WO2014119535A1 - Body taste imparter - Google Patents

Body taste imparter Download PDF

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Publication number
WO2014119535A1
WO2014119535A1 PCT/JP2014/051745 JP2014051745W WO2014119535A1 WO 2014119535 A1 WO2014119535 A1 WO 2014119535A1 JP 2014051745 W JP2014051745 W JP 2014051745W WO 2014119535 A1 WO2014119535 A1 WO 2014119535A1
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WO
WIPO (PCT)
Prior art keywords
acid
glu
kokumi
food
added
Prior art date
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PCT/JP2014/051745
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French (fr)
Japanese (ja)
Inventor
貴志 宮木
黒田　素央
Original Assignee
味の素株式会社
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Priority to JP2014559675A priority Critical patent/JP6314841B2/en
Publication of WO2014119535A1 publication Critical patent/WO2014119535A1/en

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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
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A23L27/22—Synthetic spices, flavouring agents or condiments containing amino acids containing glutamic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/82—Acid flavourants

Definitions

  • the present invention relates to a “kokumi” imparting agent and use thereof.
  • Kokumi is a taste that cannot be expressed with the basic taste.
  • Kokumi '' is not only the basic taste, but also the taste (marginal tastes) and flavor of basic taste such as thickness, growth (mouthfulness), continuity, harmony, etc. Taste with enhanced (marginal flavor).
  • the technique which provides a "brilliance" effectively with respect to food-drinks has been calculated
  • ⁇ -glutamyltripeptides such as glutathione ( ⁇ -Glu-Cys-Gly) and ⁇ -Glu-Val-Gly
  • ⁇ -glutamyldipeptides such as ⁇ -Glu-Met and ⁇ -Glu-Thr are known (Patent Documents 1 and 2).
  • Patent Document 2 discloses that these ⁇ -glutamyl peptides can be used in the form of any pharmacologically acceptable salt, and examples of the salt include salts with succinic acid and maleic acid. ing.
  • Succinic acid, maleic acid, and methylmalonic acid are all dicarboxylic acids and have similar structures to each other.
  • succinic acid is known as an umami substance.
  • the “kokumi” is further enhanced by using a “kokumi” imparting substance such as ⁇ -Glu-Val-Gly together with a dicarboxylic acid such as succinic acid.
  • the present invention has an object to provide a technique for effectively imparting “brillant taste” to foods and drinks.
  • ⁇ -Glutamyl peptide selected from the group consisting of ⁇ -Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and ⁇ -Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys)
  • a “kokumi” imparting agent comprising a dicarboxylic acid selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid.
  • ⁇ -Glutamyl peptide selected from the group consisting of ⁇ -Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and ⁇ -Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys)
  • a method for producing a food and drink with a “kokumi” taste which comprises adding a dicarboxylic acid selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid to the food or drink or a raw material thereof.
  • the concentration is a concentration based on mass unless otherwise specified. That is, for example, “%” indicates “mass%” unless otherwise specified, and “ppm” indicates “mass ppm” unless otherwise specified.
  • the “eating concentration” of a certain component refers to the concentration of the component in the food or drink when eating the food or drink containing the component. That is, the “food concentration” of a component specifically refers to, for example, a food or drink manufactured by adding the “kokumi” imparting agent of the present invention containing the component or a food or drink manufactured by adding the component. The concentration of the component in the food and drink when eating the product.
  • “Kokumi” imparting agent of the present invention relates to ⁇ -Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and ⁇ -Glu-Y (Y represents an amino acid other than Cys or Comprising one or more ⁇ -glutamyl peptides selected from the group consisting of amino acid derivatives) and one or more dicarboxylic acids selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid, Provides a “kokumi” imparting agent.
  • the “kokumi” imparting agent is also referred to as “the“ kokumi ”imparting agent of the present invention”.
  • the ⁇ -glutamyl peptide and the dicarboxylic acid are also collectively referred to as “active ingredients”.
  • ⁇ -glutamyl peptide used in the present invention is represented by the general formula: ⁇ -Glu-X-Gly (X represents an amino acid or an amino acid derivative excluding Cys). It is selected from the group consisting of ⁇ -glutamyl tripeptide and the general formula: ⁇ -Glu-Y (Y represents an amino acid or amino acid derivative other than Cys) and ⁇ -glutamyl dipeptide.
  • ⁇ - means that X or Y is bonded via a carboxyl group at the ⁇ -position of glutamic acid.
  • the ⁇ -glutamyl peptide one ⁇ -glutamyl peptide may be used, or two or more ⁇ -glutamyl peptides may be used in combination.
  • amino acids include neutral amino acids such as Gly, Ala, Val, Leu, Ile, Ser, Thr, Cys, Met, Asn, Gln, Pro and Hyp, acidic amino acids such as Asp and Glu, and Lys. , Basic amino acids such as Arg and His, aromatic amino acids such as Phe, Tyr and Trp, homoserine, citrulline, ornithine, ⁇ -aminobutyric acid, norvaline, norleucine and taurine.
  • amino acid excluding Cys include, for example, those other than Cys.
  • amino group residues mean the following amino acids.
  • Amino acid derivatives refer to various derivatives of amino acids as described above.
  • Examples of amino acid derivatives include special amino acids, unnatural amino acids, amino alcohols, and amino acids in which one or more functional groups such as terminal carbonyl group, terminal amino group, and cysteine thiol group are substituted with various substituents.
  • substituents include an alkyl group, an acyl group, a hydroxyl group, an amino group, an alkylamino group, a nitro group, a sulfonyl group, and various protective groups.
  • amino acid derivatives include Arg (NO 2 ): N- ⁇ -nitroarginine, Cys (SNO): S-nitrocysteine, Cys (S-Me): S-methylcysteine, Cys (S— allyl): S-allyl cysteine, Val-NH 2 : Valinamide, Val-ol: Valinol (2-amino-3-methyl-1-butanol), Met (O): Methionine sulfoxide, and Cys (S-Me) ( O): S-methylcysteine sulfoxide.
  • ⁇ -glutamyl peptide examples include ⁇ -Glu-Val-Gly, ⁇ -Glu-Nva-Gly, ⁇ -Glu-Abu, and ⁇ -Glu-Nva.
  • ⁇ -Glu-Val-Gly is preferable.
  • the ⁇ -glutamyl peptide is a free form, a salt thereof, or a mixture thereof unless otherwise specified.
  • Salt is not particularly limited as long as it can be taken orally.
  • specific examples of salts for acidic groups such as carboxyl groups include ammonium salts, salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium and magnesium, aluminum salts, and zinc salts.
  • Salts with organic amines such as triethylamine, ethanolamine, morpholine, pyrrolidine, piperidine, piperazine and dicyclohexylamine, and salts with basic amino acids such as arginine and lysine.
  • a salt for a basic group such as an amino group specifically, a salt with an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, hydrobromic acid, acetic acid, citric acid, benzoic acid, Organics such as maleic acid, fumaric acid, tartaric acid, succinic acid, tannic acid, butyric acid, hybenzic acid, pamoic acid, enanthic acid, decanoic acid, teocric acid, salicylic acid, lactic acid, oxalic acid, mandelic acid, malic acid, methylmalonic acid Examples thereof include salts with carboxylic acids and salts with organic sulfonic acids such as methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • 1 type of salt may be used and 2 or more types of salts may be used in combination.
  • ⁇ -glutamyl peptide a commercially available product may be used, or a product produced and obtained as appropriate.
  • the peptide production method is not particularly limited, and for example, a known method can be used.
  • Known methods include, for example, (1) a method of chemically synthesizing a peptide and (2) a method of synthesizing a peptide by enzymatic reaction.
  • a method of chemically synthesizing a peptide For the synthesis of a relatively short peptide having 2 to 3 amino acid residues, it is particularly convenient to use a chemical synthesis method.
  • the peptide When a peptide is chemically synthesized, the peptide can be synthesized or semi-synthesized using a peptide synthesizer.
  • a method for chemically synthesizing a peptide include a peptide solid phase synthesis method.
  • the synthesized peptide can be purified by conventional means, for example, ion exchange chromatography, reverse phase high performance liquid chromatography, or affinity chromatography.
  • Such peptide solid-phase synthesis methods and subsequent peptide purification are well known in the art.
  • a method described in International Publication Pamphlet WO 2004/011653 can be used. Specifically, for example, an amino acid or dipeptide in which a carboxyl group is esterified or amidated, and an amino acid in which the amino group is free (for example, an amino acid in which the carboxyl group is protected) are reacted in the presence of a peptide-forming enzyme.
  • the dipeptide or tripeptide can be synthesized by reacting with.
  • the synthesized dipeptide or tripeptide can be appropriately purified.
  • Examples of the peptide-forming enzyme include a culture of a microorganism having the ability to produce a peptide, a culture supernatant separated from the culture, a cell separated from the culture, a treated product of the microorganism, and separated from them. Peptide-forming enzyme.
  • the peptide-generating enzyme one appropriately purified as necessary can be used.
  • ⁇ -glutamyl peptide can be produced by culturing a microorganism capable of producing the ⁇ -glutamyl peptide and recovering the ⁇ -glutamyl peptide from the culture solution or cells.
  • a yeast containing a ⁇ -glutamyl peptide such as ⁇ -Glu-Abu at a high concentration can be obtained by the method described in JP 2012-213376.
  • the ⁇ -glutamyl peptide may or may not be purified to a desired degree.
  • the ⁇ -glutamyl peptide one having a purity of 50% or more, 70% or more, 90% or more, or 95% or more may be used.
  • a material containing the ⁇ -glutamyl peptide may be used.
  • Specific examples of the material containing ⁇ -glutamyl peptide include, for example, fermentation products such as a culture solution obtained by culturing a microorganism having the ability to produce ⁇ -glutamyl peptide, bacterial cells, and culture supernatant. And processed products thereof. Examples of such processed products include yeast extract containing ⁇ -glutamyl peptide (Japanese Patent Laid-Open No. 2012-213376).
  • the dicarboxylic acid used in the present invention is selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid. Succinic acid, maleic acid, and methylmalonic acid have similar structures to each other. As the dicarboxylic acid, one kind of dicarboxylic acid may be used, or two or more kinds of dicarboxylic acids may be used in combination.
  • dicarboxylic acids are free forms, salts thereof, or mixtures thereof.
  • the description of the salt for the acidic group such as a carboxyl group of the ⁇ -glutamyl peptide can be applied mutatis mutandis.
  • dicarboxylic acid a commercially available product may be used, or an appropriately manufactured and acquired product may be used.
  • the production method of the dicarboxylic acid is not particularly limited, and for example, a known method can be used.
  • dicarboxylic acid can be produced by chemical synthesis.
  • the dicarboxylic acid can be produced by culturing a microorganism having the ability to produce the dicarboxylic acid and recovering the dicarboxylic acid from the culture solution or the cells.
  • succinic acid can be produced using microorganisms by the method described in JP-A-2008-011714.
  • dicarboxylic acid can be manufactured by recovering from agricultural, aquatic and livestock products containing the dicarboxylic acid.
  • the dicarboxylic acid may or may not be purified to a desired level.
  • a dicarboxylic acid having a purity of 50% or more, 70% or more, 90% or more, or 95% or more may be used.
  • a material containing a dicarboxylic acid for example, a culture solution obtained by culturing a microorganism capable of producing the dicarboxylic acid, a bacterial product, a fermentation product such as a culture supernatant, and the dicarboxylic acid Agricultural, aquatic and livestock products contained therein, and processed products thereof are mentioned.
  • the “kokumi” imparting agent of the present invention includes a component corresponding to both ⁇ -glutamyl peptide and dicarboxylic acid, for example, a dicarboxylate salt of ⁇ -glutamyl peptide, this component is the “kokumi” of the present invention. It serves as both ⁇ -glutamyl peptide and dicarboxylic acid in the imparting agent.
  • the “kokumi” imparting agent of the present invention contains components corresponding to both ⁇ -glutamyl peptide and dicarboxylic acid, for example, a dicarboxylate salt of ⁇ -glutamyl peptide, Separately, ⁇ -glutamyl peptide and / or dicarboxylic acid may or may not be contained.
  • the “kokumi” imparting agent of the present invention may be composed of only the above-mentioned active ingredient or may contain other ingredients.
  • ingredients are not particularly limited as long as they can be taken orally, and for example, those used in seasonings, foods and drinks, or pharmaceuticals can be used.
  • proline is a free form, a salt thereof, or a mixture thereof unless otherwise specified.
  • proline salt the above-mentioned description of the salt of ⁇ -glutamyl peptide can be applied mutatis mutandis.
  • examples of the “other components” include compounds having “kokumi” imparting activity and compounds having calcium receptor stimulating activity other than the ⁇ -glutamyl peptide used in the present invention.
  • Specific examples of the compound having “kokumi” imparting activity include glutathione and alliin.
  • Specific examples of compounds having calcium receptor stimulating activity include, for example, cations such as calcium and cadolinium; basic peptides such as polyarginine and polylysine; polyamines such as putrescine, spermine and spermidine; proteins such as protamine; phenylalanine, Peptides such as glutathione; cinacalcet.
  • those capable of forming a salt may be used in the form of a salt.
  • the description of the salt of the ⁇ -glutamyl peptide described above can be applied mutatis mutandis.
  • sugars such as sugar, honey, maple syrup, sucrose, glucose, fructose, isomerized sugar, oligosaccharide and the like; sugar alcohols such as xylitol and erythritol; natural or Artificial sweeteners; inorganic salts such as sodium chloride, sodium chloride and potassium chloride; organic acids such as acetic acid and citric acid and salts thereof; amino acids such as glutamic acid and glycine and salts thereof; nucleic acids such as inosinic acid, guanylic acid and xanthylic acid And salts thereof; dietary fiber, pH buffer, fragrance, edible oil, ethanol, water.
  • salt the description of the salt of the ⁇ -glutamyl peptide described above can be applied mutatis mutandis.
  • the form of the “kokumi” imparting agent of the present invention is not particularly limited, and may be any form such as powder, granule, liquid, paste, or cube.
  • the concentration of the active ingredient in the “kokumi” imparting agent of the present invention is not particularly limited as long as it can impart “kokumi” to foods and drinks using the “kokumi” imparting agent of the present invention. It can be set as appropriate according to various conditions such as the eating concentration of the active ingredient and the amount of the “kokumi” imparting agent of the present invention.
  • the total concentration of active ingredients in the “kokumi” imparting agent of the present invention is not particularly limited, and may be, for example, 0.01 ppm or more, 0.1 ppm or more, 1 ppm or more, or 10 ppm or more. Further, the total concentration of the active ingredients in the “kokumi” imparting agent of the present invention is not particularly limited, but may be, for example, 100% or less, 10% or less, or 1% or less.
