KR20160066986A - (2S) -1-O-linolenoyl-3-O-? -D-galactopyranosyl-sn-glycerol as an active ingredient - Google Patents

Abstract

The present invention relates to a composition for preventing gray hair and alleviating leukoplakia and, more specifically, to a composition which promotes melanotrichia growth, prevents gray hair growth in advance by promoting melanin synthesis, is effective in improving leukoplakia, and also activates melanocytes through increasing the MITF expression of the melanocytes by comprising (2S)-1-O-linolenoyl-3-O-beta-D-galactopyranosyl-sn-glycerol as an active ingredient.

Description

(2S) -1-O-linolenoyl-3-O-? -D-galactopyranosyl-sn-glycerol as an active ingredient. of leucoplakia containing (2S) -1-O-linolenoyl-3-0- beta -D-galactopyranosyl-sn-glycerol}

( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol as an active ingredient, and more particularly, (MITF) expression of melanocytes, thereby promoting melanocyte synthesis and promoting melanin synthesis, thereby preventing the induction of white moths in advance, promoting the induction of black cohosh, and also being effective in improving vitiligo .

Since white moth generally occurs when aging progresses, it gives strong impression of old age. Therefore, a lot of dyes have been studied for dyeing white moths in order to hide white moths. However, dyeing is a temporary method and must be stained again by the growth of white hair. In addition, oxidized black hair dye which is widely used at present causes skin damage by the use of an oxidizing agent and the like.

As an inhibitor of wheat bloom, black sesame seeds, horseradish, hanshiksu, and honey can be used as supplementary ingredients, such as Sukjipu, Chunmundong, and Maekmundong. The method of boiling at a temperature of 50 ° C and then keeping the black bean black in the chemical solution, using black sesame seeds, black sesame leaf, kelp, using aqua extract extract, using pituitary hormone, cAMP (3'-5 '-cyclic adenosine monophosphate), vitamin D3, and the like have been disclosed, but the effect that can be sensed is not shown.

On the other hand, ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol has been known to have anticancer and anti-inflammatory effects (Cha BJ et al., Glycosyl glycerides from hydrophobic Panax ginseng inhibited NO production in LPS-stimulated RAW264.7 cells, Journal of Ginseng Research (2014), doi: 10.1016 / j.jgr.2014.10.005), and no other activity was known.

Cha BJ et al., Glycosyl glycerides from hydrophobic Panax ginseng inhibited NO production in LPS-stimulated RAW 264.7 cells, Journal of Ginseng Research (2014), doi: 10.1016 / j.jr.2014.10.005

Accordingly, the present inventors have found that ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol increases the expression of MITF and inhibits the white hair progression in transformed melanocytes The effect of giving was observed.

Accordingly, it is an object of the present invention to provide a composition for preventing white spot and for improving leukosis.

In order to achieve the above-mentioned object, the present invention relates to a method for preventing or inhibiting wheat blight containing ( 2S ) -1- O -linolenoyl-3-0- ? -D-galactopyranosyl- sn -glycerol as an active ingredient ≪ / RTI >

The composition of the present invention increases melanocyte MITF expression by containing ( 2S ) -1- O -linolenoyl-3-0- ? -D-galactopyranosyl- sn -glycerol as an active ingredient, Promotes melanin synthesis, thereby preventing the induction of white moths in advance, promoting the induction of the gray pigments, and also improving the vitiligo.

The composition according to the present invention can provide an anti-whitening effect or an anti-irritant effect by containing ( 2S ) -1- O -linolenoyl-3-0- ? -D-galactopyranosyl- sn -glycerol as an active ingredient have.

The ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol used in the present invention has a structure represented by the following formula (1).

[Chemical Formula 1]

The ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol of the present invention is a glycosylglyceride extracted from ginseng (Cha BJ et al. Glycosyl glycerides from hydrophobic Panax ginseng inhibited NO production in LPS-stimulated RAW264.7 cells, Journal of Ginseng Research (2014), doi: 10.1016 / j.jgr.2014.10.005), but the present invention is not limited thereto. May be extracted from plants, synthesized according to methods known in the art, and commercially available ones may be used.

The composition according to the present invention is (2S) -1- O - Reno Reno il -3-O- β-D - galacto-pyrazol nosil - sn - 0.001 ~ 50% by weight relative to the total weight of the composition of glycerol, preferably from 0.01 To 30% by weight, and more preferably from 0.1% to 10% by weight. If the content of ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol is less than 0.001% by weight, %, There is a problem of skin safety or shape.

The cause of white moths is the disappearance of melanocyte stem cells and the degradation of melanocytes. Especially, it is known that white moths caused by aging are mainly caused by loss of stem cells, and white moths including mites are caused by degradation of melanocytes due to environmental and mental stress of modern society.

