Antibacterial agent, antibacterial oral composition, antibacterial topical preparation for skin, and method for inhibiting bacterial growth in food and drink

Abstract

To provide an antimicrobial agent, an antimicrobial oral composition, an antimicrobial skin external preparation, and a method of inhibiting microbial growth in food and drink products.SOLUTION: The antimicrobial agent, antimicrobial oral composition and antimicrobial skin external preparation employ as an active ingredient a compound represented by the formula (I) in the figure. Microbial growth in food and drink products can be inhibited by mixing the compound represented by the formula (I) in the food and drink products.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an antibacterial agent, an antibacterial oral composition, an antibacterial topical preparation for skin, and a method for inhibiting bacterial growth in foods and beverages. [Background technology]

[0002] Antibacterial agents are widely used in cosmetics, pharmaceuticals, food and beverages, and other products to prevent microbial contamination and deterioration (spoilage and spoilage) of products, as well as to prevent infectious diseases, and are extremely useful in terms of quality control and public health.

[0003] Cosmetics, food, beverages, and other products have the problem of contamination and deterioration (spoilage and spoilage) caused by the proliferation of bacteria such as Escherichia (e.g., Escherichia coli), Staphylococcus (e.g., Staphylococcus aureus), and Bacillus (e.g., Bacillus subtilis). In particular, food and beverages are at risk of food poisoning due to the proliferation of bacteria such as Escherichia (e.g., Escherichia coli) and Staphylococcus (e.g., Staphylococcus aureus). For this reason, antibacterial agents are sometimes used to maintain the quality of products.

[0004] A rich and diverse range of bacteria inhabit the human intestine and skin, maintaining homeostasis by maintaining a balance among them. However, an imbalance in the microbiota can cause various diseases. For example, Escherichia bacteria (e.g., Escherichia coli) are known to cause gastroenteritis, urinary tract infections, and food poisoning due to secondary contamination of food and water. Staphylococcus bacteria (e.g., Staphylococcus aureus) can also cause atopic dermatitis. In particular, Staphylococcus aureus is known to produce various protein toxins. For example, the epidermal exfoliative toxin produced by Staphylococcus aureus acts on the skin throughout the body via the bloodstream, cleaving desmoglein 1, a desmosome-forming protein, and causing intraepidermal blisters. Furthermore, toxic shock syndrome toxins act on T lymphocytes, causing severe inflammation and resulting in a systemic toxic disease characterized by sudden fever, hypotension, scarlet fever-like erythema, and multiple organ failure (Non-Patent Document 1). Enterotoxins produced when Staphylococcus aureus proliferates in food are known to cause food poisoning, the main symptom of which is emetic toxins (Non-Patent Document 2). Furthermore, Staphylococcus aureus is known as a major causative bacterium of hospital-acquired pneumonia. Antibacterial agents may also be used to prevent, treat, or improve such diseases.

[0005] Patent Document 1 describes an antibacterial agent characterized by containing hydroxylated fullerene as an active ingredient. Patent Document 2 describes an antibacterial agent comprising a glyceryl ascorbic acid derivative or a salt thereof. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-179615 [Patent Document 2] Japanese Patent Application Laid-Open No. 2015-3894 [Non-patent literature]

[0007] [Non-Patent Document 1] Hiroshi Shimizu, "New Dermatology: 3rd Edition," Nakayama Shoten Publishing, February 15, 2018, pp. 514-531 [Non-patent document 2] Food Hygiene, Vol. 51, No. 4, 2005, pp. 81-90 Summary of the Invention [Problem to be solved by the invention]

[0008] However, frequent use of the same antibacterial agent can lead to the emergence of bacteria resistant to that agent, making it impossible to suppress bacterial growth. Therefore, there is a need for the development of new antibacterial agents.

[0009] The present invention aims to provide an antibacterial agent, an antibacterial oral composition, and an antibacterial topical skin preparation. It also aims to provide a method for inhibiting bacterial growth in foods and beverages. [Means for solving the problem]

[0010] In order to solve the above problems, the antibacterial agent of the present invention is characterized by containing a compound represented by the following formula (I) as an active ingredient. The antibacterial oral composition and antibacterial topical skin preparation of the present invention are characterized by incorporating a compound represented by the following formula (I). Furthermore, the method of the present invention for inhibiting bacterial growth in food and beverages is characterized by incorporating a compound represented by the following formula (I) into the food and beverage.

