JP2001316259A - Preparation of polyphenols - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a preparation of polyphenols reducing astringency and bitterness derived from the polyphenols, and forming aqueous dispersion thereof excellent in stability. SOLUTION: This preparation of the polyphenols is obtained by the treatment of the first step for micronizing the polyphenols in an oil and fat containing a fatty acid ester of a polyhydric alcohol, and the second step for emulsifying the oil and fat containing the micronized polyphenols and obtained at the first step, in the presence of the fatty acid ester of the polyhydric alcohol to provide an oil-in-water type emulsion.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a preparation containing a polyphenol as a physiologically active ingredient, and to a food containing the preparation.

[0002]

2. Description of the Related Art Polyphenols are expected to be used in a wide range of fields such as pharmaceuticals, cosmetics, feeds, etc., in addition to being used for adding / enhancing physiological functions of foods or as antioxidants due to specific physiological actions. In particular, the research results of polyphenols in recent years are remarkable, and in addition to the anti-carcinogenic and anti-aging effects derived from the antioxidant effects of polyphenols, blood LDL lowering effect, blood pressure increase suppressing effect, intestinal regulating effect, sterilizing / antibacterial effect, Deodorizing effects have been reported. However, polyphenols have specific bitterness and astringency, so that they are limited in use for food applications, and are disadvantageous in that they are easily discolored by oxidation, heat and light and are unstable.

As a method for stabilizing polyphenols, a method of suppressing discoloration of polyphenols by blending a compound having two or more alcoholic hydroxyl groups (Japanese Patent Laid-Open No. Hei 6-239716); A method of cross-linking with a cross-linking agent such as succinyl or adipoyl chloride to prepare microcapsules based on the cross-linking has been proposed (Japanese Patent Application Laid-Open No. 8-508677). However, the composition prepared by the former method has polyphenols in a free and dissolved state,
Has intense astringency and bitterness derived from polyphenols,
Restricted for use in food applications. In the latter method, although the stability of the composition is improved, the microcapsules themselves are composed of a crosslinked polyphenol, so that the astringency and bitterness derived from polyphenols are not reduced. Compounds used as agents have disadvantages such as being restricted by the Food Sanitation Law.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide a water-dispersible polyphenol preparation which keeps polyphenols stable for a long period of time and which has excellent taste and bioabsorbability.

[0005]

Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that solid particles of polyphenols are finely divided in fats and oils containing polyhydric alcohol fatty acid esters. The process of the first step and the second step of emulsifying the oil or fat containing the finely divided polyphenols obtained in the first step into an oil-in-water type in the presence of a polyhydric alcohol fatty acid ester is more specific to polyphenols. Astringency and bitterness are masked, and excellent stability is imparted, and at the same time, it has unprecedented excellent bioabsorbability and bioavailability. The inventors discovered that improvements were made, and completed the present invention.

That is, the present invention provides a first step in which solid particles of polyphenols are refined in fats and oils containing a polyhydric alcohol fatty acid ester, and the oils and fats containing finely divided polyphenols obtained in the first step. The present invention relates to a polyphenol preparation obtained by a second step of emulsifying in the form of oil-in-water in the presence of a polyhydric alcohol fatty acid ester, and a food containing the polyphenol preparation.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The polyphenols in the present invention are not particularly limited as long as they can be ingested by the human body. Flavonoids such as flavone, flavonol, flavanone, isoflavone, anthocyanin, flavanol, and other non-flavonoids And derivatives thereof,
Polymers and the like may be used any of plants and plant extracts containing the above compound, but it is preferably a solid which is insoluble in fats and oils and is physically crushed by a laser diffraction type particle size distribution analyzer. It is preferable that the fine particles have an average particle diameter of 3 μm or less. Specific examples of the polyphenols are shown below, but are not limited thereto.

Specific examples of polyphenols include catechin, epicatechin, gallocatechin, catechin gallate,
Epicatechin gallate, gallocatechin gallate, epigallocatechin gallate, epigallocatechin, tannic acid,
Gallotannin, ellagitannin, caffeic acid, dihydrocaffeic acid, chlorogenic acid, isochlorogenic acid, gentisic acid, homogentisic acid, gallic acid, ellagic acid, rosmarinic acid, rutin, quercetin, quercetagine, quercetagetin, gossypetin, anthocyanin, leuco anthocyanin, proanthocyanidin , Enocyanine, and at least one or a mixture of two or more selected from derivatives, polymers, and stereoisomers thereof.

