Food

Abstract

Provided is a food / beverage article containing one or more compounds represented by general formula (I): [in the formula R1 and R3 each independently represent a hydrogen atom or a C2-6 alkenyl group, R2 and R4 each independently represent a hydrogen atom or a C1-4 alkyl group, R5 and R7 each independently represent a hydrogen atom or a hydroxyl group, R6 represents a hydrogen atom or a C2-6 alkenyl group, X represents a coupling means, -CH2-, -CH=, or -C(=O)-, and Y represents -CH2-, -CH=, or -C(=O)-], the total concentration of the one or more compounds being 1 ppm or higher.

Description

[Technical field]

[0001] The present invention relates to a food or drink containing an oxygen-containing heterocyclic compound. [Background technology]

[0002] In recent years, due to the increasing health consciousness of consumers, food and drink products with low salt content and low mold resistance, such as reduced-salt soy sauce and straight soup, have been distributed. If lactic acid bacteria are mixed into such food and drink products with low mold resistance, spoilage will occur, and there is a problem that the quality of the product will be significantly impaired due to changes in pH caused by the production of lactic acid and decarbonation of amino acids, and deformation of the container due to the generation of carbon dioxide gas (for example, Non-Patent Document 1). In addition, if flat sour bacteria are mixed into food and drink products with low mold resistance, the contents will become sour due to the production of acid, and the quality of the product will be significantly impaired (for example, Non-Patent Document 2). [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] Journal of the Brewing Society of Japan, 2008, Vol. 103, No. 2, pp. 94-99 [Non-Patent Document 2] B. coagulans, Takeo Fujii (ed.), Fundamentals of Food Microbiology, Kodansha, 2015, p.15 Summary of the Invention [Problem to be solved by the invention]

[0004] As a means for suppressing the deterioration of the quality of food and drink due to contamination by lactic acid bacteria and / or flat sour bacteria, for example, the addition of synthetic preservatives, increasing the amount of salt and / or alcohol, and acidifying by lowering the pH can be mentioned. However, none of the above methods can be said to be desirable from the viewpoint of health consciousness, the viewpoint of the taste of food, etc.

[0005] An object of the present invention is to provide foods and beverages that can suppress deterioration in quality due to contamination with lactic acid bacteria and / or flat sour bacteria without relying on these methods. [Means for solving the problem]

[0006] As a result of extensive research to solve the above problems, the inventors have discovered that oxygen-containing heterocyclic compounds represented by the following general formula (I), such as lycoricidin, exhibit antibacterial activity against lactic acid bacteria and / or flat sour bacteria, and have completed the present invention based on this finding.

[0007] That is, the present invention relates to a compound represented by the following general formula (I): [ka] [In the formula, R 1 and R 3 are each independently a hydrogen atom or C 2-6 R represents an alkenyl group. 2 and R 4 are each independently a hydrogen atom or C 1-4 R represents an alkyl group. 5 and R 7 each independently represents a hydrogen atom or a hydroxyl group; R 6 is a hydrogen atom or C 2-6 represents an alkenyl group, X represents a bond, -CH2-, -CH=, or -C(=O)-, Y represents -CH2-, -CH=, or -C(=O)-, [ka] The bond represented by represents a single bond or a double bond. The present invention provides a food or drink that contains one or more compounds represented by the following formula (hereinafter also referred to as "compound (I)"), and has a total concentration of the compounds of 1 ppm or more. Since the food or drink of the present invention contains compound (I) at 1 ppm or more, it exhibits antibacterial activity against lactic acid bacteria and / or flat sour bacteria, and can suppress deterioration of the quality of the food or drink caused by contamination with lactic acid bacteria and / or flat sour bacteria.

[0008] Compound (I) is preferably at least one selected from the group consisting of lycoricidine, gancaonin I, 8-(γ,γ-dimethylallyl)-wighteone, glycicomarin, gliasperin C, glycyrin, isoangstone A and lycoallylcoumarin.

[0009] The food or drink of the present invention may be a liquid seasoning or a food. The liquid seasoning may be soy sauce, stock, soup, sauce, dressing, or cooking vinegar, and the food may be lightly pickled.

[0010] The present invention also provides an antibacterial agent against lactic acid bacteria and / or flat sour bacteria, which contains compound (I) as an active ingredient.

