JP4074652B1 - Method for producing catechin derivative - Google Patents

Abstract

Kind Code: A1 A catechin derivative having weak side effects and having an excellent lipolytic action, a food preparation comprising the same, a cosmetic, and an anti-obesity drug.
Any of catechin and caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methylstearic acid, lauric acid, and 14-methylpalmitic acid A catechin derivative having a lipolytic action formed by ester bonding with a heel. The catechin derivative is obtained by adding green tea leaf pulverized product, fatty acids and transesterification lipase and heating, or fermenting with green tea leaf pulverized product and fish, soybean and natto, and extracting with vegetable oil. A food preparation, cosmetic or anti-obesity drug containing the catechin derivative.
[Selection figure] None

Description

The present invention relates to a method for producing a catechin derivative having a lipolytic action .

The relationship between the increase in visceral fat due to the accumulation of fat as shown in metabolic syndrome and lifestyle-related diseases has become a hot topic, and the review of meals and the introduction of exercise have been enlightened as measures to improve lifestyle. However, it is said that the number of patients with metabolic syndrome or the number of reserve groups is 10 million or 20 million (see, for example, Non-Patent Document 1).

In addition, treatment costs and drug costs for hypertension, diabetes, arteriosclerosis, and hyperlipidemia, which are diseases related to metabolic syndrome, amount to several trillion yen annually, and the burden of national medical expenses is very large. Health Japan 21 aims to reduce this lifestyle-related disease and medical expenses.

The source of metabolic syndrome leading to lifestyle-related diseases has been reported to be fat accumulation (see, for example, Non-Patent Document 2).

Although various efforts have been made to reduce fat in order to solve the metabolic syndrome, it has not yet completely solved the accumulation of body fat.

Clofibrate, which is used as a pharmaceutical, has the function of suppressing the synthesis of neutral fat in the liver, but hepatic dysfunction is observed as a side effect. And side effects of liver damage have been observed (see, for example, Non-Patent Document 3).

As useful ingredients for reducing naturally occurring neutral fat, globin proteolysate, oolong tea polymerized polyphenol, diacylglycerol and the like are known as commercially available foods for specified health use. However, the action of each component is mild, and it is necessary to continue large intakes.

Green tea contains catechins and essential oil components, and has the property of eliminating excess fat by regulating water content and breaking down fat, and has a strong function in the use of fats, but the absorption rate of catechins into the body is high. There is also the problem of low.

Focusing on these points, as an invention for reducing neutral fat using components derived from green tea, one or more components selected from capsinoids are 0.001 to 10% by weight and one or more A food composition characterized in that it contains 0.001 to 90% by weight of two or more energy accumulation inhibiting components and the total amount of capsinoids and energy accumulation inhibiting components is in the range of 0.002 to 99% by weight. Inventions related to objects are seen (for example, see Patent Document 1).

In addition, there is an invention of a slimming skin cosmetic using a parsley extract and one or more selected from a lipolysis accelerator, an astringent, a blood circulation accelerator, and a moisturizer (see, for example, Patent Document 2). ).

However, in any of the above-described inventions, components or derivatives identified as useful substances have not been identified, and their functions are not clear.

In view of these current conditions, pharmaceuticals, cosmetics, foods, and other industries have natural side effects that have few side effects, have excellent effects, and can be used for a long period of time against the metabolic syndrome that imposes public health and medical costs. Plant-derived ingredients are desired, and pharmaceuticals, cosmetics, and foods using the ingredients are desired.
JP 2006-212021 A JP 2004-059520 A Health Bureau General Affairs Division Lifestyle Disease Control Office, May 8, 2006 announcement, 2004 National Health and Nutrition Survey results summary. Jun Kawada et al., Japanese Journal of Gastroenterology, 102, 1384-1391, 2005. Yoji Hirakawa et al., Japanese Pharmacology Journal, 118, 389-395, 2001.

Although globin proteolysate, oolong tea polyphenols, diacylglycerol, etc. have been used as materials for reducing neutral fat in the past, their functions are mild and there is no sufficient fat reduction effect, so that metabolic syndrome can be solved. The law is insufficient.

Chemically synthesized lipolytic compounds such as mazindol are addictive, pulmonary hypertension, dry mouth, constipation, vomiting, insomnia, headache, weakness, dizziness, dullness, irritation, nervousness, Side effects such as excitement, palpitation and blood pressure fluctuations have been reported, and since they are resistant to action, there is a problem that they cannot be taken for a long time.

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 method for producing a catechin derivative having low side effects and having an excellent lipolytic action.

In order to achieve the above object, the invention according to claim 1 is to extract a fermented product obtained by adding natto bacteria to edible fish, pulverized green tea leaves, and soybeans, followed by heating and fermentation with vegetable oil. This is a method for producing a catechin derivative represented by the following formula (1).

  X is any selected from caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid, lauric acid, 14-methyl palmitic acid Or one.

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

According to the catechin derivative of claim 1, the side effects are weak and an excellent lipolytic action is exhibited.

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

First, a catechin derivative represented by the following formula (1) having a lipolytic action will be described.

  X is any selected from caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid, lauric acid, 14-methyl palmitic acid Or one.

In the first place, catechin is a polyphenol biosynthesized by plants and microorganisms, such as epicatechin and epigallocatechin, and is preferable because epigallocatechin is structurally stable when it forms an ester bond.

The catechin derivative as used herein means that, as represented by the above formula (1), catechin includes caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, Any one selected from stearic acid, methyl stearic acid, lauric acid, and 14-methyl palmitic acid is an ester-linked derivative.

The catechin derivatives include catechin hydroxyl group and caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid, lauric acid, 14-methyl. The carboxylic acid of any substance of palmitic acid has an ester bond.

Although the catechin is widely distributed in green tea leaves, stems, leaves and roots, the structure of catechin is unstable, there is a drawback that it is easy to polymerize, the catechin derivative is structurally stable, It is preferable because it easily infiltrates adipose tissue and has an excellent lipolytic action.

The catechin derivative is any of caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid, lauric acid, and 14-methylpalmitic acid. As a result, the lipid solubility increases, so that it easily enters the target adipose tissue and adipocytes, the structure of the catechin derivative is stabilized, and the lipolytic action is higher than that of catechin itself. Are better.

The catechin derivative induces an enzyme that degrades neutral fat, phospholipid, and the like, exhibits a lipolytic action, and decomposes accumulated neutral fat.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. In addition, it easily penetrates into neutral fats and phospholipids, activates lipolytic enzymes such as lipase and phospholipase, and decomposes fat. Examples of the phospholipase include phospholipase A, phospholipase C, and phospholipase D.

Furthermore, the catechin derivative suppresses the growth of adipocytes in adipose tissues and organs, and activates lipolytic enzymes such as lipases and phospholipases that degrade neutral fats and phospholipids. Disassemble. In particular, it suppresses the growth of fat cells that have entered the organ and breaks down fat.

The catechin derivatives are caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid, lauric acid, 14 having high fat-soluble characteristics. -Since any one selected from methyl palmitate is bound, it is easier to adapt to the cell membranes of the small intestine and skin than catechin, and is easily absorbed by the body.

When the catechin derivative is ingested and absorbed excessively, the excess amount is decomposed by the esterase in the blood, and catechin and the respective caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha -Since it is decomposed into any of lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid, lauric acid, and 14-methylpalmitic acid, each of which has been confirmed to be safe, the above catechin derivatives are also safe. high.

Among the above catechin derivatives, when X is caprylic acid, the medium-chain saturated fatty acid residue of caprylic acid penetrates into the cell membrane, is easily absorbed into cells, works easily on adipose tissue, and enhances lipolytic action. To preferred.

Among the above catechin derivatives, when X is palmitic acid, it is preferable because saturated fatty acid residues of palmitic acid penetrate into the cell membrane, are easily absorbed into cells, work on adipose tissue, and enhance lipolytic action. .

Among the above catechin derivatives, when X is eicosapentaenoic acid, the unsaturated fatty acid residue of eicosapentaenoic acid exhibits an inflammatory prostaglandin production inhibitory action, so that it acts on lipase while suppressing inflammatory action. It is preferable because the decomposition action is stably exhibited.

Among the above catechin derivatives, when X is docosahexaenoic acid, the unsaturated fatty acid residue of docosahexaenoic acid exhibits an inflammatory prostaglandin production inhibitory action. Is preferable because it is stably exhibited.

Among the above catechin derivatives, when X is docosapentaenoic acid, the unsaturated fatty acid residue of docosapentaenoic acid exhibits inflammatory prostaglandin production inhibitory action, and thus acts on lipase while suppressing inflammatory action. Therefore, it is preferable because the lipolytic action is stably exhibited.