[0011] [ka] [Effects of the Invention]

[0012] According to the present invention, by using the compound represented by the above formula (I) as an active ingredient, it is possible to provide an antibacterial agent, an antibacterial oral composition, and an antibacterial topical skin preparation having excellent antibacterial activity. Furthermore, by incorporating the compound represented by the above formula (I) into food and drink, it is possible to provide a method for inhibiting bacterial growth in food and drink. DETAILED DESCRIPTION OF THE INVENTION

[0013] Hereinafter, an embodiment of the present invention will be described. The antibacterial agent according to this embodiment contains a compound represented by the following formula (I) as an active ingredient.

[0014] [ka]

[0015] The compound represented by the formula (I) is a cinnamic acid derivative also known as 3-(4-hydroxy-3-methoxyphenyl)propionic acid. Hereinafter, in this specification, the compound represented by the formula (I) may be referred to as compound (I).

[0016] Compound (I) can be produced, for example, by isolating and purifying from a plant extract containing compound (I). In this case, such a plant extract containing compound (I) can be obtained by a method commonly used for plant extraction. Examples of plants containing compound (I) include rice, barley, wheat, soybean, adzuki bean, corn, etc.

[0017] Compound (I) can also be produced by, for example, fermenting 3-(4-hydroxy-3-methoxyphenyl)propenoic acid or a derivative thereof, or a composition containing the same (e.g., a crushed plant material or extract, etc.) with a microorganism having a phenolic acid reductase to convert the 3-(4-hydroxy-3-methoxyphenyl)propenoic acid to Compound (I), followed by extracting, isolating, and purifying the resulting fermented product. Examples of compositions containing 3-(4-hydroxy-3-methoxyphenyl)propenoic acid include crushed materials and extracts of plants such as coffee, wheat, corn, tomato, yerba mate, mugwort, and burdock. Furthermore, because 3-(4-hydroxy-3-methoxyphenyl)propenoic acid is a component of lignin in woody and herbaceous plants, lignin or a composition containing the same may be used as the fermentation raw material. On the other hand, examples of microorganisms having phenolic acid reductase include lactic acid bacteria such as Lactobacillus plantarum, Lactobacillus fermentum, Lactobacillus gasseri, Lactobacillus johnsonii, Lactobacillus crispatus, Lactobacillus acidophilus, Lactobacillus amylovorus, Lactobacillus delbrueckii, Lactobacillus buchneri, Lactobacillus kefiranofaciens, Lactobacillus gallinarum, and Enterococcus faecalis.

[0018] The method for extracting, isolating, and purifying compound (I) from the above-mentioned plant or fermented product is not particularly limited, and can be carried out according to a conventional method. For example, the extraction process can be carried out by drying the above-mentioned plant or fermented product as the extraction raw material, and then subjecting it to extraction with an extraction solvent either directly or after pulverization using a crusher. Drying can be carried out in the sun or using a commonly used dryer. In addition, the plant or fermented product can be used as the extraction raw material after pretreatment such as degreasing with a nonpolar solvent such as hexane. Pretreatment such as degreasing allows for efficient extraction with a polar solvent.

[0019] As the extraction solvent, it is preferable to use a polar solvent, such as water or a hydrophilic organic solvent, which is preferably used alone or in combination of two or more at room temperature or a temperature below the boiling point of the solvent.

[0020] Water that can be used as an extraction solvent includes pure water, tap water, well water, mineral water, hot spring water, spring water, fresh water, etc., as well as water that has undergone various treatments. Treatments that can be applied to water include, for example, purification, heating, sterilization, filtration, ion exchange, osmotic pressure adjustment, buffering, etc. Therefore, water that can be used as an extraction solvent in this embodiment also includes purified water, hot water, ion-exchanged water, physiological saline, phosphate buffer, phosphate-buffered physiological saline, etc.

[0021] Examples of hydrophilic organic solvents that can be used as extraction solvents include lower aliphatic alcohols having 1 to 5 carbon atoms, such as methanol, ethanol, propyl alcohol, and isopropyl alcohol; lower aliphatic ketones, such as acetone and methyl ethyl ketone; and polyhydric alcohols having 2 to 5 carbon atoms, such as 1,3-butylene glycol, propylene glycol, and glycerin.

