JP2009013104A - Xanthone derivative having anti-oxidizing action, method for producing the same, and cosmetics comprising the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a xanthone derivative having weak side-effects and having excellent anti-oxidizing actions, to provide a method for producing the same, and to provide cosmetics containing the same. <P>SOLUTION: This xanthone derivative having the anti-oxidizing action is a chitosan dimer, a chitosan trimer, or a chitosan polymer comprising 32 xanthone molecules, and is obtained by adding arginine to a crushed product of Garcinia mangostana, heating, and extracting with a vegetable oil, or is obtained by adding an apple juice and a lipase for transesterification to the crushed product of Garcinia mangostana, heating and extracting with a vegetable oil. The method for producing the xanthone derivative comprises a process of adding Bacillus natto to the crushed product of Garcinia mangostana, arginine and soybeans, fermenting the mixture to form a fermented product and extracting the fermented product with a vegetable oil. The cosmetic comprises a composition containing the xanthone derivative and a fruit juice extract. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

In order to search for substances that exhibit superior antioxidant action than vitamin C and vitamin E, the search for substances having an antioxidant action based on radical scavenging action from marine plants, algae, microorganisms, animal organisms and plants has been promoted. Alternatively, astaxanthin is isolated from algae such as cryptococcus and hematococcus, and ubiquinone is isolated from cultured yeast and myocardial tissue (see, for example, Non-Patent Document 1).

Each substance has its characteristics. For example, astaxanthin exhibits an antioxidative action about 50 times stronger than vitamin E, but has many technical difficulties or economic burdens in its separation, and coenzyme Q10 is a kind of ubiquinone. Manufacture requires time and labor, and its industrial use is limited (see, for example, Non-Patent Document 2).

In addition, ubiquinone is a mitochondria of the heart and muscles that acts on energy production as a cause of the electron transport system, but on the other hand, its consumption is violent and has the disadvantages that it is easily oxidized in vivo, astaxanthin, procyanidins, etc. Polyphenols have high water solubility, are easily excreted, and have low drawbacks (see, for example, Non-Patent Document 3).

Naturally-occurring antioxidants containing these polyphenols also have drawbacks that their effects are temporary, easily disappear, and tissue accumulation is low (see, for example, Non-Patent Document 4). Therefore, an antioxidant that is well absorbed by the living body and exhibits an antioxidant action with high stability is desired.

Inventions related to antioxidants include, for example, foods with enhanced in vivo antioxidant capacity containing proanthocyanidins and fat-soluble antioxidants. As fat-soluble antioxidants, astaxanthin, ubiquinone, lignans, curcumin There is a report on a composition using a curcumin derivative (see Patent Document 1).

Moreover, there exists an antioxidant characterized by containing at least one of the xanthone derivatives as an invention relating to the antioxidant action by xanthone which is a kind of polyphenol (see Patent Document 2).

Furthermore, there is a cosmetic invention based on the platelet activating factor inhibitory action of xanthone (see Patent Document 3).

However, since xanthone is unstable, commercialization has not been carried out, and an invention of a better xanthone derivative and its utilization method are desired.
Japanese Patent Laid-Open No. 2005-21098 JP 2006-89661 A JP 2004-137210 A Simpson KL et al., Annu Rev Nutr, 1981: 1, 351-374. Lorenz RT et al., Trend Biotechnol 2000: 18, 160-167. Mortensen A et al., Arch Biochem Biophys 2001: 385, 13-19. Scalbert A et al., Biofactors. 2000: 13, 115-120.

Conventionally, polyphenols such as catechin, procyanidin, ubiquinone and astaxanthin derived from natural products have been known to have strong antioxidant action due to radical scavenging action, but their absorption rate is low, and excretion is fast and stable. There is a problem that it is poor in performance and costs are required for production.

Polyphenols have skin irritation, coloration, astringency and bitterness, and their use in food preparations and cosmetic preparations is limited.

Furthermore, natural vitamins, ubiquinone, alpha-lipoic acid and astaxanthin have a problem that they have poor durability, are easily decomposed, are difficult to handle, and are restricted in industrial use.

In addition, chemically synthesized antioxidants have the problem that side effects are reported and users and consumers are shunned.

Further, xanthone alone has a problem that it is poor in stability and it is difficult to obtain an antioxidant action continuously. In addition, the source of xanthone is not specified, and the utilization of xanthone for industry is restricted.

The present invention has been made paying attention to the problems existing in the prior art as described above. The purpose is to provide a xanthone derivative having weak side effects and having an excellent antioxidant action.

Another object of the present invention is to provide a xanthone derivative having an excellent antioxidative effect with weak side effects obtained by adding arginine to a pulverized mangosteen, heating it, and extracting it with a vegetable oil.

It is another object of the present invention to provide a xanthone derivative having an excellent antioxidative effect with less side effects obtained by adding apple juice and lipase for transesterification to a pulverized mangosteen, heating and extracting with vegetable oil.

Also, to provide an efficient production method of an xanthone derivative having an antioxidant action comprising a step obtained by extracting a fermented material obtained by adding fermented natto to fermented mangosteen, arginine and soybean with a vegetable oil. It is in.

In addition, an object of the present invention is to provide a cosmetic product exhibiting an excellent anti-aging effect due to weak side effects comprising a composition containing 0.05 to 1 weight of juice extract per 1 weight of xanthone derivative having an antioxidant action.

In order to achieve the above object, the invention described in claim 1 relates to a xanthone derivative represented by the following formula (1) having an antioxidant action.

  n is 0-30.

The invention described in claim 2 has an antioxidant action in which n is 0 among the xanthone derivatives of claim 1 obtained by adding arginine to a pulverized mangosteen, heating, and extracting with vegetable oil. The present invention relates to a xanthone derivative represented by the following formula (2).

The invention according to claim 3 is obtained by adding apple juice and lipase for transesterification to a pulverized mangosteen, heating and extracting with vegetable oil, wherein n is 1 The present invention relates to a xanthone derivative represented by the following formula (3) having a certain antioxidant action.

Invention of Claim 4 consists of the process obtained by extracting the fermented material which added the fermented natto to fermented mangosteen, arginine, and soybean with vegetable oil, The antioxidant action of Claim 1 is comprised It is related with the manufacturing method of the xanthone derivative which has.

The invention according to claim 5 is a cosmetic comprising a composition containing 0.1 to 1 weight of a fruit juice extract in 1 weight of the xanthone derivative having antioxidant activity according to claim 1 or claim 2 or claim 3. It is about.

Since this invention is comprised as mentioned above, there exist the following effects.

According to the xanthone derivatives according to claims 1 to 3, the side effects are weak and an excellent antioxidant action is exhibited.

According to the method for producing a xanthone derivative according to claim 4, the target xanthone derivative can be obtained efficiently.

