JP2004313189A - Catechin containing food or drink and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a food or drink containing catechin in high concentration and excellent in succulent and flavor. <P>SOLUTION: The catechin containing food or drink contains ≥70 wt.% of ester type catechins of (-)EGCg, (-)ECg, (-)GCg and (-)Cg, in the total catechin content, and the sum of the (-)GCg and (-)Cg is ≥40 wt.% in the ester type catechins, the content of (-)ECg is ≤20 wt.% in the ester type catechins and the content of (-)GCg is larger than that of (-)ECg. The catechin food or drink satisfying the requirement has an excellent serum cholesterol cut-down efficacy of catechin and excellent in succulent and flavor, and used for health drink or a diet drink which is easy to ingest. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a catechin-containing food and drink containing catechin at a higher concentration than tea or the like, and a method for producing the same.

  Tea contains tannin (mainly catechin), amino acids, caffeine, sugars, saponins, and the like as water-soluble components. In recent years, various pharmacological effects of these water-soluble components have been clarified, and tea is now attracting attention not only as a drink as a luxury item but as a health drink, and each of the water-soluble components of tea is also used as a pharmacologically active component.

  Among them, catechin has received particular attention, and many drugs containing catechin as an active ingredient have been disclosed. For example, "cholesterol elevation inhibitor (JP-A-60-156614)", "anti-tumor agent (JP-A-60-190719)", "anti-cariogenic and anti-periodontal disease composition (JP-A-60-190719)" 64-00922), "Diarrhea virus infection inhibitor (Japanese Patent Application Laid-Open No. 01-265023)", "Caries Prevention Agent (Japanese Patent Application Laid-Open No. 02-0254313)", "Platelet aggregation inhibitor (Japanese Patent Application Laid-open No. 02-184626), "Influenza virus infection preventive agent (JP-A-03-101623)", "Mycoplasma infection preventive agent (JP-A-03-106820)", "α-amylase activity inhibitor" (Japanese Unexamined Patent Application Publication No. 03-133828), a "hyperglycemia inhibitor (Japanese Unexamined Patent Application Publication No. 04-253918)", a "composition for preventing colorectal cancer (Japanese Unexamined Patent Application Publication No. 04-264027)", " Inflammatory, Gastric or Duodenal Ulcer Prevention Composition (JP-A-05-139972), "Anti-atherosclerotic Agent (JP-A-06-056866)", "Anti-mutagenic activity and superoxide gym star" Tea catechins having ze-like activity (Japanese Patent Application Laid-Open No. 06-128168), "antidote (Japanese Patent Application Laid-Open No. 09-059154)", "Method for enhancing the efficacy of anticancer agents (Japanese Patent Application Laid-Open No. 10-036260)" "," Active oxygen generation inhibitor and active oxygen-induced disease preventive agent (JP-A-10-175858) "," telomerase inhibitor (JP-A-11-246402) "," gastrin secretion inhibitor and gastric acid " Secretion inhibitor (JP-A-11-193239) "and the like.

  By the way, catechin is a compound having a flavan-3-ol skeleton, and (-)-epigallocatechin gallate (EGCg), (-)-epicatechin gallate (ECg), (-)- Epigallocatechin (EGC), (−)-epicatechin (EC), (−)-gallocatechin gallate (GCg), (−)-catechin gallate (Cg), (±) -gallocatechin (GC) and The existence of eight kinds of (±) -catechin (C) is known, and it is classified into ester type catechin having a gallate group and free catechin having no gallate group, or epi-form and non-epi-form. can do.

  On the other hand, each of the above water-soluble components also functions as a taste component of tea. Tannin (catechin) is involved in bitterness and astringency, caffeine and saponin are involved in bitterness, amino acids are involved in umami and sweetness, and sugars are involved in sweetness, and constitute the taste of tea.

  Among them, catechins are generally involved in bitterness and astringency as described above, but taste tendencies vary depending on the type of catechin. That is, free catechins such as (-)-epicatechin (EC) and (-)-epigallocatechin (EGC) have low bitterness and mild bitterness, while (-)-epigallocatechin gallate ( Galate-type ester-type catechins such as EGCg) and (−)-epicatechin gallate (ECg) have a strong bitter taste (see Shizuoka Prefectural Tea Industry Chamber, “New Tea Industry Zensho”, pp. 476-477). (October 1, 1988)).

  Conventionally, catechin-containing foods and drinks containing catechin at a high concentration have been disclosed in order to efficiently ingest catechin having excellent pharmacological action.

  For example, Patent Document 1 discloses that the total concentration of four kinds of catechins of epicatechin, epigallocatechin, epicatechin gallate, and epigallocatechin gallate is 40 mg / 100 ml or less and 20 mg / 100 ml or more in a packaged state after sterilization. And wherein the total concentration of epicatechin gallate and epigallocatechin gallate among the four types of catechins is in the range of 30% to 40% with respect to the total concentration of the four types of catechins, wherein the temperature is below room temperature. Disclosed is a packaged green tea beverage sold in a cooled state.

  Patent Document 2 discloses that (A) non-epicate catechins and (B) catechins of epi-form catechins are dissolved and contained, and the content thereof is as follows: A) + (B) = 460-2500 mg, (b) (A) = 160-2250 mg, (c) (A) / (B) = 0.67-5.67, and pH is 3-7. A packaged beverage is disclosed.

  Patent Document 3 contains (A) non-epitopic catechins, (B) epi-catechins, and (C) cyclic dextrin, and their content is per 500 mL of container-packed beverage, (A) (A) + (B) = 460-1300 mg, (b) (A) = 160-1040 mg, (c) (A) / (B) = 0.54-4.0, (d) (C) = 750-5000 mg. In addition, it discloses a packaged beverage in which the haze value of the beverage is 22 or less.

  Patent Literature 4 discloses that a concentrate of a tea extract is dissolved in a medium selected from water, carbonated water and an extract of teas, and the component (A) which is a non-polymer and is in a dissolved state in water is a non-epi form The catechins and the content of the component (B) epi-form catechins were determined as follows: (A) + (B) = 460 to 2500 mg, (B) (A) = 160 to 2250 mg, per 500 mL of packed beverage. (C) A packaged beverage that is adjusted so that (A) / (B) = 0.54 to 9.0 is disclosed.