[0022] When a mixture of two or more polar solvents is used as an extraction solvent, the mixture ratio can be any and can be adjusted appropriately. For example, when a mixture of water and a hydrophilic organic solvent is used as an extraction solvent, the mixture can be mixed at any ratio, i.e., between more than 0:100 and less than 100:0 (volume ratio, hereinafter the same), and can be adjusted appropriately. For example, when a mixture of water and a lower aliphatic alcohol is used as the extraction solvent, the mixing ratio (volume ratio) of water to lower aliphatic alcohol can be 9:1 or more, or even 7:3 or more, or the mixing ratio of water to lower aliphatic alcohol can be 1:9 or less, or even 2:8 or less. When a mixture of water and a polyhydric alcohol is used, the mixing ratio of water to polyhydric alcohol can be 8:2 or more, or 1:9 or less, and when a mixture of water and a lower aliphatic ketone is used, the mixing ratio of water to lower aliphatic ketone can be 9:1 or more, or 2:8 or less.

[0023] The extraction process is not particularly limited as long as it can dissolve the soluble components contained in the extraction raw material into the extraction solvent, and can be carried out according to conventional methods. For example, the extraction raw material is immersed in an extraction solvent in an amount (mass ratio) 5 to 15 times the amount of the extraction raw material, and the soluble components are extracted at room temperature or under reflux heating, followed by filtration to remove the extraction residue, thereby obtaining an extract. The solvent is distilled off from the obtained extract to obtain a paste-like concentrate, which is then further dried to obtain a dried product.

[0024] The method for isolating and purifying Compound (I) from the extract, concentrate, or dried extract obtained as described above is not particularly limited and can be carried out by a conventional method. For example, the extract may be dissolved in a developing solvent and subjected to column chromatography using a porous material such as silica gel or alumina, or a porous resin such as a styrene-divinylbenzene copolymer or polymethacrylate, to recover a fraction containing Compound (I). In this case, the developing solvent may be appropriately selected depending on the stationary phase used. For example, when the extract is separated by normal phase chromatography using silica gel as the stationary phase, the developing solvent may be chloroform:methanol=95:5. Furthermore, the fraction containing Compound (I) obtained by column chromatography may be purified using any organic compound purification means, such as reversed-phase silica gel chromatography using ODS, recrystallization, liquid-liquid countercurrent extraction, or column chromatography using an ion-exchange resin.

[0025] The compound (I) obtained as described above has an excellent antibacterial effect and can be used as an active ingredient of an antibacterial agent. Furthermore, the compound (I) can be used to produce an antibacterial agent. The antibacterial agent of this embodiment can be used in a wide range of applications, such as pharmaceuticals, quasi-drugs, cosmetics, and food and beverage products.

[0026] Note that, instead of isolated Compound (I), a composition containing Compound (I) may be used as the active ingredient of the antibacterial agent according to this embodiment. Here, the "composition containing Compound (I)" in this embodiment includes an extract obtained using a plant containing Compound (I) as an extraction raw material, a fermented product containing Compound (I), and an extract obtained using the fermented product as an extraction raw material. Furthermore, the "extract" includes an extract obtained by extraction treatment, a diluted or concentrated solution of the extract, or a dried product obtained by drying the extract.

[0027] When a composition containing compound (I) is used as the active ingredient of the antibacterial agent according to this embodiment, the content of compound (I) in the composition is preferably 0.1% by mass or more, more preferably 5% by mass or more, and particularly preferably 50% by mass or more. By using compound (I) with an increased purity as the active ingredient, an antibacterial agent with even more excellent action and effect can be obtained.

[0028] The antibacterial agent of this embodiment may consist solely of compound (I) or a composition containing compound (I), or may be a formulation of compound (I) or a composition containing compound (I).

[0029] The antibacterial agent of this embodiment can be formulated into any dosage form, such as powder, granules, tablets, or liquid, using a pharmaceutically acceptable carrier such as dextrin, cyclodextrin, or any other auxiliary agent, according to a conventional method. In this case, examples of auxiliary agents that can be used include excipients, binders, disintegrants, lubricants, stabilizers, and flavoring and odor-correcting agents. The antibacterial agent can be incorporated into other compositions (e.g., topical skin preparations, oral compositions, etc., as described below) and used, or can be used as an ointment, topical liquid, patch, etc.

