Novel sugar compound or a salt thereof

Abstract

The present invention aims to provide a novel sugar compound. 【Solution means】A sugar compound or a salt thereof containing a chemical structure derived from an amino acid and a chemical structure derived from a sugar, wherein the chemical structure derived from the amino acid is a 2-amino-3-phenylpropyl group or the like, and the chemical structure derived from the sugar contains a repeating unit derived from one or more hexoses and / or a repeating unit derived from one or more uronic acids, the hexose being glucose or the like; the uronic acid being glucuronic acid, a sugar compound or a salt thereof (however, the sugar compound or a salt thereof excludes compound (A): a sugar compound or a salt thereof in which the chemical structure derived from the amino acid is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, and the chemical structure derived from the sugar is only the repeating unit derived from the hexose).

Description

Technical Field

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

Background Art

[0002] The decomposed eggshell membrane obtained by decomposing the eggshell membrane inside the eggshell of eggs such as chicken eggs is said to have effects such as beauty and health promotion. For example, Patent Document 1 describes a method for producing a hydrolyzable eggshell membrane by hydrolyzing eggshell membrane powder in an alkaline aqueous solution. However, what is described in this Patent Document 1 has problems that the production process is complicated and costly. Further, in the decomposition by alkaline water as in that described in Patent Document 1, there is a problem that useful components such as collagen, hyaluronic acid, chondroitin, and glucosamine, which are contained in the eggshell membrane at a high concentration and have high effects as beauty components, are also decomposed. In particular, hyaluronic acid and chondroitin, which have high water retention, are components that are expected to enhance the moisture retention of the skin and improve the effect of wrinkles caused by dryness. However, there has been a concern that if these are decomposed, the effects when used as raw materials for cosmetics, supplements, etc. will decrease. Therefore, the applicant of the present application disclosed in Patent Document 2 a method for producing a fermented decomposed eggshell membrane for producing a decomposed eggshell membrane by decomposing an eggshell membrane with a degrading enzyme produced by koji by fermentation, characterized in that it comprises an eggshell membrane fermentation step of fermenting by mixing koji and an eggshell membrane to produce a fermented decomposed eggshell membrane solution.

[0003] By the way, sugars are contained in the biological tissues of plants and animals. For example, honey, fruits, etc. contain a lot of sugar components. In particular, glucose is important as an energy source for organisms. Also, DNA and RNA contain sugars called deoxyribose and ribose. And the sugar chain composed of consecutive sugars is called the "third life chain" and has been attracting great attention in recent years. It has been found that sugar chains and sugar compounds, like DNA and proteins, play important roles in life. Therefore, novel sugar compounds derived from organisms are in demand.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0005] The present invention aims to provide a novel sugar compound. Further, the present invention aims to obtain a novel compound from the decomposed eggshell membrane obtained by decomposing the eggshell membrane with a degrading enzyme produced by Aspergillus oryzae through fermentation.

Means for Solving the Problems

[0006] As a result of intensive studies by the present inventors, a novel compound was found from the decomposed eggshell membrane. The present invention has been completed based on such findings.

[0007] That is, the present invention is as follows. Item 1. A sugar compound or a salt thereof containing a chemical structure derived from an amino acid and a chemical structure derived from a sugar, wherein the chemical structure derived from the amino acid is 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, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or a tyrosine residue, wherein the chemical structure derived from the sugar is comprising at least one repeating unit derived from one or more hexoses and / or one or more repeating units derived from one or more uronic acids, wherein the hexose is glucose, galactose, mannose, and at least one selected from the group consisting of fructose; wherein the uronic acid is glucuronic acid, a sugar compound or a salt thereof (wherein the order of the repeating unit derived from the hexose and the repeating unit derived from the uronic acid is not limited, and the bonding form may be alternating, block, or random. Also, the bond between the repeating unit derived from the hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. Also, the bond between the chemical structure derived from the amino acid and the repeating unit derived from the hexose or the repeating unit derived from glucuronic acid may be an α-bond or a β-bond.) (However, the sugar compound or a salt thereof excludes the compound (A): the chemical structure derived from the amino acid is a phenylalanine residue, 2-amino-3-phenylpropyl group, or a tyrosine residue, and the chemical structure derived from the sugar is a sugar compound or a salt thereof consisting only of the repeating unit derived from the hexose.)).