According to the cosmetic comprising the composition containing 0.01 to 1 weight of the fruit juice extract in 1 weight of the xanthone derivative according to claim 5, the side effects are weak and an excellent anti-aging action is exhibited.

Hereinafter, the best mode for carrying out the present invention will be described in detail.

First, the xanthone derivative represented by the following formula (1) having an antioxidant action will be described.

  n is 0-30.

In the first place, xanthone is a polyphenol that is biosynthesized by plants and microorganisms, and is characterized by being contained in plants of the family Hypericaceae. Among the plants of the family Hypericaceae, mangosteen and hypericum are rich in xanthone.

The xanthone derivative referred to here is a xanthone polymer as represented by the formula (1).

In the first place, the mother nucleus of xanthone is represented by xanthen-9-one and consists of 13 carbons, 8 hydrogens, and 2 oxygens. The basic structure of the xanthone derivative is represented by 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one.

This xanthone derivative has one 6-position hydroxyl group of 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one and another 1,3,6-trihydroxy-7-mesoxy-xanthene-9- One is a polymer in which the hydroxyl group at the 1-position is bonded through oxygen.

Further, 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one is bonded to the same 6-position and another 1-position hydroxyl group to the above polymer.

In the xanthone derivative here, the number of n indicating the number of bonds is in the range of 0 to 30.

When the number of n indicating the number of bonds is 0, it is a dimer. Further, when the number of n indicating the number of bonds is 1, it is a trimer.

When this xanthone derivative is polymerized, the number of hydroxyl groups increases and exhibits strong antioxidant properties.

The xanthone derivative is preferable because it is structurally stable, easily infiltrates into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and maintains an antioxidant effect.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by esterase in the blood to be decomposed into a single xanthone, and its safety has already been confirmed. Is also safe.

When this xanthone derivative is extracted from a plant, it is necessary to use a Hypericaceae plant, especially mangosteen fruit, flesh, pericarp, leaves, stems, flowers and roots, Hypericum perforatum, Fukugi, Crussia rosea, Hypericum tricolor, Hypericum calicinum Leaves, bark, flowers, fruits and roots such as Terihaboku, Hypericum calcinum, Hypericum hydracoat, Hypericum androsaemum are preferable.

In particular, in the food industry, mangosteen peel is removed during processing, discarded as waste, and not used. Extracting or refining the skin as a raw material is preferable because it effectively uses waste and reduces the amount of waste.

The mangosteen here is represented by the scientific name Garcinia mangostana, and is a tree of the camellia Hypericaceae family Fukugi or Garcinia, which grows in tropical regions such as Southeast Asia, South America and Africa, and bears fruit several times a year. .

The mangosteen used here may be from any of Southeast Asia, South America, and Africa.

The part used for mangosteen may be whole fruit, pulp, pericarp, bark, or root. Of these, the whole fruit, pulp, and peel are preferred because they have a long experience in eating and use as folk medicines and have established safety.

The whole fruit, flesh and pericarp of the plant can be used either in a fresh state or in a dried state, but it is preferable because the desired xanthone derivative is obtained from the dried fruit.

Also, green tea leaves and stems, lotus seeds, fruits and berries, roots, leaves and stems, plants such as ercampule, kotarahim, gyoja garlic, onion, garlic, soybeans, scallops, licorice, vermicelli, barley leaves, barley Flowers, capsicum, oysters, pears, chestnuts, cod, horseradish, bracken, rice, wheat, corn, radish, rape blossoms, cherry blossoms, pine, red mushrooms, red mushrooms, red crocodiles, whales , Wild mushroom, Ibukisawaku, Ukogi, peony, Udo, Ume, Vulture, Shrimp, Ouren, Psyllium, Okera, Okra, Hypericum, Onamomi, Ominae, Oyster, Ivy, Alaska Leopard, Catalpa, Yellowfin, Yellow-billed, Goldworm, Horsetail, Horsetail, Kuzu, Gardenia, Kohonone, Kobushi, Pikachi, Soybean, Sartorii Rose Bucket, Sanshuyu, Janohige, Silane, Honeysuckle, Seri, Assembly, Tamushiba , Crocodile carrot, azalea, tochinoki, tochibanin ginseng, nanten, green rose, chickweed, pearl barley, scallops, baboon, cypress, hithitoba, loquat, fuki, fukujusou, fuji, matatabi, swordfish, yam, cypress Leaves, stems, flowers, fruits or roots are preferred because they are easily available.

The xanthone derivative is preferably extracted from the above-mentioned Hypericaceae plant, Kotarahim, Elcampure or the above-mentioned plant body with the above-mentioned organic solvent or vegetable oil. That is, as vegetable oil, palm oil, palm oil, soybean oil, olive oil, rapeseed oil, rice oil, germ oil, corn oil, safflower oil, linseed oil, almond oil, sesame oil, cacao oil, canola oil, grape seed oil, Oils used in edible or cosmetic products such as sesame oil, wheat germ oil, rice bran oil, safflower oil, perilla oil, tea oil, camellia oil, pumpkin seed oil, peanut oil, grape oil, hazelnut oil, cottonseed oil, peanut oil Further, it is more preferable that the target derivative is stably maintained by using a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract.

Furthermore, the above-mentioned xanthone derivative can be obtained by supercritical extraction using liquefied carbon dioxide from the above-mentioned hypericaceae plant and other plants, fermented fermented products and chemically synthesized reactants. It is preferable because it can be obtained well.

When the xanthone derivative is obtained by a chemical synthesis reaction, it is preferable that the mangosteen peel components are heated together with a metal catalyst such as magnesium or aluminum. These raw materials are put in a reaction tank and a reaction is performed together with a solvent. The reaction product is preferably obtained by extracting the produced xanthone derivative with the above acidic aqueous solution and removing the solvent to obtain a crude product, since the cost required for purification can be reduced.

It is preferable to obtain the above xanthone derivative by fermentation using microorganisms or yeasts because it is confirmed that food safety is safe and food experience is abundant. In this case, the microorganisms used are natto, lactic acid bacteria, red yeast rice Bacillus subtilis and yeast include brewer's yeast and alcoholic yeast, and natto bacteria are particularly preferred because of their excellent transesterification.

When the above fermentation is extracted from a plant, a Hypericaceae plant, in particular, mangosteen fruit, flesh, pericarp, leaves, stems, flowers and roots, Hypericum perforatum, Fukugi, Crussia rosea, Hypericum tricolor, Hypericum calicinum In addition to leaves, bark, flowers, fruits and roots such as Terihaboku, Hypericum calcinum, Hypericum hydracoat, Hypericum androsaemum, etc., microorganisms or yeast are added to fermentation bases such as soybeans using a fermentation tank Is done.

After the fermentation, the desired xanthone derivative can be obtained from a mixture of microorganisms or yeast and fermentation broth. In this case, it is preferable to extract with the said vegetable oil or a solvent.

