JPS61216648A - food and drink - Google Patents

Abstract

PURPOSE:To obtain a food and drink having improved anticarious effect, foul breath preventing effect and periodonitis preventing effect, by incorporating a water-soluble compound derived from chitin with other foods and drinks. CONSTITUTION:A food and drink obtained by incorporating a water-soluble compound derived from chitin, e.g. water-soluble oligomer of chitin or chitosan or water-soluble partially deacetylated chitin, preferably a compound exhibiting >=0.1mg solubility in 100g water in an amount within 1ppm-50wt%, preferably 1ppm-10wt% range based on the total food and drink with other various foods and drinks, e.g. confectionery, refreshing drink or seasoning.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to foods and drinks that have excellent caries prevention effects, halitosis prevention effects, and periodontal disease prevention effects by incorporating water-soluble compounds derived from chitin.

Conventional technology and its problems As is well known, dental caries is mainly caused by streptococci, a type of oral streptococcus.
It is a multifactorial disease caused by infection with Tococcus mutans) in the presence of sucrose. That is, S. mutans produces water-insoluble extracellular glucan by the action of glucosyltransferase (GTF) using silasugar as a substrate, and this adheres firmly to the tooth surface to form dental plaque. In addition, the Stretkotsukas-Mutan Prize was awarded to the free 7-lactose produced during the process of forming dental plaque, the monosaccharide produced from sucrose through the action of invertase, or the production of acid by decomposing sugars in the diet. This acid demineralizes tooth enamel and causes caries.

Therefore, in order to prevent dental caries, it is necessary to suppress the production of water-insoluble extracellular glucan by the action of glucosyltransferase using cytetrasaccharide as a substrate, and to suppress this extracellular glucan. It is desirable to prevent glucan from adhering to teeth and forming dental plaque, and for this purpose it is preferable to reduce the intake of sila sugar. Therefore, in foods and beverages such as confectionery and beverages, conventionally used ingredients such as coupling cigars, carcinose, xylose, stevioside, reduced maltose, and assu #5 +
- Add non-fermentable or low-fermentable sweeteners such as mushroom sugar instead of mushroom sugar, or reduce the amount of mushroom sugar used.
Efforts are being made to prevent caries.

However, all of the above-mentioned food and drink products using sweeteners as substitutes for citrus sugar have the disadvantage that they are significantly inferior to citrus sugar in terms of taste. Furthermore, these sweeteners have problems such as exhibiting a temporary laxative effect when ingested in large quantities at once, having a low degree of sweetness, or being unstable against heat treatment. In addition, even if the food or drink itself does not contain sucrose, it is not possible to remove sucrose from all foods, so it is recommended that you eat foods and drinks that contain sucrose at the same time. In such cases, you may end up ingesting sila sugar), which poses a problem in preventing dental caries. For this reason, there has been a demand for food and drink products that contain coriander sugars but do not cause caries, or foods and drinks that can be taken together with coriander sugars to prevent caries.

SUMMARY OF THE INVENTION In view of the above circumstances, the present inventors conducted extensive research into suppressing the caries-promoting effect of foods and beverages containing citric acid, and as a result, discovered that the present inventors have developed a method for suppressing the caries-promoting effect of foods and beverages containing citric acid. When a water-soluble compound is added, the caries-promoting effect of foods and drinks is suppressed and caries is prevented, and the above objectives are effectively achieved, and furthermore, periodontal disease and bad breath prevention are also achieved. I found out that.

That is, in the present invention, by incorporating water-soluble compounds derived from chitin into foods and drinks, Streptococcus minitans converts water-insoluble extracellular glucan using sulfate sugar as a substrate through the action of glucosyltransferase. production and the strong adhesion of water-insoluble extracellular glucan to the tooth surface. Therefore, Streptococcus minitans is inhibited from aggregating on the tooth surface and producing acid, and caries is prevented. Furthermore, this suppresses the formation of tartar, which causes periodontal disease, and prevents periodontal disease.It also suppresses the formation of dental plaque, which is a mass of bacteria, so microbial metabolism The generation of mercaptan compounds is suppressed,
This prevents a musty odor.

In this case, the food/drink containing the water-soluble compound derived from chitin may or may not contain chitin sugar; Even when water-soluble compounds derived from
When another food/beverage containing sucrose is ingested together with this, the caries-promoting effect of the sucrose can be effectively suppressed.

