JP2007119411A - Method for stabilizing capillin - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for suppressing declining in antibacterial/antifungal effects that is caused by capillin volatilization in antibacterial/antifungal objects while retaining high antimicrobial effects inherent in capillin. <P>SOLUTION: In using capillin in food, cosmetics or general industrial products, etc. for the purpose of giving them antibacterial/antifungal effects, capillin and a cyclodextrin or its derivative are made to coexist in such objects, thereby enabling capilling decrease attributable to capillin volatilization in these objects to be suppressed without impairing high antimicrobial effects inherent in capillin, thus providing the method for maintaining its antibacterial/antifungal effects over a long period. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to the stabilization of capillin with cyclodextrins.

  Synthetic preservatives such as benzoic acid, sorbic acid, and salts thereof are used as synthetic preservatives for foods and the like because they have bacteriostatic action and growth / rotation inhibiting action. Synthetic preservatives used in foods have their use standards set by the Food Sanitation Law to ensure safety, and there are thorough standards for safety. There is a remarkable movement away from preservatives, and accordingly, additives derived from natural products for the purpose of preservation and improvement of shelf life are demanded.

  As a kind of preservatives derived from natural products, the wormwood extract containing capilin described in Non-Patent Document 1 and Patent Document 1 is known. Capillin is a compound having the following structural formula.

“Additional List of Items Listed in Existing Additives List”, 1999, p. 162 JP 2003-265152 A JP 2003-238310 A

  Non-Patent Document 1 discloses that the Artemisia extract has antibacterial and antifungal properties, and the active ingredient of antibacterial and antifungal properties is capilin.

  On the other hand, Patent Document 1 discloses a capilin-containing extract from which components having a specific odor are removed by extracting a capilin-containing extract from pearl millet and further distilling the extract under reduced pressure under high vacuum. Since this extract contains capilin, it will exhibit antibacterial and antifungal properties.

  In order for the antibacterial and antifungal compound to fully exhibit its antibacterial and antifungal action, it is necessary that the concentration of the antibacterial and antifungal compound be equal to or higher than the minimum growth inhibitory concentration (MIC value). On the other hand, when the concentration of the antibacterial and antifungal compound is less than the MIC value, the higher the concentration, the higher the antibacterial and antifungal activity. This is no exception for Capilin. That is, it is a condition for exhibiting good antibacterial and antifungal properties that capilin is stably present in the antibacterial and antifungal target without decreasing.

  According to the capilin-containing extract disclosed in Patent Document 1, no measures for stabilizing capilin are taken. Since capilin is a volatile substance, when a capilin-containing extract is added to an antibacterial antifungal object, it will be reduced by volatilization. When microorganisms or the like are mixed into the antibacterial and antifungal target after the reduction of capillin, the antibacterial and antifungal action is reduced because the concentration of capillin is reduced. As a result, the period for maintaining antibacterial and antifungal properties is not sufficient. In order to prolong the period of the antibacterial and antifungal properties of capillin, it may be possible to solve the problem by increasing the content of kabilin in the antibacterial and antifungal target. Will be accompanied by deterioration of the flavor of food and food.

  In view of the circumstances as described above, an object of the present invention is to provide a method for suppressing a decrease in capilin due to volatilization while having excellent antibacterial properties of capilin.

  As a result of intensive research to solve the above problems, the present inventors have suppressed the decrease in capillin without impairing the excellent antibacterial properties of capillin by using cyclodextrin or a derivative thereof together with capilin. As a result, the present invention has been completed.

  According to the present invention, a method for suppressing the decrease in capillin can be provided without impairing the antibacterial properties of capillin, and thus the method can exhibit antibacterial properties for a long period of time.

The present invention is described in detail below. The capilin used in the present invention is an essential oil component contained in the Asteraceae capillaris chumb., Which is used as a herbal medicine. Capillin can be extracted from the above-ground part of the sagebrush, and as extraction solvents, lower alcohols such as methanol, ethanol and isopropyl alcohol, polyhydric alcohols such as glycerin, propylene glycol and 1,3-butylene glycol, acetone, methyl ethyl ketone and the like Organic solvents such as ketones, hydrocarbons such as hexane, cyclohexane and petroleum ether, ethers such as methyl ether, and a solvent miscible with water can be used as a mixed solvent with water. It can be used as it is if it is an extract that uses an extraction solvent that does not interfere with the intended use, but it may be necessary to add a large amount of capilin, so the solvent may be completely distilled off or moderately removed. It is desirable to use it after concentration. At that time, in the case of an extract with a lower alcohol or hydrous alcohol, capyrin distills azeotropically when concentrated under normal pressure or reduced pressure. In order to prevent this, glycerin, 1,3-butylene glycol, It is preferable to add and concentrate propylene glycol, glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, medium chain fatty acid triglyceride, various animal and vegetable oils and the like. Moreover, you may use the essential oil component containing the capilin etc. which were obtained by steam distillation from Kawara mugwort as it is. Furthermore, the essential oil component obtained by solvent extraction or steam distillation may be used after separating or increasing the content of capyline by column chromatography, high performance liquid chromatography or the like. In addition, capilin synthesized by chemical synthesis may be used.