[0008] Item 2. wherein the chemical structure derived from the sugar is at least one repeating unit derived from one or more glucoses, at least one repeating unit derived from one or more galactoses, at least one repeating unit derived from one or more mannoses, and at least one repeating unit derived from one or more fructoses selected from the group consisting of, and The saccharide compound according to item 1 or a salt thereof, which has a repeating unit derived from 1 or 2 or more glucuronic acids. Item 3. The saccharide compound is represented by the following general formula (1):

[0009]

Chemical formula

[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 is a repeating unit derived from glucose, a repeating unit derived from galactose, a repeating unit derived from mannose, and at least one repeating unit derived from a hexose selected from the group consisting of a repeating unit derived from fructose, or a repeating unit derived from glucuronic acid. l represents an integer from 1 to 40. When l is 2 or more, the order of two or more Gs is not limited, and the bonding form may be alternating, block, or random. Also, when l is 2 or more, the bond between the repeating unit derived from the hexose and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. Also, the bond between O (oxygen atom) and the G (repeating unit derived from hexose or repeating unit derived from glucuronic acid) may be an α-bond or a β-bond.) The saccharide compound according to item 1 or a salt thereof, which is a compound represented by (However, the saccharide compound or a salt thereof is wherein R 11 is a hydrogen atom or a hydroxyl group, wherein R 12 is a hydrogen atom or an oxo group, wherein l is an integer from 1 to 40, Excluding compounds or salts thereof that are composed only of repeating units derived from the hexasaccharides.) Item 4. The sugar compound is represented by the following general formula (1A):

[0011] [Chemical formula]

[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 is a repeating unit derived from glucose, a repeating unit derived from galactose, a repeating unit derived from mannose, and represents at least one repeating unit derived from a hexasaccharide selected from the group consisting of repeating units derived from fructose. G 2 is a repeating unit derived from glucuronic acid. When m is 2 or more and n is 1 or more, the order of G 1 and G 2 is not limited, and the bonding form may be alternating, block, or random. m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. The bond between the said G 1 and G 2 may be an α-bond or a β-bond. Also, the bond between O (oxygen atom) and the said G 1 (repeating unit derived from hexasaccharide) or G 2 (repeating unit derived from glucuronic acid) may be an α-bond or a β-bond.). The sugar compound or a salt thereof according to Item 1 (However, the sugar compound or a salt thereof 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, n is a compound when it is 0 or its salt is excluded). Item 5. The sugar compound is represented by the following general formula (2):

[0013]

Chemical formula

[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 and are a hydrogen atom, 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. However, among R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 , at least one of them is 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 It is a tyrosine residue. m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. When m is 2 or more and n is 1 or more, the order of each repeating unit enclosed by m and n is not limited, and the bonding form may be alternating, block, or random. The bonding site represented by the wavy line may be an α-bond or a β-bond.) The saccharide compound or a salt thereof according to Item 1, which is a compound represented by (However, the saccharide compound or a salt thereof R 1 is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, m is an integer from 0 to 20, except for the compound when n is 0.) Item 6. The saccharide compound is a compound represented by the following general formula (2A-1) or a compound represented by the following general formula (2G-1)

[0015]

Chemical formula

[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 from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. When m is 2 or more and n is 1 or more, the order of each repeating unit enclosed by m and n is not limited, and the bonding form may be alternating, block, or random. The bonding site represented by the wavy line may be an α-bond or a β-bond.) The saccharide compound or a salt thereof according to Item 1. Item 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]

Chemical formula

[0018] (In the formula, R 12 represents a hydrogen atom or a hydroxyl group. m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. When m is 2 or more and n is 1 or more, the order of each repeating unit enclosed by m and n is not limited, and the bonding form may be alternating, block, or random. The bonding site represented by the wavy line may be an α-bond or a β-bond.) The sugar compound or a salt thereof according to item 1, which is as described above. Item 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]

Chemical formula

[0020] (In the formula, m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. When m is 2 or more and n is 1 or more, the order of each repeating unit enclosed by m and n is not limited, and the bonding form may be alternating, block, or random. The bonding site represented by the wavy line may be an α-bond or a β-bond.) The sugar compound or a salt thereof according to item 1, which is as described above. Item 9. A food composition containing the sugar compound or a salt thereof according to item 1. Item 10. A functional food composition containing the sugar compound according to Item 1 or a salt thereof.

