Vitamin K stabilization method

By coexisting vitamin K with chitosan oligosaccharide and using a chitosan-degrading enzyme, the instability of vitamin K is addressed, resulting in a stable composition that maintains vitamin K's functionality in products.

JP7785277B2Active Publication Date: 2025-12-15IKEDA SHOKKEN KK
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Patent Information

Application Number
JP2021102020
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2020-06-01
Filing Date
2021-05-10
Publication Date
2025-12-15
Estimated Expiration
2041-05-10

AI Technical Summary

Technical Problem

Vitamin K is unstable to light and heat, and existing stabilization methods are inadequate for maintaining its stability in various products.

Method used

Stabilizing vitamin K by coexisting it with chitosan oligosaccharide, and treating the aggregate of vitamin K-containing compositions with a chitosan-degrading enzyme to form a stable composition.

Benefits of technology

The method effectively stabilizes vitamin K, preventing its degradation during storage and maintaining its functionality in products, thereby enhancing the value of vitamin K-containing products.

✦ Generated by Eureka AI based on patent content.

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Abstract

To provide a method for stabilizing vitamin K and a stabilized vitamin K composition.SOLUTION: It has been found out that the coexistence of vitamin K with chitosan oligosaccharide can stabilize vitamin K and the present invention has been completed.SELECTED DRAWING: None
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Description

[Technical Field]

[0001] The present invention relates to a method for stabilizing vitamin K and a composition for stabilizing vitamin K. [Background technology]

[0002] Vitamin K is a fat-soluble vitamin that is involved in blood coagulation and bone formation. Naturally occurring forms of vitamin K exist as two molecular families: phylloquinone (vitamin K1) and menaquinone (vitamin K2). Vitamin K is known to be derived from plants, animals, or microorganisms. Both phylloquinone and menaquinone are thought to be converted to menaquinone-4 in the body and utilized. Microbial forms are produced by microorganisms belonging to the genera Arthrobacter and Bacillus, and are known to be effective in preventing osteoporosis and arteriosclerosis.

[0003] Patent Document 1 describes a method for recovering vitamin K2, which includes a step of treating a sample containing vitamin K2 with chitosan, and a step of extracting vitamin K2 adsorbed to the chitosan with an organic solvent.

[0004] On the other hand, vitamin K is unstable to light, heat, etc., and various studies have been conducted on stabilizing vitamin K. For example, Patent Document 2 describes a method for producing a stabilized complex, which is characterized by including a compound having an isoprenoid structure and / or a quinone structure in γ-cyclodextrin (γCD). [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2006-325597 [Patent Document 2] Japanese Patent Application Laid-Open No. 2006-249050 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention provides a method for stabilizing vitamin K and a composition for stabilizing vitamin K. [Means for solving the problem]

[0007] The inventors have discovered that vitamin K can be stabilized by coexisting it with chitosan oligosaccharide, and have completed the present invention.

[0008] That is, the present invention relates to the following aspects [1] to [8]. [1] A method for stabilizing vitamin K by coexisting vitamin K with chitosan oligosaccharide. [2] The method for stabilizing vitamin K according to [1], wherein 0.02 to 10 g of chitosan oligosaccharide is coexistent per 1 mg of vitamin K. [3] A method for stabilizing vitamin K according to [1] or [2], characterized in that an aggregate of a vitamin K-containing composition and chitosan is treated with a chitosan-degrading enzyme. [4] A vitamin K stabilization composition comprising vitamin K and chitosan oligosaccharide. [5] The vitamin K stabilization composition according to [4], which contains 0.02 to 10 g of chitosan oligosaccharide per 1 mg of vitamin K. [6] The stabilized vitamin K composition according to [4] or [5], which is obtained by treating an aggregate of a vitamin K-containing composition and chitosan with a chitosan-degrading enzyme. [7] A stabilized vitamin K composition stabilized by the stabilization method according to any one of [1] to [3]. [8] A food, drink, pharmaceutical, feed or cosmetic product comprising the vitamin K stabilization composition according to any one of [4] to [7]. [Effects of the Invention]

