WO2010114022A1 - ペプチドのコク味付与用途 - Google Patents
ペプチドのコク味付与用途 Download PDFInfo
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- WO2010114022A1 WO2010114022A1 PCT/JP2010/055856 JP2010055856W WO2010114022A1 WO 2010114022 A1 WO2010114022 A1 WO 2010114022A1 JP 2010055856 W JP2010055856 W JP 2010055856W WO 2010114022 A1 WO2010114022 A1 WO 2010114022A1
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- glu
- food
- abu
- drink
- beverage
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- RXHXBGASUVBEAD-CTZLJUBGSA-N C#[N][C@@H](CCC(NC(C1)([C@@H]1SN=O)C(NCC(O)=O)=O)=O)C(O)=O Chemical compound C#[N][C@@H](CCC(NC(C1)([C@@H]1SN=O)C(NCC(O)=O)=O)=O)C(O)=O RXHXBGASUVBEAD-CTZLJUBGSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT 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
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT 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
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT 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
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. Moreover, this invention relates to the seasoning which contains the peptide which shows CaSR agonist activity more than fixed concentration.
- kokumi There are various taste patterns in the above-mentioned “kokumi”, but there is a high need for a kokumi imparting agent that can give a kokumi taste whose taste pattern is a first taste type. Moreover, since the substance imparting richness is usually used in foods and the like, it is required to have excellent stability. Furthermore, it is industrially desired that the substance imparting richness can be produced more simply and at low cost.
- the present invention searches for many variation compounds having CaSR agonist activity, has a more excellent body taste imparting action, in particular, a taste-type body taste imparting action, is excellent in stability, and is produced simply and at low cost.
- a substance capable of imparting kokumi that can be obtained, to provide a kokumi imparting agent comprising the substance, and to provide a complex kokumi imparting agent comprising the substance in combination with another substance having CaSR agonist activity Is an issue. Furthermore, it aims at providing the seasoning containing this substance more than a fixed density
- ⁇ -Glu-Abu L- ⁇ -glutamyl-L-2-aminobutyric acid
- the taste pattern can give a rich taste that is a pioneer type.
- the found ⁇ -Glu-Abu exhibits a preferable taste pattern that is superior in stability and stronger in taste than the similar dipeptide ⁇ -Glu-Cys.
- the found ⁇ -Glu-Abu can be a useful body taste imparting agent by itself, and can be a complex body taste imparting agent formed by using the substance in combination with other substances having CaSR agonist activity.
- the headline and the present invention were completed.
- the present invention provides a rich taste imparting agent comprising ⁇ -Glu-Abu.
- the present invention also relates to (a) ⁇ -Glu-Abu, (b) ⁇ -Glu-X-Gly (X represents an amino acid or amino acid derivative), ⁇ -Glu-Val-Y (Y is an amino acid or amino acid).
- ⁇ -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) (O), ⁇ -Glu-Leu, ⁇ -Glu-Ile, ⁇ -Glu-t-Leu Beauty provide ⁇ -Glu-Cys (S-Me) 1 kind selected from the group consisting of two or more amino acids or peptides, comprising in combination a composite body taste imparting agents.
- the present invention also relates to (a) ⁇ -Glu-Abu, (b) ⁇ -Glu-X-OCH (Z) CO 2 H (X represents an amino acid or amino acid derivative, and Z represents H (hydrogen atom) or CH 3 (methyl group)), or a complex richness-imparting agent comprising a combination of one or more peptides selected from the formula ⁇ -Glu-Val-Y (Y is GlyA or LacA) I will provide a.
- the present invention provides a seasoning containing ⁇ -Glu-Abu at 1000 ppm by weight or more, preferably 2000 ppm by weight or more, more preferably 2500 ppm by weight or more (hereinafter also referred to as “the seasoning of the present invention”). To do.
- the present invention also includes a step of adding a food / beverage material containing ⁇ -Glu-Abu of 1000 ppm by weight or more, preferably 2000 ppm by weight or more, more preferably 2500 ppm by weight or more to another food / beverage product material, and Provided, if necessary, a method for producing a food / beverage product or a food / beverage product intermediate product, and a food / beverage product / food product / manufactured product intermediate product comprising a step of further cooking the resulting food / beverage material mixture .
- the present invention also relates to a food / beverage product or an intermediate product of the food / beverage product, wherein ⁇ -Glu-Abu: 20 to 200 ppm by weight, lactic acid, citric acid, apple based on the standard of the food / beverage product or food / beverage product intermediate product At least one organic acid selected from acid and succinic acid or a salt thereof, 0.005 to 0.1% by weight, and sodium chloride 0.01 to 0.5% by weight; and a food and beverage acceptable carrier, And / or the food / beverage products or the manufacturing intermediate goods of food / beverage products containing 1 or 2 or more seasoning raw materials are provided.
- the present invention also includes a step of adding to the food or drink a composition containing ⁇ -Glu-Abu of 400 ppm by weight or more, preferably 1000 ppm by weight or more, more preferably 2000 ppm by weight or more, and even more preferably 2500 ppm by weight or more.
- a method for enhancing the taste of food and drink is provided.
- the taste pattern has an excellent body taste imparting action of a unique taste type having a profile as 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 seasoning which contains the substance which has the outstanding rich taste imparting effect more than a fixed density
- concentration can be provided.
- the taste pattern is similar to the taste pattern of salt, so it is possible to impart a salty-like richness and a taste / punch to the taste of low-salt foods.
- FIG. 1 shows a taste profile (taste pattern) of a taste-rich body taste imparting agent.
- the richness-imparting agent of the present invention is composed of ⁇ -Glu-Abu, but it may be essentially composed of ⁇ -Glu-Abu from the viewpoint of taste, and the inclusion of other components to the extent that does not substantially affect the taste. Permissible.
- the richness imparting agent of the present invention that is, ⁇ -Glu-Abu is an amino acid such as sodium glutamate (MSG), nucleic acids such as inosine monophosphate (IMP), inorganic salts such as sodium chloride, citric acid and the like.
- a preferred seasoning with a richer taste by using it in combination with at least one other seasoning ingredient selected from organic acids, various yeast extracts, etc., compared to the case where other seasoning ingredients are used alone. Can be provided.
- the concentration in the case of using ⁇ -Glu-Abu in combination with the above other seasoning ingredients can be appropriately set by those skilled in the art through examination such as sensory evaluation.
- the seasoning of the present invention that is, the seasoning containing ⁇ -Glu-Abu in an amount of 1000 ppm by weight or more can also be used in combination with other seasoning ingredients to provide another more preferable seasoning.
- 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 enhancing the five basic tastes expressed by sweetness, salty taste, acidity, bitterness, and umami, and accompanying peripheral tastes such as thickness, spread, sustainability, and unity. That means. This can also be expressed as a taste enhancing action. Therefore, ⁇ -Glu-Abu which is the rich taste imparting agent of the present invention can also be expressed as a flavor enhancer.
- ⁇ -Glu-Abu which is a body taste imparting agent of the present invention can also 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).
- the evaluation divided into three categories it is difficult to concentrate on the evaluation of the eater, so the evaluation divided into two categories is usually used.
- the effect of a substance having CaSR activity on kokumi and taste patterns can be confirmed by methods such as a human taste test.
- human taste sensory tests include, but are not limited to, the tests shown in the examples of the present specification.
- 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 60% or more, preferably 80% or more, more preferably 90% or more of the above sequence as long as it encodes a protein having a CaSR function. 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 upon addition of calcium.
- 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 embryonic kidney cells. This can be achieved by introducing a plasmid carrying a foreign gene into which a CaSR gene has been cleaned and introducing a 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. Concentration dependence is measured by changing the calcium concentration.
- the test substance is prepared to about 1 ⁇ M to 1 mM, added to an oocyte or cultured cell, and the CaSR agonist 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.
- amino acids or peptides used in combination with ⁇ -Glu-Abu in the complex body taste imparting agent of the present invention are ⁇ -Glu-Abu, ⁇ -Glu-X-Gly (X represents an amino acid or an amino acid derivative), ⁇ - Glu-Val-Y (Y represents an amino acid or amino acid derivative), ⁇ -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) (O),
- 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.
