Composition containing lignan compounds, essential oils and fats

Abstract

To provide a high-concentration lignan compound-containing composition in which the occurrence of a starchy precipitate is suppressed.SOLUTION: The present invention has found that there is a manufacturing advantage, in which, by dissolving a lignan compound including sesamin or the like in a mixture of essential oil and oil / fat, the starchy precipitate is reduced while maintaining the high concentration of the lignan compound, and the labor of filtration is reduced.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a composition which reduces precipitation occurring during production and improves dissolution stability by blending lignan compounds with essential oils and fat mixtures. [Background technology]

[0002] Medium-chain triglycerides (MCT) are widely known as edible fats and oils capable of dissolving lignan compounds such as sesamin. For example, Patent Document 1 describes that when medium-chain triglycerides are used as a solvent, lignan compounds can be sufficiently dissolved at a blend ratio (by weight) of lignan compounds:solvent = 1:15-100, but the concentration of lignan compounds that can maintain the transparency of the composition is about 1-2.5% of the composition. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2006-306864 Summary of the Invention [Problem to be solved by the invention]

[0004] Compared with the above-mentioned prior art, the use of essential oils has enabled the solubility of lignan compounds in the composition to be increased while maintaining transparency, but after dissolving the lignan compounds to prepare a solution, a sediment-like precipitate formed, which requires the solution to be filtered using a membrane filter or the like to remove many of the precipitates. [Means for solving the problem]

[0005] As a result of extensive research into achieving the above-mentioned object, the present inventors have found that by containing lignan compounds, essential oils, and fats and oils, it is possible to suppress the occurrence of sediment-like precipitates in the capsule content liquid while maintaining a high concentration of lignan compounds in the composition, for example, in the capsule content liquid, and the transparency of the capsules.

[0006] That is, the present invention is as follows. (1) A composition containing a lignan compound, an essential oil, and a fat or oil. (2) The composition according to (1), wherein the lignan-class compound is contained in an amount of 7% by mass or more when the total amount of the composition is taken as 100% by mass. (3) The composition according to (1) or (2), wherein the lignan-class compounds include sesamin and sesamolin. (4) The composition according to any one of (1) to (3), wherein the essential oil is at least one selected from the group consisting of phenylpropanoids, bisabolane-type sesquiterpene ketones, and menthane-type ketones. (5) The composition according to any one of (1) to (4), wherein the essential oil is one or more selected from the group consisting of clove oil, cassia oil, turmeric oil, spearmint oil, dill seed oil, davana oil, tarragon oil, thyme oil, basil oil, fennel oil, star anise oil, yellow turmeric oil, and sage oil. (6) The composition according to any one of (1) to (5), wherein the oil or fat is a long-chain fatty acid triglyceride and / or a medium-chain fatty acid triglyceride. (7) The composition according to any one of (1) to (6), wherein the fat or oil contains 75% or more of long-chain fatty acid triglycerides and 25% or less of medium-chain fatty acid triglycerides, when the total amount of the fat or oil is taken as 100%. (8) The composition according to any one of (1) to (7), wherein the oil is at least one selected from the group consisting of fish oil, sesame oil, wheat germ oil, soybean oil, olive oil, safflower oil, coconut oil, and palm oil. (9) A food product containing the composition according to any one of (1) to (8). (10) A capsule comprising the composition according to any one of (1) to (9) and a shell containing the composition. (11) A method for producing a composition containing lignan-class compounds, comprising preparing a mixture of essential oil and fat, and dissolving lignan-class compounds in the mixture. [Effects of the Invention]

[0007] According to the present invention, it is possible to reduce sedimentation, which is advantageous in terms of production in that it reduces the labor required for filtration. DETAILED DESCRIPTION OF THE INVENTION

[0008] The present invention will be described in detail below.

[0009] <Lignan compounds> In the present invention, lignan compounds are a type of phenylpropanoid, a polyphenol compound derived from a plant-derived dibenzylbutane skeleton. Lignan compounds are extracted from red sesame (linseed), sesame, and Brassica vegetables, and in some cases, purified versions can be used. Examples include sesaminol, pinoresinol, syringaresinol, sesamin, sesamolin, lariciresinol, secoisolariciresinol, matairesinol, and hydroxymatairesinol. These compounds may be contained alone or in combination of two or more.

[0010] As mentioned above, lignan compounds have been reported to have cholesterol-lowering, antihypertensive, antioxidant, liver-protective, liver cancer-preventing, breast cancer-suppressing, and immunostimulating effects. Most sesamin-containing soft capsules currently on the market recommend a daily sesamin intake of 10-15 mg. In fact, when subjects experiencing severe fatigue took soft capsules containing 10 mg of sesamin and vitamin E for eight weeks, significant improvements in fatigue, beauty, and sleep were observed, and the LDL oxidation lag time was increased, leading to increased antioxidant activity in the blood. (Glob. J. Health Sci., 2015;7:1-10)

[0011] The amount of the lignan-class compound is not particularly limited and can be appropriately selected depending on the dosage form, intake form, intake (administration) amount, etc. For example, the amount of the lignan-class compound can be preferably 7% by mass or more, 10% by mass or more, 12% by mass or more, and preferably 40% by mass or less, 30% by mass or less, 25% by mass or less, when the total amount of the composition is taken as 100% by mass.