Furthermore, it is preferable from the viewpoint of efficient production that the desired xanthone derivative is obtained by heating mangosteen peel or extract under alkaline conditions. In this case, although there are several methods for setting the alkaline condition, the use of sodium hydroxide, potassium hydroxide, arginine, or lysine used for food or cosmetic processing is more preferable because safety has been confirmed.

In addition, it is preferable to react the mangosteen peel or extract with fruits or mushroom polyphenol oxidase or lipase from the viewpoint of efficiently producing the target xanthone derivative.

Further, it is preferable to use a purification operation such as a separation resin for purification and separation of the target xanthone derivative. In the case of separation, the organic solvent and vegetable oil described above are used, and further, by using the pine leaf extract-containing vegetable oil in the crude purification stage, the antioxidant and antiseptic effects of the pine leaf extract are exhibited, which is the target. Derivatives are preferred because they remain stable.

Purifying the target xanthone derivative from the reaction product or composition is preferable from the viewpoint of reducing the amount of intake when ingested as a highly pure substance.

When highly purified, a separation carrier or resin is utilized and purified. As the separation carrier or resin, porous polysaccharide, silicon oxide compound, polyacrylamide, polystyrene, polypropylene, styrene-vinylbenzene copolymer, etc. whose surface is coated as described later are used. Those having a particle size of 0.1 to 300 μm are preferable. The finer the particle size, the higher the accuracy of the separation, but the longer the separation time.

For example, a reverse phase carrier or a resin whose surface is coated with a hydrophobic compound is used for separation of a highly hydrophobic substance. Those coated with a cationic substance are suitable for the separation of anionically charged substances.

Also, those coated with an anionic substance are suitable for separating a cationically charged substance. When a specific antibody is coated, it is used as an affinity carrier or resin for separating only a specific substance.

The affinity carrier or resin is used for specific preparation of an antigen using an antigen-antibody reaction. A dispersible carrier or resin is used for isolation of substances such as silica gel (manufactured by Merck) if there is a difference in the distribution coefficient between the substances and the solvent for separation.

Among these, an adsorbent carrier or resin, a dispersible carrier or resin, a molecular sieve carrier or resin, and an ion exchange carrier or resin are preferable from the viewpoint of reducing production costs. Furthermore, the reverse phase carrier or resin and the dispersible carrier or resin are more preferable because the difference in the distribution coefficient with respect to the separation solvent is large.

When the organic solvent is used as the separation solvent, a carrier or resin having resistance to the organic solvent is used. Moreover, the carrier or resin utilized for pharmaceutical manufacture or food manufacture is preferable.

From these points, Diaion (Mitsubishi Chemical Corporation) and XAD-2 or XAD-4 (Rohm and Haas) are used as the adsorptive carrier, and Sephadex LH-20 (Amersham Pharmacia) is used as the molecular sieve carrier. Silica gel as the distribution carrier, IRA-410 (Rohm and Haas) as the ion exchange carrier, and DM1020T (Fuji Silysia) as the reverse phase carrier are more preferable. Of these, Diaion, Sephadex LH-20 and DM1020T are more preferred.

The obtained extract is suspended in a solvent for swelling the carrier for separation or the resin before separation. The amount is preferably 1 to 40 times, more preferably 3 to 20 times the weight of the extract from the viewpoint of separation efficiency. The separation temperature is preferably 4 to 60 ° C., more preferably 15 to 50 ° C., from the viewpoint of the stability of the substance.

As the separation solvent, water or a lower alcohol containing water, a hydrophilic solvent, or a lipophilic solvent is used. As the lower alcohol, methanol, ethanol, propanol and butanol are used, and ethanol used for food is preferable.

When Sephadex LH-20 is used, a lower alcohol is preferable as the separation solvent. When silica gel is used, the separation solvent is preferably chloroform, methanol, acetic acid or a mixture thereof.

When Diaion and DM1020T are used, the separation solvent is preferably a lower alcohol such as methanol or ethanol or a mixed solution of lower alcohol and water.

After collecting the separated fractions, it is preferable to remove the solvent by drying or vacuum drying to obtain the desired xanthone derivative as a powder or concentrated liquid because the influence of the solvent can be excluded.

The xanthone derivative is obtained as a liquid or a powder. The obtained xanthone derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing and fibers, plastic processing, environmental prevention materials, and the like.

As a pharmaceutical, it is used for the purpose of anti-oxidation and anti-inflammatory, and it is used as an anti-cancer agent, mutation suppressor, anti-inflammatory agent, spot, kumi and wrinkle remover, sunscreen, hyperlipidemia improving agent, It is used for the prevention and improvement of arteriosclerotic agents, metabolic syndrome and lifestyle-related diseases. In addition, as veterinary medicines used for animals and medicines used for pets, anti-inflammatory agents, lipolytic agents, anti-obesity agents, Kumi and wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerosis It is used as an agent and anticancer agent.

The above-mentioned food preparation is used for supplements for preventing or improving stains, stains and wrinkles, supplements for the purpose of preventing or improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases.

In addition, as a veterinary food or food preparation used for animals, or as a food preparation used for pets, the purpose of skin regeneration, removal of wrinkles and wrinkles, suppression of fatty liver, improvement of hyperlipidemia, suppression of arteriosclerosis and prevention of cancer, etc. Used as

Examples of the cosmetics include cosmetics, quasi-drugs, and massages that improve or prevent stains, stains, wrinkles, and sagging due to antioxidant and anti-aging effects. Used as oil. In addition, it is used as cosmetics, quasi-drugs, and beauty oils that eliminate or prevent cellulite and wrinkles on the surface due to skin oxidation and aging. It is also used as a veterinary cosmetic used for animals and a cosmetic used for pets.

The aforementioned pharmaceuticals, foods, and cosmetics exhibit an excellent therapeutic or preventive action against skin diseases associated with gene and cell oxidation.

In addition, it is also used for clothing for the purpose of antioxidation and prevention of skin smears and wrinkles by using the fibers added with the above xanthone derivatives, especially underwear, stockings, underwear, swimwear, socks, pajamas, duvets and sheets. It is used for etc.

In addition, it is used for hygiene goods for the purpose of antioxidants, daily goods used in containers, toilets, baths, etc., using the above-mentioned plastics added with xanthone derivatives.

Next, among the above xanthone derivatives obtained by adding arginine to a pulverized mangosteen, heating, and extracting with vegetable oil, the following formula (2) having an antioxidative action where n is 0 is shown. The xanthone derivative will be described.

The xanthone derivative here is a polymer of xanthone.

The mother nucleus of xanthone is indicated by xanthen-9-one, and consists of 13 carbons, 8 hydrogens, and 2 oxygens.

The basic structure of the xanthone derivative here is represented by 1,3,6-trihydroxy-7-mesoxy-xanthen-9-one.

