WO2007119741A1

WO2007119741A1 - Novel sweetener

Info

Publication number: WO2007119741A1
Application number: PCT/JP2007/057963
Authority: WO
Inventors: Toshikazu Kamiya; Shun Kayahashi
Original assignee: Kyowa Hakko Kogyo Co., Ltd.
Priority date: 2006-04-11
Filing date: 2007-04-11
Publication date: 2007-10-25

Abstract

It is intended to provide a low calorie sweetener excellent in safety and sweetness. According to the invention, the sweetener containing as an active ingredient a dipeptide selected from the group consisting of alanyl tryptophan, valyl tryptophan, lysyl tryptophan, arginyl tryptophan, arginyl tyrosine and lysyl alanine, or a salt thereof can be provided.

Description

New sweetener

Technical field

[0001] The present invention relates to a sweetener containing a dipeptide or a salt thereof as an active ingredient.

Background art

[0002] Obesity due to excessive intake of sugar and various diseases associated therewith become a problem, and sugar alcohol

Low calorie sweeteners such as oligosaccharides and high intensity sweeteners have been developed. With the recent diet boom, demand for low-calorie sweeteners is increasing.

As a low calorie sweetener that has been reported in many cases, for example, aspartame ( _α- L asvaltyl L-ferulalanin 1 methyl ester) having an aspartyl dipeptide ester structure can be mentioned (see Non-patent Document 1). Since the discovery of aspartame having a sweet taste, many groups have been investigating the potential of astrontyl dipeptide esters as sweeteners (see Non-Patent Document 2).

[0003] Further, ara-histidine, glycylproline, and glycylnoline are known as dipeptides exhibiting sweetness (see Non-Patent Document 3).

However, it is not known that alanyltryptophan, noryltryptophan, lysyltryptophan, arginyltryptophan, arginyltyrosine and lysylalanine exhibit a sweet taste.

[0004] Al-Lartribtophan is a Wakame protease digest (see Non-Patent Document 4), and Baryl Tritophan is a Wakame Hot Water Extract (see Non-Patent Document 5). Shark meat thermolysin digest (Patent Document 1) It is known that lysyl tributophane is contained in wakame hot water extract (see Non-Patent Document 5), and arginyltyrosine is contained in a fish protease degradation product (see Patent Document 2)! /!

Patent Document 1: Japanese Patent Laid-Open No. 2001-261698

Patent Document 2: Japanese Patent Laid-Open No. 06-166697

Non-Patent Literature 1: “Journal of the American American Chemical Society” The American Chemical Society), 1969, No. 91, No. 10, p. 2684- 2691

Non-Patent Document 2: “A taste and odor chemistry” edited by the Japanese Society of Agricultural Sciences, 1st edition, Academic Publishing Center, 197 November 2006, p. 93-100

Non-Patent Document 3: “Physiology and Behavior”, 1976, pp. 523-535

Non-Patent Document 4: “Journal of Agricultual and Food Chemistry” 2002, 50th, No. 21, p. 6245-6252

Non-Patent Document 5: “Journal of Nutritional Biochemistry”, 2004, 15th, p. 267-272

Disclosure of the invention

Problems to be solved by the invention

[0005] An object of the present invention is to provide a low calorie sweetener excellent in safety and sweetness.

Means for solving the problem

[0006] The present invention relates to the following (1) to (3).

(1) A sweetener containing as an active ingredient a dipeptide selected from the group consisting of ara-l tryptophan, noryl tryptophan, lysyl tryptophan, arginyl tryptophan, arginyl tyrosine and lysylalanine.

(2) An oral or oral composition obtained by adding the sweetener of (1) above.

(3) The oral or oral composition according to (2) above, which is a pharmaceutical product, quasi-drug, food or drink, food additive, feed or feed additive.

The invention's effect

[0007] According to the present invention, safety comprising a dipeptide selected from the group consisting of ara-l tryptophan, noryl tryptophan, lysyl tryptophan, arginyl tryptophan, arginyl tyrosine and lysyl alanine as an active ingredient Therefore, it is possible to provide a low calorie sweetener excellent in sweetness. BEST MODE FOR CARRYING OUT THE INVENTION

[0008] In the sweetener of the present invention, the constituent amino acids of each of the dipeptides of ara-l tryptophan, noryl tryptophan, lysyl tryptophan, arginyl tryptophan, arginyl tyrosine or lysylalanine (hereinafter also referred to as the dipeptide of the present invention). Each of alanine, tryptophan, norin, lysine, arginine and tyrosine may be either L-form or D-form, but L-form is preferred.

