JP7610395B2 - Oral Compositions - Google Patents

Description

The present invention relates to an oral composition.

Polyalkoxyflavonoids such as nobiletin and tangeretin are found in extracts of citrus plants, and are useful ingredients that are expected to contribute to improving and supporting memory by extending neurites in the brain in response to nerve growth factor (NGF).

However, polyalkoxyflavonoids have a solubility in water of less than 0.01 mg/mL, which is a particularly low solubility in water among poorly water-soluble polyphenols, making it difficult to effectively use them in foods, beverages, medicines, and the like. Therefore, various techniques for solubilizing polyalkoxyflavonoids in water have been studied. For example, a method in which nobiletin or a nobiletin-containing substance is dissolved in a 20 to 90% by volume ethanol aqueous solution and the resulting solution is dried to obtain a solid dispersion in which nobiletin is dispersed in an amorphous state (Patent Document 1), a method in which nobiletin or a nobiletin-containing substance is mixed with a water-soluble hesperidin derivative, heated and melted, then cooled and solidified to obtain a solid dispersion in which nobiletin is dispersed in an amorphous state (Patent Document 2), and a method in which nobiletin is mixed with a polypeptide and a polysaccharide, heated and melted, then cooled and solidified to obtain a solid dispersion in which nobiletin is dispersed in an amorphous state in the polypeptide and polysaccharide (Patent Document 3) are known.

JP 2019-167336 A JP 2018-131432 A JP 2016-49105 A

In examining the application of polyalkoxyflavonoids to oral compositions, the present inventors found that, due to the low solubility of polyalkoxyflavonoids in water, when polyalkoxyflavonoids are orally taken directly or in the form of an instant drink, they feel rough on the tongue, which is an obstacle to continued intake, and that when they are made into a packaged drink, they are prone to become cloudy, which mars the aesthetic appearance of the drink and leads to a decrease in consumer willingness to purchase them. Furthermore, the above-mentioned prior art requires that the polyalkoxyflavonoid be in the form of an amorphous solid dispersion in order to impart water solubility to the polyalkoxyflavonoid, and they found that there is room for improvement in terms of more easily solubilizing polyalkoxyflavonoids in water.

The present invention aims to improve the solubility of polyalkoxyflavonoids in water and more easily provide an oral composition that suppresses the roughness felt on the tongue when orally taken and the cloudiness in beverage form that are caused by polyalkoxyflavonoids.

In view of the above problems, the present inventors have conducted extensive research and found that by incorporating a specific polyphenol in a specific mass ratio to a specific amount of polyalkoxyflavonoid, the solubility of the polyalkoxyflavonoid in water is improved, and the roughness on the tongue when taken orally and the cloudiness when made into a beverage can be suppressed.

That is, the present invention provides the following [1] to [5].
[1] A composition for oral administration comprising the following components (A) and (B), wherein the mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30:
A solid composition for oral administration comprising the following components (A) and (B), wherein the mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30: (A) 3 to 50 mass% of a polyalkoxyflavonoid represented by the following formula (1), and (B) chlorogenic acids.
(A) 3 to 50 mass % of a polyalkoxyflavonoid represented by the following formula (1), and (B) a chlorogenic acid [3]. A liquid composition for oral administration comprising the following components (A) and (B), wherein the mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30:
A method for suppressing roughness on the tongue caused by polyalkoxyflavonoids when orally ingested, comprising: (A) 0.03 mass% or more of a polyalkoxyflavonoid represented by the following formula (1); and (B) chlorogenic acids [4]. The method comprises the following components (A) and (B), with the components (A) and (B) coexisting in a mass ratio of 1 to 30, [(B)/(A)]:
(A) a polyalkoxyflavonoid represented by the following formula (1), and (B) a chlorogenic acid [5]. A method for suppressing turbidity in a beverage caused by a polyalkoxyflavonoid, comprising: (A) a polyalkoxyflavonoid represented by the following formula (1), and (B) a chlorogenic acid [5]. The method comprises causing the following components (A) and (B) to coexist in a mass ratio of component (A) to component (B) [(B)/(A)] of 1 to 30:
(A) a polyalkoxyflavonoid represented by the following formula (1), and (B) a chlorogenic acid

[In the formula, ^R1 represents a hydrogen atom or a _C1-6 alkyl group, ^R2 , ^R3 and ^R4 each independently represent a hydrogen atom or a _C1-6 alkoxy group, and ^R5 and ^R6 each independently represent a _C1-6 alkyl group.]