This xanthone derivative has one 6-position hydroxyl group of 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one and another 1,3,6-trihydroxy-7-mesoxy-xanthene-9- One is a polymer in which the hydroxyl group at the 1-position is bonded through oxygen.

The xanthone derivative as used herein has 0 as the number of bonds indicating the number of bonds, that is, it is a dimer.

When this xanthone derivative is polymerized, the number of hydroxyl groups increases and exhibits strong antioxidant properties.

The xanthone derivative is preferable because it is structurally stable, easily infiltrates into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and maintains an antioxidant effect.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by esterase in the blood to be decomposed into a single xanthone, and its safety has already been confirmed. Is also safe.

Xanthone derivatives are obtained by adding arginine to the desired pulverized mangosteen, heating, and extracting with vegetable oil.

The mangosteen here is represented by the scientific name Garcinia mangostana, and is a tree of the camellia Hypericaceae family Fukugi or Garcinia, which grows in tropical regions such as Southeast Asia, South America and Africa, and bears fruit several times a year. .

The mangosteen used here may be from any of Southeast Asia, South America, and Africa.

The part used for mangosteen may be whole fruit, pulp, pericarp, bark, or root.

Of these, the whole fruit, pulp, and peel are preferred because they have a long experience in eating and use as folk medicines and have established safety.

The whole fruit, flesh and pericarp of the plant can be used either in a fresh state or in a dried state, but it is preferable because the desired xanthone derivative is obtained from the dried fruit.

Arginine is a basic amino acid and is also produced by natural plants and fermentation. Ajinomoto arginine is preferred because of its high safety.

As for arginine added with respect to 1 weight of mangosteen, 0.1-2 weight is preferable. When the amount of arginine added is less than 0.1 weight, the reaction product may decrease.

On the other hand, when the amount of arginine added exceeds 1 weight, the alkalinity becomes strong, and the product may be discolored and decomposed.

These are warmed. Mangosteen and arginine are placed in a clean reaction vessel and heated.

As conditions for this heating, the temperature is preferably 20 to 60 ° C, more preferably 30 to 50 ° C.

The heating time is preferably 1 to 24 hours, more preferably 3 to 12 hours.

This reactant is extracted with vegetable oil. Vegetable oils used include palm oil, palm oil, soybean oil, olive oil, rapeseed oil, rice oil, germ oil, corn oil, safflower oil, linseed oil, almond oil, sesame oil, cacao oil, canola oil, grape seed oil, sesame seed oil Oils used in edible or cosmetic products such as oil, wheat germ oil, rice bran oil, safflower oil, perilla oil, tea oil, camellia oil, pumpkin seed oil, peanut oil, grape oil, hazelnut oil, cottonseed oil, peanut oil are used It is done.

In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

As this extraction temperature, 30-90 degreeC is preferable and 40-80 degreeC is more preferable. Moreover, the obtained extract exhibits liquid or powder form.

The xanthone derivative is obtained as a liquid or a powder.

The obtained xanthone derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing and fibers, plastic processing, environmental prevention materials, and the like.

As a pharmaceutical, it is used for the purpose of anti-oxidation and anti-inflammatory, anti-cancer agent, mutation inhibitor, anti-inflammatory agent, Kusumi and wrinkle remover, sunscreen, hyperlipidemia improving agent, anti-arteriosclerosis It is used for prevention and improvement of drugs, metabolic syndrome and lifestyle-related diseases.

In addition, as veterinary medicines used for animals and medicines used for pets, anti-inflammatory agents, lipolytic agents, anti-obesity agents, Kumi and wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerosis It is used as an agent and anticancer agent.

The above-mentioned food preparation is used for supplements for preventing or improving stains, stains and wrinkles, supplements for the purpose of preventing or improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases.

In addition, as veterinary foods and food preparations used for animals, and food preparations used for pets, skin regeneration, removal of stains, wrinkles and wrinkles, suppression of fatty liver, improvement of hyperlipidemia, suppression of arteriosclerosis and prevention of cancer Used for purposes.

The cosmetics are used as cosmetics, quasi-drugs and massage oils for improving or preventing stains, rashes, wrinkles and sagging for the purpose of improving and preventing blemishes, wrinkles, wrinkles and sagging caused by antioxidant reactions. The

In addition, it is used as cosmetics, quasi-drugs, and beauty oils that eliminate or prevent cellulite that has generated unevenness on the surface due to skin oxidation.

It is also used as a veterinary cosmetic used for animals and a cosmetic used for pets.

The aforementioned pharmaceuticals, foods, and cosmetics exhibit an excellent therapeutic or preventive action against skin diseases associated with gene and cell oxidation. In addition, it is also used for clothing for the purpose of antioxidation and prevention of skin stains, rashes and wrinkles using fibers added with the above xanthone derivatives, especially underwear, stockings, underwear, swimwear, socks, pajamas, futons Used for sheets and sheets.

In addition, it is used for hygiene goods for the purpose of antioxidants, daily goods used in containers, toilets, baths, etc., using the above-mentioned plastics added with xanthone derivatives.

Next, among the xanthone derivatives obtained by adding apple fruit juice and lipase for transesterification to the pulverized mangosteen, heating and extracting with vegetable oil, n is 1, and the following formula (3 Xanthone derivatives represented by

The xanthone derivative here is a polymer of xanthone.

The mother nucleus of xanthone is indicated by xanthen-9-one, and consists of 13 carbons, 8 hydrogens, and 2 oxygens.

The basic structure of the xanthone derivative here is represented by 1,3,6-trihydroxy-7-mesoxy-xanthen-9-one.

This xanthone derivative has one 6-position hydroxyl group of 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one and another 1,3,6-trihydroxy-7-mesoxy-xanthene-9- One is a polymer in which the hydroxyl group at the 1-position is bonded through oxygen.

Further, 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one is bonded to the same 6-position and another 1-position hydroxyl group to the above polymer.

The number of n indicating the number of bonds is 1, that is, a trimer.

When this xanthone derivative is polymerized, the number of hydroxyl groups increases and exhibits strong antioxidant properties.

The xanthone derivative is preferable because it is structurally stable, easily infiltrates into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and maintains an antioxidant effect.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by esterase in the blood to be decomposed into a single xanthone, and its safety has already been confirmed. Is also safe.

It is obtained by adding arginine to the desired pulverized mangosteen, heating and extracting with vegetable oil.

The mangosteen here is represented by the scientific name Garcinia mangostana, and is a tree of the camellia Hypericaceae family Fukugi or Garcinia, which grows in tropical regions such as Southeast Asia, South America and Africa, and bears fruit several times a year. .

The mangosteen used here may be from any of Southeast Asia, South America, and Africa.

The part used for mangosteen may be whole fruit, pulp, pericarp, bark, or root. Of these, the whole fruit, pulp, and peel are preferred because they have a long experience in eating and use as folk medicines and have established safety.

The whole fruit, flesh and pericarp of the plant can be used either in a fresh state or in a dried state, but it is preferable because the desired xanthone derivative is obtained from the dried fruit.

