JP2017063768A - Manufacturing method of stigmasterol-containing composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a simple manufacturing method of a stigmasterol-containing composition that contains the stigmasterol at a high concentration.SOLUTION: (1) A manufacturing method of a stigmasterol-containing composition including obtaining a fermentation product by fermenting rice bran and/or rice embryo, after that, obtaining a fermentation extract by extracting the fermentation product with a polar solvent, and, after that, distributing the fermentation extract. (2) A manufacturing method of a stigmasterol-containing composition according to the (1), in which the rice bran and/or rice embryo is defatted rice bran and/or rice embryo. (3) A manufacturing method of a stigmasterol-containing composition according to the (1) or (2), in which the distribution is a liquid-liquid distribution that is carried out with hexane and water, and a hexane layer is separated. (4) A manufacturing method of a stigmasterol-containing composition according to any one of the (1) to (3), in which the fermentation product is obtained by fermenting with Aspergillus.SELECTED DRAWING: None

Description

  The present invention relates to a method for producing a stigmasterol-containing composition.

Aspergillus has long been used in the production of sake, miso, and soy sauce in Japan, and is an indispensable fungus for our lives. These fermented products are attracting attention as functional foods as well as mere foods, and various physiologically active substances may be newly produced with fermentation.

On the other hand, it is known that blood cholesterol is lowered by ingestion of phytosterols. Phytosterols are plant sterols found in small amounts in vegetable oils such as corn, beans or other vegetable oils, which occur as free sterols, fatty acid esters and glycosides. Phytosterols are structurally similar to cholesterol, with the main difference occurring in the carbon skeleton of their side chains. Many different phytosterol structures have been found in nature. The most common are campesterol, beta-sitosterol and stigmasterol. In particular, stigmasterol has a remarkable effect of lowering cholesterol in blood (Non-patent Document 1).

Batta et al. 2006, Metabolism Clinical and Experimental 55: 292-29

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

The technical features of the present invention for solving the above-described problems are as follows.
(1) Fermenting rice bran and / or rice germ to obtain a fermented product,
Thereafter, the fermented product is extracted with a polar solvent to obtain a fermented product extract,
Then, the fermented product extract is dispensed,
A method for producing a stigmasterol-containing composition.
(2) The method for producing a stigmasterol-containing composition according to (1), wherein the rice bran and / or rice germ is defatted.
(3) The method for producing a stigmasterol-containing composition as described in (1) or (2) above, wherein the distribution is liquid-liquid distribution, and the hexane layer is separated by distributing with hexane and water.
(4) The method for producing a stigmasterol-containing composition as described in any one of (1) to (3) above, wherein the fermented product is fermented with koji mold.

It is a figure which shows the method of manufacturing a stigmasterol containing composition. It is a NMR spectrum of Compound A.

The present invention is described in detail below.
The method for producing a stigmasterol-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, The fermented product extract is separated with a polar solvent for separation.

For “rice bran and / or rice germ”, ginger produced in the rice milling process of brown rice may be used. Brown rice is composed of pericarp, seed coat, endosperm and germ, and there is a thin layer called a paste layer on the outer layer of the endosperm tissue. As the milling progresses, not only the pericarp and seed coat, but also the glue layer is eliminated as rice bran (ginger). If necessary, a mixture of pericarp, seed coat, rice germ or paste can be used, or a mixture of pericarp, seed coat, rice germ or paste can be used.

The rice bran and / or rice germ is preferably used with a defatted one. This is because a composition containing a higher concentration of stigmasterol can be obtained. This degreasing method is not particularly limited,
At this time, preferable degreasing solvents include n-hexane, acetone and the like. In particular, n-hexane is preferably used as a 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. These degreasing solvents may be used alone or in combination of two or more.
Microorganisms used in the above “fermentation” are not particularly limited, and koji molds, yeasts, citric acid bacteria, lactic acid bacteria, acetic acid bacteria, and the like can be used. Of these, Neisseria gonorrhoeae is preferred.
Although it does not specifically limit as said "gonococcus", For example, at least 1 thing chosen from sake for sake, shochu, awamori, miso, or soy sauce can be used.
For example, Aspergillus kawachii, Aspergillus awamori, Aspergillus oryzae, Aspergillus sojae, Aspergillus sasperi (Aspergillus saitoi), Aspergillus sasperi (Aspergillus sasperi) At least one selected,
Although the temperature of fermentation is not specifically limited, 10-60 degreeC, Furthermore, 20-40 degreeC, Especially 25-35 degreeC is preferable. It is because it is the optimal temperature for the fermentation by Aspergillus to progress by setting it as these ranges.
Moreover, fermentation time is not specifically limited, It is preferable to carry out for 1 to 7 days, and also for 2 to 4 days.