Here, chitin is represented by the general formula (A) in which N-acetylated glucosamine is β-1
, 4, which are bound together, exist naturally as organic skeletal substances in arthropods and molluscs, and in plants, they exist in fungal hyphae and spores, and can be obtained from them. For example, when using the shells of crabs, shrimp, krill, etc. as food, the shells are crushed and then treated with hydrochloric acid to remove calci and rum, and then treated with caustic soda to remove protein and other impurities. After removal, washing with water, and drying, chitin can be obtained as a white 7-lake-like substance. Furthermore, chitosan derived from chitin is a deacetylated product of chitin, and can be obtained as a white flake-like material by, for example, treating bovine chitin with an alkali. Chitosan, for example, is available from Kyowa Yushi Kogyo Co., Ltd. as "Frona.

It can be obtained as NJe (trade name).

Chitin and chitosan have chemical structures similar to cellulose, but their resistance to chemicals is much greater than that of cellulose, and because they have acetamide and amino groups in their molecules, many It has some interesting properties. However, the reality is that chitin and chitosan have extremely low utilization rates compared to cellulose and other polysaccharides. By converting chitin and chitosan into water-soluble derivatives, we discovered that water-soluble compounds derived from chitin are effective in preventing dental caries, periodontal disease, and bad breath. This invention is based on this knowledge.

The present invention will be explained in more detail below.

Structure of the Invention The food and beverage according to the present invention contains one or more water-soluble compounds derived from chitin.

In this case, as the water-soluble compound derived from chitin, for example, those exemplified below can be suitably used.

(1) -? Water-soluble olico-9mer of chitin or chitosan, which is obtained by decomposing chitin or chitosan into a low molecular weight product (provided that the degree of polymerization of glucosamine units is greater than 1).

Such oligomers can be obtained by ordinary molecular weight reduction methods, such as nitrite decomposition method, zeic acid decomposition method, chlorine decomposition method (Japanese Patent Application No. 1982-43282), enzymatic or microbial decomposition method. This can be obtained through legal means.

(2) Water-soluble partially deacetylated chitin with a degree of deacetylation preferably from 40 to 60%.

For example, it can be obtained by controlling the degree of deacetylation of chitin according to the method disclosed in JP-A-53-47479.

(Salts of xatone organic or inorganic acids; specific examples of organic acids include acetic acid, phosphorous acid, citric acid, ascorbic acid, etc.; examples of inorganic acids include hydrochloric acid,
Sulfuric acid%! l'i1 etc. are exemplified.

(4) A derivative made by introducing a hydrophilic group into chitin or tosan to make it water-soluble. Specific examples of this include the following.

■ Chin or chitosan in diethylene and polyoxypropylene in Delio
Poq. , H (however, t1 15*m4w0-J5+
t+m field 0) R2 knee H or one+EO±6・吋po?
, 2H (however, t2=0~5.m2-0~5.z2+m
240>R,: -H or +EO+t, ・+PO radiation, H (however, t3-0-5 m ln3-0~5 a
t3 +In3'e O). Here, EO represents an oxyethylene chain, PO represents an oxypropylene chain,
In addition, the order of combining EO and PO does not matter; for example,
First, PO may be added to the D-glucosamine skeleton, and then the ship may be added, or EO and PO may be added at random. Moreover, in each bonded D-glucosamine skeleton, R1e R2e R,5,! 11 tn2
aR5et1*t2-15 may be the same or different. ] This polio-containing diethylene/polypropylene glycol chitin or chitosan is prepared by adding 1 chlorohydroxyethylene, chlorohydromal dipropylene, ethylene oxide, or glopylene oxide to alkali chitin or tosan at room temperature and pressure or at 50 to 6 QC.
K can be obtained by reacting under pressure of ~5 kII.

■ Cal&-p dimethyl chitin or chitosan [wherein n:>I R4: -H or 10OCR.

R5: -H, -CH2COOH, -CH3COONa
, -CH2COOK or 10H2C0ONH4 R6: -H, -CH2COOH, -CH3COONa
, -CH2COOK or -CH2COONH4. However, R5 and R6 are never both -H. Moreover, % R4+ R5+ R6 of each D-glucosamine skeleton connected may be the same or different. ] This Cal? Mesomethyl chitin or chitosan can be obtained by reacting alkali chitin or chitosan with monochloroacetic acid at room temperature and pressure.

■ Phosphorylated chitin or chitosan [In the formula, n:〉1 0M.

Heat R,: -H, -COCI(2 or -P-0(M,
and M20M2 is -H*Na*K or -NH4)0M3 Station R8: -H or -P0 (M3 and M4 are -H2
0M4 Na, K or -NH4) 0M5' R,: -H or -P-0 (M, and M6 are -H9
0M6 Na, K or -NH4), but R8 and R9 are K at the same time
-H, OM never becomes.