[0012] <Sesamin> Sesamin is a lignan compound found in large amounts in sesame oil and Japanese pepper, and has the following structural formula: [ka] Structural formula of sesamin

[0013] <Sesamolin> Sesamolin, like sesamin, is a lignan compound found in large amounts in sesame oil and Japanese pepper, and has the following structural formula: [ka] Structural formula of sesamolin

[0014] <Sesame extract> The lignan compounds used in the composition of the present invention preferably contain sesamin and are sesamin concentrates, such as sesame extract, obtained by extraction and / or purification from food-derived materials such as sesame oil. Sesamin can be added in addition to those obtained from sesame oil, etc. The composition of the present invention preferably contains sesamolin. Sesamolin can be added in addition to those obtained from sesame oil, etc. The concentrations of sesamin and sesamolin in sesame seeds have been reported (Bull. Natl. Inst. Crop Sci., 2008;9:27-61). According to this literature, the sesamin:sesamolin concentration ratio in sesame seeds varies depending on the variety. For example, the sesamin and sesamolin concentrations in sesame extract AKY-2885 (Inabata Aromatics Co., Ltd.) are 39.7% sesamin and 46.5% sesamolin.

[0015] <Essential oil> In the present invention, the lignan compounds can be used by dissolving them in essential oils and fats. The essential oil is preferably at least one of phenylpropanoid, bisabolane-type sesquiterpene ketone, and menthane-type ketone. Phenylpropanoids are compounds formed by the condensation of multiple 1-phenylpropane units derived from phenylalanine, and their derivatives. Examples include lignan compounds such as coumaric acid, cinnamic acid, caffeic acid, eugenol, anethole, estragole, thymol, apiol, sinapyl alcohol, ferulic acid, and sesamin. Essential oils rich in phenylpropanoids include cassia oil, clove leaf oil, clove bud oil, anise oil, fennel oil, tarragon oil, thyme oil, parsley seed oil, basil oil, and Illicium verum (star anise) oil. Bisabolane sesquiterpene ketones are a type of monocyclic sesquiterpene formed by the condensation of three isoprene molecules. Monocyclic sesquiterpenes are classified into bisabolane, germacrane, elemane, and humulane types depending on the shape of the ring and the position of the functional groups. The bisabolane skeleton has one six-membered ring and a 2,6-dimethylhexyl group attached to that ring. Among the bisabolane sesquiterpenes, compounds with a carbonyl group are bisabolane sesquiterpene ketones. Examples include α-bisabolene, β-bisabolene, γ-bisabolene, α-curcumene, β-curcumene, zingiberene, β-sesquiphellandrene, α-turmerone, β-turmerone, AR-turmerone, β-atlantone, and xanthorrhizol. Essential oils that contain these ingredients in abundance include turmeric oil, cumin seed oil, ginger oil, yellow turmeric oil, zedoary oil, medicinal turmeric oil, purple zedoary oil, turmeric oil, mango zedoary oil, mango ginger oil, ginger oil, mountain ginger oil, bitter ginger oil, Chinese ginger oil, rhubarb oil, and turmeric oil. Menthane ketones are part of a monocyclic monoterpene group formed by the condensation of two isoprene molecules. Menthane is a molecule with a methyl group and an isopropyl group at the para position of a six-membered ring. Menthane ketones are a group of compounds that contain a menthane skeleton as part of their molecular structure and at least one ketone group. Examples include carvone, dihydrocarvone, thujonone, α-thujone, β-thujone, camphor, piperitone, piperitenone, and pulegone. Essential oils rich in these compounds include peppermint oil, spearmint oil, pennyroyal mint oil, watermint oil, cornmint oil, Asian mint oil, Australian mint oil, Japanese mint oil, bergamot mint oil, malva mint oil, ginger mint oil, sage oil, and eucalyptus divesiculosus oil. Among these, cassia oil, clove oil, turmeric oil, cumin seed oil, spearmint oil, dill seed oil, davana oil, tarragon oil, thyme oil, basil oil, fennel oil, star anise oil, and sage oil are preferred, and cassia oil, clove oil, spearmint oil, dill seed oil, thyme oil, basil oil, fennel oil, star anise oil, and sage oil are particularly preferred. These may be contained alone or in combination of two or more.

[0016] The cassia oil, clove oil, turmeric oil, cumin seed oil, spearmint oil, dill seed oil, davana oil, tarragon oil, thyme oil, basil oil, fennel oil, star anise oil, and sage oil that can be used in the composition of the present invention are not limited in any way by their origin, form, production method, etc.

[0017] For example, cassia oil is obtained by steam distillation of the bark and leaves of the Cinnamomum cassia tree, but it also includes oils obtained from different parts of the same plant and from related species in the genus Cinnamomum. Clove oil is obtained by steam distillation of the leaves and buds of Syzygium aromaticum, but also includes oils from different parts of the same plant and from related species in the Myrtaceae genus. Turmeric oil is obtained by steam distillation of the rhizomes of Curcuma longa, but it also includes oils obtained from different parts of the same plant and from related plants in the Zingiberaceae family and Curcuma genus. Cumin seed oil is obtained by steam distillation of the seeds of Cuminum cyminum, but it also includes oils obtained from different parts of the same plant and from related species of the genus Cuminum. Spearmint oil is obtained by steam distillation of the leaves of Mentha spicata, but it also includes oils obtained from different parts of the same plant. Dill seed oil is obtained by steam distillation of the seeds of Anethum graveolens, but it also includes oils obtained from different parts of the same plant. Davana oil is obtained by steam distillation of the whole Artemisia pallens plant, but it also includes oils obtained from different parts of the same plant. Tarragon oil is obtained by steam distillation of the leaves of Artemisia dracunculus, but it also includes oils obtained from different parts of the same plant. Thyme oil is obtained by steam distillation of the whole Thymus plant, but it can also include oils obtained from different parts of the same plant. Basil oil is obtained by steam distillation of the whole plant Ocimum basilicum, but also includes oils obtained from different parts of the same plant. Fennel oil is obtained by steam distillation of the seeds of Foeniculum vulgare, but also includes oils obtained from different parts of the same plant. Star anise oil is obtained by steam distillation of the fruits of Illicium verum, but it also includes oils obtained from different parts of the same plant. Sage oil is obtained by steam distillation of the whole plant Salvia officinalis Linnaeus, but it also includes oils obtained from different parts of the same plant.

