JP3155466B2 - Water-soluble quercetin glycoside-containing material and method for producing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a water-soluble quercetin glycoside-containing substance and a method for producing the same. For more information,
The present invention relates to a water-soluble quercetin glycoside-containing substance obtained by allowing a specific enzyme to act on a mixture of α-glucosylated rutin and rutin, or a mixture of monoglucosyl rutin and rutin, and a method for producing the same.

[0002] A water-soluble quercetin glycoside-containing substance is obtained when monoglucosyl rutin is separated from a mixture of α-glucosylated rutin and rutin or a mixture of monoglucosyl rutin and rutin.

[0003]

Technical background of the present invention and its problems Rutin is contained in buds and buckwheat of enju, and has an effect of returning blood vessels weakened together with vitamin C to prevent bleeding, and has an anti-inflammatory and analgesic effect. Its use is wide, such as having.
However, since rutin is poorly soluble in water, its use is limited. Therefore, α-glucosylated rutin in which a sugar is transferred (added) to rutin has been developed (Japanese Unexamined Patent Publication No. 3-27293) and is commercially available under the trade name “α-G rutin”. This “α-G rutin” is a mixture of α-glucosylated rutin and rutin having different numbers of transferred (added) glucose units (see “Food Industry”, May 30, 1990 (published)). Rutin itself shows the same pharmacological and physiological actions as rutin, and is remarkably excellent in water solubility, about 5,000 times as much as rutin. Furthermore, if the purity of α-glucosylated rutin in the product can be significantly increased, it is expected that the use of “αG rutin” in, for example, pharmaceuticals and cosmetics can be further expanded.

[0004] As a method for separating monoglucosyl rutin, which is one kind of α-glucosylated rutin, from a substance containing α-glucosylated rutin and rutin, such as “αG rutin”, for example, chromatographic methods A method using chromatography, a method using an adsorption resin and an enzyme reaction, and the like are known.

[0005] Chromatographic separation methods (eg;
The separation of α-glucosylated rutin from a mixture of α-glucosylated rutin and rutin in the 1989 Agricultural Chemistry Lecture Abstracts, p.
Glucosylated rutin (monoglucosyl rutin) is obtained. However, monoglucosyl rutin and rutin, which are one kind of α-glucosylated rutin, have very similar properties. Therefore, this method cannot efficiently separate α-glucosylated rutin from rutin. There was a point.

In the method using an adsorbent resin, first, an "αG rutin" solution is passed through the adsorbent resin to obtain an "αG rutin" solution.
The less hydrophobic α-glucosylated rutin with more saccharide units in “G rutin” is leaked from the adsorption resin. Next, when the α-glucosylated rutin leaked from the adsorption resin is decomposed by glucoamylase, monoglucosyl rutin is obtained. Alternatively, “αG-rutin” is adsorbed on the adsorption resin in advance, and α-glucosylated rutin with a large number of saccharide units having weak adhesion to the resin is desorbed with, for example, a low-concentration alcohol or the like. After that, monoglucosyl rutin can be obtained by decomposition with glucoamylase. However, in these methods, the efficiency is determined by the difference in adhesion between rutin and α-glucosylated rutin to the adsorption resin.
In this method, it is extremely efficient to produce rutin-free α-glucosylated rutin and monoglucosyl rutin from “αG rutin” in this method because the difference in adhesion between -glucosylated rutin and the adsorption resin is not so large. bad.

The present inventors have also found that a water-soluble quercetin glycoside containing isoquercitrin and monoglucosyl rutin obtained in the process of producing such monoglucosyl rutin is also useful. I was

[0008]

SUMMARY OF THE INVENTION The object of the present invention is to solve the problems associated with the prior art as described above, and to obtain a mixture of α-glucosylated rutin and rutin or a mixture of monoglucosyl rutin and rutin. An object of the present invention is to provide a water-soluble quercetin glycoside-containing substance produced in the process of efficiently separating glucosyl rutin, and a method for producing the same.

[0009]

SUMMARY OF THE INVENTION The water-soluble quercetin glycoside-containing composition according to the present invention is characterized in that it contains isoquercitrin and monoglucosyl rutin.

A first method for producing a water-soluble quercetin glycoside-containing substance according to the present invention comprises reacting a mixture of monoglucosyl rutin and rutin (B) with α-1,6-rhamnosidase to convert rutin into isocyanate. It is characterized by changing to elcitrin.