The oral composition of the present invention has improved solubility of polyalkoxyflavonoid in water, which can reduce roughness on the tongue when taken orally and cloudiness when made into a beverage.

[Oral Composition]
In this specification, "oral composition" refers to a composition that is unlikely to be harmful to human health and is taken orally in normal social life, and is not limited to administrative classifications such as food, medicine, quasi-drug, etc. Therefore, the oral composition of the present invention means a wide range of foods and drinks that constitute general foods, health foods (functional food and drink), health functional foods (foods for specified health uses, foods with nutrient functions, foods with functional claims), quasi-drugs, medicines, etc., that are taken orally.

The oral composition of the present invention contains, as component (A), a polyalkoxyflavonoid represented by the following formula (1):

[In the formula, ^R1 represents a hydrogen atom or a _C1-6 alkyl group, ^R2 , ^R3 and ^R4 each independently represent a hydrogen atom or a _C1-6 alkoxy group, and ^R5 and ^R6 each independently represent a _C1-6 alkyl group.]

In formula (1), the _C1-6 alkyl group in ^R1 , R5 ^, and ^R6 may be either linear or branched, so long as it has 1 to 6 carbon atoms. Specific examples include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Of these, a _C1-3 alkyl group is preferred, a methyl group or an ethyl group is more preferred, and a methyl group is even more preferred.
Furthermore, the _C1-6 alkoxy group in ^R2 , ^R3 , and ^R4 may be either linear or branched, so long as it has 1 to 6 carbon atoms. Specific examples include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. Of these, a _C1-3 alkoxy group is preferred, a methoxy group and an ethoxy group are more preferred, and a methoxy group is even more preferred.

Among these, from the viewpoint of providing excellent physiological effects, component (A) is preferably one or more selected from nobiletin and tangeretin, and more preferably nobiletin.

Among the components (A), if nobiletin is contained, it will extend neurites in the brain in response to NGF, and can be expected to contribute to improving or supporting memory, etc. Therefore, the oral composition of the present invention can be used as an oral composition for improving memory, an oral composition for supporting memory, or an oral composition for extending neurites. These compositions may contain nobiletin as an active ingredient, or may contain chlorogenic acids, which are component (B) described below, as an active ingredient, or may contain both nobiletin and chlorogenic acids as active ingredients. Note that, with regard to the memory improvement or memory support of component (B) chlorogenic acids, the contents described in International Publication No. 2007/091613 (applicant: University of Tsukuba) and JP-A-2018-39797 (applicant: Kao Corporation) can be used.

Component (A) may be contained in the form of a commercially available reagent or an extract of a plant containing polyalkoxyflavonoid. The plant may be any plant commonly used in the food and beverage industry, but is not particularly limited thereto. For example, nobiletin is contained in plants of the Rutaceae family. Examples of plants belonging to the family Rutaceae include Citrus depressa, Citrus unshiu, Citrus tangerina, Citrus erythrosa, Citrus aurantium, Citrus natsudaidai, Citrus grandis, Citrus junos, Citrus rericulata, Citrus limon, Citrus trifoliata, and Citrus medica L., all of which belong to the genus Citrus. One or more kinds of plants can be used. Among them, lemon citrus, satsuma mandarin, and bitter orange are preferred. Concentrates or purified products of the plant extracts may be used. There are no particular limitations on the methods and conditions for extraction, concentration, and purification, and known methods and conditions can be used.