Among the above catechin derivatives, when X is alpha-lipoic acid, the fatty acid residue of alpha-lipoic acid exhibits an antioxidant action, so that it inhibits lipid oxidation and peroxidation and works on lipolytic enzymes. It is preferable because lipolysis is stably increased.

Among the above catechin derivatives, when X is gamma-linolenic acid, unsaturated fatty acid residues of gamma-linolenic acid suppress cytokines excreted from adipocytes and act on lipase to stably exhibit lipolytic action. Is preferable.

Among the above catechin derivatives, when X is stearic acid, the saturated fatty acid residue of stearic acid penetrates into the cell membrane and is easily absorbed into the adipose tissue, and acts on the target lipase to enhance the lipolytic action. To preferred.

Among the above catechin derivatives, when X is methyl stearic acid, saturated fatty acid residues of methyl stearic acid penetrate into the cell membrane and are easily absorbed into the adipose tissue, and act on the target lipase to enhance the lipolytic action. Is preferable.

Among the above catechin derivatives, when X is lauric acid, a saturated fatty acid residue of lauric acid penetrates into the cell membrane, is easily absorbed into the cell, works on fat, and enhances the lipase activation action.

Among the above catechin derivatives, when X is 14-methylpalmitic acid, saturated fatty acid residues of 14-methylpalmitic acid penetrate into the cell membrane, are easily absorbed into cells, work easily on lipases, and enhance lipolysis Is preferable.

In addition, it is preferable that a catechin derivative is processed using green tea leaves or green tea stems as raw materials, pulverized, extracted with an organic solvent or vegetable oil, and purified, because it is easily available and economical.

Here, as the organic solvent used for extraction, methanol, ethanol, chloroform, hexane, ethyl acetate, benzene, ether or the like is used, and among them, ethanol for food processing or ethanol containing water is preferable because of its high use range. In addition, it is more preferable to use an organic solvent containing a pine leaf extract, a kokushi extract, a chrysanthemum extract, or a bamboo leaf extract because the target derivative is stably maintained by an antioxidant action.

Vegetable oils used for extraction include palm oil, palm oil, soybean oil, olive oil, rapeseed oil, rice oil, germ oil, corn oil, safflower oil, linseed oil, almond oil, sesame oil, cacao oil, canola oil, grape seed oil , Sesame 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. In addition, it is more preferable to use a vegetable oil containing a pine leaf extract, a kokushi extract, a chrysanthemum extract, or a bamboo leaf extract because the target derivative is stably maintained.

Furthermore, it is preferable to purify fatty acids used for catechin derivatives from plants, beans, and edible fish, or to use purified fats and oils.

For example, these fatty acids can be obtained from Fuji Oil, Nissin Oil, Nissui Pharmaceutical, Nissui Fisheries, Toyo Fisheries, and can be synthesized by biosynthesis using a binding enzyme or chemically.

When catechin derivatives are obtained from these raw materials by biochemical enzymatic reaction, enzymes that cause an ester bond reaction such as lipase AY “Amano” 30G, lipase G “Amano” 50, lipase F-AP15 manufactured by Amano Enzyme. Neurase F3G and the like are used.

In addition, in the case of chemical synthesis reaction, it is heated together with a metal catalyst such as magnesium or aluminum. These raw materials are put into a reaction tank, and the reaction is performed together with the organic solvent. It is preferable to extract this reaction product using the above-mentioned organic solvent and remove the solvent to obtain a crude product, because the cost required for purification can be reduced.

The target catechin derivative can be obtained by extracting the natural catechin derivative from a natural material using the organic solvent or vegetable oil and further purifying it. Natural materials include plants such as green tea leaves, seaweed, mushrooms, edible animals, edible fish, mollusks, insects, and crustaceans. In particular, green tea leaves, edible fish heads and eel heads have a high content and are therefore easy to extract.

Industrially, the heads of edible fish are removed during the processing of edible fish, are discarded as waste, and are not used. Extracting or refining the edible fish head or eel head using the organic solvent or vegetable oil as a raw material is preferable because the waste is effectively used and the amount of waste is reduced.

Obtaining the above catechin derivative by fermentation using microorganisms or yeast is preferable because it is confirmed to be safe for food and has abundant food experience. 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.

The fermentation is performed using a fermentation tank by adding the microorganism or yeast to a fermentation base such as green tea leaves, edible fish, edible fish heads and internal organs, soybeans and milk. After the fermentation, the desired catechin derivative can be obtained from a mixture of microorganisms or yeast and fermentation broth by using the organic solvent or vegetable oil.

When extracting from plants, plants such as green tea leaves and stems, lotus seeds, fruits and berries, roots, leaves and stems, garlic, garlic, onion, garlic, soybeans, scallops, licorice, vermicelli, hanai kada, barley young leaves, kuzu Flowers, capsicum, oysters, pears, chestnuts, cod, horseradish, bracken, rice, wheat, corn, radish, rape blossoms, cherry blossoms, pine, red mushrooms, red squirrels, akebi, echidna , Ibukizasou, Ukogi, Moray eel, Udo, Ume, Vulture, Ebisu rush, Oren, Psyllium, Okera, Okra, Hypericum, Onamomi, Ominae, Oyster, Red-crowned, Pteropus Da, Kiran Sow, Goldworm, Scarlet, Horseshoe, Scrap, Gardenia, Kahone, Kobushi, Saikachi, Sabonsou, Sarutara Rose Bucket, Sanshuyu, Janohige, Silane, Honeysuckle, Seri, Senburi, Tamashiba, Taranoki, Dandelion, Nigella Carcinus, Tochiban carrot, Nanten, Neubara, Octopus, Hazel, Hahakogusa, Hikikoshi, Hishi, Hitotsuba, Biwa, Fuki, Fukujusou, Fuji, Matabi, Mehajiki, Yamanoimo, Yukinoshita, Mugwort, Gentian, Gentian, Gentian Flowers, fruits or roots are preferred because they are readily available.

Green tea here may be Japanese native varieties such as Yabukita, Kanaya Midori, Kurasawa, etc., and may be any of Assam varieties, and the production area is in Japan, Asian countries such as Korea, Taiwan and China, Germany Any of those collected in European countries such as the United States, continental countries such as the United States and Brazil, Australia and New Zealand are preferred. Furthermore, what was made into the powder with the grinder after freeze-drying and natural drying is more preferable.

Green tea is a camellia plant and the scientific name of green tea is Camellia sinensis.

Of these, green tea leaves and stems are preferred because they have rich food experience and can stably supply the desired catechin derivatives.

The fat-soluble catechin derivative is extracted with the 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 It is further 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.

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

Purifying the target catechin derivative from the reaction product or composition is preferable from the viewpoint that the intake amount can be reduced when ingested as a highly pure substance. When highly purified, a separation carrier or resin is utilized and purified. As the separation carrier or resin, porous polysaccharide, silicon oxide compound, polyacrylamide, polystyrene, polypropylene, styrene-vinylbenzene copolymer, etc. whose surface is coated as described later are used. Those having a particle size of 0.1 to 300 μm are preferable. The finer the particle size, the higher the accuracy of the separation, but the longer the separation time.

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

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

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

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

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

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

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

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

When Sephadex LH-20 is used, a lower alcohol is preferable as the separation solvent. When silica gel is used, the separation solvent is preferably chloroform, methanol, acetic acid or a mixture thereof. When Diaion and DM1020T are used, the separation solvent is preferably a lower alcohol such as methanol or ethanol or a mixed solution of lower alcohol and water.

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

The catechin derivative is obtained as a liquid or a powder. The obtained catechin derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing, fibers, plastics and the like.

Drugs include anti-obesity agents, topical lipolytic agents, anti-cellulite agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, prevention of metabolic syndrome and lifestyle-related diseases, etc. Used for Further, it is also used as a veterinary medicine used for animals and a medicine used for pets as a lipolytic agent, an anti-obesity agent, a wrinkle removing agent, a fatty liver inhibitor, a hyperlipidemia improving agent, an anti-arteriosclerosis agent and the like.

The food preparation is used in supplements for preventing or improving obesity, supplements for the purpose of preventing cellulite, reducing local fat, metabolic syndrome and lifestyle-related diseases. Also for veterinary foods and food preparations used for animals or food preparations used for pets, the purpose of lipolysis, obesity improvement and prevention, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and prevention It is used as such.

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

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

Moreover, it uses for the container for the purpose of lipolysis, a toilet, a bath, etc. using the plastic which added the said polyphenol derivative.

Next, among the catechin derivatives represented by the above formula (1) obtained by adding caprylic acid and lipase for transesterification to the pulverized green tea leaf, heating and extracting with vegetable oil, X is caprylic acid. A catechin derivative represented by the following formula (2) having a certain lipolytic action will be described.

