KR20150019545A - Composition for antioxidant and anti-imflamation - Google Patents

Abstract

The present invention relates to an anti-oxidant and anti-inflammatory composition. According to the present invention, eleutheroside D inhibits generation of free radicals and thus has an anti-oxidant effect. In addition, eleutheroside D inhibits generation of NO and thus has an anti-inflammatory effect. Therefore, the composition can be used as a pharmaceutical composition, an external use skin formulation, a cosmetic composition, or health food. The composition includes a compound represented by chemical formula 1 as an active ingredient.

Description

Composition for antioxidant and anti-inflammation [

The present invention relates to compositions for antioxidant and anti-inflammation.

Active oxygen introduced from the outside of the living body or generated in the living body causes many problems such as promoting aging of the living body or generating cancer. Therefore, the development and research of antioxidants that inhibit oxidation by active oxygen have been performed. Antioxidants are widely distributed in copper and plants. Many phenolic compounds, flavonoids, tocopherols, vitamin C and selenium are known in fruits and vegetables. However, the antioxidant substances present in nature can not be expected to have practically sufficient effects in skin application. Therefore, although synthetic antioxidants having excellent antioxidant ability and low cost are widely used, their use is restricted due to safety concerns such as human side effects.

In addition, inflammation is an immune response of a human body in response to a wound or disease, and oxidative stress such as ultraviolet rays, active oxygen, free radicals, etc. activate inflammatory factors and cause aging of various diseases and skin. The vasoactive polypeptide, kinin, plasmin and complement, have vasodilatory and contraction and chemotaxis effects, as well as lymphokines such as interleukin-6 (IL-6) Phosphorus and arachidonic acid are responsible for inflammation. Arachidonic acid is metabolized through inflammatory mediators such as prostaglandin and lukotrienes via two pathways: cyclooxygenase or lipooxygenase, mediating a variety of inflammatory responses.

On the other hand, in order to eliminate inflammation, elimination of inflammation source, reduction of vital reaction and symptoms is called anti-inflammatory. To date, substances used for antiinflammatory purposes include flutenamic acid, ibuprofen, benzydamine, indomethacin, and steroids, prednisolone, , Dexamethasone, and the like. It is also known that allantoin, azene, hydrocortisone and the like are effective for antiinflammation. However, these materials are limited in their use due to safety of skin, .

Therefore, it is strongly desired to develop a composition having antioxidant and antiinflammatory activity, which is more safe than a living body, has a stable active ingredient, and is more effective than a conventional antioxidant and antiinflammatory agent.

Thus, the inventors of the present invention confirmed that Eleutheroside D scavenges free radicals to exhibit an antioxidative effect, suppresses NO production, and exhibits an anti-inflammatory effect, thus completing the present invention.

Accordingly, an object of the present invention is to provide an antioxidant and anti-inflammatory composition comprising, as an active ingredient, a compound represented by the following general formula

[Chemical Formula 1]

As means for solving the above problems,

There is provided a pharmaceutical composition for antioxidant and antiinflammation comprising a compound represented by the following formula (1) as an active ingredient.

 [Chemical Formula 1]

As another means for solving the above problems,

There is provided an antioxidant and anti-inflammatory external preparation for skin comprising as an active ingredient a compound represented by the following formula (1).

[Chemical Formula 1]

As another means for solving the above problems,

There is provided a cosmetic composition for antioxidant and anti-inflammation comprising as an active ingredient a compound represented by the following formula (1).

[Chemical Formula 1]

As another means for solving the above problems,

There is provided a health food for antioxidant and antiinflammation comprising a compound represented by the following formula (1) as an active ingredient.

[Chemical Formula 1]

Eleutheroside D according to the present invention shows antioxidative effect by eliminating free radicals and exhibits an anti-inflammatory effect by inhibiting NO production involved in inflammatory reaction, and thus can be used in medicines, cosmetics or health foods .

Hereinafter, the configuration of the present invention will be described in detail.