- the amino acid or peptide used in combination with ⁇ -Glu-Abu in the complex rich taste imparting agent of the present invention may be a peptide derivative having a structure of ⁇ -Glu-X-OCH (Z) CO 2 H.
- X represents an amino acid or an amino acid derivative
- Z represents H (hydrogen atom) or CH 3 (methyl group).
- ⁇ -Glu-Val-Y a compound in which Y is GlyA or LacA may be used. Specific examples include ⁇ -Glu-Val-GlyA, ⁇ -Glu-tLeu-GlyA, ⁇ -Glu-Abu-GlyA, ⁇ -Glu-Val-LacA, ⁇ -Glu-tLeu-LacA, and ⁇ -Glu- Suitable examples include Abu-LacA.
- GlyA represents glycolic acid
- LacA represents butyric acid. Butyric acid may be either S-form or R-form, but is preferably S-form. The structural formulas of these compounds are shown below.
- the body taste imparting agent of the present invention is composed of ⁇ -Glu-Abu and has an excellent body taste imparting action of a unique taste type having a profile as shown in FIG.
- Peptides having different profiles are preferably used in combination with, for example, ⁇ -Glu-Val-Gly.
- 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.
- ⁇ -Glu-Abu used in the present invention is L- ⁇ -glutamyl-L-2-aminobutyric acid.
- the ⁇ -Glu-Abu and the amino acid or peptide used in combination with the ⁇ -Glu-Abu of the present invention may be commercially available when they are commercially available, or (1) a method of chemically synthesizing, 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 easier. Since ⁇ -Glu-Abu used in the present invention has a short amino acid residue of 2 residues, the chemical synthesis method is simple, and the number of amino acid residues contained is 3 residues.
- the oligopeptide can be synthesized by using a peptide synthesizer or semi-synthesized.
- 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-Abu and an amino acid or peptide used in combination therewith by enzymatic reaction for example, the method described in International Publication Pamphlet WO 2004/011653 may be used. Good. 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 salts thereof, and various yeast extracts.
- the low salt 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 sodium chloride, and particularly a food having a reduced salt content.
- Low salt food includes not only solid food but also beverages, and is synonymous with low salt food and drink.
- Such low-salt foods include dairy products such as butter and cheese, animal oils and / or vegetable oils such as margarine, sauces and roux, emulsified foods such as dressings and mayonnaise, various curries and stews, and various snacks. And various soups including meat extracts and creams.
- brewed foods such as miso and soy sauce, soy sauce and sauces using brewed foods, pickled vegetables, processed vegetables such as pickles, processed meat such as ham and sausage, processed fishery products such as salmon, dried fish and boiled fish, cooked meatballs Hamburger, fried food, yakitori.
- the low salt food those having a salt content of 0.01 to 0.5% by mass at the time of eating are preferable.
- the salty taste enhancing effect is further improved.
- the present invention also provides a food or drink containing 20 to 200 ppm by weight of ⁇ -Glu-Abu and 0.01 to 0.5% by weight of sodium chloride.
- the food or drink preferably further contains 0.005 to 0.1% by weight of at least one organic acid selected from lactic acid, citric acid, malic acid and succinic acid or a salt thereof.
- ⁇ -Glu-Abu and the amino acid or peptide used together in the present invention also include a salt form.
- the salt may be any pharmacologically acceptable, for example, an acidic group such as a carboxyl group.
- 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, pyrrolidine, piperidine, piperazine, Examples thereof include salts with organic amines such as dicyclohexylamine and 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 kokumi imparting agent or the complex kokumi imparting agent of the present invention can be used in any form without limitation on the physical properties such as dry powder, paste, and solution.
- the rich taste imparting agent or the complex rich taste imparting agent of the present invention can be used by blending with foods, beverages, seasonings and the like.
- the final amount of ⁇ -Glu-Abu and the amount of amino acid or peptide used in combination when the kokumi imparting agent or complex kokumi imparting agent of the present invention is used in foods, beverages, seasonings and the like are desired.
- the amount of ⁇ -Glu-Abu and / or the amount of amino acid or peptide is 1 mass ppb for each, based on the total mass of food, beverage or seasoning, etc. ⁇ 99.9 mass%, preferably 10 mass ppb to 10 mass%, more preferably about 1 mass ppm to 1 mass%.
- This invention provides the manufacturing method of a seasoning including the process of mixing the richness imparting agent of this invention with the carrier accept
- the ⁇ -Glu-Abu concentration of the seasoning produced here is particularly preferably 400 to 500,000 ppm by weight.
- a method for producing a seasoning comprising the steps of mixing the richness-imparting agent of the present invention with other seasoning ingredients, and the step of setting the ⁇ -Glu-Abu concentration of the seasoning to be produced to 400 to 500,000 ppm by weight Is preferred.
- This invention also provides the manufacturing method of food / beverage products including the process of adding the richness imparting agent of this invention to another food / beverage product raw material.
- the ⁇ -Glu-Abu concentration of the food and drink produced here is particularly preferably 20 to 200 ppm by weight.
- the method for producing a food or drink wherein the step of adding the richness imparting agent of the present invention to another food or drink raw material comprises the step of setting the ⁇ -Glu-Abu concentration of the produced food or drink to 20 to 200 ppm by weight. Is preferred.
- the food, beverage, seasoning, etc. in which the rich taste imparting agent or complex rich taste imparting agent of the present invention is blended are further blended with any solid or liquid carrier acceptable for food and drink, suitable seasoning ingredients, etc. You may let them.
- 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 seasoning of the present invention contains ⁇ -Glu-Abu at 1000 ppm by weight or more, preferably 2000 ppm by weight or more, more preferably 2500 ppm by weight or more, and the taste effect of ⁇ -Glu-Abu is particularly suitable. Is done.
- the proportion of ⁇ -Glu-Abu in the seasoning of the present invention is preferably 3000 ppm by weight or more, more preferably 5000 ppm by weight or more, further preferably 1% by weight or more, and particularly preferably 3% by weight or more. 99.9% by weight or less is also preferable.
- the ingredients other than ⁇ -Glu-Abu of the seasoning of the present invention are not particularly limited, and examples thereof include the above-mentioned carriers and seasonings acceptable for food and drink. More specific seasonings of the present invention include yeast extract containing ⁇ -Glu-Abu at 2500 ppm by weight or more.
- 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, and further subjected to heat treatment, enzyme treatment, concentration, powdering treatment, etc. It may be good.
- a method for producing a yeast extract containing ⁇ -Glu-Abu at 2500 ppm by weight or more is not particularly limited.
- the seasoning of the present invention can be used in any form without limitation on physical properties such as dry powder, paste, and solution.
- the seasoning of this invention can be mix
- This invention provides the manufacturing method of another seasoning including the process of adding the seasoning of this invention to the other seasoning raw material or the carrier accept
- the ⁇ -Glu-Abu concentration of the seasoning produced here is particularly preferably 400 to 500,000 ppm by weight.
- a method for producing a seasoning comprising the steps of adding the seasoning of the present invention to other seasoning ingredients and the step of setting the ⁇ -Glu-Abu concentration of another seasoning to be produced to 400 to 500,000 ppm by weight
- This invention provides the manufacturing method of food-drinks including the process of adding the seasoning of this invention to another food-drinks raw material.
- the ⁇ -Glu-Abu concentration of the food and drink produced here is particularly preferably 20 to 200 ppm by weight.
- a method for producing a food or drink wherein the step of adding the seasoning of the present invention to another food or drink raw material comprises the step of setting the ⁇ -Glu-Abu concentration of the produced food or drink to 20 to 200 ppm by weight. .
- the present invention is also characterized in that ⁇ -Glu-Abu is added to a production intermediate product such as food, beverage or seasoning so that 1 mass ppb to 99.9 mass% is contained.
- a production intermediate product such as food, beverage or seasoning
- foods, beverages, seasonings and the like low salt foods are preferable.
- the present invention also provides a method for producing a food or beverage, characterized by adding the seasoning of the present invention to a food or beverage intermediate product.
- the food or beverage is preferably a low salt food.
- the food / beverage material containing 1000 ppm by weight or more of ⁇ -Glu-Abu, which is added to another food / beverage material has a high concentration, for example.
