KR20130069034A - Composition for improving skin wrinkle - Google Patents
Composition for improving skin wrinkle Download PDFInfo
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- KR20130069034A KR20130069034A KR1020110136554A KR20110136554A KR20130069034A KR 20130069034 A KR20130069034 A KR 20130069034A KR 1020110136554 A KR1020110136554 A KR 1020110136554A KR 20110136554 A KR20110136554 A KR 20110136554A KR 20130069034 A KR20130069034 A KR 20130069034A
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- rasatiol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
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- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
The present invention relates to a composition for improving skin wrinkles, in particular a cosmetic composition for improving skin wrinkles.
Because the skin has many opportunities to interact with various external stimuli, it is more prone to wrinkles than other organs. Among them, facial skin is directly exposed to sunlight, dry air, and pollutants, so that wrinkles occur earlier than other skin.
The most characteristic change due to the aging of the skin tissue is a change in the matrix (matrix), the aging of the human skin fibroblast (dermal skin fibroblast) is reduced the ability to produce fibers and substrates. The amount of the substrate is generally decreased, the thickness of the skin is thinned, and the elasticity of the skin is lowered to form the wrinkles. That is, as aging progresses, the skin becomes weaker in elasticity, disorder of blood circulation, weakening of skin barrier, and the like.
Many cosmetics have been studied to reduce skin wrinkles caused by such external environment or internal mechanism. Recently, the development of cosmetics is derived from natural substances that have been proven to have side effects through long-term use, and interest in the development of cosmetics using substances having the effect of treating various symptoms of the skin is increasing.
Therefore, the technical problem to be achieved by the present invention is to provide a composition, in particular a cosmetic composition excellent safety and wrinkle improvement effect.
In order to achieve the above technical problem, the present invention provides a composition for improving skin wrinkles, preferably a cosmetic composition, comprising rasatiol represented by the following formula (1) as an active ingredient.
The present inventors confirmed that administration of rasatiol not only promotes the growth of skin fibroblasts, but also has a very useful effect in improving skin wrinkles by promoting the production of collagen, elastin, fibronectin, TGF-β1, etc. in fibroblasts. The present invention was completed. Based on the experimental results according to the present invention, it is thought that the rasathiol of the present invention is superior to other skin wrinkle improving materials.
Rasathiol included as an active ingredient in the composition for improving skin wrinkles of the present invention has the structure of Formula 1. Such rasathiol may be obtained through chemical synthesis well known in the art to which the present invention pertains, and may also be obtained through extraction and / or purification methods well known in the art to which the present invention belongs. As a conventional solvent extraction method, it can be extracted using a suitable solvent such as ethanol, methanol, butanol, chloroform, dichloromethane, hexane, ethyl acetate, or also obtained by supercritical extraction method. Can be obtained.
The present invention also provides a composition for improving skin wrinkles comprising a butanol fraction of a lower alcohol extract having 1 to 4 carbon atoms as a seed ingredient of Rabokus sativus (seed). The present invention is based on the surprising results that the skin wrinkle improvement effect of the butanol fraction of the lower alcohol extract among the various extracts of the moths and various fractions of these extracts using various solvents is much superior.
Therefore, the present invention also provides a step of extracting (S1) nabokja (Muscle) with lower alcohol having 1 to 4 carbon atoms; And (S2) fractionating the obtained extract with butanol.
The present invention also comprises the steps of extracting (S1) nabokja (Muscle) with a lower alcohol having 1 to 4 carbon atoms; And (S2) provides a method for improving the skin wrinkle improvement effect of the moth extract extract comprising the step of fractionating the obtained extract with butanol.
The composition for improving skin wrinkles of the present invention may be prepared in the form of medicines, health functional foods and cosmetics. Such medicines, nutraceuticals and cosmetics may include pharmaceutically acceptable excipients or additives. The composition for improving skin wrinkles of the present invention may be administered alone or in combination with any convenient carrier, excipient or the like, and such a dosage form may be a single dose or a repeated dosage form.