[0018] Essential oils are lipophilic compositions typically obtained by steam distillation of plant leaves, stems, roots, fruits, seeds, or flowers, although the oils used in the compositions of the present invention may also be obtained by expression or extraction methods. Alternatively, the extract may be dried and refined to form an absolute, which may then be dissolved in oil again. Essential oils may originate from India, Indonesia, China, France, or Spain, but those from other countries may also be used. Furthermore, synthetic essential oils containing at least one of the phenylpropanoids, bisabolane-type sesquiterpene ketones, and menthane-type ketones contained in the essential oils may be used, either extracted and refined, or synthesized.

[0019] Essential oils are mixtures of volatile oily compounds with boiling points between 150°C and 300°C. Essential oils do not contain fatty acid triglycerides, such as the medium-chain triglycerides and long-chain triglycerides described below, but contain molecules such as phenylpropanoids, bisabolane-type sesquiterpene ketones, and menthane-type ketones. In addition to the above compounds, essential oils may also contain terpenes, such as α-pinene, β-pinene, limonene, and β-caryophyllene, as well as alcohols, such as linalool, geraniol, and hexanol, as their main components. Essential oils may also contain black pepper oil, orange oil, bergamot oil, and geranium oil.

[0020] The amount of essential oil is not particularly limited and can be appropriately selected depending on the dosage form, intake form, intake (administration) amount, etc. For example, the amount of essential oil can be preferably 10% by mass or more, 40% by mass or more, 60% by mass or more, and preferably 90% by mass or less, 85% by mass or less, 80% by mass or less, when the total amount of the composition is taken as 100% by mass.

[0021] <Oils and fats> In the present invention, the fats and oils may include medium-chain fatty acid triglycerides and long-chain fatty acid triglycerides.

[0022] <Medium-chain triglyceride> Medium-chain triglycerides (MCTs) are fats and oils in which three molecules of fatty acids (medium-chain fatty acids) with 5 to 12 carbon atoms form an ester bond with glycerin. Specifically, they refer to fatty acid triglycerides containing fatty acids such as valeric acid, caproic acid, heptyl acid, caprylic acid, pelargonic acid, and capric acid. While the above fatty acids are saturated, the constituent fatty acids can also be unsaturated. MCTs can be made from coconut oil or palm oil. MCTs are a mixture of non-volatile oily compounds obtained by pressing coconut or palm, with a boiling point between 150 and 170°C.

[0023] <Long-chain fatty acid triglyceride> Long-chain triglycerides (LCTs) are fats and oils in which three molecules of fatty acids (long-chain fatty acids) with 13 or more carbon atoms (LCTs) form an ester bond with glycerin. Specifically, they refer to fatty acid triglycerides containing fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, and arachidic acid. While the above fatty acids are saturated, the constituent fatty acids can also be unsaturated fatty acids such as palmitoleic acid, oleic acid, linoleic acid, linolenic acid, docosahexaenoic acid, eicosapentaenoic acid, and arachidonic acid. LCTs can also be made from sesame oil, black sesame oil, white sesame oil, salad oil, olive oil, perilla oil, flaxseed oil, fish oil, wheat germ oil, soybean oil, and safflower oil. LCT is a mixture of non-volatile oily compounds obtained by pressing sesame, black sesame, white sesame, rapeseed, cottonseed, safflower, sunflower, corn, rice, rice bran, rice germ, grape seed, olive, perilla, linseed, fish, wheat germ, soybean, etc., and has a boiling point between 250°C and 500°C.

[0024] The amount of fat or oil is not particularly limited and can be appropriately selected depending on the dosage form, intake form, intake (administration) amount, etc. For example, the amount of fat or oil can be preferably 5% by mass or more, 10% by mass or more, 15% by mass or more, and preferably 50% by mass or less, 40% by mass or less, 30% by mass or less, when the total amount of the composition is 100% by mass.

[0025] <Method of producing the composition> The method for producing the lignan-class compound-containing composition of the present invention comprises preparing a mixture of essential oil and fat, and dissolving the lignan-class compound in the mixture. After mixing the essential oil and fats (long-chain fatty acid triglycerides, medium-chain fatty acid triglycerides), the lignan compounds are added and mixed, and dissolved by heating, preferably at 75-100°C for 5-15 minutes, more preferably at 85°C for 10 minutes. The solution is then cooled to room temperature with water and allowed to stand overnight. After standing, the sample is centrifuged at 15°C and 10,000 rpm for 5 minutes. The resulting supernatant and precipitate are separated, and the mass of the precipitate is measured. The precipitate is recorded as a sediment or a crystal.