[0011] The present invention also provides a method for inhibiting the growth of lactic acid bacteria and / or flat sour bacteria in a food or drink, the method comprising adjusting the total concentration of compound (I) in the food or drink to 1 ppm or more. Effect of the Invention

[0012] According to the present invention, it is possible to provide a food or drink that can suppress deterioration in quality due to contamination with lactic acid bacteria and / or flat sour bacteria. Furthermore, according to the present invention, it is possible to provide a novel antibacterial agent against lactic acid bacteria and / or flat sour bacteria. Furthermore, according to the present invention, it is possible to provide a method for suppressing the proliferation of lactic acid bacteria and / or flat sour bacteria in a food or drink. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] Preferred embodiments of the present invention will be described in detail below, however, the present invention is not limited to the following embodiments.

[0014] The food and drink according to this embodiment comprises a compound represented by the following general formula (I): [ka] [In the formula, R 1 and R3 are each independently a hydrogen atom or C 3-6 R represents an alkenyl group. 2 and R 4 are each independently a hydrogen atom or C 1-4 R represents an alkyl group. 5 and R 7 each independently represents a hydrogen atom or a hydroxyl group; R 6 is a hydrogen atom or C 2-6 represents an alkenyl group, X represents a bond, -CH2-, -CH=, or -C(=O)-, and Y represents -CH2-, -CH=, or -C(=O)-, [ka] The bond represented by represents a single bond or a double bond. The compound represented by the formula (I) is contained in an amount of 1 ppm or more.

[0015] In this specification, "C 1-4 The term "alkyl group" refers to a straight or branched alkyl group having 1 to 4 carbon atoms. 1-4 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.

[0016] In this specification, "C 2-6 The term "alkenyl group" means a straight or branched alkenyl group having 2 to 6 carbon atoms. 2-6Examples of the alkenyl group include vinyl, propen-1-yl, propen-2-yl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 5-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 4-methyl-1-butenyl, 1-methyl- Examples of such alkyl groups include a 2-butenyl group, a 2-methyl-2-butenyl group, a 3-methyl-2-butenyl group, a 4-methyl-2-butenyl group, a 1-methyl-3-butenyl group, a 2-methyl-3-butenyl group, a 3-methyl-3-butenyl group, a 4-methyl-3-butenyl group, a 1,2-dimethyl-1-propenyl group, a 1,1-dimethyl-2-propenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, and a 6-hexenyl group.

[0017] In the above general formula (I), R 1 is preferably a hydrogen atom, a 3-methyl-2-butenyl group, or a 1,1-dimethyl-2-propenyl group.

[0018] In the above general formula (I), R 2 is preferably a hydrogen atom or a methyl group.

[0019] In the above general formula (I), R 3 is preferably a hydrogen atom or a 3-methyl-2-butenyl group.

[0020] In the above general formula (I), R 4 is preferably a hydrogen atom or a methyl group.

[0021] In the above general formula (I), R 6 is preferably a hydrogen atom or a 3-methyl-2-butenyl group.

[0022] Compound (I) may exist in the form of isomers such as stereoisomers and tautomers. These isomers are also included within the scope of the present invention.

[0023] Specific examples of compound (I) include lycoricidine, gancaonin I, 8-(γ,γ-dimethylallyl)-wighteone, glycycoumarin, gliasperin C, glycyrin, isoangstone A, and lycoallylcoumarin.

[0024] Lycoricidin is also known as 4-[(R)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)chroman-3-yl]-2-(3-methyl-2-butenyl)-1,3-benzenediol and has the following formula: [ka] It is a known compound represented by the formula:

[0025] Gankhaonin I is also known as 5-(3-methyl-2-butenyl)-2-(2,4-dihydroxyphenyl)-4,6-dimethoxybenzofuran and has the following formula: [ka] It is a known compound represented by the formula:

[0026] 8-(γ,γ-dimethylallyl)-wighteone is also known as 6,8-bis(3-methyl-2-butenyl)-3-(4-hydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one and has the following formula: [ka] It is a known compound represented by the formula:

[0027] Glycyclumarin, also known as 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, has the following formula: [ka] It is a known compound represented by the formula:

[0028] Gliasperin C is also known as (3R)-3β(2,4-dihydroxyphenyl)-5-methoxy-6-(3-methyl-2-butenyl)-3,4-dihydro-2H-1-benzopyran-7-ol and has the following formula: [ka] It is a known compound represented by the formula:

[0029] Glycyrrin is also known as 3-(2,4-dihydroxyphenyl)-5,7-dimethoxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one and has the following formula: [ka] It is a known compound represented by the formula:

[0030] Isoangstone A is also known as 3-[3,4-dihydroxy-5-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-chromen-4-one and has the following formula: [ka] It is a known compound represented by the formula:

[0031] Licoaryl coumarin is also known as 3-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8-(2-methyl-3-buten-2-yl)coumarin and has the following formula: [ka] It is a known compound represented by the formula:

[0032] Compound (I) may be synthesized by a method known to those skilled in the art, or may be a commercially available product. It is known that lycoricidin, gancaonin I, 8-(γ,γ-dimethylallyl)-wighteone, glycycoumarin, gliasperin C, glycyrin, isoangstone A, and licoryl coumarin are compounds contained in licorice oil extract. Therefore, in the food and drink according to this embodiment, the licorice oil extract containing compound (I) can be used as it is, or the compound (I) contained in the licorice oil extract can be isolated and used.

[0033] The food and drink according to the present embodiment may contain only one type of compound (I), or may contain two or more types. When the food and drink according to the present embodiment contains two or more types of compound (I), the concentration of compound (I) means the total concentration of each compound.

[0034] In the food and drink according to this embodiment, the lower limit of the concentration of compound (I) may be 1 ppm or more. This makes it possible to suppress the deterioration of the quality of the food and drink due to the contamination of lactic acid bacteria and / or flat sour bacteria. The concentration of compound (I) can be appropriately set in the range of 1 ppm or more depending on the purpose, salt concentration, alcohol concentration, pH, etc. of the food and drink, but from the viewpoint of further enhancing the antibacterial activity against lactic acid bacteria and / or flat sour bacteria, it may be, for example, 5 ppm or more, 10 ppm or more, 25 ppm or more, or 50 ppm or more.

[0035] In the food and drink according to this embodiment, the upper limit of the concentration of compound (I) is not particularly limited, but from the viewpoint of sufficient dissolution in the target food and drink, it may be, for example, 10,000 ppm or less.

[0036] The concentration of compound (I) can be measured, for example, by liquid chromatography-tandem mass spectrometry (LC / MS / MS).

[0037] The food and drink according to this embodiment may be any food and drink without any particular limitation, so long as it contains 1 ppm or more of compound (I). Examples of the food and drink according to this embodiment include liquid seasonings such as soy sauce, stock, soup, sauce, dressing, etc.; semi-solid seasonings such as miso paste and mayonnaise; pickled plums, pickles, side dishes, etc. The food and drink according to this embodiment is preferably a liquid seasoning or food, from the viewpoint of further suppressing the deterioration of quality due to contamination with lactic acid bacteria and / or flat sour bacteria. As liquid seasonings, soy sauce, stock, soup, sauce, dressing, or cooking vinegar are preferred. As food, lightly pickled pickles are preferred.

[0038] The salt concentration of the food and beverage according to this embodiment is not particularly limited, but from the viewpoint of enhancing antibacterial activity against lactic acid bacteria and / or flat sour bacteria without increasing the amount of salt, the salt concentration may be, for example, 12% (w / v) or less, 8% (w / v) or less, 4% (w / v) or less, or 0% (w / v) (salt-free).

[0039] The salt concentration can be measured by a known method such as potentiometric titration, Mohr's method, or atomic absorption spectrometry.

[0040] The alcohol concentration of the food and beverage according to this embodiment is not particularly limited, but from the viewpoint of enhancing antibacterial activity against lactic acid bacteria and / or flat sour bacteria without increasing the amount of alcohol, it may be, for example, 10% (v / v) or less, 5% (v / v) or less, or 0% (v / v).

[0041] The alcohol concentration can be measured, for example, by gas chromatography.

