Oral composition and collagen smell masking agent

Abstract

To provide a novel oral composition and a collagen smell masking agent.SOLUTION: An oral composition contains collagen and agrimol B. The oral composition has a mass ratio between the collagen and the agrimol B (collagen / agrimol B) of 400 or more and 1,000,000 or less. There is also provided a collagen smell masking agent which contains agrimol B.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to an oral composition and a masking agent for collagen odor.

Background Art

[0002] Collagen is a protein that constitutes the connective tissue of animals. Most of the collagen is composed of a repeating structure of glycylprolylhydroxyproline or glycylprolylalanine. Collagen is a major component of the dermis, and a decrease in collagen is considered to cause skin wrinkles and sagging. Collagen that has become water-soluble by hydrolysis treatment, those obtained by reducing the molecular weight of hydrolyzed collagen, gelatin obtained by heating, extracting, and purifying collagen, and collagen peptides obtained by reducing the molecular weight of gelatin by enzymatic decomposition or the like are distributed as food raw materials, etc., and their beauty effects have attracted particular attention.

[0003] However, the raw materials derived from these collagens are made from raw materials such as pigskin, fish scales, and fish skin and have an odor peculiar to the raw materials (hereinafter referred to as collagen odor), and those with a reduced molecular weight have a bitter taste. Therefore, methods for masking them are required. For example, Patent Document 1 proposes a mixture of ethyl octanoate, geraniol, and β-damascenone as a masking agent that reduces the collagen odor and bitterness of hydrolyzed collagen and makes it odorless and tasteless.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] An object of the present invention is to provide a novel oral composition and a masking agent for collagen odor.

Means for Solving the Problems

[0006] Means for solving the problems of the present invention are as follows. 1. An oral composition characterized by containing collagen and agrimol B, wherein the mass ratio of collagen to agrimol B (collagen / agrimol B) is 400 or more and 1,000,000 or less. 2. A collagen odor masking agent characterized by containing agrimol B.

Effects of the Invention

[0007] According to the present invention, the collagen odor can be masked. According to the present invention, it is possible to provide oral compositions such as foods and drinks, quasi-drugs, and pharmaceuticals that contain collagen but have a suppressed collagen odor.

Modes for Carrying Out the Invention

[0008] In this specification, the notation "A to B" (A and B are numerical values) means a numerical range including both ends. ·Collagen odor masking agent The collagen odor masking agent of the present invention contains agrimol B. The collagen masked by the collagen odor masking agent of the present invention is not particularly limited as long as it has a collagen odor, and may be collagen itself, collagen hydrolyzate, gelatin, collagen peptide, or the like made from collagen as a raw material. Further, the origin of collagen is not particularly limited, and it may be any of mammals such as cows and pigs, birds such as chickens, and fish such as salmon, flounder, sharks, tilapia, and tilapia.

[0009] <Agrimol B> Agrimol B is a compound represented by the following Chemical Formula 1 (molecular weight: 682.75 g / mol). Agrimol B can be a chemically synthesized product, or a product extracted and separated from natural products such as plants, purified as necessary, and can also be used as a mixture. Commercially available products can also be used.

[0010]

Chem.

[0011] As a chemical synthesis of agrimol B, it can be synthesized using phloroglucinol or the like as a starting material. For example, it can be synthesized by the method described in Acta Pharmaceutica Sinica 1989, 24(6): 431-437 or the method disclosed in JP-A-11-335256. In addition, as agrimol B obtained by synthesis, there are two types, (S)-(+)-agrimol B and its optical isomer (R)-(-)-agrimol B. However, agrimol B may be a single compound composed of any one of these, or a mixture composed of two types.

[0012] From the viewpoint of safety, agrimol B derived from plants is preferred. The plant containing agrimol B is not particularly limited as long as it contains agrimol B, but Agrimonia pilosa (scientific name: Agrimonia pilosa, alias: Longyacao) is preferred. Agrimonia pilosa is a perennial herb of the genus Agrimonia in the Rosaceae family. In Japan, it grows wild at the edges of forests, in fields, along roadsides, etc. in Honshu, Shikoku, Kyushu, etc. As Agrimonia pilosa, the whole plant that has grown wild or been cultivated can be collected and used after being naturally dried or heat-dried. Also, the dried product of Agrimonia pilosa commercially available as a raw material for Kampo crude drugs, folk remedy drugs, and health foods can be used. Incidentally, the dried whole plant of Agrimonia pilosa is commercially available under the crude drug name of Xianhecao.

