JP2005304401A - Fermentation treatment product and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a fermentation treatment product safe as a food material or food, unlike those produced using metal catalyst, through the fermentation treatment with microorganisms, capable of obtaining tetrahydrocurcumines in high yield, high in the content of the tetrahydrocurcumines having remarkable antioxidant activity, therefore having high antioxidant activity, thus highly useful as a food material and food, to provide a method for producing the fermentation treatment product, and to provide food materials and food using the same. <P>SOLUTION: The fermentation treatment product is characterized by containing tetrahydrocurcumines that are obtained by adding a cyclodextrin to curcumines followed by making a fermentation treatment. In this product, it is preferable that the curcumines are represented by formula(1)( wherein, R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>and R<SP>4</SP>are each H, OH or a lower alkoxy ) and derived from a turmeric plant and the fermentation treatment is performed using microorganisms including yeasts. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a fermented product obtained by adding a cyclodextrin to curcumin and subjecting it to a fermented product, a method for producing the fermented product, and a food material and food containing the fermented product.

  Curcumin is a large amount of curcuma perennial turmeric, especially in its rhizomes, spicy, turmeric rhizome dry turmeric used as a coloring agent, antioxidant, anti-inflammatory, cholesterol-reducing, Since it has been clarified to have a medicinal effect such as a carcinogenic inhibitory effect, it is used as a safe medicinal component derived from food. It is known that tetrahydrocurcumin, which is a reduced form of such curcumins, has a stronger antioxidant effect than curcumins, and has an anti-cataract effect and a colon cancer suppression effect higher than those of curcumins (for example, Patent Document 1). 2). As a method for producing tetrahydrocurcumin, a production method by hydrogenation of curcumin using a metal catalyst is known. However, using synthetic tetrahydrocurcumin produced by this method for food and drink is a problem in food hygiene. There is. As a method for producing edible tetrahydrocurcumin, a method for producing tetrahydrocurcumin in which microbial cells and curcumin are mixed and kept warm is known (for example, see Patent Document 3).

  However, the solubility of curcumin in water is as low as 0.1 μg / ml or less at room temperature, and when performing a fermentation treatment using microorganisms such as bacteria, curcumins that are hardly soluble in water are organic solvents that dissolve curcumins such as ethanol. First, it is used after being dissolved, but there are disadvantages that the type of organic solvent to be used is limited due to ingestion of the fermented product, and that when the amount used is increased, bacteria and the like are inactivated. Although an emulsification technique is known as a technique for dispersing a poorly water-soluble compound in water without using an organic solvent, it does not change the structure of the compound. As a method for obtaining tetrahydrocurcumin whose structure has been changed from curcumin, microorganisms are allowed to act on curcumin in the presence of an emulsion obtained by mixing and processing an oil and fat component, an emulsifier or a surfactant, and an aqueous medium. A method for producing a composition containing tetrahydrocurcumin has been reported (for example, see Patent Document 4), but further improvement in the conversion rate to tetrahydrocurcumin is desired.

  On the other hand, cyclodextrin is an oligosaccharide in which a plurality of glucopyranose groups are linked by α-1,4-glucoside bonds to form a ring, and a hydrophobic compound is encapsulated in the molecule by van der Waals bonds or hydrogen bonds. It is known to be used as a host for clathrate compounds in contact. A method of obtaining a curcumin-cyclodextrin complex in which curcumin extracted by contacting turmeric powder with carbon dioxide in a supercritical state is dissolved in a mixed solvent of water and ethanol and encapsulated in cyclodextrin (see, for example, Patent Document 5) ) Has been reported. However, these methods are intended to remove off-flavors and bitterness. By developing specific components, the antioxidant activity can be enhanced, and specific components can be selectively increased. It is not considered at all to utilize the fermented processed product as a food or food material.

JP-A-2-49747 Japanese Patent Laid-Open No. 2-51595 JP 11-235192 A JP 2003-33195 A JP-A-6-9479

  An object of the present invention is to provide a process for producing tetrahydrocurcumin capable of efficiently obtaining tetrahydrocurcumin safe as a food material or food from curcumin, a fermented processed product, a food material or food obtained. .

