JP6645791B2 - Method for producing ergosterol peroxide-containing composition - Google Patents

Description

  The present invention relates to a method for producing an ergosterol peroxide-containing composition.

Koji mold (Aspergillus) has been used in the production of sake, miso, and soy sauce for a long time in Japan, and is an indispensable bacterium for our daily lives. These fermented products are attracting attention not only as foods but also as functional foods, and various bioactive substances may be newly produced with the fermentation.
On the other hand, Japanese Unexamined Patent Publication No. 2005-73502 (Patent Document 1) describes a food or food material having an apoptosis-inducing ability, which comprises an extract of Kotake mushroom obtained by extracting Kotake mushroom. The publication also discloses that the extract of Kotake mushroom exhibits cancer-suppressing and prophylactic effects, and that the food or food material having the ability to induce apoptosis is composed of ergosterol peroxide derived from Kotake mushroom. ing. As described above, there is a need for a method for producing a composition containing ergosterol peroxide in an even easier and higher concentration. Further, there is a need for a method of manufacturing from raw materials that are more accessible and readily available than Kotake mushrooms.

JP 2005-73502 A

Under such a background, the present inventor has found that a composition containing a high concentration of ergosterol peroxide can be obtained by fermenting rice bran and rice germ, and completed the present invention.
That is, an object of the present invention is to provide a simple method for producing an ergosterol peroxide-containing composition containing a high concentration of ergosterol peroxide.

The technical features of the present invention for solving the above problems are as follows.
(1) Fermenting rice bran and / or rice germ to obtain a fermented product,
Thereafter, the fermentation product is extracted with a polar solvent to obtain a fermentation product extract,
Thereafter, distributing the fermented product extract,
A method for producing an ergosterol peroxide-containing composition.
(2) The method for producing an ergosterol peroxide-containing composition according to (1), wherein the rice bran and / or rice germ is defatted.
(3) The method for producing an ergosterol peroxide-containing composition according to (1) or (2), wherein the distribution is a liquid-liquid distribution, and the solvent for distribution is hexane and methanol.
(4) The method for producing an ergosterol peroxide-containing composition according to any one of (1) to (3), wherein the fermented product is obtained by fermenting with a koji mold.

It is a figure showing the method of manufacturing an ergosterol peroxide containing composition. It is an NMR spectrum of Compound D.

Hereinafter, the present invention will be described in detail.
The method for producing an ergosterol peroxide-containing composition of the present invention comprises fermenting rice bran and / or rice germ to obtain a fermented product, and then extracting the fermented product with a polar solvent to obtain a fermented product extract, Thereafter, the fermented product extract is separated with a separating liquid polar solvent.

As the "rice bran and / or rice germ", it is preferable to use raw bran produced in the milling process of brown rice. Brown rice is composed of skin, seed coat, endosperm and germ, and the outer layer of endosperm tissue has a thin layer called aleurone layer. As the rice polishing proceeds, not only the pericarp and seed coat but also the aleurone layer is eliminated as rice bran (raw bran). If necessary, a mixture of pericarp, seed coat, rice germ or aleurone, or a mixture of the pericarp, seed coat, rice germ or aleurone can be used.

The rice bran and / or rice germ is preferably used after being defatted. This is because a composition containing a higher concentration of ergosterol peroxide can be obtained. The method of this degreasing is not particularly limited,
At this time, preferable solvents for degreasing include n-hexane, acetone and the like. In particular, it is preferable to use n-hexane as the degreasing solvent. This is because the extracted oil can be used as an edible oil and the defatted extract can be easily used as a food material or the like. These degreasing solvents may be used alone or in combination of two or more.
Microorganisms used in the above-mentioned "fermentation" are not particularly limited, but koji mold, yeast, citric acid bacteria, lactic acid bacteria, acetic acid bacteria and the like can be used. And among these, koji mold is preferable.
The “Koji mold” is not particularly limited, and for example, at least one selected from koji molds for sake, shochu, awamori, miso, or soy sauce can be used.
For example, Aspergillus kawachii, Aspergillus awamori, Aspergillus oryzae, Aspergillus sojae, Aspergillus sasami (Aspergillus sasagi) At least one or more selected,
The fermentation temperature is not particularly limited, but is preferably 10 to 60C, more preferably 20 to 40C, and particularly preferably 25 to 35C. This is because the temperature within these ranges is the optimum temperature for the fermentation by the koji mold to proceed.
The fermentation time is not particularly limited, and is preferably 1 to 7 days, more preferably 2 to 4 days.

As the "polar solvent", a polar solvent such as water, methanol, ethanol, isopropyl alcohol, 1,3-butylene glycol, ethylene glycol, propylene glycol, glycerin, and ethyl acetate can be used. Two or more of these solvents may be mixed.
Desirably, when water ethanol or water-containing ethanol which is a mixture thereof is used as an extraction solvent, the active ingredient is efficiently extracted.

  When water-containing ethanol is used as the extraction solvent, the concentration of ethanol is not particularly limited, but the ethanol concentration is preferably 10 to 90% (wt / wt), and more preferably the ethanol concentration is 20 to 80% (wt / wt). The reason why the ethanol concentration is set to 90% or less (wt / wt) is that if the ethanol concentration is too high, the oil component in the fermented product tends to dissolve into the aqueous ethanol.

  The extraction may be performed at a temperature of 20 to 80 ° C, preferably about 40 to 50 ° C. If the extraction temperature is too low, it is difficult to extract the active ingredient, and if the extraction temperature is too high, the active ingredient is decomposed and the physiological activity (health functionality) decreases.

  As the extraction method, any method such as stirring extraction, continuous extraction, immersion extraction, countercurrent extraction, and supercritical extraction can be adopted, and any device can be used at room temperature or under reflux heating.

