WO2014168018A1 - Composition édulcorante, son procédé de fabrication, et son utilisation - Google Patents

Composition édulcorante, son procédé de fabrication, et son utilisation Download PDF

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Publication number
WO2014168018A1
WO2014168018A1 PCT/JP2014/058922 JP2014058922W WO2014168018A1 WO 2014168018 A1 WO2014168018 A1 WO 2014168018A1 JP 2014058922 W JP2014058922 W JP 2014058922W WO 2014168018 A1 WO2014168018 A1 WO 2014168018A1
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Prior art keywords
sugar
fructose
glucose
psicose
sweetener composition
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PCT/JP2014/058922
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English (en)
Japanese (ja)
Inventor
知也 新谷
諒 吉川
プシュパ キラン グラッパリ
何森　健
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松谷化学工業株式会社
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Priority claimed from JP2013080574A external-priority patent/JP6250946B2/ja
Application filed by 松谷化学工業株式会社 filed Critical 松谷化学工業株式会社
Priority to CN201480020243.XA priority Critical patent/CN105163603A/zh
Priority to KR1020157032013A priority patent/KR102213209B1/ko
Publication of WO2014168018A1 publication Critical patent/WO2014168018A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7004—Monosaccharides having only carbon, hydrogen and oxygen atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/06—Preparations for care of the skin for countering cellulitis
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00—Glucose; Glucose-containing syrups
    • C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K11/00—Fructose
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K13/00—Sugars not otherwise provided for in this class
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K3/00—Invert sugar; Separation of glucose or fructose from invert sugar

Definitions

  • the present invention relates to a method for producing a target sweetener composition using sugar as a raw material, and the produced sweetener composition and use thereof.
  • sugar obtained by hydrolyzing sugar
  • the present invention relates to a method for producing a sweetener composition containing D-psicose in glucose, and fructose, or a mixed sugar mainly composed of glucose and fructose, and the obtained sweetener composition and use thereof. .
  • Isomerized sugar produced by saccharifying starch into a saccharified solution and treating it with glucose isomerase is equivalent to the sweetness of sugar and low in production costs. Widely used as a sweetener, the world's total production of isomerized sugar has reached 17.3 million tons (2009 statistics).
  • a typical production method of this isomerized sugar is that starch is hydrolyzed with an enzyme to obtain a hydrolyzed starch (dextrin), then hydrolyzed with another enzyme to obtain a glucose solution (saccharified solution), and then glucose isomerase. This is a method for isomerizing glucose into fructose.
  • the ratio of glucose to fructose in the isomerized sugar obtained by this production method is usually about 58:42. Furthermore, purified fructose may be added in order to eliminate the lack of sweetness. In this case, the ratio of glucose to fructose is generally about 45:55.
  • Rare sugars have attracted attention because they have various physiological effects, and research has been actively conducted. However, in order to be widely used industrially, these rare sugars are efficiently produced. It is essential. Rare sugars are “naturally-occurring monosaccharides” represented by D-glucose (glucose), which are abundant in nature, among the simple sugars that are the basic units of sugar. Monosaccharide "is defined. The abundance of rare sugar is very small, and the abundance is overwhelmingly small compared to D-glucose (glucose).
  • D-psicose is a D-form of psicose classified as ketohexose and is a hexose.
  • D-allose is a D-form of allose classified as an aldohexose, which is also a hexose.
  • Non-patent Document 1 When D-ketohexose 3-epimerase (Patent Document 1) is allowed to act, it is produced in a yield of 20 to 25%. ⁇ When 3-epimerase (Non-patent Document 3) is allowed to act, it is produced in a yield of about 30%, and when boric acid is used in combination, it is reported that it is produced in a yield of about 60% ( Non-patent document 4).
  • D-allose it is known that L-arabinose isomerase is allowed to act on a solution containing D-psicose to produce D-allose from D-psicose (Patent Document 2).
  • rare sugars are obtained by allowing specific enzymes to act on specific raw sugars, but some other acquisition methods are also disclosed.
  • isomerization reactions of aldoses and ketoses via enediol have been known, which is called Robry de Bruin-fan Eckenstein (Lobry de Bruyn and Alberda van Ekenstein) rearrangement reaction.
  • This isomerization reaction is a reaction that can be isomerized to another sugar by placing a certain sugar under alkaline conditions.
  • Non-Patent Document 5 an isomerized product containing a rare sugar at a concentration exhibiting the above physiological activity.
  • problems such as requiring reaction time that does not match the actual industrial production efficiency, coloring of products due to side reactions such as caramelization, and subsequent purification being difficult. It is considered difficult to use.
  • the disadvantage of sweetness is that isomerized sugar (the composition consisting mainly of glucose and fructose obtained by the decomposition of starch, etc.) is used as a raw material, and the isomerized sugar contains oligosaccharide and has a different composition. Since it is considered that the sweetness and sweetness are different from sugar, it was decided to try to produce a sweetener containing rare sugar from sugar. Since sugar was expensive before the spread of isomerized sugar, it has continued to be replaced by isomerized sugar, but now it is produced around 180 million tons worldwide. Has also become relatively stable.
  • sugar By using sugar as a raw material, the high-quality sweetness of sugar can be used, and since sugar is a disaccharide in which glucose and fructose are combined, it can also be used as a feedstock for glucose and fructose. It is thought that it will become cheaper in cost. Furthermore, as described above, sweeteners containing rare sugars using sugar as a raw material also have an advantage that they have less miscellaneous taste than sweeteners using isomerized sugar as a raw material. Based on these assimilating sugars, it is desired to market sweeteners that are superior in sweetness and physical properties and do not cause these diseases.