As the “polar solvent”, polar solvents 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 hydrous ethanol is used as the extraction solvent, the ethanol concentration is not particularly limited, but in particular, the ethanol concentration is 10 to 90% (wt / wt), and desirably the ethanol concentration is 20 to 80% (wt / wt). The reason why the ethanol concentration is 90% (wt / wt) or less is that if the ethanol concentration is too high, the oil in the fermented product is easily dissolved in the water-containing ethanol.

  The extraction temperature is 20 to 80 ° C, preferably about 40 to 50 ° C. This is because if the extraction temperature is too low, it becomes 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) is reduced.

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

The method of “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 partitioning the fermented extract with hexane and water and separating the hexane layer.

The stigmasterol-containing composition produced by the above method can be applied to various uses. Applications include pharmaceuticals, reagents, and compositions for ingestion (eg, health foods, functional foods, supplements, foods for specific uses, and supplements for pets).

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

Examples of the excipient include sodium chloride and sodium citrate, and examples of the carrier include sterilized water, physiological saline, and various buffers. Examples of additives include thickeners, buffer materials, preservatives, preservatives, and the like.

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

Oral preparations such as tablets, capsules, granules, fine granules, powders and the like are produced according to a conventional method using, for example, starch, lactose, sucrose, trehalose, mannitol, carboxymethylcellulose, corn starch, inorganic salts, The compounding quantity of the compound of this invention in these formulations is not specifically limited, It can set suitably. In this type of preparation, binders, disintegrants, surfactants, lubricants, fluidity promoters, corrigents, colorants, fragrances and the like can be used as appropriate.

In the case of a parenteral preparation, the dose is adjusted according to the age, weight, disease level, etc. of the patient, and for example, intravenous administration, intravenous infusion, subcutaneous injection, intramuscular injection or the like is used. This parenteral preparation is produced according to a conventional method, and distilled water for injection, physiological saline and the like can be generally used as a diluent. Furthermore, you may add a bactericidal agent, antiseptic | preservative, a stabilizer, etc. as needed. In addition, from the viewpoint of stability, this parenteral preparation can be frozen after filling into a vial or the like, the water can be removed by ordinary freeze-drying treatment, and the liquid preparation can be re-prepared from the freeze-dried product immediately before use. Further, if necessary, an isotonic agent, a stabilizer, an antiseptic, a soothing agent and the like may be added. Examples of other parenteral agents include liquid preparations for external use, coating agents such as ointments, suppositories for rectal administration, etc., and these are also produced according to conventional methods.

When the present invention is used for health foods (including functional indication foods, foods for specified health use, health drinks and supplements), the compound of the present invention is added to the health foods as raw materials for various health foods, or dextrin as necessary It can be processed into pellets, tablets, granules, etc. together with excipients such as lactose and starch, fragrances, pigments, etc., or coated with gelatin and formed into capsules to produce health foods.

