WO2011081186A1 - コク味付与剤 - Google Patents

コク味付与剤 Download PDF

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Publication number
WO2011081186A1
WO2011081186A1 PCT/JP2010/073722 JP2010073722W WO2011081186A1 WO 2011081186 A1 WO2011081186 A1 WO 2011081186A1 JP 2010073722 W JP2010073722 W JP 2010073722W WO 2011081186 A1 WO2011081186 A1 WO 2011081186A1
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WO
WIPO (PCT)
Prior art keywords
glu
gly
food
nva
taste
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PCT/JP2010/073722
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English (en)
French (fr)
Japanese (ja)
Inventor
貴志 宮木
直宏 宮村
恵 金子
裕右 網野
礼子 安田
譲 江藤
高穂 田島
Original Assignee
味の素株式会社
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Application filed by 味の素株式会社 filed Critical 味の素株式会社
Priority to SG2012048146A priority Critical patent/SG181978A1/en
Priority to CA2783415A priority patent/CA2783415C/en
Priority to AU2010339306A priority patent/AU2010339306B2/en
Priority to CN201080063730.6A priority patent/CN102753041B/zh
Priority to JP2011547717A priority patent/JP5850399B2/ja
Priority to RU2012132448/10A priority patent/RU2532106C2/ru
Priority to MX2012007244A priority patent/MX2012007244A/es
Priority to KR1020127019882A priority patent/KR101512627B1/ko
Priority to NZ601030A priority patent/NZ601030A/en
Publication of WO2011081186A1 publication Critical patent/WO2011081186A1/ja
Priority to IL220527A priority patent/IL220527A0/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • 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
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids

Definitions

  • the present invention relates to a body taste imparting agent and a composite body taste imparting agent comprising a peptide exhibiting CaSR agonist activity.
  • the present invention also relates to a food composition containing a peptide having CaSR agonist activity at a certain concentration or more.
  • Patent Document 1 describes that ⁇ -Glu-X-Gly (X is an amino acid or an amino acid derivative) is a compound having CaSR agonist activity, etc., but ⁇ -Glu-Nva-Gly is described. Is not described in detail in the examples, and is not disclosed specifically. In addition, the content of patent document 1 and 2 shall be contained in description of this specification.
  • the present invention searches for many variation compounds having CaSR agonist activity and has a more excellent body taste imparting action, in particular, an aftertaste type and high potency body taste imparting action, and has excellent stability. It is an object of the present invention to find a substance capable of imparting a taste, and to provide a kokumi imparting agent comprising the substance and a complex kokumi imparting agent comprising the substance in combination with another substance having CaSR agonist activity. It is another object of the present invention to provide a food composition containing the substance at a certain concentration.
  • ⁇ -Glu-Nva-Gly L- ⁇ -glutamyl-L-norvalyl-glycine
  • CaSR agonist activity a substance that is a carboxylic acid
  • ⁇ -Glu-Nva-Gly has an imparting effect, and in particular, its taste pattern can impart a rich taste that is a medium aftertaste type.
  • ⁇ -Glu-Nva-Gly has an extremely high titer of 10 times or more compared with the same tripeptide ⁇ -Glu-Val-Gly, and has excellent stability. And it discovered that the preferable taste pattern that a middle aftertaste was strong was shown.
  • ⁇ -Glu-Nva-Gly can be a useful body taste imparting agent by itself. Further, it has been found that by adding ⁇ -Glu-Nva-Gly, a preferable food composition with enhanced richness can be obtained. Furthermore, it discovered that it could become a complex body taste imparting agent formed by using this substance together with another substance having CaSR agonist activity, and completed the present invention.
  • the present invention provides a rich taste imparting agent comprising ⁇ -Glu-Nva-Gly.
  • the present invention also provides a food composition containing ⁇ -Glu-Nva-Gly (hereinafter also referred to as “the food composition of the present invention”).
  • the present invention also relates to (a) ⁇ -Glu-Nva-Gly, (b) ⁇ -Glu-X-Gly (X represents an amino acid or amino acid derivative, except Nva), ⁇ -Glu-Val- Y (Y represents an amino acid or amino acid derivative), ⁇ -Glu-Nva, ⁇ -Glu-Abu, ⁇ -Glu-Ala, ⁇ -Glu-Gly, ⁇ -Glu-Cys, ⁇ -Glu-Met, ⁇ - Glu-Thr, ⁇ -Glu-Val, ⁇ -Glu-Orn, Asp-Gly, Cys-Gly, Cys-Met, Glu-Cys, Gly-Cys, Leu-Asp, D-Cys, ⁇ -Glu-Met ( O), ⁇ -Glu- ⁇ -Glu-Val, ⁇ -Glu-Val-NH 2 , ⁇ -Glu-Val-ol, ⁇ -Glu-Ser, ⁇ -Glu-Tau, ⁇ -Glu-Cys (S- Me) (
  • the present invention has a very excellent body taste imparting action, in particular, a unique medium aftertaste type having a profile whose taste pattern is shown in FIG.
  • a rich body taste imparting agent and a complex body taste imparting agent that can be produced easily and at low cost can be provided.
