Novel saccharide compound or salt of the same

Abstract

To provide a novel saccharide compound.SOLUTION: Provided is a saccharide compound containing an amino acid-derived chemical structure and a saccharide-derived chemical structure, or a salt thereof, where the amino acid-derived chemical structure is 2-amino-3-phenyl propyl group or the like, the saccharide-derived chemical structure contains one or more hexose-derived repeating unit, and / or one or more uronic acid-derived repeating unit, the hexose is glucose or the like; and the uronic acid is glucuronic acid (note that the saccharide compound or a salt thereof excludes a compound (A): a saccharide compound or a salt thereof in which the amino acid-derived chemical structure is phenylalanine residue, 2-amino-3-phenyl propyl group, or tyrosine residue, and the saccharide-derived chemical structure is the hexose-derived repeating unit only).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a novel sugar compound or a salt thereof. [Background technology]

[0002] Decomposed eggshell membranes, which are obtained by decomposing the eggshell membranes inside the shells of eggs such as chicken eggs, are said to have effects such as beauty and health promotion. For example, Patent Document 1 describes a method for producing hydrolyzable eggshell membranes by hydrolyzing eggshell membrane powder in an alkaline aqueous solution. However, the product described in Patent Document 1 has problems such as a complicated and expensive manufacturing process. Furthermore, decomposition using alkaline water as described in Patent Document 1 also decomposes useful components such as collagen, hyaluronic acid, chondroitin, and glucosamine, which are contained in high concentrations in eggshell membrane and are highly effective as beauty ingredients. In particular, hyaluronic acid and chondroitin, which have high water retention properties, are ingredients that are expected to increase the skin's moisturizing properties and improve wrinkles caused by dryness. However, there was concern that if these ingredients were to be broken down, their effectiveness would be reduced when used as ingredients in cosmetics, supplements, etc. Therefore, in Patent Document 2, the present applicant has disclosed a method for producing decomposed eggshell membranes by fermentation, in which eggshell membranes are decomposed using decomposing enzymes produced by koji through fermentation, and the method is characterized by including an eggshell membrane fermentation step in which koji and eggshell membranes are mixed and fermented to produce a fermentation-decomposed eggshell membrane liquid.

[0003] Sugars are found in the biological tissues of plants and animals, and are found in large amounts in honey, fruits, etc. Glucose, in particular, is an important energy source for living organisms. DNA and RNA also contain the sugars deoxyribose and ribose. Glycans, which are chains of sugars, are called the "third chain of life" and have been attracting a great deal of attention in recent years. Like DNA and proteins, glycans and sugar compounds have been found to play important roles in life. Therefore, there is a demand for novel sugar compounds derived from living organisms. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Patent No. 6410229 [Patent Document 2] Patent No. 7237293 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide novel sugar compounds and to obtain novel compounds from decomposed eggshell membranes obtained by decomposing eggshell membranes with decomposing enzymes produced by koji mold during fermentation. [Means for solving the problem]

[0006] As a result of extensive research, the present inventors have discovered a novel compound from decomposed eggshell membranes. The present invention was completed based on this finding.

[0007] That is, the present invention is as follows. Section 1. Chemical structures derived from amino acids, and A sugar compound or a salt thereof containing a sugar-derived chemical structure, The amino acid-derived chemical structure is 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or is a tyrosine residue, The sugar-derived chemical structure is Contains one or more repeating units derived from hexose and / or one or more repeating units derived from uronic acid, The hexose sugar is glucose, galactose, Mannose, and at least one selected from the group consisting of fructose; The uronic acid is A sugar compound or a salt thereof, which is glucuronic acid (Here, the order of the repeating units derived from the hexose and the repeating units derived from the uronic acid is not limited, and the bonding pattern may be alternating, block, or random. Furthermore, the bond between the repeating unit derived from a hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. Furthermore, the bond between the amino acid-derived chemical structure and the hexose-derived repeating unit or the glucuronic acid-derived repeating unit may be an α-bond or a β-bond. (However, the sugar compound or its salt is a compound (A): the amino acid-derived chemical structure is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, and The sugar-derived chemical structure excludes sugar compounds or salts thereof in which the sugar-derived chemical structure is composed only of repeating units derived from the hexose sugar.

[0008] Section 2. The sugar-derived chemical structure is one or more glucose-derived repeat units, one or more galactose-derived repeat units, one or more mannose-derived repeat units, and At least one hexose-derived repeating unit selected from the group consisting of one or more fructose-derived repeating units, and Item 1. A sugar compound or a salt thereof according to Item 1, which has one or more repeating units derived from glucuronic acid. Section 3. The sugar compound is The following general formula (1):

[0009] [ka]

[0010] (In the formula, R 11 represents a hydrogen atom or a hydroxyl group. R 12 represents a hydrogen atom, a hydroxyl group, or an oxo group. G, Repeating units derived from glucose, Galactose-derived repeating units, a repeating unit derived from mannose, and at least one hexose-derived repeating unit selected from the group consisting of fructose-derived repeating units, or The repeating units derived from glucuronic acid are shown. l represents an integer of 1 to 40. When l is 2 or more, the order of the two or more Gs is not limited, and the bonding form may be alternating, block, or random. When 1 is 2 or more, the bond between the repeating unit derived from a hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. Furthermore, the bond between O (oxygen atom) and the G (a repeating unit derived from a hexose sugar or a repeating unit derived from glucuronic acid) may be an α-bond or a β-bond. Item 1, wherein the sugar compound or salt thereof is a compound represented by the formula: (However, the sugar compound or its salt is R 11 is a hydrogen atom or a hydroxyl group, R 12 is a hydrogen atom or an oxo group, wherein l is an integer of 1 to 40; The compounds or salts thereof in which G consists solely of repeating units derived from the hexose are excluded. Section 4. The sugar compound is The following general formula (1A):

[0011] [ka]

[0012] (In the formula, R 11 represents a hydrogen atom or a hydroxyl group. R 12 represents a hydrogen atom, a hydroxyl group, or an oxo group. G 1 but, Repeating units derived from glucose, Galactose-derived repeating units, a repeating unit derived from mannose, and At least one hexose-derived repeating unit selected from the group consisting of fructose-derived repeating units. G 2 but, The repeating units derived from glucuronic acid are shown. If m is 2 or more and n is 1 or more, G 1 and G 2 The order of is not limited, and the bonding style may be alternating, block, or random. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. G 1 and G 2 The bond to may be an α-bond or a β-bond. Also, O (oxygen atom) and the G 1 (hexose-derived repeating unit) or G 2 (the bond to the repeating unit derived from glucuronic acid) may be an α-bond or a β-bond.) (However, the sugar compound or its salt is R 11is a hydrogen atom or a hydroxyl group, R 12 is a hydrogen atom or an oxo group, m is an integer from 0 to 20; (Excluding compounds or salts thereof where n is 0). Section 5. The sugar compound is represented by the following general formula (2):