[0013] When agrimonolide B is of plant origin, one or more of the following can be used: an extract, an extract obtained by purifying and concentrating the extract, a distillate obtained by steam distillation, a ground product of a plant containing agrimonolide B, a juice squeezed from this ground product, or a powder obtained by solidifying a liquid containing such agrimonolide B by methods such as liquid fractionation under reduced pressure, spray drying, or freeze drying. Among these, since they contain a high concentration of agrimonolide B, an extract with water or an organic solvent, or an extract obtained from this extract, a dry extract is preferred.

[0014] Extraction can be carried out by known extraction methods using water, various organic solvents, or a mixed solvent thereof as the extraction solvent. Before performing the extraction operation, the raw material can be washed with a hydrophobic solvent, a hydrophilic solvent, or a mixed solvent, either as it is or after being roughly chopped, to remove unnecessary substances such as pigments. Examples of organic solvents used for washing include lower alcohols (e.g., methyl, ethyl, n-propyl, isobutyl, or butyl alcohol), ketones such as acetone and methyl ethyl ketone, nitriles such as acetonitrile, halogenated hydrocarbons such as dichloromethane and chloroform, ethers such as diethyl ether, tetrahydrofuran, and petroleum ether, ethyl acetate, hexane, cyclohexane, toluene, benzene, and the like. Also, before performing the extraction operation, water can be appropriately added to the raw material to moisten it.

[0015] As the extraction solvent, water, the above-mentioned organic solvents, and a mixed solvent thereof can be used. Among these, water, lower alcohols, and a mixed solvent of water and lower alcohols are preferred, and ethanol is preferred as the lower alcohol. To perform extraction with water, for example, 0.5 to 10 parts by weight of water can be added to 1 part by weight of the raw material, and extraction can be carried out at 40 to 120 °C for 5 minutes to 2 hours, preferably for 10 to 60 minutes, more preferably for 10 to 20 minutes. At this time, the extraction efficiency can also be enhanced by stirring. Further, the extraction can also be carried out by heating under reflux. After extraction, filtration or pressing is performed using a filter cloth, a filter, a wire mesh, etc. In this case, pressure can be applied to enhance the working efficiency. Alternatively, an extract can also be obtained by centrifugation (1000 to 20000 rpm). In order to increase the recovery rate, this extraction and filtration process can be repeated 1 to 5 times.

[0016] To perform extraction with an organic solvent, for example, 0.5 to 10 parts by weight of an organic solvent can be added to 1 part by weight of the raw material, and an extract can be obtained in the same manner as extraction with water. As the solvent to be used, the above-mentioned organic solvents can be used alone or in combination of two or more, and a water-containing solvent can also be used. In particular, when the raw material is washed with a hydrophobic solvent before extraction to remove unnecessary substances such as pigments, and when the crude extract after extraction is washed with a hydrophobic solvent as described below, the solvents used for extraction are preferably water, a lower alcohol, a 50 to 80% (v / v) water-containing lower alcohol, and ethanol is preferably used as the lower alcohol. Removal of the solvent can be carried out according to conventional methods such as filtration, centrifugation, and distillation.

[0017] A preferred extraction method from *Kinmizuhiki* can be carried out, for example, as follows. Collect the whole plant grown naturally or cultivated, and use the one that has been naturally dried or heat-dried. Then, cut it into small pieces and immerse it in about 10 times the amount of water or ethyl alcohol with a water content concentration of 0 to 99.5% (v / v), preferably ethyl alcohol with a water content concentration of 1 to 50%, particularly preferably ethyl alcohol with a water content concentration of 5 to 10% for 3 to 5 days for extraction at room temperature, or attach a reflux condenser and extract at 50 to 80 °C for 5 to 24 hours, and filter to recover the extract. This extract is dried to obtain a dry extract by removing water and ethanol using a vacuum drying apparatus under reduced pressure such as a rotary evaporator or a freeze-drying apparatus.