[0011] A second method for producing a water-soluble quercetin glycoside-containing substance according to the present invention comprises the step of simultaneously adding glucoamylase and α-1,6-rhamnosidase to a mixture (A) of α-glucosylated rutin and rutin. Alternatively, they act separately to convert α-glucosylated rutin into monoglucosyl rutin and also convert rutin into isoquercitrin.

According to the method for producing a water-soluble quercetin glycoside-containing substance of the present invention, a water-soluble quercetin glycoside-containing substance is prepared from a mixture of α-glucosylated rutin and rutin or a mixture of monoglucosyl rutin and rutin. Obtainable.

[0013]

DETAILED DESCRIPTION OF THE INVENTION Hereinafter, the water-soluble quercetin glycoside-containing substance according to the present invention and a method for producing the same will be described in detail.

The water-soluble quercetin glycoside-containing substance according to the present invention contains isoquercitrin and monoglucosyl rutin as described above. As described in detail below, such a water-soluble quercetin glycoside-containing substance is obtained in the process of producing monoglucosyl rutin by allowing a specific enzyme to act on a mixture (B) of monoglucosyl rutin and rutin. Can be That is, a mixture of monoglucosyl rutin and isoquercitrin obtained by reacting this mixture (B) with α-1,6-rhamnosidase to convert rutin into isoquercitrin [(C): water-soluble It is called quercetin glycoside-containing substance. ].

As described in detail below, this water-soluble quercetin glycoside-containing substance is obtained by reacting two kinds of specific enzymes with a mixture (A) of α-glucosylated rutin and rutin, Obtained in the process of separating glucosyl rutin.
That is, glucoamylase and α were added to this mixture (A).
-1,6-rhamnosidase simultaneously or separately,
It is a water-soluble quercetin glycoside-containing substance obtained by changing glucosylated rutin to monoglucosyl rutin and converting rutin to isoquercitrin.

In the present invention, monoglucosyl rutin may be separated from such a water-soluble quercetin glycoside-containing substance by a method described below. Hereinafter, the water-soluble quercetin glycoside-containing substance and the method for producing the same will be specifically described with reference to Table 1 below in the description of the method for separating monoglucosyl rutin. In the table, R represents rutinose, and G represents glucose.

[0017]

[Table 1]

In the second separation method of monoglucosyl rutin, a mixture (A) of α-glucosylated rutin and rutin is used as a raw material, and this mixture (A) is usually
It is commercially available under the trade name of “αG rutin” (manufactured by Toyo Seika Co., Ltd.).

This α-glucosylated rutin is represented by the following formula (b):

[0020]

Embedded image

(Wherein, in the formula (B), G is a glucose residue, R is a rhamnose residue, n is an integer of 1 to several tens), and the number of glucose residues at the α-position (n) is 1 It is a mixture of α-glucosylated rutin in the range of 数 to several tens, on average, n is about 4 to 5. This α-glucosylated rutin has
Monoglucosyl rutin in which the number (n) of glucose residues at the α-position is 1 is included.

This α-glucosylated rutin has a high solubility in water, alcohol, etc., and is soluble in 50 g or more per 100 g of water.
Dissolve 0 g or more.

Α-Glucosylated rutin is produced, for example, as follows. That is, in the following equation (a)

[0024]

Embedded image

Very poorly soluble in water (solubility:
A composition comprising rutin as a sugar donor and a partial hydrolyzate thereof (eg, dextrin, maltose) added to rutin, which is about 0.01 g per 100 g of water, and glucose residues such as amylase, glycosidase, and transglycosidase are added. Transfer (addition) of sugar (glucose) from starch or its partial degradation product to rutin by the action of transferase
By doing so, α-glucosylated rutin is obtained.

As a method for producing such α-glucosylated rutin, various conventionally known methods can be employed. Specifically, for example, Japanese Patent Publication No. 54-3207
No. 3 or JP-B-58-54799 can be employed.

The reaction product thus obtained usually contains a small amount of unreacted rutin or quercetin which is a decomposition product of rutin, in addition to α-glucosylated rutin. In this specification, the term “α-glucosylated rutin” includes monoglucosyl rutin unless it is contrary to the gist thereof.

In the present invention, the above-mentioned water-soluble quercetin glycoside-containing substance is obtained by enzymatic treatment from a mixture containing at least such α-glucosylated rutin and rutin. Hereinafter, first, the main reaction steps of the present invention will be described in detail. However, in the case where each enzyme used has a common action in adjacent steps such as the first step and the second step, In the enzyme used in the previous step,
The subsequent reaction in the subsequent step can usually be allowed to proceed.

