JP5543655B1 - Beverages that stably contain useful ingredients in turmeric - Google Patents

Abstract

An object of the present invention is to provide a beverage that stably contains bisaclone by suppressing the decomposition of bisaclone and can retain the effect of bisaclone for a long time.
A beverage containing bisaclone and having a pH in the range of 3.1 or higher.
[Selection figure] None

Description

  The present invention relates to a beverage that stably contains bisaclone by suppressing the decomposition of bisaclone and can retain the effect of bisaclone for a long time.

  Turmeric is a plant belonging to the genus Turmeric belonging to the ginger family cultivated in tropical and subtropical regions around the world, mainly in Southeast Asia. Since it has a unique aroma and flavor, it has long been used as a spice and as a herbal medicine. Recently, curcumin contained in rhizomes has been reported to have various effects such as anti-inflammatory, anti-tumor, liver function improvement, and prevention of sickness, and turmeric is attracting attention as a health food.

  Today, focusing on the usefulness of turmeric, various foods and beverages containing turmeric ingredients have been developed. Among them, acidic drinks containing turmeric ingredients have a unique earthy odor and bitterness that are easy to drink and are popular. high.

  The present inventors have identified bisaclone as one of the active ingredients that turmeric brings so far, and confirmed that bisaclone has the effect of reducing blood ethanol concentration and the effect of suppressing hangover symptoms. doing.

  In addition, the present inventors have so far described that bisaclone is very unstable in an aqueous solution, particularly in an acidic aqueous solution, and when bisaclone is included in a beverage or the like, it immediately decomposes and its amount is remarkably reduced. It has been found that the desired effect of bisaclone is significantly attenuated. Therefore, the present inventors added a general decomposition inhibitor (such as an antioxidant or a chelating agent) of a compound to an aqueous solution containing bisaclone in order to suppress the decomposition of bisaclone in the aqueous solution. It was confirmed that the inhibitor could not sufficiently or at all inhibit the decomposition of bisaclone.

  Then, an object of this invention is to provide the drink which suppresses decomposition | disassembly of a bisaclone and contains bisaclone stably and can hold | maintain the effect which a bisaclone brings long.

As a result of diligent research to solve the above-mentioned problems, the present inventors can remarkably suppress the degradation rate of bisaclone in the beverage by setting the pH value of the beverage containing bisaclone to 3.1 or more. As a result, the present invention has been completed.
That is, the present invention has the following features.

[1] A beverage containing bisaclone and having a pH in the range of 3.1 or higher.
[2] The beverage according to [1], wherein bisaclone is derived from a turmeric extract.
[3] The beverage according to [1] or [2], containing 0.5 mg or more of bisaclone per oral intake.
[4] The beverage according to [1] or [2], containing 0.15 mg or more of bisaclone per oral intake.
[5] The beverage according to any one of [1] to [4], wherein the pH is in the range of 3.1 or more and 5 or less.
[6] The beverage according to any one of [1] to [4], having a pH of 3.1 or more and less than 4.0.
[7] A packaged beverage in which the beverage according to any one of [1] to [6] is placed.

[8] A method for improving the stability of bisaclone in a beverage, comprising a step of mixing a beverage material and bisaclone and adjusting the pH of the resulting mixture to a range of 3.1 or higher.
[9] The method according to [8], wherein bisaclone is derived from a turmeric extract.

[10] A method for producing a bisaclone-containing beverage comprising a step of mixing a beverage material and bisaclone and adjusting the pH of the resulting mixture to a range of 3.1 or higher.
[11] The method according to [10], wherein bisaclone is derived from a turmeric extract.
[12] The method according to [10] or [11], wherein the pH is adjusted to a range of 3.1 or more and 5 or less.
[13] The method according to [10] or [11], wherein the pH is adjusted to a range of 3.1 or more and less than 4.0.

  ADVANTAGE OF THE INVENTION According to this invention, the drink which suppresses decomposition | disassembly of a bisaclone and contains bisaclone stably and can hold | maintain the effect which a bisaclone brings long can be provided.

FIG. 1 shows the results of a storage test for bisaclone in beverages with different pH values. FIG. 2 shows the effect of suppressing hangover symptoms by ingesting bisaclone (0.15 mg).

本明細書におけるビサクロンとは上記化合物の光学異性体も包含する概念である。 In the present invention, bisaclone refers to a compound represented by the following formula or a salt thereof, and is a compound classified as a bisaborane-type sesquiterpene:

Bisaclone in the present specification is a concept including optical isomers of the above compounds.