  • the present invention provides a novel sweetener, a method for producing the same, and a use thereof, which overcome the above-mentioned disease risk by ingesting isomerized sugar, and defects in the production process or taste quality of rare sugar-containing syrup. It is something to be offered.
  • the inventors of the present invention have made extensive studies to solve the above-mentioned problems.
  • an acid and / or enzyme is allowed to act on sugar under specific conditions to produce glucose (D-glucose) and fructose (D-fructose).
  • D-glucose glucose
  • D-fructose fructose
  • the present inventors have found that a sweetener composition having a composition can be obtained, and have completed the present invention.
  • the present invention comprises the following methods (1) to (9) for producing a sweetener composition.
  • (1) Using sugar as a raw material to obtain a mixture of sugar, D-glucose and D-fructose, or a mixture of D-glucose and D-fructose by hydrolysis of the raw sugar, and the sugar A mixture of rare sugars including sugar, D-glucose, D-fructose and at least D-psicose, or D-glucose, D-fructose and at least D-psicose, which are end products by isomerizing the hydrolyzate
  • the raw material sugar hydrolysis step is a step of isomerizing a sugar hydrolyzate by decomposition using an acid and / or an enzyme, and an alkali isomerization, an isomerization using calcium ion catalysis and / or The manufacturing method of the sweetener composition of the said (1) description performed by enzyme isomerization.
  • Alkaline isomerization produces rare sugars including D-psicose, D-allose, D, L-sorbose, D-tagatose, and D-mannose.
  • the final product consists of these monosaccharides, sugar,
  • the method for producing a sweetener composition according to the above (2) which is a mixture of D-glucose and D-fructose or a mixture of D-glucose and D-fructose.
  • Enzymatic isomerization produces only D-psicose from fructose, and the final product is a mixture of D-psicose and sugar, D-glucose and D-fructose, or D-glucose and D-
  • the present invention comprises the following sweetener composition (11), foods and drinks (12) and (13), pharmaceuticals (14) and (15), quasi drugs and cosmetics.
  • (11) A sweetener composition obtained by the production method according to any one of (1) to (10) above.
  • (12) A food or drink comprising the sweetener composition according to (11) above.
  • (12) The food or drink according to (12) above, which is labeled to suppress an increase in body weight and an increase in body fat accumulation.
  • a pharmaceutical, quasi-drug, or cosmetic comprising the sweetener composition as described in (11) above.
  • sugar is used as a raw material, the high-quality sweetness of sugar can be used, and since sugar is a disaccharide in which glucose and fructose are combined, it can also be used as a feedstock for glucose and fructose.
  • a sweetener that is cheaper than isomerized sugar as a raw material, is excellent in sweetness and physical properties, and does not cause these diseases, based on these assimilating sugars.
  • a new sweetener, a method for producing the same, and a use thereof which overcomes the risk of morbidity associated with diabetes and obesity caused by ingestion of isomerized sugar, and defects in the production process or taste quality of rare sugar-containing syrup can do.
  • the present invention it is possible to provide a sweetener composition close to the taste of sugar containing rare sugars such as sugar, D-glucose, D-fructose, and D-psicose in a well-balanced manner.
  • the present invention is a production method that is excellent not only in physical properties but also in cost performance, it can be used inexpensively and safely for pharmaceuticals or quasi drugs, oral compositions, cosmetics and foods, and food additives.
  • An agent can be provided.
  • the product of the present invention is a sweetener with better taste and functionality than isomerized sugar or sugar itself, it has anti-obesity agents, antifeedants, insulin resistance improvers, Or it becomes possible to give the quality as a low-calorie sweetener.
  • the manufacturing flow of the sweetener containing rare sugar which uses sugar as a raw material is shown.
  • the area under a blood glucose level curve when each sweetener composition of the present invention is ingested by a human is shown.
  • the area under the insulin concentration curve when a human being ingested each sweetener composition of the present invention is shown.
  • the present invention relates to a sweetener composition using sugar as a raw material and containing sugar, D-glucose, D-fructose, rare sugar (D-psicose, etc.), etc. in a specific composition ratio, a method for producing the same, and use thereof Consists of. It is possible to adjust the sugar content in the finally obtained sweetener composition by the degree of hydrolysis reaction of the raw sugar, and finally, depending on the degree of isomerization reaction in the next step. Although the content of rare sugar in the resulting sweetener composition can be adjusted, in order to obtain the taste-quality effect of the present invention, the sugar in the final sweetener composition should be 3 to 80%.
  • D-psicose is contained in an amount of 3% or more (hereinafter, unless otherwise specified,% indicates mass% in the sugar composition (solid)), but the sweetness prepared so as not to contain sugar. Even when the compositions are compared, a sweetener composition with less miscellaneous taste is obtained by using sugar as a raw material than when isomerized sugar is used as a raw material.
  • a taste effect is obtained when the D-psicose content in the sweetener composition of the present invention is 3% or more, but the alkali isomerization described later was selected as the isomerization method performed after the decomposition of sugar.
  • D-mannose, D-sorbose, L-sorbose and the like are produced in addition to rare sugars such as D-allose, D-tagatose, and D-altrose other than D-psicose.
