JP6310625B1 - Beverages containing tiliroside and chlorogenic acids - Google Patents

Abstract

An object of the present invention is to provide a beverage having improved bitterness and astringency caused by tiriloside, and to provide a method for improving the bitterness and astringency caused by tiriloside in the beverage. A beverage containing 0.008 to 1.0 mg / 100 ml of tiliroside contains 5 to 350 mg / 100 ml of chlorogenic acids. [Selection figure] None

Description

  The present invention relates to a beverage containing tiliroside and chlorogenic acids.

  Polyphenols such as flavonols, flavanones, and flavanols are known to have excellent physiological effects, and in order to express these physiological effects more effectively, it is effective to continuously ingest more polyphenols. is there. And there exists a drink as a form which can ingest a lot of polyphenols simply. However, since beverages containing a high concentration of polyphenol have a bitterness or astringent taste peculiar to polyphenols, they tend to be an obstacle to continuous consumption. Thus, various methods for reducing the bitterness and astringency of polyphenols have been proposed. For example, a method for reducing the astringency of polyphenols by sucralose (Patent Document 1) or collagen-derived peptide (Patent Document 2) has been proposed. Yes.

  On the other hand, it is known that plants such as rosehip contain tiliroside, which is a kind of polyphenol. Rosehip is a fruit of a plant belonging to the genus Rosaceae, and its rich nutritional components can provide high skin-beautifying effects, antibacterial, antiviral and immunity enhancement effects, It is known that an effect relating to a decrease in fat percentage and a decrease in neutral lipids in the liver can be obtained (Patent Document 3). And the application to the drink which anticipated these physiological effects is examined.

JP 2008-99677 A JP 2006-271259 A Patent No. 3790767

  As described above, tiliroside and a rosehip extract containing the same are effective materials that can be expected to eliminate obesity through the action of reducing body fat. However, in the study of the use of tiliroside by the present inventors, the unique bitterness and astringent taste of tiliroside can be felt, and the bitterness and astringent taste of tiliroside are particularly pronounced in neutral and low-sweetness beverages. It turned out to be.

  Then, an object of this invention is to provide the drink by which the bitterness and the astringent taste resulting from tiliroside were improved.

As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that a predetermined amount of chlorogenic acids has a particularly excellent effect on improving bitterness and astringent taste derived from tiliroside in beverages. Based on this finding, the present inventors have completed the present invention. The present invention is not limited to this, but relates to the following.
(1) A beverage containing 0.008 to 1.0 mg / 100 ml of tiliroside and 5 to 350 mg / 100 ml of chlorogenic acids.
(2) The beverage according to (1), wherein the content of tiliroside is 0.01 to 0.1 mg / 100 ml.
(3) The beverage according to (1) or (2), which is a coffee beverage.

  According to the present invention, it is possible to provide a beverage with improved bitterness and astringency due to tiliroside. Tiriloside is also a material that can be used for food and drink, as it is contained in natural plants such as rosehips. Therefore, it is considered that the beverage provided by the present invention has high safety and few side effects. Although the detailed mechanism of action is not clear and is not intended to be particularly limited, the unique bitterness and astringent taste caused by tiliroside and the bitterness, astringent taste, and unique flavor caused by chlorogenic acids It is thought that the bitter and astringent tastes derived from tiriloside are less likely to be felt as a result of canceling each other.

  One aspect of the present invention is a beverage containing 0.008 to 1.0 mg / 100 ml of tiliroside and 5 to 350 mg / 100 ml of chlorogenic acids.

(Tiriloside)
Tiliroside contained in the beverage of the present invention is a kind of organic compound classified as a flavonoid glycoside, and is a compound having the structure of the following formula (1). Another name for Tiriloside is also called Kaempferol-3-O-glucoside-6 ″ -E-coumaroyl, and its CAS registry number is 20316-62-5. As is obvious from the structure name and structural formula, tiriloside is composed of kaempferol, coumaric acid, and glucose.

  Thus, tiliroside has a characteristic structure not found in other flavonoids or glycosides. Having a bitter or astringent taste when using tiliroside in a beverage form is not easily imagined from this unique structure.

  Tiriloside is a known compound that is commercially available. In the present invention, tiliroside can be used in the form of a pure product or a plant extract. Examples of commercial products of Tiriroside include those sold by Funakoshi and those sold by Merck KGaA. Examples of the plant extract containing tiliroside include rosehip extract manufactured by Morishita Jintan and strawberry seed extract manufactured by Oriza Oil.