- the aforementioned yeast extract containing ⁇ -Glu-Abu may be used, and isolated ⁇ -Glu-Abu obtained by chemical or enzymatic synthesis methods, or isolated ⁇ -Glu- Abu dilution product may be used.
- Examples of the diluted product of ⁇ -Glu-Abu include those obtained by diluting the powdery raw material of ⁇ -Glu-Abu with any solid or liquid carrier that is acceptable as a food or beverage as described above.
- another food / beverage material refers to any food / beverage material that is usually used as a food / beverage material other than “a food / beverage material containing 1000 ppm by weight or more of ⁇ -Glu-Abu”.
- a food or beverage material containing 1000 ppm by weight or more of ⁇ -Glu-Abu.
- the following may be listed as a food or drink or an intermediate product of the food and drink.
- the method for producing a food / beverage product or a food / beverage product intermediate product of the present invention comprises a food / beverage material mixture obtained by adding a food / beverage material containing 1000 ppm by weight or more of ⁇ -Glu-Abu to another food / beverage material
- “cooking” includes any cooking step normally used in the art. Examples of the cooking process include, but are not limited to, baking, boiling, frying, steaming, cutting, crushing, rubbing, grating, crushing, crushing, grinding, mixing, sieving and tapping.
- Examples of foods and beverages produced by the method of the present invention or intermediate products for foods and beverages include dairy products such as butter and cheese, foods containing animal fats and / or vegetable fats and oils such as margarine, sauces and roux, dressings and mayonnaise Emulsified foods such as various curries and stews, various snacks, various soups including meat extracts and creams, brewed foods such as miso and soy sauce, related soups, sauces, pickles, pickles, processed vegetables such as ham, Examples include processed meat products such as sausages, processed fishery products such as salmon, dried fish, and boiled fish, cooked meatballs, hamburgers, fried foods, and yakitori.
- dairy products such as butter and cheese
- foods containing animal fats and / or vegetable fats and oils such as margarine, sauces and roux, dressings and mayonnaise Emulsified foods such as various curries and stews, various snacks, various soups including meat extracts and creams, brewed foods such as miso and soy sauce, related soups
- the food and drink in the present invention includes food or beverage as a final product that is generally distributed and eaten, and the production intermediate of the food and drink is a production intermediate in any form before becoming the final product. It is used in the meaning including.
- a food or beverage production intermediate is used as a seasoning material containing ⁇ -Glu-Abu
- the production intermediate is 400 to 500,000 ppm by weight, preferably about 4,000 to 40,000 ppm by weight.
- the final product preferably contains about 20 to 200 ppm by weight of ⁇ -Glu-Abu at the time of eating, that is, as the concentration in the food or drink as the final product.
- it can be produced by adding a food / beverage material containing 1000 ppm by weight or more of ⁇ -Glu-Abu to such a concentration.
- the step of adding a food and beverage material containing ⁇ -Glu-Abu to another food and beverage product material is preferably a food and beverage product production intermediate product.
- the method for producing a food or beverage according to the present invention comprises adding a food or beverage production intermediate product to another food or beverage raw material, The method further includes the step of setting the ⁇ -Glu-Abu concentration of the product to 20 to 200 ppm by weight.
- the step of adding a food or drink raw material containing ⁇ -Glu-Abu to another food or drink raw material preferably has a ⁇ -Glu-Abu concentration of 20 to 200 wt. including the step of ppm.
- the manufacturing method of the food / beverage products of this invention is suitable, for example, when food / beverage products are low salt foods.
- at least one organic acid or salt thereof selected from lactic acid, citric acid, malic acid and succinic acid, preferably lactic acid and malic acid has a concentration in the food and drink of 0.005 to 0.1% by weight. It is preferable to include the process of adding to food-drinks raw material so that it may become, and it is preferable to include the process of adding a small quantity of salt to food-drinks raw material rather than the case where corresponding existing food-drinks are manufactured.
- Examples of the small amount of sodium chloride include an amount such that the salt in the low-salt food is reduced by at least 5%, preferably 10%, with respect to the salt concentration in the existing food and drink.
- the food / beverage products of the present invention may be provided in any form normally used in the food / beverage products industry, and may be provided, for example, as a retort container, canned food, bottling, or the like.
- the present invention will be described in more detail with reference to examples, but these do not limit the present invention.
- Triethylamine (3.2 ml, 22.57 mmol), HOBt (1-hydroxybenzotriazole, 3.053 g, 22.57 mmol) and WSC ⁇ HCl (1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 4 .326 g, 22.57 mmol) was added to the solution and stirred overnight at room temperature.
- the reaction solution was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (220 ml).
- the solution was partitioned with 5% aqueous citric acid solution (100 ml), and the aqueous layer was further extracted with ethyl acetate (60 ml).
- Step 2 Ethanol (160 ml) was added to ZL-Glu-L-Val-OBzl (11.71 g, 20.86 mmol), and then 10% palladium carbon (2.3 g) and then water (10 ml) were added. In addition, the mixture was stirred overnight at room temperature in a hydrogen atmosphere. During the reaction, water (100 ml) was added in small portions. Palladium carbon was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from a small amount of water and ethanol to obtain ⁇ -L-Glu-L-Val (5.0 g). Yield: 97.23% The characteristic values are as follows.
- 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.
- ⁇ -Glu-Abu showed strong CaSR activity similar to ⁇ -Glu-Cys. It is known that a low molecular weight peptide having CaSR action activity is useful as a body taste imparting agent (Patent Document 1), suggesting that ⁇ -Glu-Abu is a particularly excellent body taste imparting agent.
- Example 1 Evaluation of kokumi imparting activity The strength of kokumi imparting activity of ⁇ -Glu-Abu was examined by a quantitative sensory evaluation test.
- the quantitative sensory evaluation test was performed as follows. In distilled water containing sodium glutamate (0.05 g / dl), inosinic acid monophosphate (0.05 g / dl) and sodium chloride (0.5 g / dl), the test compound was added in an amount of 0.001 to 0.5 g / dl. The strength of the kokumi imparting activity when mixed in dl was measured.
- a linear scaling method was used, and a method of entering the corresponding scoring as a position on a straight line indicating positions of ⁇ 5 to 0 to 5 points was used.
- a wide range of richness-imparting activity was exhibited at the above-mentioned added concentrations.
- Table 2 shows the results of typical concentrations.
- Table 2 also shows the results of the same evaluation for ⁇ -Glu-Ala. Both of them are high-priority types, but ⁇ -Glu-Abu was found to be an extremely potent dipeptide.
- ⁇ -Glu-Abu has an excellent kokumi-imparting activity, and that the taste rises in the taste pattern. This leading edge is one of the advantages over ⁇ -Glu-Cys.
- ⁇ -Glu-Abu is excellent in stability, which is also an advantage over ⁇ -Glu-Cys.
- ⁇ -Glu-Abu since ⁇ -Glu-Abu has a short amino acid residue of 2 residues, it can be produced more easily and at a lower cost than a tripeptide having 3 amino acid residues. This is very advantageous from an industrial point of view.
- Example 2 Strength measurement of kokumi imparting activity For ⁇ -Glu-Abu, a test method for obtaining subjective equivalent value (PSE; Point of Subjective Equality) from the limit method (“Statistical Sensory Test Method”, Shin Sato (writing), Using the Japan Science and Technology Federation), the strength of the richness imparting activity was examined. Sensory evaluation was performed as follows. As a solution for sensory evaluation, distilled water containing sodium glutamate (0.05 g / dl), inosinic acid monophosphate (0.05 g / dl), and sodium chloride (0.5 g / dl) was used. ⁇ -Glu-Val was used as a dipeptide having an existing kokumi imparting effect for comparison.
- PSE Point of Subjective Equality
- ⁇ -Glu-Cys has the same strong effect as ⁇ -Glu-Val, but the taste is not particularly strong and the taste is different.
- ⁇ -Glu-Ala is weaker than ⁇ -Glu-Val and has a strong acidity, requiring pH adjustment and difficult to handle.
- ⁇ -Glu-Ser is also difficult to handle because it is weaker than ⁇ -Glu-Val and generates a different flavor.
