WO2018193897A1 - Agent de diminution de composé phénolique dans le corps biologique - Google Patents

Agent de diminution de composé phénolique dans le corps biologique Download PDF

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WO2018193897A1
WO2018193897A1 PCT/JP2018/014905 JP2018014905W WO2018193897A1 WO 2018193897 A1 WO2018193897 A1 WO 2018193897A1 JP 2018014905 W JP2018014905 W JP 2018014905W WO 2018193897 A1 WO2018193897 A1 WO 2018193897A1
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branched
vivo
glucan mixture
reducing agent
glucose
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PCT/JP2018/014905
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English (en)
Japanese (ja)
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了大 高▲柿▼
美文 谷口
岳夫 櫻井
光 渡邊
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株式会社林原
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Priority to JP2019513560A priority Critical patent/JP7141387B2/ja
Publication of WO2018193897A1 publication Critical patent/WO2018193897A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to an in vivo phenolic compound reducing agent, and more specifically, includes an in vivo phenolic compound reducing agent that improves intestinal microflora and reduces in vivo phenolic compounds when ingested by humans. It relates to food and drink for reducing in vivo phenolic compounds.
  • intestinal bacteria A wide variety of bacteria (intestinal bacteria) have settled in the human intestine (especially the large intestine), forming a group of bacteria called intestinal flora (intestinal flora).
  • the intestinal flora is said to be composed of 100 types or more and 100 trillion intestinal bacteria, and is known to be closely related to human (host) health. Intestinal bacteria proliferate using food residues, secretions from the digestive tract, and the like that humans could not digest, and are excreted out of the body as feces.
  • Bifidobacterium Bacteroides, Eubacterium, Clostridium, Escherichia coli, lactobacilli, enterococci and the like are known. It is said that the balance of bacteria in the intestinal flora is almost unchanged at the time of health from the time of newborn to adulthood, even though there are individual differences. However, due to various factors such as stress, overwork, overdrinking / overeating, unbalanced eating, climate / temperature, medicine, infection, aging, etc., the balance is lost, and good bacteria such as bifidobacteria are reduced and welsh bacteria, E. coli, etc. It has been pointed out that an increase in bad bacteria may cause various diseases such as diarrhea, constipation, infection due to decreased immunity, and carcinogenesis due to increased intestinal rot 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 bifidobacteria is reduced and the intestinal flora is disturbed, and it has been pointed out that the deterioration of the intestinal flora may promote aging.
  • Bad bacteria in the intestine produce harmful spoilage products (ammonia, amine compounds, phenolic compounds, indole compounds, etc.). It is said that these spoilage products directly damage the intestinal tract and are partially absorbed into the blood and are involved in the development of various diseases and rough skin around the body.
  • Probiotics means living microorganisms and foods that contain such microorganisms in a living state, which improves the intestinal environment and brings about intestinal regulation and immunoregulatory effects, and has beneficial effects on humans. It is a live fungus taken by dairy products. Prebiotics, on the other hand, are not decomposed and absorbed in the upper digestive tract, become a selective nutrient source of beneficial bacteria that live in the large intestine, promote their growth, and maintain the composition of the intestinal flora It means a food ingredient that improves the balance and helps maintain and improve human health.
  • oligosaccharides galactooligosaccharides, fructooligosaccharides, soybean oligosaccharides, dairy oligosaccharides, xylooligosaccharides, isomalyoligosaccharides, raffinose, lactulose, coffee bean manno-oligosaccharides, gluconic acid, etc.
  • dietary fibers polydextrose, inulin, etc.
  • Non-Patent Documents 1, 4 and 5 disclose that when rats / mouses are bred using feed containing tyrosine as a raw material for phenol and p-cresol as intestinal spoilage products, galactooligosaccharide and / or lactic acid bacteria It has been reported that the intake of Bifidobacterium fermented milk reduces serum phenol and p-cresol. In Non-Patent Document 2, phenols produced by intestinal bacteria adversely affect the skin of hairless mice.
  • Non-Patent Document 3 phenols produced by intestinal bacteria are human skin. Have been reported to inhibit fibroblast differentiation. Further, in Non-Patent Document 6, it is said that when rats fed with tyrosine-containing feed were ingested together with high amylose starch, the increase in p-cresol in the living body was suppressed, and further, Non-Patent Document 7 describes bifidobacteria It has been reported that fermented milk improves the intestinal environment of humans, reduces phenolic compounds in the blood, and exhibits cosmetic effects such as maintaining the skin's keratin water content.
  • Non-Patent Document 6 reports that inulin did not show the effect of reducing p-cresol in a test in which rats were fed inulin, which is known as one of dietary fiber and prebiotics. Therefore, just because it is a probiotic or prebiotic that can improve the gut microbiota, it does not necessarily mean that phenol compounds that are harmful metabolites in the body can be reduced. Under such circumstances, it is a water-soluble dietary fiber material that functions as a prebiotic that can be consumed steadily and safely on a daily basis, with a low sweetness or tastelessness, and only improves the intestinal flora. However, it would be extremely useful if a new material capable of reducing in-vivo phenol compounds such as phenol and p-cresol produced as intestinal spoilage products is provided.
  • the present invention when ingested by humans, improves the intestinal microflora and has the effect of reducing in vivo phenolic compounds, which itself is low in sweetness and tasteless and has a wide range of uses, and is easy and safe on a daily basis. It is an object of the present invention to provide an in vivo phenol compound reducing agent containing a substance that can be continuously ingested as an active ingredient, and a food and drink for reducing the in vivo phenol compound comprising the same.
  • a branched ⁇ -glucan mixture that has a branched structure of degree 1 or more and generates isomaltose by digestion with isomaltodextranase, when ingested, not only improves intestinal flora, but also in vivo phenol It has been found that the compound has the effect of significantly reducing the compound. Based on this new finding, the present inventors themselves have an in vivo phenolic compound reducing agent comprising the branched ⁇ -glucan mixture, which is low in sweetness and tasteless and has a wide range of uses, and a living product comprising the same. A food and drink for reducing phenol compounds in the body was established and the present invention was completed.
  • an in vivo phenol compound reducing agent comprising a branched ⁇ -glucan mixture having the following characteristics (A) to (C) as an active ingredient.
  • Isomaltose is produced by isomalt dextranase digestion.
  • the branched ⁇ -glucan mixture having the above characteristics is an ⁇ -glucan obtained from starch and the like as a raw material and is not only a safe edible material but also has a low sweetness or tastelessness. While improving the flora, it has the effect of significantly reducing in vivo phenolic compounds. Therefore, the branched ⁇ -glucan mixture having the above characteristics (A) to (C) is extremely useful as an active ingredient of the in vivo phenol compound reducing agent.
  • this invention solves said subject by providing the food / beverage for in-vivo phenolic compound reduction containing the said in-vivo phenolic compound reducing agent.
