TW201347687A - Polyphenol stabilizer, and composition and processed goods containing said stabilizer - Google Patents

Abstract

The present invention addresses the problem of providing: a polyphenol stabilizer which, in processed goods which contain polyphenols such as cacao procyanidins or tea catechins, can minimize the epimerization of epicatechins or the decrease of procyanidins, the epimerization and the decrease occurring either during thermal extraction or heat sterilization or in storage under neutral or alkaline conditions; and a composition, food, drink, drug or cosmetic that contains the stabilizer. The stabilization of a polyphenol can be attained by making a stabilizer containing ellagic acid and/or punicalagin coexist with the polyphenol. The stabilizer may be a plant extract such as pomegranate extract, purified ellagic acid, purified punicalagin or a mixture of two or more of them.

Description

Polyphenol stabilizer, composition and processed product containing the stabilizer

The present invention relates to a stabilizer for a polyphenol and a polyphenol composition containing the stabilizer. Further, the present invention relates to a processed product containing polyphenols for foods and drinks, pharmaceuticals or cosmetics produced by using the above polyphenol composition. More specifically, the present invention relates to an epimerization inhibitor and/or a proanthocyanidin-lowering inhibitor of the epic catechins, a polyphenol composition containing the inhibitors, and Processed products containing polyphenols.

Polyphenols are contained in various plants such as fruits or vegetables. It is generally known that ingesting polyphenols is beneficial for healthy maintenance.

For example, cocoa contains cocoa polyphenols. Cocoa polyphenols are known to have various physiological effects such as anti-oxidation, tartar formation inhibition, anti-tumor action, anti-stress action, and cancer prevention. Representative components of cocoa polyphenols are epicatechin, catechin, procyanidin B2, proanthocyanidin B5, proanthocyanidin C1, Cinnamtannin A2 and the like.

In addition, teas such as green tea, black tea, and oolong tea are rich in tea polyphenols. Tea polyphenols are known to have antioxidant activity, antibacterial action, and inhibit bile Various physiological effects such as sterol rise. Representative components of tea polyphenols are broadly classified into non-epidermal catechins and epiphytic catechins. Non-epidermal catechins include catechins, gallocatechin, catechin gallate, gallocatechin gallate, and the like. Further, the epicatechin catechins include epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate, and the like.

Polyphenols are known to change structure with pH or temperature changes due to heating. For example, epicatechins contained in cocoa polyphenols are known to be present as (-)-epicatechin during extraction, but epimerized to (-)-catechin in a hot water-soluble solution. Prime. On the other hand, as a method of minimizing the above-described epimerization, a method of lowering the heating temperature, lowering the pH, and/or shortening the heating time has been proposed (Patent Document 1). Further, regarding the components contained in the tea polyphenol, it is known that the step of producing the tea beverage in the container, in particular, the step of extracting the tea leaves by warm water or the step of sterilizing after filling the extract in the container causes a natural type Isomerization of catechins. On the other hand, as a method of suppressing the isomerization of the natural catechins, it is proposed to add L-ascorbic acid to the tea extract or the extraction water, and adjust the pH of the tea extract to 5 or less, followed by heating. Method of sterilization (Patent Document 2).

Prior technical literature Patent literature

Patent Document 1: Special Table 2008-544762

Patent Document 2: JP-A-2006-191851

Non-patent literature

Non-Patent Document 1: J. Agric. Food Chem., Vol. 55 No. 23, 9559-9570, 2007

Non-Patent Document 2: Biosci. Biotechnol. Biochem., Vol. 64 No. 12, 2581-2587, 2000

Non-Patent Document 3: J. Agric. Food Chem., Vol. 45 No. 12, 4624-4628, 1997

Non-Patent Document 4: Food Chemistry 68 (2000) Yinrong Lu, L. Yeap Foo "Antioxidant and radical scavenging activities of polyphenols from apple pomace"

Non-Patent Document 5: J. Agric. Food Chem., Vol. 25 No. 6, 1268-1273, 1977

In the processed product containing polyphenols, in order to exert the physiological function of polyphenols, it is desirable that the formulated polyphenols can be stably present, and the physiological effects can be maintained even in the processed products.

However, in the production of processed products such as general foods and drinks, conditions such as pH 4 or higher and 37 ° C or higher are applied in the treatment steps such as storage, heating, and sterilization. Under these conditions, polyphenols are usually not safe Definite existence. For example, when the epicatechin catechins are stored at a pH of 4 or higher, they are epimerized into non-epidermal catechins. Moreover, when the proanthocyanidins are heated and stored at pH 4 or higher, the structure changes, and the total amount in the processed product to be tested is reduced over time.

As seen in Patent Documents 1 and 2, the stabilization technique of the polyphenol proposed so far is related to the adjustment of the conditions of pH, heating temperature, and heating time. According to this past method, the pH of the processed article or the processing conditions in the manufacturing steps thereof are limited. Therefore, a means for stabilizing polyphenols in a simpler manner is required.

An object of the present invention is to provide a stabilizer for effectively stabilizing polyphenols. In particular, the present invention intends to provide a stabilizer which is effective in the stabilization of polyphenols, as means for inhibiting epimerization of epicatechins and/or means for suppressing reduction of proanthocyanidins. Another object of the present invention relates to a polyphenol-containing composition which contains a stabilizer of the above polyphenol and which can stably maintain the original physiological function after the preparation of the polyphenol, and a processed product comprising the composition.

The inventors of the present invention actively reviewed various components having an effect of stabilizing polyphenols. As a result, it was found that plant extracts such as red pomegranate extract are useful for the stabilization of polyphenols. In particular, ellagic acid and punicalagin, which are abundant in red pomegranate extract, have a significant effect on the stabilization of polyphenols. The present invention has been completed based on the findings, and is characterized by the matters described below.

(1) A stabilizer which is a stabilizer for polyphenols and which comprises at least one of ellagic acid and punica glucoside.

(2) The stabilizer according to the above (1), wherein the content of at least the ellagic acid is 15% by weight or more based on the total weight of the stabilizer, or the content of the punica glucoside is 30% by weight. %the above.

(3) The stabilizer according to the above (1) or (2), wherein the polyphenol stabilizer is an epimerization inhibitor of epicatechins.

(4) The stabilizer according to the above (1) or (2), wherein the polyphenol stabilizer is a reduction inhibitor of proanthocyanidins.

The stabilizer of any one of the above-mentioned (1) to (4), wherein the stabilizer is a plant extract containing at least one of ellagic acid or punical glucoside.

The stabilizer of any one of the above (1) to (5), wherein the plant extract is a red pomegranate extract.

(7) A composition comprising a polyphenol, and a stabilizer for at least one of ellagic acid and guaranuridine.

The composition of the stabilizer according to any one of the above (1) to (6), wherein the composition of the polyphenol is 100% with respect to the above polyphenol 100. The stabilizer is contained in an amount of at least 1.5 parts by weight or more, or at least 5 parts by weight or more of the above ellagic acid.

(9) The composition according to the above (7) or (8), wherein the polyphenol is at least one selected from the group consisting of proanthocyanidins and catechins.

(10) The composition according to any one of the above (7), wherein the stabilizer is at least one of ellagic acid or guaranol Plant extracts.

(11) The composition according to any one of the above (7), wherein the plant extract is a red pomegranate extract.

(12) A processed product comprising a polyphenol, which is selected from the group consisting of food and beverage, pharmaceuticals, and cosmetics, which is composed of the composition according to any one of the above (7) to (11) .