[0009] The plant containing a polyphenol in the present invention is not particularly limited. That is, the plant that performs photosynthesis generally contains polyphenols, so long as it can extract polyphenols and can extract the extract into the human body. Specific examples of plants are shown below, but are not limited thereto.

Specific examples of the plant include a camellia plant such as tea, a grape plant such as grape, a Rubiaceae plant such as coffee, a capitaceae plant such as cacao, and a Polygonaceae plant such as buckwheat.
Saxifragaceous plants such as gooseberries, blackcurrants, and red berries, ericaceae plants such as blueberries, white berries, black hackleberries, cranberries, and bilberries; gramineous plants such as red rice and purple corn; mulberry plants such as mulberry; and elders. Berries, honeysuckle family plants such as chrominacea, plums, European blackberries, loganberries, salmonberries,
Strawberry, strawberry, oak strawberry,
Rosaceae plants such as Dutch strawberry, black strawberry, morello cherry, yoshino cherry, yoshino cherry, sweet tea, apple, etc., enju, red beans, soybeans, tamarind, mimosa,
Leguminous plants such as pegua senyaku, yam plants such as purple yam, oyster plants such as oysters, asteraceous plants such as mugwort and spring chrysanthemum, Musaceae plants such as bananas, convolvulaceous plants such as yamakawalamurasakiimo, roselle etc. Malvaceae plants, Labiatae plants such as red perilla, cruciferous plants such as red cabbage and the like, depending on these plants fruit, pericarp,
Parts such as flowers, leaves, stems, bark, roots, tubers, seeds, seed coats and the like are arbitrarily selected. The form of the extract obtained from the plant may be a solid, preferably insoluble in fats and oils, and fine particles having an average particle size of 3 μm or less by a laser diffraction type particle size distribution analyzer by physical crushing. Those having the property that can be used are good.

The average particle size of the polyphenols refined by the first step of the present invention is not particularly limited, but is preferably 3 μm or less, more preferably 2 μm or less, further preferably 1 μm or less, and most preferably 0 μm or less. .5
μm or less. When the average particle size is larger than 3 μm,
If the surface of the fine particles is further coated with a fat or oil, the particle size becomes too large and the aqueous dispersibility is impaired. As for the physical crushing method, use of a wet crusher such as a bead mill may be mentioned, but it is not particularly limited as long as it has a capability of forming fine particles having an average particle size of 3 μm or less by a laser diffraction type particle size distribution analyzer. It does not do.

Although the content of the polyphenol of the present invention is not particularly limited, it is 1 to 70% by weight in the finely divided product.
Is more preferably 5 to 50% by weight, and still more preferably 10 to 40% by weight. When the content of the polyphenols is less than 1% by weight, the amount of the polyphenols, which is the main ingredient, becomes small, and the polyphenols are not used. On the other hand, when the content of the polyphenols is more than 70% by weight, the structural viscosity of the finely divided product becomes extremely high and the fluidity is lost, so that the subsequent processing characteristics are significantly narrowed.

The polyhydric alcohol fatty acid ester used in the first step of the present invention is not particularly limited as long as it can be provided to food, but a nonionic surfactant is preferably selected. Specific examples of the polyhydric alcohol fatty acid ester are shown below, but are not limited thereto.
Specific examples of polyhydric alcohol fatty acid esters include monoglycerin monofatty acid ester, monoglycerin difatty acid ester, monoglycerin fatty acid organic acid ester, polyglycerin fatty acid ester and polyglycerin condensed ricinoleate, particularly monoglycerin monostearate, Glycerin monooleate, monoglycerin monomyristate, monoglycerin monocaprylate, monoglycerin distearate, monoglycerol dioleate, monoglycerin stearate citrate,
Monoglycerin stearic acid acetate, monoglycerin stearic acid succinate, monoglycerin caprylic acid succinate, monoglycerin stearic acid lactic acid ester, monoglycerin stearic acid diacetyltartaric acid ester, polyglycerin having an average degree of polymerization of 2 to 10 and carbon number Fatty acid ester of 6 to 22 and average degree of polymerization of 2
Glycerin fatty acid esters such as polyglycerin having a condensation degree of 2 to 4 and polyglycinoleic acid having a condensation degree of 2 to 4, propylene glycol fatty acid esters such as propylene glycol monostearate and propylene glycol monooleate, sorbitan distearate, One or a mixture of two or more sorbitan fatty acid esters such as sorbitan tristearate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, etc., is more preferable. One or a mixture of two or more selected from glycerin fatty acid esters, more preferably polyglycerin fatty acid ester and polyglycerin condensed ricinoleate, particularly average weight A polyglycerol having a degree of 2 to 10 and a fatty acid ester having 6 to 22 carbon atoms, and a polyglycerin having an average degree of polymerization of 2 to 10 and an ester of polyricinoleic acid having a degree of condensation of 2 to 4 or a mixture of two or more kinds thereof. good. When a polyglycerin fatty acid ester is used, the degree of esterification is preferably 75% or more, or the HLB is preferably 4 or less.