The content of component (A) in the solid content of the oral composition of the present invention is 3% by mass or more, preferably 4% by mass or more, more preferably 4.5% by mass or more, from the viewpoint of providing an excellent physiological effect, and is 50% by mass or less, preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 8% by mass or less, from the viewpoint of suppressing roughness on the tongue when taken orally, suppressing turbidity when made into a beverage form, and suppressing the bitterness and astringency of the polyalkoxyflavonoid itself. The content of component (A) in the solid content of the oral composition of the present invention is 3 to 50% by mass, preferably 4 to 40% by mass, more preferably 4.5 to 30% by mass, even more preferably 4.5 to 20% by mass, and even more preferably 4.5 to 8% by mass. In this specification, the term "solid content" refers to the residue obtained by drying 1 g of a sample in an electric thermostatic dryer at 105°C for 3 hours and removing volatile substances, and the term "solid content amount" refers to the mass of the residue. In addition, in this specification, the content of component (A) is defined based on the total amount of the compound represented by the above formula (1). Furthermore, the content of component (A) can be measured by an analytical method suitable for the condition of the measurement sample among commonly known measurement methods, for example, it can be analyzed by liquid chromatography. Specifically, the method described in the Examples below can be mentioned. In addition, when measuring, the sample may be freeze-dried to fit the detection range of the device, or impurities in the sample may be removed to fit the separation ability of the device, and other appropriate treatments may be performed as necessary.

The oral composition of the present invention contains chlorogenic acids as component (B). In this specification, "chlorogenic acids" is a collective term for monocaffeoylquinic acids, i.e., 3-caffeoylquinic acid, 4-caffeoylquinic acid, and 5-caffeoylquinic acid, monoferuloylquinic acids, i.e., 3-feruloylquinic acid, 4-feruloylquinic acid, and 5-feruloylquinic acid, and dicaffeoylquinic acids, i.e., 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid. In the present invention, it is sufficient to contain at least one of the nine types of chlorogenic acids mentioned above.

Chlorogenic acids may also be in the form of salts. Examples of salts include salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as magnesium and calcium, salts with organic amines such as monoethanolamine, diethanolamine, and triethanolamine, and salts with basic amino acids such as arginine, lysine, histidine, and ornithine.

Component (B) may be contained in the form of a commercially available reagent or an extract of a plant containing chlorogenic acids. The plant is not particularly limited as long as it contains chlorogenic acids and is commonly used in the field of food and beverages, and examples thereof include sunflower seeds, unripe apples, coffee beans, Simon leaves, cones of pinaceae plants, seed shells of pinaceae plants, sugarcane and nandina leaves, burdock, eggplant skin, plum fruit, coltsfoot, and grape family plants. One or more types of plants can be used. Among them, coffee beans are preferred. The coffee beans may be green coffee beans or roasted coffee beans, but green coffee beans are preferred in terms of the chlorogenic acid content. The type of coffee tree may be any of Arabica, Robusta, Liberica, and Arabusta. The plant extract may be a concentrate or a purified product thereof. The method and conditions for extraction, concentration, and purification are not particularly limited, and known methods and conditions can be adopted.
Furthermore, as the chlorogenic acids, commercially available preparations containing chlorogenic acids may be used, for example, Flavor Holder RC (Hasegawa Fragrance Co., Ltd.).

The content of component (B) in the solid content of the oral composition of the present invention is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, and even more preferably 80% by mass or more, from the viewpoint of suppressing roughness on the tongue when taken orally and suppressing turbidity when made into a beverage, and is preferably 97% by mass or less, more preferably 96% by mass or less, and even more preferably 95.5% by mass or less, from the viewpoint of suppressing the bitterness and astringency of the oral composition. The content of component (B) in the solid content of the oral composition of the present invention is preferably 50 to 97% by mass, more preferably 60 to 96% by mass, even more preferably 70 to 96% by mass, and even more preferably 80 to 95.5% by mass. In this specification, the content of component (B) is defined based on the total amount of the above nine kinds. The content of component (B) can be measured by an analytical method suitable for the condition of the measurement sample among commonly known measurement methods, and can be analyzed by liquid chromatography, for example. Specifically, the method described in the examples below can be mentioned. In addition, when performing measurements, samples may be freeze-dried to fit the detection range of the device, or impurities may be removed from the sample to fit the separation capabilities of the device, or other appropriate processing may be performed as necessary.

The oral composition of the present invention has a mass ratio of component (A) to component (B) [(B)/(A)] of 1 or more, preferably 2 or more, more preferably 4 or more, even more preferably 12 or more, and even more preferably 16 or more, from the viewpoint of suppressing roughness on the tongue when orally taken, and from the viewpoint of suppressing bitterness and astringency of the oral composition, it is 30 or less, preferably 27 or less, more preferably 24 or less, even more preferably 22 or less, and even more preferably 21 or less. The oral composition of the present invention has a mass ratio of component (A) to component (B) [(B)/(A)] of 1 to 30, preferably 2 to 27, more preferably 4 to 24, even more preferably 12 to 22, and even more preferably 16 to 21.

