JP2001103930A - Isoflavone compound-enriched food - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an isoflavone compound-enriched food. SOLUTION: This isoflavone compound-enriched food is obtained by adding a malonyl isoflavone glycoside (preferably at least one kind selected from a malonyl daidzin and malonyl genistin) and/or isoflavone glycoside (preferably at least one kind selected from a daidzin and genistin) each derived from soybeans during processes for manufacturing various foods and drinks.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a malonyl isoflavone glycoside derived from soybean and an isoflavone compound-enriched food to which an isoflavone compound mainly composed of isoflavone glycoside is added.

[0002]

2. Description of the Related Art Conventionally, soybeans contain daidzin, glycitin, genistin, acetyldaidin and acetylgenistin as isoflavone compounds or daidzein, glycitein, genistein as their aglycones.
It has been confirmed that it has many pharmacological effects including antioxidant and anticancer effects. On the other hand, recently some soybeans

[0003]

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[0004]

Embedded image The presence of malonyl isoflavone glycosides such as malonyl daidzin and malonyl genistin shown in Table 1 was confirmed, and these were found to be the main components of the isoflavone compounds in soybean. This malonyl isoflavone glycoside is easily soluble in water, has an antioxidant effect itself, is expected to have the above-mentioned pharmacological effects due to its structural similarity, and is also expected to be used as an active ingredient of bath salts. Things.

[0005] For this reason, soybeans are extracted with water, the aqueous extract is brought into contact with an adsorbent to adsorb the malonyl isoflavone glycoside, and the malonyl isoflavone glycoside is eluted with an aqueous alcohol solution to convert the malonyl isoflavone glycoside. A method for obtaining the information has also been proposed (Japanese Patent Laid-Open No. 8-283283). In addition, soybean hypocotyls used for feeds and the like have a large content of isoflavone compounds, and malonyl isoflavone glycosides can be obtained from this as a raw material. Further, a method has been proposed in which okara, which is a by-product of tofu and soy milk production, is extracted with water to obtain malonyl isoflavone glycoside.

The isoflavone compounds in soybeans are mainly malonyl isoflavone glycosides such as malonyl daidzin and malonyl genistin (80-85%), followed by isoflavone glycosides such as daidzin and genistin in 10-15%.
Occupy. Aglycones such as daidzein and genistein account for the remaining several percent.

[0007]

As described above, isoflavone compounds in soybean extracts have various physiological activities. Recently, these compounds are processed into tablets or capsules and sold as health foods. Have been. However, such a form of health food has a disadvantage that it must be eaten for the purpose.

[0008]

Means for Solving the Problems The present inventors added malonyl isoflavone glycosides and isoflavone compounds mainly composed of isoflavone glycosides to various foods to provide foods enriched with isoflavone compounds, so that the foods were eaten without much effort. I realized that I could take isoflavone compounds without it,
The present invention has been completed. That is, the present invention is an isoflavone compound-enriched food to which malonyl isoflavone glycoside and / or isoflavone glycoside derived from soybean are added. Although X-enriched foods in which a certain component X is added to various foods are known, soybean-derived malonyl isoflavone glycosides and foods to which isoflavone glycosides are added have not been known so far.

Conventionally, there is a strong idea that isoflavone aglycone has physiological activity, and that glycosides must undergo enzymatic degradation in the body after ingestion, and therefore, development of aglycone-based substances has been promoted. However, aglycone did not dissolve in water and had a harsh taste. For example, JP-A-11-243928 is an invention relating to a beverage to which isoflavone aglycone is added, and a suspending agent, a dispersant,
Although a surfactant or the like is used, it is extremely difficult to completely dissolve even with this. Furthermore, it has an unpleasant taste, such as an astringent taste, and especially in beverages, this unpleasant taste is fatal.
However, glycosides are easily soluble in water, and in particular, malonyl isoflavone glycosides are hydrophilic and have no harsh taste, so that there is no problem in adding them to various foods including beverages.