  Bisacron may be extracted or purified from plant materials or artificially synthesized, but from the viewpoint of safety, it may be extracted or separated / purified from plant materials. preferable.

  The plant raw material is preferably a ginger family plant, particularly preferably Curcuma longa (Curcuma), Curcuma aromatica, Curcuma zedoaria, Curcuma phaeocaulis, Curcuma kwangsiensis, Curcuma wenyujin, Curcuma xanthorrhiza. Appropriate parts such as rhizomes of plant raw materials can be used as raw materials for the production of active ingredients in the original form, in a form cut into an appropriate size or shape, or in the form of a pulverized product. These raw materials may be appropriately dried.

  The extraction method of bisaclone from plant materials is not particularly limited. For example, water, ethanol, methanol, isopropanol, propylene glycol, diethyl ether, petroleum ether, hexane, acetone, acetonitrile, ethyl acetate, animal and vegetable oils and fats, or a mixture of two or more of these solvents can be dissolved. Solvent-soluble components are extracted from plant materials using a suitable solvent. As the extraction solvent, water and / or a hydrophilic extraction solvent, specifically, alcohol or water is preferable. Ethanol is preferred as the alcohol. The mixing ratio when using a mixture of alcohol and water is not particularly limited, but for example, the weight ratio is preferably in the range of 10:90 to 90:10, and more preferably in the range of 20:80 to 50:50.

  The obtained plant raw material extract is further subjected to purification means such as solvent fractionation, chromatography (column chromatography, high performance liquid chromatography (HPLC), etc.) and / or recrystallization, if necessary, and bisaclone May be separated or purified. For example, bisaclone obtains a methanol extract of turmeric as a plant raw material, elutes the extract with a silica gel column using methanol and chloroform, and more than curcuminoids (mixture of curcumin, demethoxycurcumin, bisdemethoxycurcumin) It can be separated or purified from the highly polar fraction using a preparative HPLC column.

  In the present invention, bisaclone may be in the form of an extract of plant raw material, or may be in a form separated / purified from the extract of plant raw material. That is, an extract of a plant material containing a predetermined amount of bisaclone can be blended in the bisaclone-containing beverage of the present invention.

  The bisaclone-containing beverage of the present invention can contain 0.15 mg or more, preferably 0.5 mg or more of bisaclone per oral intake. The “single oral intake” means the amount at which the bisaclone-containing beverage of the present invention is taken orally at once, or continuously at short time intervals (for example, 10 minutes or less, preferably 5 minutes or less). Refers to the total amount taken orally in multiple doses, for example 50 ml to 500 ml (typically 50 ml, 100 ml, 150 ml, 200 ml, 250 ml, 300 ml, 350 ml, 400 ml, 450 ml or 500 ml ml). Hereinafter, “single oral intake” is used in this sense. Further, in the present invention, “bisaclone 0.15 mg or more” and “bisaclone 0.5 mg or more” means that at least the production of the bisaclone-containing beverage of the present invention is completed, that is, the bisaclone-containing beverage of the present invention is at least a manufacturing plant as a finished product. Means “containing bisaclone 0.15 mg or more” and “bisaclone 0.5 mg or more”. The amount of bisaclone in the beverage was determined by high performance liquid chromatography using a solution obtained by mixing the beverage with ethyl acetate and centrifuging the supernatant to remove ethyl acetate from the supernatant and then dissolving it in acetonitrile. It can be determined by attaching to (HPLC).

  The pH of the bisaclone-containing beverage of the present invention has a value selected from the range of 3.1 or higher, preferably 3.2 or higher, more preferably 3.5 or higher, and still more preferably 3.7 or higher. In the present invention, the pH value refers to a value measured at a product temperature of 20 ° C.

  The lower limit of pH can be set based on the stability of bisaclone. That is, when the pH value of the beverage is smaller than 3.1, the stability of bisaclone contained in the beverage is not improved, and the decomposition of bisaclone contained in the beverage proceeds without being suppressed. On the other hand, when the pH value of the beverage is 3.1 or more, preferably 3.2 or more, more preferably 3.5 or more, and even more preferably 3.7 or more, the stability of bisaclone contained in the beverage is improved as the pH value increases. The decomposition of bisaclone contained in the beverage is suppressed. As a result, the beverage can maintain the action and effect of bisaclone for a long time. In the present invention, “the stability of bisaclone is improved” and “the decomposition of bisaclone is suppressed” means that the decomposition rate of bisaclone in a beverage is a decomposition rate of bisaclone in a beverage having a pH of less than 3.1. This means that it is milder than that, and it is not always necessary to completely stop the decomposition of bisaclone.

