JPWO2018193897A1 - In vivo phenolic compound reducing agent - Google Patents

Abstract

An object of the present invention is to provide an in vivo phenolic compound reducing agent and a food and drink for reducing an in vivo phenolic compound comprising the same, wherein a branched α-glucan mixture having the following characteristics (A) to (C) is used as an active ingredient: The above object is achieved by providing an in vivo phenolic compound reducing agent and a food and drink for reducing an in vivo phenolic compound comprising the same: (A) glucose as a constituent sugar, (B) α-1, A non-reducing terminal glucose residue located at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via 4 bonds, and a branch of a degree of polymerization of 1 or more linked via a bond other than α-1,4 bond It has a structure, and (C) isomaltose is produced by isomaltodextranase digestion.

Description

  The present invention relates to an in vivo phenolic compound reducing agent, and in particular, when taken by a human, improves intestinal flora and reduces an in vivo phenolic compound, and includes the same. The invention relates to a food or beverage for reducing a phenolic compound in a living body.

  A wide variety of bacteria (intestinal bacteria) are settled in the human intestine (particularly the large intestine), and form a group of bacteria called intestinal flora (intestinal flora). The intestinal flora is said to be composed of 100 trillion or more trillion intestinal bacteria, and is known to be closely related to human (host) health. Intestinal bacteria proliferate using food residues and secretions from the gastrointestinal tract that humans cannot digest, and are excreted as stool outside the body.

  Known bacteria constituting the intestinal flora include Bifidobacterium (Bifidobacterium), Bacteroides, Eubacterium, Clostridium, Escherichia coli, Lactobacillus, Enterococcus, and the like. Although the balance of bacteria in the intestinal flora varies from person to person, it is said that the person's own balance hardly changes when he is healthy from neonatal to adulthood. However, due to various factors such as stress, overwork, overdrinking and overeating, unbalanced eating, climate and temperature, medicine, infection, and aging, the balance is disrupted, and good bacteria such as bifidobacteria decrease, and It has been pointed out that an increase in bad bacteria causes various diseases such as diarrhea, constipation, infection due to reduced immunity, and carcinogenesis due to an increase in intestinal putrefaction products.

  The intestinal environment is thought to be involved not only in various diseases but also in aging. It is said that in the elderly, the number of bacteria of bifidobacteria decreases and the intestinal flora is disturbed, and it has been pointed out that deterioration of the intestinal flora may promote aging. Bad bacteria in the intestinal tract produce harmful spoilage products (ammonia, amine compounds, phenolic compounds, indole compounds, etc.). It is said that these putrefaction products directly damage the intestinal tract, are partially absorbed into blood, and are involved in the development of various diseases and rough skin around the body.

  As a method for improving the intestinal flora, a method of taking probiotics or prebiotics is well known. Probiotics mean living microbes and foods that contain such microbes in a living state that improve the intestinal environment, produce intestinal and immunomodulatory effects, and have beneficial effects on humans. It is a probiotic that is ingested by dairy products. On the other hand, prebiotics (Prebiotics) are not decomposed and absorbed in the upper gastrointestinal tract, and serve as selective nutrients for beneficial bacteria that coexist in the large intestine, promote their growth, and make the composition of the intestinal flora healthy. It means a food ingredient that improves the balance and helps maintain and improve human health. Up to now, oligosaccharides (galactooligosaccharides, fructooligosaccharides, soybean oligosaccharides, nectar oligosaccharides, xylo-oligosaccharides, isomalisaccharides, raffinose, lactulose, coffee bean mannooligosaccharides, gluconic acid, etc.) and dietary fiber (polydextrose, inulin, etc.) ) Is known as a food ingredient that satisfies the requirements as a prebiotic.

  Improving intestinal flora by taking probiotics and prebiotics could reduce the amount of harmful intestinal spoilage products (ammonia, amine compounds, phenolic compounds, indole compounds, etc.) mentioned above. . Non-Patent Documents 1, 4 and 5, etc., when breeding rats / mouse using a feed containing tyrosine as a raw material of phenol and p-cresol as intestinal putrefaction products, galacto-oligosaccharide and / or lactic acid bacteria. It has been reported that ingestion of fermented milk of bifidobacteria reduces phenol and p-cresol in serum. In addition, Non-Patent Document 2 discloses that phenols produced by intestinal bacteria adversely affect the skin of hairless mice, and Non-Patent Document 3 discloses that phenols produced by intestinal bacteria are human skin. Inhibition of fibroblast differentiation in E. coli has been reported. In addition, Non-Patent Document 6 states that when rats fed on a tyrosine-containing feed were ingested together with high amylose starch, an increase in p-cresol in the living body was suppressed. It has been reported that fermented milk improves human intestinal environment, reduces blood phenolic compounds, and has cosmetic effects such as maintaining the keratin moisture content of the skin.

  However, Non-Patent Document 6 reports that in a test in which rats were ingested inulin, which is known as one of dietary fiber and prebiotics, inulin did not show a p-cresol reducing effect. Therefore, just because a probiotic or prebiotic can improve the intestinal flora does not necessarily mean that phenol compounds, which are harmful metabolites in the living body, can be reduced. Under such circumstances, it is a water-soluble dietary fiber material that functions as a prebiotic that is low in sweetness or tasteless, has a wide range of use, can be ingested easily and safely on a daily basis, and only improves intestinal flora. In addition, it would be very useful if a new material capable of reducing phenol compounds in the living body such as phenol and p-cresol produced as intestinal putrefaction products was provided.

Kawakami et al., "Journal Nutrition Science Vitaminology (J. Nutr. Sci. Vitaminol.)", Vol. 51, pp. 182-186 (2005). Iizuka et al., "Microbiological Ecology in Health and Disease, Vol. 21, pp. 50-56 (2009). Iizuka et al., "Microbiological Ecology in Health and Disease, Vol. 21, pp. 221-227 (2009). Kawakami et al., Yakult Research Institute Research Report, Vol. 29, pp. 15-26 (2010) Ishii et al., "Fragrance Journal", No. 5, 2014 Chen et al., "Luminacoid Research," Vol. 20, No. 1, pp. 31-38, (2016) Yakult Honsha Co., Ltd., news release, “Bifidobacterium fermented milk improves rough skin”, February 4, 2013

  The present invention, when ingested by humans, improves the intestinal flora and has the effect of reducing phenolic compounds in the living body. An object of the present invention is to provide an in vivo phenolic compound reducing agent containing a substance that can be continuously taken as an active ingredient, and a food and drink for reducing the in vivo phenolic compound containing the same.

  As a result of diligent research efforts to solve the above problems, the present inventors have found that the present applicant has disclosed a branched α-glucan mixture disclosed in WO 2008/136331 pamphlet, specifically, glucose Is a constituent sugar, and is connected via a bond other than the α-1,4 bond to a non-reducing terminal glucose residue of a linear glucan having a degree of polymerization of glucose of 3 or more connected via an α-1,4 bond. A branched α-glucan mixture having a branched structure having a degree of 1 or more and producing isomaltose by digestion with isomaltodextranase, when ingested, not only improves intestinal flora, but also improves phenol in vivo. It has been found that the compound has an effect of remarkably reducing the compound. Based on this new finding, the inventors of the present invention have proposed an in vivo phenolic compound reducing agent containing the branched α-glucan mixture as an active ingredient, which is low in sweetness or tasteless and has a wide range of use, and a product comprising the same. A food and drink for reducing phenolic compounds in the body was established, and the present invention was completed.

That is, the present invention solves the above-mentioned problems by providing an in vivo phenol compound reducing agent containing a branched α-glucan mixture having the following characteristics (A) to (C) as an active ingredient.
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue located at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) Isomaltose is produced by isomalt dextranase digestion.

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

  Further, the present invention solves the above-mentioned problems by providing a food and drink for reducing a phenol compound in a living body, which comprises the agent for reducing a phenol compound in a living body.

  The in vivo phenolic compound reducing agent of the present invention has a wide range of use because the branched α-glucan mixture as an active ingredient is low in sweetness or tasteless, and when ingested by humans, it not only improves intestinal flora. Since phenol compounds known as intestinal putrefaction products can be reduced in the living body, they are useful for maintaining skin health and beauty, and further maintaining the health of the living body. In addition, a food or drink comprising the in vivo phenolic compound reducing agent of the present invention can reduce phenolic compounds in a living body simply, safely and effectively by ingesting the same.

The present invention relates to an in vivo phenolic compound reducing agent containing a branched α-glucan mixture having the following characteristics (A) to (C) as an active ingredient.
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue located at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) Isomaltose is produced by isomalt dextranase digestion.

  The in vivo phenolic compound reducing agent referred to in the present specification is a phenolic compound contained in a living body while improving the intestinal flora by increasing a so-called good bacterium in the intestine when taken orally or by gavage by a human. Means an agent that reduces the amount of phenolic compounds contained in biological samples such as cecal contents, serum, urine, feces, skin, etc. It can be confirmed by comparing the case with the case without. Here, the “phenol compound” means phenol, p-cresol (p-methylphenol) and the like. In addition, it is said that these "phenol compounds" produce tyrosine, which is an amino acid derived from a protein taken by humans, by intestinal bacteria and the like and is produced as intestinal putrefaction products.

  As suggested in Non-Patent Document 7, if a phenol compound in a living body, in particular, a phenol compound in blood or skin can be reduced, in skin, maintenance of keratin moisture content and normalization of keratinization of epidermis are performed. It is expected to lead to maintenance of skin health and beauty. In addition, it has been reported that phenolic compounds in the body are associated with carcinogenesis in the large intestine (see Non-Patent Document 6), and if this can be reduced, it is expected that the risk of carcinogenesis and various diseases will be reduced. You.