[0026] <Stabilized precipitation> When lignan compounds are dissolved in a solvent (essential oil, fat, etc.) by heating and then cooled, precipitation occurs if the solvent used has low solubility for the compounds contained in the lignan compounds. In the case of sesame extract, two types of precipitates are formed. One is a white crystalline precipitate with a particle size of 0.1 mm or more. This is sesamin and sesamolin. The other is a brown precipitate with a particle size of less than 0.1 mm, which is a sediment-like precipitate. The sediment-like precipitate is non-crystalline impurities other than sesamin and sesamolin contained in the sesame extract.

[0027] <Filtration process> The sediment can be removed by centrifugation, but because centrifugation is difficult to use on a scale of 10 kg or more, it can be removed by pressure filtration using a membrane filter. As the sediment increases relative to the solution mass, the membrane filter becomes clogged, increasing the filtration time. Therefore, reducing the sediment shortens the filtration time, which is advantageous in production.

[0028] As described in the above-mentioned manufacturing method, the composition of the present invention can be prepared by mixing essential oils and fats (long-chain fatty acid triglycerides, medium-chain fatty acid triglycerides) and then adding and mixing lignan compounds, thereby preventing the occurrence of sedimentation. As the fats and oils, long-chain fatty acid triglycerides and medium-chain fatty acid triglycerides can be used alone or in combination. When long-chain fatty acid triglycerides and medium-chain fatty acid triglycerides are combined, it is preferable that the long-chain fatty acid triglycerides account for 75% or more and the medium-chain fatty acid triglycerides for 25% or less, and more preferably 80% or more and 20% or less, of the total amount of fats and oils taken as 100%.

[0029] The composition of the present invention is preferably provided in the form of a food (functional food, health supplement, nutrient functional food, food for special dietary uses, food for specified health uses, nutritional supplement, dietary food, health food, supplement, etc.), as well as a beverage, pharmaceutical, quasi-drug, cosmetic, etc. The present invention can also be provided in the form of a health food such as a tablet, capsule, powder, granule, or drink (including a solution or suspension), or in the form of a soft drink, tea drink, dairy product such as yogurt or lactic acid bacteria drink, seasoning, processed food, dessert, confectionery (for example, gum, candy, jelly), etc., but is not limited to these.

[0030] <Food and beverages> When the present invention is provided as a food or drink, the food or drink is not particularly limited, and examples thereof include capsules, beverages, foods (processed foods), confectioneries, and the like. The food and drink may be a food with health claims (for example, a food for specified health uses or a food with nutrient functions), or may be a supplement, feed, food additive, or the like. The capsules are not particularly limited, and examples thereof include the capsules exemplified above, such as seamless capsules and soft capsules. The capsule shells and other capsule forms (shells, etc.) of the capsules are also exemplified below. The manner of use of the composition (a composition in which sesamin is dissolved in a mixture of essential oils and fats) in foods and beverages is not particularly limited and may be selected depending on the type of food and beverage. For example, when the composition is made into capsules as described above, the composition may be contained in the capsules (e.g., the capsule core and / or shell), or the composition may be added (blended) to foods and beverages (using the composition as a food and beverage additive). When the composition is added in this manner, the food or drink to be used is not particularly limited, and examples thereof include foods such as noodles (soba, udon, Chinese noodles, instant noodles, etc.), confectioneries, breads, processed seafood or livestock foods (kamaboko, ham, sausage, etc.), dairy products (processed milk, fermented milk, etc.), oils and oil-processed foods (salad oil, tempura oil, margarine, mayonnaise, shortening, whipped cream, dressing, etc.), seasonings (sauces, etc.), retort foods (curry, stew, rice bowls, porridge, rice porridge, etc.), frozen desserts (ice cream, sherbet, etc.), fried foods, and beverages (tea drinks, soft drinks, carbonated drinks, nutritional drinks, fruit drinks, lactic acid drinks, etc.).

[0031] The compositions of the present invention may contain any desired ingredients as long as they do not impair their effects. For example, they may contain bioactive ingredients such as vitamins such as vitamin D and vitamin E, fats and oils such as DHA and EPA, minerals, hormones, nutritional components, and flavorings. Other ingredients may be selected and added depending on the desired function, form, use, and target of application. Examples of suitable ingredients include, but are not limited to, carriers, excipients, binders, disintegrants, lubricants, coating agents, colorants, flavorings, stabilizers, emulsifiers, surfactants, absorption enhancers, gelling agents, pH adjusters, preservatives, antioxidants, refreshing agents, bioactive substances, bioactive substances, microorganisms, foods and beverages, botanicals, sweeteners, acidulants, seasonings, and tonics. These other ingredients may be used alone or in combination.

[0032] When the composition of the present invention is used in a capsule, the capsule having a shell (membrane) that houses the composition may be a soft capsule, a hard capsule, or a seamless capsule. "Soft capsules" include rotary die soft capsules, which are manufactured by using a rotary die to fill the contents between two film sheets while molding and punching them out, and seamless capsules, which are manufactured by a dropping method using a double nozzle. Capsules include hard capsules, some of which are made of gelatin, but the compounding ingredients described below are often encapsulated in liquid form, so they are particularly intended for use in soft capsules.