Effect of the Invention

[0021] According to the present invention, a novel compound can be provided. Further, according to the present invention, a novel compound can be obtained from the decomposed eggshell membrane obtained by decomposing the eggshell membrane with a degrading enzyme produced by koji by fermentation.

Brief Description of the Drawings

[0022]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Mode for Carrying Out the Invention

[0023] Saccharide compound or its salt The sugar compound of the present invention or a salt thereof 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 chemical structure derived from the amino acid is 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residue, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or is a tyrosine residue, the chemical structure derived from the sugar is contains a repeating unit derived from one or more hexasaccharides and / or a repeating unit derived from one or more uronic acids, the hexasaccharide is glucose, galactose, mannose, and is at least one selected from the group consisting of fructose; the uronic acid is glucuronic acid, a sugar compound or a salt thereof. Here, the order of the repeating unit derived from the hexasaccharide and the repeating unit derived from the uronic acid is not limited, and the bonding form may be alternating, block, or random. In addition, the bond between the repeating unit derived from the hexasaccharide and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. In addition, the bond between the chemical structure derived from an amino acid and the repeating unit derived from the hexasaccharide or the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. However, the sugar compound or a salt thereof is compound (A): the chemical structure derived from the amino acid is a phenylalanine residue, a 2-amino-3-phenylpropyl group, or a tyrosine residue, and excludes a sugar compound or a salt thereof in which the chemical structure derived from the sugar is only the repeating unit derived from the hexasaccharide. The chemical structure derived from the amino acid can be referred to as an amino acid unit. The chemical structure derived from the sugar can be referred to as a sugar unit.

[0024] The sugar structure preferably has a structure having one or more repeating units derived from the hexasaccharide and one or more repeating units derived from the glucuronic acid. The number of repeating units derived from the hexasaccharide is one or more, preferably two or more, more preferably 1 to 20, and particularly preferably 1 to 10. The number of repeating units derived from the 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 represents a group represented by the following formula (A1). The 2-amino-1-hydroxy-3-phenylpropyl group represents a group represented by the following formula (A2). The phenylalanine residue represents a group represented by the following formula (A3). The 2-amino-3-(4-hydroxyphenyl)propyl group represents a group represented by the following formula (A4). The 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group represents a group represented by the following formula (A5). The tyrosine residue represents a group represented by the following formula (A6).

[0026] [Chemical formula]

[0027] In the above formula, "·" means the bonding site. A residue means the remaining structure after removing "OH" from the carboxylic acid group of an amino acid.

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

[0029] [Chemical formula]

[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 is a repeating unit derived from glucose, a repeating unit derived from galactose, a repeating unit derived from mannose, and At least one repeating unit derived from a hexasaccharide selected from the group consisting of repeating units derived from fructose, or represents a repeating unit derived from glucuronic acid. l represents an integer from 1 to 40. When l is 2 or more, the order of two or more Gs is not limited, and the bonding form may be alternating, block, or random. Also, when l is 2 or more, the bond between the repeating unit derived from the hexasaccharide and the repeating unit derived from glucuronic acid may be an α-bond or a β-bond. Also, the bond between O (oxygen atom) and the G (repeating unit derived from hexasaccharide or repeating unit derived from glucuronic acid) may be an α-bond or a β-bond.) is a compound represented by (provided that the sugar compound or its salt the R 11 is a hydrogen atom or a hydroxyl group, the R 12 is a hydrogen atom or an oxo group, the l is an integer from 1 to 40, the G excludes a compound or its salt that is only the repeating unit derived from the hexasaccharide.) More preferably, the following general formula (1A):

[0031]

Chemical formula

[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 is a repeating unit derived from glucose, a repeating unit derived from galactose, a repeating unit derived from mannose, and It shows at least one repeating unit derived from a hexasaccharide selected from the group consisting of repeating units derived from fructose. G 2 represents a repeating unit derived from glucuronic acid. When m is 2 or more and n is 1 or more, G 1 and G 2 The order is not limited, and the bonding form may be alternating, block, or random. m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. The said G 1 and G 2 The bond between them may be an α-bond or a β-bond. Also, the bond between O (oxygen atom) and the said G 1 (repeating unit derived from hexasaccharide) or G 2 (repeating unit derived from glucuronic acid) may be an α-bond or a β-bond. It is a compound represented by (However, the said sugar compound or its salt 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, n is 0 excluding the compound.); Or, The following general formula (1B):