  The in vivo phenolic compound reducing agent of the present invention contains the above-mentioned branched α-glucan mixture (hereinafter, referred to as “the present branched α-glucan mixture”) as an active ingredient. The present branched α-glucan mixture can be obtained by various production methods as described below, and the resulting branched α-glucan mixture usually has a large number of branched α-glucans having various branched structures and glucose polymerization degrees (molecular weights). -In the form of a mixture of glucans, it is not possible with the current technology to isolate or quantify each branched α-glucan. For this reason, although the structure of each branched α-glucan, that is, the binding mode and the binding order of glucose residues as constituent units cannot be determined for each molecule of the branched α-glucan, the present branched α-glucan mixture The structure can be characterized as a whole mixture by various physical, chemical or enzymatic methods commonly used in the art.

  Specifically, the structure of the present branched α-glucan mixture is characterized by the above-mentioned features (A) to (C) as the whole mixture. That is, the present branched α-glucan mixture is a glucan having glucose as a constituent sugar (feature (A)), and is connected to one end of a linear glucan having a glucose polymerization degree of 3 or more linked via α-1,4 bonds. It has a branched structure with a glucose polymerization degree of 1 or more linked to the located non-reducing terminal glucose residue via a bond other than α-1,4 bond (feature (B)). In addition, the “non-reducing terminal glucose residue” referred to in the characteristic (B) means a glucose residue located at a terminal which does not show reducing property in a glucan chain connected via an α-1,4 bond. "The bond other than the α-1,4 bond” literally means a bond other than the α-1,4 bond.

  Further, the present branched α-glucan mixture produces isomaltose by isomaltodextranase digestion (feature (C)). Isomaltodextranase digestion referred to in the feature (C) means that isomaltdextranase is allowed to act on the main branched α-glucan mixture and hydrolyzed. Isomaltodextranase is an enzyme having an enzyme number (EC) of 3.2.1.94, and α-1,2, α-1 adjacent to the reducing end of the isomaltose structure in α-glucan. , 3, α-1,4 and α-1,6 bonds. Suitably, isomaltodextranase from Arthrobacter gloviformis (eg, Sawai et al., Agricultural and Biological Chemistry, Vol. 52, No. 2, No. Pages 495-501 (1988)).

  The generation of isomaltose by isomalt-dextranase digestion means that the branched α-glucan molecule constituting the branched α-glucan mixture has an isomaltose structure that can be hydrolyzed by isomalt-dextranase. According to the feature (C), the present branched α-glucan mixture has a structural feature that, when viewed as a mixture as a whole, contains an isomaltose structure that can be hydrolyzed by isomaltdextranase. Can be characterized by enzymatic techniques.

  As the present branched α-glucan mixture, isomaltose is usually 5% by mass to 70% by mass, preferably 10% by mass to 60% by mass, based on the solid matter of the digested product, by digestion with isomaltodextranase. More preferably, those produced in an amount of 20% by mass or more and 50% by mass or less are preferably used because they are more suitable for improving the intestinal flora and more excellent in reducing the phenol compound concentration in the living body. .

  That is, as described below, the effect of the present branched α-glucan mixture on the improvement of the intestinal flora and the effect of reducing the concentration of phenolic compounds in the living body are such that the present branched α-glucan mixture is isomaltose digested by isomaltodextranase. It is thought that having the structural feature of generating is deeply involved. That is, a branched α-glucan mixture having an isomaltose production amount of less than 5% by mass in isomaltdextranase digestion has a structural characteristic close to maltodextrin having a small branched structure, and conversely, isomaltdextranase The branched α-glucan mixture having an isomaltose production amount of more than 70% by mass in digestion has a structural characteristic close to that of dextran which is a glucose polymer connected by α-1,6 bonds, and the above-mentioned characteristic (B) In any case, the structural characteristics considered to be involved in the improvement of the intestinal flora and, consequently, the reduction of phenolic compounds in the living body are diminished, and isomaltose by isomaltodextranase digestion. There is a suitable range for the amount of

  Further, as a more preferred embodiment of the present branched α-glucan mixture, there is a feature (D) that the content of water-soluble dietary fiber determined by high performance liquid chromatography (enzyme-HPLC method) is 40% by mass or more. Are included.

  "High performance liquid chromatography (enzyme-HPLC method)" (hereinafter simply referred to as "enzyme-HPLC method") for determining the content of water-soluble dietary fiber is the nutrition labeling standard of the Ministry of Health and Welfare Notification No. 146, May 1996. This is the method described in Section 8, "Dietary Fiber" in "Methods for Analyzing Nutritional Components, etc. (Methods Listed in Nutrition Labeling Standard Appended Table 1, Column 3)". It is as follows. That is, the sample is subjected to a decomposition treatment by a series of enzyme treatments with a heat-stable α-amylase, a protease and a glucoamylase, and proteins, organic acids, and inorganic salts are removed from the treatment solution by an ion exchange resin, thereby preparing a sample for gel filtration chromatography. Prepare solution. Next, the gel solution was subjected to gel filtration chromatography to determine the peak areas of undigested glucan and glucose in the chromatogram, and to determine the respective peak areas and the glucose in the sample solution determined by the glucose oxidase method separately by a conventional method. The amount is used to calculate the water soluble dietary fiber content of the sample. In addition, throughout this specification, “water-soluble dietary fiber content” means the content of water-soluble dietary fiber determined by the aforementioned “enzyme-HPLC method” unless otherwise specified.

  The water-soluble dietary fiber content indicates the content of α-glucan that is not decomposed by α-amylase and glucoamylase, and the feature (D) is that the structure of the present branched α-glucan mixture is expressed by an enzymatic method as a whole. This is one of the indices characterized by

  As described above, the effect of improving the intestinal flora by the present branched α-glucan mixture and the effect of reducing phenolic compounds in the living body are deeply characterized by the structural feature that isomaltose is generated by digestion with isomaltodextranase. It is believed that this characteristic structural portion, of course, is involved in the higher the water-soluble dietary fiber content of the present branched α-glucan mixture, in other words α-amylase and glucoamylase. It is considered that the larger the content of the branched α-glucan that is not decomposed in the above, the more it reaches the large intestine without being digested, and shows an intestinal flora improving effect. Therefore, as the present branched α-glucan mixture which is an active ingredient of the in vivo phenolic compound-reducing agent of the present invention, the higher the water-soluble dietary fiber content, the more preferable. The preferable water-soluble dietary fiber content is usually 40% by mass. However, it is more preferably 60% by mass or more, and still more preferably 75% by mass or more. There is no particular upper limit of the suitable water-soluble dietary fiber content, and the higher the technically possible, the better, and preferably 100% by mass or less or less than 100% by mass.

Further, a more preferred embodiment of the present branched α-glucan mixture includes a branched α-glucan mixture having the following features (E) and (F).
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is in the range of 1: 0.6 to 1: 4,
(F) The sum of α-1,4 bonded glucose residues and α-1,6 bonded glucose residues accounts for 55% or more of all glucose residues.

  In addition, whether or not the branched α-glucan mixture has the above characteristics (E) and (F) can be confirmed by methylation analysis. As is well known, methylation analysis is a method generally used as a method for determining the binding mode of a monosaccharide constituting a polysaccharide or an oligosaccharide (Cicanu et al., Carbohydrate). -Research (Carbohydrate Research), Vol. 131, No. 2, pp. 209-217 (1984)). When the methylation analysis is applied to the analysis of the binding mode of glucose in glucan, first, all free hydroxyl groups in glucose residues constituting the glucan are methylated, and then the fully methylated glucan is hydrolyzed. Next, the methylated glucose obtained by the hydrolysis is reduced to methylated glucitol in which the anomeric form has been eliminated, and further, a free hydroxyl group in the methylated glucitol is acetylated to obtain a partially methylated glucitol acetate (in addition, a methylated glucitol acetate). , "Partially methylated glucitol acetate" may be referred to simply as "partially methylated product"). By analyzing the obtained partially methylated product by gas chromatography, various partial methylated products derived from glucose residues having different binding modes in glucan have a peak area occupying the peak area of all partial methylated products in the gas chromatogram. Can be expressed as a percentage (%). Then, from the peak area%, the abundance ratio of glucose residues having different binding modes in the glucan, that is, the abundance ratio of each glucoside bond can be determined. The “ratio” for a partially methylated product means “ratio” of a peak area in a gas chromatogram of a methylation analysis, and the “%” for a partially methylated product means “area%” in a gas chromatogram of a methylation analysis. Shall be.

  The “α-1,4 bonded glucose residue” in the above features (E) and (F) refers to glucose bonded to another glucose residue only through a hydroxyl group bonded to the 1-position and 4-position carbon atoms. Residue, which is detected as 2,3,6-trimethyl-1,4,5-triacetylglucitol in methylation analysis. The “α-1,6-bonded glucose residue” in the above features (E) and (F) refers to a bond to another glucose residue only through a hydroxyl group bonded to the 1- and 6-position carbon atoms. And is detected as 2,3,4-trimethyl-1,5,6-triacetylglucitol in methylation analysis.

  The ratio (characteristic (E)) of α-1,4 linked glucose residues to α-1,6 linked glucose residues obtained by methylation analysis, and α-1,4 linked glucose residues The ratio of α-1,6-linked glucose residues to all glucose residues (characteristic (F)) is used as one of indexes for characterizing the structure of the present branched α-glucan mixture as a whole by a chemical method. be able to.

  The definition of the above feature (E) that “the ratio of α-1,4 linked glucose residue to α-1,6 linked glucose residue is in the range of 1: 0.6 to 1: 4” When the branched α-glucan mixture is subjected to methylation analysis, 2,3,6-trimethyl-1,4,5-triacetylglucitol and 2,3,4-trimethyl-1,5,5 are detected. It means that the ratio of 6-triacetylglucitol is in the range from 1: 0.6 to 1: 4. In addition, the above-mentioned feature (F) defines that “the sum of α-1,4 bonded glucose residues and α-1,6 bonded glucose residues accounts for 55% or more of all glucose residues”. This methylated α-glucan mixture showed 2,3,6-trimethyl-1,4,5-triacetylglucitol and 2,3,4-trimethyl-1,5,6-triacetylglu It means that the sum with the sitol accounts for 55% or more of the partially methylated glucitol acetate. Normally, starch does not have glucose residues bonded only at the 1-position and 6-position, and α-1,4 bonded glucose residues occupy the majority of all glucose residues. The fact that the α-glucan mixture has the characteristics (E) and (F) means that the present branched α-glucan mixture has a structure completely different from that of starch.