The composition for improving skin wrinkles of the present invention may be a solid preparation, a semisolid preparation or a liquid preparation. Solid preparations include, but are not limited to, powders, granules, tablets, capsules, suppositories, and the like. Solid form preparations may include, but are not limited to, excipients, flavoring agents, binders, preservatives, disintegrants, lubricants, fillers, and the like. Examples of the semi-solid preparation include a cream, a lotion, an emulsifier, a liniment, and the like, but the present invention is not limited thereto, and can be produced by adding a suitable colorant, a flavoring agent, a stabilizer, a tackifier, a surfactant, and the like. Examples of the liquid preparation include water, alcohols, solutions such as solutions of propylene glycol, suspensions, emulsions and the like, but not limited thereto, and they can be prepared by adding appropriate coloring agents, flavoring agents, stabilizers, tackifiers and the like.
For example, powders may be prepared by simply mixing the active ingredient of the present invention with a suitable pharmaceutically acceptable excipient such as lactose, starch, microcrystalline cellulose. Granules are the active ingredient of the present invention; Suitable excipients which are pharmaceutically acceptable; And a suitable pharmaceutically acceptable binder such as polyvinylpyrrolidone and hydroxypropylcellulose, followed by wet granulation using a solvent such as water, ethanol or isopropanol or dry granulation using a compressive force . Further, the tablet may be prepared by mixing the above granule with a suitable pharmaceutically acceptable salt such as magnesium stearate and then tableting it using a tablet machine. Also, for example, the external skin preparation may be a pharmaceutically acceptable suitable base such as petrolatum or stearyl alcohol; Pharmaceutically acceptable suitable surfactants such as polysorbate, sorbitan sesquioleate and the like; Pharmaceutically acceptable humectants, such as glycerin; Pharmaceutically acceptable solvents; And a conventional external preparation for skin preparation in which a flavoring agent, a coloring agent, a stabilizer, a tackifier and the like are homogeneously mixed.
However, the composition according to the present invention is preferably a cosmetic composition, and the cosmetic composition is a cosmetic composition, such as cosmetics, essences, oils, creams, Powders, packs, foundations, makeup bases, sticks and the like formulations can be prepared and used. The cosmetic composition may also be applied in various forms such as liquid, cream, paste, solid, and may be prepared by a conventional cosmetic preparation method.
For example, the composition of the present invention may be prepared in a flexible softener using carbomer, butylene glycol, glycerin, PEG, ethanol, polyoxyethylene hardened castor oil, triethanolamine, purified water, or cetearyl Alcohol, Glyceryl Stearate / Pig-100 Stearate, Polysorbate 60, Sorbitan Sesquioleate, Cetyl Octanoate, Squalane, Apricode Canal Oil, Butylene Glycol, Carbomer, Xanthan Gum, Preservatives, purified water, arginine and the like can be prepared in a lotion type, but the present invention is not limited to these formulations.
In the composition according to the present invention, the content of rasathiol is preferably 0.0001 to 10% by weight based on the total weight of the composition.
The present invention also provides a method for preventing or ameliorating skin wrinkles comprising applying an effective amount of rasathiol or a specific moth extract according to the invention to the skin of a subject in need of improvement of the skin wrinkles.
In order to achieve the object of the present invention of treating, preventing or improving skin wrinkles, the rasathiol of the present invention may be administered from about 0.01 mg / kg to about 10 g / kg daily, and from about 0.1 mg / kg to about 1 g. A daily dose of / kg is preferred. However, the dosage may vary depending on the route and formulation of administration, the condition of the patient (age, sex, weight, etc.), the severity of the condition being treated, the purity and content of the moth butaneol fraction according to the extraction method. For convenience, the total daily dose may be divided as needed and divided into several doses throughout the day.
The present invention provides a composition useful for improving skin wrinkles, comprising rasatiol as an active ingredient, or a moth extract extract prepared through a specific procedure.
The present invention also comprises the steps of extracting (S1) nabokja (Muscle) with a lower alcohol having 1 to 4 carbon atoms; And (S2) fractionating the obtained extract with butanol.
The present invention also comprises the steps of extracting (S1) nabokja (Muscle) with a lower alcohol having 1 to 4 carbon atoms; And (S2) provides a method for improving the skin wrinkle improvement effect of the moth extract extract comprising the step of fractionating the obtained extract with butanol.
BRIEF DESCRIPTION OF THE DRAWINGS The accompanying drawings, which are incorporated in and constitute a part of the specification, illustrate exemplary embodiments of the invention and, together with the description of the invention, It should not be construed as limited.