[0013] [ka]

[0014] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are the same or different, hydrogen atoms, 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or A tyrosine residue is indicated. However, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 At least one of the 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or It is a tyrosine residue. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. Item 1, wherein the sugar compound or salt thereof is a compound represented by the formula: (However, the sugar compound or its salt is R 1 is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, m is an integer from 0 to 20; (Excluding compounds where n is 0). Section 6. The sugar compound is a compound represented by the following general formula (2A-1) or a compound represented by the following general formula (2G-1):

[0015] [ka]

[0016] (In the formula, R 11 represents a hydrogen atom or a hydroxyl group. R 12 represents a hydrogen atom, a hydroxyl group, or an oxo group. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. Item 2. The sugar compound or salt thereof according to Item 1, Section 7. The sugar compound is a compound represented by the following general formula (2A-2) or a compound represented by the following general formula (2G-2):

[0017] [ka]

[0018] (In the formula, R 12 represents a hydrogen atom or a hydroxyl group. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. Item 2. The sugar compound or salt thereof according to Item 1, Section 8. The sugar compound is a compound represented by the following general formula (2A-3) or a compound represented by the following general formula (2G-3):

[0019] [ka]

[0020] (In the formula, m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. Item 2. The sugar compound or salt thereof according to Item 1, Section 9. Item 1. A food composition comprising the sugar compound or a salt thereof according to Item 1. Section 10. Item 1. A functional food composition comprising the sugar compound or a salt thereof according to Item 1. [Effects of the Invention]

[0021] According to the present invention, novel compounds can be provided. Furthermore, according to the present invention, novel compounds can be obtained from decomposed eggshell membranes obtained by decomposing eggshell membranes with decomposing enzymes produced by koji during fermentation. [Brief explanation of the drawings]

[0022] [Figure 1] FIG. 1 is an explanatory diagram of the MALDI-TOF MS_linear negative chart of the sugar compound of the present invention. [Figure 2] FIG. 2 is a chart of MALDI-TOF MS_linear negative of the sugar compound of the present invention. [Figure 3] FIG. 3 is a 1H-NMR chart of the sugar compound of the present invention. [Figure 4] FIG. 4 is a 13C-NMR chart of the sugar compound of the present invention. [Figure 5] FIG. 5 is an explanatory diagram of the 1H-NMR chart of the sugar compound of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0023] Sugar compounds or their salts The sugar compound or a salt thereof of the present invention is a sugar compound or a salt thereof containing a chemical structure derived from an amino acid and a chemical structure derived from a sugar, The amino acid-derived chemical structure is 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or is a tyrosine residue, The sugar-derived chemical structure is Contains one or more repeating units derived from hexose and / or one or more repeating units derived from uronic acid, The hexose sugar is glucose, galactose, Mannose, and at least one selected from the group consisting of fructose; The uronic acid is It is a sugar compound that is glucuronic acid or a salt thereof. Here, the order of the hexose-derived repeating unit and the uronic acid-derived repeating unit is not limited, and the bond type may be alternating, block, or random. Furthermore, the bond between the repeating unit derived from a hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. Furthermore, the bond between the amino acid-derived chemical structure and the hexose-derived repeating unit or the glucuronic acid-derived repeating unit may be an α-bond or a β-bond. However, the sugar compound or a salt thereof is a compound (A): the amino acid-derived chemical structure is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, and The sugar compounds and salts thereof in which the sugar-derived chemical structure is composed only of repeating units derived from the hexose sugar are excluded. The chemical structure derived from an amino acid can be referred to as an amino acid unit, and the chemical structure derived from a sugar can be referred to as a sugar unit.

[0024] The sugar structure preferably has one or more repeating units derived from the hexose and one or more repeating units derived from the glucuronic acid. The number of repeating units derived from the hexose is 1 or 2 or more, preferably 2 or more, more preferably 1 to 20, and particularly preferably 1 to 10. The number of repeating units derived from uronic acid is 1 or 2 or more, preferably 2 or more, more preferably 1 to 20, and particularly preferably 1 to 10.

[0025] The 2-amino-3-phenylpropyl group refers to a group represented by the following formula (A1). The 2-amino-1-hydroxy-3-phenylpropyl group refers to a group represented by the following formula (A2). The phenylalanine residue refers to a group represented by the following formula (A3). The 2-amino-3-(4-hydroxyphenyl)propyl group refers to a group represented by the following formula (A4). The 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group refers to a group represented by the following formula (A5). The tyrosine residue refers to a group represented by the following formula (A6).

[0026] [ka]

[0027] In the above formula, "·" indicates the binding site. The residue refers to the structure remaining after removing "OH" from the carboxylic acid group of an amino acid.

[0028] The sugar compound is preferably represented by the following general formula (1):

[0029] [ka]

[0030] (In the formula, R 11 represents a hydrogen atom or a hydroxyl group. R 12 represents a hydrogen atom, a hydroxyl group, or an oxo group. G, Repeating units derived from glucose, Galactose-derived repeating units, a repeating unit derived from mannose, and at least one hexose-derived repeating unit selected from the group consisting of fructose-derived repeating units, or The repeating units derived from glucuronic acid are shown. l represents an integer of 1 to 40. When l is 2 or more, the order of the two or more Gs is not limited, and the bonding form may be alternating, block, or random. When 1 is 2 or more, the bond between the repeating unit derived from a hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. Furthermore, the bond between O (oxygen atom) and the G (a repeating unit derived from a hexose sugar or a repeating unit derived from glucuronic acid) may be an α-bond or a β-bond. is a compound represented by (However, the sugar compound or its salt is R 11 is a hydrogen atom or a hydroxyl group, R 12 is a hydrogen atom or an oxo group, wherein l is an integer of 1 to 40; The compounds in which G consists solely of repeating units derived from the hexose or salts thereof are excluded. More preferably, The following general formula (1A):

[0031] [ka]

[0032] (In the formula, R 11 represents a hydrogen atom or a hydroxyl group. R 12 represents a hydrogen atom, a hydroxyl group, or an oxo group. G 1 but, Repeating units derived from glucose, Galactose-derived repeating units, a repeating unit derived from mannose, and At least one hexose-derived repeating unit selected from the group consisting of fructose-derived repeating units. G 2 but, The repeating units derived from glucuronic acid are shown. If m is 2 or more and n is 1 or more, G 1 and G 2 The order of is not limited, and the bonding style may be alternating, block, or random. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. G 1 and G 2 The bond to may be an α-bond or a β-bond. Also, O (oxygen atom) and the G 1 (hexose-derived repeating unit) or G 2 The bond to (the repeating unit derived from glucuronic acid) may be an α-bond or a β-bond. (However, the sugar compound or its salt is R 11 is a hydrogen atom or a hydroxyl group, R 12 is a hydrogen atom or an oxo group, m is an integer from 0 to 20; Excluding compounds where n is 0; or The following general formula (1B):