  As defined by the above features (E) and (F), in one preferred embodiment, the present branched α-glucan mixture is substantially free from “α-1,6-linked glucose residues” which are not normally present in starch. Although those having a more complicated branch structure can be expected to have higher effects, in addition to α-1,4 bond and α-1,6 bond, α-1,3 bond and / or α- It preferably has 1,3,6 bonds. Here, the “α-1,3,6 bond” refers to “a glucose residue bonded to another glucose (α-1,3,6 bonded) at three positions of hydroxyl groups at the first, third, and sixth positions. "Group". If it has α-1,3 bond and / or α-1,3,6 bond in addition to α-1,4 bond and α-1,6 bond, it will have a more complicated branch structure. Therefore, basically, it is sufficient that the present branched α-glucan mixture contains α-1,3 bond and / or α-1,3,6 bond, and the ratio is not particularly limited, For example, it is preferable that the α-1,3 linked glucose residue is 0.5% or more and less than 10% of the total glucose residue, and the α-1,3,6 linked glucose residue is the total glucose residue. It is preferably at least 0.5%.

  The above-mentioned “α-1,3 bonded glucose residue is 0.5% or more and less than 10% of all glucose residues” means that the present branched α-glucan mixture was subjected to methylation analysis, and 2,4,6 It can be confirmed by the fact that trimethyl-1,3,5-triacetylglucitol is present in an amount of 0.5% to less than 10% of the partially methylated glucitol acetate. In addition, the above-mentioned “α-1,3,6-linked glucose residues are 0.5% or more of all glucose residues” means that the present branched α-glucan mixture was subjected to methylation analysis, It can be confirmed by the presence of dimethyl-1,3,5,6-tetraacetylglucitol at 0.5% or more and less than 10% of the partially methylated glucitol acetate.

  The present branched α-glucan mixture can also be characterized by the weight average molecular weight (Mw) and the value (Mw / Mn) obtained by dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn). The weight average molecular weight (Mw) and the number average molecular weight (Mn) can be determined using, for example, size exclusion chromatography. Further, since the average glucose polymerization degree of the branched α-glucan constituting the present branched α-glucan mixture can be calculated based on the weight average molecular weight (Mw), the present branched α-glucan mixture is characterized by the average glucose polymerization degree. It can also be attached. The average glucose polymerization degree can be determined by subtracting 18 from the weight average molecular weight (Mw) and dividing by 16 corresponding to the molecular weight of the glucose residue. The branched α-glucan mixture used as an active ingredient of the in vivo phenol compound reducing agent preferably has an average glucose polymerization of usually from 8 to 500, preferably from 15 to 400, more preferably from 20 to 300. The branched α-glucan mixture exhibits the same properties as ordinary glucan in that the viscosity increases as the average glucose polymerization degree increases, and the viscosity decreases as the average glucose polymerization degree decreases. Therefore, according to the embodiment of the in vivo phenolic compound reducing agent of the present invention, the present branched α-glucan mixture having an average degree of polymerization of glucose suitable for the required viscosity can be appropriately selected and used.

  Mw / Mn, which is a value obtained by dividing the weight-average molecular weight (Mw) by the number-average molecular weight (Mn), is a variation in the degree of glucose polymerization of the branched α-glucan molecules constituting the branched α-glucan mixture, the closer to 1 the composition is. Means smaller. Although the present branched α-glucan mixture used as an active ingredient of the in vivo phenol compound reducing agent can be used without any problem if the Mw / Mn is usually 20 or less, it is preferably 10 or less, more preferably 5 or less. Those are preferred. In addition, when a main branched α-glucan mixture having a relatively uniform glucose polymerization degree is required as an active ingredient of the in vivo phenolic compound reducing agent according to the present invention, Mw / Mn is closer to 1 and the glucose polymerization degree varies. The smaller is, the better.

  The present branched α-glucan mixture may be produced by any method as long as it has the above-mentioned characteristics (A) to (C). For example, a branched structure having a glucose polymerization degree of 1 or more linked via an α-1,6 bond to a non-reducing terminal glucose residue of a linear glucan having a glucose polymerization degree of 3 or more linked via an α-1,4 bond. A branched α-glucan mixture obtained by allowing an enzyme having an action of introducing glycerol to act on starch can be suitably used in the practice of the present invention. As a more preferable example, WO 2008/136331 Examples include a branched α-glucan mixture obtained by allowing an α-glucosyltransferase disclosed in a pamphlet to act on starch. In addition to the α-glucosyltransferase, an amylase such as maltotetraose-forming amylase (EC 3.2.1.60) or a starch debranching enzyme such as isoamylase (EC 3.2.1.68) is used. When used in combination, the branched α-glucan mixture can be reduced in molecular weight, so that the molecular weight, the degree of glucose polymerization and the like can be adjusted to desired ranges. Further, cyclomaltodextrin glucanotransferase (EC 2.4.1.19), starch branching enzyme (EC 2.4.1.18), and the degree of polymerization disclosed in JP-A-2014-054221. The combined use of an enzyme having an activity of transferring two or more α-1,4 glucans to α-1,6 transfer to a glucose residue inside amylaceous starch in combination with a branched α-glucan constituting a branched α-glucan mixture further improves the branched α-glucan mixture. It can also be highly branched to increase the water soluble dietary fiber content of the branched α-glucan mixture. The thus obtained branched α-glucan mixture may be further reacted with a saccharide hydrolase such as glucoamylase to further form a branched α-glucan mixture having a higher content of water-soluble dietary fiber. (EC 5.4.9.15) to introduce a trehalose structure into the reducing terminal of the branched α-glucan constituting the branched α-glucan mixture, or to reduce the reducing terminal of the branched α-glucan by hydrogenation. Alternatively, the reducing power of the branched α-glucan mixture may be reduced, and it is also possible to obtain a branched α-glucan mixture having a desired molecular weight by performing fractionation by size exclusion chromatography or the like. It is.

  The amount of the present branched α-glucan mixture contained in the in vivo phenolic compound reducing agent of the present invention is not particularly limited as long as the intended in vivo phenolic compound reducing effect is exhibited. It may be contained in an amount of 1 to 100% by mass, preferably 3 to 100% by mass, more preferably 5 to 100% by mass. In addition, the in vivo phenolic compound reducing agent of the present invention includes, in addition to the present branched α-glucan mixture, if necessary, water, minerals, flavors, stabilizers, excipients, bulking agents, pH adjusters, and the like. One or two or more components selected from the following may be used by appropriately mixing them at a ratio of 0.01 to 50% by mass, preferably 0.1 to 40% by mass.

  The in vivo phenolic compound reducing agent of the present invention may be taken in an amount that exhibits the effect of reducing the amount of the phenolic compound in the living body, and there is no particular limitation on the amount of ingestion. The amount of the glucan mixture to be taken is generally in the range of 0.5 to 100 g, preferably in the range of 1 to 50 g, more preferably in the range of 1.5 to 10 g, more preferably 3 per adult (60 kg body weight). So that the in vivo phenolic compound reducing agent of the present invention is taken as it is, or dissolved in a beverage such as water, tea, coffee or the like, or added to a food or beverage and taken. Good. The in vivo phenolic compound reducing agent of the present invention may, of course, be taken before or after taking a food or beverage.

  The in vivo phenolic compound reducing agent of the present invention is in the form of powder, granule, granule, liquid, paste, cream, tablet, capsule, caplet, soft capsule, tablet, rod, plate, block, It can be in an appropriate form such as pill, solid, gel, jelly, gummy, wafer, biscuit, candy, chewable, syrup, stick and the like. In addition, the in vivo phenolic compound reducing agent of the present invention is intended to prevent or ameliorate lifestyle-related diseases such as foods for specified health use, functionally labeled foods, dietary supplements, and health foods by being incorporated into foods and drinks. It can be in the form of food or drink that is ingested for the purpose.

  Specific examples of food and drink for in vivo phenolic compound reduction comprising the in vivo phenolic compound reducing agent of the present invention include carbonated drinks, milk drinks, jelly drinks, sports drinks, vinegar drinks, soy milk drinks, iron-containing drinks, Lactic acid bacteria drinks, beverages such as green tea, black tea, cocoa, coffee, rice, rice porridge, bread, noodles, soup, miso soup, yogurt, etc., soft candy, hard candy, gummy, jelly, cookies, soft cookies, rice crackers, hail, Okoshi, fertilizer, rice cake, warabi mochi, steamed bun, seaweed, bean paste, yokan, mizuyokan, nishikidama, jelly, pectin jelly, castella, biscuit, cracker, pie, pudding, butter cream, custard cream, cream puff, waffle, Sponge cake, hot cake, muffin, donut, chocolate, moth Ash, cereal bar, chewing gum, caramel, nougat, flower paste, peanut paste, fruit paste, jam, marmalade, etc., ice cream, sherbet, gelato, etc., and soy sauce, powdered soy sauce, miso, powdered miso, Moromi, Hoshio, Furikake, Mayonnaise, Dressing, Vinegar, Three tablespoons vinegar, Powdered sushi vinegar, Chinese ingredients, Tentsuyu, Noodle soup, Sauce, Tomato sauce, Ketchup, Grilled meat sauce, Yakitori sauce, Fried flour, Tempura flour, Cararou , Stew ingredients, soup ingredients, dash ingredients, complex seasonings, mirin, new mirin, table sugar, coffee sugar, and various other seasonings and cooked products. Further, the in vivo phenolic compound reducing agent of the present invention may be a solution, a syrup, a tube feeding agent, a tablet, a capsule, a troche, a sublingual agent, a granule, for preventing or improving (treating) a lifestyle-related disease. It can also be incorporated into drugs in the form of powders, powders, emulsions, sprays and the like. Further, the in vivo phenolic compound reducing agent of the present invention can also be incorporated into pet food, feed, and feed that are taken by animals other than humans.

  The in vivo phenolic compound reducing agent of the present invention and the food and drink for reducing the in vivo phenolic compound containing the same may be administered to the stomach or digestive tract by parenteral administration such as tube administration, if necessary. Can also.