[0009] The present invention makes it possible to simply stabilize vitamin K, which has low stability, and to provide a vitamin K stabilized composition in which vitamin K is stabilized.By suppressing the decrease of vitamin K during storage in products containing vitamin K, it is possible to stably contain highly functional vitamin K, thereby increasing the value of the product. DETAILED DESCRIPTION OF THE INVENTION

[0010] In the present invention, vitamin K can be stabilized by allowing it to coexist with chitosan oligosaccharide, and a vitamin K stabilized composition containing vitamin K and chitosan oligosaccharide can be produced. Examples of vitamin K to be stabilized include phylloquinone (vitamin K1), menaquinone (vitamin K2), and menadione (vitamin K3). Furthermore, the menaquinone may be any of menaquinone-1 to -14, with menaquinone-4 and menaquinone-7 being preferred, and the composition may be a vitamin K-containing composition.

[0011] In the present invention, the ratio of vitamin K to chitosan oligosaccharide is not particularly limited as long as vitamin K can be stabilized, but it is sufficient if the ratio is such that 0.02 to 10 g, more preferably 0.05 to 5 g, and even more preferably 0.1 to 2 g of chitosan oligosaccharide coexists per 1 mg of vitamin K.

[0012] Vitamin K can be stabilized by allowing vitamin K and chitosan oligosaccharide to coexist. For example, a vitamin K-containing composition and chitosan oligosaccharide may be mixed, but it is preferable to mix the vitamin K-containing composition with chitosan and treat the mixture with a chitosan-degrading enzyme. For example, the vitamin K-containing composition can be mixed with a chitosan solution to form aggregates, and the aggregates can be treated with a chitosan-degrading enzyme to allow vitamin K and chitosan oligosaccharide to coexist. The ratio of the vitamin K-containing composition to chitosan can be appropriately set, but is preferably 1 to 200 parts by weight, more preferably 10 to 100 parts by weight, of chitosan per 100 parts by weight of the dry weight of the vitamin K-containing composition.

[0013] The chitosan oligosaccharide used in the present invention may be any oligosaccharide obtained by hydrolyzing chitosan with an acid or enzyme, preferably an oligosaccharide having about 2 to 8 glucosamine units polymerized therein, and preferably one produced using a chitosan-degrading enzyme. The chitosan-degrading enzyme is not particularly limited as long as it is an enzyme that hydrolyzes chitosan, but an enzyme that degrades chitosan into oligosaccharides having two or more glucosamine units polymerized therein is preferred. Chitosanase derived from microorganisms or insects can be used, and enzyme preparations such as Chitosanase L (manufactured by HI Corporation) can be used. Chitosan can be a purified product obtained by deacetylating chitin contained in the exoskeleton of crustaceans such as shrimp and crab, or in the mycelium or fruiting body of fungi. Commercially available chitosan can be used, but it can also be used as a solution prepared by dissolving it in an acidic aqueous solution containing citric acid, acetic acid, hydrochloric acid, or the like, preferably at a concentration of 0.1 to 20 wt %, more preferably 0.2 to 10 wt %.

