WO2020090137A1

WO2020090137A1 - Packaged drink

Info

Publication number: WO2020090137A1
Application number: PCT/JP2019/017627
Authority: WO
Inventors: 森脇　将光; 小関　誠
Original assignee: 太陽化学株式会社; 森脇　将光; 小関　誠
Priority date: 2018-10-30
Filing date: 2019-04-25
Publication date: 2020-05-07
Also published as: JP6931747B2; JPWO2020090137A1

Abstract

A packaged drink containing a flavonoid clathrate, the flavonoid clathrate being obtained through a detachment step of treating a poorly-soluble flavonoid having a rhamnoside structure with an enzyme having rhamnosidase activity in the presence of cyclodextrin to detach rhamnose. The present invention enables prevention of deterioration in quality during processing and storage of packaged drinks and can be favorably used in the food field.

Description

Packaged beverages

The present invention relates to a packaged beverage and a method for producing the same.

Flavonoids are used for preventing flavor deterioration of foods, preventing discoloration of pigments, etc. because they have an antioxidant effect, and flavonoids are the active ingredient in Japanese food additives, existing additives, and antioxidant lists. Catechin, enzyme-treated rutin, rutin extract, tea extract, bayberry extract and the like have been reported.

Flavonoids are known to be contained in vegetables, fruits, tea, etc., and more than 3000 kinds are known. However, since many of them are sparingly soluble in water, soft drinks, liquid medicines, and other foods and beverages that need to be easily soluble in water. , Difficult to use in medicine. For example, since the solubility of hesperidin, which is a typical flavonoid, and rutin in water is 0.01% or less, it is difficult to use it in beverages and the like.

As a method for improving the solubility of a sparingly soluble flavonoid, a method of improving water solubility characterized by combining a sparingly soluble flavonoid and a water-soluble flavonoid glycoside (Patent Documents 1 and 2, Patent Document 3), sparingly soluble flavonoid- A water-soluble flavonoid characterized by containing β-cyclodextrin and glycosyl hesperidin is disclosed (Patent Document 4).

Among soft drinks, tea-based drinks are more susceptible to problems of quality deterioration than other drinks, and deterioration deteriorates product value and product life, so it is necessary to maintain quality. ..

A method of using an antioxidant such as ascorbic acid is disclosed to suppress the quality deterioration of tea beverages. For example, adding ascorbic acid or ascorbic acid salt to a tea-based beverage, or using a combination technique of cyclodextrin and ascorbic acid (Patent Document 5), and extracting with an aqueous extraction solvent containing burned green tea leaves and ascorbic acid. By adding the instant green tea (Patent Document 6) in which deterioration and deterioration due to photooxidation are suppressed, and the antioxidant-treated powdered tea obtained by subjecting powdered tea to antioxidant treatment to the tea extract, Instant green tea (Patent Document 7) in which generation of discoloration and altered odor is suppressed, ascorbic acid, and an aqueous solution containing an antioxidant such as sodium ascorbate, ground tea leaves are pulverized and extracted and atomized into water. Is disclosed (Patent Document 8), which discloses a method for producing a dispersion tea having an effect of suppressing photodegradation.

Regarding tea beverages, many methods for suppressing deterioration have been disclosed as techniques for suppressing flavor deterioration during distribution and storage of packaged tea beverages such as green tea, black tea, and oolong tea. For example, in a tea extraction step, a method for producing a tea beverage capable of preserving quality such as flavor by performing extraction under a high pressure condition of about 300 MPa at a low temperature of 100 ° C. or lower (Patent Document 9), a conventional amount A tea beverage that retains the original flavor of tea for a long period of time by mixing more than 100 tea extract residues in the tea extract (Patent Document 10), and is being stored by adding trehalose to the black tea extract. A black tea extract (Patent Document 11) in which thermal deterioration such as browning and flavor deterioration is prevented is disclosed.

Furthermore, by preparing the tea beverage in a transparent container that was adjusted to pH 5.5 to 7.0 after being acidified to pH 3.0 to 5.0, there was no occurrence of sediment even after long-term heating. , A tea beverage filled in a transparent container that retains the original taste and aroma of the tea extract as well as little color deterioration (Patent Document 12) is an extract of Echinacea purpurea, Echinacea angustifolia and Echinacea parida. Disclosed is a fermented tea beverage or semi-fermented tea beverage packaged in a container in which a flavor deterioration inhibitor containing one or more of the above is added and in which generation of an offensive odor due to long-term storage is suppressed (Patent Document 13). However, none of these is sufficient for suppressing the deterioration of the tea beverage.

In a packaged beverage, the flavor of the entire beverage after storage is significantly reduced because the flavor deteriorates during storage during sterilization and during storage before production and sale. For example, when a green tea extract is contained in a non-tea beverage such as a sports drink, a deteriorated flavor derived from the green tea extract occurs during storage of the beverage after production, and the flavor is not suitable as a non-tea beverage. Will end up. In addition, cases of selling tea-based beverages at hot vendors in winter are increasing. Long-term storage under high temperature conditions is a rather severe condition for beverage storage. Therefore, there is a problem that the flavor in the beverage deteriorates before the packaged beverage is stored in the hot vendor and sold.

Also in the beverage processed vegetables and fruits, when processing the beverage processed vegetables and fruits into a packaged beverage, through a sterilization process such as heating, in the heat sterilization process, acrid vegetables and fruits, bitterness, Problems such as deterioration of the original flavors such as sourness, astringency and earthy odor occur. Further, there is a problem that the flavor deteriorates with time during storage.

Coffee is obtained by grinding roasted coffee beans with a coffee mill or the like and then extracting with hot water or water by a method such as a drip or siphon method. Coffee just after extraction has a high aroma and is delicious, but the aroma and flavor of coffee are very delicate and unstable, and the aroma and flavor immediately after extraction change with the passage of time and cannot be retained for a long time. Absent. In the industrial production of coffee beverages, coffee beans and heated water are in contact with each other for a long time, and because heat sterilization is performed for storage, important scent of coffee disappears and flavor greatly changes. Therefore, the industrially produced container-packed coffee beverage has a significant difference in aroma and flavor from regular coffee brewed at home.

Therefore, various ideas have been proposed for realizing the taste of regular coffee with a packaged beverage filled in cans and the like. For example, a method for suppressing the oxidation of a coffee extract and stabilizing the flavor by adding L-ascorbic acid and an alkali metal carbonate (Patent Document 14), rutin, rosemary extract, sage extract and / or citric acid. A method of stabilizing the quality of a coffee extract by adding sodium acidate (Patent Document 15), by using trehalose as at least a part of sugars, the pH does not change after heat sterilization, and the sweetness and flavor are low. A method for obtaining a canned coffee having a refreshing aftertaste, which does not leave the acridness of coffee beans (Patent Document 16), a mixture of one or more kinds selected from peptides and / or amino acids, and tocopherols and polyphenols. Method for stabilizing the flavor of coffee extract by containing it (Patent Document 17), L-histidine hydrochloride in coffee beverage Characterized in that the addition 0.01 to 1.5% by mass, heat sterilization treatment coffee with improved-flavor such as retort odor and potato odor (Patent Document 18), and the like. In addition, high-quality coffee with excellent taste and aroma is obtained by a two-step extraction method in which coffee beans are first extracted with hot water at high temperature (50 ° C to 90 ° C) and then extracted with low temperature water (0 ° C to 40 ° C). Attempts have also been made to improve the flavor of industrial coffee beverages by devising manufacturing conditions such as extraction conditions and sterilization conditions, such as the method for obtaining beverages (Patent Document 19).

Furthermore, additives for coffee beverages that can enhance the coffee flavor are being developed. For example, it consists of an extract obtained by extracting roasted and ground coffee beans with a water-ethanol mixed solvent at 10 to 40 ° C. for 10 to 60 days, which is excellent when added to a coffee base for beverages. There is a taste improver for coffee drinks and milk drinks (Patent Document 20) capable of imparting aroma, taste, richness, bitterness, and after-breakage.

On the other hand, ethyl isovalerate (Ethyl Isovalerate) has a fruit-like aroma such as apple scent, and is known to be added to foods for flavoring such as citrus flavor (Patent Document 21). It is not known to have a flavor enhancing effect.

Also, in the manufacture of milk-containing beverages including milk-containing coffee beverages, the "sterilization" step is an important quality step. In the sterilization process, usually 250 g cans are sterilized by heating at 125 ° C. for 20 minutes, but the characteristic flavor deterioration occurs after the sterilization by heating. However, there is known an economical production method in which a basic substance and / or a basic amino acid is added to a coffee component, and the mixture is mixed with milk and then sterilized by heating to prevent generation of a precipitate and improve flavor. (Patent Document 22).

Japanese Patent No. 4902151 Japanese Patent No. 3833775 JP-A-7-10898 Japanese Patent No. 50000373 JP-A-2004-73057 Japanese Patent Laid-Open No. 2005-58142 JP, 2006-254819, A JP, 2007-289115, A JP-A-5-49401 JP-A-7-59513 JP, 2001-245592, A JP, 2005-198531, A JP, 2005-80436, A Japanese Patent Publication No. 6-28542 Japanese Patent Publication No. 6-75470 Japanese Unexamined Patent Publication No. 8-298932 JP, 2002-119210, A JP, 2005-137266, A JP-A-6-70682 JP-A-2003-116464 Japanese Patent Laid-Open No. 2005-15686 JP, 2002-186425, A

However, in the case of packaged beverages, the quality deterioration prevention methods disclosed in the above-mentioned prior art documents are not sufficiently satisfactory, and further improvement is desired.

An object of the present invention is to provide a packaged beverage with suppressed quality deterioration and a method for producing the same.

The present invention relates to the following [1] to [23].
[1] A packaged beverage containing a flavonoid inclusion compound, wherein the flavonoid inclusion compound treats a poorly soluble flavonoid having a rhamnoside structure with an enzyme having rhamnosidase activity in the presence of cyclodextrin to remove rhamnose. A packaged beverage, which is obtained through a desorption step of separating.
[2] The packaged beverage according to [1], which further contains rhamnose.
[3] The sparingly soluble flavonoid having the rhamnoside structure is rutin, hesperidin, naringin, diosmin, eriocitrin, myricitrin, neohesperidin, luteolin-7-rutinoside, delphinidin-3-rutinoside, cyanidin-3-rutinoside, isorhamnetin- The packaged beverage according to [1] or [2], which is at least one member selected from the group consisting of 3-rutinoside, kaempferol-3-rutinoside, and acacetin-7-rutinoside.
[4] The container according to any one of [1] to [3], wherein the cyclodextrin is one or more selected from the group consisting of β-cyclodextrin, branched β-cyclodextrin, and γ-cyclodextrin. Packed beverage.
[5] A packaged beverage containing a flavonoid clathrate compound, wherein the flavonoid clathrate compound is a compound in which a flavonoid having no rhamnoside structure is clathrated in cyclodextrin, and the flavonoid and cyclone in the flavonoid clathrate compound are included. A packaged beverage having a molar ratio with cyclodextrin (cyclodextrin / flavonoid) of 0.01 to 10.0.
[6] The flavonoid in the flavonoid inclusion compound is isoquercitrin, hesperetin-7-glucoside, naringenin-7-glucoside (purin), diosmethine-7-glucoside, myricetin, eriodictyol-7-glucoside, luteolin-7. -Glucoside, delphinidin-3-glucoside, cyanidin-3-glucoside, isorhamnetin-3-glucoside, kaempferol-3-glucoside, apigenin-7-glucoside, quercetin, hesperetin, naringenin, acacetin-7-glucoside, and these The packaged beverage according to [5], which comprises at least one selected from the group consisting of derivatives.
[7] The packaged beverage according to [5] or [6], wherein the cyclodextrin contains one or more selected from the group consisting of β-cyclodextrin, branched-β-cyclodextrin, and γ-cyclodextrin. ..
[8] The flavonoid inclusion compound is a flavonoid inclusion compound in which isoquercitrin is included in γ-cyclodextrin, and a molar ratio of the isoquercitrin and the γ-cyclodextrin (γ-cyclodextrin / Isoquercitrin) is 1.0 to 3.0, and the solubility of the isoquercitrin in water is 0.01% or more, and the packaged beverage according to any one of [5] to [7].
[9] The flavonoid inclusion compound is a flavonoid inclusion compound in which isoquercitrin is included in γ-cyclodextrin, and a molar ratio of the isoquercitrin to the γ-cyclodextrin (γ-cyclodextrin / Isoquercitrin) is 0.9 to 4.0, and the solubility of the isoquercitrin in water is 0.01% or more, and the packaged beverage according to any one of [5] to [7].
[10] The flavonoid inclusion compound is a flavonoid inclusion compound in which isoquercitrin is included in β-cyclodextrin, and a molar ratio of the isoquercitrin to the β-cyclodextrin (β-cyclodextrin / Isoquercitrin) is 1.0 to 3.0, and the solubility of the isoquercitrin in water is 0.01% or more, and the packaged beverage according to any one of [5] to [7].
[11] The flavonoid inclusion compound is a flavonoid inclusion compound in which hesperetin-7-glucoside is included in cyclodextrin, and a molar ratio of the hesperetin-7-glucoside and the cyclodextrin (cyclodextrin / hesperetin- 7-Glucoside) is 1.0 to 3.0, and the solubility of hesperetin-7-glucoside in water is 0.01% or more. [5] to [7].
[12] The packaging according to any one of [5] to [11], further comprising rhamnose, wherein the flavonoid in the flavonoid inclusion compound and the rhamnose have a molar ratio (rhamnose / flavonoid) of 0.1 to 10. Beverage.
[13] The packaged beverage according to [12], wherein the flavonoid in the flavonoid inclusion compound and the rhamnose have a molar ratio (rhamnose / flavonoid) of 0.8 to 1.2.
[14] A packaged beverage containing a flavonoid glycoside composition, wherein the flavonoid glycoside composition treats a flavonoid inclusion compound with a glycosyltransferase to form a glycoside. The flavonoid clathrate compound is obtained by subjecting a sparingly soluble flavonoid having a rhamnoside structure to an enzyme having rhamnosidase activity in the presence of cyclodextrin to eliminate rhamnose. The obtained packaged beverage.
[15] The packaged beverage according to [14], wherein the glycoside conversion step is performed in an aqueous medium having a pH of 3 to 7.
[16] The glycoside composition is an isoquercitrin glycoside composition represented by the following general formula (1), wherein the content of the glycoside of n = 0 in the glycoside composition is Is 10 mol% or more and 30 mol% or less, the content of glycosides with n = 1 to 3 is 50 mol% or less, and the content of glycosides with n = 4 or more is 30 mol% or more The packaged beverage according to [14] or [15].

