JP5869217B2 - Method for producing chafroside-rich tea aqueous solution - Google Patents

Description

  The present invention relates to a method for producing an aqueous tea solution containing a high amount of chafurosides, and particularly to an improvement of a treatment method for an aqueous solution of tea extract or tea extract dry residue.

  Chafuroside is a natural compound that is naturally present only in a trace amount, and therefore has been isolated from oolong tea for the first time in recent years and whose structure has been determined (Patent Document 1). They have the structural formula shown below, and are classified into flavone C glycosides, which are a kind of flavone derivative, and are named chafloside A and chafloside B, respectively.

  As an effective action of chafuroside, an antiallergic action used as an index at the time of determining the isolated structure or a carcinogenesis suppressing action (Patent Document 2) is known. In addition, oolong tea from which chafuroside has been isolated has become a very common drink in Japan in recent years, and further elucidation of the effects of chafuroside and supply to the market are awaited. Since the content in is small and the purification is troublesome, securing the amount is a big problem.

  As its solution, a synthesis method using 1,1′-azobis N, N′-dimethylformamide, tri-n-butylphosphine using isovitexin and vitexin contained in herbs as raw materials, or Patent Document 3; A first step of binding a saccharide to a benzene ring in an aprotic solvent in the presence of a Lewis acid catalyst, a step of reacting a saccharide-benzene ring binding compound with azodicarboxylic acid amide or the like in an aprotic solvent. A synthesis method through two stages (Patent Document 4) has been reported.

On the other hand, teas are roughly classified into three types according to the degree of fermentation during the production process: unfermented tea typified by green tea, semi-fermented tea typified by oolong tea, and fully fermented tea typified by black tea. Widely used around the world. As representative effects of green tea, carcinogenesis suppression, anti-oxidation, antibacterial (antiviral), arousal, blood pressure / blood glucose level lowering, deodorization, and tooth decay prevention are known. As the action of oolong tea, an antioxidant action, an antiallergic action, an anti-inflammatory action, an α-glucosidase inhibitory action, a glucosyltransferase inhibitory action and the like are known.

  However, the content of chafloside in tea leaves as Oolong tea active compound (OTAC) is the highest in oolong tea, 24.8 μg / g (tea leaves) according to HPLC analysis, and 80 ng in green tea / G (tea leaves), roasted tea is 2.4 μg / g (tea leaves), and black tea is about 80 ng / g (tea leaves) (Patent Document 2). Alternatively, in Patent Document 5, chafloside A and B have a large difference between tea, the content in green tea and black tea is tens of ng per gram of tea leaves, there is almost no difference between brands, and variation between roasted tea and oolong tea However, the content is several μg per gram of tea leaves, and it is described that there is no significant difference between brands in roasted tea and there is a large difference in oolong tea (same paragraph number 0083).

  In this way, the content of chafuroside in tea leaves is expected despite the expected prevention and treatment effects for various diseases and habitual diseases caused by continuous intake in our daily lives. Has the problem of being very low.

  Therefore, attempts have been made to increase the content of chafuroside in tea leaves. That is, Patent Document 2 states that “Roasted tea is obtained by treating green tea at a high temperature of 180 ° C. or higher. However, by heat-treating the same tea leaf, the content of OTAC (chafroside A) increases several times. Example 1 was disclosed, and tea leaves such as green tea having a low content were also subjected to heat treatment (for example, high-temperature treatment at 180 ° C. or higher), thereby efficiently producing OTAC (chafroside A). It is described that it is possible to obtain (Same paragraph number 0031). However, the increase is only five times at most (the same paragraph number 0050). In Patent Document 5, chaflosides A and B are produced by heating in tea leaves, and the optimum temperature is in the range of 160 to 180 ° C. for tea leaves, decomposition when the temperature is too high, 160 ° C., about It is disclosed that the amount of generation becomes maximum by heating for 40 minutes (same paragraph number 0091). Specifically, the contents of chafuroside A and B before heat treatment, 50 ng / g tea leaves and 39 ng / g tea leaves (Table 2 in the same paragraph number 0081) are about 180 times when heated at a maximum of 160 ° C. for 80 minutes ( 8.872 μg / g tea leaf) and 210 times (7.995 μg / g tea leaf) (Table 4 in paragraph 0090). Patent Document 6 discloses a method of heat-treating tea leaves at 115 to 125 ° C. for 100 to 350 minutes, or 125 to 150 ° C. for 10 to 240 minutes (the same claim 5). The shortest heating time is a heat treatment at 150 ° C. for 10 minutes, and at that time, chafloside is increased by 286 times (18 μg / g tea leaves) (Example 3).

JP 2004-035474 A JP 2006-342103 A JP 2005-289888 A JP-A-2005-314260 WO2010 / 0776879 JP 2009-131161 A

However, the quantification of the chafloside content in the tea leaves after the heat treatment is performed by extracting the heat-treated tea leaves using a 50% methanol aqueous solution (Patent Document 5) or a 40-60 wt% methanol aqueous solution (Patent Document 6). It is carried out using liquid. Naturally, it is predicted that the value will be higher than the value obtained by extracting normal water (preferably hot water) at the time of tea beverage production, and it is unknown how much content will be in actual tea beverage . Also, because tea leaves are bulky materials, it is difficult to heat a large amount of tea leaves at the same time due to the size of the heating kettle, and there are technical difficulties in heating a large amount of tea leaves evenly. is expected. Above all, as described above, when heat treatment is performed at a high temperature for a long time, there is a disadvantage that the quality of tea leaves itself (tea fragrance, flavor, color, etc.) is deteriorated. Therefore, when the tea leaves subjected to such heat treatment are put to practical use and finally used as a beverage or the like, there are not a few problems. Also, in terms of actual production, in order to heat at 150 ° C. or higher as described above, a facility in place of heating with normal pressurized steam is required, which is economically impractical.
In the present invention, as described above, the disadvantages associated with high-temperature heat treatment of tea leaves are improved, and the quality of tea beverage (tea fragrance, flavor, color, etc.) is not impaired, and at a relatively low temperature for a short time. The purpose of the present invention is to provide a method for producing a tea beverage containing a high amount of chafurosides by heat treatment of

  In view of the above circumstances, tea leaves, tea leaf powder, or tea astringents are heated for a long time at a high temperature to obtain tea leaves, tea leaf powders, or tea astringents containing a high amount of chafuroside, instead of either acid, base, or salt, Alternatively, in the presence of a mixture thereof, a water (preferably hot water) extract obtained from tea leaves, tea leaf powder, or tea astringent is heated at 100 to 150 ° C. in the range of pH 5 to 10.6, A method for producing a tea aqueous solution containing a high amount of chafurosides was clarified while maintaining tea quality, and the present invention was completed.

That is, the present invention is a method for producing an aqueous chafroside-containing tea aqueous solution from tea leaves or tea astringents, or a tea extract obtained from tea leaves or tea astringent powder, or a tea extract dry residue, and the production method comprises the following steps: (1) It is a manufacturing method characterized by including (3).
(1) A step of adding an acid, a base, a salt, or a mixture thereof in any process prior to the heating step described below,
(2) In the step (1), a step of adjusting the pH of the aqueous solution to be subjected to the following heating step to 5 to 10.6, and (3) a pH-adjusted tea extraction aqueous solution obtained through the step (2), The process of heat-processing at 100-150 degreeC, and obtaining the chaflocide high content tea aqueous solution.

  The method for producing a chafroside-rich tea aqueous solution according to the present invention is a method for producing a chafrosides-rich tea aqueous solution, characterized in that the chafrosides are chafroside A and / or chafloside B.

  The method for producing a chafroside-rich tea aqueous solution according to the present invention is characterized in that the acid, base, and salt used in the step (1) are a food additive acid, base, and salt. This is a method for producing a high-content tea aqueous solution.