The method of the “distribution” is not particularly limited, but liquid-liquid distribution is preferably performed.
The solvent used in the liquid-liquid distribution is not particularly limited, and for example, water, methanol, ethanol, isopropyl alcohol, 1,3-butylene glycol, ethylene glycol, propylene glycol, glycerin, hexane, ethyl acetate, chloroform and the like can be used. Of these, hexane, methanol and chloroform are preferably used.

Specifically, it can be obtained by distributing a fermented product extract with hexane and water and separating a hexane layer.

The ergosterol peroxide-containing composition produced by the above method can be applied to various uses. Uses include pharmaceuticals, reagents, and compositions for oral ingestion (eg, health foods, functionally labeled foods, supplements, special-purpose foods, pet supplements, and the like).

The pharmaceutical composition containing the ergosterol peroxide-containing composition may contain an excipient, carrier or additive. The excipient, carrier, and additive are not particularly limited as long as they are commonly used and pharmaceutically acceptable, and the type and composition can be appropriately changed.

Excipients include sodium chloride, sodium citrate and the like, and carriers include sterile water, physiological saline, various buffers and the like. Examples of the additive include a thickener, a buffer, a preservative, and a preservative.

The dosage form of the pharmaceutical composition is not particularly limited and may be appropriately selected as needed. For example, oral preparations such as tablets, capsules, granules, fine granules, and powders; injections And parenteral preparations such as suppositories and liniments.

Tablets, capsules, granules, fine granules, oral preparations such as powders, for example, starch, lactose, sucrose, trehalose, mannitol, carboxymethylcellulose, corn starch, manufactured according to conventional methods using inorganic salts, The amount of the compound of the present invention in these preparations is not particularly limited, and can be appropriately set. In this type of preparation, a binder, a disintegrant, a surfactant, a lubricant, a fluidity promoter, a flavoring agent, a coloring agent, a flavor, and the like can be appropriately used.

In the case of parenteral preparations, the dosage is adjusted according to the patient's age, body weight, degree of disease and the like, and administered by intravenous injection, intravenous drip infusion, subcutaneous injection, intramuscular injection, and the like. This parenteral preparation is produced according to a conventional method, and generally, distilled water for injection, physiological saline and the like can be used as a diluent. Further, a bactericide, a preservative, a stabilizer and the like may be added as necessary. In addition, from the viewpoint of stability, this parenteral preparation can be frozen after filling into a vial or the like, and water can be removed by a usual freeze-drying treatment, and a liquid preparation can be prepared from the freeze-dried product immediately before use. If necessary, tonicity agents, stabilizers, preservatives, soothing agents and the like may be added. Examples of other parenteral preparations include liquid preparations for external use, ointments and other suppositories, suppositories for rectal administration, and the like, which are also produced according to conventional methods.

When the present invention is used for health foods (including functionally labeled foods, foods for specified health use, health drinks and supplements), the compounds of the present invention may be added to health foods as raw materials for various health foods, and dextrins may be added as necessary. It can be processed into pellets, tablets, granules, etc. together with excipients such as lactose, starch and the like, flavors, pigments and the like, or can be coated with gelatin or the like and molded into capsules to produce health foods.

The mixing ratio of the ergosterol peroxide-containing composition to be mixed with the health food is not particularly limited as long as the expected effect can be obtained from the ergosterol peroxide-containing composition. Is about 0.0001 to 2000 mg.

These health foods can be blended with various components depending on the type, for example, glucose, fructose, sucrose, maltose, sorbitol, stevioside, corn syrup, lactose, citric acid, tartaric acid, malic acid, Succinic acid, lactic acid, L-ascorbic acid, dl-α-tocopherol, sodium erysorbate, glycerin, propylene glycol, glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, gum arabic Food materials such as carrageenan, casein, gelatin, pectin, agar, vitamins B, nicotinamide, calcium pantothenate, amino acids, calcium salts, pigments, flavors and preservatives can be used. In addition, ergosterol peroxide-containing compositions having a health-preserving function include other antioxidants and health food ingredients, such as antioxidants (reduced ascorbic acid (vitamin C), vitamin E, reduced Glutatine, tocotrienol, vitamin A derivative, lycopene, lutein, astaxanthin, zeaxanthin, fucoxanthin, uric acid, ubiquinone, coenzyme Q10, folic acid, garlic extract, allicin, sesamin, lignans, catechin, isoflavone, chalcone, tannins, flavonoids , Coumarin, isocoumarins, blueberry extract), health food materials (V. (vitamin) A, V.B1, V.B2, V.B6, V.B12, VC, VD, VE, VP, choline, niacin, pantothene Acid, calcium folate, EPA, oligosaccharides, dietary fiber, squalene, soybean lecithin , Taurine, donariella, protein, octacosanol, DHA, egg yolk lecithin, linoleic acid, lactoferrin, magnesium, zinc, chromium, selenium, potassium, heme iron, oyster meat extract, chitosan, chitin oligosaccharide, collagen, chondroitin, turmeric, licorice, Kukushi, Cahi, Hawthorn, Ginger, Ganoderma, Ganoderma sardine, Squid extract, Turtle, Chamomile, Chamomile, Dandelion, Hibiscus, Honey, Bohren, Royal jelly, Lime, Lavender, Rosehip, Rosemary, Bifidobacterium, Faecalis fungus, Lacris, Wheat germ Oil, sesame oil, perilla oil, soybean oil, medium-chain fatty acids, agaricus, ginkgo leaf extract, turmeric, chondroitin, brown rice germ extract, litchi, onion, DPA, tencha, cordyceps, garlic, bee pup, papaya, Puer, Propolis, Meguri Tree, Aphidium, Saw Palmetto, Hyaluronic Acid, Collagen, Gaba, Harp Seal Oil, Shark Cartilage, Glucosamine, Lecithin, Phosphatidylserine, Tanashi Carrot, Mulberry Leaf, Soybean Extract, Echinacea, Eleuthero, Barley Extract Thing, olive leaf, olive fruit, gymnema, banana, saracia, garcinia, chitosan, St. John's wort, jujube, carrot, passionflower, broccoli, placenta, adlay, grape seed, peanut seed coat, bilberry, black cohosh, maria thistle, laurel, sage , Rafuma, black vinegar, bitter melon, maca, safflower, flax, oolong tea, flower spines, caffeine, capsaicin, xylo-oligosaccharides, glucosamine, buckwheat, citrus, dietary fiber, protein, prunes, sugar Lurina, barley young leaf, nucleic acid, yeast, shiitake mushroom, plum meat, amino acid, deep sea shark extract, noni, oyster meat, champignon, plantain, acerola, pineapple, banana, peach, apricot, melon, strawberry, raspberry, orange, fucoidan, Mesimakobu, cranberry, chondroitin sulfate, zinc, iron, ceramide, silk peptide, glycine, niacin, chest tree, L-cysteine, red wine leaf, millet, horsetail, biotin, centella asiatica, haskap, pycnogenol, fuki, rhubarb, Clove, catechin, puer, citric acid, brewer's yeast, melilot, black ginger, ginger, gadget, nattokinase, Benikouji, tocotrienol, lactoferrin, cinnamon, tartary buckwheat, cocoa, yuzu seed extract, perilla Seed extract, litchi seed extract, evening primrose extract, black rice extract, α-lipoic acid, green coffee bean extract, Satsuma mandarin extract, triterpenoid, kiwi seed extract, red ginger extract, astaxanthin, walnut extract, resveratrol, red rice extract, White jellyfish polysaccharide, strawberry seed extract, strawberry seed extract, leek seed extract, lingonberry extract, cherry blossom extract, sasacreht yodake extract, makiberry extract, rice polyamine, wheat polyamine) and the like can also be added.