[0014] The conditions for the enzymatic treatment using a chitosan-degrading enzyme are not particularly limited as long as they allow the enzymatic reaction. For example, the amount of enzyme added is preferably 1 to 1,000 parts by weight, more preferably 10 to 500 parts by weight, based on 100 parts by weight of chitosan solids in the enzyme preparation. The treatment conditions can be appropriately set taking into account the optimal pH and temperature of the enzyme, as well as pH and temperature stability. Examples of suitable treatment conditions include treatment at pH 3 to 9 and 10 to 80°C, with pH 4 to 8 and 30 to 70°C being preferred. Treatment time can be adjusted appropriately depending on the treatment conditions, with examples ranging from 10 minutes to 48 hours being preferred, with 20 minutes to 24 hours being preferred. Furthermore, a heating step at 85 to 130°C for 6 seconds to 1 hour, preferably 90 to 100°C, for 1 to 30 minutes may be performed after the enzymatic treatment. In addition to the enzyme treatment, a shearing treatment may be carried out using a device having physical shearing ability, such as a high-pressure homogenizer, colloid mill, ultrasonic emulsifier, homomixer, or homodisper, or two or more types of device may be combined. The shearing treatment may be carried out during, before, or after the enzyme treatment using the chitosan-degrading enzyme, and is preferably carried out in parallel with the enzyme treatment. The enzyme treatment should be sufficient to almost completely eliminate precipitation due to aggregation and produce a suspended liquid. When the liquid is passed through a standard sieve conforming to JIS Z 8801-1, with a nominal mesh size of 1 mm (hereinafter referred to as "16 mesh"), it is preferable that 80% by weight or more, and more preferably 90% by weight or more, pass through.

[0015] The vitamin K-containing composition described in the present invention is not particularly limited as long as it contains vitamin K, and may be a vitamin K-containing composition derived from a plant, animal, or microorganism, or may be one to which vitamin K has been added, such as tea or algae. However, vitamin K-containing microbial cells are preferred because they contain a high amount of vitamin K. Examples of such cells include microorganisms belonging to the genus Bacillus, such as Bacillus subtilis, the genus Flavobacterium, such as Flavobacterium aquaticae, and the genus Arthrobacter, such as Arthrobacter nicotinae, and lactic acid bacteria. These may be vitamin K-producing microbial cells or microbial cells enriched with vitamin K, and may be live or killed microbial cells.

[0016] Bacillus subtilis is preferred as a vitamin K-producing microorganism belonging to the genus Bacillus. While there are no particular limitations on the vitamin K-producing Bacillus subtilis, B. subtilis subsp. subtilis is more preferred. Bacillus subtilis NBRC3009, Bacillus subtilis NBRC3013, Bacillus subtilis NBRC3335, Bacillus subtilis NBRC13169, and other natto strains are even more preferred, and are available from the National Institute of Technology and Evaluation (NITE). Furthermore, the use of a sporulation-deficient strain allows for the preparation of killed cells under mild sterilization conditions at 100°C or below, thereby minimizing the impact of heat sterilization on the vitamin K concentration in natto cells. The vitamin K content in the cells is preferably 0.02 to 2% by weight, more preferably 0.05 to 1.5% by weight, and even more preferably 0.1 to 1% by weight, based on the dry cells.

[0017] A conventional bacterial culture medium can be used for culturing microorganisms, and the culture conditions for the microorganisms can be set appropriately. Liquid culture or solid culture can be selected, but aerobic liquid culture using aeration, shaking, stirring, etc. is preferred. The culture temperature can be, for example, 10 to 50°C, preferably 20 to 40°C. The culture time can be, for example, 2 to 72 hours, preferably 4 to 48 hours, and more preferably 6 to 36 hours. The pH of the medium can be, for example, 4.0 to 9.0, preferably 5.0 to 7.5.

[0018] The microorganisms may be sterilized after cultivation. The sterilization conditions are not particularly limited as long as they are common methods, but for example, the heating temperature is 70 to 150°C, and the heating time may be determined depending on the temperature, but is usually 1 to 60 minutes. When a sporulation-deficient strain is used, sterilization can be carried out under mild conditions of 100°C or less, such as heating at 70 to 100°C for 5 to 20 minutes.

