KR20180138386A - Whitening cosmetic composition comprising yuza seed extract as an active ingredient - Google Patents
Whitening cosmetic composition comprising yuza seed extract as an active ingredient Download PDFInfo
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Abstract
Description
The present invention relates to a cosmetic composition for whitening, and more particularly to a cosmetic composition having an antioxidative and whitening activity comprising an extract of yuzu or a limonoid aglycon derived from yuza seed as an active ingredient.
Skin is a very important tissue that has the biochemical and physical functions to protect the human body in direct contact with the external environment. This organization is divided into three major categories: epidermis, dermis, and subcutaneous tissue. The skin color of a person varies depending on the number, size, type and distribution of melanosomes containing melanin mainly contained in skin cells.
Melanomas are produced by melanocytes, and melanin, a black pigment produced by the epidermis, is produced in cells called melanocytes. Melanin absorbs ultraviolet light energy in the sunlight, preventing deeper cells from being damaged by ultraviolet light. Such abnormal production of melanin causes skin lesions such as vitiligo. On the contrary, if melanin is excessively synthesized by ultraviolet rays or the like, it not only damages the skin but also forms spots and freckles, and furthermore it causes skin cancer.
The most important role in melanin formation is known as tyrosinase enzyme, which produces dopaquinone that acts on the amino acid tyrosine present in the tissue and undergoes several stages of autoxidation from the dopaquinone Melanin, a black pigment, is produced. Accordingly, the whitening composition can be prepared by various methods depending on which of the steps that can inhibit melanin formation.
First, it contains a component capable of blocking ultraviolet rays, which is a main cause of melanin production. The composition according to this method contains a light scattering agent or a light blocking agent to reduce DNA damage or inflammation due to ultraviolet rays, By inhibiting the synthesis of core carbohydrates necessary to show activity, it is possible to inhibit melanin production (acting at the whitening A step). The second is to use substances that interfere with the function of tyrosinase involved in melanin production, such as enzymatic acids (kojic acid), lucinol, eric acid, or arbutin (acting on the whitening B step). Thirdly, there is a way to stabilize dopachrome and inhibit its progression to melanin (Eu-Melanin) (action at whitening C stage). The fourth is the use of substances such as Vitamin C (acting on the whitening D stage) that can exert a strong antioxidative effect and whitening effect, while the tyrosine undergoes complex oxidation and condensation reactions via dopa and dopa chrome. Fifthly, it is possible to remove and reduce the generated melanin from the stratum corneum by using enzyme or AHA (Alpha Hydroxy Acid) (acting on the whitening E step).
As a whitening ingredient in the conventional cosmetics field, for example, substances inhibiting tyrosinase enzyme activity such as kojic acid and arbutin, hydroquinone, L-ascorbic acid, And derivatives thereof and various plant extracts have been used. However, the substances inhibiting the tyrosinase enzyme activity are limited in their use due to degradation and coloration due to low stability in the prescription system, the generation of offensive odor, efficacy at a biological level, unclear effects and safety problems, to be.
Therefore, the present inventor sought to find a material derived from a natural substance that is stable to the human body and capable of exhibiting excellent whitening effect. As a result of experimenting with the effect of the extract of yuza as a cosmetic material, The present inventors have completed the present invention by confirming that it is possible to effectively inhibit the synthesis of melanin by inhibiting melanin production in a concentration-dependent manner in a cell.
Accordingly, an object of the present invention is to provide a cosmetic composition which is stable to human body and is excellent in antioxidative activity and melanin inhibitory activity and is effective for skin whitening.
In order to achieve the above-mentioned object of the present invention,
The present invention provides a whitening cosmetic composition comprising an extract of citrus peel as an active ingredient.
In one embodiment of the present invention, the extract may be at least one extract selected from the group consisting of citrus peel, sea bass and cetaceous.
In one embodiment of the present invention, the extract may be extracted with at least one solvent selected from the group consisting of lower alcohols having 1 to 4 carbon atoms, ethyl acetate, acetone, water and hexane.
In one embodiment of the present invention, the extract may be an ethanol extract.
In addition, the present invention provides a cosmetic composition for whitening comprising a limonoid aglycon derived from yuzu as an active ingredient.
