KR101695002B1 - Composition of skin external application containing propanoid derivatives - Google Patents

Abstract

The present invention relates to a composition for external application for skin containing a propanoid derivative, and more particularly, to a composition for external application for skin comprising a propanoid derivative substituted with a phenyl group to provide a skin anti-aging effect, a skin moisturizing power improving effect, , A whitening effect, and the like.

Description

[0001] The present invention relates to a skin external application composition containing a propanoid derivative,

The present invention relates to a composition for external application for skin containing a propanoid derivative, and more particularly, to a composition for external application for skin comprising a propanoid derivative substituted with a phenyl group to provide a skin anti-aging effect, a skin moisturizing power improving effect, , A whitening effect, and the like.

The human skin undergoes changes due to various internal and external factors as it gets older. In other words, internally, secretion of various hormones that regulate metabolism is reduced, the function of immune cells and the activity of cells are lowered, and the biosynthesis of immune proteins and biocompatible proteins necessary for the living body is reduced, and ozone layer destruction As the content of ultraviolet rays reaching the surface of the sunlight increases and environmental pollution is further intensified, free radicals and active harmful elements increase, thereby reducing the thickness of the skin, increasing the wrinkles and reducing the elasticity Skin color is grayish, skin troubles occur frequently, and spots, freckles and black blots also increase.

As the aging progresses, the content and arrangement of collagen, elastin, hyaluronic acid and glycoprotein, which constitute the skin, are changed or decreased, and oxidative stress due to free radicals and active noxious oxygen is experienced. In addition, most of the cells constituting the skin undergo aging or ultraviolet rays, Cox-2 (cyclooxygenase), an enzyme that produces a proinflammatory cytokine known to cause inflammation, And the biosynthesis of matrix metalloproteinase (MMP), which is an enzyme that degrades skin tissue, is increased by these inflammatory factors, and nitric oxide (NO) production by iNOS (inducible nitric oxide synthase) Respectively. In other words, there is a decrease in cell activity due to natural endogenous aging and a decrease in the biosynthesis of substrate materials due to microinflammation, an increase in stress due to various harmful environments, and an increase in active coral species caused by sunlight As the degradation and denaturation are accelerated, the skin substrate is destroyed and thinned, and various symptoms of skin aging appear. Therefore, it is a reality that many researches have been conducted on the active ingredients which can prevent and improve such aging phenomena.

Several factors are involved in determining the skin color of a person, including the activity of the melanocyte that makes the melanin pigment, the distribution of blood vessels, the thickness of the skin, and the presence or absence of pigment in and out of the body, such as carotenoids and bilirubin It is important.

Especially, the most important factor is melanin, a melanin pigment produced by various enzymes such as tyrosinase in melanocytes in the human body. The formation of melanin pigment affects genetic factors, hormonal secretion, physiological factors such as stress, and environmental factors such as ultraviolet irradiation.

The melanin pigment produced in melanocytes of body skin is a phenolic polymer substance having a complex form of black pigment and protein. It protects the subcutaneous skin organs by blocking ultraviolet rays irradiated from the sun, and at the same time, free radicals And protects proteins and genes in the skin.

Melanin, which is produced by stress stimuli inside and outside the skin, is a stable substance that does not disappear until the skin is excreted through skin keratinization even if the stress disappears. However, when melanin is produced more than necessary, it induces hypercholesterolemia such as spots, freckles, and dots, resulting in poor cosmetic results.

Today, oriental women prefer white, clean skin like white whites, and this is an important criterion of beauty, so there has been a growing demand for treatment and cosmetic problems for hyperpigmentation.

In response to such demands, substances having ascorbic acid, kojic acid, arbutin, hydroquinone, glutathione, derivatives thereof, or tyrosinase inhibiting activity have been conventionally used in cosmetics or pharmaceuticals, The use thereof is limited due to a whitening effect, a safety problem to the skin, a problem of formulation and stability in combination with cosmetics, and the like.

The most important function of the epidermis located on the outermost part of the skin is to protect against various external stimuli (physical and chemical stimulants such as chemicals, air pollutants, dry environment, ultraviolet rays) , And this protective function can maintain its function only when the stratum corneum composed of keratinocytes is normally formed. The stratum corneum (horney layer), which is the outermost part of the epidermis, is formed from keratinocytes and consists of keratinocytes with complete differentiation and a surrounding lipid layer (J. Invest. Dermatol. 1983; 80: 49). The keratinocyte is a characteristic cell in which the basal cell that continuously proliferates in the lowest epidermis undergoes a stepwise change in morphology and function and is elevated to the surface of the skin. After a certain period of time, This process is called "epidermal cell differentiation" or "keratinization" because the new keratinocyte replaces its function. During keratinization, keratinocytes form the stratum corneum while producing natural moisturizing factors (NMF) and intercellular lipids (ceramides, cholesterol, fatty acids), making the stratum corneum firm and flexible, As shown in Fig.

However, such a stratum corneum can easily lose its function due to excessive skin cleansing, lifestyle factors such as nourishment, environmental factors such as dry air and pollutants, and endogenous diseases such as atopic skin and senile skin, Due to the increasing number of factors in the modern age, there has been an increasing tendency in recent years to appeal to people with dry skin symptoms and disorders. Therefore, in order to maintain proper skin moisture, studies have been conducted to supply moisture from the outside or to prevent water loss from the body, and a variety of moisturizers having moisture retention ability have been developed, It is widely used in the area.

However, as the risk factors for humans increase in the living environment and the aging population rapidly increases, the turnover rate of the stratum corneum is delayed, the lipid synthesis ability of the keratinocytes decreases, The cells are not smoothly divided, maturated and differentiated, and the amount of moisturizing factors and lipids in the stratum corneum is decreased, so that the normal stratum corneum does not maintain its function. Namely, .

Due to the abnormal division and differentiation of the epidermal cells, the skin causes various skin diseases such as dry skin, atopy and psoriasis. Such a disease can alleviate the symptoms only with a conventional moisturizing agent having only moisture holding function , But it is difficult to expect fundamental healing.

In general, sebaceous glands in the skin, including the scalp and face, play a role in preventing moisturization and microbial invasion of the skin. However, excessive secretion of sebum promotes hair loss, worsens acne, promotes enlargement of pores caused by acne, And many other diseases are caused.

The hypersecretion of sebaceous glands is caused by various causes, and the most important one is the activation of sebaceous glands by the amount of dihydrotestosterone (DHT), which is one of the hormones involved in promoting sebaceous secretion in the activity of sebaceous glands, Is overdone. That is, testosterone (T) is converted into dihydrotestosterone, one of the male hormones, by 5-alpha-reductase type 2 in cells in the hair loss, (5-α-reductase type 1) in the skin or the sebaceous glands. The testosterone is converted to dihydrotestosterone by the action of 5-α-reductase type 1, Activation to promote differentiation promotes sebum in the sebaceous glands and causes acne (J. Invest Dermatol 105: 209-214 Diane etc.).

Acne and hair loss, which are skin troubles other than simple sebum hypersecretion, are further exacerbated by the minute inflammatory reaction of the skin. If you look at the development of acne, excess sebum accumulates in the hair follicle, activating acne bacteria and causing inflammation.

It has antioxidant effect with excellent antioxidant effect, inhibiting the production of prostaglandin, especially prostaglandin E2 (PGE2) in cell inflammation reaction, inhibiting the production of nitric oxide (NO) by iNOS, It is possible to alleviate the skin troubles.

However, there are not many raw materials that can reduce sebum secretion as a skin-safe natural material through fundamental causes and at the same time to relieve inflammation.

Accordingly, the present inventors have found that propranoid derivatives substituted with a phenyl group can provide not only anti-aging, skin wrinkle improvement, whitening, moisturizing, but also acne and skin troubles and atopic symptoms, And the present invention has been completed.

Accordingly, an object of the present invention is to provide a composition for external application for skin, which contains a propanoid derivative substituted with a phenyl group to improve the overall condition of the skin.

In order to achieve the above object, the present invention provides an anti-aging external preparation for skin comprising a propanoid-substituted derivative of a phenyl group as an active ingredient.

The present invention also provides a composition for external application for moisturizing skin containing a propanoid derivative substituted with a phenyl group as an active ingredient.

The present invention also provides a composition for external application for skin for improving acne, which comprises a propanoid derivative substituted with a phenyl group as an active ingredient.

The present invention also provides a composition for external application for skin improvement and skin tone improvement comprising a propanoid derivative substituted with a phenyl group as an active ingredient.

The present invention also provides a composition for external application for skin pore reduction comprising a propanoid derivative substituted with a phenyl group as an active ingredient.

The present invention also provides a composition for external application for skin for slimming comprising a propanoid derivative substituted with a prenyl group.

The present invention also provides a whitening dermatological external preparation composition.

The composition of the present invention contains a propanoid derivative substituted with a phenyl group to give an anti-aging effect, a skin wrinkle improving effect, a skin whitening effect, a skin moisturizing effect and an atopic symptom improvement effect, an acne and skin trouble improving effect, It can also provide a slimming effect and an ultraviolet blocking effect.

The composition for external application for skin according to the present invention contains a propanoid derivative substituted with a phenyl group as an active ingredient.

The propanoid derivative substituted with a phenyl group used in the present invention has a structure represented by the following formula (1)

From here,

R ₁ is H or -CH ₃ ,

R ₂ is H or -CH ₃ ,

R < ₃ > is H or -OH,

또는

이며,R ₄ is H, -OCH ₃ ,

or

Lt;

이고,X is H or

ego,

또는

이며,Y is H,

or

Lt;

,

,

,

또는

이다.Z is H, -CH _3,

,

,

,

or

to be.

The propanoid derivative substituted with a phenyl group used in the present invention may be selected from the group consisting of broussonin A, brassonin B, brassonin C, brassonin D, bromonon E, brsonin F, kazinol C, It is preferable to use at least one selected from the group consisting of casinol D, casinol F, casinol G, casinol J, casinol K, casinol L, casinol M and casinol N, The casinol is shown in Table 1 below.