[0033]

Chemical formula

[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 represents a repeating unit derived from glucose, a repeating unit derived from galactose, A repeating unit derived from mannose, and represents at least one repeating unit derived from a hexasaccharide selected from the group consisting of repeating units derived from fructose. G 2 represents a repeating unit derived from glucuronic acid. 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 form may be alternating, block, or random. m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. Said G 1 and G 2 The bond between may be an α-bond or a β-bond. Also, the bond between O (oxygen atom) and said G 2 (repeating unit derived from glucuronic acid) or G 1 (repeating unit derived from hexasaccharide) 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, m is an integer from 0 to 20, n is 0, excluding the compound or its salt.).

[0035] Repeating unit derived from hexasaccharide The repeating unit derived from hexasaccharide (also referred to as the chemical structure derived from hexasaccharide) means 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 hexasaccharide (hexose) is a monosaccharide having six carbon atoms. Hexasaccharides include aldohexoses having an aldehyde group at the 1-position and ketohexoses having a ketone group at the 2-position. Examples of aldohexoses include glucose, galactose, mannose, etc. Examples of ketohexoses include fructose, etc. The molecular weight of these repeating units derived from hexasaccharides is about 162.

[0036] Repeating unit derived from glucose The repeating unit derived from glucose (also referred to as the chemical structure derived from glucose) is a compound obtained by removing one or two hydrogen atoms from glucose. In the present disclosure, in any of the hydroxyl groups at the 1-position, 2-position, 3-position, 4-position, and 6-position of the sugar compound or its salt, the chemical structure derived from the above amino acid and / or the chemical structure derived from glucuronic acid may be substituted. Glucose, also known as dextrose, is represented by the following (Glc):

[0037] [Chemical formula]

[0038] It is a compound represented by. The molecular formula is C6H 12 O6, and the molecular weight is 180.16. In the present disclosure, glucose may be in the α-form, β-form, or aldehyde form.

[0039] Glucose is a type of monosaccharide and is an aldohexose classified as a hexose (six-carbon monosaccharide) and an aldose. Glucose can have two isomers that are mirror images of each other, namely D-glucose and L-glucose, but only D-glucose exists exclusively in nature. Organisms selectively take up this D-glucose into cells and metabolize it within the cells as a basic energy source. On the other hand, L-glucose, which does not exist in nature, cannot be utilized by normal cells.

[0040] Repeating unit derived from galactose The repeating unit derived from galactose (also referred to as the chemical structure derived from galactose) is a compound obtained by removing one or two hydrogen atoms from galactose. In the present disclosure, in the sugar compound or its salt, the chemical structure derived from the above-mentioned amino acid and / or the chemical structure derived from glucuronic acid may be substituted at any of the hydroxyl groups at the 1st, 2nd, 3rd, 4th, and 6th positions of galactose. Note that the hydroxyl group at the 6th position means the hydroxyl group of the carboxyl group at the 5th position. Galactose is a type of monosaccharide classified as an aldohexose and is represented by the following (Gal):

[0041]

Chemical formula

[0042] It is a compound represented by. The molecular formula is C6H 12 O6, the molecular weight is 180.16 (the same as glucose). The configuration is such that the -OH at the 2nd position (the second from the top in the Fischer projection formula), the 5th position are in the same direction, and the 3rd and 4th positions are in opposite directions. The configuration at the 5th position of D-galactose is the same as that of D-glyceraldehyde. It is the 4-epimer of glucose. Naturally, mostly D-galactose exists. Note that in the present disclosure, galactose may be in the α-form, β-form, or aldehyde form.

[0043] Repeating unit derived from mannose The repeating unit derived from mannose (also referred to as the chemical structure derived from mannose) is a compound obtained by removing one or two hydrogen atoms from mannose. In the present disclosure, in any of the hydroxyl groups at the 1st, 2nd, 3rd, 4th, and 6th positions of the sugar compound or its salt, the chemical structure derived from the above-mentioned amino acid and / or the chemical structure derived from glucuronic acid may be substituted. Mannose is a kind of monosaccharide classified as an aldohexose, and is represented by the following (Man):

[0044]

Chem.