  • the alkali isomerization reaction proceeds excessively, the coloration proceeds remarkably and subsequent purification is difficult. Therefore, the composition of D-psicose and D-allose is determined as the degree of isomerization reaction that does not cost this purification step.
  • the sweetener composition of the present invention exhibits characteristics that can be used as an anti-obesity agent, an antifeedant, and an insulin resistance improving agent. It can also be used.
  • the sugar used as a raw material in the present invention may be any sugar containing D-glucose (glucose) and D-fructose (fructose) combined.
  • Different manufacturing methods such as sugar and dense sugar, and product categories such as white disaccharide, medium disaccharide, granulated sugar, super white sugar, tri-warm sugar, invert sugar, sugar cube, rock sugar, brown sugar, red sugar, and Wasanbon
  • any sugar solution in the sugar refining process may be used.
  • oligosaccharides containing three or more sugars including sugar can be used as the raw material sugar.
  • the concentration of the raw sugar solution is 3 to 80%, preferably 10 to 60%, and more preferably 20 to 40%.
  • the concentration of the raw sugar solution is 3 to 80%, preferably 10 to 60%, and more preferably 20 to 40%.
  • the concentration of the raw sugar solution is 3 to 80%, preferably 10 to 60%, and more preferably 20 to 40%.
  • the concentration of the raw sugar solution is 3 to 80%, preferably 10 to 60%, and more preferably 20 to 40%.
  • the concentration of the raw sugar solution is 3 to 80%, preferably 10 to 60%, and more preferably 20 to 40%.
  • about 3 to 40% is more preferable.
  • the raw material having a sugar concentration of 100% that is, the powder or the powder is produced by spraying acid or alkali. Is also possible.
  • the raw sugar hydrolysis step is performed by decomposition using an acid and / or an enzyme.
  • An acid acidic solution
  • Decomposition with an acid is carried out using an inorganic acid, sulfonic acid or carboxylic acid as the acidic solution.
  • the acidic solution includes inorganic acids (hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, hypochlorous acid, perchloric acid, phosphoric acid, boric acid, fluorosulfonic acid, etc.), sulfone Acids, carboxylic acids (acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, etc.) can be used as appropriate, but hydrochloric acid is preferred from the viewpoint of safety and cost.
  • the optimum acid concentration depends on the reaction time and temperature, but it is usually preferable to contain about 0.01 to 5 mol / l in the raw sugar solution.
  • the acid decomposition reaction temperature is preferably 20 ° C. or higher, more preferably 30 ° C. to 100 ° C.
  • an enzyme can be used instead of the above acid decomposition.
  • Degradation using an enzyme is performed using invertase.
  • the enzyme include saccharase; invertase (IUPAC-IUB strain name is ⁇ -D-fructofuranosidase (EC 3.2.1.26)), and the strain origin is particularly limited.
  • the enzyme concentration varies depending on the substrate concentration and reaction time, it is usually preferable to use 100 unit / mg enzyme at 0.00075-0.003% (w / w) relative to the substrate.
  • the reaction temperature of the enzyme is preferably 20 ° C.
  • invertase enzyme for immobilization, commercially available invertase is dissolved in a buffer solution (pH 7) and allowed to pass through the column-filled resin at 4 ° C., so that the invertase enzyme protein is bound to the ion exchange resin. Get the enzyme.
  • hydrolysis of raw sugar can be performed by either acid or decomposition using invertase, but in general, it can be used properly depending on the composition of the product to be obtained. Only one of them can be used, or they can be used together.
  • the step of isomerizing the sugar hydrolyzate is performed by alkali isomerization, isomerization using calcium ion catalysis and / or enzymatic isomerization.
  • enzyme isomerization will be described.
  • a method using an isomerization (epimerization) enzyme such as tagatose-3 epimerase or psicose-3 epimerase can be selected.
  • the origin of the microorganism strain from which the isomerase, tagatose-3-epimerase or psicose-3 epimerase, is obtained is not particularly limited, but is a safe species that can also be used for food. From high-yield D-fructose to D-psicose from bacterial species that are listed on the existing additive list that is approved for use in food production It is desirable to be a bacterium belonging to the genus Arthrobacter (Patent Document 5) that produces a novel ketose 3-epimerase that catalyzes isomerization, more preferably an genus Arthrobacter globiformis, and Arthrobacter globiformis M30 (Deposit number NITE BP-1111) is more preferable.
  • the reaction temperature for carrying out the enzyme isomerization is preferably 20 ° C. or higher, more preferably 30 ° C. to 80 ° C. Practically, around 45 ° C. is preferable.
  • the above Arthrobacter globiformis will be described.
  • the ketose 3-epimerase that can be used in the present invention belongs to the genus Arthrobacter , cultivates a microorganism having the ability to produce ketose 3-epimerase, and ketose 3-epimerase from the cells grown in the culture solution. It can be prepared by collecting epimerase.
  • the Arthrobacter globiformis M30 (deposition number NITE BP-1111) strain and mutants thereof can be advantageously used.
  • the M30 strain has a relatively high ability to produce ketose 3-epimerase and is suitable for obtaining the enzyme of the present invention.
  • the M30 strain is based on NITE P-1111 deposited on June 22, 2011 at the Japan Patent Evaluation Depositary Center for Product Evaluation Technology (2-5-8 Higashi Kazusa Kamashika, Kisarazu City, Chiba, Japan). A transfer to the deposit under the Budapest Treaty was requested on May 2, 2012, and the deposit was made internationally under the deposit number NITE BP-1111.