The propanoid derivatives substituted with the phenyl group of the present invention may be extracted from plants, synthesized, or commercially available ones. It is also preferable to use a pharmaceutical composition containing at least one of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Brosonin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, , Casinol L, casinol M and casinol N can be obtained from mulberry extracts. Mackerel roots used at this time can be used as long as they are in the mackerel tree. Specifically, mackerel (Broussonetia kazinoki Sieb), Broussonetia papyrifera Vent, and Broussonetia kazinoki var. Humilis can be used. The mulberry extract is not only contained in the leached liquid obtained by leaching from the mulberry tree, but also the concentrate obtained by partially or entirely concentrating the leach solution or the dregs, premix, seasoning, fluid extract and mulberry produced by drying the concentrate again It includes all of the plant itself as well as the chemicals that have the primary effect, and extracts from all parts of the mulberry tree, including stem, root, leaf, flower, and fruit, are available and are not limited to any particular part of the extract. In addition, a known method can be used for extracting the propanoid derivative substituted with the phenyl group from the mulberry extract.

Specifically, the mulberry extract can be extracted from mulberry leaves after extraction with water or an organic solvent by a method well known in the art. The organic solvent used in the present invention may be selected from the group consisting of ethanol, methanol, butanol, ether, ethyl acetate, chloroform and a mixed solvent of these organic solvents and water, preferably 80% ethanol. At this time, the extraction temperature is preferably 10 to 80 ° C, and the extraction can be performed for 3 to 24 hours. If the extraction temperature and the extraction time are exceeded, the extraction efficiency may be deteriorated or the component may be changed. The propanoid derivative substituted with a phenyl group used in the present invention may be obtained through synthesis according to a method known in the art, or a commercially available propanoid derivative may be purchased and used.

The composition according to the present invention may contain the propanoid derivative substituted with the above-mentioned prenyl group in an amount of 0.001 to 50% by weight based on the total weight of the composition. If the content of the propanoid derivative substituted with the above-mentioned prenyl group is less than 0.001% by weight, the effect and effect of the above-mentioned components are insufficient. If the content is more than 50% by weight, skin safety or shape problems may occur.

The composition of the present invention can be used as a composition for external application for skin for anti-aging, which is excellent in improving skin elasticity and improving wrinkles.

The composition of the present invention can be used as a composition for external application for moisturizing skin, which can enhance the skin barrier function and induce differentiation of dermal keratinocytes. Therefore, it can be effectively used as a composition for external application for skin, which prevents or improves skin dryness, atopic dermatitis, contact dermatitis, psoriasis or the like caused by incompleteness of epidermal differentiation.

The composition of the present invention can be used as a composition for external application for skin for improving acne, and has excellent antimicrobial effect, especially antimicrobial effect against acne causing bacteria, and also provides anti-inflammatory effect.

The composition of the present invention can be used as a composition for external application of skin for improving color and skin tone. It expands capillary blood vessels when applied to skin and promotes circulation of blood, thereby smoothly supplying nutrients to skin and suppressing skin aging, The effect is excellent.

The composition of the present invention can be used as a composition for external application for skin for reducing pores, controlling sebum and improving skin troubles. It can suppress sebum secreted excessively when applied to skin, promote active oxygen elimination and collagen synthesis, , And suppression of skin troubles due to decreased expression of inflammatory factors. In addition, excellent antioxidant power can prevent the generation of skin irritation.

The composition of the present invention can be used as a composition for external application for skin for slimming, which has the effect of decomposing triglycerides and decreasing cellulite, and thus has a slimming effect of slimming the subcutaneous fat when administered as a skin-type formulation.

The composition of the present invention can be used as a whitening composition, which can provide an excellent whitening effect by inhibiting tyrosinase activity and inhibiting the production of melanin.

In addition, the composition of the present invention can be used as a composition for external skin application for ultraviolet rays having an excellent ultraviolet blocking effect.

The composition according to the invention may be formulated containing a cosmetically or dermatologically acceptable medium or base. These are all formulations suitable for topical application, for example as a solution, a gel, a solid, a paste anhydrous product, an emulsion obtained by dispersing an oil phase in water, a suspension, a microemulsion, a microcapsule, a microgranule or an ionic form (liposome) In the form of ionic fibrin dispersions, or in the form of creams, skins, lotions, powders, ointments, sprays or conical sticks. It can also be used in the form of a foam or in the form of an aerosol composition further containing a compressed propellant. These compositions may be prepared according to conventional methods in the art.

In addition, the composition according to the present invention may further comprise at least one selected from the group consisting of fatty substances, organic solvents, solubilizers, thickening agents, gelling agents, softening agents, antioxidants, suspending agents, stabilizing agents, Such as fillers, emulsifiers, emulsifiers, fillers, sequestering agents, chelating agents, preservatives, vitamins, blockers, moisturizers, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or any other ingredient commonly used in cosmetics May contain adjuvants commonly used in the field of cosmetics or dermatology. Such adjuvants are introduced in amounts commonly used in the cosmetics or dermatological fields.

In addition, the composition of the present invention may contain a skin absorption promoting substance to increase the skin improving effect.

Hereinafter, the constitution and effects of the present invention will be described in more detail with reference to test examples and formulation examples. However, these test examples and formulation examples are provided for illustrative purposes only for the sake of understanding of the present invention, and the scope and scope of the present invention are not limited by the following examples.

[Test Example 1] Elastase activity inhibition assay

The inhibitory activity of elastase activity of the propanoid derivatives substituted with a prenyl group was measured in comparison with EGCG. The elastase and substrate used were commercially purchased (Cat. No. E0127) from Sigma-Aldrich, USA, and the propanoid derivatives substituted with a prenyl group were obtained from SIGMA, LANCASTER, and TCI.

The elastase activity inhibitory activity was tested by the following test method.

L of Tris-HCl buffer (pH 8.0) was prepared in a 96-well plate, and 50 μL of the test substance shown in Table 2 and 50 μL of 20 μg / mL elastase type III solution were mixed. EGCG 250 μM was used as a positive control, and negative control group, distilled water, was used. Thereafter, 100 μL of 0.4514 mg / mL of N-SUCCINYL-ALA-ALA-ALA-p-NITROANILIDE prepared as the buffer solution was added and reacted at 25 ° C for 15 minutes. After completion of the reaction, the absorbance at a wavelength of 415 nm was measured. A blank test was carried out in the same manner and corrected.

The method for calculating the activity of inhibiting the activity of the elastase was as shown in the following formula (1), and the results are shown in Table 2 below.

A: Absorbance at 415 nm at the wavelength of the enzyme addition,

B: absorbance at a wavelength of 415 nm in the absence of the sample added with the enzyme and no addition of the enzyme

C: Absorbance at wavelength 415 nm in addition of experimental sample and enzyme addition

D: absorbance at a wavelength of 415 nm in the addition of an experimental sample and no enzyme addition

compound % Inhibition Untreated group 0 EGCG 65 Brosonin A 50 Brosonin B 75 Brosonin C 90 Brosonin D 85 Brosonin E 76 Brosonin F 87 Casinol C 85 Casinol D 92 Casinol F 93 Casinol G 90 Casinol J 80 Casinol K 85 Casinol L 95 Casinol M 60 Casinol N 74

As shown in Table 2, the degree of suppression of the elastase activity of the propanoid derivatives substituted with the prenyl group was remarkably superior to that of EGCG, which is substantially higher than that of EGCG, which is known as an inhibitor of elastase activity. It is confirmed that the propanoid derivative substituted with a nitro group is superior in the effect of inhibiting elastase activity.

[Test Example 2] Collagenase (MMP-1)

The ability of the propanoid derivatives substituted with the phenyl group of the present invention to inhibit collagenase production was measured in comparison with retinoic acid.

Human fibroblasts were plated at 5,000 cells / well in a 96-well microtiter plate containing 2.5% fetal calf serum-containing DMEM (Dulbecco's Modified Eagle's Media) And incubated at 37 ° C in an incubator with CO _{2 of} 5% until it grew to about 80%. The propanoid derivative substituted with a prenyl group was treated at a concentration of 10 占 퐂 / ml for 24 hours, and the cell culture solution was collected.

The degree of collagenase production in the cell culture was measured using a commercially available collagenase assay device (Amersham Pharmacia, USA, Catalog #: RPN 2610). First, the cell culture solution collected on a 96-well plate uniformly coated with primary collagenase antibody was added and the antigen-antibody reaction was performed in a thermostatic chamber for 3 hours. After 3 hours, the second collagen antibody bound to the chromophore was placed in a 96-well plate and reacted for another 15 minutes. After 15 minutes, the color development substance (3,3 ', 5,5'-tetramethylbenzidine, sigma) was added and color development was induced at room temperature for 15 minutes. When 1 M sulfuric acid was added to stop the color development reaction, the color of the reaction solution became yellow And the degree of yellowing was different according to the progress of the reaction.

The absorbance of a yellow 96-well plate was measured at 405 nm using a spectrophotometer and the degree of synthesis of collagenase was calculated by the following equation (2) Respectively. At this time, the reaction absorbance of the cell culture fluid collected from the non-treated group was used as a control.

compound Expression level (%) Untreated group 100 Retinoic acid 75 Brosonin A 69 Brosonin B 70 Brosonin C 75 Brosonin D 80 Brosonin E 85 Brosonin F 76 Casinol C 67 Casinol D 65 Casinol F 72 Casinol G 73 Casinol J 80 Casinol K 60 Casinol L 65 Casinol M 75 Casinol N 60

As shown in Table 3, it can be seen that collagenase expression inhibition effect is similar to that of retinoic acid, in which the degree of collagenase expression of a propanoid derivative substituted with a phenyl group is known as a collagenase expression inhibitor .

From these results, it can be confirmed that the propanoid derivative substituted with the phenyl group of the present invention has an effect of inhibiting the substrate metalloprotease (MMP-1).

