JP2005171003A - Antioxidant - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a useful antioxidant which is safe, is easily available, has usefulness for cosmetics, foods, drinks, food additives, and the like, and has a strong anti-oxidizing ability. <P>SOLUTION: It has been found that 4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-2-naphtalenecarboxylic acid (compound 1) isolated from Acanthopanax sessiliflorus has a strong antioxidizing action, and the antioxidant contains the same. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention is effective for the prevention and treatment of cosmetic disorders such as adult diseases, various diseases that impair health maintenance such as malignant rheumatoid arthritis, trauma such as burns, acne, spots, buckwheat, and skin inflammation. The present invention provides a novel antioxidant and a medicine, food or cosmetic using the same.

In recent years, it has become clear that lipid peroxides produced from active oxygen and unsaturated lipids have adverse effects on living bodies such as aging and the development of adult diseases, and various studies have been conducted. Search for so-called antioxidants that have an effect of scavenging reactive oxygen and inhibiting the production of lipid peroxide, arteriosclerosis, hyperlipidemia, cerebral infarction, heart disease, and their sequelae and stress ulcers Ischemic disorders such as cancer, adult diseases such as cancer, malignant rheumatism, Behcet's disease, Coulomb disease, ulcerative colitis, intractable diseases such as hepatitis, nephritis, Parkinson's disease, diseases caused by chemical substances such as agricultural chemicals, light Some attempts have been made to apply them as therapeutic agents for hypersensitivity and radiation damage. In addition, active oxygen and lipid peroxide are known to cause stains, buckwheat, acne, wrinkles, tarmi, skin inflammation, and the like, as well as to deteriorate food quality and cause a decline in taste quality and nutrition.
On the other hand, Patent Document 1 focuses on the antioxidant action of lemon balm, which is a natural product, and from this, a novel compound having an antioxidant action is isolated and attempted to be applied to pharmaceuticals and the like.
Similarly, in Patent Document 2, active oxygen scavenging action is found in extracts of herbal medicines such as sun pens, gokahi, and dicoppi, and these are being applied to pharmaceuticals and the like.
Japanese Patent Laid-Open No. 11-12270 JP-A-8-283172

At present, typical antioxidants include α-tocopherol, which is a natural product, (vitamin E), ascorbic acid (vitamin C), and BHT (3,5-tert-butyl-4-hydroxy) which is a synthetic compound. Toluene), superoxide dismutase (hereinafter referred to as SOD), which is a biological enzyme, and the like. Moreover, as a typical anti-inflammatory agent, licorice extract, which is a natural product, indomethacin, which is a synthetic compound, and the like can be given.
However, since SOD, which is a biological enzyme, is an enzyme protein, it has disadvantages such as high production yield with high purity and difficulty in maintaining blood concentration when administered in vivo. ing.
On the other hand, vitamin E and vitamin C have the disadvantage that the action of eliminating active oxygen in the living body is not sufficient.
Moreover, it cannot be said that the compounds and active oxygen scavengers described in Patent Document 1 and Patent Document 2 exhibit an antioxidant action have sufficient antioxidant ability. In particular, Patent Document 2 merely uses an ethanol extract of a specific crude drug as it is, and there is no mention of a compound having activity.
Therefore, it was an object to obtain a safe and easily available, useful antioxidant as a pharmaceutical, cosmetic, food and drink, food additive and the like, having a stronger antioxidant ability.

