A method for inhibiting aggregation of steviol glycosides in water, and a stevia preparation in which aggregation in water is inhibited.

Abstract

To provide a method for suppressing aggregation of a steviol glycoside in an aqueous solution and a formulation used therein.SOLUTION: A method for suppressing aggregation of a steviol glycoside in an aqueous solution includes a step of allowing the steviol glycoside and a Siraitia grosvenorii extract to coexist in the aqueous solution.SELECTED DRAWING: None

Description

[Technical Field] , , , , 【0004】 , , , 【0001】 The present invention relates to a method for suppressing aggregation of steviol glycosides in water. The present invention also relates to a preparation used for suppressing aggregation of steviol glycosides in water. Further, the present invention relates to a stevia preparation in which aggregation in water is suppressed. [Background Art] 【0002】 Steviol glycosides are known as sweet components contained in the leaves and stems of Stevia rebaudiana Bertoni (scientific name: Stevia rebaudiana (Bertoni) Bertoni), which belongs to the genus Stevia of the Asteraceae family. The steviol glycosides and stevia extracts containing the same have been widely used as food additives and pharmaceutical additives (Non-Patent Documents 1 and 2). [Prior Art Documents] [Non-Patent Documents] 【0003】 [Non-Patent Document 1] Ministry of Health, Labour and Welfare, Consumer Affairs Agency, "The 9th Edition of the Food Additives Standards 2018", pages 725-726, "Stevia Extract", pages 726-727, "Steviol Glycosides" [Non-Patent Document 2] Ministry of Health, Labour and Welfare, Pharmaceutical and Life Hygiene Bureau, Pharmaceutical Review and Management Division, "Pharmaceutical Additive Standards 2018", pages 413-415, "Purified Stevia Extract" [Non-Patent Document 3] Ministry of Health, Labour and Welfare, Consumer Affairs Agency, "The 9th Edition of the Food Additives Standards 2018", pages 975-976, "Racantha Extract" [Summary of the Invention] [Problems to be Solved by the Invention] 【0004】 Through their ongoing research, the inventors have discovered that formulations containing steviol glycosides, such as stevia extract, have low stability in water, and crystals precipitate and aggregate over time. This tendency becomes more pronounced with increasing purity of the steviol glycoside. However, no technology is known to improve the water stability of steviol glycosides, particularly to suppress aggregation in water. 【0005】 Therefore, the object of the present invention is to provide a method for suppressing the aggregation of steviol glycosides in water. Furthermore, the object of the present invention is to provide a formulation for use in said method, and further to provide a steviol glycoside-containing formulation (stevia formulation) in which aggregation in water is suppressed. [Means for solving the problem] 【0006】 The inventors of the present invention have diligently conducted research to solve the aforementioned problems and have found that by co-administering monk fruit extract with steviol glycosides in an aqueous solution, the crystallization and aggregation of steviol glycosides in water are significantly suppressed, and an aqueous solution containing steviol glycosides with good storage stability can be prepared. The present invention was completed based on this finding and further research, and encompasses the following embodiments. 【0007】 (I) Formulation for inhibiting aggregation of steviol glycosides in aqueous solution (I-1) A formulation for inhibiting aggregation of steviol glycosides in an aqueous solution, characterized in that the formulation contains monk fruit extract. (I-2) The formulation according to (I-1), wherein the steviol glycoside is at least one selected from the group consisting of rebaudioside A, rebaudioside B, rebaudioside D, and stevioside, preferably rebaudioside A and / or stevioside. 【0008】 (II) Stevia preparations (II-1) A stevia preparation containing a steviol glycoside and the preparation described in (I-1). 