Cosmetic composition derived from natural products for improving skin health

Abstract

The present application relates to cosmetic compositions containing resveratrol for improving skin health.

Description

Technical Field

[0001] This application relates to cosmetic compositions containing resveratrol for improving skin health. Background Technology

[0002] Resveratrone is a compound derived from the natural product resveratrol. The structure of this compound and its manufacturing method have been patented [Korean Patent Publication No. 1294993, US Patent Publication No. 10787607]. Furthermore, there have been reports on the anticancer effects of resveratrone [Korean Patent Publication No. 2169585], but its efficacy related to skin health remains unclear. Summary of the Invention

[0003] Technical issues

[0004] This application aims to provide a cosmetic composition containing resveratrol for improving skin health.

[0005] However, the technical problems to be solved by this application are not limited to the above-mentioned technical problems, and those skilled in the art can clearly understand other problems not mentioned from the following description.

[0006] Technical solution

[0007] The first aspect of this application provides a cosmetic composition comprising a compound represented by the following chemical formula 1 as an active ingredient:

[0008] [Chemical Formula 1]

[0009]

[0010] In the chemical formula 1,

[0011] R 1 It is hydrogen; halogen; straight-chain or branched carbon. 1-6 Alkyl; C 3-6 Cycloalkyl; straight-chain or branched C 1-6 Alkoxy groups; C groups containing N, O, or S as heteroatoms 2-6 Heterocyclic alkyl groups; or groups selected from halogen atoms, amino groups, nitrile groups, nitro groups, C 1-10 Alkyl, C 2-10 alkenyl, C 1-10 Alkoxy, C 3-6 Cycloalkyl groups, C groups containing N, O, or S as heteroatoms 2-6 Heterocyclic alkyl, C 6-16 Aryl groups and C groups containing N, O, or S as heteroatoms 5-15At least one substituent in the heteroaryl group is a phenyl group that is substituted or unsubstituted.

[0012] R 2 and R 3 Each is independently selected from hydroxyl, straight-chain or branched C. 1-6 Alkyl and benzoyl groups.

[0013] The second aspect of this application provides a single-function or multi-function cosmetic comprising a cosmetic composition according to the first aspect.

[0014] Invention Effects

[0015] The cosmetic composition containing resveratrol compounds according to embodiments of this application has the following characteristics: it can induce cell proliferation, thus having a skin regeneration effect; it can remove reactive oxygen species, thus having an antioxidant effect; and it can inhibit melanin synthesis and inhibit tyrosinase activity, thus having a skin whitening effect.

[0016] The cosmetic composition containing resveratrol compounds according to embodiments of this application has the following characteristics: it can promote collagen synthesis, thus improving skin elasticity and wrinkles; it can inhibit the growth of bacteria that cause acne, thus having an antibacterial (anti-acne) effect on the skin; and it has an ultraviolet protection effect. Attached Figure Description

[0017] Figure 1 This is a graph showing the cell proliferation efficacy evaluation results of resveratrol compounds in one embodiment of this application.

[0018] Figure 2 This is a graph showing the results of the antioxidant efficacy evaluation (DPPH determination) of resveratrol compounds in one embodiment of this application.

[0019] Figure 3 This is a graph showing the results of the whitening efficacy evaluation (inhibition of melanin synthesis in B16F10 cells) of resveratrol compounds in one embodiment of this application.

[0020] Figure 4 This is a graph showing the results of the whitening efficacy evaluation (B15F10 extracellular melanin synthesis inhibition ability) of resveratrol compound in one embodiment of this application.

[0021] Figure 5 This is a graph showing the whitening efficacy evaluation (tyrosinase activity inhibition ability) results of resveratrol compound in one embodiment of this application.

[0022] Figure 6 This is a graph showing the results of evaluating the wrinkle-improving efficacy (collagen synthesis efficacy) of resveratrol compounds in one embodiment of this application.

[0023] Figure 7 This is a graph showing the results of the evaluation of the anti-acne efficacy of resveratrol compounds (antibacterial efficacy against Propionibacterium acnes) in one embodiment of this application.

[0024] Figure 8 This is the absorption spectrum of a resveratrol compound in one embodiment of this application.