（２）下記式で表される
4-(3,4-Dihydroxyphenyl)-6,7-dihydroxy-2-naphtalenecarboxylic acid（化合物Ｉ）及び／又はその生理的に許容される塩を含有する植物の乾燥体又は抽出物を含む抗酸化剤。

（３）植物はマンシュウウコギ（Acanthopanax sessiliflorus）である上記（２）に記載の抗酸化剤。
（４）上記（１）〜（３）に記載の抗酸化剤を含有する食品。
（５）上記（１）〜（３）に記載の抗酸化剤を有効成分とする医薬組成物。
（６）上記（１）〜（３）に記載の抗酸化剤を含有する化粧料。 The present inventor has solved the above-mentioned problems, and as a result of intensive research, the present inventors have isolated 4- (3,4-Dihydroxyphenyl)-isolated from Acanthopanax sessiliflorus. It was found that 6,7-dihydroxy-2-naphtalenecarboxylic acid (Compound I) has a strong antioxidant action, and the present invention was completed.
That is, the present invention has the following configuration.
(1) Represented by the following formula
An antioxidant containing 4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid (Compound I) and / or a physiologically acceptable salt thereof.

(2) Represented by the following formula
Antioxidant containing dried plant or extract containing 4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid (Compound I) and / or physiologically acceptable salts thereof .

(3) The antioxidant according to (2) above, wherein the plant is Acanthopanax sessiliflorus.
(4) A food containing the antioxidant according to (1) to (3) above.
(5) A pharmaceutical composition comprising the antioxidant according to (1) to (3) as an active ingredient.
(6) Cosmetics containing the antioxidant according to (1) to (3) above.

  4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid (hereinafter referred to as “Compound I”) of the present invention is excellent in that it has a strong antioxidant action. In addition, since Compound I is a natural product and obtained from Manchuriagi used as a crude drug, it is preferable in that it has little influence on the biological system. Therefore, the antioxidant containing the compound I of the present invention and / or a physiologically acceptable salt thereof (hereinafter sometimes simply referred to as “compound I etc.”) can be applied to pharmaceuticals, foods and cosmetics. In particular, it is effective for the prevention and treatment of aging, adult diseases, spots, buckwheat, acne, skin inflammation and the like.

Compound I used in the present invention is obtained from the leaves of Acanthopanax sessiliflorus, which is a genus of the urchinaceae, but if it contains the same compound, the production area is particularly limited. The type of plant is not particularly limited as long as it is a plant containing the compound of the present invention.
Acanthopanax sessiliflorus in the present invention is also called Goka, and its root bark is used as a raw material for traditional Chinese medicines such as nutrition tonic and fatigue recovery.

  In the present invention, Acanthopanax sessiliflorus can be used at any site containing Compound I of the present invention. It is all parts such as leaves, stems, buds, flowers, woody parts, above-ground parts of bark parts (bark) and underground parts such as roots and tubers, seeds, fruits, resins, and the like.

Further, a dried product obtained by drying the plant itself, a pulverized product thereof, a juice obtained by squeezing and extracting the product itself, a crude extract using water or a solvent such as ethyl alcohol, methyl alcohol, diethyl ether, acetone, Compound I obtained by stepwise purification of the extract by various chromatographies such as partitioning and column chromatography can be used. The obtained extract fraction may be concentrated by an appropriate method, or spray-dried or freeze-dried. These may be used alone or in combination of two or more.
For example, an antioxidant obtained by adding 3 L of 99.5% ethanol extract to 1 kg of dried plant of Acanthopanax sessiliflorus and soaking overnight at room temperature is used as an antioxidant and food containing them. These may be used as pharmaceuticals or cosmetics, or may be purified by combining various chromatographies.

The extract containing compound I or the like is preferably an ethyl acetate-soluble fraction obtained by liquid-liquid partitioning of a hot water extract of mankokogi using ethyl acetate / water.
Further, as described above, Compound I and the like may be extracted and purified from the plant of Manchucogi, but the present compound can also be obtained by chemical synthesis. For example, the present compound can be synthesized by a known method as described in the following references.
Reference: Phytochemistry, Vol. 28, no. 3, pp 867-869, 1989

It has never been known that the compound I and the like according to the present invention has an antioxidant action, and is a new finding obtained by the present invention.
Moreover, since compound I etc. have a strong antioxidant effect | action, it can be used as an antioxidant. Further, by using them as foods, medicines or cosmetics containing them, it is possible to prevent and treat aging, adult diseases, spots, buckwheat, acne, wrinkles, tarmi, skin inflammation and the like.