  • the outstanding food composition which contains the substance which has the outstanding richness imparting effect
  • the rich taste imparting agent of the present invention can impart a fat-like richness and smoothness to the taste of low-fat foods, so even if the fat content in fat-containing foods is reduced, it is the same as the original food Can maintain a rich sense of health and can be made into a health-conscious food. Examples of such foods include meat-containing foods and dairy products.
  • a food containing the richness-imparting agent of the present invention is eaten, there is an advantage that a fat-like richness and smoothness can be felt afterwards without being eaten.
  • FIG. 1 shows a taste profile of a medium aftertaste type body taste imparting agent.
  • ⁇ -Glu-Nva-Gly targeted in the present invention includes L- ⁇ -glutamyl-L-norvalyl-glycine formed by peptide bonding of three amino acids and / or a salt thereof, particularly an edible salt. Since ⁇ -Glu-Nva-Gly has an excellent body taste imparting effect, it can be used as a body taste imparting agent. ⁇ -Glu-Nva-Gly is 0.1 ppb to 99.9% by mass, preferably 1 ppb to 10% by mass, more preferably 0.01 ppm to 1% by mass with respect to the weight of the food composition imparting a rich taste. % Can be added and used.
  • another aspect of the present invention relates to a food composition containing ⁇ -Glu-Nva-Gly, preferably a food composition containing 0.1 ppb to 99.9% by mass of ⁇ -Glu-Nva-Gly. . More preferably, the present invention relates to a food composition containing 0.01 to 50 ppm by weight of ⁇ -Glu-Nva-Gly.
  • the body taste imparting agent of the present invention is composed of amino acids such as sodium glutamate (MSG), nucleic acids such as inosine monophosphate (IMP), inorganic salts such as sodium chloride,
  • amino acids such as sodium glutamate (MSG)
  • nucleic acids such as inosine monophosphate (IMP)
  • inorganic salts such as sodium chloride
  • the term “kokumi” means five basic tastes represented by sweet taste, salty taste, sour taste, bitter taste, and umami. It means a taste that cannot be expressed in terms of basic taste, as well as thickness, thickness (mounthfulness), continuity, harmony, etc. The taste is also enhanced.
  • “kokumi impartation” means to enhance the five basic tastes expressed by sweetness, salty taste, acidity, bitterness, umami, and to give a taste around the basic tastes such as thickness, spread, and unity. Say. This can also be expressed as a taste enhancing action. Therefore, ⁇ -Glu-Nva-Gly, which is the body taste imparting agent of the present invention, can also be expressed as a flavor enhancer.
  • ⁇ -Glu-Nva-Gly which is a body taste imparting agent of the present invention can be used as a sweetness enhancer, salty taste enhancer, sour taste enhancer, bitterness enhancer or umami enhancer.
  • the taste changes with the passage of time after eating, but they are called an initial taste, a middle taste, and an after taste in order from immediately after eating.
  • taste, medium and aftertaste are tastes to be felt from 0 to 2 seconds, from 2 to 5 seconds, and after 5 seconds, respectively, after eating. Further, the period from 0 to 5 seconds is called “first taste”, and the period from about 2 seconds to about 30 seconds is called “medium after taste” (see FIG. 1).
  • CaSR means a calcium sensing receptor (Calcium® Sensing® Receptor), which belongs to the class C of the 7-transmembrane receptor, and is also referred to as a calcium receptor.
  • the “CaSR agonist” means a substance that binds to the CaSR and activates the CaSR.
  • activate CaSR means that a ligand binds to CaSR and activates a guanine nucleotide-binding protein to transmit a signal. The property of binding to CaSR and activating CaSR is referred to as “CaSR agonist activity”.
  • a test substance is added to a CaSR activity measurement system for measuring CaSR activity, and the CaSR activity is measured.
  • the CaSR activity when the test substance is added is compared with the CaSR activity when the test substance is not added.
  • the measurement of CaSR activity can be performed using, for example, a measurement system using cells that express CaSR.
  • the cell may be a cell that endogenously expresses CaSR or a recombinant cell into which a CaSR gene has been introduced exogenously.
  • the CaSR activity measurement system can detect binding (reaction) between an activator and CaSR when an extracellular ligand (activator) specific to CaSR is added to the cell expressing CaSR. It can be used without particular limitation as long as it can transmit a detectable signal in the cell in response to the binding (reaction) between the activator and CaSR.
  • CaSR activity is detected by reaction with the test substance, it is determined that the test substance has CaSR stimulating activity.
  • CaSR examples include human CaSR encoded by the human CaSR gene registered under GenBank Accession No. NM_000388.
  • CaSR is not limited to the protein encoded by the gene of the above sequence, and as long as it encodes a protein having a CaSR function, it is 60% or more, preferably 80% or more, more preferably 90% or more. It may be a protein encoded by a homologous gene.
  • the CaSR function can be examined by expressing these genes in cells and measuring changes in current and intracellular calcium ion concentration when calcium is added.
  • the origin of the CaSR is not particularly limited, and examples include CaSR derived from any animal including mice, rats, dogs and the like as well as the human CaSR.
  • the CaSR activity can be confirmed using a living cell expressing CaSR or a fragment thereof, a cell membrane expressing CaSR or a fragment thereof, an in vitro system containing a protein of CaSR or a fragment thereof, or the like.
