JP2009013105A - Xanthone derivatives having collagen-increasing action, method for producing the same, cosmetics and food preparation comprising the derivatives - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide xanthone derivatives having weak side effects and having an excellent collagen-increasing action, to provide a method for producing the same, to provide food preparations and cosmetics comprising the derivatives. <P>SOLUTION: The xanthone derivative having the collagen-increasing action is a compound obtained by binding xanthone with one selected from palmitic acid, para-coumaric acid, sinapic acid, xanthone carboxylic acid, trans-cinnamic acid and coffeic acid. The method for producing the xanthone derivative comprises a process of fermenting the crushed product of Garcinia mangostana and soybeans with Bacillus natto and extracting the fermentation product with a vegetable oil, or a process of extracting the crushed product of Garcinia mangostana with liquefied carbon dioxide. The cosmetic and the food preparation each is a composition comprising the xanthone derivative, a vegetable oil containing a chrysanthemum flower extract and a vegetable oil containing a pine leaf extract. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

Collagen is a protein that constitutes a cell matrix, and is present in skin, bone, cartilage, blood vessels, and membrane tissues in various tissues. There are more than 10 types, and their functions are diverse, such as the construction of the skeleton of the parenchyma, bone construction, protection of the tissue from inflammation, suppression of cancer invasion and prevention of metastasis.

Fibroblasts produce collagen, and the production involves fibroblast proliferation stimulation and growth factors, and activation of transcription factors induces collagen production at the gene level (see, for example, Non-Patent Document 1). ).

The living body is decomposed by an enzyme that degrades collagen, collagenase, or matrix metalloprotease to become a peptide or amino acid, and its function disappears. This collagenase is induced and activated by inflammation and cancer cells.

Further, even with arthritis, collagenase is produced by inflammatory cells such as inflammatory tissue and neutrophils produced around cartilage sites and muscles, and collagen is degraded and disappeared, resulting in disordered tissue construction (for example, non-patent literature) 2).

As a method of increasing collagen, there are a method of increasing collagen production of fibroblasts and inhibition of collagenase activity or suppression of induction, etc. It is preferable to use both methods in combination. Research and development of extraction methods are underway.

Methods for increasing collagen, drugs, foods, and cosmetics include cancer cell metastasis, suppression of angiogenesis related to cancer metastasis, suppression of cancer cell proliferation, suppression of arthritis, improvement of inflammation, suppression of osteoporosis, suppression of cellulite, Since it is effective in improving, preventing and preventing wrinkles and talmi, methods for increasing collagen have been studied.

Plants and herbs contain active ingredients that increase collagen, and these active ingredients are being isolated and purified (for example, see Non-Patent Document 3).

Although anti-inflammatory agents such as fenbuchen, indomethacin, and ipflofen are known as chemically synthesized collagenase inhibitors, side effects such as dry cough and gastrointestinal disorders have been reported for each, and ingredients and preparations with fewer side effects (For example, refer nonpatent literature 4).

As an invention for increasing collagen, there is a composition containing a phenol compound derived from mimosa, and the composition comprising an effective amount of a biologically active phenol compound-containing extract or its active fraction obtained from white mulberry (For example, refer to Patent Document 1).

As an invention of a substance that inhibits collagenase, there is a collagenase activity inhibitor containing at least one of magnolol and honokiol as an active ingredient. Here, honoki leaves, bark (shoku), trunk material, root bark, etc. And the component contained in these is utilized (for example, refer patent document 2).

In addition, as terpenes derived from herbs and plants, there is an invention concerning the use of at least one of saponin or sapogenol that is cosmetically acceptable as a cosmetic agent for increasing collagen in the dermis-epidermal junction (for example, (See Patent Document 3).

However, in any of the inventions, the effect is limited due to either the enhancement of collagen production or the inhibition of collagenase, and the utilization as an industry is limited.
Japanese Patent No. 3626727 Japanese Patent No. 2886623 Special table 2002-516837 Booth B et al., Biochim Biophys Acta, 607, 145-160, 1980. Peel N et al., Bayliers Clin Rheumatol, 6, 351-372, 1992. Niizawa A et al., Clin. Exp. Rheumatol, 21, 57-62, 2003. Crossley R, Am. J. et al. Med, 75, 84-90, 1983.

As described above, a chemically synthesized anti-inflammatory agent or substance exhibiting a collagenase inhibitory action has a problem that side effects such as dry cough and gastrointestinal disorders occur.

On the other hand, there is a problem that although the safety of a naturally derived substance is high, its effect is mild. Therefore, a natural product-derived substance that has weak side effects and exhibits an excellent collagen-increasing action with an anti-inflammatory effect is desired.

The present invention has been made paying attention to the problems existing in the prior art as described above. The object is to provide a xanthone derivative that has low side effects and exhibits an excellent collagen increasing action.

Among the xanthone derivatives obtained by adding palmitic acid and lipase for transesterification to the pulverized mangosteen, heating and extracting with vegetable oil, providing a xanthone derivative having an action of increasing collagen in which X is palmitic acid. is there.

Of xanthone derivatives obtained by adding para-coumaric acid and lipase for transesterification to pulverized mangosteen, heating and extracting with vegetable oil, xanthone derivatives having an action of increasing collagen, wherein X is para-coumaric acid, Is to provide.

Among the xanthone derivatives obtained by adding sinapinic acid and lipase for transesterification to a pulverized mangosteen, heating and extracting with vegetable oil, providing a xanthone derivative having an action of increasing collagen, wherein X is sinapinic acid is there.

Among the xanthone derivatives obtained by adding xanthone carboxylic acid and transesterification lipase to a pulverized mangosteen, heating, and extracting with vegetable oil, a xanthone derivative having an action of increasing collagen in which X is xanthone carboxylic acid is provided That is.

It is an object of the present invention to provide a method for producing a xanthone derivative having a collagen increasing action comprising a step obtained by extracting a pulverized mangosteen and a fermented product obtained by adding natto to fermented soybeans with a vegetable oil.

An object of the present invention is to provide a method for producing a xanthone derivative having an action of increasing collagen, comprising a step of adding liquefied carbon dioxide to a pulverized mangosteen and extracting it.

Provided is a cosmetic product comprising a composition containing 0.05 to 0.8 weight of chrysanthemum flower extract-containing vegetable oil and 0.05 to 0.8 weight of pine leaf extract-containing vegetable oil to 1 weight of xanthone derivative having an action of increasing collagen. It is to be.

A food preparation comprising a composition containing 1 to 1 weight of xanthone derivative having an action of increasing collagen, 0.01 to 0.5 weight of vegetable oil containing chrysanthemum flower extract and 0.01 to 0.5 weight of vegetable oil containing pine needle extract. Is to provide.

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 a collagen increasing action.

  X is any one selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthonecarboxylic acid, transcinnamic acid, and caffeic acid.

The invention according to claim 2 is obtained by adding palmitic acid and transesterification lipase to a pulverized mangosteen, heating and extracting with a vegetable oil, wherein X is palmitic in the xanthone derivative according to claim 1. The present invention relates to a xanthone derivative represented by the following formula (2) having an action to increase collagen, which is an acid.

The invention according to claim 3 is obtained by adding para-coumaric acid and lipase for transesterification to a pulverized mangosteen, heating and extracting with a vegetable oil. Among the xanthone derivatives according to claim 1, X Relates to a xanthone derivative represented by the following formula (3), which has a collagen-increasing action, wherein is para-coumaric acid.

The invention according to claim 4 is obtained by adding sinapinic acid and transesterification lipase to a pulverized mangosteen, heating and extracting with a vegetable oil, and among the xanthone derivatives according to claim 1, X is The present invention relates to a xanthone derivative represented by the following formula (4) having an action of increasing collagen, which is icosapentaenoic acid.

The invention according to claim 5 is obtained by adding xanthonecarboxylic acid and lipase for transesterification to a pulverized mangosteen, heating and extracting with vegetable oil, and among the xanthone derivatives according to claim 1, X is The present invention relates to a xanthone derivative represented by the following formula (5) having an action of increasing collagen, which is xanthone carboxylic acid.

The invention described in claim 6 relates to a xanthone derivative having an action of increasing collagen according to claim 1, obtained by extracting a fermented product obtained by adding fermented natto to fermented soybeans and fermented natto to mangosteen. It is.

Invention of Claim 7 is related with the manufacturing method of the xanthone derivative which has the collagen increase effect | action of Claim 1 which consists of the process which adds and extracts liquefied carbon dioxide to the ground material of mangosteen.

The invention according to claim 8 is a chrysanthemum flower extract added to 1 weight of the xanthone derivative having the collagen-increasing action according to claim 1, claim 2, claim 3, claim 4, claim 5, or claim 6. The present invention relates to a cosmetic comprising a composition containing 0.05 to 0.8 weight of vegetable oil and 0.05 to 0.8 weight of pine leaf extract-containing vegetable oil.

The invention according to claim 9 is a chrysanthemum flower extract added to 1 weight of the xanthone derivative having the collagen-increasing action according to claim 1, claim 2, claim 3, claim 4, claim 5, or claim 6. The present invention relates to a food preparation comprising a composition containing 0.01 to 0.5 weight of vegetable oil and 0.01 to 0.5 weight of pine leaf extract-containing vegetable oil.