In addition to the compound I obtained as described above, physiologically acceptable salts of this compound can also be used as the antioxidant of the present invention. In this case, compound I and one of its salts may be used alone or in admixture of two or more.
Such salts are not particularly limited as long as they are physiologically acceptable. For example, salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium and magnesium, and the like. And salts with amines such as ammonia, triethylamine, and triethanolamine, and salts with basic amino acids such as arginine and lysine.
In addition, when a modified product of Compound I is used as a pharmaceutical product, it is administered to the human body and metabolized in the body, and when this metabolite exerts a medicinal effect for the first time, the modified product (prodrug) is also included in the pharmaceutical product of the present invention. It is a range. Examples of such modified products include salts and esters of Compound I.

The antioxidant of the present invention is an antioxidant containing Compound I and / or a physiologically acceptable salt thereof, but instead of Compound I, a structure such as Compound II represented by the following formula: Can also be used. That is, the hydrogen atom of the 2-position carboxylic acid group (—COOH) of the naphthalene skeleton of Compound I is replaced with another group. For example, R is a residue obtained by removing a hydroxyl group from alcohols or phenols. In particular, a hydrocarbon group having 10 or less carbon atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group is preferable, and may be a phenyl group.

  The antioxidant referred to in the present invention is also referred to as an antioxidant, and is an agent added to prevent deterioration (antioxidant action) due to oxidation by oxygen. An agent having an erasing action. In the present invention, this antioxidant action is evaluated by measuring singlet oxygen scavenging action, superoxide scavenging action, and hydroxy radical scavenging action described later.

[Antioxidants, medicines]
Either the oral administration or the parenteral administration can be adopted for the antioxidant of the present invention or the medicine containing them. Examples of parenteral administration include transdermal administration, rectal administration, and injection. The solid or liquid non-toxic pharmaceutical carrier suitable for each administration method can be mixed with the antioxidant of the present invention, and can be administered in the form of a conventional pharmaceutical preparation. Examples of such preparations include solid preparations such as tablets, granules, powders and capsules, solutions such as solutions, suspensions and emulsions, lyophilized preparations and the like, which are prepared by conventional means on preparations. can do.

  Examples of the non-toxic pharmaceutical carrier include glucose, lactose, sucrose, starch, mannitol, dextrin, fatty acid glyceride, polyethylene glycol, hydroxyethyl starch, ethylene glycol, polyoxyethylene sorbitan fatty acid ester, amino acid, gelatin, Examples include albumin, water, and physiological saline. Further, if necessary, conventional additives such as a stabilizer, a wetting agent, an emulsifier, a binder, and an isotonic agent can be appropriately added.

[Food]
As a food, it can be blended as it is, with various nutritional components added, or together with optional components usually used in foods. For example, it is included in confectionery, drinks, bread, etc. and is eaten as a health food or food material useful for the prevention and treatment of aging, adult diseases, spots, buckwheat, acne, skin inflammation, and the like. For example, after adding an appropriate auxiliary agent to Compound I etc., it can be used for edible by using conventional means and forming it into an edible form, for example, granule, granule, tablet, capsule, paste, etc. Well, various foods such as processed foods such as ham and sausage, fishery processed foods such as kamaboko and chikuwa, bread, confectionery, butter, powdered milk, fermented dairy products, water, fruit juice, You may add and use for drinks, such as milk, tea, and a soft drink.

  In the present invention, an effective intake amount of Compound I or the like is appropriately selected and determined according to the age, weight, symptoms, administration route, administration schedule, formulation form, strength of the inhibitory activity of the material, etc. For example, in the case of oral administration, it is generally about 0.001 to 1000 mg / kg body weight per day, and may be administered in several divided doses.

  Compound I and the like of the present invention have low toxicity. For example, even when Compound I is orally administered to rats for a long period of 1000 mg / kg daily for 100 days, no deaths are observed and no change in body weight is observed. It was.