(In the general formula (1), Glc means a glucose residue, and n means 0 or an integer of 1 or more.)
[17] The glycoside composition is a hesperetin-7-glucoside glycoside composition represented by the following general formula (2), wherein n = 0 in the glycoside composition: The content is 10 mol% or more and 30 mol% or less, the content of the glycoside of n = 1 to 3 is 50 mol% or less, and the content of the glycoside of n = 4 or more is 30 mol% or more The packaged beverage according to [14] or [15].

(In the general formula (2), Glc means a glucose residue, and n means 0 or an integer of 1 or more.)
[18] The glycoside composition is an aggregon glycoside composition represented by the following general formula (3), wherein the content of the glycoside of n = 0 is 10 in the glycoside composition. Mol% or more and 30 mol% or less, the content of glycosides with n = 1 to 3 is 50 mol% or less, and the content of glycosides with n = 4 or more is 30 mol% or more, [ 14] or the packaged beverage according to [15].

(In the general formula (3), R 1 to R 9 are each independently —H, —OH, —OCH ₃ , —O-Glc- (Glc) n, where Glc is a glucose residue and n is 0. Alternatively, it means an integer of 1 or more, and at least one or more substituents of R1 to R9 is —O—Glc- (Glc) n.)
[19] Any of [14] to [18], further comprising rhamnose, wherein the flavonoid glycoside composition has a molar ratio (rhamnose / flavonoid) of rhamnose in terms of flavonoids of 0.1 to 10. Or a packaged beverage as described above.
[20] The packaged beverage according to [19], wherein the flavonoid glycoside composition has a flavonoid-equivalent number of moles and the rhamnose has a molar ratio (rhamnose / flavonoid) of 0.8 to 1.2.
[21] Tea-based beverages, coffee-based beverages, cocoa-based beverages, non-alcoholic beer-taste beverages, fruit juice beverages, vegetable beverages, carbonated beverages, functional beverages, mineral water, alcoholic beverages, dairy beverages, or soup-based beverages, The packaged beverage according to any one of [1] to [20].
[22] A method for producing a packaged beverage containing a flavonoid inclusion compound, which comprises treating a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having a rhamnosidase activity in the presence of cyclodextrin to eliminate rhamnose. A manufacturing method including a step.
[23] A method for producing a packaged beverage containing a flavonoid glycoside composition, which comprises treating a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having a rhamnosidase activity in the presence of cyclodextrin to eliminate rhamnose. A production method comprising a desorption step and a glycoside conversion step of treating the flavonoid inclusion compound obtained through the desorption step with a glycosyltransferase to form a glycoside.

According to the present invention, it is possible to provide a packaged beverage with suppressed quality deterioration and a method for producing the same.

When the present inventors examined the above-mentioned problems, a flavonoid compound obtained by removing rhamnose by using an enzyme (enzymatic method) in the presence of cyclodextrin, a sparingly soluble flavonoid having a rhamnoside structure, was obtained. It has also been found that by adding a flavonoid glycoside composition obtained by adding sugar to the flavonoid compound to a packaged beverage, the deterioration of the quality of the packaged beverage can be significantly suppressed. Although the mechanism is unknown, for example, flavonoid glycosides (eg, rutin) obtained by the dissolution method or the mixing method are included in the inclusion of cyclodextrin in the flavonoid glycosides A-C and B-rings. And, it is randomly included with the sugar part (PLOS ONE, 10 (3), e0120858, 2015), but when the inclusion compound was prepared by the enzymatic method, the joining site and the ratio of the flavonoid glycosides included with the cyclodextrin. However, with a certain regularity, it is expected that a certain site will be strongly clathrated, and the flavonoid glycoside composition prepared from the clathrate compound has a unique flavonoid glycoside molar composition ratio. Therefore, it is estimated that the stability of flavonoids becomes high, and the effect of suppressing the quality deterioration of the packaged beverage, the effect of preventing flavor deterioration, the effect of preventing oxidation, etc. will become extremely strong. In the following description, an embodiment using cyclodextrin will be described as an example, but the present invention is not limited to this, and other cyclic oligosaccharides can be similarly used. Here, the cyclic oligosaccharide refers to a compound in which monosaccharides are connected in a cyclic form, and more specifically, examples thereof include cyclodextrin, cyclodextran, cyclofructan, and cycloaltanan.

The packaged beverage of the present invention contains the flavonoid inclusion compound and / or flavonoid glycoside composition obtained by the production method described below.

The content of the flavonoid clathrate compound, when expressed based on the content of the flavonoid in the flavonoid clathrate compound, in the packaged beverage of the present invention, the content as the flavonoid is preferably 0.001% by mass or more. , More preferably 0.005 mass% or more, further preferably 0.01 mass% or more, from the viewpoint of suppressing flavor deterioration and quality deterioration of the packaged beverage, and economical. From this viewpoint, the amount is preferably 1% by mass or less, and more preferably 0.1% by mass or less. The content in the case of containing two or more flavonoid clathrate compounds refers to the total amount thereof.

When the content of the flavonoid glycoside composition is expressed based on the content of the flavonoid in the flavonoid glycoside composition, the content of the flavonoid in the packaged beverage of the present invention is preferably 0.001% by mass or more. From the viewpoint of suppressing flavor deterioration and quality deterioration of the packaged beverage, it is more preferably 0.005% by mass or more, further preferably 0.01% by mass or more. From an economical viewpoint, the amount is preferably 1% by mass or less, more preferably 0.1% by mass or less. The content in the case of containing two or more flavonoid glycoside compositions refers to the total amount thereof.

When the flavonoid clathrate compound and the flavonoid glycoside composition are used in combination, the total content thereof is 0.001 to 1% by mass in the packaged beverage when the flavonoid content is displayed as a reference. Preferably.

The method for producing a flavonoid clathrate compound for use in a packaged beverage according to the present invention, a sparingly soluble flavonoid having a rhamnoside structure is treated with an enzyme having rhamnosidase activity in the presence of cyclodextrin to eliminate rhamnose. including.

Therefore, as a method for producing a packaged beverage containing the flavonoid inclusion compound of the present invention, a sparingly soluble flavonoid having a rhamnoside structure is treated with an enzyme having a rhamnosidase activity in the presence of cyclodextrin to remove rhamnose. The manufacturing method includes a separation step.

The elimination step is a step of eliminating rhamnose from a sparingly soluble flavonoid having a rhamnoside structure to obtain an inclusion compound of a flavonoid having no rhamnoside structure and cyclodextrin (also referred to as “flavonoid inclusion compound”). The desorption step can be carried out while standing in a solvent such as water or while stirring, and in order to prevent oxidation or browning during the reaction, the air in the headspace of the reaction system is replaced with an inert gas such as nitrogen. May be substituted with, and an antioxidant such as ascorbic acid may be added to the reaction system. The elimination step can be completed by a known method such as a method of inactivating the enzyme by heating the reaction solution.

Incidentally, in the present specification, a liquid obtained by filtering the prepared liquid after the elimination step, and further powdered by a spray dryer or freeze-drying after that is referred to as a "flavonoid inclusion compound-containing composition" containing rhamnose, Further, a liquid obtained by removing rhamnose by dialysis, resin or the like, or a dried product is described as "flavonoid inclusion compound".

As the sparingly soluble flavonoid having a rhamnoside structure, those having a structure in which one or more, preferably two or more, hydroxy groups are bonded to the benzene ring of the flavonoid skeleton and which has a rhamnose can be used. Here, “poorly soluble” means that the solubility in water at 25 ° C. is 0.01% by mass or less. Specifically, rutin, hesperidin, naringin, diosmin, eriocitrin, myricitrin, neohesperidin, luteolin-7-rutinoside, delphinidin-3-rutinoside, cyanidin-3-rutinoside, isorhamnetin-3-rutinoside, kaemperol-3- Examples thereof include rutinoside, acacetin-7-rutinoside and derivatives thereof. Examples of the derivative include acetylated products, malonylated products, and methylated products.

Although the amount of the sparingly soluble flavonoid having a rhamnoside structure is not particularly limited, it is preferably 0.1 to 20% by mass, more preferably 1 to 15% by mass, further preferably 2 to 14% in the reaction system. It can be mass%. When two or more kinds of hardly soluble flavonoids having a rhamnoside structure are used, the amount used means the total amount thereof.

A raw material containing a sparingly soluble flavonoid having a rhamnoside structure need not be particularly purified, but is preferably purified. The content of the sparingly soluble flavonoid having a rhamnoside structure in the raw material is not particularly limited and is preferably 20% or more, more preferably 50% or more, further preferably 80% or more, and further preferably 90% or more can be used.

The cyclodextrin that is present in the elimination step is a kind of cyclic oligosaccharide in which D-glucose is bonded by an α-1,4 glycoside bond to form a cyclic structure, and seven bonded are β-cyclodextrin. What is bound eight is γ-cyclodextrin. The cyclodextrin (CD) is not particularly limited, but is preferably β-cyclodextrin (β-CD), branched β-cyclodextrin (branched β-CD), and γ-cyclodextrin (γ-CD). One or more selected from the group consisting of) can be used. A branched β-CD is one in which one or more glucose residues, a galactosyl group, or a hydroxypropyl group is linked to β-CD as a side chain. Maltosyl β-CD (G2-β-CD), hydroxy Examples include propyl-β-CD (HP-β-CD). In addition, "in the presence of cyclodextrin" refers to a state in which cyclodextrin is contained in the elimination reaction system.

Although the amount of cyclodextrin to be present is not particularly limited, it is preferably 0.01 to 60% by mass, more preferably 1 to 50% by mass, further preferably 3 to 40% by mass in the reaction system. be able to. The amount when two or more cyclodextrins are used refers to the total amount.

From the viewpoint of efficiency, the molar ratio of cyclodextrin to the sparingly soluble flavonoid having a rhamnoside structure (cyclodextrin / flavonoid) is preferably 0.01 or more, more preferably 0.1 or more, and further preferably It is 0.9 or more, preferably 10 or less, more preferably 6 or less, and further preferably 4 or less from the viewpoint of economy.

The origin of the enzyme having rhamnosidase activity is not limited, and any origin derived from animals, plants, microorganisms, etc. can be used. Further, it may be a gene recombinant enzyme. The form of the enzyme is not particularly limited.

Specific examples of the enzyme having rhamnosidase activity include hesperidinase, naringinase, β-glucosidase, pectinase and the like.

The amount of the enzyme having rhamnosidase activity used varies depending on the type of enzyme used, the reaction conditions, the type of sparingly soluble flavonoids having a rhamnoside structure as a raw material, and for example, in the case of hesperidinase, naringinase, and β-glucosidase, rhamnoside is used. It is preferably 0.01 to 1000 U per 1 g of the slightly soluble flavonoids having a structure. Regarding the reaction conditions, the reaction temperature and the pH of the reaction solution can be selected in accordance with the characteristics of the enzyme used, but it is preferably pH 3 to 7, and more preferably pH 3.5 to 6.5. In addition, it is also possible to dissolve hardly soluble flavonoids having a rhamnoside structure in the alkaline region and then carry out an enzymatic reaction at pH 7 or less. Examples of the solvent used in the reaction system include an aqueous medium. In the present specification, the aqueous medium refers to water or an aqueous solution of an organic solvent. Examples of water include tap water, distilled water, ion-exchanged water, and purified water. The organic solvent is not particularly limited as long as it can be uniformly mixed with water. Ethanol is preferable as the organic solvent from the viewpoint of being applicable to foods. The reaction temperature is preferably 10 to 80 ° C, more preferably 40 to 75 ° C. The reaction time varies depending on the type of enzyme and the like, but can be, for example, 1 to 100 hours, preferably 2 to 24 hours.

Enzymes having rhamnosidase activity may also have glucosidase activity, and due to glucosidase activity, from sparingly soluble flavonoids having a rhamnoside structure (such as hesperidin, rutin, naringin, myricitrin) to aglycone inclusion compounds (quercetin inclusion compounds, hesperetin). Inclusion compounds, naringenin inclusion compounds, myricetin inclusion compounds, etc.) are not limited, and these are also included in the flavonoid inclusion compounds according to the present invention.

The generated flavonoid inclusion compound is an inclusion compound of a flavonoid having no rhamnoside structure and cyclodextrin as described above. Here, the clathrate compound refers to a compound that is generated by the inclusion of the other chemical species by forming a space on the molecular scale by one of the chemical species and matching the shape and size to the space.

Examples of flavonoids having no rhamnoside structure include isoquercitrin, hesperetin-7-glucoside, naringenin-7-glucoside (purinine), diosmethine-7-glucoside, myricetin, eriodictyle-7-glucoside, luteolin-7-glucoside. , Delphinidin-3-glucoside, cyanidin-3-glucoside, isorhamnetin-3-glucoside, kaempferol-3-glucoside, apigenin-7-glucoside, quercetin, hesperetin, naringenin, acacetin-7-glucoside, and derivatives thereof Is mentioned.

Specific examples of structural formulas of a sparingly soluble flavonoid having a rhamnoside structure and a flavonoid having no rhamnoside structure are shown below. Rutin having a rhamnoside structure (RTN), hesperidin (HSP), naringin (NRG), and isoquercitrin having no rhamnoside structure (IQC), quercetin (QCT), hesperetin-7-glucoside (HPT-7G), hesperetin (HPT), naringenin-7-glucoside (purnin) (NGN-7G, prunin), naringenin (NGN) have the following structural formulas.

From the viewpoint of efficiency, the molar ratio (cyclodextrin / flavonoid) in the inclusion complex of cyclodextrin with respect to the flavonoid having no rhamnoside structure is preferably 0.01 or more, more preferably 0.1 or more. Yes, more preferably 0.9 or more, further preferably 1.0 or more, from the viewpoint of economic efficiency, preferably 10.0 or less, more preferably 6.0 or less, and further preferably It is 4.0 or less.

The yield of the produced flavonoid inclusion compound is preferably 40 to 100%, more preferably 70 to 100%, and further preferably 90 to 100%. The yield is the conversion rate of a sparingly soluble flavonoid having a rhamnoside structure to a flavonoid having no rhamnoside structure, and can be calculated by the method described in Examples below.

In the produced flavonoid clathrate compound or flavonoid clathrate compound-containing composition (both may be referred to as “flavonoid clathrate compound etc.”), the solubility of the flavonoid moiety in water is determined by the sparingly soluble flavonoid having the rhamnoside structure used. And, depending on the type and amount of cyclodextrin, 0.001% or more, preferably 0.015% or more, more preferably 0.02% or more, still more preferably 1.0% or more, It is more preferably 2.0% or more, further preferably 2.5% or more, and further preferably 3% or more. The upper limit is not particularly limited, but may be 20% or less, for example. In the present specification, the solubility of the flavonoid moiety in water is a mass percent concentration at 25 ° C, and can be measured by the method described in Examples below.