[Formulation Examples 1 to 15 and Comparative Formulation Example 1]

Nutritive creams were prepared according to the compositions of Tables 4 and 5 in the conventional manner (unit: wt%).

Compounding ingredient Formulation Example 1 Formulation Example 2 Formulation Example 3 Formulation Example 4 Formulation Example 5 Formulation Example 6 Formulation Example 7 Formulation Example 8 Purified water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 Brosonin A 0.1 - - - - - - - Brosonin B - 0.1 - - - - - - Brosonin C - - 0.1 - - - - - Brosonin D - - - 0.1 - - - - Brosonin E - - - - 0.1 - - - Brosonin F - - - - - 0.1 - - Casinol C - - - - - - 0.1 - Casinol D - - - - - - - 0.1 Vegetable hydrogenated oil 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Stearic acid 0.60 0.60 0.60 0.60 0.60 0.60 0.60 0.60 Glycerol stearate 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Stearyl alcohol 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Polyglyceryl-10pentastearate and behenyl alcohol and sodium stearoyl lactylate 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Arachidyl behenyl alcohol and arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucoside 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 PEG-100 Stearate & Glycerololate & Propylene Glycol 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Caprylic / carboxy triglyceride 11.00 11.00 11.00 11.00 11.00 11.00 11.00 11.00 Cyclomedicone 6.00 6.00 6.00 6.00 6.00 6.00 6.00 6.00 Preservative, incense Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Triethanolamine 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1

Compounding ingredient Formulation Example 9 Formulation Example 10 Formulation Example 11 Formulation Example 12 Formulation Example 13 Formulation Example 14 Formulation Example 15 Comparative Formulation Example 1 Purified water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 Casinol F 0.1 - - - - - - - Casinol G - 0.1 - - - - - - Casinol J - - 0.1 - - - - - Casinol K - - - 0.1 - - - - Casinol L - - - - 0.1 - - - Casinol M - - - - - 0.1 - - Casinol N - - - - - - 0.1 - Vegetable hydrogenated oil 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Stearic acid 0.60 0.60 0.60 0.60 0.60 0.60 0.60 0.60 Glycerol stearate 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Stearyl alcohol 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 Polyglyceryl-10pentastearate and behenyl alcohol and sodium stearoyl lactylate 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Arachidyl behenyl alcohol and arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucoside 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 PEG-100 Stearate & Glycerololate & Propylene Glycol 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Caprylic / carboxy triglyceride 11.00 11.00 11.00 11.00 11.00 11.00 11.00 11.00 Cyclomedicone 6.00 6.00 6.00 6.00 6.00 6.00 6.00 6.00 Preservative, incense Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Suitable amount Triethanolamine 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1

[Test Example 3] Confirmation of improving skin elasticity

In order to confirm the skin elasticity improvement effect in humans, the formulations of Formulation Examples 1 to 15 and Comparative Formulation Example 1 were evaluated as follows.

160 healthy women in 30-40 age groups were divided into 16 groups of 10 for each of the 16 groups of Formulation Examples 1 to 15 and Comparative Formulation 1, and the nutritional cream was applied to the face for 1 week for 12 weeks, Skin elasticity was measured using Cutometer SEM 575, C + K Electronic Co., Germany). The results are shown in Table 6 below. The results in Table 6 are reported as ΔR8 (R8 (left) -R8 (right)) of Cutometer SEM 575, where R8 values indicate the properties of viscoelasticity.

Experimental product Skin elasticity effect Formulation Example 1 0.13 Formulation Example 2 0.10 Formulation Example 3 0.17 Formulation Example 4 0.13 Formulation Example 5 0.12 Formulation Example 6 0.16 Formulation Example 7 0.15 Formulation Example 8 0.27 Formulation Example 9 0.18 Formulation Example 10 0.25 Formulation Example 11 0.21 Formulation Example 12 0.18 Formulation Example 13 0.19 Formulation Example 14 0.23 Formulation Example 15 0.24 Comparative Formulation Example 1 0.10

As shown in Table 6, Formulations 1 to 15 containing a propanoid derivative substituted with a phenyl group of the present invention had more skin elasticity than the group to which Comparative Formulation 1 was applied.

Therefore, it can be confirmed that the composition containing the propanoid derivative substituted with the phenyl group of the present invention is very effective for improving skin elasticity.

[Test Example 4] Confirmation of skin wrinkle improving effect

Formulation Examples 1 to 15 and Comparative Formulation Example 1 were used in order to confirm the wrinkle-reducing effect of the composition of the present invention in humans.

In order to confirm the effect of improving the wrinkles of Formulation Examples 1 to 15 and Comparative Formulation Example 1, the following evaluation was made. 160 healthy women were divided into 16 groups of 10 in each of the 16 groups of Formulation Examples 1 to 15 and Comparative Example 1, and the nutritional cream was applied to the face for 12 weeks once a day, The state of the wrinkles was measured by an image analyzer (visiometer, SV600, Courage + Khazaka electronic GmbH, Germany). The results are shown in Table 7 below. The values in Table 7 below are the average values obtained by subtracting the pre-application parameter values from the respective parameter values after 12 weeks of application.

After 8 weeks of use
Clinical outcome R1 R2 R3 R4 R5 Formulation Example 1 0.18 0.16 0.12 0.02 0.02 Formulation Example 2 0.19 0.17 0.13 0.01 0.03 Formulation Example 3 0.20 0.23 0.14 0.03 0.02 Formulation Example 4 0.17 0.17 0.11 0.02 0.03 Formulation Example 5 0.15 0.16 0.09 0.01 0.03 Formulation Example 6 0.19 0.18 0.13 0.02 0.02 Formulation Example 7 0.21 0.21 0.16 0.03 0.01 Formulation Example 8 0.20 0.23 0.15 0.02 0.03 Formulation Example 9 0.19 0.20 0.14 0.03 0.03 Formulation Example 10 0.18 0.19 0.12 0.03 0.02 Formulation Example 11 0.21 0.21 0.16 0.02 0.01 Formulation Example 12 0.15 0.17 0.14 0.01 0.02 Formulation Example 13 0.19 0.18 0.13 0.03 0.03 Formulation Example 14 0.23 0.21 0.17 0.02 0.02 Formulation Example 15 0.21 0.22 0.15 0.01 0.02 Comparative Formulation Example 1 0.27 0.26 0.21 0.03 0.03

R1: Difference between the maximum value and the minimum value of the wrinkle contour line

R2: The wrinkle contour line is arbitrarily divided into 5 squares, and the average of R1 values

R3: the highest value of R1 divided by 5

R4: Average value obtained by subtracting the value of each apex and valley from the baseline of the wrinkle contour line

R5: Difference between the baseline of the wrinkle contour line minus the contour of each wrinkle

As shown in Table 7, it was found that the compositions for external application of Formulation Examples 1 to 15 were excellent in the effect of improving skin wrinkles.

[Test Example 5]

In order to evaluate the skin blood circulation promoting effect of the cosmetic composition according to the present invention, the degree of blood circulation in the skin was measured using LDPI (Laser Doppler Perfusion Imager). LDPI is a widely used and widely used device for measuring blood circulation in skin. It is a highly sensitive device that can measure not only blood velocity and quantity in the capillaries of the skin, but also flow in the small artery and the parenchyma.

The face was soaked in a constant temperature and humidity chamber, and then adapted for 30 minutes. Initial values were measured using LDPI. First, the initial blood flow in the lower part of the forehead of 30 women with cold hands and feet was measured by LDPI. Table 8 below shows the results of comparing blood flow measured with the initial measurement values (skin blood flow change) measured after using Formulation Examples 1 to 15 and Comparative Formulation Example 1 for a week.

LDPI results before and after using cosmetics - skin blood flow Test substance Percent change of skin blood flow after 1 week use (%) Formulation Example 1 15 Formulation Example 2 20 Formulation Example 3 24 Formulation Example 4 35 Formulation Example 5 26 Formulation Example 6 23 Formulation Example 7 35 Formulation Example 8 26 Formulation Example 9 27 Formulation Example 10 35 Formulation Example 11 15 Formulation Example 12 29 Formulation Example 13 30 Formulation Example 14 26 Formulation Example 15 34 Comparative Formulation Example 1 5

In the results of Table 8, the cosmetic composition of the present invention significantly increased skin blood flow rate compared with Comparative Formulation Example 1 which did not contain a propanoid derivative substituted with a phenyl group, and the hemoglobin was improved by promoting blood circulation . This suggests that a cosmetic composition containing a propanoid derivative substituted with a phenyl group according to the present invention can ultimately contribute to effectively transmit nutrients of the skin and inhibit and delay skin aging.

[Test Example 6] Skin tone improvement effect

To evaluate the skin tone improvement effects of Formulation Examples 1 to 15 and Comparative Formulation Example 1, 30 subjects were used (once a day / one day for a total of one week), and then facial stage DM-3 (Moritex, Japan ) Device to evaluate the degree of skin tone improvement. The improvement rate of the skin tone was determined as the brightness and color value of the skin and the change of the brightness and color of the skin. The results are shown in Table 9 below.

Test substance Skin tone improvement rate (%) Brightness (mean ± standard deviation) Color (mean ± standard deviation) Formulation Example 1 16 ± 3.24 14 ± 2.34 Formulation Example 2 20 ± 2.04 25 ± 2.58 Formulation Example 3 23 ± 2.56 29 ± 2.14 Formulation Example 4 30 ± 2.42 30 ± 2.36 Formulation Example 5 25 ± 2.25 20 ± 2.14 Formulation Example 6 23 ± 2.35 23 ± 2.15 Formulation Example 7 30 ± 3.05 30 ± 2.24 Formulation Example 8 28 ± 2.05 25 ± 2.35 Formulation Example 9 27 ± 2.46 29 ± 2.03 Formulation Example 10 33 ± 2.58 30 ± 2.08 Formulation Example 11 19 ± 2.64 19 ± 2.14 Formulation Example 12 29 ± 3.04 25 ± 3.12 Formulation Example 13 35 ± 3.12 30 ± 2.36 Formulation Example 14 25 ± 2.05 25 ± 3.06 Formulation Example 15 30 ± 2.14 32 ± 2.54 Comparative Formulation Example 1 5 ± 2.34 5 ± 2.05

In the results of Table 9, Comparative Formulation Example 1, which does not contain a propanoid derivative substituted with a phenyl group according to the present invention, shows no significant skin tone-improving effect, whereas a propanoid derivative substituted with a phenyl group as an active ingredient Of Formulation Examples 1 to 15 showed much improved skin tone after use than before use.