  Patent Document 5 discloses that a concentrate of a tea extract is dissolved in a medium selected from water, carbonated water, and an extract of teas, and the component (A), which is a non-polymer and is in a dissolved state in water, is a non-epi form The catechins and the content of the component (B) epi-form catechins were determined as follows: (A) + (B) = 460 to 2500 mg, (B) (A) = 160 to 2250 mg, per 500 mL of packed beverage. (C) A packaged beverage that is adjusted so that (A) / (B) = 0.54 to 9.0 is disclosed.

  Also, if the catechin content is increased by increasing the extraction concentration, bitterness and retort odor become a problem, so that carbon dioxide-containing green tea can drinks blown with carbon dioxide to improve this are also disclosed. (See Non-Patent Document 1).

JP-A-6-343389 Japanese Patent No. 3329799 (JP-A-2002-142677) Japanese Patent No. 3342698 (JP-A-2002-238518) Japanese Patent No. 3338705 (Japanese Patent Application Laid-Open No. 2002-272373) JP-A-2002-238519 Kazuhiko Takashima, "Development of New Favorite Green Tea Can Drinks", News from Miyazaki Prefectural Agricultural Experiment No. 136, 2000, pp. 43-44

  An object of the present invention is to provide a catechin-containing food or drink that contains catechin at a high concentration, is excellent in taste and aroma, and preferably does not generate secondary dust after production, from a new viewpoint.

The present invention contains ester-type catechins (-) EGCg, (-) ECg, (-) GCg and (-) Cg in total of 70% by weight or more of the total content of all catechins, and A catechin-containing food or drink characterized by satisfying the conditions (1) to (3) is proposed.
(1) The total content of (−) GCg and (−) Cg is 40% by weight of the total content of (−) EGCg, (−) ECg, (−) GCg and (−) Cg which are ester catechins. % Or more.
(2) The content of (-) ECg is 20% by weight or less of the total content of (-) EGCg, (-) ECg, (-) GCg, and (-) Cg, which are ester catechins.
(3) The content of (-) GCg is not less than the content of (-) ECg.

The present inventors have conducted intensive studies on the pharmacological activity of catechins, and found that all four ester-type catechins have excellent pharmacological activities related to serum cholesterol lowering effect and the like. It was also found that if only catechins were included in food and drink, the flavor was insufficient and it was difficult to take food and drink. Therefore, in the present invention, the food and drink are configured such that the ester-type catechin accounts for 70% by weight or more of the total content of all catechins.
In addition, among the ester-type catechins, (-) GCg and (-) Cg, which are non-epi isomers, have better pharmacological activity related to serum cholesterol lowering effect and the like than the epi-isomer. Therefore, the total content of non-epi-forms, especially (-) GCg and (-) Cg, is determined so as to account for at least 40% by weight of the total content of ester-type catechins.
Furthermore, since the pharmacological activity related to the serum cholesterol lowering effect of ECg is the smallest among ester-type catechins, the content of (−) ECg is set to 20% by weight or less of the total content of ester-type catechins. .
On the other hand, since the pharmacological activity of (-) GCg relating to the serum cholesterol lowering effect and the like is the best among the ester-type catechins, it is necessary to compensate for the low pharmacological activity of (-) ECg by the effect of (-) GCg. , (-) GCg content is set to be equal to or more than (-) ECg content.

  A catechin-containing food or drink satisfying the above conditions has excellent pharmacological activity of catechin, particularly excellent pharmacological activity related to serum cholesterol lowering effect and the like, and also has excellent nourishment and aroma. Alternatively, it can be provided as a diet beverage or the like.

Furthermore, when the content (concentration) of strictinin in catechin-containing foods and drinks, particularly beverages, is set to 6 ppm or less, a catechin-containing beverage free of secondary odor can be obtained.
In tea beverages and the like, the problem that floc-like (cotton-like) suspensions / sediments (referred to as “secondary drips”) occur during storage after production has been a problem for many years. Found that strictinin was the causative agent. That is, "Strictinin" in the tea extract is heated and decomposed into "Elagic acid", and this "Elagic acid" binds to "protein" or the like (which may also include catechin) and is secondary. It was confirmed that slime was formed, and further, it was confirmed that secondary slime was not generated when the strictinin concentration in the beverage was 6 ppm or less.

As a method for producing the catechin-containing food and drink of the present invention, a catechin solution containing a total of 500 mg / L or more of (-) EGCg, (-) ECg, (-) GCg and (-) Cg, which are ester-type catechins, is used. A production method is preferred, in which the composition is prepared, heat-treated at 80 ° C. or higher, concentrated and dried.
Alternatively, the catechin solution prepared as described above may be subjected to a heat treatment at 80 ° C. or higher, then concentrated and dried, and the resulting concentrated and dried product may be added to food or drink or food or drink material.
Furthermore, a catechin solution containing a total of 500 to 6000 mg / L of ester-type catechins (-) EGCg, (-) ECg, (-) GCg, and (-) Cg was prepared, and heat-treated at 80C or higher. It may be manufactured as follows.

(−) GCg and (−) Cg are epimers of (−) EGCg and (−) ECg, that is, diastereomers having a configuration in which one asymmetric carbon atom of (−) EGCg and (−) ECg is inverted. (All stereoisomers other than enantiomers). These (−) GCg and (−) Cg are only slightly contained in natural products (for example, tea leaves), but are often contained in natural products (for example, tea leaves) in large amounts (−) EGCg and (−). ECg can be obtained by thermal isomerization.
Therefore, in any of the above-mentioned production methods, a catechin solution containing ester-type catechins at a predetermined value or more is prepared and heat-treated to promote thermal isomerization of (−) EGCg and (−) ECg. The content of (-) GCg and (-) Cg can be increased.