[0018] Next, the dry extract is concentrated. In the concentration step, it is concentrated by washing with 0 to 40% ethyl alcohol to remove the 0 to 40% ethyl alcohol-soluble components. Specifically, the dry extract is washed with 0 to 40% ethanol, particularly preferably 10 to 30% ethanol, and after removing the 0 to 40% ethanol, particularly preferably 10 to 30% ethanol-soluble components by means such as filtration, the filter residue is dried under reduced pressure using a reduced-pressure vacuum drying device such as a rotary evaporator or a freeze-drying device, or By removing water and ethanol, a dry extract in which agrimol B is more concentrated can be obtained. The concentrated dry extract is redissolved in 50 to 99.5% ethanol, particularly preferably 70 to 90% ethanol, and a desired concentration of concentrated powder can be obtained by adding an excipient used for formulation and freeze-drying.

[0019] The collagen odor masking agent of the present invention can contain other masking agents, fragrances, etc., as long as the collagen odor masking effect by agrimol B is not impaired. The collagen odor masking agent of the present invention can be mixed with additives such as excipients, binders, disintegrants, emulsifiers, solubilizers, thickeners, lubricants, flavoring agents, coloring agents, solvents, etc., as necessary, and prepared into a desired shape (dosage form). The dosage form of the collagen odor masking agent of the present invention is not particularly limited, and can be liquid, suspension, powder, granule, paste, etc.

[0020] In the collagen odor masking agent of the present invention, the content of agrimol B is not particularly limited, and can be, for example, 0.00001 to 99.9% by mass. The collagen odor masking agent of the present invention can be used for masking the collagen odor in oral compositions such as foods and drinks, pharmaceuticals, quasi-drugs, etc. having a collagen odor. The amount of the collagen odor masking agent of the present invention used is not particularly limited as long as the effect is exhibited. For example, about 0.0000001 to 1,000,000 parts by mass of collagen can be masked by 1 part by mass of the collagen odor masking agent of the present invention.

[0021] ·Oral composition The oral composition of the present invention contains collagen and the above-mentioned collagen odor masking agent. <Collagen> In the oral composition of the present invention, the collagen is not limited to collagen itself, and may be those made from collagen such as hydrolyzed collagen, gelatin, collagen peptides, etc. Also, the origin of the collagen is not particularly limited, and it may be any of mammals such as cows and pigs, birds such as chickens, and fish such as salmon, flounder, sharks, tilapia, etc.

[0022] The oral composition of the present invention is not particularly limited as long as it is for oral ingestion, and can be food and drink products, pharmaceuticals, quasi-drugs, etc. As food and drink products, it can be in various forms such as beverages like fruit juice drinks, carbonated drinks, tea-based drinks, milk drinks, alcoholic drinks, soft drinks, etc. and powdered drinks, jelly-like foods, various snacks, baked confectioneries, cakes, chocolates, gums, candies, soups, etc. Also, it is not limited to ordinary food and drink products, and may be health foods, functional foods, dietary supplements, supplements, specific insurance foods, nutrient-functional foods, foods with functional claims, etc. The oral composition of the present invention that is a pharmaceutical or a quasi-drug can be used, for example, as oral solid dosage forms such as tablets and granules, and oral liquid preparations such as oral solutions and syrups.

[0023] In the oral composition of the present invention, the mass ratio of collagen to agrimol B (collagen / agrimol B) is preferably, for example, 400 or more and 1,000,000 or less. If this mass ratio is less than 400, the amount of agrimol B contained in the masking agent and other optional components increases, and the odor derived from these may become strong. If this mass ratio exceeds 1,000,000, the masking effect may be insufficient. The smaller this mass ratio (the more agrimol B), the higher the masking effect can be exerted on both the collagen odor and the bitterness of collagen. The content of collagen in the oral composition of the present invention is not particularly limited, but is, for example, about 0.01% by mass or more and 90% by mass or less, preferably 0.05% by mass or more and 80% by mass or less, and more preferably 0.1% by mass or more and 70% by mass or less. Further, the content of agrimol B in the oral composition of the present invention is not particularly limited, but is, for example, about 0.000001% by mass or more and 0.02% by mass or less, preferably 0.000005% by mass or more and 0.01% by mass or less.

