developed polypeptides with sebum regulation, but because of the long amino acid sequence, low yield, high cost and poor hydrolysis resistance of the product, the use in cosmetic products is not favored.
Therefore, there is a need to develop a polypeptide raw material with cost advantages, efficacy advantages and stability advantages for use in cosmetic formulations, which provides a solution for facial oil extraction as well as head oil extraction.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide peptides for regulating sebum secretion, and the prepared oil control polypeptide has excellent oil control effect when applied to oil control essence or oil control hair washing products.
The technical scheme of the invention is as follows:
In a first aspect, the present invention provides three oil control polypeptides having excellent properties, the oil control polypeptides comprising:
Oil control polypeptide-1:
The sequence of the oil control polypeptide-1 is Pal-Tyr-Gly-Gly-Phe-Leu-OH;
The structural formula of the oil control polypeptide-1 is shown as formula I:
oil control polypeptide-2:
the sequence of the oil control polypeptide-2 is Pal-Tyr- (D) Ala-Gly-Phe-Leu-OH;
the structural formula of the oil control polypeptide-2 is shown as formula II:
Oil control polypeptide-3:
The sequence of the oil control polypeptide-3 is Pal-Leu-Lys-Thr-Arg-Asn-OH;
the structural formula of the oil control polypeptide-3 is shown as formula III:
in a second aspect, the present invention provides a method for preparing an oil control polypeptide, comprising the steps of:
Step one, compound synthesis:
2-chlorotritylmethyl chloride (2-CTC resin, 1.58mmol/g loading,4 g) was weighed into a reaction tube and swollen with Dichloromethane (DCM) at room temperature for 1 hour. After the solvent was drained, a 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 1h of reaction at room temperature with shaking, the resin was washed 3 times with N, N-Dimethylformamide (DMF) and DCM in that order, and drained. The Fmoc deprotection was then performed, deprotected 2 times with 20% piperidine/DMF solution for 10min each, followed by 3 washes of the resin with DCM and DMF sequentially. After draining, the second amino acid is coupled, an activated second amino acid monomer DMF solution (comprising 5equiv amino acid monomer, 4.75equiv condensing agent HBTU and 5equiv DIEA) is added, the reaction is carried out for 1h at room temperature with shaking, and after washing the resin 3 times with DMF and DCM in sequence, draining. Repeating the steps of Fmoc protection, washing, coupling and washing till the last amino acid monomer. After all couplings were completed, fmoc deprotection, washing and draining were performed. Subsequently palmitoylation was performed, a solution of palmitoyl chloride (2 equiv) and DIEA (2.5 equiv) in DCM was added to the resin, and the reaction was carried out with shaking at room temperature for 2h, and the resin was washed with DMF and DCM 3 times in this order and dried.
Step two, compound cracking:
To the palmitoyl-pentapeptide resin, a cleavage reagent, trifluoroacetic acid (TFA)/Triisopropylsilane (TIPS)/water=95/2.5/2.5, was added and the reaction was carried out with shaking at room temperature for 2 hours. The filtrate was collected in a centrifuge tube, washed 2 times with DCM and acetonitrile, and the filtrates were combined. Drying most of the solvent by air pump, adding anhydrous diethyl ether to precipitate, mixing completely, centrifuging, pouring supernatant,
The mixture was washed 3 times to obtain a crude product.
Step three, purifying a compound:
The polypeptide is dissolved in solvents such as acetonitrile, ethyl acetate, ethanol and the like, and the crude product is further purified by washing, pulping or recrystallization.
The purification comprises the specific steps of dissolving the polypeptide in a mixed solvent of ethyl acetate and ethanol in a ratio of 2:1, heating and refluxing until the polypeptide is clarified, standing at room temperature for crystallization precipitation, and filtering to obtain the final purified polypeptide.
The purity of the oil control polypeptide prepared by the preparation method of the oil control polypeptide provided by the invention is more than 98%.
In a third aspect, the present invention provides methods for the use of oil control peptides in daily chemical products.