  The upper limit of the pH value is not particularly limited as long as the stability of bisaclone is improved, but is preferably 5 or less, more preferably less than 4. When the pH value of a beverage is higher than 5 and bisaclone is included in the form of an extract of plant material, the beverage has an unpleasant taste such as “bitterness” or “astringency” due to the extract of the plant material. There is a problem of being felt. Therefore, the upper limit of the pH value of the bisaclone-containing beverage of the present invention can be 5 or less. In addition, when the bisaclone-containing beverage of the present invention is in the form of a soft drink, the upper limit of the pH value can be less than pH 4.0. According to food-specific standards of the Food Sanitation Law, the method of sterilization and sterilization of soft drinks is greatly different at pH 4.0, and sterilization of those with a pH of less than 4.0 is centered at 65 ° C for 10 minutes. Whereas heating is required, sterilization of those having a pH of 4.0 or higher requires heating at a central temperature of 85 ° C. for 30 minutes. Therefore, it is preferable that the upper limit of the pH value is less than pH 4.0 because the load of the sterilization process can be reduced and the decomposition of bisaclone in the sterilization process can be reduced.

  The pH value of the bisaclone-containing beverage of the present invention can be adjusted by appropriately adjusting the amount of acidulant added. Examples of acidulants include those commonly used in beverage production, such as citric acid, malic acid, gluconic acid, tartaric acid, or salts thereof, and one or more of these Mixtures can be added.

  The bisaclone-containing beverage of the present invention is one in which the above components are contained in water, but one or more other components may be further contained.

  Examples of the “other components” include turmeric pigments. Turmeric pigment is obtained by extracting from the rhizome part of turmeric with hot ethanol, hot oil or propylene glycol, or room temperature to hot hexane or acetone. The pigment mainly contains curcumin. The amount of turmeric pigment in the bisaclone-containing beverage of the present invention is blended with an amount of turmeric pigment that makes curcumin 3 to 50 mg, more preferably 5 to 40 mg, particularly preferably 6 to 30 mg per single oral intake. It is good.

  Furthermore, examples of the “other ingredients” include sweeteners, thickeners, fragrances, antioxidants, vitamins and the like.

Examples of the sweetener include sugars such as fructose, glucose, and liquid sugar, and high-intensity sweeteners such as honey, sucralose, acesulfame potassium, thaumatin, and aspartame.
Thickeners include thickening polysaccharides such as gellan gum, xanthan gum, pectin, guar gum and the like.
Examples of the antioxidant include vitamin C, enzyme-treated rutin, tocopherol (vitamin E), catechin and the like.
Examples of vitamins include vitamin A, vitamin C, vitamin B1, vitamin B2, vitamin B6, vitamin E, niacin, inositol and the like.

  Sweeteners, thickeners, fragrances, antioxidants, vitamins, and the like can be appropriately blended in amounts within the range normally employed by those skilled in the art for beverages.

The bisaclone-containing beverage of the present invention can be a packaged beverage.
As a container for containing the bisaclone-containing beverage of the present invention, a container used as a beverage container can be used as appropriate. Although not limited, a container made of polyethylene terephthalate (PET), a so-called PET bottle, a metal can container, etc. Is mentioned. The form of the container is not particularly limited. The capacity of the container is not particularly limited, but for example 50 to 500 ml (typically 50 ml, 100 ml, 150 ml, 200 ml, 250 ml, 300 ml, 350 ml, 400 ml, 450 ml or 500 ml) ), Preferably 100-200 ml.
The means for accommodating the bisaclone-containing beverage of the present invention in a container is arbitrary.

  The bisaclone-containing beverage of the present invention is produced by mixing the bisaclone or the extract of the plant raw material containing bisaclone and the acidulant, if necessary, the turmeric pigment and other components as described above, and water as the balance. Can do. The amount of each component is as described above. As described above, a bisaclone-containing beverage having a pH value of 3.1 or more, preferably 3.2 or more, more preferably 3.5 or more suppresses the decomposition of bisaclone and can maintain the action / effect provided by bisaclone for a long time. , Adjusting the flavor of the plant material extract or turmeric pigment to obtain a beverage in which an unpleasant taste (bitterness, astringency, etc.) is reduced to such an extent that it does not cause discomfort or feels easy to drink it can.

  The bisaclone-containing beverage of the present invention can be used as a beverage having an action of reducing so-called hangover symptoms (especially head sensation, nausea, malaise, feeling of residual alcohol, stomach discomfort) upon waking up after alcohol consumption. .

