JP4667101B2 - Novel uses of tetrasaccharides having a branched structure, inhibitors containing these saccharides as active ingredients - Google Patents

Description

  The present invention relates to a novel use of a 3-4 saccharide having a branched structure. More specifically, the present invention relates to a technique for suppressing the bitterness and astringency of catechins by 3-4 saccharides having a branched structure.

  Catechins, which are a type of polyphenol, are useful components contained in green tea. In recent years, research on the physiological effects of these catechins has been progressing rapidly. As a result of research, it has become clear that catechins have antioxidant, antibacterial, lipid metabolism improving, antihypertensive, antihyperglycemic, deodorant, antiallergic, etc. Yes.

  For this reason, for the purpose of increasing the intake of catechins or promoting the spread of continuous intake, various foods and drinks intentionally added and blended with catechins as a functional ingredient have begun to appear. Among these types of foods and beverages, tea beverages containing high concentrations of tea catechins have already been released.

  However, since catechins have peculiar bitterness and astringency, when the viewpoint of flavor balance is taken into consideration, there is no choice but to set a limit on the blending amount. This is an obstacle to the development of foods and drinks containing catechins.

Patent Document 1 proposes a technique for glycosylating catechins with CGTase. However, a dedicated facility is required for glycosylation of catechins, which takes time. In patent document 2, the technique using a cyclodextrin is proposed. Patent Document 3 and Patent Document 4 disclose techniques that can achieve reduction in astringency and bitterness of catechins by blending oligosaccharides and other sugars.
Japanese Patent Application Laid-Open No. 07-179489. Japanese Patent Laid-Open No. 10-4919. Japanese Patent Application Laid-Open No. 2005-058209. JP 2000-287630 A.

  Although the above-mentioned conventional technology has achieved the suppression of the bitterness and astringency of catechins to some extent, the degree of the effect is not sufficient, and it can be widely used as a technique for suppressing the bitterness and astringency of catechins. It was not a simple technique. Furthermore, in the conventional method of blending cyclodextrin, there is a problem that even the “umami” of tea is suppressed, and in particular in beverages, solving this problem is an important technical issue.

  Therefore, the main object of the present invention is to provide a simple general-purpose technology that can more effectively suppress the bitterness and astringency of catechins while maintaining the umami of tea.

  The inventors of the present application are pursuing thorough and detailed research on saccharides, particularly oligosaccharides, and the non-reducing saccharides and / or reducing saccharides containing 3-4 saccharides having a branched structure are the bitter taste of catechins. It has been found that it has an excellent action and function of suppressing the taste and astringency and not impairing the flavor of tea.

  Therefore, the present invention proposes to use a 3-4 saccharide having a branched structure for the purpose of suppressing the bitter taste and / or astringency of catechins. In addition, in this invention, all the structures which use or contain any one or both of trisaccharide and tetrasaccharide which have a branched structure are included.

  Moreover, this invention provides the inhibitor of the bitterness and / or astringency of catechin which uses 3-4 saccharides which have a branched structure as an active ingredient. The form of the inhibitor can be appropriately selected according to the use and purpose, and for example, forms such as liquid, powder, granule, paste, and emulsion can be adopted. Furthermore, this invention provides the catechin containing food / beverage products which contain 3-4 saccharides which have a branched structure as a flavor adjustment component.

  Here, key technical terms related to the present invention are defined.

  First, the “branched structure” refers to a linear structure consisting only of α-1,4 glucoside bonds, α-1,1 glucoside bond, α-1,2 glucoside bond, α-1, It means a structure having a bond other than an α-1,4 glucoside bond, such as a 3 glucoside bond or an α-1,6 glucoside bond.

  The “3-4 saccharide having a branched structure” means a trisaccharide or tetrasaccharide oligo provided with the branched structure in any sugar chain. For example, panose (maltose composed of isomaltotriose, isomalttetraose, α-1,4 glucoside bond and α-1,6 glucoside bond composed only of α-1,6 glucoside bond. Non-reducing terminal glucose of 3 sugars in which glucose is α-1,6 glucoside-bonded), isopanose (trisaccharide in which glucose is α-1,6-glucoside-bonded to reducing terminal glucose of maltose), isomaltotriosyl glucose, Widely includes trisaccharide or tetrasaccharide nigerooligosaccharide having one or more α-1,3 glucoside bonds, trisaccharide or tetrasaccharide koji oligosaccharide having one or more α-1,2 glucoside bonds, and the like The reduced product of the branched oligosaccharide is also included. In addition, it is estimated that 3-4 saccharides which have these branched structures suppress these flavors by exhibiting the inclusion effect with respect to the bitterness and astringency of catechins. In the present invention, these branched oligosaccharides may be used alone or in combination.