【0009】 (III) Method for suppressing aggregation of steviol glycosides in aqueous solution (III-1) A method for suppressing aggregation of steviol glycosides in aqueous solution, The method comprises the step of coexisting a steviol glycoside and a monk fruit extract in an aqueous solution. (III-2) The method according to (III-1), wherein the steviol glycoside is at least one selected from the group consisting of rebaudioside A, rebaudioside B, rebaudioside D, and stevioside, preferably rebaudioside A and / or stevioside. (III-3) The method according to (III-1) or (III-2), wherein the aggregation is due to crystallization of the steviol glycoside in an aqueous solution. (III-4) A method for stabilizing a steviol glycoside-containing preparation or stevia extract containing 85% by mass or more, preferably 90% by mass or more, of steviol glycosides in water, as described in any of (III-1) to (III-3). [Effects of the Invention] 【0010】 According to the present invention, a method for suppressing aggregation of steviol glycosides in aqueous solution, or a formulation used in said method, can be provided. Furthermore, according to the method and formulation of the present invention, crystallization and aggregation of steviol glycosides in aqueous solution can be suppressed, and a stevia glycoside-containing formulation (stevia formulation) with good storage stability even when prepared in aqueous solution can be provided. [Modes for carrying out the invention] 【0011】 (I) Method for suppressing aggregation of steviol glycosides in aqueous solution The present invention provides a method for inhibiting aggregation of steviol glycosides in an aqueous solution (hereinafter simply referred to as "the method of the present invention"), characterized by coexisting the target steviol glycoside and monk fruit extract in an aqueous solution. 【0012】 The method of coexistence is not particularly limited, and examples include adding and dissolving monk fruit extract in an aqueous solution containing steviol glycosides, adding and dissolving steviol glycosides in an aqueous solution containing monk fruit extract, and adding and dissolving monk fruit extract in addition to steviol glycosides in an aqueous solvent. The aqueous solvent used to prepare the aqueous solution can be any solvent that is ingestible by the body, and examples include, but are not limited to, drinking water, tap water, natural water, mineral water, purified water, distilled water, deep-sea water, alkaline ionized water, hydrogen water, and pure water. 【0013】 The steviol glycosides targeted by this invention are compounds in which a monosaccharide or a disaccharide or trisaccharide or more oligosaccharides are bonded to one or two sites of the steviol skeleton. These steviol glycosides include Stevia rebaudiana bertoni (scientific name: Stevia rebaudiana The compound contains steviol glycosides found in the leaves and stems of (Bertoni)Bertoni (hereinafter also referred to as "stevia plants"). Examples include, but are not limited to, stevioside, rebaudioside A, B, C, D, and F, as well as dulcoside A, rubusoside, and steviolbioside. Preferably, it contains stevioside, rebaudioside A, rebaudioside B, and rebaudioside D, and more preferably stevioside and rebaudioside A. The steviol glycoside may contain one of the above components alone, or any two or more of them. 【0014】 For example, in one embodiment, when the target steviol glycoside is rebaudioside A, the concentration of rebaudioside A in the aqueous solution is not limited, but the lower limit is 0.5% by mass or more, preferably 0.75% by mass or more, more preferably 1% by mass or more, and the upper limit is 20% by mass or less, preferably 15% by mass or less, more preferably 10% by mass or less. 【0015】 In addition, although the concentration of the Momordica grosvenori extract used in combination therewith in the aqueous solution is not limited, in terms of the amount of mogroside V contained in the Momordica grosvenori extract, the lower limit is 0.15% by mass or more, preferably 0.3% by mass or more, more preferably 0.6% by mass or more, and the upper limit is 20% by mass or less, preferably 15% by mass or less, more preferably 10% by mass or less. Also, although not limited, the ratio of the Momordica grosvenori extract to 100 parts by mass of rebaudioside A in the aqueous solution can be selected from the range of 3 to 100 parts by mass in terms of the amount of mogroside V. Preferably it is 5 to 75 parts by mass, more preferably 10 to 50 parts by mass. 【0016】 Also, as another aspect, when the steviol glycoside is stevioside, the concentration of stevioside in the aqueous solution is not limited, but the lower limit is 0.5% by mass or more, preferably 0.75% by mass or more, more preferably 1% by mass or more, and the upper limit is 15% by mass or less, preferably 10% by mass or less, more preferably 7.5% by mass or less. 