In this specification, “food and drink” is a general term for foods and drinks, that is, foods and drinks, and includes foods and drinks.
“Food and drink” means a beverage or food as a product, and “food and drink material” means a constituent material of the food and drink.
“Ester-type catechins” include four types of catechins having gallate groups of (−) EGCg, (−) ECg, (−) GCg and (−) Cg, and free catechins having no gallate group. Can be distinguished.
“Epi-isomer” means (−) EC, (−) EGC, (−) ECg, and (−) EGCg, and “non-epi-isomer” means (−) C, (−) GC, (−) Cg and (-) GCg are meant.
The “all catechins” include eight kinds of (−) EC, (−) EGC, (−) ECg and (−) EGCg, (−) C, (−) GC, (−) Cg and (−) GCg. Catechin.
The term “the active ingredient” of “the active ingredient of (−) GCg, (−) Cg or a mixture thereof” means that the serum cholesterol lowering action of (−) GCg or (−) Cg is not inhibited. It includes the meaning that other components such as (-) EC, (-) ECg, (-) EGCg and the like may be contained.
Further, a polymer of (−) GCg, a copolymer of (−) GCg and another catechin, a polymer of (−) Cg, or a copolymer of (−) Cg and another catechin is “( −) GCg, (−) Cg or a mixture thereof ”.
In addition, the numerical range specified by the present invention is equivalent to the numerical range even if it deviates from the upper limit and the lower limit as long as it has the same operation and effect as the numerical range. Includes the meaning to include.

  Next, an embodiment of the present invention will be described.

(First embodiment)
The amount of “(−) GCg, (−) Cg or a mixture thereof” is finally adjusted to a desired concentration, and any food or drink (including water) or food or drink material (including water) The catechin-containing food / drink of the present invention can be produced by adding the catechin to the food. It is possible to appropriately mix other components or perform other processing.

(−) GCg and (−) Cg can be obtained by a conventionally known method or a method known in the future.
Although (-) GCg and (-) Cg are hardly present in natural plants including tea leaves, for example, "(-) EGCg, (-) ECg or a mixture thereof" is subjected to heat treatment at 80 ° C. or higher. It can be obtained by isomerization (epimerization).
Therefore, “(−) GCg, (−) Cg or a mixture thereof” is, for example, “(−)” such as purified (−) EGCg or (−) ECg or a mixture thereof, or a tea extract or infusion. A catechin solution containing EGCg and (−) ECg ”is heated at 80 ° C. or higher to promote thermal isomerization of catechin, thereby increasing the concentration of (−) GCg or (−) Cg. It can be obtained by separating and purifying (-) GCg, (-) Cg or a mixture thereof, or a mixture containing these at a high concentration from the heat-treated product.
At this time, it is preferable to heat the catechin solution after adjusting the pH to 5 to 6. At a pH of 4.5 or less, catechin may hardly be thermally isomerized (Seto et al .: Biosci. Biotech. Biochem. 61 (9), 1434 (1997)).

  The composition of the “catechin solution containing (−) EGCg and (−) ECg” catechin solution is preferably prepared so as to contain a total of 500 mg / L or more of ester-type catechins. For example, it is preferable to prepare (-) EGCg and (-) ECg so as to contain 200 to 6000 mg / L, more preferably (-) EGCg and (-) ECg at 300 to 3000 mg / L.

  As a method for separating and purifying “(−) GCg, (−) Cg or a mixture thereof”, a conventionally known method or a method known in the future can be adopted. As an example, the liquid to be treated (eg, a tea extract) is subjected to, for example, reverse-phase HPLC using a mixed solution of water-acetonitrile-phosphoric acid as a mobile phase, and a gradient is applied at an acetonitrile concentration to obtain (−) GCg and ( -) Each Cg can be separated.

  "(-) GCg, (-) Cg or a mixture thereof" can be blended as a single active ingredient, respectively. However, other catechins such as (-) EC, (-) ECg, (-) EGCg It can be mixed with any food or drink (including water) or food and drink material (including water) in a state of being mixed with any one or a mixture of two or more of these.

"Food and drink materials" to be blended include water, carbonic acid, excipients (including granulating agents), diluents, and also sweeteners, flavors, flour, starch, sugars, fats, and other proteins, and carbohydrate raw materials. And one or more selected from food and drink materials such as vitamins and minerals. For example, the catechin-containing beverage may be dissolved in purified water or physiological saline to a desired concentration.
On the other hand, as the "foods" to be blended, currently known foods and drinks, for example, sports drinks, fruit drinks, milk drinks, tea drinks, vegetable juices, milky drinks, alcoholic drinks, jelly, jelly drinks, carbonated drinks, chewing gum, Chocolate, candy, biscuits, snacks, bread, dairy products, fish paste products, animal meat products, frozen desserts, dried foods, supplements and the like can be mentioned. Above all, if a food or drink is prepared by adding (-) GCg, (-) Cg, or a mixture thereof, or a catechin solution containing the mixture to a food or drink containing a large amount of fat, cholesterol may be added to the amount of fat contained. Therefore, it can be provided as a low-cholesterol food or drink or a diet food or drink.

(Second embodiment)
Next, a method for producing the catechin-containing beverage of the present invention from tea will be described.

As described above, (-) GCg and (-) Cg hardly exist in natural tea, but (-) EGCg, (-) ECg, or a mixture thereof, which is contained in natural tea in a large amount, is determined. It can be obtained by performing a heat treatment at a temperature not lower than the temperature.
Therefore, a “catechin solution” containing desired amounts of (−) EGCg, (−) ECg, (−) GCg, and (−) Cg (may contain other than these) is prepared, and this is prepared at a desired temperature. By performing the heat treatment, a catechin-containing beverage containing desired amounts of (−) GCg and (−) Cg can be produced.
For example, a tea extract (containing (−) EGCg and (−) ECg) obtained by extracting tea is added to water or the like in a predetermined amount, and (−) EGCg, (−) ECg, (−) GCg and ( −) A “catechin solution” containing desired amounts of Cg (or may contain other than these) is prepared and heated at a desired temperature to obtain (−) GCg and (−) Cg in desired amounts. A tea-derived catechin-containing beverage having a desired composition can be produced.

  At this time, the “tea” as a raw material is not particularly limited as to its type and site as long as it contains (−) EGCg and (−) ECg. For example, raw tea leaves, fermented teas such as black tea and pu-erh tea, semi-fermented teas such as oolong tea and wrapping tea, unfermented teas such as green tea, pot-roasted green tea, and roasted tea, or two or more of these Or a mixture of those obtained by extracting each mixture.