In one embodiment of the present invention, the limonoid aglycon derived from Yuzu is selected from the group consisting of limonin, nomilin, obacunone, deacetylnomilin, Ring lactone (limonate A-ring lactone).
In one embodiment of the present invention, the cosmetic composition may be at least one selected from the group consisting of a soft lotion, a gel, a water-soluble liquid, a milk lotion, a nutritional cream, a massage cream, an essence, an oil in water emulsion, , Oil dispersions in aqueous phase using microspheres, ionic lipid vesicles, nonionic lipid vesicles, ointments, cleansing foams, cleansing waters, packs, body oils, oil-in-oil makeup bases, watershed makeup bases, foundations, skins And may be one type of formulation selected from the group consisting of a cover, a lipstick, a lip gloss, a face powder, a two-way cake, an eye shadow, a mascara, a cheek color and an eyebrow pencil.
Since the yuzu seed extract of the present invention and the yuza seed-derived limonoid aglycon can effectively inhibit melanin production in addition to excellent safety and antioxidative activity, the composition of the present invention containing it as an active ingredient can inhibit melanin pigment And thus can be usefully used as a functional cosmetic composition. In particular, the yuzu seed extract of the present invention and the limonoid aglycon derived from yuza seed are natural materials, and the cosmetic composition of the present invention having the same has a safety advantage for long-term use.
FIG. 1 is a photograph showing Yuza of Goheung County in 2016.
2 is a photograph showing a milking process for obtaining oil from citron seeds.
Fig. 3 is a photograph showing seed husks, seeds and seeds separated from yuzu seeds after milking.
4 is a view showing the process of extracting citrus seeds according to the present invention.
Fig. 5 shows the result of analysis of a remoteonoid component contained in a limonoid aglycone derived from yuzu seeds (seed, bark, seed) of the present invention by HPLC.
Fig. 6 shows the result of analyzing the remoteonoid component contained in the yuza-derived limonoid aglycon of the present invention by HPLC / MS.
7A is a graph showing the results of cytotoxicity evaluation of melanoma cells treated with yuza-derived limonoid aglycon of the present invention at different concentrations (25, 50, and 100 μg / ml), and 7b shows the results of yuza seed The results of cytotoxicity evaluation by treatment of melanoma cells with concentration of each of the radonoid glycosides (25, 50, and 100 μg / ml) are shown.
FIG. 8 shows the results of confirming melanin production inhibitory activity by treatment of melanoma cells with each of the melanoma cells (25, 50, and 100 μg / ml) according to the present invention.
9 is a graph showing the amount of protein expression of whitening-related substances (tyrosinase, TRP1, TRP2) after treatment of melanoma cells with concentration (25, 50 μg / ml) Respectively.
The present invention is characterized by providing a whitening cosmetic composition comprising an extract of Yuzu citrus as an active ingredient.
In one embodiment of the present invention, the extract may be at least one extract selected from the group consisting of citrus peel, sea bass and cetaceous.
As used herein, the term " seed shell " means the outermost shell of the seed of Yuza.
As used herein, the term 'sea bream' refers to a brown film between the seed coat and the seed of the seed, and may be referred to as a coat or an absorbent.
As used herein, the term " suture " refers to a tissue which removes the bark and the sea bream of citron, and supplies the nutrients necessary for germination and growth of the seed, and may also be referred to as an endosperm or an endosperm.
In the present invention, it was confirmed that yujia seed extract has excellent antioxidative and whitening activity and thus can be used as a material for functional cosmetics.
The extract of citrus peel according to the present invention can be obtained by extracting and separating from nature using an extraction and separation method known in the art, and the 'extract' defined in the present invention can be obtained by extracting citrus fruit For example, yuza seed extract, polar solvent-soluble extract or non-polar solvent-soluble extract.
In one embodiment of the present invention, the yuzu seed extract may be a seed bark extract of yuzu seed, a yuzu seed extract, and a yuzu seed extract.
As an appropriate solvent for extracting the extract from the citron seeds (seedshells, sea bass, and seeds), any pharmaceutically acceptable organic solvent may be used, and water or an organic solvent may be used, For example, alcohols having 1 to 4 carbon atoms such as purified water, methanol, ethanol, propanol, isopropanol, and butanol, acetone, ether Various solvents such as benzene, chloroform, ethyl acetate, methylene chloride, hexane and cyclohexane may be used alone or in combination. Water (distilled water) or ethanol (alcohol) may be preferably used in view of safety and the like.