[Test Example 7] Pore reduction effect

<Collagen biosynthesis promotes pore reduction effect>

The propanoid derivative substituted with the phenyl group according to the present invention was measured for its promoting effect on promoting collagen biosynthesis in comparison with TGF-β. First, fibroblasts were seeded at 10 ⁵ per well in 24 wells and cultured until they grew to about 90%. This process was a serum-free DMEM culture medium by serum-free for the propane cannabinoid derivatives and TGF-β substituted prenyl of the present invention dissolved in medium, respectively 10ng / ml for 24 hours, CO ₂ And cultured in an incubator for 24 hours. The supernatant was removed and the procolagen (I) ELISA kit (procollagen type (I)) was used to determine whether procollagen was increased or decreased. The results are shown in Table 10, and the total performance of the collagen was compared with that of the untreated group as 100.

Test substance Collagen Total Performance (%) Untreated group 100 TGF-beta 183.5 Brosonin A 175.5 Brosonin B 178.6 Brosonin C 183.2 Brosonin D 179.5 Brosonin E 186.3 Brosonin F 190.1 Casinol C 189.5 Casinol D 192.3 Casinol F 185.3 Casinol G 195.4 Casinol J 194.3 Casinol K 178.5 Casinol L 182.3 Casinol M 191.1 Casinol N 186.3

From the results shown in Table 10, it was confirmed that the propanoid derivative substituted with a phenyl group according to the present invention exhibited excellent collagen synthesis performance equivalent to or higher than that of the positive control group TGF-β. Thus, it has been confirmed that the propanoid derivative substituted with the phenyl group according to the present invention can increase the amount of collagen produced around the pore, thereby widening the pores.

<Pore reduction effect>

To evaluate the pore reduction effect of Formulation Examples 1 to 15 and Comparative Formulation Example 1, the following evaluation was made. 160 subjects were selected and divided into 16 groups of 10 subjects each having a large pore size. The nutritional creams of Formulation Examples 1 to 15 and Comparative Formulation Example 1 were applied to the face for each group for 4 weeks on each face. The evaluation of the effectiveness of the pore reduction was made by a visual evaluation of experts by taking pictures before and after the experiment. The results are shown in Table 11 below (rating scale: 0 - no reduction at all; 5 - very shrunk).

Test substance Rating Rating Formulation Example 1 One Formulation Example 2 One Formulation Example 3 2 Formulation Example 4 One Formulation Example 5 2 Formulation Example 6 3 Formulation Example 7 3 Formulation Example 8 3 Formulation Example 9 2 Formulation Example 10 3 Formulation Example 11 4 Formulation Example 12 4 Formulation Example 13 3 Formulation Example 14 4 Formulation Example 15 3 Comparative Formulation Example 1 0

From the results of Table 11, Comparative Formulation Example 1 shows no effect of reducing the pores, but in the case of Formulation Examples 1 to 15, the effect of reducing the pores to a degree that can be visually confirmed is exhibited. Thus, the propanoid derivative It was found that the effect of reducing the size of pores was excellent.

Test Example 8 Effect of suppressing sebum secretion

&Lt; 5a-reductase inhibitory effect &lt; RTI ID = 0.0 &gt;

In order to confirm 5α-reductase inhibitory effect, the ratio of [ ¹⁴ C] testosterone to [ ¹⁴ C] dihydrotestosterone (DHT) in HEK293-5αR2 cells was measured. HEK293 cells were transfected with p3 x FLAG-CMV-5αR2, and cultured in 2.5 × 10 ⁵ cells / well in a 24-well plate (Park et al., 2003, JDS Vol. 31, pp. 191-98). The next day, the medium was changed to a new medium supplemented with an enzyme substrate and an inhibitor. 0.05 [mu] Ci [ ¹⁴ C] testosterone (Amersham Pharmacia biotech, UK) was used as the substrate of the medium.

To confirm the degree of inhibition of 5? -Reductase activity, the propanoid derivatives substituted with the phenyl group shown in the following Table 12 were added and cultured in a 5% CO ₂ incubator at 37 ° C for 2 hours. At this time, no propranoid derivative substituted with a prenyl group was used as a negative control, and finasteride was used as a positive control. Thereafter, the culture medium was collected, and the steroid was extracted with 800 쨉 l of ethyl acetate. The upper organic solvent layer was separated, dried, and the remaining residue was again dissolved in 50 쨉 l ethyl acetate to obtain a silica plastic sheet kiesel gel 60 F254 ) Using ethyl acetate-hexane (1: 1) as the solvent.

After drying the plastic sample in air, the bath system was used to measure the amount of isotope. The dried plastic sheet and x-ray film were put together in a bath cassette, and after 1 week, the testosterone remaining in the film and isotopes of dihydrotestosterone The conversion and inhibition rates were calculated according to the following equations (3) and (4), respectively, and the results are shown in Table 12 below.

Test substance Conversion Rate (%) Inhibition rate (%) Negative control group 48.0 - Positive control group 27.6 42.5 Brosonin A 25.4 47.1 Brosonin B 20.1 58.1 Brosonin C 24.5 48.9 Brosonin D 35.4 26.2 Brosonin E 24.7 48.5 Brosonin F 23.8 50.4 Casinol C 35.5 26.1 Casinol D 26.4 45.0 Casinol F 24.3 49.3 Casinol G 35.1 26.8 Casinol J 20.3 57.7 Casinol K 29.5 38.5 Casinol L 30.8 35.8 Casinol M 26.4 45 Casinol N 24.4 49.1

In the results shown in Table 12, testosterone is converted into dihydrotestosterone, which binds to the receptor protein in the cytoplasm to enter the nucleus, activates the sebaceous gland, accelerates differentiation, and induces 5α-reductase Was effectively inhibited by the propanoid derivative substituted with the phenyl group according to the present invention, thereby blocking the conversion of testosterone to dihydrotestosterone. Thus, it was confirmed that the propanoid derivative substituted with the phenyl group according to the present invention effectively inhibited the activity of 5? -Redoxytase, thereby suppressing the hypersecretion of sebum.

&Lt; Effect of suppressing sebum secretion &

In order to examine the inhibitory effects of sebum secretion of Formulation Examples 1 to 15 and Comparative Formulation Example 1, the following evaluation was made. Thirty male and female subjects who felt that sebum secretion was high were selected and the nutritional creams of Formulation Examples 1 to 15 and Comparative Formulation Example 1 were made every day for 4 weeks at designated areas. The results of the evaluation of the effect of reducing sebum were measured by using a sebum analyzer (Sebumeter SM810, C + K Electronic Co., Germany) after 2 weeks and 4 weeks, Respectively.

Test substance Sebum reduction rate (%) After 2 weeks After 4 weeks Formulation Example 1 19.4 25.4 Formulation Example 2 15.3 20.1 Formulation Example 3 13.5 24.5 Formulation Example 4 18.4 35.4 Formulation Example 5 17.7 24.7 Formulation Example 6 13.7 23.8 Formulation Example 7 15.6 35.7 Formulation Example 8 16.7 26.3 Formulation Example 9 14.4 24.8 Formulation Example 10 15.1 35.6 Formulation Example 11 16.2 20.6 Formulation Example 12 19.2 29.6 Formulation Example 13 15.9 30.3 Formulation Example 14 16.5 26.2 Formulation Example 15 14.8 24.5 Comparative Formulation Example 1 5 5

The results of Table 13 show that Formulation Examples 1 to 15 containing the propanoid-substituted derivative of the present invention as an active ingredient can effectively inhibit excessive sebum secreted from Comparative Formulation Example 1, .

[Test Example 9] Measuring effect of increasing skin moisturizing power

Formulations 1 to 15 and Comparative Formulation Example 1 were used to measure the effect of the propanoid derivatives substituted with the phenyl group on the increase in skin moisturizing ability and evaluated as follows.

160 men and women in the 40s and 50s classified as dry skin were divided into 16 groups of 10 persons for each of Formulation Examples 1 to 15 and Comparative Formulation Example 1 to apply the nutritional cream twice daily for 4 weeks to the face. (24 ° C, relative humidity 40%) after 1 week, 2 weeks, and 4 weeks after application, and after 2 weeks (total 6 weeks) (Corneometer CM825, C + K Electronic Co., Germany). The results are shown in Table 14 below. The results in Table 14 are the percentages of the increase in the measured value after treatment for a certain period based on the skin moisture meter measured immediately before the start of the test.

Test group Moisture growth rate (%) 1 week Two weeks 4 weeks 6 weeks Formulation Example 1 34.1 36.4 36.3 32.1 Formulation Example 2 38.1 37.1 37.2 36.1 Formulation Example 3 38.6 41.6 40. 32.6 Formulation Example 4 32.2 34.2 34.6 29.5 Formulation Example 5 34.6 34.9 34.8 28.6 Formulation Example 6 33.5 35.2 35.4 31.6 Formulation Example 7 36.2 38.2 38.7 34.3 Formulation Example 8 38.8 39.8 39.3 35.9 Formulation Example 9 37.6 37.8 37.2 31.5 Formulation Example 10 35.3 34.3 34.4 29.8 Formulation Example 11 36.6 35.5 35.8 37.1 Formulation Example 12 35.6 36.8 36.3 32.6 Formulation Example 13 32.4 33.9 33.6 32.5 Formulation Example 14 31.1 34.2 34.2 30.1 Formulation Example 15 33.5 36.4 36.7 28.7 Comparative Formulation Example 1 30 32 32 15

The result of Table 14 shows that when Comparative Formulation Example 1 is applied, the moisture increase rate is about 30% until 4 weeks of application, but after the application is stopped, the amount of skin moisture decreases, In the case of Formulation Examples 1 to 15 containing the propanoid derivative of the present invention was applied, it was confirmed that the skin moisture increase rate was mostly 30% or more even after the application was stopped. Thus, it can be seen that the composition of the present invention containing a propanoid derivative substituted with a phenyl group has excellent skin moisturizing effect.

