WO2021220948A1 - ステビオール配糖体組成物の製造方法 - Google Patents

ステビオール配糖体組成物の製造方法 Download PDF

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Publication number
WO2021220948A1
WO2021220948A1 PCT/JP2021/016400 JP2021016400W WO2021220948A1 WO 2021220948 A1 WO2021220948 A1 WO 2021220948A1 JP 2021016400 W JP2021016400 W JP 2021016400W WO 2021220948 A1 WO2021220948 A1 WO 2021220948A1
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Prior art keywords
steviol glycoside
treatment liquid
mass ppm
rebaugioside
additive
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PCT/JP2021/016400
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English (en)
French (fr)
Japanese (ja)
Inventor
亮輝 三井
聡一郎 浦井
芳明 横尾
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Suntory Holdings Ltd
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Suntory Holdings Ltd
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Priority to BR112022021643A priority Critical patent/BR112022021643A2/pt
Priority to JP2022517700A priority patent/JP7678799B2/ja
Priority to CN202610116506.1A priority patent/CN121867387A/zh
Priority to CN202180044864.1A priority patent/CN115996642A/zh
Publication of WO2021220948A1 publication Critical patent/WO2021220948A1/ja
Anticipated expiration legal-status Critical
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof

Definitions

  • the present invention relates to a method for producing a steviol glycoside composition and a method for increasing the concentration of steviol glycoside in a steviol glycoside-containing solution.
  • the present invention also relates to foods and drinks containing a steviol glycoside composition produced by the above production method.
  • Stevia rebaudiana in the family Stevia contain a secondary metabolite called Steviol, which is a type of diterpenoid, and steviol glycosides are about 300 times as sweet as sugar, so they are calories. It is used in the food industry as a sweetener for les. Obesity is developing internationally as a serious social problem, and the demand for calorie-less sweeteners is increasing day by day from the viewpoint of improving health and reducing medical costs.
  • artificially synthesized amino acid derivatives Aspartame and Acesulfame Potassium are used as artificial sweeteners, but naturally occurring calorie-less sweeteners such as steviol glycosides are more common. It is expected that it will be safe and easy to obtain public acceptance.
  • Patent Document 1 a steviol glycoside composition is obtained by extracting from the leaves of a Stevia rebaudiana plant containing rebaudioside M at a concentration higher than the general relative concentration. The method is described.
  • the present invention provides a novel method for producing a steviol glycoside composition and a method for increasing the concentration of steviol glycoside in a steviol glycoside-containing solution.
  • the present invention also provides foods and drinks containing the steviol glycoside composition produced by the above production method.
  • treatment solution including A method for producing a steviol glycoside composition, wherein the first additive is added so that the first treatment liquid has a pH of 10 to 13.
  • the additive is an alkaline agent.
  • the alkaline agent contains one or more compounds selected from the group consisting of alkali metal hydroxides, alkaline earth metal hydroxides, silicates, carbonates and bicarbonates.
  • the steviol glycoside composition is selected from the group consisting of rebaugioside A, rebaugioside B, rebaugioside M, rebaugioside C, rebaugioside D, stevioside, rebaugioside F, zulucocid A, rebaugioside G, rebaugioside N, rubusoside and steviolbioside.
  • the production method according to any one of [1] to [3], which comprises one or more kinds of steviol glycosides.
  • [5] The production method according to any one of [1] to [4], wherein the first treatment liquid is held for 1 minute to 3 days after the first treatment liquid is prepared.
  • [5A] The production method according to any one of [1] to [4], wherein the treatment liquid is held for 1 minute to 3 days after the treatment liquid is prepared.
  • [6] Further comprising adding a second additive to the first treatment liquid to prepare a second treatment liquid.
  • the treatment liquid further comprises adding a second additive to prepare a second treatment liquid.
  • the first treatment liquid and / or the second treatment liquid is selected from the group consisting of aluminum sulfate, polyaluminum chloride, iron (III) chloride or a hydrate thereof, polyacrylamide hydrolysate, alginic acid, chitin and chitosan.
  • the production method according to [6], wherein one or more compounds to be added are further added.
  • the treatment liquid and / or the second treatment liquid is selected from the group consisting of aluminum sulfate, polyaluminum chloride, iron (III) chloride or a hydrate thereof, polyacrylamide hydrolysate, alginic acid, chitin and chitosan 1
  • the production method according to [6A] wherein more than a species of compound is further added.
  • [8] Preparing a steviol glycoside-containing solution containing stevia extract and To prepare a first treatment liquid by adding a first additive to the steviol glycoside-containing solution.
  • [8A] Preparing a steviol glycoside-containing solution containing stevia extract and The treatment liquid is prepared by adding an additive to the steviol glycoside-containing solution.
  • [11] A food or drink containing the steviol glycoside composition according to [10].
  • the present invention it is possible to provide a novel method for producing a steviol glycoside composition. Further, according to the present invention, it is possible to provide a method for increasing the concentration of the steviol glycoside composition in the steviol glycoside-containing solution.