  The method for producing a chafloside-rich tea aqueous solution according to the present invention comprises the acid, base and salt used in the step (1) with respect to the tea extract or diluted aqueous solution thereof, or the tea extract dry residue or aqueous solution thereof. Either or a mixture thereof is added to obtain a pH-adjusted tea extraction aqueous solution.

  The method for producing a chafloside-rich tea aqueous solution according to the present invention uses tea leaves or tea astringents or tea leaves using an aqueous solution to which any of the acid, base, salt, or mixture thereof used in the step (1) is added. Alternatively, a tea astringent powder is extracted to obtain a pH-adjusted tea extraction aqueous solution.

  The method for producing a chaflocide-rich tea aqueous solution according to the present invention comprises the acid, base or salt concentration used in the step (1) in the pH-adjusted tea extraction aqueous solution, or the total of the mixture thereof. The concentration is 0.625 to 100 mmol, and the pH-adjusted tea extraction aqueous solution is prepared by using water at a ratio of 1 L with respect to 5 g of tea leaves or tea astringent or tea leaves or tea astringent powder. It is the manufacturing method of the chafroside high content tea aqueous solution characterized.

  The method for producing a chafrosides-rich tea aqueous solution according to the present invention is a method for producing a chafrosides-rich tea aqueous solution, wherein the pH in the step (2) is 5 to 7.

  The method for producing a chafrosides-rich tea aqueous solution according to the present invention is a method for producing a chafrosides-rich tea aqueous solution, characterized in that the heat treatment in the step (3) has a heating time of 15 seconds to 8 minutes. .

  The method for producing a chafloside high tea aqueous solution according to the present invention is characterized in that the heat treatment in the step (3) is a heat treatment using a microwave or a heat exchanger. It is a manufacturing method.

  In the method for producing a chafroside-rich tea aqueous solution according to the present invention, the pH in the step (2) is 6 to 8, and the heat treatment in the step (3) is performed at a heating temperature of 130 to 150 ° C. and a heating time of 15 seconds. It is a manufacturing method of the chafroside high content tea aqueous solution characterized by being -2 minutes.

  When the pH in the step (2) is basic, the method for producing a chafroside-rich tea aqueous solution according to the present invention is the pH of the chafroside-rich tea aqueous solution obtained after the heat treatment in the step (3). Is adjusted to 5-7 using the acid for food additives, It is a manufacturing method of the chaflocide high content tea aqueous solution characterized by the above-mentioned.

  Furthermore, this invention is the drink or foodstuff containing the chaflocide high content tea aqueous solution concerning this invention.

  The production method of tea aqueous solution containing a high amount of chafrosides of the present invention increases the content of chafrosides efficiently at a relatively low temperature and within a heating time of several minutes by a simple heating method represented by high-pressure steam. It is possible to provide a chafroside-rich tea aqueous solution.

  The method for producing a chafroside-enriched tea aqueous solution of the present invention comprises chafrosides containing a very high proportion of chafrosides known to have antioxidant, anti-allergic, anti-inflammatory and carcinogenic effects. An aqueous tea solution can be provided.

  The method for producing a chafroside-rich tea aqueous solution of the present invention is a method capable of producing a chafrosides-rich tea aqueous solution while maintaining tea quality (tea aroma, flavor, color, etc.). As a result, it is possible to provide a tea aqueous solution containing a high quality and high content of chafuroside.

  The chafroside-rich tea aqueous solution produced by the method for producing the chafloside-rich tea aqueous solution of the present invention contains a very high proportion of chafrosides, so that the health based on the chafrosides is maintained. Foods with various effects (preventive effects), especially beverage products, can be provided, foods for specified health use, special nutritional foods, beverages as dietary supplements, other nutritional beverages, health drinks, health Can be used as tea.

  Furthermore, in the method for producing chafrosides-rich tea astringent of the present invention, the tea leaves mainly from the relatively fragile parts such as the bud parts of tea leaves, or those that have hardened, reduce the tea quality, You can effectively use tea astringents that are considered to be a source of pollution.

Hereinafter, embodiments of the present invention will be described in detail.
In the present invention, examples of tea leaves used for tea leaves or tea leaf powders include, but are not limited to, tea leaves for green tea, tea leaves for roasted tea, tea leaves for black tea, and oolong tea. Any tea made from the buds and leaves of camellia plant tea (scientific name Camellia sinensis) can be used without limitation as a raw tea leaf. Depending on the processing method, it can be roughly classified into non-fermented tea, semi-fermented tea, and fermented tea. As non-fermented tea, Camellia genus, for example, C.I. var. sinensis (including Yabutaki species), C.I. var. Illustrative are green teas such as stem tea, stick tea, bud tea, bancha, strawberry tea and kettle tea made from tea selected from assamica and hybrids thereof. Examples of semi-fermented teas include iron kannon, color varieties, golden katsura, daffodil, wuwei daffodil, wuwei rock tea, daffodil sen, white leaves, honey orchid, shibori incense, four seasons spring, and grape seeds, which are collectively called oolong tea. The Examples of fermented tea include Darjeeling, Uba, Keyman, Carabeni, India and the like called black tea.

  The above-mentioned tea leaves may be blended and used at an appropriate ratio. As tea astringents, powdered tea from a relatively brittle portion such as a bud portion of tea leaves or a solidified product can be used in the production process of green tea. Of course, the tea leaves used may be fresh tea leaves or dry tea leaves, and the method for crushing these tea leaves or tea astringents is not particularly limited.

  Each tea leaf is generally made as follows. Green tea is steamed after fresh young leaves, then cooled immediately, dried at a temperature of about 80 ° C. while being swirled by hand while being heated, and tea is made. Black tea is made by bending a young leaf over about 8 hours, draining the water, and then subjecting it to oxidative fermentation with a hand for several hours, and then drying with a hot air of about 90 ° C. in a short time. Oolong tea is bent for 2 to 3 hours by sunbathing, and is moderately fermented while shaking on a bamboo basket in the room, and then the enzyme is killed in a short time by hot air at 160 to 260 ° C. In particular, tea is made while drying at about 90 ° C. Roasted tea is made by roasting green tea at 160 to 200 ° C. for a short time.

  As a method for preparing a tea extract from raw tea leaves or tea astringents, the above-described raw tea leaves, tea astringents or powders thereof may be extracted by a general method. For example, after preparing tea leaves in an extraction kettle, immersing them in a predetermined amount of water or a water-alcohol mixture for a certain period of time, then removing the tea husk and insoluble matter by filtration or centrifugation, For example, a method of obtaining a predetermined amount of an extract by feeding a constant flow of water after filling tea leaves. The water used for extraction is not particularly limited and can be appropriately selected according to the purpose. For example, tap water, ion exchange water, distilled water, pure water, ultrapure water, natural water, natural mineral water, Examples include deaerated water and ascorbic acid-dissolved water. Furthermore, as a mode for carrying out the steps (1) and (2) from the beginning in the extraction stage of tea leaves, etc., tea is prepared using pH-adjusted water (including any of acid, base, salt, or a mixture thereof). The extract may be adjusted. As alcohol, C1-C3 methanol, ethanol, and a propanol are mentioned. The amount of the solvent used for the extraction is not particularly limited as long as the raw tea leaves, tea astringents or their powders are sufficiently immersed, and the amount of the solvent may be determined according to the purpose of extraction. The amount is preferably 5 times or more, more preferably 10 to 2000 times the mass of the raw tea leaves, tea astringents or their powders. Although the solvent temperature at the time of extraction will not be specifically limited if it is the temperature which can be extracted, Usually, it is about 4-95 degreeC, Preferably it is 30-90 degreeC. The extraction time is not particularly limited, but is usually about 1 minute to 12 hours, preferably 5 minutes to 6 hours.