R1°: -H, -COCH, or -P-0 (Ma and M80M8 represent -HeNa*Ki or -NH). In addition, in each linked D-/”lucosamine skeleton, R
, R8, R, and R1° are the same; or may be different. ] This phosphorylated chitin or chitosan is dissolved or suspended in methanesulfonic acid.
It can be obtained by reacting niline pentoxide under cooling. This method is described in Proceedings of the 48th Autumn Annual Meeting of the Chemical Society of Japan, p. 570 (Norio Nishi et al.).

■ Sulfated medium tenten or medium tenten :In the formula, n:〉1 0M.

R,: -H, -COCH3t or -8-0 (M, -H2Na, K or -NH4) 0M10 R12: -H or -8-0 (M, -H+Na,
K or -NH4) OMl.

R, 3 Knee H or -8-0 (M,, is -H, Na5K
'! or -NH4) 0M12 J4: -H*-COCH3 or -8-0 (M, 2
represents -H2Na*K or -NH4). Moreover, R11# R12' R15e R14 may be the same or different in each of the bonded D-glucosamine skeletons. [References:
M.L., Wolfrom et al. + TheS.
Ulfnation of Chitosan y
J, Axn, Boa-e 81 *1764-1766
(1959)).

■ N-glycidyltrimethylammonium chloride [in the formula,
N-glycidyltrimethylammonicum chitosan with n:〉1 (X, ct or Br) (x2 is ct or Br) is produced by adding glycidyltrimethylammonium chloride to medium tosan under a high concentration alkali catalyst under high temperature and high pressure. This can be obtained by adding .

[In the formula, n:〉■ R,,: -H or 10OCR.

R18: -H or -CH2-CH-CH20HH R1,: -H or 10H2-CM-CH20HH. However, R18 and R19 do not become -H at the same time. ] This dihydroxyglobil chitin or chitosan is converted into alkaline chitin or chitosan under high temperature.
It can be obtained by ring opening and addition of phosphorus.

[In the formula, n:〉1 0HO (M, 5 is Na * K or -NH4) 0HO (M, 4 is Na, K or -Nu4) 0 However, % "20 and R21 become -H at the same time There isn't.

] Tosan in N-2-hydroxyglobylsulfonic acid can be obtained by adding glycidyl sulfonic acid to tosan in N-2-hydroxyglobylsulfonic acid under an alkali catalyst at high temperature and pressure.

Note that the above-mentioned method for producing water-soluble substituted tin or chitosan does not limit the method for producing chitin or chitosan used in the present invention.

Here, in the present invention, it is particularly preferable to use partially deacetylated chitin among the above-mentioned compounds.

Furthermore, the water-soluble compound derived from chitin used in the present invention is preferably one that exhibits solubility in water with a pH of 7 and has a solubility of o, i w or more per 100 PK of water.

The amount of water-soluble compounds derived from chitin is as follows:
IPPM ~ 50% by weight of the entire food and drink, especially 1 ppm ~
It is preferable to set it as 10 weight.

In the present invention, there is no particular restriction on the food/beverage products to which the water-soluble compound derived from chitin is blended, and various food/beverage products include confectionery, instant foods, soft drinks, seasonings, and the like. Specifically, sweets such as drops, candies, medium yamel, starch syrup, chiso collate, biscuits, kutsky, cakes, marshmallows, castella, yokan, manju, oban-yaki, imayo-yaki, taiyaki, uirou, amanatto, Fried sweets such as senbei, arare, and kashinto, ice cream, jelly, pudding, anmitsu, jam, sugared fruit, shiruko, ohagi, rakugan, denbu, omelet, powdered soup, coffee milk, lactic acid bacteria drinks, and dill. Crystal,
Examples include sugar, salad dressing, etc., and these foods and drinks can be manufactured by known methods and formulations. Note that these foods and drinks may or may not contain sulfate sugar.

As described in detail of the invention, the food and beverage according to the present invention contains a water-soluble compound derived from chitin.
In addition to being highly effective in preventing caries, it also has excellent effects in preventing periodontal disease and bad breath. in this case,
The above effects are well exhibited even when citrus sugar is added to food and drink products, so instead of using an alternative sweetener, citrus sugar, which humans naturally prefer, is added - it tastes good and does not cause caries. Food and beverages can be provided. In addition, the water-soluble compound derived from Nakachin has no taste or odor, and can be incorporated into any food or drink without impairing its flavor. 1 more
゛Kitin LD. is highly safe with a value of 5 or more, and water-soluble compounds derived from it are also highly safe; for example, the LD5 of nitrite-decomposed low molecular weight chitosan
゛ is 5 or more koji, Cal is I of chi in oxymethyl, D-5゜ is 1 or more per 1 l, LD of ethylene glycol chitosan. has an IP of 7 kg or more], and other water-soluble compounds derived from chitin are similarly safe.