Hereinafter, the present invention will be described in detail. The malonyl isoflavone glycoside and isoflavone glycoside used in the present invention are derived from soybean, and include a water extract of soybean, a water extract of soybean hypocotyl, a water extract of okara, and a soybean whey. Can be obtained from About the method of obtaining the isoflavone glycoside from the aqueous extract of soybean or soybean whey, it can be obtained by the method described in JP-A-8-283283. be able to. That is, ordinary okara obtained as a by-product of tofu, fried or soymilk, or a residue generated in the process of producing isolated soybean protein is used as a raw material, and such okara is extracted with water. The temperature of the water used for the extraction is not limited. That is, any of room temperature water, warm water and hot water may be used.

The water used for the extraction is made into a dilute acid solution having a pH of 4 to 5 with hydrochloric acid, phosphoric acid, acetic acid, lactic acid or the like, thereby stabilizing the isoflavone glycoside to be extracted and, at the same time, extracting the okara after the extraction. Has an acidic effect, which has the effect of suppressing the progress of spoilage by microorganisms. In addition, the extraction rate of the isoflavone glycoside can be improved by making the water used for the extraction into a dilute alkaline solution having a pH of 8 to 10 with sodium hydroxide, potassium hydroxide or the like. Furthermore, the extraction efficiency can also be increased by adding ethanol to the water to be extracted so as to be 5 to 30%.

In order to extract okara using such extracted water, 1 to 10 times (w / w) amount of extracted water is added to okara, and the mixture is thoroughly stirred and mixed. Solid-liquid separation is performed by a separation device, for example, a filter-type filter, a screw decanter, or the like. The obtained extract is used as it is, or a filtrate from which the protein is removed using an ultrafiltration membrane as needed, or a protein is precipitated by adjusting the pH to about 4.0 to 5.0 with hydrochloric acid, and the supernatant is adsorbed. Contact with the agent.

The above-mentioned extract, filtrate or supernatant is directly contacted with an adsorbent,
After adjusting to about 8.0, there is a method of contacting. In the former case, the amount of adsorption to the adsorbent is increased, and in the latter case, there is an advantage that it is easy to separate daidzin and genistin mixed with malonyl isoflavone glycoside. In any case, the adsorbent used is, for example, a synthetic adsorbent, activated carbon, alumina or the like, and specifically, Diaion HP-2
0 (manufactured by Mitsubishi Chemical), purified Shirasagi activated carbon (manufactured by Takeda Pharmaceutical), activated alumina (manufactured by Wako Pure Chemical Industries), and the like. The contact may be a general method such as a batch method or a column method,
For example, the extraction can be performed by passing the extract through a column filled with the adsorbent, whereby most of the isoflavone glycosides in the extract are adsorbed by the adsorbent.

Next, the isoflavone glycoside adsorbed on the adsorbent is eluted using an aqueous alcohol solution or an aqueous alkaline alcohol solution. The obtained solution is concentrated under reduced pressure, or concentrated under reduced pressure, and then freeze-dried to obtain a concentrated solution or a dry powder of isoflavone glycoside.

The above-mentioned concentrated liquid or dry powder is daidzin,
It is a mixture of genistin, malonyl daidzin and malonyl genistin. These can be easily added to various foods because they are soluble in water.

In order to obtain malonyl daidzin and malonyl genistin efficiently, the following method is preferred. That is, until the extract of okara is brought into contact with the adsorbent, the same as above, but elution is performed sequentially by changing the concentration of the aqueous alcohol solution, and roughly malonyl daidzin,
Malonylgenistin or daidzin and genistin are separated, and these eluates are purified by an ODS column. According to the present invention, malonyl daidzin, malonyl genistin or daidzin and genistin can be easily separated from the extract of okara in this way. In addition, malonyl daidzin and malonyl genistin can be converted into daidzin and genistin by using these as raw materials by treating with acid or alkali.