The oral composition of the present invention may be in any suitable form, either solid or liquid.
Suitable embodiments of the oral composition of the present invention include, for example, a solid oral composition and a liquid oral composition described below.

[Solid composition for oral administration]
The oral solid composition of the present invention is not particularly limited in shape as long as it is solid at room temperature (20°C ± 15°C), and examples thereof include various shapes such as powder, granules, tablets, rods, plates, and blocks. The oral solid composition of the present invention usually has a solid content of 95% by mass or more, preferably 97% by mass or more. The upper limit of the solid content is not particularly limited, and may be 100% by mass.

The oral solid composition of the present invention contains a polyalkoxyflavonoid represented by the above formula (1) as component (A). The specific structure of the polyalkoxyflavonoid is as described above.

From the viewpoint of providing excellent physiological effects, component (A) is preferably one or more selected from nobiletin and tangeretin, and more preferably nobiletin.

The content of component (A) in the oral solid composition of the present invention is 3% by mass or more, preferably 4% by mass or more, more preferably 4.5% by mass or more, from the viewpoint of providing an excellent physiological effect, and is 50% by mass or less, preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 20% by mass or less, and even more preferably 8% by mass or less, from the viewpoint of suppressing roughness on the tongue when orally taken and suppressing the bitterness and astringency of the polyalkoxyflavonoid itself. The content of component (A) in the oral solid composition of the present invention is 3 to 50% by mass, preferably 4 to 40% by mass, more preferably 4.5 to 30% by mass, even more preferably 4.5 to 20% by mass, and even more preferably 4.5 to 8% by mass. The method of analysis of component (A) is as described above.

The oral solid composition of the present invention contains chlorogenic acids as component (B). The specific composition of the chlorogenic acids is as described above.

The content of component (B) in the oral solid composition of the present invention is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, and even more preferably 80% by mass or more, from the viewpoint of suppressing roughness on the tongue when orally taken, and is preferably 97% by mass or less, more preferably 96% by mass or less, and even more preferably 95.5% by mass or less, from the viewpoint of suppressing bitterness and astringency of the oral solid composition. The content of component (B) in the oral solid composition of the present invention is preferably 50 to 97% by mass, more preferably 60 to 96% by mass, even more preferably 70 to 96% by mass, and even more preferably 80 to 95.5% by mass. The method of analysis of component (B) is as described above.

In the oral solid composition of the present invention, the mass ratio of component (A) to component (B) [(B)/(A)] is 1 or more, preferably 2 or more, more preferably 4 or more, even more preferably 12 or more, and even more preferably 16 or more, from the viewpoint of suppressing roughness on the tongue when orally taken, and is 30 or less, preferably 27 or less, more preferably 24 or less, even more preferably 22 or less, and even more preferably 21 or less, from the viewpoint of suppressing bitterness and astringency of the oral solid composition. In addition, in the oral solid composition of the present invention, the mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30, preferably 2 to 27, more preferably 4 to 24, even more preferably 12 to 22, and even more preferably 16 to 21.

The oral solid composition of the present invention may contain, as desired, one or more additives such as sweeteners, acidulants, amino acids, proteins, vitamins, minerals, flavorings, fruit juices, plant extracts, esters, colorants, emulsifiers, milk components, cocoa powder, seasonings, vegetable oils and fats, antioxidants, preservatives, pH adjusters, gelling agents, and carriers. The content of the additives may be appropriately set within a range that does not impair the object of the present invention.

The type of oral solid composition of the present invention is not particularly limited and can be appropriately selected depending on the purpose. Examples include instant drinks; dairy products such as cheese; frozen desserts such as ice cream; confectioneries such as candy, gum, chocolate, cookies, bread, etc.; noodles such as soba and udon; health, beauty, and nutritional supplements such as supplements; pharmaceuticals and quasi-drugs such as powders, tablets, granules, capsules, and lozenges.