  • the method for producing a steviol glycoside composition of the present invention (hereinafter, also referred to as “the production method of the present invention”) is a steviol glycoside-containing solution containing a stevia extract (hereinafter, also referred to as “the production method of the present invention”). (Simply also referred to as “steviol glycoside-containing solution”) is prepared, and the first additive is added to the steviol glycoside-containing solution to prepare a first treatment liquid. The first additive is added so that the first treatment liquid has a pH of 10 to 13.
  • the production method of the present invention includes preparing a steviol glycoside-containing solution containing a stevia extract and preparing a treatment liquid by adding an additive to the steviol glycoside-containing solution. , The additive is added so that the treatment solution has a pH of 10 to 13. According to the production method of the present invention, by adjusting the pH of the steviol glycoside-containing solution to 10 to 13, a specific steviol glycoside in the resulting steviol glycoside composition can be obtained. The concentration can be increased.
  • Stevia leaves contain a wide variety of components in addition to steviol glycosides, and when a steviol glycoside composition is prepared with stevia extract as the main component, it is included in the steviol glycoside composition.
  • the components other than the steviol glycosides are substantially derived from Stevia, unless other components are optionally added.
  • Stevia-derived components other than such steviol glycosides include water-soluble components and insoluble components.
  • Water-soluble components include polysaccharides such as water-soluble dietary fiber, secondary metabolites such as alkaloids and flavonoids and terpenoids, methanol, polyphenols, minerals, vitamins, amino acids, organic acids, water-soluble proteins, and various other configurations. Examples include sugars.
  • insoluble components include insoluble polysaccharides including insoluble dietary fiber, insoluble proteins and lipids.
  • insoluble components include insoluble polysaccharides including insoluble dietary fiber, insoluble proteins and lipids.
  • insoluble polysaccharides including insoluble dietary fiber, insoluble proteins and lipids.
  • steviol glycosides bound to some of these stevia-derived components are dissociated from the binding by increasing pH. It is considered that the amount of purification increases and the concentration in the finally obtained steviol glycoside composition increases.
  • the increase in the concentration of steviol glycoside is compared with the concentration of steviol glycoside in the steviol glycoside composition obtained without adjusting the steviol glycoside-containing solution to a predetermined pH.
  • concentration of steviol glycosides increases. That is, the increase in the concentration may be relative, and the concentration of the steviol glycoside does not necessarily have to be equal to or higher than a specific value.
  • the increase in the concentration of steviol glycoside can be expressed as the rate of increase (%) when the above comparative control is used as a reference.
  • the concentration of steviol glycoside can be measured by a method using LC / MS or HPLC.
  • the steviol glycoside compositions obtained by the production method of the present invention include rebaugioside A, rebaugioside B, rebaugioside M, rebaugioside C, rebaugioside D, stevioside, rebaugioside F, zulcoside A, rebaugioside G, rebaugioside N, rubusoside and steviolbioside. Contains one or more steviol glycosides selected from the group consisting of.
  • the steviol glycoside composition obtained by the production method of the present invention includes, for example, rebaudioside E, rebaugioside I, rebaugioside J, rebaugioside K, rebaugioside M, and rebaugioside O. It may further contain one or more steviol glycosides selected from the group consisting of rebaugioside Q, rebaugioside R, zulucocid C, steviol and steviol monoside.
  • the steviol glycoside composition obtained by the production method of the present invention is selected from the group consisting of rebaugioside A, rebaugioside C, stevioside, rebaugioside F, rebaugioside G and rubusoside among the steviol glycosides listed above. It is an increase in concentration above the seed.
  • the rate of increase in the concentration of rebaugioside A when the first treatment liquid or the treatment liquid is adjusted to a predetermined pH is 101 to 150%, 101 to 140%, 103 to 140%, 105.
  • the rate of increase in the concentration of rebaugioside C when the first treatment liquid or the treatment liquid is adjusted to a predetermined pH is 101 to 170%, 101 to 165%, 101 to 160%, 105.
  • the rate of increase in the concentration of stevioside when the first treatment liquid or the treatment liquid is adjusted to a predetermined pH is 101 to 200%, 101 to 190%, 101 to 185%, 101 to 180%, 110-180%, 120-180%, 125-180%, 130-180%, 135-180%, 140-180%, 145-180%, 150-180%, 151-180%, 152- It may be 180%, 153 to 180%, 154 to 180%, 155 to 180%, 156 to 180%, 157 to 180%, 158 to 180%, 159 to 180% or 160% to 180%.
  • the rate of increase in the concentration of rebaugioside F when the first treatment liquid or the treatment liquid is adjusted to a predetermined pH is 101 to 150%, 101 to 140%, 103 to 140%, 105.
  • the rate of increase in the concentration of rebaugioside G when the first treatment liquid or the treatment liquid is adjusted to a predetermined pH is 101 to 350%, 101 to 340%, 101 to 330%, 110. ⁇ 330%, 120-330%, 130-330%, 140-330%, 150-330%, 160-330%, 170-330%, 180-330%, 190-330%, 200-330%, 210 It may be ⁇ 330%, 220-330%, 230-330%, 240-330%, 250-330% and the like.