When the present invention is used as a health food, the ergosterol peroxide-containing composition can be used in the form of various general foods and drinks.
Here, "can be used as a dosage form of various general foods and drinks" means that a general food and drink is selected as a dosage form for the purpose of exhibiting the effect as the ergosterol peroxide-containing composition. Means that only those who desire the expected effect from the ergosterol peroxide-containing composition are intended to eat, and even those who do not expect the effect as the ergosterol peroxide-containing composition. It does not mean that everyone can eat widely, including.
The amount of the ergosterol peroxide-containing composition to exert its effect is not particularly limited, but the total content of the active ingredient in the food or drink is preferably 1 to 20% by weight.
Although not particularly limited as a general food or beverage to be blended, for example, edible oil (salad oil), confectionery (gum, candy, caramel, chocolate, cookie, snack, jelly, gummy, tablet confectionery, etc.), noodles (buckwheat, Udon, ramen, etc.), dairy products (milk, ice cream, yogurt, etc.), seasonings (miso, soy sauce, etc.), soups, beverages (juice, coffee, tea, tea, carbonated beverages, sports drinks, etc.), etc. Can be

  In these general foods and drinks, various components can be blended depending on the type, for example, glucose, fructose, sucrose, maltose, sorbitol, stevioside, corn syrup, lactose, citric acid, tartaric acid, malic acid, Succinic acid, lactic acid, L-ascorbic acid, dl-α-tocopherol, sodium erysorbate, glycerin, propylene glycol, glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, gum arabic Food materials such as carrageenan, casein, gelatin, pectin, agar, vitamins B, nicotinamide, calcium pantothenate, amino acids, calcium salts, pigments, flavors and preservatives can be used. Furthermore, the above-mentioned composition containing ergosterol peroxide having a health maintenance function includes a distribution of other antioxidants and health food materials, such as antioxidants (reduced ascorbic acid (vitamin C), vitamin E, Reduced glutatin, tocotrienol, vitamin A derivative, lycopene, lutein, astaxanthin, zeaxanthin, fucoxanthin, uric acid, ubiquinone, coenzyme Q10, folic acid, garlic extract, allicin, sesamin, lignans, catechin, isoflavone, chalcone, tannins, flavonoids , Coumarin, isocoumarins, blueberry extract), health food materials (V. (vitamin) A, V.B1, V.B2, V.B6, V.B12, VC, VD, VE, VP, choline, niacin, Pantothenic acid, calcium folate, EPA, oligosaccharides, dietary fiber, squalene, soybean Tin, taurine, donariella, protein, octacosanol, egg yolk lecithin, linoleic acid, lactoferrin, magnesium, chromium, selenium, potassium, heme iron, oyster meat extract, chitosan, chitin oligosaccharides, collagen, chondroitin, turmeric, licorice, kukoshi, keihi , Hawthorn, ginger, reishi, shijimi extract, licorice, kukushi, cauliflower, hawthorn, ginger, reishi, plantain, chamomile, chamomile, dandelion, hibiscus, honey, boren, royal jelly, lime, lavender, rosehip, rosemary, Sage, bifidobacteria, faecalis, lacris, wheat germ oil, sesame oil, perilla oil, soybean oil, medium chain fatty acids, agaricus, ginkgo biloba extract, turmeric, chondroitin, brown rice germ extract, litchi, onion, DHA, EPA, DPA, Tencha, Cordyceps, Garlic, Bee, Papaya, Pu'er, Propolis, Megusuri Tree, Yabushitake, Royal Jelly, Saw Palmetto, Hyaluronic Acid, Collagen, Gaba, Harp Seal Oil, Shark Cartilage, Glucosamine, Lecithin , Phosphatidylserine, Nanatsu carrot, Mulberry leaf, Soybean extract, Echinacea, Eleuthero, Barley extract, Olive leaf, Olive fruit, Gymnema, Banaba, Salacia, Garcinia, Chitosan, St. John's wort, Jujube, Carrot, Passion flower, Broccoli , Placenta, adlay, grape seeds, peanut seed coat, bilberry, black cohosh, Maria thistle, laurel, sage, rosemary, rafuma, black vinegar, bitter gourd, maca, safflower, flax, oolong tea, flower spines, caffeine, capsa Syn, xylooligosaccharide, glucosamine, buckwheat, citrus, dietary fiber, protein, prunes, spirulina, barley young leaves, nucleic acids, yeast, shiitake mushrooms, plum meat, amino acids, deep sea shark extract, noni, oyster meat, turkey, champignon, psyllium, Acerola, pineapple, banana, peach, apricot, melon, strawberry, raspberry, orange, fucoidan, meshimakobu, cranberry, chondroitin sulfate, zinc, iron, ceramide, silk peptide, glycine, niacin, chest tree, L-cysteine, red wine leaf, Millet, horsetail, biotin, centella asiatica, haskap, pycnogenol, butterbur, rhubarb, clove, rosemary, catechin, puer, citric acid, brewer's yeast, melilot, black zinger, ginger, gadget, na Tow Kinase, Benikouji, Tocotrienol, Lactoferrin, Cinnamon, Tartar Buckwheat, Cocoa, Yuzu Seed Extract, Perilla Seed Extract, Lychee Seed Extract, Evening Primrose Extract, Black Rice Extract, α-Lipoic Acid, Gaba, Raw Coffee Bean Extract, Fuki Extract, Kiwi Seed extract, Unshu mandarin orange extract, red ginger extract, astaxanthin, walnut extract, leek seed extract, red rice extract, kanka extract, white jellyfish polysaccharide, fucoxanthin, lingonberry extract, cherry blossom extract, makiberry extract, Sasakurehi Toyotake extract, rice Polyamine, wheat polyamine) and the like.