The blending ratio of the stigmasterol-containing composition to be blended in the health food is not particularly limited as long as the effect expected from the stigmasterol-containing composition can be obtained, but the amount of intake per serving is usually 0.0001. About 2,000 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 erythorbate, 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, vitamin Bs, nicotinic acid amide, calcium pantothenate, amino acids, calcium salts, pigments, fragrances and preservatives can be used. In addition, stigmasterol-containing compositions with health maintenance functions include other antioxidants and health food ingredients such as antioxidants (reduced ascorbic acid (vitamin C), vitamin E, reduced glutatin). , Tocotrienol, vitamin A derivatives, 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 ingredients (V. (vitamin) A, V.B1, V.B2, V.B6, V.B12, VC, VD, VE, VP, choline, niacin, pantothenic acid, Calcium folate, EPA, oligosaccharide, dietary fiber, squalene, soy lecithin, tauri , 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, kokushi, Keihi, hawthorn, ginger, ganoderma, swordfish extract, turtle, chamomile, chamomile, dandelion, hibiscus, honey, boren, royal jelly, lime, lavender, rosehip, rosemary, bifidobacteria, faecalis, lacris, wheat germ oil, Sesame oil, perilla oil, soybean oil, medium chain fatty acid, agaricus, ginkgo biloba extract, turmeric, chondroitin, brown rice germ extract, litchi, onion, DPA, green tea, cordyceps, garlic, bee, papaya, puer, Propolis, Meguri Tree, Yabushitake, Saw Palmetto, Hyaluronic Acid, Collagen, Gabba, Harp Seal Oil, Shark Cartilage, Glucosamine, Lecithin, Phosphatidylserine, Padlock Carrot, Mulberry Leaf, Soybean Extract, Echinacea, Ezoukogi, Barley Extract, Olive leaf, olive fruit, Gymnema, banaba, Salacia, Garcinia, chitosan, St. John's wort, jujube, carrot, passionflower, broccoli, placenta, pearl barley, grape seeds, peanut seed coat, bilberry, black cohosh, maria thistle, laurel, sage, raffma , Black vinegar, bitter gourd, maca, safflower, flax, oolong tea, flower spine, caffeine, capsaicin, xylooligosaccharide, glucosamine, buckwheat, citrus, dietary fiber, protein, prunes, spirulina, Wheat leaf, nucleic acid, yeast, shiitake mushroom, plum meat, amino acid, deep sea potato extract, noni, oyster meat, champignon, plantain, acerola, pineapple, banana, peach, apricot, melon, strawberry, raspberry, orange, fucoidan, mesimacob, Cranberry, Chondroitin sulfate, Zinc, Iron, Ceramide, Silk peptide, Glycine, Niacin, Chest tree, L-cysteine, Red wine leaf, Millet, Horsetail, Biotin, Centella Asiatica, Hascup, Pycnogenol, Fuki, Rhubarb, Clove, Catechin, puer, citric acid, brewer's yeast, merirot, black zinger, ginger, gadget, nattokinase, benichouji, tocotrienol, lactoferrin, cinnamon, buckwheat, cocoa, yuzu seed extract, perilla seed extract, Lychee seed extract, evening primrose extract, black rice extract, α-lipoic acid, fresh coffee bean extract, Unshu orange extract, triterpenoid, kiwi seed extract, red ginger extract, astaxanthin, walnut extract, resveratrol, red rice extract, white fungus polysaccharide Strawberry seed extract, strawberry seed extract, leek seed extract, lingon berry extract, cherry blossom extract, Sasa Kurihito yotake extract, maqui berry extract, rice polyamine, wheat polyamine) and the like.

When the present invention is used as a health food, the stigmasterol-containing composition can be used as a dosage form for various general foods and drinks.
Here, “can be used as a dosage form for various general foods and beverages” means that the general food and drink can be selected as a dosage form for the purpose of exhibiting the effect as the stigmasterol-containing composition. It is meant to be eaten only by those who desire the effect expected from the stigmasterol-containing composition, and is widely eaten by everyone including those who do not expect the effect as the stigmasterol-containing composition. It doesn't mean you can.
Moreover, although the compounding quantity for exhibiting an effect as said stigmasterol containing composition is not specifically limited, It is preferable that the content of an active ingredient is 1-20 wt% in total with respect to food-drinks.
Moreover, although it does not specifically limit as general food / beverage products to mix | blend, For example, edible oil (salad oil), confectionery (gum, candy, caramel, chocolate, cookie, snack, jelly, gummi, tablet confection etc.), noodles (soba, Udon, ramen, etc.), dairy products (milk, ice cream, yogurt, etc.), seasonings (miso, soy sauce, etc.), soups, beverages (juice, coffee, tea, tea, carbonated drinks, sports drinks, etc.) It is done.