  • a preferred ketose 3-epimerase that can be used in the present invention is a ketose 3-epimerase that can be obtained from a microorganism belonging to the genus Arthrobacter and has the following substrate specificities (A) and (B). .
  • A) Epimerize position 3 of D- or L-ketose to produce the corresponding D- or L-ketose.
  • B) Among D- or L-ketoses, the substrate specificity for D-fructose and D-psicose is the highest.
  • the ketose 3-epimerase derived from Arthrobacter globiformis M30 has a subunit molecular weight of about 32 kDa by SDS-PAGE, a molecular weight of 120 kDa by gel filtration, and a subunit molecular weight of 120 kDa. It has a 32 kDa homotetramer structure, has the following physicochemical properties (a) to (e), and has the following substrate specificity: ⁇ 8. (See Patent Document 5).
  • Mn 2+ divalent manganese ions
  • Co 2+ divalent cobalt ions
  • Ca 2+ calcium
  • Mg 2+ magnesium ions
  • the relative activity when D-fructose is used as a substrate is 43.8%, 2. 100% activity when D-psicose is used as a substrate, 3.
  • the relative activity when using D-sorbose as a substrate is 1.13%, 4).
  • the relative activity when D-tagatose is used as a substrate is 18.3%, 5.
  • the relative activity when using L-fructose as a substrate is 0.97%, 6).
  • the relative activity when L-psicose is used as a substrate is 21.2%, 7).
  • the relative activity when using L-sorbose as a substrate is 16.6%, 8.
  • the relative activity is 44.0% when L-tagatose is used as a substrate.
  • the activity for each ketose is shown as a relative activity, where the epimerization activity of D-psicose is 100.
  • the crude enzyme solution can be collected as a crude enzyme solution from a solution of disrupted cells obtained by digesting the polysaccharide components present on the cell walls of the body to destroy the cells.
  • the crude enzyme solution is passed through the ion-exchange resin packed in the column at a low temperature (4 ° C), the crude enzyme protein is bound to the ion-exchange resin, purified water is passed through and washed, and the immobilized enzyme is washed.
  • An immobilization system that can withstand continuous production in terms of stability (maintenance of activity) completely satisfactory for commercial production was obtained. A large amount of epimerization reaction can be continuously performed using the obtained immobilized enzyme.
  • active ketose 3-epimerase is added to the supernatant obtained after heat treatment at 40 to 70 ° C. for 5 to 60 minutes after crushing treatment with 0.1 to 2% sodium chloride and lysozyme. Since it was found that many can be obtained, a separate patent application is planned.
  • the means for isomerization after decomposing the raw material sugar is not limited to the isomerization (epimerization) by the above enzyme, and a method utilizing alkali isomerization can also be selected.
  • alkaline solution used for the alkali isomerization reaction include sodium hydroxide, potassium hydroxide, ammonia, calcium hydroxide, calcium oxide, barium hydroxide, lead hydroxide, strontium hydroxide, magnesium hydroxide, hydroxide Although tin and aluminum hydroxide are mentioned, sodium hydroxide and calcium hydroxide are preferable in terms of safety and cost.
  • the optimum alkali concentration depends on whether or not an ion exchange resin is used in combination, but usually it is preferably contained in a hexose (hexasaccharide) solution in an amount of 0.005 mol / l or more.
  • the reaction temperature for the alkali isomerization is preferably 20 ° C. or higher, more preferably 30 ° C. to 100 ° C.
  • isomerization using the catalytic action of calcium ions is carried out by advancing the isomerization reaction of hexose in the presence of a calcium salt that generates calcium ions.
  • Patent Document 3 describes a method for isomerizing glucose using calcium chloride.
  • an isomerization reaction using a catalytic action of calcium ions can also be performed.
  • the isomerization reaction of hexose proceeds in the presence of a calcium salt that generates calcium ions, for example, calcium chloride, that is, for example, a sugar composition containing D-psicose and D-allose from fructose. Can be manufactured.
  • the calcium salt is desirably in the presence of an alkali, and is preferably contained in the sugar solution by 0.005 mol / l or more. In a system in which a calcium salt is present, the coexistence of a basic ion exchange resin is not always necessary.
  • the sugar content in the final product is adjusted according to the degree of hydrolysis of the raw sugar.
  • the final product includes sugar, D-glucose, D-fructose, and a rare sugar containing at least D-psicose in a specific proportion, or includes D-glucose, D-fructose, and at least D-psicose.
  • Rare sugar was included at a specific composition ratio. Alkaline isomerization produces rare sugars including D-psicose, D-allose, D, L-sorbose, D-tagatose, and D-mannose, and the final products are these simple sugars, sugars, glucose, And a mixture of fructose.
  • Isomerization using calcium ion catalysis produces rare sugars including D-psicose and D-allose from fructose, and the final product is a mixture of these monosaccharides, sugar, glucose and fructose.
  • Enzymatic isomerization produces only D-psicose from fructose and the final product is a mixture of D-psicose, sugar, glucose and fructose, or a mixture of D-psicose, glucose and fructose .
  • alkaline isomerization or enzymatic isomerization can be selected depending on the amount of hydrolysis and the composition of the product to be obtained. Either one can be used or both can be used. Can do.