The cyclodextrin used in the present invention is not particularly limited, and a commercially available product may be used as it is, or may be produced by a known method such as causing amylase derived from Bacillus macerans to act on starch. In the present specification, cyclodextrin includes α-, β- and γ-cyclodextrins composed of 6, 7 and 8 cyclic α- (1 → 4) linked D-glucopyranose units, respectively. In addition, for example, these chemically modified products such as methyl, propyl, monoacetyl, triacetyl, monochlorotriazinyl, glucosyl-α-cyclodextrin, maltosyl-α-cyclodextrin, etc. These branched cyclodextrins are also included.

The amount of capillin to be stabilized in the present invention can be arbitrarily set according to the amount added to the object imparting antibacterial properties, and is not particularly limited. Capillin is added in an amount sufficient to contain 0.1 μg / g or more, preferably 0.2 to 100 μg / g, more preferably 0.5 to 50 μg / g of an object to be given antibacterial properties such as industrial products. As shown in Patent Document 2, the minimum growth inhibitory concentration on the medium for capillin against Aspergillus niger is 1 ppm (μg / g). In the case where the amount of the nutrient component is small or the water activity is low, antibacterial and antifungal properties are exhibited at capillin of 0.1 ppm or more. Moreover, even if it mix | blends 100 ppm or more of capilin with respect to the object which provides antimicrobial property, an effect does not change and it is not economical.

  On the other hand, the amount of cyclodextrin used in the present invention can be arbitrarily set according to the amount of capilin to be stabilized or the stability of capilin in the antibacterial anti-antifungal object, and further the purity of cyclodextrin, Although not limited, higher stability can be shown by using together 1 to 20000 weight part with respect to 1 weight part of capillin, Preferably 15 to 5000 weight part is used together. Addition of 20,000 parts or more does not increase the effect and is not economical.

  Here, capillin and cyclodextrin may be added separately to the object, or those mixed as a preparation may be used. Furthermore, after mixing both, it is good also as a powdery clathrate by a well-known method, such as making it dry by spray drying etc.

  Moreover, although the present invention uses cyclodextrin as an essential component for the stabilization of capilin, other various components can be optionally blended depending on the purpose of use. Ingredients that can be optionally blended when used in foods are not particularly limited as long as they are food materials and food additives. Water, polyhydric alcohols such as glycerin, sugar alcohols such as sorbitol, medium chain fatty acids Oils such as triglycerides and various animal and vegetable oils as solvents, food emulsifiers such as glycerin fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters, and lecithin as solubilizers, and also dextrin and soluble Starch etc. can be illustrated as an excipient. In addition, the components that can be optionally blended when used in cosmetics are not particularly limited as long as they are components that are usually used in cosmetics. Solvents include water, polyhydric alcohols such as glycerin, and sorbitol. Examples include sugar alcohols such as sugars, hydrocarbons such as liquid paraffin and squalane, ester oils such as cetyl isooctanoate and octyldodecyl myristate, oils such as medium chain fatty acid triglycerides and various animal and vegetable oils, etc. Examples of the agent include surfactants such as polyglycerin fatty acid ester, sucrose fatty acid ester, polyoxyethylene hydrogenated castor oil, and polyoxyethylene alkyl ether. Also in general industrial products, any components other than components that adversely affect the products can be blended arbitrarily.

  The present invention also provides basic foods such as various foods such as breads, confectionery, noodles, dairy products, side dishes and pickles, beverages such as soft drinks, fruit drinks and milk drinks, lotions, emulsions and creams. , Hand creams, body cosmetics such as body lotions, skin cleansers such as face wash, body shampoo, hair shampoos, rinses, treatments, hair styling agents, hair color cosmetics, foundations, Antibacterial in general industrial products such as eyeliner, mascara, lipstick and other make-up products, oral cosmetics such as toothpaste, dishwashing agent, water-based ink for inkjet, water-based ink for ballpoint pen, water-based paint, etc. It can be applied to any product that requires the addition of a substance having the property to prevent the product itself from being spoiled. Further, the present invention is also applicable to antifungal agents that spray or apply to bathroom tile joints and the like to prevent mold generation, and cleaning and disinfecting agents such as fruits and vegetables.

