Gingerol-containing beverages

Abstract

In beverages containing gingerol, the photodegradation of gingerol is suppressed. [Solution] Copper ions are added to a beverage containing gingerol, and the ratio of the copper ion content (B: ppm) to the gingerol content (A: ppm) (B / A) is adjusted to 0.00004 or higher.

Description

Technical Field

[0001] The present invention relates to a beverage containing gingerol, a method for producing the same, a method for suppressing the decomposition of gingerol, and the like.

Background Art

[0002] Ginger contains gingerol and the like, which have the effect of promoting blood circulation and warming the body, and is a very familiar plant that is widely used in diet and traditional Chinese medicine prescriptions. Gingerol has been reported to have strong activity of inhibiting the aggregation of tau protein (Patent Document 1) and is expected to be promising for the prevention of Alzheimer's dementia (Non-Patent Document 1). Therefore, the development of beverages containing gingerol at a high concentration is required.

[0003] On the other hand, since the α,β-unsaturated carbonyl group contained in the structure of gingerol is epoxidized and isomerized by light irradiation, gingerol is known to have the property of being photodecomposed in solution (Non-Patent Documents 2 and 3). In this regard, it has been reported that the discoloration of chlorophyll can be suppressed by adjusting the content ratio of copper ions and zinc ions in a beverage containing chlorophyll (Patent Document 2). Also, in the production of green juice beverages, it has been reported that a fresh green color of the green juice beverage can be maintained by adding metal ions, adjusting the pH to a certain range, and then sterilizing (Patent Document 3). However, while gingerol is a kind of polyphenol, chlorophyll has a structure in which phytol (long-chain alcohol) is ester-bonded to tetrapyrrole, and the chemical structures of the two are completely different. Therefore, the findings obtained for chlorophyll cannot be applied to gingerol. And, a method for suppressing the photodecomposition of gingerol has not been reported so far.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

[0005] [Non-Patent Document 1] Clinical Neurology 2014;54:1178-1180 [Non-Patent Document 2] Catalysts 2017;7:337 [Non-Patent Document 3] J. Org. Chem. 2018;83:13051-13062 [Disclosure of the Invention] [Problems that the invention aims to solve]

[0006] The object of the present invention is to suppress the photodegradation of gingerol in beverages containing gingerol. [Means for solving the problem]

[0007] To solve the above problems, the inventors conducted diligent research using various metal ions and found that by adding copper ions to a beverage containing gingerol and adjusting the ratio of copper ion content (B:ppm) to gingerol content (A:ppm) to gingerol content (B / A) to 0.00004 or higher, the photodegradation of gingerol can be suppressed. Furthermore, they found that the photodegradation-suppressing effect of gingerol can be further improved by adjusting the gingerol content and copper ion content to a predetermined range.

[0008] In other words, the present invention relates to, but is not limited to, the following. (1) A beverage containing gingerol and copper ions, The beverage wherein the ratio of the copper ion content (B: ppm) to the gingerol content (A: ppm) (B / A) is 0.00004 or more. (2) The beverage described in (1), having a pH of 8.0 or less. (3) The beverage described in (1) or (2), having a copper ion content of 0.001 to 10 ppm. (4) A beverage as described in any of (1) to (3), having a gingerol content of 0.1 to 300 ppm. (5) A beverage as described in any of (1) to (4), which contains copper ions as copper salts or copper yeast. (6) The beverage according to (5), wherein the copper salts are copper sulfate or copper gluconate. (7) A beverage in a clear container, as described in any of (1) to (6). (8) A method for producing a beverage containing gingerol, The process includes adding gingerol and copper ions to the beverage. The method, wherein the ratio (B / A) of the copper ion content (B: ppm) to the gingerol content (A: ppm) in the beverage is 0.00004 or more. (9) A method for suppressing the decomposition of gingerol in a beverage, The process includes adding gingerol and copper ions to the beverage. The method, wherein the ratio (B / A) of the copper ion content (B: ppm) to the gingerol content (A: ppm) in the beverage is 0.00004 or more. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a beverage containing gingerol in which the photodegradation of gingerol is suppressed. In other words, the present invention makes it possible to provide a beverage in which gingerol is stably maintained for a long period of time. [Modes for carrying out the invention]

[0010] Unless otherwise specified, "ppm" as used herein refers to ppm in weight / volume (w / v).