(13) The processed product containing polyphenols according to the above (12), wherein the polyphenol-containing processed product has a pH of 4.0 to 8.0.

(14) A method for producing a processed article containing a polyphenol, comprising the steps of: (a) modulating the composition according to any one of the above (7) to (11), b) a step of preparing a processed article containing polyphenol using the above composition, and (c) a step of heating the processed article containing polyphenol to a temperature of 37 ° C or higher.

(15) A processed product containing polyphenols, which is selected from the group consisting of foods, foods, pharmaceuticals, and cosmetics, which are produced by the production method described in the above (14).

(16) A method for the stabilization of polyphenols, which comprises at least 1.5 parts by weight or more of ellagic acid or 5 parts by weight or more of guaranuric acid based on 100 parts by weight of the polyphenol.

According to the present invention, it is possible to provide polyphenol stability which can effectively stabilize polyphenols in a pH or temperature range in which the polyphenol structure changes in common sense. Chemical agent. Further, according to the present invention, it is possible to provide a polyphenol composition which can stably maintain the physiological function of the polyphenol when it is applied to a processed product by allowing the stabilizer to coexist with the polyphenol. Further, various processed products containing polyphenols such as foods and drinks, pharmaceuticals, and cosmetics using the above composition can be provided. The processed product containing polyphenol of the present invention can be applied by extraction treatment using hot water and retort sterilization treatment, and can be stored for a long period of time in the form of a liquid product in a neutral pH region. In general, under such treatment and storage conditions, epimerization or proanthocyanidins of epiphytic catechins are known to be reduced. However, according to the present invention, with the above stabilizer, the polyphenol can be stably maintained in a state of being formulated.

The disclosure of the present invention is the subject of Japanese Patent Application No. 2012-63334, the entire disclosure of which is incorporated herein by reference.

FIG. 1 is a chart relating to Example 1. This chart shows the reduction inhibitory effect of proanthocyanidins obtained from various plant extracts (before and after heat sterilization).

2 is a chart relating to Example 1. This chart shows the epimerization inhibition effect (before and after heat sterilization) obtained from various plant extracts.

Fig. 3 is a chart relating to Example 2. This chart shows the reduction inhibitory effect of proanthocyanidins obtained by various plant extracts (in warming retention).

4 is a graph relating to Example 2. This chart shows the epimerization inhibition effect (heating retention) obtained with various plant extracts.

Fig. 5 is a chart relating to Example 3. The graph shows the reduction inhibitory effect of proanthocyanidins obtained from red pomegranate extract (90% ellagic acid) (before and after heat sterilization).

Fig. 6 is a chart relating to Embodiment 3. The graph shows the epimerization inhibition effect (before and after heat sterilization) obtained from the pomegranate extract (90% ellagic acid content).

Fig. 7 is a chart relating to Embodiment 3. The graph shows that the proanthocyanidins obtained by the red pomegranate extract (90% ellagic acid content) have a reduced inhibitory effect (in warm storage).

Fig. 8 is a chart relating to Example 3. The graph shows the epimerization inhibition effect (in warm storage) obtained with red pomegranate extract (90% ellagic acid content).

Fig. 9 is a chart relating to Example 4. The graph shows the reduction inhibitory effect of proanthocyanidins obtained before and after heat sterilization with various red pomegranate extracts (15-40% ellagic acid content, 30% guaranuric acid content).

Fig. 10 is a chart relating to Example 4. The graph shows the epimerization inhibition effect (before and after heat sterilization) obtained from various red pomegranate extracts (15 to 40% ellagic acid content and 30% guaranuril content).

Figure 11 is a graph of Example 4. The graph shows the reduction inhibitory effect of proanthocyanidins obtained by extracting red pomegranate (40% ellagic acid) (in warm storage).

Figure 12 is a chart relating to Example 4. The chart shows the redstone The epimerization inhibitory effect (in warm storage) obtained from the extract of scent (40% ellagic acid).

Figure 13 is a chart of Example 4. The graph shows the reduction inhibitory effect of proanthocyanidins obtained by extracting red pomegranate (15% ellagic acid) (in warm storage).

Figure 14 is a chart relating to Example 4. The graph shows the epimerization inhibition effect (in warm storage) obtained with red pomegranate extract (15% ellagic acid content).

Figure 15 is a chart relating to Example 4. The graph shows the reduction inhibitory effect of proanthocyanidins obtained by extracting red pomegranate (30% guaranzol) (in warm storage).

Figure 16 is a chart relating to Example 4. The graph shows the epimerization inhibition effect (in warm storage) obtained with red pomegranate extract (30% guaranol content).

Figure 17 is a chart relating to Example 5. The graph shows the reduction inhibitory effect of proanthocyanidins obtained by ellagic acid purified product (test drug) and purified pomegranate (test drug) (before and after heat sterilization).

Fig. 18 is a chart relating to Example 5. The graph shows the epimerization inhibition effect (before and after heat sterilization) obtained by ellagic acid purified product (test drug) and purified pomegranate product (test drug).

Fig. 19 is a chart relating to Example 5. The graph shows the reduction inhibitory effect of proanthocyanidins obtained by purifying ellagic acid (test drug) and purified pomegranate (test drug) (in warm storage).

Figure 20 is a chart relating to Example 5. The chart shows the flower The effect of the isomerization inhibition obtained by the acid purified product (test drug) and the purified pomegranate product (test drug) (in warm storage).

Figure 21 is a chart relating to Example 6. This graph shows the epimerization inhibition effect (before and after heat sterilization) of catechins obtained by ellagic acid purified product (test drug).

Figure 22 is a chart relating to Example 7. This graph shows the epimerization inhibitory effect of catechins obtained before and after various concentrations of ellagic acid purified product (test drug) (before and after heat sterilization).

Figure 23 is a chart relating to Example 7. This graph shows the epimerization inhibitory effect (in warm storage) of catechins obtained by purifying ellagic acid (test drug) at various concentrations.

Figure 24 is a chart relating to Example 8. This graph shows the effect of reducing the inhibitory effect of proanthocyanidins in a beverage containing cocoa polyphenol (pH 6.5).

Figure 25 is a chart relating to Example 8. This chart shows the epimerization inhibition effect in a beverage containing cocopolyphenol (pH 6.5).

Fig. 26 is a chart regarding Comparative Example 1. This chart shows the results of the test for reducing the inhibitory effect of proanthocyanidins obtained by gallic acid.

Fig. 27 is a chart regarding Comparative Example 1. This chart shows the test results of the epimerization inhibition effect obtained with gallic acid.

28 is a graph relating to Reference Example 1. This chart shows the relationship between the antioxidant activity of various plant extracts and the residual rate of proanthocyanidins.

29 is a graph relating to Reference Example 1. This chart shows the relationship between the total amount of polyphenols in various plant extracts and the residual rate of proanthocyanidins.

The details of the invention are described below.

<安定化剂>

The first aspect of the present invention is a polyphenol stabilizer which is characterized by comprising at least one of ellagic acid and punica glucoside. Details are as follows.

(Ellagic acid)

The term "ellaric acid" as used in the present invention means a substance represented by the following structural formula (Chemical Formula 1).

(an pomegranate)

The "anatillin" of the present invention means a substance represented by the following structural formula (Chemical Formula 2). Angina is a kind of ellagitannin contained in plants such as red pomegranate. Thistle tannin is a hydrolyzed tannin having hexahydroxydiphenoyl.鞣 Flower tannins produce ellagic acid upon acid decomposition.