Among these, supplements, powders, tablets, granules, and instant drinks are preferred. Oral solid compositions such as supplements, powders, tablets, and granules are in a form to be directly taken, and are preferred embodiments of the present invention because they provide excellent physiological effects due to component (A) and/or component (B).
In addition, an instant beverage is a preferred embodiment of the present invention, since it provides excellent physiological effects due to the components (A) and/or (B) when diluted with a liquid according to a prescribed method of use and orally ingested as a reconstituted beverage. The liquid is not particularly limited as long as it can be reconstituted into a beverage, and examples of the liquid include water, carbonated water, milk, soy milk, etc., and the temperature of the liquid does not matter. The dilution ratio may be in accordance with the prescribed method of use, and is usually 20 to 600 times by mass, preferably 80 to 600 times by mass. The reconstituted beverage prepared from the instant beverage according to the prescribed method of use can have the same configuration as the oral liquid composition described below in terms of the contents of the components (A) and (B), the mass ratio [(B)/(A)], and the pH in the reconstituted beverage.

Instant beverages can be, for example, bottled and measured out with a spoon or the like to drink one cupful, cup-type beverages that contain one cupful, or stick-type beverages that are individually packaged for one cupful. The capacity of the cup is preferably 30-320 mL, and the content of the individually packaged beverages can be set appropriately to suit the cup capacity. The individually packaged beverages can be packaged in packaging materials such as aluminum vapor deposition film. The container and packaging material may be filled with nitrogen gas, and packaging materials with low oxygen permeability are preferred in terms of maintaining quality.

[Oral liquid composition]
The form of the oral liquid composition of the present invention is not particularly limited as long as it has fluidity at room temperature (20° C.±15° C.), and it may be, for example, in a concentrated form. Examples of the oral liquid composition of the present invention include RTD (beverages); concentrated beverages; dairy products such as yogurt, processed milk, and fermented milk; oils and fats and processed oils and fats such as salad oil, tempura oil, margarine, mayonnaise, shortening, whipped cream, and dressing; seasonings such as sauces and sauces; and health, beauty, and nutritional supplements such as drinks.

Among these, RTD (beverages) are preferred because they are easy to enjoy the effects of the present invention. The RTD (beverages) may be packaged beverages. The container is not particularly limited as long as it is a normal packaging container, and examples include molded containers whose main component is polyethylene terephthalate (so-called PET bottles), metal cans, paper containers combined with metal foil or plastic film, bottles, etc.

The oral liquid composition of the present invention contains a polyalkoxyflavonoid represented by the above formula (1) as component (A). The specific structure of the polyalkoxyflavonoid is as described above.

From the viewpoint of providing excellent physiological effects, component (A) is preferably one or more selected from nobiletin and tangeretin, and more preferably nobiletin.

The content of component (A) in the oral liquid composition of the present invention is 0.03% by mass or more, preferably 0.04% by mass or more, from the viewpoint of providing an excellent physiological effect, and is preferably 1% by mass or less, more preferably 0.6% by mass or less, from the viewpoint of suppressing turbidity of the liquid and suppressing the bitterness and astringency of the polyalkoxyflavonoid itself. The content of component (A) in the oral liquid composition of the present invention is preferably 0.03 to 1% by mass, more preferably 0.04 to 0.6% by mass. The method for analyzing the content of component (A) is as described above.

The oral solid composition of the present invention contains chlorogenic acids as component (B). The specific composition of the chlorogenic acids is as described above.

The content of component (B) in the oral liquid composition of the present invention is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, even more preferably 0.4% by mass or more, and even more preferably 0.6% by mass or more, from the viewpoint of suppressing turbidity of the liquid, and is preferably 2% by mass or less, more preferably 1.2% by mass or less, and even more preferably 0.8% by mass or less, from the viewpoint of suppressing bitterness and astringency of the oral liquid composition. The content of component (B) in the oral liquid composition of the present invention is preferably 0.05 to 2% by mass, more preferably 0.1 to 1.2% by mass, even more preferably 0.2 to 1.2% by mass, even more preferably 0.4 to 1.2% by mass, and even more preferably 0.6 to 0.8% by mass. The method of analysis of the content of component (B) is as described above.

In the oral liquid composition of the present invention, the mass ratio of component (A) to component (B) [(B)/(A)] is 1 or more, preferably 2 or more, more preferably 4 or more, even more preferably 8 or more, even more preferably 12 or more, even more preferably 16 or more, from the viewpoint of suppressing turbidity of the liquid, and is 30 or less, preferably 27 or less, more preferably 24 or less, even more preferably 22 or less, even more preferably 21 or less, from the viewpoint of suppressing bitterness and astringency of the oral liquid composition. In addition, in the oral liquid composition of the present invention, the mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30, preferably 2 to 27, more preferably 4 to 24, even more preferably 8 to 24, even more preferably 12 to 22, even more preferably 16 to 21.