Specific modes are shown below.

Aspect 1-1
A flavonoid inclusion compound in which isoquercitrin is included in γ-cyclodextrin, and a molar ratio (γ-cyclodextrin / isoquercitrin) in the inclusion body of isoquercitrin and γ-cyclodextrin. From the viewpoint of suppressing the production cost, it is preferably 0.9 to 4.0, more preferably 1.0 to 3.0, and still more preferably 1.0 to 1.8. The water solubility of isoquercitrin is 0.01% or more, preferably 2% or more, more preferably 2.5% or more, still more preferably 3% or more.

Aspect 1-2
A flavonoid inclusion compound in which isoquercitrin is included in β-cyclodextrin, and a molar ratio (β-cyclodextrin / isoquercitrin) in the inclusion complex of isoquercitrin and β-cyclodextrin. Is 1.0 to 3.0, the solubility of the isoquercitrin in water is 0.01% or more, preferably 0.02% or more, more preferably 0.03% or more. , And more preferably 0.05% or more.

Aspect 1-3
A flavonoid inclusion compound in which hesperetin-7-glucoside is included in cyclodextrin, the molar ratio of the inclusion complex of the hesperetin-7-glucoside and the cyclodextrin (cyclodextrin / hesperetin-7-glucoside). Is 1.0 to 3.0, the solubility of hesperetin-7-glucoside in water is preferably 0.01% or more, more preferably 0.02% or more, and further preferably It is 0.03% or more.

According to the above-mentioned method for producing a flavonoid clathrate compound, a flavonoid clathrate compound-containing composition containing a flavonoid clathrate compound and rhamnose can be obtained when it is unpurified. In this case, the molar ratio of the flavonoid in the flavonoid inclusion compound to the released rhamnose (rhamnose / flavonoid) is 0.8 to 1.2.

The above-mentioned method for producing a flavonoid inclusion compound is not particularly limited in purification as necessary in addition to the desorption step, and includes a resin treatment step (adsorption method, ion exchange method, etc.), a membrane treatment step (limitation). It can be purified by an outer filtration membrane treatment method, a reverse osmosis membrane treatment method, a zeta potential membrane treatment method, etc.), and an electrodialysis method, salting out, acid precipitation, recrystallization, a solvent fractionation method and the like. For example, a composition containing a flavonoid inclusion compound containing rhamnose obtained in the desorption step is adsorbed with a porous synthetic adsorbent, washed with water to remove rhamnose and the like, then eluted with alcohol, and spray-dried. A purified flavonoid inclusion compound powder can be obtained, and after elution with alcohol, a diluent material or other additive may be contained as a component other than the composition. Rhamnose and the like can be fractionated and used in the fields of foods, pharmaceuticals, quasi drugs, and cosmetics.

The diluent material is not particularly limited, and examples thereof include sugars such as sugar, glucose, dextrin, starches, trehalose, lactose, maltose, starch syrup, and liquid sugar; alcohols such as ethanol, propylene glycol, and glycerin; sorbitol, mannitol, Examples thereof include sugar alcohols such as xylitol, erythritol, maltitol, reduced starch syrup, and mannitol; or water. Examples of additives include phosphates, organic acids, auxiliaries such as chelating agents, and antioxidants such as ascorbic acid.

Next, a method for producing the flavonoid glycoside composition used in the packaged beverage of the present invention will be described.

The method for producing a flavonoid glycoside composition includes a glycosylation step of treating the flavonoid inclusion compound obtained by the above-described method for producing a flavonoid inclusion compound with glycosyltransferase to form a glycoside. That is, a sparingly soluble flavonoid having a rhamnoside structure, in the presence of cyclodextrin, an elimination step of eliminating rhamnose by treating with an enzyme having a rhamnosidase activity, and a flavonoid inclusion compound obtained through the elimination step, It includes a glycosylation step of treating with a glycosyltransferase to form a glycoside.

Therefore, as a method for producing a packaged beverage containing the flavonoid glycoside composition of the present invention, a sparingly soluble flavonoid having a rhamnoside structure is treated with an enzyme having a rhamnosidase activity in the presence of cyclodextrin to release rhamnose. And a glycosylation step of treating the flavonoid inclusion compound obtained through the above-mentioned elimination step with a glycosyltransferase to form a glycoside.

The desorption step and the flavonoid inclusion compound obtained through the desorption step are as described above. It should be noted that the phrase "obtained through the desorption process" does not mean to exclude those including processes other than the desorption process, but also includes those obtained through an optional purification process or the like.

The glycosylation step is a step in which a glycosyltransferase is allowed to act on the flavonoid inclusion compound obtained through the elimination step to form a glycoside, thereby obtaining a flavonoid glycoside composition. Further, the glycoside conversion step can be carried out in a solvent such as water while stirring or stirring as in the desorption step, and in order to prevent oxidation or browning during the reaction, the head of the reaction system is The air in the space may be replaced with an inert gas such as nitrogen, or an antioxidant such as ascorbic acid may be added to the reaction system. The glycosylation step can be completed by a known method such as a method of inactivating the enzyme by heating the reaction solution.

In the glycoside conversion step, the flavonoid clathrate compound cyclodextrin serves as a sugar donor, and a flavonoid glycoside composition can be produced, but there is no limitation on additional supply of the sugar donor. Specific examples of the sugar donor additionally donated include starch, partially hydrolyzed starch such as dextrin and maltooligosaccharide, xylo-oligosaccharide, and their inclusions.

The glycosyltransferase is not particularly limited as long as it is an enzyme having a sugar-transferring activity for the flavonoid inclusion compound obtained through the elimination step. The origin of the glycosyltransferase is not limited, and any origin such as animal origin, plant origin, microorganism origin and the like can be used. Further, it may be an artificial enzyme by gene recombination technology, partial hydrolysis or the like. The form of the glycosyltransferase is not particularly limited, and a dried product of the enzyme protein, an enzyme immobilized with an insoluble carrier, a liquid containing the enzyme protein, and the like can be used.

Specific examples of the glycosyltransferase include cyclodextrin glucanotransferase, glucosyltransferase, α-glucosidase, β-glucosidase, α-galactosidase, β-galactosidase, α-amylase, xylanase, pullulanase and arabinofuranosidase. ..

The amount of glycosyltransferase used varies depending on the type of enzyme used, the conditions of the glycosyl transfer reaction, the type of sugar, etc. For example, in the case of cyclodextrin glucanotransferase, 1 to 10000 U is preferable for 1 g of the flavonoid inclusion compound. When saccharifying a sparingly soluble flavonoid, it is common to make the sparingly soluble flavonoid solubilize so that the enzyme reaction is carried out on the alkaline side. However, in the alkaline region above pH 7, the stability of the flavonoid becomes poor and the decomposition occurs. -In addition to being easily browned, a step of removing brown matter is required, and a desalting step by neutralization with an alkali is also required. However, in the flavonoid clathrate compound obtained by the production method of the present invention, since the poorly soluble flavonoid is solubilized at a high concentration even at pH 7 or lower, the enzymatic reaction is efficiently glycosylated even at pH 7 or lower. Therefore, from the viewpoint of production efficiency and quality, the pH is preferably 3 to 7, and more preferably 6 to 6.8. However, it is also possible to transfer the sugar in the alkaline range, or to adjust the pH to 7 or less after the preparation in the alkaline range to transfer the sugar. Examples of the solvent used in the reaction system include an aqueous medium. The reaction temperature is preferably 40 to 70 ° C, more preferably 50 to 65 ° C. The reaction time varies depending on the type of enzyme and the like, but can be, for example, 0.5 to 120 hours, preferably 1 to 30 hours. In addition, from the viewpoint of production efficiency, it is preferable that the temperature and pH are optimally changed continuously after the elimination step, and a glycosyltransferase is added to carry out the glycoside conversion step.

The binding mode of the sugar that binds to the flavonoid may be α-bond or β-bond. The type of sugar to be bound is not particularly limited, but at least one selected from 5 to 6 monosaccharides such as glucose, galactose, fructose and the like is preferable. The number of sugar bonds is preferably 1 to 30, more preferably 1 to 25, still more preferably 1 to 20, further preferably 1 to 15, and further preferably. It is 1 to 10. The flavonoid glycoside composition refers to one containing a mixture of glycosides in which the above-mentioned saccharides are bound to flavonoids, and there is no limitation on the ratio of the number of bonds of each glycoside, but from the viewpoint of not impairing the flavor of foods and drinks. The following aspects are preferable.

Aspect 2-1
An isoquercitrin glycoside composition represented by the following general formula (1), wherein the content of the glycoside with n = 0 in the glycoside composition is 10 mol% or more and 30 mol% or less. The isoquercitrin glycoside composition, wherein the content of the glycoside of n = 1 to 3 is 50 mol% or less, and the content of the glycoside of n = 4 or more is 30 mol% or more. Preferably, the content of the glycoside of n = 0 is 10 mol% or more and 30 mol% or less, and the content of the glycoside of n = 1 to 3 is 35 mol% or more and 45 mol% or less, n The content of glycosides of 4 or more is 30 mol% or more and 50 mol% or less.

(In the general formula (1), Glc means a glucose residue, and n means 0 or an integer of 1 or more.)

Aspect 2-2
A hesperetin-7-glucoside glycoside composition represented by the following general formula (2), wherein the content of the glycoside of n = 0 in the glycoside composition is 10 mol% or more and 30 mol% or less. And the content of glycosides with n = 1 to 3 is 50 mol% or less, and the content of glycosides with n = 4 or more is 30 mol% or more, hesperetin-7-glucoside glycoside Composition. Preferably, the content of the glycoside of n = 0 is 10 mol% or more and 25 mol% or less, and the content of the glycoside of n = 1 to 3 is 35 mol% or more and 50 mol% or less, n The content of glycosides of 4 or more is 30 mol% or more and 50 mol% or less.

(In the general formula (2), Glc means a glucose residue, and n means 0 or an integer of 1 or more.)

Aspect 2-3
The aggregon glycoside composition represented by the following general formula (3), wherein the content of the glycoside with n = 0 in the glycoside composition is 10 mol% or more and 30 mol% or less, n Aglycon glycoside composition having a glycoside content of 1 to 3 of 50 mol% or less and a glycoside content of n of 4 or more of 30 mol% or more. Preferably, the content of the glycoside of n = 0 is 10 mol% or more and 25 mol% or less, and the content of the glycoside of n = 1 to 3 is 35 mol% or more and 50 mol% or less, n The content of glycosides of 4 or more is 30 mol% or more and 50 mol% or less.

(In the general formula (3), R 1 to R 9 are each independently —H, —OH, —OCH ₃ , —O-Glc- (Glc) n, where Glc is a glucose residue and n is 0. Alternatively, it means an integer of 1 or more, and at least one or more substituents of R1 to R9 is —O—Glc- (Glc) n.)

The number of glucose group bonds (n number) can be adjusted arbitrarily. For example, a flavonoid glycoside composition can be prepared by treating various amylase (α-amylase, β-amylase, glucoamylase, α-glucosidase, etc.) alone or in combination after the flavonoid glycoside composition is produced. The number of glucose sugar chains in the molecule can be reduced to obtain a flavonoid glycoside composition having an arbitrary glucose sugar chain length.

According to the above-described method for producing a flavonoid glycoside composition, a flavonoid glycoside composition containing a flavonoid glycoside and rhamnose can be obtained when it is unpurified. In this case, the flavonoid-rhamnose molar ratio (rhamnose / flavonoid) in the flavonoid glycoside is 0.8 to 1.2.

In the method for producing the flavonoid glycoside composition, the purification step is not particularly limited as necessary in addition to the desorption step and the glycosylation step, and the resin treatment step (adsorption method, ion exchange method) Etc.), membrane treatment process (ultrafiltration membrane treatment method, reverse osmosis membrane treatment method, zeta potential membrane treatment method, etc.), and electrodialysis, salting out, acid precipitation, recrystallization, solvent fractionation, etc. be able to. For example, the flavonoid glycoside composition obtained in the glycoside conversion step is adsorbed on the glycoside composition by a porous synthetic adsorbent, washed with water, eluted with alcohol, and then spray-dried to obtain a purified powder. Obtainable. After elution of alcohol, a diluent material or other additive may be contained as a component other than the composition.

Specific examples of the diluted material are the same as those described in the method for producing flavonoid inclusion compounds.

The solubility in water of the flavonoid glycoside composition obtained by the above production method is preferably 0.015% or more, more preferably 0.02% or more, still more preferably 0, in terms of flavonoid conversion value. 0.1% or more, more preferably 0.5% or more. The upper limit is not particularly limited, but may be 20% or less, for example.

The packaged beverage of the present invention may further contain rhamnose from the viewpoint of preventing flavor deterioration and quality deterioration. When the packaged beverage of the present invention contains rhamnose, it is preferable to blend the above flavonoid inclusion compound-containing composition or the flavonoid glycoside composition to which sugar is added to the composition.

When the packaged beverage of the present invention contains rhamnose, the molar ratio of the flavonoid inclusion compound and rhamnose (rhamnose / flavonoid) or the molar ratio of the flavonoid glycoside composition and rhamnose (rhamnose / flavonoid) is deteriorated in flavor. From the viewpoint of prevention and prevention of quality deterioration, it is preferably 0.1 to 10.0, and more preferably 0.8 to 1.2.

The packaged beverage of the present invention is, in addition, foods such as sugars, salts, acidulants, sweeteners, flavors, antioxidants, emulsifying agents, coloring agents, reinforcing agents, thickening stabilizers, bittering agents, glycerin, and propylene glycol. Additives and ingredients such as citrus extract, vegetable extract, fruit extract, Chinese herb extract and the like such as foods and Chinese herbs can be optionally contained.

Since the packaged beverage of the present invention can suitably suppress deterioration of quality, tea-based beverages, coffee-based beverages, cocoa-based beverages, non-alcoholic beer-taste beverages, fruit juice beverages, vegetable beverages, carbonated beverages, functionality It can be suitably used for various kinds of packaged beverages such as beverages, mineral water, alcoholic beverages, milk-based beverages, soup-based beverages and the like.

Examples of the tea-based beverage in the present invention include those made from leaves of tea trees (Camellia family, Camellia genus), but are not particularly limited, and mainly tea leaves (scientific name: Camellia sinensis) Manufactured by using green tea, black tea, oolong tea, Puer tea and other teas, brown rice, wheat, and other various plant materials blended to these teas, or mainly leaves and stems of various plants other than tea trees, A liquid beverage obtained by extracting raw materials such as rhizomes, roots, flowers, fruits and the like and blending them with an aqueous solvent.