Antioxidant and antiinflammatory components have high antioxidant and antiinflammatory activity at a low concentration in order to exert an excellent effect when they are applied to actual skin, have excellent ability to permeate and absorb the skin, and are sufficient to exhibit antioxidant and antiinflammatory effects It is preferable to have a low volatility so as to be able to stay for a period of time, to stably maintain the active ingredient on the composition or on the skin, to be easily formulated into medicines or cosmetics, and to be safe for the skin. However, the components satisfying all of the above-mentioned characteristics among the known components are not common. For example, some antioxidant and antiinflammatory components have excellent antioxidant and antiinflammatory activity even at a low concentration in vitro, but they are difficult to be applied to real skin because of their ability to permeate through the skin. Other active ingredients have low hydrophilicity and are difficult to formulate into medicines or cosmetics. In addition, some antioxidant and antiinflammatory components may be degraded or transformed into other compounds when they are exposed to heat, light, or oxygen, and the effects may be lost before they are applied to the skin.

As can be seen in the following examples, Eleutheroside D has remarkably excellent antioxidative and anti-inflammatory effects at a low concentration. Therefore, Eleutheroside D is an effective ingredient for medicines, cosmetics, and health foods for antioxidant and anti- Can be used.

Accordingly, the present invention provides a pharmaceutical composition for antioxidant and anti-inflammation, which comprises a compound represented by the following general formula (1) as an active ingredient.

[Chemical Formula 1]

(2S, 3R, 4S, 5S, 6R) -2- [4 - [(3S, 3aS, 6S, 6aR) -6- [ , 4S, 5S, 6R) -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydropyran-2-yl] oxy- phenyl] -1,3,3a, 4,6,6a-hexahydrofuro [ c] furan-3-yl] -2,6-dimethoxy-phenoxy] -6- (hydroxymethyl) tetrahydropyran-3,4,5-trio and is also called Eleutheroside D.

The compound of formula (1) may be synthesized or a commercially available compound may be used.

The pharmaceutical composition for antioxidant and antiinflammation of the present invention may include a pharmaceutically acceptable salt of the compound of formula (1).

The pharmaceutically acceptable salt of the compound of Formula 1 may be an acid addition salt formed using an organic acid or an inorganic acid, and the organic acid may be, for example, formic acid, acetic acid, propionic acid, lactic acid, butyric acid, isobutyric acid, trifluoroacetic acid The organic acid may be selected from the group consisting of hydrochloric acid, hydrobromic acid, hydrochloric acid, hydrobromic acid, hydrobromic acid, hydrobromic acid, hydrobromic acid, hydrobromic acid, malic acid, maleic acid, malonic acid, fumaric acid, succinic acid, monoamide, glutamic acid, tartaric acid, oxalic acid, citric acid, glycolic acid, glucuronic acid, , Benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid-based salts, and the inorganic acid includes, for example, hydrochloric acid, bromic acid, sulfuric acid, phosphoric acid, nitric acid, carbonic acid and boric acid-based salts. Preferably in the hydrochloride or acetate form, more preferably in the hydrochloride form.

The above-mentioned acid addition salts may be obtained by a) directly mixing the compound of formula 1 and an acid, or b) dissolving and mixing one of them in a solvent or a water solvent, or c) Lt; RTI ID = 0.0 > acid < / RTI > in a solvent and mixing them.

In addition to the above, additionally saltable forms include, but are not limited to, the salts of gabapentin, pregabalin, nicotinate, adipate, hemimarate, cysteine, acetylcysteine, methionine, arginine, Aspartate and the like.

When the compound of Chemical Formula 1 of the present invention is used as a medicine, it may further contain one or more active ingredients showing the same or similar functions. For example, known antioxidant and anti-inflammatory components. The addition of additional antioxidant and anti-inflammatory ingredients may further enhance the antioxidant and anti-inflammatory effects of the compositions of the present invention. When the above ingredients are added, skin safety, easiness of formulation, and stability of effective ingredients can be considered according to the combined use. In one embodiment of the present invention, the composition is a skin regeneration component known in the art comprising retinoic acid, TGF, protein from animal placenta, betulinic acid and chlorella extract, antioxidant components known in the art, such as tocopherol, selenium , Vitamin C and phenolic compounds, whitening ingredients known in the art, substances inhibiting the activity of tyrosinase enzymes such as kojic acid and arbutin, hydroquinone, vitamin C (L- Ascorbic acid, derivatives thereof, and various plant extracts. The additional component may be included in an amount of 0.0001 to 10% by weight based on the total weight of the composition, and the content range may be adjusted according to requirements such as skin safety, ease of formulation of the compound of Formula 1 .