The polyhydric alcohol fatty acid ester used in the first step of the present invention is blended in an amount of 0.1 to 100% by weight, preferably 0.2 to 50% by weight, more preferably 0.5 to 20% by weight based on the fat or oil. % By weight is good. 0.1% by weight
If the amount is less than 100%, it is impossible to sufficiently disperse the solid fine particles of the polyphenols. If the amount is more than 100% by weight, when the composition is newly dispersed in an aqueous system, the polyphenols contained therein are eluted by emulsification inversion. Are likely to occur, which hinders the construction of a stable W / O / W dispersion system.

The fats and oils used in the first step of the present invention are not particularly limited. However, if the fats and oils which are in a liquid state at normal temperature are used, solid / liquid dispersion cannot be maintained in the aqueous dispersion state of the polyphenol preparation of the present invention. Since the liquid / liquid emulsified state is obtained and the stability is lowered, it is preferable to form a solid at room temperature, and a material having a melting point of 30 ° C. or higher is usually used. From the viewpoint of the masking effect of the astringent / bitter taste of the polyphenols and the stability of the polyphenols preparation of the present invention against physical stress during aqueous dispersion, the melting point is more preferably 35 ° C.
The melting point is more preferably 40 ° C. or higher, and most preferably 50 ° C. or higher. Specific examples of fats and oils are shown below, but are not limited thereto. Specific examples of oils and fats include soybeans, rice, rapeseed, cacao, palm, sesame,
Common vegetable oils and fats obtained from palm, cotton, peanut, avocado, kapok, poppy, burdock, wheat, evening primrose, tsubaki, corn, sunflower, etc. and their hardened products and cows, milk, pork, sardines, mackerel, shark And animal fats and oils obtained from seafood, saury, tara and the like, and hardened products thereof. One or a mixture of two or more kinds of these fats and oils can be used. In addition, even if phospholipids, sterols, waxes, and the like originally contained therein coexist, there is no problem.

In the first step of the present invention, there is obtained a state in which the finely divided polyphenol solid particles are uniformly dispersed in a fat or oil containing a polyhydric alcohol fatty acid ester (hereinafter, referred to as a finely divided product). In the second step of the present invention, a system capable of stably dispersing the finely divided product in an aqueous system using a polyhydric alcohol fatty acid ester is constructed. Specifically, in the second step of the present invention, the finely divided product is liquefied by heating at a temperature equal to or higher than the melting point of fats and oils contained in the finely divided product, and emulsified in an aqueous system using a polyhydric alcohol fatty acid ester, and then cooled to room temperature. Cool.