  Next, when the pH-adjusted water is not used at the time of extraction, the obtained tea extract may be directly used for the step (1), or the tea extract may be used to adjust the final concentration of chafurosides. If necessary, the process may proceed to step (1) after dilution with water. Alternatively, the tea extract is concentrated and dried under a reduced pressure, preferably under a reduced pressure of 10 to 500 mmHg, at an appropriate temperature, that is, usually 10 to 30 ° C. higher than the boiling point of the solvent used. The removed tea extraction dry residue can be obtained. Furthermore, the tea-dried residue is subjected to liquid-liquid distribution and column chromatography to obtain a concentrated mixture of chafuroside precursors (isovitexin-2 "-sulfate, vitexin-2" -sulfate). You can also. By performing the processes (1) to (3) using such a tea extraction dry residue or precursor concentrated mixture, a chafrosides-rich tea aqueous solution in which the concentration of chafrosides is set to a desired concentration is obtained. Can be prepared.

  As described above, the step (1) may be performed using pH-adjusted water (including any of acid, base, salt, or a mixture thereof) in the extraction stage from tea leaves or the like. For tea extract obtained by extraction with water (distilled water, ion-exchanged water, etc.), or for aqueous solution obtained by redissolving tea extract dry residue etc. in water, acid, base, It may be carried out in the form of adding any salt or a mixture thereof.

  There is no restriction | limiting in particular as an acid, a base, and a salt used by the said process (1), Although it can select suitably according to the objective, The acid, base, and salt which are approved as the food additive mentioned below are mentioned. Is preferred. Sodium hydroxide, ammonium carbonate, potassium carbonate, calcium carbonate, ammonium bicarbonate, sodium bicarbonate, sodium carbonate, magnesium carbonate, calcium dihydrogen pyrophosphate, sodium dihydrogen pyrophosphate, tetrapotassium pyrophosphate, tetrasodium pyrophosphate, polyphosphorus Sodium phosphate, potassium metaphosphate, sodium metaphosphate, phosphoric acid, calcium monohydrogen phosphate, tripotassium phosphate, tricalcium phosphate, diammonium hydrogen phosphate, dipotassium hydrogen phosphate, disodium hydrogen phosphate, phosphoric acid Trisodium, calcium dihydrogen phosphate, sodium dihydrogen phosphate, adipic acid, L-ascorbic acid, sodium L-ascorbate, sodium L-aspartate, benzoic acid, sodium benzoate, erythorbic acid, erythorbium Acid sodium, citric acid, calcium citrate, sodium ferrous citrate, iron citrate, ammonium iron citrate, trisodium citrate, gluconic acid, calcium gluconate, succinic acid, disodium succinate, acetic acid, sodium acetate Succinic acid, L-tartaric acid, potassium L-tartrate, sodium L-tartrate, sorbic acid, potassium sorbate, dehydroacetic acid, sodium dehydroacetate, lactic acid, sodium lactate, calcium pantothenate, fumaric acid, monosodium fumarate, propion Acid, calcium propionate, sodium propionate, propyl gallate, DL-malic acid, DL-sodium malate, glycine, sodium L-glutamate.

  The acid, base and salt used in the step (1) may be used as a mixture thereof, and the combination thereof is not particularly limited. Although it can select suitably according to the objective, since it heat-processes at the said process (3), it is preferable to use a buffer solution. Examples of the buffer solution include a citrate buffer solution (pH 3.0 to 6.2), an acetate buffer solution (pH 3.6 to 5.6), and a citrate-phosphate buffer solution (pH 2.6 to 7.0). , Phosphate buffer (pH 5.8 to 8.0), glycine-sodium hydroxide buffer (pH 8.6 to 10.6), carbonate-bicarbonate buffer (pH 9.2 to 10.6), etc. I can do it.

  The acid, base, salt, or mixture thereof used in the step (1) is adjusted so that its concentration is 0.625 mmol or more with respect to the tea leaf equivalent of 5 g / 1000 ml of tea leaves. For example, 0.625 to 1000 mmol, preferably 0.625 to 500 mmol, more preferably 0.625 to 100 mmol, or any of acids, bases, salts, or their The tea leaves are extracted with an aqueous solution prepared so that the mixture has such a concentration. If the addition amount is less than 0.625 mmol, the conversion reaction hardly proceeds. Further, saltiness is felt at concentrations higher than 10 mmol, but only slightly salty is felt at 10 mmol or less, and saltiness is hardly felt at 5 mmol or less. Therefore, the aqueous solution heated at a concentration of 10 mmol or less can be used as it is for a beverage without being diluted.

  In the step (2), the pH of the aqueous solution subjected to the heat treatment in the step (3) is adjusted to a desired pH in the range of 5 to 10.6 to obtain a pH-adjusted tea aqueous solution. In general, in the heat treatment in the step (3), when the pH value is increased, the generation rate of chafurosides increases, and the content concentration of chafurosides can be increased in a short time. What is necessary is just to set pH according to requirements, such as aiming at such a drink. Under acidic conditions stronger than pH 5, even if the heat treatment in the step (3) is performed, the formation of sufficient chafurosides is not recognized. On the other hand, under basic conditions stronger than pH 10.6, the formation of chafurosides is sufficiently observed, but chafrosides are easily decomposed even at relatively low heating temperatures, and are difficult to handle due to their strong basicity. This is not preferable because it is necessary to neutralize with a large amount of acid when finally making a tea beverage.

  When the pH-adjusted tea aqueous solution is obtained using the tea extract dry residue, the acid extract, the base, the salt, or a mixture thereof is prepared after making the tea extract dry residue an aqueous solution having a desired concentration. The pH may be adjusted with the above, or the dried tea extraction residue may be directly dissolved in any one of acid, base, salt, or a mixture thereof to obtain a pH-adjusted tea aqueous solution having a desired concentration.

  When the steps (1) and (2) are not performed, that is, without using any acid, base, salt, or a mixture thereof, or even if used, the pH is adjusted so as to be within a predetermined pH range. Without carrying out, when it attach | subjects to the following heating process (3), it is difficult to obtain the tea aqueous solution containing high chafurosides which is the object of the present invention.

  The heating method in the step (3) is not particularly limited. For example, even simple heating by a heating kettle (reaction kettle) using pressurized steam or a heat exchange device (plate type heat exchanger, spiral type heat exchanger, etc.) is heating using microwaves. Also good. Considering the amount of investment in the apparatus and mass processing, it is preferable to use a heat exchange apparatus having a heat exchange surface area as wide as possible in order to shorten the heating time. In the heat exchange device, continuous heat treatment can be performed while keeping the heating time constant by controlling the flow rate of the pH adjusted tea aqueous solution. In the case of using a microwave, the irradiation conditions are not particularly limited. For example, it is preferable to irradiate a microwave of 2450 ± 30 MHz with an output of preferably 30 W or more, more preferably 100 to 400 W.

  The heating temperature in the said process (3) is 100-150 degreeC, Preferably it is 120-150 degreeC, More preferably, it is 120-140 degreeC. By heating for a predetermined time in this temperature range, the concentration of chafurosides in the pH-adjusted tea aqueous solution can be dramatically increased. When heated at a temperature higher than this, the pyrolysis of the chafuroside begins to proceed at an accelerated rate, and problems with the quality of the tea beverage begin to occur. Further, at a temperature lower than this, a sufficient amount of chafuroside is hardly generated.

  Heating time is also important in order to suppress the thermal decomposition of chaflosides and not impair the quality as a tea beverage. The heating time at the above heating temperature depends on the pH of the aqueous solution at the time of the heat treatment, but it is 15 seconds to 16 minutes, and in a shorter time, generation of a sufficient amount of chafurosides is not observed, and a longer time than this. Then, decomposition of chafuroside proceeds. Therefore, it is preferably 1 to 16 minutes at 100 to 130 ° C, 15 seconds to 4 minutes, more preferably 15 seconds to 2 minutes at 130 to 150 ° C.