  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 erythorbate, 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, vitamin Bs, nicotinic acid amide, calcium pantothenate, amino acids, calcium salts, pigments, fragrances and preservatives can be used. Furthermore, the above-mentioned stigmasterol-containing composition having a health maintenance function includes other antioxidants and health food ingredients such as antioxidants (reduced ascorbic acid (vitamin C), vitamin E, reduced form). 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 ingredients (V. (vitamin) A, V.B1, V.B2, V.B6, V.B12, VC, VD, VE, VP, choline, niacin, pantothenic acid , Calcium folate, EPA, oligosaccharide, dietary fiber, squalene, soy lecithin, ta Phosphorus, Donariella, protein, octacosanol, egg yolk lecithin, linoleic acid, lactoferrin, magnesium, chromium, selenium, potassium, heme iron, oyster meat extract, chitosan, chitin oligosaccharide, collagen, chondroitin, turmeric, licorice, kokushi, keihi, hawthorn , Ginger, ganoderma, rainbow trout extract, licorice, kokushi, keihi, hawthorn, ginger, ganoderma, plantain, chamomile, chamomile, dandelion, hibiscus, honey, bohlen, royal jelly, lime, lavender, rosehip, rosemary, sage, Bifidobacterium, faecalis, lacris, wheat germ oil, sesame oil, perilla oil, soybean oil, medium chain fatty acid, agaricus, ginkgo biloba extract, turmeric, chondroitin, brown rice germ extract, litchi, onion, DHA, EPA, D PA, green tea, cordyceps, garlic, bee, papaya, puer, propolis, meguri tree, jabushitake, royal jelly, saw palmetto, hyaluronic acid, collagen, gabba, harpseal oil, shark cartilage, glucosamine, lecithin, phosphatidylserine, Tanachi Carrot, Mulberry Leaf, Soybean Extract, Echinacea, Ezoukogi, Barley Extract, Olive Leaf, Olive Seed, Gymnema, Banaba, Salacia, Garcinia, Chitosan, St. John's Wort, Jujube, Carrot, Passion Flower, Broccoli, Placenta, Barley , Grape seed, peanut seed coat, bilberry, black cohosh, maria thistle, laurel, sage, rosemary, raffma, black vinegar, bitter gourd, maca, safflower, flax, oolong tea, flower spine, caffeine, capsaicin, ki Looligosaccharide, Glucosamine, Buckwheat, Citrus, Dietary fiber, Protein, Prunes, Spirulina, Barley young leaves, Nucleic acid, Yeast, Shiitake, Plum meat, Amino acid, Deep sea potato extract, Noni, Oyster meat, Suppon, Champignon, Psyllium, Acerola, Pineapple, banana, peach, apricot, melon, strawberry, raspberry, orange, fucoidan, mesimacob, cranberry, chondroitin sulfate, zinc, iron, ceramide, silk peptide, glycine, niacin, chesttree, L-cysteine, red wine leaf, millet, Horsetail, Biotin, Centella Asiatica, Lotus Cup, Pycnogenol, Japanese cypress, Rhubarb, Clove, Rosemary, Catechin, Pual, Citric Acid, Beer Yeast, Merirot, Black Zinger, Ginger, Gajutsu, Nattokina Ze, Benikouji, Tocotrienol, Lactoferrin, Cinnamon, Persimmon Buckwheat, Cocoa, Yuzu Seed Extract, Perilla Seed Extract, Lychee Seed Extract, Evening Primrose Extract, Black Rice Extract, α-Lipoic Acid, Gabba, Fresh Coffee Bean Extract, Fuquisa Extract, Kiwi Seed Extract, Wenzhou 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, maquiberry extract, Japanese cherry extract, rice polyamine , Wheat polyamine) and the like.

The stigmasterol-containing composition can be used as a skin external preparation (including cosmetics, pharmaceuticals, and quasi drugs).
Examples of the external preparation for skin that can contain the above-described stigmasterol-containing composition include, for example, emulsion, soap, face wash, bath preparation, cream, emulsion, lotion, eau de cologne, shaving cream, shaving lotion, makeup Oil, sunscreen / sunscreen lotion, funny powder, foundation, perfume, pack, nail cream, enamel, enamel remover, eyebrow, blusher, eye cream, eye shadow, mascara, eyeliner, lipstick, lip balm, shampoo, rinse, Examples include hair dyes, dispersions, and cleaning materials. Examples of the form of pharmaceuticals or quasi drugs that can contain the stigmasterol-containing composition include ointments, creams, and liquids for external use.

In addition to the stigmasterol-containing composition, the external preparation for skin of the above-described form is a component that is blended in a skin external preparation such as cosmetics and quasi-drugs as long as the action of the stigmasterol-containing composition is not impaired , Oils, higher alcohols, fatty acids, UV absorbers, powders, pigments, surfactants, polyhydric alcohols / sugars, polymers, physiologically active ingredients, solvents, antioxidants, fragrances, preservatives, etc. it can.
Examples are listed below, but the present invention is not limited to these examples.

(1) Examples of oil components Ester-based 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, octyldodecyl myristate, isocetyl isostearate, diethyl sebacate, adipine Diisopropyl acid, isoaralkyl neopentanoate, glyceryl tri (capryl / 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, octyldodecyl linoleate, octyldodecyl isoleate, isopropyl isostearate Cetostearyl 2-ethylhexanoate, stearyl 2-ethylhexanoate, hexyl isostearate, ethyleneglycol dioctanoate , Ethylene glycol dioleate, propylene glycol dicaprate, propylene glycol di (capryl / capric acid), propylene glycol dicaprylate, neopentyl glycol dicaprate, neopentyl glycol dioctanoate, glyceryl tricaprylate, glyceryl triundecylate, triisopalmitine Glyceryl acid, glyceryl triisostearate, octyldodecyl neopentanoate, isostearyl octanoate, octyl isononanoate, hexyl decyl neodecanoate, octyldodecyl neodecanoate, isocetyl isostearate, isostearyl isostearate, octyldecyl isostearate, polyglycerin oleic acid Ester, polyglycerol 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-stearoyl hydroxystearate 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 and the like.
Animal and vegetable oils and their hydrogenated oils, and naturally occurring waxes: beef tallow, hydrogenated beef tallow, lard, hydrogenated tallow, horse oil, hydrogenated horse oil, mink oil, orange luffy oil, fish oil, hydrogenated fish oil, egg yolk oil and other animal oils and Its hardened oil, avocado oil, almond oil, olive oil, cacao butter, kiwi seed oil, apricot oil, kukui nut oil, sesame oil, wheat germ oil, rice germ oil, rice bran oil, safflower oil, shea butter, soybean oil, evening primrose oil , Perilla oil, tea seed 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, medhome oil, cottonseed oil, hardened cottonseed oil, coconut oil, hardened coconut oil and its hardened , 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 oil phase components: perfluoropolyether, fluorine-modified organopolysiloxane, fluorinated pitch, fluorocarbon, fluoroalcohol, fluoroalkyl / polyoxyalkylene co-modified organopolysiloxane, and the like.