【0017】 In addition, although the concentration of the Momordica grosvenori extract used in combination therewith in the aqueous solution is not limited, in terms of the amount of mogroside V contained in the Momordica grosvenori extract, the lower limit is 0.15% by mass or more, preferably 0.3% by mass or more, more preferably 0.6% by mass or more, and the upper limit is 20% by mass or less, preferably 15% by mass or less, more preferably 10% by mass or less. Also, although not limited, the ratio of the Momordica grosvenori extract to 100 parts by mass of stevioside in the aqueous solution can be selected from the range of 3 to 100 parts by mass in terms of the amount of mogroside V. Preferably it is 5 to 75 parts by mass, more preferably 10 to 50 parts by mass. 【0018】 The quantification of various steviol glycosides can be carried out according to the methods described in the official pharmacopoeia (see Non-Patent Documents 1 and 2). Also, the quantification of mogroside V contained in the Momordica grosvenori extract can also be carried out according to the method described in the official pharmacopoeia (see Non-Patent Document 3). 【0019】 The steviol glycoside used in the present invention may be derived from the stevia plant regardless of its origin, or may be produced by fermentation technology. Although not limited, for example, Japanese Patent Application Laid-Open No. 2018-521636 describes a method for producing steviol glycoside from a glucol-containing composition using recombinant yeast. Various steviol glycosides can be prepared from stevia plants, but for simplicity, commercially available products can be used. 【0020】 As commercially available products, although not limited, examples of products containing rebaudioside A include Rebaudios (registered trademark) J-100 (≧95%) (manufactured by Morita Chemical Industries Co., Ltd.); The numerical value in parentheses indicates the content of rebaudioside A in the preparation (the standard value of the product). Also, as commercially available products containing stevioside, although not limited, examples include Stevron (registered trademark) S-100 (≧90%) (manufactured by Morita Chemical Industries Co., Ltd.). The numerical value in parentheses indicates the content of stevioside in the preparation (the standard value of the product). 【0021】 Momordica grosvenori (scientific name: Siraitia grosvenorii (Swingle)C.Jeffrey ex A.M.Lu & Zhi Y.Zhang ( Momordica grosvenorii Swingle)) is a vine-like perennial plant of the genus Momordica in the family Cucurbitaceae native to China. The Momordica grosvenori extract targeted by the present invention is an extract containing mogroside V extracted from the fruit of Momordica grosvenori, preferably the fresh fruit of Momordica grosvenori, using an organic solvent such as water or ethanol, regardless of the place of origin. The monk fruit extract may contain mogroside V in a purified state, or it may contain other triterpene glycosides in addition to mogroside V (for example, mogrool, mogroside IE1, mogroside IA1, mogroside IIE, mogroside III, mogroside IVa, mogroside IVE, simenoside, 11-oxomogoloside, 5α,6α-epoxymogroside, etc.). These are also included in the monk fruit extract that is the subject of this invention. The mogroside V content in the monk fruit extract is preferably 20% by mass or more of the total. More preferably 25% by mass or more, and even more preferably 30% by mass or more. 【0022】 These monk fruit extracts can be prepared by extracting them from the fruit of the monk fruit and further purifying them as needed, but commercially available products can be used for convenience. Examples of commercially available products, though not limited to those mentioned, include "SunNature® M30" (containing 30% by mass of mogroside V) and "SunNature® M50" (containing 50% by mass of mogroside V) (both manufactured by San-Ei Gen F.F.I. Co., Ltd.). 【0023】 The method of the present invention can suppress the aggregation of steviol glycosides in aqueous solutions, at least under room temperature conditions. Such aggregation can occur when steviol glycosides precipitate (crystallize) in aqueous solution, and then aggregate or deposit. For this reason, the method of the present invention can also be described as a method for suppressing the precipitation (crystallization) of steviol glycosides in aqueous solutions, or a method for stabilizing their dissolution in aqueous solutions. The presence or absence of aggregation and the suppression effect can be evaluated visually according to the method described in the experimental examples below. 