  • the “total concentration of active ingredients” means the sum of the concentration of ⁇ -glutamyl peptide and the concentration of dicarboxylic acid.
  • the ratio of the active ingredient in the “kokumi” imparting agent of the present invention is not particularly limited as long as it can impart “kokumi” to foods and drinks using the “kokumi” imparting agent of the present invention. It can set suitably according to these conditions.
  • the molar ratio of dicarboxylic acid to ⁇ -glutamyl peptide may be, for example, greater than 1 (that is, the amount of dicarboxylic acid [Mol]> ⁇ -glutamyl peptide amount [mol]).
  • the molar ratio of the dicarboxylic acid to the ⁇ -glutamyl peptide may be, for example, 3 or more, 15 or more, or 30 or more. Further, in the “kokumi” imparting agent of the present invention, the molar ratio of the dicarboxylic acid to the ⁇ -glutamyl peptide may be, for example, 75000 or less, 4000 or less, or 200 or less.
  • the concentration of the ⁇ -glutamyl peptide in the “kokumi” imparting agent of the present invention may be set, for example, within a range that satisfies the ratio of the above-exemplified active ingredients to the above-mentioned active ingredients. Further, ⁇ -glutamyl peptide is included in the “kokumi” imparting agent of the present invention so that, for example, the eating concentration of ⁇ -glutamyl peptide is 0.015 ⁇ mol or more, or 0.3 ⁇ mol or more per 100 g of food or drink. It may be.
  • ⁇ -glutamyl peptide is included in the “kokumi” imparting agent of the present invention so that, for example, the eating concentration of ⁇ -glutamyl peptide is 200 ⁇ mol or less, 20 ⁇ mol or less, or 2 ⁇ mol or less per 100 g of food or drink. It may be.
  • the ⁇ -glutamyl peptide is, for example, such that the eating concentration of the ⁇ -glutamyl peptide is 0.017 ⁇ mol to 1.65 ⁇ mol, or 0.33 ⁇ mol to 1.65 ⁇ mol per 100 g of food or drink. It may be contained in the “kokumi” imparting agent.
  • the eating concentration of ⁇ -glutamyl peptide may be the sum of the eating concentrations of two or more ⁇ -glutamyl peptides.
  • the concentration of the dicarboxylic acid in the “kokumi” imparting agent of the present invention may be set, for example, within a range that satisfies the ratio of the above-exemplified total active ingredients and the above-exemplified active ingredients.
  • the dicarboxylic acid may be included in the “kokumi” imparting agent of the present invention so that the eating concentration of the dicarboxylic acid is 0.5 ⁇ mol or more, or 5 ⁇ mol or more per 100 g of food or drink.
  • the dicarboxylic acid may be contained in the “kokumi” imparting agent of the present invention so that the eating concentration of the dicarboxylic acid is 1400 ⁇ mol or less or 400 ⁇ mol or less per 100 g of food or drink.
  • the dicarboxylic acid is added to the “kokumi” imparting agent of the present invention so that, for example, the eating concentration of the dicarboxylic acid is 0.6 ⁇ mol to 1235 ⁇ mol, or 6.2 ⁇ mol to 309 ⁇ mol per 100 g of food or drink. It may be included.
  • the eating concentration of the dicarboxylic acid may be the sum of the eating concentrations of the two or more dicarboxylic acids.
  • the concentration of “other ingredients” in the “kokumi” imparting agent of the present invention is not particularly limited as long as the “kokumi” imparting agent of the present invention can be used to impart “kokumi” to foods and drinks. It can be appropriately set according to various conditions such as the kind of “component”, the eating concentration of “other components”, and the amount of the “kokumi” imparting agent of the present invention used. The eating concentration of “other components” can be appropriately set according to various conditions such as the type of “other components”.
  • proline is included in the “kokumi” imparting agent of the present invention so that the eating concentration of proline is 0.5 ⁇ mol to 2000 ⁇ mol, preferably 2 ⁇ mol to 1000 ⁇ mol, more preferably 5 ⁇ mol to 500 ⁇ mol per 100 g of food or drink. It may be.
  • each component (that is, the active ingredient and other components as required) contained in the “kokumi” imparting agent of the present invention may be mixed with each other and contained in the “kokumi” imparting agent of the present invention. Each of these may be contained in the “kokumi” imparting agent of the present invention separately or in any combination. If the active ingredient coexists in the food and drink produced by adding the “kokumi” imparting agent of the present invention, the effect of enhancing “kokumi” can be obtained.
  • the present invention is selected from the group consisting of ⁇ -Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and ⁇ -Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys). Adding one or more ⁇ -glutamyl peptides, and one or more dicarboxylic acids selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid to a food or drink or a raw material thereof The manufacturing method of the food / beverage products to which "kokumi" was provided is provided.
  • Such a method for producing a food or drink with a “kokumi” taste is also referred to as a “method of the present invention”.
  • the food / beverage products provided with the “boiled taste” thus produced are also referred to as “the food / beverage products of the present invention”.
  • the term “kokumi” refers to five basic tastes (five basic taste) represented by sweetness (sweet taste), salty taste (salty taste), sour taste (sour taste), bitterness (bitter taste), and umami ) Means a sense that cannot be expressed, not only the basic taste, but also the tastes of the basic tastes such as thickness, growth (mouthfulness), continuity, harmony, etc. (marginal tastes) Taste with enhanced flavor and marginal flavor.
  • “giving a“ kokumi ”” includes enhancing the basic taste and adding or enhancing the surrounding taste of the basic taste such as thickness, spreading, sustainability, and unity.
  • the food and drink is not particularly limited, and includes all kinds of food and drink.
  • foods and beverages include beverages such as water, fruit juice, milk, tea, alcoholic beverages, soups; processed meat products such as ham and sausage; processed fishery products such as kamaboko and chikuwa; milk such as butter, fermented milk, and powdered milk Products: bread, noodles, confectionery, sauce, etc.
  • fruit juice include apple juice.
  • sauce include tomato sauce. Specifically, for example, minestrone soup, potage soup (corn, potato, etc.), consomme soup (chicken, pork, beef, etc.), ramen soup (soy sauce, miso, pork bone, salt, etc.), Chinese soup, Examples include miso soup.
  • the food and drink of the present invention can be produced by the same method using the same raw materials as those of ordinary food and drink, except that the “kokumi” imparting agent or active ingredient of the present invention is added.
  • the “kokumi” imparting agent or the active ingredient of the present invention may be added at any stage of the production process of the food or drink. That is, the “kokumi” imparting agent or active ingredient of the present invention may be added to a raw material for food or drink, may be added to a food or drink in the middle of manufacture, or may be added to a finished food or drink.
  • the “kokumi” imparting agent or active ingredient of the present invention may be added only once, or may be added in two or more times.
  • each active ingredient when the “kokumi” imparting agent of the present invention is added, when the “kokumi” imparting agent of the present invention contains each active ingredient separately or separately in any combination, each active ingredient May be added to the food or drink or its raw material at the same time, or may be added to the food or drink or its raw material individually or in any combination. Moreover, when adding an active ingredient, each active ingredient may be simultaneously added to food / beverage products or its raw material, and may be added to food / beverage products or its raw material separately separately or in arbitrary combinations. Good.
  • the amount added is not particularly limited as long as it can impart “kokumi” to foods and drinks, and in the type of active ingredient, the “kokumi” imparting agent of the present invention. It can set suitably according to various conditions, such as the density
  • the “kokumi” imparting agent of the present invention may be added in an amount of 0.01 ppm to 50% or 0.1 ppm to 10% with respect to the food or drink or its raw material.
  • the “kokumi” imparting agent of the present invention may be added to a food or drink or its raw material so that the eating concentration of each active ingredient is within the eating concentration range of each active ingredient exemplified above.
  • each active ingredient may be added to a food or drink or its raw material so that the eating concentration of each active ingredient is within the eating concentration range of each active ingredient exemplified above.
  • each active ingredient may be added with respect to food-drinks or its raw material by the ratio of the active ingredient in the "boiled taste" imparting agent of this invention illustrated above, for example.
  • a component corresponding to both ⁇ -glutamyl peptide and dicarboxylic acid for example, a dicarboxylate salt of ⁇ -glutamyl peptide
  • the component also serves as both ⁇ -glutamyl peptide and dicarboxylic acid. That is, when components corresponding to both ⁇ -glutamyl peptide and dicarboxylic acid, for example, dicarboxylate of ⁇ -glutamyl peptide, are added, ⁇ -glutamyl peptide and / or dicarboxylic acid may be added separately. Not necessary.
  • the method of the present invention may further include adding other components.
  • other components here, the description of “other components” in the above-described “kokumi” imparting agent of the present invention can be applied mutatis mutandis.
  • proline can be added as the “other components”.
  • the addition of “other components” may be performed in the same manner as the addition of the active ingredients described above.
  • proline may be added to a food or drink or its raw material so that the eating concentration of proline is within the eating concentration range of proline exemplified above.
  • Example 1 Evaluation of “bitter taste” imparting effect by the combined use of ⁇ -Glu-Val-Gly and succinic acid
  • ⁇ -Glu-Val-Gly and disodium succinate were added to food and drink.
  • the “kokumi” imparting effect was evaluated.
  • Example 2 Evaluation of the “kokumi” imparting effect by the combined use of ⁇ -Glu-Val-Gly and succinic acid (free and salt)
  • ⁇ -Glu-Val-Gly and succinic acid (free) Alternatively, disodium succinate was added to foods and drinks, and the “kokumi” imparting effect was evaluated.
  • Example 3 Evaluation of the “kokumi” imparting effect by the combined use of ⁇ -Glu-Val-Gly, succinic acid, and proline
  • ⁇ -Glu-Val-Gly and succinic acid free form
  • proline was added to the food and drink, and the “kokumi” imparting effect was evaluated.
  • evaluation samples S1 to S5 shown in Table 3 were prepared by adding each alone or in combination.
  • Example 4 Evaluation of the “kokumi” imparting effect by the combined use of ⁇ -Glu-Val-Gly and succinic acid
  • ⁇ -Glu-Val-Gly and disodium succinate were added to food and drink at various concentrations. It added and evaluated about the "kokumi” provision effect.
  • Example 5 Evaluation of the effect of imparting “kokumi” by combining various ⁇ -glutamyl peptides and succinic acid
  • various ⁇ -glutamyl peptides and disodium succinate were added to foods and drinks to impart “kokumi” The effect was evaluated.
  • Example 6 Evaluation of the effect of imparting “kokumi” by the combined use of ⁇ -Glu-Val-Gly and various dicarboxylic acids
  • ⁇ -Glu-Val-Gly and various dicarboxylic acids similar to succinic acid (free form) was added to foods and drinks, and evaluated for the effect of imparting “kokumi”.
  • Example 7 Evaluation of the “kokumi” imparting effect of the combination of ⁇ -Glu-Val-Gly and succinic acid in potage soup
  • ⁇ -Glu-Val-Gly and disodium succinate were added to the potage soup Then, the “kokumi” imparting effect was evaluated.
  • a commercial potage soup (manufactured by Knorr Foods Co., Ltd .: prepared according to product instructions) was used as an evaluation system, and a sample to which nothing was added was used as a control.
  • ⁇ -Glu-Val-Gly has a eating concentration of 0.0005 g / 100 g (1.65 ⁇ mol / 100 g)
  • disodium succinate has a eating concentration of 0.0025 g / 100 g (15.43 ⁇ mol / 100 g).
  • Example 8 Evaluation of “Kokumi” imparting effect by combined use of ⁇ -Glu-Val-Gly and succinic acid in chicken consomme soup
  • ⁇ -Glu-Val-Gly and disodium succinate were combined with chicken consomme soup. The effect of imparting “kokumi” was evaluated.
  • Example 9 Evaluation of “Kokumi” imparting effect of ⁇ -Glu-Val-Gly and succinic acid in soy sauce ramen soup
  • ⁇ -Glu-Val-Gly and disodium succinate were combined with soy sauce ramen soup. The effect of imparting “kokumi” was evaluated.
  • Example 10 Evaluation of the effect of imparting “kokumi” by combining ⁇ -Glu-Val-Gly and succinic acid in pork bone ramen soup
  • ⁇ -Glu-Val-Gly and disodium succinate were added to pork bone. It was added to ramen soup and evaluated for its “kokumi” imparting effect.
  • Example 11 Evaluation of the effect of imparting “kokumi” by the combined use of ⁇ -Glu-Val-Gly and succinic acid in Chinese soup
  • ⁇ -Glu-Val-Gly and disodium succinate were added to Chinese soup Then, the “kokumi” imparting effect was evaluated.
  • Example 12 Evaluation of “kokumi” imparting effect by combined use of ⁇ -Glu-Val-Gly and succinic acid in miso soup
  • ⁇ -Glu-Val-Gly and disodium succinate were added to miso soup, The “kokumi” imparting effect was evaluated.
  • the present invention can provide a “kokumi” imparting agent that can effectively impart “kokumi” to foods and drinks. Moreover, the food / beverage products to which "kokumi” was provided can be manufactured using the "kokumi” imparting agent provided by this invention.

Abstract

Provided is a technique whereby a "body taste" is effectively imparted to a food or beverage. One or more γ-glutamylpeptides selected from the group consisting of γ-Glu-X-Gly (X represents an amino acid other than Cys or an amino acid derivative) and γ-Glu-Y (Y represents an amino acid other than Cys or an amino acid derivative) and one or more dicarboxylic acids selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid are added to a food or beverage or to a raw material therefor, thereby producing a food or beverage having a "body taste" imparted thereto.

Description

コク味付与剤Kokumi imparting agent
　本発明は、「コク味」付与剤およびその利用に関するものである。 The present invention relates to a “kokumi” imparting agent and use thereof.
　食品領域では呈味物質が古くから利用されてきた。特に、甘味(sweet taste)、塩味(salty taste)、酸味(sour taste)、苦味(bitter taste)、うま味(umami)で表される５基本味(five basic taste)を有する物質やこれらを増強する物質が調味料として広く利用されている。 In the food field, taste substances have been used for a long time. In particular, substances that have five basic tastes (five basic taste) represented by sweet taste, salty taste, sourstaste, bitter taste, and umami and enhance these Substances are widely used as seasonings.