  The beverage of the present invention contains 0.008 to 1.0 mg / 100 ml of tiliroside. If the content of tiliroside in the beverage is within the above range, the bitterness and astringent taste derived from tiliroside can be effectively improved by chlorogenic acids described later while demonstrating the beneficial physiological action of tiliroside. However, if the content of tiliroside in the beverage exceeds 1.0 mg / 100 ml, the bitterness or astringent taste of tiliroside becomes too strong, and the effects of the present invention may not be obtained. From the viewpoint of effect and flavor, the content of tiliroside in the beverage of the present invention is preferably 0.01 mg / 100 ml or more, more preferably 0.02 mg / 100 ml or more. Moreover, the content of tiliroside in the beverage of the present invention is preferably 0.5 mg / 100 ml or less, or 0.3 mg / 100 ml or less, more preferably 0.1 mg / 100 ml or less.

The content of tiliroside in the present invention can be measured using high performance liquid chromatography (HPLC). The measurement conditions by HPLC are shown below.
・ Eluent: 37.5% acetonitrile ・ Flow rate: 1 mL
・ Detection: UV 254 nm
・ Column: Shiseido CAPCELL PAK C18 (4.6 x 250 mm)

(Chlorogenic acids)
The beverage of the present invention contains chlorogenic acids. The chlorogenic acids in the present invention are 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3-ferlaquinic acid, 4-ferlaquinic acid, 5-ferlaquinic acid, and 3,4-dicaffee. Oil quinic acid, 3,5-dicaffeoyl quinic acid, and 4,5-dicaffeoyl quinic acid, the content of chlorogenic acids in the beverage of the present invention is the sum of these compounds in the beverage of the present invention The content (mg / 100ml) is meant. The content of chlorogenic acids can be measured by high performance liquid chromatography (HPLC). The measurement conditions by HPLC are shown in the Examples described later. In the measurement of chlorogenic acids, if necessary, the beverage of the present invention is appropriately diluted with pure water, filtered through a 0.45 μm filter, and injected into HPLC.

  The content of chlorogenic acids in the beverage of the present invention is 5 to 350 mg / 100 ml. If the content of chlorogenic acids in the beverage is within the above range, the bitterness and astringent taste derived from tililoside can be effectively improved. The content of chlorogenic acids in the beverage of the present invention is preferably 10 mg / 100 ml or more, more preferably 20 mg / 100 ml or more. The content of chlorogenic acids in the beverage of the present invention is preferably 250 mg / 100 ml or less, 230 mg / 100 ml or less, 200 mg / 100 ml or less, or 180 mg / 100 ml or less, more preferably 150 mg / 100 ml or less.

  In the present invention, chlorogenic acids may be natural products containing chlorogenic acids, particularly those extracted from plants or purified products thereof, or those produced industrially by chemical synthesis. In a preferred embodiment of the present invention, the chlorogenic acids are derived from plant extracts. Examples of plants containing chlorogenic acids include coffee beans, southern leaves, apples and the like. The preparation of such a plant extract is not particularly limited, and can be performed using methods known to those skilled in the art.

(Beverage)
The beverage of the present invention is a beverage containing a specific amount of tiliroside and chlorogenic acids, and reduces the bitterness and astringent taste of tiliroside that tends to remain as a aftertaste by using a predetermined amount of chlorogenic acid, thereby improving the taste of the beverage. Is. According to the study by the present inventors, the bitterness and astringency of tiriloside tend to be strong particularly when the beverage is neutral. Therefore, a preferred aspect of the present invention is that the beverage is neutral. Specifically, the beverage of the present invention preferably has a pH of 5-7, more preferably a pH of 5.5-7.

  In order to adjust pH in the said range, the drink of this invention can be made to contain a pH adjuster. As the pH adjuster, for example, any one or more selected from the group consisting of sodium bicarbonate, calcium carbonate, sodium citrate, and sodium hydroxide can be used.

  Further, according to the study by the present inventors, a low sweetness beverage whose sweetness is suppressed to a certain level or less is more prominent in the bitterness and astringency of tiriloside than a beverage having a higher sweetness. There is a tendency. Therefore, a beverage with low sweetness is a preferred embodiment of the beverage of the present invention because of its remarkable effect. Here, the “low-sweetness beverage” specifically refers to a beverage having a sweetness level of 2 or less, preferably 1.5 or less, more preferably 1 or less, and even more preferably 0.5 or less. In addition, a lower limit is 0 or more, Preferably it is 0.01 or more. The sweetness degree is a scale indicating the intensity of sweetness, and is a relative ratio when the sweetness of 1% by weight of sucrose (20 ° C.) is 1. The sweetness level of a beverage is calculated by converting the amount (weight concentration) of each sweetening component contained in the beverage to an equivalent amount of sucrose based on the relative ratio of sweetness of the sweetening component to sweetness 1 of sucrose, Subsequently, it can obtain | require by totaling the sucrose sweet-equivalent amount of all the sweetening components contained in the said drink. The relative ratio of sweetness of various sweetening ingredients to sweetness 1 of sucrose can be determined from a known sugar sweetness conversion table (McMurally Organic Chemistry (7th edition), page 988).