The tea-based beverage of the present invention includes green tea, which is non-fermented tea, oolong tea, which is semi-fermented tea as fermented tea, fermented black tea, and pickled tea, post-fermented tea, and processed tea that are microbial fermented teas. Specifically, as green tea which is unfermented tea, matcha, steamed green tea, gyokuro, kabusecha, sencha, gyokuro tea, Japanese tea that is bancha, and roasted green tea that is roasted green tea, pearl tea, Examples include eyebrow tea, jade green tea (Ureshino tea, Aoyagi tea), and Chinese tea that is bancha. Examples of the semi-fermentation include white tea which is withered, and blue tea which is withered / semi-fermented (Hukin-cha and Tetsu Kannon, Wuyiwan tea, Oolong tea which is Red Oolong). Examples of the fermented tea include Chinese black tea such as Ximen and Tenjiang, British black tea such as Darjeeling, Assam and Sri Lanka, Japanese black tea, Awabancha and Puar tea. Pickled tea which is microbial fermented tea includes nien such as kamicha, mien, pellets and the like, goishi tea, awabancha and the like, and post-fermented tea includes black tea of China and Japan. Examples of the processed tea include roasted green tea, green tea such as red tea, red red tea, and black black tea, and flavored tea (flower tea) such as jasmine tea, katsura tea, and orchid tea. Tea such as flavoring tea, which is further blended with brown rice, wheat, and various other plant raw materials, or raw materials such as leaves, stems, rhizomes, roots, flowers, and fruits of various plants other than tea trees A liquid beverage obtained by extracting the blended product with an aqueous solvent can be mentioned. The tea leaves are not limited as long as they can be extracted and consumed, and leaves, stems and the like can be used as appropriate. Further, its form is not limited to large leaves or powder.

The tea leaves used in the tea beverage of the present invention are obtained by cutting or powdering the tea leaves if necessary, and then extracting the mixture by mixing water, an organic solvent, or a mixture thereof. Examples of the organic solvent to be extracted include lower alcohols such as ethanol, methanol, propanol and the like, ethers such as acetone, ethyl acetate, diethyl ether and the like, but it is preferable to extract with warm water from the viewpoint of flavor.

The coffee-based beverage in the present invention refers to a beverage product produced by using a coffee component as a raw material and undergoing a heat sterilization process. The type of product is not particularly limited, but mainly includes “coffee”, “coffee beverage”, and “soft drink with coffee” which are the definitions of the “fair competition rules regarding the labeling of coffee beverages” certified in 1977. .. In addition, beverages that are made from coffee and have a milk solid content of 3.0% by mass or more are subject to the "Fair competition agreement regarding the labeling of drinkable milk" and are treated as "milk beverages." Also, for convenience, it shall be included in the coffee beverage of the present invention.

Here, the coffee content refers to a solution containing a component derived from coffee beans, for example, a coffee extract, that is, a solution obtained by extracting roasted and ground coffee beans with water or warm water. Can be mentioned. In addition, a solution obtained by preparing an appropriate amount of a coffee extract obtained by concentrating a coffee extract, a dry coffee obtained by drying a coffee extract, or the like with water or warm water is also included as the coffee content.

Note that, in the present specification, a coffee beverage produced by using a dairy component as a raw material and undergoing a heat sterilization process may be referred to as a “coffee beverage with milk”. Here, the dairy component refers to a component added to impart a milk flavor and a milky feel to a coffee beverage, and mainly refers to milk, milk and dairy products, for example, raw milk, milk, special milk, Partially skimmed milk, skim milk, processed milk, milk beverages and the like, examples of dairy products include cream, concentrated whey, concentrated milk, skimmed concentrated milk, unsweetened good milk, sweetened skim milk, whole milk powder, skim milk powder, Examples include cream powder, whey powder, buttermilk powder, modified milk powder and the like.

The cocoa-based beverage of the present invention is powdered cocoa powder or a beverage in which cocoa powder is melted, and examples thereof include cocoa and chocolate beverages. Cocoa-based beverages include those to which milk is added or emulsifiers and stabilizers are added for the purpose of improving the dispersibility of powdered cocoa powder according to taste.

In the present invention, the non-alcoholic beer-taste beverage is a beverage that does not substantially contain alcohol and has a beer-like taste and aroma, and gives a drinker a feeling of drinking beer when drinking. Refers to beverages. The alcohol concentration of the non-alcoholic beer-taste beverage is less than 1% by volume, and may be, for example, 0.5% by volume or less, 0.1% by volume or less, less than 0.005% by volume, and does not contain alcohol at all. Good. In the present specification, alcohol means ethanol unless otherwise specified.

The non-alcoholic beer taste beverage may be effervescent or non-effervescent. Non-foaming means that the gas pressure at 20 ° C is less than 0.049 MPa (0.5 kg / cm2), and foaming means that the gas pressure at 20 ° C is 0.049 MPa (0.5 kg / cm2). That is the above. In the case of foaming, the upper limit of gas pressure may be about 0.294 MPa (3.0 kg / cm 2).

The fruit juice drink in the present invention includes, but is not particularly limited to, 100% fruit juice drink, fruit juice drink, low fruit juice soft drink, fruit-containing fruit drink, pulp drink and the like. The juice drink according to the present invention is a concentrated juice obtained by concentrating the juice as it is, or a concentrated juice obtained by concentrating the juice as is generally known, or a concentrated reduction obtained by diluting the concentrated juice. In the state of fruit juice, it is manufactured by mixing it with other raw materials such as sugars, flavors and acidulants, and then subjecting it to sterilization. The fruit juice drink thus obtained usually has a flavor derived from the fruit used as the raw material.

The fruit juice beverage may contain fruit juice and particles derived from fruits, and the fruit juice is, for example, juice obtained by crushing and squeezing fruits. The fruit-derived particles are obtained, for example, by subjecting the fruit to a treatment such as crushing. Specifically, when the fruits are citrus fruits, pulp components obtained by crushing pericarp, swordfish, agate, and agate membrane are included.

The type of fruit used as a raw material for fruit juice and fruit-derived particles is not particularly limited, but examples thereof include grapes such as Muscat and Kyoho; mandarin orange, orange, lemon, grapefruit, lime, mandarin, yuzu, and seeker. , Tangerine, temple orange, tangero, calamancy, decopon, ponkan, yoyokan, banpeille and other citrus fruits; strawberry, blueberry, raspberry, acai, kiwifruit, peach, apple, pineapple, guava, banana, mango, acerola, prunes, papaya, Passion fruits, plums, pears, apricots, lychees, melons, watermelons, cherries, pears, plums and the like can be mentioned.

The vegetable drink in the present invention includes tomato drink, vegetable drink, mixed fruit and vegetable drink, smoothie, etc., but is not particularly limited.

In the present invention, the vegetable drink means a drink containing vegetable juice. In the present invention, the vegetable juice means a squeezed liquid of vegetables, a crushed vegetable product (vegetable puree) or a mixture thereof. Vegetable juice can be obtained by a known production method. The vegetable used as the raw material of the vegetable juice used in the production method of the present invention is not limited, and any one can be selected, and one or more kinds of fruit vegetables, leaf vegetables, and root vegetables can be used. Above all, the effect of the production method of the present invention becomes remarkable in the production of a vegetable beverage using as a raw material a vegetable juice having at least one of the peculiar blue odor, bitterness, astringency, and astringent taste. For example, watercress, broccoli, cabbage, arugula, komatsuna, kale, Japanese radish, cabbage radish, radish and other vegetables belonging to the crucifer family, carrots, celery, parsley, vegetables belonging to the aeri family such as tomorrow leaves, pumpkin, cucumber, bitter gourd, zucchini. , Vegetables belonging to Cucurbitaceae such as Hechima, vegetables belonging to Mallowaceae such as okra, vegetables belonging to Asteraceae such as spinach, vegetables belonging to Asteraceae such as artichoke, burdock and lettuce, vegetables belonging to Chrysanthemum vines such as asparagus, Vegetables belonging to the lindenaceae family such as Morohaya, vegetables belonging to the Tsurumurasaki family such as Tsurumurasaki, tomato, citrus, eggplant, peppers, vegetables belonging to the Solanaceae family such as paprika, leek, vegetables belonging to the lily family such as leek, green beans, green soybeans, Vegetables belonging to legumes such as peas and broad beans, Seo, sage, vegetables belonging to the Labiatae basil, because strong inherent smell of the effect of the manufacturing method of the present invention becomes remarkable when using a vegetable juice obtained from any of these vegetables. For example, the total amount of vegetable juice obtained from any of these vegetables is 0.001% by mass or more, preferably 0.01% by mass or more, and more preferably 0.1% by mass in terms of a straight line with respect to the total amount of the vegetable drink. A form containing at least 1% by mass, particularly preferably at least 0.5% by mass, and particularly preferably at least 1% by mass.

In the present invention, fruit juice may be mixed with vegetable juice. In the present invention, fruit juice refers to fruit juice, crushed fruit (fruit puree) or a mixture thereof. The fruit juice can be obtained by a known production method. The raw material of the fruit juice used in the production method of the present invention is not limited. Examples thereof include citrus fruits such as oranges and oranges, and fruit juices such as apples.

The carbonated drinks of the present invention include cola flavored drinks, transparent carbonated drinks, fruit juice-based carbonated drinks, carbonated drinks with milk, ginger ale, sugar-free carbonated drinks and the like. The carbonated beverage according to the present invention is a soft drink containing carbon dioxide gas in the beverage liquid by pressurizing carbon dioxide gas (carbon dioxide) into the beverage liquid, and means a beverage in which the carbon dioxide gas is dissolved. Carbonated beverages are produced by the stimulating sensation, etc. obtained when the carbonated gas in the beverage foams when passing through the mouth and throat when drinking, and the carbonated sensation makes the drinker feel refreshed and refreshed. ..

Also, carbonated drinks are not limited to sugar-containing types that contain sugars such as fructose-glucose liquid sugar and sugar, and sugar-free types that do not contain sugars. Although not particularly limited, sweeteners other than sugars, for example, high-sensitivity sweeteners such as aspartame may also be contained.

Also, it is possible to add flavors to carbonated drinks. The type of fragrance is not particularly limited, and may be a natural fragrance extracted from plants and animals, a chemically synthesized fragrance, or a mixed fragrance prepared by mixing a plurality of kinds of fragrances. Further, in the present embodiment, the ratio of the added flavor and the like in the beverage can be appropriately set by those skilled in the art according to the expected flavor and the like of the beverage, and is not particularly limited.

Examples of the fragrances used include lemon flavor, lime flavor, grapefruit flavor, orange flavor, sweetie flavor, shiqua surf flavor, yuzu flavor, mandarin orange flavor, sudachi flavor, karin flavor, perilla flavor, apple flavor, cream flavor, tropical fruit flavor. , Milk flavors, melon flavors, mint flavors, honey flavors, yogurt flavors, berry flavors, grape flavors, acerola flavors, avocado flavors, apricot flavors, strawberry flavors, fig flavors, persimmon flavors, kaki flavors, cassis flavors, cassis flavors, cassis flavors. Cherry flavor, watermelon flavor Plum flavor, bayberry flavor, durian flavor, pineapple flavor, papaya flavor, banana flavor, blueberry flavor, muscat flavor, mango flavor, peach flavor, pear flavor, lychee flavor, raspberry flavor, strawberry flavor, ume flavor, tea, greenery. Flavors, black tea flavors, cocoa flavors, chocolate flavors, coffee flavors, cassia flavors, rosemary flavors, peach flavors, matsubusa flavors, morohaya flavors, yakchi flavors, eucalyptus flavors, cinnamon flavors, ginger flavors, thyme flavors, nutmeg flavors. Flavor, Matatabiff Flavor, macchi flavor, pine flavor, pine tree flavor, mushroom flavor, matsutake flavor, bean flavor, marigold flavor, vanilla flavor, spice flavor, nut flavor, liquor flavor, flower flavor, vegetable flavor, etc. ..

Also, it can be a functional drink, for example, a non-tea drink such as enhanced water, sports drink, near water, etc.

Further, the functional beverage in the present invention, the maintenance of health, refers to beverages containing ingredients that are said to help promote, food drinks, health support beverages, functional soft drinks, pouch jelly, but are not particularly limited. Beverages, sports drinks, energy drinks and the like.
The food-based drink in the present invention is not particularly limited, but among the nutritional drinks of the soft drink standard, pharmaceuticals and beverages having a taste similar to that of a medicinal drink that is a quasi drug, and a nutritional tonic function are expected. Is. The functional soft drink in the present invention is a soft drink water containing a component which is not particularly limited but has a function of regulating biological activity, and catechin, various amino acids, collagen, calcium, oligosaccharides, dietary fiber, Beverages containing various vitamins and other ingredients that help maintain good health. The sports drink in the present invention is not particularly limited, but it is a drink or the like which is expected to supplement energy with sugars by adjusting the ion concentration with sodium chloride, magnesium chloride or the like to promote water absorption. The pouch jelly beverage in the present invention is not particularly limited, but it is a pouch jelly beverage enclosed in a pouch with a spout, or the like. The pouch jelly beverage of the present invention is obtained by mixing the gelling agent and the base formulation, filling the container, and cooling the mixture as necessary. In the jelly beverage of the present invention, as a gelling agent that has a large effect on mouthfeel exclusively, gellan gum, xanthan gum, locust bean gum, agar, high-strength agar, carrageenan, glucomannan, guar gum, tara gum, tamarind gum, amylose, amylopectin. , Agarose, agaropectin, furceleran, alginic acid, pectin, dextran, pullulan, cellulose, curdlan, gelatin and the like can be used. Among these gelling agents, it is preferable to use at least one selected from gellan gum, xanthan gum, locust bean gum and agar, and more preferably one selected from agar and gellan gum, xanthan gum and locust bean gum. The above is used, and more preferably gellan gum, xanthan gum, roast bean gum and agar are all used.

The mineral water in the present invention refers to beverages that comply with the “Quality Labeling Guidelines for Mineral Waters” established in 1990 by the Ministry of Agriculture, Forestry and Fisheries, although not particularly limited. In the present invention, mineral water refers to natural water, natural mineral water, and mineral water. Natural water refers to groundwater pumped up from the stratum, and natural mineral water is water in which inorganic salts have dissolved out into water. All indicate water that has been subjected to natural filtration or heat sterilization without chemical sterilization. The mineral water in the present invention is, among natural mineral water, artificial sterilization treatment, water purification treatment, or component preparation, and can be modified for the purpose of stabilizing the quality of the product. The bottled water in the present invention includes not only groundwater but also water taken from water sources such as rivers and distilled water, and is applied as drinking water.