As the extraction method, any one of the methods such as hot water extraction method, cold extraction method, reflux cooling extraction method, solvent extraction method, steam distillation method, ultrasonic extraction method, elution method and compression method can be selected and used. In addition, the desired extract may be further subjected to a conventional fractionation process or may be purified using a conventional purification method. There is no limitation on the method for producing the citron extract of the present invention, and any known method can be used.
For example, the citrus seed extract contained in the composition of the present invention can be prepared into a powdery state by an additional process such as vacuum distillation, freeze-drying, or spray drying, have. Further, the primary extract can be further purified by using various chromatographies such as silica gel column chromatography, thin layer chromatography, high performance liquid chromatography and the like, You can get it.
Therefore, in the present invention, the citron extract is a concept including all of the extract, fraction and purified product obtained in each step of extraction, fractionation or purification, a diluted solution thereof, a concentrate or a dried product.
Hereinafter, a method for preparing the citron extract according to an embodiment of the present invention will be described in detail.
After the process of milking (extracting the oil), the remaining solid part of the citron was dried, and then the seed husks (yellowish white), the septum (brown film between the shell and the seed milk) and the cecum were separated. ) Can be added and extracted with hot water or ethanol, and the extract can be used by lyophilization.
The yuzu seed extract of the present invention has an excellent antioxidative activity and particularly has an antioxidative activity remarkably superior to the extract of other parts (bark, catechol) in extracts of citrus peel part, and is useful as a functional material for skin whitening Can be used.
In addition, the present invention provides a cosmetic composition for whitening comprising a limonoid aglycon derived from yuzu as an active ingredient.
The limonoid aglycon derived from yuza of the present invention may be selected from the group consisting of limonin, nomilin, obacunone, deacetylnomilin and limonate A-ring lactone).
The limonoid aglycon derived from yuzu seeds of the present invention has safety because it does not show cytotoxicity even at a high concentration and has excellent melanin production inhibitory effect against limonin which is known in the prior art whitening function and is useful as a functional material for skin whitening .
In one embodiment of the present invention, the yuzu seed extract or the yuza seed-derived limonoid aglycon may be contained in the cosmetic composition at a concentration of 0.001 to 10,000 μg / ml.
Examples of products to which the cosmetic composition of the present invention can be added include cosmetics such as astringent lotion, softening longevity lotion, nutrition lotion, various creams, essences, packs, foundation and the like, cleansing, cleanser, soap, .
Specific formulations of the cosmetic composition of the present invention may include, but are not limited to, softening lotion, gel, water-soluble liquid, milk lotion, nutritional cream, massage cream, essence, oil in water emulsion, water in oil type emulsion, facial anhydrous product, A lipid, a lipid, a lipid, a lipid, a lipid, a lipid, a lipid, a lipid, a lipid, a lipid, Lipstick, lip gloss, face powder, two-way cake, eye shadow, mascara, cheek color, and eyebrow pencil.
According to a preferred embodiment of the present invention, the content of the active ingredient of the present invention (limonoid aglycon derived from yuza seed extract or citron) is 0.00001-40 wt%, preferably 0.0005-40 wt% By weight, and more preferably 0.0005 to 20% by weight. If the content of the active ingredient is less than 0.00001% by weight, the effect of skin whitening is greatly reduced. If the content of the active ingredient is more than 20% by weight, skin irritation may be caused.
On the other hand, the cosmetic composition according to the present invention can be formulated by stabilizing the active ingredient (containing yuza seed extract or yuza seed-derived limonoid aglycon) in the nanoliposome. When the active ingredient (the yuza seed extract or the yuza seed-derived limonoid aglycon) is contained in the inside of the nanoliposome, the active ingredient is stabilized and the problems such as precipitation formation, discoloration, and deterioration upon formulation can be solved, The transdermal absorption rate can be increased and the efficacy expected from the extract can be maximally expressed.