(2) Examples of higher alcohols include lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, behenyl alcohol, 2-ethylhexanol, hexadecyl alcohol, octyldodecanol 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, arachidic acid, arachidonic acid, behenic acid , Erucic acid, 2-ethylhexanoic acid and the like.

(4) Examples of UV 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-2-diparamethoxycinnamate Glyceryl ethylhexanoate, isopropyl paramethoxycinnamate, diethanolamine salt of paramethoxyhydrocinnamic acid, diisopropyl diisopropylcinnamic acid Stealth mixture, urocanic acid, ethyl urocanate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenone sulfonic acid and its salts, dihydroxymethoxybenzophenone, dihydroxymethoxybenzophenone sodium disulfonate, dihydroxybenzophenone, dihydroxydimethoxybenzophenone, hydroxyoctoxybenzophenone, tetrahydroxybenzophenone, Butylmethoxydibenzoylmethane, 2,4,6-trianilino-p- (carbo-2-ethylhexyl-1-oxy) -1,3,5-triazine, 2- (2-hydroxy-5-methylphenyl) benzotriazole , Methyl-O-aminobenzoate, 2-ethylhexyl-2-cyano-3, 3-diphenyl acrylate, 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 and pigments Red 104, Red 201, Yellow 4, Blue 1, Black 401 and other dyes, Yellow 4 AL lake, Yellow 203 BA lake and other lake dyes, nylon powder , Silk powder, urethane powder, Teflon (registered trademark) powder, silicone powder, polymethyl methacrylate powder, cellulose powder, starch, silicone elastomer spherical powder, polyethylene powder, yellow iron oxide, red iron oxide, black Colored pigments such as iron oxide, chromium oxide, carbon black, ultramarine and bitumen, white pigments such as zinc oxide, titanium oxide and cerium oxide, extender pigments such as talc, mica, sericite, kaolin and barium sulfate plate, titanium mica Pearl pigments such as barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, metal salts such as magnesium silicate, Inorganic powders such as Rica and alumina, metal soaps such as aluminum stearate, magnesium stearate, zinc palmitate, zinc myristate, magnesium myristate, zinc laurate, zinc undecylenate, bentonite, smectite, boron nitride, etc. It is done. There are no particular restrictions on the shape of these powders (spherical, rod-like, needle-like, plate-like, irregular shape, flake-like, spindle-like, etc.) and particle diameter. These powders are conventionally known surface treatments such as 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, The surface treatment may or may not be performed 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 , Alkylamide sulfate, alkyl phosphate, POE alkyl phosphate, alkylamide phosphate, alkyloylalkyl taurine salt, N-acyl amino acid salt, POE alkyl ether carboxylate, alkyl sulfosuccinate, alkyl sulfoacetic acid Sodium, acylated hydrolyzed collagen peptide salt, perfluoroalkyl phosphate, etc. are mentioned.
Cationic surfactant: alkyltrimethylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium bromide, cetostearyltrimethylammonium chloride, distearyldimethylammonium chloride, stearyldimethylbenzylammonium chloride, behenyltrimethylammonium bromide, benzalkonium chloride , Behenic acid amidopropyldimethylhydroxypropylammonium chloride, stearic acid diethylaminoethylamide, stearic acid dimethylaminopropylamide, lanolin derivative quaternary ammonium salts, and the like.
Amphoteric surfactants: carboxybetaine type, amide betaine type, sulfobetaine type, hydroxysulfobetaine type, amide sulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type, amidoamine type and the like.
Nonionic surfactant: Propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE sorbitan fatty acid ester, POE sorbitol fatty acid ester, POE glycerin fatty acid ester, POE akyle ether, POE fatty acid ester, POE cured castor Oil, POE castor oil, POE / POP copolymer, POE / POP alkyl ether, polyether-modified silicone lauric acid alkanolamide, alkylamine oxide, hydrogenated soybean phospholipid, and the like.
Natural surfactant: lecithin, saponin, sugar surfactant 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. These chemically modified compounds can also be used.