　上記基本味では表せない味覚として「コク味」がある。「コク味」とは、基本味だけではなく、厚み(thickness)、ひろがり(growth (mouthfulness))、持続性(continuity)、まとまり(harmony)等の基本味の周辺の味(marginal tastes)や風味（marginal flavor）をも増強した味覚をいう。これまで、飲食品に対して効果的に「コク味」を付与する技術が求められてきた。 “Kokumi” is a taste that cannot be expressed with the basic taste. `` Kokumi '' is not only the basic taste, but also the taste (marginal tastes) and flavor of basic taste such as thickness, growth (mouthfulness), continuity, harmony, etc. Taste with enhanced (marginal flavor). Until now, the technique which provides a "brilliance" effectively with respect to food-drinks has been calculated | required.
　「コク味」を付与することのできる物質（「コク味」付与物質）としては、例えば、グルタチオン（γ－Ｇｌｕ－Ｃｙｓ－Ｇｌｙ）やγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ等のγ－グルタミルトリペプチド、およびγ‐Ｇｌｕ‐Ｍｅｔやγ‐Ｇｌｕ‐Ｔｈｒ等のγ－グルタミルジペプチドが知られている（特許文献１、２）。特許文献２には、これらγ－グルタミルペプチドは薬理学的に許容される任意の塩の形態でも用いることができ、塩としてはコハク酸との塩やマレイン酸との塩が例示できることが開示されている。 Examples of substances that can impart “kokumi” (“kokumi” imparting substances) include, for example, γ-glutamyltripeptides such as glutathione (γ-Glu-Cys-Gly) and γ-Glu-Val-Gly, In addition, γ-glutamyldipeptides such as γ-Glu-Met and γ-Glu-Thr are known (Patent Documents 1 and 2). Patent Document 2 discloses that these γ-glutamyl peptides can be used in the form of any pharmacologically acceptable salt, and examples of the salt include salts with succinic acid and maleic acid. ing.
　コハク酸、マレイン酸、およびメチルマロン酸は、いずれもジカルボン酸であり、互いに類似の構造を有する。例えば、コハク酸はうま味物質として知られている。 Succinic acid, maleic acid, and methylmalonic acid are all dicarboxylic acids and have similar structures to each other. For example, succinic acid is known as an umami substance.
　しかしながら、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ等の「コク味」付与物質とコハク酸等のジカルボン酸とを併用することで「コク味」がさらに増強されることは知られていない。 However, it is not known that the “kokumi” is further enhanced by using a “kokumi” imparting substance such as γ-Glu-Val-Gly together with a dicarboxylic acid such as succinic acid.
特許第１４６４９２８号公報Japanese Patent No. 1464928 国際公開第２００７／０５５３９３号パンフレットInternational Publication No. 2007/055393 Pamphlet
　本発明は、飲食品に対して効果的に「コク味」を付与する技術を提供することを課題とする。 The present invention has an object to provide a technique for effectively imparting “brillant taste” to foods and drinks.
　本発明者らは、上記課題を解決するために鋭意研究を行った結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ等の「コク味」付与物質とコハク酸等のジカルボン酸とを併用することで、「コク味」がさらに増強されることを見出し、本発明を完成させた。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have used a “kokumi” imparting substance such as γ-Glu-Val-Gly in combination with a dicarboxylic acid such as succinic acid. It was found that “kokumi” was further enhanced, and the present invention was completed.
　すなわち、本発明は以下のとおり例示できる。
［１］
　γ－Ｇｌｕ－Ｘ－Ｇｌｙ（ＸはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）およびγ－Ｇｌｕ－Ｙ（ＹはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）からなる群より選択されるγ－グルタミルペプチド、ならびにコハク酸、マレイン酸、およびメチルマロン酸からなる群より選択されるジカルボン酸を含む、「コク味」付与剤。
［２］
　前記γ－グルタミルペプチドに対する前記ジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が１より大きい、［１］に記載の「コク味」付与剤。
［３］
　前記γ－グルタミルペプチドに対する前記ジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が７５０００以下である、［１］または［２］に記載の「コク味」付与剤。
［４］
　前記γ－グルタミルペプチドが、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙである、［１］～［３］のいずれかに記載の「コク味」付与剤。
［５］
　前記ジカルボン酸が、コハク酸である、［１］～［４］のいずれかに記載の「コク味」付与剤。
［６］
　さらにプロリンを含む、［１］～［５］のいずれかに記載の「コク味」付与剤。
［７］
　［１］～［６］のいずれかに記載の「コク味」付与剤を飲食品またはその原料に添加することを含む、「コク味」の付与された飲食品の製造方法。
［８］
　γ－Ｇｌｕ－Ｘ－Ｇｌｙ（ＸはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）およびγ－Ｇｌｕ－Ｙ（ＹはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）からなる群より選択されるγ－グルタミルペプチド、ならびにコハク酸、マレイン酸、およびメチルマロン酸からなる群より選択されるジカルボン酸を、飲食品またはその原料に添加することを含む、「コク味」の付与された飲食品の製造方法。
［９］
　添加されるγ－グルタミルペプチドに対する添加されるジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が１より大きい、［８］に記載の方法。
［１０］
　添加されるγ－グルタミルペプチドに対する添加されるジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が７５０００以下である、［８］または［９］に記載の方法。
［１１］
　前記γ－グルタミルペプチドが、喫食濃度が飲食品１００ｇあたり０．０１７μｍｏｌ～１．６５μｍｏｌとなるように添加される、［８］～［１０］のいずれかに記載の方法。
［１２］
　前記ジカルボン酸が、喫食濃度が飲食品１００ｇあたり０．６μｍｏｌ～１２３５μｍｏｌとなるように添加される、［８］～［１１］のいずれかに記載の方法。
［１３］
　前記γ－グルタミルペプチドが、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙである、［８］～［１２］のいずれかに記載の方法。
［１４］
　前記ジカルボン酸が、コハク酸である、［８］～［１３］のいずれかに記載の方法。
［１５］
　さらにプロリンを添加することを含む、［８］～［１４］のいずれかに記載の方法。
［１６］
　前記ジカルボン酸の純度が９０％以上である、［８］～［１５］のいずれかに記載の方法。 That is, the present invention can be exemplified as follows.
[1]
γ-Glutamyl peptide selected from the group consisting of γ-Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and γ-Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys) And a “kokumi” imparting agent comprising a dicarboxylic acid selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid.
[2]
The “kokumi” imparting agent according to [1], wherein a molar ratio of the dicarboxylic acid to the γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is greater than 1.
[3]
The “kokumi” imparting agent according to [1] or [2], wherein a molar ratio of the dicarboxylic acid to the γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is 75000 or less.
[4]
The “kokumi” imparting agent according to any one of [1] to [3], wherein the γ-glutamyl peptide is γ-Glu-Val-Gly.
[5]
The “kokumi” imparting agent according to any one of [1] to [4], wherein the dicarboxylic acid is succinic acid.
[6]
The “kokumi” imparting agent according to any one of [1] to [5], further comprising proline.
[7]
[1] A method for producing a food or drink with a “kokumi” imparted thereto, which comprises adding the “kokumi” imparting agent according to any one of [1] to [6] to the food or drink or a raw material thereof.
[8]
γ-Glutamyl peptide selected from the group consisting of γ-Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and γ-Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys) And a method for producing a food and drink with a “kokumi” taste, which comprises adding a dicarboxylic acid selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid to the food or drink or a raw material thereof.
[9]
The method according to [8], wherein the molar ratio of the added dicarboxylic acid to the added γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is greater than 1.
[10]
The method according to [8] or [9], wherein the molar ratio of the added dicarboxylic acid to the added γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is 75000 or less.
[11]
The method according to any one of [8] to [10], wherein the γ-glutamyl peptide is added so that the eating concentration is 0.017 μmol to 1.65 μmol per 100 g of food or drink.
[12]
The method according to any one of [8] to [11], wherein the dicarboxylic acid is added so that a food concentration is 0.6 μmol to 1235 μmol per 100 g of food or drink.
[13]
The method according to any one of [8] to [12], wherein the γ-glutamyl peptide is γ-Glu-Val-Gly.
[14]
The method according to any one of [8] to [13], wherein the dicarboxylic acid is succinic acid.
[15]
The method according to any one of [8] to [14], further comprising adding proline.
[16]
The method according to any one of [8] to [15], wherein the purity of the dicarboxylic acid is 90% or more.
　以下、本発明を詳細に説明する。なお、本発明において、アミノ酸およびアミノ酸誘導体は、特記しない限りいずれもＬ－体である。また、本発明において、濃度は、特記しない限り質量を基準とする濃度である。すなわち、例えば、「％」は特記しない限り「質量％」を、「ｐｐｍ」は特記しない限り「質量ｐｐｍ」を示す。また、本発明において、ある成分の「喫食濃度」とは、当該成分を含む飲食品を喫食する際の、当該飲食品における当該成分の濃度をいう。すなわち、ある成分の「喫食濃度」とは、具体的には、例えば、当該成分を含む本発明の「コク味」付与剤を添加して製造した飲食品または当該成分を添加して製造した飲食品を喫食する際の、当該飲食品における当該成分の濃度をいう。 Hereinafter, the present invention will be described in detail. In the present invention, amino acids and amino acid derivatives are both L-forms unless otherwise specified. In the present invention, the concentration is a concentration based on mass unless otherwise specified. That is, for example, “%” indicates “mass%” unless otherwise specified, and “ppm” indicates “mass ppm” unless otherwise specified. In the present invention, the “eating concentration” of a certain component refers to the concentration of the component in the food or drink when eating the food or drink containing the component. That is, the “food concentration” of a component specifically refers to, for example, a food or drink manufactured by adding the “kokumi” imparting agent of the present invention containing the component or a food or drink manufactured by adding the component. The concentration of the component in the food and drink when eating the product.
＜１＞本発明の「コク味」付与剤
　本発明は、γ－Ｇｌｕ－Ｘ－Ｇｌｙ（ＸはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）およびγ－Ｇｌｕ－Ｙ（ＹはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）からなる群より選択される１またはそれ以上のγ－グルタミルペプチド、ならびにコハク酸、マレイン酸、およびメチルマロン酸からなる群より選択される１またはそれ以上のジカルボン酸を含む、「コク味」付与剤を提供する。以下、同「コク味」付与剤を、「本発明の「コク味」付与剤」ともいう。また、以下、同γ－グルタミルペプチドおよび同ジカルボン酸を総称して「有効成分」ともいう。 <1> “Kokumi” imparting agent of the present invention The present invention relates to γ-Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and γ-Glu-Y (Y represents an amino acid other than Cys or Comprising one or more γ-glutamyl peptides selected from the group consisting of amino acid derivatives) and one or more dicarboxylic acids selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid, Provides a “kokumi” imparting agent. Hereinafter, the “kokumi” imparting agent is also referred to as “the“ kokumi ”imparting agent of the present invention”. Hereinafter, the γ-glutamyl peptide and the dicarboxylic acid are also collectively referred to as “active ingredients”.
＜１－１＞本発明のγ－グルタミルペプチド
　本発明において用いられるγ－グルタミルペプチドは、一般式：γ－Ｇｌｕ－Ｘ－Ｇｌｙ（ＸはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）で表されるγ－グルタミルトリペプチドおよび一般式：γ－Ｇｌｕ－Ｙ（ＹはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）で表されるγ－グルタミルジペプチドからなる群より選択される。上記一般式において、「γ－」とは、グルタミン酸のγ位のカルボキシル基を介してＸまたはＹが結合していることを意味する。γ－グルタミルペプチドとしては、１種のγ－グルタミルペプチドを用いてもよく、２種またはそれ以上のγ－グルタミルペプチドを組み合わせて用いてもよい。 <1-1> γ-glutamyl peptide of the present invention The γ-glutamyl peptide used in the present invention is represented by the general formula: γ-Glu-X-Gly (X represents an amino acid or an amino acid derivative excluding Cys). It is selected from the group consisting of γ-glutamyl tripeptide and the general formula: γ-Glu-Y (Y represents an amino acid or amino acid derivative other than Cys) and γ-glutamyl dipeptide. In the above general formula, “γ-” means that X or Y is bonded via a carboxyl group at the γ-position of glutamic acid. As the γ-glutamyl peptide, one γ-glutamyl peptide may be used, or two or more γ-glutamyl peptides may be used in combination.
　アミノ酸として、具体的には、例えば、Ｇｌｙ、Ａｌａ、Ｖａｌ、Ｌｅｕ、Ｉｌｅ、Ｓｅｒ、Ｔｈｒ、Ｃｙｓ、Ｍｅｔ、Ａｓｎ、Ｇｌｎ、Ｐｒｏ、Ｈｙｐ等の中性アミノ酸、Ａｓｐ、Ｇｌｕ等の酸性アミノ酸、Ｌｙｓ、Ａｒｇ、Ｈｉｓ等の塩基性アミノ酸、Ｐｈｅ、Ｔｙｒ、Ｔｒｐ等の芳香族アミノ酸、ホモセリン、シトルリン、オルニチン、α－アミノ酪酸、ノルバリン、ノルロイシン、タウリンが挙げられる。すなわち、「Ｃｙｓを除くアミノ酸」として、具体的には、例えば、これらの内、Ｃｙｓ以外のものが挙げられる。 Specific examples of amino acids include neutral amino acids such as Gly, Ala, Val, Leu, Ile, Ser, Thr, Cys, Met, Asn, Gln, Pro and Hyp, acidic amino acids such as Asp and Glu, and Lys. , Basic amino acids such as Arg and His, aromatic amino acids such as Phe, Tyr and Trp, homoserine, citrulline, ornithine, α-aminobutyric acid, norvaline, norleucine and taurine. Specifically, examples of the “amino acid excluding Cys” include, for example, those other than Cys.
　なお、本発明において、アミノ基残基の略号は以下のアミノ酸を意味する。
（１）Ｇｌｙ：グリシン
（２）Ａｌａ：アラニン
（３）Ｖａｌ：バリン
（４）Ｌｅｕ：ロイシン
（５）Ｉｌｅ：イソロイシン
（６）Ｍｅｔ：メチオニン
（７）Ｐｈｅ：フェニルアラニン
（８）Ｔｙｒ：チロシン
（９）Ｔｒｐ：トリプトファン
（１０）Ｈｉｓ：ヒスチジン
（１１）Ｌｙｓ：リジン
（１２）Ａｒｇ：アルギニン
（１３）Ｓｅｒ：セリン
（１４）Ｔｈｒ：トレオニン
（１５）Ａｓｐ：アスパラギン酸
（１６）Ｇｌｕ：グルタミン酸
（１７）Ａｓｎ：アスパラギン
（１８）Ｇｌｎ：グルタミン
（１９）Ｃｙｓ：システイン
（２０）Ｐｒｏ：プロリン
（２１）Ｏｒｎ：オルニチン
（２２）Ｓａｒ：サルコシン
（２３）Ｃｉｔ：シトルリン
（２４）Ｎｖａ：ノルバリン
（２５）Ｎｌｅ：ノルロイシン
（２６）Ａｂｕ：α－アミノ酪酸
（２７）Ｔａｕ：タウリン
（２８）Ｈｙｐ：ヒドロキシプロリン
（２９）ｔ－Ｌｅｕ：ｔｅｒｔ－ロイシン In the present invention, abbreviations for amino group residues mean the following amino acids.