Apple fruit juice is the fruit juice part of an apple. Apples are used both in Japan and overseas. The whole apple or pulp extract. This apple juice contains an enzyme that polymerizes polyphenols.

The transesterification lipase used here is, for example, a lipozyme or novozyme 435 manufactured by Novozyme, a lipase PL or lipase QLM manufactured by Meisho Sangyo, or a lipase AY “Amano” manufactured by Amano Enzyme. High quality products such as 30G, lipase G “Amano” 50, lipase F-AP15, and neurase F3G are used, and these are preferable because their safety has been confirmed.

The apple juice added to 1 weight of mangosteen is preferably 0.01 to 1 weight. When the addition amount of apple juice is less than 0.01 weight, the reaction product may decrease.

On the other hand, when the addition amount of apple juice exceeds 1 weight, the sourness of fruit juice becomes strong, and the product may be discolored and decomposed.

The amount of lipase for transesterification added to 1 weight of mangosteen is preferably 0.001 to 0.1 weight. When the addition amount of the lipase for transesterification is less than 0.001 weight, the reaction product may be reduced. On the other hand, when the addition amount of the transesterification lipase exceeds 0.1 weight, the reaction proceeds excessively and the solubility may be lowered.

These are then warmed. That is, mangosteen, apple juice and lipase for transesterification are put in a clean reaction container and heated.

As a heating condition, the temperature is preferably 20 to 50 ° C, more preferably 30 to 40 ° C. The heating time is preferably 1 to 24 hours, more preferably 3 to 12 hours.

This reactant is extracted with vegetable oil. Vegetable oils used include palm oil, palm oil, soybean oil, olive oil, rapeseed oil, rice oil, germ oil, corn oil, safflower oil, linseed oil, almond oil, sesame oil, cacao oil, canola oil, grape seed oil, sesame seed oil Oils used in edible or cosmetics such as oil, wheat germ oil, rice bran oil, safflower oil, perilla oil, tea oil, camellia oil, pumpkin seed oil, peanut oil, grape oil, hazelnut oil, cottonseed oil, peanut oil are used In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract, or a pine leaf extract because the target derivative is stably maintained.

As this extraction temperature, 30-90 degreeC is preferable and 40-80 degreeC is more preferable. The resulting extract exhibits a liquid or powder.

The xanthone derivative is obtained as a liquid or a powder. The obtained xanthone derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing and fibers, plastic processing, environmental prevention materials, and the like.

As a pharmaceutical, it is used for the purpose of anti-oxidation and anti-inflammatory, and it is used as an anti-cancer agent, mutation suppressor, anti-inflammatory agent, spot, kumi and wrinkle remover, sunscreen, hyperlipidemia improving agent, It is used for the prevention and improvement of arteriosclerotic agents, metabolic syndrome and lifestyle-related diseases. In addition, veterinary medicines used for animals and pharmaceuticals used for pets include anti-inflammatory agents, lipolytic agents, anti-obesity agents, stains, scum and wrinkle removers, fatty liver inhibitors, antihyperlipidemic agents, It is used as an arteriosclerotic agent and anticancer agent.

The above-mentioned food preparation is used for supplements for preventing or improving stains, stains and wrinkles, supplements for the purpose of preventing or improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases. In addition, as veterinary foods and food preparations used for animals, and food preparations used for pets, skin regeneration, removal of stains, wrinkles and wrinkles, suppression of fatty liver, improvement of hyperlipidemia, suppression of arteriosclerosis and prevention of cancer Used for purposes.

Examples of the cosmetics include cosmetics, quasi-drugs, and massages that improve or prevent stains, stains, wrinkles, and sagging due to antioxidant and anti-aging effects. Used as oil. In addition, it is used as cosmetics, quasi-drugs, and beauty oils that eliminate or prevent wrinkles and cellulite that have caused unevenness on the surface due to skin oxidation and aging. It is also used as a veterinary cosmetic used for animals and a cosmetic used for pets.

The aforementioned pharmaceuticals, foods, and cosmetics exhibit an excellent therapeutic or preventive action against skin diseases associated with gene and cell oxidation. In addition, it is also used for clothing for the purpose of antioxidation and prevention of skin stains, rashes and wrinkles using fibers added with the above xanthone derivatives, especially underwear, stockings, underwear, swimwear, socks, pajamas, futons Used for sheets and sheets.

In addition, it is used for hygiene goods for the purpose of antioxidants, daily goods used in containers, toilets, baths, etc., using the plastics to which the xanthone derivative is added.
Next, the manufacturing method of the xanthone derivative which has the antioxidant effect | action consisting of the process obtained by extracting the fermented material which added the fermented natto bacteria to soybean and fermented natto bacteria with soybeans is demonstrated.

Next, the manufacturing method of the xanthone derivative which has the antioxidant effect | action consisting of the process obtained by extracting the fermented material which added the fermented natto to fermented mangosteen, arginine, and soybean with vegetable oil is demonstrated.

A xanthone derivative here is a polymer of xanthone.

In the first place, the mother nucleus of xanthone is represented by xanthen-9-one and consists of 13 carbons, 8 hydrogens, and 2 oxygens.

The basic structure of the xanthone derivative here is represented by 1,3,6-trihydroxy-7-mesoxy-xanthen-9-one.

This xanthone derivative has one 6-position hydroxyl group of 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one and another 1,3,6-trihydroxy-7-mesoxy-xanthene-9- One is a polymer in which the hydroxyl group at the 1-position is bonded through oxygen.

Further, 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one is bonded to the same 6-position and another 1-position hydroxyl group to the above polymer.

In the xanthone derivative here, the number of n indicating the number of bonds is in the range of 0 to 30.

When the number of n indicating the number of bonds is 0, it is a dimer. Further, when the number of n indicating the number of bonds is 1, it is a trimer.

When this xanthone derivative is polymerized, the number of hydroxyl groups increases and exhibits strong antioxidant properties.

The xanthone derivative is preferable because it is structurally stable, easily infiltrates into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and maintains an antioxidant effect.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by esterase in the blood to be decomposed into a single xanthone, and its safety has already been confirmed. Is also safe.

The mangosteen used here is the scientific name Garcinia mangostana, which is a tree of the camellia Hypericaceae genus Fukugi or Garcinia, which grows in tropical regions such as Southeast Asia, South America and Africa, and produces fruits several times a year. Bear fruit.

The mangosteen used here may be from any of Southeast Asia, South America, and Africa.

The part used for mangosteen may be whole fruit, pulp, pericarp, bark, or root. Of these, the whole fruit, pulp, and peel are preferred because they have a long experience in eating and use as folk medicines and have established safety.

The whole fruit, flesh and pericarp of the plant can be used either in a fresh state or in a dried state, but it is preferable because the desired xanthone derivative is obtained from the dried fruit.