Next, an experimental example will be shown to concretely demonstrate the effects of the present invention. [Experimental Example] Streptococcus ξ&tans strain 6715 was cultured for 48 hours in a semi-selective medium, 4 G m1.
lif 9 acid f) 9 a4-7a glucosyltransferray crude enzyme solution (0,411F protein/
wLl) was obtained. Next, 0.4 M of the sample aqueous solution shown in Table 1 containing various water-soluble medium-strength compounds, 2.6 M of the 1.5-tish sugar aqueous solution, and 1 sl of the above crude enzyme solution were placed in a test tube at 37°C. After reacting for 20 hours, the turbidity at 550 nm was measured to obtain the following turbidity index.

Turbidity Index A turbidity index with the turbidity of the control as 100 was used as an index representing the effect of suppressing glucan production or adhesion. Therefore, clauses with smaller numbers are valid. In addition, if glucan was generated and did not adhere to the wall of this test tube,
Alternatively, if it is brittle even if attached, it will flow out of the system at the same time as the internal liquid is discharged, resulting in a small value.

The results are shown in Table 1. Note that the average molecular weight and degree of deacetylation in the table were measured as follows.

(1) Average molecular weight measurement method Shimadzu high performance liquid chromatograph LC-5A, RID
-2A to empty A 5hin-pack OHB-805
Dechustran (manufactured by Sigma) was used as a standard substance.
It was measured by the GPC method using

(2) Deacetylation degree measurement method Using methylene blue as an indicator, the nitrogen content was determined by a colloidal titration method in which a stock solution of chitosan in acetic acid was titrated with an aqueous solution of potassium 4-rivinyl sulfate, and was converted to the degree of deacetylation.

The results in Table 1 show that when water-soluble chitins are added to a system containing sucrose, the production of water-insoluble extracellular glucan due to the action of glucosyltransferase is significantly suppressed, and It was found that glucan adhesion was inhibited.

Based on this fact, it has been recognized that people can prevent caries, periodontal disease, and bad breath by adding citrus sugar as a sweetener to food and drink products and simultaneously using water-soluble chines. It will be done.

Examples will be shown below, but the present invention is not limited to the following examples.

[Example 1] Solid mouth freshener venona mint oil 1 lumon oil 0.2 oil nol
0.1 anethole
0.2 Kargin
0.3 Nitrite decomposed low molecular weight chitosan 30
Licorice powder 42 pieces 1 ear
10 oris root end
10 Chikeihi powder 3
Is it blasphemous? Shiri Powder 2 Technique Powder 1 [Example 2] Mud, Gushi Sugar 80 1 Glucose 16.5 Citric Acid
1.1 Caldexymethyl chitosan Na salt 1.0 Fragrance
Appropriate amount of pitaci socholate
22 Tishitsu sugar 40
Milk powder 21 cocoa butter
16 [Example 4] Bart biscuit, tofu flour 62.2 Chishi ■
-toning lO sulfate sugar
15 salt
0.5 whole milk powder 1.
8 Leavening agent 0.5゜ [Example 5] Coffee milk Whole fat milk 40% skim milk 19 Sugar
8 Coffee infusion 30 Caramel
0.3 fragrance
0.1 nitrite decomposition is marchitosan 1 total
100 [Example 6] Lactic acid bacteria beverage fermented skimmed milk 37 Ticil sugar 14 Stabilizer
0.35 fragrance
0.05 dye
Appropriate amount of Calxymethylchitin Na salt
3 water
Balance total 1
00% [Example 7] Ice cream whole milk 50 1 Sweetened skimmed condensed milk 23454 Fresh cream 20 Soda sugar
5 Emulsifier/stabilizer 0.5 Degree of deacetylation 40-60% Chitosan 1.5
Total 100 pieces [Example 8] Carbonated beverage Wenzhou IA concentrated fruit juice 20 ? Grani gourd - sugar 240. P citric acid
3.5? citric acid soda
0.2 P vitamin K
O,15j' carotene base
2/- orange essence
2.5 Gokaloxymethylchitosan N
a Salt 2P Add water to the above ingredients and make IQ
Add QQIJ and 1009m of carbonated water for a total of 200
0117.

[Example 9] Soup powder salt 35% Glutakin soda 22 Chicken oil -15

Claims (1)

[Scope of Claims] 1. A food or drink product comprising one or more water-soluble compounds derived from chitin. 2. The food or drink according to claim 1, wherein the water-soluble compound derived from chitin is partially deacetylated chitin.