WO2010032510A1 - Nouveau glucane ramifié, son procédé de production et son utilisation - Google Patents

Nouveau glucane ramifié, son procédé de production et son utilisation Download PDF

Info

Publication number
WO2010032510A1
WO2010032510A1 PCT/JP2009/057609 JP2009057609W WO2010032510A1 WO 2010032510 A1 WO2010032510 A1 WO 2010032510A1 JP 2009057609 W JP2009057609 W JP 2009057609W WO 2010032510 A1 WO2010032510 A1 WO 2010032510A1
Authority
WO
WIPO (PCT)
Prior art keywords
branched
sugar
megalosaccharide
glucan
food
Prior art date
Application number
PCT/JP2009/057609
Other languages
English (en)
Japanese (ja)
Inventor
亘 佐分利
由香里 上村
祐一郎 大畑
山本　健
正保 高田
Original Assignee
日本食品化工株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=41591577&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2010032510(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by 日本食品化工株式会社 filed Critical 日本食品化工株式会社
Publication of WO2010032510A1 publication Critical patent/WO2010032510A1/fr

Links

Images

Classifications

    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/66—Proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/152—Milk preparations; Milk powder or milk powder preparations containing additives
    • A23C9/156—Flavoured milk preparations ; Addition of fruits, vegetables, sugars, sugar alcohols or sweeteners
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • A23G9/34—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds characterised by carbohydrates used, e.g. polysaccharides
    • 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
    • A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/50—Poultry products, e.g. poultry sausages
    • A23L13/55—Treatment of original pieces or parts
    • A23L13/57—Coating with a layer or stuffing
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/54—Mixing with gases
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin

