JP3054776B2 - Method for controlling sweetness of glycyrrhizin - Google Patents

Description

The present invention relates to a method for suppressing only the sweetness of glycyrrhizin without impairing its pharmacological action.

[Conventional technology]

Glycyrrhizin is a triterpene-based glycoside extracted from licorice, and it is used to improve the sweetness and taste of foods and beverages in the form of unrefined licorice extract because it exhibits a strong sweetness of about 200 times that of sugar. ing.

On the other hand, glycyrrhizin has anti-inflammatory, anti-allergic, anti-tumor, anti-viral, anti-fibrinolytic activities, and also has a complement inhibitory effect, detoxification effect, liver function improving effect, decholesterolizing effect, central nervous system inhibitory effect, It has many pharmacological effects, such as regulatory effects, sex hormone-like effects, and corticosteroid-like effects, and has been widely used as a material for herbal medicines and other medicines and so-called functional foods from an early age.

When glycyrrhizin is combined with food or drink or a drug to be orally administered in the expectation of the above-mentioned pharmacological action, the strong and lasting sweetness of glycyrrhizin does not need to be present, but rather it is often disturbing. There was no way to control it.

[Problems to be solved by the invention]

Accordingly, an object of the present invention is to provide a method for suppressing the sweetness of glycyrrhizin without impairing the pharmacological action of glycyrrhizin, and to make glycyrrhizin easier to use in applications other than sweeteners than before.

[Means for solving the problem]

The present invention provides a method of using glycyrrhizin that does not require the sweetness of glycyrrhizin. A method for suppressing sweetness is provided.

Cyclodextrin has a donut-like molecular structure, and when allowed to coexist with a compound having a lipophilic group in an aqueous solution,
The lipophilic group of the coexisting compound is incorporated into the cavity to produce various inclusion compounds. Such properties of cyclodextrin have been conventionally used in glycyrrhizin-based sweeteners and other seasonings for the purpose of improving the taste (JP-A-60-188).
036). In that case, cyclodextrin is considered to improve the taste quality of the glycyrrhizin-based seasoning by including an impurity that causes bitterness or unpleasantness. However, in the present invention, glycyrrhizin itself is included in cyclodextrin, thereby preventing glycyrrhizin from exhibiting an inherent sweetness.In this respect, it is completely different from conventional sweetness improvement. is there.

The cyclodextrin used for suppressing sweetness in the present invention also eliminates foaming of the solution by including glycyrrhizin, and further significantly improves the solution stability.

Α-cyclodextrin in which cyclodextrin has six α-1,4 linked glucose units in a cyclic manner,
Although there are three types of 7 β-cyclodextrins and 8 γ-cyclodextrins, γ-cyclodextrin has the greatest glycyrrhizin inclusion force, and is therefore preferred as the cyclodextrin used in the present invention. However, it is not necessary to use one consisting only of the γ-isomer, and a mixture of the above three types of cyclodextrin which are easily available on the market may be used.

The sweetness suppression of glycyrrhizin according to the present invention can range from the case where the sweetness of glycyrrhizin is suppressed to a level that does not hinder practical use to the case where it is substantially eliminated. In addition, when the sweetness is suppressed to such an extent that there is no practical problem, the “sweetness that does not cause practical problems” differs depending on the use of glycyrrhizin. Therefore, although the preferred amount of cyclodextrin to glycyrrhizin cannot be uniformly shown, in most cases, when the most effective γ-cyclodextrin is used, about 1 part by weight of glycyrrhizin is used.
When the content is 0.1 to 100 parts by weight, the purpose of suppressing sweetness can be achieved, and about 1 part by weight or more is required to substantially eliminate sweetness.

Glycyrrhizin easily becomes an inclusion compound when mixed with cyclodextrin in an aqueous solution state, and loses or suppresses sweetness. Therefore, when practicing the present invention, glycyrrhizin may be mixed in advance with cyclodextrin in water, and all or a part of the mixture may be used as a substantially unsweetened clathrate before use.
At the stage of manufacturing pharmaceuticals, functional foods, and the like containing glycyrrhizin, an inclusion compound may be generated in situ by mixing glycyrrhizin and cyclodextrin with other raw materials.

Glycyrrhizin, the sweetness of which has been suppressed by the method of the present invention, may not show some of the pharmacological actions inherent to glycyrrhizin by being an inclusion compound in that state. Alternatively, cyclodextrin is hydrolyzed by intestinal bacteria and the inclusion compound is decomposed to form free glycyrrhizin, which is in a state where the original pharmacological action can be exhibited.