In the present invention, nanoliposome refers to a liposome having a typical liposome form and having an average particle diameter of 10 to 500 nm. According to a preferred embodiment of the present invention, the average particle diameter of the nanoliposome is 50 to 300 nm, more preferably 100 to 200 nm. When the average particle diameter of the nanoliposome exceeds 500 nm, improvement of skin penetration and improvement of formulation stability is very weak among technical effects to be achieved in the present invention.
According to the present invention, the nanoliposome used for stabilizing the active ingredient (the yuzu seed extract or the yuza seed-derived limonoid aglycon) is prepared by a mixture comprising a polyol, an oily component, a surfactant, a phospholipid, a fatty acid and water .
The polyol used in the nanoliposome of the present invention is not particularly limited and is preferably a polyol such as propylene glycol, dipropylene glycol, 1,3-butylene glycol, glycerin, methylpropanediol, isopropylene glycol, pentylene glycol, erythritol, , Sorbitol, and mixtures thereof. The amount thereof is 10 to 80% by weight, preferably 30 to 70% by weight, based on the total weight of the nanoliposome.
The oil component used in the preparation of the nanoliposome of the present invention may be selected from a variety of oils known in the art and is preferably a hydrocarbon oil such as hexadecane and paraffin oil, Vegetable oils such as silicon oil such as dimethicone and cyclomethicone, sunflower oil, corn oil, soybean oil, avocado oil, sesame oil and fish oil, ethoxylated alkyl ether oils, propoxylated alkyl ether oils 40 is a fatty alcohol, and mixtures thereof -, phytosphingosine, sphingosine, and scan non-ping the same scan pinggo cannabinoid lipid, cholesterol side-by celebrity, sitosterol cholesteryl sulfate, cholesteryl sulfate, cytokines, C 10. The amount thereof may be 1.0 to 30.0% by weight, and preferably 3.0 to 20.0% by weight based on the total weight of the nanoliposome.
Any surfactant known in the art may be used as the surfactant used in the preparation of the nanoliposome of the present invention. For example, anionic surfactants, cationic surfactants, amphoteric surfactants and nonionic surfactants can be used. Preferred are anionic surfactants and nonionic surfactants. Specific examples of anionic surfactants include alkyl acyl glutamates, alkyl phosphates, alkyl lactylates, dialkyl phosphates and trialkyl phosphates. Specific examples of nonionic surfactants include alkoxylated alkyl ethers, alkoxylated alkyl esters, alkyl polyglycosides, polyglyceryl esters and sugar esters. Particularly preferred surfactants are polysorbates belonging to nonionic surfactants. The amount thereof may be 0.1 to 10% by weight, preferably 0.5 to 5.0% by weight, based on the total weight of the nanoliposome.
The phospholipid, another component used in the preparation of the nanoliposomes of the present invention, is a lipophilic lipid that is used with both affinity lipids and is composed of natural phospholipids (e.g., egg yolk lecithin or soy lecithin, sphingomyelin) Dipalmitoyl phosphatidylcholine or hydrogenated lecithin), preferably lecithin. In particular, unsaturated lecithin or saturated lecithin derived from natural origin extracted from soybean or egg yolk is preferable. Normally, the amount of phosphatidylcholine is 23 to 95% and the amount of phosphatidylethanolamine is 20% or less in natural derived lecithin. In the production of the nanoliposome of the present invention, the amount of the phospholipid to be used is 0.5 to 20.0% by weight, preferably 2.0 to 8.0% by weight based on the total weight of the nanoliposome.
Fatty acid to be used in nano-liposome preparation of the present invention is a higher fatty acid, preferably a C 12 - 22 as a saturated or unsaturated fatty acid of the alkyl chain, e.g., lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid and linoleic acid . The amount thereof may be 0.05 to 3.0% by weight, preferably 0.1 to 1.0% by weight, based on the total weight of the nanoliposome.
The water used in the preparation of the nanoliposome of the present invention is generally deionized distilled water, and the amount thereof may be 5.0-40 wt% based on the total weight of the nanoliposome.
The preparation of nanoliposomes can be accomplished through a variety of methods known in the art, but most preferably is made by applying a mixture comprising the ingredients to a high pressure homogenizer. The preparation of a nanoliposome by a high pressure homogenizer can be carried out under various conditions (for example, pressure, number of times, etc.) depending on a desired particle size, and preferably at a high pressure homogenizer So that the nanoliposome can be produced.