[0030] When the antibacterial agent of this embodiment is formulated, the content of compound (I) or a composition containing compound (I) is not particularly limited and can be set appropriately depending on the purpose.

[0031] If necessary, the antibacterial agent of this embodiment can be used as an active ingredient by blending other natural extracts or the like having antibacterial activity with compound (I) or a composition containing compound (I).

[0032] The antibacterial agent of this embodiment can be administered to a patient by transdermal administration, oral administration, etc., and a method suitable for prevention or treatment may be selected appropriately depending on the type of disease. The dose of the antibacterial agent of this embodiment may also be increased or decreased appropriately depending on the type and severity of the disease, individual differences between patients, the administration method, the administration period, etc.

[0033] The antibacterial agent of this embodiment can be used regardless of the type of bacteria to which it is applied. Among these, gram-negative bacteria and gram-positive bacteria are preferred as the bacteria to which it is applied. Examples of gram-negative bacteria include Escherichia (e.g., Escherichia coli), Salmonella, Pseudomonas (e.g., Pseudomonas aeruginosa), Helicobacter, and Neisseria (e.g., Neisseria gonorrhoeae and Neisseria meningitidis). Examples of Gram-positive bacteria include Staphylococcus (e.g., Staphylococcus aureus, Staphylococcus epidermidis), Enterococcus, Streptococcus (e.g., diplococcus, tetrastreptococcus, octastreptococcus, etc., Streptococcus pneumoniae, Streptococcus hemolyticus, and Clostridium mutans), Bacillus (e.g., Bacillus anthracis, Bacillus subtilis), Clostridium (e.g., Clostridium tetani, Clostridium botulinum), Micrococcus (e.g., Micrococcus luteus), Corynebacterium (e.g., Corynebacterium xerosis, Corynebacterium diphtheriae), and Propionibacterium (e.g., Propionibacterium acnes). Among these, from the viewpoint of more effectively exerting the antibacterial effect of this embodiment, bacteria of the genus Escherichia, Staphylococcus, and Bacillus are particularly preferred, and Escherichia coli, Staphylococcus aureus, and Bacillus subtilis are even more preferred.

[0034] The antibacterial agent of this embodiment can inhibit the growth of bacteria through the antibacterial action of compound (I), thereby preventing contamination and deterioration (putrefaction and deterioration) of compositions containing the antibacterial agent (for example, topical skin preparations and foods and beverages described below), and also enabling the antibacterial agent to be administered to humans and the like to prevent, treat, or ameliorate various infectious diseases. More specifically, for example, by adding it to food and beverages, it is possible to inhibit the growth of bacteria that can cause contamination or deterioration (putrefaction or deterioration) of food and beverages, such as Bacillus (e.g., Bacillus subtilis), Escherichia (e.g., Escherichia coli) and Staphylococcus (e.g., Staphylococcus aureus), which can cause food poisoning, and thereby maintain the quality of the food and beverages. Furthermore, by administering the compound to humans or the like, it is possible to prevent, treat, or ameliorate diseases (e.g., gastroenteritis, urinary tract infections, food poisoning, etc.) caused by bacteria of the genus Escherichia (e.g., Escherichia coli). It is also possible to prevent, treat, or ameliorate diseases (e.g., skin infections such as atopic dermatitis and blisters, systemic toxic diseases, food poisoning, pneumonia, etc.) caused by bacteria of the genus Staphylococcus (e.g., Staphylococcus aureus). However, the antibacterial agent of this embodiment can be used for all applications in which it is significant to exert the antibacterial activity of Compound (I) in addition to these applications.

[0035] The antibacterial agent of this embodiment has excellent antibacterial activity and can therefore be suitably used as a reagent for research into the mechanism of action thereof.

[0036] Compound (I) has excellent antibacterial activity and is therefore suitable for incorporation into, for example, topical skin preparations and oral compositions including foods and beverages. In this case, Compound (I) may be incorporated as is, or an antibacterial agent formulated from Compound (I) may be incorporated.

