JP2001046037A - Method for reducing astringent taste of proanthocyanidin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To markedly reduce the astringent taste of proanthocyanidin that is useful as an antioxidant for foods and the like inexpensively, efficiently in a large amount and safely without quantitative loss by adding protein and polysaccharide to the extract mainly comprising specific proanthocyanidin. SOLUTION: The astringent taste of proanthocyanidin is reduced by adding (B) protein and/or (C) polysaccharide to (A) an extract from plant bodies, mainly comprising proanthocyanidin. The weight ratio of proanthocyanidin to the mixture of the components B/C is preferably in the range of from 1/1-1/100. The component A is preferably selected as an extract from the grape fermentation food or seeds of grape or the like. The component B is defatted powdery milk and/or separated soybean protein, while the component C is preferably starch and/or agar-agar.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for reducing the astringency of an extract containing proanthocyanidin as a main component obtained by extracting a plant.

[0002]

2. Description of the Related Art Proanthocyanidins obtained by extracting plants such as grape seeds, bark, squeezed lees or bark and beans have a strong antioxidant action and are used as antioxidants in foods and the like. ing. Also, since it has various physiological activities, it is recently used as a health food material. Proanthocyanidins are a type of polyphenol and have the formula

[0003]

Embedded image (Wherein R ₁ is a hydrogen atom or a hydroxyl group, R ₂ and R ₆ are each independently a hydrogen atom, a hydroxyl group or a methoxy group, R ₄ , R ₃ , R
₇ and R ₈ each independently represent a hydroxyl group or a methoxy group, and R ₅ represents a galloyl group or a glucopyranosyl group), represented by flavan-3-ol or flavan-3,4-diol as a constituent unit. A group of compounds linked by condensation or polymerization at the 4th or 4th to 8th positions, and are condensed tannins present in various plants. In addition, chemical formula 1 shows only the case where condensation is performed at the 4-8 position to facilitate understanding. These are given the name because they produce anthocyanidins such as cyanidin, delphinidin and pelargonidin by acid treatment. The dimer, the trimer, the tetramer, and the 10 to 30-mer or more of the above structural units include proanthocyanidins such as procyanidin, prodelphinidin, and properargonidine, and stereoisomers thereof.

However, since proanthocyanidin has a unique strong astringency, its amount is naturally restricted when added to food as an antioxidant, or when it is eaten as a health food, severe numbness in the oral cavity is caused. It is extremely difficult to take large quantities of proanthocyanidins as they are due to the accompanying discomfort.

[0005] For these reasons, in the field of health foods containing proanthocyanidin as a main component, there are many forms of tablets (including sugar-coated tablets) or capsules, and powder or granule type products are not found.

[0006] By the way, various methods for reducing bitterness have been proposed in the field of medicine and the like.
In the same way as the taste, unlike the taste buds, it can be felt in places other than taste buds (for example, the inner wall of the mouth, the back of the tongue, etc.)
It is akin to tactile and painful sensations. That is, the method of reducing bitterness, which is the taste, cannot be used to reduce astringency close to touch or pain. A typical example of tannin-based "astringent food" is persimmon astringent tannin. Etc. are known. However, in these, persimmon fruit cells undergo anaerobic respiration to generate acetaldehyde, which polymerizes persimmon astringent tannins, resulting in insolubilization of the tannins. It is not possible to reduce the astringency of this product by this method. Other methods of reducing the astringency of foods containing a tannin-based astringency include a method of adding an alkali-treated gelatin to black tea to form a jelly (JP-A-4-49984), and a method of reducing the astringency of foods containing astringent components such as tannin. A method of adding protamine (JP-A-5-328935, JP-A-6-138875), a method of glycosylating astringent components with an enzyme (JP-A-7-327602, JP-B-6-327602)
88908), a method of adsorbing and removing astringent components with a resin or activated carbon (JP-A-8-173084, 9-220055, 11-103817),
Masking method using cyclodextrin
327602, 9-309902, and 10-4919) have been proposed. However, all of these are methods of masking the astringency of tannin contained in a very small amount, methods of removing tannin itself, or methods of adding expensive or generally unused substances, There has been no known method for reducing the astringency in a safe, inexpensive, efficient, and safe manner without the loss of proanthocyanidins.