(anti-setting agent)

The stabilizer of the present invention contains at least one of the above ellagic acid and the above-mentioned punica glucoside as an active ingredient. Although it is not particularly limited, in one embodiment of the present invention, the content of the ellagic acid is preferably 15% by weight or more based on the total weight of the stabilizer. Further, the content of the punny glucoside is preferably 30% by weight or more based on the total weight of the stabilizer. When the stabilizer is contained in at least one of ellagic acid and punical glucoside in the above content range, the stabilization of the polyphenol can be facilitated by the stabilizer. Further, the stabilizer of the present invention may be mixed with ellagic acid and punical glucoside, and the ratio thereof is not particularly limited. The stabilizer of the present invention is not particularly limited as long as it does not substantially affect the effects obtained by the above respective components, and may include other various components conventionally known to those skilled in the art.

The above ellagic acid and the above-mentioned punical guava are known to exist in many plants such as fruits. Plants rich in ellagic acid are listed, for example, as red pomegranate. Strawberries, raspberries, cranberries, grapes, chestnuts, walnuts, etc. A plant extract containing at least one of ellagic acid and punica glucoside may also be used as the stabilizer for the present invention. For example, the stabilizer of the present invention may use a plant extract of red pomegranate extract, strawberry extract, raspberry extract, cranberry extract, grape extract, chestnut extract, and walnut extract. Preferably listed as red pomegranate extract. The above plant extract is preferably a juice or a concentrated juice. In one embodiment of the present invention, a commercially available red pomegranate extract containing at least one of ellagic acid and guaranurin can be used as a stabilizer. For example, as an embodiment of the stabilizer of the present invention, a red pomegranate extract (containing 40% of ellagic acid) manufactured by NATURAX and a pomegranate extract (containing 90% or more of ellagic acid) manufactured by BIO ACTIVES of Japan are listed. , the red pomegranate extract made by ARJUNA (15-20% of ellagic acid after hydrolysis), Pomella (registered trademark) by OMNICA (containing more than 30% of pomegranate).

In the present invention, as the stabilizer, a purified product of ellagic acid and/or punical glucoside may be used in addition to the above plant extract. The above purified product may be one in which the concentration of ellagic acid or punical glucoside of the above plant extract is increased to 90 to 100% by weight according to a conventional method. Further, the purified product may be ellagic acid or punical glucoside which is sold as a reagent. That is, in the present invention, a group consisting of a purified product of ellagic acid, a purified pomegranate, and a plant extract containing at least one of ellagic acid and guaranuric acid, preferably a red pomegranate extract, may be used. One or more selected ones are used as stabilizers.

In one embodiment of the stabilizer of the present invention, The content of ellagic acid is from 15 to 100% by weight, preferably from 30 to 100% by weight, more preferably from 40 to 100% by weight, most preferably from 90 to 100% by weight, based on the total weight of the tempering agent. In another embodiment of the stabilizer of the present invention, the content of guavaside is 30 to 100% by weight, preferably 40 to 100% by weight, more preferably 80 to 100% by weight. Further, in another embodiment of the stabilizer of the present invention, when the content of ellagic acid is 15 to 100% by weight based on the weight of the total stabilizer, the guaranol is in the range of 85 to 0% by weight. Any ratio exists. Further, similarly, when the content of punical guavaside is 30 to 100% by weight, the ellagic acid is present in an arbitrary ratio in the range of 70 to 0% by weight.

The form of the stabilizer of the present invention is not limited, and may be any of liquid, powder, granules and the like.

(polyphenol)

The term "polyphenol" as used in the present invention means a compound having a structure in which two or more hydroxyl groups are present on a benzene ring. However, the above polyphenol does not contain ellagic acid and punical glucoside as a stabilizer in the present invention. Polyphenols are classified into simple phenols, flavonoids, hydrolyzed tannins, and condensed tannins (proanthocyanidins). An example of the above simple phenols is exemplified by dihydroxy acids and hydroxycaffeic acid derivatives. One example of the above flavonoids is flavonoids, flavonols, isoflavones, flavans, flavanols (catechins), flavanones, flavanones (flavanonol). ), chalcone, anthocyanins (anthocyanidin) class. In particular, an example of the above catechins is catechin and epicatechin. The hydrolyzed tannins are polymers of the above simple phenols, and the condensed tannins (proanthocyanidins) are polymers of the above flavonoids. In particular, one of the above anthocyanins is exemplified by proanthocyanidins.

Although it is not particularly limited, in one embodiment of the present invention, the polyphenol is preferably at least one selected from the group consisting of proanthocyanidins and catechins. More specifically, cocopolyphenol and tea polyphenol are preferred, and cocoa polyphenol is preferred. The above-mentioned cocoa polyphenol is a proanthocyanidin obtained from a raw material of cocoa. On the other hand, the above tea polyphenols are catechins obtained from tea raw materials.

(stabilization of polyphenols)

The "stabilization of polyphenols" in the present invention means to suppress the structural change of the above polyphenols due to pH or heat. More specifically, it means that the stabilizer of the present invention inhibits the processing conditions such as storage, heating and sterilization which are applied at a pH of 4.0 or higher, more specifically, at a pH of 4.0 or more and 37 ° C or more. The structural changes of the phenol can maintain the polyphenols in an initial state. The above structural change can be confirmed by, for example, a change in the ratio of the epimers in the epicatechin catechins and a decrease in the amount of detection of the proanthocyanidins. The details of the mechanism of action of the stabilizer of the present invention are not clear, but it is presumed that the stabilizer can maintain the polyphenol compound as an initial stereospecific ligand when the stabilizer is acted as a differential conformation inhibitor. The way it works.

(catechins)

The above-mentioned "catechins" described in the present invention are a general term for epicatechin catechins and non-epitopic catechins. Specific examples of the above-mentioned "epidermal catechins" include epicatechin, epigallocatechin, and epigallocatechin gallate. Specific examples of the "non-epidermal catechins" include catechins, gallocatechin, and gallocatechin gallate.

(Inhibition of epimerization of epigenetic catechins)

It is known that the above-mentioned epigenetic catechins cause epimerization and change to non-epithelial catechins under the conditions of pH 4.0 or higher. For example, under conditions of pH 4.0 or higher, (-)-epicatechin contained in cocoapolyphenol or the like is epimerized to (-)-catechin. Similarly, the (-)-epigallocatechin gallate-containing gallate contained in the tea extract is epimerized to (-)-gallocatechin gallate. Furthermore, epigallocatechin is separately epimerized to gallocatechin, and epicatechin gallate is epimerized to catechin gallate. On the other hand, by allowing the stabilizer of the present invention to coexist with the epicatechin catechin, the epimerization can be effectively suppressed.

Although not particularly limited, in one embodiment of the present invention, the isomerization of cocoa polyphenols is carried out by using a stabilizer of 15% by weight or more of ellagic acid based on the total weight of the stabilizer. Both the inhibition of the inhibition and the inhibition of the isomerization of the tea polyphenol can give good results. And, based on the weight of the stabilizer, by using 30 weights A stabilizer of more than 5% of pomegranate can obtain good results for the inhibition of epimerization of cocoa polyphenol.

(original anthocyanins)

The term "proanthocyanidin" in the present invention means a substance having a structure in which a basic skeleton of flavonoids is polymerized. Proanthocyanidins are contained in cocoa, grape seeds, grape skins, apples, pine bark, and the like. Representative proanthocyanidins contained in cocoa polyphenols include proanthocyanidin B2, proanthocyanidin B5, proanthocyanidin C1, cassia tannin A2, and the like. The "proanthocyanidins" described in the present invention comprise a total of 6 components derived from epicatechin, catechin, proanthocyanidin B2, proanthocyanidin B5, proanthocyanidin C1, and cinnabarin A2.