These mineral waters can be obtained by a known manufacturing method. In the mineral water of the present invention, one or more flavor improving agents can be added, if necessary. Examples of the fragrances used include lemon flavor, lime flavor, grapefruit flavor, orange flavor, sweetie flavor, shiqua surf flavor, yuzu flavor, mandarin orange flavor, sudachi flavor, karin flavor, perilla flavor, apple flavor, cream flavor, tropical fruit flavor. , Milk flavors, melon flavors, mint flavors, honey flavors, yogurt flavors, berry flavors, grape flavors, acerola flavors, avocado flavors, apricot flavors, strawberry flavors, fig flavors, persimmon flavors, kaki flavors, cassis flavors, cassis flavors, cassis flavors. Cherry flavor, watermelon flavor, Peach flavor, bayberry flavor, durian flavor, pineapple flavor, papaya flavor, banana flavor, blueberry flavor, muscat flavor, mango flavor, peach flavor, pear flavor, lychee flavor, raspberry flavor, strawberry flavor, ume flavor, tea flavor. Oolong Tea Flavor, Tea Flavor, Cocoa Flavor, Chocolate Flavor, Coffee Flavor, Cassia Flavor, Rosemary Flavor, Momoki Flavor, Matsubusa Flavor, Morohei Ya Flavor, Yakuchi Flavor, Eucalyptus Flavor, Cinnamon Flavor, Ginger Flavor, Time Flavor, Natsume Flavor, Natsume Flavor. Mint flavor, matata bifre Bar, macchi flavor, pine flavor, pine tree flavor, mushroom flavor, matsutake flavor, bean flavor, marigold flavor, vanilla flavor, spice flavor, nut flavor, liquor flavor, flower flavor, vegetable flavor, etc. ..

The liquor in the present invention is not particularly limited, but a beverage having an alcohol content of 1 degree or more in liquor tax law (mixing water etc. to an extent such that it can be used for drinking to dilute the alcohol content to make a beverage having a degree of 1 degree or more. Including those that can be made and drinks that can be dissolved with water etc. to make a drink with an alcohol content of 1 degree or more.). The types are classified into four types, such as sparkling liquors, brewed liquors, distilled liquors and mixed liquors, according to the production method and properties of liquor.

For example, the sparkling liquor is not particularly limited, and examples thereof include beer, sparkling liquor, and other sparkling liquors. The beer in the present invention is fermented from malt, hops and water as a raw material and has an alcohol content of less than 20 degrees, and fermented from malt, hops, water and wheat and other articles specified by a Cabinet Order as raw materials. It also includes those with alcohol content less than 20 degrees. Happoshu in the present invention refers to alcoholic beverages having malt or wheat as a part of the raw material and having a foaming property, and having an alcohol content of less than 20 degrees. The other sparkling liquors in the present invention are liquors other than beer and happoshu, which have an alcohol content of less than 10 degrees and have sparkling properties.

Brewed liquors include, but are not limited to, sake, fruit liquor, and other brewed liquors. Sake in the present invention is fermented from rice, rice koji and water as a raw material and has an alcohol content of less than 22 degrees, and rice, rice koji, water and sake lees and other articles specified by a Cabinet Order are raw materials. It is fermented as, and includes those with an alcohol content of less than 22 degrees. The fruit liquor in the present invention is fermented from fruit as a raw material, alcohol content is less than 20 degrees and fermented by adding sugars to the fruit, alcohol content is less than 15 degrees. .. The other brewed liquor in the present invention is fermented from cereals, sugars and the like as a raw material, and has an alcohol content of less than 20 degrees and an extract content of 2 times or more.

For example, distilled spirits include, but are not limited to, continuous distilled shochu, single distilled shochu, whiskey, brandy, raw material alcohol, spirits and the like. The continuous distillation shochu in the present invention is obtained by distilling an alcohol-containing substance with a continuous distillation machine and having an alcohol content of less than 36 degrees. The single-distilled shochu in the present invention is obtained by distilling an alcohol-containing substance by a distiller other than a continuous distiller and having an alcohol content of 45 degrees or less. The whiskey in the present invention means a product obtained by distilling an alcohol-containing substance obtained by saccharifying and fermenting germinated grains and water as raw materials. The brandy in the present invention refers to a product obtained by distilling an alcohol-containing substance obtained by fermenting fruits or fruits and water as raw materials. The raw material alcohol in the present invention is obtained by distilling an alcohol-containing material and has an alcohol content of more than 45 degrees. Spirits in the present invention, sake, synthetic sake, continuous distilled shochu, single-distilled shochu, mirin, beer, fruit wine, sweet fruit wine, whiskey, brandy, raw alcohol, sparkling wine, any other brewed sake Not applicable to alcoholic beverages whose extract content is less than 2 times.

For example, mixed liquors include, but are not limited to, synthetic sake, mirin, sweet fruit liquor, liqueur, powdered liquor, miscellaneous liquor and the like. Synthetic sake in the present invention is an alcoholic liquor produced from alcohol, shochu or sake and glucose and other articles specified by a Cabinet Order as a raw material, its flavor, color and other properties are similar to sake, the alcohol content is 16 degrees. The extract content is less than 5 times or more. Mirin in the present invention means rice, rice koji and shochu or alcohol added thereto, which has an alcohol content of less than 15 degrees and an extract content of 40 degrees or more. The sweet fruit liquor in the present invention means fruit liquor mixed with sugar or brandy. The liqueur in the present invention refers to liquor made from liquor and sugars as a raw material and having an extract content of 2 or more times. The powdered liquor in the present invention refers to powdered liquor that can be dissolved to give a beverage having an alcohol content of 1 degree or more. The miscellaneous sake in the present invention means sake, synthetic sake, continuous distilled shochu, simple distilled shochu, mirin, beer, fruit sake, sweet fruit sake, whiskey, brandy, raw alcohol, happoshu, other brewed spirits, spirits , Liqueurs, and alcoholic beverages that do not fall under the category of powdered sake. When the classification and definition of liquor in the Liquor Tax Law is changed, the above liquor will be changed in accordance with the law.

The dairy drink in the present invention is not particularly limited, but collectively refers to products obtained by processing milk or dairy products as a main raw material or an auxiliary raw material, and contains 3% or more of dairy ingredients according to relevant laws and fair competition rules. Only those (excluding 1 part of lactic acid bacteria drink) are in the range of milk. The dairy drinks are roughly classified into three types, dairy drinks, fermented milk, and lactic acid bacterium drinks, which are specified by the Ordinance of the Ministry of Health and Welfare. The milk drink is a drink obtained by processing or a main ingredient of milk, raw milk or special milk, or a food produced using these as a raw material, and examples thereof include a coffee milk beverage and a fruit milk beverage. Fermented milk is obtained by fermenting milk or milk containing non-fat milk solids equivalent to or higher than this with lactic acid bacteria or yeast to give a paste or liquid, and the number of lactic acid bacteria or yeast per ml is 10 million or more. There are yogurts, for example. A lactic acid bacterium beverage is a beverage obtained by processing or fermenting milk or the like with lactic acid bacterium or yeast, or as a main raw material, and in the case of a dairy product having a non-fat milk solid content of 3.0% or more, lactic acid bacterium per 1 ml thereof. Alternatively, the number of yeasts is 10 million or more, such as Yakult. In the case of a non-dairy product having a non-fat milk solid content of less than 3.0%, the number of lactic acid bacteria or yeast per ml is 1 million or more, and for example sour milk. In addition, fermented milk and lactic acid bacterium beverages must, in principle, have a certain number of lactic acid bacteria or yeasts alive, but with the exception approval, and if labeled on the product, it should be sterilized after lactic acid fermentation and preserved. Supply is also possible.

The soup-based beverage according to the present invention is not particularly limited, and examples thereof include soy milk, soup, miso soup, amazake, oshiruko, and the like.

For example, soy milk is not particularly limited, but examples include soy milk, prepared soy milk, soy milk drink and the like. Soymilk in the present invention is a milky beverage obtained by elution of protein and other components from hot soybeans except powdered ones and defatted ones, and a soybean solid content obtained by removing fiber. Is 8% or more. The prepared soybean milk in the present invention is a soybean milk-like beverage obtained by adding seasonings such as soybean oil and other vegetable oils and fats, sugar and salt to a soybean milk liquid, a soybean solid content of 6% or more, and defatted soybean ( Soybean oil and vegetable oils and other ingredients such as soybean oil and sugar and salt are added to the product obtained by eluting proteins and other components with hot water etc. An added milky beverage (hereinafter referred to as “prepared defatted soybean soybean milk liquid”) having a soybean solid content of 6% or more can be mentioned. With the soymilk beverage in the present invention, powdered soybean protein in prepared soybean milk liquid or prepared defatted soybean soybean milk (soybean soybean milk, prepared soybean milk liquid or prepared defatted soybean soybean milk liquid in powder form or soybean as a raw material The powdery vegetable protein obtained by removing the fibrous material is the same as the above. The milky beverage (prepared soymilk or defatted soybean soymilk) is the main ingredient. Hereinafter referred to as “prepared powder soybean soymilk”) having a soybean solid content of 4% or more, or prepared soybean milk liquid, prepared defatted soybean soybean milk liquid or prepared powdered soybean soybean milk liquid and fruit juice (fruit juice and fruit juice). A mixture of a fruit juice and a fruit Piuret. The same shall apply hereinafter.), Vegetable juice, milk or dairy products, a milky beverage to which a flavor material such as shell powder is added (the solid content of the flavor ingredient is It is less than soybean solids, and the juice of fruit is In the case of added ones, the ratio of the mass of the raw material of fruit juice is less than 10%, in the case of added milk or dairy products, the milk solid content is less than 3%, and lactic acid bacteria. Non-beverage) and soybean solids content of 4% or more (2% or more if the proportion of the weight of the raw material of fruit juice is 5% or more and less than 10%). Be done. When the standards and definitions in the Japanese Agricultural Standards for soy milk are changed, the soy milk is changed in accordance with the standard.

The soup in the present invention is a dish in which the ingredients such as meat, fish, and vegetables are seasoned, but the soup is not particularly limited, and includes soup stock extracted from meat and vegetables. Examples of the soup in the present invention include consomme, potage, chowder, minestrone, gaspacho, miso soup and the like.

The amazake in the present invention is not particularly limited, but amazake refers to rice syrup and rice made from steamed rice and rice syrup by adding hot water to saccharify.

The tout in the present invention is not particularly limited, but refers to a food obtained by adding rice cake, white egg dumplings, chestnut simmered in the soup, which is sweetly boiled red beans and the like.

The form of the container of the packaged beverage of the present invention includes a metal container such as a can, a molded container containing polyethylene terephthalate as a main component (so-called PET bottle), a paper container combined with a metal foil or a plastic film, a bottle, a pouch bottle. However, the present invention is not limited thereto. For example, a sterilized packaged product can be manufactured through a method of performing heat sterilization such as retort sterilization after filling the beverage of the present invention into a container, or a method of sterilizing the beverage and filling into the container. The packaged beverage of the present invention is not limited to being directly drunk from a container, but can also be served by pouring a bulk container such as a back-in-box or a potion container into a separate container at the time of drinking. In addition, the concentrated liquid can be diluted when it is given for drinking. In that case, it goes without saying that the effects of the present invention can be obtained if the concentration of each component when used for drinking is within the concentration range of the present invention. Therefore, these beverages are also an aspect of the present invention.

Also, the packaged beverage of the present invention may be heat-sterilized. The heat sterilization method is not particularly limited as long as it complies with the conditions stipulated by applicable laws and regulations (Food Sanitation Act in Japan). For example, a retort sterilization method, a high temperature short time sterilization method (HTST method), an ultra high temperature sterilization method (UHT method), etc. can be mentioned. Further, it is also possible to appropriately select the heat sterilization method depending on the type of container of the packaged beverage, for example, in the case where the container can be heat sterilized after filling the beverage with the beverage, such as a metal can. Retort sterilization can be adopted. As for PET bottles and paper containers that cannot be sterilized by retort, aseptic filling, hot pack filling, etc., in which the beverage is heat-sterilized in advance under the same sterilization conditions as above and sterilized in a sterile environment, is filled. Can be adopted.

Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples. In addition, "%" means "mass%" unless otherwise specified.

Preparation of Flavonoid Inclusion Compound-containing Composition Preparation Examples 1 to 3
A sparingly soluble flavonoid having a rhamnoside structure (rutin or hesperidin) and cyclodextrin were added to a beaker having a volume of 1000 ml as shown in Table 1, and water was added to make 1000 g, and the temperature was adjusted to 70 ° C and pH 4.5. Then, with stirring, 3 to 30 g of naringinase (Amano Enzyme Co., Ltd. 155 u / g) was added, and the mixture was reacted for 24 hours, filtered at room temperature, and then powdered by spray drying with a spray dryer to give rhamnose-containing flavonoids. An inclusion-containing composition was obtained. In the obtained flavonoid inclusion-containing composition, the rhamnose content was measured (HPLC analysis method, calibration curve prepared by rhamnose (Wako), detection: suggestive refractometer RID-10A (SHIMADZU)), and then the rhamnose molar concentration was calculated. The molar ratio of rhamnose to flavonoid (rhamnose / flavonoid) was calculated from the molar concentration of flavonoid of the clathrate compound (absorbance analysis method), and was 0.8 to 1.2.

Preparation Examples 4-6
Without adding cyclodextrin, the concentrations of rutin and hesperidin shown in Table 1 were added, the enzyme reaction was carried out at a capacity of 100 kg, followed by filtration and cooling, and the precipitated isoquercitrin and hesperetin-7-glucoside were collected and dried. By doing so, powders of Preparation Examples 4 and 5 (content of 96% or more) were prepared. As Preparation Example 6, a composition containing only cyclodextrin containing no flavonoid having no rhamnoside structure (isoquercitrin or hesperetin-7-glucoside) was prepared. β-Cyclodextrin was dissolved in 15% and γ-cyclodextrin in 15%, and a part of the preparation liquid (1 kg) was pulverized with a spray dryer (β-cyclodextrin 50%, γ-cyclodextrin 50%). ..

Molar ratio of rhamnose and flavonoid in flavonoid clathrate (rhamnose / (flavonoid of flavonoid clathrate)), rhamnose and flavonoid in flavonoid glycoside composition (rhamnose / (flavonoid glycoside composition Flavonoids of things))
After measuring the rhamnose content (HPLC analysis method, creating a calibration curve by rhamnose (Wako), detection: suggestive refractometer RID-10A (SHIMADZU)), the rhamnose molar concentration was calculated, and the flavonoid molar concentration of the inclusion compound (absorbance Analytical method), the molar ratio of rhamnose to flavonoid (rhamnose / flavonoid) was calculated from the flavonoid-equivalent molar concentration of the flavonoid glycoside composition (HPLC method).