  • the in vivo phenolic compound reducing agent of the present invention has a wide range of use because the branched ⁇ -glucan mixture, which is its active ingredient, has low sweetness or tastelessness, and not only improves the intestinal flora when ingested by humans. Since phenol compounds known as intestinal spoilage products can be reduced in vivo, it is useful for maintaining skin health, beauty and further maintaining health of the body. Moreover, the food and drink which contains the in-vivo phenol compound reducing agent of this invention can reduce the in-vivo phenol compound simply and safely effectively by ingesting this.
  • the present invention relates to an in vivo phenol compound reducing agent comprising a branched ⁇ -glucan mixture having the following characteristics (A) to (C) as an active ingredient.
  • A glucose as a constituent sugar
  • B Linked to a non-reducing terminal glucose residue located at one end of a linear glucan having a degree of glucose polymerization of 3 or more linked via an ⁇ -1,4 bond via a bond other than an ⁇ -1,4 bond.
  • Isomaltose is produced by isomalt dextranase digestion.
  • the in vivo phenol compound reducing agent referred to in the present specification is an improvement in the intestinal flora by increasing so-called good bacteria in the intestine when humans are taken orally or by tube, and the phenol compound contained in the living body Means that the amount of phenolic compounds contained in biological samples such as cecal contents, serum, urine, feces, skin, etc. This can be confirmed by comparing with and without cases.
  • the “phenol compound” here means phenol, p-cresol (p-methylphenol), and the like.
  • Non-Patent Document 7 if the phenolic compound in the living body, especially the phenolic compound in the blood or skin, can be reduced, maintenance of the keratin water content and normalization of the keratinization of the epidermis in the skin, etc. Expected to lead to the maintenance of skin health and beauty. In addition, it has been reported that in vivo phenolic compounds are associated with carcinogenesis of the large intestine (see Non-Patent Document 6), and if this can be reduced, it is expected to lead to reduction of cancer and various disease risks.
  • the in vivo phenolic compound reducing agent of the present invention comprises the branched ⁇ -glucan mixture (hereinafter referred to as “the branched ⁇ -glucan mixture”) as an active ingredient.
  • the branched ⁇ -glucan mixture can be obtained by various production methods as described later, and the obtained branched ⁇ -glucan mixture usually has a number of branched ⁇ -having various branched structures and glucose polymerization degrees (molecular weights). -In the form of a mixture of glucans, it is impossible to isolate and quantify each branched ⁇ -glucan with the current technology.
  • each branched ⁇ -glucan that is, the binding mode and order of binding of glucose residues as the constituent units cannot be determined for each branched ⁇ -glucan molecule
  • the structure can be characterized as a whole mixture by various physical, chemical or enzymatic techniques commonly used in the art.
  • the structure of the present branched ⁇ -glucan mixture is characterized by the characteristics (A) to (C) as a whole. That is, this branched ⁇ -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 ⁇ -1,4 bonds. It has a branched structure having a glucose polymerization degree of 1 or more linked to a non-reducing terminal glucose residue located through a bond other than an ⁇ -1,4 bond (feature (B)).
  • non-reducing terminal glucose residue in the feature (B) means a glucose residue located at the terminal that does not exhibit reducing property among the glucan chains linked through ⁇ -1,4 bonds.
  • the “bond other than ⁇ -1,4 bond” literally means a bond other than ⁇ -1,4 bond.
  • this branched ⁇ -glucan mixture produces isomaltose by digestion with isomalt dextranase (feature (C)).
  • the digestion with isomaltodextranase in the feature (C) means that isomaltdextranase is allowed to act on the branched ⁇ -glucan mixture to cause hydrolysis.
  • Isomalt dextranase is an enzyme to which the enzyme number (EC) 3.2.1.94 is assigned, and ⁇ -1,2, ⁇ -1 adjacent to the reducing end of the isomaltose structure in ⁇ -glucan. , 3, ⁇ -1,4, and ⁇ -1,6 linkages, the enzyme has the characteristic of hydrolyzing.
  • isomalt dextranase from Arthrobacter globiformis eg, Sawai et al., Agricultural and Biological Chemistry, Vol. 52, No. 2, No. 2) Pp. 495-501 (1988)).
  • the generation of isomaltose by digestion with isomaltdextranase means that the branched ⁇ -glucan molecules constituting the branched ⁇ -glucan mixture have an isomaltose structure that can be hydrolyzed by isomaltdextranase.
  • the feature (C) has the structural feature that the branched ⁇ -glucan mixture contains an isomaltose structure that can be hydrolyzed with isomalt dextranase when viewed as a whole mixture. Can be characterized by enzymatic techniques.
  • isomaltose is usually 5% by mass or more and 70% by mass or less, preferably 10% by mass or more and 60% by mass or less, based on the digested solid by digestion with isomalt dextranase. More preferably, those produced at 20% by mass or more and 50% by mass or less are suitable for improving the gut microbiota, and are preferably used because they are considered to be superior in the effect of reducing the concentration of phenolic compounds in the living body. .
  • the branched ⁇ -glucan mixture has an effect of improving the intestinal flora and reducing the concentration of phenolic compounds in the living body. It is thought that it is deeply involved that it has the structural feature of generating That is, a branched ⁇ -glucan mixture having an isomaltose production amount of less than 5% by mass in digestion with isomaltodextranase has structural characteristics similar to maltodextrin having a small branched structure, and conversely, isomaltdextranase.
  • a branched ⁇ -glucan mixture having an isomaltose production amount of more than 70% by mass in digestion has a structural feature close to that of dextran, which is a glucose polymer linked by ⁇ -1,6 bonds.
  • dextran which is a glucose polymer linked by ⁇ -1,6 bonds.
  • the present branched ⁇ -glucan mixture it has the feature (D) that the water-soluble dietary fiber content determined by high performance liquid chromatography (enzyme-HPLC method) is 40% by mass or more. Are listed.
  • “High-performance liquid chromatographic method (enzyme-HPLC method)” (hereinafter simply referred to as “enzyme-HPLC method”) for determining water-soluble dietary fiber content is the nutrition labeling standard of the Ministry of Health and Welfare Notification No. 146 in May 1996. , "Methods for analysis of nutritional components, etc. (methods listed in the first column of the first column of the nutrition labeling standard)", the method described in "Food fiber”, the outline of which is described below. It is as follows.
  • a sample for gel filtration chromatography is prepared by decomposing the sample by a series of enzyme treatments with heat-stable ⁇ -amylase, protease, and glucoamylase, and removing proteins, organic acids, and inorganic salts from the treatment solution with an ion exchange resin. Prepare the solution. Next, it is subjected to gel filtration chromatography, and the peak areas of undigested glucan and glucose in the chromatogram are obtained. The respective peak areas and glucose in the sample solution obtained separately by the glucose oxidase method by a conventional method are obtained. The amount is used to calculate the water soluble dietary fiber content of the sample.
  • water-soluble dietary fiber content means the water-soluble dietary fiber content determined by the “enzyme-HPLC method” unless otherwise specified.