  • An example using living cells is shown below, but is not limited thereto.
  • CaSR is expressed in cultured cells such as Xenopus oocytes, hamster ovary cells, and human fetal kidney cells. This can be achieved by introducing a plasmid carrying a foreign gene into which a CaSR gene has been cleaned and introducing the plasmid state or cRNA using it as a template.
  • an electrophysiological technique or a fluorescent indicator reagent for increasing intracellular calcium can be used.
  • CaSR expression is first confirmed by a response with calcium or a specific activator.
  • An oocyte in which an intracellular current is observed or a cultured cell in which fluorescence of a fluorescent indicator reagent is observed is used with respect to calcium having a concentration of about 5 mM. The concentration dependence is measured by changing the calcium concentration.
  • the test substance is prepared to about 1 ⁇ M to 1 mM, added to the oocyte or cultured cell, and the CaSR activity of the test substance is measured by measuring the CaSR activity in the presence of the test substance. taking measurement.
  • examples of the CaSR agonist activity test include, but are not limited to, the tests shown in the test examples of the present specification.
  • the amino acid or peptide used in combination with ⁇ -Glu-Nva-Gly in the complex rich taste imparting agent of the present invention is ⁇ -Glu-X-Gly (X represents an amino acid or amino acid derivative other than Nva), ⁇ -Glu- Val-Y (Y represents an amino acid or amino acid derivative), ⁇ -Glu-Nva, ⁇ -Glu-Abu, ⁇ -Glu-Ala, ⁇ -Glu-Gly, ⁇ -Glu-Cys, ⁇ -Glu-Met, ⁇ -Glu-Thr, ⁇ -Glu-Val, ⁇ -Glu-Orn, Asp-Gly, Cys-Gly, Cys-Met, Glu-Cys, Gly-Cys, Leu-Asp, D-Cys, ⁇ -Glu- Met (O), ⁇ -Glu- ⁇ -Glu-Val, ⁇ -Glu-Val-NH 2 , ⁇ -Glu-Val-ol, ⁇ -Glu-Ser, ⁇ -Glu-Tau, ⁇ -G 1 selected
  • Neutral amino acids acidic amino acids such as Asp and Glu, basic amino acids such as Lys, Arg and His, aromatic amino acids such as Phe, Tyr and Trp, homoserine, citrulline, ornithine, ⁇ -aminobutyric acid, norvaline, norleucine , Taurine and the like are also included. Further, it may be a non-natural (non-protein constituent) amino acid such as tert-leucine, cycloloinsine, ⁇ -aminoisobutyric acid, L-penicillamine and the like.
  • X may be any of the above amino acids or derivatives thereof, but an amino acid other than Cys or a derivative thereof is preferred.
  • ⁇ -Glu-Val-Gly, ⁇ -Glu-Abu-Gly, ⁇ -Glu-tLeu-Gly, ⁇ -Glu-Nva, ⁇ -Glu-Abu and the like are preferable.
  • the body taste imparting agent of the present invention is composed of ⁇ -Glu-Nva-Gly and has a unique medium aftertaste type excellent body taste imparting action having a profile as shown in FIG. It is preferably used in combination with a peptide having a different profile from ⁇ -Glu-Abu-Gly, ⁇ -Glu-Abu, etc.
  • an amino acid residue means the following amino acids.
  • amino acid derivatives are various derivatives of the above amino acids.
  • amino acids side chains such as special amino acids, unnatural amino acids, amino alcohols, terminal carbonyl groups, amino groups, cysteine thiol groups, and the like are substituted with various substituents. Substituted ones are mentioned.
  • 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.
  • Val-NH 2 Valinamide
  • Val-ol Valinol (2-amino- 3-methyl-1-butanol) and the like.
  • ⁇ -Glu-Cys (SNO) -Gly has the following structural formula
  • ⁇ -Glu-Met (O) and ⁇ -Glu-Cys (S-Me) (O (O) in the formula means a sulfoxide structure.
  • ( ⁇ ) of ⁇ -Glu means that another amino acid is bonded via a carboxyl group at the ⁇ position of glutamic acid.
  • the ⁇ -Glu-Nva-Gly and the amino acid or peptide used in combination with the ⁇ -Glu-Nva-Gly of the present invention may be a commercially available product, in addition, (1) a chemical synthesis method, or ( 2) Although it can be obtained by appropriately using a known method such as a method of synthesizing by an enzymatic reaction, chemical synthesis is simpler. Since ⁇ -Glu-Nva-Gly used in the present invention has a short amino acid residue of 3 residues, the chemical synthesis method is relatively simple and industrially advantageous.
  • the oligopeptide is synthesized or semi-synthesized using a peptide synthesizer.
  • the chemical synthesis method include a peptide solid phase synthesis method.
  • the peptide thus synthesized can be purified by conventional means such as ion exchange chromatography, reverse phase high performance liquid chromatography, affinity chromatography and the like. Such peptide solid phase synthesis methods, and subsequent peptide purification, are well known in the art.