The catechin derivative here is the catechin derivative described above, and is a derivative in which carboxylic acid of caprylic acid is ester-bonded to catechin.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat and phospholipid, and improves or prevents the accumulation of fat and phospholipid.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. It easily penetrates into fat and activates lipolytic enzymes such as lipase and phospholipase to break down fat. In particular, it suppresses the proliferation of adipocytes that have entered the organs, and degrades neutral fats and phospholipids.

In the above catechin derivatives, saturated fatty acid residues of caprylic acid penetrate into the cell membrane, are easily absorbed into fat cells, work easily on lipolytic enzymes such as lipases in the target fat, and the lipolytic action is enhanced. Therefore, it is preferable.

The catechin derivative can be obtained by adding caprylic acid and lipase for transesterification to a pulverized green tea leaf, heating the mixture, and extracting with vegetable oil.

Green tea here may be Japanese native varieties such as Yabukita, Kanaya Midori, Kurasawa, etc., and may be any of Assam varieties, and the production area is in Japan, Asian countries such as Korea, Taiwan and China, Germany Any of those collected in European countries such as the United States, continental countries such as the United States and Brazil, Australia and New Zealand are preferred. Furthermore, what was made into the powder with the grinder after freeze-drying and natural drying is more preferable.

Green tea is a camellia plant and the scientific name of green tea is Camellia sinensis.

Of these, green tea leaves and stems are preferred because they have rich food experience and can stably supply the desired catechin derivatives.

It is also used as a cosmetic raw material as green tea leaves, green tea extracts and the like. Of these, green tea made in Japan and China is preferable because it can track the history of pesticide use, has stable quality, and is inexpensive. The green tea leaves may be either fresh or dried. Furthermore, it is preferable that the collected green tea leaves are washed with tap water.

Green tea leaves are 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.

Caprylic 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 green tea leaf pulverized product, caprylic acid and lipase for transesterification 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 caprylic acid is preferably 0.02 to 2 weight, and the amount of lipase for transesterification is preferably 0.0001 to 0.08 weight with respect to 1 weight of the pulverized green tea leaf to be added.

As said heating temperature, 10-42 degreeC is preferable and 18-39 degreeC is more preferable.

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 fat-soluble catechin 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, and other oils used for food or cosmetics are used In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

Among these, pine needle extract-containing vegetable oil is a vegetable oil having an excellent antioxidative action and containing an oil-soluble polyphenol extracted by adding vegetable oil to pulverized pine needles. 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.

The vegetable oil to be added is preferably 0.4 to 4 weights with respect to 1 weight of the pulverized green tea leaf to be added.

The separated catechin derivative is absorbed into the body, and then an excessive amount is decomposed by esterase and further metabolized in the liver. Therefore, safety is high and there are few side effects.

Separating and purifying the target catechin derivative from the reaction product is preferable because 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 catechin derivative by separation with an appropriate separation solvent, purification, and removal of the solvent.

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

The obtained catechin derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing, fibers, plastics and the like.

Drugs include anti-obesity agents, topical lipolytic agents, anti-cellulite agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, prevention of metabolic syndrome and lifestyle-related diseases, etc. Used for Further, it is also used as a veterinary medicine used for animals and a medicine used for pets as a lipolytic agent, an anti-obesity agent, a wrinkle removing agent, a fatty liver inhibitor, a hyperlipidemia improving agent, an anti-arteriosclerosis agent and the like.

The food preparation is used in supplements for preventing or improving obesity, supplements for the purpose of preventing cellulite, reducing local fat, metabolic syndrome and lifestyle-related diseases. Also for veterinary foods and food preparations used for animals or food preparations used for pets, the purpose of lipolysis, obesity improvement and prevention, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and prevention It is used as such.

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

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

Also, it is used for containers, toilets, baths, etc. for the purpose of lipolysis using the above-mentioned plastic mixed with a polyphenol derivative.

Next, among the catechin derivatives represented by the above formula (1) obtained by adding palmitic acid and lipase for transesterification to the pulverized green tea leaf, heating and extracting with vegetable oil, X is palmitic acid. A catechin derivative represented by the following formula (3) having a certain lipolytic action will be described.

The catechin derivative here is the catechin derivative described above, which is a derivative in which carboxylic acid of palmitic acid is ester-bonded to catechin.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat and phospholipid, and improves or prevents the accumulation of fat and phospholipid.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. It easily penetrates into fat and activates lipolytic enzymes such as lipase and phospholipase to break down fat. In particular, it suppresses the proliferation of adipocytes that have entered the organs, and degrades neutral fats and phospholipids.

The catechin derivative suppresses the growth of fat cells in adipose tissue and organs, and decomposes accumulated fat by activating a lipolytic enzyme such as lipase or phospholipase that decomposes neutral fat. In particular, it suppresses the growth of fat cells that have entered the organ and breaks down fat.

In the above catechin derivatives, saturated fatty acid residues of palmitic acid penetrate into the cell membrane, are easily absorbed into fat cells, work easily on the lipase in the target fat, and are preferred because the lipolytic action is enhanced.

The produced fat-soluble catechin 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, and other oils used for food or cosmetics are used In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

Green tea here may be Japanese native varieties such as Yabukita, Kanaya Midori, Kurasawa, etc., and may be any of Assam varieties, and the production area is in Japan, Asian countries such as Korea, Taiwan and China, Germany Any of those collected in European countries such as the United States, continental countries such as the United States and Brazil, Australia and New Zealand are preferred. Furthermore, what was made into the powder with the grinder after freeze-drying and natural drying is more preferable.

Green tea is a camellia plant and the scientific name of green tea is Camellia sinensis. Of these, green tea leaves and stems are preferred because they have rich food experience and can stably supply the desired catechin derivatives.

It is also used as a cosmetic raw material as green tea leaves, green tea extracts and the like. Of these, green tea made in Japan and China is preferable because it can track the history of pesticide use, has stable quality, and is inexpensive. The green tea leaves may be either fresh or dried. Furthermore, it is preferable that the collected green tea leaves are washed with tap water.

The green tea leaves are crushed. For pulverization, a pulverizer is used. For example, a free mill, super free mill, sample mill, goblin, super clean mill, micros manufactured by Nara Machinery Co., Ltd. as a pulverizer, and a small vacuum manufactured by Toyo Riko as a vacuum dryer. A dryer, a small vacuum heat transfer type 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 green tea leaf pulverized product, 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 palmitic acid is preferably 0.02 to 0.5 weight and the transesterification lipase is preferably 0.0001 to 0.04 weight with respect to 1 weight of the pulverized green tea leaf to be added.

As said temperature of heating, 10-30 degreeC is preferable and 13-27 degreeC is more preferable.

The heating time is preferably 1 to 24 hours, more preferably 2 to 14 hours.

The heating is preferably performed while stirring, and a rate of 8 to 120 times per minute is preferable.

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

The produced fat-soluble catechin 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, and other oils used for food or cosmetics are used In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

The pine needle extract-containing vegetable oil here is a vegetable oil containing an oil-soluble polyphenol that is extracted by adding vegetable oil to a pulverized pine needle and is excellent in antioxidant 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.

The vegetable oil to be added is preferably 0.4 to 3% by weight with respect to 1 weight of the pulverized green tea leaf.

After the separated catechin derivative is absorbed into the body, the excess amount is decomposed by esterase and further metabolized in the liver. Therefore, safety is high and there are few side effects.

Separating and purifying the target catechin derivative from the reaction product is preferable because 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 catechin derivative by separation with an appropriate separation solvent, purification, and removal of the solvent.

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

The obtained catechin derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing, fibers, plastics and the like.

Drugs include anti-obesity agents, topical lipolytic agents, anti-cellulite agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, prevention of metabolic syndrome and lifestyle-related diseases, etc. Used for Further, it is also used as a veterinary medicine used for animals and a medicine used for pets as a lipolytic agent, an anti-obesity agent, a wrinkle removing agent, a fatty liver inhibitor, a hyperlipidemia improving agent, an anti-arteriosclerosis agent and the like.

The food preparation is used in supplements for preventing or improving obesity, supplements for the purpose of preventing cellulite, reducing local fat, metabolic syndrome and lifestyle-related diseases. Also for veterinary foods and food preparations used for animals or food preparations used for pets, the purpose of lipolysis, obesity improvement and prevention, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and prevention It is used as such.

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

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

Moreover, it uses for the container for the purpose of lipolysis, a toilet, a bath, etc. using the plastic which added the said polyphenol derivative.

Next, among the catechin derivatives represented by the above formula (1) obtained by adding eicosapentaenoic acid and lipase for transesterification to the pulverized green tea leaf, heating and extracting with vegetable oil, X is eicosapentaene. A catechin derivative represented by the following formula (4) having a lipolytic action as an acid will be described.