  • the water-soluble dietary fiber content indicates the content of ⁇ -amylase and ⁇ -glucan that is not decomposed by glucoamylase, and the feature (D) shows that the structure of the branched ⁇ -glucan mixture as a whole is expressed by an enzymatic method. It is one of the indices that characterize.
  • the branched ⁇ -glucan mixture improves the intestinal flora, and reduces the amount of in vivo phenolic compounds.
  • the structural feature of producing isomaltose by digestion with isomaltdextranase is profound. This characteristic structural part, which is considered to be involved, is of course the higher the water-soluble dietary fiber content of the branched ⁇ -glucan mixture, in other words, ⁇ -amylase and glucoamylase. It is considered that the higher the content of branched ⁇ -glucan that is not decomposed by, the more it reaches the large intestine without being digested and the effect of improving the intestinal flora.
  • a higher water-soluble dietary fiber content is preferable, and a suitable water-soluble dietary fiber content is usually 40% by mass.
  • the thing of 60 mass% or more is more preferable, More preferably, it is 75 mass% or more.
  • the suitable water-soluble dietary fiber content There is no particular upper limit on the suitable water-soluble dietary fiber content, and the higher the technically possible value, the better, and preferably 100% by mass or less or less than 100% by mass.
  • a more preferable embodiment of the present branched ⁇ -glucan mixture includes a branched ⁇ -glucan mixture having the following characteristics (E) and (F).
  • E the ratio of ⁇ -1,4 linked glucose residues to ⁇ -1,6 linked glucose residues is in the range of 1: 0.6 to 1: 4;
  • F The sum of ⁇ -1,4-bonded glucose residues and ⁇ -1,6-bonded glucose residues accounts for 55% or more of all glucose residues.
  • methylation analysis is a generally used method for determining the binding mode of monosaccharides constituting a polysaccharide or oligosaccharide (Ciucanu et al., Carbohydrate). -Research (Carbohydrate Research), Vol. 131, No. 2, pp. 209-217 (1984)).
  • methylation analysis is applied to analysis of glucose binding mode in glucan, first, all free hydroxyl groups in glucose residues constituting glucan are methylated, and then fully methylated glucan is hydrolyzed.
  • methylated glucose obtained by hydrolysis is reduced to form methylated glucitol from which the anomeric form has been eliminated, and further, a free hydroxyl group in this methylated glucitol is acetylated to give partially methylated glucitol acetate (note that , “Partially methylated glucitol acetate” is sometimes simply referred to as “partially methylated product”).
  • Partially methylated glucitol acetate is sometimes simply referred to as “partially methylated product”.
  • 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 from the peak area%.
  • “Ratio” for partially methylated product means “ratio” of peak area in gas chromatogram of methylation analysis
  • “%” for partially methylated product means “area%” in gas chromatogram of methylated analysis.
  • the “ ⁇ -1,4-bonded glucose residue” in the above features (E) and (F) means glucose bonded to other glucose residues only through hydroxyl groups bonded to the 1st and 4th carbon atoms. It is a residue and is detected as 2,3,6-trimethyl-1,4,5-triacetylglucitol in methylation analysis.
  • the “ ⁇ -1,6-bonded glucose residue” in the above features (E) and (F) is bound to other glucose residues only through the hydroxyl groups bonded to the 1st and 6th carbon atoms. It is detected as 2,3,4-trimethyl-1,5,6-triacetylglucitol in methylation analysis.
  • Ratio of ⁇ -1,4-bonded glucose residue and ⁇ -1,6-bonded glucose residue obtained by methylation analysis, and ⁇ -1,4-bonded glucose residue
  • the ratio of the ⁇ -1,6-linked glucose residues to the total glucose residues is used as one of the indicators for characterizing the structure of the branched ⁇ -glucan mixture as a whole by chemical methods. be able to.
  • the present branched ⁇ -glucan mixture in a preferred embodiment, has a considerable amount of “ ⁇ -1,6-linked glucose residues” that are not usually present in starch.
  • ⁇ -1,4 bonds and ⁇ -1,6 bonds ⁇ -1,3 bonds and / or ⁇ - It preferably has 1,3,6 bonds.
  • ⁇ -1,3,6 bond means “residue of glucose that is bonded to other glucose ( ⁇ -1,3,6 bond) at three positions of hydroxyl groups at the 1-position, 3-position and 6-position”. Means "group”.
  • the branched ⁇ -glucan mixture contains ⁇ -1,3 bonds and / or ⁇ -1,3,6 bonds, and the ratio is not particularly limited.
  • ⁇ -1,3 linked glucose residues are preferably 0.5% or more and less than 10% of all glucose residues, and ⁇ -1,3,6 linked glucose residues are It is preferable that it is 0.5% or more.
  • ⁇ -1,3-bonded glucose residues are 0.5% or more and less than 10% of all glucose residues.
  • this branched ⁇ -glucan mixture is subjected to methylation analysis, and 2,4,6 This can be confirmed by the presence of trimethyl-1,3,5-triacetylglucitol in an amount of 0.5% to less than 10% of the partially methylated glucitol acetate.
  • ⁇ -1,3,6-linked glucose residues are 0.5% or more of the total glucose residues.
  • this branched ⁇ -glucan mixture is subjected to methylation analysis, and 2,4- This can be confirmed by the presence of dimethyl-1,3,5,6-tetraacetylglucitol in an amount of 0.5% to less than 10% of the partially methylated glucitol acetate.
  • This branched ⁇ -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.
  • the average glucose polymerization degree of the branched ⁇ -glucan constituting the branched ⁇ -glucan mixture can be calculated based on the weight average molecular weight (Mw), the branched ⁇ -glucan mixture is characterized by the average glucose polymerization degree. It can also be attached.
  • the average glucose polymerization degree can be obtained by subtracting 18 from the weight average molecular weight (Mw) and dividing by 162 corresponding to the molecular weight of the glucose residue.
  • the branched ⁇ -glucan mixture used as an active ingredient of the in vivo phenol compound reducing agent preferably has an average glucose polymerization of usually 8 to 500, preferably 15 to 400, more preferably 20 to 300.
  • the branched ⁇ -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 ⁇ -glucan mixture having an average degree of glucose polymerization 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 ⁇ -glucan molecules constituting the branched ⁇ -glucan mixture that is closer to 1 Means small.
  • the present branched ⁇ -glucan mixture used as an active ingredient of the in vivo phenol compound reducing agent can be used without problems as long as the Mw / Mn is usually 20 or less, but is preferably 10 or less, more preferably 5 or less. Those are preferred.
  • Mw / Mn is closer to 1 and the glucose polymerization degree varies. Smaller is preferable.
  • the present branched ⁇ -glucan mixture may be produced by any method as long as it has the characteristics (A) to (C).
  • a branched structure having a glucose polymerization degree of 1 or more linked to a non-reducing terminal glucose residue of a linear glucan having a glucose polymerization degree of 3 or more linked through an ⁇ -1,4 bond via an ⁇ -1,6 bond A branched ⁇ -glucan mixture obtained by allowing an enzyme having an action of introducing sucrose to act on starch can be suitably used in the practice of the present invention.