The polyhydric alcohol fatty acid ester used in the second step of the present invention is not particularly limited as long as it can be provided to foods. Specific examples of polyhydric alcohol fatty acid esters include monoglycerin monofatty acid ester, monoglycerin difatty acid ester, monoglycerin fatty acid organic acid ester, polyglycerin fatty acid ester and polyglycerin condensed ricinoleate, particularly monoglycerin monostearate, Glycerin monooleate, monoglycerin monopalmitate, monoglycerin monomyristate, monoglycerin monocaprylate, monoglycerin monolaurate, monoglycerin monobehenate, monoglycerin monoerucate, monoglycerin Distearate ester, monoglycerin dioleate ester, monoglycerin dicaprylate ester, monoglycerin dilaurin Ester, monoglycerin tallow hardened oil fatty acid ester, monoglycerin rapeseed hardened oil fatty acid ester, monoglycerin soybean hardened oil fatty acid ester, monoglycerin cottonseed oil fatty acid ester, monoglycerin safflower oil fatty acid ester, monoglycerin stearate citrate ester, monoglycerin Stearic acid acetate, monoglycerin stearic acid succinate, monoglycerin caprylic acid succinate, monoglycerin stearic acid lactate, monoglycerin stearic acid diacetyl tartaric acid ester, polyglycerin having an average degree of polymerization of 2 to 10 and carbon number of 6 to 6 22 fatty acid esters and an average degree of polymerization of 2
Glycerin fatty acid esters such as polyglycerin 10 and polyricinoleic acid ester having a degree of condensation of 2 to 4, and propylene glycol fatty acid esters such as propylene glycol monostearate, propylene glycol monooleate and propylene glycol monobehenate. Sorbitan monostearate, sorbitan sesquistearate, sorbitan distearate, sorbitan tristearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate,
Sorbitan monolaurate ester, sorbitan monomyristate ester, sorbitan monopalmitate ester, sorbitan monobehenate ester, sorbitan monoerucate ester, etc., sorbitan fatty acid esters, sucrose palmitate ester, sucrose stearate ester, etc. Sugar fatty acid esters, soy lecithin,
Examples thereof include, but are not limited to, lecithins such as egg yolk lecithin and enzyme-decomposed lecithin, and saponins such as enjusaponin, quillajasaponin, soybean saponin, and yucca saponin. .

The polyhydric alcohol fatty acid ester used in the second step of the present invention is blended in an amount of 0.1 to 100% by weight, preferably 0.2 to 50% by weight, based on the refined product obtained in the first step of the present invention. And more preferably 0.5 to 20% by weight. If the added amount is less than 0.1% by weight, it is impossible to sufficiently disperse the finely divided product in an aqueous system. If the added amount is more than 100% by weight, the contained polyphenol fine particles are eluted due to emulsification phase inversion. Easy and stable W / O
/ W dispersion system is hindered.

The polyphenol preparation of the present invention is prepared as described above. In addition, in the second step of the present invention, a stabilizer, a preservative, a pH adjuster and the like generally used in foods are blended to further improve aqueous dispersibility and storage stability. Can be better,
A water-soluble excipient may be compounded, and dried into powder by spray drying or the like. Further, the powder product can be formed into granules using a granulator such as a flow coater. The dried and powdered polyphenol preparation of the present invention is extremely stable in storage stability, and shows the same good dispersibility even when dispersed again in an aqueous system.

The polyphenol preparation of the present invention may be taken orally as it is as a food, or may be dairy products such as milk, milk drink, cheese, powdered milk, juice, juice, etc.
Soft drinks such as lactic acid drinks and lactic acid drinks, favorite drinks such as coffee, tea, green tea, candy, gum, chocolate, cookies, biscuits, Japanese sweets, rice cakes, sweets such as cakes and pies, bread, noodles and cakes Flour products such as mix, ice cream, ice dessert, pudding, jelly,
Desserts such as yogurt and jam, seasonings such as soy sauce, sauces, miso, sweeteners, spices, dressings, soups such as miso soup, noodle soup, soups, fish ham and sausage, fishery products, fishery processing such as canned seafood It can also be blended in products, pickles, processed agricultural products such as canned agricultural products and fruits, processed livestock products such as livestock meat hams and sausages, livestock meat canned foods, and other various foods. Hereinafter, the present invention will be described with reference to Examples and Test Examples, but the present invention is not limited thereto.

[0021]

Example 1 <Step 1> Example 1 <Pulverized Polyphenol> 52.5 parts by weight of rapeseed extremely hardened oil (melting point 65 ° C.) and polyglycerin fatty acid ester (Sun Fat PS-66,
12.5 parts by weight of esterification degree 75%, HLB = 4, manufactured by Taiyo Chemical Co., Ltd.) were mixed and melted by heating, and 5.0 parts by weight of polyglycerin condensed ricinoleate (Sunsoft 818H, manufactured by Taiyo Chemical Co., Ltd.) ) Was mixed, and while maintaining the temperature at 65 ° C to 70 ° C with hot water bath, an oily suspension to which 30 parts by weight of tea polyphenol (Sanphenon DCF-1, manufactured by Taiyo Kagaku Co., Ltd.) was added was prepared. (Manufactured by Shinko Pantech Co., Ltd.) to obtain a finely divided polyphenol having an average particle size of tea polyphenol of 1.0 μm as measured by laser diffraction type particle size distribution.