(Reduction inhibition of proanthocyanidins)

The proanthocyanidins are reduced by heating and storage under conditions of pH 4.0 or higher, more specifically pH 4.0 or higher and 37 ° C or higher. However, by allowing the stabilizer of the present invention to coexist with the proanthocyanidins, the reduction of the proanthocyanidins can be effectively suppressed.

<Composition containing stabilizers>

A second aspect of the present invention relates to a composition comprising a stabilizer of at least one of polyphenols, ellagic acid and punical guava. That is, the polyphenol composition of the present invention is characterized by comprising a raw material containing a polyphenol and a stabilizer of the first aspect of the present invention. In one embodiment of the present invention, the stabilizer may be a plant extract containing at least one of ellagic acid and punical glucoside, preferably For red pomegranate extract. Furthermore, in another embodiment, the stabilizer may be a purified ellagic acid product or a purified product of punica glucoside.

In the composition of the present invention, the amount of the stabilizer to be used is not particularly limited. However, in one embodiment, the stabilizer is blended in an amount of at least 1.5 parts by weight or more of the ellagic acid or 5 parts by weight or more based on 100 parts by weight of the polyphenol. As will be understood from the examples described later, by using the stabilizer in the above ratio, it is easy to maintain the polyphenol in the composition stably. The polyphenol is preferably one or more selected from the group consisting of proanthocyanidins and catechins. More specifically, it is preferably cocopolyphenol and/or tea polyphenol, preferably cocopolyphenol. Further, the composition of the present invention may contain other various components known to those skilled in the art as long as it does not substantially affect the stabilization effect of the polyphenol. The polyphenol composition of the present invention can be used as a raw material of a processed product such as a food additive, or can be used as a processed product such as a food.

According to the composition of the present invention, in a processed product having a pH of 4.0 or higher or a processed product which is subjected to heat treatment at a temperature of 37 ° C or higher, when the composition is formulated, the physiological property of the polyphenol can be imparted to the processed product. function. Further, according to the above composition, the polyphenol state before the above processing can be maintained stably after processing or storage.

<Processed Products Containing Polyphenols>

A third aspect of the present invention relates to a polyphenol-containing processed article comprising a stabilizer of at least one of polyphenols, ellagic acid and punical guava. Specific examples of the above processed products include foods and drinks, pharmaceuticals, and cosmetics. Not yet In particular, in one embodiment of the present invention, the processed product is preferably a food or beverage. Among them, beverages are preferred, and beverages are preferably packaged in containers.

The processed product may be formed by using the polyphenol composition of the second aspect of the present invention as a raw material or as a part of the raw material. That is, in the embodiment of the processed product of the present invention, the composition may be intentionally made to contain an additional component depending on the desired form of the processed product. In such an embodiment, the amount of the stabilizer to be used is not particularly limited. However, in one embodiment of the present invention, it is preferred to blend the above stabilizer with at least 1.5 parts by weight or more of the ellagic acid or 5 parts by weight or more of the guaiac acid in an amount of at least 100 parts by weight of the polyphenol. . By using the above stabilizer in the above ratio, it becomes easy to stably maintain the polyphenol in the processed product. On the other hand, the upper limit of the amount of the stabilizer is not particularly limited, and may be set in consideration of taste, flavor, and cost. For example, it may be blended in the processed product in an amount of from 1.5 to 350 parts by weight, and/or from 5 to 350 parts by weight of guaranuric acid, based on 100 parts by weight of the polyphenol contained in the processed product.

(food and drink)

Hereinafter, foods and drinks will be specifically described as an example of the processed product of the present invention. The food and beverage products include polyphenols and the above-mentioned stabilizers, and others are well known to those skilled in the art. Specific examples of the food and drink are, for example, beverages, cocoa, coffee, chewing gum, soft candy, jelly, alpaca, SHERPET, and dairy products. The form of the food or drink is not particularly limited, but is preferably a food having a high water content or a beverage or food having a heat sterilization process after the container is packaged. The water content of the above food is preferably 10% by weight or more.

The pH of the above foods and drinks is not limited. However, it is known that when pH is 4.0 or more, it causes an undesirable phenomenon of epimerization of epicatechin catechins or reduction of pomegranate. Moreover, it is known that such phenomena are promoted by heating. However, according to the present invention, the above-mentioned undesired phenomenon can be effectively suppressed by using the above-mentioned stabilizer in the processed product. Therefore, the pH of the processed article of the present invention may be 4.0 or more. From the viewpoint of the stabilization effect of the above-mentioned stabilizer, the pH of the food or beverage is preferably from 4.0 to 8.0, more preferably from 4.0 to 7.5, still more preferably from 5.5 to 6.5.

Further, the food or beverage may be one which has a pH in the above range and is heated at a temperature of 37 ° C or higher. In particular, the food or beverage may be produced by a step of heat sterilization at a temperature of 120 ° C or higher. In addition, the above-mentioned "step of heating at a temperature of 37 ° C or higher" includes not only the production of foods and drinks, but also the step of storing and selling the food and beverage at 37 ° C or higher.

In the present invention, the polyphenol content in the above foods and drinks is not particularly limited. In general, the polyphenol content in foods and drinks is set in such a manner that the physiological function of the object can be exerted. Therefore, in the present invention, the amount of the stabilizer to be used may be determined by setting the amount of the polyphenol in the food or beverage. For example, the stabilizer may be formulated in an amount of at least 1.5 parts by weight of ellagic acid or 5 parts by weight or more of guaiac with respect to 100 parts by weight of the polyphenol content.

The food or drink can be produced, for example, according to the methods (i) to (iii) below. (i) Preparation of beverages: blending 28.5mg~100mg polyphenols, A 100 ml beverage is prepared by adding 0.5 mg to 100 mg of the stabilizer and the ingredients known in the art as needed. Here, the polyphenol may be, for example, a proanthocyanidin or a catechin. Further, the stabilizer may be, for example, a purified ellagic acid product, a purified pomegranate, or at least 15% by weight of ellagic acid and 30% by weight or more of guaranuric acid based on the total weight of the stabilizer. Any of the red pomegranate extracts of at least one of them. Further, the above-mentioned known component is preferably a raw material used as a raw material or an additive of a general food or beverage. For example, the beverage product may also contain water, sugar, sugar alcohol, starch and processed starch, dietary fiber, milk, processed milk, soy milk, juice, vegetable juice, fruits and vegetables and processed products, protein, peptide, amine Base acid, animal and plant herbal extracts, natural polymers (collagen, hyaluronic acid, chondroitin, etc.), vitamins, minerals, tackifiers, emulsifiers, preservatives, colorants, perfumes, etc.

(ii) pH adjustment of the beverage: The pH of the beverage prepared as described above was adjusted to a range of 5.5 to 6.5. When adjusting, organic acids and their salts, sour agents or pH adjusters may also be used as needed. More specifically, malic acid and its salts, citric acid and its salts, tartaric acid and its salts, lactic acid and its salts, phosphoric acid and its salts, calcium carbonate and sodium hydrogencarbonate are also added to the above beverages. Sodium carbonate and the like.

(iii) Heat sterilization of the beverage: The pH-adjusted beverage is sealed in a closed container and heat-sterilized at a temperature of, for example, 121 ° C for 10 minutes.