In addition, the pharmaceutical composition for antioxidant and anti-inflammation of the present invention may further comprise a pharmaceutically acceptable carrier.

Pharmaceutically acceptable carriers may contain a variety of ingredients such as buffer, injectable sterile water, normal saline or phosphate buffered saline, sucrose, histidine, salts and polysorbates.

The pharmaceutical composition of the present invention can be administered orally or parenterally, and can be administered in the form of a general pharmaceutical preparation, for example, various forms of oral and parenteral administration at the time of clinical administration. In the case of formulation, , An extender, a binder, a wetting agent, a disintegrant, a surfactant, and the like.

Solid formulations for oral administration include tablets, pills, powders, granules, capsules and the like, which may be prepared by mixing the pharmaceutical composition of the present invention with at least one excipient such as starch, calcium carbonate, Sucrose, lactose, gelatin, and the like.

In addition to simple excipients, lubricants such as magnesium stearate talc are also used. Examples of liquid formulations for oral administration include suspensions, solutions, emulsions, syrups and the like. Various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like may be included in addition to water and liquid paraffin, which are simple diluents commonly used.

Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used as the non-aqueous solvent and suspension agent. Examples of the suppository base include witepsol, macrogol, tween 61, cacao butter, laurin, glycerogelatin and the like.

In the present invention, the term 'antioxidative effect' refers to the action of free radicals or reactive oxygen species (ROS), which are highly reactive according to oxidative stress caused by intracellular metabolism or ultraviolet rays, Refers to inhibition of oxidation, and includes removal of free radical or reactive oxygen species, thereby reducing damage to the cells.

In the present invention, the term 'anti-inflammatory effect' refers to inhibition of inflammation. The inflammation is one of defensive responses of biological tissues to certain stimuli, and involves three types of tissue degeneration, circulatory disorder, exudate, and tissue proliferation Complex lesions. More specifically, inflammation is part of congenital immunity and, like in other animals, human congenital immunity recognizes a pattern of cell surfaces that are specifically present in a pathogen. Phagocytes recognize cells with such surfaces as non-magnetic and attack pathogens. If pathogens break through the physical barriers of the body, an inflammatory reaction occurs. Inflammation is a nonspecific defense that creates hostile environments for microorganisms entering the wound. In the inflammatory response, white blood cells that are responsible for the early stage of immune response, when wounded or infected, enter the body to express cytokines. Therefore, the expression level of intracellular cytokine is an index of inflammatory response activation. Examples of skin diseases associated with inflammation include atopic dermatitis, psoriasis, radiation, chemical substances, inflammatory diseases caused by burns, acid burns, vesicular dermatosis, visceral type diseases, itching due to allergies, seborrheic eczema, rose acne, Inflammatory hair loss such as pemphigus vulgaris, polymorphous exudative erythema, erythema nodosum, erythematosus, pharyngitis, alopecia areata, skin T-cell lymphoma, and the like.

The pharmaceutical composition of the present invention can provide a desirable skin antioxidant and anti-inflammatory effect when an effective amount of the compound of Formula 1 is included. In the present invention, "effective amount" means the amount of a compound capable of inhibiting or alleviating the oxidation of cells or inhibiting inflammation. An effective amount of the compound of formula (1) contained in the composition of the present invention will vary depending on the form in which the composition is commercialized, how the compound is applied to the skin, and the time on the skin. For example, when the composition is commercialized as a pharmaceutical product, the compound of Formula 1 may be contained at a higher concentration than that of a cosmetic product that is routinely applied to skin. Accordingly, the daily dosage is 0.1 to 100 mg / kg, preferably 30 to 80 mg / kg, more preferably 50 to 60 mg / kg, based on the amount of the compound of formula (1) 6 times a day.

The pharmaceutical composition of the present invention may be used alone or in combination with other methods for achieving the intended use.

