TWI786105B - Agent for lowering the amount of phenolic compounds in a living body - Google Patents

Abstract

[Problem] The problem is to provide an agent for reducing phenolic compounds in vivo and a food and drink for reducing phenolic compounds in vivo containing it. [Solution] By providing an agent for reducing phenolic compounds in vivo containing the branched α-glucan mixture characterized by the following (A) to (C) as an active ingredient, and an agent for reducing phenolic compounds in vivo containing the same (A) with glucose as the constituent sugar, (B) with non On the reducing terminal glucose residue, a branched structure with a glucose polymerization degree of 1 or higher connected by bonds other than α-1,4 bonds, (C) Isomaltose is generated by digestion with isomaltosetranase.

Description

Phenolic compound reducer in the body

The present invention relates to an agent for reducing phenolic compounds in living organisms. Specifically, it relates to an agent for reducing phenolic compounds in living organisms that can improve intestinal flora and reduce phenolic compounds in living organisms after being ingested by humans, and a biological agent containing the same. Diet for reducing phenolic compounds in the body.

In the intestines of humans (especially the large intestine), various bacteria (intestinal bacteria) are inhabited, forming a bacterial group called the intestinal flora (enterobacteria). The intestinal flora is considered to be composed of more than 100 species and 100 trillion intestinal bacteria, and is known to be closely related to the health of humans (hosts). Intestinal bacteria multiply by feeding on food residues that humans cannot digest or secretions from the digestive tract, etc., and are excreted as feces.

As bacteria constituting the intestinal flora, there are known bifidobacterium (Bifidobacterium), Bacteroides (Bacteroides), Eubacterium (Eubacterium), Clostridium (Clostridium), Escherichia coli, Lactobacillus, Enterococcus, etc. Although the balance of bacteria in the intestinal flora varies among individuals, it is considered that the balance of the person itself is almost unchanged in health from neonatal to adulthood. However, it is said that due to various factors such as stress, overwork, overeating/overeating, partial eclipse, climate/temperature, medicine, infection, aging, etc., the balance breaks down, and good bacteria such as Bifidobacteria decrease, and the capsules are produced. When bad bacteria such as Clostridium perfringens and coliform bacteria increase, it will cause various diseases such as diarrhea, constipation, infection caused by weakened immunity, and cancer caused by increased intestinal spoilage products.

Intestinal environment is not only related to various diseases, but also considered to be related to aging. In the elderly, it is considered that the number of Bifidella bacteria decreases, and the intestinal flora is disordered. It is said that if the intestinal flora deteriorates, there is a possibility of promoting aging. Bad bacteria in the intestinal tract produce harmful spoilage products (ammonia, amine compounds, phenolic compounds, indole compounds, etc.). These spoilage products are considered to cause direct damage to the intestinal tract, and some of them are absorbed into the blood and circulated in the body, which is also related to the onset of various diseases and rough skin.

As a method of improving intestinal flora, the method of taking probiotics or prebiotics is widely known. Probiotics refer to living microorganisms that improve the intestinal environment and have intestinal regulation or immune regulation effects, or foods that contain the microorganisms in a living state, which are beneficial to humans and are derived from dairy products, etc. Bacteria in the form of ingestion. On the other hand, prebiotics refer to the selective nutrient source of beneficial bacteria that are not decomposed/absorbed in the upper digestive tract, and are symbiotic in the large intestine, promote their proliferation, and improve the composition of intestinal flora to become healthy Sexual balance, and there are food ingredients for maintaining human health enhancement. So far, known oligosaccharides (galactooligosaccharides, fructooligosaccharides, soybean oligosaccharides, lactooligosaccharides, xylooligosaccharides, isomaltooligosaccharides, raffinose, lactulose, coffee bean mannanoligosaccharides sugar, gluconic acid, etc.) or dietary fiber (polydextrose, inulin, etc.) as food ingredients satisfying the requirements for prebiotics.

It can be considered that if the intake of probiotics or prebiotics improves the intestinal flora, the amount of the aforementioned harmful intestinal spoilage products (ammonia, amine compounds, phenolic compounds, indole compounds, etc.) can be reduced. In Non-Patent Documents 1, 4, and 5, etc., it is reported that when rats/mice are fed with a feed containing tyrosine, which is a raw material of phenol and p-cresol, which are intestinal spoilage products, if they ingest galactose Oligosaccharides and/or lactic acid bacteria/Bifidelia fermented milk, the phenol and p-cresol in serum will be reduced. In addition, non-patent document 2 reports that phenols produced by intestinal bacteria have adverse effects on the skin of hairless mice, and non-patent document 3 reports that phenols produced by intestinal bacteria inhibit human Differentiation of fibroblasts in skin. Also, in Non-Patent Document 6, it is reported that when rats bred with a feed containing tyrosine ingest high-amylose starch, the increase in p-cresol in vivo is suppressed, and further, in Non-Patent Document 7, it is reported that Fermented milk containing Bifidobacteria can improve the intestinal environment of humans, reduce phenolic compounds in the blood, and maintain the skin's cutin moisture content and other cosmetic effects.

However, in Non-Patent Document 6, in a test in which rats were ingested inulin known as one of the dietary fiber and prebiotics, it was reported that inulin did not show the effect of reducing p-cresol, so although it can improve intestinal The probiotics or prebiotics in the flora do not necessarily reduce the phenolic compounds of harmful metabolites in the living body. Under such circumstances, if a water-soluble dietary fiber material that functions as a low-sweet or tasteless prebiotic that is widely used and can be easily and safely taken continuously on a daily basis is provided, and in order not only to improve the intestinal flora, Furthermore, it would be extremely useful to be a novel material that can reduce phenolic compounds in vivo, such as phenol and p-cresol, which are produced as spoilage products in the intestine. [Prior art literature] [Non-patent literature]

[Non-Patent Document 1] Kawakami et al., "J. Nutr. Sci. Vitaminol.", Vol. 51, pp. 182-186 (2005) [Non-Patent Document 2] Iizuka et al., "Microbial Ecology in Health and Disease", Vol. 21, pp. 50-56 (2009) [Non-Patent Document 3] Iizuka et al., "Microbial Ecology in Health and Disease", Vol. 21, pp. 221-227 (2009) [Non-Patent Document 4] Kawakami et al. , "Yakult Research Institute Research Report Collection", No. 29, pp. 15-26 (2010) [Non-Patent Document 5] Ishii et al., "FRAGRANCE JOURNAL", No. 5 (2014) [Non-Patent Document 6] Chen (Chen) et al., "Luminacoid Research", Vol. 20, No. 1, pp. 31-38, (2016) [Non-Patent Document 7] Yakult Co., Ltd. Headquarters, Press Release, "Bifides fermented milk Improve rough skin", February 4, 2013

[Problem to be Solved by the Invention]

The subject of the present invention is to provide human beings with the effect of improving the intestinal flora and reducing phenolic compounds in the body after ingestion. It has a wide range of applications due to its low sweetness or tasteless, and it can be easily and safely continued to ingest on a daily basis. The substance is an agent for reducing phenolic compounds in vivo as an active ingredient, and a food and drink for reducing phenolic compounds in vivo containing it. [Means to solve the problem]

As a result of repeated efforts to solve the above problems, the present inventors found that the branched α-glucan mixture previously disclosed by the applicant in the International Publication No. WO2008/136331 pamphlet is specifically based on glucose. Constituent sugars that have bonds other than α-1,4 bonds on the non-reducing terminal glucose residues of straight-chain glucans (glucan) with a glucose polymerization degree of 3 or more linked by α-1,4 bonds The branched structure with a glucose polymerization degree of 1 or more is connected by knots, and a branched α-glucan mixture of isomaltose is produced by digestion with isomaltodextranase. When ingested, it not only improves the intestinal tract Bacterial flora, and the effect of significantly reducing the phenolic compounds in the living body. Based on this novel knowledge, the inventors of the present invention have established a biophenolic compound reducing agent that uses the branched α-glucan mixture that is low in sweetness or tasteless and widely used as an active ingredient, and a product containing it. A diet for reducing phenolic compounds in the living body has been completed.

That is, the present invention solves the above-mentioned problems by providing an agent for reducing phenolic compounds in vivo, which contains a mixture of branched α-glucans having the following characteristics (A) to (C) as an active ingredient. (A) Glucose is the constituent sugar, (B) There is a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, -A branched structure with a glucose polymerization degree of 1 or higher linked by bonds other than 1, 4 bonds, (C) Isomaltose is produced by digestion with isomaltosetranase.

The branched α-glucan mixture with the above-mentioned characteristics is α-glucan obtained from starch and the like. It is not only a safe edible material, but also low-sweet or tasteless. Improve intestinal flora, and significantly reduce the effect of phenolic compounds in the body. Therefore, the branched α-glucan mixture having the above-mentioned characteristics (A) to (C) is extremely useful as an active ingredient of an agent for reducing phenolic compounds in a living body.

Furthermore, the present invention solves the above-mentioned problems by providing a diet for reducing phenolic compounds in vivo containing the above-mentioned reducing agent for reducing phenolic compounds in vivo. [Effect of Invention]

The agent for reducing phenolic compounds in the body of the present invention, the branched α-glucan mixture of the active ingredient is low-sweet or tasteless, so it can be used in a wide range. When human beings ingest it, it not only improves the intestinal flora, but also reduces Phenolic compounds are known as intestinal spoilage products, so they are useful for skin health, maintenance of beauty, and further, health maintenance of the living body. In addition, by ingesting the food and drink containing the phenolic compound reducing agent in vivo of the present invention, the phenolic compound in the living body can be reduced easily, safely and effectively.

The present invention relates to an agent for reducing phenolic compounds in a living body, which uses a mixture of branched α-glucans having the following characteristics (A) to (C) as an active ingredient. (A) Glucose is the constituent sugar, (B) There is a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, -A branched structure with a glucose polymerization degree of 1 or higher linked by bonds other than 1, 4 bonds, (C) Isomaltose is produced by digestion with isomaltosetranase.

The phenolic compound reducing agent in the body referred to in this specification means that the so-called good bacteria in the intestines are increased, the intestinal flora is improved, and compared with the situation where the agent is not ingested, the biological activity is reduced. The amount of the phenolic compound contained in the body can be measured, for example, by comparing the amount of the phenolic compound contained in a biological sample such as cecum content, serum, urine, feces, skin, etc. between ingestion of the agent and non-ingestion. amount to confirm. In addition, the "phenol compound" mentioned here means phenol, p-cresol (p-methylphenol), etc. Furthermore, these "phenolic compounds" are considered to be derived from tyrosine, an amino acid of protein ingested by humans, and are metabolized by intestinal bacteria and the like to be produced as intestinal spoilage products.