  Extraction of tea is performed by extracting tea with water, hot water or hot water, preferably hot water at 40 ° C to 100 ° C, especially hot water at 90 to 100 ° C, or an organic solvent such as an aqueous ethanol solution or ethanol harmless to the human body. Tea extract. The tea extract is further purified by a solvent extraction method, a resin adsorption method, a filtration method such as ultrafiltration or reverse osmosis filtration, etc., in a direction to increase the content of catechins, especially (−) EGC and (−) ECg. To obtain a tea extract. At the time of extraction, hydrochloric acid or the like may be added to increase the content of (−) EGC and (−) ECg, and extraction may be performed under acidic conditions.

  Also, a commercially available tea extract can be used. For example, theafuran 30A (trade name; manufactured by Itoen) or theafran 90S (trade name; manufactured by Itoen) can be preferably used. Theafuran 30A is a green tea extract obtained by subjecting green tea to hot water extraction and drying the extract to have a catechin concentration of 30%. Theafran 90S is an extract obtained by subjecting green tea to hot water extraction. It is a green tea extract having a tea polyphenol concentration of 85 to 99.5%, separated by an adsorption column using water and low and high concentration alcohols and dried. In addition, as a commercially available tea extract, "Polyphenon" manufactured by Mitsui Norin Co., Ltd., "Sunphenon" manufactured by Taiyo Kagaku Co., Ltd., "Sunoolon" manufactured by Suntory Ltd., etc. can be used.

The composition of the “catechin solution” is preferably prepared so as to contain a total of 500 mg / L of ester-type catechins. For example, it is preferable to prepare (-) EGCg and (-) ECg so as to contain 200 to 6000 mg / L, more preferably (-) EGCg and (-) ECg at 300 to 3000 mg / L.
If the concentration of the ester-type catechins in the catechin solution is less than 500 mg / L, a concentration step is required on the way, so that the production cost may be excessive.

The heat treatment of the catechin solution is preferably performed at 80 ° C. or higher. Looking at the test results, for example, heating at 100 ° C. × 15 minutes, heating at 115 ° C. × 20 minutes, heating at 120 ° C. × 3 to 30 minutes, heating at 123 ° C. × 10 minutes, heating at 131 ° C. × 30 seconds, and heating at 133 ° C. × 45 seconds In all cases, thermal isomerization of catechin has been observed.
If the heat treatment of the catechin solution is lower than 80 ° C., conversion of the ester-type catechins from an epi-isomer to a non-epi-isomer (thermal isomerization) does not easily occur, and the equilibrium shifts in the direction of the epi-isomer.
Preferably, the catechin solution is adjusted to pH 5 to 6 and then heat-treated. It has been reported that catechin may hardly thermally isomerize at a pH of 4.5 or less (Seto et al .: Biosci. Biotech. Biochem. 61 (9), 1434 (1997)).

The heat-treated solution of the catechin solution obtained as described above can be used as a catechin-containing beverage product as it is, but the product is prepared by appropriately adding a green tea extract and other substances to improve the flavor. You can also.
In addition, the catechin-containing beverage of the present invention can also be produced by further concentrating and drying the heat-treated solution of the catechin solution obtained as described above and blending the obtained solid. The concentration / drying step at this time can be performed by a usual concentration / drying method such as concentration under reduced pressure or freeze drying.

  The catechin foods and drinks obtained as described above use natural ingredients, especially ingredients obtained from tea, which are cited in large quantities on a daily basis. It can be provided as food and drink.

(composition)
A preferred composition of the catechin food and drink of the present invention is such that the ester-type catechins (-) EGCg, (-) ECg, (-) GCg and (-) Cg in total account for 70% by weight of the total content of all catechins. It contains above and satisfies the following conditions (1) to (3).
(1) The total content of (−) GCg and (−) Cg is 40% by weight of the total content of (−) EGCg, (−) ECg, (−) GCg and (−) Cg, which are ester catechins. % Or more.
(2) The content of (−) ECg is 20% by weight or less of the total content of (−) EGCg, (−) ECg, (−) GCg, and (−) Cg, which are ester catechins.
(3) The content of (-) GCg is not less than the content of (-) ECg.

As a result of the study by the present inventors, it was revealed that four types of ester catechins have a serum cholesterol lowering effect. However, if it is attempted to use only ester-type catechins, the flavor will be insufficient, and it will be difficult to ingest. Therefore, in order to improve the difficulty of ingestion by adding the green tea extract to make the concentration of (-) GC in the food and drink approximately twice as high as that of a commercially available green tea beverage, it is necessary to use the green tea extract. The amount added is at most about the same as the total catechin content of the food or drink. Therefore, the total content of the four ester-type catechins in the serum cholesterol-lowering food or beverage of the present invention is preferably 70% by weight or more of the total content of all eight catechins.
Furthermore, since the serum cholesterol lowering effect of the non-epi form is superior to that of the epi form (which has a certain effect), the non-epi form, especially the total content of (−) GCg and (−) Cg is reduced to the epi form Occupies at least 40% by weight of the total content of ester-type catechins including
Further, since the serum cholesterol lowering effect of ECg is the smallest among ester catechins, the content of (−) ECg is preferably 20% by weight or less of the total content of ester catechins.
Further, in order to compensate for the low serum cholesterol lowering effect of ECg with the GCg having the highest reduction effect, the content of (−) GCg is preferably equal to or more than the content of (−) ECg.
The serum cholesterol-lowering food and drink of the present invention that satisfies the above conditions exhibits a serum cholesterol lowering effect equal to or higher than that of food and drink containing the same amount of EGCg as the total amount of the ester-type catechin.