  • the sugar composition of the composition it is possible to adjust the sugar composition of the composition to be produced by appropriately changing the raw sugar concentration, acid concentration, alkali concentration, enzyme concentration, reaction temperature, etc. A composition adjusted to have physical properties can be obtained.
  • sugar, glucose, fructose, rare sugar and the like can be appropriately added and adjusted. If it is desired to increase the reaction time, productivity can be improved by applying pressure.
  • ion exchange resin, activated carbon, and purification by filtration usually used in the sugar industry can be appropriately used. Separation can be removed by column chromatography, or precipitation separation can be performed using an agent chelating with sugar. According to the method of the present invention, significant browning does not occur before separation by column chromatography, but generally known purification steps such as deodorization and decolorization processes using activated carbon are added to the previous stage in consideration of the lifetime of the column. You can also.
  • pseudo mobile phase chromatography is optimal for this purpose, but is not particularly limited.
  • the separation step it is possible to separate only rare sugars from the resulting reaction solution and appropriately add to the mixed sugars to obtain the target composition.
  • the remaining sugar solution can be reused. That is, a continuous plant can be constructed by recombining the residual sugar solution with the raw material sugar and guiding it again to the hydrolysis reaction step, so that the manufacturing process can be simplified.
  • a preferred embodiment of the present invention is shown schematically in FIG.
  • Step 1 is a tank for dissolving raw material sugar
  • Step 2 is a tank for acid hydrolysis of raw material sugar
  • 3 is an invertase-immobilized column for hydrolyzing raw material sugar.
  • steps 4 and 5 are an isomerization step with an alkali or an isomerization step with an enzyme, and any of them may be used.
  • Step 6 is a general purification step used for sugar purification of ion exchange resins, activated carbon, filters, and the like. Further, the process can proceed to step 7 to separate and acquire a rare sugar single product. When the rare sugar is separated and acquired in step 7, the remaining sugar, glucose, and fructose mixed sugar solution can be returned to step 1 and reused as the raw sugar.
  • [Use of final product] it is possible to obtain a sweetening composition having a low sweetness intensity and a little miscellaneous taste using sugar as a raw material.
  • a sweetening composition that enhances flavor release using sugar as a raw material can be obtained.
  • the ratio of sugar is 10 to 75 parts.
  • a sweetening composition having a feeling and a sweetness balance can be obtained.
  • this invention relates to the food / beverage products which used the said sweetener composition, the food / beverage products which attached
  • the present invention relates to a pharmaceutical comprising a sweetener composition, a quasi-drug, a cosmetic, a pharmaceutical for suppressing an increase in body weight and an increase in body fat accumulation, a quasi-drug, and a cosmetic.
  • the form is not particularly limited, and the form as it is, the form diluted with a solvent such as oil, the emulsion form, or common in the food industry Any form such as a form to which a carrier used in the preparation is added may be used.
  • target foods and drinks using the sweetener composition of the present invention include the following. That is, confectionery (pudding, jelly, gummy candy, candy, drop, caramel, chewing gum, chocolate, pastry, butter cream, custard cream, cream puff, hot cake, bread, potato chips, french fries, popcorn, biscuits, crackers, pie , Sponge cakes, castella, waffles, cakes, donuts, biscuits, cookies, rice crackers, rice crackers, rice cakes, manju, candy, etc., dry noodle products (macaroni, pasta), egg products (mayonnaise, fresh cream), beverages (functionality) Beverages, lactic acid beverages, lactic acid bacteria beverages, concentrated milk beverages, fruit juice beverages, fruitless beverages, fruit beverages, transparent carbonated beverages, carbonated beverages with fruit juice, fruit colored carbonated beverages, alcoholic beverages, beer-like beverages), luxury products (green tea, Tea, inn Tanto coffee, cocoa, canned coffee drinks), dairy products (ice cream, yogurt, coffee milk, butter, butter sauce, cheese, fermented milk, processed
  • the food and drink can also be used as functional foods, nutritional supplements, or health foods.
  • the form is not particularly limited.
  • proteins such as milk proteins with high amino acid balance, soy protein, egg albumin, etc., their degradation products, egg white oligopeptides, soybean hydrolysates, It can be used according to a conventional method together with a mixture of amino acids alone.
  • forms such as a soft capsule, a tablet, and a film.
  • Examples of the above dietary supplements or functional foods include liquid foods, semi-digested nutritional foods, ingredient nutritional foods, drinks, capsules, sugars, fats, trace elements, vitamins, emulsifiers, fragrances, etc.
  • processing forms such as enteral nutrients.
  • foods and drinks such as sports drinks and nutritional drinks, for the purpose of improving nutritional balance and flavor, further nutritional additives such as amino acids, vitamins, minerals, sweeteners, spices, A fragrance
  • the sweetener composition of the present invention can be used as a food material or food additive for the purpose of improving abnormal carbohydrate metabolism and / or abnormal lipid metabolism, and when used as a drug, It can be used in the form of capsules, solid agents such as powders and granules for use in beverages, semi-solid bodies such as jelly, liquids such as drinking water, and high-concentration solutions used after dilution. Furthermore, the sweetener composition of the present invention can be appropriately added to foods and drinks to provide health foods or sick foods for the purpose of improving abnormal sugar metabolism and / or abnormal lipid metabolism. Vitamins, carbohydrates, pigments, fragrances and the like to be added can be appropriately blended.
  • the form of the capsule may be liquid, solid, or a soft capsule encapsulated by gelatin or the like.