The sweetness suppression according to the present invention is effective for both licorice extract containing glycyrrhizin and purified glycyrrhizin. Glycyrrhizin may be either free glycyrrhizic acid or a water-soluble salt thereof. In addition to glycyrrhizin, naturally occurring 18β-glycyrrhizin and a stereoisomer 18α-glycyrrhizin obtained by heating it in a strongly alkaline solution state (Japanese Unexamined Patent Publication No.
-115797).

〔Example〕

Example 1 0.1 g of purified dipotassium glycyrrhizinate (a mixture of 80% of 18α-glycyrrhizin and 20% of 18β-glycyrrhizin).
Various amounts of cyclodextrin were added to 100 ml of a 1% aqueous solution in an aqueous solution, and the mixture was stirred. Thereafter, taste and solution properties were compared by a test method described later.

As the cyclodextrin, α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin (all products of Nippon Shokuhin Kako Co., Ltd .; purity: 98.5% or more) were used.

 The test results are shown in Tables 1 to 3.

Test method Sweetness evaluation: ++ Strong sweetness that is the same as glycyrrhizin + Very weak but sweet sweet ± Weak sweetness-No sweetness Foaming property: Put 20 ml of the aqueous solution into a 50 ml Nessler tube, and vigorously move up and down 20
Shake and measure the height of the foam after 30 seconds. The relative value is shown assuming that the foam height without cyclodextrin is 100.

Precipitation: Observe the change in properties when the pH is adjusted to 3.0 by adding acetic acid to the aqueous solution, and indicate as follows.

++ A large amount of precipitate is formed. + A small amount of precipitate is formed.-Clear without change. Example 2 A 0.5% aqueous solution of purified dipotassium glycyrrhizinate was prepared, and a cyclo, a mixture of α-form, β-form and γ-form was prepared. Dextrin preparation, Celdex CH-20 (product of Japan Food Processing Co., Ltd .; cyclodextrin content 20)
%), And the changes in sweetness and solution properties were examined in the same manner as in Example 1.

Table 4 shows the test results. In Table 4, the mixing ratio of Celdex is a weight ratio when glycyrrhizinate is set to 1.

Example 3 100 g of the same γ-cyclodextrin as used in Example 1 was dissolved in 1 warm water, and 100 g of licorice extract (glycyrrhizic acid content: 30% by weight) was added thereto, followed by stirring for 1 hour. The obtained solution was concentrated under reduced pressure, dried and pulverized to obtain 200 g of a yellow powder.

The sweetness of a 2% aqueous solution of the product of the above example was compared with the sweetness of a 1% aqueous solution of licorice extract containing no cyclodextrin by 10 panel members. As a result, all of the products of the examples confirmed that the sweetness of glycyrrhizin disappeared.

Further, the same aqueous solution as in Example 1 was used.
When the foaming test was conducted, it was found that the product of Example
The foam completely disappeared in 2 seconds, but about 5 minutes after the control, about 1/2 of the foam remained.

Furthermore, when phosphoric acid was added to the same aqueous solution to adjust the pH to 3.0, gelation was observed in the control aqueous solution, but no change was observed even in the case of the example product even when the pH was lowered to 1.5.

Example 4 The same cyclodextrin formulation used in Example 2
40g and glycyrrhizin preparation (glycyrrhizin content 17.5
%) 10 g in 50 ml of water, the solution is concentrated under reduced pressure,
0 g of an inclusion glycyrrhizin preparation was obtained.

Carbonated drinks to which the above-mentioned inclusion glycyrrhizin preparation was added were manufactured according to the formulations shown in Table 5.

Separately, a beverage having the same composition without the inclusion glycyrrhizin preparation (Comparative Example 1) and a beverage having the same composition with the glycyrrhizin preparation used for producing the inclusion glycyrrhizin preparation (Comparative Example 2) were produced.

A sensory test was conducted by 10 panel members on the obtained beverage. As a result, there was no significant difference in taste between the product of Example and Comparative Example 1; however, all of Comparative Example 2 answered that sweetness remained afterwards. Was.

Further, as an abuse test for checking the stability, each beverage was filtered through a membrane filter, frozen in a 20 ml test tube at −10 ° C. overnight, and after thawing, the transparency was observed.
In Example products and Comparative example 1, neither precipitation nor suspension was precipitated,
It was clear. On the other hand, in Comparative Example 2, some white insolubles were suspended.

Continuation of front page (58) Field surveyed (Int.Cl. ⁷ , DB name) A61K 47/40

Claims (2)

(57) [Claims] 1. Use of glycyrrhizin in applications that do not require the sweetness of glycyrrhizin, wherein cyclodextrin is included in cyclodextrin in combination with cyclodextrin in an amount of 0.1 part by weight or more per 1 part by weight of glycyrrhizin. A method for suppressing sweetness of glycyrrhizin. 2. The method according to claim 1, wherein γ-cyclodextrin is used as the cyclodextrin.