Furthermore, it is preferable that the concentration of strictinin in foods and drinks, specifically, beverages is 6 ppm or less.
“Strictinin (1-O-galloyl-4,6-O- (S) -hexahydroxydiphenoyl-β-D-glucose)” is a type of tannin extracted from tea, more specifically, a kind of ellagitannins (“Casuariin”). , Stachyurin and Strictinin, new Ellagitannins from Casuarina Stricta and Stachyurus Praecox ", Chem. Pharm. Bull. 30 (2) 766-769 (1982)).
The present inventor has found that there is a close correlation between the strictinin concentration in the liquid and the secondary ori, and the `` strictinin '' in the liquid is decomposed into `` ellagic acid '' by heat sterilization. Has been found to combine with “proteins” and the like to form secondary ori. We have also found that the strictinin concentration (content) differs depending on the source tea leaves, the place of harvest, the method of harvesting, etc., and that the strictinin concentration (content) in the beverage decreases regardless of the amount of the catechin solution. In order to do this, it is considered that the method of selecting an appropriate raw material (tea) is currently the most reliable method.
The amount of strictinin in the liquid can be measured by high performance liquid chromatography (HPLC) or the like.

(Necessary intake and content)
It is considered that the required intake of ester-type catechins in the catechin-containing food and drink of the present invention is preferably about 300 to 2100 mg per day.
Although it depends on the method of use, it is preferable that (-) GCg, (-) Cg or a mixture thereof is ingested in an amount of about 120 to 2100 mg, preferably about 250 to 1500 mg per day per adult in terms of dry weight.

Considering the above required intake, when the catechin-containing food and drink of the present invention is in a solid form, it is preferable to contain the ester-type catechins in an amount of 0.1 to 100% by weight, among which (-) GCg, (-) Cg or a mixture thereof is preferably incorporated in an amount of 0.04 to 100% by weight, particularly 0.1 to 40% by weight.
If the ester type catechins are less than 0.1% by weight, the amount of solids to be ingested may exceed 2 kg per day, which is not preferable.

On the other hand, when the catechin-containing food or drink of the present invention is in the form of a beverage, it is preferable to contain the ester-type catechins at a concentration of about 500 to 6000 mg / L, and (-) GCg, (-) Cg or a mixture thereof. Is preferably contained at a concentration of about 200 to 6000 mg / L, particularly about 300 to 3000 mg / L.
If the concentration of the ester-type catechins is less than 500 mg / L, the volume of the beverage to be consumed may exceed 4 L per day, which is not preferable. If it exceeds 6000 mg / L, the catechin concentration becomes high and the astringency is too strong, which is not preferred. More preferably, the concentration of the ester-type catechins is about 750 to 3750 mg / L.

<Test 1>
The ability of catechin to inhibit cholesterol absorption was measured, and the ability of isomerized catechin to inhibit cholesterol absorption was compared.

  Among tea catechins, (-) EGCg, (-) ECg, (-) GCg and (-) Cg as ester catechins, and (-) EGC, (-) EC, (-) GC and (-) as free catechins. The following tests were performed using a total of eight catechins C) as samples.

(Test method)
0.5 mM cholesterol, 6.6 mM Na taurocholate, 0.6 mM egg yolk lecithin and 132 mM NaCl were added to a 15 mM phosphate buffer (pH 6.8), and bile acid mixed micelles were prepared by sonication.
The bile acid micelles were sealed with argon gas, kept at 37 ° C. for 24 hours to stabilize the micelles, and then dissolved in deionized water to dissolve the eight catechins in a final concentration of 1000 μM or 2000 μM, respectively. And incubated for 1 hour. At this time, the micelle solution became cloudy and precipitated in some catechin-added groups. In addition, only the deionized water was added to the catechin-free group.
One hour after the start of the incubation, this solution was filtered through a 220 nm filter to obtain a clear micelle solution, and the cholesterol concentration in this solution was measured. The results are shown in FIG. 1 and FIG.

(result)
Referring to FIG. 1, addition of (-) EGCg, (-) ECg, (-) GCg and (-) Cg, which are ester-type catechins, to bile acid micelles depends on the amount of cholesterol in micelles in an amount dependent on the amount of addition. Reduced. The effect of (−) EGCg, (−) GCg, and (−) Cg showed a stronger lowering effect than that of (−) ECg when 1000 μM was added (P <0.05).
Among the former three catechins, (−) GCg has the strongest effect of lowering, significantly lowers (P <0.05) than (−) EGCg, and then (−) Cg, (−) EGCg. It was in order.
On the other hand, looking at FIG. 2, free catechins (−) EGC, (−) EC, (−) GC and (−) Cg hardly reduced the cholesterol concentration in the bile acid micelles.

(Discussion)
As a result, it was revealed that the gallate ester of catechin not only epi-form but also isomer precipitates cholesterol in the bile acid-mixed micelle and removes it from the micelle.
Furthermore, it can be considered that the isomers (-) GCg and (-) Cg have stronger effects than the epi-forms (-) EGCg and (-) ECg.

<Test 2>
In order to examine the synergistic effect of the isomerized catechin mixture, using the same method as in Test 1, an ester-type catechin mixture containing (-) GCg and (-) Cg (a drink of Example 1) and an ester-type catechin mixture containing no (-) GCg and (-) Cg (Theafuran 90S) and the effect of EGCg on inhibiting cholesterol absorption of the three were shown in FIG. 3 and compared.

The beverage of Example 1 below was used as an ester-type catechin mixture containing (-) GCg and (-) Cg, and bile acid-mixed micelles were prepared from this example beverage in the same manner as in Test 1.
In addition, bile acid-mixed micelles from this example beverage were used in the same manner as in Test 1 using theafran 90S (green tea extract manufactured by ITO EN, see Table 1 for composition) as an ester-type catechin mixture containing no (-) GCg and (-) Cg. Was prepared.

  As a result, it was found that a mixture of ester-type catechins, that is, a mixture containing (−) GCg and (−) Cg, exhibited higher activity than EGCg.

<Test 3>
Theafuran 90S (Catechin extract manufactured by ITO EN, see Table 1 for composition) was dissolved in warm water at 60 ° C. to a concentration of 1450 mg / L, cooled to 35 ° C., added with 300 mg / L of vitamin C, and then cyclodextrin was added. 1% by weight, 0.2% by weight of green tea extract and 300 mg / L of sodium bicarbonate were added, and finally adjusted to 1 kg with distilled water to obtain a catechin solution. At this time, 250 mg of polyphenol was contained per can.
The catechin solution thus obtained is heated to 95 ° C. and then filled in a can and subjected to a heat treatment at 123 ° C. for 10 minutes, or after heating to 95 ° C., 133.5 ° C./45 After performing heat treatment for 2 seconds, the PET bottle was filled, the content of catechin in each step was measured, and the content (mg / L) of each was shown in Table 2, and the isomerization rate (change rate%) of catechin was shown. The results are shown in Table 3.