  A coffee drink is mentioned as one of the suitable aspects of the drink of this invention. Here, the “coffee beverage” refers to a beverage produced using coffee as a raw material. The coffee content means a liquid containing a component derived from coffee beans, for example, a coffee extract, that is, a liquid obtained by extracting roasted and pulverized coffee beans using water, hot water or the like. It is done. Moreover, the liquid which adjusted the coffee extract which concentrated the coffee extract, the instant coffee which dried the coffee extract, etc. with water, warm water, etc. to an appropriate quantity is also mentioned as a coffee part. The coffee content contains chlorogenic acids. Therefore, a coffee beverage in which chlorogenic acids are contained in a part of the raw material is a preferred embodiment of the beverage of the present invention from the viewpoint of ease of production and flavor of the beverage. In particular, black coffee that does not contain components other than coffee components such as milk and sweetening components added to beverages is an example of a preferred embodiment of the present invention.

  In addition, in the beverage of the present invention, various additives and the like may be blended depending on the type of the beverage as long as it does not depart from the intended purpose of the present invention. Examples of the various additives include sweeteners, acidulants, fragrances, vitamins, pigments, antioxidants, emulsifiers, preservatives, extracts, and quality stabilizers.

  The beverage of the present invention is an easy-to-drink beverage with reduced tiriroside bitterness and astringency. Therefore, it is excellent in terms of convenience from the viewpoint of the user that a drink that can be continuously ingested in anticipation of the physiological action of tiliroside can be stored for a long period of time at room temperature and ready for drinking (RTD: Ready To Drink).

  Containerized beverages containing polyphenols tend to cause an increase in bitterness, deterioration odors and flavors, a decrease in the residual ratio of polyphenols, etc. when stored for a long period of time, and may impair the commercial value. However, the beverage of the present invention containing a predetermined amount of tiliroside and chlorogenic acid has storage stability. From such a viewpoint, a container-packed beverage obtained through a heat sterilization treatment is one embodiment of the present invention. In this case, the type of the container is not particularly limited, and any of the containers normally used in beverages such as an aluminum can, a steel can, a PET bottle, a glass bottle, and a paper container can be used.

  The beverage of the present invention can be produced by appropriately blending the components described above. Regarding the content of chlorogenic acids, for example, when using an extract of roasted coffee beans as a raw material, the content of chlorogenic acids in the beverage of the present invention is measured after measuring the amount of chlorogenic acids in the extract. Can be adjusted. Moreover, the drink of this invention can be made into a container stuffed drink through processes, such as sterilization, as needed. For example, a sterilized container-packed beverage can be produced by a method of performing heat sterilization after filling a beverage into a container, or a method of sterilizing a beverage and then filling the container in an aseptic environment. As a preferred embodiment of the present invention, the beverage of the present invention is a container-packed beverage.

  In the production of the beverage of the present invention, the blending order of various components is not particularly limited. Moreover, in the manufacture of the beverage of the present invention, a step of blending the above-described components and materials and a step of adjusting their contents can be included. About various elements, such as the kind of component in a drink in the manufacture of the drink of this invention, and its content, it is as above-mentioned regarding the drink of this invention, or it is obvious from them.

  Hereinafter, although an experiment example is shown and the detail of this invention is demonstrated concretely, this invention is not limited to this. In this specification, unless otherwise specified, numerical ranges are described as including the end points.

(Experimental example 1: Evaluation of beverage containing tiliroside)
As Tiriroside, Funakoshi (purity 99%) was used. Tiriloside was dissolved in water (pH 7 ion exchange water) so that the concentration of tiliroside in the aqueous solution was the concentration shown in Table 1. With respect to various concentrations of tiliroside solutions (pH: about 7, sweetness: 0), a panel of five people evaluated the presence or absence of bitterness and astringent taste derived from tiliroside. The evaluation was carried out by all the panel members after each person implemented the presence or absence of bitterness or astringency.

  The results are shown in Table 1. It has been found that a solution containing tiriroside at a concentration of 0.008 mg / 100 ml or more has a bitter or astringent taste of tiriroside and is a beverage that is difficult to drink.