[0037] By incorporating Compound (I) or an antibacterial agent formulated from Compound (I) into a topical skin preparation, bacterial growth in the topical skin preparation can be inhibited, and contamination and deterioration (putrefaction and deterioration) of the topical skin preparation can be inhibited. Furthermore, by incorporating Compound (I) or an antibacterial agent formulated from Compound (I) into a topical skin preparation, the topical skin preparation can be made suitable for antibacterial applications, such as the prevention, treatment, or amelioration of skin infections caused by bacteria of the genus Staphylococcus (e.g., Staphylococcus aureus). The above-mentioned action is preferable because the effect is easily exerted when it is imparted to a topical skin preparation.

[0038] Here, topical skin preparations are not limited to specific categories and include a wide range of transdermal medicines, quasi-drugs, skin cosmetics, etc. Specific examples include ointments, creams, emulsions, beauty serums, lotions, packs, foundations, lip balms, bath additives, hair tonics, hair lotions, soaps, body shampoos, etc.

[0039] The amount of compound (I) in the topical skin preparation can be adjusted as appropriate depending on the type of topical skin preparation, but a suitable blending ratio is 0.100% by mass to 100% by mass, and a particularly suitable blending ratio is 0.125% by mass to 100% by mass. In particular, when compound (I) is added to a topical skin preparation to inhibit bacterial growth, the amount of compound (I) added is not particularly limited as long as it is an amount that can inhibit bacterial growth, but is usually 0.100% by mass to 50.0% by mass, and preferably 0.125% by mass to 30.0% by mass relative to the topical skin preparation.

[0040] By incorporating Compound (I) or an antibacterial agent formulated from Compound (I) into an oral composition, bacterial growth in the oral composition can be inhibited, and contamination and deterioration (putrefaction and deterioration) of the oral composition can be inhibited. Furthermore, by incorporating Compound (I) or an antibacterial agent formulated from Compound (I) into an oral composition, an oral composition suitable for antibacterial applications (for example, for the prevention, treatment, or amelioration of various infectious diseases) can be obtained. The above-mentioned action is preferable because the action and effect are easily exhibited by imparting it to an oral composition.

[0041] An oral composition refers to a composition that is unlikely to be harmful to human health and that is taken orally or by administration through the gastrointestinal tract in normal social life, and is not limited to administrative classifications such as food, medicine, or quasi-drug. Therefore, the "oral composition" in this embodiment broadly includes orally taken general foods, feeds, health foods, health functional foods (foods for specified health uses, foods with nutrient functions, foods with functional claims), quasi-drugs, medicines, etc. The oral composition according to this embodiment is preferably an oral composition that can display the favorable effects of compound (I) on the oral composition or its packaging, and is particularly preferably a health functional food (foods for specified health uses, foods with nutrient functions, foods with functional claims), quasi-drugs, or medicines.

[0042] When compound (I) is incorporated into an oral composition, the amount can be varied as appropriate, taking into account the intended use, symptoms, gender, etc., but it is preferable to adjust the amount of extract to be ingested by an adult so that the daily intake amount is approximately 1 to 1,000 mg, taking into account the general intake amount of the oral composition to be added. Furthermore, when the oral composition to be added is in the form of granules, tablets, or capsules, the amount of compound (I) to be added is not particularly limited as long as it is an amount that can prevent, treat, or ameliorate various infectious diseases, but is usually 0.100% to 100% by mass, and preferably 0.125% to 100% by mass, of the oral composition to be added.

[0043] When producing the oral composition of this embodiment, any auxiliary agent can be added, such as sugars such as dextrin and starch; proteins such as gelatin, soy protein and corn protein; amino acids such as alanine, glutamine and isoleucine; polysaccharides such as cellulose and gum arabic; and fats and oils such as soybean oil and medium-chain fatty acid triglycerides, to form an oral composition in any shape.

[0044] Oral compositions that can contain compound (I) are not particularly limited, and specific examples include, in addition to the foods and beverages exemplified below, tablets, capsules, drinks, oral preparations such as various toothpastes, mouthwashes, lozenges, oral pastes, gum massage creams, gargles, and mouth fresheners. When compound (I) is compounded in these oral compositions, commonly used auxiliary raw materials and additives can be used in combination.

[0045] In particular, by incorporating compound (I) or an antibacterial agent formulated from compound (I) into food and beverages, it is possible to inhibit the growth of bacteria in the food and beverages, thereby inhibiting contamination and deterioration (putrefaction and deterioration) of the food and beverages and maintaining their quality.