  • the capsule is dissolved by adding water to raw material gelatin, and a plasticizer ( A gelatin film prepared by adding glycerin, D-sorbitol, etc.).
  • the sweetener composition of the present invention can be applied to feed for livestock, poultry and pets.
  • livestock feeds such as dry dog food, dry cat food, wet dog food, wet cat food, semi-moist dock food, poultry feed, cattle, and pigs.
  • livestock feeds such as dry dog food, dry cat food, wet dog food, wet cat food, semi-moist dock food, poultry feed, cattle, and pigs.
  • the feed itself can be prepared according to a conventional method.
  • These therapeutic agents and prophylactic agents include non-human animals, for example, domestic mammals such as cattle, horses, pigs and sheep, poultry such as chickens, quails and ostriches, pets such as reptiles, birds and small mammals, It can also be used for farmed fish.
  • the sweetener composition according to the present invention is a high-intensity sweetener such as aspartame, sucralose, acesulfame K, stevia, monatin, monelin, miraculin, sugar alcohols such as sorbitol, xylitol, erythritol, lactitol, maltitol, ketose, Sweeteners can be prepared by adjusting the sweetness by further mixing with a sweetener such as aldose.
  • a sweetener such as aldose.
  • the sweetener composition of the present invention is a food, health food, patient food, food material, health food material, patient food material, food additive, health food additive, patient food additive, beverage, Health drinks, patient drinks, drinking water, health drinks, patient drinks, medicines, pharmaceutical ingredients, feeds, livestock and / or feeds for patients, pharmaceuticals or quasi drugs, oral compositions, cosmetics It is possible to provide a sweetener composition that can be used for all foods that require sweetness or functionality, such as food additives, and can be used safely and conveniently.
  • a sugar composition containing a specific hexose focusing on the physiological action of the specific hexose, and a specific health food, pharmaceutical or quasi-drug using the same, and oral use
  • a composition, cosmetics, etc. can be provided.
  • it contains sugar, glucose, fructose, and D-psicose, and when an alkali isomerization reaction is selected as a means for isomerization, D-allose Can be obtained, which is superior in taste, physical properties, and physiologically, and is therefore superior in taste to assimilable sugars such as isomerized sugar and sugar.
  • the characteristics as a sweetener, anti-obesity agent, antifeedant, insulin resistance improver, low calorie sweetener, blood pressure suppressor.
  • the obtained sweetener composition of the present invention is different from the monosaccharides known so far in that it has a low calorie and has an appetite suppressing effect, and therefore has a new anti-obesity effect and the like. It has the characteristics.
  • the sweetener composition of the present invention can be widely used as a low calorie sweetener because the sweetness is close to sugar and the calories are low.
  • the said food / beverage products can be processed and manufactured by mix
  • the novel sugar composition of the present invention can be expected to be widely used as a sweetener for soft drinks and other beverages, and can be used in foods, pharmaceuticals or quasi drugs, oral compositions, and cosmetics. There is expected.
  • the sugar composition obtained by acid hydrolysis was confirmed at 90 ° C. under the acid hydrolysis conditions for a sugar 80% (w / w) solution. As a result, decomposition was confirmed.
  • the sugar composition obtained by hydrolysis with hydrochloric acid having a hydrochloric acid concentration of 0.01 to 5 mol / l is used. When confirmed, decomposition was confirmed.
  • invertase manufactured by DSM; 200 U / mg
  • an ion exchange resin resin: IRA904, column inner diameter 1.5 cm, immobilized enzyme 1500 U / wet weight (g)
  • a 30% sugar solution was fed and reacted at a temperature of 45 ° C., a feeding speed of 3 ml / min, a speed of 2 ml / min, and a speed of 1 ml / min.
  • the reaction solution eluted from the column was sampled and subjected to HPLC analysis.
  • Table 4 shows the sugar composition (%) of the obtained hydrolyzate.
  • Example F Enzymatic Isomerization of Sugar Enzyme Hydrolyzate>
  • the hydrolyzate obtained in the experimental sections C1, C3, C4, and C8 in Experimental Example 2 was extracted from Arthrobacter globiformis M30 (deposit number NITE BP-1111) and used for the enzyme immobilized on the ion exchange resin.
  • An isomerization reaction was performed (the immobilization technique is shown below).
  • Isomerization is performed by feeding the solution to a 50 ml ion exchange resin (resin: Amberlite IRA900J, column inner diameter 1.5 cm) at a temperature of 45 ° C. and a feed rate of 0.5 ml / min, and sampling the column eluate.
  • the sugar composition was analyzed.
  • the sugar composition (%) of the obtained enzyme isomerization reaction product is shown in Table 6 below.
  • E1, E3, F1, and F3 had a good balance between richness and sweetness. That is, the sugar is not completely hydrolyzed to the end, and the presence of D-psicose in this composition makes it more sweet compared to the sugar composition obtained by isomerization after complete hydrolysis of the sugar. It became clear that richness and balance improved. Moreover, when the ratio of the sugar in a sweetener is 10 parts or less, or when it exceeds 75 parts, a thick feeling and the tendency to lose
  • H1 D-psicose 10: erythritol 30: sucralose 0.1
  • H2 D-psicose 60: erythritol 20: sucralose
  • High-intensity sweeteners have a bad aftertaste (there is an odd taste) compared to low-intensity sweeteners.
  • sucralose which is a high-intensity sweetener
  • Aftertaste was bad (Table 7).