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

According to the xanthone derivative according to claim 1, the side effect is weak and an excellent collagen increasing action is exhibited.

According to the xanthone derivative obtained by adding palmitic acid and lipase for transesterification to the pulverized mangosteen according to claim 2, heating and extracting with vegetable oil, side effects are weak and an excellent collagen increasing action is exhibited. Is done.

According to the xanthone derivative obtained by adding para-coumaric acid and lipase for transesterification to the pulverized mangosteen according to claim 3, heating and extracting with vegetable oil, the side effects are weak and the collagen increasing action is excellent. Is demonstrated.

According to the xanthone derivative obtained by adding sinapinic acid and lipase for transesterification to the pulverized mangosteen according to claim 4, heating, and extracting with vegetable oil, side effects are weak and excellent collagen increasing action is exhibited. Is done.

According to the xanthone derivative obtained by adding xanthone carboxylic acid and lipase for transesterification to the pulverized mangosteen according to claim 5, heating and extracting with vegetable oil, side effects are weak and an excellent collagen increasing action is obtained. Demonstrated.

According to the method for producing a xanthone derivative obtained by extracting the fermented material obtained by adding fermented natto to fermented soybeans and fermented natto to soybeans according to claim 6, the xanthone derivative is efficiently produced.

According to the method for producing a xanthone derivative having a collagen increasing action comprising the step of adding and extracting liquefied carbon dioxide to the pulverized mangosteen according to claim 7, the xanthone derivative is efficiently produced.

According to the cosmetic comprising a composition containing 0.05 to 0.8 weight of chrysanthemum flower extract-containing vegetable oil to 1 weight of the xanthone derivative according to claim 8, the side effect is weak, and an excellent wrinkle and talmi improving action is obtained. Demonstrated.

According to the food preparation comprising a composition containing 0.01 to 0.5 weight of chrysanthemum flower extract-containing vegetable oil to 1 weight of the xanthone derivative according to claim 9, side effects are weak, and an excellent wrinkle and tarmi improving action Is demonstrated.

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

First, a xanthone derivative represented by the following formula (1) having a collagen increasing action will be described.

  X is any one selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthonecarboxylic acid, transcinnamic acid, and caffeic acid.

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 here is selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, transcinnamic acid and caffeic acid as the xanthone skeleton as shown in the above formula (1). Any one is an ester-linked derivative.

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 xanthone derivative here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which a hydroxyl group at the 3-position As substituents, organic acids such as palmitic acid, para-coumaric acid, sinapinic acid, xanthonecarboxylic acid, transcinnamic acid, and caffeic acid, phenylpropanoid organic acids and fatty acids are ester-bonded.

The above xanthone derivative is a combination of palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, and caffeic acid. It is easy to enter the cell, the structure of the xanthone derivative is stabilized, and is excellent in the collagen increasing action as compared with xanthone itself.

The xanthone derivatives here are preferred because they are structurally stable and easily infiltrate into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and the action of increasing collagen is sustained.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by the esterase in the blood, and xanthone and the respective palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, The xanthone derivatives are also highly safe because they are decomposed into caffeic acid and their respective safety has been confirmed.

Among the above xanthone derivatives, when X is palmitic acid, the saturated fatty acid residue of palmitic acid penetrates into the cell membrane, is easily absorbed into the cell, easily works on fibroblasts and interstitial tissues, and enhances the collagen increasing action. Is preferable.

Among the above xanthone derivatives, when X is para-coumaric acid, a benzene nucleus having a hydroxyl group of para-coumaric acid exhibits a blood flow dilating action, is easy to penetrate to the local area, and is preferable because collagen increasing action is enhanced. .

Among the above xanthone derivatives, when X is sinapinic acid, the benzene nucleus having the methoxy group of sinapinic acid exhibits an inhibitory action on inflammatory prostaglandin production, so that the collagen increasing action is stable while suppressing the inflammatory action. Therefore, it is preferable.

Among the above xanthone derivatives, when X is xanthone carboxylic acid, the xanthone residue of xanthone carboxylic acid exhibits an anti-inflammatory action, and thus the collagen increasing action is stably exhibited while suppressing the inflammatory action. preferable.

Among the above xanthone derivatives, when X is trans-cinnamic acid, the unsaturated fatty acid residue of trans-cinnamic acid exhibits a cell membrane stabilizing action, which is preferable because the collagen increasing action is stably exhibited.

Among the above xanthone derivatives, when X is caffeic acid, the unsaturated fatty acid residue of caffeic acid exhibits an inflammatory prostaglandin production inhibitory action, so that it acts on lipase while suppressing the inflammatory action, thereby increasing collagen. Is preferable because it is stably exhibited.

When extracting from plants, Hypericaceae plants, especially mangosteen fruit, flesh, pericarp, leaves, stems, flowers and roots, Hypericum perforatum, Fukugi, Crissia rosea, Hypericum tricolor, Hypericum calycinum, Terihaboku, Hypericum -Leaves, bark, flowers, fruits and roots such as calcinam, hypericum hydrcoat and hypericum androsaemum are preferred.

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 kotarahim, elcampure, gyoja garlic, onion, garlic, soybeans, gigishi, 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 squirrels, akabi, amachazul, amadokoroe, aloe, icarius, itadori, inokozuchi , Ibukizasou, Ukogi, Moray eels, Udo, Ume, Vultures, Ebisusa, Oren, Psyllium, Okera, Okra, Hypericum, Onamomi, Ominae, Oyster, Crows, Cranobis, Coleoptera Cowpea, yellowfin, yellow-billed, goldworm, black-headed beetle, red-headed swordfish, crap, gardenia, white-horned beetle, red-footed beetle, red-billed beetle, Sartorii rose bucket, sanshuyu, janohi, silane, honeysuckle, seri, burdock, dandelion, dandelion, dandelion, dandelion, dandelion, dandelion Azalea, Tochinoki, Tochibaninjin, Nanten, Noibaru, Octopus, Yellowtail, Hawthorn, Hikikoshi, Hishi, Hitotsuba, Biwa, Fuki, Fukujuso, Fuji, Matatabi, Swordfish, Yamanoimo, Yukinoshita, Momogi, Leopard, Leopard , Stems, flowers, fruits or roots are preferred because they are readily available.

It is preferable that the xanthone derivative is extracted from the above-mentioned Hypericaceae plant, Kotarahim, Elcampure, etc. 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 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.

Furthermore, it is an object to obtain the xanthone derivative by supercritical extraction using liquefied carbon dioxide from the above-mentioned hypericaceae plant, Kotarahim, Elcampure and other plants, fermented fermented products and chemically synthesized reactants. Since a xanthone derivative is obtained efficiently, it is preferable.

When the xanthone derivative is obtained by a chemical synthesis reaction, it is preferably 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 hydrcoat, Hypericum androsaemum, Kotarahim, and Elcampure, fermenting tanks with microorganisms or yeast added to fermentation bases such as soybeans It is implemented using.

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.

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, the pine needle extract-containing vegetable oil is used in the crude purification stage, whereby the collagen-increasing action and antiseptic action of the pine needle 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.

Moreover, what has a particle size of 0.1-300 micrometers is preferable, and a finer particle size performs high-precision separation, However, There exists a fault that separation time is long.

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 pharmaceuticals, it is used for the purpose of increasing collagen, enhancing interstitial tissue and anti-inflammatory, and it is used as an anti-inflammatory agent, local lipolytic agent, anti-cellulite agent, wrinkle removing agent, fatty liver inhibitor, hyperlipidemia It is used to prevent or ameliorate diseases, anti-atherosclerotic agents, metabolic syndrome, anticancer agents and lifestyle-related diseases.

In addition, as veterinary medicines used for animals and medicines used for pets, lipolytic agents, anti-obesity agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, anti-cancer agents, etc. Used as

The food preparation is used as a supplement for preventing or improving wrinkles, a supplement for the purpose of preventing or improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases.

Also used as veterinary foods and food preparations for animals, or food preparations for pets, for purposes such as skin regeneration, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and cancer prevention Is done.

The cosmetics are used as cosmetics, quasi-drugs and massage oils for improving or preventing wrinkles and tarmi for the purpose of improving and preventing wrinkles and tarmi caused by the collagen increasing action. It is also used as cosmetics, quasi-drugs, and beauty oils that eliminate or prevent cellulite that has been crushed on the surface due to a decrease in collagen.

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 skin diseases associated with collagen reduction.

In addition, it is also used in clothing for the purpose of increasing collagen and preventing skin wrinkles by using the fiber added with the xanthone derivative, especially for underwear, stockings, underwear, swimwear, socks, pajamas, futons and sheets. Used.

In addition, it is used for sanitary goods for the purpose of increasing collagen using plastics added with the above xanthone derivative, daily goods used in containers, toilets, baths, and the like.

Next, among the xanthone derivatives represented by the above formula (1) obtained by adding palmitic acid and transesterification lipase to the pulverized mangosteen, heating and extracting with vegetable oil, X is palmitic acid. The xanthone derivative represented by the following formula (2) having a collagen increasing action will be described.

The xanthone derivative here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the hydroxyl group at the 3-position It is a derivative in which carboxylic acid of palmitic acid is ester-bonded.