  • ⁇ -Glu-Nva-Gly and an amino acid or peptide used in combination therewith by an enzymatic reaction for example, the method described in International Publication Pamphlet WO 2004/011653 is used. May be. That is, an amino acid or dipeptide in which the carboxyl terminus of one amino acid or dipeptide is esterified or amidated, and an amino acid in which the amino acid is free (for example, an amino acid in which the carboxyl group is protected) are combined in the presence of a peptide-forming enzyme. It is also possible to produce by producing the dipeptide or tripeptide produced by reacting in the above.
  • the peptide-forming enzyme examples include a culture of a microorganism having the ability to produce a peptide, a microbial cell separated from the culture, a treated product of the microorganism, or a peptide-generating enzyme derived from the microorganism.
  • the matters described in WO 2004/011653 are included in the description of this specification.
  • the peptides used in the present invention may be present in plants such as vegetables and fruits, microorganisms such as yeast, and other natural products. If they exist in nature, they can be extracted from these and used.
  • the kokumi imparting agent or the complex kokumi imparting agent of the present invention can be used as a seasoning as it is or by mixing it with a carrier and other seasoning ingredients that are acceptable for food and drink.
  • seasoning materials include, for example, flavorings, sugars, sweeteners, dietary fibers, vitamins, amino acids such as sodium glutamate (MSG), nucleic acids such as inosine monophosphate (IMP), and inorganic substances such as sodium chloride. Examples thereof include organic acids such as salts and citric acid, and various yeast extracts.
  • the low fat food preferable as a food composition containing the rich taste imparting agent or the complex rich taste imparting agent of the present invention is a food originally containing fat, and particularly a food having a reduced fat content.
  • fat is synonymous with “oil and fat”, includes both solid and liquid, and may be either animal fat or vegetable fat.
  • Such low-fat foods include dairy products such as milk, yogurt, butter and cream, margarine, milk for coffee, foods containing animal oils and / or vegetable oils such as sauces, roux, emulsified foods such as dressings and mayonnaise, etc. And various curries and stews containing cooked meat, and various soups containing meat extracts.
  • steaks and grilled meat made of cooked low-fat beef and baked snacks that are not subjected to normal frying are also included.
  • the low-fat food those whose normal fat content is 1/2 to 1/3 are preferable.
  • the rich taste-imparting agent of the present invention in the low-fat foods, when these foods are eaten, the fat-like richness and smoothness can be felt next, not first.
  • milk and yogurt normal products are 3-4% fat, while zero fat products (about 0.1% fat) are also known.
  • the savoriness imparting agent or the complex savoriness imparting agent of the present invention is also effective for these zero fat products.
  • the present invention also provides a food composition containing ⁇ -Glu-Nva-Gly and pork ingredients.
  • the food containing the pork raw material is not particularly limited, and examples thereof include pork extract, sausage, and instant noodle soup.
  • the content of the pork raw material is not particularly limited, and examples thereof include a food composition of the present invention that is about 0.005 to 80% by weight.
  • the present invention also provides a food composition containing ⁇ -Glu-Nva-Gly and a beef raw material.
  • a foodstuff containing a beef raw material For example, beef extract, corn beef, beef use soup, beef use sauce, etc. are mentioned.
  • a food composition may be about 0.005 to 80% by weight.
  • ⁇ -Glu-Nva-Gly and the amino acid or peptide used together in the present invention also include a salt form.
  • the salt may be a pharmacologically acceptable edible salt.
  • acidic groups such as groups, ammonium salts, salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium and magnesium, aluminum salts, zinc salts, triethylamine, ethanolamine, morpholine
  • alkali metals such as sodium and potassium
  • alkaline earth metals such as calcium and magnesium
  • aluminum salts such as calcium and magnesium
  • zinc salts triethylamine, ethanolamine, morpholine
  • organic amines such as pyrrolidine, piperidine, piperazine and dicyclohexylamine
  • salts with basic amine acids such as arginine and lysine.
  • salts with inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, hydrobromic acid, acetic acid, citric acid, benzoic acid, maleic acid, fumaric acid, tartaric acid, succinic acid, Salts with organic carboxylic acids such as tannic acid, butyric acid, hibenzic acid, pamoic acid, enanthic acid, decanoic acid, teocric acid, salicylic acid, lactic acid, oxalic acid, mandelic acid, malic acid, methanesulfonic acid, benzenesulfonic acid, p And salts with organic sulfonic acids such as toluenesulfonic acid.
  • inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid, hydrobromic acid, acetic acid, citric acid, benzoic acid, maleic acid, fumaric acid, tartaric acid, succin
  • the rich taste imparting agent, food composition, or complex rich taste imparting agent of the present invention can be used in any form without limitation on physical properties such as dry powder, paste, and solution.
  • the rich taste imparting agent, food composition, or complex rich taste imparting agent of the present invention can be used by blending it with various foods and beverages such as foods, beverages and seasonings.
  • the amount of the amino acid or peptide used in combination is not particularly limited as long as the desired effect is obtained, but the amount of ⁇ -Glu-Nva-Gly and / or the amount of amino acid or peptide may be food, beverage or seasoning, etc. From about 0.1 ppb to 99.9% by weight, preferably from 1 ppb to 10% by weight, and more preferably from about 0.01 ppm to 1% by weight.
  • any solid or liquid carrier that is acceptable for foods and beverages may be further blended.