As arginine used as a raw material, Ajinomoto arginine is preferable because of its high safety and quality. Arginine is a basic amino acid. By making it alkaline, production of a xanthone derivative is promoted.

The weight of arginine is preferably 0.01 to 0.5 weight relative to 1 weight of pulverized mangosteen.

The soybeans used as raw materials here can be from any origin, such as those from Japan, China, the United States, and Russia, and can be pulverized by a pulverizer such as DM-6 manufactured by Nakayama Technical Research Laboratory. preferable.

The Bacillus natto used here is a kind of Bacillus subtilis used for the processing of natto and food. Natto bacteria manufactured by Natto Motopo are preferred because they are suitable for fermentation.

As for each addition amount regarding the said fermentation, 0.1-3 weight is preferable for soybean, and 0.001-0.03 weight is preferable for Bacillus natto with respect to 1 weight of pulverized mangosteen. In addition, the fermentation is preferably carried out in a clean culture tank, and the materials are preferably mixed with tap water.

Mangosteen pulverized product, arginine and soybean, and Bacillus natto are fermented in a clean culture vessel.

This fermentation is heated to 30 to 40 ° C., and the fermentation is performed for 24 to 72 hours. After fermentation, in order to carry out the extraction efficiently, it is diluted with tap water.

The xanthone derivative produced by the fermentation is extracted with vegetable oil. Vegetable oils include palm oil, palm oil, soybean oil, olive oil, rapeseed oil, rice oil, germ oil, corn oil, safflower oil, linseed oil, almond oil, sesame oil, cacao oil, canola oil, grape seed oil, and sesame oil , Wheat germ oil, rice bran oil, safflower oil, perilla oil, tea oil, camellia oil, pumpkin seed oil, peanut oil, grape oil, hazelnut oil, cottonseed oil, peanut oil, and other oils used for food or cosmetics are used .

In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

The above chrysanthemum flower extract-containing vegetable oil is a vegetable oil with an excellent anti-oxidation effect containing an oil-soluble polyphenol extracted by adding vegetable oil to the ground product of chrysanthemum flowers and stably separating the desired derivative. it can.

The pine leaves used in the chrysanthemum flower extract-containing vegetable oil can be used from any of Japan, China and Taiwan.

Chrysanthemum flowers cultivated without using pesticides are preferred because they can avoid the dangers caused by pesticides.

The above-mentioned pine leaf extract-containing vegetable oil is a vegetable oil having an excellent antioxidative effect and containing an oil-soluble polyphenol extracted by adding a vegetable oil to a pulverized pine leaf and stably separating a target derivative. it can.

The pine leaves used for the pine leaf extract-containing vegetable oil may be any of Japanese, Chinese and Taiwanese.

Pine leaves cultivated without using pesticides are preferred because they can avoid the danger of pesticides.

The addition amount of the pine needle extract-containing vegetable oil is 0.02 to 2 weights per 1 weight of the fermented material. In this case, extraction by stirring is preferable, the stirring temperature is preferably 10 to 30 ° C., and the stirring time is preferably 0.5 to 3 hours.

After the stirring, it is preferable to collect the pine leaf extract-containing vegetable oil separated in the upper layer and remove the water. In order to remove moisture, a dryer such as TGD-250LF2 manufactured by Toyo Giken is used.

After the separated xanthone derivative is absorbed into the body, the excess amount is decomposed by digestive enzymes such as esterase and further metabolized in the liver, so that it is highly safe and has few side effects.

Separating and purifying the target xanthone derivative from the reaction product is preferable from the viewpoint that the intake can be reduced as a highly pure substance. As a purification method, it is preferable to use a purification operation such as a separation resin.

As the separation carrier or resin, porous polysaccharide, silicon oxide compound, polyacrylamide, polystyrene, polypropylene, styrene-vinylbenzene copolymer, etc., whose surface is coated, are used. It is preferable to obtain the desired xanthone derivative by separation with an appropriate separation solvent, purification, and removal of the organic solvent.

As the solvent for separation, methanol, ethanol, chloroform, hexane, ethyl acetate, benzene, ether, and the like are used. Of these, ethanol for food processing or ethanol containing water is preferable because of its high use range.

The xanthone derivative thus obtained is obtained as a liquid or a powder.

The obtained xanthone derivative is used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing, fibers, plastics and the like.

Drugs include anti-inflammatory agents, topical lipolytic agents, anti-cellulite agents, stains, kusumi and wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerosis agents, metabolic syndrome and lifestyle-related diseases Used for prevention and improvement. In addition, as veterinary medicines used for animals and medicines used for pets, as lipolytic agents, anti-obesity agents, stains, kumi and wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, etc. Used.

As the above-mentioned food preparation, supplements for preventing or improving stress caused by antioxidant action, supplements for the purpose of preventing or improving neural activity or local fat loss, cancer, metabolic syndrome and lifestyle-related diseases, etc. used.

In addition, veterinary foods and food preparations used for animals, and food preparations used for pets are also used for the purpose of removing kusumi and wrinkles, inhibiting fatty liver, improving hyperlipidemia, inhibiting arteriosclerosis and preventing.

The cosmetics are used as cosmetics for improving or preventing sagging caused by fat accumulation, quasi drugs and massage oils. In addition, it is used as cosmetics, quasi-drugs, and massage oils that eliminate or prevent cellulite that has produced unevenness on the surface due to fat accumulation.

It is also used as a veterinary cosmetic used for animals and a cosmetic used for pets.

The aforementioned pharmaceuticals, foods and cosmetics exhibit excellent therapeutic or preventive action against metabolic syndrome and skin diseases derived therefrom. It is also used for clothing intended to remove fat using the fiber added with the xanthone derivative, particularly for underwear, stockings, underwear, swimwear, socks, pajamas, futons and sheets.

In addition, it is used for containers, toilets, baths, etc. for the purpose of lipolysis using the plastics to which the above xanthone derivatives are added.

Next, a cosmetic comprising a composition containing 0.05 to 1 weight of a fruit juice extract with respect to 1 weight of the xanthone derivative having an antioxidant action will be described.

The xanthone derivative having an antioxidant action here is a polymer of the above xanthone xanthone.

In the first place, the mother nucleus of xanthone is represented by xanthen-9-one and consists of 13 carbons, 8 hydrogens, and 2 oxygens.

The basic structure of the xanthone derivative here is represented by 1,3,6-trihydroxy-7-mesoxy-xanthen-9-one.

This xanthone derivative has one 6-position hydroxyl group of 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one and another 1,3,6-trihydroxy-7-mesoxy-xanthene-9- One is a polymer in which the hydroxyl group at the 1-position is bonded through oxygen.

Further, 1,3,6-trihydroxy-7-mesoxy-xanthene-9-one is bonded to the same 6-position and another 1-position hydroxyl group to the above polymer.