[0046]

[0039] The foods and beverages that can be blended with Compound (I) are not particularly limited, and specific examples thereof include beverages such as soft drinks, carbonated drinks, nutritional drinks, fruit drinks, and lactic acid drinks (including concentrated concentrates and powders for adjusting these beverages); frozen desserts such as ice cream, ice sherbet, and shaved ice; noodles such as soba noodles, udon noodles, vermicelli, gyoza wrappers, shumai wrappers, Chinese noodles, and instant noodles; sweets such as candy, chewing gum, candies, chewing gum, chocolate, candy tablets, snacks, biscuits, jelly, jam, cream, and baked goods; processed seafood and livestock foods such as kamaboko, ham, and sausage; dairy products such as processed milk and fermented milk; oils and fats and oil-based foods such as salad oil, tempura oil, margarine, mayonnaise, shortening, whipped cream, and dressing; condiments such as sauces and dressings; soups, stews, salads, side dishes, and pickles; and various other forms of health functional foods. When compound (I) is formulated into these oral compositions, commonly used auxiliary raw materials and additives can be used in combination.

[0047] When compound (I) is added to a food or beverage to inhibit bacterial growth, the amount of compound (I) added is not particularly limited as long as it is an amount that can inhibit bacterial growth, but is usually 0.100% by mass to 90.0% by mass, preferably 0.125% by mass to 50.0% by mass, and more preferably 30.0% by mass to 50.0% by mass relative to the food or beverage to which it is added.

[0048] The antibacterial agent, topical skin preparation, and oral composition including food and beverage of the present embodiment may be appropriately formulated with, for example, moisturizers, antioxidants, stabilizers, inorganic salts, pH adjusters, plant extracts, etc., depending on the form and purpose, within a range that does not inhibit the antibacterial effect.

[0049] The antibacterial agent, topical skin preparation, and oral composition including food and beverages of this embodiment are suitable for use in humans, but can also be applied to animals other than humans (e.g., mice, rats, hamsters, dogs, cats, cows, pigs, monkeys, etc.) as long as their respective effects are achieved. [Example]

[0050] The present invention will be specifically described below by showing test examples, but the present invention is not limited to the following examples. In these test examples, Compound (I) (Tokyo Chemical Industry Co., Ltd., 3-(4-Hydroxy-3-methoxyphenyl)propionic Acid, Sample 1) was used as the test sample.

[0051] [Test Example 1] Antibacterial activity test against Escherichia coli Sample 1 was dissolved and diluted with distilled water to prepare a 10% (w / v) sample solution, which was then sterilized. After sterilization, the sample solution was dispensed into a petri dish, and 10 mL of standard agar medium (manufactured by Nissui Pharmaceutical Co., Ltd.) was added to adjust the concentration of Sample 1 to that shown in Table 1. The added sample solution and standard agar medium were mixed in the petri dish, and the medium was then solidified.

[0052] A suspension of Escherichia coli was applied to the surface of the prepared medium and allowed to stand at 37° C. for 1 to 2 days, after which the presence or absence of colony formation was determined with the naked eye. The evaluation method is as follows. +: Colony formation was observed -: No colony formation was observed The results are shown in Table 1.

[0053] [Table 1]

[0054] [Test Example 2] Antibacterial activity test against Staphylococcus aureus Sample 1 was dissolved and diluted with distilled water to prepare a 10% (w / v) sample solution, which was then sterilized. After sterilization, the sample solution was dispensed into a petri dish, and 10 mL of standard agar medium (manufactured by Nissui Pharmaceutical Co., Ltd.) was added to make the concentration of Sample 1 as shown in Table 2. The added sample solution and standard agar medium were mixed in the petri dish, and the medium was then solidified.

[0055] A suspension of Staphylococcus aureus was applied to the surface of the prepared medium and allowed to stand at 37°C for 1 to 2 days, after which the presence or absence of colony formation was determined with the naked eye. The evaluation method is as follows. +: Colony formation was observed -: No colony formation was observed The results are shown in Table 2.