【0024】 (II) Formulations for inhibiting aggregation of steviol glycosides in aqueous solution The present invention provides a formulation for suppressing aggregation of steviol glycosides in aqueous solution (hereinafter referred to as "aggregation inhibitor" for convenience). The present invention's flocculation inhibitor is characterized by containing monk fruit extract as an active ingredient. 【0025】 The proportion of monk fruit extract in the flocculation inhibitor is not particularly limited as long as it does not interfere with the amount used as described later, and can be appropriately selected and prepared up to a maximum of 100%. 【0026】 As mentioned above, the origin of the monk fruit extract is not particularly important, as long as it contains mogroside V. It can be extracted from the fruit of the monk fruit and further purified as necessary, or a commercially available product can be used. As mentioned above, it is preferable that the monk fruit extract contains 20% by mass or more of mogroside V. More preferably 25% by mass or more, and even more preferably 30% by mass or more. 【0027】 The amount of the flocculation inhibitor used in the present invention is not particularly limited, as long as it is an amount that can suppress the flocculation of the steviol glycoside by having the monk fruit extract coexist with the steviol glycoside to be flocculated in an aqueous solution. 【0028】 For example, if the steviol glycoside is rebaudioside A, the amount of flocculation inhibitor used can be adjusted to fall within the following ranges. In this case, the concentration of the steviol glycoside (rebaudioside A) in the aqueous solution is not limited, but the lower limit is 0.5% by mass or more, preferably 0.75% by mass or more, more preferably 1% by mass or more, and the upper limit is 20% by mass or less, preferably 15% by mass or less, more preferably 10% by mass or less. 【0029】 [Monk fruit extract] Concentration of aqueous solution: Converted to the amount of mogroside V, the lower limit is 0.15% by mass or more, preferably 0.3% by mass or more, more preferably 0.6% by mass or more, and the upper limit is 20% by mass or less, preferably 15% by mass or less, more preferably 10% by mass or less. Ratio to 100 parts by mass of rebaudioside A: Converted to the amount of mogroside V, 3 to 100 parts by mass, preferably 5 to 75 parts by mass, more preferably 10 to 45 parts by mass. 【0030】 In another embodiment, when the steviol glycoside is stevioside, the amount of flocculation inhibitor used can be adjusted to fall within the following ranges. In this case, the concentration of the steviol glycoside (stevioside) in the aqueous solution is not limited, but the lower limit is 0.5% by mass or more, preferably 0.75% by mass or more, more preferably 0.85% by mass or more, and the upper limit is 15% by mass or less, preferably 10% by mass or less, more preferably 7.5% by mass or less. 【0031】 [Monk fruit extract] Concentration of aqueous solution: Converted to the amount of mogroside V, the lower limit is 0.15% by mass or more, preferably 0.3% by mass or more, more preferably 0.6% by mass or more, and the upper limit is 20% by mass or less, preferably 15% by mass or less, more preferably 10% by mass or less. The ratio relative to 100 parts by mass of stevioside can be selected from a range of 3 to 100 parts by mass, preferably 5 to 75 parts by mass, and more preferably 10 to 50 parts by mass, when converted to the amount of mogroside V. 【0032】 The form of the flocculation inhibitor of the present invention is not particularly limited and includes solids such as powders, granules, tablets, and pills, as well as liquids, but is preferably in powder or granular form. The flocculation inhibitor of the present invention is used by adding it together with the aqueous solution when preparing an aqueous solution containing steviol glycosides by dissolving steviol glycosides in water. In this way, by having steviol glycosides and monk fruit extract coexist in the aqueous solution, the precipitation (crystallization) and flocculation of steviol glycosides in the aqueous solution can be suppressed. In other words, the flocculation inhibitor of the present invention can be suitably used to maintain or improve the stability (solubility stability) of steviol glycosides in aqueous solutions. 【0033】 (III) Stevia preparations The stevia preparation of the present invention is a steviol glycoside-containing preparation that contains the aforementioned steviol glycoside and the aforementioned monk fruit extract as an aggregation inhibitor. The formulations include solids such as powders, granules, tablets, and pills, as well as liquids. Powders or granules are preferred. 