  • the rate of increase in the concentration of rubusoside when the first treatment liquid or the treatment liquid is adjusted to a predetermined pH is 101 to 700%, 101 to 690%, 101 to 680%, 101 to 670%, 110-670%, 120-670%, 130-670%, 140-670%, 150-670%, 160-670%, 170-670%, 180-670%, 190-670% or 200- It may be 670% or the like.
  • the rate of increase in the concentration of each of the above steviol glycosides is 30 times the amount of ion-exchanged water (60) of the raw material stevia dried leaves (moisture content: 3 to 4% by weight). This is a case where a steviol glycoside-containing solution containing a stevia extract obtained by extracting once at (° C. ⁇ 5 ° C.) is used.
  • the production method of the present invention includes preparing a steviol glycoside-containing solution containing a stevia extract.
  • Examples of the method for obtaining a Stevia extract include extracting dried leaves of a Stevia plant with an aqueous solvent to obtain an extract (extract).
  • the dried leaf of a stevia plant means a leaf having a reduced water content by drying the fresh leaf of the stevia plant.
  • the water content of the dried leaves of the Stevia plant is preferably 1 to 10% by weight, more preferably 2 to 8% by weight, and particularly preferably 3 to 4% by weight.
  • Extraction of steviol glycosides from dried leaves can be performed using a solvent such as water, alcohol, or a mixed solution thereof.
  • Preferred extraction solvents include ion-exchanged water, pure water (for example, milliQ water), and an aqueous ethanol solution.
  • the dried leaves may or may not be crushed.
  • the extraction process may be performed using a kneader extractor (SKN-R100, manufactured by Sanyu Kikai Co., Ltd.) or the like.
  • the steviol glycoside can be extracted more efficiently by heating the aqueous solvent.
  • the temperature at the time of extraction may be, for example, 25 to 80 ° C., 30 to 75 ° C., 35 to 70 ° C., 40 to 65 ° C., 45 to 70 ° C., preferably 45 to 70 ° C.
  • the lower limit value and the upper limit value of the temperature may be, for example, ⁇ 1 ° C., ⁇ 2 ° C., ⁇ 3 ° C., ⁇ 4 ° C., ⁇ 5 ° C. of each temperature.
  • Extraction may be performed not only once but multiple times. By performing multiple extractions, more steviol glycosides contained in the leaves are extracted. From the viewpoint of efficiency, it is preferable that the extraction is performed twice.
  • the steviol glycoside-containing solution may be the stevia extract itself obtained by the above method.
  • the steviol glycoside-containing solution is a steviol glycoside composition produced by any other method (for example, a method using a steviol glycoside hydrolase) as long as it contains a stevia extract. May be further added.
  • the obtained stevia extract may be solid-liquid separated.
  • the solid-liquid separation treatment is not particularly limited as long as the solid and liquid are sufficiently separated, and examples thereof include treatment using a centrifuge and a filter press, and gravity filtration using a filter and a mesh.
  • the solid-liquid separation treatment may use a plurality of means, for example, a second solid-liquid separation treatment may be performed after the first solid-liquid separation treatment.
  • the first additive or additive is added to the steviol glycoside-containing solution to prepare the first treatment liquid or treatment liquid.
  • the production method of the present invention is prepared by the method of (A) above. This includes adding a first additive to a steviol glycoside-containing solution to prepare a first treatment liquid.
  • the production method of the present invention includes adding an additive to the steviol glycoside-containing solution prepared by the method (A) above to prepare a treatment liquid.
  • the first additive or additive is an alkaline agent. Examples of the alkaline agent include alkali metal hydroxides, alkaline earth metal hydroxides, silicates, carbonates, and hydrogen carbonates.
  • alkali metal hydroxide examples include sodium hydroxide, potassium hydroxide and the like.
  • alkaline earth metal hydroxide examples include calcium hydroxide and magnesium hydroxide.
  • silicate examples include sodium metasilicate, sodium orthosilicate, potassium metasilicate, potassium orthosilicate and the like.
  • carbonate examples include sodium carbonate, potassium carbonate and the like.
  • hydrogen carbonate examples include sodium hydrogen carbonate, potassium hydrogen carbonate and the like. Among them, sodium hydroxide, potassium hydroxide and calcium hydroxide are particularly preferable. Further, these alkaline agents may be used alone or in combination of two or more.
  • the first additive or additive is added to the steviol glycoside-containing solution so that the first treatment liquid or treatment liquid has a pH of 10 to 13. That is, the addition amount of the first additive or the additive is not particularly limited as long as the pH of the first treatment liquid or the treatment liquid is within the above range, and depends on the amount of the steviol glycoside-containing solution. , The first treatment liquid or the treatment liquid may be added while being appropriately adjusted so that the pH of the treatment liquid is 10 to 13.
  • the pH of the first treatment liquid or the treatment liquid is pH 10 to 13, pH 10 to 12.5, pH 10.1 to 12.5, pH 10.2 to 12.5, pH 10. 3 to 12.5, pH 10.4 to 12.5, pH 10.5 to 12.5, pH 10.6 to 12.5, pH 10.7 to 12.5, pH 10.8 to 12.5, pH 10.9 to 12.5, pH 11 to 13, pH 11 to 12.5, pH 11.1 to 12.5, pH 11.2 to 12.5, pH 11.3 to 12.5, pH 11.4-12.5, pH 11.5 to 12.5, pH 11.6-12.5, pH 11.7 to 12.5, pH 11.8 to 12.5, pH 11.9 to 12.5, pH 11 to 12.2, pH 11.1 to 12.2, pH 11.2 to 12.2, pH 11.3 to 12.2, pH 11.4 to 12.2, pH 11.5-12.2, pH 11.6 to 12.2, pH 11.7 to 12.2, pH 11. It may be 8 to 12.2 or pH 11.9 to 12.2 and the like.