The application forms of the oil control peptide in the daily chemical products comprise, but are not limited to, oil control essence, oil control cream, oil control facial mask, oil control scalp essence, oil control shampoo, acne removal essence and other products, and the application method of the oil control peptide in the daily chemical products is that the oil control peptide is dispersed in solvents such as glycerol, propylene glycol and butanediol and then added into the daily chemical products.
The cosmetic is oil control essence;
The oil control essence comprises the following components in percentage:
phase A comprises water balance, EDTA-2Na 0.1%, sodium hyaluronate 0.04%, acrylic acid (ester) copolymer sodium 0.3%, xanthan gum 0.1%, arginine 0.08%;
Phase B, phenoxyethanol 0.4%, hexanediol 0.8% and ethylhexyl glycerol 0.1%;
2% of propylene glycol, and 2% of oil control polypeptide-1 or 2 or 3;
The percentage content of the oil control polypeptide is that the oil control polypeptide is-1.2 percent, or the oil control polypeptide is-2.15 percent, or the oil control polypeptide is-3.1 percent;
the preparation method for the oil control and refining comprises the following steps:
Sequentially adding the phase A into a reaction container, stirring and dispersing, heating to 75 ℃, preserving heat and stirring for 15-30 minutes, adding the phase B after the phase A is completely dispersed, stirring and cooling to below 40 ℃, adding the uniformly mixed phase C, and stirring and dispersing uniformly to obtain the final oil control essence.
The daily chemical product is oil-control hair washing water;
the oil control shampoo comprises the following components in percentage:
63.23% of water, 0.2% of guar hydroxypropyl trimethyl ammonium chloride, 0.2% of polyquaternium-11, and 0.07% of citric acid;
15% of lauryl hydroxysulfobetaine and 14% of sodium laureth sulfate;
phase C comprises polysiloxane quaternary ammonium salt-16.5%, phenoxyethanol 0.5%, sodium benzoate 0.5%, essence 0.6% and salt 1%;
3% of propylene glycol, and 0.3% of oil control polypeptide-1 or oil control polypeptide-2 or oil control polypeptide-3;
The preparation method of the oil control shampoo comprises the following steps:
Sequentially adding the phase A into a reaction container, stirring and dispersing, heating to 75 ℃, preserving heat and stirring for 15-20 minutes, sequentially adding the phase B after the phase A is completely dispersed, preserving heat and stirring for 20 minutes, uniformly mixing the phase A and the phase B, cooling to 40 ℃, adding the phase C, stirring and dispersing, adding the premixed phase D, and stirring and dispersing uniformly to obtain the final oil control shampoo.
The invention has the technical effects and beneficial effects as follows:
1) The invention designs and develops a group of oil control peptides with excellent performance, which comprises oil control polypeptide-1:pal-Tyr-Gly-Gly-Phe-Leu-OH, oil control polypeptide-2:pal-Tyr- (D) Ala-Gly-Phe-Leu-OH, oil control polypeptide-3:pal-Leu-Lys-Thr-Arg-Asn-OH;
2) The invention provides a preparation method of oil control peptide, and the purity of the prepared oil control peptide is more than 98%;
3) The designed and developed oil control peptide has excellent 5 alpha-reductase inhibition effect, wherein the 5 alpha-reductase inhibition rate of 0.1% of the oil control peptide 1 is up to 39.00%, the 5 alpha-reductase inhibition rate of 0.1% of the oil control peptide 2 is up to 30.94%, and the 5 alpha-reductase inhibition rate of 0.1% of the oil control peptide 3 is up to 40.31%;
4) The sebum secretion inhibition rate of the oil control essence containing the oil control peptide is more than 30%.
Drawings
FIG. 1 is a LCMS spectrum of oil control polypeptide-1;
FIG. 2 is a LCMS spectrum of oil control polypeptide-2;
FIG. 3 is a LCMS spectrum of oil control polypeptide-3;
FIG. 4 is a graph showing comparison of 5. Alpha. -reductase inhibition ratios.