The details used in Table 1 are shown below.
RTN: 50 kg of Enju bud, which is a rutin bean family plant prepared below, was immersed in 500 L of hot water for 3 hours, and then the filtrate obtained by filtration was obtained. Then, the mixture was cooled to room temperature, the precipitated component was filtered off, and the precipitated portion was washed with water, recrystallized, and dried to obtain 3190 g of rutin having a content of 96% or more. It was confirmed by HPLC using the reagent rutin (Wako) that the peaks were the same.
HSP: Hesperidin (content 97% or more, manufactured by Hamari Pharmaceutical Co., Ltd.)
β-CD: β-Cyclodextrin (made by Pearl Ace)
γ-CD: γ-Cyclodextrin (made by Pearl Ace)

Conversion rate of rutin to isoquercitrin Area ratio of HPLC (SHIMADZU) (peak area of isoquercitrin / peak area of rutin) <HPLC conditions; column: CAPCELL PAK C18 SIZE 4.6 mm x 250 mm (SHISEIDO), eluent : 20% (v / v) acetonitrile / 0.1% phosphoric acid aqueous solution, detection: 351 nm, flow rate: 0.4 ml / min, column temperature: 70 ° C.>. Isoquercitrin was confirmed to have the same peak by HPLC using the reagent isoquercitrin (Wako). The conversion rates in Preparation Examples 1, 2, and 4 were all 96% or more.

Conversion rate of hesperidin to hesperetin-7-glucoside Area ratio of HPLC (SHIMADZU) (peak area of hesperetin-7-glucoside / peak area of hesperidin) <HPLC condition; column: CAPCELL PAK C18 SIZE 4.6 mm × 250 mm (SHISEIDO) ), Eluent: 40% (v / v) acetonitrile / 0.1% phosphoric acid aqueous solution, detection: 280 nm, flow rate: 0.4 ml / min, column temperature: 70 ° C.>. Hesperetin-7-glucoside was confirmed to have the same peak by HPLC using a dried product confirmed to be hesperetin-7-glucoside by NMR. The conversion rates in Preparation Examples 3 and 5 were all 96% or more.

Isoquercitrin (IQC) concentration (absorbance analysis method)
The reaction-terminated liquids of Preparation Examples 1, 2, and 4 were allowed to stand at room temperature, and 1 ml of the supernatant liquid was filtered to obtain a measurement sample. After making a calibration curve with an absorbance of 351 nm (0.1% phosphoric acid solution) using the reagent rutin (Wako), the rutin concentration was calculated from the absorbance of the measurement sample, and after correction with the conversion rate 0.761 (isoquercitrin / It was calculated as the isoquercitrin concentration by multiplying the molecular weight ratio of rutin (464.38 / 610.52 = 0.761)). The results are shown in Table 1.

Hesperetin-7-glucoside (HPT-7G) concentration (Absorptiometry)
The reaction-completed liquids of Preparation Examples 3 and 5 were allowed to stand at room temperature, and 1 ml of the supernatant liquid was filtered to obtain a measurement sample. After creating a calibration curve with an absorbance of 280 nm (0.1% phosphoric acid solution) using the reagent hesperidin (Wako), the hesperidin concentration was calculated from the absorbance of the measurement sample, and after correction with the conversion rate of HPLC analysis, 0.761 ( The hesperetin-7-glucoside concentration was calculated by multiplying the molecular weight ratio of hesperetin-7-glucoside / hesperidin (464.42 / 610.56 = 0.761). The results are shown in Table 1.

Solubility (IQC solubility, HPT-7G solubility)
The dried product prepared above was added to a beaker with a capacity of 100 ml containing 50 ml of water at 50 ° C. with stirring until it could not be completely dissolved and precipitated. After standing at room temperature (25 ° C.), 1 ml of the supernatant was filtered with a filter, and the concentration of isoquercitrin and hesperetin-7-glucoside were calculated by the absorbance analysis method and used as the solubility. However, when the amount of dried product was insufficient at the time of solubility measurement, the required amount was obtained by repeating the same preparation example experiment, and the solubility was measured. The conditions for HPLC are the same as the conditions for the above conversion rate. In addition, it was confirmed that flavonoids were included in cyclodextrin in Preparation Examples 1 to 3 and that Isoquercitrin and hesperetin-7-glucoside were prepared in Preparation Examples 4 and 5 by using a differential scanning calorimeter (DSC) and a nuclear magnetic field. It was confirmed by resonance (NMR) and Fourier transform infrared spectrophotometer (FT-IR). The results are shown in Table 1.

Notes to Table 1 (1) β-Cyclodextrin concentration at the start of reaction (mass%)
(2) γ-Cyclodextrin concentration at the start of reaction (mass%)
(3) Rutin concentration (% by mass) at the start of the reaction
(4) Cyclodextrin / rutin (molar ratio) at the start of the reaction
(5) Isoquercitrin concentration (mass%) of the filtrate after the reaction is completed
(6) Cyclodextrin / isoquercitrin (molar ratio) of the filtrate after completion of the reaction
(7) Isoquercitrin solubility (mass%) of the dried filtrate after the reaction
(8) Isoquercitrin content (mass%) of the dried filtrate after the reaction
(9) Hesperidin concentration (% by mass) at the start of the reaction
(10) Cyclodextrin / hesperidin (molar ratio) at the start of heating and stirring
(11) Hesperetin-7-glucoside concentration (mass%) of the filtrate after heating and stirring
(12) Cyclodextrin / hesperetin-7-glucoside (molar ratio) of filtrate after heating and stirring
(13) Hesperetin-7-glucoside solubility (mass%) of the dried filtrate after heating and stirring
(14) Hesperetin-7-glucoside content (mass%) of the dried filtrate after the completion of the reaction

<Flavor evaluation>
For the evaluation of flavor, sensory evaluation (change in taste and aroma) was carried out by 10 skilled panelists. The packaged beverages of the respective Examples and Comparative Examples prepared below were stored at 4 ° C. and 37 ° C. for 1 week and 4 weeks in the light of 3,000 lux, and the samples stored for the same period were stored at 4 ° C. The change in the prepared beverage at 37 ° C. with respect to the prepared beverage was calculated as an average point according to the following evaluation criteria. The same taste and odor as those stored under refrigeration for the same period were evaluated 5, and the additive-free product stored at 3000 lux in the bright place at 50 degrees for the same period had the strongest off-taste and off-odor. Was set to 1. Taste is judged to be sourness, bitterness, astringency, umami, and saltiness comprehensively as "unusual", and odor is comprehensively defined as sourness, fermentation odor, oxidized odor, and offensive odor intensity. It was judged. The results are shown in Tables 2-23.

Evaluation criteria of off-flavor 1: Sensitive changes in off-flavors 2: Sensitive changes on off-flavours 3: Sensitive changes on off-flavors 4: Sensitive changes on off-flavours 5: No changes on off-flavours

Evaluation criteria of offensive odor 1: Strong offensive odor 2: Strong offensive odor 3: Offensive odor
4: Smelling offensive odor 5: No offensive odor

Preparation of Green Tea Packaged Beverages Examples 1-9, Comparative Examples 1-3
90 kg of sencha extract was prepared by adding 10 kg of hot water at about 70 ° C. to 1 kg of commercially available dry sencha leaves and stirring for 10 minutes, and then 90 mg of sencha extract was obtained according to the formulations shown in Table 2 in Preparation Examples 1 to 6. The composition thus obtained was added and subjected to UHT sterilization treatment and then filled in a PET container of 500 ml to obtain a beverage packed in a green tea container.

Notes to Tables 2 to 23 (15) Kind of composition used in manufacturing packaged beverage (16) Blend amount (%) of composition used in manufacturing packaged beverage
(17) Isoquercitrin concentration in packaged beverage (%)
(18) Hesperetin-7-glucoside concentration (%) in packaged beverages

Preparation of Oolong Tea Packaged Beverages Examples 10-18, Comparative Examples 4-6
To 1 kg of commercially available dry oolong tea leaves, 10 kg of warm water at about 70 ° C. was added and stirred for 10 minutes, and then filtered with a filter cloth to prepare 92 kg of oolong tea extract, which were obtained in Preparation Examples 1 to 6 by the formulations shown in Table 3. The composition thus obtained was added and subjected to UHT sterilization treatment and then filled in a PET container of 500 ml to obtain a oolong tea container-packaged beverage.

Preparation of Black Tea Container Beverage Examples 19-27, Comparative Examples 7-9
92 kg of black tea extract was prepared by adding 10 kg of hot water of about 70 ° C. to 1 kg of commercially available dry black tea leaves and stirring for 10 minutes, and then the black tea extract was obtained in Preparation Examples 1 to 6 according to the formulation shown in Table 4. The composition thus obtained was added and subjected to UHT sterilization treatment and then filled in a PET container of 500 ml to obtain a tea-packaged beverage.

Preparation of Microbial Fermented Tea Container Beverages Examples 28-29, Comparative Examples 10-12
90 kg of Awabancha extract was prepared by adding 10 kg of hot water of about 70 ° C. to 1 kg of commercially available dry Awabancha leaves and stirring for 10 minutes, and then preparing Examples 1 to 6 according to the formulation shown in Table 5. The composition obtained in (1) was added, and after UHT sterilization treatment, it was filled in a 500 ml PET container to obtain a microbial fermented tea container-packaged beverage.

Preparation of Beverages for Flower Tea Packaging Examples 31 to 33, Comparative Examples 13 to 15
50 kg of flower tea leaves and 1500 kg of deoxygenated and deionized reverse osmosis water (80 ° C., dissolved oxygen amount 1 mg / L or less) were added to a closed extraction tank. Extraction was carried out for 20 minutes to obtain a flower tea extract. The extract was cooled by a plate cooler, then transferred to a closed holding tank and centrifuged for 7 minutes. After centrifugation, the tea extract was filtered with a filter cloth to obtain a tea clarified liquid or juice. Transfer the tea clarification liquid or juice to a closed mixing tank for mixing, add deoxygenated and deionized reverse osmosis water to a final mass of 10 tons, and then add 5.0 kg of ascorbic acid. It was The obtained mixture was stirred uniformly to obtain a mixed liquid. The compositions obtained in Preparation Examples 1 to 6 were added according to the formulations shown in Table 6, UHT sterilization treatment was performed, and the resulting mixture was filled in a PET container of 500 ml to obtain a beverage packed in a tea container.

Preparation of Coffee Packaged Beverages Examples 34 to 36, Comparative Examples 16 to 18
Granulated sugar (47 g) was added to Bx3.0 coffee extract that was extracted with hot water (extraction efficiency 28%) using 600 g of roasted coffee beans, and the pH was adjusted to 7.4 with baking soda. And The mass-adjusted coffee mix was homogenized using a high-pressure homogenizer at a temperature of 65 to 75 ° C. and a pressure of 15 MPa, and the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 7 and added to a can container. After the filling, retort sterilization was performed at 121 ° C. for 30 minutes to obtain a coffee packaged beverage.

Preparation of Milk Coffee Packaged Beverages Examples 37-45, Comparative Examples 19-21
1500g of milk and 47g of granulated sugar were added to a Bx3.0 coffee extract solution extracted with hot water (extraction efficiency 28%) using 600g of roasted coffee beans, and the pH was adjusted to 7.4 with baking soda, and then water was added. The total amount was 10 kg. The mass-adjusted coffee mix was homogenized using a high-pressure homogenizer at a temperature of 65 to 75 ° C. and a pressure of 15 MPa, and the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 8 and added to a can container. After the filling, retort sterilization was performed at 121 ° C. for 30 minutes to obtain a milk-coffee packaged beverage.

Preparation of cocoa packaged beverage Examples 46-48, Comparative Examples 22-24
150 g of cocoa powder was dissolved in a small amount of water, 300 g of granulated sugar, 150 g of skim milk powder and water were added to prepare 10 kg of a cocoa beverage having a cocoa component of 1.5%. The prepared cocoa mix was homogenized using a high-pressure homogenizer at a temperature of 65 to 75 ° C. and a pressure of 15 MPa, and the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 9 and filled in a can container. Then, retort sterilization was performed at 121 ° C. for 30 minutes to obtain a cocoa-packaged beverage.

Preparation of non-alcoholic beer taste packaged beverage Examples 49 to 51, Comparative Examples 25 to 27
The harvested barley was soaked in water to germinate appropriately and then roasted with hot air to produce malt. The malt was crushed by a conventional method. Next, mashed malt and warm water were added to a charging tank and mixed to prepare a maichet. The maichet was prepared by holding it at 50 ° C. for 30 minutes. Then, the starch was saccharified by using the malt-derived enzyme by gradually raising the temperature of the maichet and holding it at a predetermined temperature for a certain period of time. The saccharification treatment was performed by holding at 64.5 ° C for 10 minutes and at 70 ° C for 10 minutes. After the saccharification treatment, the mixture was kept at 78 ° C. for 5 minutes, and then the mash was filtered in a wort filtration tank to obtain transparent wort. Maltose was added to the obtained wort to adjust the Brix value to 35.07 (maltose concentration 46.3% by mass). Further, hydrochloric acid was added to this to adjust the pH to 3.5. 800 ml of wort with adjusted Brix value and pH was cooled to 5 ° C. The cooled wort was transferred to an Erlenmeyer flask, and 1 × 10 ⁶ mud yeast (brewer's yeast) was added per 1 ml of wort. The temperature of the fermented liquid was maintained at 5 ° C. and the fermentation was allowed to stand for 2 days. When the ethanol concentration of the fermentation liquid was measured, the fermentation liquid had an ethanol concentration of 0.0035% by volume. The compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 10, filtered through a membrane filter having a pore size of 10 μm, and filled in can containers to obtain non-alcoholic beer taste packaged beverages.

Preparation of Barley Tea Packaged Beverages Examples 52 to 54, Comparative Examples 28 to 30
Using 1 kg of commercially available unroasted barley, add 10 kg of water to explode the barley by explosive treatment to make it easier for water to penetrate, raise the temperature to about 90 ° C., stir for 20 minutes, and then use a filter cloth. After filtration, 92 kg of barley tea extract was prepared, the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 11, UHT sterilization treatment was performed, and then the mixture was filled in a 500 ml PET container and packed in a barley tea container. I got a drink.

Preparation of Tomato Juice Packaged Beverages Examples 55-57, Comparative Examples 31-33
Using commercially available tomato juice (Kagome tomato juice: manufactured by Kagome Co., Ltd.), the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 12, and sterilized at a temperature of 90 ° C., and then 500 ml. The PET container was filled in to obtain a beverage packed in a tomato juice container.