- the concentration of ⁇ -Glu-Val showing taste with the same strength with respect to a solution containing 0.005 g / dl ⁇ -Glu-Abu in the solution for sensory evaluation the solution for sensory evaluation was set to 0.
- a ⁇ -Glu-Val solution having a concentration changed on a logarithmic scale of 50% was prepared.
- the concentration of ⁇ -Glu-Val was 0.0030 to 0.0337 g / dl in 7 levels.
- the confidence threshold is the average of the lower threshold and the upper threshold.
- the PSE subjective equivalent value of ⁇ -Glu-Val for 50 ppm (0.0050 g / dl) ⁇ -Glu-Abu is the sum of the lower threshold confidence threshold and the upper threshold confidence threshold ⁇ 2.
- the concentration (PSE) of ⁇ -Glu-Val that is equivalent to 0.0050 g / dl of ⁇ -Glu-Abu is estimated to be around 0.0100 g / dl from the number of evaluators in Table 4.
- the PSE calculated from the upper and lower threshold concentrations of ⁇ -Glu-Val that each individual evaluates to be equal is 0.0122 g / dl.
- the strength of ⁇ -Glu-Abu was about 2.4 times that of ⁇ -Glu-Val, and it was a dipeptide with extremely high strength.
- ⁇ -Glu-Abu can be said to be a valuable dipeptide that is cheaper than ever and can exert a rich taste in a wide range of foods.
- Example 3 Evaluation of salty taste enhancement ⁇ -Glu-Abu was examined for salty taste enhancement by a quantitative sensory evaluation test.
- the sensory evaluation test was performed as follows. An amount considered to be the optimum amount of the test compound was added to distilled water containing sodium chloride (0.5 g / dl), and the salty strength 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. As for sensory scores, 0 point is an additive-free control, that is, 0.5 g / dl sodium chloride solution, 5 points is 0.75 g / dl sodium chloride solution, and the scale is -5 points to 0 points to 5 points.
- “Taste” is a taste that is felt after 2 seconds from the start of eating, and “medium aftertaste” is felt after 2 seconds, that is, the time from the content to the aftertaste.
- a linear scaling method was used, and a method of entering the corresponding scoring as a position on a straight line indicating positions of ⁇ 5 to 0 to 5 points was used. Those who have experienced the development of seasoning for food for more than a year and can determine that the difference in titer between ⁇ -Glu-Cys-Gly and ⁇ -Glu-Val-Gly added to the umami salty solution is around 10 times ( Regularly confirmed) was the panel. The evaluation results are shown in Table 6.
- ⁇ -Glu-Val-Gly which is a tripeptide having a high potency for imparting rich taste
- ⁇ -Glu-Abu of the present invention which is a dipeptide
- ⁇ -Glu-Val-Gly has higher taste imparting strength than ⁇ -Glu-Abu.
- ⁇ -Glu-Val-Gly significantly decreases the salty balance.
- ⁇ -Glu-Abu exhibits an extremely well-balanced salty taste enhancement and is particularly suitable as a salty taste enhancement peptide.
- Example 4 Evaluation of Combined Effect with Organic Acid Improvement of the salty taste enhancing effect of ⁇ -Glu-Abu by combined use with an organic acid was examined by a quantitative sensory evaluation test.
- the sensory evaluation test was performed as follows. A commercially available Ajinomoto Co., Inc. salt-reserved “Marutori Gara Soup” was dissolved in hot water so that the salt concentration would be 0.48 g / dl, an appropriate amount of the test compound was dissolved, and the salty strength was measured. There was no difference such as a decrease in pH between the sample dissolved and the additive-free control, and no pH adjustment was performed. In sensory evaluation, no influence of acidity was observed.
- the salty taste of the control 3 points
- n 6.
- a linear scaling method was used, and a method of entering the corresponding scoring as a position on a straight line indicating the position of 1 to 3 to 5 points was used.
- the evaluation results are shown in Table 7.
- Lactic acid and malic acid, which are organic acids have extremely good compatibility with ⁇ -Glu-Abu, and the combined use of lactic acid and malic acid, which are organic acids, further improves the salty taste enhancing effect of ⁇ -Glu-Abu.
- ⁇ -Glu-Abu that enhances the salty taste in a balanced manner can be further improved by the combined use of organic acids. Therefore, ⁇ -Glu-Abu is a very useful compound that can further enhance its effect by a cheap and commonly used material.