  • the temperature of the first additive or the steviol glycoside-containing solution when the additive is added is 1 to 60 ° C., 5 to 60 ° C., 10 to 60 ° C., 15 to 60 ° C., 20 to 60 ° C., 25 to 60 ° C, 30-60 ° C, 40-60 ° C, 50-60 ° C, 1-50 ° C, 5-50 ° C, 10-50 ° C, 15-50 ° C, 20-50 ° C, 25-50 ° C, 30- 50 ° C, 1-40 ° C, 5-40 ° C, 10-40 ° C, 15-40 ° C, 20-40 ° C, 25-40 ° C, 30-40 ° C, 1-30 ° C, 5-30 ° C, 10- It may be 30 ° C., 15 to 30 ° C., 20 to 30 ° C., or the like.
  • the first treatment liquid or the treatment liquid may be held for a predetermined time before preparing the second treatment liquid described later.
  • to hold the first treatment liquid or the treatment liquid means to prepare the first treatment liquid or the treatment liquid, and then add a second additive to prepare the second treatment liquid described later. It means to maintain a predetermined pH value or range until it is used.
  • the first treatment liquid or the treatment liquid is held, it may be held without any treatment, or may be held after some treatment.
  • the time for holding the first treatment liquid or the treatment liquid is, for example, 1 minute to 3 days, 1 minute to 2 days, 1 minute to 24 hours, 1 minute to 12 hours, 1 minute to 10 hours, 1 minute to 8 hours, 1 minute to 6 hours, 1 minute to 4 hours, 1 minute to 3 hours, 1 minute to 2 hours, 2 minutes to 2 hours, 3 minutes to 2 hours, 4 minutes to 2 hours, 5 minutes to 2 hours 10 minutes to 2 hours, 15 minutes to 2 hours, 20 minutes to 2 hours, 25 minutes to 2 hours, 30 minutes to 2 hours, 35 minutes to 2 hours, 40 minutes to 2 hours, 45 minutes to 2 hours, 50 Minutes to 2 hours, 55 minutes to 2 hours, 1 to 2 hours, and the like can be mentioned.
  • a first additive or an additive is added to a steviol glycoside-containing solution to adjust the pH to a range of 10 to 13, and the steviol glycoside composition contains a specific steviol.
  • the concentration of glycosides increases.
  • the first treatment liquid or treatment liquid once adjusted to the pH range of 10 to 13 is stable without a decrease in the increased concentration of steviol glycosides even when the treatment liquid is subsequently retained until the addition of the second additive. Is.
  • the temperature at which the first treatment liquid or the treatment liquid is held may be, for example, room temperature (about 25 ° C.).
  • the second treatment liquid is prepared by adding the second additive to the first treatment liquid or the treatment liquid.
  • the production method of the present invention is to add the second additive to the first treatment liquid. Is further included to prepare a second treatment liquid. Further, the production method of the present invention further includes adding a second additive to the treatment liquid to prepare a second treatment liquid.
  • the second additive is an additive having an action of lowering pH. Any such additive can be used as long as it has a pH-lowering effect, and for example, an organic pH adjuster such as citric acid, lactic acid, acetic acid, phosphoric acid, hydrochloric acid, etc. Examples thereof include inorganic pH adjusters such as sulfuric acid and carbon dioxide. Further, a compound such as aluminum sulfate, polyaluminum chloride, iron (III) chloride or a hydrate thereof, which will be described later, may be used. These second additives may be used alone or in combination of two or more.
  • the second additive is added to the first treatment liquid or treatment liquid so that the second treatment liquid has a pH of 2 to 10. That is, the amount of the second additive added is not particularly limited as long as the pH of the second treatment liquid is within the above range, and the second treatment liquid or the second treatment liquid is added according to the amount of the first treatment liquid or the treatment liquid. It may be added while appropriately adjusting the pH of the treatment liquid to be 2 to 10. When a compound such as aluminum sulfate, polyaluminum chloride, iron (III) chloride or a hydrate thereof is used, the addition amount may be adjusted in consideration of the agglutination reaction described later.
  • a first additive or an additive is added to a steviol glycoside-containing solution to adjust the pH to a range of 10 to 13, and the steviol glycoside composition contains a specific steviol.
  • the concentration of glycosides increases.
  • the first treatment liquid or treatment liquid once adjusted to the pH range of 10 to 13 is then adjusted to the pH range of 2 to 10 by adding a second additive, but the concentration of steviol glycosides is increased. Is stable without decreasing.
  • the second treatment liquid has pH 2 to 10, pH 2.5 to 9.5, pH 3 to 9, pH 3.5 to 8.5, pH 4 to 8, and pH 4.5 to 8.