[0025] Figure 9 This is a photograph showing the UV protection factor of a cream containing resveratrol compounds in one embodiment of this application. Detailed Implementation

[0026] The embodiments and examples of the present invention will now be described in detail with reference to the accompanying drawings to enable those skilled in the art to readily implement them. However, this application can be implemented in many different forms and is not limited to the embodiments and examples described herein. For the purpose of clearly describing the invention in the accompanying drawings, parts unrelated to the description have been omitted, and similar reference numerals have been assigned to similar parts throughout the specification.

[0027] Throughout this application, when referring to a part being “connected” to another part, this includes not only the case of a “direct connection” but also the case of another element being located between them to form an “electrical connection”.

[0028] Throughout this application, when it is mentioned that a component is "on" another component, this includes not only the case where the component is in contact with the other component, but also the case where there is another component between them.

[0029] Throughout this application, when a reference is made that a part “includes” a component, it means, unless otherwise stated to the contrary, that other components may also be included without excluding them.

[0030] As for the degree-related terms "about," "basically," etc. used in this specification, these terms are used to indicate the value or close to the value when given the manufacturing and material tolerances inherent in the meaning mentioned, and are intended to prevent malicious infringers from improperly using the disclosure content that mentions accurate or absolute values ​​in order to help understand this application.

[0031] The terms “perform the step of” or “the step of” used throughout the specification of this application do not mean “the step of”.

[0032] Throughout this application, the term "one or more combinations thereof" included in the Markus type description refers to at least one mixture or combination of the components selected from the group consisting of the components described in the Markus type description, which means including at least one selected from the group consisting of the said components.

[0033] Throughout the description of this application, the phrase “A and / or B” means “A or B, or A and B”.

[0034] The embodiments of the present invention are described in detail below, but the present invention is not limited thereto.

[0035] The first aspect of this application provides a cosmetic composition comprising a compound represented by the following chemical formula 1 as an active ingredient:

[0036] [Chemical Formula 1]

[0037]

[0038] In the chemical formula 1,

[0039] R 1 It is hydrogen; halogen; straight-chain or branched carbon. 1-6 Alkyl; C 3-6 Cycloalkyl; straight-chain or branched C 1-6 Alkoxy groups; C groups containing N, O, or S as heteroatoms 2-6 Heterocyclic alkyl groups; or groups selected from halogen atoms, amino groups, nitrile groups, nitro groups, C 1-10 Alkyl, C 2-10 alkenyl, C 1-10 Alkoxy, C 3-6 Cycloalkyl groups, C groups containing N, O, or S as heteroatoms 2-6 Heterocyclic alkyl, C 6-16 Aryl groups and C groups containing N, O, or S as heteroatoms 5-15 At least one substituent in the heteroaryl group is a phenyl group that is substituted or unsubstituted.

[0040] R 2 and R 3 Each is independently selected from hydroxyl, straight-chain or branched C. 1-6 Alkyl and benzoyl groups.

[0041] In one embodiment of this application, the compound represented by chemical formula 1 can be represented by the following chemical formula 2:

[0042] [Chemical Formula 2]

[0043]

[0044] In the chemical formula 2,

[0045] R 1 It is hydrogen; halogen; straight-chain or branched carbon. 1-6 Alkyl; C 3-6 Cycloalkyl; straight-chain or branched C 1-6 Alkoxy groups; C groups containing N, O, or S as heteroatoms 2-6 Heterocyclic alkyl groups; or groups selected from halogen atoms, amino groups, nitrile groups, nitro groups, C 1-10 Alkyl, C 2-10 alkenyl, C 1-10 Alkoxy, C 3-6 Cycloalkyl groups, C groups containing N, O, or S as heteroatoms 2-6 Heterocyclic alkyl, C 6-16 Aryl groups and C groups containing N, O, or S as heteroatoms 5-15 At least one substituent in the heteroaryl group is a phenyl group that is substituted or unsubstituted.

[0046] R 2 and R 3 Each is independently selected from hydroxyl, straight-chain or branched C. 1-6 Alkyl and benzoyl groups.

[0047] In one embodiment of this application, the compound represented by chemical formula 1 may be selected from... But it doesn't have to be limited to this.