Preparation of Vegetable Juice Packaged Beverages Examples 58-60, Comparative Examples 34-36
Using commercially available vegetable juice (one day's vegetables: manufactured by Itoen Co., Ltd.), the compositions obtained in Preparation Examples 1 to 6 were added according to the formulations shown in Table 13, and sterilized at a temperature of 90 ° C. Then, it filled in a PET container of 500 ml and obtained the vegetable juice container packed drink.

Preparation of carbonated bottled beverages Examples 61 to 63, Comparative Examples 37 to 39
Grapefruit concentrated fruit juice 10.0%, glucose / fructose mixed liquid sugar 1.9%, maltitol 4.0%, acidulant 0.6%, and flavor 0.2% were used as base concentrates and blended as shown in Table 14. The compositions obtained in Preparation Examples 1 to 6 were added and sterilized at a temperature of 90 ° C., and then an equal amount of carbonated water was added to fill a 500 ml PET container to obtain a carbonated packaged beverage.

Preparation of functional packaged beverage Examples 64-66, Comparative Examples 40-42
A commercially available sports drink powder (Aquarius powder manufactured by Coca-Cola) was dissolved in a predetermined volume of water, and the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 15 to reach 90 ° C. After sterilization at high temperature, it was filled in a PET container of 500 ml to obtain a functional packaged beverage.

Preparation of Bottled Beverage for Mineral Water Examples 67 to 69, Comparative Examples 43 to 45
The composition obtained in Preparation Examples 1 to 6 was added according to the formulation shown in Table 16 using mineral water with lemon concentrated juice of 0.05% and fragrance of 0.01%, followed by UHT sterilization treatment, and then a 500 ml PET container. To obtain a beverage packed in a bottle of mineral water.

Preparation of alcohol-packaged beverage Examples 70-72, Comparative Examples 46-48
The harvested barley was soaked in water to germinate appropriately and then roasted with hot air to produce malt. The malt was crushed by a conventional method. Next, mashed malt and warm water were added to a charging tank and mixed to prepare a maichet. The maichet was prepared by holding it at 50 ° C. for 30 minutes. Then, the starch was saccharified by using the malt-derived enzyme by gradually raising the temperature of the maichet and holding it at a predetermined temperature for a certain period of time. The saccharification treatment was performed by holding at 64.5 ° C for 10 minutes and at 70 ° C for 10 minutes. After the saccharification treatment, the mixture was kept at 78 ° C. for 5 minutes, and then the mash was filtered in a wort filtration tank to obtain transparent wort. Maltose was added to the obtained wort to adjust the Brix value to 35.07 (maltose concentration 46.3% by mass). Further, hydrochloric acid was added to this to adjust the pH to 3.5. 800 ml of wort with adjusted Brix value and pH was cooled to 5 ° C. The cooled wort was transferred to an Erlenmeyer flask, and 1 × 10 ⁸ mud yeast (brewer's yeast) was added per 1 ml of wort. The temperature of the fermented liquid was maintained at 20 ° C., and the fermentation was allowed to stand for 11 days. When the ethanol concentration of the fermentation liquid was measured, the fermentation liquid had an ethanol concentration of 4.7% by volume. The compositions obtained in Preparation Examples 1 to 6 were added according to the formulations shown in Table 17, filtered through a membrane filter having a pore size of 10 μm, and filled into cans to obtain alcohol-packaged beverages.

Preparation of Milk-Packed Beverages Examples 73 to 75, Comparative Examples 49 to 51
A milk drink product was obtained using commercially available cider vinegar (acidity 4.5%). Table 18 shows 10 kg of skim milk powder, 50 kg of milk, 40 kg of apple cider vinegar, 100 kg of sugar syrup, 0.4 kg of stevia sugar transfer product, and 2 kg of pectin to prepare a base solution by dissolving, and the total amount becomes 1000 kg. The compositions obtained in Preparation Examples 1 to 6 were added by blending, homogenized with a homogenizer, sterilized at 85 ° C. for 30 minutes, cooled, and then filled in a 500 ml PET container to prepare a milky packaged beverage. Obtained.

Preparation of Soymilk Container Beverage Examples 76-78, Comparative Examples 52-54
Using commercially available soybean milk (delicious unprepared soybean milk: manufactured by Kikkoman Corporation), the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 19, filled in cans, and retort sterilized at 121 ° C. for 30 minutes. Then, a soymilk-packaged beverage was obtained.

Preparation of Soup Container Beverages Examples 79 to 81, Comparative Examples 55 to 57
Using a corn soup in which 30 kg of commercially available soup (corn potage: manufactured by Campbell), 30 kg of milk, and 20 g of salt were mixed, the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 20, and the mixture was filled in a can container. Then, retort sterilization was performed at 121 ° C. for 30 minutes to obtain a soup-packed beverage.

Preparation of Miso Soup Container Beverage Examples 82 to 84, Comparative Examples 58 to 60
Using the miso soup prepared by mixing 330 kg of water with 30 kg of commercially available miso (dashi broth-containing restaurant: Sanjirushi Brewery Co., Ltd.), the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 21, and added to a can container. After the filling, retort sterilization was performed at 121 ° C. for 30 minutes to obtain a miso soup container-packed beverage.

Preparation of Amazake Bottled Beverages Examples 85 to 87, Comparative Examples 61 to 63
Using 30 kg of commercially available amazake (Amazake: manufactured by Yamak Foods Co., Ltd.), the compositions obtained in Preparation Examples 1 to 6 were added according to the formulation shown in Table 22, and the resulting mixture was filled in cans and retort sterilized at 121 ° C. for 30 minutes. Was carried out to obtain a packaged beverage of amazake.

Preparation of Oshiruko Container Beverage Examples 88-90, Comparative Examples 64-66
To 25 kg of commercially available red beans, 50 kg of water was added and cooked. After discarding hot water, 50 kg of water was added again and boiled. The composition obtained in Preparation Examples 1 to 6 was prepared according to the formulation shown in Table 23 by using oshiko liquid in which 20 kg of sugar and 20 g of salt were added after the hot water had been thrown away until the azuki beans were completely rubbed, and the adzuki beans were crushed while heating. After adding and filling in a can container, retort sterilization was performed at 121 ° C. for 30 minutes to obtain a oshiroko container-packaged beverage.

As is clear from Tables 2 to 23, the packaged beverages of Examples 1 to 90 containing the flavonoid inclusion compound-containing compositions obtained in Preparation Examples 1 to 3 contained the flavonoid inclusion compound-containing compositions. Deterioration of flavor was suppressed as compared with Comparative Examples 1 to 66 which were not used. In particular, the packaged beverage in which Preparation Example 6 containing no flavonoid compound was significantly deteriorated in flavor.

Although not shown in Tables 2 to 23, instead of the flavonoid clathrate compound-containing compositions of Preparation Examples 1 to 3, the flavonoid clathrate compounds of Preparation Examples 1 to 3 from which rhamnose was removed by dialysis were packaged in a packaged beverage. Was prepared and subjected to a sensory evaluation under the same conditions (IQC concentration (mass%), HPT-7G concentration (mass%), etc. in the packaged beverage) is the same), and as a result, a flavonoid inclusion compound-containing composition containing rhamnose. The sensory evaluation value was about 0.2 to 0.4 lower than that of Example 1, but the deterioration of flavor was suppressed as compared with Comparative Examples 1 to 66.

Preparation of flavonoid glycoside composition Preparation Example 10
A sparingly soluble flavonoid having a rhamnoside structure (rutin or hesperidin) and cyclodextrin were added to a 1000 ml beaker as shown in Table 24, and water was added to 1000 g to adjust the pH to 70 ° C and 4.5. Thereafter, with stirring, 3 to 30 g of naringinase (155 u / g of Amano Enzyme Co., Ltd.) was added and reacted for 24 hours to obtain a reaction solution. A small amount of alkali was added to the resulting reaction solution (70 ° C, pH 4.5, isoquercitrin concentration 2.3% by mass) to adjust the pH to 60 ° C and pH 6.5, and then cyclodextrin glucanotransferase (CGTase: Amano). 20 g of Enzyme Co., Ltd., trade name "Contizyme", 600 U / ml) was added to start the reaction, and the reaction was maintained for 24 hours. The obtained reaction liquid was sterilized by heating, filtered, and then freeze-dried to obtain 158 g of an isoquercitrin glycoside composition containing the compound represented by the general formula (1). As a result of HPLC analysis (SHIMADZU), glycoside of the following formula n = 0: 16.2 mol%, total of n = 1 to 3: 40.7 mol%, n = 4 or more: 43.1 mol%, The ratio (rhamnose / isoquercitrin) of rhamnose to the number of moles converted to isoquercitrin was 1.05.

Isoquercitrin equivalent value of isoquercitrin glycoside composition (HPLC method)
An isoquercitrin conversion value was calculated by comparing the sum of each peak area by HPLC analysis (the same conditions as isoquercitrin concentration analysis) and the peak area of the calibration curve by the reagent isoquercitrin (Wako).

Further, the compositions of Preparation Examples 7 to 9 and 11 to 22 were prepared in the same manner as in Preparation Example 10 except that the compositions shown in Table 24 were used. Isoquercitrin containing the compound represented by the general formula (1) was prepared. A glycoside composition is obtained, wherein n = 0 is 10 mol% or more and 30 mol% or less, the content of the glycoside of n = 1 to 3 is 50 mol% or less, and n = 4 or more. The content of glycosides was 30 mol% or more, and the ratio of rhamnose to the number of moles converted to isoquercitrin (rhamnose / isoquercitrin) was 0.8 to 1.2.

Preparation Example 28
A small amount of alkali was added to a reaction solution (70 ° C., pH 4.5, hesperetin-7-glucoside concentration 2.9% by mass) prepared in the same manner as in Preparation Example 10 except that the composition was as shown in Table 24, and 60 ° C. After adjusting the pH to 6.5, 5 g of cyclodextrin glucanotransferase (CGTase: Amano Enzyme Inc., trade name "Contizyme", 600 U / ml) was added to start the reaction, and the reaction was maintained for 24 hours. The obtained reaction liquid was sterilized by heating, filtered, and then spray-dried to obtain 136 g of a hesperetin-7-glucoside glycoside composition containing the compound represented by the general formula (2). As a result of HPLC analysis (SHIMADZU), in the glycoside composition, the glycoside of the following formula n = 0: 19.5 mol%, the sum of n = 1 to 3: 40.9 mol%, n = 4 or more : 39.6 mol%, and the ratio of rhamnose to hesperetin-7-glucoside-converted mol number (rhamnose / hesperetin-7-glucoside) was 0.98.

Hesperetin-7-glucoside glycoside composition converted into hesperetin-7-glucoside (HPLC method)
The converted hesperetin-7-glucoside value was calculated by comparing the sum of the peak areas by HPLC analysis (the same conditions as the hesperetin-7-glucoside concentration analysis) and the peak area of the calibration curve by the reagent Hesperetin-7-glucoside (Chem Faces). ..

Further, the compositions of Preparation Examples 23 to 27 and 29 to 37 were prepared in the same manner as in Preparation Example 28 except that the compositions shown in Table 24 were obtained. As a result, hesperetin-7 containing the compound represented by the general formula (2) was prepared. A glucoside glycoside composition is obtained, n = 0 is 10 mol% or more and 30 mol% or less, the content of the glycoside of n = 1 to 3 is 50 mol% or less, and n = 4 or more The content of glycosides was 30 mol% or more, and the ratio (rhamnose / hesperelin-7-glucoside) of rhamnose to the number of mols of hesperelin-7-glucoside was 0.8 to 1.2.

Effect of Preventing Quality Deterioration by Flavonoid Glycoside Compositions In place of the examples using Preparation Examples 2 and 3 in Tables 2 to 23, the flavonoid glycoside compositions of Preparation Examples 10 and 28 were used to produce isoquel. A packaged beverage having the same concentration as the citrin equivalent value and the same concentration as the hesperetin-7-glucoside equivalent value was prepared. The flavor evaluation was carried out in the same manner as in each Example, and as a result of comparison, the sensory evaluations were almost the same. In addition, a rhamnose-containing flavonoid glycoside with rhamnose removed by dialysis was also prepared under the same conditions (the IQC concentration (mass%) in the packaged beverage, HPT-7G concentration (mass%), etc. are the same). As a result of the sensory evaluation, the sensory evaluation value was about 0.1 to 0.2 lower than that of the flavonoid glycoside composition containing rhamnose. Was suppressed.

Prescription Example of Packaged Beverage Composition Containing Inclusion Compound Formulation Example 1: Green Tea-based Packaged Beverage Composition In order to prevent flavor deterioration, isoquercitrin (IQC) / β-cyclodextrin inclusion compound-containing composition prepared in Preparation Example 1 was prepared. A dried product of the composition containing the isoquercitrin (IQC) · γ-cyclodextrin inclusion compound of Example 2 and the composition containing the hesperetin-7-glucoside (HPT-7G) · β-cyclodextrin inclusion compound of Preparation Example 3 was prepared. A packaged beverage containing it was prepared. This product can be suitably used as a packaged beverage.