  Further, the in vivo phenolic compound reducing agent of the present invention can reduce the amount of a phenolic compound produced in the living body due to food and drink, as shown in the experimental section described below, so that the phenolic compound exerts an effect on the skin. It has the effect of reducing adverse effects on skin, maintaining or improving skin health, and specifically, optimizing and improving skin turnover.

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

In the following experiments, a branched α-glucan mixture produced according to the method described in Example 5 of WO 2008/136331 was used. That is, according to the method described in Example 5, sodium bisulfite was added to a 27.1% by mass corn starch liquefied liquid (hydrolysis rate: 3.6%) so as to have a final concentration of 0.3% by mass. After adding calcium chloride to a final concentration of 1 mM, the mixture was cooled to 50 ° C., and Bacillus circulans PP710 (prepared by the method described in Example 1 of WO 2008/136331) was added thereto. A crude enzyme solution of α-glucosyltransferase derived from FERM BP-10771) was added at 11.1 units per gram of solid, and the mixture was allowed to act at 50 ° C. and pH 6.0 for 68 hours. The reaction solution was kept at 80 ° C. for 60 minutes, cooled, filtered, and the resulting filtrate was decolorized with activated carbon, desalted with H-type and OH-type ion resins, purified, and further concentrated, according to a conventional method. The branched α-glucan mixture produced by spray drying was used in Experiment 1 below. In addition, the obtained branched α-glucan mixture was subjected to the isomaltodextranase digestion test method, α-glucosidase and glucoamylase digestion test method described in paragraphs 0079 and 0080 of WO 2008/136331 pamphlet, paragraph 0076. As a result of analysis by the methylation analysis method described in any of (1) to (0078), it had the following characteristics (a) to (c).
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) Isomaltose was produced by digestion with isomaltodextranase at 35% by mass per solid of the digest.

In addition, when the obtained branched α-glucan mixture was analyzed by the enzyme-HPLC method, the branched α-glucan mixture had the following characteristics (d) in addition to the above characteristics. From the results of the analysis by the methylation analysis method, it was found that the sample had the following characteristics (e) to (h).
(D) a water-soluble dietary fiber content of 82.9% by mass;
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is 1: 2.1,
(F) The total of α-1,4 bonded glucose residues and α-1,6 bonded glucose residues was 73.8% of all glucose residues.
(G) α-1,3 linked glucose residues were 2.1% of all glucose residues.
(H) α-1,3,6-linked glucose residues were 5.6% of all glucose residues.

  Further, when the branched α-glucan mixture was subjected to molecular weight distribution analysis by gel filtration HPLC described in paragraph 0081 of WO 2008/136331, the weight average molecular weight (Mw) was 5,000 daltons (average Mw / Mn was 2.1 when converted to a glucose polymerization degree of about 30).

  As described above, the branched α-glucan mixture used in this experiment was composed of glucose as a constituent sugar, and a non-reducing terminal glucose residue of a linear glucan having a degree of polymerization of glucose of 3 or more linked via α-1,4 bond. (A) to (C), which have a branched structure having a degree of polymerization of glucose of 1 or more linked through a bond other than an α-1,4 bond, and produce isomaltose by digestion with isomaltodextranase. It had the following. Further, the branched α-glucan mixture used in this experiment is characterized in that isomaltose is produced by digestion with isomaltodextranase in an amount of 5% by mass or more and 70% by mass or less based on the solid matter of the digested matter. (D), wherein the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is 1: 0.6 to 1: 4. (E) and (F), wherein the total of glucose residues having α-1,4 bond and α-1,6 bond accounts for 55% or more of all glucose residues. Was satisfied.

  Further, the branched α-glucan mixture has α-1,3 linked glucose residues in a range of 0.5% or more and less than 10% of the total glucose residues, and α-1,3,6 linked glucose residues. The groups were in the range of 0.5% or more of the total glucose residues.

  In the following experiments, rats were used as experimental animals, and a feed supplemented with and supplemented with tyrosine, an amino acid serving as a raw material of a phenol compound in a living body (hereinafter referred to as “tyrosine feed”), was given as a feed. As drinking water, water or a branched α-glucan mixture aqueous solution obtained by dissolving the above-mentioned branched α-glucan mixture at a specific concentration in water is fed for a certain period of time while feeding, and then the amount of phenolic compounds in various biological samples collected from rats. Was measured.

<Experiment 1: Feeding of tyrosine feed and breeding of rats by drinking water of branched α-glucan mixture>
Twenty-four Wistar rats (male, 6 weeks old, sold by Japan SLC, Inc.) were purchased and reared for 5 days while being fed a normal feed ("CE-2", breeding and breeding, sold by Nippon Clea Co., Ltd.) to be acclimated. Was. Next, the acclimated rats were divided into four groups of six rats, and the rats of each group were fed as shown in Table 1 below, that is, any of the AIN-93G modified feed and the tyrosine feed described later, and also as shown in Table 1. Drinking water, that is, water or an aqueous solution obtained by dissolving the branched α-glucan mixture obtained above in water to 2% (w / v) or 5% (w / v) (hereinafter referred to as “2% branch, respectively”). α-glucan mixture ”or“ 5% branched α-glucan mixture ”) and bred for 3 weeks.

  The “AIN-93G modified feed” and “tyrosine feed” shown in Table 1 are feeds having the compositions shown in Table 2 below, respectively, and were obtained by outsourcing to CLEA Japan. The AIN-93G modified feed is a standard feed “AIN-93G” sold by CLEA Japan, where the composition of corn starch is 39.7486% by mass, modified to 51.9486% by mass, and α -The same composition as AIN-93G except that the composition of corn starch was changed from 13.2% by mass to 1% by mass. As shown in Table 2, the tyrosine feed was obtained by substituting 5% by mass of corn starch of the AIN-93G modified feed with tyrosine.

  Table 3 shows the weight, food consumption, and water consumption of the rats in each group during the breeding period. Furthermore, the amount of feces and urine for one day each collected from one rat was measured using a metabolic gauge on the 19th to 20th days of breeding. Table 4 shows the average value and standard deviation of 6 animals in each group. Indicated.

  As shown in Table 3, the rats in the four groups tested exhibited similar values in body weight, food consumption, and water consumption, and no significant difference was observed between the groups. This indicates that rats in the normal diet group fed with AIN-93G modified feed as feed and water as drinking water, rats in the control group fed with tyrosine feed as feed, and a specific concentration of drinking water This indicates that rats in the test group to which the branched α-glucan mixture was ingested were bred in a stable test system in which there was no significant difference between the groups. In addition, when calculated from the amount of food consumed, the daily intake of tyrosine in the rats that took the tyrosine feed was about 4 g / kg-body weight. In addition, regarding the rats that have been ingested with the aqueous solution of the branched α-glucan mixture, the daily intake of the branched α-glucan mixture is 1.9 g / kg in the 2% branched α-glucan mixture group, calculated from the amount of water consumed. -Body weight was 5.1 g / kg-body weight in the 5% branched α-glucan mixture group.

  In addition, as for the amount of feces and urine during breeding, as shown in Table 4, the control group fed with a tyrosine feed and given water as drinking water showed higher values in the amount of feces than the other groups. However, no significant difference was observed between the groups. The results indicate that, as in the case of body weight, food consumption, and water consumption shown in Table 3, rats were bred in a stable test system in which there was no large difference between the groups. .

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

<Experiment 2-1. Collection of various samples from rats>
A total of 24 rats in 4 groups bred in Experiment 1 were each euthanized by collecting whole blood from the posterior vena cava under pentobarbital anesthesia. After euthanasia, the cecum and liver were dissected out, collected and weighed. After shaving the flank, the skin was collected from two places with a size of 1 cm square, and the subcutaneous tissue was removed to obtain a skin sample. Table 5 summarizes the weights of the collected liver, cecal tissue, and cecal contents, and the pH of the cecal contents. The pH of the cecal contents was measured directly with a pH meter.

  As shown in Table 5, the weight of the cecal tissue and cecal contents was significantly heavier in the 2% branched α-glucan mixture group and the 5% branched α-glucan mixture group than in the control group. The cecal contents of the normal diet group and the control group showed a greenish color, while the cecal contents of the 5% branched α-glucan mixture group showed a yellowish color. In the 2% branched α-glucan mixture group, the caecal contents showed a ratio of 4 yellowish tones and 2 greenish tones, indicating that the branched α-glucan mixture was It was suggested that the intestinal flora had changed in the ingested group. In addition, the pH of the cecal contents of the group to which the branched α-glucan mixture was ingested was significantly lower than that of the control group.

<Experiment 2-2. Pretreatment of each sample for measurement of phenolic compounds in vivo>
In addition to the urine and feces collected in Experiment 1, each sample collected in Experiment 2-1, ie, cecal contents, blood (serum), skin, and liver, was used as a pretreatment for phenol compound measurement, respectively. The processing shown was performed.

<Caecal contents>: Thawed frozen and stored at -80 ° C after collection, weighed 0.3 g, diluted 10-fold with 3 mL of 0.1 M phosphate buffer (pH 5.5), Using a homogenizer (5 mL) made of tetrafluoroethylene, the mixture was homogenized and centrifuged (3,000 rpm, 800 × g, 10 minutes) to prepare a crude extract, which was stored frozen at −80 ° C.
<Serum>: The collected blood was centrifuged (3,000 rpm, 800 × g, 10 minutes) to separate serum, and stored frozen at −80 ° C.
<Urine>: After centrifugation (3,000 rpm, 800 × g, 10 minutes) to remove precipitates (feed, etc.), the mixture was stored frozen at −80 ° C.
<Feces>: Thawed at -80 ° C after collection, thawed, diluted 10-fold with 0.1 M phosphate buffer (pH 5.5), stirred for about 5 minutes, and then homogenized with polytetrafluoroethylene ( (10 mL), and the mixture was centrifuged (3,000 rpm, 800 × g, 10 minutes) to prepare a crude extract, which was stored frozen at −80 ° C.
<Skin>: After collection, the cryopreserved at -80 ° C. was thawed, 0.2 g was weighed, cut with scissors, taken in a plastic tube, added with 2 mL of a phosphate buffer, and homogenized (“Polytron PT10-”). 35 "). 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) to collect a supernatant, which was frozen and stored at −80 ° C.
<Liver>: Thawed at −80 ° C. after collection, thawed, weighed 0.2 g of the left outer lobe of the liver, placed in a 1.5 mL plastic tube, added 1 mL of phosphate buffer, and added polytetrafluoroethylene. The mixture was homogenized with a homogenizer and centrifuged (3,000 rpm, 800 × g, 10 minutes) to prepare a crude extract, which was frozen and stored at −80 ° C.