The ergosterol peroxide-containing composition can be used as an external preparation for skin (including cosmetics, pharmaceuticals, and quasi-drugs).
Examples of the form of an external preparation for skin that can be blended with the ergosterol peroxide-containing composition include, for example, emulsions, soaps, facial cleansers, bath salts, creams, emulsions, lotions, colognes, shaving creams, and shaving lotions. , Makeup oil, suntan / sunscreen lotion, powdery white powder, foundation, perfume, pack, nail cream, enamel, enamel remover, eyebrows, blusher, eye cream, eye shadow, mascara, eyeliner, lipstick, lip balm, shampoo, Rinsing, hair coloring, dispersions, washings and the like can be mentioned. Examples of the form of a drug or a quasi-drug in which the above-mentioned ergosterol peroxide-containing composition can be blended include an ointment, a cream, and a liquid for external use.

In the skin external preparation of the above-mentioned form, in addition to the above-mentioned ergosterol peroxide-containing composition, cosmetics, quasi-drugs and other skin external preparations as long as the action of the ergosterol peroxide-containing composition is not impaired Ingredients, oils, higher alcohols, fatty acids, UV absorbers, powders, pigments, surfactants, polyhydric alcohols / sugars, polymers, bioactive ingredients, solvents, antioxidants, fragrances, preservatives, etc. Can be blended.
Examples are listed below, but the present invention is not limited to these examples.

(1) Examples of oil components Ester oil phase components: glyceryl tri-2-ethylhexanoate, cetyl 2-ethylhexanoate, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isostearic acid Isocetyl, butyl stearate, butyl myristate, ethyl linoleate, isopropyl linoleate, ethyl oleate, isocetyl myristate, isostearyl myristate, isostearyl palmitate, octyl dodecyl myristate, isocetyl isostearate, diethyl sebacate, adipine Diisopropyl acid, isoaraky neopentanoate, glyceryl tri (caprylate / caprate), trimethylolpropane tri-2-ethylhexanoate, trimethylol triisostearate Propane, pentaerythritol tetra-2-ethylhexanoate, cetyl caprylate, decyl laurate, hexyl laurate, decyl myristate, myristyl myristate, cetyl myristate, stearyl stearate, decyl oleate, cetyl ricinoleate, isolaurate Stearyl, isotridecyl myristate, isocetyl myristate, isostearyl myristate, isocetyl palmitate, isostearyl palmitate, octyl stearate, isocetyl stearate, isodecyl oleate, octyl dodecyl oleate, octyl dodecyl linoleate, isopropyl isostearate, Cetostearyl 2-ethylhexanoate, stearyl 2-ethylhexanoate, hexyl isostearate, ethylene glycol dioctanoate Ethylene glycol dioleate, propylene glycol dicaprate, propylene glycol di (caprylate / caprate), propylene glycol dicaprylate, neopentyl glycol dicaprate, neopentyl glycol dioctanoate, glyceryl tricaprylate, glyceryl triundecylate, triisopalmitin Glyceryl acid, glyceryl triisostearate, octyl dodecyl neopentanoate, isostearyl octanoate, octyl isononanoate, hexyl decyl neodecanoate, octyl dodecyl neodecanoate, isocetyl isostearate, isostearyl isostearate, octyldecyl isostearate, polyglycerol oleate Ester, polyglycerin isostearate, dipropyl carbonate, charcoal Dialkyl (C12-18), triisocetyl citrate, triisoaralkyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, cetyl lactate, octyl decyl lactate, triethyl citrate, acetyl triethyl citrate, acetyl tributyl citrate, Trioctyl citrate, diisostearyl malate, 2-ethylhexyl hydroxystearate, di-2-ethylhexyl succinate, diisobutyl adipate, diisopropyl sebacate, dioctyl sebacate, cholesteryl stearate, cholesteryl isostearate, cholesteryl hydroxystearate, olein Cholesteryl acid, dihydrocholesteryl oleate, phytosteryl isostearate, phytosteryl oleate, 12-stearoylhydroxystearate Cetyl, 12-stearoyl-hydroxystearic acid stearyl 12-stearoyl-hydroxystearic acid isostearate, and the like.
Hydrocarbon oil phase components: squalane, liquid paraffin, α-olefin oligomer, isoparaffin, ceresin, paraffin, liquid isoparaffin, polybutene, microcrystalline wax, petrolatum, etc.
Animal and vegetable oils and their hardened oils, and naturally derived waxes: animal oils such as tallow, hardened tallow, lard, hardened lard, horse oil, hardened horse oil, mink oil, orange roughy oil, fish oil, hardened fish oil, egg yolk oil, and the like. Its hardened oil, avocado oil, almond oil, olive oil, cocoa butter, kiwi seed oil, apricot kernel oil, cucumber oil, sesame oil, wheat germ oil, rice germ oil, rice bran oil, safflower oil, shea butter, soybean oil, evening primrose oil , Perilla oil, teaseed oil, camellia oil, corn oil, rapeseed oil, hydrogenated rapeseed oil, palm kernel oil, hydrogenated palm kernel oil, palm oil, hydrogenated palm oil, peanut oil, hydrogenated peanut oil, castor oil, hydrogenated castor oil Vegetable oils such as, sunflower oil, grape seed oil, jojoba oil, hardened jojoba oil, macadamia nut oil, medohome oil, cottonseed oil, hardened cottonseed oil, coconut oil, hardened coconut oil and the like , Beeswax, high acid value beeswax, lanolin, reduced lanolin, hydrogenated lanolin, liquid lanolin, carnauba wax and montan wax.
Silicone oil phase components: dimethylpolysiloxane, methylphenylpolysiloxane, methylcyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, methylhydrogenpolysiloxane, polyether-modified organopolysiloxane, dimethyl Siloxane / methylcetyloxysiloxane copolymer, dimethylsiloxane / methylstearoxysiloxane copolymer, alkyl-modified organopolysiloxane, terminal-modified organopolysiloxane, amino-modified silicone oil, amino-modified organopolysiloxane, dimethiconol, silicone gel, acrylic Examples include silicone, trimethylsiloxysilicic acid, and silicone RTV rubber.
Fluorine-based oil phase component: perfluoropolyether, fluorine-modified organopolysiloxane, pitch fluoride, fluorocarbon, fluoroalcohol, fluoroalkyl / polyoxyalkylene co-modified organopolysiloxane, and the like.