[0011] 1. Beverages containing gingerol In one embodiment, the present invention relates to a beverage containing gingerol and copper ions, wherein the ratio of the copper ion content (B: ppm) to the gingerol content (A: ppm) (B / A) is 0.00004 or more. By adding copper ions to a beverage containing gingerol and adjusting the ratio of the copper ion content (B: ppm) to the gingerol content (A: ppm) (B / A) to 0.00004 or more, the photodegradation of gingerol can be suppressed.

[0012] (1) Gingerol Ginger contains pungent components such as gingerol and shogaol, but the majority of the pungent component is gingerol, with only a very small amount of shogaol. On the other hand, shogaol has the effect of promoting blood circulation and warming the body, as well as having strong tau protein aggregation inhibitory activity (Patent Document 1), and is therefore expected to be promising for the prevention of Alzheimer's disease (Non-Patent Document 1). Gingerol includes 6-gingerol, 8-gingerol, 10-gingerol, etc., with 6-gingerol being the main component. Shogaol is produced when each gingerol is converted to 6-shogaol, 8-shogaol, 10-shogaol, etc. In one embodiment, "shogaol" in this specification may be a general term for 6-shogaol, 8-shogaol, and 10-shogaol.

[0013] The upper limit of the content of gingerol contained in the beverage of the present invention is not particularly limited, but for example, it is 300 ppm, 250 ppm, 200 ppm, 150 ppm, 100 ppm, 50 ppm, 45 ppm, 25 ppm, or 20 ppm. Also, the lower limit of the content of gingerol contained in the beverage of the present invention is not particularly limited, but for example, it is 0.1 ppm, 0.5 ppm, 1 ppm, 2 ppm, 3 ppm, or 4 ppm. Further, the content range of gingerol contained in the beverage of the present invention is not particularly limited, but for example, it is 0.1 to 300 ppm, 0.5 to 250 ppm, 1 to 200 ppm, 2 to 150 ppm, 2 to 100 ppm, 3 to 50 ppm, 3 to 45 ppm, 4 to 25 ppm, or 4 to 20 ppm. By setting the content within this range, the photodegradation inhibitory effect of gingerol can be further improved by adding a certain amount of copper ions.

[0014] When manufacturing the beverage of the present invention, purified or isolated gingerol may be used, a raw material containing gingerol may be used, or both of them may be used. Examples of the raw material containing gingerol include Zingiberaceae plants such as ginger and flower ginger, and their extracts. When using such a raw material in the present invention, such a raw material may be used alone or in combination of two or more.

[0015] The content of gingerol can be measured by ion exchange chromatography, size exclusion chromatography, HPLC method, LC-MS method, LC-MS / MS method, etc., but it is preferably measured by the HPLC method.

[0016] (2) Copper ions The upper limit of the copper ion content in the beverage of the present invention is not particularly limited, but for example, it is 10 ppm, 5 ppm, 1 ppm, 0.5 ppm, or 0.25 ppm. The lower limit of the copper ion content in the beverage of the present invention is not particularly limited, but for example, it is 0.001 ppm, 0.0025 ppm, 0.005 ppm, 0.01 ppm, 0.015 ppm, or 0.025 ppm. Furthermore, the range of copper ion content in the beverage of the present invention is not particularly limited, but for example, it is 0.001 to 10 ppm, 0.0025 to 5 ppm, 0.01 to 1 ppm, 0.015 to 0.5 ppm, or 0.015 to 0.25 ppm. By setting the content within this range, the photodegradation inhibitory effect of gingerol can be further improved.