Here, when the contribution ratio of the (−) EGCg, (−) GCg, (−) ECg and (−) Cg in the beverage with respect to the cholesterol lowering effect was determined, from Test 1, it was found that (−) EGCg, (−) GCg, Since (-) ECg and (-) Cg have a residual cholesterol concentration in micelles of 272, 244, 337, and 262 at 100 μM, the precipitated cholesterol differs from the initial value of 425 μM by 153, 181 and 88. , 163, and the cholesterol precipitating ability per 1 μM is 1.53, 1.81, 0.88, 1.63.
On the other hand, the composition of catechin contained in 190 mL of the test beverage was (-) EGCg: (-) GCg: (-) ECg: (-) Cg = 51.3 mg (589.5 µM): 62.7 mg (720.5 µM). ): 19.0 mg (226.2 μM): Assuming 17.0 mg (202.4 μM), the contribution rate of catechin contained in 190 mL of the test beverage to the cholesterol-lowering effect from the cholesterol precipitation ability per 1 μM is as follows: (−) EGCg: (−) GCg: (−) ECg: (−) Cg = 33.0: 47.7: 7.3: 12.0 (%)

<Test 4>
1) Subjects The present study was conducted on 42 healthy subjects aged 20 years or older who had serum total cholesterol in the boundary region of 200 mg / dL to 280 mg / dL and mildly high serum cholesterol. Extracted by physicians who do not participate directly in
The subject must be a patient who has not been treated at the hospital, who has taken medications such as lipid-lowering drugs or antihypertensive drugs due to hospitalization or hospital visit, severe liver dysfunction, renal disorder, respiratory disorder, Individuals with endocrine and cardiovascular disorders were excluded from the study.
At the start of the test, 42 subjects were divided into three groups, Group A, Group B, and Group C, and each group had 14 subjects. There were no differences in blood pressure or total cholesterol levels in each group at the start.

2) Test Beverage In this test, 190 g of a beverage containing 150 mg of tea catechin (250 mg as a tea polyphenol: trade name Tearfuran 90S, manufactured by Itoen Co., Ltd.) was used. Table 4 shows the tea catechin composition in the test beverage.
To the test beverage, tea catechin, green tea extract containing no tea catechin, cyclodextrin, and vitamin C were added.
In addition, drinks of the same components other than tea catechin were used as placebo drinks.

3) Test schedule The test was performed by a double blind method. The test schedule is shown in FIG. All groups performed blood tests at the beginning and end of each period.
Group A received three control drinks per day, group B received two test drinks per day, and group C received three test drinks per day. Each group was fed one by one with meals.
In addition, in Group B, one control drink was ingested only at lunch, in order to match the total daily intake other than tea catechin with Groups A and C.

4) Observation items Total cholesterol (TC), HDL-cholesterol (HDL-C), LDL-cholesterol (LDL-C), and neutral fat (TG) were measured as serum lipids for all subjects.
TC, HDL-C and TG were measured by an enzymatic method. LDL-C was calculated by the formula of Friedewa1d et al. (LDL-C = TC-HDL-C-TG / 5).
In order to confirm the health status, BUN, uric acid, total protein, ALP, GOT, GPT, LDH, γ-GTP, CPK, Na, K, Ca, Cl, Fe, UIBC, ferritin, HbA ₁ c, hemoglobin, erythrocyte The number, white blood cell count, platelet count and hematocrit were measured. In addition, a meal survey and a locomotor activity survey were performed for three days before each blood sampling. The subjects were asked to fill out a meal questionnaire, and the nutrition was calculated according to the "Fiveth Edition Japanese Food Standard Composition Table". As for the amount of exercise, a pedometer (registered trademark) was distributed to all the subjects, and the total number of steps per day was entered.
The blood was collected on an empty stomach in the early morning. On each blood collection day, a medical examination was performed by a doctor to observe changes in physical condition.

5) Statistical analysis Each measured value was shown as an average value ± standard deviation. Analysis of significance was performed using a SAS statistical analysis program with a risk factor of less than 5%.
In the test of each measured value, when normality was recognized, a multiple comparison test (Dunnett method) was performed. When normality was not recognized, the test was performed by the Stea1 method.

6) Results (1) Nutrient intake and exercise The daily nutrition intake and exercise during the test period are shown in Table 5. The diet survey and the exercise amount survey were shown as the average values of three days before each blood sampling and on weekdays. The average value of the energy intake was low as 1638 to 1846 kcal / day throughout, but as a result of interviews with the doctors, all subjects were occupants. It was also determined that there was a tendency to eat more with alcohol on holidays.
There was no significant difference in energy intake between each group. At 4 weeks after the start of ingestion, the cholesterol intake was significantly lower in group C (106.1 ± 95.6 mg / d1) than in group A (198.O ± 69.3 mg / d1), but it was generally temporary. The level of cholesterol intake was not immediately reflected in the serum cholesterol level, and in fact, there was no difference in the serum lipid concentration of each group at this time, so it was considered that there was no particular effect. No difference was observed in the nutrient intake and exercise amount of each of the other subjects.

(2) Serum lipid Table 6 shows changes in serum lipid-related test values during the test period. In group C (3 bottles / day), the TC value was 226.9 ± 20.2 mg / dl (at the start of ingestion) to 203.0 ± 22.7 mg / dl (after 8 weeks), which was significant (ρ <O.05 by Dunnett-test).
The TC value of group A (control drink group) 8 weeks after the start was also significantly (ρ <0.01) lower than the TC value of 236.0 ± 19.1 mg / dl. Similarly, the LDL-C value also decreased significantly (ρ <0.01) from 141.6 ± 22.3 mg / dl (at the start of ingestion) to 116.9 ± 14.4 mg / dl (after 8 weeks) at the start of ingestion. The LDL-C value of the group A (control drink group) after a week was also significantly (ρ <0.01) lower than the LDL-C value of 147.3 ± 22.3 mg / d1.
In the B group (2 bottles / day), the TC value also changed from 236.O ± 25.8 mg / d1 (at the start of ingestion) to 219.1 ± 21.Omg / d1 (after 8 weeks). The TC value of the group A (control drink group) tended to be lower than the TC value of 236.0 ± 19.1 mg / d1 (ρ <0.1). On the other hand, HDL-C, TG, and each value of HbA ₁ c B group, significant difference as compared to the beginning ingestion with C group was not observed. No significant difference was observed with respect to Group A (control drink group).