  EXAMPLES Hereinafter, although this invention is shown concretely based on an Example, this invention is not limited to these.

<Production Example 1>
2.5 kg of 99.5% ethanol was added to 500 g of dried ears of Kawaramugi, soaked at 40 ° C. for 20 hours, extracted, and then filtered to obtain an extract. Ethanol was distilled off to make the total amount 500 g, and then 500 g of purified water was added and stirred well. Liquid-liquid extraction was performed by adding 400 ml of n-hexane. This extraction was repeated twice, and the extracted n-hexane extract was concentrated to obtain 8.6 g of a paste. Capillin was fractionated from this paste by preparative high performance liquid chromatography under the following conditions. After extraction with hexane, hexane was distilled off to obtain 0.71 g of capilin. In addition, it was confirmed by GC-MS that this was capilin.
Preparative high performance liquid chromatography LC-8A system manufactured by Shimadzu Corporation Column: STR ODS-2 manufactured by Shinwa Kako Co., Ltd.
20.0 mmI. D. × 250mmL
Mobile phase: 80% methanol, 15 mL / min
Detector: UV280nm
Sample: Dilute to 4.5% with mobile phase, inject 5.0 mL each time

<Production Example 2>
2.5 kg of 99.5% ethanol is added to 500 g of dried peach tree ears, soaked at 40 ° C. for 20 hours for extraction, filtered, and the residue is washed with 2.0 kg of 99.5% ethanol to wash it. An extract was obtained. Ethanol was distilled off to make the total amount 400 g, and then 500 g of purified water was added and stirred well. Liquid-liquid extraction was performed by adding 400 mL of n-hexane. This extraction was repeated twice, and the extracted n-hexane extract was concentrated to obtain 8.6 g of a paste.

<Test Example 1>
Using the purified capilin described in Production Examples 1 and 2 and the extract of Kawamomogi, aqueous solutions of Examples 1 to 6 and Comparative Example 1 described in Table 1 were prepared. Table 1 shows the stability of capillin over time in a 40 ° C. storage state of the present composition. The capillin concentration is determined by high performance liquid chromatography, and the residual rate is a value calculated from the residual rate (%) = after 14 days concentration / initial concentration × 100.

表１から分かるように、シクロデキストリンを配合していない比較例１に対し、各種シクロデキストリンを配合した実施例１〜６については、いずれもカピリンの残存率が上昇していることが確認できる。また、この中でも特にα−シクロデキストリンについては安定性が著しく向上していることがわかる。

As can be seen from Table 1, it can be confirmed that in Examples 1 to 6 in which various cyclodextrins were blended with respect to Comparative Example 1 in which no cyclodextrin was blended, the remaining ratio of capillin was increased. Further, among these, it can be seen that the stability of α-cyclodextrin is particularly improved.

<Test Example 2>
About the aqueous solution of Examples 1-6 and the comparative example 1, the antibacterial property with respect to black Aspergillus niger ( Aspergillus niger ) was confirmed. 20 mL each of the aqueous solutions of Examples 1 to 6 and Comparative Example 1 immediately after preparation and after storage at 40 ° C. for 14 days were placed in a sterilized test tube (28 mmφ × 200 mmH). After inoculation to be about 02 × 10 ² cfu / mL, it was stoppered. Antibacterial properties were evaluated from the appearance after standing at room temperature for 7 days.
・ Evaluation criteria of antibacterial test ○: Mycelial growth cannot be confirmed after 7 days.
Δ: Slight growth of mycelium can be confirmed after 7 days.
X: Growth of hyphae can be confirmed after 7 days.
The results of the antibacterial test are shown in Table 1.

As specifically described in Examples and Test Examples, the present invention greatly improves the stability of kabilin in antibacterial and antifungal objects, contributing to the maintenance of long-term antibacterial properties in antibacterial and antifungal objects. There is a lot to do.

Claims (3)

  A method for stabilizing capillin characterized in that cyclodextrin is allowed to coexist in the system together with capilin.   2. The method according to claim 1, wherein the cyclodextrin is α-cyclodextrin or a derivative thereof.   3. The method for stabilizing capillin according to claim 1, wherein capillin and cyclodextrin are allowed to coexist in a weight ratio of 1:15 to 1: 5000.