  • WO2008 / 136331 examples thereof include branched ⁇ -glucan mixtures obtained by allowing ⁇ -glucosyltransferase disclosed in the pamphlet to act on starch.
  • an amylase such as maltotetraose-producing amylase (EC 3.2.1.60) or a starch debranching enzyme such as isoamylase (EC 3.2.1.68) is used.
  • the branched ⁇ -glucan mixture can be reduced in molecular weight, so that the molecular weight, glucose polymerization degree, etc. can be adjusted to a desired range.
  • the degree of polymerization disclosed in cyclomaltodextrin glucanotransferase (EC 2.4.1.19), starch branching enzyme (EC 2.4.1.18), and JP-A No. 2014-054221 is further obtained by using two or more ⁇ -1,4 glucans together with an enzyme having an activity of transferring ⁇ -1,6 to an internal glucose residue of starch. It can also be highly branched to increase the water-soluble dietary fiber content of the branched ⁇ -glucan mixture.
  • the branched ⁇ -glucan mixture thus obtained can be further treated with a saccharide hydrolase such as glucoamylase to further increase the water-soluble dietary fiber content, thereby producing a branched ⁇ -glucan mixture.
  • a saccharide hydrolase such as glucoamylase
  • the reducing power of the branched ⁇ -glucan mixture may be reduced by, for example, and it is optional to obtain a branched ⁇ -glucan mixture having a desired molecular weight by performing fractionation by size exclusion chromatography or the like. It is.
  • the amount of the branched ⁇ -glucan mixture contained in the in vivo phenolic compound reducing agent of the present invention is not particularly limited as long as the desired in vivo phenolic compound reducing effect is exhibited. It may be contained in the range of 1 to 100% by mass, preferably 3 to 100% by mass, more preferably 5 to 100% by mass.
  • the in vivo phenol compound reducing agent of the present invention includes, in addition to the present branched ⁇ -glucan mixture, water, minerals, flavoring agents, stabilizers, excipients, extenders, pH adjusters and the like as necessary.
  • One or two or more components selected from the above can be used by appropriately blending in a proportion of 0.01 to 50% by mass, preferably 0.1 to 40% by mass.
  • the in vivo phenol compound reducing agent of the present invention may be ingested in an amount that exerts the effect of reducing the amount of in vivo phenol compound, and the intake amount is not particularly limited.
  • the intake of glucan mixture is usually 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, even more preferably 3 per adult (60 kg body weight)
  • the in vivo phenol compound reducing agent of the present invention is taken as it is or dissolved in beverages such as water, tea, coffee, etc., or added to foods or beverages so as to be in the range of 8 to 8 g. Good.
  • the in vivo phenolic compound reducing agent of the present invention may be ingested before or after ingestion as well as during ingestion of food or beverage.
  • the in vivo phenolic compound reducing agent of the present invention is in the form of powder, granules, granules, liquid, paste, cream, tablet, capsule, caplet, soft capsule, tablet, rod, plate, block, Appropriate forms such as pill, solid, gel, jelly, gummy, wafer, biscuit, bowl, chewable, syrup, and stick can be used.
  • the in vivo phenolic compound reducing agent of the present invention can prevent or ameliorate lifestyle-related diseases such as food for specified health use, functional indication food, nutritional supplement, or health food by containing it in food and drink. It can be made into the form of the food / drink ingested for the purpose.
  • the in vivo phenolic compound reducing agent of the present invention is a liquid, syrup, tube feeding, tablet, capsule, troche, sublingual, granule for preventing or improving (treating) lifestyle-related diseases. It can also be incorporated into drugs in the form of powders, powders, emulsions, sprays and the like. Furthermore, the in vivo phenolic compound reducing agent of the present invention can also be blended in pet food, feed, and feed consumed by animals other than humans.
  • the in vivo phenol compound reducing agent of the present invention and foods and drinks for reducing in vivo phenol compounds comprising the same may be administered to the stomach or digestive tract by parenteral administration methods such as tube administration, as necessary. You can also.
  • the in vivo phenol compound reducing agent of the present invention can reduce the amount of the phenol compound produced in the living body due to food and drink, as shown in the experimental section described later, the skin affected by the phenol compound This has the effect of reducing adverse effects on the skin, maintaining or improving the health of the skin, specifically, optimizing and improving the skin turnover.
  • Example 5 a branched ⁇ -glucan mixture produced according to the method described in Example 5 of International Publication No. WO2008 / 136331 was used. That is, following the method described in Example 5, sodium bisulfite was added to 27.1% by mass corn starch liquor (hydrolysis rate 3.6%) so that the final concentration was 0.3% by mass. Moreover, after adding calcium chloride so that it might become final concentration of 1 mM, it cooled to 50 degreeC, and this was also made into Bacillus circulans PP710 (by the method described in Example 1 of the international publication WO2008 / 136331 pamphlet).
  • a concentrated crude enzyme solution of ⁇ -glucosyltransferase derived from FERM BP-10771) was added in an amount of 11.1 units per gram of the solid, and allowed to act at 50 ° C. and pH 6.0 for 68 hours.
  • the reaction solution is kept at 80 ° C. for 60 minutes, then cooled and filtered, and the filtrate obtained is decolorized with activated carbon, purified by desalting with H-type and OH-type ion resins, and concentrated.
  • the branched ⁇ -glucan mixture produced by spray drying was used in Experiment 1 below.
  • the obtained branched ⁇ -glucan mixture was added to the isomaltdextranase digestion test method, ⁇ -glucosidase and glucoamylase digestion test method described in paragraphs 0079 and 0080 of International Publication No. WO2008 / 136331, paragraph 0076.
  • the following characteristics (a) to (c) were obtained.
  • the branched ⁇ -glucan mixture had the following feature (d) in addition to the above features, and From the results of analysis by the methylation analysis method, it was found that the following characteristics (e) to (h) were obtained.
  • the ⁇ -1,3-linked glucose residues were 2.1% of the total glucose residues.
  • the ⁇ -1,3,6-linked glucose residues were 5.6% of the total glucose residues.
  • the branched ⁇ -glucan mixture used in this experiment is a non-reducing terminal glucose residue of a linear glucan having a glucose polymerization degree of 3 or more and having glucose as a constituent sugar and linked via ⁇ -1,4 bonds.
  • (A) to (C) are characterized by having a branched structure having a glucose polymerization degree of 1 or more linked to each other via bonds other than ⁇ -1,4 bonds, and generating isomaltose by digestion with isomaltodextranase. It was what had.
  • the branched ⁇ -glucan mixture used in this experiment is characterized by producing isomaltose in an amount of 5% by mass or more and 70% by mass or less per digested solid by digestion with isomalt dextranase, and has a water-soluble dietary fiber content.
  • the feature of the above (D) that it is 40% by mass or more, and the ratio of ⁇ -1,4-bonded glucose residue to ⁇ -1,6-bonded glucose residue is 1: 0.6 to 1: 4 (E) and (F), wherein the total of ⁇ -1,4-bonded glucose residues and ⁇ -1,6-bonded glucose residues occupies 55% or more of all glucose residues. It met.