[0048] In one embodiment of this application, the compound represented by Chemical Formula 1 may be in the form of a cosmetically acceptable salt. In one embodiment of this application, the salt may be an acid addition salt formed from an inorganic acid or an organic acid. The inorganic acid may include at least one selected from hydrochloric acid, phosphoric acid, hydrobromic acid, nitric acid, carbonic acid, tartaric acid, boric acid, and carbonic acid. The organic acid may include at least one selected from formic acid, acetic acid, lactic acid, butyric acid, citric acid, propionic acid, isobutyric acid, trifluoroacetic acid, malic acid, maleic acid, malonic acid, fumaric acid, succinic acid, succinic acid monoamide, glutamic acid, dichloroacetic acid, aminooxyacetic acid, tartaric acid, oxalic acid, citric acid, glycolic acid, glucuronic acid, galacturonic acid, ascorbic acid, benzoic acid, phthalic acid, salicylic acid, anthranilic acid, benzenesulfonic acid, p-toluenesulfonic acid, or methanesulfonic acid, but may not be limited thereto. In one embodiment of this application, the acid addition salt can be prepared by conventional salt preparation methods, wherein the compound represented by the chemical formula 1 is directly mixed with an acid or mixed in the presence of a solvent.

[0049] The second aspect of this application provides a single-function or multi-function cosmetic comprising a cosmetic composition according to the first aspect.

[0050] In one embodiment of this application, the multifunctionality may include at least one selected from skin regeneration, skin whitening, skin wrinkle improvement, anti-acne, ultraviolet protection, and antioxidant.

[0051] In one embodiment of this application, the skin regeneration refers to the recovery of skin tissue damaged by inflammation and wounds due to the regeneration of skin cells, and the cosmetics used for the skin regeneration can have the effect of accelerating skin regeneration because the compounds represented by the chemical formula 1 promote cell proliferation.

[0052] In one embodiment of this application, the skin whitening refers to brightening the skin color and improving skin pigmentation such as melasma and freckles, and the cosmetics used for the skin whitening can have a skin whitening effect because the compound represented by chemical formula 1 inhibits the synthesis of melanin in the skin and inhibits the activity of melanin synthase.

[0053] In one embodiment of this application, the skin wrinkle improvement refers to improving or inhibiting the formation of skin wrinkles by increasing skin elasticity, and the cosmetics used for the skin wrinkle improvement can have the effect of improving skin elasticity and skin wrinkle improvement because the compound represented by the chemical formula 1 helps the skin's collagen synthesis.

[0054] In one embodiment of this application, the skin anti-acne (antibacterial) property refers to inhibiting or hindering the growth of bacteria on the skin. The skin antibacterial function may be due to the inhibition of the growth of bacteria that cause skin acne by a compound represented by chemical formula 1.

[0055] In one embodiment of this application, the antioxidant effect can be achieved by removing reactive oxygen species from the skin using a compound represented by Chemical Formula 1.

[0056] In one embodiment of this application, the cosmetic has the following characteristics: it can simultaneously possess the effects of skin regeneration, whitening, wrinkle improvement, antibacterial, skin anti-oxidation, and ultraviolet protection by including the cosmetic composition, and each function can have different degrees of functionality depending on the content of the compound represented by Chemical Formula 1, and multiple products can be manufactured by changing the content according to the purpose. In one embodiment of this application, the cosmetic can be a cosmetic for skin regeneration, skin whitening, wrinkle improvement, antibacterial (anti-acne), skin anti-oxidation, and ultraviolet protection.

[0057] In one embodiment of this application, the dosage form of the cosmetic product may be selected from surfactants, rinses, oils, foundations, hair dyes, and waxes in products such as lotions, essences, lotions, creams, gels, powders, packs, soaps, or shampoos, but is not limited to these. In another embodiment of this application, the cosmetic product may also contain cosmetically acceptable additives selected from surfactants, water, emulsifiers, fillers, fragrances, stabilizers, solubilizers, gelling agents, fatty substances, alcohols, and thickeners, but is not limited to these.

[0058] In one embodiment of this application, the dosage form of the cosmetic product may be a topical skin agent selected from ointments, gels, creams, sprays and patches, but is not limited to these.

[0059] The present application will be described in more detail below through embodiments, but the following embodiments are merely examples to help understand the present application, and the content of the present application is not limited to the following embodiments.

[0060] Forms of implementing the invention

[0061] [Example]

[0062] <Example 1: Synthesis of resveratrone>

[0063] Referring to existing technical documents [Korean Patent Publication No. 1294993], resveratrol, represented by the following chemical formula 3, was synthesized according to the following method.