Definitions

  • the present invention relates to a glucan having a branched structure at least at a non-reducing end and a method for producing the glucan.
  • the present invention also relates to uses of the branched glucan and foods and pharmaceuticals containing the same.
  • Starch is a natural polysaccharide composed of glucose as the only saccharide, and a branched structure is formed by binding a number of similar glucan chains to the main chain consisting of ⁇ -1,4-linkages through ⁇ -1,6-linkages. It is composed of amylopectin having a tufted structure and linear amylose having no branched structure. Starch is generally insoluble in water, but becomes water-soluble by denaturation by heat or hydrolysis to some extent by acid or enzyme to lower the molecular weight. Thereafter, by proceeding with decomposition, dextrin, maltooligosaccharide and glucose are obtained, and these are generally called starch sugar. The degree of starch degradation is expressed in terms of glucose equivalent (DE). Dextrins are obtained by relatively mildly degrading starch, but those with a DE of 10 or less are called dextrins and those with 10-20 are called maltodextrins.
  • DE glucose equivalent
  • the starch degradation products with different DEs have different physical properties depending on the DE. That is, the higher the degree of degradation, the higher the degree of sweetness and the maximum for glucose with the highest DE.
  • the lower the DE the stronger the aging property, which is the original property of starch as a raw material, and in an aqueous solution, it aggregates due to aging and produces a white precipitate. Further, this aging property becomes more prominent as the branched structure is smaller, and amylose not having a branched structure is significantly aged and cannot be stored in an aqueous solution state. Also, the viscosity of the solution strongly depends on DE.
  • starch when starch is used as a raw material for foods and drinks, it can be said that it is impractical to use a liquid product from the viewpoints of aging, viscosity, and storage stability. For this reason, starch and dextrin are generally distributed in powder form.
  • starch When starch is used in foods and drinks, the aging properties of starch and dextrin often affect the quality. That is, white turbidity due to insolubilization due to aging in beverages, and deterioration of food texture in foods. For this reason, starch and dextrin excellent in aging resistance have been demanded, and various studies have been made. In order to produce starch sugar having excellent aging resistance and excellent storage stability, starch is decomposed to such an extent that it does not exhibit aging property, that is, the degree of polymerization is 10 or less, or the starch is treated so as to have a dense branched structure. There was a need.
  • ⁇ -limit dextrin obtained by degrading starch to the limit with ⁇ -amylase and then removing the resulting maltose has many short-chain branched structures, and has excellent aging resistance even at low DE. Have.
  • ⁇ -limit dextrin it was necessary to remove maltose by fractionation.
  • a water-soluble macrocyclic glucan is formed by allowing a branching enzyme (branching enzyme), 4- ⁇ -glucanotransferase or cyclodextrin-forming enzyme to synthesize starch branch chains to act on the starch liquefaction solution.
  • Patent Document 3 Japanese Patent Laid-Open No. 8-134104 (Patent Document 3)). Furthermore, a branching starch having a branching structure with a glucose polymerization degree of 6 or 7 is formed using glucose-1-phosphate and maltooligosaccharide as substrates using a branching enzyme (SBE-II) derived from barley and phosphorylase. A method of causing this is proposed (Japanese Patent Laid-Open No. 2002-78497 (Patent Document 4)).
  • SBE-II branching enzyme
  • polyphenols are plant components having a plurality of phenolic hydroxyl groups in the molecule, and catechins, anthocyanins, chlorogenic acids and the like are known as typical polyphenols.
  • Polyphenols have been reported to have many physiological effects beneficial to health promotion.
  • catechin has an antioxidant action, an antibacterial action, an action to improve lipid metabolism, an action to suppress an increase in blood pressure, and an action to suppress an increase in blood glucose level. , Deodorant action, antiallergic action, etc. Utilizing such physiological activity, green tea beverages and near water containing catechins at high concentrations are widely sold as health beverages.
  • polyphenols exhibit strong bitterness and astringency. That is, due to the strong bitterness and astringency of polyphenols, foods and drinks containing polyphenols at a high concentration are difficult to eat and drink due to the bitterness and astringency. For this reason, although polyphenols have various beneficial physiological functions, it is a problem that it is difficult to ingest high concentrations.
  • ⁇ -cyclodextrin has an ADI value (daily acceptable intake) of 5 mg / kg / day, and there is a problem that the amount of use is limited. There was a problem that even the taste was reduced.
  • Patent Document 6 discloses a method for suppressing the bitterness and / or astringency of catechins by using a flavor regulator containing a 3-4 sugar having a branched structure as an active ingredient. .
  • a flavor regulator containing a 3-4 sugar having a branched structure as an active ingredient.
  • the lower the sugar the stronger the sweetness, and the higher the sugar content of 3-4 sugars, the more sweetness is unavoidable, which limits the use of low-sweet foods such as green tea beverages. .
  • JP-A-2008-61593 discloses a method for reducing the bitterness and astringency of polyphenols by blending maltohexaose and / or maltoheptaose in a range of 1.5 to 6% by mass. Is disclosed. However, the maltohexaose and maltoheptaose-containing syrups used in this document also contain low-molecular sugars and are easy to feel sweetness, so the amount used is limited in low-sweet drinks such as green tea drinks for the same reason as above. There was a problem of being.
  • the inventors of the present invention when an enzyme having a sugar transfer action is allowed to act on a starch liquefaction solution together with a cyclodextrin-forming enzyme, hardly produces cyclodextrin and has a degree of polymerization of about 11 to 35 having a branched structure at the non-reducing end.
  • glucan can be produced.
  • the present inventors have also shown that a glucan having a branched structure at the non-reducing end and having a polymerization degree of about 11 to 35 has extremely high aging resistance as compared with a linear maltodextrin, and improves flavor and texture. It was found that it is extremely effective.
  • the present invention is based on these findings.
  • a glucan having a degree of polymerization of 11 to 35 and having a branched structure at least at the non-reducing end, or a reduced product thereof (hereinafter referred to as “megalosaccharide according to the present invention”).
  • the glucan or reduced product thereof according to any one of (1) to (3) which comprises a step of allowing a cyclodextrin-forming enzyme and an enzyme having a glycosyltransferase action to act on a starch raw material.
  • (6) The production method according to (5), wherein a debranching enzyme is further acted on in addition to the cyclodextrin-forming enzyme and the enzyme having a glycosyltransferase effect.
  • cyclodextrins synthase Paenibacillus sp (Paenibacillus sp.), Bacillus coagulans (Bacillus coagulans), Bacillus stearothermophilus (Bacillus stearothermophilus), or Bacillus Mazeransu (Bacillus Macelans) is derived from, (5) Or the manufacturing method as described in (6).
  • the debranching enzyme is selected from the group consisting of isoamylase, pullulanase, and combinations thereof.
  • the debranching enzyme is selected from the group consisting of an isoamylase derived from Myroides odoratus, an isoamylase derived from Pseudomonas amyloderamosa, a Klebsiella pneumoniae- derived pullulanase, and a combination thereof.
  • a food additive or a pharmaceutical additive comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • the flavor improvement is a reduction in bitterness and / or astringency, a reduction in sourness, a reduction in taste and / or an unpleasant taste, an enhanced richness, a reduction in unpleasant odor, or a reduction in alcoholic feeling.
  • a texture improving agent comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • a homogeneous ice freezing agent comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • a shine and / or gloss improver for food comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • a method for improving flavor comprising adding the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4) to food. Or a method for producing a food with improved flavor.
  • a method for reducing bitterness and / or astringency, or a method for producing a food with reduced bitterness and / or astringency comprising: (22) The method for reducing bitterness and / or astringency according to (21) or the food having reduced bitterness and / or astringency, wherein the food having a bitterness and / or astringency is a polyphenol-containing food. Production method.
  • Polyphenol-containing foods are tea-based beverages, fruit beverages, carbonated beverages, vegetable beverages, sports beverages, dairy beverages, alcoholic beverages, other beverages, ice creams, jellies, mousses, sweets, gums, fillings,
  • An unpleasant taste comprising adding the glucan according to any one of (1) to (3) or a reduced product thereof or the liquid sugar or powdered sugar according to (4) to a pharmaceutical product Masking method or a method for producing a pharmaceutical product with an unpleasant taste masked.
  • Improvement of texture comprising adding the glucan or reduced product thereof according to any one of (1) to (3) or the liquid sugar or powdered sugar according to (4) to food.
  • Glucan according to any one of (1) to (3) or a reduced product thereof or liquid sugar or powdered sugar according to (4) is added to water in which the additive is uniformly dissolved or dispersed.
  • Irradiation of food comprising adding the glucan according to any one of (1) to (3) or a reduced product thereof or the liquid sugar or powdered sugar according to (4) to the food, and A method for improving the gloss or / or a method for producing food with improved shine and / or gloss.
  • a food comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • a polyphenol-containing food comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • the glucan according to any one of (1) to (3) or the reduced product thereof is contained in an amount of 1.6 to 50% by mass with respect to 0.13% by mass of the polyphenols. Foods containing polyphenols.
  • Polyphenol-containing foods are tea-based beverages, fruit beverages, carbonated beverages, vegetable beverages, sports beverages, dairy beverages, alcoholic beverages, other beverages, ice creams, jellies, mousses, sweets, gums, fillings,
  • a pharmaceutical comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • a milk protein-containing beverage comprising the glucan according to any one of (1) to (3) or a reduced product thereof, or the liquid sugar or powdered sugar according to (4).
  • the branched megalosaccharide according to the present invention has excellent aging resistance, as well as excellent storage stability and operability.
  • the branched megalosaccharide according to the present invention also has a taste improving action such as masking unpleasant taste.
  • the branched megalosaccharide according to the present invention further has an action of improving and promoting ice uniformity when added to water containing a mixed component such as saccharide.
  • the branched megalosaccharide according to the present invention also has an effect of improving the shine and gloss of food.
  • the branched megalosaccharide according to the present invention has a low sweetness and does not affect the original flavor of food even when added to food.
  • the branched megalosaccharide according to the present invention can also prevent milk protein aggregation and precipitation and allow milk protein to exist stably. Therefore, the branched megalosaccharide and its reduced product according to the present invention, and liquid sugar and powdered sugar containing the same can be widely used as food additives and pharmaceutical additives.
  • the branched megalosaccharide according to the present invention can be produced simply and with high yield. Therefore, the production method according to the present invention opens up the industrial production of branched megalosaccharide according to the present invention.
  • the branched megalosaccharide according to the present invention is a glucan having a polymerization degree of 11 to 35 composed of a linear glucan and a branched structure, and a branched structure is introduced at least at the non-reducing end of the linear glucan. It is a glucan.
  • the “linear glucan” means a linear glucan composed of glucose molecules bonded by a single glucoside bond.
  • branched megalosaccharide according to the present invention include a structure comprising a linear glucan composed of ⁇ -1,4-glucoside bonds and a branched structure introduced at least at the non-reducing end of the linear glucan. And branched megalosaccharide having a polymerization degree of 11 to 35. Further specific examples of the branched megalosaccharide according to the present invention include a linear glucan constituted by ⁇ -1,4-glucoside bonds and a branched structure introduced only at the non-reducing end of the linear glucan. And a branched megalosaccharide having a polymerization degree of 11 to 35.
  • the “branched structure” means a glucan residue composed of one or more glucose residues bonded to a linear glucan by a glucoside bond other than an ⁇ -1,4-glucoside bond.
  • glucoside bonds other than ⁇ -1,4-glucoside bonds include ⁇ -1,6-glucoside bonds, ⁇ -1,3-glucoside bonds, and ⁇ -1,2-glucoside bonds.
  • the branch structure introduced into the non-reducing end can be changed by selecting an enzyme having a glycosyltransferase effect used in the production method according to the present invention.
  • the number of glucose residues constituting the branched glucan residue is not particularly limited as long as the degree of polymerization of the branched megalosaccharide according to the present invention is satisfied, but preferably 1 to several, more preferably 1 to 6, 1 There can be ⁇ 4, 1-3, or 1-2.
  • the branched structure is a glucan residue composed of disaccharide units
  • examples of the branched structure include cordobiose, nigerose, maltose, isomaltose structure, and more specifically, the non-reducing end of a linear glucan.
  • cordobiose, nigerose, maltose, or isomaltose is bonded in a bonding mode other than ⁇ -1,4-bond.
  • the branched structure may be a glucan composed only of a single glucoside bond such as isomaltotriose or nigerotriose, or a plurality of glucoside bonds such as panose. More specifically, a single glucoside bond such as isomaltotriose or nigerotriose is used at the non-reducing end of a linear glucan with a binding mode other than ⁇ -1,4-linkage. And a structure in which a glucan composed of a plurality of glucoside bonds such as panose is bound.
  • the “reducing terminal” means a sugar residue that exhibits reducing properties.
  • the “non-reducing terminal” means a sugar residue that does not exhibit reducing properties, that is, a terminal sugar residue other than the “reducing terminal”.