[0019] When vitamin K-containing microbial cells are used as the vitamin K-containing composition, a culture containing the cells may be used as is, or cells recovered from a culture containing the cells by solid-liquid separation may be used. The cells can be recovered, for example, by removing the medium using filtration, a centrifuge, etc. Alternatively, the cells may be washed with a buffer solution, physiological saline, sterilized water, etc., and then recovered by solid-liquid separation using filtration, a centrifuge, etc. Alternatively, the culture or recovered cells may be dried by spray drying, drum drying, air drying, vacuum drying, freeze drying, etc.

[0020] A method for stabilizing vitamin K in vitamin K-containing microbial cells includes, for example, adding a chitosan solution to a liquid containing microbial cells, such as a culture solution or a cell suspension, treating the resulting aggregates with a chitosan-degrading enzyme, passing them through a mesh, and spray-drying them to form a powder; alternatively, adding chitosan oligosaccharide to a liquid containing microbial cells, such as a culture solution or a cell suspension, and similarly powdering the mixture to form a vitamin K-stabilizing composition.

[0021] The vitamin K stabilized composition may be used as a concentrate by processing using a concentrator or the like, but is preferably dried by known drying methods such as spray drying, drum drying, air drying, vacuum drying, and freeze drying, and more preferably as a powder with good dispersibility. For example, a liquid containing the vitamin K-containing composition and chitosan oligosaccharide can be powdered by a conventional method, such as passing it through a mesh and then spray drying it to obtain a powder. Alternatively, an excipient such as dextrin may be added and the mixture may be dried, or a granule may be produced using a granulator or the like. A standard sieve conforming to JIS Z 8801-1 can be used as the mesh pass, but to obtain a powder with good dispersibility, a sieve with a nominal mesh size of 1 mm (hereinafter referred to as "16 mesh") is used, and preferably 80% by weight or more, more preferably 90% by weight or more, of the liquid containing the vitamin K-containing composition and chitosan oligosaccharide passes through it.

[0022] The vitamin K stabilization composition of the present invention can be added to various products because the vitamin K is stabilized. The composition may be added in liquid, frozen, or dried form. It can be added to various products, such as food and beverage products (e.g., instant foods, dairy products, confectioneries, seasonings, beverages, and supplements), pharmaceuticals, feed, and cosmetics, to produce food and beverage products, pharmaceuticals, feed, or cosmetics containing the vitamin K stabilization composition. In particular, powdered vitamin K stabilization compositions have excellent dispersibility, so that even when added to food and beverage products (e.g., powdered soups, powdered beverages, and powdered milk), they can be dispersed in liquids (e.g., water or hot water) without any problems at the time of consumption. It is preferable to add the vitamin K stabilization composition to food and beverage products so that the intake of vitamin K is 1 to 150 μg / day. [Example]

[0023] The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples. In the present invention, all % is by weight unless otherwise specified. [Example]

[0024] (1-1. Preparation of Vitamin K-containing bacterial culture medium) A sporulation-deficient strain, Bacillus subtilis NBRC3335, a type of vitamin K-producing microorganism, was isolated by spontaneous mutation utilizing a catabolite repression-like phenomenon. The spontaneous mutation used in TIFF0007785277000001.tif9170 was carried out by the method described in the Examples of Japanese Patent No. 6019528, and it was confirmed that the strain was deficient in sporulation ability by the method described in that publication.

[0025] The strain was inoculated into a liquid medium consisting of 2% yeast extract, 5% glucose, and 93% tap water, and cultured at 37°C, pH 6.5, for 24 hours with aeration and agitation. After that, the culture was sterilized by heating at 90°C for 10 minutes to prepare 1200 g of culture solution containing 8.76 g of sterilized cells containing vitamin K in terms of dry cell weight.