[0064] 1) Dissolve resveratrol in methanol at a concentration of 0.1 g / L to 1.0 g / L.

[0065] 2) Use a lamp equipped with UV-B (λ) max A special ultraviolet reactor (306nm) irradiates the resveratrol solution with ultraviolet light.

[0066] 3) After the reaction, the solution was concentrated and resveratrol was separated using a Prep-HPLC device.

[0067] [Chemical Formula 3]

[0068]

[0069] <Experimental Example 1: Evaluation of the Cell Proliferation Efficacy of Resveratrol>

[0070] 1) Human normal fibroblasts were cultured.

[0071] 2) An appropriate number of cells were inoculated and then subjected to starvation treatment for 24 hours after 24 hours.

[0072] 3) Cells were cultured for 72 hours in culture media treated with different concentrations of samples.

[0073] 4) Cell viability was determined and analyzed using the MTT assay.

[0074] like Figure 1 As shown, in the test group treated with 10 μM resveratrol, the number of cells increased by 20%, thus confirming the cell proliferation effect.

[0075] <Experimental Example 2: Evaluation of the antioxidant efficacy of resveratrol (DPPH determination)>

[0076] 1) 115 μL of 70% ethanol was dispensed into each well of the 96-well plate.

[0077] 2) Each sample and positive control was dispensed in 5 μL, and the absorbance was measured at 517 nm. The absorbance value before the reaction was also measured.

[0078] 3) 80 μL of DPPH solution was dispensed into each container.

[0079] 4) The absorbance after the reaction was measured at 517 nm, and the results were analyzed using the absorbance values ​​before and after the reaction.

[0080] like Figure 2 As shown, the free radical scavenging ability was confirmed in the resveratrol test group at concentrations ranging from 1 μM to 50 μM.

[0081] <Experimental Example 3: Evaluation of the skin-whitening effect of resveratrol (inhibition of melanin synthesis in B16F10 cells)>

[0082] 1) B16F10 cells were cultured.

[0083] 2) After inoculating an appropriate number of cells, all groups except the blank group were treated with α-MSH and samples after 24 hours.

[0084] 3) The cells were cultured for 72 hours in the culture medium that had been treated with each sample.

[0085] 4) The cells were dissolved and the supernatant was separated, and then the absorbance of the supernatant was measured.

[0086] 5) The protein content in each supernatant was determined and analyzed using the BCA method.

[0087] 6) The melanin synthesis value measured in the supernatant was corrected using protein content, and then the amount of melanin synthesized per unit cell was calculated.

[0088] like Figure 3 As shown, inhibition of melanin synthesis was confirmed in the test groups treated with resveratrol at concentrations ranging from 10 μM to 50 μM (arbutin: positive control).

[0089] <Experiment Example 4: Evaluation of the skin-whitening effect of resveratrol (inhibition of extracellular melanin synthesis in B15F10 cells)>

[0090] 1) B16F10 cells were cultured.

[0091] 2) After inoculating an appropriate number of cells, all groups except the blank group were treated with α-MSH and samples after 24 hours.

[0092] 3) Cells were cultured for 72 hours in culture media treated with each sample.

[0093] 4) The absorbance of the cell culture medium was measured.

[0094] 5) The cells were dissolved and the supernatant was separated. The protein content was then determined by the BCA method and the amount of melanin synthesis was corrected.

[0095] 6) The measured melanin synthesis value was corrected with protein content, and then the amount of melanin synthesized per unit cell was calculated.

[0096] like Figure 4 As shown, inhibition of melanin synthesis was confirmed in the test groups treated with resveratrol at concentrations ranging from 10 μM to 50 μM (arbutin: positive control).

[0097] <Experimental Example 5: Evaluation of the skin-whitening effect of resveratrol (tyrosinase activity inhibition ability)>

[0098] 1) An appropriate amount of human normal pigment cells were inoculated and cultured for 1 day.

[0099] 2) The culture medium was replaced with the one used for each sample and cultured for 72 hours.

[0100] 3) The cells were dissolved and the supernatant was separated. The absorbance was measured at 475 nm every 30 minutes while the supernatant was reacted with dopa, which was the reaction substrate, at 37 °C.