[0042] The pH of the food and beverage of this embodiment is not particularly limited, but from the viewpoint of providing a good taste to the food and beverage, it may be, for example, 3.0 or more, 4.0 or more, or 4.2 or more, and may be 7.0 or less, 6.0 or less, or 5.8 or less.

[0043] The food and beverage products according to this embodiment can be produced, for example, by adding a licorice oil extract containing compound (I) or compound (I) to a base food and beverage product (preferably a liquid seasoning or food product) to a concentration of 1 ppm or more, and, if necessary, diluting, concentrating (degassing, heating, drying, heating and degassing under reduced pressure, etc.), adding various additives, etc.

[0044] As confirmed in the following examples, compound (I) exhibits antibacterial activity against lactic acid bacteria and / or flat sour bacteria. Thus, as one embodiment of the present invention, an antibacterial agent against lactic acid bacteria and / or flat sour bacteria containing compound (I) as an active ingredient is provided.

[0045] The antibacterial agent according to this embodiment can be used against various harmful lactic acid bacteria (for example, lactic acid bacteria contained in the genera Lactobacillus, Streptococcus, Lactococcus, etc.) and flat sour bacteria (for example, Bacillus coagulans, etc.).

[0046] The antibacterial agent according to the present embodiment may be in any form, such as a solid (e.g., powder), liquid (e.g., solution or suspension), paste, etc. Also, it may be in any form, such as a powder, granules, tablets, capsules, liquid, suspension, syrup, etc. The above-mentioned various preparations can be prepared by mixing lycoricidin with additives (excipients, binders, lubricants, disintegrants, emulsifiers, surfactants, bases, solubilizers, suspending agents, etc.) and shaping as necessary.

[0047] The antibacterial agent according to the present embodiment can be added to any food or drink. Examples of such food or drink include liquid seasonings such as soy sauce, stock, broth, sauce, soup, dressing, and cooking vinegar; semi-solid seasonings such as miso paste and mayonnaise; pickled plums, pickles, and side dishes.

[0048] In addition, as confirmed in the following examples, compound (I) exhibits an effect of inhibiting the proliferation of lactic acid bacteria and / or flat sour bacteria. Thus, as one embodiment of the present invention, there is provided a method for inhibiting the proliferation of lactic acid bacteria and / or flat sour bacteria in a food or drink, comprising adjusting the total concentration of compound (I) in the food or drink to 1 ppm or more. EXAMPLES

[0049] The present invention will be described in more detail below with reference to examples, although the present invention is not limited to the following examples.

[0050] [Test Example 1: Antibacterial effect of edible plant extracts against lactic acid bacteria] (Preparation of Extract) The leaves, stems, or roots of commercially available edible plants (listed in Tables 1 and 2) were ground, and an equal amount of sterilized water was added to the ground material, stirred and mixed using a vortex, and left to stand at room temperature for 1 hour. To this mixture, ethanol was added in an amount three times that of the sterilized water, and extraction was carried out for 3 hours in an incubator at 50°C and 120 rpm (reciprocating shaking) to obtain a 75% ethanol extract. This extract was centrifuged at 3000 rpm for 10 minutes to obtain each extract. (Preparation of soy sauce) Commercially available reduced-salt soy sauce (Kikkoman Corporation) was diluted two-fold with sterilized water, adjusted to pH 4.8 with sodium hydroxide, and sterilized by heating to prepare reduced-salt soy sauce for testing. (Evaluation of antibacterial activity) In a test tube, add 11.3 mL of test reduced-salt soy sauce, 0.7 mL of each extract, and lactic acid bacteria (Lactobacillus rennini and Lactobacillus acidipiscis) to a final concentration of 10 5 The test tubes were added at a concentration of about cfu / mL, and the tubes were then sealed with a silicone stopper and allowed to stand at 30°C for anaerobic cultivation. As the lactic acid bacteria proliferate, a precipitate is formed in the bacterial cells. The precipitate formed at the bottom of the test tube was observed over time, and the number of days until a precipitate formed was compared between the control (75% ethanol aqueous solution was added instead of the extract) and the test in which each extract was added, to evaluate the antibacterial activity. The results are shown in Tables 1 and 2.