[0056] [Table 2]

[0057] [Test Example 3] Antibacterial activity test against Bacillus subtilis Sample 1 was dissolved and diluted with distilled water to prepare a 10% (w / v) sample solution, which was then sterilized. After sterilization, the sample solution was dispensed into a petri dish, and 10 mL of standard agar medium (manufactured by Nissui Pharmaceutical Co., Ltd.) was added to make the concentration of Sample 1 as shown in Table 3. The added sample solution and standard agar medium were mixed in the petri dish, and the medium was then solidified.

[0058] A suspension of Bacillus subtilis was applied to the surface of the prepared medium and allowed to stand at 37°C for 1 to 2 days, after which the presence or absence of colony formation was determined with the naked eye. The evaluation method is as follows. +: Colony formation was observed -: No colony formation was observed The results are shown in Table 3.

[0059] [Table 3]

[0060] As shown in Tables 1 to 3, it was confirmed that compound (I) (sample 1) exhibited excellent antibacterial activity.

[0061] [Formulation example 1] A cream having the following composition was prepared by a conventional method. Compound (I) 0.5g Sophora root extract 0.1g Scutellaria root extract 0.1g Liquid paraffin 5.0g White beeswax 4.0g Squalane 10.0g Cetanol 3.0g Lanolin 2.0g Stearic acid 1.0g Polyoxyethylene sorbitan oleate (20E.O.) 1.5g Glyceryl monostearate 3.0g Oil-soluble licorice extract 0.1g 1,3-butylene glycol 6.0g Methyl parahydroxybenzoate 1.5g Fragrance 0.1g Purified water Remainder (total amount is 100g)

[0062] [Formulation example 2] An emulsion was prepared in a conventional manner according to the following composition. Compound (I) 0.15g Jojoba oil 4.00g 1,3-butylene glycol 3.00g Arbutin 3.00g Polyoxyethylene cetyl ether (20E.O.) 2.50g 2.00g olive oil Squalane 2.00g Cetyl alcohol 2.00g Glyceryl monostearate 2.00g Polyoxyethylene sorbitan oleate (20E.O.) 2.00g Methyl parahydroxybenzoate 0.15g Stearyl glycyrrhetinate 0.10g Phellodendron bark extract 0.10g Dipotassium glycyrrhizinate 0.10g Ginkgo biloba extract 0.10g Conchiolin 0.10g Phellodendron bark extract 0.10g Chamomile extract 0.10g Fragrance 0.05g Purified water Remainder (total amount is 100g)

[0063] [Formulation example 3] A cosmetic essence having the following composition was prepared by a conventional method. Compound (I) 1.0g Chamomile extract 0.1g Carrot extract 0.1g Xanthan gum 0.3g Hydroxyethyl cellulose 0.1g Carboxyvinyl polymer 0.1g 1,3-butylene glycol 4.0g Dipotassium glycyrrhizinate 0.1g Glycerin 2.0g Potassium hydroxide 0.25g Fragrance 0.01g Preservative (methyl parahydroxybenzoate) 0.15g Ethanol 2.0g Purified water Remainder (total amount is 100g)

[0064] [Formulation example 4] Tablets having the following composition were prepared by a conventional method. Compound (I) 5.0 mg Dolomite (contains 20% calcium and 10% magnesium) 83.4mg Casein phosphopeptide 16.7mg Vitamin C 33.4mg Maltitol 136.8mg Collagen 12.7mg Sucrose fatty acid ester 12.0mg

[0065] [Formulation example 5] An oral liquid preparation having the following composition was prepared by a conventional method. <Composition in 1 ampoule (100 mL)> Compound (I) 0.5% by mass Sorbitol 12.0% by mass Sodium benzoate 0.1% by mass Fragrance 1.0% by mass Calcium sulfate 0.5% by mass Purified water remainder (100% by mass) [Industrial Applicability]

[0066] The antibacterial agent of the present invention can make a significant contribution to, for example, the prevention, treatment or amelioration of various infectious diseases, and the prevention of contamination and deterioration (spoilage and spoilage) of products.

Claims

1. An antibacterial agent characterized by comprising a compound represented by the following formula (I) as an active ingredient: 【Chemical 1】

2. A method for inhibiting bacterial growth in food and drink by adding a compound represented by the following formula (I) to the food and drink: 【Chemistry 2】

3. An antibacterial oral composition comprising a compound represented by the following formula (I): 【Chemistry 3】

4. An antibacterial skin preparation for external use, characterized by comprising a compound represented by the following formula (I): 【Chemistry 4】

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