(1) Gly: glycine (2) Ala: alanine (3) Val: valine (4) Leu: leucine (5) Ile: isoleucine (6) Met: methionine (7) Phe: phenylalanine (8) Tyr: tyrosine (9 ) Trp: tryptophan (10) His: histidine (11) Lys: lysine (12) Arg: arginine (13) Ser: serine (14) Thr: threonine (15) Asp: aspartic acid (16) Glu: glutamic acid (17) Asn: Asparagine (18) Gln: Glutamine (19) Cys: Cysteine (20) Pro: Proline (21) Orn: Ornithine (22) Sar: Sarcosine (23) Cit: Citrulline (24) Nva: Norvaline (25) Nle: Norleucine (26) Abu: α-aminobutyric acid (2 ) Tau: taurine (28) Hyp: hydroxyproline (29) t-Leu: tert- leucine
　アミノ酸誘導体とは、上記のようなアミノ酸の各種誘導体をいう。アミノ酸誘導体としては、例えば、特殊アミノ酸、非天然アミノ酸、アミノアルコール、ならびに末端カルボニル基、末端アミノ基、およびシステインのチオール基等の官能基の１またはそれ以上が各種置換基により置換されたアミノ酸が挙げられる。置換基として、具体的には、例えば、アルキル基、アシル基、水酸基、アミノ基、アルキルアミノ基、ニトロ基、スルフォニル基、および各種保護基が挙げられる。アミノ酸誘導体として、具体的には、例えば、Ａｒｇ（ＮＯ2）：Ｎ－γ－ニトロアルギニン、Ｃｙｓ（ＳＮＯ）：Ｓ－ニトロシステイン、Ｃｙｓ（Ｓ－Ｍｅ）：Ｓ－メチルシステイン、Ｃｙｓ（Ｓ－ａｌｌｙｌ）：Ｓ－アリルシステイン、Ｖａｌ－ＮＨ2：バリンアミド、Ｖａｌ－ｏｌ：バリノール（２－アミノ－３－メチル－１－ブタノール）、Ｍｅｔ（Ｏ）：メチオニンスルホキシド、およびＣｙｓ（Ｓ－Ｍｅ）（Ｏ）：Ｓ－メチルシステインスルホキシドが挙げられる。 Amino acid derivatives refer to various derivatives of amino acids as described above. Examples of amino acid derivatives include special amino acids, unnatural amino acids, amino alcohols, and amino acids in which one or more functional groups such as terminal carbonyl group, terminal amino group, and cysteine thiol group are substituted with various substituents. Can be mentioned. Specific examples of the substituent include an alkyl group, an acyl group, a hydroxyl group, an amino group, an alkylamino group, a nitro group, a sulfonyl group, and various protective groups. Specific examples of amino acid derivatives include Arg (NO 2 ): N-γ-nitroarginine, Cys (SNO): S-nitrocysteine, Cys (S-Me): S-methylcysteine, Cys (S— allyl): S-allyl cysteine, Val-NH 2 : Valinamide, Val-ol: Valinol (2-amino-3-methyl-1-butanol), Met (O): Methionine sulfoxide, and Cys (S-Me) ( O): S-methylcysteine sulfoxide.
　γ－グルタミルペプチドとして、具体的には、例えば、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ、γ－Ｇｌｕ－Ｎｖａ－Ｇｌｙ、γ－Ｇｌｕ－Ａｂｕ、γ－Ｇｌｕ－Ｎｖａが挙げられる。これらの中では、例えば、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙが好ましい。 Specific examples of the γ-glutamyl peptide include γ-Glu-Val-Gly, γ-Glu-Nva-Gly, γ-Glu-Abu, and γ-Glu-Nva. Among these, for example, γ-Glu-Val-Gly is preferable.
　本発明において、γ－グルタミルペプチドは、特記しない限り、いずれもフリー体、もしくはその塩、またはそれらの混合物である。 In the present invention, the γ-glutamyl peptide is a free form, a salt thereof, or a mixture thereof unless otherwise specified.
　塩は、経口摂取可能なものであれば特に制限されない。例えば、カルボキシル基等の酸性基に対する塩としては、具体的には、アンモニウム塩、ナトリウム、カリウム等のアルカリ金属との塩、カルシウム、マグネシウム等のアルカリ土類金属との塩、アルミニウム塩、亜鉛塩、トリエチルアミン、エタノールアミン、モルホリン、ピロリジン、ピペリジン、ピペラジン、ジシクロへキシルアミン等の有機アミンとの塩、アルギニン、リジン等の塩基性アミノ酸との塩が挙げられる。また、例えば、アミノ基等の塩基性基に対する塩としては、具体的には、塩酸、硫酸、リン酸、硝酸、臭化水素酸等の無機酸との塩、酢酸、クエン酸、安息香酸、マレイン酸、フマル酸、酒石酸、コハク酸、タンニン酸、酪酸、ヒベンズ酸、パモ酸、エナント酸、デカン酸、テオクル酸、サリチル酸、乳酸、シュウ酸、マンデル酸、リンゴ酸、メチルマロン酸等の有機カルボン酸との塩、メタンスルホン酸、ベンゼンスルホン酸、ｐ－トルエンスルホン酸等の有機スルホン酸との塩が挙げられる。なお、塩としては、１種の塩を用いてもよく、２種またはそれ以上の塩を組み合わせて用いてもよい。 Salt is not particularly limited as long as it can be taken orally. For example, specific examples of salts for acidic groups such as carboxyl groups include ammonium salts, salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium and magnesium, aluminum salts, and zinc salts. , Salts with organic amines such as triethylamine, ethanolamine, morpholine, pyrrolidine, piperidine, piperazine and dicyclohexylamine, and salts with basic amino acids such as arginine and lysine. Further, for example, as a salt for a basic group such as an amino group, specifically, a salt with an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, hydrobromic acid, acetic acid, citric acid, benzoic acid, Organics such as maleic acid, fumaric acid, tartaric acid, succinic acid, tannic acid, butyric acid, hybenzic acid, pamoic acid, enanthic acid, decanoic acid, teocric acid, salicylic acid, lactic acid, oxalic acid, mandelic acid, malic acid, methylmalonic acid Examples thereof include salts with carboxylic acids and salts with organic sulfonic acids such as methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid. In addition, as a salt, 1 type of salt may be used and 2 or more types of salts may be used in combination.
　γ－グルタミルペプチドとしては、市販品を用いてもよく、適宜製造して取得したものを用いてもよい。 As the γ-glutamyl peptide, a commercially available product may be used, or a product produced and obtained as appropriate.
　ペプチドの製造方法は特に制限されず、例えば公知の方法を利用できる。公知の方法としては、例えば、（１）化学的にペプチドを合成する方法や（２）酵素的な反応によりペプチドを合成する方法が挙げられる。アミノ酸残基数が２～３残基の比較的短いペプチドの合成には、特に、化学的に合成する方法を用いるのが簡便である。 The peptide production method is not particularly limited, and for example, a known method can be used. Known methods include, for example, (1) a method of chemically synthesizing a peptide and (2) a method of synthesizing a peptide by enzymatic reaction. For the synthesis of a relatively short peptide having 2 to 3 amino acid residues, it is particularly convenient to use a chemical synthesis method.
　化学的にペプチドを合成する場合、ペプチド合成機を用いてペプチドを合成あるいは半合成することができる。化学的にペプチドを合成する方法としては、例えば、ペプチド固相合成法が挙げられる。合成されたペプチドは通常の手段、例えば、イオン交換クロマトグラフィー、逆相高速液体クロマトグラフィー、アフィニティークロマトグラフィーによって精製することができる。このようなペプチド固相合成法、およびそれに続くペプチド精製はこの技術分野においてよく知られたものである。 When a peptide is chemically synthesized, the peptide can be synthesized or semi-synthesized using a peptide synthesizer. Examples of a method for chemically synthesizing a peptide include a peptide solid phase synthesis method. The synthesized peptide can be purified by conventional means, for example, ion exchange chromatography, reverse phase high performance liquid chromatography, or affinity chromatography. Such peptide solid-phase synthesis methods and subsequent peptide purification are well known in the art.
　酵素的な反応によりペプチドを合成する場合、例えば、国際公開パンフレットＷＯ２００４／０１１６５３号に記載の方法を用いることができる。具体的には、例えば、カルボキシル基がエステル化またはアミド化されたアミノ酸またはジペプチドと、アミノ基がフリーの状態であるアミノ酸（例えばカルボキシル基が保護されたアミノ酸）とを、ペプチド生成酵素の存在下で反応させることにより、ジペプチドまたはトリペプチドを合成することができる。合成されたジペプチドまたはトリペプチドは、適宜精製することができる。ペプチド生成酵素としては、例えば、ペプチドを生成する能力を有する微生物の培養物、該培養物から分離した培養上清、該培養物から分離した菌体、該微生物の菌体処理物、それらから分離したペプチド生成酵素が挙げられる。ペプチド生成酵素としては、必要に応じて適宜精製されたものを用いることができる。 When a peptide is synthesized by an enzymatic reaction, for example, a method described in International Publication Pamphlet WO 2004/011653 can be used. Specifically, for example, an amino acid or dipeptide in which a carboxyl group is esterified or amidated, and an amino acid in which the amino group is free (for example, an amino acid in which the carboxyl group is protected) are reacted in the presence of a peptide-forming enzyme. The dipeptide or tripeptide can be synthesized by reacting with. The synthesized dipeptide or tripeptide can be appropriately purified. Examples of the peptide-forming enzyme include a culture of a microorganism having the ability to produce a peptide, a culture supernatant separated from the culture, a cell separated from the culture, a treated product of the microorganism, and separated from them. Peptide-forming enzyme. As the peptide-generating enzyme, one appropriately purified as necessary can be used.
　また、例えば、γ－グルタミルペプチドは、当該γ－グルタミルペプチドの生産能を有する微生物を培養し、培養液または菌体から当該γ－グルタミルペプチドを回収することで製造することができる。具体的には、例えば、特開2012-213376に記載の方法により、γ－Ｇｌｕ－Ａｂｕ等のγ－グルタミルペプチドを高濃度に含有する酵母が得られる。 Further, for example, γ-glutamyl peptide can be produced by culturing a microorganism capable of producing the γ-glutamyl peptide and recovering the γ-glutamyl peptide from the culture solution or cells. Specifically, for example, a yeast containing a γ-glutamyl peptide such as γ-Glu-Abu at a high concentration can be obtained by the method described in JP 2012-213376.
　γ－グルタミルペプチドは、所望の程度に精製されていてもよく、そうでなくてもよい。例えば、γ－グルタミルペプチドとしては、純度が５０％以上、７０％以上、９０％以上、または９５％以上のものを用いてもよい。また、例えば、γ－グルタミルペプチドとしては、当該γ－グルタミルペプチドを含有する素材を用いてもよい。γ－グルタミルペプチドを含有する素材として、具体的には、例えば、当該γ－グルタミルペプチドの生産能を有する微生物を培養して得られた培養液、菌体、培養上清等の発酵生産物、およびそれらの加工品が挙げられる。そのような加工品としては、例えば、γ－グルタミルペプチドを含有する酵母エキス（特開2012-213376）が挙げられる。 The γ-glutamyl peptide may or may not be purified to a desired degree. For example, as the γ-glutamyl peptide, one having a purity of 50% or more, 70% or more, 90% or more, or 95% or more may be used. For example, as the γ-glutamyl peptide, a material containing the γ-glutamyl peptide may be used. Specific examples of the material containing γ-glutamyl peptide include, for example, fermentation products such as a culture solution obtained by culturing a microorganism having the ability to produce γ-glutamyl peptide, bacterial cells, and culture supernatant. And processed products thereof. Examples of such processed products include yeast extract containing γ-glutamyl peptide (Japanese Patent Laid-Open No. 2012-213376).
＜１－２＞本発明のジカルボン酸
　本発明において用いられるジカルボン酸は、コハク酸、マレイン酸、およびメチルマロン酸からなる群より選択される。コハク酸、マレイン酸、およびメチルマロン酸は、互いに類似の構造を有する。ジカルボン酸としては、１種のジカルボン酸を用いてもよく、２種またはそれ以上のジカルボン酸を組み合わせて用いてもよい。 <1-2> Dicarboxylic Acid of the Present Invention The dicarboxylic acid used in the present invention is selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid. Succinic acid, maleic acid, and methylmalonic acid have similar structures to each other. As the dicarboxylic acid, one kind of dicarboxylic acid may be used, or two or more kinds of dicarboxylic acids may be used in combination.
　本発明において、ジカルボン酸は、特記しない限り、いずれもフリー体、もしくはその塩、またはそれらの混合物である。ジカルボン酸の塩については、上述のγ－グルタミルペプチドのカルボキシル基等の酸性基に対する塩の記載を準用できる。 In the present invention, unless otherwise specified, all dicarboxylic acids are free forms, salts thereof, or mixtures thereof. Regarding the salt of the dicarboxylic acid, the description of the salt for the acidic group such as a carboxyl group of the γ-glutamyl peptide can be applied mutatis mutandis.
　ジカルボン酸としては、市販品を用いてもよく、適宜製造して取得したものを用いてもよい。 As the dicarboxylic acid, a commercially available product may be used, or an appropriately manufactured and acquired product may be used.
　ジカルボン酸の製造方法は特に制限されず、例えば公知の方法を利用できる。例えば、ジカルボン酸は、化学合成により製造することができる。また、例えば、ジカルボン酸は、当該ジカルボン酸の生産能を有する微生物を培養し、培養液または菌体から当該ジカルボン酸を回収することで製造することができる。具体的には、例えば、特開2008-011714に記載の方法により、微生物を利用してコハク酸を製造することができる。また、例えば、ジカルボン酸は、当該ジカルボン酸を含有する農水畜産物から回収することで製造することができる。 The production method of the dicarboxylic acid is not particularly limited, and for example, a known method can be used. For example, dicarboxylic acid can be produced by chemical synthesis. In addition, for example, the dicarboxylic acid can be produced by culturing a microorganism having the ability to produce the dicarboxylic acid and recovering the dicarboxylic acid from the culture solution or the cells. Specifically, for example, succinic acid can be produced using microorganisms by the method described in JP-A-2008-011714. Moreover, for example, dicarboxylic acid can be manufactured by recovering from agricultural, aquatic and livestock products containing the dicarboxylic acid.