The catechin derivative here is the catechin derivative described above, and is a derivative in which carboxylic acid of eicosapentaenoic acid is ester-bonded to catechin.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat and phospholipid, and improves or prevents the accumulation of fat and phospholipid.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. In addition, eicosapentaenoic acid suppresses inflammatory cytokines such as tumor necrosis factor and IL-6 released from fat, and activates lipolytic enzymes such as lipase to suppress fat while suppressing inflammation.

The catechin derivative suppresses the growth of fat cells in adipose tissue and organs, and decomposes accumulated fat by activating a lipolytic enzyme such as lipase or phospholipase that decomposes neutral fat. In particular, it suppresses the growth of fat cells that have entered the organ and breaks down fat.

In the above catechin derivatives, unsaturated fatty acid residues of eicosapentaenoic acid penetrate into the cell membrane, are easily absorbed into fat cells, work easily on lipolytic enzymes such as lipases in the target fat, and enhance lipolytic action This is preferable.

The catechin derivative is obtained by adding eicosapentaenoic acid and lipase for transesterification to a pulverized green tea leaf, heating and extracting with vegetable oil.

The green tea here may be Japanese native varieties such as Yabukita, Kanaya Midori, Kurasawa, or any of the Assam varieties, and the production area is in Japan, Asian countries such as Korea, Taiwan, China, Germany, etc. Any of those collected in European countries, the Americas such as the United States and Brazil, Australia, and New Zealand are preferred. Furthermore, what was made into the powder with the grinder after freeze-drying and natural drying is more preferable.

Green tea is a camellia plant and the scientific name of green tea is Camellia sinensis.

Of these, green tea leaves and stems are preferred because they have rich food experience and can stably supply the desired catechin derivatives.

  It is also used as a cosmetic raw material as green tea leaves, green tea extracts and the like. Of these, green tea made in Japan and China is preferable because it can track the history of pesticide use, has stable quality, and is inexpensive. The green tea leaves may be either fresh or dried. Furthermore, it is preferable that the collected green tea leaves are washed with tap water.

Green tea leaves are 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.

The eicosapentaenoic acid used here is preferably derived from fish and extracted from fish oil and purified, since it has few impurities. Eicosapentaenoic acid manufactured by Nippon Suisan is preferred because of its stable quality.

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 green tea leaf pulverized product, eicosapentaenoic 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 eicosapentaenoic acid is preferably 0.02 to 0.5 weight and the amount of lipase for transesterification is preferably 0.0001 to 0.04 weight with respect to 1 weight of the pulverized green tea leaf to be added.

As said temperature of heating, 10-30 degreeC is preferable and 13-27 degreeC is more preferable.

The heating time is preferably 1 to 24 hours, more preferably 2 to 14 hours.

The heating is preferably performed while stirring, and a rate of 8 to 120 times per minute is preferable.

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

The produced fat-soluble catechin 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, and other oils used for food or cosmetics are used In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

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

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

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

The vegetable oil to be added is preferably 0.4 to 3% by weight with respect to 1 weight of the pulverized green tea leaf.

After the separated catechin derivative is absorbed into the body, the excess amount is decomposed by esterase and further metabolized in the liver. Therefore, safety is high and there are few side effects.

Separating and purifying the target catechin derivative from the reaction product is preferable because 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 catechin derivative by separation with an appropriate separation solvent, purification, and removal of the solvent.

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

The obtained catechin derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing, fibers, plastics and the like.

Drugs include anti-obesity agents, topical lipolytic agents, anti-cellulite agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, prevention of metabolic syndrome and lifestyle-related diseases, etc. Used for Further, it is also used as a veterinary medicine used for animals and a medicine used for pets as a lipolytic agent, an anti-obesity agent, a wrinkle removing agent, a fatty liver inhibitor, a hyperlipidemia improving agent, an anti-arteriosclerosis agent and the like.

The food preparation is used in supplements for preventing or improving obesity, supplements for the purpose of preventing cellulite, reducing local fat, metabolic syndrome and lifestyle-related diseases. Also for veterinary foods and food preparations used for animals or food preparations used for pets, the purpose of lipolysis, obesity improvement and prevention, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and prevention It is used as such.

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

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

In addition, it is used for containers, toilets, baths, etc. for the purpose of lipolysis using the above-mentioned plastic added with a catechin derivative.

Next, docosahexaenoic acid and lipase for transesterification are added to the pulverized green tea leaf, heated, and extracted from the vegetable oil. Among the catechin derivatives represented by the above formula (1), X is docosahexaenoic acid. A catechin derivative represented by the following formula (5) having a certain lipolytic action will be described.

The catechin derivative here is the catechin derivative described above, which is a derivative in which carboxylic acid of docosahexaenoic acid is ester-bonded to catechin.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat and phospholipid, and improves or prevents the accumulation of fat and phospholipid.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. In addition, docosahexaenoic acid activates lipolytic enzymes such as lipase and inhibits fat while suppressing inflammation by inhibiting tumor necrosis factor and IL-6 released from fat.

The above catechin derivatives inhibit the growth of adipocytes in adipose tissues and organs, and activate fat-degrading enzymes such as lipase that degrades neutral fat and phospholipase that degrades phospholipids. Disassemble. In particular, it suppresses the growth of fat cells that have entered the organ and breaks down fat.

In the above catechin derivatives, unsaturated fatty acid residues of docosahexaenoic acid penetrate into the cell membrane, are easily absorbed into fat cells, work easily on lipases such as lipases and phospholipases in target fats, and enhance lipolytic action Is preferable.

The catechin derivative is obtained by adding docosahexaenoic acid and lipase for transesterification to a pulverized green tea leaf, heating and extracting with vegetable oil.

The green tea here may be Japanese native varieties such as Yabukita, Kanaya Midori, Kurasawa, or any of the Assam varieties, and the production area is in Japan, Asian countries such as Korea, Taiwan, China, Germany, etc. Any of those collected in European countries, the Americas such as the United States and Brazil, Australia, and New Zealand are preferred. Furthermore, what was made into the powder with the grinder after freeze-drying and natural drying is more preferable.

Green tea is a camellia plant and the scientific name of green tea is Camellia sinensis.

Of these, green tea leaves and stems are preferred because they have rich food experience and can stably supply the desired catechin derivatives.

It is also used as a cosmetic raw material as green tea leaves, green tea extracts and the like. Of these, green tea made in Japan and China is preferable because it can track the history of pesticide use, has stable quality, and is inexpensive. The green tea leaves may be either fresh or dried. Furthermore, it is preferable that the collected green tea leaves are washed with tap water.

Green tea leaves are 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, 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 docosahexaenoic acid used here is preferably derived from fish and extracted from fish oil and purified, since it has few impurities. Docosahexaenoic acid manufactured by Nippon Suisan is preferred because of its stable quality.

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 green tea leaf pulverized product, docosahexaenoic 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 docosahexaenoic acid is preferably 0.02 to 0.5 weight, and the amount of lipase for transesterification is preferably 0.0001 to 0.04 weight with respect to 1 weight of the pulverized green tea leaf to be added.

As said temperature of heating, 10-30 degreeC is preferable and 13-27 degreeC is more preferable.

The heating time is preferably 1 to 24 hours, more preferably 2 to 14 hours.

The heating is preferably performed while stirring, and a rate of 8 to 120 times per minute is preferable.

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

The produced fat-soluble catechin 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, and other oils used for food or cosmetics are used In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

The pine needle extract-containing vegetable oil here is a vegetable oil containing an oil-soluble polyphenol that is extracted by adding vegetable oil to a pulverized pine needle and is excellent in antioxidant 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.

The vegetable oil to be added is preferably 0.4 to 3% by weight with respect to 1 weight of the pulverized green tea leaf.

After the separated catechin derivative is absorbed into the body, the excess amount is decomposed by esterase and further metabolized in the liver. Therefore, safety is high and there are few side effects.

Separating and purifying the target catechin derivative from the reaction product is preferable because 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 catechin derivative by separation with an appropriate separation solvent, purification, and removal of the solvent.

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

The obtained catechin derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing, fibers, plastics and the like.

Drugs include anti-obesity agents, topical lipolytic agents, anti-cellulite agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, prevention of metabolic syndrome and lifestyle-related diseases, etc. Used for Further, it is also used as a veterinary medicine used for animals and a medicine used for pets as a lipolytic agent, an anti-obesity agent, a wrinkle removing agent, a fatty liver inhibitor, a hyperlipidemia improving agent, an anti-arteriosclerosis agent and the like.

The food preparation is used in supplements for preventing or improving obesity, supplements for the purpose of preventing cellulite, reducing local fat, metabolic syndrome and lifestyle-related diseases. Also for veterinary foods and food preparations used for animals or food preparations used for pets, the purpose of lipolysis, obesity improvement and prevention, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and prevention It is used as such.

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

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

Moreover, it uses for the container for the purpose of lipolysis, a toilet, a bath, etc. using the plastic which added the said polyphenol derivative.