  As a method for obtaining tetrahydrocurcumin having a remarkable antioxidant action by reducing curcumin, the present inventors have used a method of fermentation of microorganisms as a method for producing tetrahydrocurcumin that is safe as a food material or food. As a result of earnest research on whether or not curcumin, which is sparingly soluble in water, can be applied to fermentation treatment of microorganisms in the presence of water, we added cyclodextrin to curcumin and conducted fermentation treatment. As a result, the inventors have obtained knowledge that tetrahydrocurcumins can be obtained very efficiently, and have completed the present invention.

  That is, the present invention relates to a fermented product characterized by containing a tetrahydrocurcumin obtained by adding a cyclodextrin to a curcumin and then performing a fermentation treatment. Preferably, the curcumin is represented by the formula (1). )

[Wherein, R ¹ , R ² , R ³ and R ⁴ independently represent a hydrogen atom, a hydroxy group or a lower alkoxy group. And the tetrahydrocurcumin is represented by the formula (2)

Wherein, R ^1, R ^2, R ³ and R ⁴ are the same meanings as R ^1, R ^2, R ³ and R ⁴ in Formula (1). The fermented processed product according to claim 1 (Claim 2) or the curcumin derived from a turmeric plant, wherein the fermented processed product according to claim 1 or 2 is derived from a turmeric plant (Claim 1). The fermented product (Claim 4) according to any one of claims 1 to 3, wherein the fermentation process is a process using a microorganism containing yeasts.

  The present invention also provides a method for producing a fermented product containing tetrahydrocurcumin, characterized in that a fermentation treatment is performed after adding cyclodextrin to curcumin (Claim 5), (1)

[Wherein, R ¹ , R ² , R ³ and R ⁴ independently represent a hydrogen atom, a hydroxy group or a lower alkoxy group. And the tetrahydrocurcumin is represented by the formula (2)

Wherein, R ^1, R ^2, R ³ and R ⁴ are the same meanings as R ^1, R ^2, R ³ and R ⁴ in Formula (1). The process for producing a fermented product containing tetrahydrocurcumin according to claim 5 (Claim 6) or the curcumin is derived from a turmeric plant. The method for producing a fermented processed product containing the tetrahydrocurcumin according to claim 5 or 6 (claim 7) or the fermenting process is a process using a microorganism containing yeasts. The present invention relates to a method for producing a fermented product containing any of the tetrahydrocurcumins (claim 8).

  Moreover, this invention relates to the foodstuff material or foodstuff (Claim 9) characterized by including the fermented material of any one of Claims 1-4.

  The method for producing a fermented product according to the present invention is safe as a food material or food because it can be obtained by fermenting microorganisms, unlike a method using a metal catalyst, and has a high yield of tetrahydrocurcumin. Can be obtained at a rate. The fermented product of the present invention has a high content of tetrahydrocurcumin having a remarkable antioxidant action, and has high utility value as a pharmaceutical composition having excellent antioxidant action, a food material, and a food material.

  The fermented product of the present invention is not particularly limited as long as it contains tetrahydrocurcumin obtained by fermentation after adding cyclodextrin to curcumin.

  The curcumin in the present invention is represented by the formula (1)

Wherein R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, a hydroxy group or a lower alkoxy group such as a methoxy group, an ethoxy group, a propyloxy group, or a butoxy group. These alkoxy groups may have a substituent such as an alkyl group. As curcumins, any one of these, or a mixture of two or more thereof may be used, and these may be used directly in the form of powder or the like or dissolved or dispersed in a solvent such as ethanol.