(3) Blood components / minerals and other findings Table 7 shows changes in blood components and minerals of the test subjects. During the intake period, there were no significant changes in the red blood cell count, white blood cell count, platelet count, hemoglobin, hematocrit, ferritin, and each of Fe, Ca, K, Cl, and Na compared to those at the start of both groups B and C. I was not able to admit.
No significant difference was observed between the groups.
After the follow-up period, a significant (ρ <0.01) increase in Na in group C (141.7 ± 1.3 mg / d1 → 143.4 ± 1.3 mg / d1) compared to that at the start of ingestion was significant in Ca in group B (ρ <0.01). <0.05) (4.7 ± 0.2 mg / d1 → 4.9 ± 0.1 mg / d1), but both were within the normal range, and were judged to be medically acceptable by a physician.
During the test period, no significant change was observed in γ-GTP, GOT, and GPT, and no findings considered to be adverse events were observed at the doctor's visit.

7) Discussion In this test, two or three drinks containing 250 mg of tea polyphenol and 150 mg of tea catechin (EGCg51.3 mg, GCg62.7 mg, ECg19.Omg, Cg17.0 mg) per day were given to each subject. For 8 weeks. Therefore, the daily intake is 500 mg of tea polyphenol and 300 mg of tea catechin (EGCg 102.6 mg, GCg 125.4 mg, ECg38.Omg, Cg34.Omg) in group B, 750 mg of tea polyphenol and 450 mg of tea catechin (EGCg153 in group C). .9 mg, GCg 188.1 mg, ECg57.Omg, Cg51.Omg). The daily intake of 450 mg of tea catechin in the group C corresponds to the amount of tea catechin for 8 to 9 cups of normal green tea.
Ingested catechins form insoluble precipitates with dietary cholesterol, endogenous cholesterol excreted in the intestinal tract and cholesterol in bile acid micelles, thereby inhibiting cholesterol absorption from the small intestine and causing bile acids and cholesterol in the feces. Is excreted. In particular, ester-type catechins have a higher ability to release cholesterol from bile acid micelles than other catechins.Therefore, the effect of this beverage mainly containing ester-type catechins is due to inhibition of cholesterol absorption from the intestinal tract. It is presumed that there is.
In addition, it is known that tea catechin changes intestinal flora, such as by growing intestinal lactic acid bacteria. Dietary fiber derived from diet is easily assimilated by lactic acid bacteria and the like, and as a result, the amount of propionic acid produced increases. It has been reported that the produced propionic acid inhibits hepatic HMG-CoA synthase activity and suppresses cholesterol synthesis. Introductory contributions are also conceivable. That is, during the period of tea catechin intake, 1) inhibition of reuptake of endogenous cholesterol excreted in the intestinal tract, 2) inhibition of cholesterol synthesis caused by growth of lactic acid bacteria, 3) cholesterol caused by bile acid being inhibited by intestinal circulation. It is thought that the endogenous cholesterol pool is reduced and the cholesterol saturation in bile is also reduced due to the increased synthesis of cholesterol into bile acids. It is considered that after the end of tea catechin intake, the endogenous cholesterol pool recovers and bile acid synthesis decreases, and then excess endogenous cholesterol flows out into the blood, leading to an increase in serum cholesterol level. However, taking into account that it takes 4 weeks after the start of tea catechin intake until the decrease in serum cholesterol level becomes remarkable, it takes some time for the serum cholesterol level of the subject to return before the start of intake. It is presumed that there was a delay.
On the other hand, in this test, no decrease in serum mineral level due to tea catechin was observed. In addition, there were no significant changes in serum iron, UIBC, hemoglobin, and hematocrit.
This result is consistent with the report by Record et al. That tea consumption does not affect the absorption of trace metal elements. Therefore, although this study was conducted for 8 weeks, it was confirmed that ingestion of a tea beverage containing tea catechin could be ingested for a long period of time without lowering the serum mineral values.

<Test 5: Sensory test>
In a sensory test, a panel of ITO EN Co., Ltd. conducted a preliminary test on whether or not the astringent taste of tea and astringent taste could be identified in advance, and then selected 10 men and women each. In order to avoid the influence, the mixture was poured into a red glass and given to the panel, and evaluated by a 1 to 5 (higher is better palatability) scoring method.

  Catechin-containing beverage: A beverage obtained by dissolving the theafran 90S and tea extract extract in warm water was retorted at 123 ° C for 10 minutes after filling in a can, and refrigerated at 10 ° C was subjected to a panel test.

  Beverage A: A 200 mL can filled with a catechin solution obtained by dissolving the above-mentioned theafuran 90S in warm water and refrigerated at 10 ° C, and a retort treatment at 123 ° C for 10 minutes after filling the can, followed by cooling to 60 ° C and further cooling to 10 ° C. Refrigerated at ℃ was tested.

  Beverage B: 200 mL can of a catechin solution obtained by dissolving the above-mentioned theafuran 90S and polyphenone 60 (manufactured by Mitsui Norin Co., Ltd.) in warm water such that the ester-type catechins account for 70% by weight of all catechins. And refrigerated at 10 ° C, and after retort treatment at 123 ° C for 10 minutes after filling the can, cooled to 60 ° C and further refrigerated at 10 ° C.

  Beverage C: 200 mL of a catechin solution obtained by dissolving the above-mentioned theafuran 90S and polyphenone 60 (manufactured by Mitsui Norin Co., Ltd.) in warm water such that the ester-type catechins account for 50% by weight of all catechins. And refrigerated at 10 ° C, and after retort treatment at 123 ° C for 10 minutes after filling the can, cooled to 60 ° C and further refrigerated at 10 ° C.

  Table 8 shows these analytical values. Table 9 shows the results of the panel test.