The present invention can also provide a formulation of an external skin preparation for antioxidant and anti-inflammation comprising the compound of formula 1 as an active ingredient.

When the compound of formula (1) is used as an external preparation for skin, it may further comprise at least one selected from the group consisting of fatty substances, organic solvents, solubilizers, thickeners and gelling agents, softeners, antioxidants, suspending agents, stabilizers, foaming agents, , Water, ionic or nonionic emulsifiers, fillers, sequestering agents and chelating agents, preservatives, vitamins, blocking agents, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or external preparations for skin And any other ingredients used in the skin sciences. The components can also be introduced in amounts commonly used in the field of dermatology.

When the compound of Formula 1 is provided as an external preparation for skin, it may have a formulation such as, but not limited to, ointments, patches, gels, creams or sprays.

The present invention can also provide formulations of antioxidant and anti-inflammatory cosmetics containing the compound of Formula 1 as an active ingredient.

When the compound of Chemical Formula 1 is used as a cosmetic, the cosmetic product containing the compound of Chemical Formula 1 as an active ingredient may be prepared in the form of a general emulsified formulation and a solubilized formulation. For example, creams, essences, cosmetic creams, sprays, gels, packs, sunscreens, make-up bases, liquids such as lotions such as lotion, facial lotion, body lotion, A powder, a cleansing lotion, a makeup removing agent such as a cleansing oil, a cleaning agent such as a cleansing foam, a soap, a body wash and the like.

The cosmetic composition may further contain, in addition to the compound of Formula 1, a lipid, an organic solvent, a solubilizing agent, a thickening agent and a gelling agent, a softening agent, an antioxidant, a suspending agent, a stabilizer, a foaming agent, a fragrance, , Ionic or nonionic emulsifiers, fillers, sequestering and chelating agents, preservatives, vitamins, barrier agents, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or cosmetics And may contain adjuvants commonly used in the cosmetics field, such as any of the other ingredients.

In the case of a wash-off type cosmetic such as a make-up removing agent, a detergent, etc. in which the active ingredient remains on the skin in a short period of time when the compound of formula (1) is produced into a cosmetic product, . On the other hand, in the case of leave-on type cosmetics, such as lotion, cream, essence, etc., in which the active ingredient remains on the skin for a long period of time, It may be included. In one embodiment of the present invention, although not limited thereto, the composition may contain 0.0001 wt% to 10 wt% (preferably 0.0001 wt% to 1 wt%) of the compound of Formula 1 based on the total weight of the composition . If the composition of the present invention contains less than 0.0001% by weight of the compound of the formula 1, sufficient antioxidative and anti-inflammatory effects can not be expected. If the composition contains more than 10% by weight, This is to prevent safety problems.

The present invention also relates to an antioxidant and anti-inflammatory health food comprising the compound of formula (1).

The term 'health food' as used herein means a food prepared by adding the compound of formula (1) to food materials such as beverage, tea, spice, gum and confectionery, or by encapsulation, powdering or suspension, But it has the advantage that there are no side effects that can occur when a drug is used for a long period of time using a food as a raw material.

The health food of the present invention thus obtained can be taken on a daily basis, so that a high antioxidant and anti-inflammatory effect can be expected, which is very useful.

When the compound of Chemical Formula 1 is used as a food additive, the compound of Chemical Formula 1 may be added as it is or may be used together with other food or food ingredients, and may be suitably used according to a conventional method. The amount of the active ingredient to be mixed can be suitably determined according to its intended use (prevention, health or therapeutic treatment). Generally, the composition of the present invention is added in an amount of not more than 15 parts by weight, preferably not more than 10 parts by weight, based on the raw material, when the food or beverage is produced. However, in the case of long-term consumption intended for health and hygiene purposes or for health control purposes, the amount may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount exceeding the above range .

There is no particular limitation on the kind of the food. Examples of the food to which the above substance can be added include dairy products including meat, sausage, bread, chocolate, candy, snack, confectionery, pizza, ramen, other noodles, gums, ice cream, various soups, drinks, tea, Alcoholic beverages, and vitamin complexes, all of which include healthy foods in a conventional sense.