From the viewpoint of suppressing bitterness and astringency, the oral liquid composition of the present invention has a pH (20°C) of preferably 3 or more, more preferably 3.5 or more, even more preferably 4 or more, and preferably 7 or less, more preferably 6.8 or less, even more preferably 6.5 or less. The oral liquid composition of the present invention has a pH (20°C) of preferably 3 to 7, more preferably 3.5 to 6.8, even more preferably 4 to 6.5. The pH is measured with a pH meter after adjusting the temperature to 20°C.

The oral liquid composition of the present invention may be a tea beverage or a non-tea beverage. Examples of non-tea beverages include soft drinks, carbonated beverages, tea beverages, fruit juice beverages, vegetable beverages, dairy beverages, and alcoholic beverages.

When the oral liquid composition of the present invention is a packaged beverage, it may have already been heat sterilized. There are no particular limitations on the heat sterilization method, so long as it complies with the conditions stipulated in the applicable laws and regulations (in Japan, the Food Sanitation Act). For example, the beverage may be filled into a container, sealed or sealed, and then sterilized, or the beverage may be sterilized in a sterilizer equipped with a thermometer or the like, or sterilized in a filter or the like, and then automatically filled into a container, which may then be sealed or sealed. More specifically, examples of the method include retort sterilization, high temperature short time sterilization (HTST method), and ultra-high temperature sterilization (UHT method). The container is as described above.

The oral liquid composition of the present invention has improved solubility in water of polyalkoxyflavonoid and excellent dispersibility, so that the turbidity of the liquid is suppressed. For example, when the content of component (A) in the oral liquid composition is adjusted to 0.05% by mass, the turbidity (OD660) of the packaged beverage can be 0.35 or less, preferably 0.31 or less, more preferably 0.2 or less, and even more preferably 0.2 or less. The lower limit of the turbidity (OD660) is not particularly limited and may be 0. Here, in this specification, "turbidity" refers to the absorbance at a wavelength of 660 nm measured at 20°C using a spectrophotometer in a 90° transmission scattering comparison method. Specifically, it can be measured by the method described in the Examples below. The lower the turbidity (OD660) value, the clearer the beverage.

The oral composition of the present invention can be produced according to a conventional method, and any suitable method can be used. For example, it can be produced by mixing components (A) and (B) and, if necessary, other components, and adjusting the content of component (A) and the mass ratio [(B)/(A)]. The order of mixing components (A) and (B) is not particularly limited, and they may be added and mixed in any order, or both may be added and mixed at the same time.
As the mixing method, an appropriate method such as stirring or shaking can be adopted, and a mixing device may be used. The mixing method of the mixing device may be a container rotation type or a container fixed type. As the container rotation type, for example, a horizontal cylinder type, a V type, a double cone type, a cube type, etc. can be adopted. As the container fixed type, for example, a ribbon type, a screw type, a conical screw type, a paddle type, a fluidized bed type, a Phillips blender, etc. can be adopted. In addition, when the oral composition of the present invention is an oral solid composition, it may be granulated by a known granulation method. Examples of the granulation method include spray granulation, fluidized bed granulation, compression granulation, rolling granulation, stirring granulation, extrusion granulation, and powder coating granulation. The granulation conditions can be appropriately selected depending on the granulation method. In addition, when making into tablets, either wet tableting or dry tableting may be used, and a known compression molding machine can be used. Furthermore, in the case of a concentrated liquid, known concentration methods can be used, such as an atmospheric concentration method in which the solvent is evaporated at atmospheric pressure, a reduced pressure concentration method in which the solvent is evaporated at reduced pressure, and a membrane concentration method in which the solvent is removed by membrane separation.

When the oral composition of the present invention is an oral solid composition, it is possible to easily produce an oral solid composition that suppresses roughness on the tongue when taken orally, even without the step of dissolving component (A) in an aqueous ethanol solution during the manufacturing process. Also, when the oral composition of the present invention is an oral liquid composition, it is possible to easily produce a beverage that suppresses liquid turbidity, even without the step of dissolving component (A) in an aqueous ethanol solution during the manufacturing process. That is, from the viewpoint of easily producing an oral composition, it is preferable that the present invention does not include a step of dissolving component (A) in an aqueous ethanol solution during the manufacturing process.