　ジカルボン酸は、所望の程度に精製されていてもよく、そうでなくてもよい。例えば、ジカルボン酸としては、純度が５０％以上、７０％以上、９０％以上、または９５％以上のものを用いてもよい。また、例えば、ジカルボン酸としては、当該ジカルボン酸を含有する素材を用いてもよい。ジカルボン酸を含有する素材として、具体的には、例えば、当該ジカルボン酸の生産能を有する微生物を培養して得られた培養液、菌体、培養上清等の発酵生産物、当該ジカルボン酸を含有する農水畜産物、およびそれらの加工品が挙げられる。 The dicarboxylic acid may or may not be purified to a desired level. For example, a dicarboxylic acid having a purity of 50% or more, 70% or more, 90% or more, or 95% or more may be used. For example, as dicarboxylic acid, you may use the raw material containing the said dicarboxylic acid. Specifically, as a material containing a dicarboxylic acid, for example, a culture solution obtained by culturing a microorganism capable of producing the dicarboxylic acid, a bacterial product, a fermentation product such as a culture supernatant, and the dicarboxylic acid Agricultural, aquatic and livestock products contained therein, and processed products thereof are mentioned.
＜１－３＞本発明の「コク味」付与剤
　本発明の「コク味」付与剤は、上記有効成分を含む。 <1-3> “Kokumi” imparting agent of the present invention The “kokumi” imparting agent of the present invention contains the above-mentioned active ingredient.
　なお、本発明の「コク味」付与剤がγ－グルタミルペプチドおよびジカルボン酸の両方に該当する成分、例えばγ－グルタミルペプチドのジカルボン酸塩、を含む場合、同成分は本発明の「コク味」付与剤においてγ－グルタミルペプチドおよびジカルボン酸の両方を兼ねる。すなわち、本発明の「コク味」付与剤がγ－グルタミルペプチドおよびジカルボン酸の両方に該当する成分、例えばγ－グルタミルペプチドのジカルボン酸塩、を含む場合、本発明の「コク味」付与剤は別途γ－グルタミルペプチドおよび／またはジカルボン酸を含んでいてもよく、含んでいなくともよい。 In addition, when the “kokumi” imparting agent of the present invention includes a component corresponding to both γ-glutamyl peptide and dicarboxylic acid, for example, a dicarboxylate salt of γ-glutamyl peptide, this component is the “kokumi” of the present invention. It serves as both γ-glutamyl peptide and dicarboxylic acid in the imparting agent. That is, when the “kokumi” imparting agent of the present invention contains components corresponding to both γ-glutamyl peptide and dicarboxylic acid, for example, a dicarboxylate salt of γ-glutamyl peptide, Separately, γ-glutamyl peptide and / or dicarboxylic acid may or may not be contained.
　本発明の「コク味」付与剤は、上記有効成分のみからなるものであってもよく、その他の成分を含むものであってもよい。 The “kokumi” imparting agent of the present invention may be composed of only the above-mentioned active ingredient or may contain other ingredients.
　「その他の成分」は、経口摂取可能なものであれば特に制限されず、例えば、調味料、飲食品、または医薬品に配合して利用されるものを利用できる。 The “other ingredients” are not particularly limited as long as they can be taken orally, and for example, those used in seasonings, foods and drinks, or pharmaceuticals can be used.
　「その他の成分」として、具体的には、例えば、プロリンが挙げられる。本発明において、プロリンは、特記しない限り、フリー体、もしくはその塩、またはそれらの混合物である。プロリンの塩については、上述のγ－グルタミルペプチドの塩の記載を準用できる。 Specific examples of “other components” include proline. In the present invention, proline is a free form, a salt thereof, or a mixture thereof unless otherwise specified. Regarding the proline salt, the above-mentioned description of the salt of γ-glutamyl peptide can be applied mutatis mutandis.
　また、「その他の成分」としては、例えば、本発明において用いられるγ－グルタミルペプチド以外の、「コク味」付与活性を有する化合物やカルシウム受容体刺激活性を有する化合物が挙げられる。「コク味」付与活性を有する化合物として、具体的には、例えば、グルタチオンやアリインが挙げられる。カルシウム受容体刺激活性を有する化合物として、具体的には、例えば、カルシウム、カドリニウム等のカチオン；ポリアルギニン、ポリリジン等の塩基性ペプチド；プトレッシン、スペルミン、スペルミジン等のポリアミン；プロタミン等のタンパク質；フェニルアラニン、グルタチオン等のペプチド；シナカルセットが挙げられる。これらの化合物についても、塩を形成し得るものは塩の形態で利用されてもよい。塩については、上述のγ－グルタミルペプチドの塩の記載を準用できる。 Further, examples of the “other components” include compounds having “kokumi” imparting activity and compounds having calcium receptor stimulating activity other than the γ-glutamyl peptide used in the present invention. Specific examples of the compound having “kokumi” imparting activity include glutathione and alliin. Specific examples of compounds having calcium receptor stimulating activity include, for example, cations such as calcium and cadolinium; basic peptides such as polyarginine and polylysine; polyamines such as putrescine, spermine and spermidine; proteins such as protamine; phenylalanine, Peptides such as glutathione; cinacalcet. As for these compounds, those capable of forming a salt may be used in the form of a salt. Regarding the salt, the description of the salt of the γ-glutamyl peptide described above can be applied mutatis mutandis.
　また、「その他の成分」として、具体的には、例えば、砂糖、蜂蜜、メープルシロップ、スクロース、グルコース、フルクトース、異性化糖、オリゴ糖等の糖類；キシリトール、エリスリトール等の糖アルコール類；天然または人工甘味料；食塩、塩化ナトリウム、塩化カリウム等の無機塩類；酢酸、クエン酸等の有機酸類およびその塩；グルタミン酸、グリシン等のアミノ酸類およびその塩；イノシン酸、グアニル酸、キサンチル酸等の核酸類およびその塩；食物繊維、ｐＨ緩衝剤、香料、食用油、エタノール、水が挙げられる。塩については、上述のγ－グルタミルペプチドの塩の記載を準用できる。 Further, as the “other components”, specifically, for example, sugars such as sugar, honey, maple syrup, sucrose, glucose, fructose, isomerized sugar, oligosaccharide and the like; sugar alcohols such as xylitol and erythritol; natural or Artificial sweeteners; inorganic salts such as sodium chloride, sodium chloride and potassium chloride; organic acids such as acetic acid and citric acid and salts thereof; amino acids such as glutamic acid and glycine and salts thereof; nucleic acids such as inosinic acid, guanylic acid and xanthylic acid And salts thereof; dietary fiber, pH buffer, fragrance, edible oil, ethanol, water. Regarding the salt, the description of the salt of the γ-glutamyl peptide described above can be applied mutatis mutandis.
　これらの成分は、単独で、あるいは任意の組み合わせで利用されてよい。 These components may be used alone or in any combination.
　本発明の「コク味」付与剤の形態は特に制限されず、例えば、粉末状、顆粒状、液状、ペースト状、キューブ状等のいかなる形態であってもよい。 The form of the “kokumi” imparting agent of the present invention is not particularly limited, and may be any form such as powder, granule, liquid, paste, or cube.
　本発明の「コク味」付与剤における有効成分の濃度は、本発明の「コク味」付与剤を利用して飲食品に「コク味」を付与できる限り特に制限されず、有効成分の種類、有効成分の喫食濃度、本発明の「コク味」付与剤の使用量等の諸条件に応じて適宜設定することができる。 The concentration of the active ingredient in the “kokumi” imparting agent of the present invention is not particularly limited as long as it can impart “kokumi” to foods and drinks using the “kokumi” imparting agent of the present invention. It can be set as appropriate according to various conditions such as the eating concentration of the active ingredient and the amount of the “kokumi” imparting agent of the present invention.
　本発明の「コク味」付与剤における有効成分の総濃度は、特に制限されないが、例えば、０．０１ｐｐｍ以上、０．１ｐｐｍ以上、１ｐｐｍ以上、または１０ｐｐｍ以上であってよい。また、本発明の「コク味」付与剤における有効成分の総濃度は、特に制限されないが、例えば、１００％以下、１０％以下、または１％以下であってよい。なお、「有効成分の総濃度」とは、γ－グルタミルペプチドの濃度およびジカルボン酸の濃度の合計を意味する。 The total concentration of active ingredients in the “kokumi” imparting agent of the present invention is not particularly limited, and may be, for example, 0.01 ppm or more, 0.1 ppm or more, 1 ppm or more, or 10 ppm or more. Further, the total concentration of the active ingredients in the “kokumi” imparting agent of the present invention is not particularly limited, but may be, for example, 100% or less, 10% or less, or 1% or less. The “total concentration of active ingredients” means the sum of the concentration of γ-glutamyl peptide and the concentration of dicarboxylic acid.
　本発明の「コク味」付与剤における有効成分の比率は、本発明の「コク味」付与剤を利用して飲食品に「コク味」を付与できる限り特に制限されず、有効成分の種類等の諸条件に応じて適宜設定することができる。本発明の「コク味」付与剤において、γ－グルタミルペプチドに対するジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）は、例えば、１より大きくてよい（すなわち、ジカルボン酸量［ｍｏｌ］＞γ－グルタミルペプチド量［ｍｏｌ］）。また、本発明の「コク味」付与剤において、γ－グルタミルペプチドに対するジカルボン酸のモル比は、例えば、３以上、１５以上、または３０以上であってよい。また、本発明の「コク味」付与剤において、γ－グルタミルペプチドに対するジカルボン酸のモル比は、例えば、７５０００以下、４０００以下、または２００以下であってよい。 The ratio of the active ingredient in the “kokumi” imparting agent of the present invention is not particularly limited as long as it can impart “kokumi” to foods and drinks using the “kokumi” imparting agent of the present invention. It can set suitably according to these conditions. In the “kokumi” imparting agent of the present invention, the molar ratio of dicarboxylic acid to γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) may be, for example, greater than 1 (that is, the amount of dicarboxylic acid [Mol]> γ-glutamyl peptide amount [mol]). Further, in the “kokumi” imparting agent of the present invention, the molar ratio of the dicarboxylic acid to the γ-glutamyl peptide may be, for example, 3 or more, 15 or more, or 30 or more. Further, in the “kokumi” imparting agent of the present invention, the molar ratio of the dicarboxylic acid to the γ-glutamyl peptide may be, for example, 75000 or less, 4000 or less, or 200 or less.
　本発明の「コク味」付与剤におけるγ－グルタミルペプチドの濃度は、例えば、上記例示した有効成分の総濃度と上記例示した有効成分の比率を満たすような範囲に設定されてよい。また、γ－グルタミルペプチドは、例えば、γ－グルタミルペプチドの喫食濃度が、飲食品１００ｇあたり、０．０１５μｍｏｌ以上、または０．３μｍｏｌ以上となるように、本発明の「コク味」付与剤に含まれていてよい。また、γ－グルタミルペプチドは、例えば、γ－グルタミルペプチドの喫食濃度が、飲食品１００ｇあたり、２００μｍｏｌ以下、２０μｍｏｌ以下、または２μｍｏｌ以下となるように、本発明の「コク味」付与剤に含まれていてよい。γ－グルタミルペプチドは、具体的には、例えば、γ－グルタミルペプチドの喫食濃度が、飲食品１００ｇあたり、０．０１７μｍｏｌ～１．６５μｍｏｌ、または０．３３μｍｏｌ～１．６５μｍｏｌとなるように、本発明の「コク味」付与剤に含まれていてもよい。なお、２またはそれ以上のγ－グルタミルペプチドを用いる場合、γ－グルタミルペプチドの喫食濃度とは、２またはそれ以上のγ－グルタミルペプチドの喫食濃度の合計であってよい。 The concentration of the γ-glutamyl peptide in the “kokumi” imparting agent of the present invention may be set, for example, within a range that satisfies the ratio of the above-exemplified active ingredients to the above-mentioned active ingredients. Further, γ-glutamyl peptide is included in the “kokumi” imparting agent of the present invention so that, for example, the eating concentration of γ-glutamyl peptide is 0.015 μmol or more, or 0.3 μmol or more per 100 g of food or drink. It may be. In addition, γ-glutamyl peptide is included in the “kokumi” imparting agent of the present invention so that, for example, the eating concentration of γ-glutamyl peptide is 200 μmol or less, 20 μmol or less, or 2 μmol or less per 100 g of food or drink. It may be. Specifically, the γ-glutamyl peptide is, for example, such that the eating concentration of the γ-glutamyl peptide is 0.017 μmol to 1.65 μmol, or 0.33 μmol to 1.65 μmol per 100 g of food or drink. It may be contained in the “kokumi” imparting agent. When two or more γ-glutamyl peptides are used, the eating concentration of γ-glutamyl peptide may be the sum of the eating concentrations of two or more γ-glutamyl peptides.
　本発明の「コク味」付与剤におけるジカルボン酸の濃度は、例えば、上記例示した有効成分の総濃度と上記例示した有効成分の比率を満たすような範囲に設定されてよい。ジカルボン酸は、例えば、ジカルボン酸の喫食濃度が、飲食品１００ｇあたり、０．５μｍｏｌ以上、または５μｍｏｌ以上となるように、本発明の「コク味」付与剤に含まれていてよい。また、ジカルボン酸は、例えば、ジカルボン酸の喫食濃度が、飲食品１００ｇあたり、１４００μｍｏｌ以下、または４００μｍｏｌ以下となるように、本発明の「コク味」付与剤に含まれていてよい。ジカルボン酸は、具体的には、例えば、ジカルボン酸の喫食濃度が、飲食品１００ｇあたり、０．６μｍｏｌ～１２３５μｍｏｌ、または６．２μｍｏｌ～３０９μｍｏｌとなるように、本発明の「コク味」付与剤に含まれていてもよい。なお、２またはそれ以上のジカルボン酸を用いる場合、ジカルボン酸の喫食濃度とは、２またはそれ以上のジカルボン酸の喫食濃度の合計であってよい。 The concentration of the dicarboxylic acid in the “kokumi” imparting agent of the present invention may be set, for example, within a range that satisfies the ratio of the above-exemplified total active ingredients and the above-exemplified active ingredients. For example, the dicarboxylic acid may be included in the “kokumi” imparting agent of the present invention so that the eating concentration of the dicarboxylic acid is 0.5 μmol or more, or 5 μmol or more per 100 g of food or drink. Moreover, the dicarboxylic acid may be contained in the “kokumi” imparting agent of the present invention so that the eating concentration of the dicarboxylic acid is 1400 μmol or less or 400 μmol or less per 100 g of food or drink. Specifically, the dicarboxylic acid is added to the “kokumi” imparting agent of the present invention so that, for example, the eating concentration of the dicarboxylic acid is 0.6 μmol to 1235 μmol, or 6.2 μmol to 309 μmol per 100 g of food or drink. It may be included. When two or more dicarboxylic acids are used, the eating concentration of the dicarboxylic acid may be the sum of the eating concentrations of the two or more dicarboxylic acids.