The health beverage composition of the present invention may contain various flavors or natural carbohydrates as an additional ingredient such as ordinary beverages. Such natural carbohydrates are monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, and polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol and erythritol. Examples of sweeteners include natural sweeteners such as tau martin and stevia extract, synthetic sweeteners such as saccharin and aspartame, and the like. The ratio of the natural carbohydrate is generally about 0.01 to 0.04 g, preferably about 0.02 to 0.03 g per 100 mL of the composition of the present invention.

In addition to the above, the health food of the present invention may contain various nutrients, vitamins, electrolytes, flavors, colorants, pectic acids and salts thereof, alginic acid and its salts, organic acids, protective colloid thickeners, pH adjusting agents, stabilizers, preservatives, , A carbonating agent used in carbonated drinks, and the like. In addition, the health food of the present invention may contain flesh for the production of natural fruit juice, fruit juice drink and vegetable drink. These components may be used independently or in combination. The proportion of such additives is not critical, but is generally selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the composition of the present invention.

Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are illustrative of the present invention, and the present invention is not limited to the following examples.

Reference Example  One: Eleutheroside  D ( Eleutheroside  D) Material information

(2S, 3R, 4S, 5S, 6R) -6- [3,5-dimethoxy-4 - [(2S, 3R, 4S, 5S, 6R) -2- [ -3,4,5-trihydroxy-6- (hydroxymethyl) tetrahydropyran-2-yl] oxy-phenyl] -1,3,3a, 4,6,6a-hexahydrofuro [3,4- c] yl] -2,6-dimethoxy-phenoxy] -6- (hydroxymethyl) tetrahydropyran-3,4,5-trio

CAS No .: 79484-75-6

Molecular Formula: C ₃₄ H ₄₆ O ₁₈

Molecular Weight: 742.72

Where to buy: Tauto Biotech Co., Ltd.

Origin and Sink Plants: Acanthopanax senticosus

Example  1: Antioxidant effect - Free radical  Erasure rate

To determine the antioxidant activity of Eleutheroside D, free radical scavenging activity was measured. Free radical scavenging activity was measured using DPPH. DPPH was purchased from Sigma Co. (Sigma Co., Ltd., USA) and used. First, a standard DPPH ethanol solution of 1.5 mM (0.06 mg / ml) was prepared. Then, ethanol was added to ascorbic acid, which is an antioxidant, as a standard compound and a compound of formula (1) to prepare samples at concentrations of 50 / / . Then, the sample and standard DPPH solution were added at the same ratio, stirred well, reacted at 37 ° C for 30 minutes, and absorbance was measured at 520 nm. At this time, ethanol was added instead of the sample to give a control group. Free radical scavenging activity and the results are obtained for the IC ₅₀ half maximal inhibitory concentration (median inhibition) shown in Table 1 below. IC ₅₀ is a common method of expressing free radical scavenging activity with the concentration of ascorbic acid and the compound of formula 1 required to remove 50% of the free radicals of the no-added control group.

 Free radical scavenging rate (%) sample Free radical scavenging rate (ug / ml; ppm) Ascorbic acid 8 The compound of formula (1) 31

As shown in Table 1, the compound of the formula (I) is lower in activity than ascorbic acid (Vitamin C), which is a typical strong antioxidant, but it is stable as an antioxidative effect with excellent level as a natural substance, .

Example  2: Anti-inflammatory effect - NO  Production inhibitory effect

In order to confirm the antiinflammatory effect and the skin trouble relieving effect of the compound of the formula (1), the nitric oxide (NO) formation inhibition test was carried out by the GRIESS method using the RAW264.7 cell line (ATCC number: CRL-2278).