  • the “degree of polymerization” refers to the number of glucose residues constituting a glucan and includes not only the number of glucose residues constituting a linear glucan but also the number of glucose residues constituting a branched structure. .
  • the degree of polymerization of the branched saccharide can be measured by high performance liquid chromatography (HPLC) method.
  • the degree of polymerization of megalosaccharide according to the present invention is 11 to 35, but the degree of polymerization may be in the range of 15 to 35.
  • a glucan having a degree of polymerization of 11 to 35 is sometimes simply referred to as “megalosugar”.
  • reduced product refers to a product in which the aldehyde group of the glucosyl group at the reducing end of the sugar is reduced to form a hydroxyl group.
  • Methods for obtaining a reduced product of sugar are well known to those skilled in the art.
  • Examples of usable reduction methods include a method using a hydride reducing agent, a method using a metal in a protic solvent, an electrolytic reduction method, and a catalytic hydrogenation reaction. Methods and the like.
  • the method using a hydride reducing agent is convenient and convenient without requiring a special apparatus, while on the other hand, when carried out on an industrial scale, A method using a catalytic hydrogenation reaction is preferred because it is economical and has few by-products.
  • the catalytic hydrogenation reaction is a reaction in which hydrogen is added to the double bond portion of an unsaturated organic compound in the presence of a catalyst, and is generally also referred to as a hydrogenation reaction.
  • the method for producing the reduced product according to the present invention will be specifically described.
  • the branched megalosaccharide according to the present invention is dissolved in water, an appropriate amount of Raney nickel catalyst is added thereto, hydrogen gas is added, and reduction is performed under high temperature conditions. Next, decolorization / deionization treatment is performed to obtain a branched megalosaccharide reducing sugar composition.
  • the catalyst that can be used in the catalytic hydrogenation reaction is not particularly limited as long as it is a known hydrogenation catalyst.
  • nickel-supported on various supports such as Raney nickel, reduced nickel, diatomaceous earth, alumina, pumice, silica gel, and acid clay.
  • Nickel catalysts such as supported catalysts; cobalt catalysts such as Raney cobalt, reduced cobalt, cobalt-supported catalysts; copper catalysts such as Raney copper, reduced copper, copper-supported catalysts; palladium black, palladium oxide, colloidal palladium, palladium-carbon, Palladium catalysts such as palladium-barium sulfate, palladium-magnesium oxide, palladium-alumina; platinum catalysts such as platinum-support catalysts such as platinum black, colloidal platinum, platinum oxide, platinum sulfide, platinum-carbon; colloidal rhodium, rhodium-carbon Rhodium catalysts such as rhodium oxide; Platinum group catalysts such as um catalyst; -; copper chromium oxide catalyst; molybdenum trioxide catalyst; vanadium oxide catalyst; tungsten oxide catalyst; dinitrogen rhenium, rhenium rhenium catalyst such as carbon such as silver catalyst.
  • Raney nickel such as Raney nickel
  • the hydrogen pressure is usually in the range of 10 to 250 kg / cm 2 , preferably 50 to 200 kg / cm 2 .
  • the reaction temperature varies depending on the amount of catalyst and the type of solvent, but is usually preferably in the range of 80 to 200 ° C, more preferably 90 to 160 ° C.
  • branched megalosaccharide according to the present invention is intended to include a reduced product.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same can be produced by allowing a cyclodextrin-forming enzyme and an enzyme having a sugar transfer action to act on a starch raw material.
  • the starch raw material it is preferable to cause the starch raw material to act together with a cyclodextrin-producing enzyme and an enzyme having a sugar transfer action.
  • ⁇ -glucosidase acts on the non-reducing end of dextrin contained in starch raw material, or on the non-reducing end of dextrin that has been reduced in molecular weight in any of hydrolysis, coupling, or disproportionation of cyclodextrin-forming enzyme. Then, the ⁇ -1,4-bond is cleaved, and the glucosyl group is linked to another or the same non-reducing terminal glucosyl group by ⁇ -1,6-bond, ⁇ -1,2-bond, or ⁇ -1, 3- Add with a bond.
  • the cyclodextrin-producing reaction by the cyclodextrin-producing enzyme occurs only in the early stage of the reaction, and the cyclodextrin produced by the coupling reaction of the cyclodextrin-producing enzyme is opened and used as a substrate for the transglycosylation reaction by ⁇ -glucosidase. Supplied.
  • cyclodextrin produced in the early stage of the reaction is almost completely decomposed in the later stage of the reaction, and almost no cyclodextrin remains in the later stage of the reaction.
  • a debranching enzyme coexists in the reaction solution, the starch branch chain is cleaved and linear dextrin is supplied. Since linear dextrin also functions as an acceptor molecule in the coupling reaction, it is considered that the reaction can proceed efficiently.
  • the enzymatic reaction for producing branched megalosaccharide from starch raw material can be carried out at a temperature at which the enzymatic reaction proceeds, and can usually be carried out in a temperature range up to around 60 ° C.
  • the preferred reaction temperature is 30-55 ° C.
  • the enzymatic reaction for producing branched megalosaccharide from the starch raw material can be carried out at a pH at which the enzymatic reaction proceeds, and can usually be carried out in the range of pH 5-9.
  • a suitable reaction pH is in the range of pH 5.5-7.
  • the amount of enzyme used and the reaction time are closely related, and the reaction time can be appropriately adjusted according to the progress of the target enzyme reaction.
  • a starch liquefied liquid can be used as a starch raw material.
  • the starch concentration of the starch liquefaction solution used as a raw material can be set to 10 to 45% by mass from the viewpoint of the efficiency of enzyme reaction, the solubility of starch, and the like.
  • the reaction can proceed well even if the substrate concentration exceeds 45% by mass.
  • the DE of the starch liquefaction liquid is usually preferably in the range of DE 2 to 25, more preferably in the range of DE 3 to 10.
  • starch gelatinized material may be used as a starch raw material.
  • the amount of cyclodextrin-producing enzyme used in the enzyme reaction in the production method according to the present invention can be 0.2 to 10 units per gram of substrate (solid) from the viewpoint of reaction efficiency and production cost.
  • 1 unit of cyclodextrin-producing enzyme means the amount of enzyme necessary to produce 1 mg of ⁇ -cyclodextrin per minute under the conditions of the method for measuring the activity of cyclodextrin-producing enzyme described later.
  • the amount of ⁇ -glucosidase added is 0.01 to 30 units per gram of substrate (solid) from the viewpoint of reaction efficiency and production cost. can do.
  • one unit of ⁇ -glucosidase refers to the amount of enzyme required to hydrolyze 1 ⁇ mol of maltose per minute under the conditions of the ⁇ -glucosidase activity measurement method described later.
  • a debranching enzyme can be further acted in addition to the cyclodextrin-forming enzyme and the enzyme having a sugar transfer action.
  • a debranching enzyme is allowed to act, since the residual amount of dextrin components exceeding the degree of polymerization of 35 remaining after the branching megalosaccharide production reaction is small and the amount of branched megalosaccharide production is increased, the branched megalosaccharide is efficiently produced.
  • the debranching enzyme is preferably allowed to act on the starch raw material together with the cyclodextrin-forming enzyme and the enzyme having a sugar transfer action.
  • the amount of isoamylase added can be 10 to 1000 units per gram of substrate (solid) from the viewpoint of reaction efficiency and production cost.
  • the amount of pullulanase added may be 0.001 to 0.1% by mass per substrate (solid) from the viewpoint of reactivity and production cost. it can.
  • 1 unit of isoamylase is an enzyme titer that increases the absorbance at 610 nm by 0.01 under the conditions of the method for measuring the activity of isoamylase described later.
  • addition amount of the debranching enzyme other than isoamylase and pullulanase those skilled in the art can determine the addition amount according to the addition amount of isoamylase or pullulanase.
  • the origin of the starch used as the raw material for the production method according to the present invention is not particularly limited.
  • Subsurface starches such as starch starch and waste starch can be used.
  • amylose, amylopectin, starch partial decomposition product, etc. obtained from starch can be used as a raw material.
  • These starches can be liquefied or gelatinized and used in the production method according to the present invention.
  • a starch liquefied liquid obtained by allowing a liquefying enzyme such as amylase to act on starch can be used as a starch raw material in the production method according to the present invention.
  • Methods for liquefying starch and gelatinizing are well known to those skilled in the art, and any method can be used.
  • the enzyme used in the production method according to the present invention may be a purified enzyme or a crude enzyme as long as a branched megalosaccharide can be prepared, and it may be a free enzyme or an immobilized enzyme. Also good.
  • the reaction format may be any of batch, semi-continuous and continuous.
  • a known method such as a carrier bonding method (for example, a covalent bonding method, an ionic bonding method, or a physical adsorption method), a crosslinking method, or a comprehensive method (lattice type or microcapsule type) should be used. Can do.
  • cyclodextrin-producing enzyme used in the production method according to the present invention, a commercially available product or a product isolated from a microorganism may be used.
  • the microorganism as an isolation source may be a recombinant microorganism having the ability to produce a cyclodextrin-producing enzyme, or a mutant strain obtained by mutating a naturally-occurring microorganism, in addition to a naturally-occurring microorganism.
  • Microbial origin of "cyclodextrin forming enzyme” is not particularly limited, for example, Paenibacillus sp (Paenibacillus sp.), Bacillus coagulans (Bacillus coagulans), Bacillus stearothermophilus (Bacillus stearothermophilus), and Bacillus Mazeransu (Bacillus macelans) from Can be used.
  • Examples of the “enzyme having glycosyltransferase effect” used in the production method according to the present invention include ⁇ -glucosidase, 6- ⁇ -glucosyltransferase, dextrin dextranase, and cyclic maltosyl maltose producing enzyme.
  • ⁇ -glucosidase a commercially available product or a product isolated from a microorganism may be used.
  • the microorganism as an isolation source may be a recombinant microorganism having the ability to produce an ⁇ -glucosidase-producing enzyme, or a mutant strain obtained by mutating a naturally-occurring microorganism, in addition to a naturally-occurring microorganism.
  • the microbial origin of ⁇ -glucosidase is not particularly limited. For example, those derived from Aspergillus niger and Acremonium sp. can be used.
  • Examples of the “branching enzyme” used in the production method according to the present invention include isoamylase and pullulanase, and it is preferable to use an isoamylase that can easily cleave a long branched chain.
  • the isoamylase a commercially available product or a product isolated from a microorganism may be used.
  • the microorganism as an isolation source may be a recombinant microorganism having isoamylase-producing ability or a mutant strain obtained by mutating a naturally-occurring microorganism in addition to a naturally-occurring microorganism.
  • microbial origin isoamylase is not particularly limited, for example, Mairoidesu Odoratasu (Myroides odoratus) and Pseudomonas Amiroderamosa (Pseudomonas amyloderamosa) can be used those derived from.
  • pullulanase a commercially available product or a product isolated from a microorganism may be used.
  • the microorganism as an isolation source may be a recombinant microorganism having pullulanase-producing ability or a mutant strain obtained by mutating a naturally-occurring microorganism in addition to a naturally-occurring microorganism.
  • microbial origin of pullulanase is not particularly limited, for example, Klebsiella pneumoniae (Klebseilla pneumoniae) and brevis (Bacillus brevis) can be used those derived from.
  • pullulanase “Amano” 3 manufactured by Amano Enzyme can be preferably used.
  • the branched megalosaccharide according to the present invention can be obtained in the reaction product. Whether a branched structure is introduced at the non-reducing end of the megalo sugar present in the reaction product is determined by ⁇ -amylase that hydrolyzes ⁇ -1,4-bonds in units of two sugars from the non-reducing end of maltodextrin or starch Can be confirmed by not undergoing hydrolysis.
  • the ⁇ -amylase that can be used is not particularly limited. For example, soybean-derived ⁇ -amylase can be used.
  • ⁇ -amylase As with ⁇ -amylase, it is possible to use maltodextrin or glucoamylase that hydrolyzes ⁇ -1,4-linkage from the non-reducing end of starch, but this enzyme is ⁇ -1,6- Since it also has a binding resolution, it is preferable to use ⁇ -amylase.
  • branched megalosaccharide in which a glucose residue is bonded to the non-reducing end by an ⁇ -1,3-glucoside bond can be produced.
  • the branched structure of the branched megalosaccharide includes a structure in which glucose is branched by ⁇ -1,3-bonds, a structure in which maltose is branched by ⁇ -1,3-bonds, and nigerose is formed by ⁇ -1,3-bonds.
  • a branched structure a structure in which maltotriose is branched by an ⁇ -1,3-bond, a structure in which maltosyl- ⁇ -1,3-glucose is branched by an ⁇ -1,3-bond, nigerosyl- ⁇ -1,4- Examples include a structure in which glucose is branched by an ⁇ -1,3-bond, and a structure in which nigerotriose is branched by an ⁇ -1,3-bond.
  • the branched structure is a glucan that is bonded to the non-reducing end of the linear glucan of the substrate by an ⁇ -1,3-linkage, and is a glucoside constituting the branched structure
  • the bond may be a glucan composed of ⁇ -1,4-bond and / or ⁇ -1,3-bond.
  • the branched megalosaccharide according to the present invention can be produced in a high yield, and in particular, a relatively high degree of polymerization with a degree of polymerization of 15 to 35. Therefore, it is possible to produce a highly branched megalosaccharide with high efficiency.
  • the branched structure of the branched megalosaccharide includes a structure in which glucose is branched by an ⁇ -1,6-bond, a structure in which maltose is branched by an ⁇ -1,6-bond, and an isomaltose in an ⁇ -1,6-bond.
  • Branched structure maltotriose branched by ⁇ -1,6-bond, isopanose branched by ⁇ -1,6-bond, panose branched by ⁇ -1,6-bond
  • An example is a structure in which maltotriose is branched by ⁇ -1,6-bonds.
  • the branched structure is a glucan that is bonded to the non-reducing end of the linear glucan of the substrate by an ⁇ -1,6-bond, and the glucoside constituting the branched structure
  • the bond may be a glucan having an ⁇ -1,4-bond and / or an ⁇ -1,6-bond.