The xanthone derivative exhibits a collagen increasing action, increases collagen in skin, systemic organs and interstitial tissues, and improves or prevents wrinkles and talmi.

Since the xanthone derivative has a fatty acid side chain of palmitic acid, it easily penetrates into interstitial tissues and promotes collagen production. In addition, it suppresses bacterial growth and cancer tissue invasion and metastasis by collagen in the organ.

In the above xanthone derivatives, saturated fatty acid residues of palmitic acid penetrate into the cell membrane, are easily absorbed into fat cells, work easily on target fibroblasts and stromal tissues, and enhance collagen-increasing action. preferable.

The xanthone derivative is obtained by adding palmitic acid and transesterification lipase to a 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.

The raw material mangosteen is crushed. A pulverizer is used for pulverization. For example, a free mill, super free mill, sample mill, goblin, super clean mill, micros manufactured by Nara Machinery Co., Ltd., a small vacuum dryer manufactured by Toyo Riko as a vacuum dryer, stock A compact decompression heat transfer dryer DPTH-40 manufactured by Matsui Co., Ltd., clean dry VD-7, VD-20 manufactured by AKM Kyushu Technos Co., Ltd., etc. are used.

Palmitic acid used here is obtained from coconut oil, vegetable oil, rapeseed oil, cottonseed oil, corn oil, safflower oil, sesame oil, rice oil, sunflower oil, olive oil, etc., such as Ryoshoku, Nisshin Oil and Fuji Oil Co., Ltd. What was extracted and refine | purified from plants, such as a palm and a soybean, is preferable from there being few impurities.

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 pulverized mangosteen, palmitic acid and transesterification lipase are added to a clean stainless steel cylinder and heated. Here, it is preferable to add tap water as a solvent from the viewpoint of smoothing the reaction.

The amount of palmitic acid is preferably 0.02 to 2 weight, and the amount of lipase for transesterification is preferably 0.001 to 0.1 weight with respect to 1 weight of the pulverized mangosteen to be added.

The heating temperature is preferably 15 to 48 ° C, more preferably 18 to 39 ° C.

The heating time is preferably 2 to 48 hours, more preferably 6 to 28 hours.

The heating is preferably performed while stirring, and a rate of 40 to 140 times per minute is preferable.

It is cooled after being warmed. The cooling method is preferably natural cooling or water cooling.

The produced xanthone derivative 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, etc. The

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.

Among them, the pine needle extract-containing vegetable oil is a vegetable oil containing an oil-soluble polyphenol extracted by adding a vegetable oil to a pulverized pine needle and is excellent in collagen-increasing action. Can be separated.

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.

As for the vegetable oil to add, 2-10 weight is preferable with respect to 1 weight of pulverized mangosteens to add.

The separated xanthone derivative is absorbed into the body, and then the excess amount is decomposed by esterase and further metabolized in the liver. Therefore, the xanthone derivative 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 separate and purify with an appropriate separation solvent and remove the solvent to obtain the desired xanthone derivative.

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 that increase collagen, local anti-wrinkle agents, anti-cellulite agents, fatty liver inhibitors, hyperlipidemic agents, anti-arteriosclerosis agents, metabolic syndrome, anticancer agents, life Used to prevent or improve habitual diseases. In addition, it is also used as a wrinkle remover, a fatty liver suppressant, a hyperlipidemia ameliorating agent, an anti-arteriosclerotic agent and the like as a veterinary medicine used for animals and a medicine used for pets.

The food preparation is used as a supplement for the purpose of improving and preventing wrinkles and tarmi, a supplement for the purpose of preventing and improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases. In addition, it is used as a veterinary food or food preparation used for animals or a food preparation used for pets for the purpose of wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression or prevention.

As said cosmetics, it is utilized as a massage oil for the improvement and prevention of a wrinkle and a sagging resulting from collagen reduction, a quasi-drug, and a wrinkle prevention. It is also used as cosmetics, quasi-drugs, and massage oils that eliminate or prevent cellulite that has been crumpled on the surface due to collagen reduction and 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 anti-inflammatory effects due to increased collagen, metabolic syndrome and skin diseases derived therefrom. In addition, it is also used for clothing intended to remove fat using the fiber added with the xanthone derivative, in particular underwear for atopy, stockings, underwear, swimwear for anti-inflammatory effect due to increased collagen, Used for socks, pajamas, futons and sheets.

In addition, it is used for containers, toilets, bath products and the like for the purpose of anti-inflammatory action by increasing collagen using the above-mentioned plastic mixed with xanthone derivative.

Next, among the xanthone derivatives represented by the above formula (1) obtained by adding para-coumaric acid and lipase for transesterification to the pulverized mangosteen, heating and extracting with vegetable oil, X is para- A xanthone derivative represented by the following formula (3) having a collagen increasing action which is coumaric acid will be described.

The xanthone derivative here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the hydroxyl group at the 3-position Is a derivative in which carboxylic acid of para-coumaric acid is ester-bonded.

The xanthone derivative exhibits a collagen increasing action, increases collagen in skin, systemic organs and interstitial tissues, and improves or prevents wrinkles and talmi.

Since the xanthone derivative has a benzene side chain of para-coumaric acid, it easily penetrates into the interstitial tissue and promotes collagen production. In addition, it suppresses bacterial growth and cancer tissue invasion and metastasis by collagen in the organ.

In the above xanthone derivatives, the hydroxybenzene group of para-coumaric acid improves blood flow in the blood vessels and reaches the target fibroblasts and stromal tissues, and the collagen increasing action is enhanced. To preferred.

The xanthone derivative is obtained by adding para-coumaric acid and lipase for transesterification to 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.

The raw material mangosteen is crushed. A pulverizer is used for pulverization. For example, a free mill, super free mill, sample mill, goblin, super clean mill, micros manufactured by Nara Machinery Co., Ltd., a small vacuum dryer manufactured by Toyo Riko as a vacuum dryer, stock A compact decompression heat transfer dryer DPTH-40 manufactured by Matsui Co., Ltd., clean dry VD-7, VD-20 manufactured by AKM Kyushu Technos Co., Ltd., etc. are used.

The para-coumaric acid used here is obtained from coffee, green coffee, cocoa, propolis, and the like, and para-coumaric acid manufactured by Api Co., Ltd. is preferred because it is purified and has few impurities.

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 pulverized mangosteen, para-coumaric acid and transesterification lipase are added to a clean stainless steel cylinder and heated. Here, it is preferable to add tap water as a solvent from the viewpoint of smoothing the reaction.

The amount of para-coumaric acid is preferably 0.03 to 3 weights, and the amount of transesterified lipase is preferably 0.001 to 0.2 weights with respect to 1 weight of the pulverized mangosteen to be added.

The heating temperature is preferably 14 to 50 ° C, and more preferably 25 to 39 ° C.

The heating time is preferably 2 to 48 hours, more preferably 6 to 24 hours.

The heating is preferably performed while stirring, and a rate of 50 to 140 times per minute is preferable.

It is cooled after being warmed. The cooling method is preferably natural cooling or water cooling.

The produced xanthone derivative 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, etc. The

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.

Among them, the pine needle extract-containing vegetable oil is a vegetable oil containing an oil-soluble polyphenol extracted by adding a vegetable oil to a pulverized pine needle and is excellent in collagen-increasing action. Can be separated.

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.

As for the vegetable oil to add, 2-10 weight is preferable with respect to 1 weight of pulverized mangosteens to add.

The separated xanthone derivative is absorbed into the body, and then the excess amount is decomposed by esterase and further metabolized in the liver. Therefore, the xanthone derivative 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 separate and purify with an appropriate separation solvent and remove the solvent to obtain the desired xanthone derivative.

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 that increase collagen, local anti-wrinkle agents, anti-cellulite agents, fatty liver inhibitors, hyperlipidemic agents, anti-arteriosclerosis agents, metabolic syndrome, anticancer agents, life Used to prevent or improve habitual diseases. In addition, it is also used as a wrinkle remover, a fatty liver suppressant, a hyperlipidemia ameliorating agent, an anti-arteriosclerotic agent and the like as a veterinary medicine used for animals and a medicine used for pets.

The food preparation is used as a supplement for the purpose of improving and preventing wrinkles and tarmi, a supplement for the purpose of preventing and improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases. In addition, it is used as a veterinary food or food preparation used for animals or a food preparation used for pets for the purpose of wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression or prevention.

As said cosmetics, it is utilized as a massage oil for the improvement and prevention of a wrinkle and a sagging resulting from collagen reduction, a quasi-drug, and a wrinkle prevention. It is also used as cosmetics, quasi-drugs, and massage oils that eliminate or prevent cellulite that has been crumpled on the surface due to collagen reduction and 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 anti-inflammatory effects due to increased collagen, metabolic syndrome and skin diseases derived therefrom. In addition, it is also used for clothing intended to remove fat using the fiber added with the xanthone derivative, in particular underwear for atopy, stockings, underwear, swimwear for anti-inflammatory effect due to increased collagen, Used for socks, pajamas, futons and sheets.

In addition, it is used for containers, toilets, bath products and the like for the purpose of anti-inflammatory action by increasing collagen using the above-mentioned plastic mixed with xanthone derivative.