When the oral composition of the present invention is a solid oral composition, it is possible to easily produce an oral solid composition that suppresses roughness on the tongue when taken orally, even without a step of heating and dissolving component (A) during the manufacturing process. Also, when the oral composition of the present invention is a liquid oral composition, it is possible to easily produce a beverage that suppresses liquid turbidity, even without a step of heating and dissolving component (A) during the manufacturing process. That is, from the viewpoint of easily producing an oral composition, it is preferable that the present invention does not include a step of heating and dissolving component (A) during the manufacturing process. Specifically, the heating temperature of component (A) is preferably less than 90°C, more preferably less than 50°C, and most preferably does not substantially include a heating step.

[Inhibition method]
The method of the present invention for suppressing roughness on the tongue during oral intake and cloudiness in a beverage form caused by polyalkoxyflavonoids is to make components (A) and (B) coexist in a ratio in which the mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30. This can improve the solubility of polyalkoxyflavonoids in water. A preferred embodiment is, for example, an embodiment in which chlorogenic acids are contained in an oral product containing polyalkoxyflavonoids. The contents of components (A) and (B) in the solid content of the oral product and the mass ratio [(B)/(A)] are as described above. Specific embodiments of components (A) and (B) and the oral product are also as described above.

1. Analysis of Polyalkoxyflavonoids Using a high performance liquid chromatograph manufactured by Agilent Technologies Inc. and equipped with a column L-Column ODS-2 (4.6 mmφ×50 mm, 2 μm) manufactured by Chemicals Evaluation and Research Institute, Japan, the analysis was carried out by a gradient method at a column temperature of 40° C.

The analysis conditions are as follows.
The sample injection volume was 10 μL, mobile phase A was a 0.1% by mass aqueous trifluoroacetic acid solution, and B was acetonitrile, and the liquids were delivered at a rate of 1.0 mL/min.

Concentration gradient conditions (volume%)
Time Eluent A Eluent B
0 minutes 99% 1%
1 minute 99% 1%
4 minutes 5% 95%
5 minutes 5% 95%
5.01 minutes 99% 1%
6 minutes 99% 1%

Nobiletin was detected by quantifying absorbance at a wavelength of 320 nm. In addition to the above-mentioned method, nobiletin and tangeretin can also be analyzed using the method described in JP 2015-202065 A.

2. Analysis of chlorogenic acids The analytical equipment used was HPLC. The model numbers of the components of the equipment are as follows:
・UV-VIS detector: SPD-20A (Shimadzu Corporation)
Column oven: CTO-20AC (Shimadzu Corporation)
Pump: LC-20AD (Shimadzu Corporation)
・Autosampler: SIL-20AC (Shimadzu Corporation)
Column: Cadenza CD-C18, inner diameter 4.6 mm x length 150 mm, particle size 3 μm (Intact Co., Ltd.)

The analysis conditions are as follows.
Sample injection volume: 10 μL
・Flow rate: 1.0mL/min
UV-VIS detector setting wavelength: 325 nm
Column oven temperature setting: 35°C
Eluent C: 50 mM acetic acid, 0.1 mM 1-hydroxyethane-1,1-diphosphonic acid, 10 mM sodium acetate, 5 (V/V)% acetonitrile solution Eluent D: acetonitrile

Concentration gradient conditions (volume%)
Time Eluent C Eluent D
0.0 minutes 100% 0%
10.0 minutes 100% 0%
15.0 minutes 95% 5%
20.0 minutes 95% 5%
22.0 minutes 92% 8%
50.0 minutes 92% 8%
52.0 minutes 10% 90%
60.0 minutes 10% 90%
60.1 minutes 100% 0%
70.0 minutes 100% 0%

・3-caffeoylquinic acid: 5.3 min
・5-caffeoylquinic acid: 8.8 min
・ 4-caffeoylquinic acid: 11.6 min
・ 3-ferulic acid: 13.0 min
・ 5-ferulaquinic acid: 19.9 min
・ 4-ferulic acid: 21.0 min
・ 3,4-dicaffeoylquinic acid: 36.6 min
・ 3,5-dicaffeoylquinic acid: 37.4 min
・ 4,5-dicaffeoylquinic acid: 44.2 min
From the area % thus determined, the content (mass %) of chlorogenic acids was calculated using 5-caffeoylquinic acid (Tokyo Chemical Industry Co., Ltd.) as a standard substance.