For example, a solution in which malonyl daidzin and malonyl genistin are dissolved is adjusted to pH 8 to 13 with ammonia, caustic soda, sodium carbonate, or the like, and left for at least 0.5 hour to be converted into daidzin and genistin. In the alkali treatment, the higher the pH, the higher the conversion. In addition, a solution in which malonyl daidzin and malonyl genistin are dissolved is 70 to 1
By heating at 50 ° C. for 0.5 to 12 hours, these malonyl compounds can be converted into daidzin and genistin. The higher the heating temperature and the longer the heating time, the faster the conversion speed. The conversion rate can be further increased by combining the pH of the solution and the heating temperature. The daidzin and genistin thus converted are adsorbed to the ODS resin, eluted with an aqueous alcohol solution, concentrated under reduced pressure, and lyophilized to obtain purified daidzin and genistin.

The thus obtained isoflavone compound is added to various foods, for example, processed soybean foods such as tofu and soymilk drinks, beverages, breads, confections, ice creams and the like. The addition may be made at any time during the production process of various foods, and the amount added is 10 to 10,000 as an isoflavone glycoside.
0 ppm, preferably 50 to 5,000 ppm.
By doing so, an isoflavone compound-enriched food is obtained.

The present invention is a food in which malonyl isoflavone glycoside derived from soybean and an isoflavone compound mainly composed of isoflavone glycoside are added and fortified. It is possible to take isoflavone compounds.

[0019]

The present invention will be described in detail with reference to the following examples. Example 1 <Production of isoflavone compound powder from okara> Dilute acid solution 2 was added to 10 tons of okara discharged in a normal tofu production process.
0KL (0.05N hydrochloric acid solution) was added, mixed and stirred (pH
After 4.2), solid-liquid separation was performed with a screw decanter to obtain 18 KL of an extract. This extract contains malonyl isoflavone glycoside 34 ppm, isoflavone glycoside 36 ppm
It was contained.

[0020] This extract is used as a synthetic adsorbent DIAION HP-2.
0 (manufactured by Mitsubishi Chemical Corporation) (350 L, diameter 1.
(2 m, length 1 m) at a flow rate of 1 KL / hr to adsorb isoflavone glycosides, and then washed with 2 KL of distilled water. Next, the isoflavone compound was eluted from the resin with 1 KL of a 50% aqueous ethanol solution, and the ethanol solution was adjusted to pH 4.5 with dilute hydrochloric acid, concentrated to 20 L with a vacuum concentrator, and freeze-dried to obtain 4.2 kg of powder. Was.
The amount of malonyl isoflavone glycoside in this powder is 124 m
g / g and the amount of isoflavone glycoside were 113 mg / g.

Example 2 <Production of isoflavone compound powder from defatted soybeans> 3 tons of defatted soybeans were immersed and extracted in 30 KL of warm water at 50 ° C for 2 hours while adjusting to pH 8.0 to obtain 25 KL of an extract. The extract was adjusted to pH 4.0 with concentrated hydrochloric acid and filtered. 20 KL of the filtrate is used as the synthetic adsorbent DIAION HP-20
70L / h in a column (25L) packed with (Mitsubishi Chemical)
The solution was passed at a flow rate of r to adsorb the isoflavone compound, and then washed with 2 KL of distilled water. Then, the mixture was eluted with a 40% aqueous ethanol solution and concentrated under reduced pressure at 50 ° C. to about 100 L to obtain a concentrated liquid containing 3,370 g of malonyl daidine glycoside and 250 g of isoflavone glycoside. 14.4 kg were obtained.

Example 3 <Production of tofu with reinforced isoflavone compound> 100 kg of soybean (Fukuyutaka) was washed with water and immersed in water at room temperature for 18 hours.
After draining the water-soaked soybeans, the soybeans were ground while adding 400 L of water, and heated to 95 ° C. with a closed heating device.
Hold for minutes. Then, it was pressed to obtain 330 L of soymilk having a protein concentration of 6.5% and 160 kg of okara. The soymilk was cooled to 10 ° C. after removing the air mixed in a degassing tank.