(Other processed products)

As described above, the food and beverage product will be described as an example of the embodiment of the processed product of the present invention. However, according to the present invention, a composition comprising a polyphenol and a stabilizer containing at least one of ellagic acid and guaranuric acid may be used to constitute a pharmaceutical product (including a quasi-drug) or other processed product of the cosmetic. In the case of constituting a pharmaceutical product as a processed product, the above-mentioned pharmaceutical product contains components well known to those skilled in the art in addition to the above components. For example, in one embodiment of the present invention, the pharmaceutical product preferably contains a polyphenol, the stabilizer, a pharmaceutical medicinal ingredient, and a pharmaceutical preparation that is not a pharmacy drug or a quasi-drug. Substances other than ingredients. Specific examples of the above substances include excipients, disintegrators, binders, fluidizers, flavoring agents, perfumes, colorants, sweeteners, solvents, fats and oils, tackifiers, surfactants, and gelling agents. , stabilizers, preservatives, buffers, suspending agents, thickeners, etc. The form of the pharmaceutical product is not particularly limited. The pH of the above pharmaceutical product may be 4.0 or more based on the same viewpoint as the above-mentioned food and drink. The pH of the above-mentioned pharmaceutical product is from 4.0 to 8.0, more preferably from pH 4.0 to 7.5, more preferably from pH 5.5 to 6.5, from the viewpoint of the stabilization effect of the above stabilizer. Further, the above-mentioned pharmaceutical product may be produced by a step of heating at 37 ° C or higher.

On the other hand, when the cosmetic is constituted as a processed product, the cosmetic may contain components well known to those skilled in the art in addition to the above components. For example, in one embodiment of the present invention, the cosmetic comprises a polyphenol, the stabilizer, and a component which can be used as a cosmetic via a core. As the above-mentioned components, for example, perfumes, metals, ceramics or excipients, disintegrators, binders, fluidizers, slip agents, colorants, solvents, greases, surfactants, tackifiers, gelatinization are exemplified. Agents, etc. The form of cosmetics, not Special restrictions. The pH of the above cosmetic may be 4.0 or more based on the same viewpoint as the above food and beverage. From the viewpoint of the stabilization effect of the above stabilizer, the pH of the above cosmetic is preferably from 4.0 to 8.0, more preferably from 4.0 to 7.5, still more preferably from 5.5 to 6.5. Further, the above-mentioned cosmetics may be manufactured by a step of heating at 37 ° C or higher.

<Method for Producing Processed Article Containing Polyphenols>

The fourth aspect of the present invention relates to a method of producing a processed article containing polyphenol. The above production method comprises the steps of: (a) preparing a composition comprising a polyphenol and a stabilizer containing at least one of ellagic acid and punical guaranurine, and (b) using the above composition to prepare a polyphenol The step of processing the product, (c) the step of heating the processed product containing the polyphenol to a temperature of 37 ° C or higher. In the above production method, the above-mentioned processed product is preferably the same as the third aspect of the present invention. In one embodiment of the production method of the present invention, in the step (a), it is preferred that at least 1.5 parts by weight of ellagic acid or 5 parts by weight of guaranuric acid are added to 100 parts by weight of the polyphenol. The above stabilizers coexist. The pH of the above-mentioned polyphenol-containing processed product is preferably in the range of 4.0 to 8.0. Further, the polyphenol is preferably at least one of a proanthocyanidin and a catechin.

<Method for the stabilization of polyphenols>

The fifth aspect of the present invention relates to a method for the stabilization of polyphenols, which is characterized in that at least 1.5 parts by weight of ellagic acid or 5 parts by weight or more of guaranuric acid coexist with respect to 100 parts by weight of polyphenol. Above polyphenols, on The ellagic acid, the above proanthocyanidins are as previously described. As explained earlier, an undesirable phenomenon of epimerization or reduction of proanthocyanidins of epicatechins can be seen at pH 4.0 or higher. Therefore, from the viewpoint of effectively carrying out the stabilization method of the present invention, the above stabilization is preferably carried out under conditions of pH 4.0 or higher. The pH condition of the above stabilization is preferably from 4.0 to 8.0, more preferably from 4.0 to 7.5, and most preferably from 5.5 to 6.5.

Under the above-mentioned pH conditions, structural changes of the above polyphenols are promoted by application of heating. Therefore, in view of more effective implementation of the stabilization of the present invention, in addition to the above-mentioned pH conditions, it is preferred to carry out the above stabilization under the conditions of heating at 37 ° C or higher, preferably at 120 ° C or higher. .

Another aspect of the present invention relates to a processed article containing polyphenols which is selected from the group consisting of foods, foods, pharmaceuticals, and cosmetics manufactured by the method of the third aspect of the present invention. Further, in other aspects, at least one of ellagic acid and punica glucoside is used as a polyphenol stabilizer.

The above description is based on the representative aspect of the present invention. However, the present invention is not limited to the illustrated embodiments, and various modifications can be made without departing from the spirit and scope of the invention.

Example

Hereinafter, the present invention will be specifically described by way of examples. However, the embodiments of the present invention are not limited to the following embodiments.

In the examples and comparative examples, the quantitative analysis of each component is as follows. Implemented as follows.

(ellagic acid, pomegranate)

The quantitative analysis of ellagic acid and punical glucoside is carried out by referring to the method described in Non-Patent Document 1 (J. Agric. Food Chem., Vol. 55 No. 23, 9559-9570, 2007).

(epidermal catechins, non-epi catechins)

Epigenetic catechins (epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate) and non-epidermal Quantitative analysis of the tea catechins (catechin, gallic acid catechin, catechin gallate, gallic acid catechin gallate) is based on Non-Patent Document 2 (Biosci. The method described in Biotechnol. Biochem., Vol. 64 No. 12, 2581-2587, 2000) was carried out.

(original anthocyanins)

Quantitative analysis of proanthocyanidins (catechin, epicatechin, proanthocyanidin B2, proanthocyanidin B5, proanthocyanidin C1, cassia tannin A2) is based on Non-Patent Document 3 (J. Agric. Food Chem., Vol. 45 No. 12) , 4624-4628, 1997) Implementation.

The cocopolyphenols used in the examples and comparative examples were prepared as follows.

(Modulation method of cocoa polyphenol)

The cocoa beans which have been dried in the production area are ground and further degreased by pressing, and a 20-fold amount of 50% aqueous ethanol solution is added and stirred at 50 ° C for 30 minutes. Next, the undesired component is removed by centrifugation to obtain a crude extract of cocoa.

Next, in the column packed with the cation exchange resin (Amberlite (registered trademark) IR-120B) to which hydrogen ion exchange treatment was previously applied, the above-mentioned crude extract of cocoa was introduced at a flow rate of SV=5. Next, deionized water at 25 ° C was passed through the column, and the eluate was separated. Cocoa polyphenol (proanthocyanidin content of about 16% by weight) was obtained by freeze-drying the above-mentioned eluate.

(Example 1)

Polyphenol stabilization effect of various plant extracts (before and after sterilization)

(i) modulation of beverages

To 350 mg of the plant extract (or reagent) shown in Table 1 and 625 mg of the cocoa polyphenol (100 mg of proanthocyanidin) obtained by the above method, water was added to prepare 350 ml of a solution. The above solution was adjusted to pH 5.5 using 0.1 M hydrochloric acid or 0.1 M sodium hydroxide to prepare a beverage.