(8) Examples of polymers Acrylic ester / methacrylic acid ester copolymer (plus size, manufactured by Kyoyo Chemical), vinyl acetate / crotonic acid copolymer (resin 28-1310, manufactured by NSC), vinyl acetate / croton Acid / vinyl neodecanate copolymer (28-2930, manufactured by NSC), methyl vinyl ether maleic acid half ester (Gantrez ES, manufactured by ISP), T-butyl acrylate / ethyl acrylate / methacrylic acid copolymer (rubymer) , BASF), vinyl pyrrolidone / vinyl acetate / vinyl propionate copolymer (Rubicol VAP, BASF), vinyl acetate / crotonic acid copolymer (Rubiset CA, BASF), vinyl acetate / croton Acid / vinyl pyrrolidone copolymer (Rubiset CAP, manufactured by BASF), vinyl pyrrolidone / acrylate copolymer (Rubiflex, BAS) F), acrylate / acrylamide copolymer (Ultrahold, BASF), vinyl acetate / butyl maleate / isobornyl acrylate copolymer (Advantage, ISP), carboxyvinyl polymer (Carbopol, BF Goodrich), anionic polymer compounds such as acrylic acid / alkyl methacrylate copolymer (Pemulene, BF Goodrich), and acetic acid amphoteric products of dialkylaminoethyl methacrylate polymers (Yukaformer, Mitsubishi Chemical) Amphoteric polymer compounds such as octyl acrylate acrylate / hydroxypropyl acrylate / butylaminoethyl methacrylate copolymer (AMPHOMER, NSC), quaternized vinylpyrrolidone / dimethylaminoethyl methacrylate (GAFQUAT, ISP) , Methyl vinyl imidazolium chloride / Cationic polymer compounds such as vinylpyrrolidone copolymer (rubicoat, manufactured by BASF), polyvinylpyrrolidone (rubiscol K, manufactured by BASF), vinylpyrrolidone / vinyl acetate copolymer (rubiscol VA, manufactured by BASF) Nonionic polymer compounds such as vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (copolymer 937, manufactured by ISP), vinylcaprolactam / vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (copolymer VC713, manufactured by ISP), etc. is there. Cellulose or derivatives thereof, keratin and collagen or derivatives 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 derived polymer compounds such as galactan, gum karaya, gum tragacanth, alginic acid, albumin, casein, curdlan, gellan gum and dextran can also be suitably used.