Specifically, RAW264.7 cells, macrophages of mice, were subcultured several times, placed in 24-well plates at 3 × 10 ⁵ per well, and cultured for 24 hours. Subsequently, the compound of Chemical Formula 1 was diluted with the concentrations shown in the following Table 2 and replaced with the cell culture medium containing the compound. This concentration means the concentration of the compound of formula (I) dissolved in the medium used for the evaluation. The concentration is 1% = 10 mg / ml, 0.1% = 1 mg / ml, 0.01 = 0.1 mg / ml and 0.001 = 0.01 mg / ml . On the other hand, L-NMMA (L-NG-Monomethylarginine), a NO-production inhibitor, was treated as a positive control and cultured for 30 minutes. Lipopolysaccharide (LPS) 100 μl of the supernatant was transferred to a 96-well plate, and 100 μl of the GRIESS solution was added thereto, followed by reaction at room temperature for 10 minutes. Absorbance at 540 nm was measured. The NO inhibitory effect of the compound of Chemical Formula 1 was compared with the negative control treated with LPS only and the NO inhibitory substance was not treated, and the results are shown in Table 2 below.

NO generation inhibitory effect sample NO production inhibition rate (%) L-NMMA (positive control, 0.001%) 27.80 Compound (1) (0.001%) 11.22 The compound of formula (1) (0.01%) 20.63 Compound (1) (0.1%) 31.94 Compound (1) (1) 39.76

As shown in Table 2, the compound of Chemical Formula 1 has low activity compared to the typical anti-inflammatory substance NMMA, but exhibits excellent activity as a natural substance. Therefore, anti-inflammatory effect plays an auxiliary role in whitening and wrinkle improvement, Can be expected.

Formulation example  1: Preparation of pharmaceutical preparations

1. Manufacturing of powder

0.001 g of the compound of formula (1)

Lactose 1g

The above components were mixed and packed in airtight bags to prepare powders.

2. Preparation of tablets

0.2 mg of the compound of formula (1)

100 mg of corn starch

100 mg of milk

Stearic acid  Magnesium 2 mg

After mixing the above components, tablets were prepared by tableting according to a conventional method for producing tablets.

3. Preparation of capsules

0.2 mg of the compound of formula (1)

100 mg of corn starch

100 mg of milk

Stearic acid  Magnesium 2 mg

After mixing the above components, the capsules were filled in gelatin capsules according to the conventional preparation method of capsules.

4. Manufacture of rings

0.003 g of the compound of formula (1)

Lactose 1.5 g

Glycerin 1 g

Xylitol  0.5 g

After mixing the above components, they were prepared so as to be 4 g per one ring according to a conventional method.

5. Manufacture of granules

2 mg of the compound of formula (1)

Soybean extract 50 mg

200 mg of glucose

600 mg of starch

After mixing the above components, 100 mg of 30% ethanol was added and dried at 60 캜 to form granules, which were then filled in a capsule.

Formulation example  2: Manufacture of cosmetics

1. Manufacture of softening longevity (skin lotion)

As the following composition, the number of softening times containing the compound of formula (1) as an active ingredient was prepared according to a conventional method.

0.1% by weight of the compound of formula (1)

Beta-1,3-glucan 1.0 wt%

Butylene glycol 2.0 wt%

Propylene glycol 2.0 wt%

Carboxyvinyl polymer 0.1 wt%

0.2% by weight of phage-12 nonylphenyl ether

Polysorbate 80 0.4 wt%

Ethanol 10.0 wt%

0.1% by weight triethanolamine

Preservative 0.05 wt%

0.05% by weight of pigment

0.05% by weight fragrance

Purified water to 100%

2. Manufacture of nutrition lotion (milk lotion)

As in the following composition, a nutritional lotion containing the compound of the formula (1) as an active ingredient was prepared by a conventional method.

0.1% by weight of the compound of formula (1)

Beta-1,3-glucan 1.0 wt%

4.0 wt%

Polysorbate 60 1.5 wt%

1.5% by weight of sorbitan sesquioleate

0.5% by weight liquid paraffin

Caprylic / capric triglyceride 5.0 wt%

Glycerin 3.0 wt%

3.0% by weight of butylene glycol

3.0% by weight of propylene glycol

Carboxyvinyl polymer 0.1 wt%

0.2% by weight triethanolamine

Preservative 0.05 wt%

0.05% by weight of pigment

0.05% by weight fragrance

Purified water to 100%

3. Manufacture of nutritional cream

A nutritional cream containing the compound of formula (1) as an active ingredient was prepared according to a conventional method, as shown below.