  • ⁇ -glucosidase derived from Aspergillus niger is used, ⁇ -1,2-bonds and ⁇ -1,3-bonds may be included in the branched structure, although in very small amounts.
  • 6- ⁇ -glucosyltransferase When 6- ⁇ -glucosyltransferase is used as a glycosyltransferase, a branched megalosaccharide in which one molecule of glucose is bonded to the non-reducing end of a linear glucan by ⁇ -1,6-linkage is obtained.
  • dextrin dextranase When dextrin dextranase is used as a glycosyltransferase, a branched megalosaccharide in which a branched structure consisting of 1 to 6 glucose residues is bonded to the non-reducing end of a linear glucan by an ⁇ -1,6-bond is obtained. It is done.
  • This branched glucan is mainly composed of ⁇ -1,6-bonds, but may contain a few ⁇ -1,4-linkages.
  • a cyclic maltosyl maltose-producing enzyme is used as a glycosyltransferase
  • a branched megalosaccharide in which maltose or maltosyl- ⁇ -1,6-maltose is bonded to the non-reducing end of a linear glucan by an ⁇ -1,6-linkage Is obtained.
  • the product obtained by the enzymatic reaction can be directly used as a branched megalosaccharide product. Further, if necessary, the product obtained by the enzyme reaction is centrifuged or filtered to remove insoluble matters, and the water-soluble fraction is concentrated, whereby the target branched megalosaccharide solution according to the present invention is obtained. It can also be obtained. Or what was decolored with activated carbon as needed, and what removed the ionic component with the appropriate ion exchange resin may be concentrated. In the storage and subsequent use, it is preferable to concentrate the decolorized and ion-removed product until the water activity is such that the propagation of microorganisms does not become a problem. Or it can also be dried and obtained as a powder so that it may be easy to use depending on a use. For drying, a method such as freeze drying, spray drying or drum drying can be used. The dried product is desirably pulverized as necessary.
  • liquid sugars and powdered sugars containing 10 to 60% by mass, preferably 15 to 55% by mass, of the branched megalosaccharide according to the present invention per solid content.
  • powdered sugar shall be used with the meaning containing powdered rice cake.
  • the product obtained by the enzymatic reaction of the present invention usually contains a small amount of cyclodextrin, dextrin, oligosaccharide having a polymerization degree of 10 or less, or a mixture thereof, together with the branched megalosaccharide according to the present invention.
  • This product can be used as it is for foods and the like as described later, but if necessary, these components may be removed to obtain a purified branched megalosaccharide.
  • oligosaccharides having a polymerization degree of less than 5 may be removed from these products.
  • the product obtained by the enzyme reaction of the present invention has a branched structure derived from the starch raw material in the middle part of the linear glucan in addition to the non-reducing end, that is, the sugar residue other than the terminal residue.
  • the branched megalosaccharide is slightly contained, and such a branched megalosaccharide is also within the scope of the present invention.
  • the branched megalosaccharide according to the present invention thus obtained does not show turbidity due to aging compared to ordinary dextrin even when the solution is left at a low temperature or as a high-concentration solution having a solid content of about 75% by mass. It has the characteristic of having remarkable aging resistance. Moreover, it has the characteristics that the viscosity in the solution state of about 75 mass% of solid content is low and it is excellent in operativity. In addition, the content of low-molecular-weight oligosaccharide components such as glucose after saccharification reaction is small, and the varicella is also characterized by extremely low sweetness.
  • liquid sugars and powdered sugars containing branched oligosaccharides according to the present invention from which oligosaccharides having a polymerization degree of 4 or less have been removed have not only aging resistance but also low sweetness. And is advantageous in that it can be used for flavor improvement.
  • branched megalo sugar [ use for food]
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same can be added to foods. Therefore, according to the present invention, a food additive comprising the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same is provided.
  • the branched megalosaccharide according to the present invention and the food to which the liquid sugar and powdered sugar containing it can be added are not particularly limited.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same have a taste improving effect and a texture improving effect, and are characterized by low sweetness. Therefore, by adding the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same to the food, it is advantageous in that the flavor and texture of the food can be improved without impairing the original flavor of the food.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same also have an effect of uniformly freezing water in which the additive is dissolved or dispersed. Therefore, it is advantageous in that ice having a uniformly dispersed additive can be produced by adding the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same to water in which the additive is dissolved or dispersed. .
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it can also improve the shine and gloss of food. Therefore, by adding the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it to the food, it is advantageous in that a product with improved shine and gloss can be provided.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same can also suppress milk protein aggregation and precipitation. Therefore, by adding the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same to the milk protein-containing beverage, milk protein aggregation and precipitation are suppressed, and the milk protein-containing beverage is stabilized. Is advantageous in that it can be provided.
  • a person skilled in the art can appropriately select a branched megalosaccharide and liquid sugar and powdered sugar containing the same according to the present invention according to the method for producing the food. Even if it manufactures, it may mix
  • the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same can also be used by adding to pharmaceuticals. Therefore, according to the present invention, there are provided a pharmaceutical additive comprising the branched megalosaccharide according to the present invention, and liquid sugar and powdered sugar containing the same.
  • a pharmaceutical additive comprising the branched megalosaccharide according to the present invention, and liquid sugar and powdered sugar containing the same.
  • the medicinal product to which the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing it can be added and examples thereof include preparations for oral administration, preferably tablets, powders, granules, fine powders, and the like. Granules, liquids, syrups (including dry syrups), capsules, lozenges and the like.
  • the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same have a flavor improving effect. Therefore, by adding the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it to a pharmaceutical product, the taste of the active ingredient and other additive ingredients can be corrected or masked, and can also be used as an excipient. Is advantageous.
  • composition methods and pharmaceutical additives as raw materials for pharmaceuticals are well known to those skilled in the art, and branched megalosaccharides according to the present invention and liquid sugars and powdered sugars containing them are used as active ingredients and other pharmaceutical additives. Can be produced in accordance with a conventional method.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same can improve the flavor of foods and the like as shown in the formulation examples described later. Therefore, according to the present invention, there are provided a flavor-improving agent and a masking agent for preparations comprising the branched megalosaccharide according to the present invention, and liquid sugar and powdered sugar containing the same.
  • examples of flavor improvement include improvement of unpleasant taste and odor peculiar to foods and food additives, for example, reduction of bitterness and / or astringency (for example, reduction of bitterness and astringency of polyphenols).
  • Reduction of acidity e.g., mitigation of acidity derived from vinegar and acidulants
  • reduction of egg taste and / or taste e.g., reduction of unpleasant taste of preservatives such as gluconic acid
  • reduction of alcoholic feeling e.g., Reduction of alcohol feeling such as vodka and whiskey
  • reduction of acid odor and other unpleasant odor for example, reduction of glucono delta lactone odor (gluconic acid odor) and dextrin odor
  • Examples of the flavor improvement include enhancement of richness (for example, enhancement of fruit juice feeling and milky feeling).
  • Examples of the product whose flavor is improved by the flavor improving agent according to the present invention include the foods described above.
  • the taste corrected or masked in the pharmaceutical preparation includes an unpleasant taste (for example, bitter taste, astringency, sour taste, and savory taste) peculiar to active ingredients and other additives for pharmaceutical preparations.
  • an unpleasant taste for example, bitter taste, astringency, sour taste, and savory taste
  • the flavor improving agent according to the present invention can be preferably used as a bitterness and / or astringency reducing agent.
  • the flavor improving agent according to the present invention is preferably a bitterness and / or astringency of polyphenols. It can be used as a reducing agent.
  • Polyphenols mean components having a plurality of phenolic hydroxyl groups in the molecule, and examples thereof include catechin, anthocyanin, chlorogenic acid and the like. Polyphenols are known to have various physiological functions favorable to living organisms, but most polyphenols exhibit strong bitterness and astringency, making it difficult to ingest high concentrations. Since the branched megalosaccharide according to the present invention effectively reduces the bitterness and / or astringency caused by polyphenols, the flavor improving agent according to the present invention is advantageous in that it allows high-concentration intake of polyphenols.
  • the branched megalosaccharide according to the present invention is also low in sweetness, which is advantageous in that the flavor can be improved without impairing the original flavor of the food even when the flavor improver according to the present invention is added to the food.
  • a method for improving flavor and a method for producing food with improved flavor comprising adding the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same to food.
  • the bitter and / or astringent taste comprising the addition of the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same to foods having a bitter and / or astringent taste.
  • a reduction method and a method for producing a food with reduced bitterness and / or astringency As described above, the branched megalosaccharide according to the present invention effectively reduces the bitterness and / or astringency derived from polyphenols. Therefore, as a food having a bitterness and / or astringency, a polyphenols-containing food is used. Can be mentioned.
  • the polyphenol-containing food is not particularly limited as long as it contains polyphenols, and foods to which polyphenols are added as well as foods originally containing polyphenols are also applicable.
  • the form of the food is not particularly limited, and includes not only solids but also semisolids and liquids.
  • Specific examples of polyphenol-containing foods include beverages such as tea beverages (green tea beverages, tea beverages, oolong tea beverages, etc.), fruit beverages, carbonated beverages, vegetable beverages, sports beverages, milk beverages, alcoholic beverages, and ice creams. , Jelly, mousse, candy, gum, filling, health food, supplements and the like.
  • the term “food product” is used to include beverages.
  • an unpleasant taste masking method or an unpleasant taste masked pharmaceutical comprising adding the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same to the pharmaceutical.
  • a manufacturing method is provided.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same can also improve the texture of foods and the like. Therefore, according to the present invention, there is provided a texture improving agent comprising the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same.
  • examples of the texture improvement include suppression of a feeling of dryness, imparting a moist feeling, and maintaining a soft texture.
  • examples of the food whose texture is improved by the flavor improving agent according to the present invention include foods whose food texture is required to be improved, and examples of such foods include breads, cookies, and cooked rice. , Cakes, noodles, frozen foods.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it can be added to foods for the purpose of improving the texture, but it goes without saying that they may also be added for the purpose of improving the flavor.
  • the texture improving effect of preventing the puffiness is obtained, but the shelf life improver added to the cooked rice (for example, , Glucono delta lactone and gluconic acid) and the like can be reduced.
  • a method for improving texture and a method for producing food with improved texture comprising adding the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same to food. Provided.
  • the branched megalosaccharide and liquid sugar and powdered sugar containing the same according to the present invention can uniformly freeze water in which the additive is dissolved or dispersed. Therefore, according to the present invention, there is provided a uniform ice freezing agent comprising the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same.
  • a uniform ice freezing agent comprising the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same.
  • uniform freezing of ice means freezing water containing the additive in a state where the additive is uniformly dissolved or dispersed.
  • water in which an additive is dissolved or dispersed includes a solution in which components other than water, such as fruit juice itself and plant extract itself, are originally mixed.
  • the homogeneous ice is obtained, which comprises freezing the water in which the additive is uniformly dissolved or dispersed by adding the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same.
  • a freezing method or a method for producing uniformly frozen ice is provided.
  • branched megalosaccharide according to the present invention By adding the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same, water can be frozen in a state where the additive is uniformly dissolved or dispersed. Therefore, for example, when the obtained ice is used as a frozen dessert, an iced dessert having a uniform color, texture, taste, etc. without unevenness and unevenness can be provided.
  • the ice uniform freezing agent according to the present invention is added to a beverage such as a fruit juice beverage or a sports beverage and frozen, a beverage that becomes a uniform solution even when partly thawed can be provided. .
  • the ice produced by the method for producing ice according to the present invention is used as it is or after processing, for example, ice confectionery such as sherbet, shaved ice, flake ice, ice candy, shake, sorbet; fruit juice drink, sports drink, amino acid drink Beverages such as jelly and yogurt.