1 is a view showing a process for separating rasatiol from the moth (Raphanus sativus seeds).
Figure 2 is a TLC result (left photo) of the nachos methanol extract and fractions and HPLC chromatogram of the isolated compound.
Figure 3 is the result of evaluating the effect of rasatiol according to the present invention on the production of collagen and elastin in fibroblasts.
Figure 4 is the result of evaluating the effect of the specific extract of the moth according to the invention on the production of collagen.
Hereinafter, embodiments of the present invention will be described in detail to facilitate understanding of the present invention. However, the embodiments according to the present invention can be modified into various other forms, and the scope of the present invention should not be construed as being limited to the following embodiments. Embodiments of the invention are provided to more fully describe the present invention to those skilled in the art.
<Isolation and Identification of Rasatiol>
After 3Kg of moths were ground to a size of 100 mesh using a grinder, about 30 L (about 1:10 weight / volume) of methanol was added, followed by cold extraction for 5 days, and concentrated under reduced pressure using a rotary evaporator. Solvent fractionation was carried out on the methanol extract (230 g) and the collagen synthesis promotion effect was evaluated to confirm that the butanol layer had the best effect. 57 g of butanol fractions were subjected to silica gel chromatography (ODS open chromatography, Eluent: C / M = 100/1 → 1/1). Among the five fractions, the third fraction was the most effective. The third fraction was again subjected to silica gel chromatography (ODS open chromatography, Eluent: C / M = 20/1 → 1/1) to confirm that the fourth fraction of the four fractions obtained had the best efficacy, and the compound C1 Named this. Compound C1 was subjected to HPLC (Grom-sil 120 ODS-3 CP, 10 μm column (250 × 4.6 mm) 30 → 70% MeOH gradient) to obtain 245 mg of pure single component (see FIGS. 1 and 2).
The structure of the compound was estimated by 1 H NMR and 13 C NMR spectra, 2D NMR spectra such as HMBC, HMQC, COSY and ESI-mass spectrometry [m / z = 777.2 (M + Na) + ]. It was confirmed that it is rasathiol. 1 H NMR and 13 C NMR spectra and mass spectrometry of the compounds isolated according to the present invention are shown.
1 HNMR (500 MHz, DMSO-d 6) δ ppm: 3.17 (1 H, m); 3.29 (1 H, m); 3.47 (1 H, m); 3.62 (1 H, m); 3.67 (1 H, m); 3.77 (2H, s); 3.80 (2H, s); 3.82 (1 H, m); 4.11 (1H, t, J = 9.0 Hz); 4.17 (1H, doublet of doublets, J = 11.7 Hz, 7.2 Hz); 4.24 (1H, doublet of doublets, J = 14.4 Hz, 8.1 Hz); 4.45 (1H, doublet, J = 11.7 Hz); 4.66 (1H, t, J = 6.3 Hz); 5.29 (1H, doublet, J = 3.6 Hz); 5.40 (1H, doublet, J = 8.1 Hz); 5.57 (1H, doublet, J = 6.3 Hz); 6.48 (1H, doublet, J = 15.3 Hz); 6.53 (1H, doublet, J = 16.2 Hz); 7.00 (4H, doublet, J = 6.3 Hz); 7.54 (1H, doublet, J = 15.3 Hz); 7.60 (1H, doublet, J = 16.2 Hz); 8.95 (2H, s).
13 CNMR (125 MHz, DMSO-d6) δ ppm: 55.6 (2C), 55.7 (2C), 61.9, 63.2, 63.9, 69.7, 70.2, 71.0, 72.2, 72.7, 76.8, 82.5, 90.5, 102.7, 105.8 (4C), 114.3, 114.4, 123.9, 124.0, 137.9 (2C), 144.9, 145.4, 147.6 (2C), 147.7 (2C), 165.1, 166.3.
Polymer mass spectrum (ESI, m / z): 777.2215 (C 34 H 42 0 19 Na, Calcd. 777.2218; Δ = 0.39 ppm).
<Efficacy evaluation method>
In the following examples, the efficacy of the extracts and compounds according to the present invention was evaluated as follows.