[0051] [Table 1]

[0052] [Table 2]

[0053] [Test Example 2: Sensory Evaluation] A trained panel member conducted a sensory evaluation based on the following criteria to determine whether the 19 extracts that showed antibacterial activity (a difference of 7 days or more until proliferation compared to the control) were suitable as ingredients in terms of aroma and taste. The results are shown in Table 3. In the table, 1 indicates seeds (seed coat) or fruits (fruit skin), 2 indicates leaves, stems, flowers or trunks, and 3 indicates roots. Evaluation criteria ○: Suitable as a material △: Not very suitable as a material ×: Clearly not suitable as a material -:Not rated

[0054] [Table 3]

[0055] From Table 3, the licorice powder extract was evaluated as the most suitable ingredient in the overall evaluation. In addition, the extract was added to commercially available reduced-salt soy sauce (manufactured by Kikkoman Corporation) at 100 ppm, and a sensory evaluation of the aroma and taste was carried out by five trained panelists. It was confirmed that the extract did not impair the flavor of the reduced-salt soy sauce and was suitable as an ingredient.

[0056] [Test Example 3: Identification of substances in licorice powder that have antibacterial activity against lactic acid bacteria] (Preparation of Extract) 1 kg of licorice powder (Nihon Funwa Yakuhin Co., Ltd.) was mixed with 5 L of chloroform (Kanto Chemical Special Grade) and stirred at room temperature for 2 hours, then filtered using pleated filter paper (5C). The filtrate was concentrated and dried using an evaporator to obtain 11 g of extract. (Fraction of substances with antibacterial activity) A column (3 L) was packed with silica gel (Disogel IR-60-40 / 63A Cat. 1002A), and about 11 g of the extract obtained above was dissolved in about 30 ml of chloroform. The extract was fractionated into 13 fractions (A to M in elution order) using the following solvents in order at a flow rate of 40 ml / min and monitored by TLC analysis at 220 nm. 1) Hexane (6L) 2) Hexane:Ethyl acetate = 4:1 (10L) 3) Hexane:Ethyl acetate = 3:1 (12L) 4) Hexane:Ethyl acetate = 2:1 (10L) (Evaluation of antibacterial activity of each fraction) Each fraction was added to BCP-added plate count agar (Nissui) at a concentration of 200 μg / mL, 67 μg / mL, 22 μg / mL, or 7 μg / mL. Lactic acid bacteria (Lactobacillus rennini and Lactobacillus acidipiscis; 10 6 ~10 7 A loopful of bacterial solution containing 100% lactic acid bacteria (cfu / mL) was applied to the sample and cultured anaerobically at 30°C for 8 days to evaluate the effect of inhibiting the proliferation of lactic acid bacteria. The evaluation was carried out by calculating the antibacterial unit of each fraction using the following formula (1), and calculating the contribution rate to the antibacterial action from the antibacterial unit of each fraction obtained using the following formula (2). The results are shown in Table 4. Formula (1): Antibacterial unit of each fraction = 100 / concentration at which antibacterial activity was exerted × fraction amount Equation (2) Contribution rate to antibacterial activity (%) = (antibacterial units of each fraction / antibacterial units of all fractions) x 100

[0057] [Table 4]

[0058] From Table 4, it was found that fractions F and I had strong antibacterial activity, and it was strongly suggested that fraction I in particular contained the main antibacterial component in licorice powder. Therefore, in order to identify the antibacterial component contained in fraction I, 13 C-NMR spectrum measurement was performed. As a result, the antibacterial component was estimated to be lycoricidin, and the standard sample (manufactured by ChemFaces) 13 A comparison of the C-NMR spectrum confirmed that the two were identical. In addition, time-of-flight mass spectrometry was performed on the antibacterial component, and the same [M+H] peak at m / z 425 as lycoricidin was found. + It was confirmed that the peak was

[0059] [Test Example 4: Antibacterial effect of lycoricidin against lactic acid bacteria in liquid seasoning (1)] (1) Manufacture of liquid seasonings (Soy sauce production) Commercially available whole soybean soy sauce (Kikkoman Corporation) was subjected to electrodialysis and then concentrated under reduced pressure to produce soy sauce with a salt concentration of 0% (w / v) and an alcohol concentration of 0% (v / v). Next, salt and / or alcohol were added to the soy sauce obtained above, followed by heat treatment to produce soy sauces with the salt and alcohol concentrations shown in Table 5 below. The pH of each soy sauce was 4.9 to 5.0.