【0034】 The stevia preparation can be prepared according to standard methods depending on its form. For example, stevia preparations in the form of powder or granules can be prepared by mixing the powders of the aforementioned steviol glycoside and monk fruit extract to form a powder mixture; by spray-drying a solution containing steviol glycoside and monk fruit extract to form a powder; or by mixing steviol glycoside and monk fruit extract, dispersing them in a solution to form a slurry, and then extruding them into granules. The drying can be carried out by any method, such as spray drying, drum drying, or freeze-drying. 【0035】 One embodiment of the stevia preparation of the present invention is a preparation in which the steviol glycoside is rebaudioside A and contains monk fruit extract. The stevia preparations include those containing, per 100 parts by mass of rebaudioside A, 3 to 100 parts by mass, preferably 5 to 75 parts by mass, and more preferably 10 to 50 parts by mass of monk fruit extract, converted to the amount of mogroside V. 【0036】 Another embodiment of the stevia preparation of the present invention includes a preparation in which, when the steviol glycoside is stevioside, the preparation contains 3 to 100 parts by mass, preferably 5 to 75 parts by mass, more preferably 10 to 50 parts by mass, of monk fruit extract in terms of mogroside V amount, per 100 parts by mass of stevioside. 【0037】 The stevia formulation of the present invention can be used as a cooking sweetener or table sweetener on its own, for the purpose of replacing sugar and other sweeteners that are commonly used as sweeteners, and can also be incorporated into any edible product (e.g., food and beverages, oral medicines, mouthwashes, mouthwashes, toothpastes, etc.) as a sweetener. The stevia preparation of the present invention is characterized in that, when dissolved in water to prepare an aqueous solution with a concentration of, for example, 20% by mass or less, preferably 10% by mass or less, the stability (solubility) of the steviol glycoside in aqueous solution is good, and the precipitation (crystallization) and aggregation of the steviol glycoside are suppressed. 【0038】 In this specification, the terms “contains” and “includes” include the meanings of “consisting of” and “substantially consisting of.” [Examples] 【0039】 The present invention will be described below using experimental examples to aid in understanding its structure and effects. However, the present invention is not limited in any way by these experimental examples. Unless otherwise specified, the following experiments were conducted at room temperature (25±5℃) and under atmospheric pressure conditions. Unless otherwise specified, "%" below means "mass percent" and "parts" means "parts by mass". 【0040】 The formulations used in the following experiments are as follows: (1) Rebaudioside A preparation: Rebaudio® J-100 (dried powder, manufactured by Morita Chemical Industry Co., Ltd.), a preparation containing 90% or more of Rebaudioside A. (2) Stevioside preparations: Stevilon® S-100 (dried powder, manufactured by Morita Chemical Industry Co., Ltd.), preparations containing 90% or more stevioside. (3) Luo Han Guo extract 1: Sun Nature (registered trademark) M30 (dried powder, manufactured by San-Ei Gen F.F.I. Co., Ltd.), a preparation containing 30% mogroside V. (4) Luo Han Guo Extract 2: Sun Nature (registered trademark) M50 (dried powder, manufactured by San-Ei Gen F.F.I. Co., Ltd.), a preparation containing 50% mogroside V. 【0041】 Experimental Example 1: Aggregation of steviol glycosides in aqueous solution and its suppression (Part 1) We evaluated the aggregation of "rebaudioside A" as a steviol glycoside in aqueous solution and the inhibitory effect of monk fruit extract on this aggregation. 【0042】 (1) Experimental method To 20 mL of an aqueous solution containing a 5% concentration of rebaudioside A preparation, monk fruit extract 1 (Example 1a), monk fruit extract 2 (Example 1b), or sugar (Comparative Example) was added as an agglutination inhibitor to the concentrations (W / V%) shown in Table 1. The solution was dissolved at room temperature and placed in a transparent glass container with a lid (27 mm diameter x 55 mm height) and left to stand in the dark at room temperature for 1 hour to 7 days. 