Next, among the xanthone derivatives represented by the above formula (1) obtained by adding sinapinic acid and transesterification lipase to the pulverized mangosteen, heating and extracting with vegetable oil, X is sinapinic acid The xanthone derivative represented by the following formula (4) having a collagen increasing action will be described.

The xanthone derivative here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the hydroxyl group at the 3-position Is a derivative in which carboxylic acid of sinapinic acid is ester-linked.

The xanthone derivative exhibits a collagen increasing action, increases collagen in skin, systemic organs and interstitial tissues, and improves or prevents wrinkles and talmi.

Since the xanthone derivative has a mesoxybenzene side chain of sinapinic acid, it easily penetrates into the interstitial tissue and promotes collagen production. In addition, it suppresses bacterial growth and cancer tissue invasion and metastasis by collagen in the organ.

The xanthone derivative is preferable because the benzene nucleus having a methoxy group of sinapinic acid exhibits an inflammatory prostaglandin production inhibitory action, and the collagen increasing action is stably exhibited while suppressing the inflammatory action.

The xanthone derivative is obtained by adding sinapinic acid and lipase for transesterification to a 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.

The raw material mangosteen is crushed. A pulverizer is used for pulverization. For example, a free mill, super free mill, sample mill, goblin, super clean mill, micros manufactured by Nara Machinery Co., Ltd., a small vacuum dryer manufactured by Toyo Riko as a vacuum dryer, stock A compact decompression heat transfer dryer DPTH-40 manufactured by Matsui Co., Ltd., clean dry VD-7, VD-20 manufactured by AKM Kyushu Technos Co., Ltd., etc. are used.

The sinapinic acid used here is obtained from propolis, cinnamon bark, clove, etc., and sinapinic acid manufactured by Anri Japan is preferred because it is purified and contains few impurities.

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 pulverized mangosteen, sinapinic acid and transesterification lipase are added to a clean stainless steel cylinder and heated. Here, it is preferable to add tap water as a solvent from the viewpoint of smoothing the reaction.

The amount of sinapinic acid is preferably 0.04 to 4 weights and the amount of lipase for transesterification is preferably 0.003 to 0.3 weights with respect to 1 weight of the pulverized mangosteen to be added.

The heating temperature is preferably 14 to 45 ° C, more preferably 25 to 37 ° C.

The heating time is preferably 2 to 48 hours, more preferably 6 to 24 hours.

The heating is preferably performed while stirring, and a rate of 40 to 140 times per minute is preferable.

It is cooled after being warmed. The cooling method is preferably natural cooling or water cooling.

The produced xanthone derivative 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, etc. The

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.

Among them, the pine needle extract-containing vegetable oil is a vegetable oil containing an oil-soluble polyphenol extracted by adding a vegetable oil to a pulverized pine needle and is excellent in collagen-increasing action. Can be separated.

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.

As for the vegetable oil to add, 2-10 weight is preferable with respect to 1 weight of pulverized mangosteens to add.

The separated xanthone derivative is absorbed into the body, and then the excess amount is decomposed by esterase and further metabolized in the liver. Therefore, the xanthone derivative 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 separate and purify with an appropriate separation solvent and remove the solvent to obtain the desired xanthone derivative.

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 that increase collagen, local anti-wrinkle agents, anti-cellulite agents, fatty liver inhibitors, hyperlipidemic agents, anti-arteriosclerosis agents, metabolic syndrome, anticancer agents, life Used to prevent or improve habitual diseases. In addition, it is also used as a wrinkle remover, a fatty liver suppressant, a hyperlipidemia ameliorating agent, an anti-arteriosclerotic agent and the like as a veterinary medicine used for animals and a medicine used for pets.

The food preparation is used as a supplement for the purpose of improving and preventing wrinkles and tarmi, a supplement for the purpose of preventing and improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases. In addition, it is used as a veterinary food or food preparation used for animals or a food preparation used for pets for the purpose of wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression or prevention.

As said cosmetics, it is utilized as a massage oil for the improvement and prevention of a wrinkle and a sagging resulting from collagen reduction, a quasi-drug, and a wrinkle prevention. It is also used as cosmetics, quasi-drugs, and massage oils that eliminate or prevent cellulite that has been crumpled on the surface due to collagen reduction and 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 anti-inflammatory effects due to increased collagen, metabolic syndrome and skin diseases derived therefrom. In addition, it is also used for clothing intended to remove fat using the fiber added with the xanthone derivative, in particular underwear for atopy, stockings, underwear, swimwear for anti-inflammatory effect due to increased collagen, Used for socks, pajamas, futons and sheets.

In addition, it is used for containers, toilets, bath products and the like for the purpose of anti-inflammatory action by increasing collagen using the above-mentioned plastic mixed with xanthone derivative.

Next, among the xanthone derivatives represented by the above formula (1) obtained by adding xanthone carboxylic acid and lipase for transesterification to the pulverized mangosteen, heating and extracting with vegetable oil, X is xanthone carboxylic acid The xanthone derivative represented by the following formula (5) having the collagen increasing action will be described.

The xanthone derivative here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the hydroxyl group at the 3-position It is a derivative in which a carboxylic acid of xanthonecarboxylic acid is ester-linked.

The xanthone carboxylic acid here has a carboxyl group bonded to the 2-position of xanthone.

The xanthone derivative exhibits a collagen increasing action, increases collagen in skin, systemic organs and interstitial tissues, and improves or prevents wrinkles and talmi.

Since the xanthone derivative has a xanthone side chain of xanthone carboxylic acid, it acts on fibroblasts and promotes collagen production. In addition, it suppresses bacterial growth and cancer tissue invasion and metastasis by collagen in the organ.

The xanthone derivative is preferable because the xanthone group of the xanthone carboxylic acid exhibits an anti-inflammatory action, and the collagen increasing action is stably exhibited while suppressing the inflammatory action.

The xanthone derivative is obtained by adding xanthone carboxylic acid and transesterification lipase to a pulverized mangosteen, heating, and extracting with a 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.

The raw material mangosteen is crushed. A pulverizer is used for pulverization. For example, a free mill, super free mill, sample mill, goblin, super clean mill, micros manufactured by Nara Machinery Co., Ltd., a small vacuum dryer manufactured by Toyo Riko as a vacuum dryer, stock A compact decompression heat transfer dryer DPTH-40 manufactured by Matsui Co., Ltd., clean dry VD-7, VD-20 manufactured by AKM Kyushu Technos Co., Ltd., etc. are used.

The xanthone carboxylic acid used here is obtained from mangosteen, Hypericum perforatum, etc., and xanthone carboxylic acid manufactured by Anri Japan is preferred because it is purified and contains few impurities.

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 pulverized mangosteen, xanthone carboxylic acid and transesterification lipase are added to a clean stainless steel cylinder and heated. Here, it is preferable to add tap water as a solvent from the viewpoint of smoothing the reaction.

The amount of xanthonecarboxylic acid is preferably 0.03 to 5 weight, and the amount of lipase for transesterification is preferably 0.001 to 0.3 weight with respect to 1 weight of the pulverized mangosteen to be added.

The heating temperature is preferably 14 to 60 ° C, and more preferably 25 to 45 ° C.

The heating time is preferably 2 to 48 hours, more preferably 6 to 24 hours.

The heating is preferably performed while stirring, and a rate of 40 to 140 times per minute is preferable.

It is cooled after being warmed. The cooling method is preferably natural cooling or water cooling.

The produced xanthone derivative 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, etc. The

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.

Among them, the pine needle extract-containing vegetable oil is a vegetable oil containing an oil-soluble polyphenol extracted by adding a vegetable oil to a pulverized pine needle and is excellent in collagen-increasing action. Can be separated.

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.

As for the vegetable oil to add, 2-10 weight is preferable with respect to 1 weight of pulverized mangosteens to add.

The separated xanthone derivative is absorbed into the body, and then the excess amount is decomposed by esterase and further metabolized in the liver. Therefore, the xanthone derivative 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 separate and purify with an appropriate separation solvent and remove the solvent to obtain the desired xanthone derivative.

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 that increase collagen, local anti-wrinkle agents, anti-cellulite agents, fatty liver inhibitors, hyperlipidemic agents, anti-arteriosclerosis agents, metabolic syndrome, anticancer agents, life Used to prevent or improve habitual diseases. In addition, it is also used as a wrinkle remover, a fatty liver suppressant, a hyperlipidemia ameliorating agent, an anti-arteriosclerotic agent and the like as a veterinary medicine used for animals and a medicine used for pets.

The food preparation is used as a supplement for the purpose of improving and preventing wrinkles and tarmi, a supplement for the purpose of preventing and improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases. In addition, it is used as a veterinary food or food preparation used for animals or a food preparation used for pets for the purpose of wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression or prevention.

As said cosmetics, it is utilized as a massage oil for the improvement and prevention of a wrinkle and a sagging resulting from collagen reduction, a quasi-drug, and a wrinkle prevention. It is also used as cosmetics, quasi-drugs, and massage oils that eliminate or prevent cellulite that has been crumpled on the surface due to collagen reduction and 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 anti-inflammatory effects due to increased collagen, metabolic syndrome and skin diseases derived therefrom. In addition, it is also used for clothing intended to remove fat using the fiber added with the xanthone derivative, in particular underwear for atopy, stockings, underwear, swimwear for anti-inflammatory effect due to increased collagen, Used for socks, pajamas, futons and sheets.