[0033] [ka]

[0034] (In the formula, R 11 represents a hydrogen atom or a hydroxyl group. R 12 represents a hydrogen atom, a hydroxyl group, or an oxo group. G 1 but, Repeating units derived from glucose, Galactose-derived repeating units, a repeating unit derived from mannose, and At least one hexose-derived repeating unit selected from the group consisting of fructose-derived repeating units. G 2 but, The repeating units derived from glucuronic acid are shown. If m is 2 or more and n is 1 or more, G 1 and G 2 The order of is not limited, and the bonding style may be alternating, block, or random. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. G 1 and G 2 The bond to may be an α-bond or a β-bond. Also, O (oxygen atom) and the G 2 (glucuronic acid-derived repeating unit) or G 1 The bond to the repeating unit derived from a hexose may be an α-bond or a β-bond. (However, the sugar compound or its salt is R 11 is a hydrogen atom or a hydroxyl group, R 12 is a hydrogen atom or an oxo group, m is an integer from 0 to 20; Excluding compounds or salts thereof in which n is 0.

[0035] Repeating units derived from hexose sugars A repeating unit derived from a hexose (also referred to as a chemical structure derived from a hexose) refers to a repeating unit derived from glucose, a repeating unit derived from galactose, a repeating unit derived from mannose, or a repeating unit derived from fructose. A hexose is a monosaccharide having six carbon atoms. Hexoses include aldohexoses, which have an aldehyde group at position 1, and ketohexoses, which have a ketone group at position 2. Examples of aldohexoses include glucose, galactose, and mannose. Examples of ketohexoses include fructose. The molecular weight of these repeating units derived from a hexose is approximately 162.

[0036] Glucose-derived repeating units A glucose-derived repeating unit (also referred to as a glucose-derived chemical structure) is a compound in which one or two hydrogen atoms have been removed from glucose. In the present disclosure, the sugar compound or a salt thereof may have any of the hydroxyl groups at the 1st, 2nd, 3rd, 4th, and 6th positions of glucose substituted with the above amino acid-derived chemical structure and / or glucuronic acid-derived chemical structure. Glucose, also known as grape sugar, is the following (Glc):

[0037] [ka]

[0038] It is a compound represented by the molecular formula CH 12 O6, molecular weight is 180.16. In the present disclosure, glucose may be in the α-type, β-type, or aldehyde type.

[0039] Glucose is a type of monosaccharide, an aldohexose, classified as a hexose (six monosaccharides) and an aldose. Glucose can exist in two mirror-image isomers, D-glucose and L-glucose, but only D-glucose exists in nature. Living organisms selectively take up D-glucose into their cells and metabolize it there as a basic energy source. On the other hand, L-glucose, which does not exist in nature, cannot be utilized by normal cells.

[0040] Galactose-derived repeating units A galactose-derived repeating unit (also referred to as a galactose-derived chemical structure) is a compound in which one or two hydrogen atoms have been removed from galactose. In the present disclosure, in a sugar compound or a salt thereof, any of the 1st, 2nd, 3rd, 4th, and 6th hydroxyl groups of galactose may be substituted with a chemical structure derived from the amino acid and / or a chemical structure derived from glucuronic acid. The 6th hydroxyl group refers to the hydroxyl group of the 5th carboxyl group. Galactose is a monosaccharide classified as an aldohexose, as shown below (Gal):

[0041] [ka]

[0042] It is a compound represented by the molecular formula CH 12 D-galactose has a molecular weight of 180.16 (the same as glucose). The configuration is the same for the -OH at the 2-position (second from the top in the Fischer projection) and 5-position, with the -OH at the 3- and 4-positions pointing in the opposite direction. The configuration at the 5-position of D-galactose is the same as that of D-glyceraldehyde. It is a 4-epimer of glucose. Most naturally occurring forms are D-galactose. Note that, in the present disclosure, galactose may be in the α-, β-, or aldehyde form.

[0043] Mannose-derived repeating units A mannose-derived repeating unit (also referred to as a mannose-derived chemical structure) is a compound in which one or two hydrogen atoms have been removed from mannose. In the present disclosure, the sugar compound or a salt thereof may have any of the hydroxyl groups at the 1st, 2nd, 3rd, 4th, and 6th positions of mannose substituted with the above amino acid-derived chemical structure and / or glucuronic acid-derived chemical structure. Mannose is a monosaccharide classified as an aldohexose, and is shown below (Man):

[0044] [ka]

[0045] It is a compound represented by the molecular formula CH 12 O6, and its molecular weight is 180.16 (the same as glucose). Mannose is the 2-epimer of glucose, but its properties are significantly different from those of glucose. In solution, it exists as a 6-membered ring mannopyranose. In the present disclosure, mannose may be in the α-form, β-form, or aldehyde form.

[0046] Repeating units derived from fructose A fructose-derived repeating unit (also referred to as a fructose-derived chemical structure) is a compound in which one or two hydrogen atoms have been removed from fructose. In the present disclosure, the sugar compound or a salt thereof may have any of the hydroxyl groups at the 1st, 2nd, 3rd, 4th, and 6th positions of fructose substituted with the above amino acid-derived chemical structure and / or glucuronic acid-derived chemical structure. Fructose, also known as fruit sugar, is a monosaccharide and includes α-D-fructopyranose represented by the following formula (Fru 1), β-D-fructopyranose represented by the formula (Fru 2), α-D-fructofuranose represented by the formula (Fru 3), and β-D-fructofuranose represented by the formula (Fru 4).

[0047] [ka]

[0048] The molecular formula is CH 12 Its molecular weight is 180.16 (the same as glucose). Fructose is a six-carbon polyhydroxyketone. The ketone group at C2 of the linear D-fructose easily forms an intramolecular hemiacetal with the hydroxyl group at C5 or C6, resulting in a cyclic structure. The formation of the cyclic structure results in the asymmetric formation of the C2 carbon, resulting in the production of α and β isomers. As a result, the cyclic structure of D-fructose can have four types of structures: α-D-fructopyranose, β-D-fructopyranose, α-D-fructofuranose, and β-D-fructofuranose, depending on the combination of "cyclization at C5 or C6" and "α or β type."