  • the carrier include glucose, lactose, sucrose, starch, mannitol, dextrin, fatty acid glyceride, polyethylene glycol, hydroxyethyl starch, ethylene glycol, polyoxyethylene sorbitan fatty acid ester, gelatin, albumin, amino acid, water, and physiological saline. Water etc. are mentioned.
  • the seasoning raw material may be any seasoning raw material used in the art and is not particularly limited, but more specifically, the above-mentioned ones are already mentioned.
  • the content of any of the above carriers and other seasoning ingredients is not particularly limited.
  • the yeast extract is not particularly limited in any of the cells from which it is derived, its culture conditions, and the extraction treatment method, and any yeast extract can be used. Further, heat treatment, enzyme treatment, concentration, powder It may be one that has been processed.
  • the present invention also provides a method for producing various foods and drinks, characterized in that ⁇ -Glu-Nva-Gly is added to the production intermediate product of various foods and drinks so that 1 mass ppb to 99.9% by mass is contained. provide.
  • various foods and drinks low-fat foods are preferable.
  • This invention also provides the manufacturing method of various food-drinks characterized by adding the food composition of this invention to the manufacture intermediate goods of various food-drinks.
  • various foods and drinks low-fat foods are preferable.
  • a taste enhancer comprising ⁇ -Glu-Nva-Gly is used as a raw material for foods and beverages (for example, umami raw material, protein hydrolyzate, animal meat extract).
  • a method for producing food or drink or a food intermediate for producing food or drink which includes a step of adding to and mixing, and, if necessary, a step of further cooking the resulting food or drink raw material mixture, is preferred.
  • the step of adding and mixing the taste enhancer composed of ⁇ -Glu-Nva-Gly to the raw material for the food and drink, the concentration of ⁇ -Glu-Nva-Gly in the intermediate product of the food and drink is 0.01-999900 ppm by weight
  • it includes a step of adjusting to 0.1 to 200,000 ppm by weight.
  • the intermediate product of the food and drink is added to another food and drink raw material (for example, agricultural products, marine products, livestock meat, dairy products, or processed foods thereof), and the resulting food and drink ⁇ -Glu-Nva-Gly It is preferable to further include a step of adjusting the concentration to 0.01 to 50 ppm by weight, preferably 0.05 to 20 ppm by weight.
  • the step of adding and mixing the taste enhancer comprising ⁇ -Glu-Nva-Gly to the food / beverage product raw material has a concentration of ⁇ -Glu-Nva-Gly of the food / beverage product of 0.01 to 50 ppm by weight, preferably 0 It is preferable to include a step of setting the content to 0.05 to 20 ppm by weight.
  • food / beverage products are the foodstuffs containing a pork raw material. In this case, it is preferable to contain 0.01 to 50 ppm by weight of ⁇ -Glu-Nva-Gly, 0.005 to 80% by weight of pork ingredients, and other food ingredients.
  • food / beverage products are the foodstuffs containing a beef raw material. In this case, it is preferable to contain 0.01 to 50 ppm by weight of ⁇ -Glu-Nva-Gly, 0.005 to 80% by weight of beef ingredients, and other food ingredients.
  • the target foods of the present invention are foods such as ice cream, honey, marmalade, and strawberry jam (sweet foods) such as desserts and confectionery (sweet foods), and salty tastes such as chicken soup
  • foods such as processed foods, side dishes and snacks (savory foods) are also preferred.
  • the reaction solution was kept at 0 ° C., and triethylamine (Et 3 N, 3.13 ml, 1.1 eq, 22.4 mmol), HOBt ⁇ H 2 O (1-Hydroxybenzotriazole hydrate, 3.44 g, 1.1 eq, 22.4 mmol) and WSC ⁇ HCl (1 -Ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride, 4.30 g, 1.1 eq, 22.4 mmol) was added. The temperature of the reaction solution was gradually raised and stirred at room temperature overnight (16 hours).
  • the reaction mixture was concentrated under reduced pressure, ethyl acetate (150 ml) was added to the residue, and the organic layer was washed twice with water (50 ml) and 5% aqueous citric acid solution (50 ml), saturated brine (50 ml), 5
  • the extract was washed twice with an aqueous sodium hydrogen carbonate solution (50 ml) and with saturated brine (50 ml), and dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure.
  • Boc-Nva-Gly-OBzl (6.88 g, 18.9 mmol) as crystals.
  • Boc-Nva-Gly-OBzl (6.88 g, 18.9 mmol) was added 4N HCl / dioxane solution (94.5 ml), and the mixture was stirred at room temperature for 1 hour.
  • Dioxane was removed by concentration under reduced pressure, and the operation of adding n-hexane (30 ml) to the residue and concentrating under reduced pressure was repeated three times to obtain H-Nva-Gly-OBzlHCl in a quantitative yield.
  • H-Nva-Gly-OBzlHCl was dissolved in methylene chloride (130 ml), and the reaction solution was kept at 0 ° C.