[0026] (1-2. Stabilization of Vitamin K-Containing Compositions) 60 g of a chitosan solution prepared by dissolving 5% KitoGreen (Kitosan derived from koji mold, manufactured by Seti Co., Ltd., chitosan content: 80%) in a 5% citric acid solution was added to 600 g of the culture broth obtained in 1-1 above, and the mixture was stirred and mixed at 25°C for 10 minutes to form aggregates of vitamin K-containing fungi and chitosan. The aggregates were then collected by solid-liquid separation using a centrifuge, washed with tap water, and further separated by a centrifuge to collect aggregates of vitamin K-containing fungi and chitosan. Tap water was added to the collected aggregates to make a total of 100 g, and 1 g of Chitosanase L (manufactured by HI Corporation), a chitosan-degrading enzyme preparation that produces chitosan oligosaccharides (approximately 2 to 8 sugars), was added. The mixture was treated with stirring at 60°C for 2 hours at pH 5.5, followed by sterilization and enzyme inactivation at 90°C for 10 minutes to obtain enzyme-treated aggregates. Next, the enzyme-treated product was passed through a 16-mesh sieve and then spray-dried to obtain 5 g of Example 1 vitamin K-containing composition (powder) (moisture content: 3.0%, number of dead bacteria: 6.0 × 10 10 The resulting aggregates (particles / g) were only 10% of the total weight of the aggregates before enzyme treatment passed through a 16-mesh sieve, and the aggregates remaining on the 16-mesh sieve were unsuitable for spray drying. Therefore, when freeze-dried and then pulverized, the resulting dried and pulverized material tended to settle in water and had poor water dispersibility. On the other hand, 99% of the total weight of the enzyme-treated product passed through a 16-mesh sieve, making it possible to powder it by spray drying, and the resulting powder had good water dispersibility.

[0027] [Comparative Example 1] Regarding 600 g of the culture solution obtained in 1-1, the cells recovered by solid-liquid separation using a centrifuge were washed with tap water and then further subjected to solid-liquid separation using a centrifuge to recover the cells containing vitamin K. Tap water was added to the recovered cells to make 100 g, and 3 g of Pindex (registered trademark) #2 (manufactured by Matsutani Chemical Industry Co., Ltd.), which is dextrin as an excipient, was added and dissolved. After treating at 90 °C for 10 minutes for sterilization, a vitamin K-containing cell suspension containing dextrin was obtained. Next, after passing the cell suspension through a 16-mesh sieve, it was spray-dried to obtain 5 g of a vitamin K-containing composition (powder) of Comparative Product 1 (moisture: 3.8%, number of cells (dead cells): 6.5×10 10 cells / g). Among the total weight of the cell suspension, 99% passed through a 16-mesh sieve, and it was possible to obtain a powder that could be powdered by spray-drying and had good water dispersibility.

[0028] [Evaluation Test 1] An accelerated storage test at 50 °C for 23 days was conducted on Product 1 and Comparative Product 1. For each sample before and after storage, the content of menaquinone-7, which is a type of vitamin K, was measured, and the residual rate was calculated. The content of menaquinone-7 was measured by the following method using HPLC. The results are shown in Table 1.

[0029] <HPLC Measurement Conditions> ·Detector: UV detector (270 nm) ·Column: InertSustain C18 (inner diameter 4.6 mm, length 250 mm) ·Mobile phase: Methanol ·Flow rate: 1.0 ml / min ·Column temperature: 40 °C ·Standard: A menaquinone-7 standard product (purity: 98%, manufactured by FUJIFILM Wako Pure Chemical Corporation) was dissolved in ethanol to prepare a calibration curve. ·Sample: Each sample was dissolved in ethanol and then appropriately diluted.