As taught in Non-Patent Document 7, if the phenolic compounds in the body, especially the phenolic compounds in the blood or skin, can be reduced, the maintenance of the moisture content of the cutin in the skin or the normalization of the keratinization of the epidermis are expected, and then it is expected to cause Skin health and maintenance of beauty. In addition, phenolic compounds in the body have been reported to be involved in carcinogenesis of the large intestine (see Non-Patent Document 6), and if they can be reduced, it is expected to also reduce the risk of carcinogenesis or various diseases.

The biophenolic compound reducing agent of the present invention contains the aforementioned branched α-glucan mixture (hereinafter referred to as "this branched α-glucan mixture") as an active ingredient. This branched α-glucan mixture can be obtained by various production methods as described later, and the obtained this branched α-glucan mixture is usually a branch with various branch structures and a large number of glucose polymerization degrees (molecular weight) The form of the mixture of α-glucans is impossible to isolate or quantify branched α-glucans one by one under the current technology. Therefore, although the structure of each branched α-glucan cannot be determined for each branched α-glucan molecule, that is, the bonding pattern and bonding order of the glucose residues constituting the unit, the branched α-glucan The structure of the sugar mixture can be characterized as a whole by various physical methods, chemical methods or enzymatic methods generally used in this field.

Specifically, the structure of this branched α-glucan mixture, as a whole, is characterized by the above-mentioned features (A) to (C). That is, this branched α-glucan mixture is a glucan with glucose as a constituent sugar (feature (A)), and has a straight chain at a degree of polymerization of 3 or more in glucose linked by α-1,4 bonds. A branched structure with a glucose polymerization degree of 1 or higher linked to the non-reducing terminal glucose residue at one end of the dextran through a bond other than the α-1,4 bond (feature (B)). Furthermore, the "non-reducing terminal glucose residue" referred to in feature (B) refers to the glucose residue at the terminal that does not show reducing properties among the glucan chains linked by α-1,4 bonds, " "A bond other than an α-1,4 bond" literally means a bond other than an α-1,4 bond.

Furthermore, the α-glucan mixture of this branch is digested with isomaltose to generate isomaltose (feature (C)). The "isomaltoglucanase digestion" referred to in feature (C) means that the isomaltglucanase acts on the α-glucan mixture of this branch to hydrolyze. Isomaltoglucanase is an enzyme with enzyme number (EC) 3.2.1.94, which is α-1,2, α-1,3 adjacent to the reducing end side of the isomaltose structure in α-glucan , α-1,4, and α-1,6 linkages all have enzymes that are characteristic of hydrolysis. Isomaltglucanase derived from Arthrobacter globiformis is suitably used (for example, see Sawai et al., Agricultural and Biological Chemistry, Vol. 52, No. 2, pp. 495-501 (1988)).

Isomaltose is produced by digestion with isomaltosetranase, which means that the isomaltose structure with branched α-glucan molecules constituting the mixture of branched α-glucans can be hydrolyzed by isomaltosetranase, characterized by (C), when the α-glucan mixture of this branch is observed as a whole, it can be known by enzymatic method that it has the structural feature of isomaltose structure that can be hydrolyzed by isomaltosetranase .

This branched α-glucan mixture is digested by isomaltodelucanase, relative to the solid matter of the digestate, usually 5% by mass to 70% by mass, preferably 10% by mass to 60% by mass % or less, more preferably 20% to 50% by mass of isomaltose, is considered to be more suitable for improving the intestinal flora, and has a better effect of reducing the concentration of phenolic compounds in the living body, so it is suitable for use.

That is, as will be described later, it can be considered that the improvement effect of the intestinal flora and the effect of reducing the concentration of phenolic compounds in the living body by the mixture of α-glucans of this branch have the same effect as that of the mixture of α-glucans of this branch. The structural features of isomaltose produced by isomaltoglucanase digestion are deeply related. That is, the branched α-glucan mixture in which the amount of isomaltose digested by isomaltoglucanase is less than 5% by mass has structural characteristics close to those of maltodextrin with less branched structure. On the contrary, isomaltose Isomaltose digested by glucanase produces a branched α-glucan mixture with an amount of more than 70% by mass, which has structural characteristics close to the glucose polymer linked by α-1,6 bonds, namely polydextran (dextran), Because the branching structure specified by the above-mentioned feature (B) becomes less, it does not become a structural feature that can be considered to be related to the improvement of the intestinal flora and the reduction of phenolic compounds in the body. There is an appropriate range for the amount of isomaltose.

In addition, a more suitable aspect of the branched α-glucan mixture can be cited as having a water-soluble dietary fiber content obtained by high-speed liquid chromatography (enzyme-HPLC method) of 40% by mass or more (D )By.

The "high-speed liquid chromatography (enzyme-HPLC method)" (hereinafter referred to as "enzyme-HPLC method") for obtaining the content of water-soluble dietary fiber refers to the Ministry of Health and Welfare Announcement No. 146 of May 1996. Nutritional expression standards, "Analysis methods, etc. of nutritional components, etc. (methods disclosed in the third column of the first column of the nutritional expression standard category table)", the method described in "Dietary fiber" in item 8, and its outline is as follows stated. That is, the sample is decomposed by a series of enzyme treatments of thermostable α-amylase, protease, and glucoamylase, and proteins, organic acids, and inorganic salts are removed from the treatment solution by ion exchange resin, and Prepare a sample solution for gel filtration chromatography. Next, perform gel filtration chromatography to obtain the peak areas of undigested dextran and glucose in the chromatogram, use the respective peak areas, and the sample obtained by the glucose/oxidase method in addition to the general method The amount of glucose in the solution is used to calculate the water-soluble dietary fiber content of the sample. Furthermore, throughout this specification, unless otherwise specified, "water-soluble dietary fiber content" means the water-soluble dietary fiber content obtained by the aforementioned "enzyme-HPLC method".

The content of water-soluble dietary fiber is the content of α-glucan that has not been decomposed by α-amylase and glucoamylase. Feature (D) is the structure of the α-glucan mixture of this branch by enzymatic method. One of the indicators that give characteristics as a whole.

Furthermore, as mentioned above, it can be considered that the improvement effect of the intestinal flora caused by this branched α-glucan mixture, the effect of reducing phenolic compounds in the body, and the production of isomaltose by digestion with isomaltoglucanase Of course, it can be considered that if the content of water-soluble dietary fiber in the branched α-glucan mixture is higher, in other words, the content of branched α-glucan that is not decomposed by α-amylase and glucoamylase The more there is, the more this characteristic structural part will reach the large intestine without being digested, and the intestinal flora improvement effect will be shown. Therefore, the higher the water-soluble dietary fiber content of the branched α-glucan mixture, which is the active ingredient of the agent for reducing phenolic compounds in vivo, the better, and the suitable water-soluble dietary fiber content is usually 40% by mass or more. More preferably, it is at least 60% by mass, and more preferably at least 75% by mass. There is no particular upper limit to the suitable water-soluble dietary fiber content, the higher the better within the technically feasible range, preferably less than 100% by mass or less than 100% by mass.

Furthermore, a more suitable aspect of the branched α-glucan mixture includes a branched α-glucan mixture having the following characteristics (E) and (F). (E) The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is in the range of 1:0.6 to 1:4, (F) α-1,4-bonded The sum of glucose residues and α-1,6-bonded glucose residues accounts for more than 55% of all glucose residues.

Furthermore, whether the branched α-glucan mixture has the above characteristics (E) and (F) can be confirmed by methylation analysis. Methylation analysis, as is well known, refers to a method generally used as a method for determining the bonding pattern of monosaccharides constituting it in polysaccharides or oligosaccharides (Ciucanu et al., Carbohydrate Research, Vol. 131, No. 2 No., pp. 209-217 (1984)). When methylation analysis is applied to the analysis of the bonding pattern of glucose in dextran, firstly all the free hydroxyl groups in the glucose residues constituting dextran are methylated, and then the fully methylated glucose residues are methylated. Glycan hydrolysis. Then, the methylated glucose obtained by hydrolysis is reduced to become methylated sorbitol that eliminates the metameric isomer, and further, by acetylating the free hydroxyl groups in the methylated sorbitol, a part of the methylated sorbitol is obtained. Methylated sorbitol acetate (in addition, there are those who collectively refer to "partially methylated sorbitol acetate" as "partially methylated substances"). By analyzing the obtained partial methylated products by gas chromatography, various partial methylated products derived from glucose residues with different bonding patterns in dextran can be represented by the peak area in the gas chromatography. Expressed by the percentage (%) of the peak area of the partial methylated product. Then, the ratio of the presence of glucose residues with different bonding patterns in the dextran, that is, the ratio of the presence of each glycosidic bond, can be determined from the peak area %. The "ratio" of partial methylation refers to the "ratio" of the peak area in the gas chromatography of the methylation analysis, and the "%" of the partial methylation refers to the gas chromatography of the methylation analysis. The "area%".

The "α-1,4-bonded glucose residue" in the above-mentioned features (E) and (F) means that it is bonded to other glucose residues only through the hydroxyl group bonded to the carbon atom at the 1-position and the 4-position The glucose residue was detected as 2,3,6-trimethyl-1,4,5-triacetylsorbitol in the methylation analysis. In addition, the "α-1,6-bonded glucose residue" in the above-mentioned features (E) and (F) means that it is bonded to other glucose only through the hydroxyl group bonded to the carbon atom at the 1-position and the 6-position The glucose residue was detected as 2,3,4-trimethyl-1,5,6-triacetylsorbitol in the methylation analysis.

The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues obtained by methylation analysis (feature (E)), and α-1,4-bonded The ratio of glucose residues to α-1,6-bonded glucose residues relative to all glucose residues (feature (F)) can be used as a chemical method for the structure of this branched α-glucan mixture, for the mixture as a whole It is one of the indicators that give characteristics.