Next, a catechin derivative having a lipolytic action obtained by extracting a fermented product obtained by adding natto bacteria to edible fish, green tea leaves and soybeans and fermenting them with vegetable oil will be described.

The catechin derivative having a lipolytic action here is the catechin derivative described above.

That is, catechin is selected from caprylic acid, palmitic acid, lauric acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid Any one of these is a derivative bonded.

This catechin derivative is caprylic acid, palmitic acid, lauric acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid The carboxylic acid group of the substance has an ester bond.

The catechin derivatives here include caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, and methyl stearic acid. By bonding, the structure of catechin is stabilized.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat, and prevents fat accumulation.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. It also enhances blood flow and lymph flow to activate lipolytic enzymes such as lipases and phospholipid degrading enzymes, and to break down fat.

The catechin derivative suppresses the growth of fat cells in adipose tissue and organs, and decomposes accumulated fat by activating a lipolytic enzyme such as lipase or phospholipase that decomposes neutral fat. In particular, it suppresses the growth of fat cells that have entered the organ and breaks down fat.

In the catechin derivatives described above, unsaturated fatty acid residues and saturated fatty acid residues penetrate the cell membrane and are easily absorbed into fat cells, and easily act on lipolytic enzymes such as lipases and phospholipases in the target fat, thereby causing lipolysis. It is preferable because the action is enhanced.

The catechin derivatives are caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid having high fat-soluble characteristics Since any one selected from methyl stearic acid is bonded, it has a feature that it can be easily adapted to and absorbed by the cell membrane of the small intestine and skin.

When the catechin derivative is ingested and absorbed in excess, the excess amount is decomposed by the esterase in the blood and catechin and the respective caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, Docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, and methyl stearic acid have been confirmed to be safe. high.

Among the above catechin derivatives, when X is caprylic acid, the medium-chain saturated fatty acid residue of caprylic acid penetrates into the cell membrane, is easily absorbed into cells, works easily on adipose tissue, and enhances lipolytic action. To preferred.

Among the above catechin derivatives, when X is palmitic acid, it is preferable because saturated fatty acid residues of palmitic acid penetrate into the cell membrane, are easily absorbed into cells, work on adipose tissue, and enhance lipolytic action. .

Among the above catechin derivatives, when X is eicosapentaenoic acid, the unsaturated fatty acid residue of eicosapentaenoic acid exhibits an inflammatory prostaglandin production inhibitory action, so that it acts on lipase while suppressing inflammatory action. It is preferable because the decomposition action is stably exhibited.

Among the above catechin derivatives, when X is docosahexaenoic acid, the unsaturated fatty acid residue of docosahexaenoic acid exhibits an inflammatory prostaglandin production inhibitory action. Is preferable because it is stably exhibited.

Among the above catechin derivatives, when X is docosapentaenoic acid, the unsaturated fatty acid residue of docosapentaenoic acid exhibits inflammatory prostaglandin production inhibitory action, and thus acts on lipase while suppressing inflammatory action. Therefore, it is preferable because the lipolytic action is stably exhibited.

Among the above catechin derivatives, when X is alpha-lipoic acid, the fatty acid residue of alpha-lipoic acid exhibits an antioxidant action, so that it inhibits lipid oxidation and peroxidation and works on lipolytic enzymes. It is preferable because lipolysis is stably increased.

Among the above catechin derivatives, when X is gamma-linolenic acid, unsaturated fatty acid residues of gamma-linolenic acid suppress cytokines excreted from adipocytes and act on lipase to stably exhibit lipolytic action. Is preferable.

Among the above catechin derivatives, when X is stearic acid, the saturated fatty acid residue of stearic acid penetrates into the cell membrane and is easily absorbed into the adipose tissue, and acts on the target lipase to enhance the lipolytic action. To preferred.

Among the above catechin derivatives, when X is methyl stearic acid, saturated fatty acid residues of methyl stearic acid penetrate into the cell membrane and are easily absorbed into the adipose tissue, and act on the target lipase to enhance the lipolytic action. Is preferable.

Among the above catechin derivatives, when X is lauric acid, a saturated fatty acid residue of lauric acid penetrates into the cell membrane, is easily absorbed into the cell, works on fat, and enhances the lipase activation action.

Among the above catechin derivatives, when X is 14-methylpalmitic acid, saturated fatty acid residues of 14-methylpalmitic acid penetrate into the cell membrane, are easily absorbed into cells, work easily on lipases, and enhance lipolysis Is preferable.

The catechin derivative is obtained by extracting a fermented product obtained by adding natto bacteria to edible fish, green tea leaves and soybeans and fermenting them with vegetable oil. As used herein, edible fish refers to fish used for food, and among them, eels have abundant food experience.

Eel head and internal organs have dietary experience, caprylic acid, lauric acid, palmitic acid, 14-methyl palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid It is preferable because it contains methyl stearic acid.

In the fishery, eel heads and internal organs are discarded in the processing process, which is preferable because waste can be used effectively.

Of these, eels grown and grown on the shores of Lake Hamana are preferred. Moreover, it is preferable to dismantle after slaughtering at a dismantling site, cut the head and internal organs, and collect.

It is preferable to cut the collected eel head and internal organs with a knife and pulverize them with DM-6 manufactured by Nakayama Institute of Technology.

The green tea here may be Japanese native varieties such as Yabukita, Kanaya Midori, Kurasawa, or any of the Assam varieties, and the production area is in Japan, Asian countries such as Korea, Taiwan, China, Germany, etc. Any of those collected in European countries, the Americas such as the United States and Brazil, Australia, and New Zealand are preferred. Furthermore, what was made into the powder with the grinder after freeze-drying and natural drying is more preferable.

Green tea is a camellia plant and the scientific name of green tea is Camellia sinensis.

Of these, green tea leaves and stems are preferred because they have rich food experience and can stably supply the desired catechin derivatives.

It is also used as a cosmetic raw material as green tea leaves, green tea extracts and the like. Of these, green tea made in Japan and China is preferable because it can track the history of pesticide use, has stable quality, and is inexpensive. The green tea leaves may be either fresh or dried. Further, the green tea leaves are preferably pulverized by a pulverizer such as DM-6 manufactured by Nakayama Technical Research Institute.

Soybean here can be used from any origin, such as from Japan, China, the United States, or Russia, and is preferably pulverized by a pulverizer such as DM-6 manufactured by Nakayama Technical Research Laboratory.

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 said fermentation, 0.03-0.3 weight is preferable for green tea leaves with respect to 1 weight of edible fish, 0.1-3 weight is preferable for soybeans, and 0.001-0 for Bacillus natto. 0.03 weight is preferred. 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 30-40 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 fat-soluble catechin derivative produced by the fermentation is extracted with vegetable oil. Vegetable oils include palm oil, palm oil, soybean oil, olive oil, rapeseed oil, rice oil, germ oil, corn oil, safflower oil, linseed oil, almond oil, sesame oil, cacao oil, canola oil, grape seed oil, and sesame oil , Wheat germ oil, rice bran oil, safflower oil, perilla oil, tea oil, camellia oil, pumpkin seed oil, peanut oil, grape oil, hazelnut oil, cottonseed oil, peanut oil, and other oils used for food or cosmetics are used In addition, it is more preferable to use a vegetable oil containing a bamboo leaf extract, a kokushi extract, a chrysanthemum extract or a pine leaf extract because the target derivative is stably maintained.

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

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

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

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

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

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

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

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

After the separated catechin 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 catechin derivative from the reaction product is preferable because 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 catechin 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 catechin derivative thus obtained is obtained as a liquid or a powder.

The obtained catechin derivatives are used for pharmaceuticals, food preparations, cosmetics, hygiene tools, clothing, fibers, plastics and the like.

Drugs include anti-obesity agents, topical lipolytic agents, anti-cellulite agents, wrinkle removal agents, fatty liver inhibitors, hyperlipidemia improving agents, anti-arteriosclerotic agents, prevention of metabolic syndrome and lifestyle-related diseases, etc. Used for Further, it is also used as a veterinary medicine used for animals and a medicine used for pets as a lipolytic agent, an anti-obesity agent, a wrinkle removing agent, a fatty liver inhibitor, a hyperlipidemia improving agent, an anti-arteriosclerosis agent and the like.

The food preparation is used in supplements for preventing or improving obesity, supplements for the purpose of preventing cellulite, reducing local fat, metabolic syndrome and lifestyle-related diseases. Also for veterinary foods and food preparations used for animals or food preparations used for pets, the purpose of lipolysis, obesity improvement and prevention, wrinkle removal, fatty liver suppression, hyperlipidemia improvement, arteriosclerosis suppression and prevention It is used as such.

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

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

Moreover, it uses for the container for the purpose of lipolysis, a toilet, a bath, etc. using the plastic which added the said polyphenol derivative.