(Experimental example 2: Tililoside bitter and astringent taste reduction effect by chlorogenic acid (1))
In the same manner as in Experimental Example 1, a sample solution having a tiliroside content of 0.02 mg / 100 ml was prepared (Sample 2-1). In addition, tiliroside (funakoshi, purity 99%) and chlorogenic acid hemihydrate (Nacalai Tesque) were dissolved in ion-exchanged water at pH 7 so that the concentrations shown in Table 2 were obtained. Was prepared (pH: about 7, sweetness: 0) (Samples 2-2 to 2-11). For each sample solution, the strength of bitterness and astringent taste derived from tiriloside was evaluated by a panel of five people. Evaluations were conducted by each panel based on the following criteria, and the evaluation points were determined in consultation with all the panels.
5 points: Does not feel the bitterness and astringency unique to tiriroside.
4 points: Little bitterness and astringent taste peculiar to tiliroside are felt.
3 points: A bitter and astringent taste peculiar to tiriloside is felt, but it does not remain in the aftertaste.
2 points: There are bitterness and astringent taste peculiar to tiliroside, and it remains in the aftertaste.
1 point: The bitter and astringent taste peculiar to tiliroside is strong and remains in the aftertaste.

  The results are shown in Table 2. Beverages containing tiliroside at a concentration of 0.02 mg / 100 ml felt strongly the bitter and astringent taste of tiliroside and were difficult to drink, but by containing 5 mg / 100 ml or more of chlorogenic acid, the bitterness of tiliroside The astringent taste was effectively reduced (reduced).

  In addition, when 500 mg / 100 ml of chlorogenic acid was contained, some panels evaluated that the bitterness resulting from chlorogenic acid was strongly felt and it was not suitable for drinking. Therefore, it was suggested that the chlorogenic acid content effective in reducing the bitterness and astringent taste derived from tiliroside including ease of drinking of beverages is 5 to 350 mg / 100 ml.

(Experimental Example 3: Tililoside Bitterness / Astringency Taste Reduction Action by Chlorogenic Acid (2))
In the same manner as in Experimental Example 2, sample solutions having the concentrations shown in Table 3 were prepared (pH: about 7, sweetness level: 0) (Samples 3-1 to 3-3). Sensory evaluation was performed on the various sample solutions using the same methods and criteria as in Experimental Example 2.

  The results are shown in Table 3. Even when the amount of tiliroside was 0.05 mg / 100 ml, the bitterness and astringent taste derived from tiliroside could be effectively reduced by containing a specific amount of chlorogenic acid.

(Experimental Example 4: Tililoside Bitter / Astringent Taste Reduction Action by Chlorogenic Acid (3))
In the same manner as in Experimental Example 2, sample solutions having the concentrations shown in Table 4 were prepared (pH: about 7, sweetness: 0) (Samples 4-1 to 4-9). Sensory evaluation was performed on the various sample solutions using the same methods and criteria as in Experimental Example 2.

  The results are shown in Table 4. Even when the amount of tiliroside was 0.008 to 1.0 mg / 100 ml, the bitterness and astringent taste derived from tiliroside could be effectively reduced by containing 5 to 350 mg / 100 ml of chlorogenic acid. On the other hand, when the tiriloside content in the beverage is 2.0 mg / 100 ml, the bitterness and astringency of tiriloside are too strong, and even if a large amount of chlorogenic acids are added, the bitterness and astringency of tiriloside can be reduced. could not.

(Experimental Example 5: Tililoside Bitter / Astringent Taste Reduction Action by Chlorogenic Acid (4))
In the same manner as in Experimental Example 2, sample solutions having the concentrations shown in Table 5 were prepared (pH: about 7, sweetness: 0) (Samples 5-1 to 5-6). Sensory evaluation was performed on the various sample solutions using the same methods and criteria as in Experimental Example 2.

  The results are shown in Table 5. Even when the concentration of tiliroside was 0.01 mg / 100 ml to 0.1 mg / 100 ml, the bitterness and astringent taste derived from tiliroside could be effectively reduced by containing a specific amount of chlorogenic acid.

(Experimental example 6: Evaluation of coffee drink containing tiriroside (1))
The coffee content was used as a source of chlorogenic acids, and the bitterness and astringent taste derived from tiriloside were evaluated.