[0033] <Capsule shell> The capsule shell of the present invention is made of gelatin or a plant-derived polysaccharide, and since these compounds usually account for the largest proportion in the capsule shell composition, the capsule shell can be said to be gelatin-based or plant-based. Gelatin is derived from collagen, which is the main protein component of the skin, bones, tendons, etc. of cattle, sheep, pigs, chickens, fish, etc., and gelatin made from cattle bones, cattle hides, or pigskins is easily available as an industrial raw material, but the origin is not particularly limited. Gelatin is a denatured form of collagen obtained by treating the above-mentioned raw material with acid or alkali and then extracting it with warm water. The treatment method can be acid treatment or alkali treatment, but the present invention is not particularly limited to this treatment method. The shell of a vegetable capsule may usually contain a film-forming component (film-forming base, film-forming agent). The film-forming component is not particularly limited and can be appropriately selected depending on the intended use of the capsule, and examples thereof include polysaccharides (or derivatives thereof) {e.g., seaweed-derived polysaccharides [e.g., agar, carrageenan, alginic acid or its salts (e.g., alkali metal salts (sodium salt, potassium salt, etc.), alkaline earth metal salts (calcium salt, magnesium salt, etc.), iron salts, tin salts, etc.), furcellaran, curdlan, etc.], resin-derived polysaccharides (e.g., gum ghatti, gum arabic, etc.), microbial-derived polysaccharides (e.g., pullulan, welan gum, xanthan gum, gellan gum, etc.), plant-derived polysaccharides (e.g., tragacanth gum, pectin, glucomannan, starch, polydextrose, dextrin, maltodextrin, cyclodextrin, indigestible dextrin, etc.), seed-derived polysaccharides, etc. Examples of suitable additives include sugars [e.g., guar gum or its derivatives (e.g., hydroxypropyl guar gum, cationized guar gum, guar gum hydrolysates (guar gum enzymatic hydrolysates, etc.)), tara gum, tamarind seed gum, locust bean gum, psyllium seed gum, and flax seed gum], fermented polysaccharides (e.g., diutan gum), cellulose derivatives (e.g., hydroxypropyl cellulose, hydroxypropylmethyl cellulose, methyl cellulose, carboxymethyl cellulose), chitosan, synthetic resins (e.g., polyvinyl alcohol), proteins (e.g., casein, zein), and sugar alcohols (e.g., sorbitol, maltitol, lactitol, palatinit, xylitol, mannitol, galactitol, and erythritol). The film-forming components may be used alone or in combination of two or more.

[0034] The film-forming component may be capable of forming a hydrophilic colloid, and depending on the type, may function as a plasticizer, sweetener, dietary fiber, bulking agent, etc. Commercially available film-forming components may be used.

[0035] The coating may contain plasticizers, colorants, sweeteners, flavorings, antioxidants, preservatives, and the like. For example, the coating may contain a plasticizer to adjust the coating strength, etc. Examples of plasticizers include polyhydric alcohols (e.g., (poly)alkylene glycols such as ethylene glycol, propylene glycol, polyethylene glycol, and polypropylene glycol; polyols having three or more hydroxyl groups such as glycerin), sugars (e.g., monosaccharides (e.g., glucose, fructose, glucose, and galactose), disaccharides (e.g., sucrose, maltose, trehalose, and coupling sugar), oligosaccharides (e.g., maltooligosaccharides), etc.), sugar alcohols (e.g., sorbitol, maltitol, lactitol), and the like. Examples of suitable plasticizers include the sugar alcohols exemplified above, such as ethanol, palatinit, xylitol, mannitol, galactitol, and erythritol, polysaccharides and derivatives thereof (for example, starch, starch derivatives (for example, polydextrose, dextrin, maltodextrin, indigestible dextrin, cyclodextrin (α, β, or γ)), cellulose derivatives (for example, hydroxypropyl cellulose, hydroxypropylmethyl cellulose, methyl cellulose, carboxymethyl cellulose), polyvinyl alcohol, and triacetin. Plasticizers may be used alone or in combination of two or more. As mentioned above, sugar alcohols, starch, starch derivatives, etc. can also be used as film-forming components.

[0036] In a capsule having a core, the core may be in a solid state, a liquid state, etc. The liquid state also includes a colloidal state, an emulsion state, a jelly state, etc. As described above, the core may contain other components than the composition of the present invention, and may also contain other ingredients. The core may generally be non-dissolving (non-eroding) with respect to the coating (or the portion in contact with the coating).

[0037] <Transparency assessment> The composition of the present invention can dissolve lignan compounds such as sesamin (particularly sesame extract) at high concentrations, while maintaining a transparent solution and reducing the occurrence of precipitation. Transparency can be evaluated by total light transmittance, haze, or transparency using a see-through watch, or by evaluating transmittance based on turbidity. When a composition containing lignan compounds is filled into a soft capsule with a transparent coating, transparency is important in the present invention because a transparent content without precipitation results in a beautiful appearance and improved consumer appeal. [Example]

[0038] The present invention will be further explained below with reference to examples, but the present invention is not limited to these examples.