[0007]

SUMMARY OF THE INVENTION In view of the above circumstances, an object of the present invention is to provide a method for reducing the astringency of proanthocyanidin-based extracts obtained by extracting plants. is there.

[0008]

Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, have found that an extract containing proanthocyanidin as a main component obtained by extracting a plant body has a specific protein content. Alternatively, they have found that the addition of polysaccharides can significantly reduce the astringency of proanthocyanidins, and have completed the present invention.

Hereinafter, the present invention will be described in detail. First, a proanthocyanidin-based extract obtained by extracting a plant object of the present invention is a grape, a persimmon, an apple, a pine, a soybean, a soybean, a plant such as red bean is extracted with water or an organic solvent. The resulting extract, the main component of which is proanthocyanidins. Among them, a grape seed extract is preferable because it has a high content and a low content of impurities such as saccharides, so that high-purity proanthocyanidins can be easily obtained by extraction.

Except for the extract from grape seeds, the extract from red beans (Ariga et al., Agric. Biol. Chem.) 45, 2709
-2712, 1981), extract from pine bark (RWHemin
gway et al., Phytochemistry No. 22
Vol., Pp. 275-281, 1983).

The proanthocyanidin-based extract obtained as described above is obtained in a liquid or semi-solid form, and the extraction solvent is distilled off therefrom under reduced pressure.
If removed by a known method such as spray drying or freeze drying, it can be used as it is as a proanthocyanidin-containing concentrate or dried product. As shown in the examples of JP-A-11-80148, a proanthocyanidin composition having a high purity of 90% or more can be easily obtained by using optimal raw materials and extraction conditions.

Next, the protein / polysaccharide to be added to proanthocyanidin to reduce the astringency is essentially any protein / polysaccharide as long as the astringency is reduced. There are no restrictions on the source material, place of production, timing, production method, and the like. However, since proanthocyanidins whose astringency has been reduced by addition are mainly used as foods, it is preferable to use edible proteins / polysaccharides or foods containing proteins / polysaccharides.
Also, since the principle of astringency reduction is thought to be based on the hydrophobic bond (or hydrogen bond) between proanthocyanidin and the protein / polysaccharide, the contact of both molecules is efficient in terms of time and area. To be performed, proteins / polysaccharides that are water soluble or dispersible in water are preferred.
Further, since the choice of proanthocyanidins with reduced astringency (that is, the proanthocyanidin-protein / polysaccharide conjugate) as foods is broadened,
It is desirable that the astringency-reduced product (combined body) itself be soluble or dispersible in water. In addition, to take advantage of its excellent physiological activity, adults need to take about 50-500 mg of proanthocyanidin per day, but if economic factors are not satisfied, it is practical to take this amount. Is impossible. In this sense, it is desired that the protein / polysaccharide or the food containing the protein / polysaccharide used here is inexpensive, that a large quantity of a certain quality can be easily obtained.

From such a viewpoint, the protein is preferably a protein derived from milk and a protein derived from soybean. For example, commercially available foods include milk, whole-fat milk powder, whole-fat condensed milk, skim milk powder, casein, milk whey, lactalbubin, soy milk, powdered isolated soy protein, and the like. In addition, examples of proteins satisfying the above conditions include gelatin, collagen, ovalbumin, soluble wheat protein, and the like.However, skim milk powder and powdery separated soy protein are used because they are easy to measure and inexpensive. It is suitable.

Similarly, as the polysaccharide, starch and agar are preferable, and particularly, in the case of starch, pregelatinized one is preferable. In commercial foods, starches such as flour, corn starch, potato starch (starch),
Examples of agar such as rice flour include powder agar, stick agar, flake agar, and thread agar. In addition, examples of polysaccharides satisfying the above conditions include dietary fiber such as psyllium, pectin, dextran, chondroitin sulfate, and the like. It is suitable.