  • the pH may be 5 to 8 or the like.
  • the temperature at which the first treatment liquid or the second additive is added to the treatment liquid may be, for example, room temperature (about 25 ° C.).
  • the first treatment liquid or treatment liquid and / or the second treatment liquid includes aluminum sulfate, polyaluminum chloride, iron (III) chloride or a hydrate thereof, and a polyacrylamide hydrolyzate.
  • One or more compounds selected from the group consisting of alginic acid, chitin and chitosan may be further added. These compounds may contain one or more kinds, and may contain two or more kinds in combination. Further, these compounds may be added during the step "B", may be added during the main step "C" as described above, and may be added during the step "B” and the present. It may be added in step "C".
  • the amount of the compound added is not particularly limited as long as it causes an agglutination reaction in the first treatment liquid or the treatment liquid and / or the second treatment liquid, but is, for example, with respect to the soluble solid content contained in the treatment liquid. , 3.0 to 50% by weight can be added.
  • iron (III) chloride hexahydrate it can be added in an amount corresponding to 15 to 40% by weight of the solid content in the treatment liquid, preferably 18 to 38% by weight, more preferably 20. It can be added in an amount of up to 35% by weight.
  • a 0.5% (w / v) chitosan solution it can be added in an amount corresponding to 3.0 to 10% by weight of the soluble solid content contained in the treatment liquid, preferably 4.0 to 8. It can be added in an amount of 0% by weight, more preferably 4.5 to 7.0% by weight.
  • the pH at the time of performing the aggregation treatment can be appropriately selected so as to optimize the aggregation according to the type of the above compound.
  • the pH of the first treatment liquid or treatment liquid and / or the second treatment liquid at the time of aggregation treatment is pH 2 to 13, pH 3 to 13, pH 4 to 13, pH 5 to 13 or pH 6 to. It may be 13 mag.
  • the temperature at which the coagulation treatment is performed may be performed at room temperature (about 25 ° C.) without heating or cooling.
  • the agglomerates contained in the first treatment liquid or the treatment liquid and / or the second treatment liquid are removed after the agglutination treatment and before any resin purification treatment described later. May be good.
  • the agglutination can be removed by a known method such as filtration.
  • the following treatments (D) to (F) may be further performed on the second treatment liquid, if desired.
  • the second treatment liquid prepared through each of the above treatments may be treated with a hydrophobic porous resin.
  • Steviol glycosides are amphipathic with hydrophilic and hydrophobic groups in their molecular structure and have a molecular weight of around 1,000. It is also known that it is stable at pH 2.5 to 9.0 and does not ionize even if it is acidic or basic.
  • the first treatment liquid or the treatment liquid that has undergone the aggregation treatment contains a large amount of components other than the steviol glycoside.
  • such components include components with different molecular weights from steviol glycosides, such as iron ions, and components that ionize, such as amino acids, which are hydrophobically porous. It is considered that it can be removed by processing the resin.
  • the steviol glycoside having a hydrophobic steviol skeleton is hydrophobically bound to the synthetic resin and captured.
  • highly hydrophilic impurities do not bind to the resin and are transferred to the through fraction and removed. Therefore, the treatment liquid that has undergone the coagulation treatment is added to the column packed with the above resin, and then washed with water. It is considered that the purity of steviol glycosides is improved. Further, since the bond between the steviol glycoside and the functional group of the synthetic resin is dissociated by the low-polarity solvent, there is an advantage that the steviol glycoside can be finally recovered in a high yield.
  • the hydrophobic porous resin used in the production method according to the embodiment of the present invention is not particularly limited as long as it is a porous resin having a low affinity for water, and for example, a copolymer of styrene and divinylbenzene, polypropylene, etc. , Polypropylene, polystyrene, poly (meth) acrylonitrile, polyamide and one or more hydrophobic resins selected from polycarbonate are preferred.
  • the copolymer of styrene and divinylbenzene has not been subjected to an ion exchange group introduction treatment (that is, it does not have an ion exchange group).
  • styrene and divinylbenzene are copolymerized to form a three-dimensional network structure, and then an ion exchange group is introduced into the resin. "Not done” means that such processing has not been done.
  • the hydrophobic porous resin has a hydrophobic group, and the hydrophobic group includes one or more selected from an aryl group, an alkyl group, an alkylsilyl group, an ester group and an epoxy group. included. In one embodiment of the present invention, if one or more hydrophobic groups selected from these are contained, other hydrophobic groups may be further contained.
  • Examples of the aryl group include a phenyl group, a benzyl group, a tolyl group, a xsilyl group and the like
  • examples of the alkyl group include an alkyl group of C1 to 20, for example, a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group.
  • Groups, octadecyl groups and the like can be mentioned.
  • the most frequent pore radius of the hydrophobic porous resin is 10 to 200 ⁇ . In a preferred embodiment of the invention, the most frequent pore radii are 10-150 ⁇ , 15-100 ⁇ , or 20-80 ⁇ . It is considered that the steviol glycoside is efficiently adsorbed in the pores and efficiently separated from other components by having such pore characteristics.
  • the treatment liquid may be further treated with an anion exchange resin before the treatment with the hydrophobic porous resin.