[0030]

Table 1

[0031] The menaquinone-7 residual rate of Example Product 1 after storage at 50°C for 23 days was significantly higher than that of Comparative Product 1. This indicates that treating aggregates of vitamin K-containing bacterial cells and chitosan with a chitosan-degrading enzyme not only produces bacterial cell powder with good water dispersibility, but also stabilizes the unstable vitamin K. [Example]

[0032] A liquid medium consisting of 5% yeast extract, 2% trisodium citrate, and 93% tap water was used in the same manner as in 1-1 above, except that a liquid medium consisting of 5% yeast extract, 2% trisodium citrate, and 93% tap water was used. 20 g of dried cells (menaquinone-7: 4,065 ppm) was prepared by spray-drying the culture solution obtained by culturing the cells in the same manner as in 1-1 above. 380 g of tap water was added to the culture solution and mixed for 5 minutes to obtain 400 g of cell suspension. 100 g of each suspension was added with 5 g of Koyo Oligoglucosamine WG (manufactured by Koyo Chemical Co., Ltd., crab-derived) as a chitosan oligosaccharide (Example 2-1), or 100 g of a chitosan solution prepared by dissolving 5% Koyo Chitosan (registered trademark) FL-80 (manufactured by Koyo Chemical Co., Ltd., crab-derived) as a chitosan in 0.6% aqueous hydrochloric acid solution, and 1 g of chitosanase L (Example 2-2). The mixture was stirred for 5 minutes, then stirred at 60°C for 2 hours, and then treated at 90°C for 10 minutes to sterilize and inactivate the enzyme. Next, the mixture was passed through a 30-mesh sieve (openings 0.5 mm) and then spray-dried to obtain vitamin K-containing compositions (powder) of Examples 2-1 and 2-2. Of the total weight before passing through the sieve, 99% or more passed through the 30-mesh sieve, making it possible to powderize the mixture by spray-drying, and a powder with good water dispersibility was obtained.

[0033] Comparative Example 2 To 100 g of each of the 400 g bacterial cell suspensions prepared in Example 2, 5 g of Pinedex (registered trademark) #2 dextrin (Comparative Example 2-1) or 100 g of a chitosan solution prepared by dissolving 5% Koyo Chitosan FL-80 chitosan in 0.6% aqueous hydrochloric acid (Comparative Example 2-2) was added. The mixture was stirred for 5 minutes and then sterilized at 90°C for 10 minutes. The mixture was then passed through a 30-mesh sieve (0.5 mm opening) and spray-dried to obtain a vitamin K-containing composition (powder) as Comparative Product 2-1. In Comparative Example 2-1, more than 99% of the total weight of the bacterial cell suspension passed through the 30-mesh sieve, making it possible to powder the suspension by spray-drying and yielding a powder with good water dispersibility. However, in Comparative Example 2-2, aggregates precipitated and only about 10% passed through the 30-mesh sieve, so spray-drying was abandoned.

[0034] [Evaluation Test 2] An accelerated storage test was conducted at 50°C for Example Products 2-1, 2-2, and Comparative Product 2-1. The content of menaquinone-7, a type of vitamin K, was measured for each sample before and after storage (15 and 23 days), and the residual rate was calculated. The menaquinone-7 content was measured using HPLC as described above. The results are shown in Table 2.

[0035] [Table 2]

[0036] The menaquinone-7 residual rate of Example Product 2-1 after storage at 50°C for 15 and 23 days was higher than that of Comparative Product 2-1, and the menaquinone-7 residual rate of Example Product 2-2 after storage at 50°C for 15 and 23 days was significantly higher than that of Comparative Product 2-1, demonstrating that a high vitamin K stabilization effect was observed even when crab-derived chitosan was used as the chitosan instead of the fungus-derived chitosan used in Example 1. Therefore, it was found that the coexistence of vitamin K-containing fungal cells and chitosan oligosaccharides can stabilize unstable vitamin K.