[0017] When manufacturing the beverage of the present invention, copper ions can be derived from raw materials containing gingerol or added separately. To adjust the copper ion content to the above range, copper salts or copper yeast that can be incorporated into the beverage can be added. Examples of copper salts include copper sulfate and copper gluconate. Examples of copper yeast include yeast that has incorporated copper. In one embodiment, the copper ions in the beverage of the present invention are derived from copper salts or copper yeast. Furthermore, in the beverage of the present invention, copper ions may exist in a free state from copper salts or copper yeast, or in a non-free state.

[0018] The method for measuring the copper ion content is not particularly limited as long as it is a known method, but for example, a colorimetric method using a colored complex specific to copper ions can be used.

[0019] (3) The ratio of copper ion content (B: ppm) to gingerol content (A: ppm) (B / A) In the beverage of the present invention, the ratio of copper ion content (B: ppm) to gingerol content (A: ppm) (B / A) is 0.00004 or more. The upper limit of this ratio is not particularly limited, but for example, it is 1.0, 0.4, 0.25, 0.1, 0.04, 0.025, or 0.01. The lower limit of this ratio is not particularly limited, but for example, it is 0.0001, 0.00025, 0.0004, 0.001, 0.0025, or 0.004. Furthermore, the range of this ratio is not particularly limited, but for example, it is 0.00004 to 1.0, 0.0001 to 0.4, 0.00025 to 0.25, 0.001 to 0.1, 0.001 to 0.04, or 0.0025 to 0.025. By keeping the ratio within this range, the photodegradation inhibitory effect of gingerol can be achieved.

[0020] (4) pH The pH of the beverage of the present invention is not particularly limited, but is, for example, pH 2.0 to 8.0, preferably 2.5 to 7.5, and more preferably 3.0 to 7.0. When the pH of the beverage of the present invention is 3 to 7, the photodegradation inhibitory effect of copper ions on gingerol can be further improved.

[0021] The pH adjustment of the beverage of the present invention is not particularly limited, but for example, organic acids such as citric acid, malic acid, lactic acid, and phosphoric acid; sodium salts such as disodium citrate, trisodium citrate, sodium bicarbonate, and sodium hydroxide; and potassium salts such as potassium hydroxide and potassium carbonate can be used.

[0022] (5) Types of beverages The type of beverage in the present invention is not particularly limited and may be an alcoholic beverage or a non-alcoholic beverage such as a soft drink. In the present invention, an alcoholic beverage means a beverage with an alcohol content of 1 v / v% or more, while a non-alcoholic beverage means a beverage with an alcohol content of less than 1 v / v%. Examples of non-alcoholic beverages include, but are not limited to, functional beverages, nutritional beverages, soft drinks, flavored water (near-water) beverages, sports drinks, tea-based beverages (grain tea, green tea, oolong tea, black tea, blended tea, etc.), coffee beverages, carbonated beverages, fruit juices, and vegetable beverages.

[0023] (6) Container In one embodiment, the beverage of the present invention is a packaged beverage. The type of container used is not limited, but a transparent container is preferred. Beverages filled in transparent containers are susceptible to the effects of light irradiation. Examples of transparent containers include those with a transmittance of 40% or more, preferably 50% or more, at 700 nm of visible light. Specifically, transparent plastic bottles and transparent glass bottles can be exemplified, and transparent PET bottles are particularly suitable for use in the present invention. The color of the container is not particularly limited, but it is preferred to be colorless.

[0024] Furthermore, a transparent container may be partially or entirely covered with film or the like. For example, the transparent area is not limited to containers where the label or printed area for content indication is opaque or semi-transparent and the rest is transparent, or containers where transparent and opaque areas with design elements are combined in different ways in multiple places, or opaque containers that only have a transparent area the size of a viewing window.

[0025] (7) Other ingredients The beverage of the present invention may contain various additives, such as flavorings, vitamins, colorants, antioxidants, emulsifiers, preservatives, seasonings, extracts, pH adjusters, and quality stabilizers, in the same manner as ordinary beverages, as long as they do not interfere with the effects of the present invention.