  Examples of such curcumins include 1,7-bis (4′-hydroxy-3′-methoxyphenyl) -1,6-heptadiene-3,5-dione (U1), 4-hydroxycinnamoyl (feruloyl) methane ( U2), bis (4-hydroxycinnamoyl) methane (U3), 1,7-bis (3 ′, 4′-dimethoxyphenyl) -1,6-heptadiene-3,5-dione (DMU1), 1,7 -Bis (3 ', 4'-dihydroxyphenyl) -1,6-heptadiene-3,5-dione (DHU1) and the like can be mentioned, specifically, curcumin powder (manufactured by Lion Corporation), etc. Can be used.

  The curcumin in the present invention may be derived from a turmeric plant. Specific examples of the turmeric plant include spring turmeric (Curcuma aromatica Salisbury) and autumn turmeric (Curcuma longa L.) that blooms in autumn, belonging to the genus Zingiberaceae Curcuma. The part to be used as such a turmeric plant may be any of leaves, stems, roots, etc., but the underground part such as rhizomes is suitable with a high content of curcumin, and even a living body is a dry body. However, a dried product is particularly preferable in terms of storage and the like, and a particle size of 0.1 to 3 mm is preferable because the progress of fermentation is promoted by mixing with microorganisms in the fermentation treatment.

  The cyclodextrin in the present invention is not particularly limited as long as it is an oligosaccharide in which a plurality of glucopyranose groups are bonded by α-1,4-glucoside bonds to form a ring, and α, β, γ, Any of δ and the like may be used, and specific examples include trade name: DEXIPEARL K-100 (Yokohama International Bio-Laboratory Co., Ltd.).

  Although the cyclodextrin can be added as it is, it can be added as a solution, and the solvent is not particularly limited, but it is preferable to use water in consideration of the fermentation treatment performed thereafter. The concentration of the cyclodextrin aqueous solution is 0.05 to 1% by weight, preferably around 0.1% by weight. The amount of cyclodextrin used is 0.05 to 10% by weight, preferably with respect to the curcumins. About 1% by weight.

  As the fermentation treatment in the present invention, microorganisms such as yeast, bacteria, actinomycetes, filamentous fungi, mushrooms, and algae can be used, and it is preferable to include yeasts, lactic acid bacteria, and the like as such microorganisms. Examples of yeasts include bacteria belonging to the genus Debaryomyces, Candida, and Saccharomyces. Examples of lactic acid bacteria include the genus Streptococcus and Lactobacillus. ), Leuconostoc, Pediococcus, Bifidobacterium, Tetragenococcus and the like. These fungi can be used alone or in combination. When used in combination, each fungus can be used after being cultured and mixed in advance before being added to the medium. The amount of these fungi used can be 2 to 500 parts by weight with respect to the curcumin. Fermentation of these fungi can be performed using a natural medium, semi-synthetic medium, synthetic medium, or the like used for normal culture in which these fungi can grow, and employing a liquid culture method, a stirring culture method, or the like as a fermentation format. In order to promote the progress of fermentation, it is preferable that the water is present in an amount of 1 to 1000 parts by weight, preferably about 100 to 1000 parts by weight with respect to the curcumins. The fermentation temperature is 10 to 80 ° C., preferably 10 to 60 ° C., particularly preferably 20 to 40 ° C., pH 2 to 11, pH 3 to 10, preferably pH 5 to 8. For adjusting the pH of the medium, ammonia water or An ammonium carbonate solution or the like can be used.

  In addition to the above microorganisms, a crude enzyme can be used for the fermentation treatment in the present invention, and examples of the crude enzyme include a crude enzyme of porcine small intestinal epithelium.

  As the fermentation treatment in the present invention, the fermentation time can be appropriately selected according to the progress of fermentation under conditions such as pH and the number of bacteria, and preference, but within 48 hours when the production scale is expanded, more preferably For example, in the case of a test tube level, if the fermentation temperature is 30 ° C. and the pH is 4 to 5, it is preferably about 1 hour.