[0049] Repeating units derived from glucuronic acid A glucuronic acid-derived repeating unit (also referred to as a glucuronic acid-derived chemical structure) is a compound in which one or two hydrogen atoms have been removed from glucuronic acid. In the present disclosure, a sugar compound or a salt thereof may have any of the hydroxyl groups at the 1st, 2nd, 3rd, 4th, and 6th positions of glucuronic acid substituted with a chemical structure derived from an amino acid and / or a chemical structure derived from a hexose. The hydroxyl group at the 6th position refers to the hydroxyl group of the carboxyl group at the 5th position. Glucuronic acid is a carboxylic acid formed by oxidizing the 6th carbon of a 6-carbon glucose, i.e., by oxidizing the hydroxymethyl group of glucose to convert it into a carboxy group, and is represented by the following formula (GlcA):

[0050] [ka]

[0051] It is a compound represented by the molecular formula CH 10 O7, with a molecular weight of 194.1408. Note that in the present disclosure, glucuronic acid may be in the α-type, β-type, or aldehyde type.

[0052] Compounds in which the hydroxymethyl group at the end of the sugar has been oxidized to a carboxyl group are collectively called uronic acids. Among these uronic acids, glucuronic acid is known as a representative uronic acid. Glucuronic acid is an optical isomer, and only the D-isomer is known to occur naturally.

[0053] When m+n is 2 or greater, the chemical structure derived from the hexose sugar and the chemical structure derived from the uronic acid are combined, resulting in a sugar classified as a disaccharide, trisaccharide, tetrasaccharide, oligosaccharide, or polysaccharide. Each sugar is bonded by a glycosidic bond. Generally, glycosidic bonds are classified as α-glycosidic bonds and β-glycosidic bonds, and the numbers 1, 4, and 6 identify the carbon atoms that make up the glycosidic bond.

[0054] An α-glycosidic bond attaches the substituents below the plane of the sugar structure (axially). β-glycosidic bonds are oriented above the plane of the sugar structure (equatorial). When two sugar molecules are linked by a glycosidic bond, a disaccharide is formed. For example, when m+n is 2, the hexose sugar and glucuronic acid are linked by a β-1,4-glycosidic bond or an α-1,4-glycosidic bond. When three or more sugar molecules are bonded, the hexose and glucuronic acid may be bonded via a β-1,4-glycosidic bond or an α-1,4-glycosidic bond.

[0055] In the sugar compound represented by the above general formula (1) or a salt thereof, the substituent G is bonded to the chemical structure derived from the above amino acid. Specifically, in the sugar compound represented by general formula (1) or a salt thereof, a 2-amino-3-phenylpropyl group, a 2-amino-1-hydroxy-3-phenylpropyl group, a phenylalanine residue, a 2-amino-3-(4-hydroxyphenyl)propyl group, a 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or a tyrosine residue substitutes for one of the oxygen atoms in the hydroxyl group of the hexose, the hydroxyl group of glucuronic acid, or the carboxylic acid group.

[0056] The sugar compound represented by the general formula (1A) or a salt thereof has a substituent G 1 is bonded to the above amino acid-derived chemical structure, and the substituent G 2 G 1 is bonded to. Specifically, the sugar compound represented by the general formula (1A) or a salt thereof has a 2-amino-3-phenylpropyl group, a 2-amino-1-hydroxy-3-phenylpropyl group, a phenylalanine residue, a 2-amino-3-(4-hydroxyphenyl)propyl group, a 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or a tyrosine residue substituted for any one of the oxygen atoms in the hydroxyl group of glucose, and a substituent G 2 may substitute for one of the remaining hydroxyl groups of the hexose sugar.

[0057] When there are two or more substituents G and the Gs are different groups, the order of the substituents G is not limited, and the bonding form may be alternating, block, or random.

[0058] G 1 and G 2 The order of is not limited, and the bonding style may be alternating, block, or random. Alternating means, for example, G 1 -G 2 -G 1 , G 2 -G 1 -G 2 , G 1 -G 2 -G 1 -G 2 , G 2 -G 1 -G 2 -G 1 etc. A block is, for example, G 1 -G 1 -G 2 , G 2 -G 2 -G 1 , G 1 -G 1 -G 1 -G 2 , G1 -G 1 -G 2 -G 2 , G 1 -G 2 -G 2 -G 2 , G 1 -G 2 -G 2 -G 1 , G 2 -G 1 -G 1 -G 1 , G 2 -G 2 -G 1 -G 1 , G 2 -G 2 -G 2 -G 1 etc. Random means G 1 and G 2 This means that there is no order in the arrangement of

[0059] The sugar compound or a salt thereof may have another chemical structural formula, for example, the following general formula (2):

[0060] [ka]

[0061] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are the same or different, hydrogen atoms, 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or A tyrosine residue is indicated. However, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 At least one of the 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or It is a tyrosine residue. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. It can be expressed as:

[0062] Among them, preferred sugar compounds or salts thereof are those represented by the following general formula (2A-1):

[0063] [ka]

[0064] (In the formula, R 11 represents a hydrogen atom or a hydroxyl group. R 12 represents a hydrogen atom, a hydroxyl group, or an oxo group. m represents an integer of 1 to 20. n represents an integer of 0 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. A compound represented by the formula (I) or a salt thereof;

[0065] The following general formula (2B-1):

[0066] [ka]

[0067] (In the formula, R 11 , R 12 , m, and n have the same meanings as defined above. The bond site represented by the wavy line may be an α-bond or a β-bond. A compound represented by the following formula (I) or a salt thereof;

[0068] The following general formula (2C-1):

[0069] [ka]

[0070] (In the formula, R 11 , R 12 , m, and n are as defined above, or a salt thereof;

[0071] The following general formula (2D-1):

[0072] [ka]

[0073] (In the formula, R 11 , R 12 , m, and n have the same meanings as defined above. The bond site represented by the wavy line may be an α-bond or a β-bond. A compound represented by the following formula (I) or a salt thereof;

[0074] The following general formula (2E-1):

[0075] [ka]

[0076] (In the formula, R 11 , R 12 , m, and n have the same meanings as defined above. The bond site represented by the wavy line may be an α-bond or a β-bond. A compound represented by the following formula (I) or a salt thereof;

[0077] The following general formula (2F-1):

[0078] [ka]

[0079] (In the formula, R 11 , R 12 , m, and n have the same meanings as defined above. The bond site represented by the wavy line may be an α-bond or a β-bond. A compound represented by the following formula (I) or a salt thereof;

[0080] The following general formula (2G-1):

[0081] [ka]

[0082] (In the formula, R 11 , R 12 , m, and n have the same meanings as defined above. The bond site represented by the wavy line may be an α-bond or a β-bond. A compound represented by the following formula (I) or a salt thereof; Or,

[0083] The following general formula (2H-1):

[0084] [ka]

[0085] (In the formula, R 11 , R 12 , m, and n have the same meanings as defined above. The bond site represented by the wavy line may be an α-bond or a β-bond.