[0060] [Table 5]

[0061] (Production of bonito stock) The bonito stock was produced using the ingredients shown in Table 6 below. Specifically, the components contained in bonito flakes were extracted with alcohol and water, and the resulting extract was mixed with sugar, salt and seasonings and heated to produce the bonito stock. The salt concentration of the resulting bonito stock was 0.2% (w / v), the alcohol concentration was 0.15% (v / v) and the pH was 6.1.

[0062] [Table 6]

[0063] (Sauce production) A sauce was produced using the ingredients shown in Table 7 below. Specifically, the sauce was produced by mixing and heating the dark soy sauce (Kikkoman Corporation), granulated sugar, potato starch, and water in the amounts shown in Table 7 below. The salt concentration of the obtained sauce was 5.3% (w / v), the alcohol concentration was 0.8% (v / v), and the pH was 5.0.

[0064] [Table 7]

[0065] (Soup production) The soup was made using the ingredients shown in Table 8 below. Specifically, the components contained in the dried bonito were extracted with water, and the resulting extract was mixed with dark soy sauce (Kikkoman Corporation), sugar and salt, and heated to make the soup. The salt concentration of the resulting soup was 3% (w / v), the alcohol concentration was 0.4% (v / v), and the pH was 5.5.

[0066] [Table 8]

[0067] (2) Evaluation of antibacterial activity Lycoricidin (ChemFaces) was added to each of the liquid seasonings produced in (1) above at concentrations of 1 ppm, 5 ppm, 10 ppm, 25 ppm, and 50 ppm, and then 10 mL of the lactic acid bacteria shown in Table 9 below was added. 6 ~10 7 Each was added so that the concentration was lycoricidin / mL, and the mixture was cultured at 30°C for 7 days. After culture, the number of lactic acid bacteria was measured using GAM agar medium "Nissui", and the antibacterial activity was evaluated by comparing the number of lactic acid bacteria in a control group, which was a liquid seasoning without added lycoricidin. The evaluation was performed using the following criteria. The results are shown in Tables 10 to 16. (Evaluation Criteria) A: The number of bacteria was reduced to less than 10% of the control group. B: The number of bacteria was reduced to 10% or more but less than 50% of the control group. C: The number of bacteria was reduced to 50% or more but less than 100% of the control group. D: The number of bacteria is the same as the control group

[0068] [Table 9]

[0069] [Table 10]

[0070] [Table 11]

[0071] [Table 12]

[0072] [Table 13]

[0073] [Table 14]

[0074] [Table 15]

[0075] [Table 16]

[0076] It was confirmed that lycoricidin exhibited antibacterial activity against various lactic acid bacteria under conditions of various salt and alcohol concentrations.

[0077] [Test Example 5: Antibacterial effect of lycoricidin against lactic acid bacteria in liquid seasoning (2)] (Soy sauce production) Commercially available whole soybean soy sauce (Kikkoman Corporation) was subjected to electrodialysis and then concentrated under reduced pressure to produce soy sauce with a salt concentration of 0% (w / v) and an alcohol concentration of 0% (v / v). Next, salt and / or alcohol were added to the soy sauce obtained above, and then hydrochloric acid or an aqueous sodium hydroxide solution was added to adjust the pH to the desired level. Sterile purified water was added, followed by heat treatment to produce soy sauces with the salt concentrations, alcohol concentrations, and pHs shown in Table 17 below. (Evaluation of antibacterial activity) Lycoricidin (ChemFaces) was added to each of the soy sauces obtained at concentrations of 1 ppm, 5 ppm, 10 ppm, 25 ppm, and 50 ppm, and then lactic acid bacteria (Lactobacillus rennini (DSM 20253)) was added at 10 ppm. 6 ~10 7 Each was added to the soy sauce so that the concentration was lycoricidin / mL, and the mixture was cultured at 30°C for 7 days. After the culture, the number of lactic acid bacteria was measured using GAM agar medium "Nissui", and the antibacterial activity was evaluated by comparing the number of lactic acid bacteria in the control group, which was soy sauce without added lycoricidin. The evaluation was performed using the same criteria as in Test Example 4. The results are shown in Tables 18 and 19.