(2) Examples of higher alcohols Lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol, 2-ethylhexanol, hexadecyl alcohol, octyl dodecanol, and the like.

(3) Examples of fatty acids: caprylic acid, capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid, arachinic acid, arachidonic acid, behenic acid , Erucic acid, 2-ethylhexanoic acid and the like.

(4) Examples of ultraviolet absorbers paraaminobenzoic acid, amyl paraaminobenzoate, ethyldihydroxypropyl paraaminobenzoate, glyceryl paraaminobenzoate, ethyl paraaminobenzoate, octyl paraaminobenzoate, octyldimethyl paraaminobenzoate, ethylene glycol salicylate, salicylic acid Octyl, triethanolamine salicylate, phenyl salicylate, butylphenyl salicylate, benzyl salicylate, homomenthyl salicylate, benzyl cinnamate, octyl paramethoxycinnamate, 2-ethylhexyl paramethoxycinnamate, mono-diparamethoxycinnamate Glyceryl ethylhexanoate, isopropyl paramethoxycinnamate, diethanolamine salt of paramethoxyhydrocinnamate, diisopropyl / diisopropylcinnamate Stell mixture, urocanic acid, ethyl urocanate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenonesulfonic acid and salts thereof, dihydroxymethoxybenzophenone, sodium dihydroxymethoxybenzophenone disulfonate, dihydroxybenzophenone, dihydroxydimethoxybenzophenone, hydroxyoctoxybenzophenone, tetrahydroxybenzophenone, Butylmethoxydibenzoylmethane, 2,4,6-trianilino-p- (carb-2-ethylhexyl-1-oxy) -1,3,5-triazine, 2- (2-hydroxy-5-methylphenyl) benzotriazole , Methyl-O-aminobenzoate, 2-ethylhexyl-2-cyano-3, 3-diphenylacrylate, phenylbenzimidazole sulfate, 3- (4-methylbenzylidene) can Le, isopropyl dibenzoylmethane, 4- (3,4-dimethoxyphenyl methylene) 2-ethylhexyl-2,5-dioxo-1-imidazolidin propionate,, and polymer derivatives and silane derivatives thereof.

(5) Examples of powders / pigments Dyes such as Red No. 104, Red No. 201, Yellow No. 4, Blue No. 1, Black No. 401, etc., Lake Dyes such as Yellow No. 4 AL Lake, Yellow No. 203 BA Lake, Nylon Powder , Silk powder, urethane powder, Teflon (registered trademark) powder, silicone powder, polymethyl methacrylate powder, cellulose powder, starch, silicone elastomer spherical powder, polymer such as polyethylene powder, yellow iron oxide, red iron oxide, black Colored pigments such as iron oxide, chromium oxide, carbon black, ultramarine, navy blue, etc., white pigments such as zinc oxide, titanium oxide, and cerium oxide; extender pigments such as talc, mica, sericite, kaolin, and plate-like barium sulfate; titanium mica Pearl pigments, metal salts such as barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, magnesium silicate, etc. Inorganic powders such as lica and alumina, aluminum stearate, magnesium stearate, zinc palmitate, zinc myristate, magnesium myristate, zinc laurate, zinc undecylenate and other metal soaps, bentonite, smectite, boron nitride, etc. Can be The shape (particle shape, spherical shape, rod shape, needle shape, needle shape, irregular shape, flake shape, spindle shape, etc.) and particle size of these powders are not particularly limited. Note that these powders are conventionally known surface treatments, for example, fluorine compound treatment, silicone treatment, silicone resin treatment, pendant treatment, silane coupling agent treatment, titanium coupling agent treatment, oil agent treatment, N-acylated lysine treatment, It may or may not have been surface-treated in advance by polyacrylic acid treatment, metal soap treatment, amino acid treatment, lecithin treatment, inorganic compound treatment, plasma treatment, mechanochemical treatment, or the like.