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Abstract
Description
一方、カルシウムセンシング受容体(Calcium Sensing Receptor:CaSR)は、カルシウム受容体とも呼ばれるが、当該受容体シグナルは種々の生体内機能を調節し、CaSRアゴニスト活性を有する物質はコク味付与剤として用いることができる(特許文献1、3、非特許文献4)。
一方、γ-グルタミンをN末端に有するいくつかのγ-グルタミルペプチドについては、酵素活性の研究等において基質として合成された例は知られているが(特許文献2、非特許文献1~3)、γ-Glu-Abuがコク味付与剤や調味料として用いられたり食品用途に用いられた例は知られていない。尚、特許文献1及び3の内容は、本明細書の記載に含まれるものとする。
また、本発明は、(a)γ-Glu-Abuに、(b)γ-Glu-X-OCH(Z)CO2H(Xはアミノ酸又はアミノ酸誘導体を表し、ZはH(水素原子)又はCH3(メチル基)を表す)、または、前記式γ-Glu-Val-Y(YはGlyAまたはLacA)から選択される1種又は2種以上のペプチドを併用してなる複合コク味付与剤を提供する。
更に本発明は、γ-Glu-Abuを1000重量ppm以上、好ましくは2000重量ppm以上、より好ましくは2500重量ppm以上含有する調味料(以下、「本発明の調味料」ともいう。)を提供する。
また、本発明は、1000重量ppm以上、好ましくは2000重量ppm以上、より好ましくは2500重量ppm以上のγ-Glu-Abuを含有する飲食品原料を別の飲食品原料に添加する工程、及び、必要に応じて、得られる飲食品原料混合物をさらに調理する工程を含む、飲食品又は飲食品の製造中間品の製造方法及び該製造方法により得られる飲食品又は飲食品の製造中間品を提供する。
また、本発明は、飲食品又は飲食品の製造中間品であって、該飲食品又は飲食品の製造中間品基準で、γ-Glu-Abu:20~200重量ppm、乳酸、クエン酸、リンゴ酸およびコハク酸から選択される少なくとも1の有機酸もしくはその塩0.005~0.1重量%、および、食塩0.01~0.5重量%、ならびに、飲食品的に許容しうる担体、及び/又は、1もしくは2以上の調味原料を含有する、飲食品又は飲食品の製造中間品を提供する。
また、本発明は、400重量ppm以上好ましくは1000重量ppm以上、より好ましくは2000重量ppm以上、更に好ましくは2500重量ppm以上のγ-Glu-Abuを含有する組成物を飲食品に添加する工程を有する、飲食品の呈味増強方法を提供する。
本発明のコク味付与剤を用いると、その呈味パターンが食塩の呈味パターンに類するため、減塩食品の呈味に塩味様濃厚感及び先味・パンチを付与できるので、食品中の食塩の含有量を低下させても、元の食品と同様の塩味感を保持でき、健康志向の高い食品にすることができる。このような食品としては、各種スープや各種ソースなどがあげられる。特に、本発明のコク味付与剤を含有する食品を喫食すると、食べたとたんに、塩味様濃厚感及び先味・パンチを感じることができるという利点がある。
本発明のコク味付与剤、すなわち、γ-Glu-Abuは、グルタミン酸ナトリウム(MSG)などのアミノ酸類、イノシン一リン酸(IMP)などの核酸類、塩化ナトリウムなどの無機塩類、クエン酸などの有機酸類、種々の酵母エキスなどから選択される少なくとも1種の他の調味原料と組み合わせて用いることにより、他の調味原料を単独で用いる場合に比べて、よりコク味の増した、好ましい調味料を提供することができる。γ-Glu-Abuを上記の他の調味原料と組み合わせて用いる場合の濃度は、当業者であれば官能評価等の検討を経て適宜設定することができる。
本発明の調味料、すなわちγ-Glu-Abuを1000重量ppm以上含有する調味料も同様に、他の調味原料と組み合わせて用いることにより、より好ましい別の調味料を提供することができる
コク味及び呈味パターンに対するCaSR活性を有する物質の効果は、ヒトによる味覚試験などの方法によって確認することができる。このようなヒトによる味覚官能試験としては例えば本願明細書の実施例で示される試験が挙げられるが、これらに限定されない。
1)CaSR活性を測定するためのCaSR活性測定系に被検物質を添加して、CaSR活性を測定する。
2)被検物質を添加したときのCaSR活性と、被検物質を添加しなかったときのCaSR活性を比較する。
3)被検物質を添加したときにCaSRアゴニスト活性を示す被検物質を選択する。
上記CaSRは、その由来は特に制限されず、上記ヒトのCaSRのみならず、マウス、ラット、イヌなどを含むあらゆる動物由来のCaSRが挙げられる。
以下に生きた細胞を用いた一例を示すが、これに限定されるものではない。
CaSRは、アフリカツメガエル卵母細胞やハムスター卵巣細胞やヒト胎児腎臓細胞等の培養細胞に発現させる。これは外来遺伝子を保持するプラスミドにCaSR遺伝子をクリーニングしたものを、プラスミドの状態もしくはそれを鋳型にしたcRNAを導入することで可能となる。反応の検出には電気生理学的手法や細胞内カルシウム上昇の蛍光指示試薬を用いることができる。
CaSRの発現は、初めにカルシウムもしくは特異的活性化剤による応答で確認する。5mM程度の濃度のカルシウムに対して、細胞内電流が観察された卵母細胞もしくは蛍光指示試薬の蛍光が観察された培養細胞を使用する。カルシウムの濃度を変えて濃度依存性を測定する。次に、被検物質を1μM~1mM程度に調製し、卵母細胞もしくは培養細胞に添加し、上記被検物質存在下でのCaSR活性を測定することで、上記被検物質のCaSRアゴニスト活性を測定する。
又、より具体的には、CaSRアゴニスト活性試験としては例えば本願明細書の試験例で示される試験が挙げられるが、これらに限定されない。
また本発明の複合コク味付与剤においてγ-Glu-Abuと併用されるアミノ酸又はペプチドは、γ-Glu-X-OCH(Z)CO2Hの構造を有するペプチド誘導体であってもよい。ここに、式中Xはアミノ酸又はアミノ酸誘導体を表し、ZはH(水素原子)又はCH3(メチル基)を表す。また、前記式γ-Glu-Val-Yにおいて、YがGlyAまたはLacAである化合物であってもよい。具体例としては、γ-Glu-Val-GlyA、γ-Glu-tLeu-GlyA、γ-Glu-Abu-GlyA、γ-Glu-Val-LacA、γ-Glu-tLeu-LacA、及びγ-Glu-Abu-LacA等が好適に挙げられる。なお、GlyAとは、グリコール酸を表し、LacAとは、酪酸を表す。酪酸はS体とR体のいずれでも良いが、好ましくはS体である。これらの化合物の構造式を以下に記す。
(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:アルパラギン
(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)N-Val(又は、Nva):ノルバリン (2-アミノ吉草酸)
(25)N-Leu(又は、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
(30)Cle:シクロロイシン
(31)Aib:α-アミノイソブチル酸(α-aminoisobutyric acid、2-メチルアラニン)
(32)Pen:L-ペニシラミン(penicillamine)
(33)allo-Thr:アロスレオニン
(34)allo-Ile:アロイソロイシン
さらに、上述したような酵素的な方法や化学的合成方法以外にも本発明において用いられるペプチドが、野菜や果物等の植物、酵母等の微生物、その他の天然物中に存在する場合がある。天然に存在する場合には、これらから抽出して用いることも可能である。
本発明のコク味付与剤あるいは複合コク味付与剤は、そのままで、又は飲食品的に許容しうる担体や他の調味原料と混合して、調味料とすることができる。他の調味原料としては、例えば、香料、糖類、甘味料、食物繊維類、ビタミン類、グルタミン酸ナトリウム(MSG)などのアミノ酸類、イノシン一リン酸(IMP)などの核酸類、塩化ナトリウムなどの無機塩類、クエン酸などの有機酸やその塩類が挙げられ、更には種々の酵母エキスも挙げられる。
尚、本発明のコク味付与剤あるいは複合コク味付与剤を含有する食品組成物として好ましい低塩食品は、元来食塩を含む食品であり、特に、その食塩含量が低減された食品である。低塩食品としては、固形の食品のみならず飲料をも含み、低塩飲食品と同義である。
このような低塩食品としては、バター、チーズ等の乳製品、マーガリン、 ソース、ルーなどの動物油脂及び/又は植物油脂含有食品、ドレッシング、マヨネーズなどの乳化食品等、各種カレーやシチュー、各種スナック、肉エキス・クリームを含む各種スープなどがあげられる。又、味噌、醤油など醸造食品や醸造食品を用いたつゆ・たれ類、漬物、ピクルスなど野菜加工食品、ハム・ソーセージなど畜肉加工食品、蒲鉾、干物、佃煮など水産加工食品、調理済みのミートボール、ハンバーグ、揚げもの、焼き鳥どもあげられる。これらのうち、低塩食品としては、喫食時の食塩含有量が0.01~0.5質量%であるものが好ましい。さらに、乳酸、クエン酸、リンゴ酸およびコハク酸から選択される少なくとも1の有機酸もしくはその塩を0.005~0.1重量%で併用することがより好ましく、併用により、γ-Glu-Abuの塩味増強効果がさらに向上する。
本発明は、又、20~200重量ppmのγ-Glu-Abuと0.01~0.5重量%の食塩とを含有する飲食品を提供する。ここで該飲食品は更に、乳酸、クエン酸、リンゴ酸およびコハク酸から選択される少なくとも1の有機酸もしくはその塩を0.005~0.1重量%含有するのが好ましい。
本発明のコク味付与剤を上記低塩食品に含有させることにより、これらの食品を喫食した時、最初に、塩味様濃厚感及び先味・パンチを感じることができる。
本発明のコク味付与剤あるいは複合コク味付与剤は、食品、飲料、調味料等に配合して用いることができる。