<Experiment 2-3. Determination of phenol compounds in each sample>
Since most of the phenolic compounds in the pretreated sample prepared in Experiment 2-2 are in the form of glycosides, the phenolic compound in the form of glycosides is hydrolyzed by treating the pretreated sample with hydrochloric acid. Was measured as a phenolic compound after changing to the free form. That is, in this measurement, two phenol compounds of phenol and p-cresol were measured, and phenol and p-cresol which existed in the form of a glycoside in a living body and those which existed in a free form were determined. By performing the acid treatment, it was collectively determined as free phenol and p-cresol, respectively. As a specific operation, the pretreatment sample described above was centrifuged (4,700 rpm, 10 minutes) to collect a supernatant, and then 0.8 mL was taken into a tube with a screw (in the case of urine, 220 mL was used). (Double dilution)), 32 μL of 4-ethylphenol, an internal standard substance adjusted to a concentration of 100 μg / mL, and 0.8 mL of 2N hydrochloric acid were added, and the mixture was boiled for 60 minutes. After the solution subjected to the boiling treatment was allowed to cool at room temperature, about 0.75 mL of 2N sodium hydroxide was added to neutralize the solution. Take 0.8 mL of the neutralized solution into a plastic tube, add 0.8 mL of acetonitrile, stir, centrifuge (12,000 × g, 5 minutes) to remove insolubles, and add 0.3 mL to 0.45 μm The mixture was filtered with a filter to obtain 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 × 150 mm, manufactured by Showa Denko KK);
Equipment: "Prominence" system (manufactured by Shimadzu Corporation)
Use "LabSolutions" as analysis software;
Pump: LC-20AD 2 units;
Column heater: “CTO-20AC”;
Degasser: "DGU-20A _3R ";
Autosampler: "SIL-20AC";
Detector: Fluorescence detector RF-20A (excitation wavelength: 260 nm, fluorescence wavelength: 305 nm)
Mobile phase: Isocratic elution with water / acetonitrile (70/30) Column temperature: 30 ° C
Sample injection volume: 10 μL
In the determination of phenol and p-cresol, phenol and p-cresol reagents (manufactured by Sigma-Aldrich) were used as standard products, and calibration curves were prepared for HPLC and quantified.

  Tables 6 and 7 show quantitative values of phenol compounds (phenol and p-cresol) in various samples.

  As shown in Tables 6 and 7, in rats in the normal diet group bred with AIN-93G modified feed and water, phenol was not detected in any of the cecal contents, serum, urine, feces, skin and liver, Further, p-cresol was also slightly detected in cecal contents, urine, and feces. In contrast, in rats bred on a tyrosine diet, phenol was detected in all but the skin and liver, and p-cresol was detected in greater amounts than in the normal diet group.

  As shown in Table 6, in the normal diet group of rats fed the AIN-93G modified feed and water, phenol was not detected in the cecal contents, and the amount of p-cresol per 1 g of cecal contents was also 40 ± 28 nmol. In contrast, in the case of a control group of rats fed with tyrosine feed and water, the amount of phenol and the amount of p-cresol were as high as 812 ± 443 nmol and 4522 ± 1261 nmol, respectively, per 1 g of cecal content. Formation of a phenolic compound was observed. On the other hand, in the case of the 2% branched α-glucan mixture group fed and fed with a tyrosine feed and a 2% branched α-glucan mixture aqueous solution, the amount of phenol per 1 g of cecal content is 334 ± 435 nmol, and the amount of p-cresol is 2866 ± 1652 nmol. And a phenol compound amount significantly lower than that of the control group. In the case of the 5% branched α-glucan mixture group bred by ingesting a tyrosine feed and a 5% branched α-glucan mixture aqueous solution, the amount of phenol was 12 ± 3 nmol and the amount of p-cresol was 397 ± 128 nmol per 1 g of cecal content. And a phenol compound amount significantly lower than that of the control group. This result indicates that the ingestion of tyrosine feed produces a phenolic compound in the cecal contents, and that even when a tyrosine feed in which a phenolic compound is easily produced is ingested, a certain amount or more of the branched α-glucan mixture is also consumed. This indicates that the amount of the phenol compound in the cecal contents can be significantly reduced.

  In addition, as shown in Table 6, in the rats in the normal diet group bred with the AIN-93G modified feed and water, neither phenol nor p-cresol was detected in the serum, whereas the tyrosine feed and water were not detected. In the case of a control group of rats fed and raised, the amount of phenol was 27 ± 30 nmol and the amount of p-cresol was 136 ± 35 nmol per 1 mL of serum, indicating the formation of a phenol compound. On the other hand, in the case of the 2% branched α-glucan mixture group fed and fed with a tyrosine feed and a 2% branched α-glucan mixture aqueous solution, the amount of phenol per mL of serum was 16 ± 15 nmol, and the amount of p-cresol was 101 ± 50 nmol. Although the result was not much different from that of the control group, in the case of the 5% branched α-glucan mixture group fed and fed with a tyrosine feed and a 5% branched α-glucan mixture aqueous solution, the amount of phenol per mL of serum was 5%. The amount of phenol compound was ± 0 nmol and the amount of p-cresol was 15 ± 4 nmol, which was significantly lower than that of the control group. This result indicates that a phenolic compound is detected in serum by ingestion of a tyrosine feed, and that even if a tyrosine feed in which a phenolic compound is easily produced is ingested, a certain amount or more of a branched α-glucan mixture is also consumed. This indicates that the amount of phenolic compounds in serum can be significantly reduced.

  Furthermore, in each group, urine for one day collected from one rat was analyzed, and the amount of phenolic compound excreted into urine per day was shown in μmol / day. As shown in Table 6, no phenol was detected in the urine and the amount of p-cresol was as small as 5 ± 4 μmol / day in the rats in the normal diet group, whereas the amount of phenol in the rats in the control group was small. Was 42 ± 15 μmol / day, and the amount of p-cresol was 208 ± 41 μmol / day, indicating a large amount of phenol compounds. On the other hand, in the case of 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 much different from the control group. In the case of the -glucan mixture group, the amount of phenol was 4 ± 7 μmol / day and the amount of p-cresol was 58 ± 48 μmol / day, which was significantly smaller than the control group. This result indicates that a phenolic compound is detected in urine by ingestion of a tyrosine feed, and that even when a tyrosine feed in which a phenolic compound is easily produced is ingested, a certain amount or more of a branched α-glucan mixture is also consumed. This indicates that the amount of phenolic compounds found in urine is significantly reduced.

  Furthermore, in each group, the feces for one day collected from one rat were analyzed, and the amount of phenol compound excreted into feces per day was shown as nmol / day. As shown in Table 7, no phenol was detected in the feces of the rats in the normal diet group, and the amount of p-cresol was as small as 130 ± 64 nmol / day. Was 240 ± 247 nmol / day and the amount of p-cresol was 568 ± 218 nmol / day, indicating a large amount of a phenol compound. On the other hand, in the case of the 2% branched α-glucan mixture group, the amount of phenol was 80 ± 113 nmol / day, and the amount of p-cresol was 844 ± 947 nmol / day. In the case of the -glucan mixture group, the amount of phenol was 32 ± 17 nmol / day, and the amount of p-cresol was 533 ± 326 nmol / day. Although the amount of p-cresol was not different from the control group, the value of phenol was significantly lower. showed that. This result indicates that a phenolic compound is detected in feces by ingestion of a tyrosine feed, and that even when a tyrosine feed in which a phenolic compound is easily produced is ingested, a certain amount or more of a branched α-glucan mixture is also consumed. This indicates that the amount of phenolic compounds found in feces is reduced.

  In addition, as shown in Table 7, no phenol was detected in any of the skin samples. On the other hand, p-cresol was not detected in the skin sample of the normal diet group, and was 29 nmol / g in terms of per gram of skin from the control group and the skin sample of the 2% branched α-glucan mixture group. g and 27 nmol / g were detected at about the same level as p-cresol. However, p-cresol was not detected from the skin sample of the 5% branched α-glucan mixture group (0 nmol / g in terms of 1 g of skin), and the effect of reducing the p-cresol by ingesting the branched α-glucan mixture was recognized. Was done.

  Furthermore, as shown in Table 7, no phenol was detected in any of the liver samples. On the other hand, p-cresol was not detected in the liver sample of the normal diet group, and was 26 nmol / g in terms of 1 g of liver from the control group and the liver sample of the 2% branched α-glucan mixture group. g and 20 nmol / g were detected at about the same level as p-cresol. However, p-cresol was not detected from the liver sample of the 5% branched α-glucan mixture group (0 nmol / g in terms of 1 g of liver), and the reduction effect of p-cresol by ingestion of the branched α-glucan mixture was recognized. Was done.

  As shown in the above experimental results, phenol compounds such as phenol and p-cresol were rarely detected in the living body of rats in the normal diet group bred by ingesting normal feed, whereas tyrosine was fortified / combined. A phenolic compound was remarkably detected from the living body of a control group of rats fed the prepared tyrosine feed, but a 5% branched solution in which an aqueous solution in which a branched α-glucan mixture was dissolved to a 5% concentration was ingested. Remarkably small amounts of phenol compounds were detected in the living body of the rats in the α-glucan mixture intake group. This means that even when humans consume a high protein diet and phenol compounds, which are harmful metabolites, are easily produced from tyrosine, which is a constituent amino acid of the protein, a certain amount of the branched α-glucan mixture is consumed. This indicates that phenol compounds in the living body can be significantly and effectively reduced.