  When using the thus-prepared chafuroside-containing tea aqueous solution as a tea beverage, it is packed in a predetermined container. Container-packed beverages can be manufactured under sterilization conditions stipulated in applicable regulations (in Japan, the Food Sanitation Law) if they can be sterilized by heating after filling into containers such as metal cans. . On the other hand, for PET bottles and paper containers whose demand has been growing rapidly in recent years, after sterilizing under the same sterilization conditions as above, for example, a plate heat exchanger, etc. A method of filling the container after cooling to a low temperature can be employed. Moreover, you may mix | blend another component with the filled container under aseptic conditions. Furthermore, after heat sterilization under basic or acidic conditions, it is possible to return pH to neutrality under aseptic conditions, or after heat sterilization under basic or neutral conditions, to return pH to acidic conditions under aseptic conditions. It is. Therefore, among the heating conditions in the step (3), the condition of heating at 130 to 150 ° C. for 15 seconds to 2 minutes is a condition that can also serve as the sterilization described above, and shortens the final product manufacturing process and reduces costs. It has a great merit to connect, and its industrial useful value is extremely high.

  In the beverage of the present invention, general additives used when preparing food and drink, for example, sweeteners, colorants, preservatives, antioxidants, color formers, emulsifiers, fragrances, acidulants, bitterness and astringency suppression Ingredients, vitamins, various esters, inorganic acids, inorganic acid salts, inorganic salts, seasonings, fruit juice extracts, vegetable extracts, nectar extracts, pH adjusters, quality stabilizers, etc. alone or in combination be able to. Specifically, sweeteners such as sugar, glucose, fructose, isomerized liquid sugar, fructooligosaccharide, aspartame, sorbitol, stevia; red cabbage pigment, grape skin pigment, elderberry pigment, caramel, gardenia pigment, corn pigment, saffron pigment Preservatives such as pectin degradation products, benzoic acid, sorbic acid, paraoxybenzoic acid esters, potassium sorbate; sodium alginate, propylene glycol alginate, calcium fibrin glycolate, sodium fibrin glycolate Pastes such as L-ascorbic acid, tocopherol, erythorbic acid, rutin, etc .; color formers such as ferrous sulfate, sodium nitrite, potassium nitrate; lecithin, sphingolipids, vegetable sterols, soybean saponin, argin Emulsifiers such as sodium acid, propylene glycol alginate ester caseinate, glycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, sodium chondroitin sulfate; lemon oil, eucalyptus oil, brackish oil, vanilla extract, orange oil Fragrances such as garlic oil, ethyl acetoacetate, anisaldehyde, ethyl vanillin, cinnamic acid, citronellyl acetate, citral, vanillin, butyl butyrate and esters.

  The acidulant used in the beverage of the present invention contains at least one selected from citric acid, gluconic acid, tartaric acid, lactic acid, fumaric acid, malic acid, phosphoric acid, ascorbic acid and salts thereof, In the case of a polybasic acid, it may be in the form of an anhydride. Of course, these acidulants may be used as acids or salts for addition in the step (1). Among these acids, citric acid, phosphoric acid, and ascorbic acid are preferable for obtaining an optimal acidity. These acidulants are preferably contained in the beverage of the present invention in a total of 0.01 to 1.0% by mass, further 0.1 to 0.4% by mass, particularly 0.1 to 0.3% by mass. .

  The beverage of the present invention preferably has a pH (25 ° C.) of 2 to 9, and preferably 3 to 7, and more preferably 4 to 7 from the viewpoint of flavor and appearance. Therefore, when the heat treatment of the step (3) is performed at a basic pH, the pH of the beverage of the present invention may be adjusted to the acidic side using these acidulants.

  In addition, the beverage of the present invention can be provided as a food for specified health use, a special nutrition food, a functional beverage as a dietary supplement, or other nutrition beverage, health drink, or health tea. Here, the food for specified health refers to food that can indicate that a specific health purpose can be expected. In addition, special nutritional foods are foods that can indicate the function of the nutritional components when the amount of nutritional components included in the daily intake standard amount conforms to the standards set by the government for the upper and lower limits. is there.

  The chaflosides in the present invention mean at least the chafroids A and B represented by the above chemical formula 1.

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

  The quantification of chaflosides in the present invention is carried out by the HPLC-MS / MS analysis method described in Patent Document 6, and the trade names “Agilent 1100” and “API 2000” (manufactured by Applied Bio) are used for the HPLC-MS / MS analysis. ). As a column for HPLC, a C18 column manufactured by Intact Co., Ltd. was used, and “HPLC-MS / MS analysis method of Cadenza CD-C18” using a specific solvent was performed.

Calibration curves for chafloside A and B and isovitexin 2 "-sulfate and vitexin 2" -sulfate (precursors of chafloside A and B, respectively) were prepared as follows. That is, standard solutions of 5.0 ng / ml, 50 ng / ml, 500 ng / ml and 5000 ng / ml were prepared from chafloside A and B and precursors of chafloside A and B, which were synthesized in advance. In the HPLC analysis, 10 μl of each of these standard solutions is used, the trade name “Cadenza CD-C18” (3 × 150 mm) is used for the column, and elution development is performed using a mixed solvent of H ₂ O—CH ₃ CN. A gradient method of 15-50% over 20 minutes was used. A calibration curve was created from the peak area of each compound in the obtained chromatogram. Based on the calibration curve, the above compounds in each sample in the examples were quantitatively analyzed.

In this example, the following varieties were used as tea leaves.
Green tea; carabeni, meiryoku roasted tea; carabeni, meiryoku oolong tea; narcissus, wuwei narcissus, sui narcissus, white leaves, honey orchid, bonito tea;

  In this example, each commercially available tea leaf was pulverized with a pulverizer (Iwatani Milcer, Iwatani Corporation), 1000 ml of distilled water was added to each 25 g, and extracted at 80 ° C. for 30 minutes. The contents of the precursor of chafuroside A (isovitexin-2 ″ -sulfate) and chafuroside A contained in the tea extract were measured. The results are shown in Table 1 (unit: ng / ml). As for the tea cultivar Carabeni, it is clear that there is no significant difference in the content of each component among green tea, black tea, and roasted tea, and overall, the content of each component is high in oolong tea. Unless otherwise specified, these extracts were diluted with distilled water as necessary, and adjusted to a predetermined concentration and a predetermined pH, for example, using a citrate-phosphate buffer solution, A typical example for preparing a pH 6.6 test solution with a precursor concentration of 650 ng / ml is as follows: the tea extract is diluted with distilled water and the chafuroside A precursor concentration is 1300 ng. On the other hand, 13.6 ml of 0.1 M citric acid aqueous solution and 36.4 ml of 0.2 M aqueous solution of disodium hydrogenphosphate are mixed (total 50 ml). By adding and mixing 50 ml of the above aqueous solution having a concentration of 1300 ng / ml, a test solution having a pH of 6.6 having a chafuroside A precursor concentration of 650 ng / ml can be obtained. Although it does not deviate, if the value is slightly deviated, 0.1M aqueous citric acid solution or 0.2M aqueous disodium hydrogenphosphate solution is added in small portions to adjust the pH to 6.6.