  • ice confectionery such as sherbet, shaved ice, flake ice, ice candy, shake, sorbet
  • fruit juice drink, sports drink amino acid drink Beverages such as jelly and yogurt.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it can also improve the shine and gloss of food. Therefore, according to the present invention, there is provided a food shine and / or luster improving agent comprising the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same.
  • meat is mentioned as a food in which the shimmering and / or improvement in gloss of the food is expected by the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same, and preferably chicken.
  • the method for improving the shine and / or shine of the food comprising adding the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same to the food is improved.
  • a method for producing a prepared food for example, the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same may be applied to the food in advance, and the food may be baked. After the food is baked, the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same may be applied again and baked.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the teriyaki sauce may be added, and the food may be immersed in the sauce and then baked.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it may be directly sprayed on the surface of the food before baking.
  • the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same can be used by adding to a milk protein-containing beverage. Even when the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it are added to a milk protein-containing beverage, the milk protein does not aggregate and precipitate, and the milk protein can be stabilized in the beverage. That is, when the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it are used in a milk protein-containing beverage, aggregation and precipitation of milk protein can be avoided.
  • the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing it have a lower osmotic pressure in the solution than monosaccharide, disaccharide, oligosaccharide and the like. Therefore, the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same can be preferably used by being added to an enteral nutrition or oral nutrition containing milk protein.
  • milk protein in which aggregation and / or precipitation of milk protein is suppressed comprising adding the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same to a milk protein-containing beverage.
  • a method for producing a beverage containing beverage is provided.
  • the addition timing of the branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same in these methods is not particularly limited, and may be added together with milk protein or separately from milk protein.
  • the food additive according to the present invention, the flavor improving agent, the texture improving agent, the ice uniform freezing agent, the shine and / or gloss improving agent, and the milk protein aggregation and / or precipitation inhibitor are added to the food.
  • a food product comprising an agglomeration and / or precipitation inhibitor is provided.
  • a food comprising the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same.
  • the food provided may be a polyphenol-containing food, and specific examples and preferred examples are as described above.
  • branched megalosaccharide according to the present invention and the liquid sugar and powdered sugar containing the same are used for polyphenols-containing foods, for example, when targeting foods and drinks that require sweetness, A composition having a strong sweetness such as sugar, isomerized sugar, and a high-intensity sweetener can be mixed and used.
  • a composition having a strong sweetness such as sugar, isomerized sugar, and a high-intensity sweetener can be mixed and used.
  • branched megalosaccharides alone or a mixture of branched megalosaccharides and polysaccharides, proteins, fats and the like.
  • a polyphenol-containing food containing 1.6 to 50% by mass of the branched megalosaccharide according to the present invention with respect to 0.13% by mass of the polyphenols.
  • the food to be provided may be a milk protein-containing beverage, more preferably an enteral nutrient or an oral nutrient containing milk protein.
  • the formulation additive and the formulation masking agent according to the present invention can be used in combination with a pharmaceutical product. Therefore, according to another aspect of the present invention, there is provided a pharmaceutical comprising the pharmaceutical additive according to the present invention and the pharmaceutical masking agent according to the present invention.
  • a medicinal product comprising the branched megalosaccharide according to the present invention and liquid sugar and powdered sugar containing the same.
  • the present invention will be specifically described based on the following examples, but the present invention is not limited to these examples.
  • the ratio per “solid content” or the content ratio of “solid content” means the ratio determined based on the mass of the solid component.
  • Test Example 1 Measurement of saccharifying enzyme activity 1-1: Activity measurement of cyclodextrin-forming enzyme Cyclodextrin-forming enzyme (CGTase) used in the saccharification reaction is shown below.
  • -CGTase derived from Paenibacillus sp . Alkaline CD amylase manufactured by Nagase ChemteX Corp.
  • -CGTase derived from Bacillus coagulans Neo CD amylase manufactured by Nagase ChemteX Corp.
  • CGTase derived from Bacillus mazelans Contizyme manufactured by Amano Enzyme
  • the enzyme reaction was performed by appropriately diluting water with 0.9 ml of 1% soluble starch (Nacalai Tesque) dissolved in 50 mM potassium phosphate buffer (pH 6.0). 0.1 ml of solution was added and held at 40 ° C. for 10 minutes. The reaction was stopped by adding 2.5 ml of 40 mM sodium hydroxide aqueous solution thereto. The produced ⁇ -cyclodextrin was measured by the phenolphthalein method.
  • ⁇ -glucosidase activity The ⁇ -glucosidase used in the saccharification reaction is shown below.
  • ⁇ -glucosidase derived from Aspergillus niger transglucosidase manufactured by Amano Enzyme, Amano Acremonium sp-derived ⁇ -glucosidase: manufactured by Kirin Foodtech Co., Ltd.
  • the enzyme reaction was dissolved in 50 mM sodium acetate buffer (pH 4.2). 20 ⁇ l of an enzyme solution appropriately diluted with 10 mM sodium acetate buffer (pH 4.2) containing 0.05% Triton X-100 was added to 80 ⁇ l of 25% maltose, and kept at 37 ° C.
  • the isoamylase used in the saccharification reaction is shown below.
  • -Isoamylase derived from Myroides odoratus GODO-FIA manufactured by Godo Shusei Co., Ltd.
  • Pseudomonas amyloderamosa-derived isoamylase Isoamylase produced by Hayashibara Bioscience Laboratories was prepared by adding 350 mg of 5 mg / ml waxy corn starch (Nippon Food Chemical Co., Ltd.) to 100 ⁇ l of 50 mM sodium acetate buffer solution (pH 6.0) containing 20 mM calcium chloride.
  • reaction stop solution 100 ⁇ l of an enzyme solution appropriately added with the same buffer was added to what was added and kept at 45 ° C. for 5 minutes, and kept at 45 ° C. for 15 minutes.
  • the reaction was stopped by adding 500 ⁇ l of a reaction lost iodine solution (a mixture of 2 ml of a solution consisting of 6.35 mg / ml iodine and 83 mg / ml potassium iodide and 8 ml of 0.1N hydrochloric acid).
  • the reaction stop solution was kept at room temperature for 15 minutes, and 10 ml of pure water was added thereto, and the absorbance at 610 nm was measured.
  • Test Example 2 Preparation of branched megalosaccharide The structure and physical properties of a reaction product obtained by allowing cyclodextrin-forming enzyme, ⁇ -glucosidase and debranching enzyme to act on starch liquefaction liquid were examined.
  • branched megalosaccharide was confirmed by the following method using the reaction solution. That is, 50 ⁇ L of 10 mg / mL ⁇ -amylase # 1500 (Nagase ChemteX) dissolved in 1 M sodium acetate buffer (pH 5.5) was added to 1 mL of sugar solution adjusted to 5% by mass, and the mixture was added at 55 ° C. for 1 hour. It was allowed to act to a certain extent and was inactivated by boiling. This was desalted with Amberlite MB4 (organo) and then filtered through a 0.45 ⁇ m filter for high performance liquid chromatography (HPLC). As HPLC conditions, MCI GEL CK02AS was used in the column.
  • the mobile phase was ultrapure water
  • the column temperature was 85 ° C.
  • the flow rate was 1.0 ml / min.
  • about 20 ⁇ L was subjected to chromatography. Under any condition, the content of each polymerization degree component can be determined from the peak area of the obtained chromatogram, and the content of carbohydrates having a polymerization degree of 11 or more was calculated as the branched megalosaccharide content.
  • a branched megalosaccharide having a branched structure at the non-reducing end can be obtained by allowing a cyclodextrin-forming enzyme to act on a starch liquefaction solution in the presence of ⁇ -glucosidase.
  • components other than the components in the table are low-molecular oligosaccharides having a degree of polymerization of 10 or less, and dextrin refers to a polymer component having a degree of polymerization of more than 35.
  • Test Example 3 Confirmation of Aging Resistance of Branched Megalosaccharide
  • a syrup containing a branched megalosaccharide was prepared and checked for turbidity due to aging. was used to evaluate aging resistance.
  • the resulting saccharification reaction solution (equivalent to syrup in Production Example 5 described later) was heated at 80 ° C. for 30 minutes, and ⁇ -amylase preparation Christase L1 manufactured by Daiwa Kasei Co., Ltd. was 0.005% per solid content. The reaction was continued until the iodine reaction disappeared. The enzyme was inactivated by adjusting the pH to 4.0, and then neutral sugar was purified by filtration, ion exchange purification, and activated carbon treatment. Amberlite MB3 was used for ion exchange purification, and purified white birch (Kirin Foodtech) was used for activated carbon treatment. The liquid sugar obtained by concentrating the purified sugar liquid to Bx75 was kept at room temperature for 1 month. Table 3 shows the sugar composition of the resulting sugar solution.
  • An ⁇ -amylase degradation product (corn syrup) of starch was used as a comparative control of storage stability with branched megalosaccharide-containing syrup. That is, 22.5% by mass of DE 6.5 corn starch liquefied liquid was obtained by adding 0.005% of the Christase L1 to the solid content, 0.04% of the pullulanase “Amano” 3 to the solid content, and Myloides odolatas isoamylase to the solid. 400 units were added per gram per minute and saccharified for 36 hours at pH 6.0 and 53 ° C. After heating this to 80 ° C., Christase L1 was additionally added to the solid content by 0.005% and held until the iodine reaction disappeared.
  • Neutral sugars were purified and concentrated in the same manner as above from the resulting reaction solution.
  • Table 3 shows the sugar composition of the resulting sugar solution.
  • components other than the components in the table are low-molecular oligosaccharides having a polymerization degree of 10 or less.
  • Megalosaccharide refers to a saccharide having a polymerization degree of 11 to 35, and the content in parentheses indicates branched megalosaccharide content. Refers to a polymer component having a degree exceeding 35.
  • Test Example 4 Measurement of Viscosity of Branched Megalosaccharide-Containing Syrup
  • the viscosity of the branched megalosaccharide-containing syrup produced in Test Example 3 was measured and compared with the existing oligosaccharide syrup. That is, the viscosity at 10 ° C. to 60 ° C. of the branched megalosaccharide-containing syrup prepared in Test Example 3 was measured.
  • the concentration of syrup was Bx70.
  • the viscosity was measured using VISCOMETER TVB-10 manufactured by Toki Sangyo Co., Ltd., the rotation speed of the rotor was 60 rpm, and the measurement time was 40 seconds.
  • a 300 mL sample was placed in a 300 mL tall beaker and used as a measurement sample.
  • the viscosity of the branched megalosaccharide-containing syrup at each temperature was higher than that of Fuji Oligo G67 manufactured by Nippon Shokuhin Kako Co., Ltd., which is an existing polymer maltooligosaccharide-containing syrup, the viscosity is such that there is no problem in operability even at a solid content of 70%. Met.
  • Test Example 5 Measurement of Sweetness of Branched Megalosaccharide-Containing Syrup
  • the sweetness of the branched megalosaccharide-containing syrup produced in Test Example 3 was measured by Pauli's whole series method (starch sugar related industrial analysis method) Measured according to Starch Sugar Technical Committee, pages 61-62). That is, the sweetness of the sugar aqueous solution prepared at intervals of 0.2% in the range of 0.6 to 1.4% and the branched megalosaccharide-containing syrup having a solid content of 10% is “strong”, “equal”, “weak”. Ten panelists evaluated. Based on the obtained test results, the sweetness degree was calculated by the following formula.
  • S Em / N ⁇ 100
  • Do lowest concentration of standard sugar solution
  • Du highest concentration of standard sugar solution
  • i concentration interval of standard sugar solution
  • ⁇ gr number of people judged as “strong”
  • ⁇ kl number of people judged as “weak”
  • n Number of panelists
  • S sweetness
  • N sample concentration (%)
  • the sweetness of the branched megalosaccharide-containing syrup was 10.7, and it was revealed that the sweetness was extremely low compared with the existing liquid sugar.
  • Production Example 1 Production of branched megalosaccharide (1)
  • Production of branched megalosaccharide 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Paenibacillus sp. Saccharification for 72 hours by adding 100 units per gram of odoratus isoamylase, 0.01% of pullulanase “Amano” 3 per solid, and 3.75 units of ⁇ -glucosidase of Aspergillus niger per gram of solid did. This was heated to 80 ° C., and Christase L1 was added in an amount of 0.005% to the solid content until the iodine reaction disappeared.
  • Activated charcoal was added to the inactivated enzyme at pH 4.0 and decolorized according to a conventional method, followed by filtration through diatomaceous earth to obtain a filtrate. Although this was made into a usual method, the ionic component was removed with the ion exchange resin, and the neutral sugar was obtained. This was decolorized by performing the activated carbon treatment again in the same manner as above, and filtered through diatomaceous earth to obtain a filtrate. This was concentrated under reduced pressure to 75% solids. By the above operation, a branched megalosaccharide-containing syrup was obtained at a yield of about 90% based on the solid content.
  • This product contains 20.3% of megalosaccharide per solid, and when the content of branched megalosaccharide was measured by ⁇ -amylase treatment, branched megalosaccharide having a degree of polymerization of 11 to 35 per solid was measured. It contained 17.9%.
  • the aqueous layer was removed, and 1 mL of water was newly added and stirred for 5 times, and the chloroform layer was recovered.
  • the obtained sample was subjected to gas chromatography to analyze the partially methylated monosaccharide alditol acetate.
  • TC-17 (0.25 mm ⁇ 30 m; manufactured by GL Science) was used for the column, the column temperature was kept at 50 ° C. for 1 minute, and then the column temperature was increased to 280 ° C. by 10 ° C. per minute.