In addition, it is used for containers, toilets, bath products and the like for the purpose of anti-inflammatory action by increasing collagen using the above-mentioned plastic mixed with xanthone derivative.

Next, the manufacturing method of the xanthone derivative which has the collagen increasing effect which consists of the process obtained by extracting the fermented material which added the fermented natto to fermented soybeans and fermented natto bacteria with soybeans is demonstrated.

The target xanthone derivative is a derivative in which any one selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthonecarboxylic acid, transcinnamic acid, and caffeic acid is ester-linked to the xanthone skeleton.

Furthermore, the xanthone derivative referred to here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the 3-position Palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, transcinnamic acid, caffeic acid, organic acids such as phenylpropanoid organic acids and fatty acids are ester-bonded to the hydroxyl group as a substituent.

The above xanthone derivative is a combination of palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, and caffeic acid. It is easy to enter the cell, the structure of the xanthone derivative is stabilized, and is excellent in the collagen increasing action as compared with xanthone itself.

The xanthone derivatives here are preferred because they are structurally stable and easily infiltrate into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and the action of increasing collagen is sustained.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by the esterase in the blood, and xanthone and the respective palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, The xanthone derivatives are also highly safe because they are decomposed into caffeic acid and their respective safety has been confirmed.

Among the above xanthone derivatives, when X is palmitic acid, the saturated fatty acid residue of palmitic acid penetrates into the cell membrane, is easily absorbed into the cell, easily works on fibroblasts and interstitial tissues, and enhances the collagen increasing action. Is preferable.

Among the above xanthone derivatives, when X is para-coumaric acid, a benzene nucleus having a hydroxyl group of para-coumaric acid exhibits a blood flow dilating action, is easy to penetrate to the local area, and is preferable because collagen increasing action is enhanced. .

Among the above xanthone derivatives, when X is sinapinic acid, the benzene nucleus having the methoxy group of sinapinic acid exhibits an inhibitory action on inflammatory prostaglandin production, so that the collagen increasing action is stable while suppressing the inflammatory action. Therefore, it is preferable.

Among the above xanthone derivatives, when X is xanthone carboxylic acid, the xanthone residue of xanthone carboxylic acid exhibits an anti-inflammatory action, and thus the collagen increasing action is stably exhibited while suppressing the inflammatory action. preferable.

Among the above xanthone derivatives, when X is trans-cinnamic acid, the unsaturated fatty acid residue of trans-cinnamic acid exhibits a cell membrane stabilizing action, which is preferable because the collagen increasing action is stably exhibited.

Among the above xanthone derivatives, when X is caffeic acid, the unsaturated fatty acid residue of caffeic acid exhibits an inflammatory prostaglandin production inhibitory action, so that it acts on lipase while suppressing the inflammatory action, thereby increasing collagen. Is preferable because it is stably exhibited.

Materials used in the production method described here are mangosteen pulverized product, soybean, natto, and 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.

Mangosteen is crushed. For pulverization, free mill, super free mill, sample mill, goblin, super clean mill, micros, manufactured by Nara Machinery Co., Ltd. as a pulverizer, a small vacuum dryer manufactured by Toyo Riko as a vacuum dryer, manufactured by Matsui Co., Ltd. A small decompression heat transfer type dryer DPTH-40, clean dry VD-7, VD-20, etc. manufactured by AKM Kyushu Technos Co., Ltd. are used.

Moreover, the soybean here can be used from any of the origins of Japan, China, the United States, and Brazil, and a genetically modified product can also be used. It is preferable to pulverize this soybean with the above-mentioned pulverizer from the viewpoint of efficient fermentation.

The natto bacteria here are 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, 0.6-5 weight is preferable with respect to soybean with respect to 1 weight of pulverized mangosteen, and 0.001-0.03 weight is preferable with respect to natto. In addition, the fermentation is preferably carried out in a clean culture tank, and the materials are preferably mixed with tap water.

Moreover, this fermentation is heated at 30-50 degreeC, and fermentation is performed for 24-72 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, etc. 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.

The above-mentioned chrysanthemum flower extract-containing vegetable oil is a vegetable oil containing an oil-soluble polyphenol that is extracted by adding vegetable oil to the ground product of chrysanthemum flowers, and has excellent collagen increasing action, and stably separates 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 containing an oil-soluble polyphenol that is extracted by adding vegetable oil to a pulverized pine leaf and is excellent in collagen-increasing action. 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 leaf extract-containing vegetable oil is 0.03 to 3 weights per 1 weight of the fermented material. In this case, extraction by stirring is preferable, the stirring temperature is preferably 20 to 50 ° C., and the stirring time is preferably 1 to 6 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 derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing and fibers, plastic processing, environmental prevention materials, and the like.

As pharmaceuticals, it is used for the purpose of increasing collagen, enhancing interstitial tissue and anti-inflammatory, and it is used as an anti-inflammatory agent, local lipolytic agent, anti-cellulite agent, wrinkle removing agent, fatty liver inhibitor, hyperlipidemia It is used to prevent or ameliorate diseases, anti-atherosclerotic agents, metabolic syndrome, anticancer agents and lifestyle-related diseases. In addition, as veterinary medicines used for animals and medicines used for pets, lipolytic agents, anti-obesity agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, anti-cancer agents, etc. Used as

The food preparation is used as a supplement for preventing or improving wrinkles, a supplement for the purpose of preventing or improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases. Also used as veterinary foods and food preparations for animals, or food preparations for pets, for purposes such as skin regeneration, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and cancer prevention Is done.

The cosmetics are used as cosmetics, quasi-drugs and massage oils for improving or preventing wrinkles and tarmi for the purpose of improving and preventing wrinkles and tarmi caused by the collagen increasing action.

It is also used as cosmetics, quasi-drugs, and beauty oils that eliminate or prevent cellulite that has been crushed on the surface due to a decrease in collagen. 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 skin diseases associated with collagen reduction. In addition, it is also used in clothing for the purpose of increasing collagen and preventing skin wrinkles by using the fiber added with the xanthone derivative, especially for underwear, stockings, underwear, swimwear, socks, pajamas, futons and sheets. Used.

In addition, it is used for sanitary goods for the purpose of increasing collagen using plastics added with the above xanthone derivative, daily goods used in containers, toilets, baths, and the like.

Next, the manufacturing method of the xanthone derivative which has the collagen increase effect | action consisting of the process which adds and extracts liquefied carbon dioxide to the ground material of mangosteen is demonstrated.

The target xanthone derivative is a derivative in which any one selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthonecarboxylic acid, transcinnamic acid, and caffeic acid is ester-linked to the xanthone skeleton.

Furthermore, the xanthone derivative referred to here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the 3-position Palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, transcinnamic acid, caffeic acid, organic acids such as phenylpropanoid organic acids and fatty acids are ester-bonded to the hydroxyl group as a substituent.

The above xanthone derivative is a combination of palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, and caffeic acid. It is easy to enter the cell, the structure of the xanthone derivative is stabilized, and is excellent in the collagen increasing action as compared with xanthone itself.

The xanthone derivatives here are preferred because they are structurally stable and easily infiltrate into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and the action of increasing collagen is sustained.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by the esterase in the blood, and xanthone and the respective palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, The xanthone derivatives are also highly safe because they are decomposed into caffeic acid and their respective safety has been confirmed.

Among the above xanthone derivatives, when X is palmitic acid, the saturated fatty acid residue of palmitic acid penetrates into the cell membrane, is easily absorbed into the cell, easily works on fibroblasts and interstitial tissues, and enhances the collagen increasing action. Is preferable.

Among the above xanthone derivatives, when X is para-coumaric acid, a benzene nucleus having a hydroxyl group of para-coumaric acid exhibits a blood flow dilating action, is easy to penetrate to the local area, and is preferable because collagen increasing action is enhanced. .

Among the above xanthone derivatives, when X is sinapinic acid, the benzene nucleus having the methoxy group of sinapinic acid exhibits an inhibitory action on inflammatory prostaglandin production, so that the collagen increasing action is stable while suppressing the inflammatory action. Therefore, it is preferable.

Among the above xanthone derivatives, when X is xanthone carboxylic acid, the xanthone residue of xanthone carboxylic acid exhibits an anti-inflammatory action, and thus the collagen increasing action is stably exhibited while suppressing the inflammatory action. preferable.

Among the above xanthone derivatives, when X is trans-cinnamic acid, the unsaturated fatty acid residue of trans-cinnamic acid exhibits a cell membrane stabilizing action, which is preferable because the collagen increasing action is stably exhibited.

Among the above xanthone derivatives, when X is caffeic acid, the unsaturated fatty acid residue of caffeic acid exhibits an inflammatory prostaglandin production inhibitory action, so that it acts on lipase while suppressing the inflammatory action, thereby increasing collagen. Is preferable because it is stably exhibited.

Supercritical extraction with liquefied carbon dioxide, using a supercritical fluid extraction device, bringing the supercritical fluid into a supercritical state under the condition of the critical temperature or higher and the critical pressure or higher and the raw material, This is a manufacturing method for extracting a predetermined component from a raw material.