Example 2 <finely refined polyphenol> 50.75 parts by weight of hardened coconut oil (melting point: 36 ° C.) was heated and melted, and polyglycerin condensed ricinoleate 1.7 was obtained.
5 parts by weight (Sunsoft 818DG, manufactured by Taiyo Kagaku Co., Ltd.) are mixed, and 35 parts by weight of grape seed polyphenol (Gravinol S, manufactured by Kikkoman Corporation) are added while maintaining the temperature at 65 ° C. to 70 ° C. in hot water. The oily suspension was prepared, applied to a Dynomill (manufactured by Shinmaru Enterprises Co., Ltd.), and heated and melted in advance when the average particle size of the grape seed polyphenol became 0.8 μm by laser diffraction type particle size distribution measurement. Polyglycerin fatty acid ester (Sun Fat PS-6)
8, 12.5 parts by weight of esterification degree 100%, HLB = 3, manufactured by Taiyo Chemical Co., Ltd.) were mixed to obtain a finely divided polyphenol.

Example 3 <Further refined polyphenol> 48 parts by weight of purified tallow (melting point 45 ° C.) was heated and melted, and 2 parts by weight of polyglycerin condensed ricinoleate (Sunsoft A-Z2E; 0.5 part by weight, Sunsoft) 818S
X; 1.5 parts by weight, manufactured by Taiyo Kagaku Co., Ltd.), and while maintaining the temperature at 65 ° C. to 70 ° C. in hot water bath, 40 parts by weight of epigallocatechin gallate (purity 95%, manufactured by Taiyo Kagaku Co., Ltd.) Was added to an oily suspension, which was applied to a ready mill (manufactured by Imex Co., Ltd.), and was heated and melted in advance when the average particle size of epigallocatechin gallate became 0.3 μm by laser diffraction type particle size distribution measurement. Polyglycerin fatty acid ester (Sunsoft A-1)
86E, esterification degree 86%, HLB = 4, manufactured by Taiyo Kagaku Co., Ltd.) 10 parts by weight were mixed to obtain a finely divided polyphenol.

<Second Step> Example 4 <Polyphenol Preparation> 200 parts by weight of water was previously heated to 65 to 70 ° C., and 52.7 parts by weight of dextrin (BLD No. 8) was stirred with a homomixer. , Sanmatsu Kogyo Co., Ltd.), 15 parts by weight of acid casein (ACID CASEIN EDIBLE)
30/60 MESH, manufactured by Megre Corporation), 1 part by weight of sodium carbonate, 0.6 parts by weight of glycerin fatty acid organic acid ester (Sunsoft 641C, manufactured by Taiyo Chemical Co., Ltd.), 0.7 parts by weight of polyglycerin fatty acid ester (Sunsoft Q
-18S (manufactured by Taiyo Kagaku Co., Ltd.) in order, completely dissolved, and subsequently stirred with a homomixer. 30 parts by weight of the finely divided polyphenol product of Example 1 previously heated and melted while maintaining at 65 to 70 ° C. Slowly and emulsify,
Thereafter, it was dried and powdered by spray drying to obtain a powdered product of an oil-in-water dispersion type oil- and fat-coated polyphenol preparation.

Example 5 <Preparation of polyphenols><Preparation of polyphenols>
Heat to 65 ° C and stir with a homomixer
46 parts by weight of oligosaccharide (Cupoligo P, manufactured by Nisshin Sugar Co., Ltd.), 12 parts by weight of acid casein (ACID CASEI
N EDIBLE 30 / 60MESH, manufactured by Megre Corporation), 0.8 parts by weight of sodium carbonate, 0.5 parts by weight of glycerin fatty acid organic acid ester (Sunsoft 621B, manufactured by Taiyo Chemical Co., Ltd.), 0.7 parts by weight of polyglycerin fatty acid ester (Sunsoft Q-182S, manufactured by Taiyo Kagaku Co., Ltd.) was added in sequence, completely dissolved, and subsequently stirred with a homomixer. The polyphenol fine particles of Example 2 previously heated and melted while maintaining at 55 to 65 ° C. Then, 40 parts by weight of the compound were gradually added and emulsified, and then completely cooled to room temperature to obtain an oil-in-water dispersion type oil / fat-coated polyphenol preparation.