[0045] It is a compound represented by. The molecular formula is C6H 12 O6, and the molecular weight is 180.16 (the same as glucose). Mannose is an epimer of glucose at the 2nd position, but has significantly different properties from glucose. In solution, it exists as six-membered ring mannopyranose. In the present disclosure, mannose may be in the α-form, β-form, or aldehyde form.

[0046] Repeating unit derived from fructose The repeating unit derived from fructose (also referred to as the chemical structure derived from fructose) is a compound obtained by removing one or two hydrogen atoms from fructose. In the present disclosure, in any of the hydroxyl groups at the 1st, 2nd, 3rd, 4th, and 6th positions of the sugar compound or its salt, the chemical structure derived from the above-mentioned amino acid and / or the chemical structure derived from glucuronic acid may be substituted. Fructose, also called fruit sugar, is one of the monosaccharides, and examples include 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), β-D-fructofuranose represented by the formula (Fru 4), and the like.

[0047]

Chem.

[0048] The molecular formula is C6H 12 O6, and the molecular weight is 180.16 (the same as glucose). Fructose is a six-carbon polyhydroxy ketone. The ketone group at C2 of the chain structure of D-fructose can easily form an intramolecular hemiacetal with the hydroxy group at C5 or C6, changing to a cyclic structure. With the formation of the cyclic structure, the asymmetry of C2 carbon occurs, generating α and β isomers. As a result, in the cyclic structure of D-form fructose, there are a total of four structures: α-D-fructopyranose, β-D-fructopyranose, α-D-fructofuranose, and β-D-fructofuranose, due to the combination of "cyclization at C5 or C6" and "α-form or β-form".

[0049] Repeating unit derived from glucuronic acid The repeating unit derived from glucuronic acid (also referred to as the chemical structure derived from glucuronic acid) is a compound obtained by removing one or two hydrogen atoms from glucuronic acid. In the present disclosure, the sugar compound or its salt may be substituted with the chemical structure derived from the above amino acid and / or the chemical structure derived from hexasaccharide at any of the hydroxy groups at the 1st, 2nd, 3rd, 4th, and 6th positions of glucuronic acid. Note that the hydroxy group at the 6th position means the hydroxy group of the carboxyl group at the 5th position. Glucuronic acid is a carboxylic acid in which the carbon at the 6th position of glucose with 6 carbon atoms is oxidized, that is, the hydroxymethyl group part of glucose is oxidized and converted into a carboxyl group, and is represented by the following formula (GlcA):

[0050]

Chemical formula

[0051] It is a compound represented by. The molecular formula is C6H 10 O7, and the molecular weight is 194.1408. Note that in the present disclosure, glucuronic acid may be in the α-form, β-form, or aldehyde form.

[0052] Compounds in which the hydroxymethyl group at the end of the sugar is oxidized to a carboxy group are collectively referred to as uronic acids. Among these uronic acids, glucuronic acid is known as a typical uronic acid. Glucuronic acid, as an optical isomer, is known to exist only as the D-form in nature.

[0053] When m + n is 2 or more, the chemical structure derived from the hexasaccharide and the chemical structure derived from the uronic acid are bonded, and in that case, it becomes a sugar classified as a disaccharide, trisaccharide, tetrasaccharide, oligosaccharide, or polysaccharide. Each sugar is bonded by a glycosidic bond. Generally, glycosidic bonds are classified into α-glycosidic bonds and β-glycosidic bonds, and the numbers 1, 4, and 6 identify the carbon atoms forming the glycosidic bond.

[0054] In an α-glycosidic bond, the substituent is bonded in the downward (axial) direction from the plane of the sugar structure. In a β-glycosidic bond, the bond is in the upward (equatorial) direction from the plane of the sugar structure. When two sugar molecules are glycosidically bonded, a disaccharide is formed. For example, when m + n is 2, the hexasaccharide and glucuronic acid form a β-1,4-glycosidic bond or an α-1,4-glycosidic bond. Even when three or more sugar molecules are bonded, the hexasaccharide and glucuronic acid may form a β-1,4-glycosidic bond or an α-1,4-glycosidic bond.