[Cosmetics]
The cosmetic containing the antioxidant of the present invention is used to prevent aging, spots, buckwheat, acne, wrinkles, tarmi, skin inflammation, and the like. As a cosmetic to which the present invention is applied, the dosage form is not particularly limited, and for example, it can be used for the following uses. Makeup cosmetics such as skin lotion, milky lotion, cream, beauty liquid, pack cosmetics, makeup cosmetics such as foundation, under makeup, white powder, hair makeup such as hand cream, hair tonic, hair liquid, shampoo, rinse, etc. Fees. These cosmetics can be produced in the same manner as ordinary cosmetics except that the above compound I is blended.

The amount of compound I or the like of the present invention in the cosmetic is not particularly limited, but is preferably in the range of 0.001 to 10% by weight relative to the total amount of the cosmetic, and further 0.01 to 1% by weight. It is more preferable to blend in the range of%. If the compounding amount of Compound I is less than 0.001%, the effect of preventing aging, prevention of wrinkles, stains, acne, buckwheat, skin inflammation, etc. may not be obtained sufficiently, exceeding 10% by weight In the case of blending, the effect reaches a peak and is often not economical.
In addition, when using the fraction of an extract, it can use similarly by converting into a compound density | concentration so that an effect comparable as the said density | concentration may be acquired.

  Moreover, in addition to the antioxidant containing compound I etc., various components generally used in cosmetics can be blended in the cosmetic of the present invention. For example, hydrocarbons such as petroleum jelly and liquid paraffin, esters such as jojoba oil and carnauba wax, triglycerides such as olive oil and beef tallow, higher alcohols such as stearyl alcohol and behenyl alcohol, fatty acids such as stearic acid and behenic acid, Nonionic surfactants such as glyceryl monostearate, polyoxyethylene stearic acid, polyoxyethylene hydrogenated castor oil, polyoxyethylene stearyl ether, anionic surfactants such as soap and sulfate ester, cationic surfactants such as stearylamine, Amphoteric surfactants such as alkyl betaines, polyhydric alcohols such as glycerin and propylene glycol, various powder components, moisturizers, thickeners, colorants, fragrances, pH adjusters, chelating agents, preservatives, or UV protection agents , Anti-inflammatory agents, whitening agents, etc. A.

  Furthermore, the cosmetics of the present invention can be used in combination with other substances exhibiting the same action as these other than the antioxidant containing Compound I and the like.

Next, although an example is given and explained concretely, it is not limited to this.
Production example
Extracted from the leaves of Acanthopanax sessiliflorus The leaves of Acanthopanax sessiliflorus were collected from Changbai Mountain in Jilin Province, China. 80 L of water was added to 10 kg of the dried leaf and extracted at 90 ° C. for 1 hour to obtain an extract. The extract was filtered using a 60 mesh filter, concentrated at 60 until the Brix (soluble solids concentration) was about 10, and filtered through a 250 mesh filter. This was sterilized at 130 ° C. for 30 seconds, spray dried (inlet temperature: 140 ° C., outlet temperature: 80 ° C.), and sieved with a 30 mesh filter. (Yield: 22%) was obtained.