Liquefied carbon dioxide is used as the supercritical fluid.

As a manufacturing process, a critical temperature of 31.2 ° C. or higher and a critical pressure of 72.8 atm are set as lower limits.

The pulverized product of mangosteen, which is a raw material, is extracted with carbon dioxide that has become liquid in a supercritical state.

In this case, carbon dioxide has physical and chemical properties compatible with the compound to be extracted such that the critical temperature is close to room temperature and the polarity is lower than ethanol.

Carbon dioxide is not only excellent in physical properties in the extraction process in this way, but also tasteless and odorless and does not affect the taste of the supercritical extraction product, so carbon dioxide is the most supercritical fluid used in this embodiment. preferable.

For the operation in supercritical fluid extraction, the supercritical fluid is suitable for the temperature and pressure of the treatment because it uses the property that density and solubility greatly change with a slight temperature difference and pressure difference near the critical point. A vertical width is required.

The operating temperature when using liquefied carbon dioxide is preferably 30 to 90 ° C, more preferably 32 to 50 ° C.

Moreover, 71-510 atmospheres is preferable and the pressure of a process has more preferable 73-400 atmospheres.

The flow rate of liquefied carbon dioxide is preferably 1 to 10 kg / hour, more preferably 3 to 7 kg / hour, with respect to 1 kg of pulverized mangosteen.

Although the treatment time needs to be adjusted depending on the raw material of mangosteen, 3 to 12 hours are preferable.

The property of the target xanthone derivative extracted under the above extraction conditions varies depending on the elapsed time of extraction, and may be obtained as a liquid, powder or massive solid.

When ethanol is used as an auxiliary medium, it becomes a liquid containing ethanol.

If necessary, the obtained supercritical extract may be powdered by adding excipients such as lactose and dextrin.

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 pharmaceuticals, it is used for the purpose of increasing collagen, enhancing interstitial tissue and anti-inflammatory, and it is used as an anti-inflammatory agent, local lipolytic agent, anti-cellulite agent, wrinkle removing agent, fatty liver inhibitor, hyperlipidemia It is used to prevent or ameliorate diseases, anti-atherosclerotic agents, metabolic syndrome, anticancer agents and lifestyle-related diseases.

In addition, as veterinary medicines used for animals and medicines used for pets, lipolytic agents, anti-obesity agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, anti-cancer agents, etc. Used as

The food preparation is used as a supplement for preventing or improving wrinkles, a supplement for the purpose of preventing or improving cellulite, local fat reduction, metabolic syndrome and lifestyle-related diseases. Also used as veterinary foods and food preparations for animals, or food preparations for pets, for purposes such as skin regeneration, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and cancer prevention Is done.

The cosmetics are used as cosmetics, quasi-drugs and massage oils for improving or preventing wrinkles and tarmi for the purpose of improving and preventing wrinkles and tarmi caused by the collagen increasing action.

It is also used as cosmetics, quasi-drugs, and beauty oils that eliminate or prevent cellulite that has been crushed on the surface due to a decrease in collagen. 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 skin diseases associated with collagen reduction. In addition, it is also used in clothing for the purpose of increasing collagen and preventing skin wrinkles by using the fiber added with the xanthone derivative, especially for underwear, stockings, underwear, swimwear, socks, pajamas, futons and sheets. Used.

In addition, it is used for sanitary goods for the purpose of increasing collagen using plastics added with the above xanthone derivative, daily goods used in containers, toilets, baths, and the like.

Next, a composition containing 0.05 to 0.8 weight of chrysanthemum flower extract-containing vegetable oil and 0.05 to 0.8 weight of pine leaf extract-containing vegetable oil in 1 weight of the xanthone derivative having the collagen increasing action A cosmetic product comprising:

The xanthone derivative here is a derivative in which any one selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, transcinnamic acid and caffeic acid is ester-linked to the xanthone skeleton.

Furthermore, the xanthone derivative referred to here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the 3-position Palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, transcinnamic acid, caffeic acid, organic acids such as phenylpropanoid organic acids and fatty acids are ester-bonded to the hydroxyl group as a substituent.

The above xanthone derivative is a combination of palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, and caffeic acid. It is easy to enter the cell, the structure of the xanthone derivative is stabilized, and is excellent in the collagen increasing action as compared with xanthone itself.

The xanthone derivatives here are preferred because they are structurally stable and easily infiltrate into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and the action of increasing collagen is sustained.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by the esterase in the blood, and xanthone and the respective palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, The xanthone derivatives are also highly safe because they are decomposed into caffeic acid and their respective safety has been confirmed.

Among the above xanthone derivatives, when X is palmitic acid, the saturated fatty acid residue of palmitic acid penetrates into the cell membrane, is easily absorbed into the cell, easily works on fibroblasts and interstitial tissues, and enhances the collagen increasing action. Is preferable.

Among the above xanthone derivatives, when X is para-coumaric acid, a benzene nucleus having a hydroxyl group of para-coumaric acid exhibits a blood flow dilating action, is easy to penetrate to the local area, and is preferable because collagen increasing action is enhanced. .

Among the above xanthone derivatives, when X is sinapinic acid, the benzene nucleus having the methoxy group of sinapinic acid exhibits an inhibitory action on inflammatory prostaglandin production, so that the collagen increasing action is stable while suppressing the inflammatory action. Therefore, it is preferable.

Among the above xanthone derivatives, when X is xanthone carboxylic acid, the xanthone residue of xanthone carboxylic acid exhibits an anti-inflammatory action, and thus the collagen increasing action is stably exhibited while suppressing the inflammatory action. preferable.

Among the above xanthone derivatives, when X is trans-cinnamic acid, the unsaturated fatty acid residue of trans-cinnamic acid exhibits a cell membrane stabilizing action, which is preferable because the collagen increasing action is stably exhibited.

Among the above xanthone derivatives, when X is caffeic acid, the unsaturated fatty acid residue of caffeic acid exhibits an inflammatory prostaglandin production inhibitory action, so that it acts on lipase while suppressing the inflammatory action, thereby increasing collagen. Is preferable because it is stably exhibited.

The chrysanthemum flower extract-containing vegetable oil here is an oil obtained by adding vegetable oil to a ground chrysanthemum flower and extracting it, and is excellent in collagen increasing action.

As vegetable oil used here, vegetable oil includes 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 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, etc. The oil used for is 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.

Chrysanthemum flower extract-containing vegetable oil manufactured by Toyo Fermentation Co., Ltd. is preferable because of its high quality and low impurities.

The pine leaf extract-containing vegetable oil is obtained by pulverizing pine leaves from Japan, China, and Asia with a pulverizer and extracting them with vegetable oil.

Processed raw material of pine leaves with cellulase such as Onozuka R-10, Y-NC manufactured by Yakult Pharmaceutical Co., Ltd., Cellulase A “Amano” 3 and Cellulase T “Amano” 4 manufactured by Amano Enzyme Co., Ltd. This is preferable because the extraction efficiency is improved.

The added chrysanthemum flower extract-containing vegetable oil is 0.05 to 0.8 wt., And the pine leaf extract-containing vegetable oil is 0.05 to 0.8 wt. This gives a composition.

When the weight of the chrysanthemum flower extract-containing vegetable oil is less than 0.05 weight relative to 1 weight of the xanthone derivative, the target composition may not be sufficiently obtained.

When the weight of the chrysanthemum flower extract-containing vegetable oil is more than 0.8 weight with respect to 1 weight of the xanthone derivative, the solubility of the xanthone derivative is lowered and may be precipitated.

If the weight of the pine leaf extract-containing vegetable oil is less than 0.05 weight per 1 weight of the xanthone derivative, the target composition may not be sufficiently obtained.

When the weight of the pine leaf extract-containing vegetable oil is more than 0.8 weight relative to 1 weight of the xanthone derivative, the solubility of the xanthone derivative is lowered and may be precipitated.

In order to obtain the said composition, it is preferable to heat after mixing. As heating conditions, the temperature is 30 to 45 ° C., and the heating time is 6 to 40 hours.

When the heating temperature is lower than 30 ° C, there is a possibility that sufficient reaction does not occur. When the heating temperature is higher than 45 ° 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 40 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.

Moreover, by comprising in this way, a xanthone derivative is stably maintained by the antioxidant power of a chrysanthemum flower extract containing vegetable oil, and the decomposition | disassembly by oxidation is suppressed. In particular, double bonds of unsaturated fatty acids are protected from oxidation and maintain the structure.

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 daily application amount is less than 0.01 g, there is a possibility that the treatment or prevention effect of wrinkles and tarmi may not be exhibited. When the application amount per day exceeds 10 g, the cost may increase.

The cosmetics referred to here are basic cosmetics, whitening cosmetics, hair cleansing agents, treatment agents, hair dyes, hair restorers, hair nourishing agents, body wash, quasi-drugs that are cosmetics used for humans. In addition, it is a skin improvement agent used for animals, a shampoo for pets, and a body wash.

This cosmetic exhibits an excellent wrinkle and sagging improvement effect and a preventive action by exhibiting an action of increasing collagen. That is, wrinkles and saggings are improved by increasing collagen against wrinkles and saggings caused by a decrease in collagen in interstitial tissues and subcutaneous tissues.

