JPH02110164A - Stabilization of anthocyan pigment - Google Patents

Abstract

PURPOSE:To stabilize the hue, lightness and saturation of the title pigment by preventing it from being degraded by discoloration or fading caused by heat, light, oxygen or the like by mixing an anthocyan pigment with a readily water-soluble flavonol and a water-soluble anti-oxidant. CONSTITUTION:An anthocyan pigment is mixed with a readily water-soluble flavonol which is desirably a single substance or a mixture of flavonoid O- monoglucoside obtained by the action of an enzyme capable of causing partial hydrolysis upon a flavonol glycoside (e.g., rutin) and a flavonoid glycoside obtained by the action of (trans)glucosidase, etc., upon a starch to transfer at least equimolar amount of the glucose residues and a water-soluble antioxidant (e.g., sodium erythorbate or disodium ethylenediaminetetraacetate).

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for stabilizing natural pigments, and more particularly to the stabilization of natural pigments, and more particularly, the method for stabilizing natural pigments, and more particularly, the method for stabilizing natural pigments by using a water-soluble flavonol glycoside and a water-soluble antioxidant. This invention relates to a dye stabilization method.

[Conventional technology]

Anton'an pigment is widely distributed in red cabbage, hibiscus, purple corn, berries, and other plants.The pigment is usually extracted and purified from the pigment-containing plant by squeezing the juice or using water or a water-soluble organic solvent. obtained by being
It is widely used for coloring food products, beverages, processed foods, etc. However, it is known that Anton-Ahn dyes are easily decomposed by heat, light, oxygen, etc., resulting in discoloration and fading.

In order to prevent quality deterioration due to discoloration and fading of such unstable Anton-An pigments, various measures have been proposed, including the addition of small amounts of ascorbic acid, fufuvonoids, etc.

[Problem to be solved by the invention]

However, in the method of adding a water-soluble antioxidant such as ascorbic acid or erythorbic acid, even if the amount added is increased, a satisfactory effect of preventing fading of Andonan dye cannot be obtained. In addition, when using fufuvonoids, rutin,
Examples include quercetin and morin, but in order to exhibit sufficient effects, it is necessary to increase the amount added. However, all of these fufuponoids have low solubility in water, making them difficult to handle, and, for example, they have the drawback of forming precipitates when used at high concentrations in beverages.

[Means to solve the problem]

In order to solve the drawbacks of conventional methods, the present inventors have stabilized the hue, brightness, and chroma of Andonan pigments or Andonan pigment-containing products by blending or using water-soluble flavonols and water-soluble antioxidants in combination. succeeded in improving sex.

This invention will be explained in detail below.

Anton-An pigment, which is the subject of the present invention, is widely distributed in the plant kingdom such as red kisepet, hibiscus, perilla, purple corn, grapes, berries, and other plants. It refers to the juice of containing plants, extracts with water or water-soluble organic solvents, purified processed products of extracts, and products containing these.

The water-soluble flavonols used in this invention are flavonol/l/glycosides, such as rutin, for which the patent applicant of this invention has already filed a patent application (6B-39127) on February 22, 1985. Flavonol 0-glucoside obtained by treating with an enzyme having a hydrolytic action and a single flavonol glycoside obtained by treating starch with an enzyme having a glucose residue transfer action or a combination of glucose residues Mixtures of glycosides with different L/numbers are used. Hereinafter, this will be referred to as flavonol glycoside 1.

In addition, flavonol glycosides such as rutin, godipitrin, gossypin, etc., and glucose residues or single flavonol glycosides obtained by treating starch with an enzyme having a glucose residue transfer action by a known method. seven rho
Mixtures of glycosides with different numbers are also used. Hereinafter, this will be referred to as flavonol glycoside 2.

Furthermore, one or more substances may be selected from flavonol glycoside 1 and flavonol glycoside 2 and used in combination.

The starch mentioned above is a substrate for glycosidase and transglucosidase, and one of its glucose residues is
It may be anything as long as more than one molecule can be transferred to a flavonoid molecule, and refers to amylose, amylopectin, starch, liquefied starch, dextrin, saccharified starch, cyclodequinutrins, and others.

Water-soluble antioxidants that are mixed or used in combination with water-soluble flavonol glycosides include disodium ethylenediaminetetraacetate, p-disodium ethylenediaminetetraacetate, ascorbic acid, sodium ascorbate, erythorbic acid,
Sodium erythorbate, gallic acid, chlorogenic acid,
One type or a mixture of two or more types selected from caffeic acid is employed.