The provision of "the ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues in the range of 1:0.6 to 1:4" in the above feature (E) means that this 2,3,6-Trimethyl-1,4,5-triacetylsorbitol and 2,3,4-trimethyl - The ratio of 1,5,6-triacetylsorbitol is in the range of 1:0.6 to 1:4. In addition, the provision of "the sum of α-1,4-bonded glucose residues and α-1,6-bonded glucose residues accounting for more than 55% of all glucose residues" in the above feature (F) means that this Branched α-glucan mixture in methylation analysis, 2,3,6-trimethyl-1,4,5-triacetylsorbitol and 2,3,4-trimethyl-1,5 , The total of 6-triacetyl sorbitol accounts for more than 55% of the partially methylated sorbitol acetate. Usually, starch does not have glucose residues bonded only at the 1-position and 6-position, and the α-1,4-bonded glucose residues account for more than half of all glucose residues, so this branched α-glucan mixture has The above feature (E) and feature (F) mean that the branched α-glucan mixture has a completely different structure from starch.

As defined by features (E) and (F) above, the present branched α-glucan mixture, in a preferred aspect, has a substantial degree of “α-1,6 linkages not normally present in starches. Glucose residues", but since those with more complex branch structures can expect higher effects, it is preferable to have α-1,3 bonds in addition to α-1,4 bonds and α-1,6 bonds knots and/or α-1,3,6 linkages. Here, "α-1,3,6 linkage" means "glucose that is bonded to other glucose (α-1,3,6 linkage) at the three positions of the hydroxyl group at the 1-position, 3-position, and 6-position Residues". As long as there are α-1,3 bonds and/or α-1,3,6 bonds in addition to α-1,4 bonds and α-1,6 bonds, it will have a more complicated branched structure, Therefore, basically, as long as the branched α-glucan mixture contains α-1,3 linkages and/or α-1,3,6 linkages, the ratio is not particularly limited, for example, α-1 , 3-bonded glucose residues are preferably at least 0.5% and less than 10% of all glucose residues, and α-1,3,6-bonded glucose residues are preferably at least 0.5% of all glucose residues.

The above "α-1,3 bonded glucose residues are more than 0.5% and less than 10% of the total glucose residues", the methylation analysis of the α-glucan mixture of this branch can be carried out, and by the presence of some formazan It was confirmed by 2,4,6-trimethyl-1,3,5-triacetyl sorbitol with more than 0.5% and less than 10% of sorbitol acetate. In addition, the above-mentioned "glucose residues with α-1, 3, 6 bonds are more than 0.5% of all glucose residues", the methylation analysis of this branched α-glucan mixture can be carried out, and the presence of some methyl groups Confirmed by adding 2,4-dimethyl-1,3,5,6-tetraacetyl sorbitol with more than 0.5% and less than 10% of sorbitol acetate.

The branched α-glucan mixture can also be characterized by the weight average molecular weight (Mw), and the value (Mw/Mn) of dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn). Weight average molecular weight (Mw) and number average molecular weight (Mn) can be calculated|required using size exclusion chromatography etc., for example. Also, the average glucose polymerization degree of the branched α-glucans constituting the branched α-glucan mixture can be calculated based on the weight average molecular weight (Mw), so the branched α-glucan mixture can also be polymerized by the average glucose polymerization degrees to give characteristics. The average glucose polymerization degree can be obtained by subtracting 18 from the weight average molecular weight (Mw) and dividing by 162, which is the molecular weight corresponding to the amount of glucose residues. When using the branched α-glucan mixture as an active ingredient of the agent for reducing phenolic compounds in vivo, the average degree of glucose polymerization is generally 8-500, preferably 15-400, more preferably 20-300. Furthermore, the greater the average degree of glucose polymerization, the higher the viscosity of the branched α-glucan mixture, and the smaller the average glucose polymerization degree, the lower the viscosity. This point shows the same properties as ordinary dextran. Therefore, according to the embodiment of the agent for reducing phenolic compounds in vivo of the present invention, the branched α-glucan mixture having an average degree of glucose polymerization that meets the required viscosity can be appropriately selected for use.

The value Mw/Mn of dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn) is closer to 1, which means that the deviation of the degree of glucose polymerization of the branched α-glucan molecules constituting the branched α-glucan mixture is smaller . Using this branched α-glucan mixture as an active ingredient of the agent for reducing phenolic compounds in the body, Mw/Mn can be used without problems as long as it is usually 20 or less, but preferably 10 or less, more preferably 5 or less. should. Furthermore, when a mixture of this branched α-glucan with a relatively uniform glucose polymerization degree is demanded as an active ingredient of the biophenol compound reducing agent of the present invention, the Mw/Mn is closer to 1 and the deviation of the glucose polymerization degree is smaller the better.

This branched α-glucan mixture can be produced by any method as long as it has the above-mentioned characteristics (A) to (C). For example, in the practice of the present invention, it can be suitably utilized to introduce glucose residues through α-1,4 bonds into the non-reducing terminal glucose residues of linear glucans having a degree of polymerization of glucose linked by α-1,4 linkages of 3 or more. , an enzyme that acts on a branched structure with a glucose polymerization degree of 1 or more linked by 6 bonds, and a branched α-glucan mixture obtained by acting on starch. A more suitable example can be cited International Publication No. WO2008/136331 pamphlet The branched α-glucan mixture obtained by the α-glucosyltransferase disclosed in acting on starch. Also, if amylases such as maltotetraose-forming amylase (EC 3.2.1.60) or starch debranching enzymes such as isoamylase (EC 3.2.1.68) are used in addition to the aforementioned α-glucosyltransferase , can reduce the molecular weight of the branched α-glucan mixture, so the molecular weight, glucose polymerization degree, etc. can be adjusted to the desired range. Furthermore, by using cyclomaltodextrin glucanotransferase (EC 2.4.1.19) or starch branching enzyme (EC 2.4.1.18) in combination, disclosed in JP-A-2014-054221 An enzyme that has the activity of transferring α-1,4 glucan with a degree of polymerization of 2 or more to α-1,6 to the glucose residue inside the starch, which will make the branched α-glucans that constitute the branched α-glucan mixture More highly branched glycans can also increase the water-soluble dietary fiber content of the branched α-glucan mixture. It is also possible to further make glucoamylase and other glucolytic enzymes act on the branched α-glucan mixture obtained in this way to become a branched α-glucan mixture with a higher content of water-soluble dietary fiber. Trehalose-generating enzyme (EC 5.4.99.15) acts to introduce a trehalose structure at the reducing end of branched α-glucan constituting the branched α-glucan mixture, or to reduce branched α-glucan by hydrogenation Terminal reduction, etc., to reduce the reducing power of the branched α-glucan mixture, and can also be freely distinguished by size exclusion chromatography, etc., to obtain a branched α-glucan mixture with a desired molecular weight .

The amount of the α-glucan mixture of this branch contained in the biophenolic compound reducing agent of the present invention is not particularly limited as long as the desired effect of reducing phenolic compounds in the body is exhibited, as long as it contains the α-glucan of this branch The range of the mixture is 1 to 100% by mass, preferably 3 to 100% by mass, more preferably 5 to 100% by mass. In addition, the phenol compound reducing agent in the body of the present invention, in addition to the branched α-glucan mixture, can also be composed of water, minerals, fragrances, stabilizers, excipients, bulking agents, and pH regulators. One or two or more components selected from among these are appropriately blended and utilized at a ratio of 0.01 to 50% by mass, preferably 0.1 to 40% by mass.

The agent for reducing phenolic compounds in the body of the present invention is not particularly limited as long as the ingestion can exert the effect of reducing the amount of phenolic compounds in the body. For example, as an active ingredient, the α-glucan mixture of this branch The intake amount is usually in the range of 0.5 to 100g, preferably 1 to 50g, more preferably 1.5 to 10g, and more preferably 3 to 8g for an adult (60kg body weight) per serving , The biophenol compound reducing agent of the present invention may be ingested directly or dissolved in beverages such as water, tea, coffee, or added to food or beverages. Furthermore, the agent for reducing phenolic compounds in the body of the present invention may be ingested during, before, or after ingestion of food or drink.

The biophenol compound reducing agent of the present invention can be in the form of powder, granule, granule, liquid, paste, cream, tablet, capsule, capsule lozenge, soft capsule, lozenge , stick, plate, block, pill, solid, gel, jelly, fudge, flake, biscuit, syrup, chewable lozenge, syrup, Appropriate form such as a stick. In addition, the phenolic compound reducing agent in the body of the present invention can be used as a food for specific health use, food with functional indications, nutritional supplements, or health food for the purpose of preventing or improving lifestyle-related diseases by being contained in food or drink. The form of food ingested.

Specific examples of food and drink for reducing phenolic compounds in vivo containing the phenolic compound reducing agent in vivo of the present invention include carbonated drinks, milk drinks, jelly drinks, sports drinks, vinegar drinks, soybean milk drinks, and iron-containing drinks , lactic acid bacteria drinks, green tea, black tea, cocoa, coffee and other beverages; rice, porridge, bread, noodles, soup, miso soup, yogurt and other foods; soft candy, hard candy, gambe candy, jelly, biscuits, soft Biscuits, senbei, hail cake, rice incense, gyuhi (one of the ingredients of Japanese desserts), mochi, warabi mochi, Japanese steamed buns, Uiro mochi, stuffing, yokan, water yokan, brocade jade, jelly, fruit Jelly, Honey Cake, Bisque Cookies, Soda Cake, Pie, Pudding, Butter Cream, Custard Cream, Puffs, Muffins, Sponge Cake, American Muffins, Muffins, Donuts, Chocolate, Candy Sweets such as nach, corn sticks, chewing gum, caramel, nougat, roux, peanut paste, fruit paste, jam, peel jam; ice desserts such as ice cream, sorbet, gelato; and soy sauce , powdered soy sauce, miso, powdered miso, mash, seasoning sauce, pine, mayonnaise, salad dressing, vinegar, three cups of vinegar, powdered sushi vinegar, Chinese miso, tempura dipping sauce, noodle dipping sauce, sauce , tomato sauce, ketchup, roasted pork dipping sauce, grilled chicken dipping sauce, fried rice noodles, tempura powder, curry sauce, stew miso, soup miso, dashi miso, compound seasoning, mirin, new mirin , granulated sugar, coffee sugar and other seasonings or conditioning products. Furthermore, the agent for reducing phenolic compounds in the body of the present invention can also be blended into liquids, syrups, managed nutrition, lozenges, capsules, and lozenges for preventing or improving (treating) lifestyle-related diseases , sublingual preparations, granules, powders, powders, emulsions, sprays and other forms of pharmaceuticals. Still further, the agent for reducing phenolic compounds in vivo of the present invention can also be blended into pet food, feed, or bait ingested by animals other than humans.