  • Z-Glu-OBzl N- ⁇ -Carbobenzoxy-L-glutamic acid ⁇ -benzyl ester, 7.03 g, 18.9 mmol
  • triethylamine (2.90 ml, 1.1 eq, 20.8 mmol
  • HOBt ⁇ H 2 O (3.20 g, 1.1 eq, 20.8 mmol)
  • WSC.HCl (3.98 g, 1.1 eq, 20.8 mmol) were added.
  • the temperature of the reaction solution was gradually raised and stirred at room temperature overnight (16 hours).
  • the reaction mixture was concentrated under reduced pressure, ethyl acetate (1000 ml) was added to the residue, and the organic layer was washed twice with water (100 ml) and 5% aqueous citric acid solution (100 ml), saturated brine (100 ml), 5
  • the extract was washed twice with an aqueous sodium hydrogen carbonate solution (100 ml) and with saturated brine (100 ml), and dried over anhydrous magnesium sulfate. After the solution was heated to 50 ° C., magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. When crystals began to appear, n-hexane was added to sufficiently precipitate the crystals.
  • CaSR expression plasmid was prepared as follows. Based on the DNA sequence (CaSR (calcium receptor): NM_000388, SEQ ID NO: 1, 2) registered in NCBI, synthetic oligo DNA (forward primer (SEQ ID NO: 3: ACTAATACGACTCACTATAGGGACCATGGCATTTTATAGCTGCTGCTGG)) and reverse primer (SEQ ID NO: SEQ ID NO: 1) 4: TTATGAATTCACTACGTTTTCTGTAACAG) was synthesized.
  • CaSR calcium receptor
  • PCR was carried out under the following conditions using cDNA derived from human kidney (manufactured by Clontech) as a material and the above primers and Pfu Ultra DNA Polymerase (manufactured by Stratagene). After 3 minutes at 94 ° C., 35 times of 94 ° C. for 30 seconds, 55 ° C. for 30 seconds and 72 ° C. for 2 minutes were repeated 35 times, followed by reaction at 72 ° C. for 7 minutes. After agarose electrophoresis and staining with a DNA staining reagent, it was detected whether or not amplification was performed by UV irradiation. In addition, the chain length of the PCR product was confirmed by comparison with a DNA marker of known size that was electrophoresed simultaneously.
  • Plasmid vector pBR322 was cleaved with restriction enzyme EcoRV (Takara), and the gene fragment amplified by PCR was ligated to the cleavage site using Ligation kit (Promega).
  • the Escherichia coli DH5 ⁇ strain was transformed with this reaction solution, and a transformant carrying a plasmid in which the PCR amplification product was cloned was selected, and the PCR amplification product was further confirmed by DNA nucleotide sequence analysis.
  • a human CaSR expression plasmid hCaSR / pcDNA3.1 was prepared.
  • Assay Buffer 146 mM NaCl, 5 mM KCl, 1 mM MgSO 4 , 1 mg / ml Glucose, 20 mM HEPES (pH 7.2) 200 ul / well of Ca 2+ fluorescent indicator Calcium 4 Assay Kit (Molecular Devices) dissolved in 0.75 to 1.25 mM CaCl 2 ) was added and allowed to stand at 37 ° C. for 1 hour and then at room temperature for 10 minutes to incorporate the indicator. .
  • a test compound dissolved in 0.1% BSA-containing assay buffer was added to the 96-well plate at 50 ⁇ l / well, and the change in fluorescence intensity was measured with FLEX Station (Molecular Devices) for 3 minutes.
  • Example 1 Evaluation of kokumi imparting activity
  • the strength of kokumi imparting activity of ⁇ -Glu-Nva-Gly was examined by a quantitative sensory evaluation test.
  • the quantitative sensory evaluation test was performed as follows. In a distilled water containing sodium glutamate (0.05 g / dl), inosinic acid monophosphate (0.05 g / dl), sodium chloride (0.5 g / dl), the compounds as a sample were 0.000001-0. The strength of the savoriness imparting activity when mixed at 1 g / dl was measured. About the sample which showed the acidity with respect to the additive-free control after sample dissolution, it was used according to the range of pH ⁇ 0.2 with respect to the additive-free control with NaOH.
  • control 0 points, strong: 3 points, very strong: 5 points, and ⁇ -Glu-Cys-Gly's pre-taste and after-taste were set to 3.0 points to make the scale clearer.
  • the “first taste” refers to a taste of 0 to 5 seconds after the mouth, and the aftertaste is a taste after that.
  • the test compounds exhibited a wide range of richness-imparting activity at the above addition concentrations.
  • Table 4 shows the results of typical concentrations. As a result, all the tripeptides other than ⁇ -Glu-Nva-Gly were about 10 times as high as glutathione ( ⁇ -Glu-Cys-Gly), but surprisingly, ⁇ -Glu -Nva-Gly was even higher and was shown to be 100 times more highly active.
  • ⁇ -Glu-Nva-Gly is about 100 times higher than ⁇ -Glu-Cys-Gly, and at least 10 times higher in taste-providing activity than ⁇ -Glu-Val-Gly. Furthermore, ⁇ -Glu-Nva-Gly is superior, with no off-flavors (such as aftertaste astringency), such as ⁇ -Glu-Ala-Gly, ⁇ -Glu-Abu-Gly, and ⁇ -Glu-tLeu-Gly. I understood that.