  • an anion exchange resin By pre-treating with an anion exchange resin, components bound to the hydrophobic resin such as pigments and catechins can be effectively removed.
  • an anion exchange resin is not particularly limited, and examples thereof include a basic anion exchange resin.
  • a basic anion exchange resin a 1st to 2nd secondary amino group is introduced as a functional group.
  • a weakly basic anion exchange resin or a strongly basic anion exchange resin having a quaternary ammonium group for example, a trimethylammonium group or a dimethylethanolammonium group
  • quaternary ammonium group for example, a trimethylammonium group or a dimethylethanolammonium group
  • the solution that has undergone the resin purification treatment may be further concentrated to remove the aqueous solvent.
  • Such treatment is not particularly limited, and examples thereof include a method of evaporating the aqueous solvent by heating and a method of removing the aqueous solvent by drying under reduced pressure.
  • any additional step By further adding a crystallization step after the production method of the present invention, a high-purity (purity of 95% or more) steviol glycoside composition can also be produced.
  • the present invention is a method of increasing the concentration of steviol glycoside in a steviol glycoside-containing solution (hereinafter, also referred to as "the method of the present invention"). Also referred to).
  • the method of the present invention is to prepare a steviol glycoside-containing solution containing a stevia extract, and to add a first additive to the steviol glycoside-containing solution to prepare a first treatment liquid. , And the first additive is added so that the first treatment solution has a pH of 10 to 13.
  • the method of the present invention includes preparing a steviol glycoside-containing solution containing a stevia extract and preparing a treatment liquid by adding an additive to the steviol glycoside-containing solution.
  • the additive is added so that the treatment solution has a pH of 10 to 13.
  • the method of the present invention increases the concentration of one or more steviol glycosides selected from the group consisting of rebaugioside A, rebaugioside C, stevioside, rebaugioside F, rebaugioside G and rubusoside.
  • the method of the present invention has substantially the same configuration as the method for producing a steviol glycoside composition of the present invention. Therefore, the above description of "1. Method for producing steviol glycoside composition" is also valid for the method of the present invention.
  • the present invention also relates to a steviol glycoside composition produced by the production method of the present invention (hereinafter, also referred to as “the steviol glycoside composition of the present invention”).
  • the steviol glycoside composition may be used as a sweetening composition.
  • a sweetener other than the steviol glycoside may be contained in addition to the steviol glycoside composition of the present invention.
  • Such sweeteners include, for example, fructose, sugar, fructose-glucose liquid sugar, glucose, malt sugar, high-fruit sugar liquid sugar, sugar alcohol, oligosaccharide, honey, sugar cane juice (brown sugar honey), water candy, Rakan fruit powder, Rakan fruit.
  • Natural sweeteners such as extracts, licorice powder, licorice extract, somatococcus danieri seed powder, somatococcus danerieri seed extract, and artificial sweeteners such as acesulfam potassium, sucralose, neotheme, aspartame, and saccharin can be mentioned. .. Among them, it is preferable to use a natural sweetener from the viewpoint of refreshing, easy to drink, natural taste, and imparting an appropriate richness, and in particular, fructose, glucose, maltose, sucrose, and sugar are preferably used. .. These sweeteners may contain only one kind or may contain a plurality of kinds.
  • the present invention also relates to foods and drinks containing a steviol glycoside composition produced by the production method of the present invention (hereinafter, also referred to as "foods and drinks of the present invention").
  • the food or drink of the present invention is not particularly limited as long as it contains the steviol glycoside composition of the present invention.
  • food and drink means beverages and foods.
  • the food or drink is a beverage.
  • the amount of the steviol glycoside of the present invention contained in the food or drink of the present invention varies depending on the specific food or drink, but in the case of a beverage, it is preferably approximately 1% by mass to 800% by mass, for example, 20% by mass.
  • ppm to 750 mass ppm 20 mass ppm to 700 mass ppm, 20 mass ppm to 650 mass ppm, 20 mass ppm to 600 mass ppm, 20 mass ppm to 550 mass ppm, 25 mass ppm to 550 mass ppm, 30 mass ppm to 550 mass ppm, 35 mass ppm to 550 mass ppm, 40 mass ppm to 550 mass ppm, 45 mass ppm to 550 mass ppm, 50 mass ppm to 550 mass ppm, 55 mass ppm to 550 mass ppm, 20 mass ppm to 540 mass ppm, 25 mass ppm to 540 mass ppm, 30 mass ppm to 540 mass ppm, 35 mass ppm to 540 mass ppm, 40 mass ppm to 540 mass ppm, 45 mass ppm to 540 mass ppm, 50 mass ppm to 540 mass ppm, 55 mass ppm to 540 mass ppm
  • the food and drink of the present invention may further contain a sweetener other than the steviol glycoside.
  • sweeteners include, for example, fructose, sugar, fructose-dextrose liquid sugar, glucose, malt sugar, sucrose, high fructose liquid sugar, sugar alcohol, oligosaccharide, honey, sugar cane juice (brown sugar honey), water candy, Rakanka.