  • the sample injection temperature was 300 ° C.
  • Detection was performed by FID, and the detection temperature was 300 ° C.
  • Helium was used as the carrier gas, and the flow rate was 2.5 mL / min.
  • 1,5-di-O-acetyl-2,3,4,6-tetra-O was obtained as a partially methylated derivative derived from branched megalosaccharide obtained using ⁇ -glucosidase derived from Aspergillus niger.
  • -Methylhexitol, 1,5,6-tri-O-acetyl-2,3,4-tri-O-methylhexitol and 1,4,5-tri-O-acetyl-2,3,6 , -Tri-O-methylhexitol was detected. This revealed that the branched structure of the branched megalosaccharide obtained in Production Example 1 (1) is an ⁇ -1,6-bond.
  • the reaction solution obtained by filtration through a 0.45 ⁇ m filter was concentrated and used as a fraction source. This was subjected to carbon-celite column chromatography. In this chromatography, sugar was eluted with a linear concentration gradient of 0-3% n-butanol.
  • the obtained pentasaccharide fraction was desalted with an ion exchange resin, and then filtered through a 0.45 ⁇ m filter and freeze-dried. Of this, 5 mg was subjected to methylation analysis as described above.
  • Production Example 2 Production of branched megalosaccharide (2) A 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Bacillus coagulans cyclodextrin-producing enzyme was paired with 1 unit per gram of solid content and Myloides odoratus isoamylase. Saccharification was performed for 60 hours by adding 100 units per gram of solid content, 0.01% of pullulanase “Amano” 3 per solid content, and 3.75 units of ⁇ -glucosidase of Aspergillus niger per gram of solid content.
  • Production Example 3 Production of branched megalosaccharide (3) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Bacillus stearothermophilus cyclodextrin-forming enzyme was added to 1 unit per gram of solid content, and Myloides odoratus isoform. Saccharification was performed by adding 100 units per gram of amylase, 0.01% of pullulanase “Amano” 3 per solid, and 3.75 units of ⁇ -glucosidase of Aspergillus niger per gram of solid for 60 hours.
  • Production Example 4 Production of branched megalosaccharide (4) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Bacillus mazellans cyclodextrin-forming enzyme was paired with 1 unit per gram of solids and Myloides odoratus isoamylase. Saccharification was performed for 60 hours by adding 100 units per gram of solid content, 0.01% of pullulanase “Amano” 3 per solid content, and 3.75 units of ⁇ -glucosidase of Aspergillus niger per gram of solid content.
  • Production Example 5 Production of branched megalosaccharide (5)
  • Manufacture of branched megalosaccharide 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Paenibacillus sp. 100 mg / g of Myloides odoratus isoamylase, 0.01% of pullulanase “Amano” 3 per g of solid, and 0.65 unit of ⁇ -glucosidase of Acremonium sp. Saccharified for 60 hours.
  • the subsequent operation was carried out in the same manner as in Production Example 1 to obtain a branched megalosaccharide-containing syrup having a solid content of 75% in a yield of about 90% relative to the solid content.
  • the product contained 81.3% of megalosaccharide per solid and 56.1% of branched megalosaccharide per solid.
  • 1,5-di-O-acetyl-2,3,4,6-tetra- was obtained as a partially methylated derivative derived from branched megalosaccharide obtained by using ⁇ -glucosidase derived from Acremonium sp.
  • O-methylhexitol, 1,3,5-tri-O-acetyl-2,4,6-tri-O-methylhexitol and 1,4,5-tri-O-acetyl-2,3 6-Tri-O-methylhexitol was detected.
  • This revealed that the branched structure of the branched megalosaccharide obtained in Production Example 5 (1) is an ⁇ -1,3-linkage.
  • the reaction solution obtained by filtration through a 0.45 ⁇ m filter was concentrated and used as a fraction source. This was subjected to carbon-celite column chromatography. In this chromatography, sugar was eluted with a linear concentration gradient of 0-3% n-butanol.
  • the obtained pentasaccharide fraction was desalted with an ion exchange resin, and then filtered through a 0.45 ⁇ m filter and freeze-dried. Of this, 5 mg was subjected to methylation analysis as described above.
  • Production Example 6 Production of branched megalosaccharide (6) A 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Bacillus coagulans cyclodextrin-producing enzyme was paired with 1 unit per gram of solid content and Myloides odoratus isoamylase. Saccharification was carried out by adding 100 units per gram of solid content, 0.01% of pullulanase “Amano” 3 per solid content, and 0.65 units of Acremonium sp. ⁇ -glucosidase per gram of solid content for 60 hours.
  • Production Example 7 Production of branched megalosaccharide (7) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Bacillus stearothermophilus cyclodextrin-forming enzyme was added to 1 unit per gram of solid content, and Myloides odoratus isoform. Saccharification was performed by adding 100 units per gram of amylase, 0.01% of pullulanase “Amano” 3 per solid, and 0.65 units of Acremonium sp. ⁇ -glucosidase per gram of solid for 60 hours.
  • Production Example 8 Production of branched megalosaccharide (8) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Bacillus mazellans cyclodextrin-forming enzyme was paired with 1 unit per gram of solids and Myloides odoratus isoamylase. Saccharification was carried out by adding 100 units per gram of solid content, 0.01% of pullulanase “Amano” 3 per solid content, and 0.65 units of Acremonium sp. ⁇ -glucosidase per gram of solid content for 60 hours.
  • Production Example 9 Production of branched megalosaccharide (9) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and pH 6.0, to which Paenibacillus sp. Cyclodextrin-producing enzyme was paired with 2 units per gram of solid content and Pseudomonas amylodelamosa isoamylase. Saccharification was carried out for 60 hours by adding 200 units per gram of solid content, 0.02% of pullulanase “Amano” 3 per solid content, and 3.75 units of ⁇ -glucosidase of Aspergillus niger per gram of solid content.
  • Production Example 10 Production of branched megalosaccharide (10) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Paenibacillus sp. Cyclodextrin-producing enzyme was paired with 1 unit per gram of solid content and Pseudomonas amylodelamosa isoamylase was paired. Saccharification was carried out by adding 100 units per gram of solid content, 0.01% of pullulanase “Amano” 3 per solid content, and 0.65 units of Acremonium sp. ⁇ -glucosidase per gram of solid content for 60 hours.
  • Production Example 11 Production of Branched Megalosaccharide (11) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Paenibacillus sp. Cyclodextrin-forming enzyme was paired with 1 unit per 1 g of solid content and pullulanase “Amano” 3 was paired. 0.01% per solid, Aspergillus niger ⁇ -glucosidase was added to 3.75 units per gram of solid and saccharified for 60 hours.
  • Production Example 12 Production of branched megalosaccharide (12) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Paenibacillus sp. Cyclodextrin-producing enzyme was paired with 1 unit per 1 g of solid content, and pullulanase “Amano” 3 was paired. Saccharification was carried out for 60 hours by adding 0.65 unit of ⁇ -glucosidase of 0.01% per solid and 0.01% Acremonium sp.
  • Production Example 13 Production of branched megalosaccharide (13) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Paenibacillus sp. Cyclodextrin-forming enzyme was added to 1 unit per gram of solid and Aspergillus niger ⁇ -glucosidase. Saccharification was carried out for 60 hours by adding 3.75 units per gram of the solid content. The subsequent operation was carried out in the same manner as in Production Example 1 to obtain a branched megalosaccharide-containing syrup having a solid content of 75% in a yield of about 90% relative to the solid content. The product contained 17.3% of megalosaccharide per solid and 17.0% of branched megalosaccharide per solid.
  • Production Example 14 Production of Branched Megalosaccharide (14) 30% (w / w) DE 6.5 corn starch liquefied liquid was adjusted to a temperature of 53 ° C. and a pH of 6.0, to which Paenibacillus sp. Cyclodextrin-producing enzyme was 1 unit per gram of solid content, Acremonium sp ⁇ -glucosidase Was saccharified for 60 hours by adding 0.65 units per gram of the solid content. The subsequent operation was carried out in the same manner as in Production Example 1 to obtain a branched megalosaccharide-containing syrup having a solid content of 75% in a yield of about 90% relative to the solid content. In addition, this product contained 32.6% of megalo sugar per solid content, and contained 29.2% of branched megalo sugar per solid content.
  • Production Example 15 Production of powdered koji containing branched megalo sugar (1)
  • the sugar solution obtained in Production Example 1 was pulverized using an L-12 type spray dryer (atomizer type: Okawara Chemical).
  • the spray dryer was operated at an inlet set temperature of 160 ° C., an outlet set temperature of 120 ° C., an atomizer rotational speed of 10,000 rpm, a cyclone differential pressure of about 70 mmHg, and a liquid supply amount of 5 L / h.
  • a powdered branched megalosaccharide-containing powder cake with a recovery rate of about 95% was obtained.
  • Production Example 16 Production of branched megalosaccharide-containing flour (2) The sugar solution obtained in Production Example 5 was spray-dried in the same manner as in Production Example 15 using an L-12 type spray dryer. By this operation, a powdered branched megalosaccharide-containing powder cake with a recovery rate of about 95% was obtained.
  • Production Example 17 Production of Branched Megalosaccharide Fraction Product
  • a gel filtration column (TOYOPEARL HW-40S, ⁇ 5.0 cm ⁇ 87 cm, prepared by preparing the branched megalosaccharide-containing syrup of Production Example 1 to about Brix 50 and heating to 60 ° C. Elution was carried out using purified water at a flow rate of 34 to 48 ml / h.
  • the saccharide composition of the eluate was analyzed by high performance liquid chromatography, and the fraction of branched sugars below tetrasaccharide (high molecular fraction) and the fraction of 0.5% or higher (low molecular content fraction). Min) was collected.
  • the collected fraction was concentrated to about Brix 30 by drying under reduced pressure. By repeating the above operation 11 times, 23 g of a polymer fraction and 39 g of a low-molecule-containing fraction were obtained in terms of solid content.
  • a branched megalosaccharide reduced product was prepared using NaBH 4 . That is, after cooling 10 minutes branched cytomegalovirus sugars adjusted to Bx10 (Preparation Example 5) solution 5ml in ice, and dissolved by the NaBH 4 by about 20mg added 10 times. Two drops of aqueous ammonia were added to this solution to adjust the pH to 10 or more, and then a reduction reaction was performed at room temperature for 3 hours. After the reaction, the remaining NaBH 4 was decomposed by adding Amberlite MB-4 (organo) until hydrogen generation and the color change of the resin disappeared. The liquid layer was collected while washing the resin with water and dried using a rotary evaporator. 1 ml of methanol was added to this and dissolved, and again dried. This operation was repeated 5 times. Finally, the product dissolved in purified water was used as a reduced product solution.
  • the DE of the obtained reduced product was measured according to a modified somogy method (starch sugar related industrial analysis method (Food Chemical Newspaper Co., Ltd.) (issued on November 1, 1991), pages 11 to 13). Met. The DE before the reduction was 10.2, and it was confirmed that the reducing end was completely reduced by the reduction reaction. In addition, the composition of the degree of polymerization did not change before and after the reduction reaction, and no glucoside bond breakage was observed (data not shown).
  • Formulation Example 1 Green tea beverage A green tea beverage was produced according to the formulation shown in Table 4 (mass ratio based on 100 as a whole).
  • the syrup of Production Example 5 was used as the branched megalosaccharide syrup.
  • Celldex SL-20, Celldex B-100, and Fujioligo G67 were manufactured by Nippon Shokuhin Kako Co., Ltd. (hereinafter the same).
  • Celdex SL-20 is a liquid or powder product containing 20% cyclodextrin
  • Celdex B-100 is crystalline ⁇ -cyclodextrin.
  • Fuji oligo G67 is syrup mainly composed of maltohexaose and maltoheptaose.
  • the addition ratio of the syrup-like raw material was calculated based on the mass of the solid content (hereinafter the same).
  • Table 5 shows the sugar composition and sweetness of the blended megalosaccharide syrup and Fujioligo G67.
  • the sugar composition was analyzed using HPLC. The analysis conditions were the same as in Test Example 2. The sweetness level was measured by the method described in Test Example 5.
  • the bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ), and sweetness is strong. ( ⁇ ), slightly sweet ( ⁇ ), not sweet ( ⁇ ), umami is umami ( ⁇ ), umami is a little ( ⁇ ), umami is low ( ⁇ ), umami is weak (x), overall evaluation The evaluation results were very good ( ⁇ ⁇ ), good ( ⁇ ⁇ ), not very good ( ⁇ ), and bad ( ⁇ ).
  • Formulation Example 2 High-concentration polyphenols-containing green tea beverage A high-concentration polyphenol-containing green tea beverage was produced according to the formulation shown in Table 7 (mass ratio when the whole was 100). As the branched megalosaccharide syrup, the syrup of Production Example 5 was used. Polyphenon CH manufactured by Mitsui Norin Co., Ltd. was used (hereinafter the same).
  • Ten panelists performed sensory evaluation of the produced tea beverage and evaluated the balance of bitterness / astringency and taste. Table 8 shows the evaluation results.
  • the bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ), and sweetness is strong. ( ⁇ ), slightly sweet ( ⁇ ), not sweet ( ⁇ ), umami is umami ( ⁇ ), umami is a little ( ⁇ ), umami is low ( ⁇ ), umami is weak (x), overall evaluation The evaluation results were very good ( ⁇ ⁇ ), good ( ⁇ ⁇ ), not very good ( ⁇ ), and bad ( ⁇ ).
  • the bitterness and astringency of polyphenols can be reduced, and umami can be imparted. Furthermore, these effects were obtained without breaking the balance of tea taste.
  • Formulation Example 3 Black Tea Beverage A black tea beverage was produced according to the formulation shown in Table 9 (mass ratio based on 100 as a whole).
  • the black tea used was a clear black tea extract obtained by adding 200 ml of hot water (95 ° C.) to 2 g of black tea leaves and performing extraction for 2 minutes, followed by suction filtration after extraction.
  • the syrup of Production Example 5 was used as the branched megalosaccharide syrup.
  • bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ).
  • the evaluation results were very good ( ⁇ ), good ( ⁇ ), not very good ( ⁇ ), and bad ( ⁇ ).
  • Formulation Example 4 Green tea jelly Green tea jelly was prepared in a conventional manner with the formulation shown in Table 11 (mass ratio based on 100 as a whole). As the branched megalosaccharide syrup, the syrup of Production Example 5 was used.
  • bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ). About ((circle)), there is no richness (x), and the balance of the taste was shown by the evaluation result of very good ((double-circle)), good ((circle)), not so good ((triangle
  • Formulation Example 5 Green tea beverage A green tea beverage was produced according to the formulation shown in Table 13 (mass ratio based on 100 as a whole). As the branched megalosaccharide syrup, the branched megalosaccharide syrup fraction produced in Production Example 17 was used.