  • High-intensity sweeteners have a long-lasting sweetness and off-flavor, and are often used in combination with sugar alcohols that have a refreshing sweet taste. It is very difficult to give the sweetness a unity (a sense of unity), and there is a problem that the sweetness of each sweetener is felt separately.
  • E1, E3, F1 which are the sweetening compositions of the present invention
  • F3 and F3 had a coherent and highly desirable sweetness without any drawbacks such as off-taste. That is, a sweetener containing a rare sugar containing at least D-psicose in a sweet composition comprising sugar, glucose, and fructose is obtained by adding D-psicose to a sweet composition comprising a sugar alcohol and a high-intensity sweetener.
  • composition I1 (glucose 50: fructose 38: D-psicose 12). It was.
  • a commercially available general isomerized sugar (glucose 50: fructose 45: oligosaccharide 5) is isomerized with an isomerase according to Experimental Example F, and composition I2 (glucose 50: fructose 34: D-psicose 11: Oligosaccharide 5) was obtained.
  • the taste of each sugar composition was subjected to sensory evaluation by the same evaluation method as described above ( ⁇ Sensory evaluation 1 of sugar composition>). However, the evaluation items were “strength of the start of sweet taste” and “miscellaneous taste”.
  • I1 was superior as a sweetener in terms of not only having a strong start of sweetness compared to I2, but also having less miscellaneous taste. From this, it can be said that the isomerized sweet composition obtained by the above method using sugar as a raw material is superior to the isomerized sweet composition obtained by the above method using isomerized sugar as a raw material as a sweetener. This is probably because contaminants such as oligosaccharides contained in commercially available general isomerized sugars slightly suppress the onset of the sweet taste and make it feel uncomfortable. From this result, it can be said that the sweet taste composition obtained using sugar as a raw material is more preferable as a sweetener than using a commercially available general isomerized sugar as a raw material.
  • Example 2 ⁇ Preparation of acidic beverage and sensory evaluation 1> The sugar compositions (E1, E3, F1, F3) obtained in the above Experimental Examples E and F, G1 (glucose 45: fructose 42: D-psicose 7) and G2 (glucose) prepared by appropriately mixing each sugar 51: Fructose 36: D-psicose 10) Using each saccharide composition, an acidic beverage was prepared according to the formulation shown in Table 9. About this acidic drink, the sensory evaluation by five panelists was performed similarly to Example 1. The results are shown in Table 10.
  • Acidic beverages using E2 and F4 sugar compositions had better richness and sweetness balance than acidic beverages using sugar compositions lacking either sugar or D-psicose.
  • the acidic beverage using the sweet composition containing sugar was better in both aftertaste and sweetness as compared with the acidic beverage using the sweet composition containing no sugar.
  • a saccharide sweetener and a high-intensity sweetener together.
  • a good richness and sweetness balance are obtained by including sugar. be able to.
  • the acidic beverage using F3 has a more balanced sweetness than the acidic beverage using G1, and the flavor is enhanced. From this, it was found that the sweetening composition containing D-psicose and sugar has not only a good sweetness balance but also good flavor standing.
  • Example 3 Crystallization at a low temperature of the sugar solution is a major obstacle during storage and transportation. Therefore, the number of days for crystallization of the composition containing the present sugar was compared with the composition containing no sugar. Specifically, a 70% (w / w) solution was stored at 4 ° C., and the number of days required for crystallization during refrigeration storage of compositions E3, F1, and G2 was measured. As a result, E3, F1, and the number of days required for crystallization were larger than G2, and improvement was recognized. From this, the tendency for the composition containing sugar to be harder to crystallize than the composition containing no sugar was recognized, and it became clear that it was effective during storage and transportation.
  • Example 4 ⁇ Effects of the sweetener composition of the present invention on blood glucose level and insulin secretion in humans>
  • the sweetener composition obtained by the production method of the present invention that is, the blood sugar level and insulin secretion when each human sweetener composition obtained by allowing alkali to act on the enzyme hydrolyzate of sugar is ingested by humans.
  • the effect was examined.
  • Table 16 shows the sugar composition of each sweetener composition (J1 to J4) used.
  • J1 is a raw material for obtaining each sweetener composition (manufactured by Mitsui Sugar Co., Ltd., trade name “Kami Shirasu”), and this was used as a comparative control group.
  • Each of the sweet tastes shown in Table 16 is given to 6 healthy persons who have no smoking habits (average age 34.7 years old, 4 men, 2 women, average BMI 22.1 kg / m2, average fasting blood glucose 92.4 mg / dL) After ingesting a 38.5% aqueous solution of the food composition, changes in blood glucose level and insulin concentration were measured. The test was conducted by a single blind crossover method in which an aqueous sugar composition solution described in Table 16 was ingested. Each test was conducted at an interval of about one week. First, the subjects were fasted from 12 hours before the test day, and then blood was collected on an empty stomach.
  • FIG. 2 shows the numerical results of the area under the blood glucose level curve obtained by plotting the elapsed time (minutes) from the intake of the aqueous solution of each sweetener composition on the horizontal axis and plotting the blood glucose level for each elapsed time on the vertical axis.
  • J3 was reduced to about 81.0% of J1
  • J4 was reduced to 70.0% of J1
  • J2 was reduced to about 93.1% of J1, but no significant difference was observed.