The amount of protein / polysaccharide to be added is affected by the type and purity of the protein / polysaccharide.
When each of proanthocyanidin and protein / polysaccharide is 100% pure, the weight mixing ratio is proanthocyanidin: protein / polysaccharide = 1: 1 to 1: 100,
Preferably it is 1: 1 to 1:10.

The method of adding the protein / polysaccharide to the proanthocyanidin is not limited, but it is usually preferable to add the required amount of the protein / polysaccharide to the aqueous proanthocyanidin solution at a concentration of 1 to 10% while thoroughly stirring. If the protein / polysaccharide is a solid, it may be added as it is, or may be added after being powdered, or may be added after being dissolved or dispersed in water at an appropriate concentration. The temperature at the time of addition is usually 5 to 50 ° C, preferably 15 to 40 ° C, because of the possibility of denaturation in the case of proteins. In the case of polysaccharides, the temperature is usually 5 to 90 ° C, preferably 15 to 50 ° C. Further, powdery proanthocyanidin and powdery protein / polysaccharide can be mixed in a mortar, a powder mixer or the like.

There are no particular restrictions on the form of the proanthocyanidin with reduced astringency as a food, but the form of a liquid dissolved or dispersed in water or milk, the form of a gel such as jelly,
Examples include powdery and granular forms. As a matter of course, capsules and tablets may be used as usual.

[0018]

According to the present invention, the astringency of proanthocyanidins can be reduced safely, inexpensively, in large quantities, and safely without loss of the quantity of proanthocyanidins. As a result, even if it is a powder type, the astringency is mild, and even children and elderly people who have difficulty in taking tablets or capsules can easily take proanthocyanidins and reduce astringency. The obtained proanthocyanidin composition can be widely marketed.

In the present invention, the scale of astringency is determined as follows. <Setting of Astringency Scale (Preparation of Astringency Evaluation Standard Curve)> Since there is no unit, scale or standard representing astringency intensity, grape seed extract (Kikkoman Co., Ltd.) at various concentrations
Manufactured by "Grabinol Super", proanthocyanidin purity 95%, hereinafter abbreviated as GVS. ) Was dissolved in water, and the astringency of the aqueous solution was organoleptically evaluated using 15 panelists to prepare a standard curve for evaluating astringency. The astringency evaluation points were determined as follows. ｛0 points: no astringency, 1 point; slightly bitter, 2 points; bitter, 3 points;濃度 The concentration at which the average astringency evaluation score by the panelists is 1 point is defined as the "minimum concentration for expressing astringency".

The sensory evaluation test was carried out at 25 ° C. in a room, 1 to 3 hours after lunch. After 5 mL of a sample of each concentration was contained in the oral cavity for 5 to 10 seconds in order from the one with the lowest concentration, it was swallowed and the sensory evaluation was performed. Immediately after the end of the sensory evaluation of each sample, oral gargling was performed with water, and after an interval of 2 minutes or more, the sensory evaluation of the next sample was performed. The results of a sensory evaluation test of the astringency of the GVS aqueous solution are shown in Table 1 and FIG.

[0021]

[Table 1] From the astringency evaluation standard curve in FIG. 1, it can be seen that the minimum concentration for expressing astringency of the GVS aqueous solution is about 0.06%.

[0022]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. <Example 1> Effect of reducing astringency using milk GVS was dissolved in milk at various concentrations, and the astringency was sensory evaluated using 13 panelists. Milk is manufactured by Snow Brand Milk Products Co., Ltd. 3.
Five milks were used. Table 2 and FIG. 2 show the results of the astringency evaluation test of the GVS milk solution.

[0023]

[Table 2]

From the astringency evaluation curve in FIG. 2, it can be seen that the minimum concentration of astringent taste expression of the GVS milk solution is about 1.7%. This is about 30 times the concentration of the aqueous solution, and clearly shows that milk has an astringency reducing effect. Also, since the protein in milk is about 7%, the weight ratio at the lowest concentration of astringent expression is approximately GV
S: milk protein = 1: 4.