[0039] 1. Solubility test

[0040] <Preparation of experimental materials> The sesame extract used in the experiment was AKY-2885 (trade name) (containing 40% sesamin and 47% sesamolin) purchased from Inabata Fragrance Co., Ltd. Clove oil used in the experiment was purchased from Inabata Fragrance Co., Ltd. as a steam distillate of Eugenia caryophyllata Thunberg leaves (trade name: AKY-2608). Turmeric oil used in the experiment was purchased from Inabata Fragrance Co., Ltd. and was a steam-distilled product of the rhizomes of C. longa (product name: AKY-1953). Cassia oil, a steam distillate of Cinnamomum cassia leaves (trade name: AKY-2609), was purchased from Inabata Fragrance Co., Ltd. and used in the experiment. Spearmint oil used in the experiment was steam distilled Mentha spicata leaves (trade name: KY-2238) purchased from Inabata Fragrance Co., Ltd. Dill seed oil was purchased from Inabata Fragrance Co., Ltd. as a steam distillate of Anethum graveolens seeds (trade name: AKY-2772) and used in the experiment. Basil oil used in the experiment was purchased from Inabata Fragrance Co., Ltd. as a steam distillate of the whole plant of Ocimum basilicum (trade name: AKY-2780). Star anise oil used in the experiment was purchased from Inabata Fragrance Co., Ltd. as a steam distillate of Illicium verum fruit (trade name: KY-2782). MCT was purchased from Eiwa Trading Co., Ltd. (Tokyo, Japan) as a pressed product of Elaeis guineensis fruit (trade name: MCT 70 / 30) and used in the experiment. The sesame oil used was Taihaku Sesame Oil (trade name) purchased from Takemoto Oil & Fat Co., Ltd. The wheat germ oil used was Summit Oil (trade name), an edible wheat germ oil purchased from Summit Oil Co., Ltd. The soybean oil used was J Oil Mills (trade name) refined soybean oil purchased from J Oil Mills Co., Ltd. The olive oil used was refined olive oil DCOOP (trade name) purchased from DCOOP. The salad oil used was Nisshin Oillio Safflower Salad Oil (trade name) purchased from Nisshin Oillio Co., Ltd. The refined fish oil used was a 1:1 mixture of DHA-46 (trade name) and EPA-18 (trade name) purchased from Tama Biochemical Co., Ltd. Yellow turmeric oil (product name: AKY-2607) was purchased from Inabata Fragrance Co., Ltd. and steam-distilled from the rhizomes of C. aromatica and used in the experiment.

[0041] <Sample preparation> Sesame extract AKY-2885 (40% sesamin, 47% sesamolin) was mixed with a mixture of essential oils and fats (long-chain fatty acid triglycerides, medium-chain fatty acid triglycerides) in the composition ratios (unit: mass%) shown in Tables 1 to 18 below, and dissolved by heating at 85°C for 10 minutes. The solution was then cooled to room temperature with water and allowed to stand overnight. After standing, the sample was centrifuged at 15°C, 10,000 rpm, and 5 minutes using a multipurpose centrifuge CAX-371 (Tomy Seiko Co., Ltd.). The resulting supernatant and precipitate were separated, and the mass of the precipitate was measured. The precipitate was recorded as a sediment or crystalline form.

[0042] <Filtration process> The precipitate in the obtained sample was removed by centrifugation.

[0043] <Evaluation method for solubility test> The sediment percentage is the percentage obtained by dividing the mass (g) of the sediment formed after centrifugation by the mass (g) of the dissolved sesame extract. The evaluation was carried out as follows: Evaluation 1: Evaluation when the ratio of fat to essential oil is increased That is, when the ratio of essential oil to fats was changed to 80:10, 70:20, or 60:30, compared to the amount of sediment when the ratio of essential oil to fats was 90:0, if the percentage of sediment-like sediment decreased by 5% or more, it was marked with ◎; if it decreased by 0% or more but less than 5%, it was marked with ○; if it increased by more than 0% but less than 10%, it was marked with △; and if it increased by 10% or more, it was marked with ×.

[0044] <Measurement of Sesamin and Sesamolin Concentration> The concentrations (mass%) of sesamin and sesamolin contained in the supernatants of all the samples after the above centrifugation were quantified using a UPLC-MS system (LCMS-8050, Shimadzu Corporation). Sesamin analysis was performed using a UPLC-MS system (LCMS-8050, Shimadzu Corporation) under the following conditions. The column used was a Shim-pack XR-ODSII (2.0 mm ID x 75 mm, particle size: 2.2 μm, Shimadzu Corporation). The flow rate was 0.2 mL / min. The mobile phase was a 4:1 mixture of methanol and 5 mM ammonium acetate aqueous solution. The retention time was 2.25 min. The injected solution volume was 1 μL. ESI-MS measurements were performed under the following conditions: the drift voltage was 2.5 kV. The ionization mode was positive. The ion source temperature was 100°C. The desolvation gas flow rate was 10 L / min, and the desolvation temperature was 100°C. The collision-induced dissociation gas used was argon gas at 270 kPa, with a collision energy of 11 eV. Multiple reaction monitoring was used to identify the compounds, and [M+NH4] += m / z 372.20 [M+NH4-C7H5O2-H2O] + The transition to m / z 372.20 was tracked. Sesamolin analysis was performed using the same method as the sesamin analysis described above, except for the points described below. The mobile phase was methanol:5 mM ammonium acetate aqueous solution, with the concentration changed linearly from 4:1 to 1:0 over 2.5 minutes, and then returned to 4:1 over 2.51 minutes. The retention time was 2.55 minutes. ESI was introduced using MS / MS. The drift voltage was 4.0 kV. The ion source temperature was 225°C, and the desolvation temperature was 150°C. The collision energy of argon gas was 27 eV. Multiple reaction monitoring was used to identify the compound, and [M+NH4] + = m / z 388.20 to [MC 12 H 12 O5+H] + The transition to m / z 135.00 was followed. The results are shown in Tables 1 to 18.