The amount of malonyl isoflavone glycoside in this soymilk was 2,384 ppm, and the amount of isoflavone glycoside was 1.7.
53 ppm, and the amount of isoflavone aglycone was 191.
ppm. To 1 L of this soy milk, 10 g of the isoflavone compound powder obtained in Example 1 was added and mixed. As a result, the amount of malonyl isoflavone glycoside in soy milk was 3,383 p
pm, the amount of isoflavone glycosides was 2,883 ppm, and the total amount of isoflavone compounds was 4,328 ppm at the beginning.
From 6,266 ppm, which is a 1.4-fold increase. This isoflavone compound enriched soy milk contains 0.2% magnesium chloride.
After adding and mixing each 45% solution so that 5% and calcium chloride become 0.05%, filling and sealing the container, the mixture is heated and coagulated in hot water at 85 ° C., and the isoflavone compound-reinforced tofu is removed. Obtained.

Example 4 <Manufacture of soymilk drink enriched with isoflavone compound> Dehulled soybean obtained by heating soybean (IOM) so that the soybean product temperature becomes 80 ° C., halving it with a rubber roller, cooling and separating and removing the seed coat Grinding was performed while adding 90 ° C. hot water to 100 kg, immediately heated to 105 ° C. and maintained for 60 seconds, followed by solid-liquid separation. The obtained soymilk was introduced into a deaerator and cooled to 40 ° C. to obtain 700 L of soymilk having a protein concentration of 3.5%, which was cooled to 10 ° C. The amount of malonyl isoflavone glycoside in this soymilk was 2,178 ppm, the amount of isoflavone glycoside was 487 ppm, and the amount of isoflavone aglycone was 52 ppm. As a result of adding and mixing 10 g of the isoflavone compound powder obtained in Example 2 to 1 L of this soy milk, the amount of malonyl isoflavone glycoside in soy milk was 4,5.
00 ppm, and the amount of isoflavone glycoside was 660 ppm. This soymilk was heat-sterilized at 145 ° C for 5 seconds, cooled to 10 ° C, and filled in a sterile container under a sterile atmosphere.
It sealed and obtained the isoflavone compound fortified soymilk drink.

Example 5 <Carbonated drink enriched with isoflavone compound> Sugar 4%, honey 0.2%, vitamin C 0.05%, citric acid 0.03
%, Caffeine 0.01%, niacinamide 0.02
%, Vitamin B ₆ 0.005%, vitamin B ₂ 0.005
%, Isoleucine 0.001%, threonine 0.001
%, Phenylalanine 0.001%, etc.
To L, 10 g of the isoflavone compound powder obtained in Example 2 was added, mixed and dissolved. The amount of malonyl isoflavone glycoside in this solution was 2,322 ppm, and the amount of isoflavone glycoside was 173 ppm. This solution is heated at 150 ° C,
After heat sterilization for 10 seconds, the mixture was cooled to 5 ° C., carbon dioxide gas was dissolved in a pressure-resistant container, filled in a sterilized container under a sterile atmosphere, and sealed to obtain a carbonated beverage reinforced with isoflavone compounds.

Claims (6)

[Claims] 1. An isoflavone compound-enriched food to which soybean-derived malonyl isoflavone glycoside and / or isoflavone glycoside is added. 2. The fortified isoflavone compound food according to claim 1, wherein the malonyl isoflavone glycoside is at least one member selected from malonyl daidzin and malonyl genistin. 3. The isoflavone compound-enriched food according to claim 1, wherein the isoflavone glycoside is at least one member selected from daidzin and genistin. 4. A water extract of soybean, a water extract of soybean hypocotyl, wherein the malonyl isoflavone glycoside and the isoflavone glycoside are provided.
4. The isoflavone compound-enriched food according to claim 1, which is obtained from a water extract of okara or soybean whey. 5. A processed isoflavone compound-enriched soymilk food obtained by adding malonyl isoflavone glycoside and / or isoflavone glycoside obtained from an aqueous extract of okara to soymilk and processing the resultant. 6. The processed isoflavone compound-enriched soymilk food according to claim 5, wherein the processed soymilk food is a soymilk drink or tofu.