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

[0056] The sugar compound represented by the above general formula (1A) or a salt thereof has a substituent G 1 bonded to the chemical structure derived from the above amino acid, and the substituent G 2 is bonded to G 1 . 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 substituting for any one of the oxygen atoms in the hydroxyl groups of glucose, and the substituent G 2 may substitute for one of the remaining hydroxyl groups among the hydroxyl groups of the hexasaccharide.

[0057] When there are two or more substituents G and the said Gs are different groups, the order thereof 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 form may be alternating, block, or random. By alternating is meant, 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. can be mentioned. By block is meant, 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. can be mentioned. Random means that there is no order in the arrangement of G 1 and G 2 .

[0059] The sugar compound or its salt has another chemical structural formula, for example, the following general formula (2):

[0060]

Chemical formula

[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, a hydrogen atom, 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residue, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or tyrosine residue. However, at least one of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is one of the following: 2-amino-3-phenylpropyl group, 2-amino-1-hydroxy-3-phenylpropyl group, phenylalanine residue, 2-amino-3-(4-hydroxyphenyl)propyl group, 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, or tyrosine residue. m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. When m is 2 or more and n is 1 or more, the order of each repeating unit enclosed by m and n is not limited, and the bonding form may be alternating, block, or random. The bonding site represented by the wavy line may be an α-bond or a β-bond.) It can be represented by.

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

[0063]

Chemical formula

[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 from 1 to 20. n represents an integer from 0 to 20. m + n is 2 or more. When m is 2 or more and n is 1 or more, the order of each repeating unit enclosed by m and n is not limited, and the bonding form may be alternating, block, or random. The bonding site represented by the wavy line may be an α-bond or a β-bond.) A compound represented by or a salt thereof;

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

[0066]

Chemical formula

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

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

[0069]

Chemical formula

[0070] (In the formula, R 11 , R 12 , m, and n have the same meanings as described above.) A compound represented by or a salt thereof;

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

[0072]

Chemical formula

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

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

[0075]

Chemical formula

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

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

[0078]

Chemical formula

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

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

[0081]

Chemical formula

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

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

[0084]

Chemical formula

[0085] (wherein R 11 , R 12 , m, and n are as defined above. The bonding site represented by the wavy line may be an α-bond or a β-bond.) is a compound represented by the formula or a salt thereof.

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

[0087] Even more preferred sugar compounds or salts thereof include the following general formula (2A-2):

[0088]

Chemical formula

[0089]

Chemical formula

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

[0091]

Chemical formula

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

[0093]

Chemical formula

[0094] Among the sugar compounds or salts thereof where m is 1 and n is 0, the preferred compounds or salts thereof are the compounds or salts thereof represented by the following formulas (1-m1-1) to (1-m1-3).

[0095]

Chemical formula

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

[0097]

Chemical formula

[0098] The sugar compound or salt thereof where m is 1 and n is 1 is the compound or salt thereof represented by the following formulas (1-m1n1-1) to (1-m1n1-6),

[0099]

Chemical formula

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

[0101] [Chemistry]

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

[0103] [Chemistry]

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

[0105] [Chemistry] Note that the amino acid units of the compounds represented by the above formulas (1-m1-1) to (1-m1-3), (1-n1-1) to (1-n1-6), (1-m1n1-1) to (1-m1n1-6), (1-n1m1-1) to (1-n1m1-6), (1-m2n1-1) to (1-m2n1-6), and (1-n2m1-1) to (1-n2m1-6) may be substituted at any hydroxyl group of the sugar unit. Also, two or more sugar units may be bonded at any position, and the bond in the sugar moiety may be an α-bond or a β-bond.

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

[0107] [Chemistry]

[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 and are a hydrogen atom, 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. However, among R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and, R 8 , at least one of them is 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. m represents an integer from 0 to 20. n represents an integer from 1 to 20. m + n is 2 or more. When m is 2 or more and n is 1 or more, the order of each repeating unit enclosed by m and n is not limited, and the bonding form may be alternating, block, or random. The bonding site represented by the wavy line may be an α-bond or a β-bond. Also, the wavy bond may be an α-bond or a β-bond.) It can be represented by

[0109] Also, the sugar compound or its salt is represented by the following general formula (3A-1):

[0110]

Chem.

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

[0112]

Chem.

[0113] (wherein, R 12 , the wavy line, m, and n are as defined above.) A compound represented by the formula or a salt thereof;

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

[0115]

Chem.