[Test Example 10] Measurement of promoting effect of keratinocyte differentiation

In order to examine the effect of the propanoid derivative substituted with the phenyl group on keratinocyte differentiation, the amount of CE (cornified envelope) produced upon differentiation of keratinocytes was measured by absorbance as described below.

First, keratinocytes of a primary culture separated from the epidermis of a newborn baby were put in a culture flask and adhered to the bottom. After treating the test material of Table 15 with the concentration of 5 ppm in the culture medium, The cells were cultured for 5 days until they grew to about 80%. At this time, low calcium (0.03 mM) and high calcium (1.2 mM) treatment groups were negative control and positive control, respectively. Then, the cultured cells were harvested, washed with PBS (Phosphate buffered saline), and then suspended in 10 mM Tris-HCl buffer (Tris-HCl, pH 7.4) containing 2% SDS (sodium dodecyl sulfate) and 20 mM DTT (Dithiothreitol) pH 7.4) was added, sonication, boiling, and centrifugation. The precipitate was suspended again in 1 ml of PBS and the absorbance at 340 nm was measured. Separately, a part of the solution after the sonication was taken to measure the protein content and used as a standard in evaluating the degree of cell differentiation. The results are shown in Table 15 below.

Test substance The ability to differentiate in keratinocytes (%) Low calcium (0.03 mM) solution
(Negative control) 100 High calcium (1.2 mM) solution
(Positive control group) 210 Brosonin A 190 Brosonin B 198 Brosonin C 195 Brosonin D 190 Brosonin E 205 Brosonin F 230 Casinol C 210 Casinol D 225 Casinol F 196 Casinol G 216 Casinol J 228 Casinol K 203 Casinol L 210 Casinol M 205 Casinol N 200

As shown in Table 15, when the propanoid derivative substituted with a phenyl group was treated, it was confirmed that the effect of accelerating the differentiation of keratinocytes was excellent.

[Test Example 11] Measurement of recovery effect on skin barrier function

In order to measure the effect of the propanoid derivative substituted with the phenyl group on the recovery of damaged skin barrier function due to skin damage, the following experiment was conducted. Ten adult male and female adult rats were treated with the tape stripping method to damage the skin barrier and apply the 16 groups of Formulation Examples 16 to 30 and Comparative Formulation Example 2 prepared in the compositions shown in Tables 16 to 17, (TWEL) was measured and compared with the Vapometer (Delfin, Finland) once a day for 7 days. Here, Comparative Formulation Example 2 is a vehicle as a negative control. The experimental results are shown in Table 18 below. The results in Table 18 were compared before treatment before barrier damage and after treatment before barrier damage on the basis of 100%.

Compounding ingredient Formulation Example 16 Formulation Example 17 Formulation Example 18 Formulation Example 19 Formulation Example 20 Formulation Example 21 Formulation Example 22 Formulation Example 23 Purified water 69 69 69 69 69 69 69 69 Propylene glycol 30 30 30 30 30 30 30 30 Brosonin A One - - - - - - - Brosonin B - One - - - - - - Brosonin C - - One - - - - - Brosonin D - - - One - - - - Brosonin E - - - - One - - - Brosonin F - - - - - One - - Casinol C - - - - - - One - Casinol D - - - - - - - One

Compounding ingredient Formulation Example 24 Formulation Example 25 Formulation Example 26 Formulation Example 27 Formulation Example 28 Formulation Example 29 Formulation Example 30 Comparative Formulation Example 2 Purified water 69 69 69 69 69 69 69 70 Propylene glycol 30 30 30 30 30 30 30 30 Casinol F One - - - - - - - Casinol G - One - - - - - - Casinol J - - One - - - - - Casinol K - - - One - - - - Casinol L - - - - One - - - Casinol M - - - - - One - - Casinol N - - - - - - One -

Test group TWEL Change (%) Before processing 1 day 2 days 3 days 4 days 5 days 6 days Formulation Example 16 100 112.2 87.3 62.4 45.5 36.3 25.4 Formulation Example 17 100 114.3 86.3 67.9 47.3 37.2 20.1 Formulation Example 18 100 118.3 89.6 64.5 40.8 40.8 24.5 Formulation Example 19 100 117.8 84.3 67.2 44.6 30.7 35.4 Formulation Example 20 100 109.3 87.3 63.7 44.8 34.8 24.7 Formulation Example 21 100 108.3 88.3 64.8 45.4 36.5 23.8 Formulation Example 22 100 115.3 86.1 58.9 48.7 38.7 35.7 Formulation Example 23 100 114.3 89.6 61.7 49.3 39.3 26.3 Formulation Example 24 100 108.5 84.5 60.5 47.2 37.2 24.8 Formulation Example 25 100 108.7 84.6 59.8 44.4 34.4 35.6 Formulation Example 26 100 106.3 87.2 60.7 45.8 35.8 20.6 Formulation Example 27 100 115.3 89.5 64.3 46.3 36.3 29.6 Formulation Example 28 100 114.6 88.4 67.8 43.6 33.6 30.3 Formulation Example 29 100 108.5 84.2 64.8 44.2 34.2 26.2 Formulation Example 30 100 107.4 84.5 63.4 44.5 36.7 24.5 Comparative Formulation Example 2 100 121.4 112.7 98.3 70.5 62.3 43.5

As can be seen from Table 18, when the propanoid derivative substituted with the phenyl group is treated, the amount of transdermal water loss is returned to normal and the barrier damage is recovered at a high speed.

[Formulation Examples 31 to 45 and Comparative Formulation Examples 3 to 4]

Formulations 31 to 45 and Comparative Formulations 3 to 4 were prepared according to the ingredients and the contents (% by weight) shown in Tables 19 and 20 below. Specifically, in Formulation Examples 31 to 45, a propanoid derivative substituted with a prenyl group was compounded. Comparative Formulation Example 3 contained no effective ingredient for acne skin improvement. In Comparative Formulation Example 4, As a standard, it is a standard substance that contains erythromycin, which is widely used as an acne remedy.

The manufacturing methods of Formulation Examples 31 to 45 and Comparative Formulation Examples 3 to 4 are as follows. The ingredients of the phase A of the following Tables 19 and 20 were completely dissolved and the components of the phase B were completely dissolved in a separate melting tank, and the phases of the phases B were added to the phase A to be mixed and solubilized. The components of the C phase were added thereto in accordance with the mixing ratios shown in Tables 19 and 20, and the components were mixed and homogenized and filtered to prepare the compositions.

division Formulation Example 31 Formulation Example 32 Formulation Example 33 Formulation Example 34 Formulation Example 35 Formulation Example 36 Formulation Example 37 Formulation Example 38 Formulation Example 39 A Deionized Water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 EDTA-2Na 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 glycerin 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 B ethanol 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 PEG-60 hydrogenated castor oil 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Perfume 0.04 0.04 0.04 0.04 0.04 0.04 0.04 0.04 0.04 C Brosonin A 5.0 - - - - - - - - Brosonin B - 5.0 - - - - - - - Brosonin C - - 5.0 - - - - - - Brosonin D - - - 5.0 - - - - - Brosonin E - - - - 5.0 - - - - Brosonin F - - - - - 5.0 - - - Casinol C - - - - - - 5.0 - - Casinol D - - - - - - - 5.0 - Casinol F - - - - - - - - 5.0

division Formulation Example 40 Formulation Example 41 Formulation Example 42 Formulation Example 43 Formulation Example 44 Formulation Example 45 Comparative Formulation Example 3 Comparative Formulation Example 4 A Deionized Water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 EDTA-2Na 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 glycerin 5.0 5.0 5.0 5.0 5.0 5.0 5.0 5.0 B ethanol 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 PEG-60 hydrogenated castor oil 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Perfume 0.04 0.04 0.04 0.04 0.04 0.04 0.04 0.04 C Casinol G 5.0 - - - - - - - Casinol J - 5.0 - - - - - - Casinol K - - 5.0 - - - - - Casinol L - - - 5.0 - - - - Casinol M - - - - 5.0 - - - Casinol N - - - - - 5.0 - - Erythromycin - - - - - - - 5.0

[Test Example 12] Test for antimicrobial activity against acne bacteria

Each of the cosmetic compositions prepared in the formulations of Formulation Examples 31 to 45 and Comparative Formulations 3 to 4 was tested for antibacterial activity against Propionibacterium acnes <ATCC 6919: medium-BHI broth> .

The test method for the antimicrobial activity against acne bacteria was as follows.

(1) Preparation of test strain

Propionibacterium acnes were cultured in an anaerobic culture inoculated with BHI broth.

(2) Dilution solution preparation

0.15 ml of the above test solution was added to 15 ml of BHI broth (pH 6.8) or LB broth (pH 4.5), and the mixture was used as a diluting solution.

(3) Preparation of sample

The raw cosmetic compositions prepared from Formulation Examples 31 to 45 and Comparative Formulation Examples 3 to 4 were directly used as a sample.

(4) Antimicrobial activity test

1) In a 96-well 96-well plate, place the sample in line 1 and add 200 μl of diluted solution.

2) Thoroughly mix the mixture of line 1, and then take 100 μl of the mixture, place it in the second row, mix well, and then repeat the double dilution by adding 100 μl to the third row.

3) After culturing the cells at 32 ° C for 24 hours and 48 hours, determine whether the bacteria are proliferating to the extent of suspension, and determine the minimum concentration without bacterial growth as the MIC (Minimum Inhibitory Concentration) value. If the mixture is opaque and it is difficult to judge the growth of the microorganism, check with a microscope.