Isolation and purification of 4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid The compound of the present invention was subjected to various column chromatography (hereinafter abbreviated as cc) as shown in FIG. Can be obtained by combining.
That is, the hot water extract (1630.63 g) of the leaf of Manshukogi obtained above was subjected to liquid-liquid partition using ethyl acetate and water, and the resulting ethyl acetate soluble fraction (21.27 g) was obtained. Sephadex LH-20 (2-100 μm, Pharmacia Fine Chemical Co., Ltd.) cc, and eluted with methanol, 4 fractions L-1 to L-4 (L-1: 9.69 g, L-2 : 5.69 g, L-3: 4.63 g, L-4: 0.25 g). Next, the L-4 fraction (0.25 g) was subjected to ODS (Chromatorex ODS: manufactured by Fuji Chemical Co.) cc and eluted with 50% methanol containing 0.01% trifluoroacetic acid (TFA). Nine fractions of O-9 (O-1: 13.1 mg, O-2: 7.6 mg, O-3: 5.0 mg, O-4: 117.2 mg, O-5: 34.8 mg, O-6: 4.1 mg , O-7: 34.8 mg, O-8: 62.0 mg, O-9: 10.6 mg). Furthermore, O-4 and O-5 of those combined fractions (152.0mg), Silica gel (Kieselgel 60 F 254, Merck) was subjected to cc, chloroform: methanol: water (80: 20: 2 v / v / v) 4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid (68.1 mg, yield: 0.0042%), which is the compound of the present invention, by elution using a mixed solution Got.

Spectral data Spectral data of the obtained compound I of the present invention was obtained, and the following results were obtained.
White powder
mp: 325-327 °
Molecular formula: C ₁₇ H ₁₂ O ₆
Molecular weight: 312.2
Molecular composition: C 65.39, H 3.87, O 30.74
IR (KBr): 3440, 3300, 1705, 1620, 1530 cm ^-1
1 H NMR (400 MHz, DMSO-d ₆ ):
δ = 12.71, 9.93, 9.69 (br s, 1H), 9.08 (br s, 2H), 8.19, 7.50 (d, J = 1.6 Hz;
1H), 7.30, 7.23 (s, 1H), 6.86 (d, J = 8.0 Hz; 1H), 6.82 (d, J = 2.1 Hz; 1H),
6.69 (dd, J ₁ = 2.1 Hz, J ₂ = 8.0 Hz; 1H)
¹³ C NMR (400 MHz, DMSO-d ₆ ):
δ = 167.8, 149.0, 147.2, 145.0, 144.7, 137.9, 131.4, 129.4, 128.4, 127.4,
124.6, 122.9, 120.4, 116.9, 115.7, 111.4, 108.0
UV (MeOH):
λmax (logε) 243 (4.25), 293 (sh, 3.94), 312 nm (4.00)
MS (70eV):
m / z (%) 312 (100, M ⁺ ), 268 (22), 266 (10), 249 (19), 221 (36), 165 (18), 164 (10), 163 (18), 88 (10), 63 (10), 45 (17), 43 (35).

Pharmacological test
Measurement of antioxidant effect "Singlet oxygen scavenging action"
Compound I shown in the production examples of the present invention was evaluated for singlet oxygen scavenging action. The evaluation method was measured by the ESR spin trap method using 2,2,6,6-tetramethyl-4-piperidinol (4-OH TEMP) as a spin trap agent. First, 0.1 mL of a 40% (v / v) N, N-dimethylformamide aqueous solution of a singlet oxygen scavenger (compound I) prepared at an arbitrary concentration was dropped onto a commercially available flat-bottom 96-well microplate. Subsequently, 0.02 mL of distilled water, 0.04 mL of 100 mM 4-OH TEMP aqueous solution, and 0.04 mL of 0.1 mM Rose Bengal aqueous solution were mixed in this order to obtain a mixed solution having a total amount of 0.2 mL. This was irradiated with a light emitting diode (green LED) having a maximum wavelength of 530 nm from the back surface of the microplate as a light source for photosensitization reaction for 20 minutes to generate singlet oxygen. This mixed solution was transferred to a flat aqueous solution cell for ESR, and an ESR spectrum was measured. The singlet oxygen elimination rate was determined from the ESR spectrum intensity, and this was plotted against the concentration to determine the 50% inhibition concentration IC ₅₀ value. For comparison, IC ₅₀ values of existing polyphenol compounds were simultaneously obtained. The results are shown in Table 1. The IC ₅₀ value of Compound I was 95.68 μM. From this result, it was recognized that Compound I scavenges singlet oxygen at a lower concentration compared to the polyphenol compound. That is, it was revealed that Compound I exhibits an excellent singlet oxygen scavenging action.