A concentrated mixture of chafloside A and B precursors was prepared as follows. That is, tea leaves (1 Kg, cultivar: Shosuisen) were immersed in distilled water (5000 ml) and stirred at 80 ° C. for 30 minutes. After insoluble matter was removed by filtration, about half of the volume of the water extract was added to n-BuOH to perform liquid-liquid partition. This operation was performed twice, and the obtained water fraction was adjusted to pH 4.0 with dilute hydrochloric acid and then separated into Sephaeas.
The column was subjected to SP825 (mitsubishi chemical) column chromatography and eluted sequentially with water, 20% MeOH, 50% MeOH and 100% MeOH. Next, the 50% MeOH elution part (160 g) containing the precursors of chafuroside A and B was subjected to SiO ₂ column chromatography using CHCl ₃ -MeOH-H ₂ O (60: 40: 8) as a developing solvent, A concentrated mixture (22 g) of A and B precursors was obtained. The mixing ratio of both precursors in this concentrated mixture was chafuroside A precursor: B precursor = 1: 1.1.

  For the reaction in the Neat state, a substance prepared from tea leaves as follows was used. That is, tea leaves were pulverized with a miller (manufactured by Iwatani Sangyo Co., Ltd.), water or 50% methanol was added at a ratio of 1 g of pulverized product / 100 ml of solvent, and extraction was performed with stirring at 80 ° C for 30 minutes. Subsequently, the concentrated mixture of the precursors of the chaflosides A and B was added to prepare a high content tea aqueous solution of the precursors of the chaflosides A and B and 50% methanol containing the precursors of the chaflosides A and B. A 50% methanol solution containing a high amount of precursors of chafuroside A and B was concentrated to dryness to obtain a neat reaction substance.

  For the heat treatment in this example, an oil bath with a heating device (NWB-120N manufactured by Nissin), a microwave heating device (Initiator 8 manufactured by Biotage), or a plate heat exchanger (manufactured by Nisaka Seisakusho) was used.

Sensory evaluation Sensory tests of various aqueous tea solutions before and after heating in each example were conducted by five panelists. Evaluation was based on the following criteria and averaged by 5 people.
Fragrance: Compared with the non-heated solution not subjected to the step (3),
○: Almost no change in scent.
Δ: A slight change in scent is felt.
X: Change in scent is clearly felt.
Color: In appearance comparison with a non-heated solution not subjected to the step (3),
○: Little change in turbidity and / or color is felt.
Δ: A slight change in turbidity and / or color is felt.
X: Change in turbidity and / or color is clearly felt.
Example 1

  The tea extract prepared using narcissus tea leaves by the above method was diluted with distilled water so that the concentration of the Chafloside A precursor was a predetermined concentration. Its pH was 5.2. A portion of this extract was adjusted using distilled water and an acetate buffer so that the concentration of the Chafloside A precursor was a predetermined concentration and the pH was 5.2. The pH-adjusted tea aqueous solution was heated for 2 minutes at each temperature from 100 ° C. to 180 ° C. (in increments of 10 ° C.) using a microwave heating apparatus (Example 1). As a comparative example, an aqueous solution in which only the concentration of the chafuroside A precursor was adjusted without adjusting the pH was heated under the same conditions as in Example 1 (Comparative Example 1). Moreover, the narcissus extract neat substance obtained by the said method was heated with the oil bath for 4 minutes with the neat form (comparative example 2). Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 2.

  “Pre-A” and “A” in the upper part of the table represent isovitexin-2 ”-sulfate and chafuroside A. The unit of the quantitative value of each compound shown in the table is ng / ml. It is.

In Example 1, the influence of the addition of an acid, base, or salt from the outside on the conversion efficiency of the chafuroside precursor to chafuroside was examined. In Example 1, since it was necessary to adjust to the same pH as in the case of non-adjustment, an acetate buffer was used. As is apparent from Table 2, in Example 1 in which an acid and a salt were added from the outside to the tea extract subjected to the heat treatment, the amount of chafuroside A precursor decreased in a temperature-dependent manner. The amount of A is increasing. At a temperature of 170 ° C. or higher, both compounds start to decompose, but the content of chafuroside A shows a maximum value of 404 ng / ml at 170 ° C., and the decomposition is remarkable at temperatures higher than this (both at 180 ° C.). The total amount of the compound is 362 ng / ml, which is about half the amount when not heated). In Comparative Example 1 in which no acid and salt are added from the outside, a temperature 20 to 30 ° C. higher than that in Example 1 is required. At such high temperatures, decomposition proceeds simultaneously, so the maximum value is only 172 ng / ml at 180 ° C. Since Comparative Example 2 uses an oil bath and the heating time is as long as 4 minutes, a simple comparison with Example 1 is not possible. For example, when the amount of chafloside A produced at 150 to 170 ° C. is compared, In Comparative Example 2 where no acid and salt were added from the outside, only about half of Example 1 was produced. From this result, by adding an acid and a salt from the outside, the conversion reaction from the chafuroside A precursor to the chafuroside A is promoted, and even if it is not added, the reaction does not proceed at a low temperature, specifically 150 ° C. or less. It became clear that conversion occurred.
Examples 2-3

  For the tea leaves of Takewei narcissus or carabeni green tea, distilled water and aqueous sodium hydrogen carbonate solution were used, and the concentration of the chafuroside A precursor was adjusted to a predetermined concentration and the pH was adjusted to 7.3 or 8.0. A solution without added aqueous sodium hydrogen carbonate solution was used as a comparison. Each aqueous solution was heat-treated at 130 ° C. for 1 minute or 170 ° C. for 2 minutes using a plate heat exchanger. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 3.

  In the table, “front A”, “front B”, “A”, and “B” represent isovitexin-2 ″ -sulfate, vitexin-2 ″ -sulfate, chafuroside A, and chafuroside B, respectively. . The unit of the quantitative value of each compound shown in the table is ng / ml. The abbreviations and units are the same in Tables 4 to 15 below.

In Examples 2 to 3, it was examined whether or not the conversion from the chafroside precursor to the chafloside proceeded well even when the external acid, base, or salt was not a buffer solution as in Example 1. As is apparent from the results in Table 3, the hot water extract of Takewei narcissus was adjusted to pH 7.3 using an aqueous sodium hydrogen carbonate solution, and then heated at 130 ° C. for 1 minute to contain chafuroside A and chafuroside B. The amount increased to about 8 times and about 5 times, respectively. At this time, no change was observed in the aroma and color of the tea solution. On the other hand, even when heated at 130 ° C. for 1 minute without adjusting the pH without adding an aqueous sodium bicarbonate solution, virtually no chafuroside A and chafuroside B were produced. Further, in order to promote the formation of chafloside A and chafloside B, it is found that when heated at a higher temperature of 170 ° C., chafloside A and chafuroside B are generated somewhat, but decomposition by high temperature heating occurs at a high rate. It was. Furthermore, it was confirmed that some deterioration in the quality of tea beverages such as aroma and color occurred. The same was observed in carabeni green tea (Example 3). In addition, about cultivar carabeni, although examination was also made about kettle roasted tea and black tea, the same result as the case of the green tea of Example 3 was obtained (data omitted). From the above results, it is not necessary that the acid, base or salt added from the outside be a combination acting as a buffer as in Example 1, and a considerable amount of decomposition proceeds at a high temperature of 170 ° C. At the same time, it became clear that there was a problem in quality as a tea beverage.
Examples 4-11

  About five kinds of tea leaves of Takewei narcissus, carabeni green tea, white leaves, narcissus, and grape seeds, as in Examples 2-3, distilled water and sodium bicarbonate aqueous solution were used, and the concentration of chafuroside A precursor was at a predetermined concentration. The pH was adjusted to 6.5 to 8.0. Each aqueous solution was heat-treated using a plate heat exchanger. Takewei narcissus aqueous solution is 133 ° C., 1 minute and 1.75 minutes, Carabeni green tea aqueous solution is 135 ° C., 1 minute and 1.75 minutes, white leaf and potato seed water solution is 133 ° C., 1 minute, narcissus aqueous solution Were each subjected to heat treatment at 140 ° C. for 1 minute. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 4.