  In such a fermentation treatment, a carbon source or a nitrogen source can be added as an assimilating agent for fungi or the like. Examples of the carbon source as an assimilating agent include starch, dextrin, sucrose, glucose, mannose, fructose, raffinose, rhamnose, inositol, lactose, xylose, arabinose, mannitol, molasses and the like. Furthermore, hydrocarbons, alcohols, organic acids and the like may be used depending on the assimilation ability of the bacteria. Examples of the nitrogen source include ammonium chloride, ammonium nitrate, ammonium sulfate, sodium nitrate, urea, peptone, meat extract, yeast extract, dry yeast, corn starch liquor, soybean flour, casamino acid and the like. In addition, other inorganic salts such as sodium chloride, potassium chloride, magnesium sulfate, calcium carbonate, potassium dihydrogen phosphate, ferrous sulfate, calcium chloride, manganese sulfate, zinc sulfate, copper sulfate, biotin, thiamine or nicotinic acid Minor components such as vitamins such as amino acids such as β-alanine or glutamic acid can be used as an assimilating agent. These assimilating agents may be used alone or in combination of two or more. The addition amount of these assimilating agents can be 1 to 5% by weight or the like per medium.

  After the fermentation is complete, the fermentation broth can be used as it is, or the fermentation broth can be concentrated, dried, frozen, refrigerated, freeze-dried, heated, pressurized, ultrasonically disrupted, treated with a surfactant or organic solvent, lysed enzyme, etc. Things are obtained. Formula (2) in which curcumin is converted in the fermented product

Wherein, R ^1, R ^2, R ³ and R ⁴ are the same meanings as R ^1, R ^2, R ³ and R ⁴ in Formula (1). ] The tetrahydrocurcumin represented by this is contained.

  The method for producing a fermented product containing the tetrahydrocurcumin of the present invention is not particularly limited as long as it is a method characterized by performing a fermentation treatment after adding cyclodextrin to curcumin. , Curcumins, and cyclodextrins can be the same as described above, and the fermentation treatment can include the same treatment as described above.

  Examples of the food material of the present invention include tablets, granules, capsules, etc. prepared from the fermentation processed product of the present invention itself, extracts extracted from the fermented processed product, tea bags, plastic bottles, cans, and tea leaves for drinks. In addition, there can be mentioned, for example, sprinkles obtained from the fermented product itself or granules produced from the extracted extract, and the food of the present invention includes the fermented product itself of the present invention, the extracted extract, Drinks in which granules are dissolved in drinking water, juice, etc., baked confectionery such as bread, cake, rice cracker, Japanese confectionery such as yokan, confectionery such as frozen confectionery, chewing gum, jelly, noodles such as udon and soba Fish paste products such as kamaboko, ham, fish sausage, seasonings such as miso, soy sauce, dressing, mayonnaise, sweetener, cheese, butter, yogurt, eye Cream, and dairy products of the pudding and the like, can be cited tofu, konjac, the food was blended with various side dishes such as other boiled.

  Further, the extract of the fermented product of the present invention can also be used as a pharmaceutical agent such as an antioxidant active composition, an anti-cataract agent, or a tumor suppressor, and in that case, a pharmaceutically acceptable normal carrier or binder In addition, various compounding ingredients for preparation such as a stabilizer, an excipient, a diluent, a pH buffer, a disintegrant, a solubilizer, a solubilizer, and an isotonic agent can be added. Such pharmaceutical dosage forms are generally used dosage forms such as powders, granules, capsules, syrups and suspensions, orally, or for example solutions, emulsions, suspensions, etc. In addition to the injection form, a parenteral dosage form can be used as an injection form, and an intranasal dosage form can be used as a spray form.

  EXAMPLES Hereinafter, although an Example demonstrates this invention more concretely, the technical scope of this invention is not limited to these illustrations.

[Manufacture of fermented products]
Debaryomyces hansenii (PRISCA, LACTO LABO) was cultured in YM medium (manufactured by Nissui) at 25 ° C for 2 days and centrifuged in a 50 ml selection tube at 3,000 rpm for 10 minutes to obtain bacterial cells. It was. Water was added to the obtained bacterial cells so that OD ₆₆₀ = 0.2 to 0.3 to prepare a bacterial suspension.