<Experiment 3: Effect of ingestion of branched α-glucan mixture on intestinal flora of rats>
In this experiment, Bifidobacterium spp., Bacteroides-Prevotella porphyromonas spp., And Bacteroides spp. The effect of these species and groups on the number of bacteria was investigated.

  DNA was extracted from cecal contents collected from rats of the normal diet group, the control group, the 2% branched α-glucan mixture group, and the 5% branched α-glucan mixture group, which were bred in Experiment 1. After performing PCR using the extracted DNA as a template and primers targeting a specific sequence portion contained in the rRNA gene of the bacterial species / group, a quantitative PCR method for detecting the amplification product (for example, Matsui et al., Applied and Environmental Microbiology, Vol. 68, No. 11, pp. 5445-5451 (2002)), the genus of Bifidobacterium. The numbers of bacteria, Bacteroides-Prevotella porphyromonas, and Bacteroides phylum were measured.

  Bacterial count (log (cells / g-cecal content)) in the cecal contents of the normal diet group, the control group, the 2% branched α-glucan mixture group, and the 5% branched α-glucan mixture group determined by the above method ) Are shown in Table 8.

As shown in Table 8, the intestinal flora in the cecal contents of the rats in the normal diet group, the control group, and the 2% branched α-glucan mixture group were as follows: Bifidobacterium bacterium, Bacteroides-prevotella porphyromonas. The numbers of bacteria (log (cells / g-cecal contents)) expressed as a logarithm with base 10 of bacteria and Bacteroides phylum were 6.4 to 6.7 and 10.3 to 10.4, respectively. and, distributed in the range of 10.6 to 10.7 ^(i.e., 10 ^{6.4 to 6.7, 10 10.3 to 10.4,} and ^a range of ^{10 10.6 to 10.7),} While no significant difference was observed between the groups, the number of bacteria (log (number / g-cecal contents)) expressed as a logarithm with a base of 10 of the rats of the 5% branched α-glucan mixture group was 8 .0,11.1 and 11.4 ^{(i.e., 10} 8.0, 10 ^{1 .1,} and ^{a 10 11.4)} were significantly increased about 10 times or more, respectively.

  Thus, in the rats of the 5% branched α-glucan mixture group, the numbers of Bifidobacterium, Bacteroides-Prevotella porphyromonas, and Bacteroides phylum in the cecum increased significantly. It was found that the intestinal flora was significantly improved. From this, the effect of reducing the in vivo phenolic compound in Experiment 2 was due to the fact that the ingestion of the branched α-glucan mixture showed that Bifidobacterium, Bacteroides-prevotella porphyromonas, and Bacteroides in the cecum of rats. It was presumed to be an effect resulting from an increase in the number of bacteria, that is, an improvement in the intestinal flora. From the above results using rats, it is considered that similar effects are exerted in humans by ingestion of the branched α-glucan mixture.

  The details of how the present branched α-glucan mixture acts to improve the intestinal flora and reduce the amount of phenolic compounds in the body are unknown, but the α-1 A non-reducing terminal glucose residue of a linear glucan having a degree of glucose polymerization of 3 or more linked via a 4 bond has a branched structure having a degree of glucose polymerization of 1 or more linked via a bond other than an α-1,4 bond. And has a structural feature of producing isomaltose by digestion with isomaltdextranase. More preferably, by digestion with isomaltodextranase, isomaltose is produced in an amount of 5% by mass or more and 70% by mass or less per solid matter of digested matter. It is presumed that having such structural features plays an important role in exerting its function.

  It should be noted that the branched α-glucan mixture having less than 5% by mass of isomaltose in the isomaltodextranase digestion is presumed to have a small effect on improving the intestinal flora since it has a structure close to maltodextrin with a small number of branched structures. . On the other hand, a branched α-glucan mixture in which the amount of isomaltose produced in isomalt dextranase digestion exceeds 70% by mass has a structure close to dextran, which is a glucose polymer linked by α-1,6 bonds, and conversely has a branched structure. It is presumed that the effect of improving the intestinal flora is reduced because it becomes monotonous. Further, among the present branched α-glucan mixtures, those having a water-soluble dietary fiber content of 40% by mass or more as determined by high performance liquid chromatography (enzyme-HPLC method) are difficult to digest themselves and easily reach the large intestine. Therefore, it is estimated to be more preferable.

<Experiment 4: Breeding of Hairless Rats by Feeding Tyrosine Feed and Administering Branched α-Glucan Mixture in Drinking Water>
Experiment 1 except that the Wistar rat used in Experiment 1 was replaced with a hairless rat in order to examine in more detail the effect of the formation of a phenolic compound in the living body on the skin properties and the effect of the branched α-glucan mixture. Hairless rats were bred in substantially the same manner.

  Twenty-four hairless rats (male, 6 weeks old, sold by Nippon SLC Co., Ltd.) were purchased, bred for 5 days while being fed AIN-93G modified feed, and acclimated. The acclimated rats were then divided into four groups of six each, and the same four test groups as shown in Table 1 of Experiment 1, namely, the normal diet group, the control group, the 2% branched α-glucan mixture group, and 5% Each group was bred for 3 weeks as a branched α-glucan mixture group.

  Table 9 shows the weight, food consumption, and water consumption of the hairless rats in each group during the breeding period. Furthermore, the amount of feces and urine for one day each collected from one rat was measured using a metabolic gauge on the 19th to 20th days of breeding. Table 10 shows the average value and standard deviation of 6 animals in each group. Indicated.

  As shown in Table 9, the four groups of hairless rats tested showed similar values in body weight and water consumption, and no significant differences were observed between the groups. However, the daily food consumption of the 2% branched α-glucan mixture group and the 5% branched α-glucan mixture group was about 95% and about 90%, respectively, significantly higher than that of the control group. Was few. Calculated from food consumption, the daily intake of tyrosine in the control group of hairless rats was approximately 4.4 g / kg-body weight. In addition, regarding the rats that have been ingested with the aqueous solution of the branched α-glucan mixture, the daily intake of the branched α-glucan mixture is 2.0 g / kg in the 2% branched α-glucan mixture group, calculated from the amount of water consumed. -Body weight was 5.1 g / kg-body weight in the 5% branched α-glucan mixture group.

  As shown in Table 10, the 2% branched α-glucan mixture group and the 5% branch which were fed with a tyrosine feed and a branched α-glucan mixture aqueous solution as drinking water were fed as shown in Table 10. Although the α-glucan mixture group tended to have a lower fecal volume and a higher urine volume than the other groups, no significant difference was observed between the groups.

  The results in Tables 9 and 10 show that the hairless rats differed from the Wistar rats of Experiment 1 in that the food intake was slightly reduced in the group in which the branched α-glucan mixture aqueous solution was ingested as drinking water, but at the end of breeding. There were no significant differences in body weight, water consumption, fecal volume and urine volume, indicating that hairless rats were kept in a stable test system with no significant differences between groups.

<Experiment 5: Amount of phenolic compound in various biological samples collected from hairless rats>
In this experiment, the amount of phenolic compounds produced in various samples collected from a living body was examined in the same manner as in Experiment 2, except that feces and liver were not measured. That is, as in Experiments 1 and 2-1, cecal contents, blood (serum), urine, and skin were collected from each of the four groups of hairless rats. Table 11 summarizes the weight of each of the cecal tissue and the cecal contents and the pH of the cecal contents.

  As shown in Table 11, the weight of the cecal contents was significantly heavier in the 2% branched α-glucan mixture group and the 5% branched α-glucan mixture group than in the control group. 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, phenolic compounds (phenol and p-cresol) in various samples were quantified for each of the cecal contents, blood (serum), urine, and skin samples collected in the same manner as in Experiment 2-2. Table 12 summarizes the measurement results.

  As shown in Table 12, in the hairless rats, in the normal diet group, the control group, the 2% branched α-glucan mixture group, and the 5% branched α-glucan mixture group, the cecal contents, serum, urine, and skin were observed. In, both phenol and p-cresol were detected.

  As shown in Table 12, in the normal diet group of rats fed with AIN-93G modified feed and water, the amount of phenol per g of cecal contents was 76 ± 33 nmol, and the amount of p-cresol was 14 ± 11 nmol. In contrast, in the case of hairless rats of the control group bred with tyrosine feed and water, the amount of phenol and the amount of p-cresol were 629 ± 230 nmol and 165 ± 164 nmol, respectively, per 1 g of cecal content. Generation of a large amount of phenolic compounds of 8 times or more and 11 times or more was observed. On the other hand, in the case of the 2% branched α-glucan mixture group fed and fed with a tyrosine feed and a 2% branched α-glucan mixture aqueous solution, the amount of phenol was 222 ± 109 nmol and the amount of p-cresol was 70 ± 92 nmol per 1 g of cecal content. And a phenol compound amount significantly lower than that of the control group. In the case of the 5% branched α-glucan mixture group fed and fed with a tyrosine feed and a 5% branched α-glucan mixture aqueous solution, the amount of phenol was 109 ± 66 nmol and the amount of p-cresol was 89 ± 55 nmol per 1 g of cecal content. And a phenol compound amount significantly lower than that of the control group. This result indicates that in the case of hairless rats as well as in the case of Wistar rats in Experiment 2, a large amount of a phenolic compound was produced in the cecal contents by ingestion of a tyrosine feed, and that a tyrosine feed in which a phenolic compound was easily produced was obtained. Even if it is ingested, it indicates that if a certain amount or more of the branched α-glucan mixture is ingested, the amount of the phenol compound in the cecal contents can be significantly reduced.

  Further, as shown in Table 12, in the hairless rats, in the serum, urine, and skin, both the phenol amount and the p-cresol amount increased in the control group as compared with the normal diet group, and the 2% branched α-glucan mixture group and the 5% The results or tendency to decrease both were observed in the% branched α-glucan mixture group. This result shows that, even if a tyrosine feed was ingested, as in the case of cecal contents, if a certain amount or more of the branched α-glucan mixture was ingested, the amount of phenolic compounds in serum, urine and skin Can be significantly reduced.