[0045] <Transparency evaluation test> The samples prepared in the solubility test were subjected to UV-visible absorbance measurement using a HITACHI U-3900 Spectrophotometer to quantify the transparency of the solution and solvent in the vial. Turbidity was evaluated using transmittance at 750 nm. The baseline was the transmittance of the glass cell. The results are shown in Tables 1 to 18.

[0046] Example 1 [Table 1] As shown in Table 1, when oil and fat were added, compared to Sample 41, a high lignan compound (sesamin and sesamolin) concentration of 9.3% by mass or more, especially a high sesamin concentration of 6.8% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 3 to 14%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0047] Example 2 [Table 2] As shown in Table 2, when oil and fat were added, compared to Sample 41, a high lignan compound (sesamin and sesamolin) concentration of 8.1% by mass or more, especially a high sesamin concentration of 5.9% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 7-20%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0048] Example 3 [Table 3] As shown in Table 3, when oil and fat were added, compared to Sample 41, a high lignan compound (sesamin and sesamolin) concentration of 8.6% by mass or more, especially a high sesamin concentration of 6.2% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sedimentary sediment decreased by 4 to 17%, demonstrating the effect of reducing sedimentation. This simplifies the filtration process, which is advantageous in terms of production.

[0049] Example 4 [Table 4] As shown in Table 4, when oil and fat were added, compared to Sample 41, a high lignan compound (sesamin and sesamolin) concentration of 7.9% by mass or more, especially a high sesamin concentration of 5.7% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 3 to 26%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0050] Example 5 [Table 5] As shown in Table 5, when oil and fat were added, compared to Sample 41, a high lignan compound (sesamin and sesamolin) concentration of 8.8% by mass or more, especially a high sesamin concentration of 6.4% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 9 to 30%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0051] Example 6 [Table 6] As shown in Table 6, when oil and fat were added, compared to Sample 66, a high lignan compound (sesamin and sesamolin) concentration of 9.1% by mass or more, especially a high sesamin concentration of 6.6% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 33 to 43%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0052] Example 7 [Table 7] As shown in Table 7, when oil and fat were added, compared to Sample 66, a high lignan compound (sesamin and sesamolin) concentration of 9.1% by mass or more, especially a high sesamin concentration of 6.6% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 26 to 43%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0053] Example 8 [Table 8] As shown in Table 8, when oil and fat were added, compared to Sample 66, a high lignan compound (sesamin and sesamolin) concentration of 8.9% by mass or more, especially a high sesamin concentration of 6.5% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 20-30%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0054] Example 9 [Table 9] As shown in Table 9, when oil and fat were added, compared to Sample 66, a high lignan compound (sesamin and sesamolin) concentration of 9.1% by mass or more, especially a high sesamin concentration of 6.6% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 22 to 34%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0055] Example 10 [Table 10] As shown in Table 10, when oil and fat were added, compared to Sample 66, a high lignan compound (sesamin and sesamolin) concentration of 8.1% by mass or more, especially a high sesamin concentration of 5.9% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sedimentary sediment decreased by 21 to 39%, demonstrating the effect of reducing sedimentation. This simplifies the filtration process, which is advantageous in terms of production.

[0056] Example 11 [Table 11] As shown in Table 11, when oil and fat were added, compared to Sample 104, a high lignan compound (sesamin and sesamolin) concentration of 5.0% by mass or more, especially a high sesamin concentration of 2.5% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 7 to 22%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0057] Example 12 [Table 12] As shown in Table 12, compared to sample 111, samples 113, 114, 115, and 116, which contained added oil and fat, maintained a high lignan compound (sesamin and sesamolin) concentration of 8.2% by mass or more, especially a high sesamin concentration of 5.7% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm, while reducing the rate of sediment by 2 to 9%, demonstrating the effect of reducing sedimentation. This simplifies the filtration process, which is advantageous in manufacturing.

[0058] Example 13 [Table 13] As shown in Table 13, compared to sample 125, samples 126, 129, 130, and 131, which contained added oil and fat, maintained a high lignan compound (sesamin and sesamolin) concentration of 6.1% by mass or more, especially a high sesamin concentration of 3.7% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm, while reducing the rate of sediment by 2 to 7%, demonstrating the effect of reducing sedimentation. This simplifies the filtration process, which is advantageous in manufacturing.

[0059] Example 14 [Table 14] As shown in Table 14, when oil and fat were added, compared to Sample 132, a high lignan compound (sesamin and sesamolin) concentration of 6.0% by mass or more, especially a high sesamin concentration of 3.4% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 0-19%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production.

[0060] Example 15 [Table 15] As shown in Table 15, compared to sample 139, samples 140, 142, 143, and 144, which contained added oil and fat, maintained a high lignan compound (sesamin and sesamolin) concentration of 6.3% by mass or more, especially a high sesamin concentration of 3.8% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm, while reducing the rate of sediment by 6 to 11%, demonstrating the effect of reducing sedimentation. This simplifies the filtration process, which is advantageous in manufacturing.

[0061] Example 16 [Table 16] As shown in Table 16, compared to Sample 22, Samples 24 and 27, which contain added oil and fat, maintain a high lignan compound (sesamin and sesamolin) concentration of 9.0% by mass or more, especially a high sesamin concentration of 6.5% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm, while reducing the rate of sediment by 3 to 6%, demonstrating the effect of reducing sedimentation. This simplifies the filtration process, which is advantageous in manufacturing.