  The content of 3-4 saccharides having a branched structure in the saccharide or sugar composition is determined by the exclusion type ion exchange column for obtaining the degree of polymerization distribution and the ratio of the linear oligosaccharide to the branched oligosaccharide in each degree of polymerization. It can be measured by a high-performance liquid chromatography method using an amine-bonded silica column (Food Chemical Newspaper "Starch Sugar Related Industrial Analysis Method", p 131-138, 1991).

  The “non-reducing sugar” is a saccharide composition in which the aldose is positioned at the first position or the ketose is positioned at the second position, that is, the anomeric carbon atom is not substituted. It is.

  “Catechins” are a kind of flavonoids, and include 3-hydroxyflavan derivatives having a hydroxyl group at the 3-position and their oxidation and polymerization products. Among them, tea catechins contained in green tea are famous, and a total of eight types are known: catechin, epicatechin, gallocatechin, epigallocatechin, catechin gallate, epicatechin gallate, gallocatechin gallate, and epicatecatechin gallate.

  According to the present invention, the bitterness and astringency of catechins can be remarkably suppressed while maintaining the flavor of tea. As a result, since it is possible to dispel the concern about a decrease in flavor due to the blending of catechins, it becomes possible to promote the development of foods and drinks blended with catechins at a high concentration.

  First, the saccharide samples used in the following examples are shown in the following “Table 1”.

Glucose (trade name “Anhydrous Crystal Glucose” manufactured by Showa Sangyo Co., Ltd.), sorbitol (trade name “Sorbitol Nikken SP” manufactured by Nikken Chemical Co., Ltd.), Erythritol (trade name “Erythritol Eridex ^™ ” manufactured by Nikken Chemical Co., Ltd.) , Maltose (trade name “Sanmaruto S” manufactured by Hayashibara Co., Ltd.), maltitol (trade name “Malbit” manufactured by Nikken Chemical Co., Ltd.), trehalose (trade name “Trehal” manufactured by Hayashibara Co., Ltd.), β-CD (trade name) “Dexy Pearl β-100” (manufactured by Shisui Minato Sugar Co., Ltd.) was a commercial product. The carbohydrate was obtained by separation and purification from commercially available oligosaccharides. The branched oligosaccharide was obtained by fractionation and purification using Isomalt 900 (manufactured by Showa Sangyo Co., Ltd.).

  In any case, after fractionation treatment with a continuous preparative chromatograph manufactured by Organo, purification was repeated using an ODS preparative chromatograph manufactured by YMC, and the like, and the nonreduced sample having a purity of 90% or more was prepared. For this reduced product sample, the non-reduced sample is reduced according to a known method (see Starke 26 307-312.1974) and purified by the ODS preparative chromatograph to prepare a sample having a purity of 90% or more. Obtained.

  Using the saccharide sample shown in Example 1, a sensory evaluation test was conducted on the inhibitory effect on the bitterness and astringency of catechins and the remaining degree of umami.

  Various sugar samples were added to a commercial tea beverage containing 1.2 mg / ml catechin (trade name “catechin green tea”, manufactured by Sangalia Co., Ltd.) so as to be 5% by weight (in terms of solid content).

The sensory evaluation was performed by 7 skilled panelists. There are three evaluation items: bitterness suppression, astringency suppression, and umami residual. The evaluation was performed based on a relative evaluation with the “control group” in which the same amount of sugar was added to the tea beverage. Regarding the suppression of bitterness and astringency, “◯” indicates that there is a strong effect, “Δ” indicates that there is an effect, and “X” indicates that there is no effect.
As for the remaining umami, “◯” indicates that it has not been lost, “Δ” indicates that it has not been lost, and “X” indicates that it has been lost. Comprehensive evaluation is “◎” when 3 items are 3 out of 3 items, “○” when 2 items are ○, “△” when 1 item is 1 item, and × when 1 item is 1 item. The case where there was no evaluation item was marked as “x”. The evaluation results are summarized in the following “Table 2” (for non-reducing sugars) and “Table 3” (for reducing sugars).

  As can be seen from the evaluation results shown in Tables 2 and 3 above, the 3-4 saccharides having a branched structure and the reduced products thereof had bitterness and astringency suppressed, and umami remained. On the other hand, for monosaccharides, linear oligosaccharides with only α-1,4 glucoside bonds, and branched oligosaccharides with 5 or more saccharides having bonds other than α-1,4 glucoside bonds, the evaluation is equal to or less than that of the control group. In addition, β-cyclodextrin was effective in suppressing bitterness and astringency, but the decrease in umami was significant.

Test 1.
A green tea sample prepared by adding 0.02%, 0.04%, 0.08% of a commercially available catechin preparation (trade name: Sanphenon 100S, manufactured by Taiyo Chemical Co., Ltd.) to the commercially available tea beverage used in Example 2 was prepared. The relationship between catechin concentration and umami was confirmed. Moreover, 0.15% sodium glutamate was used as a positive control for umami. Umami was measured using a taste sensor.