本発明のコク味付与剤、あるいは複合コク味付与剤を食品、飲料、調味料等に配合して用いる場合の最終的なγ-Glu-Abuの量及び併用されるアミノ酸又はペプチドの量は所望の効果が得られる量であれば特に制限されないが、γ-Glu-Abuの量及び/又はアミノ酸若しくはペプチドの量として、食品、飲料あるいは調味料等の全質量を基準として、それぞれについて1質量ppb~99.9質量%、好ましくは10質量ppb~10質量%、より好ましくは1質量ppm~1質量%程度である。
本発明は、本発明のコク味付与剤を他の調味原料又は飲食品的に許容しうる担体と混合する工程を含む、調味料の製造方法を提供する。ここで製造される調味料のγ-Glu-Abu濃度は400から500000重量ppmが特に好ましい。特に、本発明のコク味付与剤を他の調味原料と混合する工程、及び、製造される調味料のγ-Glu-Abu濃度を400から500000重量ppmとする工程を含む、調味料の製造方法が好ましい。
本発明は、又、本発明のコク味付与剤を別の飲食品原料に添加する工程を含む、飲食品の製造方法を提供する。ここで製造される飲食品のγ-Glu-Abu濃度は20~200重量ppmが特に好ましい。よって、本発明のコク味付与剤を別の飲食品原料に添加する工程が、製造される飲食品のγ-Glu-Abu濃度を20~200重量ppmとする工程を含む、飲食品の製造方法が好ましい。
上記担体としては、例えば、グルコース、乳糖、ショ糖、澱粉、マンニトール、デキストリン、脂肪酸グリセリド、ポリエチレングリコール、ヒドロキシエチルデンプン、エチレングリコール、ポリオキシエチレンソルビタン脂肪酸エステル、ゼラチン、アルブミン、アミノ酸、水、生理食塩水等が挙げられる。
上記の調味原料は、当業界で用いられるいずれの調味原料であってもよく特に制限されないが、より具体的には既に上述のものが挙げられる。
上記の担体、他の調味原料等はいずれもその含有量は特に制限されない。
本発明の調味料は、γ-Glu-Abuを1000重量ppm以上、好ましくは2000重量ppm以上、より好ましくは2500重量ppm以上含有し、γ-Glu-Abuの有する呈味効果が特に好適に発揮される。本発明の調味料においてγ-Glu-Abuの占める割合は、好ましくは3000重量ppm以上、更に好ましくは5000重量ppm以上、更に好ましくは1重量%以上、特に好ましくは3重量%以上であり、又、99.9重量%以下であるのも好ましい。本発明の調味料のγ-Glu-Abu以外の成分としては、特に限定されないが、例えば上述した、飲食品的に許容しうる担体や調味原料が挙げられる。
より具体的な本発明の調味料としては、γ-Glu-Abuを2500重量ppm以上含有する酵母エキスが挙げられる。酵母エキスは、由来となる菌体・その培養条件・抽出処理方法のいずれも特に限定されず任意の酵母エキスを用いることができ、更に加熱処理、酵素処理、濃縮、粉末化処理等が施されたものでも良い。γ-Glu-Abuを2500重量ppm以上含有する酵母エキスの製法は特に限定されないが、例えば、酵母エキスにγ-Glu-Abuを上記の濃度になるように添加して得ることができる。
本発明の調味料は、乾燥粉末、ペースト、溶液などの物性に制限なしにあらゆる形態で用いることができる。
本発明の調味料は、食品、飲料等に配合して用いることができる。
本発明は、本発明の調味料を他の調味原料又は飲食品的に許容しうる担体に添加する工程を含む、別の調味料の製造方法を提供する。ここで製造される調味料のγ-Glu-Abu濃度は400から500000重量ppmが特に好ましい。特に、本発明の調味料を他の調味原料に添加する工程、及び、製造される別の調味料のγ-Glu-Abu濃度を400から500000重量ppmとする工程を含む、調味料の製造方法が好ましい。
本発明は、本発明の調味料を別の飲食品原料に添加する工程を含む、飲食品の製造方法を提供する。ここで製造される飲食品のγ-Glu-Abu濃度は20~200重量ppmが特に好ましい。特に、本発明の調味料を別の飲食品原料に添加する工程が、製造される飲食品のγ-Glu-Abu濃度を20~200重量ppmとする工程を含む、飲食品の製造方法が好ましい。
本発明は又、食品あるいは飲料の製造中間品に、本発明の調味料を添加することを特徴とする、食品あるいは飲料の製造方法を提供する。ここで食品あるいは飲料としては、低塩食品が好ましい。
本発明の飲食品又は飲食品の製造中間品の製造方法において、別の飲食品原料に添加される、1000重量ppm以上のγ-Glu-Abuを含有する飲食品原料には、例えば、高濃度のγ-Glu-Abuを含有する前述した酵母エキスを用いてもよく、また、化学的若しくは酵素的合成方法によって得られる単離されたγ-Glu-Abu、または単離されたγ-Glu-Abuの希釈倍散品を用いても良い。γ-Glu-Abuの希釈倍散品としては、γ-Glu-Abuの原末を、上述の飲食品的に許容しうるあらゆる固体又は液体の担体により、希釈したものが挙げられる。
本発明において、「別の飲食品原料」とは、「1000重量ppm以上のγ-Glu-Abuを含有する飲食品原料」以外の飲食品の原料として通常用いられるいかなる飲食品原料であってもよく、例えば、前述した飲食品的に許容しうる担体や他の調味原料等に加え、以下に飲食品又は飲食品の製造中間品として列挙されるものであってもよい。
本発明の飲食品又は飲食品の製造中間品の製造方法は、1000重量ppm以上のγ-Glu-Abuを含有する飲食品原料を別の飲食品原料に添加する工程により得られる飲食品原料混合物を、さらに調理する工程を有していてもよいが、本発明において、「調理する」とは、当業界で通常用いられるいずれの調理工程をも包含する。調理工程の例としては、焼く、煮る、揚げる、蒸す、切る、砕く、擦る、すりおろす、潰す、すり潰す、挽く、混ぜる、ふるう及び叩く等が挙げられるが、これらに限定されない。
本発明における飲食品は、一般に流通し、喫食される形態である最終製品としての食品あるいは飲料等を含み、また、飲食品の製造中間品は、最終製品となる前のいかなる形態の製造中間品をも含む意味において用いられる。食品あるいは飲料の製造中間品が、γ-Glu-Abuを含有する調味原料として用られる場合は、該製造中間品は、400~500000重量ppm、好ましくは4000~40000重量ppm程度のγ-Glu-Abuを含有するのが好ましく、そのような製造中間品は、例えば1000重量ppm以上のγ-Glu-Abuを含有する飲食品原料をそのような濃度となるように添加することによって製造することができる。また、最終製品は、喫食時、すなわち最終製品としての飲食品中の濃度として、20~200重量ppm程度のγ-Glu-Abuを含有するを含有するのが好ましく、そのような最終品は、例えば1000重量ppm以上のγ-Glu-Abuを含有する飲食品原料をそのような濃度となるように添加することによって製造することができる。
本発明の飲食品又は飲食品の製造中間品の製造方法において、γ-Glu-Abuを含有する飲食品原料を別の飲食品原料に添加する工程は、好ましくは、飲食品の製造中間品のγ-Glu-Abu濃度を400~500000重量ppmとする工程を含み、より好ましくは、本発明の飲食品の製造方法は、飲食品の製造中間品を別の飲食品原料に添加して、飲食品のγ-Glu-Abu濃度を20~200重量ppmとする工程をさらに含む。
本発明の飲食品の製造方法において、γ-Glu-Abuを含有する飲食品原料を別の飲食品原料に添加する工程は、好ましくは、飲食品のγ-Glu-Abu濃度を20~200重量ppmとする工程を含む。
本発明の飲食品は、飲食品業界で通常用いられるいかなる形態で提供されてもよく、例えば、レトルト容器、缶詰、瓶詰め等、あるいは乾燥品等として提供されてもよい。
以下に、実施例を挙げて本発明をさらに詳しく説明するが、これらは本発明を限定するものではない。
γ-L-Glu-L-Abu(Abu:α-アミノ酪酸、Bachem Feinchemikalien AG)、γ-L-Glu-L-Ala(Bachem Feinchemikalien AG)、γ-L-Glu-L-Cys(シグマアルドリッチジャパン株式会社)、γ-L-Glu-L-Thr(国産化学株式会社)の4種類は購入品を用いた。
(工程1)Z-L-Glu-OBzl(N-α-カルボベンゾキシ-L-グルタミン酸α-ベンジルエステル,7.619g, 20.51mmol)とVal-OBzl・HCl(L-バリンベンジルエステルヒドロクロリド,5g,20.51mmol)を塩化メチレン(100ml)に溶解し、溶液を0℃に保った。トリエチルアミン(3.2ml,22.57mmol)、HOBt(1-ヒドロキシベンゾトリアゾール,3.053g,22.57mmol)及びWSC・HCl(1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミドヒドロクロリド,4.326g,22.57mmol)を溶液に加え、室温で一夜撹拌した。反応液を減圧濃縮し、残渣を酢酸エチル(220ml)に溶解した。溶液を5%クエン酸水溶液(100ml)で分液し、水層を更に酢酸エチル(60ml)で抽出した。有機層を合わせて飽和食塩水(80ml)、5%炭酸水素ナトリウム水溶液(80ml)、飽和食塩水(80ml)で洗浄した。有機層を無水硫酸マグネシウムで乾燥し、硫酸マグネシウムを濾過して除き、濾液を減圧濃縮した。残渣を酢酸エチル-n-ヘキサン(1:1)でスラリー洗浄し、濾過することによりZ-L-Glu-L-Val-OBzl(10.0273g)を得た。また、酢酸エチル-n-ヘキサン画分にn-ヘキサンを加えることにより析出した結晶を、酢酸エチル-n-ヘキサンから再結晶し、Z-L-Glu-L-Val-OBzl(1.0399g)を得た。
収率94.25%
収率:97.23%
その特性値を次に示す。
ESI-MS:(M+H)+=247.2
1H-NMR(400MHz,D2O)δ(ppm):0.86(3H,d,J=6.8 Hz),0.88(3H,d,J=6.8 Hz),2.04-2.13(3H,m),2.42-2.46(2H,m),3.74(1H,t,J=6.3 Hz),4.13(1H,d,J=5.8Hz).