【0043】 The presence or absence of crystal precipitation and aggregation was visually confirmed 1 hour, 4 hours, 1 day, 3 days, and 7 days after standing. The effectiveness of the aggregation inhibitor used was evaluated according to the following six-level criteria based on the amount of cloudy aggregates. 【0044】 [Suppression of aggregation] 0: No aggregates 1: Aggregates accumulate up to about 1 / 5 of the way down from the bottom of the solution (bottom of the container). 2: Aggregates accumulate from the bottom of the solution (container bottom) up to about 2 / 5 of the way up. 3: Aggregates accumulate from the bottom of the solution (bottom of the container) up to about 3 / 5 of the way up. 4: Aggregates accumulate from the bottom of the solution (bottom of the container) up to about 4 / 5 of the way up. 5: Aggregates accumulate throughout the solution. 【0045】 (2) Experimental results The results are shown in Table 1. 【0046】 [Table 1] 【0047】 As shown in Table 1, rebaudioside A has low stability in aqueous solutions and crystallizes and aggregates quickly (Blank). In contrast, it was confirmed that the crystallization and aggregation of rebaudioside A could be significantly suppressed by adding monk fruit extract to an aqueous solution containing rebaudioside A and keeping them together. This effect was hardly observed with sugar. 【0048】 Experimental Example 2: Aggregation of steviol glycosides in aqueous solution and its suppression (Part 2) We evaluated the aggregation of "stevioside" as a steviol glycoside in aqueous solution and the inhibitory effect of monk fruit extract on this aggregation. 【0049】 (1) Experimental method To 20 mL of an aqueous solution containing a 5% stevioside preparation, monk fruit extract 1 (Example 2a) and monk fruit extract 2 (Example 2b) were added as flocculation inhibitors to the concentrations (W / V%) shown in Table 2. The solution was dissolved at room temperature and left to stand for 1 to 7 days in a transparent glass container with a lid (27 mm diameter x 55 mm height) in the dark at room temperature. 【0050】 At 1 hour, 4 hours, 1 day, 3 days, and 7 days after standing, the presence or absence of crystal precipitation and aggregation was visually confirmed, and the effect of the aggregation inhibitor used was evaluated based on the amount of cloudy aggregates, according to the same criteria as in Experimental Example 1. 【0051】 (2) Experimental results The results are shown in Table 2. 【0052】 [Table 2] 【0053】 As shown in Table 2, stevioside is not very stable in aqueous solutions and tends to aggregate (Blank). In contrast, it was confirmed that the crystallization and aggregation of stevioside could be significantly suppressed by adding monk fruit extract to an aqueous solution containing stevioside and keeping them together.

Claims

[Claim 1] A formulation for suppressing aggregation in an aqueous solution of at least one steviol glycoside selected from the group consisting of rebaudioside A and stevioside, It contains monk fruit extract containing mogroside V as an active ingredient. The amount of mogroside V is used in a ratio of 3 to 100 parts by mass per 100 parts by mass of rebaudioside A in the aqueous solution, or / or The aforementioned aqueous solution is used in a ratio of 3 to 100 parts by mass of mogroside V per 100 parts by mass of stevioside. formulation. [Claim 2] A method for suppressing aggregation in an aqueous solution of at least one steviol glycoside selected from the group consisting of rebaudioside A and stevioside, The method includes the step of coexisting the steviol glycoside and a monk fruit extract containing mogroside V in an aqueous solution. The process in question is, A step of coexisting the aforementioned aqueous solution with monk fruit extract in a ratio of 3 to 100 parts by mass, converted to the amount of mogroside V, relative to 100 parts by mass of rebaudioside A, or / or This step involves coexisting monk fruit extract with 100 parts by mass of stevioside in the aqueous solution in a ratio of 3 to 100 parts by mass, calculated in terms of the amount of mogroside V. The aforementioned method. [Claim 3] The method according to claim 2, wherein the aggregation is due to the crystallization in an aqueous solution of at least one steviol glycoside selected from the group consisting of rebaudioside A and stevioside. [Claim 4] The method according to claim 2 or 3, which is a method for stabilizing a steviol glycoside-containing preparation or stevia extract in water, comprising 50% by mass or more of at least one steviol glycoside selected from the group consisting of rebaudioside A and stevioside.

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