In Examples 4-11, the sodium hydrogencarbonate aqueous solution was used similarly to Examples 2-3, and the effect in different varieties, the effect of heating time, and the influence of pH were investigated. As apparent from the results in Table 4, the hot water extract of tea leaves was adjusted to pH 7.5 to 8.2 using an aqueous sodium hydrogen carbonate solution, and then heated at 133 to 140 ° C. for 1 minute, whereby Chafloside A And the content of chafloside B was greatly increased. As in Examples 2-3, it was demonstrated in other varieties that it was not necessary to use a buffer. From Examples 4 and 5, it has been clarified that chafloside A and B increase in proportion to the time by increasing the heating time. Further, at this heating temperature, almost no decomposition occurred when heating for a little less than 2 minutes. Regarding the influence of the pH of the aqueous solution, as is clear from the comparison between Examples 6 and 7, the comparison between Examples 8 and 9, and the comparison between Examples 10 and 11, any of the white leaves, daffodils, and varieties have a base. The rate of increase of Chafloside A and Chafloside B was higher when the properties were higher. In general, since the varieties are different, the components and their contents in the hot water extract are different, so that a simple comparison cannot be made, but it can be seen that the conversion rate is improved as the pH increases. Moreover, when the results of heating temperatures of 133 ° C. and 140 ° C. were compared, the rate of increase of chafloside A and chafloside B was higher when the heating temperature was higher. By the way, in the narcissus tea extract pH 8.0 at 140 ° C. for 1 minute, the Chafloside A content increased 12.6 times and the Chafloside B content increased 8.8 times. Furthermore, the conversion when using an aqueous sodium hydrogen carbonate solution is not limited to basic conditions. Even when the pH is adjusted to be weakly acidic at pH 6.5 or neutral at pH 7.0, it is added. Even when the amount of sodium hydrogen carbonate was small, it was confirmed that the conversion to chafuroside proceeded (Examples 10 and 11). No changes were observed in the aroma and color of these tea aqueous solutions after heating. In addition, about cultivar carabeni, examination was also made about kettle roasted tea and black tea, but the same results as in the case of green tea of Example 5 were obtained (data not shown).
Examples 12-13

  About the tea leaves of honey orchid, it adjusted so that the density | concentration of the chafuroside A precursor might be set to predetermined | prescribed density | concentration and the pH might be 5.8 using distilled water and an acetate buffer or a citrate-phosphate buffer. Each aqueous solution was heated for 2 minutes at 100 ° C. to 180 ° C. (10 ° C. increments) using a microwave heating apparatus. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 5.

Examples 12 and 13 are experiments conducted by changing only the type of additive, and it was investigated whether or not the conversion efficiency from the chafuroside precursor to the chafuroside was affected when the additive was different at the same pH. It is. The influence of the heating temperature was also examined while keeping the heating time constant (2 minutes). As is clear from Table 5, in any of the buffer solutions, chafloside A is produced from about 110 ° C., and the production amount is increased as the heating temperature is increased. In either case, the decomposition of both compounds starts at 160 to 170 ° C. or higher, and the quality deteriorates. That is, it is considered that the kind of additive has little influence on the production amount and production rate of chafloside A. Even at the same pH, when the citrate-phosphate buffer solution is used, decomposition and deterioration start to occur at a temperature as low as 10 ° C., but the cause is not clear.
Examples 14-19

  About the tea leaves of the honey orchid, it adjusted so that the density | concentration of the chafuroside A precursor might be a predetermined density | concentration and the pH might be 4.4-7.8 using distilled water and various buffer solutions. Each aqueous solution was heated for 2 minutes at 100 ° C. to 180 ° C. (10 ° C. increments) using a microwave heating apparatus. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 6.

In Examples 14 to 19, the kind of buffer to be added was changed, and the influence of pH on the conversion of the chafroside precursor to chafroside was examined. The influence of the heating temperature was also examined while keeping the heating time constant (2 minutes). That is, from the results of Table 5 above, since the influence of the type of additive is small, in this example, the pH was swung in the range of 4.4 to 7.8 using different buffer solutions. As is clear from the results in Table 6, the reaction at pH 4.4 was very mild, and only a small amount of chafuroside A was observed when the heating temperature was increased to 160 ° C. or higher. On the other hand, it can be seen that at pH 5.0 or higher, the production amount of chaflosides A and B increases as the pH value increases. For example, the amount of increase in chafloside A at a heating temperature of 130 ° C. changes as follows. 32 ng / ml (pH 5.0) → 33 ng / ml (pH 5.8) → 270 ng / ml (pH 6.6) → 289 ng / ml (pH 7.0) → 339 ng / ml (pH 7.8). That is, as the pH increases, the maximum content of chafurosides can be obtained at a lower temperature. For example, at a pH of 7.0, the maximum content was shown at 140 to 150 ° C. On the other hand, as pH increases, the degradation of chafuroside precursors and chafuroside also occurs at lower temperatures. In addition, at pH 6.6 or higher, it is shown that the reaction proceeds to some extent even at a heating temperature of 100 ° C. This means that if the heating time is increased, a sufficient content of chafuroside can be obtained even at 100 ° C. It suggests. It can be seen that the conversion of the chafloside B precursor to the chafloside B generally requires a higher temperature of about 10 ° C. than the conversion of the chafloside A precursor to the chafloside A.
Examples 20-27

  As for the tea leaves of suisuisen, distilled water and glycine-sodium hydroxide buffer or carbonate-bicarbonate buffer are used so that the concentration of the chafuroside A precursor is a predetermined concentration and the pH is 7.5 to 10.6. Adjusted. Each aqueous solution was heated for 2 minutes at a temperature of 80 ° C. to 160 ° C. or 170 ° C. (10 ° C. increments) using a microwave heating apparatus. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 7.

In Examples 20 to 27, two types of buffer solutions were used, and the influence on the conversion from the chafuroside precursor to the chafuroside on the basic side was examined. The influence of the heating temperature was also examined while keeping the heating time constant (2 minutes). As is clear from the results in Table 7, as the pH increases, the maximum content of chafurosides can be obtained at a lower temperature, and the decomposition of chafuroside precursors and chafurosides also occurs at a lower temperature. Became. This is the same as the result of Table 6 above. On the other hand, with weak basicity (pH 9 or lower), the yield of chafuroside is better when using a carbonate-bicarbonate buffer, but when pH 9 or higher, the yield is better when using a glycine-sodium hydroxide buffer. At pH 10.2, the highest content in a series of examples with a chafroside A concentration of 478 ng / ml was obtained by heating at 140 ° C. for 2 minutes. In addition, when a carbonate-bicarbonate buffer is used, decomposition of the compound occurs even at a temperature of 130 to 150 ° C. Further, at any pH, it was revealed that the generation efficiency of chafuroside was poor at a temperature of 90 ° C. or lower, and virtually no conversion occurred at 80 ° C. or lower.
Examples 28-34

  About the tea leaves of suisuisen, distilled water and various buffers were used so that the concentration of the chafloside A precursor was a predetermined concentration and the pH thereof was adjusted to 4.0 to 10.1. Each aqueous solution was heated using an oil bath at each temperature from 90 ° C. to 180 ° C. (in increments of 10 ° C.) for 2 minutes. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 8.