Example 2 Effect of Reducing Astringency Using Soy Milk As in Example 1, GVS was dissolved at various concentrations in a commercially available soy milk drink (Nagoya Dairy Co., Ltd. “Tofu-forming soy milk”). And
Sensory evaluation of astringency was conducted using 15 panelists. Table 3 and FIG. 3 show the results of the astringency evaluation test of the GVS soymilk solution.

[0026]

[Table 3]

From the astringency evaluation curve of FIG. 3, it can be seen that the minimum concentration of astringent expression of the GVS soymilk solution is about 3.9%. This is the case for aqueous solutions
It is 60-70 times the concentration, which clearly shows that soy milk has an astringency reducing effect. Since the protein in soy milk is about 12%, the weight ratio at the lowest concentration of astringent taste expression is approximately GV
S: soy milk protein = 1: 3.

<Example 3> Reduction effect of astringency using glutinous rice flour GVS is dissolved in water so as to have a final concentration of 0.5%, and glutinous rice flour (Kami-Shirami) in various ratios there. ) Was added, mixed well and dissolved, and then the sensory evaluation of astringency was carried out by 15 panelists. Uruchi rice flour used was Yamagata Prefectural Foods Co., Ltd. Kamigaku flour (pre-alpha). Table 5 and FIG. 4 show the results of the astringency evaluation test of the GVS-glutinous rice flour mixture.

[0029]

[Table 4]

From the astringency evaluation curve of FIG. 4, it can be seen that the minimum mixing ratio of GVS / glutinous rice flour to express astringency is about 0.11. Also, since the starch in the glutinous rice flour is about 80%, the weight ratio in the minimum mixture ratio for expressing astringency is approximately GVS: glutinous rice flour starch = 1: 7.

Example 4 Method for Reducing Astringency Using Powder Agar The same operation as in Example 3 was performed, except that powder agar was used instead of glutinous rice flour, and sensory evaluation of astringency was performed by 15 panelists. Was carried out. The powder agar used was Ultra Agar AX-30 manufactured by Ina Foods Co., Ltd. The results of the astringency evaluation test of the GVS-powder agar mixture are shown in Table 6 and FIG.

[0032]

[Table 5]

From the astringency evaluation curve in FIG. 5, it can be seen that the minimum mixing ratio of GVS / powder agar for expressing astringency is about 0.30. In addition, since the agar content in the powder agar is about 70%, the weight ratio in the minimum mixture ratio for expressing astringency is approximately GVS: agar = 1: 2.

<Example 5> Effect of reducing astringency using skim milk powder The same operation as in Example 3 was performed except that skim milk powder was used instead of glutinous rice powder, and sensory evaluation of astringency was performed by 15 panelists. The test was performed. Skim milk powder is Snow Brand Milk Products Co., Ltd.
Skim milk made by the company was used. The results of the astringency evaluation test of the GVS-skim milk powder mixture are shown in Table 7 and FIG.

[0035]

[Table 6]

From the astringency evaluation curve in FIG. 6, it can be seen that the minimum mixing ratio of GVS / skim milk powder to express astringency is about 0.32. Also, since the protein in skim milk powder is about 40%, the weight ratio in the minimum astringency expression mixture ratio is approximately GVS: skim milk protein = 3: 8.

Example 6 Effect of Reducing Astringency Using Soy Protein The same operation as in Example 3 was carried out except that soy protein was used instead of glutinous rice flour, and sensory evaluation of astringency was performed by 15 panelists. The test was performed. The soybean protein used was Supro 670 manufactured by Fuji Oil Co., Ltd. The results of the astringency evaluation test of the GVS-soy protein mixture are shown in Table 8 and FIG.

[0038]

[Table 7]

From the astringency evaluation curve in FIG. 7, it can be seen that the minimum mixing ratio of GVS / soy protein to express astringency is about 0.42. In addition, since the protein in soy protein is about 80%, the weight ratio in the minimum mixing ratio for expressing astringency is approximately GVS: skim milk protein = 1: 2.