[First Step] In the present invention, glucoamylase is allowed to act on a mixture (A) of α-glucosylated rutin and rutin to convert α-glucosylated rutin into monoglucosyl rutin. Such enzymes include Glucozyme from Nagase & Co., Ltd. and Gluczyme from Amano Pharmaceutical Co., Ltd.
NL, glucoamylase such as Uniase 30 of Yakult Co., Ltd., as well as enzymes such as naringinase of Tanabe Seiyaku, Cellulase A "Amano" 3 of Amano Pharmaceutical Co., that is, α-1,4-glucosyl bond, Any enzyme having glucoamylase activity that cleaves at the glucose unit can be used freely. Further, an enzyme such as α-amylase, β-amylase or the like that cleaves α-1,4-glucosyl bond at a position other than the glucose unit can also be used. However, among these enzymes, glucoamylase having an excellent property of converting α-glucosylated rutin into monoglucosyl rutin is preferably used.

For example, glucozyme, a kind of glucoamylase, is usually used in an amount of 0.01 to 10 g, preferably 0.2 to 1 g, per 100 g of the mixture (A) of α-glucosylated rutin and rutin. In other words, the amount is usually 0.01 to 11 g, preferably 0.2 to 100 g per 100 g of the α-glucosylated rutin content in the mixture (A).
Used in an amount of 1 g. When glucozyme is used in such an amount, α-glucosylated rutin can be efficiently converted to monoglucosyl rutin (a conversion rate of about 99%).

When an enzyme such as glucoamylase is allowed to act on the mixture (A) of α-glucosylated rutin and rutin as described above, it is not determined unconditionally depending on the type and activity of the enzyme used. In glucozyme, it is preferable to adjust the pH of the solution containing the mixture (A) to about 3 to 6 using an inorganic acid, an organic acid, or the like. In addition, at the time of this monoglucosylation reaction, it is preferable to hold at a temperature of about 35 to 65 ° C. for about 1 to 60 hours.

As described above, in the second step, the mixture (B) of monoglucosyl rutin and rutin obtained by allowing an enzyme to act on α-glucosylated rutin in the mixture (A) is
The rutin in the mixture (B) is converted to isoquercitrin by the action of α-1,6-rhamnosidase.

[Second Step] In the present invention, a mixture of monoglucosyl rutin and rutin (B) is reacted with α-1,6-rhamnosidase to obtain rhamnose units from rutin in the mixture (B). Change to isoquercitrin. The mixture (B) is not limited to the mixture obtained by using the raw material (A) in the first step, but may be the raw material (B) obtained by a known method.
Can also be used.

The enzyme used in the second step can convert rutin into isoquercitrin as long as it has an α-1,6-rhamnosidase activity. As such an enzyme, hesperidinase 2 of Tanabe Seiyaku Co., Ltd.
No., Naringinase, Cellulase A from Amano Pharmaceutical Co., Ltd.
"Amano" 3 and the like.

For example, Hesperidinase No. 2 of Tanabe Seiyaku Co., Ltd. is usually used in an amount of 0.01 to 10 g per 100 g of the mixture (B) of monoglucosyl rutin and rutin.
Preferably in an amount of from 0.3 to 2 g, in other words, usually 0.05 g per 100 g of rutin content in the mixture (B).
It is used in an amount of up to 50 g, preferably in an amount of 1.5 to 10 g. When hesperidinase is used in such an amount,
Rutin can be efficiently converted to isoquercitrin (conversion efficiency of about 99%).

As will be described later, when the enzymes of the first and second steps are added to the raw material (A) and these reactions proceed substantially simultaneously, an enzyme common to both steps (eg, naringinase) Alternatively, when cellulase A “Amano”) is used, the amount can be appropriately adjusted and set.

When an enzyme such as α-1,6-rhamnosidase is allowed to act on the mixture (B) of monoglucosyl rutin and rutin, it is not determined unconditionally depending on the type and activity of the enzyme used. For example, in hesperidinase, it is preferable to maintain the pH, temperature, and reaction time of the solution containing the mixture (B) in the same manner as in the case of the monoglucosylation reaction in the first step.

In the present invention, by such a second step,
A water-soluble quercetin glycoside-containing substance which is a mixture (C) of monoglucosyl rutin and isoquercitrin is obtained. In the present invention, if necessary, monoglucosyl rutin may be further fractionated (separated) from the water-soluble quercetin glycoside-containing substance obtained in the second step (third step).