[0086] More preferred sugar compounds or salts thereof are the compounds represented by the above formula (2A-1) or salts thereof, and the compounds represented by the above formula (2G-1) or salts thereof.

[0087] More preferred sugar compounds or salts thereof are those represented by the following general formula (2A-2):

[0088] [ka] (In the formula, R 12 , the wavy line, m, and n are as defined above, or a salt thereof; The following general formula (2G-2):

[0089] [ka]

[0090] (In the formula, R 12 , the wavy line, m, and n are as defined above, or a salt thereof; The following general formula (2A-3):

[0091] [ka]

[0092] (wherein the wavy line, m, and n are as defined above) or a salt thereof; or a compound represented by the following general formula (2G-3):

[0093] [ka] (wherein the wavy line, m, and n are as defined above) or a salt thereof.

[0094] Furthermore, among the sugar compounds or salts thereof in which m is 1 and n is 0, preferred compounds or salts thereof are compounds or salts thereof represented by the following formulae (1-m1-1) to (1-m1-3).

[0095] [ka] In these compounds, the amino acid-derived chemical structure may be bonded not only to position 4 but also to positions 1, 2, 3, or 6. The bond site represented by the wavy line may be an α-bond or a β-bond.

[0096] Among the sugar compounds or salts thereof in which m is 0 and n is 1, preferred compounds or salts thereof are compounds or salts thereof represented by the following formulas (1-n1-1) to (1-n1-6). In these compounds, the amino acid-derived chemical structure may be bonded not only to the 4-position but also to the 1-position, 2-position, 3-position, or 6-position. The bond site represented by the wavy line may be an α-bond or a β-bond.

[0097] [ka]

[0098] The sugar compound or salt thereof in which m is 1 and n is 1 is a compound or salt thereof represented by the following formulae (1-m1n1-1) to (1-m1n1-6):

[0099] [ka]

[0100] Or, it is a compound represented by the following formulas (1-n1m1-1) to (1-n1m1-6) or a salt thereof. In these compounds, the amino acid-derived chemical structure may be bonded not only to position 4 but also to positions 1, 2, 3, or 6 of the sugar. The bond site represented by the wavy line may be an α-bond or a β-bond.

[0101] [ka]

[0102] The sugar compound or salt thereof in which m is 2 and n is 1 is a compound or salt thereof represented by the following formulae (1-m2n1-1) to (1-m2n1-6):

[0103] [ka]

[0104] Or, it is a compound represented by the following formulas (1-n2m1-1) to (1-n2m1-6) or a salt thereof.

[0105] [ka] In addition, the above formulas (1-m1-1) to (1-m1-3), (1-n1-1)~(1-n1-6), (1-m1n1-1)~(1-m1n1-6), (1-n1m1-1)~(1-n1m1-6), (1-m2n1-1) to (1-m2n1-6), and The amino acid units of the compounds represented by (1-n2m1-1) to (1-n2m1-6) may be substituted at any hydroxyl group of the sugar unit. Furthermore, two or more sugar units may be bonded at any position, and the bond between the sugar moieties may be an α-bond or a β-bond.

[0106] The sugar compound may have another chemical structural formula, for example, the following general formula (3):

[0107] [ka]

[0108] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5, R 6 , R 7 , and R 8 are the same or different, hydrogen atoms, 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or A tyrosine residue is indicated. However, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 At least one of the 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or It is a tyrosine residue. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The binding site represented by the wavy line may be an α- or β-bond. In addition, the bond indicated by the wavy line may be an α bond or a β bond. It can be expressed as:

[0109] The sugar compound or a salt thereof may be represented by the following general formula (3A-1):

[0110] [ka]

[0111] (In the formula, R 11 , R 12 , the wavy line, m, and n are as defined above, or a salt thereof; The following general formula (3A-2):

[0112] [ka]

[0113] (In the formula, R 12 , the wavy line, m, and n are as defined above, or a salt thereof;

[0114] The following general formula (3A-3):

[0115] [ka]

[0116] (wherein the wavy line, m, and n have the same meanings as defined above) or a salt thereof. In these compounds, the amino acid-derived chemical structure may be bonded not only to position 4 but also to positions 1, 2, 3, or 6 of the sugar. Two or more sugar units may be bonded at any position, and the bond between the sugar moieties may be an α- or β-bond.

[0117] In the present disclosure, the form of the salt is not particularly limited, and the counter ion may be either a cation or anion. Examples of salts include inorganic salts (ammonium salts, etc.), alkali metal salts (sodium salts, potassium salts, lithium salts, etc.), alkaline earth metal salts (calcium salts, etc.), metal salts (magnesium salts, aluminum salts, iron salts, zinc salts, copper salts, nickel salts, etc.), halides (fluorides, chlorides, etc.), carboxylate salts (acetates, etc.), organic amine salts (dibenzylamine salts, glucosamine salts, ethylenediamine salts, diethylamine salts, triethylamine salts, dicyclohexylamine salts, diethanolamine salts, tetramethylammonium salts, etc.), and the like.

[0118] The method for producing the salt of the sugar compound used in the present invention is not particularly limited, and the salt of the sugar compound can be produced from the above sugar compound by a conventionally used salt formation process, desalting process, salt exchange process, etc.

[0119] The sugar compound or salt thereof according to the present disclosure can be produced from fermentation-decomposed eggshell membranes obtained by the production method described in the above-mentioned Patent Document 2 (Japanese Patent No. 7237293). Specifically, Patent Document 2 describes a method for producing decomposed eggshell membranes by fermentation, in which eggshell membranes are decomposed using decomposing enzymes produced by koji through fermentation, and is characterized by including an eggshell membrane fermentation step in which koji and eggshell membranes are mixed and fermented to produce a fermentation-decomposed eggshell membrane liquid.

[0120] In the method for producing eggshell membranes through fermentation and decomposition, the eggshell membrane fermentation step may be configured to ferment sake lees in addition to the eggshell membranes.

[0121] In addition, honey or grains can be used instead of sake lees.

[0122] The method for producing eggshell membranes through fermentation and decomposition may further include a koji production step of producing the koji from seed koji prior to the eggshell membrane fermentation step.

[0123] With this configuration, by culturing koji mold from seed koji, the koji mold can produce protein-degrading enzymes such as protease and sugar-degrading enzymes such as amylase.

[0124] The method for producing fermentation-decomposed eggshell membranes may be configured to include a step of sterilizing the fermentation-decomposed eggshell membrane liquid and inactivating the enzymes therein after the eggshell membrane fermentation step.

[0125] This configuration stops the decomposition of proteins or sugars by the proteases and amylases contained in the filtered decomposition liquid, thereby halting the growth of koji mold.