In Examples 28 to 34, the effect of using an oil bath as a heat source on the conversion efficiency from a chafuroside precursor to chafuroside was examined. The pH of the test aqueous solution was in the range of 4 to 10.1, and the heating time was set to 2 minutes as in the case of microwave heating, and the influence of the heating temperature was also examined. In comparison with Table 6, in the microwave heating, sufficient chafloside formation was observed even at pH 5.0 (Example 15). However, in the case of an oil bath, conversion efficiency was promoted when the pH value was increased. In spite of the fact that it was clear, at pH 5.2, virtually no conversion occurred even at a heating temperature of 150 ° C. or higher (Example 29). Furthermore, when compared with the results described in Tables 6 and 7, Example 17 (pH 6.6), Example 30 (pH 6.5), Example 18 (pH 7.0) and Example 31 (pH 7.3). ), Example 19 (pH 7.8) and Example 32 (pH 8.0), Example 25 (pH 9.6) and Example 33 (pH 9.4), and Example 26 (pH 10.0) and Example In the comparison of 34 (pH 10.1), although the pH value is slightly different, it is clear that the conversion yield is poor when the oil bath is used as the heating source even though the same buffer is used. It is. From these results, it was found that oil bath heating is slower in heat transfer than microwave heating, and the heat efficiency is poor because it is difficult to transfer heat uniformly. Furthermore, when compared with the heating results using the heat exchangers in Tables 3 and 4, the same can be said although the types and types of additives are different. For example, 135 ° C. and 1.75 minutes (218 ng / ml) of Example 5 each having a pH of 8.0, or 140 ° C. and 1 minute (201 ng / ml) of Example 9 and Examples This is evident when comparing the results of 32 at 140 ° C. for 2 minutes (191 ng / ml). From the above results, in order to shorten the heating time and lower the thermal decomposition rate, efficient heating is necessary, and in the tested range, heating with a heat exchanger or microwave is preferable to an oil bath. understood.
Example 35

  Using a concentrated mixture of chafuroside A and B precursors (mixing ratio 1: 1.1) derived from Daffodil, the concentration of both precursors in the test solution was adjusted to a double common ratio. Citric acid / disodium hydrogen phosphate was used as an additive, each pH was set to 7.0, and it was heated in a microwave at 130 ° C. for 2 minutes. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 9.

In the examples so far, heat treatment has been performed using an aqueous solution adjusted to have a chafuroside A precursor concentration of about 650 ng / ml. However, in example 35, the concentration of chafuroside A and B precursors was increased. Whether the conversion efficiency was affected when the mixture was used and the concentration was further increased was examined. The combined maximum concentration of both precursors studied was 40.32 μg / ml, corresponding to a concentration about 30 times higher than before. As is clear from Table 9, even when the concentration was increased at a double common ratio, the chaffroside concentration increased in proportion to it, and it was clarified that the conversion efficiency was never reduced. That is, it is presumed that if the concentration is about several tens of μg / ml, the conversion efficiency is not affected at all, and even if it is several thousand μg / ml, no major problem will occur. Conversely, even a dilute solution with a precursor concentration of about half had no effect.
Examples 36-38

  For the tea leaves of honey orchid, extract neat state (Comparative Example 3), pH unadjusted aqueous solution (pH 5.4) (Comparative Example 4), and pH to 5.0 or 5.8 using acetic acid / sodium acetate The prepared aqueous solution was heated at 130 ° C. for 1 to 16 minutes using an oil bath or microwave, respectively. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 10.

In Comparative Examples 3 to 4 and Examples 36 to 38, it was examined how much the conversion from the chafuroside precursor to the chafuroside in the vicinity of pH 5.5 is affected by the heating time. In the reaction in the neat state of Comparative Example 3 to which no external acid, base, or salt was added, even if heating was continued for 16 minutes, virtually no change including decomposition occurred. Even in the acid, base or salt-free aqueous solution of Comparative Example 4, only a slight amount of chafuroside was observed. These results are the same as the results of Comparative Examples 1 and 2 in Table 2. Even if the heating time is extended, the conversion from the chafuroside precursor to the chafuroside is extremely difficult under the condition that no acid, base or salt is present. It is hard to happen. On the other hand, in Examples 36 to 38 to which acetic acid / sodium acetate was added, results supporting the results so far were obtained. Even at pH 5.0, a sufficient amount of conversion can be achieved by heating for a long time using microwaves. Results are obtained and little degradation occurs at this pH and temperature. The comparison results of Examples 37 and 38 are the same as the results of Table 8 and indicate that the microwave is 2 to 2.5 times more efficient than the oil bath. In addition, when heated for 8 minutes under the conditions of both examples, almost no decomposition occurs regardless of the heat source, but when heated for 16 minutes, about 7% or about 20% decomposition occurs in terms of simple weight. It can be seen that the microwave is more likely to be decomposed.
Examples 39-44

  For the tea leaves of honey orchid, an aqueous solution adjusted to pH 5.8 using acetic acid / sodium acetate, and an aqueous solution adjusted to pH 6.6 using citric acid / disodium hydrogen phosphate, respectively, using an oil bath, 110 Heated at a temperature of ˜130 ° C. for 1 to 16 minutes. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 11.

In Examples 39 to 44, the influence of the heating time on the formation of chafuroside when heated at a relatively low temperature (110 to 130 ° C.) in a weakly acidic pH range preferable as a beverage was examined. As is clear from the results in Table 11, it was confirmed that sufficient conversion occurred over time even at 110 ° C. using an oil bath in a weakly acidic pH range suitable as a beverage. Although it was confirmation of the results so far, the conversion yield was better as the pH and the heating temperature were higher. In Example 44, the maximum concentration of chafuroside (conversion yield of 66%) was obtained under the conditions of pH 6.6, 130 ° C., and 16 minutes heating. At the same time, in terms of weight as the total amount of chafuroside precursor and chafuroside. About 30% degradation has occurred.
Examples 45-67

  For the tea leaves of honey orchid, an aqueous solution adjusted to pH 5.0 to 7.8 using various buffer solutions is used at a temperature of 110 to 130 ° C. for 1 to 16 minutes or at 150 ° C. for 1 minute using a microwave. Within heating was performed. In addition, the aqueous solution having a pH of 8.4 prepared from the white tea leaves was similarly heat-treated. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 12.

Under the weakly acidic conditions of Examples 45 to 56, no significant decomposition occurred even when heated at 130 ° C. for 16 minutes, and the maximum content of chafuroside was obtained by heating for approximately 16 minutes at any temperature. Of course, even at 110 ° C., it can be confirmed that sufficient conversion occurs over time. Compared with the results shown in Table 11 using an oil bath, the amount of conversion generated greatly increases due to the use of the microphone. I understand. Under neutral conditions of Examples 57 to 59, at 110 to 120 ° C., decomposition began to occur from about 8 minutes, but the amount of chafuroside produced was maximized by heating for 16 minutes. At 130 ° C., decomposition starts after 4 minutes, and after 16 minutes, about 40% is decomposed, and the maximum production amount of chafuroside is achieved by heating for 8 minutes. Under the weakly basic conditions of Examples 60 to 67, as is apparent from the data so far, the conversion rate is increased and the decomposition is more likely to occur. At pH 7.8, the maximum generation of chafuroside occurs at 120 to 130 ° C. for 4 to 8 minutes (Examples 61 and 62). Further surprisingly, at 150 ° C., it has been found that a sufficient amount of conversion occurs even with a heating time of less than 1 minute, more specifically for a short time of 15-30 seconds (Example 63, 67). These facts show that a chafroside-rich tea aqueous solution can be produced at a heating temperature of 130 to 150 ° C. and a heating time of 15 seconds to 2 minutes under neutral or weakly basic conditions.
Examples 68-76

  For the tea leaves of honey orchid, an aqueous solution adjusted to be weakly acidic (pH 6.2), neutral (pH 7.0), and weakly basic (pH 7.8) using three kinds of buffer solutions, Heating was performed at a temperature of 130 to 150 ° C. for 15 seconds to 8 minutes. Each sample obtained was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 13.