(ii) sterilization

The above beverage was sealed in a sealed container and heat-sterilized at 121 ° C for 10 minutes in an autoclave.

(iii) Polyphenol analysis

The proanthocyanidins are respectively quantified according to the above-described quantitative methods for the pre-heat sterilization beverage obtained in the above (i) and the respective beverages after the heat sterilization obtained in the above (ii).

(iv) Evaluation of the reduction effect of proanthocyanidins

The amount of each component of the proanthocyanidins obtained by the above (iii) is as follows The residual rate of proanthocyanidins is calculated.

Residual rate of proanthocyanidins (%) = (sum of proanthocyanidins in beverages after heat sterilization / sum of proanthocyanidins in beverages before heat sterilization) *100

The higher the residual ratio value, the more stable the proanthocyanidins in the beverage after heat sterilization. That is, it shows that the reduction effect of the proanthocyanidins is higher. The results are shown in Figure 1.

As can be seen from Fig. 1, the red pomegranate extract (1), the red pomegranate extract (2), the orange gum extract and the hawthorn extract showed a residual rate of proanthocyanidins as high as 80% or more after heat sterilization. In particular, two red pomegranate extracts (containing 40% to 90% of ellagic acid) are shown as polyphenol stabilizers having a higher inhibitory effect on proanthocyanidins.

(v) Evaluation of inhibitory effect of epimerization

The epimer ratio was calculated by using the values of epicatechin and catechin in the proanthocyanidins quantified in the above (iii).

Epimer ratio (%) = (epicate catechins in each beverage / epicatechin amount in each beverage + catechin amount) * 100

The closer the value of the epimer ratio in each beverage after heat sterilization is the value of the ratio of the epimers in the beverage before sterilization, that is, the higher value indicates the surface of the beverage after heat sterilization. The tea is not heterogeneously converted into catechins, but is preserved with epicatechin. The results are shown in Figure 2.

As seen in Figure 2, red pomegranate extract (1), redstone The extract of the extract (2) shows a ratio of epimers higher than 70% after heat sterilization. That is, the two red pomegranate extracts (containing 40% to 90% of ellagic acid) show a polyphenol stabilizer which is a significantly higher epimerization inhibitory effect.

(Example 2)

Polyphenol stabilization effect of various plant extracts (heat preservation)

The sterilized beverage prepared in Example 1 was stored at 37 ° C for 2 weeks. The procyanidins residual ratio and the epimer ratio were calculated for each of the drinks after storage in the same manner as in Examples 1 (iii) to (v). The results of the unadded, red pomegranate extract (1), red pomegranate extract (2), and orange gum extract are shown in Fig. 3 and Fig. 4.

As can be seen from FIG. 3 and FIG. 4, the beverage to which the orange extract and the pomegranate extract were added was subjected to heat sterilization and stored at 37 ° C for 2 weeks, and the proanthocyanidins remained higher than the beverage without the added plant extract. Rate and epimer ratio. In particular, the two red pomegranate extracts (containing 40% to 90% of ellagic acid) are polyphenol stabilizers which have a low inhibitory effect on proanthocyanidins and a high inhibitory effect on epimerization under warm storage conditions.

(Example 3)

Polyphenol stability of red pomegranate extract (90% ellagic acid)

(i) modulation of beverages

Using the red pomegranate extract (1) of Example 1 (manufactured by BIO ACTIVES, Japan, 90% ellagic acid content), the beverage was prepared in the same manner as in Examples 1 (i) to (iii). However, regarding the blending amount of the above extract, 350 mg of the beverage was set to 0 mg, 1.75 mg (5 ppm), 3.5 mg (10 ppm), 8.75 mg (25 ppm), 17.5 mg (50 ppm), 35 mg (100 ppm), and 87.5 mg, respectively. 250 ppm), 175 mg (500 ppm), 350 mg (1000 ppm).

The beverage prepared in the above (i) was heat-sterilized in the same manner as in Example 1 (ii). The polyphenols were analyzed in the same manner as in Examples 1 (iii) to (v) for the beverages before and after the heat sterilization, and the residual ratio of the proanthocyanidins and the ratio of the epimers were calculated. The results are shown in Figures 5 and 6.

As can be seen from Fig. 5 and Fig. 6, by adding 5 to 1000 ppm of the above-mentioned red pomegranate extract to the beverage, the concentration of the proanthocyanidins and the ratio of epimers were increased depending on the concentration.

In other words, by adding 5 ppm or more of the red pomegranate extract containing 90% ellagic acid to the beverage containing 100 mg of proanthocyanidins (1.575 mg or more in terms of ellagic acid), it is shown that the reduction of proanthocyanidins and the inhibition of the epidermis are suppressed. The isomerization of the tea compounds.

Further, the sterilized beverage prepared in the present example was stored at 37 ° C for 2 weeks. With respect to the preserved beverage, the polyphenols of each beverage were analyzed in the same manner as in Examples 1 (iii) to (v), and the residual ratio of proanthocyanidins and the ratio of epimers were calculated. The results are shown in Figures 7 and 8.

As can be seen from Fig. 7 and Fig. 8, the beverage containing the red pomegranate extract containing 90% ellagic acid was heat-sterilized and stored at 37 ° C. After the week, there were higher procyanidins residual ratios and epimerization ratios than the beverages to which no stabilizer was added.

(Example 4)

Polyphenol stability of various red pomegranate extracts (15-40% ellagic acid content, 30% pomegranate content)

(i) modulation of beverages

Using the pomegranate extract (2) of Example 1 (manufactured by NATURAX, ellagic acid content 40%), pomegranate extract (3) (manufactured by ARJUNA, 15% ellagic acid after hydrolysis), red pomegranate extract (4) (manufactured by OMNICA, 30% guaranin content), the beverage was prepared according to the method described in Examples 1 (i) to (ii). However, regarding the blending amount of the above extract, the red pomegranate extract (2) is 250 to 1000 ppm in the beverage, and the red pomegranate extract (3) and the red pomegranate extract (4) are 50 to 500 ppm.

The beverage prepared in the above (i) was heat-sterilized in the same manner as in Example 1 (ii). The polyphenols were analyzed in the same manner as in Examples 1 (iii) to (v) for the beverages before and after the heat sterilization, and the residual ratio of the proanthocyanidins and the ratio of the epimers were calculated. The results are shown in Figures 9 and 10.

Further, the sterilized beverage prepared in the present example was stored at 37 ° C for 2 weeks. About red pomegranate extract (3) and red pomegranate extract (4), they were stored at 37 ° C for 2 months. With respect to the preserved beverage, the polyphenols of each beverage were analyzed in the same manner as in Examples 1 (iii) to (v), and the residual ratio of proanthocyanidins and the ratio of epimers were calculated. Red pomegranate extract The results of the extract (2) are shown in Fig. 11 and Fig. 12. Further, the results of the red pomegranate extract (3) are shown in Fig. 13 and Fig. 14. The results of the red pomegranate extract (4) are shown in Figs. 15 and 16.

As can be seen from Fig. 9 and Fig. 10, by adding 50 to 1000 ppm of the above-mentioned red pomegranate extracts (2) to (4) to the beverage, the concentration of the proanthocyanidins and the ratio of epimers are increased depending on the concentration. Moreover, as can be seen from Fig. 11 to Fig. 16, a beverage containing 15 to 40% ellagic acid or a pomegranate extract containing 30% punical glucoside is heat-sterilized and stored at 37 ° C. The higher the original anthocyanin residual rate and the epimerization ratio of the beverage added with the stabilizer.