I. Storage test The storage stability of bisaclone according to the pH value of bisaclone-containing beverages was tested as follows.
Examples 1-5 and Comparative Example 1 were used for the test.

  The turmeric pigment is obtained by extracting the rhizome part of turmeric (Curcuma longa) with acetone and evaporating the acetone under reduced pressure. This turmeric pigment contains 30% by weight of curcumin.

  Bisaclone was used in the form of turmeric extract. The turmeric extract is obtained by extracting the rhizome part of turmeric (Curcuma longa) using water. The amount of bisaclone in the turmeric extract is determined by high-performance liquid chromatography using a solution dissolved in acetonitrile after evaporating ethyl acetate from the supernatant obtained by mixing the extract with ethyl acetate and centrifuging. It was determined by attaching to a graphic (HPLC). HPLC was performed under the following conditions.

  The pH of each beverage was determined using citric acid and / or trisodium citrate. The pH value in the table refers to the value measured at a product temperature of 20 ° C.

  Each beverage is prepared by mixing ingredients other than water (powder raw material), adding and dissolving in water, adding the liquid raw material to make a 100 mL aqueous solution, and heating it to 93 ° C in a metal can did. Four bottles were prepared for each beverage.

  Measure the amount of bisaclone in each beverage after each test beverage was stored for 7 days, 14 days, and 30 days before heating at 93 ° C, after heating / packing at 93 ° C, and at 40 ° C. did. The amount of bisaclone in each beverage was determined by mixing the beverage with ethyl acetate and centrifuging the supernatant from the supernatant. It measured using the high performance liquid chromatography (HPLC) similarly to the measuring method of the amount of bisaclone. The bisaclone content of each sample was calculated as a percentage when the bisaclone content of the sample before heating at 93 ° C. was taken as 100%.

  The results are shown in FIG. It was shown that when the pH value of the beverage is 3.1 and 3.3 or higher, the decay rate (graph inclination) of the amount of bisaclone in the beverage is moderate as compared with the beverage having a pH value of 2.9. It is also shown that the rate of decay of the amount of bisaclone in the beverage (graph slope) is more gradual when the pH value of the beverage is 3.5 or higher than when the pH value of the beverage is 3.1 and 3.3. It was. That is, when the pH value of the beverage is 3.1 or more, it is confirmed that the decomposition of bisaclone in the beverage can be suppressed and the bisaclone can be stably contained, and when the pH value of the beverage is 3.5 or more, It was confirmed that the decomposition of bisaclone was further suppressed and bisaclone could be stably contained.

II. Sensory evaluation The influence of the pH value of a bisaclone-containing beverage on the ease of drinking was tested as follows.
In addition to Example 1 and Example 4 above, the following Examples 6-9 were used in the test.

Each test beverage was prepared in the same manner as the test beverage in “I. Preservation test” with the above composition.
Paneler IV ingested each test beverage and evaluated its ease of drinking on a five-point scale.
The sensory evaluation results of each test beverage are shown in the following table. When the pH value of the beverage was 6.0 or more, it was difficult to drink.

  From the above results, the amount of bisaclone in the beverage composition when the pH value of the beverage composition is 3.1 and 3.3 or more compared to the bisaclone in the beverage composition having a pH value of 2.9. It was shown that the decay rate (graph inclination) of the curve was slow. In addition, when the pH value of the beverage composition is 3.5 or more, the rate of decay of the amount of bisaclone in the beverage composition (graph slope) is more gradual than when the pH value of the beverage composition is 3.1 and 3.3. Was shown to be. That is, when the pH value of the beverage composition in the beverage composition is 3.1 or more, it is confirmed that the decay rate is suppressed and the storage stability is increased, and the pH value of the beverage composition is 3.5. In the case of the above, it was confirmed that the decay rate was further suppressed and the storage stability was increased.

  On the other hand, it was confirmed that the beverage composition containing bisaclone derived from the turmeric extract is difficult to drink as a beverage when the pH value is 6.0 or more.

III. Effect on hangover symptoms The effect of bisaclone on hangover symptoms was tested as follows.

1. Test beverage A test beverage containing bisaclone (Example A) is prepared by mixing ingredients other than water (powder raw material), adding and dissolving in water to make a 100 mL aqueous solution, and heating it to 93 ° C in a metal can. Made. Comparative Example a was prepared in the same manner as in Example A except that it was hot-packed and then stored at 40 ° C. for one week. The pH value of each test beverage was 3.1. By storing bisaclone in an acidic aqueous solution at 40 ° C., degradation is accelerated and bisaclone in the test beverage can be reduced.