[0009] Examples of the salt of the dipeptide of the present invention include acid addition salts, metal salts, ammonium salts, organic amine addition salts, amino acid addition salts and the like.

Acid addition salts include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, maleate, fumarate, citrate, malate, lactate, a-ketoglutaric acid Organic salts such as salts, dalconates, and power prillates.

[0010] Examples of the metal salt include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as magnesium salt and strong salt, aluminum salt, zinc salt and the like.

Ammonium salts include salts such as ammonia and tetramethyl ammonium.

Examples of the organic amine addition salt include salts of morpholine, piperidine and the like.

[0011] Examples of amino acid addition salts include salts of glycine, ferrolanine, lysine, aspartic acid, dartamic acid, and the like.

The dipeptide of the present invention may be produced by any production method such as a synthesis method, an enzymatic method or a fermentation method.

Examples of the production method of the dipeptide of the present invention by a synthesis method include a solid phase peptide synthesis method described in “Peptide Synthesis Fundamentals and Experiments” (Nobuo Izumiya et al., Maruzen Co., Ltd., 1985. 1.20). Another example is a liquid phase peptide synthesis method.

[0012] The dipeptide of the present invention can also be obtained by enzymatic hydrolysis of a natural protein having the amino acid sequence.

In addition, the dipeptide of the present invention can be obtained from St. Kokusan Kagaku Co., Ltd., Nokchem, Sigma-Aldrich, etc.

The sweetener of the present invention may be the dipeptide of the present invention or a salt thereof, If necessary, it can be mixed with other sweetening ingredients, additives and the like, and processed and produced into, for example, powders, granules, pellets, tablets, and various liquid compositions.

Other sweetening ingredients include, for example, aspartame, stevia, enzyme-treated stevia, acesulfame potassium, _a- cyclodextrin, 13-cyclodextrin, N-acetyl norregoresamine, arabinose, aliteme, isotrehalose, isomanoret Tonole, isomalto-oligosaccharides (isomaltose, isomaltotriose, panose, etc.), erythritol, oligo-N-acetylacetylcosamine, galactose, galactosylsucrose, galactosyllatatose, galactopyranosyl (j81-3) galacto Vilanosinore (1-4) Dalcoviranose, Galataviranosinore (β1-3) Dalcoviranose, Galactopyranosyl (ι8 1-6) Galactoviranosyl (j8 1-4) Dalcoviranose, Galacto Pyranosyl (j8 1-6) darcoviranose, can Elephant extract (daricyrrhizin), xylitol, xylose, xylooligosaccharide (such as xylitol triose, xylobiose), glycerol, triammonium glycyrrhizinate, tripotassium glycyrrhizinate, trisodium glycyrrhizinate, diammonium glycyrrhizinate, Dipotassium dariticorelitic acid, disodium dariticorelitic acid, knolecreline, glucose, gentio-oligosaccharides (gentiobiose, gentiotriose, gentiotetraose, etc.), cyclamate, sucrose, stachyose, zunoretin, thaumatin, sonorebitone, tenolebote Sugar, Tenriyouchiya extract, Trehalulose, Trehalose, Nigerian belly extract, -Gerooligosaccharide (-Gelose etc.), Neotame, Otrehalose, neohesperidin dihydrochalcone, palatinit, palatinose, palatinose oligosaccharide, palatinose syrup, fucose, furata oligosaccharides (kestose, nistos, etc.), furatatofuranosyl nystose, Brazilian licorice extract, fructose, polydextrose, manoletotole, manoletoose , Manoletocinole β cyclodextrin, manoletote tetrol, maltotriitol, malto-oligosaccharide (maltotriose, tetraose, pentaose, hexaose, heptaose, etc.), mannitol, miracle fruit extract, melibiose, lacan force extract, ratathitol , Lactulose, ratatose, raffinose, rhamnose, ribose, isomerized liquid sugar, reduced isomaltooligosaccharide, reduced key Roorigo sugar, instead of the original Genchioorigo sugar, reduced maltose syrup, reduced starch syrup, enzyme treatment Kanzou, enzymatic degradation cans zone ©, sugar binding syrup (coupling sugar), soy oligosaccharides, invert sugar, syrup, honey, etc. can give.