  • the analysis results of the sugar composition of the blended megalosaccharide syrup fraction and Fujioligo G67 were as follows.
  • the sugar composition was analyzed using HPLC.
  • the analysis conditions were the same as in Test Example 2.
  • the sensory evaluation of the prepared green tea beverage was performed by 23 panelists, and the balance of bitterness / astringency and taste was evaluated. The evaluation results are shown in Table 15.
  • the bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ), and sweetness is strong. ( ⁇ ), slightly sweet ( ⁇ ), not sweet ( ⁇ ), umami is umami ( ⁇ ), umami is slightly ( ⁇ ), umami is low ( ⁇ ), umami is not ( ⁇ ), balance of taste The evaluation results were very good ( ⁇ ), good ( ⁇ ), not very good ( ⁇ ), and bad ( ⁇ ).
  • Japanese Patent Application Laid-Open No. 2006-280254 discloses a method for suppressing the bitterness and astringency of catechin using a 3-4 saccharide having a branched structure as an active ingredient. Even when the sugar syrup fraction was used, the bitterness / astringency reduction effect was recognized. Further, the use of the branched megalosaccharide syrup according to the present invention, which contains almost no 3-4 saccharides, gave a high umami imparting effect.
  • Formulation Example 6 High concentration polyphenols-containing green tea beverage A high concentration polyphenols-containing green tea beverage was produced according to the formulation shown in Table 16 (mass ratio when the whole was 100). As the branched megalosaccharide syrup, the branched megalosaccharide syrup fraction produced in Production Example 17 was used.
  • bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ).
  • the evaluation results were very good ( ⁇ ), good ( ⁇ ), not very good ( ⁇ ), and bad ( ⁇ ).
  • Formulation Example 7 Black tea beverage A black tea beverage was produced according to the formulation shown in Table 18 (mass ratio based on 100 as a whole).
  • the black tea used was a clear black tea extract obtained by adding 200 ml of hot water (95 ° C.) to 2 g of black tea leaves and performing extraction for 2 minutes, followed by suction filtration after extraction.
  • As the branched megalosaccharide syrup the branched megalosaccharide syrup fraction produced in Production Example 17 was used.
  • bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ).
  • the evaluation results were very good ( ⁇ ), good ( ⁇ ), not very good ( ⁇ ), and bad ( ⁇ ).
  • Formulation Example 8 Green tea jelly Green tea jelly was prepared in a conventional manner with the formulation shown in Table 20 (mass ratio based on 100 as a whole). As the branched megalosaccharide syrup, the branched megalosaccharide syrup fraction produced in Production Example 17 was used.
  • the sensory evaluation of the produced green tea jelly was performed by 10 panelists, and the balance of bitterness / astringency and taste was evaluated. The evaluation results are shown in Table 21.
  • bitterness and astringency reduction effects in the table are shown as evaluation results of very effective ( ⁇ ), effective ( ⁇ ), almost no effect ( ⁇ ), no effect ( ⁇ ), and richness is effective
  • evaluation results of ( ⁇ ), no effect ( ⁇ ), and balance of taste were shown as evaluation results of very good ( ⁇ ), good ( ⁇ ), not very good ( ⁇ ), and bad ( ⁇ ).
  • the bitterness and astringency of polyphenols were reduced by using Fujioligo G67, Celdex SL-20, or Celdex B-100.
  • Fujioligo G67 was weaker than that of branched sugars.
  • Celdex SL-20 and Celdex B-100 reduced bitterness and astringency as much as or more than the branched megalosaccharide syrup, but the green tea flavor became difficult to feel.
  • the branched megalosaccharide syrup fraction according to the present invention when used, it was possible to suppress the bitterness and astringency of polyphenols. In addition, richness can be imparted, and the use of the branched megalosaccharide syrup fraction according to the present invention did not impair the overall taste balance.
  • Formulation Example 9 Fruit juice beverage A fruit juice beverage was prepared by blending 1% (w / w) (in terms of solid content) of the branched megalosaccharide syrup prepared in Production Example 1 with respect to a commercially available low fruit juice beverage. As a result, compared to the non-added group, the richness increased in the branched megalosaccharide added group, and it was possible to give depth to the fruit juice drink. Branched megalosaccharide can be advantageously used as a rich taste enhancer even in a low fruit juice beverage.
  • Formulation Example 10 High-sweetness sweetener-containing beverage Acesulfame K 0.05% (w / w) or aspartame 0.03% (w / w) -containing beverage 1% of the branched megalosaccharide syrup prepared in Production Example 1 A blended beverage (w / w) (solid content conversion) was prepared. The subtle sweetness of the aftertaste of branched megalo sugar worked effectively, and the bitterness of the aftertaste of high-intensity sweeteners was improved, and it was possible to make a drink that was comfortable to drink. Thus, the branched megalosaccharide according to the present invention can be advantageously used as a taste improving agent for high-intensity sweeteners.
  • Formulation Example 11 With respect to 100 parts by mass of the frozen fried egg whole eggs, 7 parts by mass of the branched megalosugar syrup prepared in Production Example 1 (in terms of solid content), 1.5 parts by mass of the modified starch, and 30 parts by mass of the soup stock are mixed.
  • Fried eggs were prepared by a conventional method. It was frozen with a quick freezer and thawed at room temperature after 2 weeks. Since this product contains a branched megalosaccharide having excellent aging resistance, it was kept fresh even after freezing and thawing. That is, it was confirmed that the branched megalosaccharide according to the present invention has an effect of maintaining freshness after freezing and thawing.
  • Formulation Example 12 2.2 parts by mass of each anti-powder yeast, 0.1 parts by mass of yeast food, 2 parts by mass of sugar, 3 parts by mass of the branched megalosaccharide syrup prepared in Production Example 1 (100 parts by mass of bread crumbs ) Solid content conversion), 2 parts by mass of sodium chloride, 2 parts by mass of skim milk powder, 6 parts by mass of fats and oils, and 67 parts by mass of water were used to prepare bread using a medium seed method. Since this product contains a branched megalosaccharide with excellent aging resistance, a bread with a soft texture was obtained. That is, it was confirmed that the branched megalosaccharide according to the present invention has an effect of giving a soft texture to food.
  • Formulation Example 13 17 parts by mass of soft cookie oil / fat, 50 parts by mass of branched megalosugar syrup (solid equivalent) prepared in Production Example 1 vs. powder, 60 parts by mass of sugar vs. powder, 50 parts by mass of whole egg Were sequentially added and mixed. After adding 0.2 parts by weight of vanilla oil to powder, 40 parts by weight of skim milk powder and powder, 100 sieved wheat flour and 0.9 parts by weight of baking powder were mixed. Firing was carried out for 13 minutes at 195 ° C. on the top and 170 ° C. on the bottom. Since this product contains a branched megalosaccharide with excellent aging resistance, it can retain a moist texture for a long period of time. That is, it was confirmed that the branched megalosaccharide according to the present invention has an effect of imparting a moist texture to food.
  • Formulation Example 14 Ice uniformity improvement / promotion effect 4% (w / w) of branched megalosaccharide syrup prepared in Production Example 5 (in terms of solid content), 5% of sugar (w / w), and 0 of pigment .4% (w / w) (Sun Red No. 5F (manufactured by San-Ei Gen FFI Co., Ltd.)) was added to prepare a mixed aqueous solution. This was frozen overnight in a ⁇ 30 ° C. freezer. Sampling was carried out over time at the time of melting at room temperature, and the elution state of branched megalosaccharide and sugar was confirmed by high performance liquid chromatography (HPLC).
  • HPLC high performance liquid chromatography
  • Formulation Example 15 Vinegar Beverage Apple Vinegar 8% (w / w), Fructose Glucose Liquid Sugar (manufactured by Nippon Shokuhin Kako Co., Ltd.) 8% (w / w) (in terms of solid content) and Branched Megalosaccharide Syrup
  • blended 1% (w / w) (solid content conversion) was evaluated. Since this product contains a branched megalosaccharide that has an excellent acidity-reducing effect, the acidity is softened and the drinking comfort can be improved. That is, it was confirmed that the branched megalosaccharide according to the present invention has a sour taste reducing effect.
  • Formulation Example 16 Mixing 154.5 parts by mass of water, 0.75 parts by mass of gluconodeltalactone and 2 parts by mass of the branched megalosaccharide syrup prepared in Production Example 1 (in terms of solid content) with 100 parts by mass of aseptic cooked rice, I cooked rice. Since it contains a branched megalosaccharide that has an excellent acid odor suppressing effect, the acid odor derived from gluconodeltalactone after cooking or during reheating was reduced. That is, the branched megalosaccharide according to the present invention has an effect of reducing the acid odor, and can be used as an acid odor reducing agent for a preservative.
  • Formulation Example 17 Fructose-glucose liquid sugar 4% (w / v) (in terms of solid content) and Production Example 5 so that the alcohol concentration is 6% (v / v) using Nikolai vodka (Kirin Seagram Co., Ltd.)
  • the alcoholic beverage blended with 1% (w / v) branched megalosaccharide syrup (converted to solid content) prepared in the above was evaluated. Since this product contains branched megalosaccharide, which is excellent in reducing alcohol feeling, the taste of alcohol is reduced and the drinking comfort is improved. That is, the branched megalosaccharide according to the present invention can be advantageously used as a taste improving agent for alcoholic beverages.
  • Formulation Example 18 Milk Beverage Milk 30% (w / w), Fructose Glucose Liquid Sugar 4% (w / w) (Solid Content) and Branched Megalosaccharide Syrup 1% (w / w) Prepared in Production Example 5 ( A solid beverage) was mixed to prepare a milk beverage. Compared to the additive-free zone, this product has improved milky taste and has a rich beverage. That is, the branched megalosaccharide by this invention can be used for the food-drinks containing milk for the purpose of the improvement of a milky taste.
  • Formulation Example 19 Jelly dextrin (TK-16 (manufactured by Matsutani Chemical Industry)) 20% (w / w), fructose-glucose liquid sugar 8% (in terms of solid content) (manufactured by Nippon Shokuhin Kako), cool agar (manufactured by Nitta Gelatin) 2% (w / w), tri-Na tricitrate 0.1% (w / w), citric acid 0.17% (w / w) and 5% of branched megalosaccharide syrup prepared in Production Example 5 (w / w) ) (In terms of solid content) was used to prepare a jelly.
  • TK-16 manufactured by Matsutani Chemical Industry
  • TK-16 is a powdery dextrin having a DE of 16-19. Since this product contains a branched megalosaccharide that is excellent in reducing the powdery odor of dextrin, the dextrin odor was alleviated even in jelly using a large amount of dextrin as in this test section. That is, the branched megalosaccharide according to the present invention can be advantageously used even when the food or drink contains a large amount of dextrin.
  • Blending Example 20 Teriyaki Sauce A Teriyaki sauce was prepared according to the blending shown in Table 22 (mass ratio when water was 200). As the branched megalosaccharide syrup, the syrup of Production Example 1 was used. Fuji oligo G67 is syrup mainly composed of maltohexaose and maltoheptaose. Chicken thighs were used and soaked overnight in a sauce that was 30% (w / w) of the weight of the meat. The chicken was steam-heated until it reached a central temperature of 70 ° C., and then poured again into the sauce, and then baked on a hot plate at 180 ° C. for 1.5 minutes on each side.
  • the teriyaki chicken produced by 10 panelists was subjected to sensory evaluation, and shine and gloss were evaluated. The evaluation results are shown in Table 23.
  • Formulation Example 21 Beverage containing milk protein (1)
  • a milk protein-containing beverage was produced according to the following procedure with the formulation shown in Table 24 (mass ratio when the whole was 40). That is, sugar or dextrin and skim milk powder shown in Table 24 were dissolved and mixed and stirred. Next, the pH was adjusted to 6.4 using citric acid, tri-Na citrate, and ascorbic acid. This aqueous solution was filled into a 50 ml Falcon tube, sealed and subjected to retort sterilization at 121 ° C. and 1.2 kgf / cm 2 (using HIGH-PRESSURE STEAM STERILIZER / BS-325 manufactured by Tommy Seiko Co., Ltd.). .
  • the syrup obtained in Production Example 5 was used as the branched megalosaccharide syrup.
  • Dextrin is Paindex # 2 (DE approx. 11 manufactured by Matsutani Chemical Industry Co., Ltd.), Paindex # 100 (DE approx. 2-5 manufactured by Matsutani Chemical Industry Co., Ltd.), Fujistar 5V (DE approx. 5 manufactured by Nippon Shokuhin Kako), Fujister 12V (DE About 12 (made by Nippon Food Chemicals), Paindex # 4 (DE about 19; made by Matsutani Chemical Industry), TK-16 (DE about 16-19 made by Matsutani Chemical Industry), cluster dextrin (DE about 2 made by Nippon Food Chemicals) did.
  • the aggregation state of milk protein in the beverage produced as described above was visually confirmed, and a stability test was performed.
  • the results are shown in Table 25.
  • the protein stability in the table is indicated by the evaluation results of stability ( ⁇ ), slightly stable ( ⁇ ), and unstable ( ⁇ ).
  • Formulation Example 22 Beverage containing milk protein (2) A milk protein-containing beverage was produced according to the following procedure with the formulation shown in Table 26 (mass ratio when the whole was 200). That is, sugar or dextrin and skim milk powder shown in Table 26 were dissolved and mixed and stirred. Next, the pH was adjusted to 6.4 using citric acid, tri-Na citrate, and ascorbic acid. This aqueous solution was filled into a 100 ml shot bottle, sealed, and subjected to retort sterilization at a temperature of 121 ° C. and 1.2 kgf / cm 2 (using a HIGH-PRESS STEAM STERIZIZER / BS-325 manufactured by Tommy Seiko Co., Ltd.). .
  • Fujioligo G67 is syrup mainly composed of maltohexaose and maltoheptaose.
  • the aggregation state of milk protein in the beverage produced as described above was visually confirmed, and a stability test was performed.
  • a 10% (w / w) aqueous solution of sugar or dextrin used was prepared, and the osmotic pressure was measured with an Osmometer (Fiske Mark 3).
  • the results are shown in Table 27.
  • the protein stability in the table is indicated by the evaluation results of stability ( ⁇ ) and instability ( ⁇ ).
  • the branched megalosaccharide according to the present invention can be easily adjusted to a low osmotic pressure as compared with monosaccharides, disaccharides, and oligosaccharides, and has less burden on the gastrointestinal tract. Moreover, since the milk protein is not destabilized as when dextrin is used, it can be advantageously used for enteral and oral nutrients that require adjustment of osmotic pressure.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Inorganic Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Seasonings (AREA)
  • Medicinal Preparation (AREA)
  • Confectionery (AREA)
  • Tea And Coffee (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Non-Alcoholic Beverages (AREA)