The results of the antimicrobial activity test against acne bacteria are shown in Table 21 below. The MIC was expressed in terms of the concentration of the active ingredient contained in the formulation.

Item pH Propionibacterium acnes Formulation Example 31 5.7 > 40 ppm Formulation Example 32 5.7 > 50 ppm Formulation Example 33 5.7 > 50 ppm Formulation Example 34 5.7 > 50 ppm Formulation Example 35 5.7 > 50 ppm Formulation Example 36 5.7 > 40 ppm Formulation Example 37 5.7 > 40 ppm Formulation Example 38 5.7 > 40 ppm Formulation Example 39 5.7 > 30 ppm Formulation Example 40 5.7 > 40 ppm Formulation Example 41 5.7 > 30 ppm Formulation Example 42 5.7 > 30 ppm Formulation Example 43 5.7 > 40 ppm Formulation Example 44 5.7 > 50 ppm Formulation Example 45 5.7 > 40 ppm Comparative Formulation Example 3 5.7 Maximum concentration (no antimicrobial activity) Comparative Formulation Example 4 5.7 > 100 ppm

The lower concentration of ppm in MIC is an effective substance against the antimicrobial activity against acne bacteria. In Formulations 31 to 45, the ppm concentration is significantly smaller than that of Comparative Formulation Example 4 using erythromycin, which is a known acne treatment agent It can be confirmed that the composition containing the propanoid derivative substituted with a prenyl group has far superior antibacterial activity to the test bacteria.

[Test Example 13] Lipogenesis inhibition test

3T3-L1 cells, a fibroblast cell line of mice, were cultured in DMEM supplemented with 10% fetal bovine serum (FBS) (Dulbecco's modified eagles medium, GIBCO BRL, Life Technologies) Lt; ⁵ &gt; cells / well in a well culture plate. After 2 days, the cells were replaced with fresh DMEM (containing 10% FBS) medium and cultured for 2 days. Then, the cultured cells were further subjected to differentiation with DMEM (containing 10% FBS) containing 1 μg / ml insulin, 0.5 mM IBMX and 0.25 μM dexamethasone, and propranoid substituted with a phenyl group Derivative and caffeine were treated with 50 μM, followed by treatment with DMEM containing insulin again for 2 days, followed by culture for 5 days. After 5 days, the cells were replaced with normal medium (DMEM, containing 10% FBS) and cultured while observing until the cells morphologically changed into adipocytes.

In order to evaluate the inhibitory effect of propranoid-substituted propanoid derivatives on the fat accumulation in adipocytes, SIII staining (S4136, sigma-aldrich) was carried out using 3T3-L1 adipocytes differentiated as above. The adipocytes were fixed with 4% paraformaldehyde (pH 7.2) in phosphate buffer at room temperature, washed with PBS (phsphate buffered saline), stained with SIII and then photographed and compared visually. The control group was fed with the test substance or the test substance without the reference substance, and 50 μM of caffeine was treated with another comparative group. The level of inhibition of fat accumulation was graded by dividing the degree of staining by +++, ++, +, -. The results are shown in Table 22.

sample % Inhibition Control group +++ Comparative group + Brosonin A + Brosonin B + Brosonin C + Brosonin D ++ Brosonin E + Brosonin F ++ Casinol C + Casinol D + Casinol F + Casinol G + Casinol J ++ Casinol K ++ Casinol L + Casinol M + Casinol N +

As shown in Table 22, it can be seen that the propanoid derivative substituted with the phenyl group used in the present invention has lipid synthesis inhibitory effect equal to or better than that of the known lipid synthesis inhibitor caffeine. Therefore, lipid synthesis is inhibited, and sebum is reduced, so that occurrence of acne can be suppressed.

[Test Example 14] Test for improvement of acne and reduction of sebum secretion and stimulation

170 persons who had acne were divided into 17 groups by 10 persons, and the subjects corresponding to each group were allowed to use the cosmetic composition prepared from Formulation Examples 31 to 45 and Comparative Formulation Examples 3 to 4 for one month. Acne improvement scale is from 1 point to 5 points, 1 point is 'No', 3 points are 'Normal' and 5 points are 'Very agree'. The experimental results are shown in Table 23 below with an average score of 10 persons.

The acne extermination period was based on the number of days of disappearance readings, and the results were based on the results after 1 month with or without recurrence of acne. The reduction of sebaceous secretion was from 1 point to 5 points, 1 point was 'No', 3 points were 'Normal' and 5 points were 'Very agree'. The experimental results are shown in Table 23 below with an average score of 10 persons. The presence or absence of skin irritation was evaluated as (number of stimuli) / (total number of test subjects).

Inflammatory acne improvement Acne-bloating period Recurrence of acne Decrease sebaceous glands Presence or absence of stimulation Formulation Example 31 4.3 1 day radish 4.1 1/10 Formulation Example 32 4.1 2 days radish 4.2 0/10 Formulation Example 33 4.2 2 days radish 4.3 0/10 Formulation Example 34 4.2 1 day radish 4.0 1/10 Formulation Example 35 4.1 2 days radish 4.2 1/10 Formulation Example 36 4.3 2 days radish 3.9 0/10 Formulation Example 37 4.1 1 day radish 4.3 0/10 Formulation Example 38 4.2 2 days radish 4.2 0/10 Formulation Example 39 4.3 2 days radish 4.1 1/10 Formulation Example 40 4.0 1 day radish 3.8 0/10 Formulation Example 41 4.2 2 days radish 4.1 0/10 Formulation Example 42 3.9 2 days radish 4.1 0/10 Formulation Example 43 4.3 1 day radish 4.3 0/10 Formulation Example 44 4.1 2 days radish 4.1 0/10 Formulation Example 45 4.1 1 day radish 4.3 0/10 Comparative Formulation Example 3 2.1 13th U 2.0 0/10 Comparative Formulation Example 4 4.2 2 days radish 4.1 9/10

As shown in Table 23, Formulation Examples 31 to 45 showed no recurrence of acne compared to Comparative Formulation Example 3, and overall, it was found that there was an excellent effect on acne improvement. On the other hand, Comparative Formulation Example 4 containing the antibacterial activity reference material shows the effect of improving acne, but there is a fear of skin irritation for long-term use due to strong stimulus in use, but the composition according to the present invention is not stimulated appear.

[Test Example 15] Inflammation improving effect

The antiinflammatory effect was evaluated by the inhibitory effect of prostaglandin production. The effects of macrophages on the effect of propanoid derivatives substituted with prenyl groups were measured. First, aspirin was added to the macrophage cells collected from the abdominal cavity of mice to a final concentration of 500 M to irreversibly inhibit the cyclooxygenase (COX) activity remaining in the cells. Then, the suspension was added to each well of a 96-well cell culture tube in an amount of 100 μl, followed by culturing in an incubator of 5% CO ₂ and 37 ° C for 2 hours to adhere macrophages to the surface of the container. Then, the adhered macrophages were washed three times with PBS and used for the inflammation improving effect test. RPMI medium containing 1% (w / v) LPS was added to the cultured macrophage 5x10 ⁴ cells / ml and cultured for 12 hours. Then, production of prostaglandin was induced and 100 μl of a propanoid derivative substituted with a phenyl group And the liberated prostaglandins were quantitated using enzyme immunoassay (ELISA).

At this time, the inhibitory activity of the propanoid derivatives substituted with the phenyl group was found to be 100% for the prostaglandins produced in the LPS-treated group and the untreated group, and the LPS- The inhibitory effect of prostaglandin production is shown in Table 24 below.

Blank 100% Control group (aspirin treatment group) 25.0% Brosonin A 19.4% Brosonin B 25.3% Brosonin C 23.5% Brosonin D 18.4% Brosonin E 27.7% Brosonin F 13.7% Casinol C 25.6% Casinol D 26.7% Casinol F 24.4% Casinol G 25.1% Casinol J 26.2% Casinol K 19.2% Casinol L 25.9% Casinol M 26.5% Casinol N 24.8%

As shown in Table 24, the inhibition effect of prostaglandin production is remarkably high even when a propanoid derivative substituted with a phenyl group is treated as in the control group treated with aspirin.

Thus, it can be seen that the propanoid derivative substituted with the phenyl group of the present invention can provide excellent inflammation improving effect.

Also, it can be seen that the propanoid derivative substituted with a phenyl group can inhibit the expression of prostaglandin, which is a skin inflammation factor, to prevent and improve skin troubles.

[Test Example 16] Inhibitory effect on the production of reactive oxygen species (ROS)

Keratinocytes isolated from human epidermal tissue were added to each well of a 24-well plate at 5 × 10 ⁴ for 24 hours. After 16 hours, the propanoid derivatives substituted with the pronomyl group of the present invention shown in Table 25 were treated with 1%. After 2 hours, the culture solution was removed, and 100 쨉 l of phosphate buffered saline (PBS) was added to each well. This keratinocyte was irradiated with ultraviolet rays at 30 mJ / cm 2 using an ultraviolet B (UVB) lamp (Model: F15T8, UV B 15 W, Sankyo Dennki, Japan), and then PBS was removed. &Lt; / RTI &gt; The propanoid derivative substituted with the phenyl group was then treated again and the amount of active oxygen species increased by ultraviolet stimulation was determined at predetermined time intervals. The amount of ROS was determined by referring to Tan's method of measuring the fluorescence of DCF-DA (dichlorofluorescin diacetate) oxidized by ROS (Tan et al., 1998, J. Cell Biol. Vol. 141, pp1423-1432) The ratios of the control group to ROS are shown in Table 25 below.