(6) Examples of surfactants Anionic surfactants: fatty acid soap, α-acyl sulfonate, alkyl sulfonate, alkyl allyl sulfonate, alkyl naphthalene sulfonate, alkyl sulfate, POE alkyl ether sulfate , Alkyl amide sulfate, alkyl phosphate, POE alkyl phosphate, alkyl amide phosphate, alkylloyl alkyl taurate, N-acyl amino acid salt, POE alkyl ether carboxylate, alkyl sulfosuccinate, alkyl sulfoacetic acid Sodium, acylated hydrolyzed collagen peptide salts, perfluoroalkyl phosphates and the like.
Cationic surfactants: alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, benzalkonium chloride , Behenic acid amidopropyldimethylhydroxypropylammonium, stearic acid diethylaminoethylamide, stearic acid dimethylaminopropylamide, lanolin derivative quaternary ammonium salts and the like.
Amphoteric surfactants include carboxybetaine type, amidobetaine type, sulfobetaine type, hydroxysulfobetaine type, amidosulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type, amidoamine type and the like.
Nonionic surfactants: Propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE sorbitan fatty acid ester, POE sorbit fatty acid ester, POE glycerin fatty acid ester, POE alkyl ether, POE fatty acid ester, POE cured castor Oil, POE castor oil, POE / POP copolymer, POE / POP alkyl ether, polyether-modified silicone lauric alkanolamide, alkylamine oxide, hydrogenated soybean phospholipid, and the like.
Natural surfactants: lecithin, saponin, sugar surfactants and the like.

(7) Examples of polyhydric alcohols and sugars ethylene glycol, diethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, glycerin, diglycerin, polyglycerin, 3-methyl-1,3-butanediol, 1,3 -Butylene glycol, sorbitol, mannitol, raffinose, erythritol, glucose, sucrose, fructose, xylitol, lactose, maltose, maltitol, trehalose, alkylated trehalose, mixed isomerized sugar, sulfated trehalose, pullulan and the like. Further, these chemically modified products can also be used.

(8) Examples of polymers Acrylic ester / methacrylic ester copolymer (plus size, manufactured by Yoyo Kagaku), vinyl acetate / crotonic acid copolymer (resin 28-1310, manufactured by NSC), vinyl acetate / croton Acid / vinyl neodecanoate copolymer (28-2930, manufactured by NSC), methyl vinyl ether maleic acid half ester (Gantrez ES, ISP), T-butyl acrylate / ethyl acrylate / methacrylic acid copolymer (rubimer) , BASF), vinylpyrrolidone / vinyl acetate / vinyl propionate copolymer (Rubiscol VAP, BASF), vinyl acetate / crotonic acid copolymer (Rubiset CA, BASF), vinyl acetate / croton Acid / vinylpyrrolidone copolymer (Rubiset CAP, manufactured by BASF), vinylpyrrolidone / acrylate copolymer (Rubiflex, BAS) F), acrylate / acrylamide copolymer (Ultrahold, manufactured by BASF), vinyl acetate / butyl maleate / isobornyl acrylate copolymer (Advantage, manufactured by ISP), carboxyvinyl polymer (Carbopol, BFGoodrich), anionic polymer compounds such as acrylic acid / alkyl methacrylate copolymer (Pemulen, BF Goodrich), and acetic acid amphoteric dialkylaminoethyl methacrylate polymer (Yukaformer, manufactured by Mitsubishi Chemical Corporation); Amphoteric polymer compounds such as octylacrylamide acrylate / hydroxypropyl acrylate / butylaminoethyl methacrylate copolymer (AMPHOMER, manufactured by NSC), and quaternized vinylpyrrolidone / dimethylaminoethyl methacrylate (GAFQUAT, manufactured by ISP) , Methyl vinyl imidazolium chloride / Polyvinylpyrrolidone (Rubiscol K, manufactured by BASF), vinylpyrrolidone / vinyl acetate copolymer (Rubiscole VA, manufactured by BASF) Nonionic polymer compounds such as vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (Copolymer 937, manufactured by ISP) and vinylcaprolactam / vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (Copolymer VC713, manufactured by ISP) is there. In addition, cellulose or a derivative thereof, keratin and collagen or a derivative thereof, calcium alginate, pullulan, agar, gelatin, tamarind seed polysaccharide, xanthan gum, carrageenan, high methoxyl pectin, low methoxyl pectin, guar gum, gum arabic, crystalline cellulose, arabino Naturally occurring polymer compounds such as galactan, karaya gum, tragacanth gum, alginic acid, albumin, casein, curdlan, gellan gum, and dextran can also be suitably used.