Commercial green tea (Itoen Co., Ltd .: Oicha)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 2: Tea-based packaged beverage In order to prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercially available black tea (Kirin Co., Ltd .: afternoon tea, lemon tea)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 3: Oolong tea-based packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercially available oolong tea (Suntory Beverage & Food Co., Ltd .: Suntory Oolong Tea)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation 4: Jasmine tea-based packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ of Preparation Example 2 -A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial Jasmine Tea (Itoen Co., Ltd .: Relaxed Jasmine Tea)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 5: Coffee-based packaged beverage In order to prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial coffee (Coca-Cola Japan Co., Ltd .: Georgia Emerald Mountain Blend) (ingredient) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 6: Milk coffee-based packaged beverage In order to prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ of Preparation Example 2 -A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial milk coffee (UCC Ueshima Coffee Co., Ltd .: milk coffee)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 7: Cocoa-based packaged beverage In order to prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial milk cocoa (Morinaga & Co., Ltd .: 190g milk cocoa)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription Example 8: Non-alcoholic wine-based packaged beverage In order to prevent flavor deterioration, isoquercitrin (IQC) / β-cyclodextrin inclusion compound-containing composition of Preparation Example 1, isoquercitrin (IQC) of Preparation Example 2 A packaged beverage containing the composition containing the γ-cyclodextrin inclusion compound and the dried product of the composition containing hesperetin-7-glucoside (HPT-7G) · β-cyclodextrin inclusion compound of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Non-alcoholic wine on the market (Chateau Katsunuma Co., Ltd .: Chateau Katsunuma Katsunuma Grape) (ingredient) (mass%)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 9: Barley tea-based packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial barley tea (Itoen Co., Ltd .: healthy mineral barley tea)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 10: Tomato juice-based packaged beverage In order to prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ of Preparation Example 2 -A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial tomato juice (Kagome Co., Ltd .: Kagome tomato juice)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 11: Vegetable-based packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial vegetable juice (Itoen Co., Ltd .: 1 day's worth of vegetables)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 12: Carbonated bottled beverage To prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercially available carbonated drinks (Asahi Soft Drinks Co., Ltd .: Mitsuya Cider)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 13: Non-alcoholic beer-based packaged beverage In order to prevent flavor deterioration, isoquercitrin (IQC) / β-cyclodextrin inclusion compound-containing composition of Preparation Example 1, isoquercitrin (IQC) of Preparation Example 2 A packaged beverage containing the composition containing the γ-cyclodextrin inclusion compound and the dried product of the composition containing hesperetin-7-glucoside (HPT-7G) · β-cyclodextrin inclusion compound of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.
The harvested barley was soaked in water to germinate appropriately and then roasted with hot air to produce malt. The malt was crushed by a conventional method. Next, mashed malt and warm water were added to a charging tank and mixed to prepare a maichet. The maichet was prepared by holding it at 50 ° C. for 30 minutes. Then, the starch was saccharified by using the malt-derived enzyme by gradually raising the temperature of the maichet and holding it at a predetermined temperature for a certain period of time. The saccharification treatment was performed by holding at 64.5 ° C for 10 minutes and at 70 ° C for 10 minutes. After the saccharification treatment, the mixture was kept at 78 ° C. for 5 minutes, and then the mash was filtered in a wort filtration tank to obtain transparent wort. Maltose was added to the obtained wort to adjust the Brix value to 35.07 (maltose concentration 46.3% by mass). Further, hydrochloric acid was added to this to adjust the pH to 3.5. 800 ml of wort with adjusted Brix value and pH was cooled to 5 ° C. The cooled wort was transferred to an Erlenmeyer flask, and 1 × 10 ⁶ mud yeast (brewer's yeast) was added per 1 ml of wort. The temperature of the fermented liquid was maintained at 5 ° C. and the fermentation was allowed to stand for 2 days. When the ethanol concentration of the fermented liquid was measured, the fermented liquid had an ethanol concentration of 0.0035% by volume and was used as a non-alcoholic beverage base.

Non-alcoholic beer taste beverage base (ingredient) (mass%)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 14: Functional beverage packaged beverage In order to prevent flavor deterioration, isoquercitrin (IQC) / β-cyclodextrin inclusion compound-containing composition of Preparation Example 1, isoquercitrin (IQC) / γ of Preparation Example 2 -A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial functional beverage (Otsuka Pharmaceutical Co., Ltd .: Pocari Sweat)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 15: Bottled beverage with mineral water To prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercially available mineral water (Suntory Beverage & Food Co., Ltd .: Morning picked orange & Suntory natural water)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 16: Alcoholic beer-based packaged beverage In order to prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ of Preparation Example 2 -A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.
The harvested barley was soaked in water to germinate appropriately and then roasted with hot air to produce malt. The malt was crushed by a conventional method. Next, mashed malt and warm water were added to a charging tank and mixed to prepare a maichet. The maichet was prepared by holding it at 50 ° C. for 30 minutes. Then, the starch was saccharified by using the malt-derived enzyme by gradually raising the temperature of the maichet and holding it at a predetermined temperature for a certain period of time. The saccharification treatment was performed by holding at 64.5 ° C for 10 minutes and at 70 ° C for 10 minutes. After the saccharification treatment, the mixture was kept at 78 ° C. for 5 minutes, and then the mash was filtered in a wort filtration tank to obtain transparent wort. Maltose was added to the obtained wort to adjust the Brix value to 35.07 (maltose concentration 46.3% by mass). Further, hydrochloric acid was added to this to adjust the pH to 3.5. 800 ml of wort with adjusted Brix value and pH was cooled to 5 ° C. The cooled wort was transferred to an Erlenmeyer flask, and 1 × 10 ⁶ mud yeast (brewer's yeast) was added per 1 ml of wort. The temperature of the fermented liquid was maintained at 5 ° C, and the fermentation was allowed to stand for 11 days. When the ethanol concentration of the fermented liquid was measured, the fermented liquid had an ethanol concentration of 4.8% by volume and was used as an alcoholic beverage base.

Alcohol beer taste beverage base
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 17: Wine-packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ-cyclo of Preparation Example 2 A packaged beverage containing a composition containing a dextrin clathrate compound and a dried product of the composition containing hesperetin-7-glucoside (HPT-7G) / β-cyclodextrin clathrate compound of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial wine (Chateau Katsunuma Co., Ltd .: 100% red from Katsunuma)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 18: Milk-based beverage packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ of Preparation Example 2 -A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercially available dairy drink (Asahi Soft Drinks Co., Ltd .: Calpis) 5-fold diluted liquid (ingredient) (mass%)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 19: Soymilk beverage packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ- of Preparation Example 2 A packaged beverage containing the cyclodextrin inclusion compound-containing composition and the dried product of the hesperetin-7-glucoside (HPT-7G) .β-cyclodextrin inclusion compound-containing composition of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial soymilk drink (manufactured by Kikkoman Corporation: delicious unprepared soymilk)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Prescription example 20: Soup packaged beverage For preventing flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ-cyclo of Preparation Example 2 A packaged beverage containing a composition containing a dextrin clathrate compound and a dried product of the composition containing hesperetin-7-glucoside (HPT-7G) / β-cyclodextrin clathrate compound of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial soup (manufactured by Pokka Sapporo Food and Beverage Co., Ltd .: Careful corn potage)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation example 21: Miso soup container-packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ-cyclo of Preparation Example 2 A packaged beverage containing a composition containing a dextrin clathrate compound and a dried product of the composition containing hesperetin-7-glucoside (HPT-7G) / β-cyclodextrin clathrate compound of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial miso soup (manufactured by Sanziru Brewing Co., Ltd .: Dashi-filled restaurant)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 22: Amazake packaged beverage In order to prevent flavor deterioration, a composition containing an isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and an isoquercitrin (IQC) / γ-cyclone of Preparation Example 2 A packaged beverage containing a composition containing a dextrin clathrate compound and a dried product of the composition containing hesperetin-7-glucoside (HPT-7G) / β-cyclodextrin clathrate compound of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial Amazake (Yamak Foods Co., Ltd .: Amazake)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

Formulation Example 23: Oshiruko container-packaged beverage In order to prevent flavor deterioration, a composition containing isoquercitrin (IQC) / β-cyclodextrin inclusion compound of Preparation Example 1 and isoquercitrin (IQC) / γ-cyclo of Preparation Example 2 A packaged beverage containing a composition containing a dextrin clathrate compound and a dried product of the composition containing hesperetin-7-glucoside (HPT-7G) / β-cyclodextrin clathrate compound of Preparation Example 3 was prepared. This product can be suitably used as a packaged beverage.

Commercial oshiruko (Made by Asahi Soft Drink Company: Asahi oshiruko can)
(Component) (% by mass)
Dried product of Preparation Example 1 (IQC mass) 0.0094 (0.015)
Dry product of Preparation Example 2 (IQC mass) 0.006 (0.015)
Dried product of Preparation Example 3 (mass of HPT-7G) 0.078 (0.015)

According to the present invention, it is possible to suppress quality deterioration during processing and storage of packaged beverages, and it can be suitably used in the food field.

Claims

A packaged beverage containing a flavonoid clathrate compound, wherein the flavonoid clathrate compound treats a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having rhamnosidase activity in the presence of cyclodextrin to release rhamnose. A packaged beverage obtained through the separation step.
The packaged beverage according to claim 1, further comprising rhamnose.
The sparingly soluble flavonoid having the rhamnoside structure is rutin, hesperidin, naringin, diosmin, eriocitrin, myricitrin, neohesperidin, luteolin-7-rutinoside, delphinidin-3-rutinoside, cyanidin-3-rutinoside, isorhamnetin-3-rutinoside. The packaged beverage according to claim 1 or 2, which is one or more selected from the group consisting of :, kaempferol-3-rutinoside, and acacetin-7-rutinoside.
The packaged beverage according to any one of claims 1 to 3, wherein the cyclodextrin is one or more selected from the group consisting of β-cyclodextrin, branched β-cyclodextrin, and γ-cyclodextrin.
A packaged beverage containing a flavonoid clathrate compound, wherein the flavonoid clathrate compound is a compound in which flavonoids having no rhamnoside structure are clathrated in cyclodextrin, and flavonoids and cyclodextrins in the flavonoid clathrate compound A packaged beverage having a molar ratio (cyclodextrin / flavonoid) of 0.01 to 10.0.
The flavonoids in the flavonoid clathrates include isoquercitrin, hesperetin-7-glucoside, naringenin-7-glucoside (purnin), diosmethine-7-glucoside, myricetin, eriodictyle-7-glucoside, luteolin-7-glucoside, Consists of delphinidin-3-glucoside, cyanidin-3-glucoside, isorhamnetin-3-glucoside, kaempferol-3-glucoside, apigenin-7-glucoside, quercetin, hesperetin, naringenin, acacetin-7-glucoside, and derivatives thereof The packaged beverage according to claim 5, comprising at least one selected from the group.
The packaged beverage according to claim 5 or 6, wherein the cyclodextrin comprises one or more selected from the group consisting of β-cyclodextrin, branched-β-cyclodextrin, and γ-cyclodextrin.
The flavonoid inclusion compound is a flavonoid inclusion compound in which isoquercitrin is included in γ-cyclodextrin, and a molar ratio of the isoquercitrin and the γ-cyclodextrin (γ-cyclodextrin / isoquercitrin ) Is 1.0 to 3.0, and the solubility of the isoquercitrin in water is 0.01% or more, and the packaged beverage according to any one of claims 5 to 7.
The flavonoid inclusion compound is a flavonoid inclusion compound in which isoquercitrin is included in γ-cyclodextrin, and a molar ratio of the isoquercitrin and the γ-cyclodextrin (γ-cyclodextrin / isoquercitrin ) Is 0.9 to 4.0, and the solubility of the isoquercitrin in water is 0.01% or more, and the packaged beverage according to any one of claims 5 to 7.
The flavonoid inclusion compound is a flavonoid inclusion compound in which isoquercitrin is included in β-cyclodextrin, and a molar ratio of the isoquercitrin and the β-cyclodextrin (β-cyclodextrin / isoquercitrin ) Is 1.0 to 3.0, and the solubility of the isoquercitrin in water is 0.01% or more, and the packaged beverage according to any one of claims 5 to 7.
The flavonoid inclusion compound is a flavonoid inclusion compound in which hesperetin-7-glucoside is included in cyclodextrin, and a molar ratio of the hesperetin-7-glucoside and the cyclodextrin (cyclodextrin / hesperetin-7-glucoside ) Is 1.0 to 3.0, and the solubility of hesperetin-7-glucoside in water is 0.01% or more, and the packaged beverage according to any one of claims 5 to 7.
The packaged beverage according to any one of claims 5 to 11, further comprising rhamnose, wherein the flavonoid in the flavonoid inclusion compound and the rhamnose have a molar ratio (rhamnose / flavonoid) of 0.1 to 10.
The packaged beverage according to claim 12, wherein a molar ratio (rhamnose / flavonoid) between the flavonoid and the rhamnose in the flavonoid inclusion compound is 0.8 to 1.2.
A packaged beverage containing a flavonoid glycoside composition, wherein the flavonoid glycoside composition is obtained through a glycoside conversion step of treating a flavonoid clathrate compound with a glycosyltransferase to form a glycoside. The flavonoid clathrate was obtained through a elimination step of eliminating rhamnose by treating a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having rhamnosidase activity in the presence of cyclodextrin. It is a packaged beverage.
The packaged beverage according to claim 14, wherein the glycosylation step is performed in an aqueous medium having a pH of 3 to 7.
The glycoside composition is an isoquercitrin glycoside composition represented by the following general formula (1), wherein the glycoside content of n = 0 in the glycoside composition is 10 mol. % Or more and 30 mol% or less, the content of the glycoside with n = 1 to 3 is 50 mol% or less, and the content of the glycoside with n = 4 or more is 30 mol% or more. 14. The packaged beverage according to 14 or 15.

(In the general formula (1), Glc means a glucose residue, and n means 0 or an integer of 1 or more.)
The glycoside composition is a hesperetin-7-glucoside glycoside composition represented by the following general formula (2), wherein the content of the glycoside of n = 0 in the glycoside composition is 10 mol% or more and 30 mol% or less, the content of the glycoside of n = 1 to 3 is 50 mol% or less, and the content of the glycoside of n = 4 or more is 30 mol% or more, The packaged beverage according to claim 14 or 15.

(In the general formula (2), Glc means a glucose residue, and n means 0 or an integer of 1 or more.)
The glycoside composition is an aggregon glycoside composition represented by the following general formula (3), wherein the content of the glycoside of n = 0 in the glycoside composition is 10 mol% or more. 15. The content of the glycoside of 30 mol% or less, the content of n = 1 to 3 is 50 mol% or less, and the content of the glycoside of n = 4 or more is 30 mol% or more. 15. The packaged beverage according to item 15.

(In the general formula (3), R 1 to R 9 are each independently —H, —OH, —OCH 3 , —O-Glc- (Glc) n, where Glc is a glucose residue and n is 0. Alternatively, it means an integer of 1 or more, and at least one or more substituents of R1 to R9 is —O—Glc- (Glc) n.)
The packaged product according to any one of claims 14 to 18, further comprising rhamnose, and a molar ratio (rhamnose / flavonoid) of the flavonoid-glycoside composition in terms of flavonoids to the rhamnose is 0.1 to 10. Beverage.
20. The packaged beverage according to claim 19, wherein the flavonoid glycoside composition has a flavonoid-equivalent number of moles and the rhamnose has a molar ratio (rhamnose / flavonoid) of 0.8 to 1.2.
A tea-based beverage, a coffee-based beverage, a cocoa-based beverage, a non-alcoholic beer-taste beverage, a fruit juice beverage, a vegetable beverage, a carbonated beverage, a functional beverage, mineral water, liquor, a milk-based beverage, or a soup-based beverage. 20. A packaged beverage according to any one of 20 to 20.
A method for producing a packaged beverage containing a flavonoid inclusion compound, which comprises a step of treating a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having rhamnosidase activity in the presence of cyclodextrin to eliminate rhamnose. ,Production method.
A method for producing a packaged beverage containing a flavonoid glycoside composition, comprising a step of treating a sparingly soluble flavonoid having a rhamnoside structure with an enzyme having rhamnosidase activity in the presence of cyclodextrin to eliminate rhamnose. And a flavonoid clathrate compound obtained through the elimination step, which is treated with a glycosyltransferase to form a glycoside.