  • Natural sweeteners such as powder, Rakan fruit extract, licorice powder, licorice extract, somatococcus danieri seed powder, somatococcus daneri seed extract, and artificial sweeteners such as acesulfam potassium, sucralose, neotame, aspartame, and saccharin. Can be mentioned.
  • a natural sweetener from the viewpoint of refreshing, easy to drink, natural taste, and imparting an appropriate richness, and in particular, fructose, glucose, maltose, sucrose, and sugar are preferably used. .. Only one kind of these sweeteners may be used, or a plurality of these sweeteners may be used.
  • the content of sweeteners other than steviol sugars is, in the case of high-sweetness sweets (eg, mogloside V, xylitol and artificial sweeteners), the steviol sugar composition of the present invention and the sweetness other than steviol sugars.
  • the composition ratio with the agent is 1:99 to 99: 1, 5:99 to 95: 5, 10:90 to 90:10, 15:85 to 85:15, 20:80 to 80:20, by weight. It may be 25: 75-75: 25, 30: 70-70: 30, 35: 65-65: 35, 40: 60-60: 40, 45: 65-65: 45 or 50:50.
  • the composition of the steviol glycoside composition of the present invention and the low sweetness sweetener are contained, the composition of the steviol glycoside composition of the present invention and the low sweetness sweetener.
  • the ratios are 1: 1000 to 1: 100, 1: 800 to 1: 100, 1: 700 to 1: 100, 1: 600 to 1: 100, 1: 500 to 1: 100, 1: 400 to weight ratios. It may be 1: 100, 1: 300 to 1: 100, or 1: 200 to 1: 100.
  • the food of the present invention is not particularly limited, but for example, confectionery, bread making, flour, noodles, cooked grains, agricultural / forest processed foods, livestock processed products, marine products processed products, milk / dairy products, fats and oils. -Processed fats and oils, seasonings or other food materials can be mentioned.
  • the beverage of the present invention is not particularly limited, but for example, a carbonated beverage, a non-carbonated beverage, an alcoholic beverage, a non-alcoholic beverage, a beer-taste beverage such as beer or a non-alcoholic beer, a coffee beverage, a tea beverage, and a cocoa beverage. , Nutritional beverages, functional beverages and the like.
  • the beverage of the present invention may be prepared as a packaged beverage in a state of being heat sterilized and packed in a container.
  • the container is not particularly limited, and examples thereof include PET bottles, aluminum cans, steel cans, paper packs, chilled cups, and bottles.
  • heat sterilization the type is not particularly limited, and for example, it can be performed using ordinary methods such as UHT sterilization and retort sterilization.
  • the temperature of the heat sterilization step is not particularly limited, but is, for example, 65 to 130 ° C., preferably 85 to 120 ° C. for 10 to 40 minutes. However, if a sterilization value equivalent to the above conditions can be obtained, there is no problem in sterilization at an appropriate temperature for several seconds, for example, 5 to 30 seconds.
  • the method for producing a food or drink of the present invention is not particularly limited as long as a food or drink containing each of the above components can be obtained.
  • the steviol glycoside composition of the present invention in the method for producing a food or drink of the present invention, is obtained, and the steviol glycoside composition is used as a food or drink or a raw material thereof. Production methods are provided that include and include. Obtaining the steviol glycoside composition of the present invention is as described in "1. Method for producing steviol glycoside composition" above.
  • the addition of the steviol glycoside composition of the present invention to a food or drink or a raw material thereof can be performed at any step in the manufacturing process of the food or drink, for example, when mixing the raw materials of the food or drink, or the food or drink. It may be done at the time of final adjustment of the taste quality of.
  • ⁇ Manufacturing example> 1 Extraction / solid-liquid separation 15 times the amount of ion-exchanged water of dried Stevia leaves (moisture content: 3-4% by weight) was heated to 60 ° C. ⁇ 5 ° C., and the dried Stevia leaves were immersed in the water. Then, extraction was performed for 60 minutes while stirring with a kneader extractor (SKN-R100, manufactured by Sanyu Kikai Co., Ltd.) with a stirring rod at 8 rpm.
  • a kneader extractor (SKN-R100, manufactured by Sanyu Kikai Co., Ltd.) with a stirring rod at 8 rpm.
  • the mixture is filtered through 18 mesh and 140 mesh, cooled with a heat exchanger using cold water, and the filtrate is solid-liquid separated by a disk-type centrifuge (9150 rpm (11601 G), 24 L / min) to be primary. An extract was obtained. Meanwhile, the filtered leaves were extracted again under the same conditions, solid-liquid separated to obtain a transparent secondary extract, and added to the primary extract to prepare a steviol glycoside composition-containing solution.
  • Example 1 The pH dependence of the concentration of steviol glycosides in the steviol glycoside-containing solution containing the stevia extract was evaluated.
  • Fig. 1 shows the changes in the concentrations of the above three types of steviol glycosides when the pH was gradually changed to about 12, and then Fig. 2 shows the changes in the content of rebaugioside A when the pH was lowered to about 7. Shown in.
  • the concentration of each steviol glycoside was determined by liquid chromatography-mass spectrometry (LC / MSMS) under the measurement conditions shown in Table 1 below.
  • the concentration of rebaugioside A increased at around pH 9, and then the concentration increased remarkably at a pH of about 12.