  As a result of the panel test, in the evaluation combining ease of drinking and astringency, the evaluation decreased slightly as the ratio of ester catechins to all catechins decreased. All samples having 70% by weight or more were evaluated as good.

<Test 6 Test for strictinin>
This test was conducted to observe the correlation between the strictinin content in beverages and the occurrence of slime.

1. Beverage preparation 1) Sample No. of test 1 In the same method for producing the raw tea leaves as in No. 5, the conditions of humidity control and kneading were adjusted, and the strictinin concentration of the tea beverage and the occurrence of secondary dust were confirmed using the obtained raw tea leaves.
That is, 20 g of each raw tea leaf sample was extracted with 800 ml of 70 ° C. distilled water (pH 5.9) for 3.5 minutes, and the residue was removed with a mesh (150 mesh). After rapidly cooling to room temperature and centrifuging (7000 rpm, 10 minutes) to remove the insoluble fraction, 300 ppm of L-ascorbic acid was added to the amount of the mess, and the pH was adjusted to 6.0 with sodium bicarbonate. The whole was made up to 2000 ml with distilled water.
2) The obtained preparation was sterilized by UHT at 133 ° C. to 135 ° C. for 30 seconds, filled in a PET bottle, and rapidly cooled to obtain a packaged tea beverage.

2. Measurement and analysis of each item 1) Strictinin content The strictinin contents of Sencha A to D prepared by extracting four types of raw tea leaves into hot water and the above-mentioned aqueous solution of theafuran 90S were measured. The prepared green tea and theafuran aqueous solution were stirred and treated with a 0.45 μM filter, and then the strictinin concentration was measured by high performance liquid chromatography (HPLC) under the following conditions (HPLC conditions, Table 10). The measurement results are shown in Table 11 below.

(HPLC conditions)
Equipment: Hitachi D-7000 Advanced HPLC, D-7000 Advanced HPLC System Manager Column: Wakosil-II5C18HG φ4.6 × (30 + 250) mm
Column temperature: 40 ° C
Flow rate: 0.6 ml / min
Detection: UV280
Mobile phase A: 15% MeOH (0.1% phosphoric acid)
Mobile phase B: 45% MeOH (0.1% phosphoric acid)

2) Occurrence of Deposits Stored at 37 ° C., and visually checked after 1, 6, 8, 12, and 15 days. Table 11 shows the results.

(Example 1)
Theafran 90S (green tea extract manufactured by ITO EN, see Table 1 for composition) was dissolved in warm water at 60 ° C. to a concentration of 1450 mg / L, cooled to 35 ° C., added with 300 mg / L of vitamin C, and then cyclodextrin. Was added at 1% by weight and baking soda at 300 mg / L, and finally adjusted to 1 kg with distilled water to obtain a catechin solution. After heating the obtained catechin solution to 95 ° C., it was filled in a can and subjected to a heat treatment at 123 ° C. for 10 minutes to produce a catechin-containing beverage having the following composition.

Catechin 150mg
(-) GCg 62.7mg
(-) 51.3 mg of EGCg
(-) ECg 19.0mg
(-) Cg 17.0mg
Vitamin C 50mg
Cyclodextrin 500mg
Adjust the whole water to 190mL

  In this catechin-containing beverage, the catechins contained therein are all ester-type catechins (that is, 100% by weight), the concentration of the ester-type catechins is 789 mg / L, and “(−) GCg + (−) Cg” in the ester-type catechins. Is 53.1% by weight, and the percentage of (-) ECg is 12.7% by weight.

3 is a graph comparing the cholesterol absorption inhibitory effects of ester-type catechins (EGCg, GCg, ECg, Cg) in Test 1. 3 is a graph comparing the cholesterol absorption inhibitory effects of free catechins (EGC, GC, EC, C) in Test 1. It is a graph which compared the cholesterol absorption inhibitory effect of the isomerized catechin mixture, the ester type catechin mixture, and EGCg in Test 2. 9 is a graph showing a test schedule of Test 4. 9 is a graph showing the change over time in the total cholesterol concentration in Test 4. 9 is a graph showing the time-dependent change in LDL-cholesterol concentration in Test 4.

Claims (7)

(-) EGCg, (-) ECg, (-) GCg and (-) Cg, which are ester-type catechins, are contained in a total amount of 70% by weight or more of the total content of all catechins, and the following (1) to (1): A catechin-containing food or drink characterized by satisfying the condition (3).
(1) The total content of (−) GCg and (−) Cg is 40% by weight of the total content of (−) EGCg, (−) ECg, (−) GCg and (−) Cg, which are ester catechins. % Or more.
(2) The content of (−) ECg is 20% by weight or less of the total content of (−) EGCg, (−) ECg, (−) GCg, and (−) Cg, which are ester catechins.
(3) The content of (-) GCg is not less than the content of (-) ECg.   The catechin-containing food or drink according to claim 1, wherein the catechin-containing food or drink contains a total of 0.1 to 100% by weight of (-) EGCg, (-) ECg, (-) GCg, and (-) Cg, which are ester-type catechins.   The catechin-containing food or drink according to claim 1, wherein the catechin-containing food or drink contains a total of 500 to 6000 mg / L of (-) EGCg, (-) ECg, (-) GCg, and (-) Cg, which are ester-type catechins.   The catechin-containing food or drink according to any one of claims 1 to 3, which contains 6 ppm or less of strictinin.   A catechin solution containing a total of 500 mg / L or more of (−) EGCg, (−) ECg, (−) GCg, and (−) Cg, which are ester-type catechins, was prepared and heated at 80 ° C. or more. A method for producing a catechin-containing food or drink, comprising concentrating and drying.   Ester-type catechins (−) EGCg, (−) ECg, (−) GCg and (−) Cg, a catechin solution containing a total of 500 mg / L or more was prepared, heated at 80 ° C. or more, concentrated, and concentrated. A method for producing a catechin-containing food or drink, comprising drying and concentrating the obtained concentrated and dried product in food or drink or food and drink material. Ester-type catechins (-) EGCg, (-) ECg, (-) GCg, and (-) A catechin solution containing 500 to 6000 mg / L in total is prepared, and heat-treating this at 80C or higher. A method for producing a catechin-containing beverage.

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