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 catechin derivative having a lipolytic action. A food preparation comprising:

The catechin derivative having a lipolytic action as used herein may be any of a crude product, a mixture, a synthesized product, a highly purified substance extracted with an organic solvent or vegetable oil and purified. , At the X position of catechin, caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid Any one selected from the above is an ester-linked derivative.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat and phospholipid, and prevents fat accumulation.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. It also enhances blood flow and lymph flow and activates lipolytic enzymes such as lipase and phospholipase to break down fat.

The catechin derivative suppresses the growth of fat cells in adipose tissue and organs, and decomposes accumulated fat by activating a lipolytic enzyme such as lipase or phospholipase that decomposes neutral fat.

In particular, it suppresses the growth of fat cells that have entered the organ and breaks down fat.

In the catechin derivatives described above, unsaturated fatty acid residues and saturated fatty acid residues penetrate the cell membrane and are easily absorbed into fat cells, and easily act on lipolytic enzymes such as lipases and phospholipases in the target fat, thereby causing lipolysis. It is preferable because the action is enhanced.

The catechin derivatives are caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid having high fat-soluble characteristics Since any one selected from methyl stearic acid is bonded, it has a feature that it can be easily adapted to and absorbed by the cell membrane of the small intestine and skin.

The chrysanthemum flower extract-containing vegetable oil here is a vegetable oil having an excellent antioxidant effect obtained by extracting a ground chrysanthemum flower with a 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. ,

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 0.01-0.5 wt. And the pine needle extract-containing vegetable oil is 0.01-0.5 wt. This gives a composition.

When the weight of the chrysanthemum flower extract-containing vegetable oil is less than 0.01 weight per 1 weight of the catechin 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 catechin derivative, the solubility of the catechin derivative is lowered and may be precipitated.

When the weight of the pine needle extract-containing vegetable oil is less than 0.01 weight relative to 1 weight of the catechin 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 relative to 1 weight of the catechin derivative, the solubility of the catechin 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 catechin derivative is gradually released gradually to form a continuous composition.

Moreover, by comprising in this way, a catechin 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 lipolytic 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 due to fat and cholesterol accumulation, improving liver function, recovering from fatigue, strengthening muscles, dieting, and nutrition.

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 catechin derivative having lipolytic action A cosmetic product consisting of

The catechin derivative having a lipolytic action herein may be any of a crude product, a mixture, a synthesized product, and a highly purified substance extracted and purified. The catechin derivative includes catechin, capryl, Any one selected from acid, lauric acid, palmitic acid, 14-methyl palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid It is a bound derivative.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat, and prevents fat accumulation.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. It also enhances blood flow and lymph flow to activate lipase and break down fat.

The catechin derivative suppresses the growth of fat cells in adipose tissue and organs and activates lipase that decomposes neutral fat, thereby decomposing accumulated fat.
In particular, it suppresses the proliferation of adipocytes that have invaded the organ and breaks down neutral fat.

In the above catechin derivatives, unsaturated fatty acid residues and saturated fatty acid residues permeate the cell membrane and are easily absorbed into fat cells, easily act on lipases in the target fat, and enhance lipolytic action. preferable.

The catechin derivatives are caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid having high fat-soluble characteristics Since any one selected from methyl stearic acid is bonded, it has a feature that it can be easily adapted to and absorbed by the cell membrane of the small intestine and skin.

The chrysanthemum flower extract-containing vegetable oil here is an oil obtained by adding vegetable oil to a ground product of chrysanthemum flowers and extracting it, and has an excellent antioxidant effect.

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. It is more preferable that the oil used in the above is used, and the use of vegetable oil containing persimmon leaf extract, kokushi extract, chrysanthemum extract or pine leaf extract, etc., because the desired 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.

If the weight of the chrysanthemum flower extract-containing vegetable oil is less than 0.05 weight per 1 weight of the catechin 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 wt. Per 1 wt.

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

When the weight of the pine needle extract-containing vegetable oil is more than 0.8 wt. Per 1 wt.

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 catechin derivative is gradually released gradually to form a continuous composition.

Moreover, by comprising in this way, a catechin 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, the treatment or prevention effect of wrinkles and sagging 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 effect of improving cellulite by exhibiting a lipolytic action. That is, cellulite is generated by the accumulation of waste products due to stagnation of blood flow around fat due to the accumulation of fat under the skin. In order to remove this cellulite, it is preferable that a substance exhibiting a lipolytic action, in which fat is easily immersed, works. In this regard, this cosmetic product has a function of removing cellulite and preventing cellulite by lipolysis.

In particular, it exhibits an excellent cellulite-removing action on cellulite in the lower limbs of women with reduced coldness and circulation. It also shows an improving effect on wrinkles and skin irregularities caused by fat cooking.

Furthermore, this cosmetic product also exhibits an improvement or preventive action by removing fat against atopy and chemical hypersensitivity caused by chemical substances and allergens that easily accumulate in fat.

Next, the anti-obesity drug comprising the catechin derivative having the lipolytic action will be described.

The catechin derivative having a lipolytic action herein may be any of a crude product, a mixture, a synthesized product, and a highly purified substance extracted and purified. The catechin derivative includes catechin, capryl, Any one selected from acid, lauric acid, palmitic acid, 14-methyl palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid It is a bound derivative.

The catechin derivative exhibits a lipolytic action such as neutral fat and phospholipid, decomposes accumulated neutral fat, and prevents fat accumulation.

Since the catechin derivative has a fatty acid side chain, it easily penetrates into adipose tissue, and as a result of suppressing the function of growth factors of adipocytes, it suppresses the increase of adipocytes. It also enhances blood flow and lymph flow, activates lipolytic enzymes such as lipase and phospholipase, and breaks down fats such as neutral fat and phospholipid.

The catechin derivative suppresses the growth of adipocytes in adipose tissue and organs, and decomposes accumulated fat by activating lipase and phospholipase that degrades neutral fat. In particular, it suppresses the proliferation of adipocytes that have invaded the organ and breaks down neutral fat.

In the above catechin derivatives, unsaturated fatty acid residues and saturated fatty acid residues permeate the cell membrane and are easily absorbed into fat cells, easily act on lipases in the target fat, and enhance lipolytic action. preferable.

The catechin derivatives are caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid having high fat-soluble characteristics Since any one selected from methyl stearic acid is bonded, it has a feature that it can be easily adapted to and absorbed by the cell membrane of the small intestine and skin.

When used as a pharmaceutical, since it is necessary to remove the influence of impurities, it is preferable to use a catechin derivative having the structure described above, which is synthesized by an enzymatic reaction and has little residual solvent.

It is used as a pharmaceutical orally or parenterally, and as a quasi-drug, it is used by blending with tablets, capsules, drinks, soaps, toothpastes and the like.

Examples of oral preparations include tablets, capsules, powders, syrups, and drinks. When mixed with the above-mentioned tablets and capsules, it can be used together with a binder, excipient, swelling agent, lubricant, sweetener, flavoring agent and the like. The tablets can also be coated with shellac or sugar.

Moreover, in the case of the said capsule, liquid carriers, such as fats and oils, can be further contained in said material. In the case of the above syrup and drink, sweeteners, preservatives, pigment flavoring agents and the like can be contained.

Examples of parenteral preparations include injections in addition to external preparations such as ointments, creams, and liquids. As the base material of the external preparation used here, petrolatum, paraffin, fats and oils, lanolin, macro gold and the like are used, and an ointment, a cream and the like can be obtained by a usual method.

Injections include liquids, and other lyophilization agents. This is used aseptically dissolved in distilled water for injection or physiological saline at the time of use.

The anti-obesity drugs mentioned here have an effect of treating or preventing excessive accumulation of fat in the skin, whole body or local area, and various diseases caused by accumulation of fat such as fatty liver, heart disease and arteriosclerosis. The target drug or quasi drug product.

The whole body fat includes visceral fat and subcutaneous fat. In particular, visceral fat accumulates in internal organs and is a malicious adipose tissue that damages the internal organs. That is, visceral fat releases lipid peroxide, destroys the cell membrane of the parenchyma, and tumor necrosis factor and interleukins that are secreted from the adipose tissue destroy the parenchyma. For example, liver disorders, bile duct disorders, kidney disorders, and heart diseases due to visceral fat accumulation are known and related to lifestyle-related diseases and metabolic syndrome. Present.

This anti-obesity drug improves liver function, kidney function, and cardiac dysfunction by reducing visceral fat, the causative agent of the disease. It is also used for removing cellulite as an external preparation for skin.

In addition, it can be used as a veterinary medicine for the purpose of improving obesity and fat accumulation in livestock and pets.

Hereinafter, the embodiment will be specifically described with reference to Examples , Reference Examples, and Test Examples. In addition, the following description is an example and can be implemented changing a form. Examples 2 to 9 shown below are described as reference examples.