(9) Examples of physiologically active ingredients Examples of physiologically active ingredients include substances that impart some physiological activity to the skin when applied to the skin. For example, whitening ingredients, immunostimulants, anti-aging agents, UV protection agents, slimming agents, tanning agents, antioxidants, hair growth agents, hair restorers, moisturizers, blood circulation promoters, antibacterial agents, bactericides, desiccants, A cooling sensation agent, a warming sensation agent, vitamins, an amino acid, a wound healing promoter, an irritation relaxation agent, an analgesic agent, a cell activator, an enzyme component, etc. are mentioned. Examples of these suitable ingredients include, for example, ashitaba extract, avocado extract, amateur extract, altea extract, arnica extract, aloe extract, apricot extract, apricot kernel extract, ginkgo biloba extract, fennel extract, turmeric extract, oolong tea extract, ages Extract, Echinacea leaf extract, Ogon extract, Oat extract, Oen extract, Barley extract, Hypericum extract, Oyster extract, Dutch mustard extract, Orange extract, Seawater dried product, Seaweed extract, Hydrolyzed elastin, Hydrolyzed wheat powder, Hydrolyzed silk , Chamomile extract, Carrot extract, Kawara mugwort extract, Licorice extract, Calcade extract, Oyster extract, Kina extract, Cucumber extract, Guanosine, Gardenia extract, Kumazasa extract, Clarae Kiss, walnut extract, grapefruit extract, clematis extract, chlorella extract, mulberry extract, gentian extract, tea extract, yeast extract, burdock extract, fermented rice bran extract, rice germ oil, comfrey extract, collagen, bilberry extract, saicin extract, psycho extract Extract Kizuta extract, hawthorn extract, elderberry extract, yarrow extract, mint extract, sage extract, mallow extract, senki Sue extract, assembly extract, soybean extract, tiso extract, thyme extract, tea extract, clove extract, chigaya extract, chimpi extract, touki extract, toshinsen extract, tonin extract, spruce extract, dokudami extract, tomato extract, natto extract, carrot extract, garlic extract, Novara extract, hibiscus extract, bacmond extract, parsley extract, honey, hamamelis extract, parietalia extract, toad extract, bisabolol, loquat extract, dandelion extract, burdock extract, bukuro extract, butcher bloom extract, grape extract, propolis, loofah extract, Safflower extract, peppermint extract, bodaige extract, button extract, hop extract, pine extract, marronnier extract, mizubasho Kiss, Mukuroji extract, Melissa extract, Peach extract, Cornflower extract, Eucalyptus extract, Yukinoshita extract, Yokuinin extract, Artemisia extract, Lavender extract, Apple extract, Lettuce extract, Lemon extract, Lotus root extract, Rose extract, Rosemary extract, Roman chamomile extract And royal jelly extract.
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 pyrrolidonecarboxylate , Moisturizing ingredients such as betaine, whey, trimethylglycine, oily ingredients such as sphingolipid, ceramide, phytosphingosine, cholesterol, cholesterol derivatives, phospholipids, ε-aminocaproic acid, glycyrrhizic acid, β-glycyrrhetinic acid, lysozyme chloride, guaiazulene, Immunostimulants such as hydrocortisone, vitamin A, vitamin B2, vitamin B6, vitamin C, vitamin D, vitamin E, calcium pantothenate, biotin, nicotinamide, vitamin C ester Vitamins, active ingredients such as allantoin, diisopropylamine dichloroacetate, 4-aminomethylcyclohexanecarboxylic acid, antioxidants such as tocopherols, carotenoids, flavonoids, tannins, lignans, saponins, α-hydroxy acids, β-hydroxy acids, etc. Cell activators, blood circulation promoters such as γ-oryzanol and vitamin E derivatives, wound healing agents such as retinol and retinol derivatives, arbutin, kojic acid, placenta extract, sulfur, ellagic acid, linoleic acid, tranexamic acid, glutathione, etc. Whitening agent, cephalanthin, licorice extract, red pepper tincture, hinokitiol, garlic iodide extract, pyridoxine hydrochloride, DL-α-tocopherol, DL-α-tocopherol acetate, nicotinic acid, nicotinic acid derivative, calcium pantothenate, D-pan Tothenyl alcohol, acetyl pantothenyl ethyl ether, biotin, allantoin, isopropylmethylphenol, estradiol, ethinyl estradiol, capronium chloride, benzalkonium chloride, diphenhydramine hydrochloride, takanal, camphor, salicylic acid, nonyl acid vanillylamide, nonanoic acid vanillylamide, pyroctone Olamine, glyceryl pentadecanoate, L-menthol, mononitroguaiacol, resorcin, γ-aminobutyric acid, benzethonium chloride, mexiletine hydrochloride, auxin, female hormone, cantalis tincture, cyclosporine, zinc pyrithione, hydrocortisone, minoxidil, monostearic acid Examples include hair growth agents such as polyoxyethylene sorbitan, mint oil, and Sasanishiki extract.

(10) Examples of antioxidants: sodium bisulfite, sodium sulfite, erythorbic acid, sodium erythorbate, dilauryl thiodipropionate, tocopherol, tolylbiguanide, nordihydroguaiaretic acid, parahydroxyanisole, butylhydroxyanisole, dibutylhydroxy Examples include plant extracts having an antioxidant effect such as toluene, ascorbyl stearate, ascorbyl palmitate, octyl gallate, propyl gallate, carotenoid, flavonoid, tannin, lignan, saponin, apple extract and clove extract.

  As a specific production method, the above-mentioned stigmasterol-containing composition is spray-dried or freeze-dried together with powdered cellulose, and this is easily contained in general foods and beverages (instant foods, etc.) by making it into powder, granules, tablets or solutions. Can be made. Further, the stigmasterol-containing composition can be dissolved in, for example, fats and oils, ethanol, glycerin or a mixture thereof to be liquid and added to a beverage or added to a solid food. If necessary, it can 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 amount of distilled water, sterilized by autoclaving, mixed with 560 mg of koji mold and 42 g of decoction, fermented at 35 ° C for 3 days, and then koji mold fermented rice germ 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 methanol extract.
According to the scheme of FIG. 1, 83 g of this methanol extract was distributed with hexane and water, and the hexane layer was separated to obtain 17.67 g of hexane soluble part (this example).
Fractionation was performed according to the fractionation scheme of FIG. 1, and 149.7 mg of Compound A component was isolated. The isolated component was subjected to NMR structural analysis. The Compound A spectrum is shown in FIG. According to FIG. 2 and the document Suttiarporn P. et al., Nutrients., 2015, 7 (3), 1672-1687 , it was confirmed that Compound A is a stigmasterol represented by the following chemical formula (1). In addition, the content of Compound A in the hexane-soluble part was 0.84%. That is, it was confirmed that the examples contain stigmasterol.