The agent for reducing phenolic compounds in the body of the present invention and the food and drink for reducing phenolic compounds in vivo containing it can also be administered to the stomach or digestive tract by parenteral administration such as administration through a tube. and.

In addition, the phenolic compound reducing agent in the body of the present invention can reduce the amount of phenolic compounds produced in the living body due to food and drink, as shown in the experimental items described later, so that it can reduce the adverse effects of phenolic compounds on the skin, The maintenance or improvement of skin health, specifically, the effect of optimizing and improving the turnover rate of the skin.

Hereinafter, the present invention will be described in more detail based on experiments.

In the following experiments, the branched α-glucan mixture prepared according to the method described in Example 5 of International Publication No. WO2008/136331 pamphlet was used. That is, according to the method described in the aforementioned Example 5, sodium bisulfite was added to the 27.1% by mass corn starch liquefaction solution (3.6% hydrolysis rate) so that the final concentration was 0.3% by mass, and calcium chloride was added so that the final concentration was After 1 mM, it was cooled to 50° C., and for every 1 gram of solid matter, PP710 ( FERM BP-10771) α-glucosyltransferase concentrated crude enzyme solution 11.1 units, acted at 50°C, pH 6.0 for 68 hours. Keep the reaction solution at 80°C for 60 minutes and then cool it down. The filtered filtrate is decolorized with activated carbon according to the general method, purified by desalination with H-type and OH-type ion resins, further concentrated, spray-dried, and the produced branch The α-glucan mixture was used in Experiment 1 below. Furthermore, the obtained branched α-glucan mixture was subjected to the isomaltodeglucanase digestion test method described in paragraphs 0079 and 0080 of International Publication No. WO2008/136331, α-glucosidase and glucose After analysis by the amylase digestion test method and the methylation analysis method described in paragraphs 0076 to 0078, it has the following characteristics (a) to (c). (a) with glucose as the constituent sugar, (b) having a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, through α -A branched structure with a glucose polymerization degree of 1 or higher linked by bonds other than 1,4 bonds quality%.

In addition, after analyzing the obtained branched α-glucan mixture by the aforementioned enzyme-HPLC method, it can be known that the aforementioned branched α-glucan mixture has the following feature (d) in addition to the above-mentioned features. From the analysis results of the above methylation analysis method, it can be seen that it has the following characteristics (e) to (h). (d) The content of water-soluble dietary fiber is 82.9% by mass, (e) The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is 1:2.1, (f)α The sum of -1,4-bonded glucose residues and α-1,6-bonded glucose residues was 73.8% of all glucose residues. (g) α-1,3 bonded glucose residues are 2.1% of all glucose residues. (h) α-1,3,6 bonded glucose residues accounted for 5.6% of all glucose residues.

Further, the weight average molecular weight (Mw) of the branched α-glucan mixture is 5,000 Daltons after the molecular weight distribution analysis is carried out by gel filtration HPLC described in paragraph 0081 of International Publication No. WO2008/136331 pamphlet (Converted to an average glucose polymerization degree of about 30), Mw/Mn was 2.1.

As mentioned above, the branched α-glucan mixture used in this experiment is a linear glucan with glucose as the constituent sugar and a degree of polymerization of 3 or more in the glucose linked by α-1,4 bonds On the non-reducing terminal glucose residues of the above-mentioned (A ) to (C) features. In addition, the branched α-glucan mixture used in this experiment satisfies the requirement that, by digestion with isomaltoglucanase, an isomalt of 5 mass % or more and 70 mass % or less is produced relative to the solid matter of the digested product. The characteristics of maltose, the characteristics of (D) above that the water-soluble dietary fiber content is 40% by mass or more, and the ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is 1 : The range of 0.6 to 1:4, the above-mentioned (E), ( Features of F).

Further, the aforementioned branched α-glucan mixture has α-1,3 bonded glucose residues in the range of more than 0.5% and less than 10% of all glucose residues, and α-1,3,6 bonded The glucose residues are in the range of 0.5% or more of the total glucose residues.

Furthermore, in the following experiments, rats were used as experimental animals, and a feed (hereinafter referred to as "tyrosine feed") fortified/mixed with tyrosine, an amino acid that is a raw material of phenolic compounds in the body, was given as Feed, and water or an aqueous solution of branched α-glucan mixture in which a specific concentration of the above-mentioned branched α-glucan mixture was dissolved was given as drinking water, and after raising for a certain period of time, various organisms collected from rats were measured. The amount of phenolic compounds in the sample.

<Experiment 1: Rats were fed with tyrosine feed bait and branched α-glucan mixture in drinking water> 24 Wistar rats (male, 6 weeks old, sold by Japan SLC Co., Ltd.) were purchased and given Common feed ("CE-2", for breeding, sold by Japan CLEA Co., Ltd.) was bred for 5 days to acclimatize. Then, the domesticated rats were divided into 4 groups of 6 each, and each group of rats was given the feed shown in Table 1 below, that is, any one of the AIN-93G adjusted feed and tyrosine feed described later, and Similarly, the drinking water shown in Table 1, that is, water or an aqueous solution of 2% (w/v) or 5% (w/v) of the branched α-glucan mixture obtained above dissolved in water (hereinafter referred to as "respectively" 2% branched α-glucan mixture”, “5% branched α-glucan mixture”), each of which was bred for 3 weeks.

In addition, "AIN-93G adjusted feed" and "tyrosine feed" shown in Table 1 are feeds each having the composition shown in Table 2 below, and were purchased from Japan CLEA Co., Ltd. Furthermore, the AIN-93G adjusted feed, in addition to the standard feed "AIN-93G" sold by Japan CLEA Co., Ltd., changed the composition of corn starch from 39.7486% by mass to 51.9486% by mass, and changed the content of α-corn starch It is the same composition as AIN-93G except that the composition is changed from 13.2% by mass to 1% by mass. Also, as seen in Table 2, the tyrosine feed was obtained by substituting 5% by mass of cornstarch in the AIN-93G adjusted feed with tyrosine.

Table 3 shows the body weight, food intake, and drinking water of each group of rats during the breeding period. Furthermore, at the time point of 19 to 20 days of feeding, the amount of feces and urine collected from each rat was measured using metabolic cages, and the average and standard deviation of 6 rats in each group are shown in the table 4.

As shown in Table 3, the body weight, bait intake, and water intake of the four groups of rats tested all showed the same level of value, and no significant difference was observed among the groups. This shows that the rats of the normal food group fed with AIN-93G adjusted feed as bait and water as drinking water, and the rats of the control group that ingested tyrosine feed as bait, and ingested a specific concentration of branch α - Rats in the test group of the dextran mixture used as drinking water were bred in a stable test line in which there was no significant difference between the groups. Furthermore, calculated from the amount of food intake, the daily intake of tyrosine in rats that ingested tyrosine feed was about 4 g/kg-body weight. Also, regarding the rats that ingested the branched α-glucan mixture aqueous solution, the daily intake of the branched α-glucan mixture was calculated from the amount of drinking water, and the 2% branched α-glucan mixture group was 1.9 g /kg-body weight, 5.1g/kg-body weight in 5% branched α-glucan mixture group.

Also, regarding the amount of feces and urine during breeding, as shown in Table 4, the control group fed with tyrosine feed and given water as drinking water showed a higher value in the amount of feces than the other groups, but each No significant differences were observed between groups. This result, like the body weight, food intake, and drinking water shown in Table 3, indicates that the rats were bred as a stable test line in which there was no significant difference among the groups.

<Experiment 2: Collection of various samples from rats, pre-treatment of samples, and quantification of phenolic compounds> Various biological samples were collected from each group of rats bred in Experiment 1, and the amount of phenolic compounds contained in each was measured.

<Experiment 2-1. Collection of various samples from rats> In Experiment 1, 4 groups of 24 rats in total were bred and euthanized by collecting whole blood from the posterior vein under pentobarbital anesthesia. After euthanasia, the animals were dissected and removed, and the cecum and liver were collected, and their weights were measured respectively. Also, after the flanks were shaved, skin was collected from two sites in a size of 1 cm square, and the subcutaneous tissue was removed as a skin sample. The respective weights of the liver, cecum tissue and cecum contents, and the pH of the cecum contents are summarized in Table 5. Furthermore, the pH of the cecal contents was measured directly with a pH meter.

As shown in Table 5, compared with the control group, the weight of cecal tissue and cecal contents, the 2% branched α-glucan mixture group and the 5% branched α-glucan mixture group were significantly heavier. The cecal contents of the normal food group and the control group showed a greenish tinge, on the other hand, the cecal contents of the 5% branched α-glucan mixture group showed a yellowish tinge. In addition, in the 2% branched α-glucan mixture group, the ratio of cecal contents with a yellowish tinge was 4, and that with a greenish tinge was 2, suggesting that the branched α-glucan mixture was ingested. Changes in the intestinal flora in the group. Also, the pH of the cecal contents of the group that ingested the branched α-glucan mixture showed a significantly lower value than that of the control group.

<Experiment 2-2. Pretreatment of samples taken for determination of phenolic compounds in the body> For the urine and feces collected in Experiment 1, and the samples collected in Experiment 2-1, ie, cecal contents, Blood (serum), skin, and liver were subjected to the following treatments, respectively, as pre-treatments for the determination of phenolic compounds.

<Cecal contents>: thaw the collected material and store it at -80°C, weigh 0.3g, add 3mL of 0.1M phosphate buffer (pH5.5) to dilute 10 times, and use a Teflon homogenizer (5mL volume) to homogenize and centrifuged (3,000 rpm, 800×g, 10 minutes) to prepare a crude extract, which was stored frozen at -80°C. <Serum>: Centrifuge the collected blood (3,000rpm, 800×g, 10 minutes) to separate the serum, and store it in a freezer at -80°C. <Urine>: Centrifuge (3,000rpm, 800×g, 10 minutes) to remove precipitates (feed, etc.), and store in a freezer at -80°C. <Feces>: thaw those collected and stored at -80°C, dilute 10 times with 0.1M phosphate buffer (pH 5.5), stir for about 5 minutes, and use a Teflon homogenizer (10mL volume) to homogenize. A crude extract was prepared by centrifugation (3,000 rpm, 800×g, 10 minutes), and stored frozen at -80°C. <Skin>: thaw the harvested and stored at -80°C, weigh 0.2g, cut it with scissors, take it into a plastic tube, add 2mL of phosphate buffer, and use a homogenizer ("Polytron PT10-35" type) homogenization. Thereafter, 20 mg of XIV protease (manufactured by Sigma) was added, and the mixture was kept at 55° C. for 3 hours. The XIV protease-treated solution was centrifuged (3,000 rpm, 800×g, 10 minutes), and the supernatant was collected and stored frozen at -80°C. <Liver>: thaw the harvested and stored at -80°C, weigh 0.2g of the left lateral lobe of the liver, put it into a 1.5mL plastic tube, add 1mL of phosphate buffer, and homogenize with a Teflon homogenizer Centrifuge (3,000 rpm, 800×g, 10 minutes), prepare a crude extract, and store at -80°C.