  • the concentrations of rebaugioside D and rebaugioside M did not increase or decrease even when the pH was changed to the basic side. From this result, it was confirmed that the pH-dependent increase in the pH-dependent concentration of rebaugioside A in the steviol glycoside-containing solution was confirmed.
  • Example 2 Regarding rebaugioside A, for which an increase in the concentration in the steviol glycoside-containing solution was confirmed in Example 1, it was evaluated whether or not the increase in the concentration changed depending on the type of alkaline agent.
  • a steviol glycoside-containing solution was prepared in the same manner as in ⁇ Example 1> above.
  • the pH of the steviol glycoside-containing solution was measured and found to be 5.8.
  • the following four samples with different types of alkaline agents were prepared, and the pH was changed to the basic side.
  • Table 2 shows the pH of each sample after pH adjustment.
  • -Sample 1 No alkaline agent (no change in pH)
  • -Sample 2 NaOH (manufactured by Nacalai Tesque, Inc., 4 mol / L sodium hydroxide solution)
  • -Sample 3 KOH (1 mol / L potassium hydroxide solution manufactured by Nacalai Tesque, Inc.)
  • -Sample 4 Baking soda (NaHCO 3 ) (manufactured by Kanto Chemical Co., Inc., product number 58024-17, purity 99.0% or more)
  • the concentration of rebaugioside A was measured for Samples 1 to 4 whose pH was adjusted in the same manner as in Example 1. The results are shown in FIG.
  • Example 3 In order to examine the manufacturing parameters of steviol glycosides in the industrial production, changes in the concentration of steviol glycosides when the pH and retention time were changed were evaluated.
  • a steviol glycoside-containing solution was prepared in the same manner as in ⁇ Example 1> above.
  • the pH of the steviol glycoside-containing solution was adjusted to 9, 10, 11, 11.8, 12, 12.2 and 12.5 using NaOH, and the pH remained unchanged for the time shown in Table 3.
  • Samples adjusted to each pH were kept at room temperature (about 25 ° C.).
  • the pH of each sample was adjusted to about 7 using citric acid, and the concentration of steviol glycoside was measured by the same method as in Example 1.
  • Tables 4 to 9 show the rate of increase in the concentration of steviol glycosides in the sample adjusted to each pH, based on the sample immediately after adjusting the pH to each specified value (0 minutes).
  • Table 4 shows the concentration of rebaugioside A
  • table 5 shows the concentration of rebaugioside C
  • table 6 shows the stevioside
  • table 7 shows the rate of increase in the concentration of lebaugioside F
  • table 8 shows the rate of increase in the concentration of lubusoside
  • table 9 shows the rate of increase in the concentration of rubusoside.

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JP2022517700A JP7678799B2 (ja) 2020-04-27 2021-04-23 ステビオール配糖体組成物の製造方法
CN202610116506.1A CN121867387A (zh) 2020-04-27 2021-04-23 甜菊醇糖苷组合物的制造方法
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Citations (4)

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Publication number Priority date Publication date Assignee Title
JPS5420000A (en) * 1977-07-18 1979-02-15 Japan Organo Co Ltd Purification of stevioside
JPS572656A (en) * 1980-06-05 1982-01-08 Shinnakamura Kagaku Kogyo Kk Decoloration and purification of stevia extract
JPS5775992A (en) * 1980-10-30 1982-05-12 Tama Seikagaku Kk Purification of stevioside
JP2019517823A (ja) * 2016-06-06 2019-06-27 テイト アンド ライル イングレディエンツ アメリカス リミテッド ライアビリティ カンパニーＴａｔｅ ＆ Ｌｙｌｅ Ｉｎｇｒｅｄｉｅｎｔｓ Ａｍｅｒｉｃａｓ Ｌｌｃ グリコシル化ステビオール配糖体組成物およびグリコシル化ステビオール配糖体組成物の製造方法

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US8790730B2 (en) * 2005-10-11 2014-07-29 Purecircle Usa Process for manufacturing a sweetener and use thereof
WO2012166163A1 (en) * 2011-05-31 2012-12-06 Purecircle Usa Stevia composition
US10517321B2 (en) * 2015-07-10 2019-12-31 Sweet Green Fields USA LLC Compositions of steviol multiglycosylated derivatives and stevia components

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5420000A (en) * 1977-07-18 1979-02-15 Japan Organo Co Ltd Purification of stevioside
JPS572656A (en) * 1980-06-05 1982-01-08 Shinnakamura Kagaku Kogyo Kk Decoloration and purification of stevia extract
JPS5775992A (en) * 1980-10-30 1982-05-12 Tama Seikagaku Kk Purification of stevioside
JP2019517823A (ja) * 2016-06-06 2019-06-27 テイト アンド ライル イングレディエンツ アメリカス リミテッド ライアビリティ カンパニーＴａｔｅ ＆ Ｌｙｌｅ Ｉｎｇｒｅｄｉｅｎｔｓ Ａｍｅｒｉｃａｓ Ｌｌｃ グリコシル化ステビオール配糖体組成物およびグリコシル化ステビオール配糖体組成物の製造方法

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