0.2% by weight of the compound of formula (1)

Beta-1,3-glucan 5.0 wt%

Wax 10.0 wt%

Polysorbate 60 1.5 wt%

≪ tb > < tb > < tb >

0.5% by weight of sorbitan sesquioleate

Liquid paraffin 10.0 wt%

Squalane 5.0 wt%

Caprylic / capric triglyceride 5.0 wt%

Glycerin 5.0 wt%

3.0% by weight of butylene glycol

3.0% by weight of propylene glycol

0.2% by weight triethanolamine

Preservative 0.05 wt%

0.05% by weight of pigment

0.05% by weight fragrance

Purified water to 100%

4. Manufacture of massage cream

A massage cream containing the compound of formula (I) as an active ingredient was prepared according to a conventional method, as shown below.

0.1% by weight of the compound of formula (1)

Beta-1,3-glucan 3.0 wt%

Wax 10.0 wt%

Polysorbate 60 1.5 wt%

≪ tb > < tb > < tb >

0.8% by weight of sorbitan sesquioleate

Liquid paraffin 40.0 wt%

Squalane 5.0 wt%

Caprylic / capric triglyceride 4.0 wt%

Glycerin 5.0 wt%

3.0% by weight of butylene glycol

3.0% by weight of propylene glycol

0.2% by weight triethanolamine

Preservative 0.05 wt%

0.05% by weight of pigment

0.05% by weight fragrance

Purified water to 100%

5. Manufacture of pack

A pack containing the compound of formula (1) as an active ingredient was prepared according to a conventional method, as shown below.

0.2% by weight of the compound of formula (1)

Beta-1,3-glucan 1.0 wt%

Polyvinyl alcohol 13.0 wt%

0.2% by weight of sodium carboxymethylcellulose,

Glycerin 5.0 wt%

Allantoin 0.1 wt%

6.0% by weight of ethanol

0.3% by weight of phage-12 nonylphenyl ether

Polysorbate 60 0.3 wt%

Preservative 0.05 wt%

0.05% by weight of pigment

0.05% by weight fragrance

Purified water to 100%

Formulation example  3: Topical  Produce

1. Manufacture of gel

As in the following composition, a gel containing the compound of formula (1) as an active ingredient was prepared according to a conventional method.

0.1% by weight of the compound of formula (1)

0.1% by weight of beta-1,3-glucan

0.05% by weight of sodium ethylenediaminetetraacetate

Glycerin 5.0 wt%

Carboxyvinyl polymer 0.3 wt%

5.0% by weight of ethanol

≪ tb > < tb > < tb >

Triethanolamine 0.3 wt%

Preservative 0.05 wt%

0.05% by weight of pigment

0.05% by weight fragrance

Purified water to 100%

2. Manufacture of ointment

An ointment containing the compound of formula (I) as an active ingredient was prepared according to a conventional method, as shown below.

0.5% by weight of the compound of formula (1)

Beta-1,3-glucan 10.0 wt%

Wax 10.0 wt%

Polysorbate 60 5.0 wt%

≪ tb > < tb > < tb >

0.5% by weight of sorbitan sesquioleate

Vaseline 5.0 wt%

Liquid paraffin 10.0 wt%

Squalane 5.0 wt%

SHARE BUTTER 3.0 wt%

Caprylic / capric triglyceride 5.0 wt%

Glycerin 10.0 wt%

Propylene glycol 10.2 wt%

0.2% by weight triethanolamine

Preservative 0.05 wt%

0.05% by weight of pigment

0.05% by weight fragrance

Purified water to 100%

3. Preparation of topical medicament (gel ointment)

A gel ointment agent containing the compound of the formula (1) as an active ingredient was prepared according to a conventional method.

0.5% by weight of the compound of formula (1)

Beta-1,3-glucan 10.0 wt%

1.5% by weight of polyacrylic acid (Carbopol 940)

5.0% by weight of isopropanol

Hexylene glycol 25.0 wt%

Triethanolamine 1.7 wt%

Deionized water to 100%

4. Preparation of topical medicines (patches)

As the following composition, a patch containing a compound of the formula (1) as an active ingredient was prepared by a conventional method.