  In the Wistar rats of Experiments 1 and 2, p-cresol was produced in a larger amount than phenol as a phenol compound, whereas in the hairless rat, phenol was produced in a larger amount than p-cresol. I was This result suggests that the intestinal flora is different between Wistar rats and hairless rats, resulting in a difference in the production of phenolic compounds.

<Experiment 6: Analysis of skin properties of hairless rats>
In the skin, homeostasis is maintained by repeating turnover (skin metabolism) in which the outer cells in contact with the outside world are debris and peel off, and the inner cells proliferate and supply new cells. If the turnover of the skin is too fast, the stratum corneum cells do not sufficiently differentiate and appear on the skin surface in a small size. Therefore, in the cosmetics field, the stratum corneum cell area is used as an index of skin health. In Non-Patent Document 2, the horny cell area of the skin is measured as an index of the adverse effect of a phenol compound on the skin of a hairless mouse, and the horny cell area of a hairless mouse to which phenol or p-cresol is administered is significantly reduced. It has been reported that it has declined. In this experiment, the skin cell area of the skin was measured for the hairless rats raised in Experiment 4.

  In addition, during turnover of the skin, if the division of undifferentiated cells called basal cells in contact with the basement membrane below the skin epidermis is accelerated, differentiation into keratinocytes is delayed and immature keratin Since the cells became cells, hairless rats bred in Experiment 4 were also examined for division of skin basal cells.

<Experiment 6-1: Measurement of stratum corneum cell area of hairless rat skin>
The horny layer of the skin was collected from a total of 24 hairless rats bred in Experiment 4 under pentobarbital anesthesia before euthanasia. The keratin is collected on the tape by pressing an adhesive tape for exfoliation (trade name “Exfoliator Checker AST-01”, 25 × 25 mm, sold by Nippon Ash Co., Ltd.) on the right back of the hairless rat for a few seconds and peeling off. After fixation with formalin vapor, hematoxylin and eosin staining was performed. Next, the corneal cells stained with hematoxylin and eosin were observed under a microscope, and 30 or more horny cells per hairless rat were examined using a microscope imaging software (trade name “cellSens Dimension”, manufactured by Olympus Corporation). To measure the cell area, and the average value was calculated. The results are shown in Table 13.

As shown in Table 13, the hairless rats of the normal diet group bred with the AIN-93G modified feed and water were fed, whereas the horny cell area was 1303 ± 96 μm ² , whereas the tyrosine feed and water were fed. The hairless rats of the control group bred and raised had a significantly lower value of 1159 ± 97 μm ² . On the other hand, in the case of the 2% branched α-glucan mixture group fed and fed with a tyrosine feed and a 2% branched α-glucan mixture aqueous solution, the horny layer cell area was 1286 ± 86 μm ² , showing an increasing tendency as compared with the control group. In the case of the 5% branched α-glucan mixture group fed and fed with a feed and a 5% branched α-glucan mixture aqueous solution, the value was 1331 ± 72 μm ^2, which was significantly higher than that of the control group and equivalent to that of the normal diet group. showed that. This result indicates that in hairless rats fed a tyrosine feed, phenolic compounds generated in vivo inhibit differentiation of stratum corneum cells in the skin, but ingestion of a branched α-glucan mixture leads to This indicates that the amount of production is reduced, does not affect the differentiation of stratum corneum cells, and that skin properties can be improved.

<Experiment 6-2: Measurement of division image of skin basal cells>
The skin of the left back was collected after euthanized from four groups of 24 hairless rats bred in Experiment 4, and immersed and stored in a 15% (v / v) formalin solution for tissue analysis. Tissue sections embedded in paraffin by a conventional method were stained with hematoxylin and eosin, and the division images of the basal cell layer were counted under a microscope. The results are shown in Table 14.

  As can be seen from Table 14, in the hairless rat of the normal diet group bred by ingesting the AIN-93G modified feed and water, the division image of the basal cells was 2.8 ± 1.1 cells / cm. In the control group of hairless rats fed a tyrosine diet and water, the control group showed a significantly large value of 5.7 ± 1.8 cells / cm, indicating that the basal cell division was enhanced by the intake of the tyrosine diet. found. On the other hand, in the case of the 2% branched α-glucan mixture group bred by ingesting the tyrosine feed and the 2% branched α-glucan mixture aqueous solution, 4.8 ± 1.8 cells / cm showed a decreasing tendency as compared with the control group, In the case of the 5% branched α-glucan mixture group bred by ingesting the tyrosine feed and the 5% branched α-glucan mixture aqueous solution, the group showed a significantly lower value of 3.2 ± 0.8 as compared to the control group, and showed a normal diet group. Was equivalent to This result shows that in hairless rats fed a tyrosine diet, phenolic compounds produced in vivo promoted division of basal cells in the skin, that is, inhibited differentiation into keratinocytes, but in hairless rats fed a tyrosine diet. Even if there is, the intake of the branched α-glucan mixture reduces the amount of phenolic compounds produced in the living body, and as a result, does not affect the differentiation of stratum corneum cells, indicating that skin properties can be improved. I have.

  From the results of Experiments 1 to 5, the present branched α-glucan mixture improves the intestinal flora when ingested and significantly reduces phenol compounds such as phenol and p-cresol in the body, which are known as intestinal putrefaction products. It turns out that it can be done. These experiments show that the present branched α-glucan mixture has a remarkable action and effect as an active ingredient of the in vivo phenol reducing agent.

  In addition, from the results of Experiment 6, when the present branched α-glucan mixture was ingested, the decrease in the area of the stratum corneum reported as an adverse effect of the phenol compound on the skin was not observed, and the division of basal cells was also enhanced. It turned out to be unseen. It is considered that the reason for this is that the intake of the present branched α-glucan mixture suppressed the production of a phenol compound in the living body, and the amount of the phenol compound which was absorbed and transferred to the skin and had an adverse effect was reduced.

  The above results show that the present branched α-glucan mixture can be advantageously used as an active ingredient of an in vivo phenolic compound reducing agent. It is said that it can be used advantageously as food and drink. In addition, the result of Experiment 6 indicates that the above-mentioned in vivo phenolic compound reducing agent reduces the amount of phenolic compound generated in the living body due to food and drink, thereby causing an adverse effect on the skin caused by the effect of the phenolic compound. In other words, it can reduce the inhibition of maturation of keratinocytes and maturate keratinocytes (increase the cell area of stratum corneum cells), thereby maintaining or improving skin health and improving skin properties. More specifically, it shows that it can be used for improving skin turnover.

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

<Biological phenol compound reducing agent>
According to the method described in Example 5 of International Publication WO 2008/136331, a branched α-glucan mixture powder was prepared and used as an in vivo phenol compound reducing agent. The obtained branched α-glucan mixture powder had the following characteristics (a) to (g).
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) isomaltose dextranase digestion produces isomaltose at 35% by mass per solid of the digest,
(D) a water-soluble dietary fiber content of 80.8% by mass;
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is 1: 2.2,
(F) the sum of α-1,4 linked glucose residues and α-1,6 linked 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 in vivo phenolic compound reducing agent containing 100% by mass of a branched α-glucan mixture as an active ingredient. The product itself is low in sweetness or tasteless, has no off-flavor, is stable at room temperature without moisture absorption or discoloration for one year or more. This product may be taken as it is, or dissolved in a beverage such as water, tea, coffee, etc., or added to a food or beverage and taken.The consumption of this product reduces phenol compounds in the body. can do. In addition, it is also advantageous to mix one or more components selected from water, minerals, flavors, stabilizers, excipients, extenders, pH adjusters, etc., with the product, if necessary. Can be implemented.

<Biological phenol compound reducing agent>
According to the method described in Experiment 2-2 of International Publication WO2008 / 136331, a branched α-glucan mixture solution having a solid content of 30% by mass was prepared, and then spray-dried according to a conventional method to obtain a branched α-glucan. A mixture powder was obtained and used as a phenolic compound reducing agent in a living body. The obtained branched α-glucan mixture powder had the following characteristics (a) to (g).
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) isomaltose dextranase digestion to produce isomaltose 27.2% by mass per solid of the digest,
(D) a water-soluble dietary fiber content of 41.8% by mass;
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is 1: 0.6,
(F) the sum of α-1,4 linked glucose residues and α-1,6 linked glucose residues is 83.0% of all glucose residues,
(G) The average degree of polymerization of glucose is 405, and Mw / Mn is 16.2.

  This product is an in vivo phenolic compound reducing agent containing 100% by mass of a branched α-glucan mixture as an active ingredient. The product itself is low in sweetness or tasteless, has no off-flavor, is stable at room temperature without moisture absorption or discoloration for one year or more. This product may be taken as it is, or dissolved in a beverage such as water, tea, coffee, etc., or added to a food or beverage and taken.The consumption of this product reduces phenol compounds in the body. can do. In addition, it is also advantageous to mix one or more components selected from water, minerals, flavors, stabilizers, excipients, extenders, pH adjusters, etc., with the product, if necessary. Can be implemented.

<Biological phenol compound reducing agent>
According to the method described in Example 6 of International Publication WO2008 / 136331, a branched α-glucan mixture powder was prepared and used as an in vivo phenol compound reducing agent. In addition, the obtained branched α-glucan mixture powder had the characteristics of (a) to (g).
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) isomaltose dextranase digestion to produce 40.6% by mass of isomaltose per solid of the digest,
(D) a water-soluble dietary fiber content of 77.0% by mass;
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is 1: 4,
(F) the sum of α-1,4 linked glucose residues and α-1,6 linked glucose residues is 67.9% of all glucose residues,
(G) The average degree of glucose polymerization is 18, and Mw / Mn is 2.0.

  This product is an in vivo phenolic compound reducing agent containing 100% by mass of a branched α-glucan mixture as an active ingredient. The product itself is low in sweetness or tasteless, has no off-flavor, is stable at room temperature without moisture absorption or discoloration for one year or more. This product may be taken as it is, or dissolved in a beverage such as water, tea, coffee, etc., or added to a food or beverage and taken.The consumption of this product reduces phenol compounds in the body. can do. In addition, it is also advantageous to mix one or more components selected from water, minerals, flavors, stabilizers, excipients, extenders, pH adjusters, etc., with the product, if necessary. Can be implemented.