The cosmetic composition of the present invention may be used alone or in combination, or it may be used in combination with other cosmetic compositions other than the present invention. Also, the cosmetic composition having excellent antioxidative and whitening effect according to the present invention can be used according to a conventional method of use, and the use frequency of the cosmetic composition can be changed according to a user's skin condition or taste.
Hereinafter, the present invention will be described in more detail with reference to Examples. These examples are for further illustrating the present invention, and the scope of the present invention is not limited to these examples.
< Example 1>
By yuzu seed portion (shell, Seam , Seeded) Preparation
<1-1> Securing Yuza
The yuza seeds used in this experiment were separated from the citron produced in November 2015 in Goheung, Jeollanam Province. The separated yuza seeds were cleaned twice or three times in flowing water to remove foreign matter and dried overnight at 50 ° C (See Fig. 1).
<1-2> Yuzu Seed Oil Milking
The oil obtained by high pressure milking process was milked and the oil acquisition yield was measured in order to secure the oil component including the specific flavor of citron and the water solubility and the fat soluble component of citron seed oil. The pressure was set at 600kg / ㎠ during the milking process and the pressure was applied for 1 hour. The yuza seeds were firstly filtered at 600mesh (23 ㎛) for the milking process of Yuza, Secondary filtration was performed at 1,200 mesh (12 탆). The final yield was determined by sedimentation for 100 hours in order to finally confirm the suspended solids eluted in the filtered citrus seed oil. The final yield of yuza seed oil was about 11.6% of dry matter weight.
<1-3> Isolation of citron after milking
After the milking process, the remaining solid portion of the yuzu seed was dried and then separated into a shell (yellowish white), a seam (brown film between the skin and the seed), and catechin.
After the milking process, a certain amount of water was supplied to the solid portion of the remaining yuzu seed, which was then kept frozen at 20 ° C for 24 hours and then dried using a hot air fan. Using a sharpener, the yuzu seeds were cut into three pieces in an easy-to-separate form, and then peeled off with citrus peel, sesame seeds, and seeds using frictional force.
< Example 2>
Yuza-derived Limonoid Aglycon and glucoside extraction
<2-1> Limonoid Aglycone extract
Three times (600 mL) of ethanol was poured into the pulverized product (200 g) obtained by crushing the seeds of citrus peel, seed, and seed obtained in Example <1-3> and extracted with stirring at 100 rpm at room temperature for 24 hours. Each extract was filtered, and the filtrate was concentrated using a vacuum concentrator to obtain a limonoid aglycon. The yields of limonoid aglycone were 12.35g, 11.16g and 14.73g, respectively, and the yield of the last limonoid aglycon was 15.44%.
<2-2> Limonoid Glucoside separation purification
Residues (residual shell, residual sebum, residual seed) from the filtration (filtration) of Example <2-1> were washed with water and dried in the shade at room temperature. To 100 g of the dried residue (shell, seed, and seed) was added 1000 mL of distilled water and the mixture was shaken at 100 rpm at room temperature for 24 hours with a shaker. After stirring and filtration, the filtrate was lyophilized for 3 to 4 days using a freeze dryer. The lyophilized concentrate was washed three times with 100% ethanol, and the ethanol was removed using a vacuum concentrator to finally obtain limonoid glucoside. At this time, the weight of the yuzu seed coat, the seed coat, and the cirrhotic limonoid glucoside were 8.12 g, 6.10 g, and 7.32 g, respectively, and the yield of the final remarnoide glucoside was 21.54%.
< Experimental Example 1>
Yuza seed Limonoid Antioxidant effect of aglycon
In this experiment, the antioxidant effect of the limonoid aglycon (peel, bark, seedling) obtained in Example 2 was examined. Antioxidant activity was investigated by ABTS radical scavenging activity and DPPH radical scavenging activity, and total polyphenol contents were further investigated.