γ-L-Glu-L-Valの合成方法に従い、Z-L-Glu-OBzlとL-Ser-OBzlを原料に使用して、γ-L-Glu-L-Serを合成した。その特性値を次に示す。
ESI-MS:(M+H)+=235.1
1H-NMR(400MHz,D2O)δ(ppm):1.98-2.09(2H,m),2.40(2H,t,J=8.0Hz),3.71-3.81(3H,m),4.33(1H,t,J=8.0Hz).
γ-L-Glu-L-Valの合成方法に従い、Z-L-Glu-OBzlとL-t-Leu-OBzlを原料に使用して、γ-L-Glu-Aibを合成した。その特性値を次に示す。
ESI-MS:(M+H)+=261.3
γ-L-Glu-L-Valの合成と類似の方法に従い、Z-L-Glu-OBzlとAib-Ot-Buを原料に使用して、γ-L-Glu-Aibを合成した。その特性値を次に示す。
ESI-MS:(M+H)+=233.3
1H-NMR(400MHz,D2O)δ(ppm):1.36(6H,s),2.00-2.06(2H,m),2.30-2.34(2H,m),3.69(1H,t,J=6.2Hz).
CaSR発現プラスミドの調製を以下のように行った。
NCBIに登録されたDNA配列(CaSR(カルシウム受容体):NM_000388、配列番号1、2)を元に、PCRに使う合成オリゴDNA(フォワードプライマー(配列番号3:ACTAATACGACTCACTATAGGGACCATGGCATTTTATAGCTGCTGCTGG)、及びリバースプライマー(配列番号4:TTATGAATTCACTACGTTTTCTGTAACAG)を合成した。
ヒト腎臓由来のcDNA(Clontech社製)を材料として、前記プライマー、及びPfu Ultra DNA Polymerase(Stratagene社製)を用い、以下の条件でPCRを実施した。94℃で3分の後、94℃で30秒、55℃で30秒、72℃で2分を35回繰り返した後、72℃で7分反応させた。アガロース電気泳動を行い、DNA染色試薬で染色した後、紫外線照射によってPCRによって増幅がなされたか否かを検出した。又、同時に電気泳動したサイズ既知のDNAマーカーと比較することで、PCR産物の鎖長を確認した。
プラスミドベクターpBR322を制限酵素EcoRV(Takara社製)によって切断し、その切断部位にPCRによって増幅された遺伝子断片をLigation kit(Promega社製)を用いて連結した。この反応溶液でエシェリヒア・コリDH5α株を形質転換し、PCR増幅産物がクローニングされたプラスミドを保持する形質転換体を選抜し、更にPCR増幅産物をDNA塩基配列解析によって確認した。
この組換えプラスミドを用いてヒトCaSR発現プラスミドhCaSR/pcDNA3.1を作製した。
293E細胞(EBNA1発現HEK293細胞、ATCC No.CRL-10852)を、200μg/mlのG418(ジェネティシン)存在下、10%のウシ胎児血清を含むDMEM/Ham's-F12(3.15/ml Glucose含有Dulbecco's modified Eagle medium、ナカライテスク)にて培養した。3×106ceells/10mlでF25フラスコに撒き、CO2インキュベータ(5%CO2、37℃)に24時間静置した後、トランスフェクション試薬Fugene6(Roche)にてヒトCaSR発現プラスミドhCaSR/pcDNA3.1をトランスフェクションした。CO2インキュベータに6~7時間置いた後、細胞を10%ウシ胎児血清含有DMEM/Ham's-F12にて回収し、70,000cells/wellでpoly-D-lysine coat 96well plate(BD-Biocoat)に播種した。
CO2インキュベータにて24時間静置した後、この細胞を播種した96 well plateから培地を除去し、Assay Buffer (146mM NaCl、5mM KCl、1mM MgSO4、1mg/ml Glucose、20mM HEPES(pH 7.2)、0.75~1.25 mM CaCl2)に溶解したCa2+蛍光指示薬Calcium 4 Assay Kit(Molecular Devices)を200μl/well添加し、37℃で1時間、次いで室温で10分静置し指示薬を取り込ませた。
この96well plateに、0.1%BSA含有Assay Bufferに溶解した被験化合物を50μl/well添加し、FLEX Station(Molecular Devices)で3分間蛍光強度変化を測定した。
化合物添加前後の蛍光強度の最大値と最小値の差(RFU(Max-Min))をFLEX Stationの自動計算にて求めた。化合物最大濃度添加時のRFU(Max-Min)を100%、被験化合物を含まない0.1%BSA含有Assay Bufferを使用時のRFU(Max-Min)を0%と定義した活性率を計算し、表計算ソフトXfitもしくはグラフパッドプリズムにてカーブフィッティングし、活性率50%時の化合物濃度であるEC50値を求めた。結果を表1に示した。
γ-Glu-Abuについて、定量的な官能評価試験によりコク味付与活性の強度を調べた。
定量的官能評価試験は以下のように実施した。グルタミン酸ナトリウム(0.05g/dl)、イノシン酸一リン酸(0.05g/dl)、塩化ナトリウム(0.5g/dl)を含有する蒸留水に、被験化合物を0.001~0.5g/dlにて混合した場合の、コク味付与活性の強度を測定した。試料溶解後に無添加コントロールに対し酸性を呈したサンプルについては、NaOHで無添加コントロールに対しpH±0.2の幅に合わせて使用した。官能評点について、コントロール:0点、強い:3点、非常に強い:5点として、n=4で実施した。また、尺度をより明確にするため、0.001g/dlのγ-Glu-Val-Glyの先味、中後味を各々3.0点とした。尚、「中後味」とは、中味から後味を合わせた時間で感じる呈味である。採点ついては、直線尺度法を用い、-5~0~5点の位置を示した直線に対し、該当する採点を位置として記入する方法を用いた。また、食品の調味開発を累積で1年以上経験し、うま味塩味溶液に添加したγ-Glu-Cys-Glyとγ-Glu-Val-Glyの力価の差が10倍前後と判定できる者(定期的に確認)をパネラーとした。上記添加濃度で幅広くコク味付与活性を示したが、代表的な濃度の結果を表2に示した。
又、γ-Glu-Alaについて同様に評価した結果も表2に示した。両者は先味の評点が高い先味タイプだが、γ-Glu-Abuは極めて力価が強いジペプチドであることが分かった。
γ-Glu-Abuについて、主観的等価値(PSE;Point of Subjective Equality)を極限法より求める試験法(「統計的官能検査法」佐藤信(筆)、日本科学技術連盟)を用いて、コク味付与活性の強度を調べた。
官能評価は以下のように実施した。官能評価用の溶液として、グルタミン酸ナトリウム(0.05g/dl)、イノシン酸一リン酸(0.05g/dl)、塩化ナトリウム(0.5g/dl)を含有する蒸留水を用いた。比較する既存のコク味付与効果を有するジペプチドとしてγ-Glu-Valを用いた。γ-Glu-Cysもγ-Glu-Valと同程度の強い効果を有するが、先味が特別強いわけでなく、味質が異なる。γ-Glu-Alaは、γ-Glu-Valより強度が弱いとともに酸味が強く、pH調整が必要で扱い難い。γ-Glu-Serも、γ-Glu-Valよりも強度が弱く、また異風味を発生するため扱い難い。
官能評価用の溶液に0.005g/dlγ-Glu-Abuを含有させた溶液に対し、同等の強度の呈味を示すγ-Glu-Valの濃度を求めるため、官能評価用の溶液に0.01g/dlγ-Glu-Valを含有させた溶液を基準に、50%の対数尺度にて濃度を変化させたγ-Glu-Val溶液を調製した。γ-Glu-Valの濃度は0.0030~0.0337g/dlで7段階であった。試料溶解後に無添加コントロールに対し酸性を呈したサンプルについては、NaOHで無添加コントロールに対しpH±0.2の幅に合わせて使用した。18名のパネラーに、γ-Glu-Val濃度が低い溶液から順に提示し、γ-Glu-Abuの0.005g/dl溶液と比較し強度が強いと感じられるまで評価を実施した。時間を空け、次に、18名のパネラーに、γ-Glu-Val濃度の高い溶液から順に提示し、γ-Glu-Abuの0.005g/dl溶液と比較し強度が弱いと感じられるまで評価を実施した。