  • ⁇ -1,3 bonded glucose residues are in the range of 0.5% to less than 10% of all glucose residues, and ⁇ -1,3,6 bonded glucose residues are present.
  • the group was in the range of 0.5% or more of the total glucose residues.
  • tyrosine feeds an amino acid used as a raw material for in vivo phenolic compounds
  • Amount of phenolic compounds in various biological samples collected from rats after drinking for a certain period while giving water or an aqueous solution of the branched ⁇ -glucan mixture obtained by dissolving the branched ⁇ -glucan mixture in water to a specific concentration as drinking water was measured.
  • Drinking water ie, water or an aqueous solution obtained by dissolving the branched ⁇ -glucan mixture obtained above in water to 2% (w / v) or 5% (w / v) (hereinafter referred to as “2% branched”, respectively)
  • 2% branched 5% branched ⁇ -glucan mixture solution
  • AIN-93G modified feed and “tyrosine feed” shown in Table 1 are feeds having the compositions shown in Table 2 below, and were obtained by outsourcing to Japan Marie Co., Ltd.
  • the AIN-93G modified feed was modified from 59.9486% by weight in the standard feed “AIN-93G” sold by Clea Japan Co., Ltd., where the composition of corn starch was 39.7486% by weight, and ⁇ -The same composition as AIN-93G, except that the composition of corn starch was 13.2% by weight, but was changed to 1% by weight.
  • the tyrosine feed was obtained by substituting tyrosine with 5% by mass of corn starch of the AIN-93G modified feed.
  • Table 3 shows the body weight, food intake, and water consumption of each group during the breeding period. Furthermore, the amount of stool and urine for one day collected from each rat was measured using a metabolic gauge at the time of breeding 19 to 20 days. Indicated.
  • the rats of the 4 groups tested showed similar values for body weight, food intake and water consumption, and no significant difference was observed between the groups.
  • rats in the normal diet group fed with AIN-93G modified feed as food and water as drinking water rats in the control group fed tyrosine food as food, and a specific concentration as drinking water
  • rats in the test group fed with the branched ⁇ -glucan mixture solution were bred in a stable test system in which no significant difference occurred between the groups.
  • the daily intake of tyrosine in the rat fed with the tyrosine diet was about 4 g / kg-body weight.
  • the daily intake of the branched ⁇ -glucan mixture was 1.9 g / kg in the 2% branched ⁇ -glucan mixture group as calculated from the amount of water consumed.
  • -Body weight 5.1 g / kg body weight in the 5% branched ⁇ -glucan mixture group.
  • Experiment 2-1 Collection of various samples from rats> Four groups of 24 rats raised in Experiment 1 were euthanized by collecting whole blood from the posterior vena cava under pentobarbital anesthesia. After being euthanized, it was dissected and the cecum and liver were excised and collected and weighed. Further, after shaving the flank, 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 cecum contents was directly measured with a pH meter.
  • the weight of the cecal tissue and cecal contents was significantly heavier in the 2% branched ⁇ -glucan mixture group and the 5% branched ⁇ -glucan mixture group than in the control group.
  • the cecal contents of the normal diet group and the control group showed a greenish hue, while the cecal contents of the 5% branched ⁇ -glucan mixture group showed a yellowish hue.
  • the cecal contents showed a ratio of 4 yellowish tones and 2 greenish tones. It was suggested that the intestinal flora changed in the ingested group.
  • the pH of the cecum contents of the group ingested the branched ⁇ -glucan mixture was significantly lower than that of the control group.
  • Example 2-2 Pretreatment of each collected sample for measurement of phenolic compounds in vivo>
  • each sample collected in Experiment 2-1 ie, cecal contents, blood (serum), skin, and liver, was pre-treated as follows for phenol compound measurement. The processing shown was performed.
  • ⁇ Cecal contents> Thawed frozen at ⁇ 80 ° C. after collection, weighed 0.3 g, added 3 mL of 0.1 M phosphate buffer (pH 5.5), diluted 10 times, The crude extract was prepared by homogenization using a tetrafluoroethylene homogenizer (5 mL volume), and centrifuged (3,000 rpm, 800 ⁇ g, 10 minutes), and stored frozen at ⁇ 80 ° C.
  • ⁇ Serum> The collected blood was centrifuged (3,000 rpm, 800 ⁇ g, 10 minutes) to separate the serum and stored frozen at ⁇ 80 ° C.
  • ⁇ Urine> Centrifugation (3,000 rpm, 800 ⁇ g, 10 minutes) was carried out to remove precipitates (eg, feed), and then stored frozen at ⁇ 80 ° C.
  • ⁇ Feces> Thawed frozen at ⁇ 80 ° C. after collection, diluted 10-fold with 0.1 M phosphate buffer (pH 5.5), stirred for about 5 minutes, and then homogenizer made of polytetrafluoroethylene ( The crude extract was prepared by centrifugation (3,000 rpm, 800 ⁇ g, 10 minutes), and stored frozen at ⁇ 80 ° C.
  • ⁇ Skin> Thawed frozen at ⁇ 80 ° C.
  • the above-mentioned pretreated sample is centrifuged (4,700 rpm, 10 minutes) and the supernatant is collected, and then 0.8 mL is taken into a tube with a screw (however, in the case of urine, it is 220).
  • Double diluted solution 32 ⁇ L of 4-ethylphenol, which is an internal standard substance adjusted to a concentration of 100 ⁇ g / mL, and 0.8 mL of 2N hydrochloric acid were added and boiled for 60 minutes. The boiled liquid was allowed to cool at room temperature and neutralized by adding about 0.75 mL of 2N sodium hydroxide.
  • Phenol and p-cresol in various samples were quantified by HPLC under the following conditions.
  • HPLC conditions Column: Shodex ODSpak F-411 ( ⁇ 4.6 ⁇ 150 mm, Showa Denko KK); Equipment: “Prominence” system (manufactured by Shimadzu Corporation) Use “LabSolutions” as analysis software; Pump: 2 LC-20AD; 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 ⁇ L In the quantification of phenol and p-cresol, phenol and p-cresol reagents (manufactured by Sigma-Aldrich) were used as standard products,
  • the amount of phenol per cecal content is 334 ⁇ 435 nmol and the amount of p-cresol is 2866 ⁇ 1652 nmol.
  • the amount of phenolic compounds was significantly lower than that of the control group.
  • the phenol amount per cecal content is 12 ⁇ 3 nmol and the p-cresol amount is 397 ⁇ 128 nmol.
  • the amount of phenolic compounds was significantly lower than that of the control group. This result shows that the ingestion of tyrosine feed produces phenolic compounds in the cecum contents, and even when ingesting tyrosine feed that is likely to produce phenolic compounds, ingesting a certain amount or more of a branched ⁇ -glucan mixture This indicates that the amount of phenolic compound in the cecal contents can be significantly reduced.