  • Example 2 Evaluation of kokumi imparting activity For ⁇ -Glu-Nva-Gly, the strength of kokumi imparting activity was examined by a quantitative sensory evaluation test in another evaluation item in order to clarify the middle aftertaste type.
  • the quantitative sensory evaluation test was performed as follows. In order to make the middle aftertaste easier to understand, the innocous acid monophosphate was not used in the evaluation solution, and the umami after the middle was reduced. That is, when the compounds as a sample were mixed at 0.000001 to 0.1 g / dl in distilled water containing sodium glutamate (0.1 g / dl) and sodium chloride (0.4 g / dl), The intensity of taste imparting activity was measured.
  • n 4.
  • the “prior taste” is a taste of 0 to 2 seconds after the mouth is contained, and the medium after taste is a taste after that.
  • the test compounds exhibited a wide range of richness-imparting activity at the above-mentioned added concentrations. Table 5 shows the results of typical concentrations.
  • ⁇ -Glu-Val-Gly was about 10 times as active as glutathione ( ⁇ -Glu-Cys-Gly), but ⁇ -Glu-Nva-Gly was even higher, slightly more than 100 times. It was shown to have a high activity.
  • ⁇ -Glu-Nva-Gly has an excellent kokumi imparting activity, has a taste of medium aftertaste, and is excellent with no off-flavors (such as astringent taste).
  • ⁇ -Glu-Nva-Gly is about 100 times higher than ⁇ -Glu-Cys-Gly, and has a kokumi imparting activity that is at least 10 times higher than ⁇ -Glu-Val-Gly. It can be used at low concentrations. Therefore, it is possible to provide a richness-imparting agent more easily and at a low cost, which is very advantageous from an industrial viewpoint.
  • Example 3 Evaluation of kokumi- taste-imparting activity in foods ⁇ -Glu-Nva-Gly is actually sensory-evaluated whether it is extremely effective compared to high-titer ⁇ -Glu-Val-Gly when used in foods. It was examined by testing. The sensory evaluation test was performed as follows. Commercially available ice cream, honey, marmalade, and strawberry jam were used as representative foods such as desserts and confectionery that mainly have sweetness (sweet foods) as foods that are thought to have a strong aftertaste.
  • ⁇ -Glu-Val-Gly As a representative of processed foods such as salty foods, side dishes, and snacks (savory foods), a commercially available chicken soup, 0.1% by weight of powdered powdered pepper and mashed potato paste, commercially available ginger, and 2% by weight of butter The paste added to the mashed potato was used. The amount of ⁇ -Glu-Val-Gly to be compared was set to 0.002% by weight where the effect was obvious. When ⁇ -Glu-Nva-Gly was mixed at 0.0000001 to 0.01% by weight, the enhancement of the overall taste (strength of kokumi imparting activity) was measured. The control is an additive-free food.
  • n 4. With respect to ⁇ -Glu-Val-Gly, the richness-enhancing activity was widely exhibited at the above-mentioned added concentrations.
  • Tables 7 and 8 show the results of concentrations that can be clearly compared. This result also shows that ⁇ -Glu-Nva-Gly has an additional 5-13 compared to ⁇ -Glu-Val-Gly, which is about 10 times as rich as glutathione ( ⁇ -Glu-Cys-Gly). It was shown to have a double strength and extremely high activity.
  • ⁇ -Glu-Nva-Gly was found to have promising kokumi imparting activity that enhances the overall taste in all foods characterized by a medium aftertaste from actual savory to sweet foods. Furthermore, it was shown that ⁇ -Glu-Nva-Gly has an extremely high body taste imparting activity of 5 to 13 times as much as ⁇ -Glu-Val-Gly in actual foods. Therefore, it is desired to improve the quality. However, even if the raw materials cannot be blended any more because of the quality stability, the quality can be improved in a very small amount by using ⁇ -Glu-Nva-Gly. Moreover, it is possible to provide a rich taste imparting agent at low cost.
  • Example 4 Effect of ⁇ -Glu-Nva-Gly on pork extract As for ⁇ -Glu-Nva-Gly, kokumi imparting activity activity is higher than ⁇ -Glu-Cys-Gly (glutathione) and ⁇ -Glu-Val-Gly After eating, it turned out that it strengthened from an early time. Therefore, ⁇ -Glu-Nva-Gly is significantly more effective than ⁇ -Glu-Cys-Gly (glutathione) and ⁇ -Glu-Val-Gly for pork extracts that are not completely medium-type and have a slightly stronger taste. It was examined by a sensory evaluation test. The sensory evaluation test was performed as follows.
  • a commercially available pork extract (solid content 55.1 wt%, salt content 9.3 wt%) was dissolved in hot water so as to be 5.0 wt% to prepare a pork extract solution.
  • ⁇ -Glu-Nva-Gly, ⁇ -Glu-Cys-Gly, or ⁇ -Glu-Val-Gly was mixed as a sample. The measurement was performed using a two-point discrimination test method.
  • Table 9 shows the number of panels in which ⁇ -Glu-Nva-Gly 0.0003% by weight was evaluated as “poke extract is stronger and more favorable without changing the balance between taste and flavor”. From these results, it is clear that ⁇ -Glu-Nva-Gly clearly shows that “Poke extract is strengthened and favored without changing the balance between taste and flavor” even at the equivalent strength value as in (1) and (3). It was shown that.