The amount of water-soluble flavonol glycosides and water-soluble antioxidants used to prevent the fading of Anton'an pigments should be determined based on the type of Anton'an pigment and its form, and the water-soluble flavonol glycosides used as anti-fading agents. Since it cannot be determined in a practical sense, it depends on the combination of the body and the water-soluble antioxidant and its composition, so specific examples will be shown.

Anton Anne pigment and purple corn pigment (color value E1 ([
= 60), when flavonol glycoside 1 prepared from quercetin 3-0CrIt-monogelcondo is used in combination with ascorbic acid, flavonol glycoside 2 is About 0.01 to 5 parts may be used, especially about 0.05 to 1 part.
The amount of anucorbic acid used is preferably about 0 parts.
．． The amount may be at least 0.01 parts, and the upper limit is not particularly limited.

10% Red Cabbage Purified Pigment (Color Value E = 60) When targeting 1α color and prevention of fading, flavonol glycoside 2 prepared from rutin and disodium ethylenediaminetetraacetate were used as water-soluble flavonol glycosides. When a combination is selected, the amount used may be about 0.01 to 5 parts of flavonol glycoside 2 in the above-mentioned red cabbage dye liquid part;
Among these, a usage amount of about 0.05 to 1 part gives preferable results. The antifading agent of the present invention may be used by blending a flavonol glycoside and a water-soluble antioxidant in advance, if desired.
Depending on the purpose of use, solvents such as water, ethanol-p1 propylene glycol, glycerin, etc., or dextrin, powdered sugar, lactose, sucrose, glucose, etc. may be blended to form liquid, paste, powder, molasses, etc. The composition may have other shapes, and if desired, a cyanogen dye may be added to the composition in advance.

When Anton Anne dye is used to color foods such as snacks, beverages, and frozen desserts, the timing of adding the antifading agent of the present invention is not particularly limited, and any timing in the manufacturing process can be selected.

The following examples will demonstrate that this invention is highly effective in preventing color fading of Anton Anne dyes.

Example 1 Quercetin 3-O-monoglucoside was prepared by treating a rutin aqueous solution with a partial hydrolase.

A mixed solution of quercetin 3-O-monoglucoside and dequinutrin was treated with cyclodextrin glucanotransferer 0 to obtain a powder of water-soluble flavonol glycoside 1.

Granulated sugar 6 parts, isomerized sugar 8 parts, anhydrous citric acid 0.3
A syrup was prepared by making 100 parts of sodium citrate and O and Oa of sodium citrate into 100 parts with fresh water.

To this syrup was added a purple corn pigment liquid (color value 10% El, = 60), flavonol glycoside 1 and erythorbic acid 1-'Jum in the amounts listed in Table 1, and the mixture was measured using a spectrophotometer. Maximum absorption wavelength in visible region (515-520
Immediately after measuring the absorbance at Fill a clear Gafnu bottle and cap it using a fade meter (Nuga Test Instruments Co., Ltd. 1).
JFAL-3 type) was used, and ultraviolet rays were irradiated for 16 hours. The absorbance after irradiation with ultraviolet rays was measured under the same conditions as before irradiation, and the dye residual rate was determined using the following formula.

As is clear from the results shown in Table 1, the anti-fading agent in combination of flavonol glycosides and sodium erythorbate of the present invention exhibited a remarkable effect of preventing fading of purple corn pigment compared to the control product.

Example 2 Rutin 10? and starch 1002 were heated and dissolved in 91 water, and cyclodextrin glucanotransferase was added to this solution and reacted at 50° C. for 40 hours to obtain water-soluble flavonol glycoside 2 powder.

To the syrup prepared under the same conditions as in Example 1, red cabbage color solution (color value E10" = 60), flavone glycoside 2 and disodium ethylenediaminetetraacetate were added in the amounts listed in Table 2, After measuring the absorbance at the maximum absorption wavelength in the visible region (534-543 nm) using a spectrophotometer, immediately fill it into a transparent Galanu bottle, cap it, and use a fade meter (FAL-'l model manufactured by Nuga Test Instruments Co., Ltd.). ) was irradiated with ultraviolet rays for 16 hours.The absorbance of the sample solution after irradiation was measured under the same conditions as before irradiation, and the dye residual rate was determined by the same method as in Example 1.