(9) Examples of Physiologically Active Ingredients Examples of the physiologically active ingredient include substances that give some physiological activity to the skin when applied to the skin. For example, whitening ingredients, immunostimulants, anti-aging agents, UV protection agents, slimming agents, tightening agents, antioxidants, hair growth agents, hair restorers, moisturizers, blood circulation promoters, antibacterial agents, bactericides, desiccants, Examples thereof include cooling agents, warming agents, vitamins, amino acids, wound healing promoters, stimulants, analgesics, cell activators, and enzyme components. Examples of these preferred components include, for example, ashitaba extract, avocado extract, amacha extract, altea extract, arnica extract, aloe extract, apricot extract, apricot nucleus extract, ginkgo extract, fennel extract, turmeric extract, oolong tea extract, and Eijitsu Extracts, Echinashi leaf extract, oak extract, oak extract, spinach extract, barley extract, hypericum extract, scotch extract, Dutch mustard extract, orange extract, seawater dried product, seaweed extract, hydrolyzed elastin, hydrolyzed wheat powder, hydrolyzed silk , Chamomile extract, carrot extract, sagebrush extract, licorice extract, carcade extract, syllium extract, kina extract, cucumber extract, guanosine, gardenia extract, kumazasa extract, clarae Kiss, walnut extract, grapefruit extract, clematis extract, chlorella extract, mulberry extract, gentian extract, black tea extract, yeast extract, burdock extract, rice bran extract, rice germ oil, comfrey extract, collagen, lingon extract, saishin extract, psycho extract , Saitai extract, Salvia extract, Sabonso extract, Sasa extract, Hawthorn extract, Sansho extract, Shiitake extract, Jio extract, Shikon extract, Perilla extract, Shinanoki extract, Shimotsusou extract, Peony extract, Shobu root extract, Birch extract, Japanese horse chestnut extract, Sailing Kizuta extract, Atlantic hawthorn extract, Western elderberry extract, Achillea millefolium extract, Common peppermint extract, Sage extract, Common mallow extract, Senki Thu extract, assemblage extract, soybean extract, lyophile extract, thyme extract, tea extract, clove extract, scotch extract, chimpanzee extract, touki extract, toad extract, tonin extract, spruce extract, dokudami extract, tomato extract, natto extract, carrot extract, garlic extract, Novarra extract, Hibiscus extract, Bakmondou extract, Parsley extract, Honey, Hamamelis extract, Parietaria extract, Hioki sorghum extract, Bisabolol, Loquat extract, Coltsfoot poppo extract, Fukinotou extract, Bucurio extract, Butcher bloom extract, Grape extract, Propolis, Loach extract, Safflower extract, peppermint extract, bodaige extract, button extract, hop extract, pine extract, marronnier extract, mugwort Kiss, mukuroji extract, melissa extract, peach extract, cornflower extract, eucalyptus extract, saxifrage extract, yokunin extract, mugwort extract, lavender extract, apple extract, lettuce extract, lemon extract, astragalus extract, rose extract, rosemary extract, roman chamomile extract And royal jelly extract.
In addition, biopolymers such as deoxyribonucleic acid, mucopolysaccharide, sodium hyaluronate, sodium chondroitin sulfate, collagen, elastin, chitin, chitosan, hydrolyzed eggshell membranes, amino acids, hydrolyzed peptides, sodium lactate, urea, sodium pyrrolidone carboxylate , Betaine, whey, moisturizing components such as trimethylglycine, sphingolipids, ceramides, phytosphingosine, cholesterol, cholesterol derivatives, oily components such as phospholipids, ε-aminocaproic acid, glycyrrhizic acid, β-glycyrrhetinic acid, lysozyme chloride, guaiazulene, Immunostimulants such as hydrocholtisone, vitamin A, vitamin B2, vitamin B6, vitamin C, vitamin D, vitamin E, calcium pantothenate, biotin, nicotinamide, and vitamin C esters Active ingredients such as vitamins, allantoin, diisopropylamine dichloroacetate, 4-aminomethylcyclohexanecarboxylic acid, antioxidants such as tocopherol, carotenoids, flavonoids, tannins, lignans, saponins, α-hydroxy acids, β-hydroxy acids, etc. Cell activators, blood circulation promoters such as γ-oryzanol, vitamin E derivatives, wound healing agents such as retinol, retinol derivatives, arbutin, kojic acid, placenta extract, sulfur, ellagic acid, linoleic acid, tranexamic acid, glutathione, etc. Whitening agent, cepharanthin, licorice extract, pepper tincture, hinokitiol, garlic iodide extract, pyridoxine hydrochloride, DL-α-tocopherol, DL-α-tocopherol acetate, nicotinic acid, nicotinic acid derivative, calcium pantothenate, D-pan Totenyl alcohol, acetyl pantothenyl ethyl ether, biotin, allantoin, isopropylmethylphenol, estradiol, ethinyl estradiol, capronium chloride, benzalkonium chloride, diphenhydramine hydrochloride, tacanal, camphor, salicylic acid, vanillyl nonylate, vanillyl nonanoate, piloctone Olamine, glyceryl pentadecanoate, L-menthol, mononitroguaiacol, resorcin, γ-aminobutyric acid, benzethonium chloride, mexiletine hydrochloride, auxin, female hormone, canthari tincture, cyclosporine, zinc pyrithione, hydrocortisone, minoxidil, monostearic acid Hair growth agents such as polyoxyethylene sorbitan, peppermint oil, Sasanishiki extract and the like.

(10) Examples of antioxidants: sodium bisulfite, sodium sulfite, erythorbic acid, sodium erysorbate, dilauryl thiodipropionate, tocopherol, tolylbiguanide, nordihydroguaiaretinic acid, parahydroxyanisole, butylhydroxyanisole, dibutylhydroxy Examples include toluene, ascorbyl stearate, ascorbyl palmitate, octyl gallate, propyl gallate, carotenoids, flavonoids, tannins, lignans, saponins, and plant extracts having an antioxidant effect such as apple extract and clove extract.

  As a specific manufacturing method, the above-mentioned ergosterol peroxide-containing composition is spray-dried or freeze-dried together with powdered cellulose, and is easily converted into powder, granules, tableting or a solution to be easily used in general foods and drinks (instant foods, etc.). Can be contained. Further, the ergosterol peroxide-containing composition can be dissolved in, for example, fats and oils, ethanol, glycerin, or a mixture thereof, and added to a beverage or a solid food. If necessary, it may be mixed with a binder such as gum arabic or dextrin to form a powder or granules, and added to a beverage or a solid food.

Hereinafter, the present invention will be described based on examples.
A mixture of 1.4 kg of defatted rice germ and an equal volume of distilled water, autoclaved, and added with 560 mg of koji mold and 42 g of incense roast were mixed and fermented at 35 ° C for 3 days. I got The fermented rice germ was subjected to warm extraction with 3 kg of methanol three times, and the extract was concentrated under reduced pressure to obtain 156.06 g of a methanol extract.
According to the scheme shown in FIG. 1, 83 g of the methanol extract was subjected to liquid separation with hexane: methanol = 6: 1 to obtain 17.67 g of a hexane-soluble portion (this example).
Fractionation was performed according to the fractionation scheme of FIG. 1, and 11.2 mg of Compound B components were isolated. The isolated components were subjected to structural analysis by NMR. FIG. 2 shows the Compound B spectrum. According to FIG. 2 and literature Mizushina Y. et al., Biol. Pharm. Bull., 1998, 21 (5), 444-448 , it was confirmed that Compound B was ergosterol peroxide represented by the following chemical formula (1). Was done. Further, the content of Compound B in the hexane-soluble portion was 0.06%. That is, it was confirmed that the examples contained ergosterol peroxide.