  The taste sensor used was a taste identification device SA402B manufactured by Intelligent Sensor Technology. For the measurement, the output of each sample with respect to a standard solution of 30 mM KCl + 0.3 mM tartaric acid was measured using seven types of sensors. The measurement was performed 5 times in total, and the average value was converted from sensor output to umami in accordance with Weber's law.

  The measurement results are shown in FIG. As shown in FIG. 1, when the catechin preparation was added, the umami strength was increased in the same manner as when sodium glutamate was added. The increase was dependent on the addition concentration.

  Next, the effect of the addition of carbohydrates on umami was confirmed using a taste sensor.

  As the used saccharide, a saccharide sample containing 50% of a non-reducing 3-4 saccharide having a branched structure as a main component, β-cyclodextrin (trade name: Doxy Pearl high purity product β-100, Shimizu Minato Sugar Co., Ltd. Made).

Test 2.
“Control group” with no addition, “Example group” with 1.5% addition of non-reducing branched 3-4 sugars, and Comparative example group (β-CD group) with 0.5% addition of β cyclodextrin were measured. The results are shown in FIG. The lower the value on the vertical axis, the lower the taste. Compared to the control group, a significant decrease in umami components was confirmed in the β-CD addition group, whereas in the example group, the degree of umami decrease was small and the tea flavor remained excellent. It was considered to have the characteristics.

  Food evaluation test using “catechin-enhanced matcha jelly”.

  50 g of gelatin was sprinkled into 500 mL of water, and after expansion, dissolved in a microwave oven by heating for about 30 seconds. After adding 2000 mL of 70 ° C. hot water to this and mixing, 40 g of matcha tea dissolved in 300 mL of hot water and 2 g of a commercially available catechin preparation (trade name: Sanphenon 100S, manufactured by Taiyo Kagaku Co., Ltd.) were added and homogenized. 300 g of a saccharide sample containing 50% of a non-reduced 3-4 saccharide having a branched structure as a main component and 300 g of sugar were added and stirred, and poured into a container when thickening occurred. After cooling to room temperature, it was stored overnight in a refrigerator.

  When this was subjected to panel evaluation, it was highly evaluated that bitterness and astringency were suppressed and the umami of tea was felt.

  Food evaluation test using “Catechin-enhanced Matcha Mousse”.

  300 mL of water, 60 g of green tea, 1 g of catechin preparation (trade name: Sanphenon 100S, manufactured by Taiyo Chemical Co., Ltd.), 300 g of sugar, 200 g of a saccharide sample containing 50% of a non-reducing 3-4 saccharide having a branched structure as a main component, swelling 50 g of the gelatin thus prepared was dissolved by heating in a low heat, and cooled to a level where thickening occurred. To this was added 800 mL of milk, and meringue adjusted with 1 egg white and 100 g of sugar and whipped cream whipped with 1000 mL of fresh cream were added and lightly mixed. This was poured into a container and cooled in a refrigerator for 2 hours.

  When this was subjected to panel evaluation, it was highly evaluated that bitterness and astringency were suppressed and the umami of tea was felt.

  The present invention can be used as a technique capable of suppressing bitterness and astringency while leaving the umami of catechins. Inhibitors according to the present invention include tea beverages, fruit beverages, carbonated beverages, vegetable beverages, sports beverages, whey beverages, alcoholic beverages and other beverages, ice creams, jellies, mousses, candy sweets, gums containing catechins Can be blended into confectionery, fillings, health foods, supplements, etc.

It is a figure (drawing substitute graph which shows that umami intensity | strength increases according to the addition density | concentration of a catechin formulation) which shows the result of the test concerning Example 3. FIG. It is a figure which shows the result of the other test concerning Example 3 (drawing substitute graph which shows the result of having measured the umami intensity | strength in a "control group", an "Example group", and a comparative example).

Claims (4)

  A tetrasaccharide having a branched structure, which is composed of an α-1,1 glucoside bond, an α-1,2 glucoside bond, an α-1,3 glucoside bond, and an α-1,6 glucoside bond in a sugar chain. Inhibitors of bitterness and / or astringency of catechins containing as an active ingredient any one or more saccharides having a branched structure selected from the group consisting of   The inhibitor according to claim 1, comprising 50% or more of the active ingredient.   The inhibitor according to claim 2, comprising 90% or more of the active ingredient.   It is the method of suppressing the bitterness and / or astringency of the food / beverage containing catechin, Comprising: The bitterness and / or astringency which add the inhibitor of any one of Claims 1 thru | or 3 to the said food / beverage. Suppression method.

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