Test substance UVB 30 mJ / cm ² Time elapsed after investigation 0hr 2 hr 3hr Vehicle 100 244 287 UVB + vehicle 100 325 381 UVB + Brosonin A 100 254 278 UVB + Brosonin B 100 256 268 UVB + Brosonin C 100 264 286 UVB + Brosonin D 100 245 263 UVB + Brosonin E 100 256 276 UVB + Brosonin F 100 248 263 UVB + casinol C 100 239 252 UVB + casinol D 100 245 265 UVB + casinol F 100 248 269 UVB + casinol G 100 278 296 UVB + casinol J 100 268 289 UVB + casinol K 100 246 267 UVB + casinol L 100 271 298 UVB + casinol M 100 268 289 UVB + casinol N 100 265 287

In the results shown in Table 25 above, the propanoid substituted derivatives of the present invention effectively inhibit the production of ROS, which is known to cause skin cell damage by ultraviolet rays, and that the amount of ROS after ultraviolet stimulation does not irradiate ultraviolet And the antioxidant activity was excellent enough to inhibit the production of ROS. Accordingly, it has been confirmed that the propanoid derivative substituted with the phenyl group according to the present invention can prevent the wrinkling of the pores by inhibiting oxidation and preventing aging, and can prevent skin irritation, thereby improving skin troubles.

[Test Example 17] Whitening effect

<Effect of tyrosinase inhibition>

The tyrosinase enzyme was extracted from Mushroom and was obtained from Sigma. First, the substrate, tyrosine, is dissolved in distilled water to make a 0.3 mg / ml solution. The solution is put into a test tube in an amount of 1.0 ml. Then, 1.0 ml of potassium phosphate buffer solution (0.1 mol concentration, pH 6.8) and 0.7 ml of distilled water .

The propanoid derivative substituted with the phenyl group of the present invention was mixed with an ethanol solution at an appropriate concentration, and 0.2 ml of each sample liquid was added to the reaction solution, followed by reaction at 37 ° C for 10 minutes. At this time, the control group was prepared by adding 0.2 ml of a solvent instead of each sample solution, and ascorbic acid was used as a positive control group. 0.1 ml of tyrosinase solution of 2500 units / ml was added to the reaction solution, followed by reaction at 37 ° C for 10 minutes. The reaction tube was immersed in ice water to quench the reaction, and the absorbance at 475 nm was measured with a photoelectron spectrometer. The results are shown in Table 26 below. Each tyrosinase inhibitory effect was calculated by the following equation (5).

Test substance Inhibition rate of tyrosinase (%) Control group (no addition) 0 Ascorbic acid 52 Brosonin A 87 Brosonin B 86 Brosonin C 89 Brosonin D 84 Brosonin E 87 Brosonin F 88 Casinol C 86 Casinol D 89 Casinol F 84 Casinol G 84 Casinol J 87 Casinol K 89 Casinol L 88 Casinol M 84 Casinol N 84

The results of Table 26 show that the cosmetic composition of Formulation Examples 1 to 15 containing a propanoid derivative substituted with a phenyl group according to the present invention has a much higher inhibition rate of tyrosinase than ascorbic acid which is a known tyrosinase inhibitor, Could know.

&Lt; B16 / F10 Melanoma Inhibitory Effect by Melanoma Cells >

A sample containing Formulation Examples 1 to 15, Comparative Formulation Example 1 and kojic acid at a concentration of 0.001% by weight was added to the culture medium of B16 / F10 melanoma cells (Korean Cell Line Bank) at a constant concentration and the cells were cultured for 3 days After the culture was removed, the cells were washed with PBS, and the cells were dissolved with 1N NaOH, and absorbance was measured at 405 nm. Cells to which the test substance was not added were used as a control group, and the melanin formation inhibition degree of each test substance was measured by comparing with the melanin content in the control group. The inhibition rate of melanin production was calculated according to Equation (6) and the results are shown in Table 27.

Test substance Melanin inhibition rate (%) Control group (no addition) 0 Kojic acid 53 Brosonin A 77 Brosonin B 88 Brosonin C 79 Brosonin D 84 Brosonin E 77 Brosonin F 83 Casinol C 87 Casinol D 82 Casinol F 87 Casinol G 84 Casinol J 83 Casinol K 84 Casinol L 88 Casinol M 82 Casinol N 79

The results of Table 27 show that the cosmetic compositions of Formulas 1 to 15 containing a propanoid derivative substituted with a phenyl group according to the present invention have a much higher inhibitory rate of melanin formation than kojic acid which is a known melanin formation inhibitor, I was able to see that it was excellent.

[Formulation Examples 46 to 60, Comparative Formulation Examples 5 to 6]

Formulation Examples 46 to 60 and Comparative Formulation Examples 5 to 6 composed of the following Tables 28 and 29 were prepared (unit: wt%). Comparative Formulation Example 6 is a cosmetic composition containing OMC (octyl 4-methoxycinnamate), which is a commonly used UV absorbent.

ingredient Formulation Example 46 Formulation Example 47 Formulation Example 48 Formulation Example 49 Formulation Example 50 Formulation Example 51 Formulation Example 52 Formulation Example 53 Formulation Example 54 Brosonin A 4 - - - - - - - - Brosonin B - 4 - - - - - - - Brosonin C - - 4 - - - - - - Brosonin D - - - 4 - - - - - Brosonin E - - - - 4 - - - - Brosonin F - - - - - 4 - - - Casinol C - - - - - - 4 - - Casinol D - - - - - - - 4 - Casinol F - - - - - - - - 4 OMC - - - - - - - - - glycerin 4 4 4 4 4 4 4 4 4 Butylene glycol 4 4 4 4 4 4 4 4 4 Hyaluronic acid 5 5 5 5 5 5 5 5 5 Beta Glucan 7 7 7 7 7 7 7 7 7 Carbomer 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Caprylic / capric triglyceride 8 8 8 8 8 8 8 8 8 Squalene 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Stearyl glucoside 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Sorbitan stearate 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Stearyl alcohol 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Purified water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100

ingredient Formulation Example 55 Formulation Example 56 Formulation Example 57 Formulation Example 58 Formulation Example 59 Formulation Example 60 Comparative Formulation Example 5 Comparative Formulation Example 6 Casinol G 4 - - - - - - - Casinol J - 4 - - - - - - Casinol K - - 4 - - - - - Casinol L - - - 4 - - - - Casinol M - - - - 4 - - - Casinol N - - - - - 4 - - OMC - - - - - - - 4 glycerin 4 4 4 4 4 4 4 4 Butylene glycol 4 4 4 4 4 4 4 4 Hyaluronic acid 5 5 5 5 5 5 5 5 Beta Glucan 7 7 7 7 7 7 7 7 Carbomer 0.1 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Caprylic / capric triglyceride 8 8 8 8 8 8 8 8 Squalene 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Stearyl glucoside 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Sorbitan stearate 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Stearyl alcohol 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Purified water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100

[Test Example 18] Measurement of ultraviolet shielding index

In order to confirm the UVB blocking effect of the cosmetic composition according to the present invention, SPF (Sun Protection Factor) was measured by a general method reported in the literature (J. Soc. Cosmet. Chem., 40, pp127-133, 1989) (SPF Analyzer, Optometrics USA, SPF290S), and the results are shown in Table 30 below.

The UVB blocking effect is indicated by the Sun Protection Factor (SPF), which is the blocking index of UVB, where the ultraviolet screening agent is applied to the amount of ultraviolet light required to produce MED (minimal erythemal) on untreated skin Is defined as the amount of ultraviolet light required to produce MED on the skin and is calculated by the following equation (7). Therefore, the higher the SPF, the better the UVB blocking effect. Here, MED refers to Minimal Erythemal Dose ("MED"), which is the minimum amount of erythema that causes skin erythema.

Test substance Sun Protection Factor (SPF) Formulation Example 46 19 Formulation Example 47 15 Formulation Example 48 13 Formulation Example 49 18 Formulation Example 50 17 Formulation Example 51 13 Formulation Example 52 15 Formulation Example 53 16 Formulation Example 54 14 Formulation Example 55 15 Formulation Example 56 16 Formulation Example 57 19 Formulation Example 58 15 Formulation Example 59 16 Formulation Example 60 14 Comparative Formulation Example 5 4 Comparative Formulation Example 6 15

As can be seen from the results of Table 30, Formulations 46 to 60 containing the propanoid substituted derivatives of the present invention were superior in UV blocking effect to Comparative Formulation Example 5 containing no UV blocking substance, Showed a UV blocking ability equal to or higher than that of Comparative Formulation Example 6 containing a known ultraviolet screening agent, OMC.

[Formulation Examples 61 to 75 and Comparative Formulation Example 7]

Slimming lotion was prepared in a conventional manner according to the composition of the following Tables 31 and 32 (unit: wt%).

ingredient Formulation Example 61 Formulation Example 62 Formulation Example 63 Formulation Example 64 Formulation Example 65 Formulation Example 66 Formulation Example 67 Formulation Example 68 Purified water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 Brosonin A 1.0 - - - - - - - Brosonin B - 1.0 - - - - - - Brosonin C - - 1.0 - - - - - Brosonin D - - - 1.0 - - - - Brosonin E - - - - 1.0 - - - Brosonin F - - - - - 1.0 - - Casinol C - - - - - - 1.0 - Casinol D - - - - - - - 1.0 Vegetable hydrogenated oil 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Stearic acid 0.60 0.60 0.60 0.60 0.60 0.60 0.60 0.60 Polyglycerol-10 Penta stearic and behenyl alcohol and sodium stearoyl lactylate 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Arachidyl behenyl alcohol and arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucoside 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 PEG-100 Stearate & Glycerololate & Propylene Glycol 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Caprylic / capric triglyceride 4.00 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Meadow Foam Berry Oil 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Cetyl octanoate 4.00 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Cyclomethicone 6.00 6.00 6.00 6.00 6.00 6.00 6.00 6.00 Methyl paraben 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Propylparaben 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 Disodium EDTA 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Trimethanolamine 0.13 0.13 0.13 0.13 0.13 0.13 0.13 0.13 glycerin 8.00 8.00 8.00 8.00 8.00 8.00 8.00 8.00 Carbomer 0.13 0.13 0.13 0.13 0.13 0.13 0.13 0.13