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

80 eels (scientific name: Angulara japonica) grown on the shores of Lake Hamana were used as raw materials. The grown eels were slaughtered at a demolition site and then disassembled, and the head and internal organs were cut and collected. The body part was edible and the head and internal organs were collected.

The collected head and internal organs of 1.9 kg were cut with a knife and pulverized with DM-6 manufactured by Nakayama Institute of Technology.

This was put into a clean culture tank, and 3.5 L of tap water was added. After washing 1.9 kg of green tea leaves collected in Shizuoka Prefecture cultivated without agricultural chemicals with tap water, they were dried with a dryer (Nishimura Kikai Co., Ltd., GZQ3 type) and DM-6 manufactured by Nakayama Technical Research Institute. Crushed. 190 g of the green tea leaf pulverized product was added to the above cylinder. Chinese soybean was washed with water, heated to 39 ° C. for 90 minutes and pulverized to obtain 1.5 kg of pulverized soybean.

To this, 19 g of natto bacteria manufactured by Natto Motopo was added. Fermentation was continued for 40 hours at 37 ° C. with stirring.

3.9 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 catechin derivative was obtained as an oily substance. This was used as the sample of Example 1.

The preparation of a catechin derivative to which caprylic acid is bound is described below.

  1 kg of green tea leaves from Miyazaki grown without pesticides were purchased, washed thoroughly with tap water, and dried with a dryer. Further, 1 kg of this green tea leaf was subjected to a pulverizer (manufactured by Sanriki Seisakusho Co., Ltd., a three-powered universal pulverizer) and pulverized to obtain a pulverized product of green tea leaves.

1 kg of green tea leaf pulverized material was put into a clean cylinder and 9 L of tap water was added. To this, 230 g of caprylic 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 32 ° C. and stirred at a rate of 65 times / minute for 10 hours to obtain a heated solution.

After cooling the cylinder containing the above-mentioned warming solution with tap water, 1.1 kg of RIKEN vitamin palm oil was added, and the oil portion was collected.

The oil portion was dried by a vacuum dryer (manufactured by AKM Kyushu Technos, Clean Dry) to obtain a catechin derivative to which caprylic acid was bound as an oily liquid. This was also used as the sample of Example 2.

The preparation of a catechin derivative to which palmitic acid is bound is described below.

2 kg of green tea leaves from Shizuoka grown without pesticides were collected, washed thoroughly with tap water, and dried with a dryer (GZQ3 type, manufactured by Nishimura Kikai). This was used as a raw green tea leaf.

2 kg of the green tea leaves were subjected to a pulverizer (manufactured by Sanriki Seisakusho Co., Ltd., a three-purpose universal pulverizer) and pulverized to obtain a pulverized product of green tea leaves.

1 kg of green tea leaf pulverized material was placed in a clean cylinder and 10 L of tap water was added. To this, 220 g of valmitic 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 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 with a vacuum dryer (manufactured by AKM Kyushu Technos, Clean Dry) to obtain a catechin derivative to which palmitic acid was bound as an oily liquid. This was also used as the sample of Example 3.

Hereinafter, preparation of a catechin derivative to which eicosapentaenoic acid is bound will be described.

3 kg of green tea leaves from Shizuoka grown without pesticides were collected, thoroughly washed with tap water, and dried with a dryer. This was used as a raw green tea leaf. This green tea leaf (2.2 kg) was subjected to a pulverizer (manufactured by Sanriki Seisakusho Co., Ltd., a three-powered universal pulverizer) and pulverized to obtain a green tea leaf pulverized product.

1.9 kg of green tea leaf pulverized product was placed in a clean cylinder and 19 L of tap water was added. To this, 300 g of Eicosapentaenoic acid manufactured by Nippon Suisan was added and stirred.

To this was added 19 g of lipase AY “Amano” 30G manufactured by Amano Enzyme, and the mixture was heated to 29 ° C. and stirred at a rate of 60 times / minute for 13 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 with a vacuum dryer (manufactured by AKM Kyushu Technos, Clean Dry) to obtain a catechin derivative to which eicosapentaenoic acid was bound as an oily liquid. This was also used as the sample of Example 4.

The preparation of a catechin derivative to which docosahexaenoic acid is bound is described below.

2.9 kg of green tea leaves from Gifu grown without pesticides were collected, washed thoroughly with tap water, and dried with a dryer (GZQ3 type, manufactured by Nishimura Kikai Co., Ltd.). This was used as a raw green tea leaf.

The green tea leaves (2.5 kg) were subjected to a pulverizer (manufactured by Sanriki Seisakusho Co., Ltd., a three-powered universal pulverizer) and pulverized to obtain a green tea leaf pulverized product.

1.1 kg of green tea leaf pulverized product was placed in a clean cylinder and 10 L of tap water was added. To this, 350 g of docosahexaenoic acid manufactured by Nissui Pharmaceutical 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 69 times / minute for 12 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 with a vacuum dryer (manufactured by AKM Kyushu Technos, Clean Dry) to obtain a catechin derivative to which docosahexaenoic acid was bound as an oily liquid. This was also used as the sample of Example 5.

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

300 g of the catechin derivative obtained in Example 4 was suspended in 500 mL of ethanol and applied to a column packed with 880 g of Diaion manufactured by Mitsubishi Chemical. This was washed with 1000 mL of water containing 5% ethanol. Further, after washing with 950 mL of water containing 20% ethanol, elution was performed with 900 mL of water containing 70% ethanol, and then a fraction of water containing 90% ethanol was collected.

This fraction was subjected to a vacuum dryer to distill off ethanol and water, and then 30 g of an oily purified product of catechin derivatives 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 catechin derivative is demonstrated.
(Test Example 1)

Each catechin derivative obtained in Example 1, Example 2, Example 3, Example 4, Example 5, Example 5 and Example 6 obtained as described above was dissolved in purified ethanol, and a high-speed instrument with a mass spectrometer was used. 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, catechin as a catechin derivative was changed to caprylic acid, lauric acid, palmitic acid, 14-methylpalmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma- Catechin derivatives bound with linolenic acid, stearic acid, and methyl stearic acid were identified.

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

Further, from the sample of Example 3, a catechin derivative in which palmitic acid was bound to catechin was identified. The carboxylic acid of palmitic acid was ester-bonded to the hydroxyl group of the catechin skeleton.

Further, from the specimens of Example 4 and Example 6, a catechin derivative in which eicosapentaenoic acid was bound to catechin was identified. The carboxylic acid of eicosapentaenoic acid was ester-bonded to the hydroxyl group of the catechin skeleton.

Further, from the sample of Example 5, a catechin derivative in which docosahexaenoic acid was bound to catechin was identified. The carboxylic acid of docosahexaenoic acid was ester-bonded with the hydroxyl group of the catechin skeleton.

Below, the test of the fat reduction effect using a SCID mouse and a human derived fat cell is demonstrated.
(Test Example 2)

The SCID mouse used here is a severe combined immunodeficient mouse, and since its immune function is reduced, various human-derived cells and tissues can be transplanted, and human-derived adipocytes can be proliferated and grown in the body. This method is rich in test examples and is used in the development and research of pharmaceuticals. A human-derived white adipocyte culture kit manufactured by Wako Pure Chemical Industries was purchased and grown by culturing to obtain human-derived adipocytes.

The back of this SCID mouse was transplanted with 100,000 human-derived adipocytes cultured as described above. A solid sample for breeding mice was fed as food. From the day after transplantation, the sample 1 obtained in Example 1 was suspended in 0.2% gum arabic water and orally administered for 14 days. In addition, 0.2% gum arabic water alone was administered to the water intake control group.

The number of animals in one group is 5, and 14 days after dosing, blood neutral blood is collected from the abdominal artery under ether anesthesia and centrifuged to obtain the amount of neutral fat in the blood (made by Wako Pure Chemical Industries, Ltd.) (Acetylacetone method).

As a result, the blood triglyceride level of SCID mice to which 1 mg of the catechin derivatives of Examples 1 to 6 was orally administered for 14 days was compared with the blood triglyceride level of the water intake control group, and the mean value was obtained. 57% for the sample of Example 1, 59% for the sample of Example 2, 61% for the sample of Example 3, 59% for the sample of Example 4, 59% for the sample of Example 5, and for the sample of Example 6 The reduction of blood triglyceride level by these specimens was confirmed by 42%.

From these results, it was confirmed that the catechin derivatives obtained in Examples 1 to 6 have an effect of reducing neutral fat.

In addition, the weight of the human-derived adipose tissue transplanted on the back of the animal to which the catechin derivative was administered was 77% for the sample of Example 1 and 81 for the sample of Example 2 as an average value compared to the value of the water intake control group. %, 68% for the sample of Example 3, 73% for the sample of Example 4, 68% for the sample of Example 5, and 57% for the sample of Example 6, and any of these samples has a fat tissue reducing effect. Admitted.