  • the amount of phenol per mL of serum is 16 ⁇ 15 nmol and the amount of p-cresol is 101 ⁇ 50 nmol.
  • the amount of phenol per 1 mL of serum was 5%.
  • ⁇ 0 nmol and the amount of p-cresol were 15 ⁇ 4 nmol, which were significantly lower than the control group.
  • the phenol amount was 40 ⁇ 41 ⁇ mol / day, and the p-cresol amount was 196 ⁇ 87 ⁇ mol / day, which was not much different from the control group, but the 5% branched ⁇ -glucan mixture group.
  • the amount of phenol was 4 ⁇ 7 ⁇ mol / day, and the amount of p-cresol was 58 ⁇ 48 ⁇ mol / day, which was significantly smaller than that of the control group.
  • the phenol amount was 80 ⁇ 113 nmol / day and the p-cresol amount was 844 ⁇ 947 nmol / day.
  • 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, but the value for phenol was significantly lower showed that.
  • phenol compounds such as phenol and p-cresol were not detected in the living body of rats in the normal diet group fed with normal feed, but tyrosine was strengthened and formulated.
  • the phenolic compounds were remarkably detected in the living body of the control group fed with the tyrosine feed, but the 5% branch was fed with an aqueous solution in which the branched ⁇ -glucan mixture was dissolved to a concentration of 5%.
  • a significantly smaller amount of phenolic compounds was detected from the living body of rats in the ⁇ -glucan mixture intake group.
  • DNA was extracted from the cecal contents collected from the rats of the normal diet group, the control group, the 2% branched ⁇ -glucan mixture group, and the 5% branched ⁇ -glucan mixture group.
  • a quantitative PCR method for detecting the amplified product for example, (See Matsui et al., Applied and Environmental Microbiology, Vol. 68, No. 11, pages 5445-5451 (2002)).
  • the number of each of the bacteria, Bacteroides-preboteller porphyromonas, and Bacteroides spp. was measured.
  • the intestinal flora in the cecal contents of rats in the normal diet group, the control group, and the 2% branched ⁇ -glucan mixture group is the Bifidobacterium genus, Bacteroides-Prevotella porphyromonas genus
  • the number of bacteria and logarithm of logarithm (log (g / g-cecal contents)) of the Bacteroides bacterium is 6.4 to 6.7, 10.3 to 10.4, respectively.
  • 10.6 to 10.7 ie, 10 6.4 to 6.7 , 10 10.3 to 10.4 , and 10 10.6 to 10.7
  • logarithm log (units / g-cecal content)
  • this branched ⁇ -glucan mixture acts to improve the intestinal flora and reduce the amount of phenolic compounds in the body are unknown.
  • having a structural feature that produces isomaltose by digestion with isomaltodextranase more preferably, isomaltose is produced by digestion with isomaltdextranase to produce isomaltose at 5% by mass or more and 70% by mass or less per solid of the digested product. It is presumed that having a structural feature that plays a role plays an important role in exerting its function.
  • the branched ⁇ -glucan mixture in which the production of isomaltose in the digestion with isomaltodextranase is less than 5% by mass has a structure close to that of maltodextrin with little branching structure, so that the effect of improving the intestinal flora is small.
  • a branched ⁇ -glucan mixture with an isomaltose production amount of more than 70% by mass in isomalt-dextranase digestion has a structure close to that of dextran, which is a glucose polymer linked by ⁇ -1,6 bonds. Since it becomes monotonous, the intestinal flora improvement effect is estimated to be small.
  • branched ⁇ -glucan mixture those having a water-soluble dietary fiber content of 40% by mass or more determined by high performance liquid chromatography (enzyme-HPLC method) are difficult to digest themselves and easily reach the large intestine. Therefore, it is estimated that it is more preferable.
  • 24 hairless rats male, 6 weeks old, sold by Japan SLC Co., Ltd.
  • the acclimatized rats were then divided into 4 groups of 6 animals, and the same 4 test groups as shown in Table 1 of Experiment 1, namely the normal diet group, the control group, the 2% branched ⁇ -glucan mixture group, and the 5%
  • Each branched ⁇ -glucan mixture group was bred for 3 weeks.
  • Table 9 shows the body weight, food intake, and water consumption of each group of hairless rats during the breeding period. Furthermore, the amount of stool and urine for one day collected from each rat was measured using a metabolic gauge at the time of breeding on the 19th to 20th day, and the average value and standard deviation of 6 animals in each group are shown in Table 10. Indicated.
  • the four groups of hairless rats tested showed similar values in terms of body weight and water consumption, and no significant difference was observed between the groups.
  • the daily food consumption of the 2% branched ⁇ -glucan mixture group and the 5% branched ⁇ -glucan mixture group was significant, about 95% and about 90%, respectively, relative to the daily food consumption of the control group. There were few. Calculated from food intake, the daily intake of tyrosine in the control hairless rats was about 4.4 g / kg body weight.
  • the daily intake of the branched ⁇ -glucan mixture is 2.0 g / kg in the 2% branched ⁇ -glucan mixture group as calculated from the amount of water consumed.
  • -Body weight 5.1 g / kg body weight in the 5% branched ⁇ -glucan mixture group.
  • Tables 9 and 10 are different from the Wistar rats in Experiment 1 in the hairless rats, although the amount of food intake was slightly reduced in the group that received the branched ⁇ -glucan mixture aqueous solution as drinking water, There were no significant differences in body weight, water consumption, stool volume, and urine volume, indicating that hairless rats were bred in a stable test system with no significant differences between groups.
  • Example 5 Amount of phenolic compound in various biological samples collected from hairless rats>
  • the amount of phenolic compounds produced in various samples collected from the living body was examined in the same manner as in Experiment 2 except that feces and liver were not measured. That is, as in Experiment 1 and Experiment 2-1, cecal contents, blood (serum), urine, and skin were collected from 4 groups of hairless rats.
  • the respective weights of the cecal tissue and cecal contents and the pH of the cecal contents are summarized in Table 11.
  • the weight of the cecal contents was significantly heavier in the 2% branched ⁇ -glucan mixture group and the 5% branched ⁇ -glucan mixture group than in the control group.
  • the pH of the cecum contents was significantly lower in the 2% branched ⁇ -glucan mixture group and the 5% branched ⁇ -glucan mixture group.
  • the phenol amount is 222 ⁇ 109 nmol and the p-cresol amount is 70 ⁇ 92 nmol per 1 g of cecal contents.
  • the amount of phenolic compounds was significantly lower than that of the control group.
  • the phenol amount per cecal content is 109 ⁇ 66 nmol and the p-cresol amount is 89 ⁇ 55 nmol.
  • the amount of phenolic compounds was significantly lower than that of the control group. This result shows that in the case of hairless rats as well as in the case of Wistar rats in Experiment 2, a large amount of phenolic compounds are produced in the cecum contents by ingestion of tyrosine diets, and tyrosine diets that are likely to produce phenolic compounds are obtained. It shows that even if ingested, a certain amount or more of a branched ⁇ -glucan mixture can be taken together to significantly reduce the amount of phenolic compound in the cecum contents.