<Experiment 2-3. Quantification of phenolic compounds in each sample> In Experiment 2-2, most of the phenolic compounds in the pre-treated samples were in the form of glycosides. Therefore, by treating the pre-treated samples with hydrochloric acid, the The phenolic compounds in the form of glycosides were hydrolyzed and turned into free forms, which were measured as phenolic compounds. That is to say, in this measurement, two kinds of phenolic compounds, phenol and p-cresol, are used as measurement objects, and phenol and p-cresol that exist in the form of glycosides in the living body are compared with those in the free form. The phenol and p-cresol were acid-treated and quantified together as free phenol and p-cresol, respectively. The specific operation is to centrifuge the above-mentioned pretreatment sample (4,700rpm, 10 minutes), take the supernatant, and take 0.8mL into a tube with a screw cap (except for urine, it is a 220-fold dilution), 32 μL of an internal standard substance 4-ethylphenol adjusted to a concentration of 100 μg/mL and 0.8 mL of 2N hydrochloric acid were added, followed by boiling for 60 minutes. After the boiled liquid was left to cool at room temperature, about 0.75 mL of 2N sodium hydroxide was added for neutralization. Take 0.8 mL of neutralizing solution into a plastic tube, add 0.8 mL of acetonitrile and stir, centrifuge (12,000×g, 5 minutes) to remove insoluble matter, filter 0.3 mL with a 0.45 μm filter, and use it as an HPLC sample.

Phenol and p-cresol in various samples were quantified by HPLC under the following conditions. (HPLC conditions) Column: Shodex ODSpak F-411 (φ4.6×150mm, manufactured by Showa Denko Co., Ltd.); Device: "Prominence" system (manufactured by Shimadzu Corporation) Analytical software using "LabSolutions"; Pump: 2 sets of LC-20AD; column heater: "CTO-20AC"; degasser: "DGU-20A _3R "; automatic sampler: "SIL-20AC"; detector: fluorescence detector RF-20A (excitation Wavelength: 260nm, Fluorescence wavelength: 305nm) Mobile phase: Isocratic eluting with water/acetonitrile (70/30) Column temperature: 30°C Sample injection volume: 10μL Furthermore, in the quantification of phenol and p-cresol , all using phenol and p-cresol reagents (manufactured by Sigma-Aldrich) as standard substances, and each was quantified by making a calibration curve in HPLC.

The quantitative values of phenolic compounds (phenol and p-cresol) in various samples are shown in Table 6 and Table 7, respectively.

As shown in Table 6 and Table 7, no phenols were detected in cecal contents, serum, urine, feces, skin and liver in rats fed with AIN-93G-adjusted feed and water in the normal food group. p-cresol was also detected to a small extent in cecal contents, urine, and feces. On the other hand, in rats fed with a tyrosine diet, phenol was detected in all but the skin and liver, and p-cresol was detected in a large amount compared with the normal food group.

As shown in Table 6, no phenol was detected in the cecal contents of the rats fed with the normal food group fed with AIN-93G adjusted feed and water, and the amount of p-cresol per 1 g of the cecal contents was also a small amount 40±28nmol, compared with this, when the rats of the control group fed with tyrosine feed and water were fed, the amount of phenol was 812±443nmol and the amount of p-cresol was 4522±1261nmol per 1g of cecal content, it was observed Formation of a large number of phenolic compounds. On the other hand, when the 2% branched α-glucan mixture group fed with tyrosine feed and 2% branched α-glucan mixture aqueous solution was fed, the phenolic content was 334±435 nmol, p- The amount of cresol was 2866±1652 nmol, which was significantly lower than that of the control group. In addition, when the 5% branched α-glucan mixture group bred by ingesting tyrosine feed and 5% branched α-glucan mixture aqueous solution was fed, the phenolic content was 12±3 nmol and p-cresol per 1 g of cecum content. The amount was 397±128 nmol, which showed a significantly lower amount of phenolic compounds compared to the control group. This result shows that phenolic compounds are produced in the cecal contents due to the intake of tyrosine feed, and even if a tyrosine feed that is prone to produce phenolic compounds is taken, as long as a certain amount of branched α-glucan mixture is taken together, Can significantly reduce the amount of phenolic compounds in the cecal contents.

Also, as shown in Table 6, in rats fed with a normal diet fed with AIN-93G adjusted feed and water, neither phenol nor p-cresol was detected in serum. In the rats of the control group raised in water, the amount of phenol was 27±30 nmol and the amount of p-cresol was 136±35 nmol per 1 mL of serum, and the formation of phenolic compounds was observed. On the other hand, when ingesting tyrosine feed and 2% branched α-glucan mixture aqueous solution to raise the 2% branched α-glucan mixture group, the amount of phenol per 1mL serum was 16±15nmol, p-cresol The amount was 101±50nmol, which was not significantly different from the control group, but when the 5% branched α-glucan mixture group was fed with tyrosine feed and 5% branched α-glucan mixture aqueous solution , the amount of phenol per 1 mL of serum was 5 ± 0 nmol, and the amount of p-cresol was 15 ± 4 nmol, which showed a significantly lower amount of phenolic compounds than the control group. This result shows that due to the intake of tyrosine feed, phenolic compounds are detected in the serum, and even if the intake of tyrosine feed that is prone to produce phenolic compounds, as long as a certain amount of branched α-glucan mixture is taken together, it is also possible Significantly reduce the amount of phenolic compounds in serum.

Furthermore, in each group, the daily urine collected from one rat was analyzed, and the daily excretion of phenolic compounds in urine was expressed in μmol/day. As shown in Table 6, no phenol was detected in the urine of the rats in the normal food group, and the amount of p-cresol was also a small amount of 5±4 μmol/day. The amount of p-cresol was 42±15 μmol/day, the amount of p-cresol was 208±41 μmol/day, and a large amount of phenolic compounds were observed. On the other hand, in the 2% branched α-glucan mixture group, the amount of phenol was 40±41 μmol/day, and the amount of p-cresol was 196±87 μmol/day, which was not significantly different from the control group. However, in the 5% branched α-glucan mixture group, the amount of phenol was 4±7 μmol/day and the amount of p-cresol was 58±48 μmol/day, which were significantly lower than those of the control group. This result shows that due to the intake of tyrosine feed, phenolic compounds are detected in urine, and even if tyrosine feed that is prone to produce phenolic compounds is ingested, as long as a certain amount of branched α-glucan mixture is ingested together, urine The amount of phenolic compounds observed is also significantly reduced.

Furthermore, in each group, one day's feces collected from one rat was analyzed, and it was expressed in nmol/day as the excretion amount of phenolic compound in feces per day. As shown in Table 7, no phenol was detected in the feces of the rats in the normal food group, and the amount of p-cresol was also a small amount of 130±64 nmol/day. The amount of p-cresol was 240±247nmol/day and the amount of p-cresol was 568±218nmol/day, and a large amount of phenolic compounds were observed. On the other hand, in the 2% branched α-glucan mixture group, the amount of phenol was 80±113nmol/day, and the amount of p-cresol was 844±947nmol/day, which was not significantly different from the control group. However, in the 5% branched α-glucan mixture group, the amount of phenol was 32±17nmol/day, and the amount of p-cresol was 533±326nmol/day. Compared with the control group, although there was no difference in the amount of p-cresol , but the phenolic series showed significantly lower values. This result shows that due to the intake of tyrosine feed, phenolic compounds are detected in feces, and even if tyrosine feed that is prone to produce phenolic compounds is ingested, as long as a certain amount of branched α-glucan mixture is ingested together, the feces The amount of phenolic compounds observed is also reduced.

Also, as shown in Table 7, no phenol was detected from the skin samples in any cases. On the other hand, p-cresol was not detected in the skin samples from the normal food group, and the skin samples from the control group and the 2% branched α-glucan mixture group were converted per 1 g of skin, respectively. p-cresol was detected at approximately the same level as 29 nmol/g and 27 nmol/g. However, p-cresol was not detected in skin samples of 5% branched α-glucan mixture (0 nmol/g in terms of skin per 1 g), and p-cresol was observed due to ingestion of branched α-glucan mixture. The reducing effect of p-cresol.

Furthermore, as shown in Table 7, no phenol was detected from the liver samples in any cases. On the other hand, p-cresol was not detected in the liver samples from the normal food group, and the liver samples from the control group and the 2% branched α-glucan mixture group were converted per 1 g of liver, respectively. p-cresol was detected at approximately the same level as 26 nmol/g and 20 nmol/g. However, p-cresol was not detected in the liver sample of the 5% branched α-glucan mixture group (0 nmol/g in terms of liver per 1 g), and p-cresol was observed due to the uptake of the branched α-glucan mixture. The reducing effect of p-cresol.

As shown in the above experimental results, phenolic compounds such as phenol and p-cresol were hardly detected in the rat organisms of the normal food group raised from the general feed. Phenolic compounds were significantly detected in the rat organisms of the control group fed with a tyrosine-based tyrosine diet, but since ingesting 5% branched α-glucan solution in an aqueous solution with a concentration of 5% branched α-glucan mixture Significantly small amounts of phenolic compounds were detected in the rat organisms of the sugar mixture intake group. This shows that even if humans eat a high-protein diet, they are prone to produce phenolic compounds derived from the harmful metabolites of tyrosine, which constitutes amino acids in the protein. By taking a certain amount of branched α-glucan mixture, it is also possible Can significantly and effectively reduce the phenolic compounds in the body.