Moreover, the skin which has developed the wound and the inflammation shows the effect | action which prevents inflammation and repairs a wound by increasing collagen.

Furthermore, this cosmetic product also works to improve or prevent atopy and chemical hypersensitivity caused by chemical substances and allergens by protecting against inflammation with collagen and accelerating healing.

Next, a composition containing 0.01 to 0.5 weight of chrysanthemum flower extract-containing vegetable oil and 0.01 to 0.5 weight of pine leaf extract-containing vegetable oil in 1 weight of the xanthone derivative having the collagen increasing action A food preparation comprising:

The xanthone derivative here is a derivative in which any one selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, transcinnamic acid and caffeic acid is ester-linked to the xanthone skeleton.

Furthermore, the xanthone derivative referred to here is represented by 3,6,8-trihydroxy-2-mesoxy-1,7-bis (3-methylbut-2-enyl) xanthene-9-one, of which the 3-position Palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, transcinnamic acid, caffeic acid, organic acids such as phenylpropanoid organic acids and fatty acids are ester-bonded to the hydroxyl group as a substituent.

The above xanthone derivative is a combination of palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, and caffeic acid. It is easy to enter the cell, the structure of the xanthone derivative is stabilized, and is excellent in the collagen increasing action as compared with xanthone itself.

The xanthone derivatives here are preferred because they are structurally stable and easily infiltrate into skin cells, adipose tissue, stromal tissue, fibroblasts and cell membranes, and the action of increasing collagen is sustained.

When the xanthone derivative is excessively ingested and absorbed, the excess amount is decomposed by the esterase in the blood, and xanthone and the respective palmitic acid, para-coumaric acid, sinapinic acid, xanthone carboxylic acid, trans-cinnamic acid, The xanthone derivatives are also highly safe because they are decomposed into caffeic acid and their respective safety has been confirmed.

Among the above xanthone derivatives, when X is palmitic acid, the saturated fatty acid residue of palmitic acid penetrates into the cell membrane, is easily absorbed into the cell, easily works on fibroblasts and interstitial tissues, and enhances the collagen increasing action. Is preferable.

Among the above xanthone derivatives, when X is para-coumaric acid, a benzene nucleus having a hydroxyl group of para-coumaric acid exhibits a blood flow dilating action, is easy to penetrate to the local area, and is preferable because collagen increasing action is enhanced. .

Among the above xanthone derivatives, when X is sinapinic acid, the benzene nucleus having the methoxy group of sinapinic acid exhibits an inhibitory action on inflammatory prostaglandin production, so that the collagen increasing action is stable while suppressing the inflammatory action. Therefore, it is preferable.

Among the above xanthone derivatives, when X is xanthone carboxylic acid, the xanthone residue of xanthone carboxylic acid exhibits an anti-inflammatory action, and thus the collagen increasing action is stably exhibited while suppressing the inflammatory action. preferable.

Among the above xanthone derivatives, when X is trans-cinnamic acid, the unsaturated fatty acid residue of trans-cinnamic acid exhibits a cell membrane stabilizing action, which is preferable because the collagen increasing action is stably exhibited.

Among the above xanthone derivatives, when X is caffeic acid, the unsaturated fatty acid residue of caffeic acid exhibits an inflammatory prostaglandin production inhibitory action, so that it acts on lipase while suppressing the inflammatory action, thereby increasing collagen. Is preferable because it is stably exhibited.

The xanthone derivative contains a chrysanthemum flower extract-containing vegetable oil and a pine leaf extract-containing vegetable oil, and is made into a composition to be a food preparation.

Here, the chrysanthemum flower extract-containing vegetable oil is an extract extracted from chrysanthemum flowers with vegetable oil.

Chrysanthemum flower extract-containing vegetable oil manufactured by Toyo Fermentation Co., Ltd. is preferable because of its high quality and low impurities.

The pine leaf extract-containing vegetable oil here is obtained by pulverizing pine leaves from Japan, China, and Asia using a pulverizer and extracting the pine leaf extract with vegetable oil.

Processed raw material of pine leaves with cellulase such as Onozuka R-10, Y-NC manufactured by Yakult Pharmaceutical Co., Ltd., Cellulase A “Amano” 3 and Cellulase T “Amano” 4 manufactured by Amano Enzyme Co., Ltd. This is preferable because the extraction efficiency is improved.

The added chrysanthemum flower extract-containing vegetable oil is 0.01-0.5 wt. And the pine leaf extract-containing vegetable oil is 0.01-0.5 wt. This gives a composition.

If the weight of the chrysanthemum flower extract-containing vegetable oil is less than 0.01% by weight of the xanthone derivative, the target composition may not be sufficiently obtained.

When the weight of the chrysanthemum flower extract-containing vegetable oil is more than 0.5 weight relative to 1 weight of the xanthone derivative, the solubility of the xanthone derivative is lowered and may be precipitated.

When the weight of the pine leaf extract-containing vegetable oil is less than 0.01 weight per 1 weight of the xanthone derivative, the target composition may not be sufficiently obtained.

When the weight of the pine leaf extract-containing vegetable oil is more than 0.5 weight with respect to 1 weight of the xanthone derivative, the solubility of the xanthone derivative is lowered and may be precipitated.

In order to obtain the said composition, it is preferable to heat after mixing. As heating conditions, the temperature is 30 to 45 ° C., and the heating time is 6 to 40 hours.

When the heating temperature is lower than 30 ° C, there is a possibility that sufficient reaction does not occur. When the heating temperature is higher than 45 ° 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 40 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.

Moreover, by comprising in this way, a xanthone derivative is stably maintained by the antioxidant power of a chrysanthemum flower extract containing vegetable oil, and the decomposition | disassembly by oxidation is suppressed. In particular, double bonds of unsaturated fatty acids are protected from oxidation and maintain the structure.

Further, the composition is processed together with other raw materials to form a food preparation. In this case, by adding to various food materials or beverage materials, for example, it can be made into a food preparation in the form of powder, tablet, liquid (drink, etc.), capsule or the like. Moreover, you may add a base material, an excipient | filler, an additive, a subsidiary material, a bulking agent, etc. suitably.

The food preparation is taken orally in several divided doses per day. The daily intake is preferably 0.2 to 10 g, more preferably 0.3 to 6 g, and even more preferably 0.5 to 4 g. When the daily intake is less than 0.2 g, there is a possibility that sufficient collagen increasing action is not exhibited. If the daily intake exceeds 10 g, the cost may increase. In addition to the above, it can be used in the form of rice cake, rice crackers, cookies, beverages and the like.

The food preparation here is a health functional food, a health supplement, a general food, a hospital food used in a hospital, an animal feed or a pet supplement, or a pet food.

This food preparation is used for the purpose of promoting lipolysis, preventing obesity, heart disease caused by fat and cholesterol accumulation, improving liver function, recovering from fatigue, strengthening muscles, dieting, and nutrition.

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

Furthermore, 10 g of natto bacteria made by Natto Motopo was added. Fermentation was continued for 40 hours at 37 ° C. with stirring.

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

1 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.

Hereinafter, preparation of xanthone derivatives to which palmitic acid is bound will be 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 palmitic acid obtained from Ryoshoku was added and stirred.

To this was added 10 g of lipase AY “Amano” 30G manufactured by Amano Enzyme, and the mixture was heated to 33 ° C. and stirred at a rate of 65 times / minute for 9 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 oil portion was dried by a vacuum dryer (manufactured by AKM Kyushu Technos, Clean Dry) to obtain a xanthone derivative to which caprylic acid was bound as an oily liquid. This was also used as the sample of Example 2.

In the following, the preparation of xanthone derivatives bound with para-coumaric acid 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, 220 g of para-coumaric acid obtained from Anri Japan was added and stirred.

To this was added 10 g of lipase AY “Amano” 30G manufactured by Amano Enzyme, and the mixture was heated to 30 ° C. and stirred at a rate of 70 times / minute for 11 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.

In the following, the preparation of xanthone derivatives bound with adipic acid is described.

Pericarp was collected from Thai mangosteen. 3 kg of mangosteen peel was collected, washed thoroughly with tap water, and dried with a dryer. This was used as the raw mangosteen peel. This mangosteen peel 2.2 kg was subjected to a pulverizer (manufactured by Sanriki Seisakusho Co., Ltd., a three-purpose universal pulverizer) and pulverized to obtain a pulverized mangosteen peel.

1.9 kg of pulverized mangosteen peel was put into a clean cylinder and 19 L of tap water was added. To this, 300 g of adipic acid manufactured by Anri Japan was added and stirred.

To this was added 20 g of lipase AY “Amano” 30G manufactured by Amano Enzyme, and the mixture was heated to 33 ° C. and stirred at a rate of 60 times / minute for 10 hours to obtain a heated solution.

After cooling the cylinder containing the warming liquid with tap water, 1 kg of Ajinomoto soybean 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 eicosapentaenoic acid was bound as an oily liquid. This was also used as the sample of Example 4.

Hereinafter, preparation of a xanthone derivative bonded with xanthone carboxylic acid will be described.

2.9 kg of mangosteen cultivated in Thailand was purchased, the pericarp was collected, washed thoroughly with tap water, and dried with a dryer (GZQ3 type, manufactured by Nishimura Kikai). This was used as the raw mangosteen peel.