[0101] 4) The protein content in the cell lysate supernatant was determined using the BCA method, and the tyrosinase (melanin synthase) measurement value was corrected accordingly.

[0102] like Figure 5 As shown, inhibition of tyrosinase activity was confirmed in test groups treated with resveratrol at concentrations ranging from 1 μM to 50 μM.

[0103] <Experimental Example 6: Evaluation of the Wrinkle-Improving Efficacy of Resveratrol (Collagen Synthesis Efficacy)>

[0104] 1) Use 2×10 5 Human normal fibroblasts were seeded and cultured in 6-well plates.

[0105] 2) It was cultured in a state of starvation for 1 day.

[0106] 3) The samples were treated with different concentrations and then cultured for 24 hours.

[0107] 4) The cells were washed, then irradiated with ultraviolet light and cultured for 48 hours.

[0108] 5) The expression level of collagen in the cell culture medium was measured and analyzed.

[0109] like Figure 6 As shown, increased collagen synthesis was confirmed in the test groups treated with resveratrol at concentrations ranging from 10 μM to 20 μM.

[0110] <Experimental Example 7: Evaluation of the anti-acne efficacy of resveratrol (antibacterial efficacy against Propionibacterium acnes)>

[0111] 1) Propionibacterium acnes, an anaerobic acne bacterium, was cultured under anaerobic bacterial culture conditions.

[0112] 2) The turbidity of the strain was adjusted to McFarland Standard 1, and then prepared by dilution at 1 / 20 in liquid medium.

[0113] 3) Liquid nutrient culture medium was treated with samples of different concentrations.

[0114] 4) 100 μL of the liquid nutrient culture medium prepared for the sample was dispensed into each container, and then 10 μL of the prepared strain was inoculated into each container.

[0115] 5) The strain was cultured under anaerobic conditions for 72 hours, and then the bacterial count was determined and analyzed.

[0116] like Figure 7 As shown, inhibition of bacterial growth was confirmed in test groups treated with resveratrol at concentrations ranging from 20 μM to 200 μM.

[0117] <Experimental Example 8: Determination of the Absorbance of Resveratrol>

[0118] 1) Resveratrol was dissolved in organic solvents at concentrations ranging from 10 μM to 50 μM.

[0119] 2) The absorbance of resveratrol was determined using a spectrophotometer.

[0120] like Figure 8 As shown, absorption across the entire ultraviolet spectrum, including UV-A (320 to 400 nm), UV-B (280 to 320 nm), and UV-C (200 to 280 nm), has been confirmed.

[0121] <Experimental Example 9: Determination of the UV Protection Index of Creams Containing Resveratrol>

[0122] 1) A cream containing resveratrol was prepared by mixing purified water (65%), glycerin (7%), olive oil wax (5%), jojoba oil (20%), and resveratrol (3%) while heating to above 75°C.

[0123] 2) Apply 2.0 mg / cm² to the back. 2 The prepared cream was evenly applied at a uniform concentration, and then the ultraviolet protection factor (SPF, UV-B protection index) and ultraviolet A protection factor (PFA, UV-A protection index) were measured according to the testing methods announced by the Ministry of Food and Drug Safety.

[0124] like Figure 9 As shown, the expected SPF index is 4.0 and the expected PFA index is 4.8, which, as a preliminary clinical test result, confirms the effectiveness of ultraviolet protection.

[0125] The foregoing description of this application is intended to be illustrative, and those skilled in the art will understand that it can be readily modified into other specific forms without altering the technical concept or essential characteristics of this application. Therefore, the above embodiments should be understood in all respects as exemplary and not restrictive. For example, each component described as a single can be implemented as distributed, and similarly, components described as distributed can be implemented as combined.

[0126] The scope of this application is set forth in the appended claims rather than in the detailed description above, and all alterations or modifications arising from the meaning and scope of the claims and their equivalents shall be construed as being included within the scope of this application.

Claims

1. The use of resveratrol, represented by the following chemical formula, in the preparation of cosmetics that produce at least one function selected from skin regeneration, skin whitening, wrinkle improvement, anti-acne, and skin anti-oxidation:

2. The use according to claim 1, wherein the dosage form of the cosmetic is selected from lotions, serums, lotions, creams, gels, powders, masks, soaps, essential oils, foundations and waxes.

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