Examples

[0024] Hereinafter, examples of the present invention will be described, but the present invention is not limited to these examples only, and various modifications are possible within the technical idea of the present invention. (1) Test sample The test materials are shown in Table 1 below.

Table 1

[0025] (2) Measurement of agrimol B content in the extract of Kinmizuhiki (Preparation of analysis sample of the extract of Kinmizuhiki) To 100 g of dried Kinmizuhiki leaves, 10 times the amount (1 kg) of 90% ethanol was added, and reflux extraction was repeated twice. The obtained extract was filtered through diatomaceous earth and concentrated under reduced pressure by a conventional method. The concentrate was dissolved and suspended in 20% ethanol heated to 50°C, and the insoluble fraction was recovered as a residue by filtration through diatomaceous earth. The residue was redissolved in 90% ethanol, treated with activated carbon, filtered through diatomaceous earth, and concentrated under reduced pressure to obtain an analysis sample.

[0026] (Quantification of agrimol B content) The sample and 10% by volume of DMSO were placed in a volumetric flask, dispersed by ultrasonic waves, and then acetonitrile was added to make the volume constant. The solution filtered through a 0.45 μm filter was used as the sample solution. The agrimol B concentration of the sample solution was measured by HPLC under the following conditions, and the agrimol B content was quantified from the measured value. (Analysis conditions) Column: Ascentis Express C18 (Supelco, 10 cm × 4.6 mm, 2.7 μm) Mobile phase: 0.1% trifluoroacetic acid in water : 0.1% trifluoroacetic acid-containing acetonitrile solution = 10:90 Column temperature: 40 °C Flow rate: 1.4 mL / min Detection: UV288 nm Injection volume: 20 μL (Quantification value of agrimol B) The extract of Cinchona bark contained 0.452% by mass of agrimol B.

[0027] (3) Evaluation method Six professional panelists conducted a sensory evaluation on each oral composition according to the criteria shown in Table 2 below.

Table 2

[0028] 「Test 1」 The raw materials shown in Table 3 below were dissolved in water to prepare an oral composition. A sensory evaluation was conducted on each oral composition. The evaluation results are shown in Table 3.

Table 3

[0029] Indigestible dextrin, β-cyclodextrin, and trehalose were reported to have a masking effect on the smell of collagen. However, the masking effects of indigestible dextrin and trehalose were slight. Although β-cyclodextrin showed a masking effect, in Example 1 of the present invention, both the smell and taste could be suppressed. Catechin, a plant extract, showed a masking effect on the smell of collagen, but its masking effect on taste (bitterness) was slight.

[0030] "Test 2" Oral compositions were prepared by changing the mixing ratio of collagen and agrimol B as shown in Table 4 below. Sensory evaluations were conducted on each oral composition. The results are shown in Table 4.

Table 4

[0031] The upper part of Table 4 shows the results with a constant amount of agrimol B, and the lower part shows the results with a constant amount of collagen peptide. According to the present invention, it was confirmed that the smell of collagen could be masked, and the masking effect on both smell and taste increased as the ratio of agrimol B to collagen increased. In particular, as shown in Examples 6 to 8, even at a high concentration of 20% by mass or more of collagen peptide, the smell of collagen could be masked. In Comparative Example 6, the amount of agrimol B relative to collagen was too small, and the masking effect was slight. In Comparative Example 7, the flavor of kinmizu hiki was too strong to be evaluated.

[0032] "Test 3" The masking effect of agrimol B on the smell of collagen was verified instead of the kinmizu hiki extract. Oral compositions were prepared in the same manner as in Test 2, except that agrimol B was used instead of the kinmizu hiki extract, and added to achieve the agrimol B concentrations corresponding to Examples 1 to 12 of Test 2. · Agrimol B Agrimol B (manufactured by Biorbyt) was dissolved and prepared in 90% ethanol to a concentration of 1 × 10 -2 mass%, and used as a stock solution. This stock solution was adjusted with water to the amounts corresponding to Examples 1 to 12 and used in the tests. As a result of the tests, the same results as in Examples 1 to 12 were shown.

Claims

1. An oral composition characterized by containing collagen and agrimol B, wherein the mass ratio of collagen to agrimol B (collagen / agrimol B) is 400 or more and 1,000,000 or less.

2. A collagen odor masking agent characterized by containing agrimol B.

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