[0062] Example 17 [Table 17] As shown in Table 17, when oil and fat were added, a high lignan compound (sesamin and sesamolin) concentration of 9.0% by mass or more, especially a high sesamin concentration of 6.6% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sedimentary sediment decreased by 14 to 18%, demonstrating the effect of reducing sedimentation, compared to Sample 41. This simplifies the filtration process, which is advantageous in terms of production.

[0063] Example 18 [Table 18] As shown in Table 18, when oil and fat were added, compared to Sample 66, a high lignan compound (sesamin and sesamolin) concentration of 9.1% by mass or more, especially a high sesamin concentration of 6.6% by mass or more, and high transparency (transmittance) of 95% or more at 750 nm were maintained, while the percentage of sediment-like precipitates decreased by 16 to 22%, demonstrating the effect of reducing precipitates. This simplifies the filtration process, which is advantageous in terms of production. [Industrial Applicability]

[0064] The composition according to the present invention can be filled into a capsule shell, which is a capsule membrane, to provide the capsule. Furthermore, the composition of the present invention can be incorporated into liquid foods such as concentrated liquids, gels, jellies, and slurries, or into solid foods such as powders, granules, tablets, rods, plates, and blocks.

Claims

1. Lignan compounds, Essential oils and A composition comprising an oil and a fat, The lignan compounds are sesamin and sesamolin, The oil or fat is a long-chain fatty acid triglyceride and / or a medium-chain fatty acid triglyceride, The essential oil is one or more selected from the group consisting of clove oil, cassia oil, turmeric oil, and basil oil; and the amount of the lignan-class compound is 5% by mass or more when the total amount of the composition is 100% by mass, wherein, when the essential oil is basil oil and the fats and oils are long-chain fatty acid triglycerides and medium-chain fatty acid triglycerides, the ratio of the essential oil to the fats and oils in the composition is 70:20 to 60:30; When the essential oil is basil oil and the fat is a long-chain fatty acid triglyceride, the ratio of the essential oil to the fat in the composition is 80:10 to 60:

30. composition.

2. The composition according to claim 1, wherein the amount of the lignan-class compound is 7% by mass or more when the total amount of the composition is 100% by mass.

3. Lignan compounds, Essential oils and A composition comprising an oil and a fat, The lignan compounds are sesamin and sesamolin, The oil or fat is a long-chain fatty acid triglyceride and / or a medium-chain fatty acid triglyceride, The essential oil is spearmint oil, When the fats and oils are long-chain fatty acid triglycerides and medium-chain fatty acid triglycerides, the ratio of the essential oil to the fats and oils in the composition is 70:20 to 60:30; when the fats and oils are long-chain fatty acid triglycerides, the ratio of the essential oil to the fats and oils in the composition is 80:10 to 70:20; and The amount of the lignan-class compound is 7% by mass or more when the total amount of the composition is 100% by mass. composition.

4. Lignan compounds, Essential oils and A composition comprising an oil and a fat, The lignan compounds are sesamin and sesamolin, The oil or fat is a long-chain fatty acid triglyceride and / or a medium-chain fatty acid triglyceride, The essential oil is star anise oil, When the fats and oils are long-chain fatty acid triglycerides and medium-chain fatty acid triglycerides, the ratio of the essential oil to fats and oils in the composition is 80:10, and when the fats and oils are long-chain fatty acid triglycerides, the ratio of the essential oil to fats and oils in the composition is 80:10 to 60:30; and The amount of the lignan-class compound is 7% by mass or more when the total amount of the composition is 100% by mass. composition.

5. Lignan compounds, Essential oils and A composition comprising an oil and a fat, The lignan compounds are sesamin and sesamolin, The oil or fat is a long-chain fatty acid triglyceride and / or a medium-chain fatty acid triglyceride, the essential oil is dill seed oil, When the fats and oils are long-chain fatty acid triglycerides and medium-chain fatty acid triglycerides, the ratio of the essential oil to fats and oils in the composition is 80:10 or 60:30, and when the fats and oils are long-chain fatty acid triglycerides, the ratio of the essential oil to fats and oils in the composition is 80:10 to 70:20; and The amount of the lignan-class compound is 7% by mass or more when the total amount of the composition is 100% by mass. composition.

6. Lignan compounds, Essential oils and A composition comprising an oil and a fat, The lignan compounds are sesamin and sesamolin, The oil or fat is a long-chain fatty acid triglyceride and / or a medium-chain fatty acid triglyceride, the essential oils are cassia oil and turmeric oil, The ratio of essential oil to fat in the composition is 70:20; and The amount of the lignan-class compound is 7% by mass or more when the total amount of the composition is 100% by mass. composition.

7. The composition according to any one of claims 1 to 6, wherein the oil or fat contains 75% or more of long-chain fatty acid triglycerides and 25% or less of medium-chain fatty acid triglycerides when the total amount of the oil or fat is taken as 100%.

8. The composition according to any one of claims 1 to 7, wherein the long-chain fatty acid triglyceride is at least one selected from the group consisting of fish oil, sesame oil, wheat germ oil, soybean oil, olive oil, and safflower oil, and the medium-chain fatty acid triglyceride is at least one selected from the group consisting of coconut oil and palm oil.

9. A food product containing the composition according to any one of claims 1 to 8.

10. A composition according to any one of claims 1 to 8; a shell containing the composition; and A capsule comprising:

11. preparing a mixture of the essential oil and the fat; dissolving the lignan-class compound in the mixture; A method for producing the composition according to any one of claims 1 to 8.

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