Detailed Description
The following detailed description of the present invention will provide further details in order to make the above-mentioned objects, features and advantages of the present invention more comprehensible.
The term "by..preparation" as used herein is synonymous with "comprising. The terms "comprising," "including," "having," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, step, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, step, method, article, or apparatus.
When an equivalent, concentration, or other value or parameter is expressed as a range, preferred range, or a range bounded by a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when ranges of "1 to 5" are disclosed, the described ranges should be construed to include ranges of "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a numerical range is described herein, unless otherwise indicated, the range is intended to include its endpoints and all integers and fractions within the range.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. The present invention may be embodied in many other forms than described herein and similarly modified by those skilled in the art without departing from the spirit of the invention, whereby the invention is not limited to the specific embodiments disclosed below.
Examples 1 to 3
The invention provides three oil control polypeptides, the sequences and structures of which are respectively as follows:
Oil control polypeptide-1:
The sequence of the oil control polypeptide-1 is Pal-Tyr-Gly-Gly-Phe-Leu-OH;
The structural formula of the oil control polypeptide-1 is shown as formula I:
LCMS spectra of oil control polypeptide-1 are shown in figure 1.
Oil control polypeptide-2:
the sequence of the oil control polypeptide-2 is Pal-Tyr- (D) Ala-Gly-Phe-Leu-OH;
the structural formula of the oil control polypeptide-2 is shown as formula II:
LCMS spectra of oil control polypeptide-2 are shown in figure 2.
Oil control polypeptide-3:
The sequence of the oil control polypeptide-3 is Pal-Leu-Lys-Thr-Arg-Asn-OH;
the structural formula of the oil control polypeptide-3 is shown as formula III:
LCMS spectra of oil control polypeptide-3 are shown in figure 3.
The oil control polypeptide is prepared by the following steps:
first step, synthesis of Compounds
2-Chlorotritylmethyl chloride (2-CTC resin, 1.58mmol/g loading,4 g) was weighed into a reaction tube and swollen with Dichloromethane (DCM) at room temperature for 1 hour. After the solvent was drained, a 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 1h of reaction at room temperature with shaking, the resin was washed 3 times with N, N-Dimethylformamide (DMF) and DCM in that order, and drained. The Fmoc deprotection was then performed, deprotected 2 times with 20% piperidine/DMF solution for 10min each, followed by 3 washes of the resin with DCM and DMF sequentially. After draining, the second amino acid is coupled, an activated second amino acid monomer DMF solution (comprising 5equiv amino acid monomer, 4.75equiv condensing agent HBTU and 5equiv DIEA) is added, the reaction is carried out for 1h at room temperature with shaking, and after washing the resin 3 times with DMF and DCM in sequence, draining. Repeating the steps of Fmoc protection, washing, coupling and washing till the last amino acid monomer. After all couplings were completed, fmoc deprotection, washing and draining were performed. Subsequently palmitoylation was performed, a solution of palmitoyl chloride (2 equiv) and DIEA (2.5 equiv) in DCM was added to the resin, and the reaction was carried out with shaking at room temperature for 2h, and the resin was washed with DMF and DCM 3 times in this order and dried.
Step two, compound cracking:
To the palmitoyl-pentapeptide resin, a cleavage reagent, trifluoroacetic acid (TFA)/Triisopropylsilane (TIPS)/water=95/2.5/2.5, was added and the reaction was carried out with shaking at room temperature for 2 hours. The filtrate was collected in a centrifuge tube, washed 2 times with DCM and acetonitrile, and the filtrates were combined. Drying most of the solvent by an air pump, adding anhydrous diethyl ether to separate out precipitate, fully mixing, centrifuging, pouring supernatant, and washing for 3 times to obtain a crude product.
Step three, purifying a compound:
Dissolving the polypeptide in a mixed solvent of ethyl acetate and ethanol in a ratio of 2:1, heating and refluxing until the mixture is clarified, standing at room temperature for crystallization precipitation, and filtering to obtain the final purified polypeptide.