  • ⁇ Experiment 6 Analysis of skin properties of hairless rats>
  • the outer cells in contact with the outside world are peeled off, and the homeostasis is maintained by repeating the turnover (skin metabolism) in which the inner cells proliferate and supply new cells. If the skin turnover is too fast, the stratum corneum cells will appear on the skin surface without being sufficiently differentiated. Therefore, in the cosmetic field, the stratum corneum cell area is used as an index of skin health.
  • Non-Patent Document 2 the stratum corneum cell area of skin was measured as an index of the adverse effects of phenolic compounds on the skin of hairless mice. In hairless mice administered with phenol or p-cresol, the stratum corneum cell area was significantly increased. It has been reported that it has declined. In this experiment, the stratum corneum cell area of the skin was measured for the hairless rats bred in Experiment 4.
  • ⁇ Experiment 6-1 Measurement of stratum corneum cell area of hairless rat skin> The stratum corneum of the skin was collected from a total of 24 hairless rats in 4 groups reared in Experiment 4 under pentobarbital anesthesia before euthanasia. The horny substance is collected on the tape by pressing and peeling the adhesive tape for collecting keratin on the right back of the hairless rat (trade name “Keratin Checker AST-01”, 25 ⁇ 25 mm, sold by Nippon Ash Co., Ltd.) After fixing with formalin vapor, hematoxylin and eosin were stained.
  • the hairless rats in the normal diet group fed with the AIN-93G modified feed and water had a stratum corneum cell area of 1303 ⁇ 96 ⁇ m 2 whereas they received tyrosine feed and water.
  • the control group hairless rats bred and showed a significantly low value of 1159 ⁇ 97 ⁇ m 2 .
  • the stratum corneum cell area was 1286 ⁇ 86 ⁇ m 2 , showing an increasing tendency compared to the control group.
  • the present branched ⁇ -glucan mixture can be advantageously used as an active ingredient of an in vivo phenolic compound reducing agent, and foods and drinks containing this in vivo phenolic compound reducing agent are used for reducing in vivo phenolic compounds. Tells us that it can be used advantageously as a food and drink.
  • the results of Experiment 6 show that the above-mentioned in vivo phenolic compound reducing agent is caused by food and drink, and the amount of the phenolic compound produced in the living body reduces the adverse effects on the skin caused by the effect of the phenolic compound.
  • branched ⁇ -glucan mixture powder was prepared and used as an in vivo phenol compound reducing agent.
  • the obtained branched ⁇ -glucan mixture powder had the following characteristics (a) to (g).
  • a branched structure having a glucose polymerization degree of 1 or more (C) Isomaltose is digested to produce 35% by mass of isomaltose per digest solids, (D) the water-soluble dietary fiber content is 80.8% by mass, (E) the ratio of ⁇ -1,4 linked glucose residues to ⁇ -1,6 linked glucose residues is 1: 2.2; (F) the sum of ⁇ -1,4 linked glucose residues and ⁇ -1,6 linked glucose residues is 72.9% of the total glucose residues; (G) Average glucose polymerization degree is 31 and Mw / Mn is 2.0.
  • This product is an in vivo phenolic compound reducing agent whose content of the branched ⁇ -glucan mixture as an active ingredient is 100% by mass.
  • the product itself is low in sweetness or tasteless, has no off-flavor, and does not absorb moisture or discolor even at room temperature, and is stable for over 1 year.
  • This product can be ingested as it is or dissolved in beverages such as water, tea, coffee, etc., or added to foods or beverages. By ingesting this product, in vivo phenolic compounds are reduced. can do.
  • branched ⁇ -glucan mixture solution having a solid content of 30% by mass is prepared, and then spray-dried according to a conventional method to branch ⁇ -glucan.
  • a mixture powder was obtained and used as an in vivo phenol compound reducing agent.
  • the obtained branched ⁇ -glucan mixture powder had the following characteristics (a) to (g).
  • a branched structure having a glucose polymerization degree of 1 or more (C) Isomaltose is digested to produce 27.2% by mass of isomaltose per digest solids, (D) the water-soluble dietary fiber content is 41.8% by mass, (E) the ratio of ⁇ -1,4 linked glucose residues to ⁇ -1,6 linked glucose residues is 1: 0.6; (F) the sum of ⁇ -1,4 linked glucose residues and ⁇ -1,6 linked glucose residues is 83.0% of the total glucose residues; (G) The average degree of glucose polymerization is 405, and Mw / Mn is 16.2.
  • This product is an in vivo phenolic compound reducing agent whose content of the branched ⁇ -glucan mixture as an active ingredient is 100% by mass.
  • the product itself is low in sweetness or tasteless, has no off-flavor, and does not absorb moisture or discolor even at room temperature, and is stable for over 1 year.
  • This product can be ingested as it is or dissolved in beverages such as water, tea, coffee, etc., or added to foods or beverages. By ingesting this product, in vivo phenolic compounds are reduced. can do.
  • branched ⁇ -glucan mixture powder was prepared and used as an in vivo phenol compound reducing agent.
  • the obtained branched ⁇ -glucan mixture powder had the characteristics (a) to (g).
  • a branched structure having a glucose polymerization degree of 1 or more (C) Isomaltose is digested to produce 40.6% by mass of isomaltose per digest of solid, (D) the water-soluble dietary fiber content is 77.0% by mass, (E) the ratio of ⁇ -1,4 linked glucose residues to ⁇ -1,6 linked glucose residues is 1: 4; (F) the sum of ⁇ -1,4 linked glucose residues and ⁇ -1,6 linked glucose residues is 67.9% of the total glucose residues; (G) The average degree of polymerization of glucose is 18, and Mw / Mn is 2.0.
  • This product is an in vivo phenolic compound reducing agent whose content of the branched ⁇ -glucan mixture as an active ingredient is 100% by mass.
  • the product itself is low in sweetness or tasteless, has no off-flavor, and does not absorb moisture or discolor even at room temperature, and is stable for over 1 year.
  • This product can be ingested as it is or dissolved in beverages such as water, tea, coffee, etc., or added to foods or beverages. By ingesting this product, in vivo phenolic compounds are reduced. can do.
  • ⁇ In-vivo phenol compound reducing agent> A branched ⁇ -glucan mixture powder according to the method described in Example 5 of International Publication No. WO2008 / 136331 except that 2 units of maltotetraose-producing amylase per gram of solid was added to the corn starch liquor. was prepared as an in vivo phenolic compound reducing agent.
  • the obtained branched ⁇ -glucan mixture powder had the characteristics (a) to (g).