＜Experiment 3: The effect of branched α-glucan mixture intake on the intestinal flora of rats＞ In this experiment, Bifidobacterium, Bacteroides-Prevotella Bacteria of the genus Porphyromonas and 3 types of Bacteroides bacteria were used as targets to investigate the effect of the intake of branched α-glucan mixture on the number of these bacteria/flora in the intestine influences.

From the cecal contents taken from the rats of the normal diet group, the control group, the 2% branched α-glucan mixture group, and the 5% branched α-glucan mixture group raised in Experiment 1, DNA was carried out. extraction. Using the extracted DNA as a template, use the primers targeting the specific sequence part contained in the rRNA gene of the bacterial species/flora as the target, and then perform PCR by detecting the amplified product of the quantitative PCR method (for example, refer to Matsui et al. , Applied and Environmental Microbiology, Volume 68, No. 11, Pages 5445-5451 (2002) reference), determination of Bifidobacterium, Bacteroides-Pyrromonas Prevot, and Bacteroides The number of bacteria in each phylum.

The number of bacteria in the cecal contents of the normal food group, control group, 2% branched α-glucan mixture group and 5% branched α-glucan mixture group obtained by the above method (log (unit/g- Cecal contents)) are shown in Table 8.

As seen in Table 8, the intestinal flora in the cecum contents of the rats of the normal food group, the control group and the 2% branched α-glucan mixture group, the Bifidobacterium genus bacteria, Bacteroides-prevopyrrole The number of bacteria in the genus Monas and Bacteroidetes bacteria expressed in logarithm to the base 10 (log (unit/g-cecal content)), respectively distributed in 6.4~6.7, 10.3~10.4, and 10.6~10.7 In the range of 10 ^6.4~6.7 , 10 ^10.3~10.4 , and 10 ^10.6~10.7 , no big difference was observed between the groups. In contrast, the 5% branched α-glucan mixture group The number of bacteria expressed in the base 10 logarithm of rats (log (unit/g-cecal content)) was 8.0, 11.1 and 11.4 (that is, 10 ^8.0 , 10 ^11.1 , and 10 ^11.4 ), each significantly increased by About 10 times more.

In this way, it can be seen that the number of bacteria belonging to the genus Bifidobacterium, bacteria belonging to the genus Bacteroides-prevot, and bacteria belonging to the genus Bacteroidetes in the rats of the 5% branched α-glucan mixture group was significantly Increased intestinal flora significantly improved. Therefore, it is speculated that the reduction effect of phenolic compounds in the living body in Experiment 2 is caused by the ingestion of the branched α-glucan mixture resulting in the Bifidobacterium genus bacteria, Bacteroides-prevopyrromonas in the rat cecum Bacteroides and Bacteroides increase the number of bacteria, that is, the effect of improving the intestinal flora. From the above results using rats, it can be considered that the same effect is exerted on humans by ingesting the branched α-glucan mixture.

How the α-glucan mixture of this branch works to improve the intestinal flora and reduce phenolic compounds in the body, although the details are not clear, it is speculated that the α-glucan mixture of this branch has the following structural characteristics: Non-reducing terminal glucose residues of straight-chain glucans with a glucose polymerization degree of 3 or higher linked by α-1,4 linkages and a glucose polymerization degree of 1 or higher linked by linkages other than α-1,4 linkages branched structure, and isomaltose is generated by digestion with isomaltoglucanase; it is more preferably digested with isomaltglucanase, with respect to the solid matter of the digest, more than 5% by mass and 70 The structural characteristics of isomaltose below mass % play an important role in its function.

Furthermore, the branched α-glucan mixture produced by the digestion of isomaltose by isomaltoglucanase is less than 5% by mass. It is presumed that the intestinal flora is improved because it is close to the structure of maltodextrin with less branched structure. The effect is small. On the other hand, the branched α-glucan mixture produced by the digestion of isomaltose by isomaltglucanase exceeds 70% by mass is presumed to be one of polydextrose close to the glucose polymer linked by α-1,6 bonds. structure, but the branching structure becomes monotonous, so the effect of improving the intestinal flora becomes smaller. In addition, among the α-glucan mixtures of this branch, the content of water-soluble dietary fiber obtained by high-speed liquid chromatography (enzyme-HPLC method) is more than 40% by mass, and it is presumed that it is not easy to be digested, and it is easier to reach The large intestine is better.

<Experiment 4: Feeding hairless rats with tyrosine feed and drinking water with a mixture of branched α-glucans> To investigate in more detail the effects of phenolic compound production in vivo on skin properties and For the purpose of the effect of the branched α-glucan mixture, hairless rats were bred in almost the same manner as in Experiment 1, except that the Wistar rats used in Experiment 1 were replaced by hairless rats.

24 hairless rats (male, 6 weeks old, sold by Japan SLC Co., Ltd.) were purchased, fed with AIN-93G adjusted feed, and bred for 5 days to acclimate them. Next, the domesticated rats were divided into 4 groups of 6 each, as the same 4 test groups as shown in Table 1 of Experiment 1, that is, normal food group, control group, 2% branched α-glucan The mixture group and the 5% branched α-glucan mixture group were reared for 3 weeks respectively.

Table 9 shows the body weight, food intake, and water intake of each group of hairless rats during the breeding period. Furthermore, at the time point of 19 to 20 days of feeding, the daily amount of feces and urine collected from each rat was measured using a metabolic cage, and it is shown in the table as the average value and standard deviation of 6 rats in each group. 10.

As shown in Table 9, the 4 groups of hairless rats tested showed the same level of body weight and water intake, and no significant difference was observed among the groups. However, the daily food intake of the 2% branched α-glucan mixture group and the 5% branched α-glucan mixture group were about 95% and about 90%, are significantly less. Calculated from the amount of food intake, the daily intake of tyrosine in the hairless rats of the control group was about 4.4 g/kg-body weight. In addition, regarding the rats that ingested the aqueous solution of the branched α-glucan mixture, the daily intake of the branched α-glucan mixture was calculated from the amount of drinking water, based on 2.0 g of the 2% branched α-glucan mixture group /kg-body weight, 5.1g/kg-body weight in 5% branched α-glucan mixture group.

In addition, regarding the amount of feces and urine during breeding, as shown in Table 10, a 2% branched α-glucan mixture group was fed with a tyrosine feed and an aqueous solution of the branched α-glucan mixture as drinking water. and 5% branched α-glucan mixture group showed a tendency to produce less feces and more urine than other groups, but no significant difference was observed among the groups.

The results in Table 9 and Table 10 show that in the hairless rats, which are different from the Wistar rats in Experiment 1, although the amount of food intake is small in the group that ingests the aqueous solution of the branched α-glucan mixture as drinking water However, there was no significant difference in body weight, drinking water, feces, and urine at the end of feeding. Hairless rats were bred with a stable test line that did not produce significant differences among groups.

<Experiment 5: The amount of phenolic compounds in various biological samples collected from hairless rats> The amount of phenolic compounds produced in various samples. That is, similarly to the cases of Experiment 1 and Experiment 2-1, cecal contents, blood (serum), urine, and skin were collected from four groups of hairless rats. The respective weights of cecal tissue and cecal contents, and the pH of cecal contents are summarized in Table 11.

As shown in Table 11, the weight of cecal contents in the 2% branched α-glucan mixture group and the 5% branched α-glucan mixture group were significantly heavier than the control group. Also, the pH of the cecal contents was significantly lower in the 2% branched α-glucan mixture group and the 5% branched α-glucan mixture group.

Next, for each sample of cecum content, blood (serum), urine, and skin collected above, phenolic compounds (phenol and p-cresol) in each sample were quantified in the same manner as in Experiment 2-2. The measurement results are summarized in Table 12.

As shown in Table 12, in the hairless rats, all the groups of the normal food group, the control group, the 2% branched α-glucan mixture group, and the 5% branched α-glucan mixture group were all in the cecum. Phenol and p-cresol were detected in substances, serum, urine and skin.

As shown in Table 12, the amount of phenol per 1 g of cecal contents in rats fed with a normal diet fed with AIN-93G adjusted feed and water was 76±33 nmol, and the amount of p-cresol was also 14±11 nmol , is a small amount. In contrast, when the hairless rats of the control group fed with tyrosine feed and water were fed, the amount of phenol was 629±230nmol and the amount of p-cresol was 165± 164 nmol, 8 times or more and 11 times or more of phenolic compounds were observed, respectively. On the other hand, when the 2% branched α-glucan mixture group fed with tyrosine feed and 2% branched α-glucan mixture aqueous solution was raised, the phenol content per 1g of cecal content was 222±109nmol, p- The amount of cresol was 70±92nmol, which showed a significantly lower amount of phenolic compounds than the control group. Also, when the 5% branched α-glucan mixture group raised by ingesting tyrosine feed and 5% branched α-glucan mixture aqueous solution was fed, the phenol content was 109±66 nmol and p-cresol per 1 g of cecum content. The amount was 89±55 nmol, which showed a significantly lower amount of phenolic compounds compared to the control group. This result shows that, similar to the case of Wistar rats in Experiment 2, even in the case of hairless rats, a large amount of phenolic compounds are produced in the cecum contents due to the intake of tyrosine feed, and phenolic compounds are easily produced even if they are ingested. As long as a certain amount of branched α-glucan mixture is ingested together with the tyrosine feed, it can also significantly reduce the amount of phenolic compounds in the cecal contents.

Also, as shown in Table 12, in hairless rats, in serum, urine, and skin, compared with the normal food group, it was observed that the amount of phenol and p-cresol in the control group also increased, and in 2% branched α-glucan mixture group and 5% branched α-glucan mixture group were observed to be the results or trends of reduction. This result shows that even if tyrosine feed is ingested, as in the case of cecal contents, as long as a certain amount of branched α-glucan mixture is ingested together, the phenols in serum, urine and skin can also be significantly reduced. amount of compound.

Furthermore, in Wistar rats of Experiments 1 and 2, p-cresol was produced in a larger amount than phenol among the phenolic compounds, whereas in hairless rats, phenol was produced in a larger amount than p-cresol. This result can be considered that the intestinal bacterial flora of Wistar rats and hairless rats are different, so there is a gap in the production of phenolic compounds.