  • the pork extract does not change the balance between taste and flavor base. It has been found that it has a very specific effect of “strengthening and favoring”. Pork ingredients are widely used worldwide for seasonings, soups, processed meat products, cooked products, confectionery, snacks, etc. Therefore, ⁇ -Glu-Nva-Gly can improve foods at a lower cost and in a minute amount, and is very advantageous from an industrial viewpoint.
  • Example 5 Effect of ⁇ -Glu-Nva-Gly on Beef Extract With ⁇ -Glu-Nva-Gly, Kokumi imparting activity is eaten from ⁇ -Glu-Cys-Gly (glutathione) and ⁇ -Glu-Val-Gly Later, it turned out that it strengthened from an early time. Therefore, ⁇ -Glu-Nva-Gly is significantly more ⁇ -Glu-Cys-Gly (glutathione) and ⁇ -Glu-Val-Gly than beef extract, which is not a perfect middle-type but has a slightly faster taste and lasts until aftertaste. Effectiveness was examined by a sensory evaluation test. The sensory evaluation test was performed as follows.
  • a commercially available beef extract (solid content: 61.2 wt%, salt content: 12.2 wt%) was dissolved in hot water to 3.0 wt% to prepare a beef extract solution.
  • ⁇ -Glu-Nva-Gly, ⁇ -Glu-Cys-Gly, or ⁇ -Glu-Val-Gly was mixed as a sample. The measurement was performed using a two-point discrimination test method.
  • Table 10 shows the number of panels in which ⁇ -Glu-Nva-Gly 0.0003% by weight was evaluated as “a beef extract is stronger and preferable without changing the balance between taste and flavor”. From these results, it is clear that ⁇ -Glu-Nva-Gly clearly “strengthens and favors beef extract without changing the balance of taste and flavor” even with the same rich taste strength as in (1) and (3) It has been shown.
  • “beef extract” can be used without changing the balance between taste and flavor base. It has been found that it has a very specific effect of “enhancing and favoring”. Beef ingredients are widely used worldwide for seasonings, soups, processed meat products, cooked products, confectionery, snacks, etc. Therefore, ⁇ -Glu-Nva-Gly can improve foods at a lower cost and in a minute amount, and is very advantageous from an industrial viewpoint.

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SG2012048146A SG181978A1 (en) 2009-12-28 2010-12-28 Flavor-enriching agent
CA2783415A CA2783415C (en) 2009-12-28 2010-12-28 Kokumi-imparting agent comprising y-glu-nva-gly
AU2010339306A AU2010339306B2 (en) 2009-12-28 2010-12-28 Kokumi-Imparting Agent
CN201080063730.6A CN102753041B (zh) 2009-12-28 2010-12-28 浓味赋予剂
JP2011547717A JP5850399B2 (ja) 2009-12-28 2010-12-28 コク味付与剤
RU2012132448/10A RU2532106C2 (ru) 2009-12-28 2010-12-28 Агент для придания кокуми
MX2012007244A MX2012007244A (es) 2009-12-28 2010-12-28 Agente para impartir kokumi.
KR1020127019882A KR101512627B1 (ko) 2009-12-28 2010-12-28 코쿠미 부여제
NZ601030A NZ601030A (en) 2009-12-28 2010-12-28 Kokumi-imparting agent
IL220527A IL220527A0 (en) 2009-12-28 2012-06-20 Kokumi-imparting agent

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WO2013133404A1 (ja) * 2012-03-09 2013-09-12 味の素株式会社 調味料
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JP2016019470A (ja) * 2014-07-11 2016-02-04 味の素株式会社 Ｗ／ｏ／ｗ型乳化物
JPWO2014123175A1 (ja) * 2013-02-07 2017-02-02 味の素株式会社 香辛料風味が増強された飲食品の製造方法
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CN112931836A (zh) * 2021-03-23 2021-06-11 东北农业大学 一种新型鲜味剂及其制备
KR20230090044A (ko) * 2021-12-14 2023-06-21 샘표식품 주식회사 깊은맛의 식물성 발효물을 위한 감마-글루타밀 펩타이드 증진 제조방법

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Publication number Priority date Publication date Assignee Title
WO2013118742A1 (ja) 2012-02-06 2013-08-15 味の素株式会社 飲食品にコク味を付与するための組成物
WO2013133404A1 (ja) * 2012-03-09 2013-09-12 味の素株式会社 調味料
WO2014017485A1 (ja) * 2012-07-25 2014-01-30 味の素株式会社 果汁含有飲食品
JPWO2014123175A1 (ja) * 2013-02-07 2017-02-02 味の素株式会社 香辛料風味が増強された飲食品の製造方法
JP2016019470A (ja) * 2014-07-11 2016-02-04 味の素株式会社 Ｗ／ｏ／ｗ型乳化物
WO2019013122A1 (ja) 2017-07-13 2019-01-17 不二製油グループ本社株式会社 ペプチド
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WO2020149287A1 (ja) 2019-01-16 2020-07-23 不二製油グループ本社株式会社 食用油脂組成物およびその製造方法

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