Melanin synthesis activity of melanocytes is significantly influenced, (2S) -1- O in accordance with the present invention the active MITF-Reno Reno il -3-O- β-D - galacto-pyrazol nosil-sn-glycerol melanocortin It is possible to significantly increase the expression of MITF at the site, thereby inhibiting white moth and promoting the induction of black blood cell.

The composition of the present invention may be formulated as an external preparation for skin, in particular as a cosmetic composition, and may be formulated containing a cosmetically or dermatologically acceptable medium or base. In addition, the composition of the present invention may be provided in any form suitable for topical application, for example, as a solution, an emulsion obtained by dispersing an oil phase in water phase, an emulsion obtained by dispersing water phase in water phase, a suspension, a solid, a gel, Pastes, foams, or aerosol compositions. Compositions of such formulations may be prepared according to conventional methods in the art.

In particular, the composition for external application for skin of the present invention is not particularly limited as a composition for hair or scalp. For example, hair tonic, hair nutritional lotion, scalp treatment, hair treatment, hair shampoo, hair rinse, Scalp hair combined treatment, and the like.

In addition, the composition according to the present invention may contain, in addition to the above-mentioned substances, other ingredients which can give a synergistic effect to the main effect, to the extent that the main effect is not impaired. The composition according to the present invention may further comprise a humectant, an emollient, an ultraviolet absorber, an antiseptic, a bactericide, an antioxidant, a pH adjuster, an organic or inorganic pigment, a perfume, a cold agent or a limiting agent. The compounding amount of the above components can be easily selected by a person skilled in the art within the range not impairing the object and effect of the present invention, and the amount thereof may be from 0.01 to 5% by weight, specifically from 0.01 to 3% by weight based on the total weight of the composition .

In addition, the composition of the present invention can be formulated as a pharmaceutical composition. When the composition according to the present invention is applied to medicines, it may be formulated into oral, parenteral or parenteral dosage forms in solid, semi-solid or liquid form by adding an inorganic or organic carrier compatible with the active ingredient used in the present invention , The pharmaceutical composition according to the present invention may be administered orally, parenterally, rectally, topically, transdermally, intravenously, intramuscularly, intraperitoneally, subcutaneously, and the like.

Examples of the formulations for oral administration include tablets, pills, granules, capsules, powders, fine granules, powders, emulsions, syrups and pellets. In addition, the formulations for parenteral administration include injections, drops, ointments, lotions, sprays, suspensions, emulsions, suppositories, and the like. The composition according to the present invention can be easily formulated into an active ingredient by carrying out the composition according to a conventional method. In this case, a surfactant, excipient, coloring agent, spice, preservative, stabilizer, buffer, suspending agent, have.

The dosage of the active ingredient of the pharmaceutical composition of the present invention will vary depending on the age, sex, body weight, pathological condition and severity of the subject to be treated, route of administration, or judgment of the prescriber. Determination of the appropriate dose based on these factors is well within the level of ordinary skill in the art and its daily dose is, for example, from 0.1 mg / kg / day to 100 mg / kg / day, more specifically from 5 mg / kg / day to 50 mg / / Day, but is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are only for illustrating the present invention and that the scope of the present invention is not construed as being limited by these embodiments.

[Referential Example 1]

( 2S ) -1- O -linolenol-3-O- beta -D-galactopyranosyl- sn -glycerol for the test of the efficacy of the composition of the present invention was prepared according to the prior art (Cha BJ et al., Glycosyl glycerides from hydrophobic Panax ginseng inhibited NO production in LPS-stimulated RAW264.7 cells, Journal of Ginseng Research (2014), doi: 10.1016 / j.jgr.2014.10.005).

Test Example 1 Test for promoting melanin production of ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol

A medium supplemented with 5% fetal bovine serum, 100 IU penicillin G and 0.2 μM TPA (12- O- tetradecanoyl phorbol-13-acetate) in RPMI medium manufactured by Rosewell Park Menorial Institute The melanocytes (melan-a) were dispensed in a 24-well microtiter plate at 50,000 cells / well. ( 2S ) -1- O -linolenol-3-O- beta -D-galactopyranosyl- sn -glycerol of Reference Example 1 as a test substance at final concentrations of 50 ppm and 100 ppm , 0.1% DMSO (dimethyl sulfoxide) as a negative control, 100 μM IBMX (3-isobutyl-1-methylxanthine) as a positive control, and then cultured at 37 ° C for 3 days. After incubation, the wells were washed with phosphate buffered saline (PBS), and 100 μl of 1N NaOH was added thereto. Melanin in the cells was dissolved. The absorbance of dissolved melanin was measured at 405 nm using a microplate reader. The measured results were compared with the negative control group of 100 and are shown in Table 1 below.