(1) Evaluation of cell growth promoting efficacy
The thymidine uptake promotion test was used to assess cell growth promotion. Human fibroblast cells pre-cultured with DMEM with 10% FBS (fetal bovine serum) were added to a 6-well plate at a concentration of 10 5 cells / ml and incubated for 18 hours in a CO 2 incubator. It was. After removing the medium and incubating for 48 hours with [ 3 H] -thymidine and a medium diluted sample without FBS, the degree of cell growth promotion was evaluated using a scintillation counter.
(2) Evaluation of TGF-β1, Fibronectin, and Collagen Synthesis Promoting Efficacy (ELSIA)
Human skin fibroblasts pre-cultured with DMEM with 10% FBS were added to a 24-well plate at a concentration of 2 × 10 5 cells / ml and incubated for 18 hours in a CO 2 incubator (37 ° C., 5% CO 2 ). After removing the medium and incubating for 48 hours by adding the diluted sample to the medium without FBS, the culture medium was taken and collagen type 1 (collagen thype I), TGF (transforming growth factor) -β and fibronectin (fibronectin) were obtained. Quantitative analysis was performed. TGF-β was assessed using the DuoSet ELISA kit (R & D system, USA), fibronectin was measured using the Fibronectin EIA Kit (TakaRa, Japan), and collagen synthesis promoting efficacy was assessed using the
(3) Evaluation of collagen and elastin synthesis promoting efficacy (Western blot)
Human fibroblasts pre-cultured with DMEM with 10% FBS were added to 6-well plates at a concentration of 2 × 10 5 cells / ml and incubated for 18 hours in a CO 2 incubator. After removing the medium, adding diluted media medium without FBS, incubating for 48 hours, lysing the cells and evaluating the effect of promoting the synthesis of the drug through SDS-PAGE electrophoresis, PVDF membrane transfer, and antibody binding. It was.
<Evaluation of Fibroblast Growth Promoting Effect of Rasathiol>
The thymidine absorption promotion test method was used. Rasathiol increased fibroblast growth derived from human skin by 123.9% and 156.9% at 25 and 50 μg / ml concentrations, respectively. The results are shown in Table 1 below.
As shown in Table 1, as the amount of added rasathiol was increased, the growth of human skin-derived fibroblasts was promoted. From these results, it can be seen that rasathiol according to the present invention is useful for improving wrinkles of the skin.
<Collagen and Elastin Synthesis Promotion Evaluation (Western Blot)>
Rasathiol concentration-dependently increased the production of
Collagen Synthesis Promotion Evaluation (ELISA)
The ELISA method was used to evaluate the effect of rasatiol according to the present invention on the
As shown in Table 2, rasathiol concentration-dependently increased the production of
<TGF-β1 synthesis promotion evaluation (ELISA)>
Rasathiol promoted TGF-β1 production in human skin fibroblasts in a concentration-dependent manner, and the results are shown in Table 3 below.
As shown in Table 3, rasathiol according to the present invention promoted the production of TGF-β1, which is known to be useful for skin wrinkle improvement.
Fibronectin Synthesis Promotion Evaluation (ELISA)
Rasathiol promoted fibronectin production in human skin fibroblasts in a concentration-dependent manner, and the results are shown in Table 4 below.
As shown in Table 4, rasathiol according to the present invention promoted the production of fibronectin, which is known to be useful for improving skin wrinkles.
<Evaluation of Collagen Synthesis Promoting Effect by Each Fraction>
As described in <Isolation and Identification of Rasathiol>, the collagen synthesis promoting efficacy of each solvent fraction of the methanol extract was evaluated, and the results are shown in FIG. 4.
As shown in Figure 4, butanol fraction was the best collagen production promoting efficacy compared to other fractions.
Claims (4)
≪ Formula 1 >
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Cited By (1)
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WO2017094959A1 (en) * | 2015-11-30 | 2017-06-08 | 한국 한의학 연구원 | Composition for improving skin aging and wrinkles, containing scutellaria baicalensis and raphanus sativus l. mixture extract as active ingredient |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2017094959A1 (en) * | 2015-11-30 | 2017-06-08 | 한국 한의학 연구원 | Composition for improving skin aging and wrinkles, containing scutellaria baicalensis and raphanus sativus l. mixture extract as active ingredient |
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