A coffee instant coffee was prepared by dissolving commercially available instant coffee in water at a predetermined ratio (sample A). When the content of chlorogenic acids in Sample A was measured using HPLC, it was 20 mg / 100 ml. As a measuring method, sample A was diluted 10-fold (w / w) with the following mobile phase A, filtered through a membrane filter (Cellulose Acetate 0.45 μm manufactured by ADVANTEC), and injected into HPLC. Then, using chlorogenic acid hemihydrate as a standard substance, 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 3-ferlaquinic acid, 4-ferlaquinic acid, 5-ferlaquina The content was determined from the peak area values of nine chlorogenic acids, acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, and 4,5-dicaffeoylquinic acid. The conditions of HPLC are as follows.
・ Column: Guard column Inertsil ODS-3 (4.0mmφx20mm) + Inertsil ODS-2 (4.6mmφx250mm) (GL Science)
-Mobile phase: A: 0.05M acetic acid, 0.1 mM 1-hydroxyethane-1,1-diphosphonic acid, 3 (V / V)% acetonitrile solution
B: 0.05 M acetic acid, 0.1 mM 1-hydroxyethane-1,1-diphosphonic acid, 97 (V / V)% acetonitrile solution Flow rate: 1.0 ml / min
・ Column temperature: 35 ℃
-Gradient conditions: 100% solution A is retained from 1 minute after the start of analysis.
From 1 minute to 20 minutes, B solution 13%,
B liquid 13% retention from 20 to 25 minutes,
From 25 minutes to 27 minutes, B solution 15%,
B liquid 15% retention from 27 to 45 minutes,
From 45 minutes to 55 minutes, B liquid 20%,
Liquid B 100% in 55 to 60 minutes
Hold B solution 100% from 60 to 70 minutes,
From 70 minutes to 75 minutes, solution A is 100%,
75% to 100 minutes A solution 100% retention and injection volume: 10.0 μl
・ Detection wavelength: 325nm
Reference material: Chlorogenic acid hemihydrate (content 99%) (Wako first grade)

  Sample A was prepared separately, and chlorogenic acid hemihydrate (Nacalai Tesque) was added thereto to prepare a sample in which the concentration of chlorogenic acids in the coffee was 50 mg / 100 ml or 150 mg / 100 ml. Tiriloside (Funakoshi, purity 99%) was added to these samples (coffee content) so that the tiliroside content was 0.02 mg / 100 ml to produce tiliroside-containing coffee beverages having different chlorogenic acid concentrations (Sample 6). -1-6-3). About the obtained coffee drink, sensory evaluation was implemented by the method and standard similar to Experimental example 2.

  The results are shown in Table 6. Even when chlorogenic acids derived from coffee were used, the bitterness and astringent taste derived from tiriloside could be effectively reduced.

(Experimental Example 7: Evaluation of Tiriloside-Containing Coffee Beverage (2))
In the same manner as in Experimental Example 6, various types of coffee beverages were prepared so that the concentration of the coffee beverage in the final form was as shown in Table 6, and each can was filled with 190 ml to make a container-packed coffee beverage. The obtained container-packed coffee beverage was sterilized by heating at 120 to 125 ° C. for 5 minutes. About the heat-sterilized container-packed coffee drink, after cooling to room temperature, sensory evaluation was implemented by five panels. As a result, all the panels evaluated that none of the coffee beverages after heat sterilization felt the bitterness or astringency of tiriloside.

  In addition, the above-mentioned heat-sterilized container-packed coffee drink was separately prepared and stored at 55 ° C. for 2 weeks, and the flavor after storage was evaluated by a panel of five people. The storage at 55 ° C. for 2 weeks means an accelerated test for long-term storage (equivalent to 10 months at room temperature). As a result of the evaluation, all of the coffee drinks are highly tasteful drinks in which all the panels have suppressed the bitterness and astringency of tiriloside even after storage, and the bitterness has not increased compared to before storage. It was judged.

(Experimental example 8: Evaluation of coffee drink containing tiriroside (3))
Heat-sterilized container-packed coffee beverages were produced in the same manner as in Experimental Example 7 except that the concentrations of tiliroside and chlorogenic acids were changed as shown in Table 7 (Samples 7-1 to 7-5). About various container-packed coffee drinks, after cooling to room temperature, sensory evaluation was performed by the same method and standard as in Experimental Example 2.

  The results are shown in Table 7. Even when the tiriloside concentration was 0.05 mg / 100 ml or 0.1 mg / 100 ml, the bitterness and astringent taste of tiriloside could be effectively reduced by containing a specific amount of chlorogenic acids derived from coffee. However, when the tiliroside concentration was 2 mg / 100 ml, the effect of reducing the bitterness and astringency of tiliroside by chlorogenic acids was not obtained.

Claims (3)

  A beverage containing 0.008 to 1.0 mg / 100 ml of tiliroside and 5 to 350 mg / 100 ml of chlorogenic acids.   The beverage according to claim 1, wherein the content of tiriloside is 0.01 to 0.1 mg / 100 ml.   The beverage according to claim 1 or 2, which is a coffee beverage.