本官能評価について、食品開発の経験者をパネラーとした。評価結果を表4に示した。
2)信頼閾(平均)は下閾および上閾の平均である。
50ppm(0.0050g/dl)γ-Glu-Abuに対するγ-Glu-Valの
PSE(主観的等価値)は、下閾の信頼閾と上閾の信頼閾の和÷2となる
。
γ-Glu-Abuについて、定量的な官能評価試験により塩味増強を調べた。
官能評価試験は以下のように実施した。塩化ナトリウム(0.5g/dl)を含有する蒸留水に、被験化合物を最適と考えられる量を添加し、塩味強度を測定した。試料溶解後に無添加コントロールに対し酸性を呈したサンプルについては、NaOHで無添加コントロールに対しpH±0.2の幅に合わせて使用した。
官能評点について、0点を無添加コントロール、すなわち0.5g/dl塩化ナトリウム溶液、5点を0.75g/dl塩化ナトリウム溶液とする、-5点~0点~5点の尺度にて、n=5で実施した。「先味」とは喫食開始から2秒後まで、「中後味」とは、2秒後以降すなわち中味から後味を合わせた時間で感じる呈味である。採点ついては、直線尺度法を用い、-5~0~5点の位置を示した直線に対し、該当する採点を位置として記入する方法を用いた。また、食品の調味開発を累積で1年以上経験し、うま味塩味溶液に添加したγ-Glu-Cys-Glyとγ-Glu-Val-Glyの力価の差が10倍前後と判定できる者(定期的に確認)をパネラーとした。評価の結果を表6に示した。
定量的な官能評価試験により、γ-Glu-Abuの塩味増強効果の有機酸の併用による向上について検討した。
官能評価試験は以下のように実施した。市販の味の素株式会社製、塩分控えめ「丸鶏がらスープ」を食塩濃度が0.48g/dlになるよう熱湯に溶解し、被験化合物を適正量溶解し、塩味強度を測定した。試料溶解後と無添加コントロールとはpHに関し、低下など差が無く、pH調整を実施しなかった。官能評価でも酸味などによる影響を認めなかった。官能評点について、尺度を明確にするため、コントロールの塩味:3点、コントロールを1.25倍に増塩したスープの塩味:4点、コントロールを1.5倍に増塩したスープの塩味:5点として、n=6で実施した。採点ついては、直線尺度法を用い、1~3~5点の位置を示した直線に対し、該当する採点を位置として記入する方法を用いた。また、食品の調味開発を累積で1年以上経験し、うま味塩味溶液に添加したγ-Glu-Cys-Glyとγ-Glu-Val-Glyの力価の差が10倍前後と判定できる者(定期的に確認)をパネラーとした。評価結果を表7に示した。
すなわち、バランス良く塩味を増強するγ-Glu-Abuの効果に関して、有機酸の併用によりさらなる向上が可能である。従って、γ-Glu-Abuは、安価通常良く用いる素材により、その効果をさらに強化することのできる極めて有用な化合物である。
Claims (14)
- γ-Glu-Abuからなるコク味付与剤。
- (a)γ-Glu-Abuに、
(b)γ-Glu-X-Gly(Xはアミノ酸又はアミノ酸誘導体を表す)、γ-Glu-Val-Y(Yはアミノ酸又はアミノ酸誘導体を表す)、γ-Glu-Ala、γ-Glu-Gly、γ-Glu-Cys、γ-Glu-Met、γ-Glu-Thr、γ-Glu-Val、γ-Glu-Orn、Asp-Gly、Cys-Gly、Cys-Met、Glu-Cys、Gly-Cys、Leu-Asp、D-Cys、γ-Glu-Met(O)、γ-Glu-γ-Glu-Val、γ-Glu-Val-NH2、γ-Glu-Val-ol、γ-Glu-Ser、γ-Glu-Tau、γ-Glu-Cys(S-Me)(O)、γ-Glu-Leu、γ-Glu-Ile、γ-Glu-t-Leuおよびγ-Glu-Cys(S-Me)からなる群より選択される1種又は2種以上のアミノ酸又はペプチド、を併用してなる複合コク味付与剤。 - γ-Glu-Abuを1000重量ppm以上含有する調味料。
- γ-Glu-Abuを2500重量ppm以上含有する請求項3記載の調味料。
- 1000重量ppm以上のγ-Glu-Abuを含有する飲食品原料を別の飲食品原料に添加する工程、及び、必要に応じて、得られる飲食品原料混合物をさらに調理する工程を含む、飲食品又は飲食品の製造中間品の製造方法。
- γ-Glu-Abuを含有する飲食品原料を別の飲食品原料に添加する工程が、飲食品の製造中間品のγ-Glu-Abu濃度を400~500000重量ppmとする工程を含む、請求項5記載の飲食品又は飲食品の製造中間品の製造方法。
- 飲食品の製造中間品を別の飲食品原料に添加して、飲食品のγ-Glu-Abu濃度を20~200重量ppmとする工程をさらに含む、請求項6記載の飲食品の製造方法。
- γ-Glu-Abuを含有する飲食品原料を別の飲食品原料に添加する工程が、飲食品のγ-Glu-Abu濃度を20~200重量ppmとする工程を含む、請求項5記載の飲食品の製造方法。
- 飲食品が低塩食品である、請求項5~8いずれか1項に記載の飲食品の製造方法。
- 更に、乳酸、クエン酸、リンゴ酸およびコハク酸から選択される少なくとも1の有機酸もしくはその塩を、飲食品中の濃度が0.005~0.1重量%となるように飲食品原料に添加する工程を含む、請求項9の製造方法。
- 請求項5~10のいずれかに記載の方法により得られる飲食品又は飲食品の製造中間品。
- 飲食品又は飲食品の製造中間品であって、該飲食品又は飲食品の製造中間品基準で、γ-Glu-Abu:20~200重量ppm、乳酸、クエン酸、リンゴ酸およびコハク酸から選択される少なくとも1の有機酸もしくはその塩0.005~0.1重量%、および、食塩0.01~0.5重量%、ならびに、飲食品的に許容しうる担体、及び/又は、1もしくは2以上の調味原料を含有する、前記飲食品又は飲食品の製造中間品。
- 400重量ppm以上のγ-Glu-Abuを含有する組成物を飲食品に添加する工程を有する、飲食品の呈味増強方法。
- 呈味増強が、コク味付与である、請求項13記載の方法。
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Also Published As
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CA2756888A1 (en) | 2010-10-07 |
KR101402639B1 (ko) | 2014-06-03 |
US20120034364A1 (en) | 2012-02-09 |
EP2415359A4 (en) | 2016-01-13 |
BRPI1013680A2 (pt) | 2015-08-25 |
US9844226B2 (en) | 2017-12-19 |
KR20110132474A (ko) | 2011-12-07 |
AU2010232296A1 (en) | 2011-10-27 |
RU2011144143A (ru) | 2013-05-10 |
RU2536934C2 (ru) | 2014-12-27 |
CN102481006A (zh) | 2012-05-30 |
JP5688687B2 (ja) | 2015-03-25 |
AU2010232296A2 (en) | 2012-02-02 |
MX2011010407A (es) | 2012-01-20 |
CA2756888C (en) | 2015-01-13 |
SG175000A1 (en) | 2011-11-28 |
TW201100021A (en) | 2011-01-01 |
EP2415359B1 (en) | 2017-04-19 |
CN102481006B (zh) | 2015-03-04 |
BRPI1013680B1 (pt) | 2019-05-28 |
MY158503A (en) | 2016-10-14 |
EP2415359A1 (en) | 2012-02-08 |
AU2010232296B2 (en) | 2014-06-19 |
NZ595939A (en) | 2013-06-28 |
TWI399180B (zh) | 2013-06-21 |
JPWO2010114022A1 (ja) | 2012-10-11 |
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