On the other hand, the weight of the human-derived adipose tissue transplanted to the back of the animal to which only the solvent was administered was 99% compared to the value of the water intake control group, and no change was observed in the adipose tissue.

Furthermore, the body weight of the animals to which the catechin derivative was administered was 89% for the sample of Example 1, 77% for the sample of Example 2, and 83 for the sample of Example 3 as an average value compared to the value of the water intake control group. %, 77% in the sample of Example 4, 81% in the sample of Example 5, and 69% in the sample of Example 6, and any sample administration also showed a body weight reducing effect.

On the other hand, the body weight of the animals to which only the solvent was administered was 101% compared to the value of the water intake control group, and no change was observed in the body weight.

From these results, the catechin derivatives obtained in Examples 1 to 6 showed the effects of weight loss, fat reduction, and blood neutral fat value reduction. However, none of the specimens showed symptoms during the dosing period, and no other abnormalities were visually observed in other organs, confirming safety.

Below, manufacture of the foodstuff formulation containing a catechin derivative is described.

100 g of the catechin derivative obtained in Example 1 was placed in a food processing mixer (Tsukasa, pow mixer, single type), and 20 g of chrysanthemum flower extract-containing vegetable oil manufactured by Toyo Fermentation Co., Ltd. was added. To this, 11 g of pine leaf extract-containing soybean oil manufactured by Toyo Fermentation Co., Ltd. was added, and this was heated at 37 ° C. for 24 hours with stirring to obtain about 125 g of a composition.

To 120 g of this composition, 300 g of edible cellulose, 1.2 g of ascorbic acid and 11 g of edible fragrance were added to a food processing mixer (Tsukasa, Pow mixer, W type) and mixed. This was pulverized by a conventional method, dried, and then filled into swine-derived gelatin hard capsules at a dose of 280 mg to obtain a food preparation. This was used as the sample of Example 7. Below, the test of the food formulation with respect to the higher neutral fat is demonstrated.
(Test Example 3)

Five males and five females having a triglyceride level of 177 to 544 mg / dL were ingested 3 tablets (840 mg) of the food preparation obtained in Example 7 three times a day for 28 days after each meal. . The blood triglyceride level was examined before the test and 28 days after ingestion.

As a result, ingestion of the food preparation of Example 7 had a neutral fat level of 29% for males and 30% for females, both of which were reduced as compared to before consumption. In addition, blood glucose levels were 19% on average for men and 18% on average for women, both showing a decrease compared to before consumption. In addition, the average body weight was 14% for men, the average for women was 18%, and a decrease was observed compared to before consumption.

There was no change in the physical condition due to the intake of food preparations, and no side effects were observed in the blood test, other blood biochemical tests, and urinalysis.

As a result, the food preparation of Example 7 decreased the neutral fat, blood glucose level and body weight with respect to the higher neutral fat. Moreover, the side effect by the food formulation intake of Example 7 was not recognized, but safety was confirmed.

Below, manufacture of the cosmetic formulation containing a catechin derivative is described.

100 g of the catechin derivative obtained in Example 2 was put into a cosmetic processing mixer (manufactured by Kotobuki Kogyo Co., Ltd., Paule Container Mixer), and 10 g of chrysanthemum flower extract-containing vegetable oil manufactured by Toyo Fermentation Co., Ltd. was added. To this, 30 g of pine leaf extract-containing soybean oil manufactured by Toyo Fermentation Co., Ltd. was added, and this was heated at 37 ° C. for 24 hours with stirring to obtain about 110 g of a composition.

This composition was put into the above mixer, 450 g of beeswax (manufactured by API) and 1 g of squalane (manufactured by Nihon Suisan) were added and mixed to obtain a cream as a cosmetic preparation. This was used as the sample of Example 8. At the same time, a cream containing a base material except for only the catechin derivative obtained in Example 2 was prepared as a control sample.

Below, the test example evaluated about the effect and side effect of cosmetics is shown.
(Test Example 6)

For 10 healthy women aged 28 to 60 years, where cellulite is observed in the thighs of both feet, 3 g of the cream obtained in Example 8 on the right foot thigh is made up of only the base material on the left foot thigh daily. A control claim 3g was applied for 14 days. After the application, the oil content (Mortex, Triple Sense) and skin elasticity (Integral, shock wave measuring device, RVM600) were measured.

As a result, the oil content of the right foot to which the cream containing the catechin derivative was applied was 62% compared to the oil content of the left foot to which only the base material was applied. Moreover, the elastic force of the skin of the right foot was 144% as compared with the left foot, and an improvement in the elastic force was recognized.

In addition, macroscopic observation of the thigh showed that cellulite decreased in the thigh of the right foot to which the cream containing the catechin derivative was applied, and the length of the circumference of the thigh and the wrinkles and irregularities visually observed. The number of children also decreased compared to the left foot. From these results, it was found that the cosmetic product of Example 8 reduced neutral fat and reduced cellulite. Furthermore, side effects such as discomfort and irritation due to the application of the cosmetic product of Example 8 were not observed, and the safety of the cosmetic product of Example 8 was confirmed.

Hereinafter, an anti-obesity drug comprising a catechin derivative will be described.

30 g of the catechin derivative obtained in Example 6 above, 130 g of lanolin, 110 g of macro gold, 20 g of beeswax, and 30 g of ozokerite were added to a clean stainless steel dissolution tank and dissolved at 37 ° C. for 1 hour. This was supplied to a kneader, mixed, dissolved in a dissolution tank, heated, and deaerated with a deaerator to obtain the desired antiobesity agent as an ointment.

A control sample using lanolin instead of the catechin derivative obtained in Example 6 was prepared, and used as a control sample in Example 9 for the test.

Hereinafter, a test using an anti-obesity drug will be described.
(Test Example 4)

A clinical trial using the anti-obesity drug was conducted. That is, to 16 women who have an obesity degree (BMI, weight (kg) divided by height (m) squared) 28 or more and body fat percentage (measured with a Tanita body fat meter) 30% or more, 5 g of the ointment obtained in Example 9 was applied to the abdomen and applied. Application was carried out once a day for 30 days. 30 days after application, the body fat percentage, body weight, and blood triglyceride level were measured.

As a result, the average value after 30 days of application was 39% lower in obesity and 45% lower in body fat than before application. In addition, the blood neutral fat amount decreased to 29%. As a result, it was confirmed that the ointment of Example 9 exhibited an improvement effect on obesity in the abdomen.

On the other hand, no abnormality was observed in macroscopic findings, subjective symptoms, blood test values, other blood biochemical tests, etc., and the safety of the anti-obesity drug of Example 9 was confirmed.

In the case of an ointment using only a base material such as lanolin as a control, obesity is 101%, body fat percentage is 99%, and blood neutral fat is 103% compared to the value before use. Neither change was observed.

The catechin derivative having lipolytic activity according to the present invention has an excellent function with weak side effects, preventing and improving excessive accumulation of systemic and visceral fats, and suffers from obesity, visceral fat accumulation, and subcutaneous fat accumulation. It is intended to improve the QOL of patients, obesity, lifestyle-related diseases or their reserves.

In addition, the food preparation comprising a catechin derivative having a lipolytic action according to the present invention improves or prevents the accumulation of visceral fat and subcutaneous fat, which are the cause of metabolic syndrome, to improve the quality of national life and reduce medical expenses. It contributes.

Furthermore, cosmetics composed of catechin derivatives having lipolytic action show an improvement or prevention effect on the unevenness of the skin due to cellulite and fat, and are excellent in preventing and preventing wrinkles, improving the national QOL. is there.

In addition, according to the anti-obesity drug comprising a catechin derivative having a lipolytic action, fat is reduced with respect to obesity causing metabolic syndrome, contributing to the improvement or prevention of obesity and improving the national life. This anti-obesity drug has few side effects and exhibits excellent lipolytic action, thereby contributing to the activation of the medical and pharmaceutical industries and the reduction of medical costs.

Green tea leaves and edible fish heads and internal organs are treated as waste. The present invention reduces waste from the point of effectively using these wastes, and as a result, can prevent environmental destruction due to soil and ocean eutrophication due to wastes, and can effectively use fishery and agricultural resources and industrial It contributes to the development of

Claims (1)

A method for producing a catechin derivative represented by the following formula (1), wherein natto bacteria are added to edible fish, pulverized green tea leaves, and soybeans, and the fermented product heated and fermented is extracted with vegetable oil. .

X is any selected from caprylic acid, palmitic acid, eicosapentaenoic acid, docosahexaenoic acid, docosapentaenoic acid, alpha-lipoic acid, gamma-linolenic acid, stearic acid, methyl stearic acid, lauric acid, 14-methyl palmitic acid Or one.