Table 3 Add the same flavonol glycoside 2 and ascorbic acid as described in Example 2 to this dye solution in the amounts listed in Table 3, and use a spectrophotometer to measure the maximum absorption wavelength in the visible region ( 5
After measuring the absorbance at 22 to 525 nm), the mixture was immediately filled into a transparent glass bottle, capped, and irradiated with ultraviolet rays for 16 hours using a fade meter (model FAL-3, manufactured by Nuga Test Instruments Co., Ltd.). The absorbance of the sample solution after irradiation was measured under the same conditions as before irradiation, and the dye residual rate was determined by the same method as in Example 1.

Table 3 As is clear from the results in Table 2, the combination of flavonol glycosides and disodium ethylenediaminetetraacetate of the present invention had a remarkable effect of preventing fading of red cabbage pigment compared to the control product. .

'474 example 3 Elderberry juice (color value E10°=33) 5 partsm A dye solution was prepared by diluting 1000 parts of the solution with clear water.

As is clear from the results in Table 3, the combination anti-fading agent of the present invention of flavonol glycosides and ascorbic acid exhibited a remarkable effect of preventing fading of elderberry juice pigment compared to the control product.

Example 4 Red grape juice (color value E 1096 = 4.2) 20
A dye solution was prepared by adding 1,000 parts to 1,000 parts with fresh water. To this dye solution, the same flavonol glycoside 1 and gallic acid as described in Example 1 were added in the amounts listed in Table 4, and the maximum absorption wavelength in the visible region (515- 52
After measuring the absorbance at 5 nm), the mixture was immediately filled into a transparent glass bottle, capped, and irradiated with ultraviolet rays for 16 hours using a fade meter (model FAL-8, manufactured by Suga Test Instruments Co., Ltd.).

The absorbance of the sample solution after irradiation was measured under the same conditions as before irradiation, and the dye residual rate was determined by the same method as in Example 1.

Table 4 As is clear from the results in Table 4, the combination anti-fading agent of flavonol glycoside 1 and gallic acid of the present invention exhibits a remarkable effect of preventing red grape juice pigment from fading compared to the control product. Ta.

Example 5 Red perilla (perilla oscimoides va.
r, Cr1spa) One part of the dried leaves was extracted with 20 parts of an ethanol solution containing diluted hydrochloric acid, and the extract was subjected to reduced pressure to prepare shisonin pigment (color value E1091α-20). MC at pH=8.0, l1vai
ne buffer solution was added with Nsonine dye, the same flavonol glycoside 1 as in Example 1, and chlorogenic acid in the amounts shown in Table 5, and the maximum absorption wavelength in the visible region (51
After measuring the absorbance at 5 to 525 nm), the mixture was immediately filled into a clear glass bottle, capped, and irradiated with ultraviolet rays for 16 hours using a fade meter (Model FAL-3, manufactured by Suga Senki Co., Ltd.). The absorbance of the sample solution after irradiation was measured under the same conditions as before irradiation, and the dye residual rate was determined by the same method as in Example 1.

Table 5 As is clear from the results in Table 5, the combination of flavonol glycoside 1 and chlorogenic acid of the present invention exhibited a remarkable effect of preventing fading of the shisonin pigment compared to the control product.

Claims (1)

[Claims] 1) A method for stabilizing Anton-An pigment using a water-soluble flavonol and a water-soluble antioxidant. 2) Water-soluble flavonol is obtained by reacting flavonol glycosides with an enzyme that has a partial hydrolyzing action, and flavonoid O-monoglucoside and glucosidase and/or transglucosidase that have a glucose residue transfer action on starch. 2. The method according to claim 1, which is a single flavonoid glycoside or a mixture of two or more flavonoid glycosides obtained by transferring equimolar or more equimolar amounts of glucose residues. 3) Flavonoids obtained by allowing water-soluble flavonol to act on flavonol glycosides and starch with glucosidase and/or transglucosidase, etc., which have a glucose residue transfer action, to transfer equimolar or more equimolar glucose residues. The method according to claim 1, which is a single glycoside or a mixture of two or more glycosides. 4) The water-soluble antioxidant is one or two selected from disodium ethylenediaminetetraacetate, disodium calcium ethylenediaminetetraacetate, ascorbic acid, sodium ascorbate, erythorbic acid, sodium erythorbate, gallic acid, chlorogenic acid, and caffeic acid. A method according to claim 1, comprising a mixture of more than one species.