<Experiment 6: Analysis of the skin properties of hairless rats> In the skin, the outer cells in contact with the outside world are repeatedly peeled off as scales, and the inner cells proliferate to provide new cell turnover (skin metabolism ) to maintain constancy. When the turnover rate of the skin is too fast, the keratinocytes are not fully differentiated and appear on the skin surface in a small size. Therefore, in the field of cosmetics, the keratinocyte area is used as an indicator of skin health. In Non-Patent Document 2, as an indicator of the adverse effect of phenolic compounds on the skin of hairless mice, the area of corneocytes in the skin was measured, and it was reported that in hairless mice administered with phenol or p-cresol, , the area of corneocytes was significantly reduced. In this experiment, the area of the keratinocytes of the skin was measured for the hairless rats bred in Experiment 4.

In addition, in the turnover rate of the skin, if the division of the undifferentiated cell group called basal cells adjacent to the basement membrane located under the skin epidermis is accelerated, the differentiation of keratinocytes is slow, and it becomes an immature horn Therefore, for the hairless rats bred in Experiment 4, the division of basal cells of the skin was also investigated.

<Experiment 6-1: Measurement of the area of keratinocytes in the skin of hairless rats> For the 4 groups of 24 hairless rats bred in Experiment 4, skin samples were taken under pentobarbital anesthesia before euthanasia. horn layer. The adhesive tape (trade name "horn tester AST-01", 25×25mm, sold by ASCH Co., Ltd., Japan) for the right back of the hairless rat was peeled off for a few seconds, so as to collect the cuticle on the tape , fixed by blowing formalin steam, and stained with hematoxylin/eosin. Then, the hematoxylin/eosin-stained corneocytes were observed under a microscope. For hairless rats, there were more than 30 corneocytes per individual, and imaging software for microscopy (trade name "cellSens Dimension", Olin Bath Co., Ltd.) measured the cell area, and calculated the average value. The results are shown in Table 13.

As shown in Table 13, in the hairless rats fed with a normal diet fed with AIN-93G adjusted feed and water, the corneocyte area was 1303±96 μm ² . In the hairless rats of the control group, a significantly lower value of 1159±97 μm ² was shown. On the other hand, when the 2% branched α-glucan mixture group fed with tyrosine feed and 2% branched α-glucan mixture aqueous solution was fed, the corneocyte area was 1286±86 μm ² , compared with the control group For the 5% branched α-glucan mixture group raised by ingesting tyrosine feed and 5% branched α-glucan mixture aqueous solution, it was 1331±72 μm ² , compared with the control group In other words, it shows a significantly high value, and shows a value equivalent to that of a normal food group. This result shows that in hairless rats that ingested tyrosine feed, phenolic compounds produced in vivo inhibited the differentiation of keratinocytes in the skin, but by ingesting a mixture of branched α-glucans, phenolic compounds in vivo The production of the compound is reduced, showing that it does not affect the differentiation of keratinocytes and can improve skin properties.

<Experiment 6-2: Determination of cleavage images of basal cells in the skin> For 4 groups of 24 hairless rats bred in Experiment 4, the left back skin was collected after euthanasia, and immersed in 15% (v/v) formam Preserved in forest fluid for tissue analysis. The paraffin-embedded tissue sections were stained with hematoxylin/eosin by a general method, and the division images of the basal cell layer were counted under a microscope. The results are shown in Table 14.

As shown in Table 14, in hairless rats fed with a normal diet fed with AIN-93G adjusted feed and water, the division pattern of basal cells was 2.8±1.1 cells/cm, compared to this, the intake of tyrosine feed and water On the other hand, the hairless rats of the control group showed a significantly larger value of 5.7±1.8 cells/cm, indicating that the division of basal cells was increased due to the intake of tyrosine feed. On the other hand, when the 2% branched α-glucan mixture group fed with tyrosine feed and 2% branched α-glucan mixture aqueous solution was 4.8±1.8/cm, compared with the control group Showing a tendency to decrease, when the 5% branched α-glucan mixture group raised by ingesting tyrosine feed and 5% branched α-glucan mixture aqueous solution was 3.2±0.8, compared with the control group, it showed significant Low value, and the same value as the usual food group. These results show that in hairless rats fed with tyrosine feed, phenolic compounds produced in vivo promote the division of basal cells in the skin, that is, hinder the differentiation of keratinocytes, but even after taking tyrosine Hairless rats fed amino acid diet, by ingesting the branched α-glucan mixture, the production of phenolic compounds in the body will also be reduced. The results show that it will not affect the differentiation of corneocytes, and can improve the skin traits.

From the results of experiments 1 to 5, it can be seen that when the α-glucan mixture of this branch is ingested, the intestinal flora can be improved, and phenols such as phenols and p-cresols known as intestinal spoilage products can be significantly reduced. compound. These experiments have shown that the branched α-glucan mixture has a remarkable effect as an active ingredient of a phenol reducing agent in the body.

Also, from the results of Experiment 6, it can be seen that when the α-glucan mixture of this branch is ingested, the decrease in the area of the corneocytes, which has been reported as an adverse effect of the phenolic compound on the skin, is not observed, and no basal cells are observed. Increased cell division. The reason can be considered that the intake of this branched α-glucan mixture inhibits the production of phenolic compounds in the body, thus reducing the amount of phenolic compounds that will be absorbed and moved to the skin to cause adverse effects.

The above results show that this branched α-glucan mixture can be advantageously used as an active ingredient of an agent for reducing phenolic compounds in the body, and the food and drink mixed with the agent for reducing phenolic compounds in the body can be advantageously used as Diet for reducing phenolic compounds in the body. In addition, the results of Experiment 6 show that the above-mentioned phenolic compound reducing agent in vivo can reduce the adverse effects on the skin caused by the influence of phenolic compounds by reducing the amount of phenolic compounds produced in the living body caused by food and drink. Influence, that is, hinder the maturation of keratinocytes, and make keratinocytes mature (increase the cell area of keratinocytes), so it can maintain or improve the health of the skin, and be used to improve skin properties, more specifically It is used to improve skin turnover rate.

Hereinafter, the present invention will be described in more detail based on examples. However, the present invention is not limited by these Examples. [Example 1]

<In vivo phenolic compound reducing agent> According to the method described in Example 5 of International Publication No. WO2008/136331 pamphlet, a branched α-glucan mixture powder was prepared as an in vivo phenolic compound reducing agent. Furthermore, the obtained branched α-glucan mixture powder has the following characteristics (a) to (g). (a) with glucose as the constituent sugar, (b) having a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, through α -A branched structure with a glucose polymerization degree of 1 or more linked by bonds other than 1, 4 bonds, (c) Digested with isomaltglucanase to produce 35% by mass of Isomaltose, (d) The content of water-soluble dietary fiber is 80.8% by mass, (e) The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is 1:2.2, ( f) The sum of α-1,4-bonded glucose residues and α-1,6-bonded glucose residues is 72.9% of all glucose residues, (g) The average degree of glucose polymerization is 31, and Mw/Mn is 2.0.

This product is an agent for reducing phenolic compounds in the body with a content of 100% by mass of the branched α-glucan mixture as the active ingredient. This product itself is low sweet or tasteless, has no peculiar smell, does not absorb moisture or change color at room temperature, and is stable for more than 1 year. This strain can be ingested directly or dissolved in water, tea, coffee and other beverages, or added to food or beverages for ingestion. By ingesting this product, phenolic compounds in the body can be reduced. In addition, it can also be advantageously implemented by blending one or more ingredients selected from water, minerals, fragrances, stabilizers, excipients, bulking agents, pH regulators, etc. in this product as needed. . [Example 2]

<In vivo phenol compound reducing agent> According to the method described in Experiment 2-2 of International Publication No. WO2008/136331 pamphlet, a branched α-glucan mixture solution with a solid content concentration of 30% by mass was prepared, and then sprayed according to the general method Dry to obtain branched α-glucan mixture powder, which is used as a phenolic compound reducing agent in vivo. Furthermore, the obtained branched α-glucan mixture powder has the following characteristics (a) to (g). (a) with glucose as the constituent sugar, (b) having a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, through α -A branched structure with a glucose polymerization degree of 1 or higher linked by bonds other than 1, 4 bonds, (c) Digested with isomaltglucanase to produce 27.2% by mass of Isomaltose, (d) The content of water-soluble dietary fiber is 41.8% by mass, (e) The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is 1:0.6, ( f) α-1,4-bonded glucose residues and α-1,6-bonded glucose residues together account for 83.0% of all glucose residues, (g) The average degree of glucose polymerization is 405, Mw/Mn is 16.2.

This product is an agent for reducing phenolic compounds in the body with a content of 100% by mass of the branched α-glucan mixture as the active ingredient. This product itself is low sweet or tasteless, has no peculiar smell, does not absorb moisture or change color at room temperature, and is stable for more than 1 year. This strain can be ingested directly or dissolved in water, tea, coffee and other beverages, or added to food or beverages for ingestion. By ingesting this product, phenolic compounds in the body can be reduced. In addition, it can also be advantageously implemented by blending one or more ingredients selected from water, minerals, fragrances, stabilizers, excipients, bulking agents, pH regulators, etc. in this product as needed. . [Example 3]

<In vivo phenolic compound reducing agent> According to the method described in Example 6 of International Publication No. WO2008/136331 pamphlet, a branched α-glucan mixture powder was prepared as an in vivo phenolic compound reducing agent. Furthermore, the obtained branched α-glucan mixture powder has the characteristics (a) to (g). (a) with glucose as the constituent sugar, (b) having a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, through α -A branched structure with a glucose polymerization degree of 1 or higher linked by bonds other than 1, 4 bonds, (c) Digested with isomaltglucanase to produce 40.6% by mass of Isomaltose, (d) The content of water-soluble dietary fiber is 77.0% by mass, (e) The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is 1:4, ( f) α-1,4-bonded glucose residues and α-1,6-bonded glucose residues together account for 67.9% of all glucose residues, (g) The average degree of glucose polymerization is 18, Mw/Mn is 2.0.