3. Measurement of turbidity (OD660) A sample having a polyalkoxyflavonoid concentration adjusted to 0.05% by mass was measured for absorbance at a wavelength of 660 nm using a spectrophotometer (U2810, manufactured by Hitachi, Ltd.) at 20° C. in a 90° transmission scattering comparison mode.

4. Measurement of pH The temperature was adjusted to 20° C., and the pH was measured using a pH meter (HORIBA Compact pH Meter, manufactured by Horiba, Ltd.).

Examples 1 to 5 and Comparative Example 1
An instant beverage was obtained by uniformly mixing the components in the proportions shown in Table 1. The obtained instant beverage was analyzed and subjected to a sensory evaluation by the following method. The results are shown in Table 1.

Sensory evaluation 1
Each instant beverage was diluted with water at 20°C so that the component (A) was 0.05% by mass after dilution, and a sensory test was carried out by a panel of five experts on the "roughness on the tongue when taken orally" of the reconstituted beverage. The sensory test was carried out after each expert panel agreed to use the following evaluation criteria for "roughness on the tongue when taken orally". The final evaluation was then determined by discussion based on the scores determined by each expert panel.

Evaluation criteria for roughness on the tongue when orally taken: Rating 5: No roughness felt (corresponding to Example 5).
4: Not very rough feeling.
3: Feels slightly rough.
2: Feels rough.
1: Strongly rough feeling (corresponding to Comparative Example 1).

Examples 6 to 10 and Comparative Example 2
The components were mixed in the proportions shown in Table 2, then sterilized at ultra-high temperature for 30 seconds (UHT sterilization, 98°C, 30 seconds), and filled into transparent PET bottles to prepare packaged beverages. The resulting packaged beverages were then analyzed and their turbidity was measured. The results are shown in Table 2.

Example 11 and Comparative Example 3
The components were mixed in the proportions shown in Table 3 to obtain a powder composition for oral administration. The obtained powder composition for oral administration was subjected to analysis and sensory evaluation. The results are shown in Table 3.

Sensory evaluation 2
After 0.1 g of each oral powder composition was placed in the oral cavity, it was dissolved in the mouth by saliva and completely disappeared. A sensory test was conducted by five expert panelists regarding "roughness on the tongue when taken orally". The sensory test was conducted after each expert panel agreed to use the following evaluation criteria for "roughness on the tongue when taken orally". The final evaluation was then determined by discussion based on the scores determined by each expert panel.

Evaluation criteria for roughness on the tongue when taken orally Rating 5: No roughness felt.
4: Not very rough feeling.
3: Feels slightly rough.
2: Feels rough.
1: There is a strong feeling of roughness.

From Tables 1 to 3, it can be seen that by incorporating chlorogenic acids at a specific mass ratio to polyalkoxyflavonoid, the solubility of polyalkoxyflavonoid in water is increased, and the roughness on the tongue when taken orally and the cloudiness when made into a beverage can be suppressed.

Claims (4)

The following components (A) and (B):
(A) 4 to 40 % by mass of nobiletin , and (B) 60 to 96% by mass of monocaffeoylquinic acid
Contains
The mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30;
Oral solid composition. The following components (A) and (B):
(A) 0.04 to 0.6 % by mass of nobiletin , and (B) 0.05 to 2% by mass of monocaffeoylquinic acid
Contains
The mass ratio of component (A) to component (B) [(B)/(A)] is 1 to 30;
Oral liquid composition. The following components (A) and (B):
(A) 4 to 40% by mass of nobiletin , and (B) 60 to 96% by mass of monocaffeoylquinic acid
and a mass ratio of component (A) to component (B) [(B ) /(A)] is 1 to 30. The following components (A) and (B):
(A) 0.04 to 0.6% by mass of nobiletin , and (B) 0.05 to 2% by mass of monocaffeoylquinic acid
and a mass ratio of component (A) to component ( B ) [(B)/(A)] is 1 to 30.