　本発明の「コク味」付与剤における「その他の成分」の濃度は、本発明の「コク味」付与剤を利用して飲食品に「コク味」を付与できる限り特に制限されず、「その他の成分」の種類、「その他の成分」の喫食濃度、本発明の「コク味」付与剤の使用量等の諸条件に応じて適宜設定することができる。「その他の成分」の喫食濃度は、「その他の成分」の種類等の諸条件に応じて適宜設定することができる。例えば、プロリンは、プロリンの喫食濃度が、飲食品１００ｇあたり、０．５μｍｏｌ～２０００μｍｏｌ、好ましくは２μｍｏｌ～１０００μｍｏｌ、さらに好ましくは５μｍｏｌ～５００μｍｏｌとなるように、本発明の「コク味」付与剤に含まれていてよい。 The concentration of “other ingredients” in the “kokumi” imparting agent of the present invention is not particularly limited as long as the “kokumi” imparting agent of the present invention can be used to impart “kokumi” to foods and drinks. It can be appropriately set according to various conditions such as the kind of “component”, the eating concentration of “other components”, and the amount of the “kokumi” imparting agent of the present invention used. The eating concentration of “other components” can be appropriately set according to various conditions such as the type of “other components”. For example, proline is included in the “kokumi” imparting agent of the present invention so that the eating concentration of proline is 0.5 μmol to 2000 μmol, preferably 2 μmol to 1000 μmol, more preferably 5 μmol to 500 μmol per 100 g of food or drink. It may be.
　また、本発明の「コク味」付与剤に含まれる各成分（すなわち、有効成分および必要によりその他の成分）は、互いに混合されて本発明の「コク味」付与剤に含まれていてもよく、それぞれ別個に、あるいは、任意の組み合わせで別個に、本発明の「コク味」付与剤に含まれていてもよい。本発明の「コク味」付与剤を添加して製造された飲食品中で有効成分が共存していれば「コク味」の増強効果が得られる。 Moreover, each component (that is, the active ingredient and other components as required) contained in the “kokumi” imparting agent of the present invention may be mixed with each other and contained in the “kokumi” imparting agent of the present invention. Each of these may be contained in the “kokumi” imparting agent of the present invention separately or in any combination. If the active ingredient coexists in the food and drink produced by adding the “kokumi” imparting agent of the present invention, the effect of enhancing “kokumi” can be obtained.
＜２＞本発明の飲食品の製造方法
　本発明の「コク味」付与剤は、飲食品に「コク味」を付与するために好適に使用できる。すなわち、本発明は、本発明の「コク味」付与剤を飲食品またはその原料に添加することを含む、「コク味」の付与された飲食品の製造方法を提供する。 <2> Manufacturing method of food and drink according to the present invention The “kokumi” imparting agent according to the present invention can be suitably used to impart “kokumi” to food and drink. That is, this invention provides the manufacturing method of the food / beverage products to which "kokumi" was provided including adding the "kokumi" provision agent of this invention to food / beverage products or its raw material.
　また、有効成分を飲食品またはその原料に添加することによって飲食品に「コク味」を付与してもよい。すなわち、本発明は、γ－Ｇｌｕ－Ｘ－Ｇｌｙ（ＸはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）およびγ－Ｇｌｕ－Ｙ（ＹはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）からなる群より選択される１またはそれ以上のγ－グルタミルペプチド、ならびにコハク酸、マレイン酸、およびメチルマロン酸からなる群より選択される１またはそれ以上のジカルボン酸を、飲食品またはその原料に添加することを含む、「コク味」の付与された飲食品の製造方法を提供する。 Moreover, you may give “boiled taste” to foods and drinks by adding active ingredients to foods and drinks or their raw materials. That is, the present invention is selected from the group consisting of γ-Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and γ-Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys). Adding one or more γ-glutamyl peptides, and one or more dicarboxylic acids selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid to a food or drink or a raw material thereof The manufacturing method of the food / beverage products to which "kokumi" was provided is provided.
　このような「コク味」の付与された飲食品の製造方法を「本発明の方法」ともいう。また、このようにして製造される「コク味」の付与された飲食品を「本発明の飲食品」ともいう。 Such a method for producing a food or drink with a “kokumi” taste is also referred to as a “method of the present invention”. Moreover, the food / beverage products provided with the “boiled taste” thus produced are also referred to as “the food / beverage products of the present invention”.
　本発明において、「コク味」とは、甘味(sweet taste)、塩味(salty taste)、酸味(sour taste)、苦味(bitter taste)、うま味(umami)で表される５基本味(five basic taste)では表せない感覚を意味し、基本味だけではなく、厚み(thickness)、ひろがり(growth (mouthfulness))、持続性(continuity)、まとまり(harmony)等の基本味の周辺の味(marginal tastes)や風味（marginal flavor）をも増強した味覚をいう。本発明において、「「コク味」の付与」には、基本味の増強や、それに伴う厚み、ひろがり、持続性、まとまりなど基本味の周辺の味を付与または増強することが含まれる。 In the present invention, the term “kokumi” refers to five basic tastes (five basic taste) represented by sweetness (sweet taste), salty taste (salty taste), sour taste (sour taste), bitterness (bitter taste), and umami ) Means a sense that cannot be expressed, not only the basic taste, but also the tastes of the basic tastes such as thickness, growth (mouthfulness), continuity, harmony, etc. (marginal tastes) Taste with enhanced flavor and marginal flavor. In the present invention, “giving a“ kokumi ”” includes enhancing the basic taste and adding or enhancing the surrounding taste of the basic taste such as thickness, spreading, sustainability, and unity.
　飲食品としては、特に制限されず、あらゆる飲食品が包含される。飲食品としては、例えば、水、果汁、牛乳、茶、アルコール飲料、スープなどの飲料；ハム、ソーセージなどの食肉加工食品；かまぼこ、ちくわなどの水産加工食品；バター、発酵乳、粉乳などの乳製品；パン、麺類、菓子、ソース等が挙げられる。果汁として、具体的には、例えば、リンゴジュースが挙げられる。ソースとして、具体的には、例えば、トマトソースが挙げられる。スープとして、具体的には、例えば、ミネストローネスープ、ポタージュスープ（コーン、ポテト等）、コンソメスープ（チキン、ポーク、ビーフ等）、ラーメンスープ（醤油、味噌、豚骨、塩等）、中華スープ、味噌汁が挙げられる。 The food and drink is not particularly limited, and includes all kinds of food and drink. Examples of foods and beverages include beverages such as water, fruit juice, milk, tea, alcoholic beverages, soups; processed meat products such as ham and sausage; processed fishery products such as kamaboko and chikuwa; milk such as butter, fermented milk, and powdered milk Products: bread, noodles, confectionery, sauce, etc. Specific examples of fruit juice include apple juice. Specific examples of the sauce include tomato sauce. Specifically, for example, minestrone soup, potage soup (corn, potato, etc.), consomme soup (chicken, pork, beef, etc.), ramen soup (soy sauce, miso, pork bone, salt, etc.), Chinese soup, Examples include miso soup.
　本発明の飲食品は、本発明の「コク味」付与剤または有効成分を添加すること以外は、通常の飲食品と同様の原料を用い、同様の方法によって製造することができる。本発明の「コク味」付与剤または有効成分の添加は、飲食品の製造工程のいずれの段階で行われてもよい。すなわち、本発明の「コク味」付与剤または有効成分は、飲食品の原料に添加されてもよく、製造途中の飲食品に添加されてもよく、完成した飲食品に添加されてもよい。本発明の「コク味」付与剤または有効成分は、１回のみ添加されてもよく、２またはそれ以上の回数に分けて添加されてもよい。また、本発明の「コク味」付与剤を添加する場合、本発明の「コク味」付与剤が各有効成分をそれぞれ別個に、あるいは、任意の組み合わせで別個に含む場合には、各有効成分は同時に飲食品またはその原料に添加されてもよいし、それぞれ別個に、あるいは、任意の組み合わせで別個に、飲食品またはその原料に添加されてもよい。また、有効成分を添加する場合、各有効成分は同時に飲食品またはその原料に添加されてもよいし、それぞれ別個に、あるいは、任意の組み合わせで別個に、飲食品またはその原料に添加されてもよい。 The food and drink of the present invention can be produced by the same method using the same raw materials as those of ordinary food and drink, except that the “kokumi” imparting agent or active ingredient of the present invention is added. The “kokumi” imparting agent or the active ingredient of the present invention may be added at any stage of the production process of the food or drink. That is, the “kokumi” imparting agent or active ingredient of the present invention may be added to a raw material for food or drink, may be added to a food or drink in the middle of manufacture, or may be added to a finished food or drink. The “kokumi” imparting agent or active ingredient of the present invention may be added only once, or may be added in two or more times. In addition, when the “kokumi” imparting agent of the present invention is added, when the “kokumi” imparting agent of the present invention contains each active ingredient separately or separately in any combination, each active ingredient May be added to the food or drink or its raw material at the same time, or may be added to the food or drink or its raw material individually or in any combination. Moreover, when adding an active ingredient, each active ingredient may be simultaneously added to food / beverage products or its raw material, and may be added to food / beverage products or its raw material separately separately or in arbitrary combinations. Good.
　本発明の「コク味」付与剤を添加する場合、その添加量は、飲食品に「コク味」を付与できる限り特に制限されず、有効成分の種類、本発明の「コク味」付与剤における有効成分の濃度、飲食品の摂取態様等の諸条件に応じて適宜設定することができる。例えば、飲食品またはその原料に対して、本発明の「コク味」付与剤を０．０１ｐｐｍ～５０％添加してもよく、０．１ｐｐｍ～１０％添加してもよい。本発明の「コク味」付与剤は、例えば、各有効成分の喫食濃度が上記例示した各有効成分の喫食濃度範囲内となるように、飲食品またはその原料に対して添加されてよい。 When the “kokumi” imparting agent of the present invention is added, the amount added is not particularly limited as long as it can impart “kokumi” to foods and drinks, and in the type of active ingredient, the “kokumi” imparting agent of the present invention. It can set suitably according to various conditions, such as the density | concentration of an active ingredient, and the intake mode of food-drinks. For example, the “kokumi” imparting agent of the present invention may be added in an amount of 0.01 ppm to 50% or 0.1 ppm to 10% with respect to the food or drink or its raw material. The “kokumi” imparting agent of the present invention may be added to a food or drink or its raw material so that the eating concentration of each active ingredient is within the eating concentration range of each active ingredient exemplified above.
　有効成分を添加する場合、各有効成分の添加量や各有効成分の添加量の比率については、上述した本発明の「コク味」付与剤の添加量や本発明の「コク味」付与剤における有効成分の比率についての記載を準用できる。すなわち、各有効成分は、例えば、各有効成分の喫食濃度が上記例示した各有効成分の喫食濃度範囲内となるように、飲食品またはその原料に対して添加されてよい。また、各有効成分は、例えば、上記例示した本発明の「コク味」付与剤における有効成分の比率で、飲食品またはその原料に対して添加されてよい。 When adding active ingredients, the ratio of the amount of each active ingredient added and the amount of each active ingredient added is the same as in the above-mentioned amount of “kokumi” imparting agent of the present invention or “kokumi” imparting agent of the present invention. The description about the ratio of active ingredients can be applied mutatis mutandis. That is, for example, each active ingredient may be added to a food or drink or its raw material so that the eating concentration of each active ingredient is within the eating concentration range of each active ingredient exemplified above. Moreover, each active ingredient may be added with respect to food-drinks or its raw material by the ratio of the active ingredient in the "boiled taste" imparting agent of this invention illustrated above, for example.
　なお、γ－グルタミルペプチドおよびジカルボン酸の両方に該当する成分、例えばγ－グルタミルペプチドのジカルボン酸塩、を添加する場合、同成分はγ－グルタミルペプチドおよびジカルボン酸の両方を兼ねる。すなわち、γ－グルタミルペプチドおよびジカルボン酸の両方に該当する成分、例えばγ－グルタミルペプチドのジカルボン酸塩、を添加する場合、別途γ－グルタミルペプチドおよび／またはジカルボン酸を添加してもよく、添加しなくともよい。 In addition, when a component corresponding to both γ-glutamyl peptide and dicarboxylic acid, for example, a dicarboxylate salt of γ-glutamyl peptide, is added, the component also serves as both γ-glutamyl peptide and dicarboxylic acid. That is, when components corresponding to both γ-glutamyl peptide and dicarboxylic acid, for example, dicarboxylate of γ-glutamyl peptide, are added, γ-glutamyl peptide and / or dicarboxylic acid may be added separately. Not necessary.
　また、本発明の方法は、さらに、その他の成分を添加することを含んでいてもよい。ここでいう「その他の成分」については、上述した本発明の「コク味」付与剤における「その他の成分」についての記載を準用できる。例えば、「その他の成分」としては、プロリンを添加することができる。「その他の成分」の添加は、上述した有効成分の添加と同様に行ってよい。例えば、プロリンは、プロリンの喫食濃度が上記例示したプロリンの喫食濃度範囲内となるように、飲食品またはその原料に対して添加されてよい。 Further, the method of the present invention may further include adding other components. Regarding the “other components” here, the description of “other components” in the above-described “kokumi” imparting agent of the present invention can be applied mutatis mutandis. For example, proline can be added as the “other components”. The addition of “other components” may be performed in the same manner as the addition of the active ingredients described above. For example, proline may be added to a food or drink or its raw material so that the eating concentration of proline is within the eating concentration range of proline exemplified above.
　本発明は、以下の実施例によって更に具体的に説明されるが、これらはいかなる意味でも本発明を限定する意図と解してはならない。 The present invention will be described more specifically with reference to the following examples, which should not be construed as limiting the present invention in any way.
実施例１：γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムを飲食品に添加し、「コク味」付与効果について評価した。 Example 1: Evaluation of “bitter taste” imparting effect by the combined use of γ-Glu-Val-Gly and succinic acid In this example, γ-Glu-Val-Gly and disodium succinate were added to food and drink. The “kokumi” imparting effect was evaluated.