Although the compounding example of the stigmasterol containing composition manufactured by the method of this invention is given to this invention below, the following compounding example does not limit this invention.
Formulation Example 1: Chewing gum (functional indication food or food for specified health use)
53.0wt% sugar
Gum base 20.0
Glucose 10.0
Minamata 16.0
Fragrance 0.5
Stigmasterol-containing composition 0.5
100.0wt%

Formulation Example 2: Gummy (Functional indication food or food for specified health use)
Reduced water tank 40.0wt%
Granulated sugar 20.0
Glucose 20.0
Gelatin 4.7
Water 9.68
Kiwi juice 4.0
Kiwi flavor 0.6
Dye 0.02
Stigmasterol-containing composition 1.0
100.0wt%

Formulation example 3: Candy (functional indication food or food for specified health use)
50.0 wt% sugar
Minamata 33.0
Water 14.4
Organic acid 2.0
Fragrance 0.2
Stigmasterol-containing composition 0.4
100.0wt%

Formulation Example 4: Yogurt (hardware / soft) (functional food or food for specified health use)
Milk 41.5wt%
Nonfat dry milk 5.8
Sugar 8.0
Agar 0.15
Gelatin 0.1
Lactic acid bacteria 0.005
Stigmasterol-containing composition 0.4
Perfume
Water residue
100.0wt%

Formulation Example 5: Soft drink (functional display food or food for specified health use)
Fructose glucose liquid sugar 30.0wt%
Emulsifier 0.5
Stigmasterol-containing composition 0.05
Perfume
Purified water residue
100.0wt%

Formulation Example 6: Soft capsule (functional indication food or food for specified health use)
Rice germ oil 87.0wt%
Emulsifier 12.0
Stigmasterol-containing composition 1.0
100.0wt%

Formulation Example 7: Tablet (Functional indication food or specified health food)
Lactose 54.0wt%
Crystalline cellulose 30.0
Starch degradation product 10.0
Glycerin fatty acid ester 5.0
Stigmasterol-containing composition 1.0
100.0wt%

Formulation Example 8: Oral granules (pharmaceuticals)
Stigmasterol-containing composition 1.0 wt%
Lactose 30.0
Cornstarch 60.0
Crystalline cellulose 8.0
Polyvinylpyrrolidone 1.0
100.0wt%

Formulation Example 9: Tablet
76.4 wt% sugar
Glucose 19.0
Sucrose fatty acid ester 0.2
Stigmasterol-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
Stigmasterol-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 soybean 10.0
Flour 25.0
Mosses 5.0
Stigmasterol-containing composition 5.0
Animal fats and oils 8.9
Oligosaccharide 0.1
Vitamin 0.5
Mineral 0.5
100.0wt%

Formulation Example 10: Cosmetic cream squalane 20.0 wt%
Beeswax 5.0
Refined jojoba oil 5.0
Glycerin 5.0
Glycerol monostearate 2.0
Polyoxyethylene (20) sorbitan-
Monostearate 2.0
Stigmasterol-containing composition 2.0
Antiseptic agent
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
Stigmasterol-containing composition 5.0
Purified water residue
100.0wt%

Formulation Example 12: Body gel macadamia nut oil 2.0 wt%
Octyldodecyl myristate 10.0
Methylphenylpolysiloxane 5.0
Behenyl alcohol 3.0
Stearic acid 3.0
Batyl alcohol 1.0
Glyceryl monostearate 1.0
Tetraoleic acid polyoxyethylene sorbit 2.0
Hydrogenated soybean phospholipid 1.0
Ceramide 0.1
Retinol palmitate 0.1
Preservative Appropriate amount Clover extract 1.0
Stigmasterol-containing composition 1.0
1,3-butylene glycol 5.0
Purified water residue
100.0wt%

Formulation Example 13: Latex 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
Stigmasterol-containing composition 0.5
Potassium hydroxide 0.1
Perfume
Purified water residue
100.0wt%

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

Claims (4)

Fermenting rice bran and / or rice germ to obtain a fermented product,
Thereafter, the fermented product is extracted with a polar solvent to obtain a fermented product extract,
Then, the fermented product extract is dispensed,
A method for producing a stigmasterol-containing composition. The method for producing a stigmasterol-containing composition according to claim 1, wherein the rice bran and / or rice germ is defatted. 3. The method for producing a stigmasterol-containing composition according to claim 1 or 2, wherein the distribution is liquid-liquid distribution, wherein the hexane layer is separated by hexane and water. The method for producing a stigmasterol-containing composition according to any one of claims 1 to 3, wherein the fermented product is fermented with koji mold.

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