[Third Step] That is, in the third step,
Monoglucosyl rutin is separated (separated) from the mixture (C) of monoglucosyl rutin and isoquercitrin obtained in the second step.

As described above, for separating (separating) monoglucosyl rutin from the mixture (C) obtained in the second step, the following methods [i] to [iv] can be exemplified.

[I] That is, first, β-glucosidase is allowed to act on the mixture (C) of monoglucosyl rutin and isoquercitrin obtained in the second step, so that isoquel in the mixture (C) is obtained. Change citrine to quercetin.

In the mixture (D) of monoglucosyl rutin and quercetin thus obtained or in an aqueous solution (D) containing them, quercetin precipitates. Can be easily separated into a solid and a liquid to obtain monoglucosyl rutin as a liquid phase.

As these enzymes, any enzymes having β-glucosidase activity can be used. One such enzyme is Cellulase from Amano Pharmaceutical Co., Ltd.
A "Amano" and the like can be mentioned.

For example, cellulase A "Amano" is usually used in an amount of 0.01 to 20 g per 100 g of a mixture (C) of monoglucosyl rutin and isoquercitrin.
It is preferably in an amount of 1 to 12 g, in other words, usually in an amount of 0.05 to 120 g, preferably 30 to 70 g, per 100 g of the isoquercitrin content in the mixture (C).
g. When β-glucosidase is used in such an amount, isoquercitrin can be efficiently converted to quercetin (conversion efficiency: about 90%).

When β-glucosidase is allowed to act on the mixture (C) of monoglucosyl rutin and isoquercitrin as described above, it is not determined unconditionally depending on the type and activity of the enzyme used. , Cellulase A "Amano" 3, the p of the solution containing the mixture (C)
It is preferable to adjust H to about 3 to 6 using an inorganic acid, an organic acid, or the like. In addition, in the case of this reaction, 35 to 65
It is preferable that the temperature is maintained at about ℃ for about 1 to 60 hours.

In the mixture (D) of monoglucosyl rutin and quercetin thus obtained or in an aqueous solution (D) containing these, quercetin precipitates.
By filtering, both monoglucosyl rutin and quercetin can be easily separated to obtain monoglucosyl rutin.

[Ii] In the present invention, the water-soluble quercetin glycoside-containing substance (C), which is a mixture of monoglucosyl rutin and isoquercitrin, obtained in the second step,
Alternatively, monoglucosyl rutin can be fractionated from the aqueous solution (C) containing these by using an adsorption resin.

As the adsorption resin, for example, intermediate polar resin XAD7, non-polar resin HP-20, HP-50, XAD
-2 or the like is used. [Iii] In the present invention, the mixture (C) of monoglucosyl rutin and isoquercitrin obtained in the second step is once dissolved in alcohol, crystallized, and then filtered to remove crystals. Monoglucosyl rutin can also be obtained by fractionation. Examples of the alcohol include lower alcohols having about 1 to 4 carbon atoms, such as methanol, ethanol, propanol, and butanol.

Prior to the crystallization of monoglucosyl rutin in the above alcohol, the mixture (C) or an aqueous solution (C) containing these is converted to the mixture (C) by using the same adsorption resin as described above. The contained saccharides, proteins, etc. may be removed.

[Iv] Further, in the present invention, a water-soluble quercetin glycoside-containing substance as a mixture (C) of monoglucosyl rutin and isoquercitrin obtained in the second step, or a mixture thereof is contained. Monoglucosyl rutin can also be fractionated from the aqueous solution (C) by using chromatographic separation.

In the present invention, such [i] to [iv]
May be appropriately combined. In the present invention, [iii] is preferable among the methods [i] to [iv]. This utilizes the difference in the solubility of monoglucosyl rutin and isoquercitrin in alcohol, so that high-purity monoglucosyl rutin can be obtained efficiently.
In the present invention, for example, when a mixture (A) of α-glucosylated rutin and rutin: “αG rutin”, which is commercially available from Toyo Seikagaku Co., Ltd., is used as a raw material, Subsequent to the reaction in the step, the reaction in the second step is performed, and monoglucosyl rutin may be separated from the resulting mixture (C) of monoglucosyl rutin and isoquercitrin.

In order to separate monoglucosyl rutin from the mixture (C), for example, [i] to [iv] in the third step
By employing one or two or more separation methods in combination, it is possible to efficiently obtain the desired high-purity monoglucosyl rutin.