[0014] When the sweetener of the present invention is in the form of powder, granules, pellets, tablets, etc., sugars such as lactose, sucrose, glucose, sucrose, mannitol, sorbitol, potato, wheat, corn, etc. Starch, calcium carbonate, calcium sulfate, sodium hydrogencarbonate, sodium chloride, inorganic substances such as sodium chloride, crystalline cellulose, plant powder such as licorice powder, gentian powder, etc., starch, agar, gelatin powder, crystalline cellulose, carmellose Disintegrants such as sodium, carmellose calcium, calcium carbonate, sodium hydrogen carbonate, sodium alginate, lubricants such as magnesium stearate, talc, hydrogenated vegetable oil, macrogol, silicone oil, polyvinyl alcohol, hydroxypropyl cellulose, methyl cellulose , Ethyl cellulose, carmelo It can be produced by adding a binder such as sugar, gelatin and starch paste, a surfactant such as fatty acid ester, and a plasticizer such as glycerin.

[0015] When the sweetener of the present invention is in the form of a liquid composition such as syrup, for example, water, sugars such as sucrose, sorbitol and fructose, glycols such as polyethylene glycol and propylene glycol, sesame oil and olive oil , Oils such as soybean oil, preservatives such as p-hydroxybenzoic acid esters, parabenzoic acid derivatives such as methyl parabenzoate, preservatives such as sodium benzoate, flavors such as strawberry flavor and peppermint Etc. can be added and processed and manufactured.

[0016] The sweetener of the present invention can be widely used for sweetening oral or oral compositions that are ingested or administered by humans and non-human animals.

Examples of the oral or oral composition include pharmaceuticals, quasi drugs, food and drink, food and drink additives, feed and feed additives.

Examples of pharmaceuticals or quasi-drugs include toothpaste, liquid toothpaste, toothpaste, mouthwash, mouth freshener, mouthwash, troche, coating agent, mouth spray, gargle, tablet, cream, ointment, Examples include patches.

[0017] The food or drink or food additive may be any food, drink or food additive, for example, coffee, coffee drink, tea drink, green tea drink, oolong tea drink, fruit drink, carbonated drink, Drinks such as nutritional drinks, cocoa drinks, soy milk drinks, powdered juices, Instant beverages including instant coffee, instant tea, powdered sardine, etc., dairy products such as starch syrup, syrup, gum syrup, ice cream, lacto ice, lactic acid bacteria beverage, yogurt, iced milk, sweetened condensed milk, sweetened defatted condensed milk , Water sheep rice cake, bun, soro, kintsuba, rice cake, sweet natto, rice confectionery, rice cake, sweet candy, chocolate, candy, chewing gum, castella, cake, cookies, biscuits, snacks, pudding, jellies, sweet bread , Cream bread, etc.) Western confectionery such as cream puff, apple pie, caramel, tablet candy, fruit 'vegetable jars' canned, jam, mamalade, boiled agricultural products such as boiled beans, chestnuts, canned marine products, fish ham 'Sausages, kamaboko and other marine products, water Delicacy, processed fishery products such as boiled seafood, mixed seasonings such as noodle soup and sauce, sauces such as soy sauce, miso, tomato sauce, wooster sauce, seasonings such as ketchup, mayonnaise, dressing, mirin, mirin-style seasonings , Liquors such as amazake and sake, soups such as beef, chicken and pork, vinegars such as rice vinegar, fruit vinegar, ponzu And nutritionally enhanced foods.

[0018] The feed or feed additive may be any feed or feed additive for non-human animals such as mammals, birds, reptiles, amphibians or fish, such as pets such as dogs, cats and rats. Feed for livestock or feed additives, feed for livestock such as sushi and pigs, feed supplements for livestock such as chickens and turkeys, feed for livestock such as chickens and turkeys, feed additives for cultured fish such as Thailand and Hamachi, etc. Is given.

[0019] The amount of the sweetener of the present invention can be arbitrarily used up to the taste necessary for the oral or oral composition to be sweetened. Specific usage in different forces target product in the for an individual oral or oral composition, as dipeptide or a salt thereof of the present invention, 0.001 to 5.0 wt ^_0/0 Power Preferably, 0 . 005 to 1.0 weight ^_0/0 force more preferable.

[0020] The method of using the sweetener of the present invention for the sweetened product may be used in the same manner as other ordinary sweeteners. For example, at the time of production of the oral or oral composition, or at the time of ingestion or administration thereof, using an appropriate method such as mixing, kneading, dissolving, soaking, infiltration, spraying, spraying, injection, etc. It can be contained in the product to be sweetened. Below, the test example which investigated the sweet taste of the dipeptide of this invention is shown.