  The turmeric pigment is obtained by extracting the rhizome part of turmeric (Curcuma longa) with acetone and evaporating the acetone under reduced pressure. This turmeric pigment contained 30% by weight of curcumin, and each test beverage contained 30 mg of curcumin.

  Bisaclone was used in the form of turmeric extract. That is, a turmeric extract containing a predetermined amount of bisaclone was blended in each test beverage. The turmeric extract is obtained by extracting the rhizome part of curcuma longa with water. The amount of bisaclone in each test beverage was determined by subjecting it to HPLC as described above.

  Example A and Comparative Example a had the following compositions. Bisaclone was 0.15 mg in Example A, and no bisaclone was detected in Comparative Example a.

2. Test subjects 13 test subjects were selected from men and women aged 20 to 65 who can drink alcoholic beverages. Those who could not drink alcoholic beverages (self-reported), those who were in the hospital, those who were taking medication, those who were ill with kidney / liver disease, and those with various types of hypersensitivity were excluded from the study subjects.

3. Test Method The hangover suppression effect was confirmed for each test beverage by the following procedure.
The following test was conducted twice in a week.

After ingesting Example A or Comparative Example a on the day before the test, alcohol was consumed while eating for 2 hours. The amount of alcohol and the menu and amount of food were managed for each individual so that the same amount of alcohol and food conditions were used in the two tests.
I went to bed after drinking, and took 7 hours as a guide. The amount of water that can be consumed after drinking was up to 200 mL. After getting up, a questionnaire about hangover was conducted.

The following matters were prohibited:
Ingestion of medicines and foods to improve hangover

4). Test schedule The test (first test) ingesting Example A as a test beverage was performed on five test subjects, and then the test (second test) was performed on Comparative Example a. Moreover, the said test (1st test) which ingests comparative example a as a test drink was performed with respect to the remaining 8 test subjects, and the said test (2nd test) was then performed about Example A. .

5. Evaluation items by questionnaire In the questionnaire, each test subject was asked to fill in the self-evaluation results by the VAS method for six items: headache, head sensation, nausea, malaise, feeling of remaining alcohol, and stomach discomfort.

  The VAS (Visual Analog Scale) method is a test that evaluates the degree of subjective symptoms by quantifying. In this method, the highest possible state is set to the right end and the lowest is set to the left end in a straight line. It is also widely used in clinical medicine for subjective evaluation, and is used especially for comparison of the condition before and after administration between subjects.

6). Test result For each evaluation item in the test ingesting each test beverage, an average value was obtained by summing up the VAS entry values of all the subjects. The results are shown in FIG.

  In Example A containing 0.15 mg of bisaclone, all the items of headache, head sensation, nausea, malaise, residual alcohol, and stomach discomfort, which are hangover symptoms, compared with Comparative Example a without bisaclone Suppression was observed, and in particular, it was confirmed that the effect of suppressing “head feeling” and “stomach discomfort” was significantly high.

  From the above results, it has been clarified that hangover symptoms can be suppressed by ingesting at least 0.15 mg of bisaclone.

Claims (12)

A heat-sterilized beverage containing 0.15 mg or more of bisaclone per oral intake and having a pH in the range exceeding 2.9 .   The beverage according to claim 1, wherein the bisaclone is derived from a turmeric extract.   The beverage according to claim 1 or 2, comprising 0.5 mg or more of bisaclone per one oral intake. The beverage according to any one of claims 1 to 3 , wherein the pH is in the range of more than 2.9 and 5 or less. The beverage according to any one of claims 1 to 3 , wherein the pH is in the range of more than 2.9 and less than 4.0. Container-packed drink in which the drink of any one of Claims 1-5 was put. A method for improving the stability of bisaclone in a beverage, comprising the step of mixing a beverage material and bisaclone and adjusting the pH of the resulting mixture to a range exceeding 2.9 . 8. The method of claim 7 , wherein the bisaclone is derived from a turmeric extract. A method for producing a bisaclone-containing beverage, comprising a step of mixing a beverage material and bisaclone and adjusting the pH of the resulting mixture to a range exceeding 2.9 . The method according to claim 9 , wherein the bisaclone is derived from a turmeric extract. The method according to claim 9 or 10 , wherein the pH is adjusted to a range of more than 2.9 and 5 or less. The method according to claim 9 or 10 , wherein the pH is adjusted to a range of more than 2.9 and less than 4.0.

Images