<Biological phenol compound reducing agent>
The branched α-glucan mixture powder was prepared according to the method described in Example 5 of WO 2008/136331, except that maltotetraose-forming amylase was further added to the corn starch liquefied liquid in an amount of 2 units per gram of solid matter. Was prepared and used as an in vivo phenolic compound reducing agent. In addition, the obtained branched α-glucan mixture powder had the characteristics of (a) to (g).
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) Isomaltose is produced by digestion with isomaltodextranase at 41.9% by mass per solid matter of digested matter,
(D) a water-soluble dietary fiber content of 69.1% by mass;
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is 1: 2.4,
(F) The sum of α-1,4 linked glucose residues and α-1,6 linked glucose residues is 64.2% of all glucose residues,
(G) The average degree of polymerization of glucose is 13, and Mw / Mn is 2.0.

  This product is an in vivo phenolic compound reducing agent containing 100% by mass of a branched α-glucan mixture as an active ingredient. The product itself is low in sweetness or tasteless, has no off-flavor, is stable at room temperature without moisture absorption or discoloration for one year or more. This product may be taken as it is, or dissolved in a beverage such as water, tea, coffee, etc., or added to a food or beverage and taken.The consumption of this product reduces phenol compounds in the body. can do. In addition, it is also advantageous to mix one or more components selected from water, minerals, flavors, stabilizers, excipients, extenders, pH adjusters, etc., with the product, if necessary. Can be implemented.

<Biological phenol compound reducing agent>
Amyloglucosidase (glucoamylase) was allowed to act on the branched α-glucan mixture obtained by the method described in Example 1, and the undegraded components were separated using gel filtration chromatography. Thereafter, the mixture was purified and spray-dried according to a conventional method to prepare a branched α-glucan mixture powder, which was used as an in vivo phenol compound reducing agent. In addition, the obtained branched α-glucan mixture had the characteristics of (a) to (g).
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) isomaltose dextranase digestion to produce isomaltose at 21% by mass per solid of the digest,
(D) a water-soluble dietary fiber content of 94.4% by mass;
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is 1: 1.9,
(F) the sum of α-1,4 linked glucose residues and α-1,6 linked glucose residues is 64% of all glucose residues,
(G) The glucose polymerization degree is 22, and Mw / Mn is 1.7.

  This product is an in vivo phenolic compound reducing agent containing 100% by mass of a branched α-glucan mixture as an active ingredient. The product itself is low in sweetness or tasteless, has no off-flavor, is stable at room temperature without moisture absorption or discoloration for one year or more. This product may be taken as it is, or dissolved in a beverage such as water, tea, coffee, etc., or added to a food or beverage and taken.The consumption of this product reduces phenol compounds in the body. can do. In addition, it is also advantageous to mix one or more components selected from water, minerals, flavors, stabilizers, excipients, extenders, pH adjusters, etc., with the product, if necessary. Can be implemented.

<Oral composition (powder juice)>
33 parts by mass of orange juice powder produced by spray drying, 10 parts by mass of an in vivo phenolic compound reducer 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 weight of citric anhydride, 0.1 part by weight of malic acid, 0.2 part by weight of 2-O-α-glucosyl-L-ascorbic acid, 0.1 part by weight of sodium citrate, and an appropriate amount of powdered flavor Mix well and stir, pulverize to a fine powder, charge it in a fluid bed granulator, set the exhaust air temperature to 40 ° C, and dissolve the branched α-glucan powder obtained by the method of Example 1 in water. An appropriate amount of the obtained solution was sprayed as a binder, granulated for 30 minutes, weighed, and packaged to obtain a product. This product is a powdered juice having a fruit juice content of about 30%. This product is a powdered juice that contains an in vivo phenolic compound reducing agent, so that it can improve intestinal flora and reduce in vivo phenolic compounds. In addition, the product has no off-flavor or odor, and has high commercial value as a juice.

<Oral composition (custard cream)>
100 parts by mass of corn starch, 30 parts by mass of a phenolic compound reducing agent in vivo obtained by the method described in Example 4, 70 parts by mass of trehalose hydrated crystal, 40 parts by mass of glucose, and 1 part by mass of sodium chloride are sufficiently mixed, Add 280 parts by mass of chicken egg and stir, add 1,000 parts by mass of boiled milk gradually, continue to heat and continue stirring, stop the fire when corn starch is completely gelatinized and the whole becomes translucent After cooling, an appropriate amount of vanilla flavor was added, followed by weighing, filling, and packaging to obtain a product. This product is a custard cream that contains an in vivo phenolic compound reducing agent, and thus can improve intestinal flora and reduce in vivo phenolic compounds. The product is a high-quality custard cream having a smooth luster, good flavor and good taste.

<Oral composition (dietary supplement)>
247 g of glucose, 217 g of an in vivo phenolic compound reducer obtained by the method described in Example 3, 8 g of an iron pyrophosphate suspension (Sunactive FeM manufactured by Taiyo Kagaku Co., Ltd.), 15 g of vitamin premix, sodium ascorbate 3 g, zinc yeast 0.5 g, chromium yeast 0.3 g, and sucralose 0.2 g were put into a granulating apparatus as raw granules. On the other hand, 15 g of coffee extracted powder and 10 g of magnesium sulfate were dissolved in 100 mL of granulation adjusting water. The granulation adjustment liquid is sprayed little by little from the tip of the nozzle into the place where the raw granulation powder is mixed in the apparatus, and granulated. Nitrogen gas is placed in an aluminum bag so as to be 5.15 g per pack or 10.3 g per pack. Filled. This product is a dietary supplement containing a phenolic compound reducing agent in the living body, and can improve the intestinal flora and reduce the phenolic compound in the living body. The product has no off-flavor or odor and has high commercial value as a dietary supplement.

<Oral composition (tea drink)>
Black tea was produced using the in vivo phenolic compound reducing agent obtained by the method described in Example 1. 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 saccharide was added to 1 L of the black tea extract, and 2%, 3%, and 4% by weight of an in vivo phenolic compound reducing agent were added to black tea beverages A, B, and C, respectively. In addition, a black tea beverage obtained by the same method as described above was used as a control except that no in vivo phenol compound reducing agent was added. A sensory evaluation was conducted by 10 men and women in their 20s and 50s. As a result, it was found that there was an effect of masking the bitterness and astringency peculiar to the polyphenol contained in the black tea beverage. Further, it was found that the cream-down phenomenon (the phenomenon that the black tea became cloudy when the black tea was gradually cooled) was suppressed in the black tea beverages A, B, and C even when stored at room temperature as compared with the control.

  This product is a black tea beverage that contains an in vivo phenolic compound reducing agent, thereby improving the intestinal flora and reducing the amount of phenolic compounds in the living body. In addition, the product has no off-flavor or odor, and has high commercial value as a black tea beverage.

  As described above, according to the in vivo phenolic compound reducing agent of the present invention containing the present branched α-glucan mixture as an active ingredient, the present branched α-glucan mixture itself as an active ingredient is low in sweetness or tasteless. It can be used in a wide range, and when ingested, it can improve the intestinal flora and significantly reduce phenolic compounds in the body, which are known as intestinal spoilage products. Is useful for the maintenance of the health of the living body. In addition, foods and drinks comprising the in vivo phenolic compound reducing agent of the present invention improve intestinal flora by ingesting in a daily diet, and effectively reduce in vivo phenolic compounds. It has the advantage that it can be done. The present invention is a truly significant invention that makes a great contribution to the art.

Claims (10)

An in vivo phenolic compound reducing agent comprising a branched α-glucan mixture having the following characteristics (A) to (C) as an active ingredient:
(A) glucose as a constituent sugar;
(B) A non-reducing terminal glucose residue located at one end of a linear glucan having a degree of polymerization of glucose of 3 or more linked via an α-1,4 bond was linked via a bond other than the α-1,4 bond. Having a branched structure having a glucose polymerization degree of 1 or more,
(C) Isomaltose is produced by isomalt dextranase digestion.   The in vivo phenol compound reducing agent according to claim 1, wherein the in vivo phenol compound is phenol and / or p-cresol.   2. The branched α-glucan mixture which produces isomaltose by digestion with isomaltodextranase in an amount of 5% by mass or more and 70% by mass or less based on the solid matter of the digested substance. Or the in vivo phenolic compound reducing agent according to 2. The in vivo phenolic compound reducing agent according to any one of claims 1 to 3, wherein the branched α-glucan mixture is a branched α-glucan mixture having the following characteristic (D):
(D) The content of water-soluble dietary fiber determined by high performance liquid chromatography (enzyme-HPLC method) is 40% by mass or more. The in vivo phenolic compound reducing agent according to any one of claims 1 to 4, wherein the branched α-glucan mixture is a branched α-glucan mixture having the following features (E) and (F):
(E) the ratio of α-1,4 linked glucose residues to α-1,6 linked glucose residues is in the range of 1: 0.6 to 1: 4; and (F) α-1,4 The combined glucose residues and α-1,6 linked glucose residues account for 55% or more of all glucose residues.   The in vivo phenolic compound reducing agent according to any one of claims 1 to 5, wherein the average glucose polymerization degree of the branched α-glucan mixture is from 8 to 500.   The in vivo phenolic compound reducing agent according to any one of claims 1 to 6, which has an action of improving intestinal flora.   A food or beverage for reducing a phenolic compound in a living body, comprising the agent for reducing a phenolic compound in a living body according to any one of claims 1 to 7.   The in vivo phenolic compound reducing agent according to any one of claims 1 to 7, which is used for improving skin properties, or the food or beverage for reducing an in vivo phenolic compound according to claim 8.   10. The in vivo phenolic compound reducing agent or the food or beverage for reducing in vivo phenolic compounds according to claim 9, wherein the improvement in skin properties is an improvement in skin turnover.