Application examples 1 to 3 and comparative examples 1 to 3
The preparation method of the product containing the oil control polypeptide comprises the following steps:
oil control essence Hua Zhibei containing oil control polypeptide:
application examples 1-3 and comparative examples 1-3 of the oil control essence were prepared according to the addition ratio of table 1, and the preparation steps are as follows:
1) Sequentially adding the phase A into a reaction container, stirring and dispersing, heating to 75 ℃, and preserving heat and stirring for 15-30 minutes;
2) After the phase A is completely dispersed, adding the phase B, stirring and cooling to below 40 ℃;
3) Adding the uniformly mixed C phase, and stirring and dispersing uniformly to obtain the final oil control essence.
Table 1 oil control and refinement application examples 1 to 3 and comparative examples 1 to 3
Application examples 4 to 6 and comparative examples 4 to 6
Preparing shampoo containing oil control polypeptide:
The application examples 4-6 and comparative examples 4-6 of the oil control shampoo were prepared according to the addition ratio of table 2, and the preparation steps are as follows:
1) Sequentially adding the phase A into a reaction container, stirring and dispersing, heating to 75 ℃, and preserving heat and stirring for 15-20 minutes;
2) After the phase A is completely dispersed, adding the phase B in sequence, and stirring for 20 minutes under heat preservation;
3) After the phase A and the phase B are uniformly mixed, the temperature is reduced to 40 ℃, the phase C is added, and stirring and dispersion are carried out;
4) Adding the premixed phase D, stirring and dispersing uniformly to obtain the final oil control shampoo.
Table 2 oil control shampoo examples and comparative examples
Effect test example 1
Test method of 5 alpha-reductase inhibition rate:
the 5 a-reductase catalyzes the conversion of testosterone to dihydrotestosterone in the presence of reduced coenzyme II, and if a5 a-reductase inhibitor is present, this reaction process is inhibited to some extent. Since reduced coenzyme II has characteristic absorption at 340nm wavelength, oxidized coenzyme II generated after participating in the reaction has characteristic absorption vanished at 340nm wavelength. The measurement by an ultraviolet spectrophotometer can reflect whether a certain substance has an inhibition effect and the magnitude of the inhibition effect on 5 a-reductase.
Measurement of blank control A4. Mu.L of testosterone T (20.747 mmol/L), 6. Mu.L of 5. Alpha. -reductase (176 mg/mL), 60. Mu.L of phosphate buffer (pH=7.4), 30. Mu.L of reduced coenzyme II were added to the reaction tube, absorbance was measured after mixing, absorbance was measured after incubation at 37℃for 60min, and the blank drop background value of reduced coenzyme II was subtracted to measure the blank drop value (. DELTA.A 0)
Measurement of inhibitor 4. Mu.L of testosterone T (20.747 mmol/L), 6. Mu.L of 5. Alpha. -reductase (176 mg/mL), 5. Mu.L of sample to be measured (specifically, as shown in Table 3), 55. Mu.L of phosphate buffer (pH=7.4), 30. Mu.L of reduced coenzyme II, measurement of absorbance after mixing, measurement of absorbance after incubation at 37℃for 60min, subtraction of background value of blank drop of reduced coenzyme II, and measurement of drop value (DeltaA n) of the sample. The test was repeated 3 times with 3 parallel samples each. The inhibition ratio was calculated according to an inhibition ratio formula, which is I (%) = (Δa 0-ΔAn)/ΔA0 ×100%.
Test structure of 5 alpha reductase inhibition ratio and results are shown in Table 3 and FIG. 4
TABLE 3 sample to be tested Table and 5 alpha reductase inhibition ratio
As can be seen from table 3 and fig. 4, the effect of the oil control polypeptide of the present invention is far superior to that of the negative control group, and the 5a reductase inhibition rate of the oil control polypeptide of the present invention is very close to that of the positive control group at the addition concentration of 0.1%, which indicates that the oil control polypeptide of the present invention has an excellent 5a reductase inhibition effect.