　市販ミネストローネスープ（キャンベル社製）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏl／１００ｇ（５ｐｐｍ）、及びコハク酸二ナトリウムを喫食濃度１５．４３μｍｏｌ／１００ｇ（２５ｐｐｍ）となるように、それぞれ単独で、または組み合わせて添加し、表１に示す評価サンプルＳ１～Ｓ３を調製した。 A commercially available minestrone soup (manufactured by Campbell) was used as an evaluation system, and a sample to which nothing was added was used as a control. Γ-Glu-Val-Gly was used as a control sample at a diet concentration of 1.65 μmol / 100 g (5 ppm), and disodium succinate at a diet concentration of 15.43 μmol / 100 g (25 ppm), either alone or in combination. Evaluation samples S1 to S3 shown in Table 1 were prepared.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏl／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a eating concentration of 1.65 μmol / 100 g. I did.
　結果を表１に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。 The results are shown in Table 1. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the strength of “thickness” and “sustainability” increased synergistically when disodium succinate was used in combination. It became clear to do.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
実施例２：γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸（フリー体および塩）の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸（フリー体）またはコハク酸二ナトリウムを飲食品に添加し、「コク味」付与効果について評価した。 Example 2: Evaluation of the “kokumi” imparting effect by the combined use of γ-Glu-Val-Gly and succinic acid (free and salt) In this example, γ-Glu-Val-Gly and succinic acid (free) Alternatively, disodium succinate was added to foods and drinks, and the “kokumi” imparting effect was evaluated.
　市販の果汁２０％リンゴジュース（コカコーラ社製）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏｌ／１００ｇ（５ｐｐｍ）、コハク酸を喫食濃度２１．１８μｍｏｌ／１００ｇ（２５ｐｐｍ）、及びコハク酸二ナトリウムを喫食濃度１５．４３μｍｏｌ／１００ｇ（２５ｐｐｍ）となるように、それぞれ単独で、または組み合わせて添加し、表２に示す評価サンプルＳ１～Ｓ５を調製した。 Commercially available 20% apple juice (manufactured by Coca-Cola) was used as an evaluation system, and a sample to which nothing was added was used as a control. As control samples, γ-Glu-Val-Gly had a eating concentration of 1.65 μmol / 100 g (5 ppm), succinic acid had a eating concentration of 21.18 μmol / 100 g (25 ppm), and disodium succinate had a eating concentration of 15.43 μmol / 100 g. Evaluation samples S1 to S5 shown in Table 2 were prepared by adding them individually or in combination so as to be (25 ppm).
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏｌ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a eating concentration of 1.65 μmol / 100 g. I did.
　結果を表２に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸またはコハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。以上より、フリー体のコハク酸及びコハク酸塩のいずれについても、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙと併用することによって、相乗的に「コク味」が強まることが示された。 The results are shown in Table 2. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the combination of succinic acid or disodium succinate synergistically increased the “thickness” and “sustainability”. It became clear that the rise. From the above, it was shown that both the free succinic acid and the succinic acid salt synergistically enhance the “kokumi” when used together with γ-Glu-Val-Gly.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
実施例３：γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ、コハク酸、およびプロリンの併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸（フリー体）に加えて、さらにプロリンを飲食品に添加し、「コク味」付与効果について評価した。 Example 3: Evaluation of the “kokumi” imparting effect by the combined use of γ-Glu-Val-Gly, succinic acid, and proline In this example, in addition to γ-Glu-Val-Gly and succinic acid (free form) Furthermore, proline was added to the food and drink, and the “kokumi” imparting effect was evaluated.
　市販の果汁２０％リンゴジュース（コカコーラ社製）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏｌ／１００ｇ（５ｐｐｍ）、コハク酸を喫食濃度２１．１８μｍｏｌ／１００ｇ（２５ｐｐｍ）、及びプロリンを喫食濃度４３．４４μｍｏｌ／１００ｇ（５０ｐｐｍ）となるように、それぞれ単独で、または組み合わせて添加し、表３に示す評価サンプルＳ１～Ｓ５を調製した。 Commercially available 20% apple juice (manufactured by Coca-Cola) was used as an evaluation system, and a sample to which nothing was added was used as a control. As control samples, γ-Glu-Val-Gly had a food concentration of 1.65 μmol / 100 g (5 ppm), succinic acid had a food concentration of 21.18 μmol / 100 g (25 ppm), and proline had a food concentration of 43.44 μmol / 100 g (50 ppm). Thus, evaluation samples S1 to S5 shown in Table 3 were prepared by adding each alone or in combination.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏｌ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a eating concentration of 1.65 μmol / 100 g. I did.
　結果を表３に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸のみを併用した場合と比較して、さらにプロリンを併用した場合には、相乗的に「厚み」の強さが上昇することが明らかとなった。以上より、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸およびプロリンとを併用することによって、相乗的に「コク味」が強まることが示された。 The results are shown in Table 3. As a result of sensory evaluation, it is clear that the strength of “thickness” increases synergistically when proline is used in combination, compared with the case where γ-Glu-Val-Gly and succinic acid alone are used together. became. From the above, it has been shown that the combined use of γ-Glu-Val-Gly, succinic acid and proline synergistically increases the “kokumi”.
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
実施例４：γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムを種々の濃度で飲食品に添加し、「コク味」付与効果について評価した。 Example 4: Evaluation of the “kokumi” imparting effect by the combined use of γ-Glu-Val-Gly and succinic acid In this example, γ-Glu-Val-Gly and disodium succinate were added to food and drink at various concentrations. It added and evaluated about the "kokumi" provision effect.
　市販トマトソース（カゴメ社製）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０１７μｍｏｌ／１００ｇ（０．０５ｐｐｍ）～１．６５μｍｏｌ／１００ｇ（５ｐｐｍ）、およびコハク酸二ナトリウムを喫食濃度０．６μｍｏｌ／１００ｇ（１．０ｐｐｍ）～１５４３μｍｏｌ／１００ｇ（２５００ｐｐｍ）となるように添加し、表４に示す評価サンプルＳ１～Ｓ１８を調製した。 Commercial tomato sauce (manufactured by Kagome) was used as an evaluation system, and a sample to which nothing was added was used as a control. As control samples, γ-Glu-Val-Gly was fed at a eating concentration of 0.017 μmol / 100 g (0.05 ppm) to 1.65 μmol / 100 g (5 ppm), and disodium succinate was fed at a eating concentration of 0.6 μmol / 100 g (1. 0 ppm) to 1543 μmol / 100 g (2500 ppm) were added to prepare evaluation samples S1 to S18 shown in Table 4.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル２名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏｌ／１００ｇとなるように単独で添加した際の強さを「＋＋」として、評点付けを行った。 官能 Sensory evaluation was performed by two specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “++” when γ-Glu-Val-Gly is added to the control sample alone at a food concentration of 1.65 μmol / 100 g. I did.
　結果を表４に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを喫食濃度０．６μｍｏｌ／１００ｇ～１５４３μｍｏｌ／１００ｇとなるように併用した場合には、相乗的に「厚み」及び「持続性」が上昇することが明らかとなった。なお、コハク酸の呈味の観点では、コハク酸二ナトリウムの喫食濃度が１２３５［μｍｏｌ／１００ｇ］以下の場合に好ましい結果が得られた。また、コハク酸の呈味の観点では、γ－グルタミルペプチドに対するジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が約７５０００以下の場合に好ましい結果が得られた。 The results are shown in Table 4. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, disodium succinate was used synergistically at a eating concentration of 0.6 μmol / 100 g to 1543 μmol / 100 g. In particular, it became clear that “thickness” and “sustainability” increased. In terms of the taste of succinic acid, preferable results were obtained when the dietary concentration of disodium succinate was 1235 [μmol / 100 g] or less. In terms of the taste of succinic acid, preferable results were obtained when the molar ratio of dicarboxylic acid to γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) was about 75,000 or less.
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
実施例５：各種γ－グルタミルペプチドとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、各種γ－グルタミルペプチドとコハク酸二ナトリウムを飲食品に添加し、「コク味」付与効果について評価した。 Example 5: Evaluation of the effect of imparting “kokumi” by combining various γ-glutamyl peptides and succinic acid In this example, various γ-glutamyl peptides and disodium succinate were added to foods and drinks to impart “kokumi” The effect was evaluated.
　市販の果汁２０％リンゴジュース（コカコーラ社製）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、コハク酸二ナトリウム、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ、γ－Ｇｌｕ－Ａｂｕ、γ－Ｇｌｕ－Ｎｖａ－Ｇｌｙ、及びγ－Ｇｌｕ－Ｎｖａを表５に示す喫食濃度となるように添加し、評価サンプルＳ１～Ｓ１３を調製した。 Commercially available 20% apple juice (manufactured by Coca-Cola) was used as an evaluation system, and a sample to which nothing was added was used as a control. To the control sample, disodium succinate, γ-Glu-Val-Gly, γ-Glu-Abu, γ-Glu-Nva-Gly, and γ-Glu-Nva were added so as to have the eating concentrations shown in Table 5. Evaluation samples S1 to S13 were prepared.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル２名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏｌ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by two specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a eating concentration of 1.65 μmol / 100 g. I did.
　結果を表５に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ、γ－Ｇｌｕ－Ａｂｕ、γ－Ｇｌｕ－Ｎｖａ－Ｇｌｙ、またはγ－Ｇｌｕ－Ｎｖａを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。以上より、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙのみならず、その他のγ－グルタミルペプチドについても、コハク酸と併用することによって、相乗的に「コク味」が強まることが示された。 The results are shown in Table 5. As a result of sensory evaluation, γ-Glu-Val-Gly, γ-Glu-Abu, γ-Glu-Nva-Gly, or γ-Glu-Nva was used in combination with disodium succinate In this case, it became clear that the strength of “thickness” and “sustainability” increased synergistically. From the above, it was shown that not only γ-Glu-Val-Gly but also other γ-glutamyl peptides are synergistically enhanced in “kokumi” when used in combination with succinic acid.
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
実施例６：γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙと各種ジカルボン酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸に類似する各種ジカルボン酸（フリー体）を飲食品に添加し、「コク味」付与効果について評価した。 Example 6: Evaluation of the effect of imparting “kokumi” by the combined use of γ-Glu-Val-Gly and various dicarboxylic acids In this example, γ-Glu-Val-Gly and various dicarboxylic acids similar to succinic acid (free form) ) Was added to foods and drinks, and evaluated for the effect of imparting “kokumi”.
　市販の果汁２０％リンゴジュース（コカコーラ社製）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙ、コハク酸、マレイン酸、及びメチルマロン酸を表６に示す喫食濃度となるように添加し、評価サンプルＳ１～Ｓ９を調製した。 Commercially available 20% apple juice (manufactured by Coca-Cola) was used as an evaluation system, and a sample to which nothing was added was used as a control. To the control sample, γ-Glu-Val-Gly, succinic acid, maleic acid, and methylmalonic acid were added so as to have the eating concentrations shown in Table 6 to prepare evaluation samples S1 to S9.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル２名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度１．６５μｍｏｌ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by two specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a eating concentration of 1.65 μmol / 100 g. I did.
　結果を表６に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸、マレイン酸、またはメチルマロン酸を併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。以上より、コハク酸のみならず、コハク酸に類似する各種ジカルボン酸についても、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙと併用することによって、相乗的に「コク味」が強まることが示された。 The results are shown in Table 6. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, when succinic acid, maleic acid, or methylmalonic acid was used in combination, “thickness” and “sustainability” It became clear that the strength of "" increased. From the above, it has been shown that not only succinic acid but also various dicarboxylic acids similar to succinic acid are synergistically enhanced in “kokumi” when used together with γ-Glu-Val-Gly.
Figure JPOXMLDOC01-appb-T000006
Figure JPOXMLDOC01-appb-T000006
実施例７：ポタージュスープにおけるγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムをポタージュスープに添加し、「コク味」付与効果について評価した。 Example 7: Evaluation of the “kokumi” imparting effect of the combination of γ-Glu-Val-Gly and succinic acid in potage soup In this example, γ-Glu-Val-Gly and disodium succinate were added to the potage soup Then, the “kokumi” imparting effect was evaluated.
　市販ポタージュスープ（クノール食品社製：製品の指示通りに調製したもの）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇ（１．６５μｍｏｌ／１００ｇ）、及びコハク酸二ナトリウムを喫食濃度０．００２５ｇ／１００ｇ（１５．４３μｍｏｌ／１００ｇ）となるように、それぞれ単独で、または組み合わせて添加し、表７に示す評価サンプルＳ１～Ｓ３を調製した。 A commercial potage soup (manufactured by Knorr Foods Co., Ltd .: prepared according to product instructions) was used as an evaluation system, and a sample to which nothing was added was used as a control. In the control sample, γ-Glu-Val-Gly has a eating concentration of 0.0005 g / 100 g (1.65 μmol / 100 g), and disodium succinate has a eating concentration of 0.0025 g / 100 g (15.43 μmol / 100 g). Were added alone or in combination to prepare evaluation samples S1 to S3 shown in Table 7.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a food concentration of 0.0005 g / 100 g. I did.
　結果を表７に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。 The results are shown in Table 7. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the strength of “thickness” and “sustainability” increased synergistically when disodium succinate was used in combination. It became clear to do.
Figure JPOXMLDOC01-appb-T000007
Figure JPOXMLDOC01-appb-T000007
実施例８：チキンコンソメスープにおけるγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムをチキンコンソメスープに添加し、「コク味」付与効果について評価した。 Example 8: Evaluation of “Kokumi” imparting effect by combined use of γ-Glu-Val-Gly and succinic acid in chicken consomme soup In this example, γ-Glu-Val-Gly and disodium succinate were combined with chicken consomme soup. The effect of imparting “kokumi” was evaluated.
　市販チキンコンソメスープ（クノール社製）１キューブを３００ｍＬの熱湯に溶解したものを評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇ（１．６５μｍｏｌ／１００ｇ）、及びコハク酸二ナトリウムを喫食濃度０．００２５ｇ／１００ｇ（１５．４３μｍｏｌ／１００ｇ）となるように、それぞれ単独で、または組み合わせて添加し、表８に示す評価サンプルＳ１～Ｓ３を調製した。 Commercially available chicken consomme soup (Kunol Co., Ltd.) 1 cube dissolved in 300 mL of hot water was used as an evaluation system, and a sample to which nothing was added was used as a control. In the control sample, γ-Glu-Val-Gly has a eating concentration of 0.0005 g / 100 g (1.65 μmol / 100 g), and disodium succinate has a eating concentration of 0.0025 g / 100 g (15.43 μmol / 100 g). Were added alone or in combination to prepare evaluation samples S1 to S3 shown in Table 8.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a food concentration of 0.0005 g / 100 g. I did.