[0078] [Table 17]

[0079] [Table 18]

[0080] [Table 19]

[0081] [Test Example 6: Antibacterial effect of oxygen-containing heterocyclic compounds against lactic acid bacteria in liquid seasonings (1)] (Soy sauce production) Commercially available whole soybean soy sauce (Kikkoman Corporation) was subjected to electrodialysis and then concentrated under reduced pressure to produce soy sauce with a salt concentration of 0% (w / v) and an alcohol concentration of 0% (v / v). Next, salt and alcohol were added to the soy sauce obtained above, and the mixture was heated to produce soy sauce with a salt concentration of 4% (w / v) and an alcohol concentration of 5% (v / v). (Evaluation of antibacterial activity) Each test substance shown in Table 20 was added to the soy sauce produced above at a concentration of 1 to 100 ppm, and then 100 ppm of lactic acid bacteria (Lactobacillus rennini (DSM 20253)) was added. 6 ~10 7 Each test substance was added to the soy sauce so that the concentration was 1 / mL, and the mixture was cultured at 30°C for 7 days. After culture, the number of lactic acid bacteria was measured using GAM agar medium "Nissui", and soy sauce without any test substance was used as a control group, and the antibacterial activity was evaluated by comparing the number of lactic acid bacteria in the control group. The evaluation was performed using the following criteria. The results are shown in Table 20. (Evaluation Criteria) A: The number of bacteria was reduced to less than 10% of the control group. B: The number of bacteria was reduced to 10% or more but less than 50% of the control group. C: The number of bacteria was reduced to 50% or more but less than 100% of the control group. D: The number of bacteria is the same as the control group -:Not rated

[0082] [Table 20]

[0083] It was also confirmed that oxygen-containing heterocyclic compounds other than lycoricidin have antibacterial activity similar to that of lycoricidin.

[0084] [Test Example 7: Antibacterial effect of oxygen-containing heterocyclic compounds against lactic acid bacteria in liquid seasonings (2)] (Evaluation of antibacterial activity) The soy sauce produced in Test Example 6 was added with each test substance shown in Table 21 at concentrations of 0.1 ppm, 0.5 ppm, 1 ppm, 5 ppm, 25 ppm, and 50 ppm, and then 10 mL of lactic acid bacteria (Lactobacillus fructivores (NBRC 13954)) was added. 4 ~10 5 Each test substance was added to the soy sauce so that the concentration was 1 / mL, and the mixture was cultured at 30°C for 7 days. After the culture, the number of lactic acid bacteria was measured using Difco Lactobacilli MRS Agar, and the antibacterial activity was evaluated by comparing the number of lactic acid bacteria in the control group, which was soy sauce without the addition of the test substance. The evaluation was performed using the following criteria. The results are shown in Table 21. (Evaluation Criteria) A: The number of bacteria was reduced to less than 10% of the control group. B: The number of bacteria was reduced to 10% or more but less than 50% of the control group. C: The number of bacteria was reduced to 50% or more but less than 100% of the control group. D: The number of bacteria is the same as the control group

[0085] [Table 21]

[0086] It was also confirmed that oxygen-containing heterocyclic compounds other than lycoricidin have antibacterial activity similar to that of lycoricidin.

[0087] [Test Example 8: Antibacterial effect of lycoricidin against flat sour bacteria in liquid seasoning] (Soup production) The soup was made using the ingredients shown in Table 22 below. Specifically, the components contained in the dried bonito were extracted with water, and the resulting extract was mixed with dark soy sauce (manufactured by Kikkoman Corporation), sugar and salt, and heated to make the soup. The salt concentration of the resulting soup was 3% (w / v), the alcohol concentration was 0.4% (v / v), and the pH was 5.2.

[0088] [Table 22]

[0089] (Evaluation of antibacterial activity) Lycoricidin (ChemFaces) was added to the above-produced soup at concentrations of 1 ppm, 5 ppm, 10 ppm, 25 ppm, and 50 ppm, and then flat sour bacteria (Bacillus coagulans (IFO12714)) were added at 10 ppm. 4 ~10 5 Each was added at a concentration of lycoricidine / mL and cultured at 45°C for 7 days. The soup without lycoricidine was used as a control, and the antibacterial activity was evaluated by comparing the pH. The evaluation was performed according to the following criteria. The results are shown in Table 23. (Evaluation Criteria) A: No change in pH compared to the control B: pH is decreased compared to the control

[0090] [Table 23]

[0091] Lycoricidin was confirmed to exhibit antibacterial activity against flat sour bacteria.