Abstract

L'invention concerne un mégalo-saccharide ramifié présentant une résistance au vieillissement, un effet améliorant la saveur et des propriétés similaires. L'invention concerne en particulier un glucane ayant un degré de polymérisation de 11 à 35.  Le glucane possède une structure ramifiée au moins au niveau d'une terminaison non réductrice.
PCT/JP2009/057609 2008-09-18 2009-04-15 Nouveau glucane ramifié, son procédé de production et son utilisation WO2010032510A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008-239570 2008-09-18
JP2008239570 2008-09-18

Publications (1)

Publication Number Publication Date
WO2010032510A1 true WO2010032510A1 (fr) 2010-03-25

Family

ID=41591577

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2009/057609 WO2010032510A1 (fr) 2008-09-18 2009-04-15 Nouveau glucane ramifié, son procédé de production et son utilisation

Country Status (2)

Country Link
JP (1) JP4397965B1 (fr)
WO (1) WO2010032510A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6366781B1 (ja) * 2017-06-02 2018-08-01 株式会社ロッテ ほぐれやすい冷菓及びその製造方法
JP2020058289A (ja) * 2018-10-10 2020-04-16 日本食品化工株式会社 果汁感が増強された果汁風味飲食品およびその製造方法
US11498939B2 (en) 2016-09-15 2022-11-15 Roquette Freres Glucose polymers for peritoneal dialysis

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5507105B2 (ja) * 2009-03-26 2014-05-28 昭和産業株式会社 新規な澱粉分解物、該澱粉分解物を含有する食品添加剤、飲食物、及び薬剤
JP5507107B2 (ja) * 2009-03-26 2014-05-28 昭和産業株式会社 澱粉分解物、該澱粉分解物を含有する食品添加剤、飲食物、薬剤、及び澱粉分解物製造方法
EP2248907A1 (fr) 2009-05-08 2010-11-10 Rijksuniversiteit Groningen Gluco-oligosaccharides comprenant des liens (alpha 1-->4) et (alpha 1-->6) glycosidiquues, leur utilisation et procédés de fabrication
JP4971511B2 (ja) * 2010-03-02 2012-07-11 昭和産業株式会社 糖組成物及び飲食品
JP5862850B2 (ja) * 2010-11-08 2016-02-16 松谷化学工業株式会社 つゆ、たれ類
JP6072499B2 (ja) * 2012-10-17 2017-02-01 松谷化学工業株式会社 分岐デキストリン及びその用途
CN102965361B (zh) * 2012-12-04 2014-05-28 昆明爱科特生物科技有限公司 一种普鲁兰酶XWPu2及其基因
US20160008392A1 (en) * 2013-03-01 2016-01-14 Hayashibara Co., Ltd. Agent for lifestyle-related disease and oral composition comprising same
JP6513908B2 (ja) * 2014-05-29 2019-05-15 日本食品化工株式会社 起泡・泡持ち向上剤
JP6470099B2 (ja) * 2015-04-24 2019-02-13 昭和産業株式会社 澱粉分解物、並びに該澱粉分解物を用いた粉飴、シラップ及び飲食品
JP6936737B2 (ja) * 2016-01-13 2021-09-22 株式会社林原 ビールテイスト飲料とその製造方法
JP7204161B2 (ja) * 2016-02-16 2023-01-16 三重化糧株式会社 液体状調味液、飲食物
JPWO2018190310A1 (ja) * 2017-04-11 2020-05-14 株式会社林原 品質改善剤並びにその用途
JP7354237B2 (ja) * 2019-05-13 2023-10-02 昭和産業株式会社 改質剤、該改質剤を含有する改質用組成物、及びこれらを用いた飲食品、医薬品、化粧品、工業製品、飼料、培地、又は肥料、並びに、これらの製品の改質方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6075296A (ja) * 1984-08-30 1985-04-27 Norin Suisansyo Shokuhin Sogo Kenkyusho 分岐デキストリンの製造方法
JPS63109790A (ja) * 1986-10-27 1988-05-14 Showa Sangyo Co Ltd 分岐オリゴ糖シラツプの連続的製造方法
JPH06209784A (ja) * 1992-10-28 1994-08-02 Enzyme Bio Syst Ltd 澱粉を非ランダムに開裂する為の方法およびそれによって製造される低いｄ．ｅ．の転化生成物
JP2001258589A (ja) * 2000-03-23 2001-09-25 Nippon Shokuhin Kako Co Ltd デキストランの製造法
JP2001294601A (ja) * 2000-04-11 2001-10-23 Akita Prefecture 高度分岐澱粉と該高度分岐澱粉の製造方法
JP2002034587A (ja) * 2000-07-26 2002-02-05 National Agricultural Research Organization 可溶性分岐α−グルカンの製造方法、可溶性分岐α−グルカンおよびα−グルカンの老化抑制処理剤
JP2005213496A (ja) * 2003-12-19 2005-08-11 Roquette Freres 可溶性の高度に分岐したグルコースポリマー
JP2006312705A (ja) * 2005-04-08 2006-11-16 Hayashibara Biochem Lab Inc 分岐澱粉とその製造方法並びに用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3410210B2 (ja) * 1994-04-18 2003-05-26 日本食品化工株式会社 冷凍パン生地類改良剤及び冷凍パン生地類の製造方法
JPH08136331A (ja) * 1994-06-21 1996-05-31 Minoru Yoshino 自動車用重量計
JP4712346B2 (ja) * 2004-10-27 2011-06-29 日本食品化工株式会社 氷の製造方法及び該方法によって得られる氷
JP4590036B2 (ja) * 2005-08-24 2010-12-01 三菱商事フードテック株式会社 硬質コーティング層と硬質コーティング製品及びその製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6075296A (ja) * 1984-08-30 1985-04-27 Norin Suisansyo Shokuhin Sogo Kenkyusho 分岐デキストリンの製造方法
JPS63109790A (ja) * 1986-10-27 1988-05-14 Showa Sangyo Co Ltd 分岐オリゴ糖シラツプの連続的製造方法
JPH06209784A (ja) * 1992-10-28 1994-08-02 Enzyme Bio Syst Ltd 澱粉を非ランダムに開裂する為の方法およびそれによって製造される低いｄ．ｅ．の転化生成物
JP2001258589A (ja) * 2000-03-23 2001-09-25 Nippon Shokuhin Kako Co Ltd デキストランの製造法
JP2001294601A (ja) * 2000-04-11 2001-10-23 Akita Prefecture 高度分岐澱粉と該高度分岐澱粉の製造方法
JP2002034587A (ja) * 2000-07-26 2002-02-05 National Agricultural Research Organization 可溶性分岐α−グルカンの製造方法、可溶性分岐α−グルカンおよびα−グルカンの老化抑制処理剤
JP2005213496A (ja) * 2003-12-19 2005-08-11 Roquette Freres 可溶性の高度に分岐したグルコースポリマー
JP2006312705A (ja) * 2005-04-08 2006-11-16 Hayashibara Biochem Lab Inc 分岐澱粉とその製造方法並びに用途

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11498939B2 (en) 2016-09-15 2022-11-15 Roquette Freres Glucose polymers for peritoneal dialysis
JP6366781B1 (ja) * 2017-06-02 2018-08-01 株式会社ロッテ ほぐれやすい冷菓及びその製造方法
WO2018221196A1 (fr) * 2017-06-02 2018-12-06 株式会社ロッテ Dessert glacé pouvant fondre facilement et son procédé de production
JP2018201398A (ja) * 2017-06-02 2018-12-27 株式会社ロッテ ほぐれやすい冷菓及びその製造方法
US11576399B2 (en) 2017-06-02 2023-02-14 Lotte Co., Ltd. Frozen confectionery easy to loosen and method for producing the same
JP2020058289A (ja) * 2018-10-10 2020-04-16 日本食品化工株式会社 果汁感が増強された果汁風味飲食品およびその製造方法
JP7508193B2 (ja) 2018-10-10 2024-07-01 日本食品化工株式会社 果汁感が増強された果汁風味飲食品およびその製造方法

Also Published As

Publication number Publication date
JP2010095701A (ja) 2010-04-30
JP4397965B1 (ja) 2010-01-13

Similar Documents

Publication Publication Date Title
JP4397965B1 (ja) 新規分岐グルカン並びにその製造方法および用途
JP6457009B2 (ja) 分岐α−グルカン及びこれを生成するα−グルコシル転移酵素とそれらの製造方法並びに用途
JP4983258B2 (ja) イソサイクロマルトオリゴ糖及びイソサイクロマルトオリゴ糖生成酵素とそれらの製造方法並びに用途
JP4568035B2 (ja) 環状マルトシルマルトース及び環状マルトシルマルトース生成酵素とそれらの製造方法並びに用途
JP6962674B2 (ja) 分岐α−グルカン混合物シラップとその用途
WO1997043435A1 (fr) Procede de preparation de compositions de glucose masse, composition de glucose masse et produits alimentaires et boissons contenant cette composition
JP5778888B2 (ja) 分岐糖類を含有する風味改善剤および製剤用マスキング剤
JP4164367B2 (ja) 分岐環状四糖とその製造方法ならびに用途
JP5255603B2 (ja) 環状マルトシルマルトース及び環状マルトシルマルトース生成酵素とそれらの製造方法並びに用途
WO2002088374A1 (fr) Processus de production d'isomaltose et utilisation de celui-ci
JP3942543B2 (ja) α−イソマルトシルグルコ糖質生成酵素活性を有するポリペプチド
JP4224401B2 (ja) イソマルトース及びイソマルチトールの製造方法とそれらの用途
JP4982716B2 (ja) 糖質混合物とその製造方法並びに用途
JP3969511B2 (ja) 飲食品の味質改良効果のある糖組成物
JP2022044983A (ja) コーヒー風味飲食品
JP2021193992A (ja) 呈味向上剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09814355

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: COMMUNICATION NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC

122 Ep: pct application non-entry in european phase

Ref document number: 09814355

Country of ref document: EP

Kind code of ref document: A1