That is, by adding 50 ppm or more of the pomegranate extract containing 30% punical guaiacin in a beverage containing 100 mg of proanthocyanidins (5.25 mg or more in terms of pomegranate), it is shown to inhibit the reduction of proanthocyanidins and inhibit the appearance of the body. The isomerization of the tea compounds.

(Example 5)

Polyphenol stability of ellagic acid purified product and purified pomegranate

(i) modulation of beverages

The beverage was prepared in the same manner as in Example 1 (i) to (ii) using ellagic acid (manufactured by Wako Pure Chemical Industries, Ltd., yttrium acid dihydrate 99.0% or more) and guavaside (manufactured by SIGMA Co., Ltd.). However, regarding the blending amount of the above extract, ellagic acid is 0 to 350 mg (1000 ppm) in 350 ml of the beverage, and garnetin is 35 mg (100 ppm).

The beverage prepared in the above (i) was heat-sterilized in the same manner as in Example 1 (ii). The polyphenols were analyzed in the same manner as in Examples 1 (iii) to (v) for the beverages before and after the heat sterilization, and the residual ratio of the proanthocyanidins and the ratio of the epimers were calculated. The results are shown in Fig. 17 and Fig. 18.

As can be seen from Fig. 17 and Fig. 18, by adding 5 to 1000 ppm of ellagic acid to the beverage, the concentration of the proanthocyanidins and the ratio of epimers were increased depending on the concentration. That is, by formulating 5 ppm (1.75 mg) or more or 100 ppm (35 mg) or more of punical punical glucoside in a beverage containing 100 mg of proanthocyanidins, it is shown that the reduction of proanthocyanidins in the beverage can be suppressed and the epicatechin catechins in the beverage can be inhibited. The difference is isomerized.

Further, the sterilized beverage prepared in the present example was stored at 37 ° C for 2 months. With respect to the preserved beverage, the polyphenols of each beverage were analyzed in the same manner as in Examples 1 (iii) to (v), and the residual ratio of proanthocyanidins and the ratio of epimers were calculated. The results of the blending of the ellagic acid beverage are shown in Figs. 19 and 20.

As can be seen from Fig. 19 to Fig. 20, the beverage added with 5 to 1000 ppm of ellagic acid, after heat sterilization and storage at 37 ° C for 2 months, has a higher residual rate of proanthocyanidins than the beverage without the stabilizer. And epimer isomer ratio.

Further, after the test beverage was stored at 37 ° C for 3 months, the ellagic acid content in the test beverage (100 ppm of ellagic acid) was measured, and the residual value was 101% with respect to the theoretical value of the blended amount.

(Example 6)

Stabilizing effect of polyphenols (catechins) from ellagic acid purified products

(i) modulation of beverages

For tea polyphenol (manufactured by Wako Pure Chemical Industries, product name: catechin mixture, derived from green tea) 625 mg and ellagic acid (manufactured by Wako Pure Chemical Industries, yroic acid dihydrate 99.0% or more) 0 mg, 35 mg (100 ppm) Water was added to prepare a 350 ml solution. The above solution was adjusted to pH 6.5 using 0.1 M hydrochloric acid or 0.1 M sodium hydroxide to prepare a beverage.

(ii) sterilization

After the above beverage was sealed in a closed container, it was heat-sterilized at 121 ° C for 10 minutes in an autoclave.

(iii) Polyphenol analysis

The beverages before the heat sterilization obtained in the above (i) and the heat-sterilized beverages obtained in the above (ii) are respectively quantified according to the above quantitative methods: 8 components of the catechin catechins and the non-epi catechins. . Further, the abbreviation of the eight components is as follows.

Epicatechin: EC

Catechin: C

Epigallocatechin: EGC

Gallocatechin: GC

Epicatechin Gallate: ECG

Catechin gallate: CG

Epigallocatechin gallate: EGCG

Gallocatechin gallate: GCG

(iv) Evaluation of the inhibitory effect of epimerization

The epimer ratio was calculated by using the numerical values of the eight components quantified in the above (iii).

(a) Epimer ratio (%) = (EC content in each beverage / EC content in each beverage + C content) * 100

(b) Epimer ratio (%) = (EGC content in each beverage / EGC content in each beverage + GC content) * 100

(c) Epimer ratio (%) = (ECG content in each beverage / ECG content in each beverage + CG content) * 100

(d) Epimer ratio (%) = (EGCG content in each beverage / EGCG content in each beverage + GCG content) * 100

(e) Epimer ratio (%) = (the sum of the surface catechins in each beverage / the total of the catechin catechins and non-epi catechins in each beverage) * 100

The closer the value of the epimer ratio of each beverage after heat sterilization is to the value of the epimer ratio in the beverage before sterilization, that is, the higher value indicates the surface of the beverage after heat sterilization. The tea catechus are not heterogeneously converted into non-epi catechins, but are preserved stably with epicatechins. The results are shown in Fig. 21.

As seen in Fig. 21, in the beverage without the stabilizer, the epicatechin catechins of the tea catechins were differentially isomerized due to heat sterilization. Non-epidermal catechins, so the ratio of epimers to any component is lower than after sterilization. On the other hand, by adding 100 ppm of ellagic acid to the beverage, the ratio of the difference to the isomer of the tea polyphenol after sterilization showed a higher value than the unadded beverage. That is, it is known that ellagic acid can be used as a polyphenol stabilizer for suppressing epimerization of epicatechins in tea beverages.

(Example 7)

Stabilization effect of polyphenols (catechins) of various concentrations of ellagic acid

(i) modulation of beverages

For ellagic acid (manufactured by Wako Pure Chemical Industries, 99.0% or more of ellagic acid dihydrate), tea polyphenols were added at 0 mg, 3.5 mg (10 ppm), 8.75 mg (25 ppm), 17.5 mg (50 ppm), and 35 mg (100 ppm), respectively. (Wako Pure Chemical Industries, product name: catechin mixture, derived from green tea) 625mg and water, prepared 350ml solution. The above solution was adjusted to pH 6.5 using 0.1 M hydrochloric acid or 0.1 M sodium hydroxide to prepare a beverage.

(ii) sterilization

After the above beverage was sealed in a closed container, it was heat-sterilized at 121 ° C for 10 minutes in an autoclave.

In the same manner as in Example 6, the epicatechin catechins and non-epi catechins in each test zone were quantified, and the epimer ratio was calculated. The results of (e) epimer ratio (all epicatechin catechins) are shown in Fig. 22 .

As can be seen from Fig. 22, by adding 10 to 100 ppm of ellagic acid to the beverage, the ratio of the difference to the isomer ratio of the tea polyphenol after sterilization showed a high value. Although not shown in Fig. 22, the ratio of the epimers (a) to (d) of the catechin components of the respective forms showed a high value depending on the concentration of ellagic acid.

Further, the sterilized beverage prepared in the present example was stored at 37 ° C for 2 months. For the preserved beverage, the polyphenols of each beverage were analyzed in the same manner as in Examples 6 (iii) to (v), and the catechin catechins and non-epi catechins in each test zone were quantified. Epimer ratio. The results of (e) epimer ratio (all epicatechin catechins) are shown in Fig. 23.

As can be seen from Fig. 23, the beverage to which 10 to 100 ppm of ellagic acid was added was subjected to heat sterilization and stored at 37 ° C for 2 months, and had a higher ratio of epimers than a beverage to which no stabilizer was added. Although not shown in Fig. 23, the epimer ratios (a) to (d) of the respective catechin components showed a high value depending on the concentration of ellagic acid.