[0116] (wherein, the wavy line, m, and n are as defined above.) It can also be shown as a compound represented by the formula or a salt thereof, etc. In addition, in these compounds, the chemical structure derived from an amino acid may be bonded not only to the 4-position but also to the 1-position, 2-position, 3-position, or 6-position of the sugar. Further, two or more sugar units may be bonded at any position, and the bond of the sugar moiety may be an α-bond or a β-bond.

[0117] In the present disclosure, the form of the salt is not particularly limited, and the counter ion may be a cation or an anion. For example, salts include inorganic salts (such as ammonium salts); alkali metal salts (such as sodium salts, potassium salts, lithium salts, etc.), alkaline earth metal salts (such as calcium salts, etc.), metal salts (such as magnesium salts, aluminum salts, iron salts, zinc salts, copper salts, nickel salts, etc.), halides (such as fluorides, chlorides, etc.), carboxylates (such as acetates, etc.), organic amine salts (such as 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 by subjecting the above sugar compound to a salt formation step, a desalting step, a salt exchange step, etc., which are conventionally used.

[0119] The sugar compound or its salt in the present disclosure can be produced from the fermented decomposed eggshell membrane obtained by the production method described in the above Patent Document 2 (Japanese Patent No. 7237293). Specifically, Patent Document 2 describes a method for producing a fermented decomposed eggshell membrane for producing a decomposed eggshell membrane by decomposing an eggshell membrane with a decomposition enzyme generated by koji through fermentation, which is characterized by comprising an eggshell membrane fermentation step of fermenting by mixing koji and an eggshell membrane to generate a fermented decomposed eggshell membrane solution.

[0120] A method for producing a fermented decomposed eggshell membrane, wherein in the eggshell membrane fermentation step, it may be configured to ferment sake lees in addition to the eggshell membrane.

[0121] Note that honey or grains can be used instead of sake lees of Japanese sake.

[0122] A method for producing a fermented decomposed eggshell membrane, which may be configured to include a koji generation step of generating the koji from a seed koji before the eggshell membrane fermentation step.

[0123] With this configuration, by culturing Aspergillus oryzae from the starter koji, Aspergillus oryzae can produce proteolytic enzymes such as protease and saccharolytic enzymes such as amylase.

[0124] A method for producing fermented and decomposed eggshell membrane may have a configuration including an inactivation step of sterilizing and inactivating enzymes in the fermented and decomposed eggshell membrane liquid after the eggshell membrane fermentation step.

[0125] With this configuration, the decomposition of proteins or sugars by protease and amylase contained in the filtered decomposition liquid can be stopped, and the growth of Aspergillus oryzae can be stopped.

[0126] A method for producing fermented and decomposed eggshell membrane may have a configuration including a solid content removal step of removing solid content from the fermented and decomposed eggshell membrane liquid after the inactivation step.

[0127] With this configuration, undigested eggshell membrane, which is solid content unnecessary as a raw material for foods, etc., and the cells of Aspergillus oryzae can be removed.

[0128] A method for producing fermented and decomposed eggshell membrane may have a configuration including a drying step of drying the fermented and decomposed eggshell membrane liquid after the solid content has been removed by the solid content removal step.

[0129] With this configuration, a user-friendly powdery fermented and decomposed eggshell membrane can be obtained.

[0130] Uses of the sugar compound or a salt thereof according to the present invention include foods such as functional foods (functionally labeled foods). As the functional food, for example, it can be prepared as a supplement in the form of tablets, pills, capsules, powders, granules, fine granules, lozenges, liquids, etc., together with various additives used in the production of general supplements. Moreover, there are no particular limitations on the compatible foods. For example, the sugar compound of the present invention or a salt thereof can be incorporated into candies, gummies, chewing gums, cookies, crackers, biscuits, chocolates, puddings, jellies, snack foods, rice cakes, steamed buns, yokan, ice creams, ice candies, sherbets, gelatos, doughnuts, cakes, bread, French bread, croissants, udon noodles, soba noodles, Chinese noodles, kishimen noodles, white rice, red rice, pilaf, curry sauce, stews, dressings, hams, sausages, kamaboko, chikuwa, fish sausages, tempura, croquettes, hamburgers, juices, tea, etc. to make functional foods. Functional foods (functionally labeled foods) can be paraphrased as functional food compositions (functionally labeled food compositions).