[0026] (8) Heat sterilization In one embodiment, the beverage of the present invention may be a sealed, bottled beverage obtained through heat sterilization. The heat sterilization conditions can be selected to obtain an effect equivalent to that stipulated in the Food Sanitation Act, for example, and can be 60 to 150°C for 1 second to 60 minutes. When using a heat-resistant container (such as glass), retort sterilization (110 to 140°C, 1 to several tens of minutes) can also be performed. Alternatively, when using a non-heat-resistant container (such as a PET bottle), the prepared liquid can be pre-sterilized at high temperature for a short time using a plate heat exchanger or the like (UHT sterilization: 110 to 150°C, 1 to several tens of seconds), cooled to a certain temperature, and then filled into the container.

[0027] 2. Method In one embodiment, the present invention relates to a method for producing a beverage containing gingerol. Specifically, the method includes the step of blending gingerol and copper ions into a beverage, wherein the ratio of the copper ion content (B: ppm) to the gingerol content (A: ppm) in the beverage (B / A) is 0.00004 or more.

[0028] The steps for adjusting the content of the above components in the beverage and the pH of the beverage are as described above or obvious from them with respect to the beverage of the present invention. The timing is also not limited. For example, the above steps may be performed simultaneously, separately, or in any order. It is sufficient that the final beverage obtained satisfies the above conditions. Furthermore, the preferred ranges for the content of the above components, the above ratios, and the pH are as described above with respect to the beverage. Furthermore, the types of beverages produced by the above method are also as described above with respect to the beverage.

[0029] The beverage produced by the manufacturing method of the present invention can suppress the photodegradation of gingerol. Therefore, in another respect, this manufacturing method is a method for suppressing the photodegradation of gingerol. [Examples]

[0030] The details of the present invention will be specifically described below with reference to experimental examples, but the present invention is not limited thereto. Furthermore, unless otherwise specified in this specification, numerical ranges are described as including their endpoints.

[0031] In this example, the gingerol content in the beverage was measured using HPLC. The specific measurement method is as follows. • HPLC system: Thermo Vanquish UHPLC system • Column: Impact UK-C18 HT (3mm x 100mm) Column temperature: 40°C Mobile phase A: Water-formic acid (99.9:0.1) Mobile phase B: Acetonitrile-formic acid (99.9:0.1) Detection: UV280nm ·Injection volume: 5μL ·Flow rate: 1.2mL / min • Gradient Program: Time (minutes) %A %B 0 85 15 0.3 85 15 3.6 0 100 4.7 0 100 4.8 85 15 6 85 15 • Standard substance: [6]-Shogaol (Tokyo Chemical Industries, Ltd.)

[0032] Example 1: Comparison of the effects of various metal ions on inhibiting the decomposition of gingerol Using ginger extract containing shogaol (Ginger Extract NE; Ikeda Sugar Refining Co., Ltd.), a pH 3.0 citrate buffer containing 8.7 ppm shogaol was prepared. Various metal ions (iron ions, manganese ions, or copper ions) were added in the salt form shown in Table 1, and the total volume was adjusted to 200 μL. Subsequently, the solutions were irradiated with light (42 kilolux, 25°C, 18 hours), and the shogaol content in each sample after irradiation was measured using the analytical method described above. The results of the shogaol retention rate (unit: %) at each metal ion concentration are shown in Table 1.

[0033] [Table 1]

[0034] As shown in Table 1, when iron ions or manganese ions were added, regardless of the type of salt, the remaining rate of shogaol decreased as the amount added increased, and it was shown that decomposition was actually promoted. On the other hand, when copper sulfate or copper gluconate was added as copper ions, the remaining rate of shogaol increased, and it was clear that the photodecomposition of shogaol was suppressed. In addition, when other metal ions (zinc ions, magnesium ions) were used, there was no change in the remaining rate of shogaol. In other words, it was clear that the photodecomposition-suppressing effect of shogaol was exerted when copper ions were added.