Example 6 <Polyphenol preparation> 200 parts by weight of water was previously heated to 60 to 70 ° C., and 10 parts by weight of enzymatically decomposed guar gum (Sunfiber, Taiyo Kagaku Co., Ltd.) while stirring with a homomixer. 15 parts by weight of oligosaccharide (Cupoligo P, manufactured by Nisshin Sugar), 13 parts by weight of acid casein (ACID CASEIN EDIBL)
E 30/60 MESH, manufactured by Maigret Co.), 0.8 parts by weight of sodium carbonate, glycerin fatty acid organic acid ester 0.
5 parts by weight (Sunsoft 621G, manufactured by Taiyo Kagaku Co., Ltd.) and 0.7 parts by weight of polyglycerin fatty acid ester (Sunsoft A-141E, manufactured by Taiyo Kagaku Co., Ltd.) were sequentially added and completely dissolved. Stirring, 60
While maintaining the temperature at ７０70 ° C., 60 parts by weight of the finely divided polyphenol of Example 3 previously heated and melted were gradually added and emulsified, and then cooled to room temperature. A powdery product of a droplet-dispersed fat / oil-coated polyphenol preparation was obtained.

Example 7 <Food containing polyphenol preparation of the present invention> Wheat flour 100 g, margarine 60 g, powdered sugar 40 g, powdered salt 1 g, baking powder 1.6 g, whole egg 30 g, water 1
0 g and 1 g of the polyphenol preparation of Example 6 (228 mg as epigallocatechin gallate) were mixed to obtain a cookie dough. After the mold was released, the mixture was baked at 180 ° C. for 11 to 12 minutes to obtain a polyphenol-added cookie.

Example 8 <Food Containing Polyphenol Preparation of the Present Invention> 98 parts by weight of the polyphenol preparation of Example 5 were mixed with spore-forming lactic acid bacteria (Lacris S, manufactured by Sankyo Co., Ltd.) and a flow coater (Freund Sangyo) was used. (1), and granulated while spraying 20 parts by weight of 1% dextrin (BLD No. 8, manufactured by Sanmatsu Kogyo Co., Ltd.) to obtain a granular polyphenol supplement.

Test Example 1 <Water-based dispersibility of polyphenol preparation> 0.5 g of the polyphenol preparation of the present invention described in Example 4 was added to 100 mL of water at 20 ° C., lightly stirred, and immediately after stirring and after 1 day at room temperature. Was confirmed in a dispersion state in water.
As a control, the tea polyphenols used in Comparative Example 1 and Example 1 shown below were used so that the tea polyphenol content was the same. Table 1 shows the results. <Comparative product 1> Heat-dissolve 50 parts by weight of rapeseed extremely hardened oil (melting point 65 ° C) and 10 parts by weight of polyglycerin condensed ricinoleate (Sunsoft 818H, manufactured by Taiyo Chemical Co., Ltd.). 40 tea polyphenols used in Example 1
After addition by weight and mixing, the mixture was sprayed into a room maintained at 20 ° C. by a nozzle type spraying device to obtain fat-coated polyphenol particles having a particle size of 200 μm to 500 μm.

[0030]

[Table 1]

From Table 1, it was confirmed that the comparative product 1 was stable because no polyphenol was eluted in water since there was no coloring of water, but it was not dispersed in water at all. However, the polyphenol preparation of Example 4 showed extremely good water dispersibility and good stability even though the tea polyphenol was coated on the hardened palm oil like the comparative product 1. .