Measurement of antioxidant action "Superoxide scavenging action"
Compound I was evaluated for its superoxide scavenging action. The evaluation method was measured by the ESR spin trap method using 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) as a spin trap agent. First, 0.05 mL of 2 mM hypoxanthine 0.1 mM phosphate buffer (pH 7.4) was added to a polypropylene tube. Subsequently, 2 mM diethylenetriamine-N, N, N ′, N ″, N ″ -5 acetic acid (DETAPAC) 0.1 mM phosphate buffer (pH 7.4) 0.015 mL, stock DMPO 0.015 mL, optional 0.1% of a 2% (v / v) N, N-dimethylformamide aqueous solution of compound (I) prepared at a concentration of 10 U was added, and finally 200 U / mL xanthine oxidase 0.1 mM phosphate buffer (pH 7.4) 0 0.02 mL was added and immediately after this, the mixture was stirred for 5 seconds using a test tube mixer. This mixed solution was transferred to a flat cell for ESR measurement, and an ESR spectrum was measured 1 minute after addition of xanthine oxidase. From the ESR spectrum intensity, the superoxide elimination rate was determined, and this was plotted against the concentration to determine the 50% inhibitory concentration value (IC ₅₀ ). For comparison, the IC ₅₀ of rosmarinic acid often used as an existing superoxide scavenger was also determined. As a result, the IC _{50 of} compound I was 17.91 μM, and the IC ₅₀ of rosmarinic acid was 34.18 μM. As is apparent from this result, it was observed that Compound I eliminates superoxide at a lower concentration compared to rosmarinic acid. That is, it was revealed that Compound I exhibits an excellent superoxide scavenging action.

Measurement of antioxidant activity "Hydroxy radical scavenging effect"
Compound I was evaluated for its hydroxy radical scavenging action. The evaluation method was measured by the ESR spin trap method using DMPO as a spin trap agent. First, 0.02 mL of 0.5 mM iron (II) sulfate aqueous solution was added to a polypropylene tube. Subsequently, 0.1 mL of 0.2 mM DETAPAC 0.1 mM phosphate buffer (pH 7.4), 0.02 mL of 100 mM DMPO aqueous solution, 0.5% (v / v) N, N-dimethylformamide aqueous solution of Compound I 0 .04 mL was sequentially added, and immediately after addition of 0.02 mL of 1 mM aqueous hydrogen peroxide solution, this mixture was transferred to a flat cell for ESR measurement, and the ESR spectrum was measured. Using a sample added with 0.04 mL of 0.5% (v / v) N, N-dimethylformamide aqueous solution not containing Compound I as a control, the hydroxy radical elimination rate was obtained from the ESR spectrum intensity and plotted against the concentration. The 50% inhibitory concentration value (IC ₅₀ ) was determined. For comparison, the IC ₅₀ of dimethyl sulfoxide (DMSO) often used as an existing hydroxy radical scavenger was also determined. As a result, the IC _{50 of} Compound I was 254.8 μM, and the IC ₅₀ of DMSO was 2.434 mM. As is clear from this result, it was observed that Compound I scavenges hydroxy radicals at a lower concentration compared to DMSO. That is, it was revealed that Compound I exhibits an excellent hydroxy radical scavenging action.

A prescription example is shown below.
Formulation Example 1
[Manufacture of tablets]
4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic obtained in Production Example
Using acid (Compound I), tablets having the following composition were produced according to a conventional method.
(Composition) (Composition: Weight%)
Compound I 24
Lactose 63
Cornstarch 12
Guar gum 1

Formulation Example 2
[Manufacture of juice]
Using the compound I obtained in Production Example, a juice having the following composition was produced according to a conventional method.
(Composition) (Composition: Weight%)
Frozen concentrated Wenzhou orange juice 5.0
Fructose glucose liquid sugar 11.0
Citric acid 0.2
L-ascorbic acid 0.02
Fragrance 0.2
Dye 0.1
Compound I 0.2
Wed 83.28