<1-1> ABTS Radical scavenging activity
In this experiment, Jeong et al. (2009) was modified and measured. The solution was diluted with PBS (pH 7.4) so that the absorbance value was 1.10 ± 0.02 by adding 2.45 mM of ABTS potassium persulfate (7 mM) dissolved in distilled water in a ratio of 1: 1. Radical stock solution was added to 800 μl of the diluted solution and 200 μl of the sample prepared for each concentration was added for 15 minutes, and the absorbance was measured. As a positive control, ascorbic acid (Sigma, USA) was used. The abstraction (IC 50 ) of the extracts against ABTS was expressed as the concentration required to reduce the absorbance of the control using only solvent by 50%.
As a result, the IC 50 value of remote solenoid aglycone extract from the bark were the antioxidant activity was the highest in 1000㎍ / mL, the remote solenoid IC 50 value of the extracted aglycone from ssijeot As shown in Table 1 is 15585㎍ / mL showed the lowest antioxidant activity.
<1-2> DPPH Radical scavenging activity
DPPH has a characteristic absorption spectrum at 517 nm due to the odd electrons it possesses. When it reacts with an electron donor providing hydrogen atom, it gets hydrogen radical to generate phenoxy radical. DPPH is purple in the radical state, and when it is reduced, it is converted to yellow 2,2-diphenyl-1-picrylhydrazine (DPPH-H). DPPH, a stable radical, converts to non-radical when it is supplied with electrons or hydrogen from antioxidants. The DPPH method is widely used as a method for measuring the antioxidative activity of a water-soluble or organic solvent extract of a natural product.
In this experiment, the antioxidant activity of Blois (Blois, 1958) was modified to measure the radical scavenging ability of the sample. 800 μl of 0.1 mM DPPH (2,2-diphenyl-1-picrylhydrazyl, Sigma, USA) dissolved in 95% ethanol and 200 μl of each test group were placed in an EP tube and vortexed for 3 minutes in a dark room for 30 minutes. The remaining concentrations of the radicals were measured at 517 nm using a UV-Visible spectrophotometer (SCINCO, Seoul, Korea) and ascorbic acid (Sigma, USA) was used as a positive control. The scavenging ability (IC 50 ) of the sample against DPPH was expressed as the concentration required to reduce the absorbance of the control using only the solvent by 50%.
As a result, as shown in Table 2, the IC 50 value of the limonoid aglycone extracted from the skin was 4648 μg / mL, which was the highest antioxidative activity, and the IC 50 value of the limonoid aglycon extracted from the sesame seeds was 57157 μg / mL showed the lowest antioxidant activity.
<1-3> By Yuza's parts Limonoid Total polyphenol activity of aglycon
Total polyphenol content was determined using the modified Folin-Denis method. Each sample was diluted by concentration, and 1 mL of the sample was mixed with 1 mL of 0.2 N Folin &Ciocalteu's phenol reagent and 1 mL of 2% Na 2 CO 3, and the mixture was reacted at room temperature for 30 minutes. Absorbance was measured at 750 nm using a UV-VIS spectrophotometer. As the reference material, gallic acid was used to obtain the calibration curve, and the total polyphenol content was measured from the calibration curve. 0.5 ml of distilled water and 0.125 ml of folin-ciocalteu's phenol reagent were added to 0.125 ml of the prepared sample for each concentration and reacted for 6 minutes. After the reaction, 1.25 mL of 7% sodium carbonate solution and 3 mL of distilled water were added and reacted for 90 minutes. OD value was measured at 760 nm using a spectrophotometer. Total polyphenol content was calculated from the standard curve determined using gallic acid.
As a result, as shown in Table 3, the total polyphenol content of the limonoid aglycon extracted from the skin was the highest at 7.0842 GAE * mg / g, and the total polyphenol content of the limonoid aglycone extracted from the beef tallow was 1.4099 GAE * mg / g.
The antioxidant activities of the limonoid aglycone by the parts of the yuza seeds were found to be higher in order of shell> sheep> sperm.
< Experimental Example 2>
Yuza-derived Limonoid Aglycone HPLC analysis
HPLC analysis was carried out using a limonoid aglycon derived from yuza seed obtained in Example <2-1> to analyze the reference material, and the retention time of the reference material was compared to confirm the content and content. The conditions are summarized in the table below.
As a result, as shown in Table 5 and FIG. 5, HPLC analysis of a standard mixture made of Limonin and nomilin showed that limonin was found at 29 minutes and nomilin was found at 35 minutes. Both limonin and nomilin were identified in 29 minutes and 35 minutes in the linoleic acid aglycone extracted from citron peel, sea bass, and seedlings.