  • a branched structure having a glucose polymerization degree of 1 or more (C) Isomaltose is digested to produce 41.9% by weight of isomaltose per solid of the digested product, (D) the water-soluble dietary fiber content is 69.1% by weight, (E) the ratio of ⁇ -1,4 linked glucose residues to ⁇ -1,6 linked glucose residues is 1: 2.4; (F) the sum of ⁇ -1,4 linked glucose residues and ⁇ -1,6 linked glucose residues is 64.2% of the total glucose residues; (G) Average glucose polymerization degree is 13 and Mw / Mn is 2.0.
  • This product is an in vivo phenolic compound reducing agent whose content of the branched ⁇ -glucan mixture as an active ingredient is 100% by mass.
  • the product itself is low in sweetness or tasteless, has no off-flavor, and does not absorb moisture or discolor even at room temperature, and is stable for over 1 year.
  • This product can be ingested as it is or dissolved in beverages such as water, tea, coffee, etc., or added to foods or beverages. By ingesting this product, in vivo phenolic compounds are reduced. can do.
  • ⁇ In-vivo phenol compound reducing agent> Amiloglucosidase (glucoamylase) was allowed to act on the branched ⁇ -glucan mixture obtained by the method described in Example 1, and components that were not decomposed were fractionated using gel filtration chromatography. Thereafter, it was purified and spray-dried according to a conventional method to prepare a branched ⁇ -glucan mixture powder, which was used as an in vivo phenol compound reducing agent.
  • the obtained branched ⁇ -glucan mixture had the characteristics (a) to (g).
  • a branched structure having a glucose polymerization degree of 1 or more (C) Isomaltose is produced by digestion with isomaltodextranase to produce 21% by mass of isomaltose per solid of the digested product, (D) the water-soluble dietary fiber content is 94.4% by mass, (E) the ratio of ⁇ -1,4 linked glucose residues to ⁇ -1,6 linked glucose residues is 1: 1.9; (F) the sum of ⁇ -1,4 linked glucose residues and ⁇ -1,6 linked glucose residues is 64% of the total glucose residues; (G) Glucose polymerization degree is 22 and Mw / Mn is 1.7.
  • This product is an in vivo phenolic compound reducing agent whose content of the branched ⁇ -glucan mixture as an active ingredient is 100% by mass.
  • the product itself is low in sweetness or tasteless, has no off-flavor, and does not absorb moisture or discolor even at room temperature, and is stable for over 1 year.
  • This product can be ingested as it is or dissolved in beverages such as water, tea, coffee, etc., or added to foods or beverages. Ingestion of this product reduces the in vivo phenolic compounds can do.
  • This product is a powdered juice with a fruit juice content of about 30%. Since this product contains an in vivo phenolic compound reducing agent, it is a powder juice that can improve the intestinal flora and reduce the in vivo phenolic compound. In addition, this product has no off-flavors and off-flavors, and has high commercial value as a juice.
  • ⁇ Oral composition (custard cream)> 100 parts by weight of corn starch, 30 parts by weight of the in vivo phenol compound reducing agent obtained by the method described in Example 4, 70 parts by weight of trehalose hydrous crystals, 40 parts by weight of glucose, and 1 part by weight of sodium chloride were mixed thoroughly. Add 280 parts by weight of chicken egg, stir in, add gradually 1,000 parts by weight of boiled milk, and continue to stir over fire. Stop when the corn starch is completely gelatinized and the whole becomes translucent. Then, this was cooled, an appropriate amount of vanilla flavoring was added, and weighed, filled and packaged to obtain a product.
  • this product contains an in vivo phenolic compound reducing agent, it is a custard cream that improves intestinal flora and can reduce in vivo phenolic compounds. Moreover, this product is a high-quality custard cream having a smooth luster, good flavor, and high quality.
  • a granulation adjustment liquid is sprayed little by little from the tip of the nozzle where the granulation powder is mixed in the apparatus to granulate, and nitrogen gas is added to the aluminum bag so that it becomes 5.15 g per pack or 10.3 g per pack. Filled.
  • This product is a dietary supplement containing an in vivo phenolic compound reducing agent, and can improve intestinal flora and reduce in vivo phenolic compounds. In addition, this product has no off-flavors and off-flavors and has high commercial value as a dietary supplement.
  • Black tea was produced using the in vivo phenol 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. Black tea beverages A, B, and C were obtained by adding 60 g of isomerized sugar to 1 L of black tea extract and further adding 2%, 3%, and 4% by weight ratio of the in vivo phenol compound reducing agent. Moreover, the tea drink obtained by the method similar to the above was made into the control
  • a sensory evaluation was conducted by 10 men and women in their 20s and 50s, and it was found that they had the effect of masking the bitterness and astringency unique to polyphenols contained in tea beverages. Furthermore, it was found that even when the black tea beverages A, B, and C were stored at room temperature, the cream-down phenomenon (a phenomenon of becoming cloudy white when the tea was gradually cooled) was suppressed as compared with the control.
  • This product is a tea beverage that improves the intestinal flora and reduces the in-vivo phenolic compound because it contains the in-vivo phenol compound reducing agent.
  • this product has no off-flavor and off-flavor, and has a high commercial value as a tea beverage.
  • the present branched ⁇ -glucan mixture as an active ingredient itself has low sweetness or tastelessness.
  • Wide range of use and ingestion can improve intestinal flora and significantly reduce in vivo phenolic compounds known as intestinal spoilage products. This is useful for maintaining the health of the living body, and for maintaining the health of the living body.
  • the food and drink comprising the in vivo phenolic compound reducing agent of the present invention improves intestinal flora and effectively reduces in vivo phenolic compounds by ingesting it in daily eating habits. Has the advantage of being able to The present invention is a truly significant invention that makes a great contribution to the world.

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Abstract

L'invention a pour objet de fournir un agent de diminution de composé phénolique dans le corps biologique, et un aliment ou une boisson destinée à la diminution de composé phénolique dans le corps biologique constitué de cet agent. Plus précisément, l'invention fournit un agent de diminution de composé phénolique dans le corps biologique ayant pour principe actif un mélange de α-glucane ramifié présentant les caractéristiques (A) à (C), et un aliment ou une boisson destinée à la diminution de composé phénolique dans le corps biologique constitué de cet agent. Afin d'atteindre le but de l'invention, les caractéristiques (A) à (C) sont telles que : (A) avoir un glucose pour sucre constitutif ; (B) avoir une structure ramifiée de degré de polymérisation de glucose supérieur ou égal à 1 qui est liée, par l'intermédiaire d'une liaison autre qu'une liaison α-1,4, à un résidu de glucose terminal non réducteur positionné à une extrémité d'un glucane linéaire de degré de polymérisation de glucose supérieur ou égal à 3 lié par l'intermédiaire d'une liaison α-1,4 ; et (C) former un isomaltose sous l'effet d'une digestion par une isomaltodextranase.
PCT/JP2018/014905 2017-04-21 2018-04-09 Agent de diminution de composé phénolique dans le corps biologique WO2018193897A1 (fr)

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JP7141387B2 (ja) 2022-09-22
TWI786105B (zh) 2022-12-11
JPWO2018193897A1 (ja) 2020-02-27
TW201902491A (zh) 2019-01-16

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