This example is based on the results shown in Table 12. If the temperature is relatively high (130 to 150 ° C.), whether or not the generation of chafloside can be sufficiently obtained within a few minutes of heating time even in a weakly acidic to neutral region. Is considered. Although it can be inferred from Table 12 that sufficient production will be observed under weakly basic conditions (pH 7.8), from the results of Examples 74 to 76, the formation of chafuroside is 4 minutes at 130 ° C. It was confirmed that the maximum amount was reached in 1 minute at 140 ° C and 30 seconds at 150 ° C. Under the conditions where this maximum value was obtained, some decomposition (calculated from the decrease in the total amount of A + A before) started to occur, and the degree was about 10 to 20%. Also, under mildly acidic conditions (pH 6.2), the amount of chafuroside generated is maximum for 8 minutes or more at 130 ° C and 140 ° C (conversion yields of 77% and 87%, respectively), and 2 minutes even at 150 ° C. (Conversion yield was 91%). This is a result that supports the results so far, and the reaction rate is still slow under acidic conditions. In these heating times, decomposition occurs to the extent of 10% or less (Examples 68 to 70). On the other hand, under neutral conditions (Examples 71 to 73), the formation of chafuroside was 8 minutes at 130 ° C. (conversion yield 94%), 2 minutes at 140 ° C., and 1 minute at 150 ° C. (both conversion yields). The rate reached about 100%). The degradation rate under neutral conditions was low, and almost no degradation was observed under conditions where the maximum value was obtained. In general, it is preferable to perform the heat treatment with an aqueous solution having a pH of 6 to 8 at a heating temperature of 130 to 150 ° C. and a heating time of 15 seconds to 2 minutes, and further, a neutral aqueous solution of pH 7 at 140 ° C. for 2 minutes, or It was considered preferable to heat at 150 ° C. for 1 minute. However, the heating conditions are not particularly limited, and there is sufficient room for appropriate selection according to the equipment conditions and purpose.
Example 77

  Extract 5 g of tea leaves of suisuisen with 1 L each of aqueous solution adjusted to a total concentration of citrate / sodium citrate from 0.625 to 50 mM using a citrate buffer solution of pH 6.4. did. Each obtained extract was heated at 140 ° C. for 1 minute using a plate heat exchanger. Each sample was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 14.

This example was carried out in order to verify the concentration range in the test aqueous solution of any of the acid, base, salt, or mixture thereof added in the step (1). When a normal buffer solution is used, the final concentration is often 50 mmol (varies depending on the type of the buffer solution and is approximately 50 to 100 mmol). However, as is apparent from the results in Table 14, additives In the presence of 50 millimoles, heating at 140 ° C. for 1 minute increased chaflosides A and B to about 12 times and about 10 times, respectively, compared with the case of no heating. Furthermore, even if the concentration of the additive is lowered to 10 millimoles and 5 millimoles, the increase in the amount of chafuroside does not decrease extremely, and even if it is reduced to 2.5 millimoles, the increase is about 4.5 times. Indicated. Incidentally, the conversion yields (number of moles formed / number of moles of raw materials) of chafuroside A and B at 5 mmol were 53% and 19%, respectively. Even at a lower concentration of 0.625 mmol, sufficient conversion occurred, and the conversion yields of chafuroside A and B were about 15% and about 6%. The fact that such a conversion yield can be obtained by heating at 140 ° C. for 1 minute seems to be sufficiently possible to achieve a yield of 90% or more if the heating time is further extended.
Example 78

  Extracted 5 g of tea leaves of suisuisen by a conventional method using 1 L of an aqueous solution adjusted to a total concentration of 10 mM citrate / disodium hydrogenphosphate using a citrate-phosphate buffer solution of pH 7.0. . The obtained extract was heated at 100 to 130 ° C. for 1 minute using a plate heat exchanger. About 110 degreeC, the heating for 2 minutes and 4 minutes was also performed. Each sample was subjected to HPLC-MS / MS analysis to quantify each component. The results are shown in Table 15.

  This example was performed in order to verify that the conversion reaction proceeds even when a plate heat exchanger is used at a low heating temperature of 100 to 130 ° C. As is clear from the results in Table 15, the conversion yield of chafurosides was improved by increasing the reaction temperature or lengthening the reaction time. Even at 100 ° C. for 1 minute, the conversion yields of chafuroside A and B were about 4% and about 1%. By increasing the reaction time to 1 minute, 2 minutes, and 4 minutes at 110 ° C., for example, the yield of chafuroside A increases from about 9% to about 14% to about 19%. From this, it can be expected that if the reaction time is further increased even at 100 ° C., a sufficient conversion yield can be obtained because almost no decomposition occurs.

  In the above examples, only the results of seven varieties of narcissus, wuwei narcissus, sui narcissus, white leaves, honey orchid, carabeni, and grape varieties have been disclosed. In the presence of any of the added acid, base, salt, or a mixture thereof, the tea extract is heated at 100-150 ° C. with a liquid property of pH 5-10. It has been found that an aqueous solution can be produced.

The method for producing a tea aqueous solution containing a high amount of chaflosides of the present invention has an antioxidant effect, an antiallergic effect, an anti-inflammatory effect, and a carcinogenesis-inhibiting effect without impairing tea quality (tea aroma, flavor, color, etc.) Therefore, it is possible to provide a tea aqueous solution containing a high amount of chafurosides containing an extremely high proportion of known chafrosides.
Therefore, the chafroside-rich tea aqueous solution produced by this method is used as a beverage product having various effects (preventive effects) for maintaining health, as a food for specified health use, a special nutritional food, and a nutritional supplement. Or other nutritional drinks, health drinks, and health teas.

Claims (6)

A method for producing a chafroside-rich tea aqueous solution consisting of chafloside A and / or chafloside B from tea leaves or tea astringents, or a tea extract obtained from tea leaves or tea astringent powder or a dry residue of tea extraction, The manufacturing method characterized by including the following processes (1)-(3).
(1) A step of adding an acid, a base, a salt, or a mixture thereof in any process prior to the heating step described below,
(2) in the step (1), a step of adjusting the pH of the aqueous solution to be subjected to the following heating step 5-7, and (3) pH adjusted tea extract solution obtained by the above step (2), 130 - A step of heat-treating at 150 ° C. for 15 seconds to 4 minutes to obtain a chafroside-rich tea aqueous solution. 2. The method for producing tea according to claim 1 , wherein the acid, base, and salt used in the step (1) are acids, bases, and salts for food additives. Manufacturing method. In the manufacturing method of Claim 1 or 2 , in the said tea extract or its diluted aqueous solution, or a tea extraction dry residue or its aqueous solution, either the acid used in the said process (1), a base, or a salt, Alternatively, a method for producing a chafroside-enriched tea aqueous solution characterized by adding a mixture thereof to obtain a pH-adjusted tea extraction aqueous solution. In the manufacturing method of Claim 1 or 2 , using the aqueous solution which added either the acid used in the said process (1), a base, a salt, or those mixtures, tea leaves or tea astringents, or tea leaves or tea astringents A method for producing a tea aqueous solution containing a high amount of chafurosides, wherein the powder is extracted to obtain a pH-adjusted tea extraction aqueous solution. In the manufacturing method in any one of Claims 1-4 , in the said pH adjusted tea extraction aqueous solution, the density | concentration in any one of the acid used in the said process (1), a base, and a salt, or those totals The concentration is 0.625 to 100 mmol, and the pH-adjusted tea extraction aqueous solution is prepared by using water at a ratio of 1 L with respect to 5 g of tea leaves or tea astringent or tea leaves or tea astringent powder. A method for producing an aqueous tea solution containing a high amount of chafuroside. In the manufacturing method in any one of Claims 1-5 , the heat processing in the said process (3) is heat processing using a microwave or a heat exchanger, The chafuroside high content tea aqueous solution characterized by the above-mentioned. Production method.