In the xanthone derivative here, the number of n indicating the number of bonds is in the range of 0 to 30.
When the number of n indicating the number of bonds is 0, it is a dimer. Further, when the number of n indicating the number of bonds is 1, it is a trimer.

When this xanthone derivative is polymerized, the number of hydroxyl groups increases and exhibits strong antioxidant properties.

The xanthone derivative is preferable because it is structurally stable, easily infiltrates into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and maintains an antioxidant effect.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by esterase in the blood to be decomposed into a single xanthone, and its safety has already been confirmed. Is also safe.

The fruit juice extract referred to here is an extract of fruit juice obtained from naturally cultivated or cultured fruit flesh, pericarp, seeds and the like. Fruits of fruit juice extract include apple, pear, cranberry, raspberry, cranberry, cherry, mandarin orange, orange, fig, apricot, mango, melon, grape, loquat, banana, watermelon, cucumber and the like.

The fruit-producing area may be derived from Japan, China, the United States, South America, Asia, or Africa.

As the fruit juice extract, any of a liquid of a pulverized fruit itself, a freeze-dried product, and a powdered product can be used.

A fruit juice extract is 0.05-1 weight with respect to 1 weight of said xanthone derivative. Moreover, when the weight of a fruit juice extract is less than 0.05 weight with respect to 1 weight of xanthone derivatives, there is a possibility that a cosmetic composition cannot be obtained sufficiently.

Furthermore, when the weight of a fruit juice extract exceeds 1 weight with respect to 1 weight of xanthone derivatives, there exists a possibility that the appearance may worsen because the pigment component of a fruit juice extract increases.

In order to obtain the said composition, it is preferable to heat after mixing. As heating conditions, the temperature is 25 to 55 ° C., and the heating time is 6 to 48 hours.

When the heating temperature is lower than 25 ° C, there is a possibility that sufficient reaction does not occur. When the heating temperature is higher than 55 ° C., the reaction product generated by oxidation may turn brown. When the heating time is less than 6 hours, a sufficient product may not be obtained.

If the heating time exceeds 48 hours, the product produced by oxidation may turn brown.

This composition is preferable because the above-described xanthone derivative is continuously released little by little and becomes a continuous composition.

Furthermore, the composition is processed together with other raw materials as a cosmetic. Thereafter, it can be used together with oils, surfactants, vitamins, ultraviolet absorbers, thickeners, moisturizers, auxiliary materials and the like in accordance with conventional methods.

It can be in the form of lotion, cream, ointment, lotion, milky lotion, pack, oil, soap, face wash, fragrance, audi cologne, bath preparation, shampoo, rinse and the like. The form of the cosmetic preparation is arbitrary, and can be used as a solution, cream, paste, gel, gel, solid, or powder.

As a cosmetic, it is applied to the skin several times a day. The daily coating amount is preferably 0.01 to 10 g, more preferably 0.05 to 3 g, and further preferably 0.1 to 2 g. When the amount of application per day is less than 0.01 g, there is a possibility that the effect of treating or preventing spots, scum, wrinkles and sagging may not be exhibited. When the application amount per day exceeds 10 g, the cost may increase.

Cosmetics as used herein are basic cosmetics, whitening cosmetics, hair cleansing agents, treatment agents, dyeing hairs, hair restorers, hair nourishing agents, bodies used for humans for the purpose of improving or preventing spots, stains, wrinkles and sagging Wash, and quasi-drug.

In addition, cosmetics or pet shampoos and body wash as skin improvers for animals.

This cosmetic exhibits excellent sunburn, stain and wrinkle improvement effects by exhibiting an antioxidant action and anti-aging. That is, it works to remove sunburn caused by ultraviolet rays and stains and wrinkles generated by the oxidizing action of the skin, and exhibits an excellent anti-aging action.

Furthermore, it can also be used as a moisture moisturizer that protects against water loss due to sunburn by preventing sunburn oxidation.

In addition, this cosmetic product also prevents wrinkles, stains, and spots by preventing oxidation against chemical and allergen-induced atopy and chemical hypersensitivity.

Hereinafter, the embodiment will be specifically described with reference to examples and test examples. In addition, the following description is an example and it can implement by changing a form.

First, the xanthone derivative obtained by fermentation will be described.

Mangosteen peel cultivated in Thailand was used as a raw material. First, the mangosteen peel was washed with water and dried. This was pulverized with a pulverizer (DM-6 manufactured by Nakayama Technical Research Institute).

1 kg of the pulverized mangosteen was put in a clean culture tank, and 3 L of tap water was added. To this was added 100 g of Ajinomoto arginine.

This was washed with Chinese soybeans, then heated to 39 ° C. for 90 minutes and pulverized to obtain 1.5 kg of pulverized soybeans.

Furthermore, 10 g of natto bacteria made by Natto Motopo was added. Fermentation was continued for 42 hours at 37 ° C. with stirring.

2 L of tap water was added to the tank after the fermentation. This was made into a fermented product.

3 kg of RIKEN vitamin palm oil was added to the fermented product, and the mixture was stirred for 3 hours and mixed.

The oil-soluble part separated by the palm oil which left this still and isolate | separated into the upper layer was extract | collected as a liquid. In order to remove water, it was subjected to TGD-250LF2 manufactured by Toyo Giken, and the desired xanthone derivative was obtained as an oily substance. This was used as the sample of Example 1.

Below, preparation of the xanthone derivative obtained by reacting the ground material of mangosteen and arginine is described.

2 kg of mangosteen peel from Thailand was thoroughly washed with tap water and dried with a dryer. Further, 1 kg of this mangosteen was subjected to a pulverizer (manufactured by Sanriki Seisakusho Co., Ltd., a three-powered universal pulverizer) and pulverized to obtain a pulverized mangosteen.

1 kg of pulverized mangosteen was put into a clean cylinder and 9 L of tap water was added. To this, 230 g of Ajinomoto arginine was added and stirred.

This was heated to 60 ° C. and stirred at a rate of 65 times / minute for 12 hours to obtain a heated solution.

After cooling the cylinder containing the warming solution with tap water, 2 kg of RIKEN vitamin palm oil was added, and the oil portion was collected. This was used as the sample of Example 2.

Below, preparation of the xanthone derivative obtained by making it react with mangosteen, apple fruit juice, and transesterification enzyme is described.

2 kg of pericarp was collected from Thai mangosteen, thoroughly washed with tap water, and dried with a dryer (GZQ3 type, manufactured by Nishimura Kikai Co., Ltd.). This was used as the raw material mangosteen.

2 kg of this mangosteen was subjected to a pulverizer (manufactured by Sanriki Seisakusho Co., Ltd., a three-purpose universal pulverizer) and pulverized to obtain a pulverized mangosteen.

1 kg of pulverized mangosteen was put into a clean cylinder and 10 L of tap water was added. To this, 1 kg of apple fruit juice obtained by crushing apples from Aomori was added and stirred.