Melanogenesis promoting effect of ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol is shown in Table 1 as compared with the control group.

Test substance Melanin determination ratio (%) for negative control DMSO 100 IBMX 116 ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 50 ppm 104 ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 100 ppm 127

As shown in Table 1, ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol promoted melanin synthesis of melanocytes, 100 ppm, the melanin production promoting effect is higher than that of the positive control group.

Test Example 2: Promotion of MITF and tyrosinase expression in melanocytes of 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol

The cells were divided into 6-well microtiter plates at 500,000 cells / well using a 501mel cell line (provided by Dr SA Rosenberg, Surgery Branch, National Cancer Institute, Bethesda, MD, USA) is a 0.1% DMSO, positive control group, 100μM IBMX, and test group is (2S) -1- O - treating the glycerol with 50ppm - Reno Reno il -3-O- β-D - galacto-pyrazol nosil - sn , And cultured at 37 ° C for 24 hours, 48 hours, and 72 hours to obtain proteins. The protein thus obtained was subjected to western blotting using MITF and tyrosinase antibodies. Protein extraction and Western blotting were routinely performed by standard methods used by those skilled in the art. The result of the Western blotting was compared with the negative control group of 100, and the results are shown in Table 2 below.

MITF Tyrosinase IBMX ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol IBMX ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 24hr 121 85 160 125 48hr 98 106 149 134 72hr 224 117 298 179

Table 2 shows that ( 2S ) -1- O -linolenoyl-3-O- beta -D-galactopyranosyl- sn -glycerol increases MITF and tyrosinase protein expression in melanocytes .

[Formulation Example 1] Hair tonic

A hair tonic was prepared according to a conventional method according to the composition shown in Table 3 below.

ingredient Weight ratio (%) ethanol 50 menthol 0.02 glycerin 3 Salicylic acid 0.05 ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 1.0 Spices and Pigments Proper amount Purified water Balance (to 100)

[Formulation Example 2] Hair lotion

Hair lotions were prepared according to the compositions shown in Table 4 below in a conventional manner.

ingredient Weight ratio (%) Cetostearyl alcohol 2.0 EDTA 2Na 0.2 Hydroxyethyl cellulose 0.5 Mineral oil 5.0 ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 1.0 antiseptic Proper amount Spices and Pigments Proper amount Purified water Balance (to 100)

[Formulation Example 3] Hair nutritional lotion

The hair nutritional lotion was prepared by a conventional method according to the composition shown in Table 5 below.

ingredient Weight ratio (%) Wax 4.0 Polysorbate 60 1.5 Sorbitan sesquioleate 0.7 Mineral oil 10.0 glycerin 3.0 Butylene glycol 3.0 Propylene glycol 3.0 Carboxyvinyl polymer 0.1 Triethanolamine 0.2 ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 1.0 antiseptic Proper amount Spices and Pigments Proper amount Purified water Balance (to 100)

[Formulation Example 4] Hair shampoo

Hair shampoos were prepared in a conventional manner according to the composition shown in Table 6 below.

ingredient weight% Purified water Balance (To 100) ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 1.0 Sodillauryl sulphite 36.0 Cocamidopropyl betaine 8.0 Palmitidine dimalate 2.0 Glycollosteralate 1.5 Polyquaternium 10 0.5 Saitric Acid 0.1 glycerin 2.0 Preservatives, coloring and flavoring Suitable amount

[Formulation Example 5] Hair rinse

Hair rinses were prepared according to the compositions shown in Table 7 below by a conventional method.

ingredient weight% Purified water Balance (To 100) ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol 1.0 Propylene glycol 2.0 Cetyltrimethylammonium chloride 1.0 Cetyl alcohol 3.0 Stearyl alcohol 3.0 Mineral oil 0.5 Saitric Acid 0.2 Polydimethylsiloxane 1.0 Preservatives, coloring and flavoring Suitable amount

While the present invention has been particularly shown and described with reference to specific embodiments thereof, those skilled in the art will readily appreciate that many modifications are possible in the exemplary embodiments without materially departing from the novel teachings and advantages of this invention. something to do. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.

Claims (4)

( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol represented by the following formula (1) as an active ingredient.
[Chemical Formula 1]

The composition for external application for skin according to claim 1, wherein the active ingredient is contained in an amount of 0.001 to 50% by weight based on the total weight of the composition. ( 2S ) -1- O -linolenoyl-3-O- ? -D-galactopyranosyl- sn -glycerol represented by the following formula 1 as an active ingredient.
[Chemical Formula 1]

4. The pharmaceutical composition according to claim 3, wherein the active ingredient is contained in an amount of 0.001 to 50% by weight based on the total weight of the composition.