[0126] The method for producing fermentation-decomposed eggshell membranes may further include a solids removal step of removing solids from the fermentation-decomposed eggshell membrane liquid after the inactivation step.

[0127] This configuration makes it possible to remove undecomposed eggshell membranes and koji mold cells, which are solid components that are unnecessary as raw materials for foods, etc.

[0128] The method for producing fermentation-decomposed eggshell membranes may also include a drying step of drying the fermentation-decomposed eggshell membrane liquid after the solid content has been removed in the solid content removal step.

[0129] This configuration makes it possible to obtain fermented and decomposed eggshell membranes in a powder form that is easy to use.

[0130] The sugar compound or salt thereof of the present invention can be used in foods such as functional foods (foods with functional claims). As a functional food, for example, it can be prepared as a supplement in the form of a tablet, pill, capsule, powder, granule, fine granule, lozenge, liquid, etc., together with various additives used in the manufacture of general supplements. In addition, there are no particular limitations on the foods that can be blended, and functional foods can be produced by blending the sugar compound of the present invention or a salt thereof into, for example, candy, gummies, chewing gum, cookies, crackers, biscuits, chocolate, pudding, jelly, snacks, rice crackers, steamed buns, yokan, ice cream, popsicles, sherbet, gelato, donuts, cakes, bread, French bread, croissants, udon, soba, Chinese noodles, kishimen, rice, red rice, pilaf, curry sauce, stew, dressing, ham, sausage, kamaboko, chikuwa, fish sausage, tempura, croquettes, hamburger steak, juice, tea, etc. Functional foods (foods with functional claims) can also be called functional food compositions (food compositions with functional claims).

[0131] When used as a functional food, the dosage of the above sugar compound or its salt may vary depending on the method of administration and the patient's age, condition, general condition, etc., but for adults, a dosage of 0.01 mg to 10 mg per kg of body weight per day is usually appropriate. [Example]

[0132] [Example 1] A fermentation-decomposition eggshell membrane production method will be described in Example 1. The fermentation-decomposition eggshell membrane production method in Example 1 includes an eggshell membrane fermentation step in which eggshell membranes are decomposed to peptides using proteolytic enzymes such as proteases produced from koji.

[0133] In Example 1, an eggshell membrane fermentation process is carried out to produce a fermentation-decomposed eggshell membrane liquid. In the eggshell membrane fermentation process, coarsely crushed eggshell membranes and sake lees (from which the alcohol has been removed) are placed in a tank and mixed with koji. Any koji can be used as the koji in Example 1, such as soy sauce koji, rice koji, or soybean koji. When 10 to 100 g of eggshell membranes are mixed with 10 to 100 g of sake lees (dry weight) and the koji is added, enzymatic decomposition occurs at approximately 45°C. When the mixture is allowed to mature in this state for 0.5 to 7 days, the protease enzymes, peptidase enzymes, and amylase secreted by the koji decompose the proteins and sugars. When fermentation is complete, a turbid liquid containing fermentation-decomposed eggshell membranes (hereinafter also referred to as "fermentation-decomposed eggshell membrane liquid") is obtained.

[0134] Fermentation does not break down proteins into amino acids, but rather ends with some of the proteins being broken down into peptides. Peptides are said to promote skin turnover. The liquid fermented eggshell membrane contains mucopolysaccharides containing amino acids such as chondroitin and hyaluronic acid, as well as collagen.

[0135] Because it contains the above-mentioned peptides, mucopolysaccharides, and collagen, it can be processed into supplements, cosmetics, etc., to produce decomposed eggshell membrane that retains components important for maintaining beauty or health.

[0136] In Example 1, eggshell membranes and sake lees were added in a 1:1 ratio for fermentation, but this is not necessarily limited to this and can be modified as appropriate. For example, eggshell membranes alone may be fermented without adding sake lees, or eggshell membranes and sake lees may be mixed in any ratio other than 1:1. Also, soy milk or honey may be used instead of sake lees.

[0137] Thus, in Example 1, a fermentation-decomposed eggshell membrane production method is used to produce decomposed eggshell membranes by decomposing eggshell membranes through fermentation using koji that secretes proteolytic enzymes, and the method comprises the steps of: The fermentation-decomposed eggshell membrane production method, which is characterized by including an eggshell membrane fermentation step in which eggshell membranes are fermented with proteolytic enzymes secreted by the koji, makes it possible to produce decomposed eggshell membranes containing components with high cosmetic effects at low cost.

[0138] [Example 2] Example 2 differs from Example 1 in that it includes a koji production step of producing koji from seed koji before the eggshell membrane fermentation step.

[0139] In the koji production process of Example 2, koji is produced from starter koji. 10 to 100 g (dry weight) of eggshell membranes, which have also been sterilized, and 10 to 100 g of glucose are added to 5 L of sterilized water, and 10 ml of koji mold liquid is added. The mixture is stirred and aerated at 25°C to 45°C for one day to one week. During this time, the koji mold produces protease or peptidase, a protein-degrading enzyme, or amylase, a glycolytic enzyme. These enzymes are then eluted into the liquid.

[0140] Next, the koji produced in the koji production step is used to carry out an eggshell membrane fermentation step to produce a fermented eggshell membrane liquid. In the eggshell membrane fermentation step, coarsely crushed eggshell membranes and sake lees are placed in a tank and mixed with the koji produced in the koji production step. Any koji, such as soy sauce koji, rice koji, or soybean koji, can be used as the koji in Example 2. Then, when 10 to 100 g of eggshell membranes are mixed with 10 to 100 g of sake lees (dry weight) and the koji is added, enzymatic decomposition occurs at approximately 45°C. When the mixture is aged in this state for 0.5 to 7 days, the protease enzymes, peptidase enzymes, and amylase secreted by the koji decompose the proteins and sugars. When fermentation is complete, a turbid liquid containing fermented and decomposed eggshell membranes (hereinafter also referred to as "fermented and decomposed eggshell membrane liquid") is produced.

[0141] The breakdown of proteins by fermentation does not result in the breakdown of amino acids, but rather ends with some of the proteins being broken down into peptides. The liquid fermented eggshell membrane contains mucopolysaccharides containing amino acids such as chondroitin and hyaluronic acid, as well as collagen.

[0142] In Example 2, 1 part of eggshell membrane is added to 1 part of sake lees for fermentation, but this is not necessarily limited to this and can be modified as appropriate. For example, eggshell membranes alone may be fermented without adding sake lees, or eggshell membranes and sake lees may be mixed in any ratio other than 1:1. Also, soy milk or honey may be used instead of sake lees.