(Example 8)

Polyphenol stabilization effect in cocoa polyphenol-containing beverage (pH 5.5)

(i) modulation of beverages

Adding water to 625 mg (proanthocyanidin content 100 mg) of cocoa polyphenol obtained according to the above method, and lyric acid (test drug) or red pomegranate extract (4) (containing punny pomegranate 30%) 35 mg (100 ppm) 350 ml solution. The above solution was adjusted to pH 6.5 using 0.1 M hydrochloric acid or 0.1 M sodium hydroxide to prepare a beverage.

The beverage prepared in the above (i) was heat-sterilized in the same manner as in Example 1 (ii). The polyphenols were analyzed in the same manner as in Examples 1 (iii) to (v) before and after heat sterilization and at a temperature of 37 ° C for two weeks, and the residual ratio of anthocyanins and the ratio of epimers were calculated. The results are shown in Figures 24 and 25.

As can be seen from Fig. 24 and Fig. 25, even for the beverage containing cocoa polyphenol at pH 6.5, the residual rate and the difference of the proanthocyanidins were obtained by adding 100 ppm of the stabilizer containing ellagic acid to the beverage. The isomer ratio also increased.

(Comparative Example 1)

Effect of gallic acid on polyphenol stability

(i) modulation of beverages

To a solution of 625 mg (proanthocyanidin content: 100 mg) of cocoa polyphenol obtained by the above method, and 35 mg (100 ppm) of each of ellagic acid (test drug) or gallic acid (test drug), water was added to prepare a 350 ml solution. The above solution was adjusted to pH 5.5 using 0.1 M hydrochloric acid or 0.1 M sodium hydroxide to prepare a beverage.

The beverage prepared in the above (i) was heat-sterilized in the same manner as in Example 1 (ii). The polyphenols were analyzed in the same manner as in Examples 1 (iii) to (v) for each of the beverages before and after the heat sterilization, and the residual ratio of the proanthocyanidins and the ratio of the epimers were calculated. The results are shown in Figures 26 and 27.

As understood from Fig. 26 and Fig. 27, gallic acid did not confirm the stabilization effect of polyphenols.

(Reference example 1)

Antioxidant activity and total polyphenol content of various plant extracts

For the plant extract (except ginger extract, ascorbic acid, and pomegranate extract (2)) used in Example 1, antioxidant activity (DPPH radical scavenging ability) and total polyphenol amount were measured.

(DPPH free radical elimination ability)

The DPPH (1,1-diphenyl-2-glycosylfluorenyl group, 1,1-Dyphenyl-2-picrylhydarzyl) radical scavenging ability was measured according to the method described in Non-Patent Document 4. The measurement method is summarized as follows.

Each of the plant extracts was dissolved in an 80% by weight aqueous methanol solution, and a solution having a stepwise dilution of 1000 ppm was prepared. To 100 μl of the above solution, 2 ml of a 0.1 mM DPPH solution was added, and after standing at room temperature for 30 minutes, the absorbance at 520 nm was measured. The DPPH solution was used as a blank group, and the absorbance value was set to 100% of the inhibition rate, and the inhibition ratio of each sample solution was calculated. The sample concentration (IC50) at which the above inhibition rate was 50% was determined by interpolation. The lower the IC50 value, the higher the DPPH radical scavenging ability (antioxidant activity). The relationship between the obtained antioxidant activity and the residual ratio of the proanthocyanidins obtained in Example 1 is shown in Fig. 28.

As understood from Fig. 28, there was no significant difference between the antioxidant activity of each plant extract used in Example 1 and the residual rate of proanthocyanidins. Relevance.

(total amount of polyphenols)

The total amount of polyphenols is obtained by quantitative analysis of each sample by referring to the method described in Non-Patent Document 5, using commercially available gallic acid as a standard. The measurement method is summarized as follows.

Each of the plant extracts was extracted with an 80% by weight aqueous methanol solution to prepare a test solution. Next, 100 μl of each test solution was added to 50 ml of distilled water, and 3 ml of a 0.1 M ammonium iron (III) sulfate-0.1 M hydrochloric acid solution was added thereto with stirring, and after 20 minutes, 3 ml of an aqueous 8 mM hexaamine iron (III) solution was added thereto. After another 20 minutes, the absorbance at 720 nm was measured. Furthermore, 100 μl of a solvent (80% by weight of methanol) of each sample solution and 80% by weight of a methanol solution of gallic acid (manufactured by SIGMA Co., Ltd.) were added to 50 ml of distilled water, and a calibration curve was prepared in the same manner to calculate a test curve. The total amount of polyphenols. The correlation between the results of the total amount of polyphenol obtained and the residual ratio of proanthocyanidins obtained in Example 1 is shown in Fig. 29.

As is understood from Fig. 29, no significant correlation was found between the total polyphenol amount of each plant extract used in Example 1 and the residual rate of proanthocyanidins.

It is presumed that the polyphenol stabilizing effect produced by the ellagic acid and punica glucoside found in the present invention is not caused by the antioxidant activity and the total amount of polyphenols.

Claims (16)

A stabilizer, which is a stabilizer for polyphenols, and comprises at least one of ellagic acid and punical aglycone. The stabilizer of Claim 1, wherein the content of at least the ellagic acid is 15% by weight or more based on the total weight of the stabilizer, or the content of the punny glucoside is 30% by weight or more. The stabilizer of claim 1 or 2, wherein the polyphenol stabilizer is an epimerization inhibitor of epie catechins. The stabilizer of Claim 1 or 2, wherein the polyphenol stabilizer is a reducing inhibitor of procyanidin. The stabilizer of any one of claims 1 to 4, wherein the stabilizer is a plant extract comprising at least one of ellagic acid or punical glucoside. The stabilizer of any one of claims 1 to 5, wherein the aforementioned plant extract is a red pomegranate extract. A composition comprising a polyphenol, and a stabilizer for at least one of ellagic acid and punical guava. The composition of claim 7, which comprises the stabilizer of any one of claims 1 to 6 and a composition of a polyphenol, wherein at least 100 parts by weight of the polyphenol is used to make the ellagic acid at least The stabilizer is contained in an amount of 1.5 parts by weight or more or 5 parts by weight or more. The composition of claim 7 or 8, wherein the polyphenol is at least one selected from the group consisting of proanthocyanidins and catechins. The composition according to any one of claims 7 to 9, wherein the stabilizer is a plant extract comprising at least one of ellagic acid or punical glucoside. The composition of any one of claims 7 to 10, wherein the aforementioned plant extract is a red pomegranate extract. A processed product containing polyphenols, which is selected from the group consisting of foods, foods, pharmaceuticals, and cosmetics, using the composition according to any one of claims 7 to 11. The processed article containing the polyphenol of claim 12, wherein the pH of the processed product containing the polyphenol is from 4.0 to 8.0. A manufacturing method which is a method for producing a processed article containing polyphenol, comprising the steps of: (a) modulating the composition of any one of claims 7 to 11, and (b) preparing the composition using the foregoing composition a step of processing a processed article containing polyphenol, (c) a step of heating the above-mentioned processed article containing polyphenol to a temperature of 37 ° C or higher. A processed product containing polyphenols selected from the group consisting of food and beverage, pharmaceuticals, and cosmetics manufactured by the manufacturing method of claim 14. A method for the stabilization of polyphenols, which comprises at least 1.5 parts by weight or more of ellagic acid or 5 parts by weight or more of guaranuric acid based on 100 parts by weight of the polyphenol.