<Example 8> Production of agar-astringency-reduced proanthocyanidin composition GVS: 24 g and Ultra agar AX-30 manufactured by Ina agar Co., Ltd .: 96 g
Was thoroughly mixed, 0.6 L of distilled water was added, and the mixture was thoroughly stirred to completely dissolve. This was freeze-dried to obtain 120 g of a powdery proanthocyanidin composition. Astringent paneler 1 of this composition
The sensory evaluation score by five persons was 0.533, and almost no astringency was felt. Also, 10 g of this composition is 50 m water at room temperature.
L was instantly dispersed.

<Example 9> Production of soybean protein-astringent taste-reduced proanthocyanidin composition GVS: 24 g and Fuji Oil Co., Ltd.'s Supro 670: 96 g were mixed well, 0.6 L of distilled water was added, and the mixture was stirred well. And completely dissolved. This was freeze-dried to obtain 120 g of a powdery proanthocyanidin composition. The sensory evaluation score of 15 a panelists of astringency of this composition was 0.333, and almost no astringency was felt. Also, 10 g of this composition could be instantaneously dispersed in 50 mL of water at room temperature.

Example 10 Granulated food was wet-granulated using water and ethanol so that one package had the following formulation, and then aluminum heat-sealed and packaged, and 2.6 g of granular food was packaged ( 400 GVS per packet
mg).

<Example 11> After the ingredients were mixed well so that one package of powdered food had the following formulation, aluminum heat seal packaging was carried out, and 2.5 g of powdered food was packaged (per packet). (Containing 400 mg as GVS).

Example 12 Tablet Foods 250 mg of tablet food was produced by mixing each component well and compressing it with a tableting machine so that one tablet had the following formulation, and produced a tablet food (GVS per tablet). 40 mg).

Example 13 Drink Preparation A drink preparation having the following formulation was produced. Contains 400mg as GVS per bottle.

[0046]

[Brief description of the drawings]

FIG. 1 is a standard curve diagram for evaluating astringency

FIG. 2 is a diagram showing the effect of reducing the astringency of milk.

FIG. 3 is a graph showing the effect of reducing the astringency of soy milk.

FIG. 4 is a diagram showing the effect of reducing the astringency of glutinous rice flour.

FIG. 5 is a diagram showing the effect of reducing the astringency of powder agar.

FIG. 6 is a diagram showing the astringency reducing effect of skim milk powder

FIG. 7 is a graph showing the astringency reducing effect of soy protein.

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[Procedure amendment]

[Submission date] August 27, 1999 (1999.8.2
7)

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0003

[Correction method] Change

[Correction contents]

[0003]

Embedded image (Wherein R ₁ is a hydrogen atom or a hydroxyl group, R ₂ and R ₆ are each independently a hydrogen atom, a hydroxyl group or a methoxy group, R ₄ , R ₃ , R
₇ and R ₈ each independently represent a hydroxyl group or a methoxy group, and R ₅ represents a galloyl group or a glucopyranosyl group), represented by flavan-3-ol or flavan-3,4-diol as a constituent unit. A group of compounds linked by condensation or polymerization at the 4th or 4th to 8th positions, and are condensed tannins present in various plants. In addition, chemical formula 1 shows only the case where condensation is performed at the 4-8 position to facilitate understanding. These are given the name because they produce anthocyanidins such as cyanidin, delphinidin and pelargonidin by acid treatment. The dimer, the trimer, the tetramer, and the 10 to 30-mer or more of the above structural units include proanthocyanidins such as procyanidin, prodelphinidin, and properargonidine, and stereoisomers thereof.

Claims (5)

[Claims] 1. A method for reducing the astringency of proanthocyanidins, comprising adding a protein and / or a polysaccharide to an extract containing proanthocyanidins as a main component obtained by extracting a plant. 2. The proanthocyanidin according to claim 1, wherein the plant extract is one selected from extracts of fermented grape food, grape seed, grape skin and grape juice cake. Astringency reduction method. 3. The method for reducing astringency of proanthocyanidins according to claim 1, wherein the protein is skim milk powder and / or isolated soy protein. 4. The method for reducing astringency of proanthocyanidins according to claim 1, wherein the polysaccharide is starch and / or agar. 5. A proanthocyanidin composition having reduced astringency, wherein a protein and / or polysaccharide is added to an extract containing proanthocyanidin as a main component obtained by extracting a plant.