Test Example 2 <Stability of polyphenols in polyphenol-added cookies> The polyphenol-added cookies obtained in Example 7 and the comparative cookies shown below were stored in a dark place at 50 ° C for 2 months, and immediately after baking. Cookies, cookies one month after storage and cookies two months after storage,
The epigallocatechin gallate content was measured in each case. That is, 15 g of a cookie immediately after baking, and 15 g of a cookie at a lapse of one month and two months after storage, were degreased with n-hexane, and then methanol / water / phosphoric acid (50/50 /
0.1) was added, and the mixture was crushed for 5 minutes in a Hiscotron (Nichion Medical Science Instrument Co., Ltd.). 1 using a volumetric flask
After adjusting to 00 mL, 1 mL was collected and filtered through a 0.45 μm filter (Advantech Toyo Co., Ltd.) to obtain a cookie extract. Next, the content of epigallocatechin gallate in the cookie extract was quantified by high performance liquid chromatography (JASCO Corporation) to calculate the residual ratio of polyphenol. The residual ratio was calculated assuming that the polyphenol extraction rate from the polyphenol preparation of Example 4 was 100%. The results are shown in FIG. For the measurement by high performance liquid chromatography, column: CAPCELLLPAK C1
8 UG120 S3, (Shiseido Co., Ltd.), column temperature: 40 ° C., flow rate: 0.8 mL / min, mobile phase: methanol / water / phosphoric acid (50/50 / 0.1), detection: U
The test was performed under the condition of V280 nm. <Comparative cookie> Polyphenol 2 used in Example 3 instead of the polyphenol preparation used in Example 7
Cookies were prepared using 40 mg.

From the results shown in FIG. 1, it was found that the polyphenol preparation of the present invention has extremely high thermal stability even in the baking operation of baked confectionery and the like, and also has good long-term storage stability thereafter.

Test Example 3 <Effect of Reducing Astringency Using Polyphenol Preparations> The astringency of the polyphenol preparations obtained in Examples 4 and 5 was evaluated using a panel of 20 persons. Sensory evaluation was performed. The sensory evaluation test was conducted in Examples 4 and 5.
5 mL of an aqueous dispersion of the polyphenol preparation in the mouth
After including for 0 second, the swallow was performed to evaluate the astringency. still,
The sensory evaluation was performed using the tea polyphenol (Comparative Product 2) used in Example 1 as a comparative control of Example 4 and the grape seed polyphenol (Comparative Product 3) used in Example 2 as a comparative control of Example 5. . The results are shown in Table 2, FIG.
The results are shown in Table 3 and FIG. The numerical values indicate the average of the evaluation points. still,
The evaluation score of astringency was determined as follows. $ 0: no astringency at all, 1 point: almost no astringency, 2 points: slight astringency, 3 points: strong astringency, 4 points: very strong astringency. ｝

[0035]

[Table 2]

[0036]

[Table 3]

From Table 2, FIG. 2, Table 3, and FIG.
In cases 3 and 3, the average sensory evaluation score was
The polyphenols preparations of Examples 4 and 5 were tested at 10 times the concentration (2% as the tea polyphenol content and the grape seed polyphenol content) while the score was higher than the score (the score of feeling slightly astringent). Even if
95% of panelists set the sensory evaluation point to 0 point (feel no astringency). Even when the polyphenol preparations of Examples 4 and 5 were taken as they were without being dispersed in water, the average sensory evaluation score was 1.35 points, respectively.
1.20 points. Therefore, it is clear that the polyphenol preparation of the present invention does not give astringency despite being completely dispersible in water.

Test Example 4 <Artificial digestion test of polyphenol preparation> Using the polyphenol preparation of Example 4, an artificial gastric juice of the first solution and an artificial test of the second solution of the test solution of the Japanese Pharmacopoeia, 10th edition, dissolution test method An artificial digestion test was performed using intestinal juice. The content of epigallocatechin gallate released into the artificial digestive juice was measured, and the polyphenol release rate in the artificial digestive juice was calculated. As a result, the release rate was 2.3% in the artificial gastric juice, whereas the release rate was 89.8% in the artificial gastric juice. This indicates that the microcapsules with the oil coating layer uniformly coated on the entire peripheral surface of the polyphenol fine particles exist extremely stably until reaching the intestinal tract, and release polyphenols after reaching the intestinal tract It has the property of having