In the present invention, for example, the raw material (A) may be combined with an enzyme such as glucoamylase used in the first step as described above and α-1,6-
An enzyme such as rhamnosidase and, if necessary, an enzyme such as β-glucosidase used in [i] of the third step may be added together to allow these reactions to proceed at substantially the same time. In addition to the order of the third step, the reaction may proceed in that order. Further, the reaction of the first step may proceed after the reaction of the second step depending on the enzyme used, and then, if necessary, , The operation of the third step, for example, the reaction [i] can be advanced.

In the present invention, when a mixture (B) of monoglucosyl rutin and rutin is used as a raw material, the above-mentioned reaction in the second step is carried out, and then the obtained monoglucosyl rutin and isoquel are used. Monoglucosyl rutin may be separated from the mixture (C) with citrine.

As described above, when the mixture (B) of monoglucosyl rutin and rutin is used as a raw material, after the above-mentioned reaction of the second step, if necessary, [i] to [iv] of the third step ], Or by appropriately combining these methods, a target high-purity monoglucosyl rutin can be efficiently obtained.

Further, the α-1,6-rhamnosidase used in the second step and the β-glucosidase used in the reaction [i] of the third step are allowed to act simultaneously to progress the reaction for converting rutin to quercetin. You can also.

The above reaction is preferably carried out in the presence of a reducing agent. As the reducing agent used herein, α-glucosylated rutin or a reducing agent having a reducing power not to excessively reduce the reaction product and having a reducing power enough to effectively prevent oxidation by dissolved oxygen or air. Preferably, in consideration of the use of monoglucosyl rutin, those having little influence on the living body are preferable. Examples of such reducing agents include ascorbic acid and ascorbate, and ascorbic acid is generally used. The amount used is α-glucosylated rutin 100
The amount is about 0.1 to 5 g per g. Such amounts of ascorbic acid are easily removed during the manufacturing process.

Monoglucosyl rutin obtained by the above separation method has high purity. If necessary, recrystallization can be further repeated to increase the purity. Such high-purity monoglucosyl rutin is preferably used for a wide range of applications such as pharmaceuticals, cosmetics, and food additives.

Further, since monoglucosyl rutin has a large amount of rutin per unit weight, by using monoglucosyl rutin instead of rutin, various properties possessed by rutin itself, such as anti-inflammatory and analgesic effects, It can exert an oxidizing action, an ultraviolet absorbing action, and the like.

[0060]

According to the present invention, a water-soluble quercetin glycoside-containing substance can be obtained from the mixture of α-glucosyl rutin and rutin or the mixture of monoglucosyl rutin and rutin by the above-described enzyme treatment. it can.

[0061]

EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.

[0062]

Example 1 100 g of a mixture of α-glucosylated rutin and rutin (A) was dissolved by adding 1000 ml of water, and then 1 g of ascorbic acid and glucozyme (manufactured by Nagase & Co., Ltd.)
1 g was added to adjust the pH to 4.5, and reacted at 55 ° C. for 24 hours. 1 g of hesperidinase No. 2 (manufactured by Tanabe Seiyaku Co., Ltd.) was added to the reaction solution (a), and the pH was adjusted to 4.0.
The reaction was carried out for 24 hours to obtain a reaction solution (b). Reaction liquid (b)
After inactivation of oxygen and filtration, the filtrate was passed through 1000 ml of the intermediate polar resin XAD-7, washed with water, and desorbed and extruded with 2000 ml of 60% ethanol and 1000 ml of water. The two liquids were combined, dealcoholized, concentrated and dried to obtain 47 g of solid (purity 65%). 99% of this solids
After adding 80 ml of methanol and dissolving by heating at 60 ° C., the mixture was allowed to stand at room temperature to precipitate crystals. The precipitated crystals are washed with a small amount of 99% methanol, dried, and solids 25 g (purity 93%)
I got

FIGS. 1 and 2 show thin-layer chromatograms of the reaction solutions (a) and (b). The development was spotted on a Kieselgel 60F ₂₅₄ thin layer plate (manufactured by Merck), and n-butanol / water /
The reaction was carried out with acetic acid = 4/5/1. In FIG. 1, the mixture (A) and the standard monoglucosyl rutin (manufactured by Hayashibara Biochemical Laboratory) were spotted as controls. The reaction solution (a) had no spots below the monoglucosyl rutin, and the generation of new monoglucosyl rutin (Rf 0.36) was confirmed due to the strong color development of the spots of the monoglucosyl rutin (mixture (B)). ). In FIG. 2, isoquercitrin (Rf 0.74) of the reaction solution (b) was confirmed from the spot of standard isoquercitrin (manufactured by Funakoshi Pharmaceutical Co., Ltd.) (mixture (C)).