Formulation Example 3
[Manufacture of cosmetics (hand cream)]
Using the compound I obtained in the production example, a hand cream having the following composition was produced according to a conventional method.
(Composition) (Composition: Weight%)
Cetanol 8.0
Stearyl alcohol 2.0
Polyoxyethylene lauryl ether 1.5
Propylene glycol 6.0
Sorbitol 1.0
Paraben 0.4
Compound I 0.5
Vitamin E 0.5
Fragrance 0.1
Purified water 66.0

Formulation Example 4
[Manufacture of cosmetics (skin lotion)]
Using the compound I obtained in the production example, a lotion having the following composition was produced according to a conventional method.
(Composition) (Composition: Weight%)
Purified water residue 1.3-Butylene glycol 8.5
Glycerin 1.5
L-serine 0.1
Mixed isomerized sugar 1.0
Parsley extract 0.1
Rosemary extract 0.3
Compound I 0.1

Formulation Example 5
[Manufacture of cosmetics (milky lotion)]
Using Compound I obtained in Production Example, an emulsion having the following composition was produced according to a conventional method.
(Composition) (Composition: Weight%)
Purified water Residue 1.3-Butyleneglyco 8.0
Carboxyvinyl polymer 0.12
Glycerin 3.0
Mixed isomerized sugar 0.5
L-threonine 0.1
Jojoba oil 1.5
Squalane 1.5
Polyoxyethylene hydrogenated castor oil 1.0
Parsley extract 0.1
Compound I 0.2
Potassium hydroxide 0.04

Formulation Example 6
[Manufacture of cosmetics (beauty liquid)]
Using the compound I obtained in Production Example, a cosmetic liquid having the following composition was produced according to a conventional method.
(Composition) (Composition: Weight%)
Purified water residue 1.3-Butylene glycol 8.0
Trimethylglycine 2.0
Glycerin 5.0
Mixed isomerized sugar 3.0
Compound I 0.2
Carboxyvinyl polymer 0.15
Potassium hydroxide 0.05
Sodium hyaluronate (1% aqueous solution) 0.5

Formulation Example 7
[Manufacture of cosmetics (pack cosmetics)]
Using the compound I obtained in Production Example, a pack cosmetic having the following composition was produced according to a conventional method.
(Composition) (Composition: Weight%)
Purified water Residue Dextran 11.5
Carboxyvinyl polymer 0.3
Diglycerin 17.0
Trimethylglycine 2.0
L-serine 0.1
Mixed isomerized sugar 0.5
Compound I 0.2
Maltitol 4.0
1.3-Butylene glycol 10.0
Polyoxyethylene hydrogenated castor oil 0.5
Sodium carboxymethylcellulose 1.4
Potassium hydroxide 0.1
Capsules containing salt 0.1

  The antioxidant of the present invention can be applied to pharmaceuticals, foods and cosmetics, and is particularly effective for the prevention and treatment of aging, adult diseases, spots, buckwheat, acne, wrinkles, tarmi, skin inflammation, etc. .

FIG. 3 is a diagram showing a method for isolating and purifying 4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid (Compound I).

Claims (6)

Represented by the following formula
An antioxidant containing 4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid (Compound I) and / or a physiologically acceptable salt thereof.

Represented by the following formula
Antioxidant containing dried plant or extract containing 4- (3,4-Dihydroxyphenyl) -6,7-dihydroxy-2-naphtalenecarboxylic acid (Compound I) and / or physiologically acceptable salts thereof .

  The antioxidant according to claim 2, wherein the plant is Acanthopanax sessiliflorus.   The foodstuff containing the antioxidant of Claims 1-3.   The pharmaceutical composition which uses the antioxidant of Claims 1-3 as an active ingredient.   Cosmetics containing the antioxidant of Claims 1-3.

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