[0092] [Test Example 9: Antibacterial effect of lycoricidin against lactic acid bacteria in liquid seasonings and foods (3)] (1) Manufacture of liquid seasonings and foods (Production of liquid dressings) A liquid dressing was produced using the ingredients shown in Table 24 below. Specifically, the liquid dressing was produced by mixing and heating the amounts of dark soy sauce (Kikkoman Corporation), vinegar, mirin, granulated sugar, kelp stock, and water shown in Table 24 below. The salt concentration of the obtained liquid dressing was 2.6% (w / v), the alcohol concentration was 0.8% (v / v), and the pH was 4.2.

[0093] [Table 24]

[0094] (Production of lightly pickled vegetables) A seasoning liquid for light pickles was produced using the ingredients shown in Table 25 below. Specifically, the amounts of light soy sauce (Kikkoman Corporation), vinegar, corn syrup, isomerized sugar, salt, granulated sugar, monosodium glutamate (MSG), lemon juice, kelp stock, and water shown in Table 25 below were mixed and heated to produce a seasoning liquid for light pickles. Chinese cabbage was thoroughly soaked in this seasoning liquid for light pickles to produce light pickles. The salt concentration of the obtained seasoning liquid for light pickles was 3.1% (w / v), the alcohol concentration was 0.01% (v / v), and the pH was 4.4.

[0095] [Table 25]

[0096] (Production of cooking vinegar) Cooking vinegar was produced using the ingredients shown in Table 26 below. Specifically, the amounts of vinegar, salt, granulated sugar, lemon juice, monosodium glutamate (MSG) and water shown in Table 26 below were mixed and heated to produce cooking vinegar. The salt concentration of the resulting cooking vinegar was 1.5% (w / v), the alcohol concentration was 0% (v / v), and the pH was 3.8.

[0097] [Table 26]

[0098] (2) Evaluation of antibacterial activity Lycoricidin was added to the liquid dressing, light pickle and cooking vinegar produced above at concentrations of 1 ppm, 5 ppm, 10 ppm, 25 ppm and 50 ppm, and then lactic acid bacteria (Lactobacillus rennini (DSM 20253)) was added at 10 ppm. 6 ~10 7Lycoricidin was added to each of the ingredients so that the concentration of lycoricidin per mL was reached, and the liquid dressing and light pickles were cultured at 30°C for 7 days, while the vinegared soy sauce was cultured at 30°C for 3 days. After culture, the number of lactic acid bacteria was measured using GAM agar medium "Nissui", and the liquid dressing, light pickles, and vinegared soy sauce to which lycoricidin had not been added were used as controls, and the antibacterial activity was evaluated by comparing the number of lactic acid bacteria in the control groups. The evaluation was performed using the same criteria as in Test Example 4. The results are shown in Table 27. (Evaluation Criteria) A: The number of bacteria was reduced to less than 10% of the control group. B: The number of bacteria was reduced to 10% or more but less than 50% of the control group. C: The number of bacteria was reduced to 50% or more but less than 100% of the control group. D: The number of bacteria is the same as the control group

[0099] [Table 27]

[0100] Lycoricidin has been confirmed to exhibit antibacterial activity against lactic acid bacteria in various liquid seasonings and foods.

Claims

1. The liquid seasoning is inhibited from deteriorating in quality due to lactic acid bacteria contamination, and contains one or more compounds selected from the group consisting of lycoricidin, 8-(γ,γ-dimethylallyl)-wigtheone, gliasperin C, isoangstone A and licorylcoumarin as active ingredients, and the total concentration of the compounds is 5 ppm or more.

2. The liquid seasoning according to claim 1 , which is soy sauce, stock, broth, sauce, dressing or cooking vinegar.

3. 3. The liquid seasoning according to claim 1 or 2, having a salt concentration of 12% (w / v) or less and an alcohol concentration of 10% (v / v) or less.

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