< Experimental Example 3>
Yuza-derived Limonoid Aglycone HPLC / MS analysis
As shown in FIG. 6, limonin, nomilin, deacetylnomilin, obacunone, and limonate A-glucuronide were detected by HPLC / MS analysis using a limonoid aglycone derived from Yuza seed obtained in Example <2-1> ring lactone, and the analysis conditions are summarized in the table below.
(50 mm x 2.1 mm, 1.8 m)
< Experimental Example 4>
Originated from Yuza Farnoid Cytotoxicity Assessment
The cytotoxicity of the yuza seed-derived limonoid aglycon / limonoid glucoside obtained through Example 2 was evaluated.
The cell line B16 / F10 (murine melanoma) used in the experiment was distributed at the Korean Cell Line Bank (KCLB). The cells were cultured in a 4% CO 2 incubator at 37 ° C with 5% FBS, 1% penicillin streptomycin, and 1 μg / mL α-MSH (α-Melanocytestimulating hormone).
MTT assay is a method for measuring the change in color of NAD (P) H-dependent oxidoreductase enzymes of cells using Tetrazolium dye, which measures the growth or death of cells. That is, when the cells are alive, MTT is reduced to change the color, but when the cell is dying or stops growing, the dye is not reduced. Using this principle, the toxicity of the extract containing the yuiza seeded limonoid aglycon / limonoid glucoside was examined, and the change in color was indirectly measured.
To evaluate the cytotoxicity, the cell lines were inoculated into 12 well plates at 1 × 10 4 cells / well and cultured for 24 hours. The MTT stock solution (5 mg / mL) was added to the culture medium to a final volume of 1/10 to the cultured cells after the sample was treated with the concentration (25 μg / mL, 50 μg / mL, 100 μg / mL) Lt; 0 > C for 4 hours. After the reaction, the culture supernatant was removed, 200 μL of DMSO was added to each well to dissolve the MTT-formazan crystals produced in the cells, and the absorbance was measured at 570 nm on an ELISA readeer.
As a result, as shown in FIG. 7A, it was confirmed that the limonoid aglycon derived from yuza seed of the present invention had no cytotoxicity up to a concentration of 100 μg / mL. On the other hand, the ulceroid glycosides derived from yuza seeds of the present invention did not show cytotoxicity up to a concentration of 50 μg / mL, and the cell survival rate was slightly reduced at a concentration of 100 μg / mL (see FIG.
From the above results, it was confirmed that the limonoid aglycon derived from citron of the present invention scarcely exhibited cytotoxicity and was excellent in safety.
Thus, in the following whitening activity experiment, the limonoid aglycone derived from yuza seed of the present invention having excellent cell safety was used.
< Experimental Example 5>
Originated from Yuza Limonoid Aglycone Whitening activity evaluation
In order to evaluate the whitening activity of the yuza seed-derived limonoid aglycon obtained through Example 2, analysis of intracellular melanin content according to the limonoid aglycone treatment of the present invention and analysis of intracellular whitening activity-related proteins (tyrosinase, TRP-1, and TRP-2) were examined.
<5-1> Analysis of melanin content
To quantify the melanin produced, B16 / F10 melanoma cells were seeded at a concentration of 1 × 10 5 cells / well in a 6-well plate and cultured at 37 ° C. and 5% CO 2 for one day. Subsequently, samples were treated with α-MSH (1 μg / ml) and concentrations (25 μg / ml, 50 μg / ml, 100 μg / ml) and cultured for 3 days. The cultured cells were centrifuged for 5 minutes and the resulting cell suspension was dissolved in 1 mL of PBS. The pellet thus obtained was dissolved in 200 uL of 1 N NaOH (+ 10% DMSO) solution and absorbance was measured at 405 nm. The untreated group was used as a control group, and the arbutin-treated group (
As a result, as shown in FIG. 8A, the amount of melanin increased by 63.79% when 1000 nM α-MSH was treated, compared with that of the untreated group (100%) and that the α-MSH 1000 nM, Treatment groups treated with 25 μg / mL, 50 μg / mL, and 100 μg / mL of concentrations were decreased to 14.1% and 39.3%, respectively.