  • the numerical value of the area under the blood glucose level curve is 50.4 mg ⁇ h / dL for J1, 46.9 mg ⁇ h / dL for J2, 40.8 mg ⁇ h / dL for J3, and 35.3 mg ⁇ h / dL for J4. Met.
  • the results of the area under the insulin concentration curve are shown in FIG. J2 was reduced to about 70.2% of J1, and J4 was reduced to 61.7% of J1, indicating that insulin secretion was significantly suppressed.
  • J3 was reduced to about 80.9% of J1, but no significant difference was observed.
  • the area under the insulin curve was 28.2 mU ⁇ h / L for J1, 19.8 mU ⁇ h / L for J2, 22.8 mU ⁇ h / L for J3, and 17.4 mU ⁇ h / L for J4. .
  • the sweetener compositions J2, J3 and J4 of the present invention were ingested, it was estimated that the same increase in blood glucose level and increase in insulin secretion amount as in J1 were observed. Was particularly significantly reduced, and in J3, the increase in blood glucose level was particularly significantly suppressed. In J4, both the blood glucose level and the amount of insulin secretion were significantly reduced. That is, the sweetener composition of the present invention can be used as a sweetener that is imparted with an effect of suppressing an increase in blood glucose level and / or insulin secretion amount when ingested, although it has a sweetness almost equivalent to that of sugar. .
  • the sweetener of the present invention has a composition in which sugar is used as a raw material and the sugar is left in the finally obtained sweetener composition. Even when sugar is added as appropriate after obtaining a sweetener composition that does not remain, a sweetener composition having the same composition can be obtained. Therefore, for reference, the sugar composition produced by the method described in Table 2010/113785 (as the composition is equivalent to the one obtained by removing the sugar portion of the sweetener composition of the present invention) When a sugar composition corresponding to the above-mentioned J2 to J4 obtained by adding A was prepared and a human test similar to that of Example 4 was performed, almost the same results were obtained.
  • the sweetener composition of the present invention is a sweetener composition having an effect of suppressing blood sugar level and / or insulin secretion, and can be said to be a sweetener composition that can be expected to reduce the risk of developing diabetes.
  • continuous intake of the sweetener may ultimately reduce body fat accumulation.
  • the novel sugar composition of the present invention can be expected to be widely used as a sweetener for soft drinks and other beverages, and can be used in foods, pharmaceuticals or quasi drugs, oral compositions, and cosmetics. There is expected. Moreover, since the novel sugar composition of the present invention can be mass-produced and provided at a low production cost, it is expected that the application range will be further expanded.

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Abstract

Le problème décrit par la présente invention concerne un nouvel édulcorant, qui est exempt de risque de maladies provoquées par l'ingestion de sucres isomérisés et qui résout les problèmes rencontrés durant la production d'un sirop contenant du sucre rare ou les inconvénients liés au goût, son procédé de fabrication, et son utilisation. La solution selon l'invention porte sur un procédé de fabrication d'une composition édulcorante, ledit procédé comprenant : le traitement du saccharose avec un acide et/ou une enzyme sous des conditions spécifiques ce qui permet de décomposer de manière efficace le saccharose en glucose et fructose ; et ensuite l'isomérisation du mélange obtenu en utilisant un agent alcalin et/ou une enzyme sous des conditions spécifiques d'une manière permettant au produit isomérisé résultant de contenir du D-psicose principalement sous la forme d'un sucre rare de sorte que le produit comprenne, sous un rapport de composition spécifique, du saccharose, du D-glucose, du D-fructose et du(des) sucre(s) rare(s) contenant au moins du D-psicose, ou le produit comprend, sous un rapport de composition spécifique, du D-glucose, du D-fructose et du(des) sucre(s) rare(s) contenant au moins du D-psicose.
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JP7508112B2 (ja) 2018-11-08 2024-07-01 国立大学法人 香川大学 希少糖含有組成物の製造方法および希少糖含有組成物

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WO2016186338A1 (fr) * 2015-05-15 2016-11-24 주식회사 삼양사 Composition de sucre mélangé à du psicose à qualité de sucrosité et cristallisation améliorées
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CN105219756A (zh) * 2015-07-17 2016-01-06 江南大学 一种l-鼠李树胶糖-1-磷酸醛缩酶在催化合成稀有糖中的应用
EP3138413A1 (fr) 2015-08-14 2017-03-08 Pfeifer & Langen GmbH & Co. KG Sucres rares
JPWO2020096006A1 (ja) * 2018-11-08 2021-09-24 国立大学法人 香川大学 希少糖含有組成物の製造方法および希少糖含有組成物
JP2021151234A (ja) * 2018-11-08 2021-09-30 国立大学法人 香川大学 希少糖含有組成物の製造方法および希少糖含有組成物
WO2020096006A1 (fr) * 2018-11-08 2020-05-14 国立大学法人香川大学 Procédé de production d'une composition contenant des sucres rare et composition correspondante
JP7002159B2 (ja) 2018-11-08 2022-02-08 国立大学法人 香川大学 希少糖含有組成物の製造方法および希少糖含有組成物
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JP7508112B2 (ja) 2018-11-08 2024-07-01 国立大学法人 香川大学 希少糖含有組成物の製造方法および希少糖含有組成物
CN113825410A (zh) * 2019-03-29 2021-12-21 Cj第一制糖株式会社 混合糖组合物
EP3925453A4 (fr) * 2019-03-29 2022-05-04 CJ Cheiljedang Corporation Composition de saccharide mixte

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