　結果を表８に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。 The results are shown in Table 8. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the strength of “thickness” and “sustainability” increased synergistically when disodium succinate was used in combination. It became clear to do.
Figure JPOXMLDOC01-appb-T000008
Figure JPOXMLDOC01-appb-T000008
実施例９：醤油ラーメンスープにおけるγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムを醤油ラーメンスープに添加し、「コク味」付与効果について評価した。 Example 9: Evaluation of “Kokumi” imparting effect of γ-Glu-Val-Gly and succinic acid in soy sauce ramen soup In this example, γ-Glu-Val-Gly and disodium succinate were combined with soy sauce ramen soup. The effect of imparting “kokumi” was evaluated.
　市販の即席醤油ラーメン（「麺職人」醤油味：日清食品社製）の別添スープ１袋を４５０ｍＬの熱湯に溶解したものを評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇ（１．６５μｍｏｌ／１００ｇ）、及びコハク酸二ナトリウムを喫食濃度０．００２５ｇ／１００ｇ（１５．４３μｍｏｌ／１００ｇ）となるように、それぞれ単独で、または組み合わせて添加し、表９に示す評価サンプルＳ１～Ｓ３を調製した。 A commercially available instant soy sauce ramen (“noodle craftsman” soy sauce taste: manufactured by Nissin Foods) dissolved in 450 mL of hot water was used as an evaluation system, and a sample to which nothing was added was used as a control. In the control sample, γ-Glu-Val-Gly has a eating concentration of 0.0005 g / 100 g (1.65 μmol / 100 g), and disodium succinate has a eating concentration of 0.0025 g / 100 g (15.43 μmol / 100 g). Were added alone or in combination to prepare evaluation samples S1 to S3 shown in Table 9.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a food concentration of 0.0005 g / 100 g. I did.
　結果を表９に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。 The results are shown in Table 9. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the strength of “thickness” and “sustainability” increased synergistically when disodium succinate was used in combination. It became clear to do.
Figure JPOXMLDOC01-appb-T000009
Figure JPOXMLDOC01-appb-T000009
実施例１０：豚骨ラーメンスープにおけるγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムを豚骨ラーメンスープに添加し、「コク味」付与効果について評価した。 Example 10: Evaluation of the effect of imparting “kokumi” by combining γ-Glu-Val-Gly and succinic acid in pork bone ramen soup In this example, γ-Glu-Val-Gly and disodium succinate were added to pork bone. It was added to ramen soup and evaluated for its “kokumi” imparting effect.
　市販即席豚骨ラーメン（マルちゃん「正麺」とんこつ味：東洋水産社製）の別添スープ１袋を５００ｍＬの熱湯に溶解したものを評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇ（１．６５μｍｏｌ／１００ｇ）、及びコハク酸二ナトリウムを喫食濃度０．００２５ｇ／１００ｇ（１５．４３μｍｏｌ／１００ｇ）となるように、それぞれ単独で、または組み合わせて添加し、表１０に示す評価サンプルＳ１～Ｓ３を調製した。 A commercially available instant pork bone ramen (Maru-chan "Senmen" Tonkotsumi: manufactured by Toyo Suisan Co., Ltd.) dissolved in 500 mL of hot water was used as an evaluation system, and a sample to which nothing was added was used as a control. In the control sample, γ-Glu-Val-Gly has a eating concentration of 0.0005 g / 100 g (1.65 μmol / 100 g), and disodium succinate has a eating concentration of 0.0025 g / 100 g (15.43 μmol / 100 g). Were added alone or in combination to prepare evaluation samples S1 to S3 shown in Table 10.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a food concentration of 0.0005 g / 100 g. I did.
　結果を表１０に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。 The results are shown in Table 10. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the strength of “thickness” and “sustainability” increased synergistically when disodium succinate was used in combination. It became clear to do.
Figure JPOXMLDOC01-appb-T000010
Figure JPOXMLDOC01-appb-T000010
実施例１１：中華スープにおけるγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムを中華スープに添加し、「コク味」付与効果について評価した。 Example 11: Evaluation of the effect of imparting “kokumi” by the combined use of γ-Glu-Val-Gly and succinic acid in Chinese soup In this example, γ-Glu-Val-Gly and disodium succinate were added to Chinese soup Then, the “kokumi” imparting effect was evaluated.
　市販即席中華スープ（クノール食品社製：１袋を１８０ｍＬの熱湯で溶解したものから具材を除いたもの）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇ（１．６５μｍｏｌ／１００ｇ）、及びコハク酸二ナトリウムを喫食濃度０．００２５ｇ／１００ｇ（１５．４３μｍｏｌ／１００ｇ）となるように、それぞれ単独で、または組み合わせて添加し、表１１に示す評価サンプルＳ１～Ｓ３を調製した。 Commercially available instant Chinese soup (Kunol Foods Co., Ltd .: 1 bag dissolved in 180 mL of hot water) was used as an evaluation system, and a sample to which nothing was added was used as a control. In the control sample, γ-Glu-Val-Gly has a eating concentration of 0.0005 g / 100 g (1.65 μmol / 100 g), and disodium succinate has a eating concentration of 0.0025 g / 100 g (15.43 μmol / 100 g). Were added alone or in combination to prepare evaluation samples S1 to S3 shown in Table 11.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a food concentration of 0.0005 g / 100 g. I did.
　結果を表１１に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。 The results are shown in Table 11. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the strength of “thickness” and “sustainability” increased synergistically when disodium succinate was used in combination. It became clear to do.
Figure JPOXMLDOC01-appb-T000011
Figure JPOXMLDOC01-appb-T000011
実施例１２：味噌汁におけるγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸の併用による「コク味」付与効果の評価
　本実施例では、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙとコハク酸二ナトリウムを味噌汁に添加し、「コク味」付与効果について評価した。 Example 12: Evaluation of “kokumi” imparting effect by combined use of γ-Glu-Val-Gly and succinic acid in miso soup In this example, γ-Glu-Val-Gly and disodium succinate were added to miso soup, The “kokumi” imparting effect was evaluated.
　市販即席みそ汁（永谷園社製「あさげ」：製品の指示通りに調製したものから具材を除いたもの）を評価系とし、何も添加しないサンプルをコントロールとした。コントロールサンプルに、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇ（１．６５μｍｏｌ／１００ｇ）、及びコハク酸二ナトリウムを喫食濃度０．００２５ｇ／１００ｇ（１５．４３μｍｏｌ／１００ｇ）となるように、それぞれ単独で、または組み合わせて添加し、表１２に示す評価サンプルＳ１～Ｓ３を調製した。 Commercially available instant miso soup ("Asage" manufactured by Nagatanien Co., Ltd .: the product prepared according to the product instructions excluding ingredients) was used as an evaluation system, and a sample to which nothing was added was used as a control. In the control sample, γ-Glu-Val-Gly has a eating concentration of 0.0005 g / 100 g (1.65 μmol / 100 g), and disodium succinate has a eating concentration of 0.0025 g / 100 g (15.43 μmol / 100 g). Were added alone or in combination to prepare evaluation samples S1 to S3 shown in Table 12.
　評価サンプルの「厚み」及び「持続性」の強さについて、専門パネル３名により官能評価を行った。官能評価は、「－；変化なし」～「＋＋＋＋＋；非常に強い」の６段階で評点を付けることにより行った。尚、ここでいう「厚み」は調和が取れた状態で呈味全体が強まること、「持続性」は口に含んで５秒以降の呈味の強さを意味する。「厚み」及び「持続性」の強さ共に、コントロールサンプルにγ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを喫食濃度０．０００５ｇ／１００ｇとなるように単独で添加した際の強さを「＋」として、評点付けを行った。 官能 Sensory evaluation was performed by three specialist panels on the strength of “thickness” and “sustainability” of the evaluation sample. The sensory evaluation was performed by assigning a score in six stages from “−; no change” to “++++++; very strong”. Here, “thickness” means that the whole taste is strengthened in a harmonious state, and “sustainability” means the strength of taste after 5 seconds in the mouth. Both “thickness” and “sustainability” are rated as “+” when γ-Glu-Val-Gly is added to the control sample alone at a food concentration of 0.0005 g / 100 g. I did.
　結果を表１２に示す。官能評価の結果、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙを単独で添加した場合と比較して、コハク酸二ナトリウムを併用した場合には、相乗的に「厚み」及び「持続性」の強さが上昇することが明らかとなった。 The results are shown in Table 12. As a result of sensory evaluation, compared with the case where γ-Glu-Val-Gly was added alone, the strength of “thickness” and “sustainability” increased synergistically when disodium succinate was used in combination. It became clear to do.
Figure JPOXMLDOC01-appb-T000012
Figure JPOXMLDOC01-appb-T000012
　本発明により、飲食品に対して効果的に「コク味」を付与できる「コク味」付与剤を提供できる。また、本発明により提供される「コク味」付与剤を用いて「コク味」の付与された飲食品を製造することができる。 The present invention can provide a “kokumi” imparting agent that can effectively impart “kokumi” to foods and drinks. Moreover, the food / beverage products to which "kokumi" was provided can be manufactured using the "kokumi" imparting agent provided by this invention.

Claims (16)

  1. 　γ－Ｇｌｕ－Ｘ－Ｇｌｙ（ＸはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）およびγ－Ｇｌｕ－Ｙ（ＹはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）からなる群より選択されるγ－グルタミルペプチド、ならびにコハク酸、マレイン酸、およびメチルマロン酸からなる群より選択されるジカルボン酸を含む、コク味付与剤。 γ-Glutamyl peptide selected from the group consisting of γ-Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and γ-Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys) And a kokumi imparting agent comprising a dicarboxylic acid selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid.
  2. 　前記γ－グルタミルペプチドに対する前記ジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が１より大きい、請求項１に記載のコク味付与剤。 The body taste imparting agent according to claim 1, wherein the molar ratio of the dicarboxylic acid to the γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is greater than 1.
  3. 　前記γ－グルタミルペプチドに対する前記ジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が７５０００以下である、請求項１または２に記載のコク味付与剤。 The richness imparting agent according to claim 1 or 2, wherein a molar ratio of the dicarboxylic acid to the γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is 75,000 or less.
  4. 　前記γ－グルタミルペプチドが、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙである、請求項１～３のいずれか１項に記載のコク味付与剤。 The body taste imparting agent according to any one of claims 1 to 3, wherein the γ-glutamyl peptide is γ-Glu-Val-Gly.
  5. 　前記ジカルボン酸が、コハク酸である、請求項１～４のいずれか１項に記載のコク味付与剤。 The richness imparting agent according to any one of claims 1 to 4, wherein the dicarboxylic acid is succinic acid.
  6. 　さらにプロリンを含む、請求項１～５のいずれか１項に記載のコク味付与剤。 The body taste imparting agent according to any one of claims 1 to 5, further comprising proline.
  7. 　請求項１～６のいずれか１項に記載のコク味付与剤を飲食品またはその原料に添加することを含む、コク味の付与された飲食品の製造方法。 A method for producing a food and drink with a rich taste, which comprises adding the body taste imparting agent according to any one of claims 1 to 6 to the food or drink or a raw material thereof.
  8. 　γ－Ｇｌｕ－Ｘ－Ｇｌｙ（ＸはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）およびγ－Ｇｌｕ－Ｙ（ＹはＣｙｓを除くアミノ酸又はアミノ酸誘導体を表す）からなる群より選択されるγ－グルタミルペプチド、ならびにコハク酸、マレイン酸、およびメチルマロン酸からなる群より選択されるジカルボン酸を、飲食品またはその原料に添加することを含む、コク味の付与された飲食品の製造方法。 γ-Glutamyl peptide selected from the group consisting of γ-Glu-X-Gly (X represents an amino acid or amino acid derivative excluding Cys) and γ-Glu-Y (Y represents an amino acid or amino acid derivative excluding Cys) And a method for producing a food or drink with a rich taste, comprising adding a dicarboxylic acid selected from the group consisting of succinic acid, maleic acid, and methylmalonic acid to the food or drink or a raw material thereof.
  9. 　添加されるγ－グルタミルペプチドに対する添加されるジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が１より大きい、請求項８に記載の方法。 The method according to claim 8, wherein the molar ratio of the added dicarboxylic acid to the added γ-glutamyl peptide (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is greater than 1.
  10. 　添加されるγ－グルタミルペプチドに対する添加されるジカルボン酸のモル比（ジカルボン酸／γ－グルタミルペプチド［ｍｏｌ／ｍｏｌ］）が７５０００以下である、請求項８または９に記載の方法。 The method according to claim 8 or 9, wherein the molar ratio of the dicarboxylic acid added to the γ-glutamyl peptide added (dicarboxylic acid / γ-glutamyl peptide [mol / mol]) is 75000 or less.
  11. 　前記γ－グルタミルペプチドが、喫食濃度が飲食品１００ｇあたり０．０１７μｍｏｌ～１．６５μｍｏｌとなるように添加される、請求項８～１０のいずれか１項に記載の方法。 The method according to any one of claims 8 to 10, wherein the γ-glutamyl peptide is added so that a food concentration is 0.017 µmol to 1.65 µmol per 100 g of food or drink.
  12. 　前記ジカルボン酸が、喫食濃度が飲食品１００ｇあたり０．６μｍｏｌ～１２３５μｍｏｌとなるように添加される、請求項８～１１のいずれか１項に記載の方法。 The method according to any one of claims 8 to 11, wherein the dicarboxylic acid is added so that a food concentration is 0.6 µmol to 1235 µmol per 100 g of food or drink.
  13. 　前記γ－グルタミルペプチドが、γ－Ｇｌｕ－Ｖａｌ－Ｇｌｙである、請求項８～１２のいずれか１項に記載の方法。 The method according to any one of claims 8 to 12, wherein the γ-glutamyl peptide is γ-Glu-Val-Gly.
  14. 　前記ジカルボン酸が、コハク酸である、請求項８～１３のいずれか１項に記載の方法。 The method according to any one of claims 8 to 13, wherein the dicarboxylic acid is succinic acid.
  15. 　さらにプロリンを添加することを含む、請求項８～１４のいずれか１項に記載の方法。 The method according to any one of claims 8 to 14, further comprising adding proline.
  16. 　前記ジカルボン酸の純度が９０％以上である、請求項８～１５のいずれか１項に記載の方法。 The method according to any one of claims 8 to 15, wherein the purity of the dicarboxylic acid is 90% or more.
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