<5-2> Whitening activity Expression of related proteins (tyrosinase, TRP-1, TRP-2) change
B16F10 cell suspension was added to each well at a concentration of 1 × 10 5 cells / ml per well in a 100 π tissue culture dish, followed by culturing for 24 hours to stabilize the cells. Then, the limonoid aglycon of the present invention , 50 [mu] g / mL). After incubation, cells were washed 2-3 times with PBS, lysed with lysis buffer, and centrifuged at 13,000 rpm for 10 min. Quantitation of protein was measured by Bradford method. Briefly, 20 μg of protein is denatured by 10% sodium dodecyl sulfate-polyacrylamide (SDS-PAGE) and transferred to a polyvinylidene difluoride (PVDF) membrane. After blocking the membrane, the primary antibody is added to Tris-buffered saline with 0.2% Tween-20 (TBST) containing 2.5% nonfat dry milk and allowed to react at room temperature for 1
As a result, as shown in FIG. 9, in the case of treatment of the limonoid aglycon of the present invention with cells, tyrosinase, TRP-1 and TRP-2, which are the core protein markers of whitening activity, As a result, it was judged that the limonoid aglycon of the present invention had a very high whitening activity.
The present invention has been described with reference to the preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. Therefore, the disclosed embodiments should be considered in an illustrative rather than a restrictive sense. The scope of the present invention is defined by the appended claims rather than by the foregoing description, and all differences within the scope of equivalents thereof should be construed as being included in the present invention.
Claims (7)
Wherein the extract is one or more extracts selected from the group consisting of citron peel, sea bream and cetal.
Wherein the extract is extracted with at least one solvent selected from the group consisting of lower alcohols having 1 to 4 carbon atoms, ethyl acetate, acetone, water and hexane.
Wherein the extract is an ethanol extract.
The limonoid aglycon derived from Yuza is selected from the group consisting of limonin, nomilin, obacunone, deacetylnomilin and limonate A-ring lactone. Wherein the cosmetic composition is a cosmetic.
The cosmetic composition may be an oil in an aqueous phase using a softening lotion, a gel, a water-soluble liquid, a milk lotion, a nutritional cream, a massage cream, an essence, an oil in water emulsion, a water in oil emulsion, a facet anhydrous product, Lipid, lip gloss, face powder, lipstick, lipstick, lipstick, lipstick, lipstick, lipstick, lipstick, lipstick, lipstick, lipstick, , Two-way cake, eye shadow, mascara, cheek color, eyebrow pencil, and the like.
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| KR1020170078545A KR20180138386A (en) | 2017-06-21 | 2017-06-21 | Whitening cosmetic composition comprising yuza seed extract as an active ingredient |
| PCT/KR2017/013125 WO2018236007A1 (en) | 2017-06-21 | 2017-11-17 | Whitening cosmetic composition containing citrus junos seed extract as active ingredient |
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| CN112266825A (en) * | 2020-10-29 | 2021-01-26 | 青岛科技大学 | Compound essential oil, preparation method thereof and application of compound essential oil in whitening and anti-wrinkle cosmetics |
| CN112745399B (en) * | 2021-02-04 | 2022-03-15 | 华南农业大学 | Extraction process of shaddock seed polysaccharide |
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| JP2002068953A (en) * | 2000-08-22 | 2002-03-08 | Ichimaru Pharcos Co Ltd | Cosmetic composition |
| KR20110047824A (en) * | 2009-10-30 | 2011-05-09 | 동국대학교 산학협력단 | Cosmetic Composition Comprising Citron Extracts |
| KR20140121605A (en) * | 2013-04-08 | 2014-10-16 | (주)내츄럴코리아 | Cosmetic compostion containing citron extract fermentation solubles and method of manufacturing the same |
| JP2015086181A (en) * | 2013-10-31 | 2015-05-07 | キッコーマン株式会社 | Citrus junos seed extract-containing composition, food product and pharmaceutical |
| KR20150139688A (en) * | 2014-06-03 | 2015-12-14 | 조정희 | The Extract Of The Citrus grandis Osbeck Having Skin Whitening Activity And Cosmetic Composition Containing The Same |
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