Effect test example 2
The essence oil control effect testing method comprises the following steps:
1) The volunteers with oily skin or mixed skin (between 18 and 40 years old) are divided into 9 groups of 10 people (5 men and 5 women);
2) Cleaning the face of a subject with the same face cleaning in a constant temperature and humidity environment;
3) Respectively smearing blank control samples on the left side of the forehead from the 1 st group to the 6 th group, respectively smearing samples of application examples 1-3 and comparative examples 1-3 on the right side of the forehead, wherein the sample amount is 2+/-0.2 g;
4) Respectively smearing samples of comparative examples 1-3 on the left side of the forehead of the 7 th group to the 9 th group, respectively smearing samples of application examples 1-3 on the right side of the forehead, wherein the sample amount is 2+/-0.2 g;
5) By means of The MB560 grease tester (CK company in Germany) measures the grease amount at the left side and the right side of the forehead for 1 hour, 6 hours and 12 hours, and three groups of data are measured at the symmetrical parts respectively and an average value is calculated;
6) According to the oil reduction rate calculation formula, the oil reduction rate is calculated, and the oil reduction rate= (amount of oil on the left side of the forehead-amount of oil on the right side of the forehead)/amount of oil on the left side of the forehead is multiplied by 100%.
The results of the oil control refinement test are shown in table 4:
TABLE 4 test results of oil control essence (human)
In table 4, the grease reduction rate of most of the group 1, group 2 and group 3 was more than 10%, and the grease reduction rate at 12 hours was more than 30% and was more than half of the population. This shows that application examples 1,2 and 3 have excellent oil control effect. In table 4, the reduction rate of grease in most of the 4 th group, 5 th group and 6 th group was less than 10%, which indicates that the comparative example also had a certain oil control effect, but the oil control effect was weak.
The group 7, group 8 and group 9 mainly concentrate on the region with the grease reduction rate of 10-30%, which indicates that the oil control effect of the application example is far better than that of the comparative example.
Effect test example 3
The method for testing the oil control effect of the shampoo comprises the following steps:
1) Oily scalp volunteers (between 18-40 years old) were divided into 9 groups of 10 persons each (5 men, 5 women);
2) Performing a semi-hair washing test for volunteers by special hair washing staff in a constant temperature and humidity environment;
3) Blank controls are respectively used on the left heads of the 1 st group to the 6 th group, samples of application examples 4-6 and comparative examples 4-6 are used on the right heads, the sample amount is 8+/-0.5 g, and the left heads and the right heads are respectively washed, massaged for 3 minutes, then washed cleanly by water and dried;
4) The samples of comparative examples 4-6 are respectively used at the left heads of the 7 th group to the 9 th group, the samples of application examples 4-6 are respectively used at the right heads, the sample amount is 8+/-0.5 g, and the left heads and the right heads are respectively washed, massaged for 3 minutes, then washed cleanly by water and dried;
5) By means of The MB560 grease tester (German CK company) measures the grease content of the first, second and third times of hair washing at 24 hours, and three groups of data are measured at the symmetrical positions respectively and an average value is calculated, wherein the time interval of the first, second and third times of hair washing is one day, for example, 8 points of hair washing in the morning today, 8 points of hair washing in the next day can be used for testing the data, and the second time of hair washing is carried out after the data are tested.
6) According to the oil-fat reduction rate calculation formula, the oil-fat reduction rate was calculated as oil-fat reduction rate= (head left-side oil-head right-side oil-fat)/head left-side oil-fat x 100%.
The test results of the oil control shampoo are shown in table 5.
TABLE 5 test results of oil control shampoo (human)
In table 5, the group 1, group 2 and group 3 mainly concentrate on the intervals of 0-10% and 10-30% of grease reduction rate, and after 3 times of hair washing, the grease reduction rate of a small part of people is 30-50%, while the group 4, group 5 and group 6 concentrate on the interval of 0-10% of grease reduction rate, and by combining the comparative use data of the application examples of the group 7, group 8 and group 9 and the comparative example, it can be seen that the grease reduction rate of the application examples is better than the comparative example, and the grease inhibition rate of more than half of people after the third use is more than 10%.