[0035] Example 2: Effect of copper ions on the decomposition inhibitory effect of gingerol Using ginger extract containing shogaol (Ginger Extract NE; Ikeda Sugar Refining Co., Ltd.), a pH 3.2 citrate buffer containing 8.7 ppm shogaol was prepared. Copper(II) sulfate pentahydrate was added as copper ions in the amounts shown in Table 2, and the total volume was adjusted to 200 μL. Subsequently, the samples were irradiated with light (42 kilolux, 25°C, 24 hours), and the shogaol content in each sample after irradiation was measured using the analytical method described above. For each sample, the residual shogaol rate was calculated and compared with the copper-free group (Samples 1, 7, 15, 23, 31). Samples with a residual rate increase of 5% or more were classified as "Significant effect: ○", samples with an increase of 1% or more were classified as "Effective: △", and samples with no change in residual rate were classified as "No effect: ×". The results are shown in Table 2.

[0036] [Table 2]

[0037] As shown in Table 2, by combining gingerol and copper ions, and setting the ratio of copper ion content (B:ppm) to gingerol content (A:ppm) to copper ion content (B / A) to 0.00004 or higher, it was found that the residual rate of gingerol increased and the photodegradation of gingerol was suppressed, regardless of the total content of gingerol and copper ions.

[0038] Example 3: Effect of pH on the inhibitory effect of copper ions on the decomposition of gingerol Samples containing 8 ppm of shogaol were prepared using ginger extract containing shogaol (Ginger Extract NE; Ikeda Sugar Refining Co., Ltd.). First, for the pH 7.0 sample, a 10 mM Bis-Tris buffer (containing 10% EtOH) containing 8 ppm of shogaol was prepared, and copper(II) sulfate pentahydrate was added as copper ions in the amounts shown in Table 3, adjusting the total volume to 200 μL. For the pH 3.2 sample, a citrate buffer (containing 10% EtOH) containing 8 ppm of shogaol was prepared, and copper(II) sulfate pentahydrate was added as copper ions in the amounts shown in Table 3, adjusting the total volume to 200 μL. Subsequently, the samples were irradiated with light (42 kilolux, 25°C, 14 hours), and the shogaol content in each sample after irradiation was measured using the analytical method described above. For each sample, the residual rate of gingerol was calculated and compared to the copper-free group (samples 41 and 43). Samples showing a residual rate increase of 5% or more were marked as "Significant effect: ○", samples showing an increase of 1% or more were marked as "Effective: △", and samples showing no change in residual rate were marked as "No effect: ×". The results are shown in Table 3.

[0039] [Table 3]

[0040] As shown in Table 3, it was found that, regardless of pH level, the inclusion of copper ions increased the remaining amount of gingerol and suppressed the photodegradation of gingerol. [Industrial applicability]

[0041] This invention provides a beverage containing gingerol in which the photodegradation of gingerol is suppressed. In other words, this invention relates to a novel means for providing a beverage in which gingerol is stably maintained for a long period of time, and therefore has high industrial applicability.

Claims

1. A beverage containing gingerol and copper ions, The beverage wherein the ratio of the copper ion content (B: ppm) to the gingerol content (A: ppm) (B / A) is 0.00004 or more.

2. The beverage according to claim 1, wherein the pH is 8.0 or less.

3. The beverage according to claim 1 or 2, wherein the copper ion content is 0.001 to 10 ppm.

4. A beverage according to any one of claims 1 to 3, wherein the gingerol content is 0.1 to 300 ppm.

5. The beverage according to any one of claims 1 to 4, wherein the copper ions are derived from copper salts or copper yeast.

6. The beverage according to claim 5, wherein the copper salts are copper sulfate or copper gluconate.

7. A beverage according to any one of claims 1 to 6, which is a beverage packaged in a transparent container.

8. A method for producing a beverage containing gingerol, The process includes adding gingerol and copper ions to the beverage. The method, wherein the ratio (B / A) of the copper ion content (B: ppm) to the gingerol content (A: ppm) in the beverage is 0.00004 or more.

9. A method for inhibiting the breakdown of gingerol in beverages, The process includes adding gingerol and copper ions to the beverage. The method, wherein the ratio (B / A) of the copper ion content (B: ppm) to the gingerol content (A: ppm) in the beverage is 0.00004 or more.

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