[0143] In this way, in Example 2, a koji production step of producing koji from koji seed is provided before the eggshell membrane fermentation step. By culturing koji mold from koji seed, the koji mold can produce protease and other proteolytic enzymes, and amylase and other glycolytic enzymes.

[0144] [Example 3] Example 3 differs from Examples 1 and 2 in that it includes a sterilization and inactivation step for inactivating the enzyme after the eggshell membrane fermentation step.

[0145] In Example 3, an inactivation step for sterilization and enzyme inactivation is carried out after the eggshell membrane fermentation step. Although the fermentation-decomposed eggshell membrane liquid still contains proteases even after filtration, the inactivation step prevents further degradation of peptides, stops the growth of koji mold, and prevents spoilage due to various bacteria.

[0146] In the inactivation step, the fermented and decomposed eggshell membrane liquid obtained in the eggshell membrane fermentation step may be heated at 60 to 90°C for 10 minutes to 3 hours, but in most cases, sterilization and enzyme inactivation can be achieved by heating at 70°C for 30 minutes.

[0147] Thus, in Example 3, the fermentation-decomposition eggshell membrane production method is configured to include a sterilization and enzyme inactivation step after the eggshell membrane fermentation step, thereby preventing further degradation of proteins or peptides by the proteases contained in the filtered decomposition solution.

[0148] [Example 4] Example 4 differs from Example 3 in that it includes a solids removal step after the inactivation step, in which solids are removed from the inactivated fermented and decomposed eggshell membrane liquid to obtain a fermented and decomposed eggshell membrane liquid.

[0149] In Example 4, after the inactivation step, a solids removal step is carried out to remove solids from the inactivated fermented decomposition eggshell membrane liquid to obtain a fermented decomposition eggshell membrane liquid. This allows the removal of undecomposed eggshell membranes and koji mold cells, which are solids that are not required as cosmetic raw materials.

[0150] Specifically, the solid content removal step can be carried out by placing the fermentation-decomposed eggshell membrane liquid in a cloth bag or the like and squeezing it. Alternatively, the solid content may be removed by filtration using filter paper or the like, or by using a centrifuge.

[0151] Thus, in Example 4, the method for producing fermentation-decomposed eggshell membranes includes a solids removal step for removing solids from the fermentation-decomposed eggshell membrane liquid after the inactivation step, which makes it possible to remove undecomposed eggshell membranes and koji mold cells, which are solids that are not required as cosmetic raw materials.

[0152] [Example 5] Example 5 differs from Example 4 in that it includes a drying step in which the fermentation-decomposed eggshell membrane liquid is dried after the solid content has been removed in the solid content removal step.

[0153] In Example 5, a drying step is carried out to dry the fermented decomposition eggshell membrane liquid after the solids have been removed in the solids removal step. The drying step can be carried out by a known method such as spray drying. The drying step makes it possible to produce a convenient powder of fermented decomposition eggshell membranes.

[0154] Thus, in Example 5, by including a drying step in which the fermented decomposition eggshell membrane liquid is dried after the solids have been removed in the solids removal step, it is possible to obtain fermented decomposition eggshell membranes in a powder form that is easy to use.

[0155] [Comparative Example] (Production of hydrolyzed eggshell membrane) To compare with the fermentation-decomposed eggshell membrane produced by the fermentation-decomposed eggshell membrane production method in Example 1, hydrolyzed eggshell membrane was produced by the conventional method described below.

[0156] First, 1.02 g of dried eggshell membrane powder (average particle size 7 μm) was added to 12.55 g of an alkaline solution (pH 12.5-14) containing dissolved sodium hydroxide, and hydrolysis was carried out by heating in a water bath at 70-75°C for 4 hours with occasional shaking.

[0157] Subsequently, in the acid addition step, hydrochloric acid was added to adjust the pH to 7.1. After standing overnight, the supernatant (6.8 g) was collected and subjected to desalting treatment to recover the hydrolyzed eggshell membrane. The residue was 0.07 g. This pale yellow powder was designated as the eggshell membrane hydrolyzate. This powder was soluble in water.

[0158] sample As a pretreatment for measurement, the aqueous solutions of the fermented and decomposed eggshell membranes obtained in Examples 1 to 3 were distilled under reduced pressure and dried to obtain sugar compounds.

[0159] measurement <MALDI Measurement> MALDI-TOF MS was performed using an ultraflex III (Nd:YAG laser; 355 nm) manufactured by Bruker Daltonics. The measurement method was set as Reflector Negative. 2,5-Dihydroxybenzoic acid was used as the matrix. The measurement sample was a 1 / 1 (v / v) mixed solution (0.4 μL) of the dried fermented and decomposed eggshell membrane (1 mg / mL -1 in methanol) and the matrix (77 mg / mL -1 in methanol), which was dropped onto a sample plate and then air-dried for use in the measurement. The measurement results are shown in Figures 1 to 3.

[0160] <NMR Measurement> The sugar compounds of Examples 1 to 3 were measured by NMR under the following measurement conditions. (Conditions) Apparatus: JEOL JNM-ECS 400 (400 MHz) Solvent: Methanol-d4, chloroform-d1 Internal standard substance: Methanol-d4: None, chloroform-d1: TMS (0.00 ppm) Measurement temperature: 25 °C Number of integrations: 1 1H-NMR: 16 times, 13 13C-NMR: 16 times The measurement results are shown in Figures 4 to 6.

[0161] result The MALDI-TOF MS measurement results (Figure 1, etc.) showed two series of periodic peaks between 300 Da and 2,000 Da. This series of peaks repeated at periodic intervals of approximately 162.0 Da and 176.0 Da. This indicated that the chemical structure contained sugar chains such as glucose, galactose, mannose, and fructose. The signal at 150.8 Da is the starting point of a series of peaks, and this value is 2-amino-3-phenylpropyloxy group (phenylalaninol) (compounds represented by formula (2a1) and formula (2g2) shown with a black circle in Figure 1), 2-amino-1-hydroxy-3-phenylpropyloxy group (compounds represented by formula (2a2) and formula (2g2) shown in ■ in Figure 1), This roughly matched the molecular weight of amino acid-derived structures such as the 2-amino-3-(4-hydroxyphenyl)propyloxy group (the compound represented by formula (2a3) and the compound represented by formula (2g3) shown in ■ in Figure 1). As mentioned above, the structure is presumed to contain sugar chains, and these peaks have amino acid-derived structures such as phenylalaninol at the end, with two types of sugar chains alternately bound to the hydroxyl group moiety. Furthermore, a series of peaks were observed at positions approximately 16 Da larger than the main series of peaks (compounds shown as ■ in Figure 1). Since 16 Da corresponds to the molecular weight of the oxygen atom, the compounds were estimated to have the chemical structures represented by formulas (2a2), (2g2), (2a3), and (2g3) in Figure 1(C). Therefore, it was found that the present compound is a sugar compound or a salt thereof containing a chemical structure derived from an amino acid and a chemical structure derived from a sugar, and has a chemical structure derived from an amino acid such as a 2-amino-3-phenylpropyl group, a 2-amino-1-hydroxy-3-phenylpropyl group, a 2-amino-3-(4-hydroxyphenyl)propyl group, or a 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, and contains one or more repeating units derived from a hexose and / or one or more repeating units derived from a uronic acid, wherein the hexose is at least one selected from the group consisting of glucose, galactose, mannose, and fructose; and the uronic acid is glucuronic acid. Due to space limitations, Figures 1(C), 2, and 5 show, as representative examples, compounds in which an amino acid-derived chemical structure and the hexose-derived repeating unit or a glucuronic acid-derived repeating unit are bonded at the 4- or 1-position of the hexose-derived repeating unit, but the amino acid-derived chemical structure could be bonded not only at the 4- or 1-position but also at the 2-, 3-, or 6-position of the sugar. It was also assumed that the bond of the sugar moiety could be an α- or β-bond. In summary, the compound was identified from the measurement results as a sugar compound represented by the above general formula (1) or (2) or a salt thereof. [Industrial Applicability]