0.5% by weight of the compound of formula (1)

Beta-1,3-glucan 3.0 wt%

Hexylene glycol 20.0 wt%

Diethylamine 0.7 wt%

1.0% by weight of polyacrylic acid (Carbopol 934P)

0.1% by weight of sodium sulfite

1.0% by weight of polyoxyethylene lauryl ether (E.O. = 9)

1.0% by weight of polyhydroxyethylene cetyl stearyl ether (Cetomacrogol 1000)

Viscous paraffin oil 2.5 wt%

2.5% by weight of caprylic acid ester / capric acid ester (Cetiol LC)

Polyethylene glycol 400 3.0 wt%

Deionized water to 100%

Formulation example  4: Manufacturing of food

Foods containing the compound of formula (I) of the present invention were prepared as follows.

1. Manufacture of Flour Food

0.05 to 1.0 part by weight of the compound of Formula 1 was added to wheat flour, and a bread, a cake, a cookie, a cracker and a noodle were prepared using the mixture to prepare a health food.

2. Manufacture of dairy products

0.2 part by weight of the compound of Formula 1 was added to milk, and various dairy products such as butter and ice cream were prepared using the milk.

3. Manufacturing of wire

Brown rice, barley, glutinous rice, and yulmu were dried by a known method and dried, and the mixture was granulated to a powder having a particle size of 60 mesh. Black soybeans, black sesame seeds, and perilla seeds were steamed and dried by a conventional method, and then they were prepared into powder having a particle size of 60 mesh by a pulverizer. The compound of Formula 1 was concentrated under reduced pressure in a vacuum concentrator, sprayed, and dried with a hot-air drier, and the resulting dried product was pulverized to a size of 60 mesh with a pulverizer to obtain a dried powder.

The grains, seeds, and dry powder of the compound of formula (1) prepared above were blended in the following proportions relative to 100 parts by weight of the mixed powder.

(30 parts by weight of brown rice, 15 parts by weight of yulmu, 20 parts by weight of barley)

Seeds (7 parts by weight of perilla, 8 parts by weight of black beans, 7 parts by weight of black sesame seeds)

(1) (0.1 part by weight),

(0.5 part by weight),

Rhubarb (0.5 Weight portion )

Formulation example  5: Manufacture of beverages

1. Manufacture of health drinks

0.1 mg of the compound of formula (1)

Citric acid 1000 mg

100 g of oligosaccharide

Plum concentrate 2 g

Taurine 1 g

Purified water  All 900 mL

The above components were mixed according to a conventional health drink manufacturing method, and the mixture was heated at 85 DEG C for about 1 hour with stirring. Then, the solution thus prepared was filtered and sterilized in a sterilized 2L-container, Lt; RTI ID = 0.0 > health < / RTI >

Although the composition ratio is a mixture of the components suitable for the preferred beverage as a preferred embodiment, the blending ratio may be arbitrarily varied according to the regional and national preferences such as the demand level, the demanding country, and the intended use.

2. Manufacture of vegetable juice

1 g of the compound of formula (I) of the present invention was added to 1,000 mL of tomato or carrot juice to prepare vegetable juice for health promotion.

3. Manufacture of fruit juice

1 g of the compound of formula (1) was added to 1,000 mL of apple or grape juice to prepare fruit juice for health promotion.

Claims (12)

A pharmaceutical composition for antioxidation comprising a compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

An external skin preparation for antioxidation comprising a compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

3. The method of claim 2,
Wherein the external preparation is a formulation of ointment, patch, gel, cream or spray.
A cosmetic composition for antioxidation comprising a compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

5. The method of claim 4,
Cosmetics, essences, lotions, creams, packs, gels, powders, foundations or detergents.
An antioxidant health food containing the compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

An antiinflammatory pharmaceutical composition comprising a compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

An antiinflammatory skin external preparation comprising a compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

9. The method of claim 8,
Wherein the external preparation is a formulation of ointment, patch, gel, cream or spray.
An anti-inflammatory cosmetic composition comprising a compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]

11. The method of claim 10,
Cosmetics, essences, lotions, creams, packs, gels, powders, foundations or detergents.
An anti-inflammatory health food containing the compound represented by the following formula (1) as an active ingredient:
[Chemical Formula 1]