[0064]

Example 2 100 g of a mixture (B) of monoglucosyl rutin and rutin obtained by the same operation as in Example 1 (purity 64
%), 150 ml of 99% methanol was added thereto, and the mixture was dissolved by heating at 60 ° C., and allowed to stand at room temperature to precipitate crystals. The precipitated crystals are washed with a small amount of 99% methanol, dried and solid content 57 g.
(84% purity).

[0065]

Example 3 To 100 g of a mixture of α-glucosylated rutin and rutin (A), 1000 ml of water was added and dissolved, 2.5 g of sodium ascorbate, 1 g of glucozyme (manufactured by Nagase & Co., Ltd.), and naringinase (Tanabe) Pharmaceutical Co., Ltd.
(0.5 g) was adjusted to pH 4.0 and reacted at 55 ° C. for 24 hours. The reaction solution is heated after inactivating oxygen and filtered,
The filtrate was passed through a non-polar resin HP-20 (1000 ml), washed with water, desorbed and extruded with 60% ethanol (2000 ml) and water (1000 ml). Combine both solutions and remove alcohol,
It was concentrated and dried to obtain 42 g of solid (purity 67%). 80 ml of 99% methanol was added to the solid content, dissolved by heating at 60 ° C., and allowed to stand at room temperature to precipitate crystals. The precipitated crystals were washed with a small amount of 99% methanol, dried and solids 23 g
(Purity 93%) was obtained.

[0066]

Example 4 1000 ml of water was added to and dissolved in 100 g of a mixture (A) of α-glucosylated rutin and rutin, and then 1 g of ascorbic acid and glucozyme (manufactured by Nagase & Co., Ltd.)
1 g, Hesperidinase 2 (manufactured by Tanabe Seiyaku Co., Ltd.) 1
g, Cellulase A “Amano” 3 (manufactured by Amano Pharmaceutical Co., Ltd.) 1
The pH was adjusted to 4.0 by adding 0 g, and the reaction was carried out at 55 ° C for 48 hours. The reaction solution was filtered by deactivating oxygen after heating, and the filtrate was passed through 1000 ml of the intermediate polar resin XAD-7, washed with water, and desorbed and extruded with 2000 ml of 60% ethanol and 1000 ml of water. Combine both solutions and remove alcohol,
It was concentrated and dried to obtain 40 g of solid (purity 80%). 80 ml of 99% methanol was added to the solid content, dissolved by heating at 60 ° C., and allowed to stand at room temperature to precipitate crystals. The precipitated crystals are washed with a small amount of 99% methanol and dried, and the solid is 22 g.
(95% purity).

[Brief description of the drawings]

FIG. 1 shows a thin-layer chromatogram of a reaction solution (a).

FIG. 2 shows a thin-layer chromatogram of a reaction solution (b).

[Explanation of symbols]

(1) ... mixture (A) (2) ... standard monoglucosyl rutin (manufactured by Hayashibara Biochemical Laboratory Co., Ltd.) (3) ... reaction solution (a) (= mixture (B)) ( 4) ・ ・ ・ Isoquercitrin (Funakoshi Pharmaceutical Co., Ltd.)
(5) ・ ・ ・ Reaction liquid (b) (= mixture (C))

──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Ikuo Takaya 1-41-41 Iwasaki Nishi, Ichihara-shi, Chiba Pref. Toyo Sugar Co., Ltd. Chiba Plant (58) Field surveyed (Int.Cl. ⁷ , DB name) ) C07H 17/07 C12P 19/14-19/60 BIOSIS (DIALOG) CA (STN)

Claims (3)

(57) [Claims] (1) A water-soluble quercetin glycoside-containing substance comprising isoquercitrin and monoglucosyl rutin. 2. A water-soluble quercetin glycoside-containing substance, characterized in that α-1,6-rhamnosidase is acted on a mixture (B) of monoglucosyl rutin and rutin to convert rutin into isoquercitrin. Manufacturing method. 3. A mixture of α-glucosylated rutin and rutin (A) is reacted with glucoamylase and α-1,6-rhamnosidase simultaneously or separately to convert α-glucosylated rutin into monoglucosyl rutin. A method for producing a water-soluble quercetin glycoside-containing substance, wherein rutin is converted to isoquercitrin.