[0021] Test Example Sensory Evaluation of Dipeptide

The dipeptides of the present invention, alanyltryptophan (hereinafter Ala-Trp, manufactured by Notchem), arginyltryptophan (hereinafter, Arg-Trp, manufactured by Kokusan Kagaku), arginyltyrosine (hereinafter Arg-Tyr, Kokusan Chemical) Lysylalanine (hereinafter Lys—Ala, manufactured by Kokusan Chemical Co., Ltd.), lysyl ribtophan (hereinafter Lys—Trp, manufactured by Kokusan Chemical Co., Ltd.) 5 mM aqueous solutions were prepared and used as test solutions.

[0022] It is known to have sweetness! /, A dipeptide such as alanyl histidine (hereinafter Ala-His, manufactured by Bacchem), glycylproline (hereinafter Gly-Pro, manufactured by Bacchem), glycylvaline ( In the following, 5 mM aqueous solutions were prepared and used as comparative solutions for Gly-Val (manufactured by Notchem).

5 mM, 20 mM, and lOOmM aqueous solutions of sucrose (Kishida Chemical Co., Ltd.) were prepared and used as standard solutions. The sweetness of each test solution and the comparison solution was evaluated by the scoring method shown in Table 1 by the panel, which was the same or close to the sweetness of which standard solution compared with the sweetness of the sucrose standard solution. The types of test solution and comparative solution were blinded on the panel.

[0023] [Table 1] Sweetness of test solution

Less sweet than 5 mM sucrose solution. 0

Same as or close to 5 mM sucrose solution. 1

Same as or close to 20 mM sucrose solution. 2

20 mM sucrose solution and 1 OOmM sucrose

Same or close to the middle of the solution. Three

1 Same or close to OOmM sucrose solution. Four

1 Sweeter than OOmM sucrose solution. Five [0024] Table 2 shows the average score of three male panels.

[0025] [Table 2]

[0026] From Table 2, it is known that the dipeptides of the present invention, Ala-Trp, Arg-Trp, Arg-Tyr, Lys-Ala, Lys-Trp and Val-Trp, have not only sucrose but also sweetness. It has become clear that the Ala-His, Gly-Pro and Gly-VaU dipeptides that have been produced are also significantly higher in sweetness.

Examples of the present invention are shown below.

Example 1

[0027] [¾3] Sweetener (1)

Component Weight%

A r g -T r p 50

A r g -Ty r 25

L ys - T rp 25 by mixing the components described above, _c Example 2 to produce a powdery sweetener

[0028] [Table 4]

Sweetener (2)

Component Weight%

A r g -T r p 0. 25

A r -Ty r 0. 25

Multi-level 99.5

_C Example 3 components were mixed in the above to produce a granular sweetener in a conventional manner

[0029] [Table 5]

Fruit drink

Completion

1Z6 concentrated Wenzhou orange juice 3.7 g

Orange pulp 3.5 g

Chenic acid (anhydrous) 0.4 g

L-ascorbic acid 0.1 2 g

A r g T r p 0. 0 3 78 g

A r g-T y r 0. 0 3 78 g

Perfume

Water remaining

u oT 21 0 m 1

The above ingredients are mixed, sterilized by heating (97 ° C 98 ° C for 15 seconds), then filled in a container and sealed to produce a fruit drink.

Example 4

Garden

Chuichi ^ Gamma Gum

Component

Gum base

D—Sorbitol solution

D—Sorbi!

Lecithin

Glycerin

Peppermin strawberry flavor

A r g -Τ r ρ

Ly s -T r p

A chewing gum is produced by the conventional method using the above components.

Example 5

[Table 7] Mizuyokan

Component amount

Agar 2.4 g

Powdered Koshian 21. 0 g

Salt 0.6 g

Sweetener of Example 2 (2) 30. 0 g

D—sorbitol 39. 0 g

30.0 g of water

Completion weight 230 g

Add agar to water, dissolve by heating, add the remaining ingredients, and boil to produce water yokan. Example 6

[0032] [Table 8] Animal feed

Component

Lard 5.

Corn oil 1.

A r g -T r p 5.

Cell square 5.

Choline chloride 0.

Vitamin mixture 3.

Corn starch 44.3 g

The animal feeds having the above-mentioned ingredients are produced by a conventional method.

Industrial applicability

[0033] According to the present invention, a low-calorie sweetener excellent in safety and sweetness can be provided.

Claims

The scope of the claims

[1] A sweetener containing, as an active ingredient, a dipeptide selected from the group consisting of ara-tryptophan, noryltryptophan, lysyltryptophan, arginyltryptophan, arginyltyrosine, and lysylalanin.

[2] An oral or oral composition comprising the sweetener according to claim 1.

[3] The oral or oral composition according to claim 2, which is a pharmaceutical product, quasi drug, food or drink, food additive, feed or feed additive.