[0162] The sugar compound or salt thereof of the present invention can be used in foods such as functional foods.

Claims

1. Chemical structures derived from amino acids, and A sugar compound or a salt thereof containing a sugar-derived chemical structure, The amino acid-derived chemical structure is a 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, a 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or is a tyrosine residue, The sugar-derived chemical structure is Contains one or more repeating units derived from hexose and / or one or more repeating units derived from uronic acid, The hexose sugar is glucose, galactose, Mannose, and at least one selected from the group consisting of fructose; The uronic acid is A sugar compound or a salt thereof, which is glucuronic acid (Here, the order of the repeating units derived from the hexose and the repeating units derived from the uronic acid is not limited, and the bonding pattern may be alternating, block, or random. Furthermore, the bond between the repeating unit derived from a hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. The bond of the sugar moiety may be an α-bond or a β-bond. (However, the sugar compound or a salt thereof is a compound (A): the amino acid-derived chemical structure is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, and The sugar-derived chemical structure excludes sugar compounds or salts thereof in which only repeating units derived from the hexose are present.

2. The sugar-derived chemical structure is one or more glucose-derived repeat units, one or more galactose-derived repeat units, one or more mannose-derived repeat units, and At least one hexose-derived repeating unit selected from the group consisting of one or more fructose-derived repeating units, and The sugar compound or salt thereof according to claim 1, which has one or more repeating units derived from glucuronic acid.

3. The sugar compound is The following general formula (1): 【Chemical 1】 (In the formula, R １１ represents a hydrogen atom or a hydroxyl group. R １２ represents a hydrogen atom, a hydroxyl group, or an oxo group. G, Repeating units derived from glucose, Galactose-derived repeating units, a repeating unit derived from mannose, and at least one hexose-derived repeating unit selected from the group consisting of fructose-derived repeating units, or The repeating units derived from glucuronic acid are shown. l represents an integer of 1 to 40. When l is 2 or more, the order of the two or more Gs is not limited, and the bonding form may be alternating, block, or random. When 1 is 2 or more, the bond between the repeating unit derived from a hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. In addition, the bond between O (oxygen atom) and the G (a repeating unit derived from a hexose sugar or a repeating unit derived from glucuronic acid) may be an α-bond or a β-bond. The sugar compound or salt thereof according to claim 1, which is a compound represented by the formula: (However, the sugar compound or its salt is The R １１ is a hydrogen atom or a hydroxyl group, The R １２ is a hydrogen atom or an oxo group, wherein l is an integer of 1 to 40; The compounds or salts thereof in which G consists solely of repeating units derived from the hexose are excluded.

4. The sugar compound is The following general formula (1A): 【Chemistry 2】 (In the formula, R １１ represents a hydrogen atom or a hydroxyl group. R １２ represents a hydrogen atom, a hydroxyl group, or an oxo group. G １ but, Repeating units derived from glucose, Galactose-derived repeating units, a repeating unit derived from mannose, and At least one hexose-derived repeating unit selected from the group consisting of fructose-derived repeating units. G ２ but, The repeating units derived from glucuronic acid are shown. When m is 2 or more and n is 1 or more, G １ and G ２ The order of is not limited, and the bonding style may be alternating, block, or random. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. The above G １ and G ２ The bond to may be an α-bond or a β-bond. Also, O (oxygen atom) and the G １ (hexose-derived repeating unit) or G ２ (the bond with the repeating unit derived from glucuronic acid) may be an α-bond or a β-bond. (However, the sugar compound or its salt is R １１ is a hydrogen atom or a hydroxyl group, R １２ is a hydrogen atom or an oxo group, m is an integer from 0 to 20; (Excluding compounds or salts thereof where n is 0).

5. The sugar compound is represented by the following general formula (2): 【Chemistry 3】 (In the formula, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ are the same or different, hydrogen atoms, a 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, a 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or A tyrosine residue is indicated. However, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , and R ８ At least one of the a 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residues, 2-amino-3-(4-hydroxyphenyl)propyl group, a 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or It is a tyrosine residue. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. The sugar compound or salt thereof according to claim 1, which is a compound represented by the formula: (However, the sugar compound or its salt is R １ is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, m is an integer from 0 to 20; (Excluding compounds where n is 0).

6. The sugar compound is a compound represented by the following general formula (2A-1) or a compound represented by the following general formula (2G-1): 【Chemistry 4】 (In the formula, R １１ represents a hydrogen atom or a hydroxyl group. R １２ represents a hydrogen atom, a hydroxyl group, or an oxo group. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. The sugar compound or salt thereof according to claim 1,

7. The sugar compound is a compound represented by the following general formula (2A-2) or a compound represented by the following general formula (2G-2): 【Chemistry 5】 (In the formula, R １２ represents a hydrogen atom or a hydroxyl group. m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. The sugar compound or salt thereof according to claim 1,

8. The sugar compound is a compound represented by the following general formula (2A-3) or a compound represented by the following general formula (2G-3): 【Chemistry 6】 (In the formula, m represents an integer of 0 to 20. n represents an integer of 1 to 20. m+n is 2 or greater. When m is 2 or more and n is 1 or more, the order of the repeating units bounded by m and n is not limited, and the bonding form may be alternating, block, or random. The bond site represented by the wavy line may be an α-bond or a β-bond. The sugar compound or salt thereof according to claim 1,

9. A food composition comprising the sugar compound or salt thereof according to claim 1.

10. A functional food composition comprising the sugar compound or salt thereof according to claim 1.

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