This mangosteen peel 2.5 kg was subjected to a pulverizer (manufactured by Sanriki Seisakusho, a three-purpose universal pulverizer) and pulverized to obtain a pulverized mangosteen peel.

1.1 kg of pulverized mangosteen peel was added to a clean cylinder and 10 L of tap water was added. To this, 350 g of xanthonecarboxylic acid manufactured by Anri Japan was added and stirred.

To this was added 11 g of lipase AY “Amano” 30G manufactured by Amano Enzyme, and the mixture was heated to 25 ° C. and stirred at a rate of 73 times / minute for 15 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 bound with docosahexaenoic acid as an oily liquid. This was also used as the sample of Example 5.

Hereinafter, a purified product of the xanthone derivative will be described.

100 g of the xanthone derivative obtained in Example 3 was suspended in 500 mL of ethanol and applied to a column packed with 900 g of Diaion made by Mitsubishi Chemical. This was washed with 1000 mL of water containing 5% ethanol. Further, after washing with 2000 mL of 20% ethanol-containing water, elution was performed with 800 mL of 70% ethanol-containing water, and then a fraction of 90% ethanol-containing water was collected.

This fraction was subjected to a vacuum dryer to distill off ethanol and water, and then 15 g of an oily purified product of xanthone derivative was obtained by a freeze dryer manufactured by Nippon FD. This was used as the sample of Example 6.

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

Each of the xanthone derivatives obtained in Example 1, Example 2, Example 3, Example 4, Example 5, Example 6 and Example 6 obtained as described above was dissolved in purified ethanol, and a high speed equipped with a mass spectrometer was obtained. Analysis was performed by liquid chromatography (HPLC, Shimadzu Corporation), and analysis was further performed by a nuclear magnetic resonance apparatus (NMR, manufactured by Bruker, AC-250).

As a result, from the specimen of Example 1, xanthone carboxylic acid, palmitic acid, lauric acid, 14-methyl palmitic acid, stearic acid, para-coumaric acid, adipic acid, and methyl stearic acid were bound to xanthone as a xanthone derivative. A xanthone derivative was identified.

Further, from the sample of Example 2, a xanthone derivative in which palmitic acid was bound to xanthone was identified. The hydroxyl group of the xanthone skeleton and the carboxylic acid of palmitic acid were ester-bonded.

In addition, from the specimens of Example 3 and Example 6, a xanthone derivative in which para-coumaric acid was bound to xanthone was identified. The carboxylic acid of para-coumaric acid was ester-bonded to the hydroxyl group of the xanthone skeleton.

Further, from the sample of Example 4, a xanthone derivative in which adipic acid was bound to xanthone was identified. The carboxylic acid of adipic acid was ester-bonded to the hydroxyl group of the xanthone skeleton.

Further, from the sample of Example 5, a xanthone derivative in which xanthone carboxylic acid was bonded to xanthone was identified.

Hereinafter, experiments using human skin-derived fibroblasts will be described. This is a test method for evaluating the collagen increasing action by using fibroblasts derived from human skin.
(Test Example 2)

Normal human adult dermal fibroblasts (Fibrocell NHDF (AD), manufactured by Kurabo Corp.) were cultured in a dedicated culture solution, and were used in Example 1, Example 2, Example 3, Example 4, Example 5, and Example. The sample obtained in 6 was dissolved in dimethyl sulfoxide (manufactured by Wako Pure Chemical Industries, Ltd.), 0.1 mg of each was added, and cultured at 37 ° C. for 48 hours.

Dimethyl sulfoxide was used as a solvent control. As a positive control, fibroblast growth factor (FGF, manufactured by Cosmo Bio) was dissolved in purified water and 0.1 mg was added. The number of cells was counted, and the amount of collagen was further observed by an antibody method (manufactured by Chondrex).

As a result, regarding the number of cells, the value of 0.1 mg of each sample of Example 1, Example 2, Example 3, Example 4, Example 5, and Example 6 was 176 with respect to the solvent control value. %, 167%, 170%, 283%, 264% and 344%, and all specimens showed fibroblast proliferation.

Since the addition of 0.1 mg of the positive control FGF was 159% relative to the value of the solvent control, Example 1, Example 2, Example 3, Example 4, Example 5, and Example It was found that each of the 6 specimens showed fibroblast proliferation stronger than FGF.

Regarding collagen production, the value of 0.1 mg of each sample of Example 1, Example 2, Example 3, Example 4, Example 5, and Example 6 is 201% with respect to the solvent control value, respectively. The specimens were 218%, 206%, 320%, 317%, and 355%, and all the specimens showed an increasing action of collagen.

Since the addition of 0.1 mg of the positive control FGF was 187% with respect to the value of the solvent control, Example 1, Example 2, Example 3, Example 4, Example 5, and Example Sample 6 was found to exhibit a stronger collagen-increasing action than FGF.

Hereinafter, cosmetics exhibiting a collagen increasing action will be described.

To 100 g of the xanthone derivative obtained in Example 1 above, 20 g of Toyo Fermented Chrysanthemum Flower Extract-containing vegetable oil and 20 g of Toyo Fermented Pine Leaf Extract-containing vegetable oil were added. This was mixed to prepare a composition.

Furthermore, 0.2 g of sodium gluconate, 0.1 g of lipase F-AP15 manufactured by Amano Enzyme, and 1 g of polyethylene glycol monostearate were added to this composition, 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 7.

Below, the test of the wrinkle improvement effect of cosmetics is demonstrated.
(Test Example 3)

Using the emulsion obtained in Example 7, an improvement test for wrinkles was conducted on 6 women aged 49 to 78 years. That is, the emulsion of Example 7 was applied to the face portion at 1 g per day for 7 days.

Before use and 7 days after use, the skin surface horny layer moisture content measuring device (IBBS, SKICON200) is used, and the skin elasticity and wrinkle length per unit area are measured using a elasticity meter (Cutometer). Was measured.

As a result, the skin surface horny layer moisture content increased to 240% after use compared to before use. The elasticity of the elasticity meter increased to 280% after use compared to before use. Furthermore, the length of the wrinkles was 75% compared to that before use, and a reduction in wrinkles was observed.

On the other hand, no particular discomfort or inconvenience was found in the feeling of use. As a result, the emulsion obtained in Example 7 was found to have a water increasing effect and a wrinkle improving effect.

The xanthone derivative having the collagen-increasing action of the present invention exhibits an excellent action with weak side effects that prevent and improve systemic and visceral collagen depletion, cancer, arteriosclerosis, wrinkles and tarmi, obesity, or QOL of its reserve army Is to improve.

In addition, the food preparation comprising xanthone derivatives having an action of increasing collagen according to the present invention improves or prevents cancer metastasis and invasion associated with collagen decrease, and contributes to improving the quality of life and reducing medical costs. It is.

Furthermore, cosmetics comprising xanthone derivatives having an action of increasing collagen are excellent in preventing and improving wrinkles and talmi, and improve the public's 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 (9)

A xanthone derivative represented by the following formula (1) having a collagen increasing action.

X is any one selected from palmitic acid, para-coumaric acid, sinapinic acid, xanthonecarboxylic acid, transcinnamic acid, and caffeic acid. The following is obtained by adding palmitic acid and transesterification lipase to a pulverized mangosteen, heating and extracting with a vegetable oil, and having the collagen-increasing action wherein X is palmitic acid among the xanthone derivatives according to claim 1 A xanthone derivative represented by the formula (2):

A collagen increase in which x is para-coumaric acid obtained by adding para-coumaric acid and lipase for transesterification to pulverized mangosteen, heating and extracting with vegetable oil. A xanthone derivative represented by the following formula (3) having an action.

Sinapinic acid and lipase for transesterification are added to the pulverized mangosteen, heated, and extracted with vegetable oil. The xanthone derivative according to claim 1, which has a collagen increasing action wherein X is sinapinic acid. A xanthone derivative represented by the formula (4):

A xanthone carboxylic acid and lipase for transesterification are added to a pulverized mangosteen, heated and extracted with vegetable oil. The xanthone derivative according to claim 1, wherein X is xanthone carboxylic acid. A xanthone derivative represented by the following formula (5).

The method for producing a xanthone derivative having an action of increasing collagen according to claim 1, comprising a step of obtaining a fermented product obtained by adding fermented natto to fermented soybeans and fermented natto bacteria to mangosteen. The method for producing a xanthone derivative having an action of increasing collagen according to claim 1, comprising a step of adding liquefied carbon dioxide to a pulverized mangosteen and extracting it. Claim 1 or claim 2 or claim 3 or claim 4 or claim 5 or claim 6 or claim 7 containing 1% by weight of a xanthone derivative having a collagen-increasing action, and chrysanthemum flower extract-containing vegetable oil 0.05 A cosmetic comprising a composition containing ~ 0.8 wt., Pine needle extract-containing vegetable oil 0.05-0.8 wt. Claim 1 or claim 2 or claim 3 or claim 4 or claim 5 or claim 6 or claim 7 containing 1% by weight of a xanthone derivative having a collagen-increasing action, chrysanthemum flower extract-containing vegetable oil 0.01 A food preparation comprising a composition containing ˜0.5 wt., Pine needle extract-containing vegetable oil 0.01˜0.5 wt.