  An aqueous solution was prepared by dissolving 1 mg of cyclodextrin (trade name: Dexipearl K-100 (manufactured by Yokohama International Bio-Laboratory Co., Ltd.) in 1 ml of water.

  After adding 100 μl of the above cyclodextrin aqueous solution to 1 mg of curcumin (manufactured by Lion Corporation) to encapsulate curcumin, 1 ml of the above bacterial suspension was added. The shaking culture was performed at 30 ° C. for 1 hour using a shaking incubator (TAITEC). After heating to 121 ° C. in an autoclave to stop fermentation, tetrahydrocurcumin in the culture solution was measured using HPLC (CLASS-VP: manufactured by Shimadzu Corporation). The HPLC measurement conditions were as follows: Column: Develosil ODS-HG-5 ID 4.6 × 250 mm, solvent: acetonitrile: water = 50: 50 (v / v) (containing 0.1% TFA), flow rate: 1 ml / min, injection Amount: 10 μl, detection: performed at 280 nm. The results are shown in Table 1 and FIG.

  As a comparative example, except that cyclodextrin was not added, fermentation treatment was performed for 1 hour in the same manner as in Example 1, and tetrahydrocurcumin in the culture solution was measured. The results are shown in Table 1 and FIG.

  Moreover, except not adding a microbe, it shaked for 1 hour like Example 1, and measured the tetrahydrocurcumin in aqueous solution. The results are shown in Table 1 and FIG.

  From the results, it is clear that the fermented product of the present invention has a high production amount of tetrahydrocurcumin, and no tetrahydrocurcumin is produced when the fermentation treatment is not performed.

  The same treatment as in Example 1 was performed except that the fermentation treatment time was changed, and tetrahydrocurcumin in the culture solution was measured in the same manner as in Example 1. The results are shown in Table 2 and FIG. From the results, it is clear that the amount of tetrahydrocurcumin produced by fermentation for about 1 hour is the highest under these conditions.

It is a figure which shows the production amount of the tetrahydrocurcumin by the fermentation time of 1 hour in the fermentation processed material of this invention. It is a figure which shows the production amount of the tetrahydrocurcumin by the difference in the fermentation processing time in the fermentation processed material of this invention.

Claims (9)

A fermented product comprising tetrahydrocurcumin obtained by adding a cyclodextrin to a curcumin and then subjecting it to a fermentation treatment. Curcumin is represented by the formula (1)
[Wherein, R ¹ , R ² , R ³ and R ⁴ independently represent a hydrogen atom, a hydroxy group or a lower alkoxy group. And the tetrahydrocurcumin is represented by the formula (2)
Wherein, R ^1, R ^2, R ³ and R ⁴ are the same meanings as R ^1, R ^2, R ³ and R ⁴ in Formula (1). The fermented processed product according to claim 1, wherein The fermented processed product according to claim 1 or 2, wherein the curcumin is derived from a turmeric plant. The fermentation treatment product according to any one of claims 1 to 3, wherein the fermentation treatment is a treatment using a microorganism containing yeasts. A method for producing a fermented product containing tetrahydrocurcumin, comprising adding a cyclodextrin to curcumin and then performing a fermenting treatment. Curcumin is represented by the formula (1)
[Wherein, R ¹ , R ² , R ³ and R ⁴ independently represent a hydrogen atom, a hydroxy group or a lower alkoxy group. And the tetrahydrocurcumin is represented by the formula (2)
Wherein, R ^1, R ^2, R ³ and R ⁴ are the same meanings as R ^1, R ^2, R ³ and R ⁴ in Formula (1). The method for producing a fermented product containing tetrahydrocurcumin according to claim 5, wherein The method for producing a fermented product containing tetrahydrocurcumin according to claim 5 or 6, wherein the curcumin is derived from a turmeric plant. The method for producing a fermented product containing tetrahydrocurcumin according to any one of claims 5 to 7, wherein the fermentation treatment is a treatment using a microorganism containing yeasts. A food material or food comprising the fermented product according to any one of claims 1 to 4.