Furthermore, 10 g of lipase AY “Amano” 30G manufactured by Amano Enzyme Inc. was added, heated to 37 ° C., and stirred at a rate of 70 times / min for 10 hours to obtain a heated solution.

After cooling the cylinder containing the warming liquid with tap water, 1 kg of RIKEN vitamin palm oil was added, and the oil portion was collected.

This was dried by a vacuum dryer (manufactured by AKM Kyushu Technos, Clean Dry) to obtain a xanthone derivative to which palmitic acid was bound as an oily liquid. This was also used as the sample of Example 3.

Below, the identification test of a xanthone derivative is demonstrated.
(Test Example 1)

Each xanthone derivative obtained in Example 1, Example 2 and Example 3 obtained as described above was dissolved in purified ethanol and analyzed by high performance liquid chromatography with a mass spectrometer (HPLC, Shimadzu Corporation). Furthermore, it analyzed with the nuclear magnetic resonance apparatus (NMR, the Bruker make, AC-250).

As a result, a dimer and a trimer of xanthone were obtained from the specimen of Example 1, and a xanthone derivative consisting of 2 to 32 xanthones was further identified.

In addition, a dimer of xanthone was identified from the specimen of Example 2. Furthermore, from the sample of Example 3, a xanthone trimer was identified.

Below, the measurement test of the antioxidant action of a xanthone derivative is demonstrated.
(Test Example 2)

Here, radical scavenging activity was measured as an index of antioxidant activity. That is, a method was used in which radicals produced by xanthine oxidase were measured using 1,1-diphenyl-2-picrylhydrazyl (DPPH, manufactured by Aldrich).

First, xanthine oxidase (manufactured by Aldrich) was dissolved in 0.01 M phosphate buffer, hypoxanthine was added thereto, and the mixture was heated to 37 ° C. to generate radicals. To this solution, the test specimen solutions of Example 1, Example 2 and Example 3 were added.

Furthermore, 0.1 M DPPH solution was added and the absorbance at 520 nm was measured. Vitamin E was used as a positive control.

As a result, the radical scavenging ability of Example 1 was 2.3 times that of astaxanthin, 8.4 times that of coenzyme Q10, and 230 times that of vitamin E.

In Example 2, the radical scavenging ability was 2.9 times that of astaxanthin, 7.9 times that of coenzyme Q10, and 350 times that of vitamin E.

Further, Example 3 exhibited radical scavenging ability 3.4 times that of astaxanthin, 10.5 times that of coenzyme Q10, and 460 times that of vitamin E.

From these results, it was concluded that all of the xanthone derivatives of Example 1, Example 2 and Example 3 exhibited excellent antioxidant action.

Below, the cosmetics which consist of a xanthone derivative are demonstrated.

To 100 g of the xanthone derivative obtained in Example 1, 10 g of grape juice extract made by Kongo Pharmaceutical was added and reacted at 30 ° C. for 6 hours to obtain a composition.

To 100 g of this composition were added 0.2 g of sodium gluconate, 0.1 g of lipase F-AP15 manufactured by Amano Enzyme, and 1 g of polyethylene glycol monostearate, and the mixture was heated at 21 ° C. for 24 hours.

After cooling, 1 g of lipophilic glyceryl monostearate, 2 g of horse oil ester and 3 g of oleic acid were heated and dissolved. Furthermore, 2 g of propylene glycol, 0.1 g of α-tocopherol and 70 g of purified water were added. These were dissolved and then cooled to obtain an emulsion. This was used as the sample of Example 4.

Below, the test of the sunburn improvement effect by the ultraviolet-ray of cosmetics is demonstrated.
(Test Example 3)

Using the emulsion obtained in Example 4, an improvement test for sunburn caused by ultraviolet rays was performed on 6 women aged 35 to 66 years.

A wrinkle improvement test against ultraviolet rays was conducted. That is, 6 cases were divided into 2 groups, and 1 g of the emulsion of Example 4 was applied to the face for 14 days. At the same time, a group using an emulsion containing only the base material was set.

The woman was exposed to ultraviolet rays for 1 hour every day with an ultraviolet irradiation device for sunburn (Neotan 888, manufactured by Emrock). Before use and 14 days after use, skin skin temperature and skin area per unit area using skin elasticity and skin surface horny layer moisture content measuring device (IBS, SKICON200) using skin elasticity and elasticity meter (Cutometer) The length of wrinkles was measured.

As a result, the skin temperature of 0.22 ° C. was reduced as an average value in the emulsion of Example 4 as compared with the use of the emulsion of only the base material. Moreover, the skin surface angle layer moisture content increased to 140% in the usage example of the emulsion of Example 4 as compared with the usage of the emulsion only of the base material. Further, the elasticity of the elasticity meter increased to 156% in the example of using the emulsion of Example 4 as compared to the emulsion of the base material alone.

The wrinkle length was 67% in the usage example of Example 4 as compared to the usage example of the emulsion containing only the base material. Clearly, the wrinkle reduction was recognized, and an excellent anti-aging action was confirmed.

On the other hand, no particular discomfort or inconvenience was found in the feeling of use. As a result, the emulsion obtained in Example 4 was found to have a skin temperature lowering effect, a skin moisture content retaining effect, and a wrinkle improving effect.

The xanthone derivative having an antioxidative action according to the present invention prevented or improved oxidation, and exhibited an excellent function with weak side effects. These xanthone derivatives improve cancer, genetic mutation, arteriosclerosis, wrinkles and sagging, lifestyle-related diseases and oxidative stress.

Furthermore, cosmetics made of xanthone derivatives having an antioxidant action are excellent in preventing, improving and anti-aging effects of sunburn, cousins, stains, wrinkles and tarmi, and improve public QOL.

Mangosteen peel is treated as waste. The present invention reduces waste from the point of effectively using these wastes, and as a result, can prevent environmental destruction caused by soil and ocean eutrophication due to wastes, and can effectively use agricultural resources and develop industries. It contributes to.

Claims (5)

A xanthone derivative represented by the following formula (1) having an antioxidant action.

n is 0-30. The xanthone derivative according to claim 1, which is obtained by adding arginine to a pulverized mangosteen, heating, and extracting with a vegetable oil. Xanthone derivatives.

The following xanthone derivatives obtained by adding apple juice and lipase for transesterification to a pulverized mangosteen, heating and extracting with vegetable oil, and having an antioxidant action wherein n is 1 A xanthone derivative represented by the formula (3).

The method for producing a xanthone derivative having an antioxidative effect according to claim 1, comprising a step obtained by extracting a fermented product obtained by adding fermented natto to fermented mangosteen, arginine and soybeans with a vegetable oil. A cosmetic comprising a composition containing 0.05 to 1 weight of a fruit juice extract with respect to 1 weight of the xanthone derivative having an antioxidant action according to claim 1, claim 2, or claim 3.