This product is an agent for reducing phenolic compounds in the body with a content of 100% by mass of the branched α-glucan mixture as the active ingredient. This product itself is low sweet or tasteless, has no peculiar smell, does not absorb moisture or change color at room temperature, and is stable for more than 1 year. This strain can be ingested directly or dissolved in water, tea, coffee and other beverages, or added to food or beverages for ingestion. By ingesting this product, phenolic compounds in the body can be reduced. In addition, it can also be advantageously implemented by blending one or more ingredients selected from water, minerals, fragrances, stabilizers, excipients, bulking agents, pH regulators, etc. in this product as needed. . [Example 4]

<In vivo phenolic compound reducing agent> In addition to adding 2 units of maltotetraose per 1 gram of solids to the cornstarch liquefaction solution to generate amylase, it follows the description in Example 5 of International Publication No. WO2008/136331 pamphlet The method is to prepare branched α-glucan mixture powder as an agent for reducing phenolic compounds in vivo. Furthermore, the obtained branched α-glucan mixture powder has the characteristics (a) to (g). (a) with glucose as the constituent sugar, (b) having a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, through α -A branched structure with a glucose polymerization degree of 1 or higher linked by bonds other than 1, 4 bonds, (c) Digested with isomaltglucanase to produce 41.9% by mass of Isomaltose, (d) The content of water-soluble dietary fiber is 69.1% by mass, (e) The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is 1:2.4, ( f) α-1,4-bonded glucose residues and α-1,6-bonded glucose residues together account for 64.2% of all glucose residues, (g) The average degree of glucose polymerization is 13, Mw/Mn is 2.0.

This product is an agent for reducing phenolic compounds in the body with a content of 100% by mass of the branched α-glucan mixture as the active ingredient. This product itself is low sweet or tasteless, has no peculiar smell, does not absorb moisture or change color at room temperature, and is stable for more than 1 year. This strain can be ingested directly or dissolved in water, tea, coffee and other beverages, or added to food or beverages for ingestion. By ingesting this product, phenolic compounds in the body can be reduced. In addition, it can also be advantageously implemented by blending one or more ingredients selected from water, minerals, fragrances, stabilizers, excipients, bulking agents, pH regulators, etc. in this product as needed. . [Example 5]

<In vivo phenolic compound reducing agent> Amyloglucosidase (glucoamylase) was applied to the branched α-glucan mixture obtained by the method described in Example 1, and undecomposed components were separated by gel filtration chromatography . Afterwards, it was purified and spray-dried according to the general method to prepare branched α-glucan mixture powder as a biophenol compound reducing agent. Furthermore, the obtained branched α-glucan mixture has the characteristics (a) to (g). (a) with glucose as the constituent sugar, (b) having a non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by α-1,4 linkages, through α -A branched structure with a glucose polymerization degree of 1 or more linked by bonds other than 1, 4 bonds, (c) Digested with isomaltglucanase to produce 21% by mass of Isomaltose, (d) The content of water-soluble dietary fiber is 94.4% by mass, (e) The ratio of α-1,4-bonded glucose residues to α-1,6-bonded glucose residues is 1:1.9, ( f) α-1,4-bonded glucose residues and α-1,6-bonded glucose residues together account for 64% of all glucose residues, (g) the degree of glucose polymerization is 22, and Mw/Mn is 1.7.

This product is an agent for reducing phenolic compounds in the body with a content of 100% by mass of the branched α-glucan mixture as the active ingredient. This product itself is low sweet or tasteless, has no peculiar smell, does not absorb moisture or change color at room temperature, and is stable for more than 1 year. This strain can be ingested directly or dissolved in water, tea, coffee and other beverages, or added to food or beverages for ingestion. By ingesting this product, phenolic compounds in the body can be reduced. In addition, it can also be advantageously implemented by blending one or more ingredients selected from water, minerals, fragrances, stabilizers, excipients, bulking agents, pH regulators, etc. in this product as needed. . [Example 6]

<Oral composition (powder fruit juice)> 10 parts by mass of biophenol compound reducing agent obtained by the method described in Example 5, 20 parts by mass of glucose, 20 parts by mass of anhydrous crystalline maltitol, 0.65 parts by mass of citric anhydride, apple 0.1 parts by mass of acid, 0.2 parts by mass of 2-O-α-glucoside-L-ascorbic acid, 0.1 parts by mass of sodium citrate, and an appropriate amount of powdered spices, fully 33 parts by mass of citrus juice powder produced by spray drying Mix and stir, pulverize to become a fine powder, feed it into a fluidized bed granulator, set the exhaust temperature at 40°C, and spray an appropriate amount on it. Dissolve the branched α-glucan powder obtained by the method in Example 1 in The solution obtained with water is used as a binder, granulated for 30 minutes, measured and packaged to obtain a product. This strain is a powdered juice with a juice content of about 30%. This product is a powdered fruit juice that can improve the intestinal flora and reduce phenolic compounds in the body because it contains an agent for reducing phenolic compounds in the body. In addition, this product has no peculiar smell and odor, and is of high commercial value as fruit juice. [Example 7]

<Oral composition (custard cream)> 100 parts by mass of corn starch, 30 parts by mass of biophenolic compound reducing agent obtained by the method described in Example 4, 70 parts by mass of trehalose hydrous crystals, 40 parts by mass of glucose and 1 part by mass of table salt are fully mixed, 280 parts by mass of eggs are added and stirred, and 1,000 parts by mass of boiling milk is slowly added to it, and further stirring is continued on the fire until the cornstarch is completely gelatinized and the whole becomes translucent Turn off the fire, cool it down, add an appropriate amount of vanilla spices, measure, fill and pack to obtain the product. This product is a custard cream that can improve the intestinal flora and reduce the phenolic compounds in the body because it contains a biophenolic compound reducing agent. Also, this product is high-quality custard cream with smooth luster and good flavor. [Example 8]

<Oral composition (nutritional supplement)> 247 g of glucose, 217 g of the biophenol compound reducing agent obtained by the method described in Example 3, 8 g of iron pyrophosphate suspension (trade name SunActive FeM manufactured by Sun Chemical Co., Ltd.), 15 g of vitamin premix, 3 g of sodium ascorbate, 0.5 g of zinc yeast, 0.3 g of chromium yeast, and 0.2 g of sucralose were put into the granulation device as granulation raw material powder. On the other hand, 15 g of coffee extract powder and 10 g of magnesium sulfate were dissolved in 100 mL of water for granulation adjustment. While mixing the granulation raw material powder in the device, the granulation adjustment liquid was sprayed in small amounts from the tip of the nozzle to form granules, and the aluminum bag was filled with nitrogen gas so as to be 5.15 g per pack or 10.3 g per pack. This product is a nutritional supplement containing phenolic compound reducers in the body, which can improve the intestinal flora and reduce phenolic compounds in the body. In addition, this product has no peculiar smell and odor, and is of high commercial value as a nutritional supplement. [Example 9]

<Oral composition (black tea drink)> Using the biophenol compound reducing agent obtained by the method described in Example 1, black tea was produced. 1 L of boiling water was added to 15 g of tea leaves, and the tea leaves were filtered to obtain 1 L of black tea extract. 60 g of isomerized sugar was added to 1 L of black tea extract, and biophenolic compound reducing agents were added at 2%, 3%, and 4% by weight, and the obtained black teas were called black tea beverages A, B, and C, respectively. Also, the control group was a black tea beverage obtained in the same manner as above except that no biophenolic compound reducing agent was added. After sensory evaluation of 10 men and women in their 20s to 50s, it was found that it has the effect of masking the unique bitterness or astringency of polyphenols contained in black tea drinks. Furthermore, it was found that even if the black tea drinks A, B, and C were stored at room temperature, compared to the control group, the phenomenon of cream down (the phenomenon of white turbidity when black tea is slowly cooled) was suppressed.

This product is a black tea beverage that can improve the intestinal flora and reduce phenolic compounds in the body because it contains a reducing agent for phenolic compounds in the body. In addition, this product has no peculiar smell and odor, and is of high commercial value as a black tea beverage. [Industrial availability]

As explained above, according to the biophenolic compound reducing agent of the present invention which uses the α-glucan mixture of this branch as an active ingredient, since the α-glucan mixture of this branch itself is low-sweet or tasteless, it It can be used in a wide range, and by ingesting it, it can improve the intestinal flora, and significantly reduce the phenolic compounds in the body known as intestinal spoilage products, so it is useful for the health of the skin, the maintenance of beauty, and the body of health maintenance. In addition, the diet containing the phenolic compound reducing agent of the present invention has the advantage of improving the intestinal flora and effectively reducing the phenolic compound in the living body by taking it in the daily diet. The present invention is a significant contribution to the field and is truly meaningful.

Claims (10)

An agent for reducing phenolic compounds in a living body, which uses a mixture of branched α-glucans with the following characteristics (A) to (C) as an active ingredient: (A) uses glucose as a constituent sugar, (B) has The non-reducing terminal glucose residue at one end of a straight-chain glucan with a glucose polymerization degree of 3 or more linked by an α-1,4 bond is a glucose polymer linked by a bond other than an α-1,4 bond For a branched structure with a degree of 1 or more, (C) isomaltose is produced by digestion with isomaltosetranase. The agent for reducing phenolic compounds in living body according to claim 1, wherein the phenolic compound in living body is phenol and/or p-cresol. The agent for reducing phenolic compounds in the living body according to claim 1 or 2, wherein the aforementioned branched α-glucan mixture is digested by isomaltoglucanase to generate more than 5% by mass relative to the solid matter of the digested matter And the branched α-glucan mixture of isomaltose with 70 mass% or less. The agent for reducing phenolic compounds in the living body according to claim 1 or 2, wherein the aforementioned branched α-glucan mixture is a branched α-glucan mixture having the following characteristics of (D): (D) through the high-speed liquid layer The water-soluble dietary fiber content obtained by the analysis method (enzyme-HPLC method) is more than 40% by mass. The agent for reducing phenolic compounds in living body according to claim 1 or 2, wherein the aforementioned branched α-glucan mixture is a branched α-glucan mixture having the following characteristics (E) and (F): (E)α The ratio of -1,4-bonded glucose residues to α-1,6-bonded glucose residues is in the range of 1:0.6 to 1:4; and (F) α-1,4-bonded glucose residues The sum of glucose residues bonded to α-1,6 accounted for more than 55% of all glucose residues. The agent for reducing phenolic compounds in vivo according to claim 1 or 2, wherein the average degree of glucose polymerization of the branched α-glucan mixture is 8 to 500. The agent for reducing phenolic compounds in living body according to claim 1 or 2, which has the effect of improving intestinal flora. The agent for reducing phenolic compounds in the body as claimed in claim 1 or 2, which is used to improve skin properties. As the agent for reducing phenolic compounds in living body according to claim 8, wherein the improvement of skin properties is the improvement of skin turnover rate. A diet for reducing phenolic compounds in the living body, which contains the phenolic compound reducing agent in the living body according to claim 1 or 2.