ingredient Formulation Example 69 Formulation Example 70 Formulation Example 71 Formulation Example 72 Formulation Example 73 Formulation Example 74 Formulation Example 75 Comparative Formulation Example 7 Purified water To 100 To 100 To 100 To 100 To 100 To 100 To 100 To 100 Casinol F 1.0 - - - - - - - Casinol G - 1.0 - - - - - - Casinol J - - 1.0 - - - - - Casinol K - - - 1.0 - - - - Casinol L - - - - 1.0 - - - Casinol M - - - - - 1.0 - - Casinol N - - - - - - 1.0 - Vegetable hydrogenated oil 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Stearic acid 0.60 0.60 0.60 0.60 0.60 0.60 0.60 0.60 Polyglycerol-10 Penta stearic and behenyl alcohol and sodium stearoyl lactylate 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Arachidyl behenyl alcohol and arachidyl glucoside 1.00 1.00 1.00 1.00 1.00 1.00 1.00 1.00 Cetylaryl Alcohol and Cetearyl Glucoside 2.00 2.00 2.00 2.00 2.00 2.00 2.00 2.00 PEG-100 Stearate & Glycerololate & Propylene Glycol 1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Caprylic / capric triglyceride 4.00 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Meadow Foam Berry Oil 3.00 3.00 3.00 3.00 3.00 3.00 3.00 3.00 Cetyl octanoate 4.00 4.00 4.00 4.00 4.00 4.00 4.00 4.00 Cyclomethicone 6.00 6.00 6.00 6.00 6.00 6.00 6.00 6.00 Methyl paraben 0.20 0.20 0.20 0.20 0.20 0.20 0.20 0.20 Propylparaben 0.10 0.10 0.10 0.10 0.10 0.10 0.10 0.10 Disodium EDTA 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02 Trimethanolamine 0.13 0.13 0.13 0.13 0.13 0.13 0.13 0.13 glycerin 8.00 8.00 8.00 8.00 8.00 8.00 8.00 8.00 Carbomer 0.13 0.13 0.13 0.13 0.13 0.13 0.13 0.13

[Test Example 19] Slimming effect

&Lt; Effect of accelerating decomposition of triglyceride in adipocytes &

3T3-L1 cells, a fibroblast cell line of mice, were cultured in DMEM supplemented with 10% fetal bovine serum (FBS) (Dulbecco's modified eagles medium, GIBCO BRL, Life Technologies) Well plate (culture plate) at 1 × 10 ⁵ cells / well. After 2 days, the cells were replaced with fresh DMEM (containing 10% FBS) medium and cultured for 2 days. Then, the cultured cells were further subjected to differentiation with DMEM (containing 10% FBS) containing 1 μg / ml insulin, 0.5 mM IBMX and 0.25 μM dexamethasone, and propranoid substituted with a phenyl group The derivative and caffeine were treated with 50 μM After 2 days, the cells were exchanged with insulin-containing DMEM for 5 days. After 5 days, the cells were replaced with normal medium (DMEM, containing 10% FBS) and cultured while observing until the cells morphologically changed into adipocytes.

Experiments were conducted using 3T3-L1 adipocytes differentiated from the above in order to evaluate the effect of the propanoid derivatives substituted with the prenyl group in promoting the triglycerol degradation in adipocytes. 3T3-L1 adipocytes were washed twice with PBS (phosphate buffered saline) and then added to colorless DMEM containing 0.5% bovine serum albumin (BSA) free of fatty acids. In the control group, the test substance or the test substance or the test substance was not added, and the other value was converted when the test result was 100%. Caffeine (50 μM) was also treated with another comparative group. The extent of lipolysis was determined by measuring the glucose concentration liberated from adipocytes into the culture medium. Glucose was determined by the color reaction method using a GPO-trinder kit purchased from Sigma (St. Louis, Mo., USA) and absorbance was measured at 540 nm using an ELISA reader. The results are shown in Table 33.

Test substance Amount of liberated glycerol (%) Control group 100 Caffeine 115 Brosonin A 125 Brosonin B 120 Brosonin C 124 Brosonin D 135 Brosonin E 124 Brosonin F 123 Casinol C 135 Casinol D 126 Casinol F 124 Casinol G 135 Casinol J 120 Casinol K 129 Casinol L 130 Casinol M 126 Casinol N 124

As shown in Table 33, the concentration of glucose liberated from the adipocytes into the culture medium was significantly increased in the group treated with the propanoid substituted derivative of the present invention, compared with the control group. In addition, it was found that the group treated with the propanoid derivative substituted with the phenyl group of the present invention had a better lipolytic effect than the group treated with caffeine as a positive control.

<Measurement of subcutaneous fat thickness>

Among the women with local obesity or cellulite, 160 adult women aged 25 to 46 years with a Body Mass Index (BMI) of 21 to 27 (kg) / height (m) ² were divided into 16 groups of 10 For women in the military, a lotion of Formulation Examples 31 to 75 and Comparative Formulation Example 7 was used together with a massage of the user at home on both thighs twice a day in the morning and evening for 4 weeks, The efficacy was assessed by instrument evaluation, researcher (dermatologist) evaluation and questionnaire evaluation.

Ultrasound-EuB 415 US scanner was used to measure the thickness (unit: mm) of the subcutaneous fat layer using ultrasound. The obtained values were compared using a Student t test or a Wilcoxon test on both sides and statistical significance was analyzed (Significance level α = 0.05). The results are shown in Table 34.

Test substance Reduction rate of subcutaneous fat thickness (%) Formulation Example 61 16 Formulation Example 62 15 Formulation Example 63 13 Formulation Example 64 18 Formulation Example 65 17 Formulation Example 66 13 Formulation Example 67 15 Formulation Example 68 16 Formulation Example 69 17 Formulation Example 70 15 Formulation Example 71 16 Formulation Example 72 19 Formulation Example 73 15 Formulation Example 74 16 Formulation Example 75 14 Comparative Formulation Example 7 0

In the results of Table 34, when Formulation Examples 31 to 75 containing a propanoid derivative substituted with a phenyl group of the present invention were used, compared with Comparative Formulation Example 7 containing no propanoid derivative substituted with a phenyl group, , Respectively. During the test period, the subject's weight did not change.

<Cellulite Observation>

The degree of cellulite was determined by a visual evaluation by a professional researcher. The degree of cellulite was evaluated by visual evaluation in five steps from 0 point to 4 points (0 point: very much cellulite, 4 points: no cellulite). The results are shown in Table 35.

Test substance Cellulite rating change
(Before Using Rating Rating - After Using Rating Rating) Formulation Example 61 2.1 Formulation Example 62 2.3 Formulation Example 63 2.4 Formulation Example 64 1.9 Formulation Example 65 1.9 Formulation Example 66 2.3 Formulation Example 67 2.1 Formulation Example 68 1.6 Formulation Example 69 2.1 Formulation Example 70 2.3 Formulation Example 71 1.6 Formulation Example 72 2.1 Formulation Example 73 2.3 Formulation Example 74 2.5 Formulation Example 75 2.6 Comparative Formulation Example 7 3.8

In the results of the above Table 35, in the evaluation of the efficacy by the researchers, the cellulite was significantly decreased and the skin elasticity was increased at the site where Formulations 61 to 75 were used as compared with Comparative Formulation Example 7. [

Claims (25)

A cosmetic composition for preventing skin aging comprising, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives include but are not limited to the following: Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol G, Cassinol J, Wherein the cosmetic composition is at least one selected from the group consisting of NOL L, CAZINOL M, and CAZINOL N. The cosmetic composition according to claim 1, wherein the composition is for inhibiting the production of active oxygen by ultraviolet rays. The composition of claim 1, wherein the composition is UV-blocking. A cosmetic composition for improving skin elasticity, which comprises a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for improving skin wrinkles, comprising a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for moisturizing comprising, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for enhancing skin barrier function, which contains, as an active ingredient, a propanoid derivative substituted with a phenyl group,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for inducing the differentiation of dermal keratinocytes, which comprises, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. Claims 1. A composition for improving acne comprising a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for antimicrobial use containing, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Nol K, Casinol L, Casinol M and Casinol N,
Wherein the composition is for antimicrobial use against Propionibacterium acnes which is a cause of acne. A cosmetic composition for anti-inflammation comprising, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Nol K, Casinol L, Casinol M and Casinol N,
Wherein the composition is for anti-inflammation against inflammation by prostaglandin. A cosmetic composition for inhibiting lipid formation, which contains a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for improving color and skin tone, which comprises, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives include, but are not limited to, Bronosin A, Bronosin B, Bronosin D, Bronosin E, Bronosin F, Cassinol D, Cassinol G, Cassinol J, Cassinol K, Cassinol L, And N, N, wherein the cosmetic composition is at least one selected from the group consisting of N, N, A cosmetic composition for shrinking pores containing a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for controlling sebum comprising a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for whitening comprising, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives include, but are not limited to, Bronosin A, Bronosin B, Bronosin D, Bronosin E, Bronosin F, Cassinol D, Cassinol G, Cassinol J, Cassinol K, Cassinol L, And N, N, wherein the cosmetic composition is at least one selected from the group consisting of N, N, A cosmetic composition for slimming comprising a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for neutral fat decomposition, which contains a propanoid derivative substituted with a prenyl group as an active ingredient,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. A cosmetic composition for removing cellulite, which contains, as an active ingredient, a propanoid derivative substituted with a prenyl group,
The propanoid derivatives are selected from the group consisting of Bronosin A, Bronosin B, Bronosin C, Bronosin D, Bronosin E, Bronosin F, Cassinol C, Cassinol D, Cassinol F, Cassinol G, Wherein the cosmetic composition is at least one selected from the group consisting of NOLK, CAZINOL L, CAZINOL M, and CAZINOL N. The cosmetic composition according to any one of claims 1 to 19, wherein the propanoid derivative substituted with a prenyl group is extracted from mackerel. The cosmetic composition according to any one of claims 1 to 19, wherein the content of the propanoid derivative substituted with the prenyl group is 0.001 to 50% by weight. delete delete delete delete