The above-mentioned embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention in any way, so that the present invention is not limited to the above-mentioned embodiments, any simple modification, equivalent variation and modification of the above embodiments according to the technical substance of the present invention still fall within the scope of the technical solution of the present invention.

Claims (2)

1. The application method of the polypeptide with the function of regulating sebum secretion in preparing the oil control hair washing product is characterized in that the oil control hair washing product is oil control hair washing water, and the application method is that the oil control polypeptide is dispersed in glycerol, propylene glycol and butanediol solvent and then added into the oil control hair washing product;
The polypeptide with the function of regulating sebum secretion is oil control polypeptide-3;
Wherein the sequence of the oil control polypeptide-3 is Pal-Leu-Lys-Thr-Arg-Asn-OH;
the structural formula of the oil control polypeptide-3 is shown as formula III:
2. the use according to claim 1, wherein the oil control shampoo comprises the following components in percentage:
63.23% of water, 0.2% of guar hydroxypropyl trimethyl ammonium chloride, 0.2% of polyquaternium-11, and 0.07% of citric acid;
15% of lauryl hydroxysulfobetaine and 14% of sodium laureth sulfate;
phase C comprises polysiloxane quaternary ammonium salt-16.5%, phenoxyethanol 0.5%, sodium benzoate 0.5%, essence 0.6% and salt 1%;
3% of propylene glycol and 0.3% of oil control polypeptide;
the preparation method of the oil control shampoo comprises the following steps:
Sequentially adding the phase A into a reaction container, stirring and dispersing, heating to 75 ℃, preserving heat and stirring for 15-20 minutes, sequentially adding the phase B after the phase A is completely dispersed, preserving heat and stirring for 20 minutes, uniformly mixing the phase A and the phase B, cooling to 40 ℃, adding the phase C, stirring and dispersing, adding the premixed phase D, and stirring and dispersing uniformly to obtain the final oil control shampoo.
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CN110105432A (en) * 2015-04-28 2019-08-09 凯尔格恩有限公司 Have effects that anti-fat and anti-diabetic peptide and its purposes
CN113301910A (en) * 2019-01-21 2021-08-24 环球科技创新有限股份公司 Skin rejuvenation and healing mixtures of peptide components and uses thereof

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FR2984127A1 (en) * 2011-12-14 2013-06-21 Oreal USE OF PROTEIN MMP-12 IN THE PREVENTION AND / OR TREATMENT OF OIL AND / OR FATTY SKIN.
FR3079749B1 (en) * 2018-04-05 2022-10-28 Sederma Sa USE OF A PEPTIDE FOR TREATMENT OF THE EPIDERMIS
CN114177107B (en) * 2021-12-10 2022-12-06 广州环亚化妆品科技股份有限公司 Acne-removing composition and preparation method and application thereof
CN116831937A (en) * 2023-04-10 2023-10-03 北京衍微科技有限公司 Application of lipopeptides and compositions thereof in inhibiting activity of 5 alpha-reductase
CN116725921A (en) * 2023-07-05 2023-09-12 香鉴香氛科技研发(广州)有限公司 Oil-control and anti-dandruff composition, oil-control and anti-dandruff shampoo and preparation method thereof
CN117357453A (en) * 2023-10-26 2024-01-09 广州大唐化妆品有限公司 Skin oil control composition and application thereof
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CN106999401A (en) * 2014-12-16 2017-08-01 赛德玛公司 Peptide compounds, the purposes for including their compositions and the compound, particularly cosmetics
CN110105432A (en) * 2015-04-28 2019-08-09 凯尔格恩有限公司 Have effects that anti-fat and anti-diabetic peptide and its purposes
CN113301910A (en) * 2019-01-21 2021-08-24 环球科技创新有限股份公司 Skin rejuvenation and healing mixtures of peptide components and uses thereof

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