Examples of the composition of the ergosterol peroxide-containing composition produced by the method of the present invention will be described below, but the following examples do not limit the present invention.
Formulation Example 1: Chewing gum (functionally labeled food or food for specified health use)
Sugar 53.0wt%
Gum base 20.0
Glucose 10.0
Syrup 16.0
Spice 0.5
Ergosterol peroxide-containing composition 0.5
100.0wt%

Formulation Example 2: Gummy (functionally labeled food or food for specified health use)
Reduced syrup 40.0wt%
Granulated sugar 20.0
Glucose 20.0
Gelatin 4.7
Water 9.68
Kiwi juice 4.0
Kiwi flavor 0.6
Pigment 0.02
Ergosterol peroxide-containing composition 1.0
100.0wt%

Formulation Example 3: Candies (functionally labeled food or food for specified health use)
Sugar 50.0wt%
Syrup 33.0
Water 14.4
Organic acid 2.0
Fragrance 0.2
Ergosterol peroxide-containing composition 0.4
100.0wt%

Formulation 4: Yogurt (hard / soft) (functionally labeled food or food for specified health use)
Milk 41.5wt%
5.8 skim milk powder
Sugar 8.0
Agar 0.15
Gelatin 0.1
Lactic acid bacteria 0.005
Ergosterol peroxide-containing composition 0.4
Fragrance trace
Water residue
100.0wt%

Formulation Example 5: Soft drink (functionally labeled food or food for specified health use)
Fructose glucose liquid sugar 30.0wt%
Emulsifier 0.5
Ergosterol peroxide-containing composition 0.05
Appropriate amount of fragrance
Purified water residue
100.0wt%

Formulation Example 6: soft capsule (functionally labeled food or food for specified health use)
Rice germ oil 87.0wt%
Emulsifier 12.0
Ergosterol peroxide-containing composition 1.0
100.0wt%

Formulation Example 7: Tablet (functionally labeled food or food for specified health use)
Lactose 54.0wt%
Crystalline cellulose 30.0
Starch degradation product 10.0
Glycerin fatty acid ester 5.0
Ergosterol peroxide-containing composition 1.0
100.0wt%

Formulation Example 8: Intragranular preparation (pharmaceutical)
Ergosterol peroxide-containing composition 1.0 wt%
Lactose 30.0
Corn starch 60.0
Microcrystalline cellulose 8.0
Polyvinyl pyrrolidone 1.0
100.0wt%

Formulation Example 9: Confectionery
Sugar 76.4wt%
Glucose 19.0
Sucrose fatty acid ester 0.2
Ergosterol peroxide-containing composition 0.5
Purified water 3.9
100.0wt%

Formulation Example 15: Cat food
Corn 34.0wt%
Flour 35.0
Meat Meal 15.0
Beef tallow 8.9
Salt 1.0
Skipjack extract 4.0
Ergosterol peroxide-containing composition 1.0
Taurine 0.1
Vitamins 0.5
Minerals 0.5
100.0wt%

Formulation Example 16: dog food
Corn 30.0wt%
Meat (chicken) 15.0
Defatted soy 10.0
Flour 25.0
Kasu bran 5.0
Ergosterol peroxide-containing composition 5.0
Animal fats and oils 8.9
Oligosaccharide 0.1
Vitamin 0.5
Mineral 0.5
100.0wt%

Formulation Example 10: Makeup cream squalane 20.0 wt%
Beeswax 5.0
Refined jojoba oil 5.0
Glycerin 5.0
Glycerin monostearate 2.0
Polyoxyethylene (20) sorbitan-
Monostearate 2.0
Ergosterol peroxide-containing composition 2.0
Preservatives qs perfume qs
Purified water residue
100.0wt%

Formulation Example 11: lotion ethanol 5.0 wt%
Glycerin 2.0
1,3-butylene glycol 2.0
Polyethylene oleyl ether 0.5
Sodium citrate 0.1
Citric acid 0.1
Ergosterol peroxide-containing composition 5.0
Purified water residue
100.0wt%

Formulation Example 12: body gel macadamia nut oil 2.0 wt%
Octyldodecyl myristate 10.0
Methylphenyl polysiloxane 5.0
Behenyl alcohol 3.0
Stearic acid 3.0
Butyl alcohol 1.0
Glyceryl monostearate 1.0
Polyoxyethylene sorbite 2.0 tetraoleate
Hydrogenated soybean phospholipid 1.0
Ceramide 0.1
Retinol palmitate 0.1
Preservatives qs
Ergosterol peroxide-containing composition 1.0
1,3-butylene glycol 5.0
Purified water residue
100.0wt%

Formulation Example 13: emulsion squalane 4.0 wt%
Vaseline 2.5
Cetanol 2.0
Glycerin 2.0
Lipophilic glyceryl monostearate 1.0
Stearic acid 1.0
L-arginine 1.0
Ergosterol peroxide-containing composition 0.5
Potassium hydroxide 0.1
Fragrance trace
Purified water residue
100.0wt%

  As described above, the present invention can provide a simple method for producing an ergosterol peroxide-containing composition containing a high concentration of ergosterol peroxide.

Claims (2)

Fermented rice bran and / or rice germ with koji mold to obtain a fermented product,
Thereafter, the fermentation product is extracted with a polar solvent to obtain a fermentation product extract,
Thereafter, distributing the fermented product extract,
A method for producing an ergosterol peroxide-containing composition. The method for producing an ergosterol peroxide-containing composition according to claim 1, wherein the rice bran and / or rice germ is defatted .

Images