[0037] Comparative Example 3 To 30 g of a vitamin K-containing composition (powder) obtained in the same manner as in Comparative Example 1, 70 g of tap water and 0 mg (Comparative Example 3-1), 30 mg (Comparative Example 3-2), 60 mg (Comparative Example 3-3), 150 mg (Comparative Example 3-4), 300 mg (Comparative Example 3-5), or 600 mg (Comparative Example 3-6) of Emix®-P20 (manufactured by Mitsubishi Chemical Corporation, total tocopherols: 16-21%, emulsified powder), a vitamin E stabilizer, were added and dissolved. The resulting solution was then treated at 90°C for 10 minutes to obtain vitamin K-containing bacterial cell suspensions containing various concentrations of vitamin E. Each bacterial cell suspension was then passed through a 16-mesh sieve and spray-dried to obtain 20 g of each of the vitamin K-containing compositions (powder) of Comparative Examples 3-1 to 3-6. 99% of the total weight of each bacterial cell suspension passed through the 16-mesh sieve, enabling it to be powdered by spray drying and yielding powders with good water dispersibility.

[0038] [Evaluation Test 3] Comparative Products 3-1 to 3-6 were subjected to an accelerated storage test at 50°C for 54 days, and the content of menaquinone-7, a type of vitamin K, was measured for each sample after refrigerated storage and after storage at 50°C. The residual menaquinone-7 percentage in Comparative Products 3-1 to 3-6 stored at 50°C was calculated compared to that in Comparative Products 3-1 to 3-6 stored at refrigerated storage. There was almost no difference in the residual menaquinone-7 percentage (66 to 70%) for all of Comparative Products 3-1 to 3-6, regardless of the presence (concentration) of vitamin E, and no vitamin K stabilization effect by vitamin E was observed. [Example]

[0039] Vitamin K composition K2 Oil P-2000 (manufactured by J-Oil Mills Co., Ltd., menaquinone-7: 2099 ppm), chitosan oligosaccharide Koyo Oligoglucosamine WG, dextrin Pinedex (registered trademark) #2, and water were mixed in the proportions shown in Table 3, and then spray-dried to obtain 5 g each of Examples 3-1, 3-2, and a blank vitamin K-containing composition (powder).

[0040] [Evaluation Test 2] An accelerated storage test was conducted at 50°C for Products 3-1 and 3-2 and the blank. The content of menaquinone-7, a type of vitamin K, was measured for each sample before and after storage (after 21 days), and the residual rate was calculated. The menaquinone-7 content was measured using HPLC as described above. The results are shown in Table 3.

[0041] [Table 3]

[0042] The menaquinone-7 residual rate of Products 3-1 and 3-2 after storage at 50°C for 21 days was higher than that of the blank, indicating that the coexistence of vitamin K and chitosan oligosaccharide can stabilize the unstable vitamin K.

Claims

1. A method for stabilizing vitamin K2, in which 0.1 to 10 g of chitosan oligosaccharide in which 2 to 8 glucosamine units are polymerized is coexisted per 1 mg of vitamin K2.

2. 2. The method for stabilizing vitamin K2 according to claim 1, wherein the aggregate of the vitamin K2-containing composition and chitosan is treated with a chitosan-degrading enzyme.

3. 3. The method for stabilizing vitamin K2 according to claim 2, wherein the vitamin K2-containing composition is a vitamin K2-containing microbial cell.

4. A vitamin K2 stabilized composition containing 0.1 to 10 g of chitosan oligosaccharide in which 2 to 8 glucosamine units are polymerized per 1 mg of vitamin K2.

5. 5. The vitamin K2 stabilized composition according to claim 4, which is obtained by treating an aggregate of a vitamin K2-containing composition and chitosan with a chitosan-degrading enzyme.

6. 6. The vitamin K2 stabilized composition according to claim 5, wherein the vitamin K2-containing composition is a vitamin K2-containing microbial cell.

7. A food, drink, pharmaceutical, feed or cosmetic product comprising the vitamin K2 stabilizing composition according to any one of claims 4 to 6.

Citation Information

Patent Citations

  • Medicinal composition

    JP1990131434A

  • Stabilized complex and process thereof

    JP2006249050A

  • Method for recovery of vitamin k2

    JP2006325597A

  • Ultraviolet absorbing agent, skin preparation for external use containing the same, and antioxidant

    JP2007217304A

  • Container for sanitary goods

    JP2010179928A