Test Example 5 <Bioabsorbability and Bioavailability of Polyphenol Preparation> The polyphenol preparation of the present invention has a microcapsule structure in which a uniform oil / fat coating layer is formed on the entire peripheral surface of polyphenol fine particles. Therefore, the preparation is excellent in stability and astringency masking effect. Therefore, it is necessary to confirm again the bioabsorbability and bioavailability when actually administered orally to the living body. Bioabsorbability and bioavailability tests were performed according to the method of Nakagawa et al.
gric. Food Chemi. , 1999,
47, 3967-3973). That is,
Thirty healthy men (23-48 year-old non-smokers) refrained from eating and drinking tea and tea-containing components for 12 hours before administration of the polyphenols preparation, and half of the 15 teas of Example 4 The polyphenol preparation containing polyphenol and the tea polyphenol used in Example 1 as a control for the remaining half of the 15 subjects were each 254 mg in total catechin content (82 g in epigallocatechin gallate content).
g) orally. Blood was collected immediately before oral ingestion and one hour after ingestion, and serum was separated, and then the epigallocatechin gallate content and the phospholipid peroxide content in the serum were measured. The epigallocatechin gallate content in serum is shown in Table 4 and FIG. 4, and the phospholipid peroxide content in serum is shown in Table 5 and FIG.

[0040]

[Table 4]

[0041]

[Table 5]

From Table 4 and FIG. 4, it was confirmed that the polyphenol preparation of the present invention of Example 4 had the same bioabsorbability as the control product. Further, from Table 5 and FIG. 5, a decrease in the phospholipid peroxide in the serum was confirmed. This is because despite the fact that the polyphenol preparation of the present invention has a microcapsule structure in which a uniform oil / fat coating layer is formed on the entire peripheral surface of the polyphenol fine particles, the bioabsorbability and bioavailability of the polyphenol are reduced. And that the microcapsules according to the present invention do not cause any obstacles.

[0043]

EFFECT OF THE INVENTION The polyphenol preparation of the present invention has a microcapsule structure in which a uniform oil / fat coating layer is formed on the entire surface of the fine particles of the polyphenol, and exhibits excellent aqueous dispersibility. This makes it possible to provide an aqueous dispersion preparation which is extremely stable and does not have astringency or bitterness. Furthermore, the polyphenol preparation of the present invention constructs a system for stably delivering polyphenols from food processing to oral ingestion, bioabsorption, and utilization in living organisms, and is extremely significant in industry.

[0044]

[Brief description of the drawings]

FIG. 1 is a graph showing heat resistance and storage stability of a polyphenol preparation.

FIG. 2 is a graph showing the astringency-reducing effect of a tea polyphenol preparation.

FIG. 3 is a graph showing the astringency-reducing effect of a grape seed polyphenol preparation.

FIG. 4 shows the bioabsorbability of a polyphenol preparation.

FIG. 5 is a diagram showing the bioavailability of a polyphenol preparation.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI theme coat ゛ (Reference) A61K 47/44 A61K 47/44 A61P 9/12 A61P 9/12 35/00 35/00 (72) Inventor Reka Raju Jenja 9-5 Akabori Shinmachi, Yokkaichi City, Mie Prefecture (72) Inventor Masahiro Yamazaki 9-5 Akabori Shinmachi, Yokkaichi City, Mie Prefecture F-term in Taiyo Chemical Co., Ltd. (Reference) 4B018 LB01 MD08 MD59 ME04 ME06 ME08 ME10 ME11 4B032 DB21 DK06 DK10 DK18 DK29 DL07 DL08 4C076 AA17 BB01 DD46F EE51 FF16 FF52 GG45 4C086 AA01 BA08 MA21 MA52 NA03 NA09 ZA36 ZB21 ZB26 ZB26B ABZ AB12 MAB

Claims (4)

[Claims] 1. A first step in which polyphenols are refined in a fat or oil containing a polyhydric alcohol fatty acid ester, and the fat or oil containing the finely divided polyphenols obtained in the first step is polyvalent. A polyphenol preparation obtained by the second step of emulsifying in the form of oil-in-water in the presence of an alcohol fatty acid ester. 2. The polyphenol preparation according to claim 1, wherein the polyphenols refined in the first step are solids having an average particle size of 3 μm or less. 3. The polyphenol preparation according to claim 1, wherein the melting point of the fat or oil is 30 ° C. or higher. 4. A food comprising the polyphenol preparation according to claim 1.