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

Example

[0132] [Example 1] The method for producing fermented and decomposed eggshell membrane in Example 1 will be described. The method for producing fermented and decomposed eggshell membrane in Example 1 includes an eggshell membrane fermentation step of decomposing the eggshell membrane into a peptide state by a proteolytic enzyme such as protease produced from koji.

[0133] In Example 1, the eggshell membrane fermentation step is carried out to produce a fermented and decomposed eggshell membrane solution. In the eggshell membrane fermentation step, the coarsely ground eggshell membrane and sake lees (with the alcohol removed) are put into a tank and koji is mixed. Any koji such as soy sauce koji, rice koji, or soybean koji can be used as the koji in Example 1. Then, when 10 g to 100 g (dry weight) of sake lees is mixed with 10 to 100 g of eggshell membrane and koji is added, enzymatic decomposition occurs at approximately 45°C. When aged for 0.5 to 7 days in this state, the protease enzyme, peptidase enzyme, and amylase secreted by the koji decompose proteins or sugars. And when the fermentation is completed, it becomes a turbid liquid containing fermented and decomposed eggshell membrane (hereinafter also referred to as "fermented and decomposed eggshell membrane solution").

[0134] Protein degradation by fermentation ends with only a part of the protein being degraded into peptides without being degraded all the way to amino acids. Peptides are said to promote skin turnover. In addition, the fermented decomposed eggshell membrane liquid in liquid form contains mucopolysaccharides containing amino acids such as chondroitin and hyaluronic acid, collagen, and the like.

[0135] Due to the inclusion of the above-mentioned peptides, mucopolysaccharides, and collagen, it is possible to obtain a decomposed eggshell membrane that retains important components for maintaining beauty or health by processing it into supplements, cosmetics, etc.

[0136] In Example 1, the eggshell membrane and sake lees were added in a ratio of 1:1 and fermented, but it is not necessarily limited to this and can be appropriately changed. For example, it may be fermented with only the eggshell membrane without adding sake lees, or the eggshell membrane and sake lees may be mixed at an arbitrary ratio instead of 1:1. Also, instead of sake lees, soy milk or honey may be used.

[0137] Thus, in Example 1, it is a method for producing a fermented decomposed eggshell membrane in which the eggshell membrane is decomposed by fermentation using koji that secretes proteolytic enzymes to produce a decomposed eggshell membrane, characterized by comprising an eggshell membrane fermentation step in which the eggshell membrane is fermented by the proteolytic enzyme secreted by the koji, and a decomposed eggshell membrane containing components with high beauty effects at low cost can be produced.

[0138] [Example 2] In Example 2, it is different 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 in Example 2, koji is produced from the starter koji. 10 to 100 g (dry weight) of eggshell membrane and 10 to 100 g of glucose, which have also been sterilized, are added to 5 l of sterilized water, 10 ml of koji mold liquid is added, and the mixture is stirred while being aerated at 25°C to 45°C for 1 day to 1 week. During this period, the koji mold produces proteolytic enzymes such as protease or peptidase, or amylases, which are carbohydrases, and these enzymes are eluted into the liquid.

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

[0141] The decomposition of proteins by fermentation ends with a part of the proteins being decomposed into peptides without being decomposed all the way to amino acids. The liquid fermented and decomposed eggshell membrane liquid contains mucopolysaccharides containing amino acids such as chondroitin and hyaluronic acid, and collagen.

[0142] In Example 2, it was configured to add sake lees to 1 part of eggshell membrane and ferment it, but it is not necessarily limited to this and can be appropriately changed. For example, it may be fermented with only the eggshell membrane without adding sake lees, or the eggshell membrane and sake lees may be mixed at an arbitrary ratio instead of 1:1. Also, instead of sake lees, soy milk or honey may be used.

[0143] Thus, in Example 2, by providing a koji production step of producing koji from the seed koji before the eggshell membrane fermentation step, koji mold is cultured from the seed koji, and the koji mold can produce proteolytic enzymes such as protease and saccharolytic enzymes such as amylase.

[0144] [Example 3] Example 3 is different from Example 1 and Example 2 in that it includes an inactivation step of sterilizing and inactivating enzymes after the eggshell membrane fermentation step.

[0145] In Example 3, after the eggshell membrane fermentation step, an inactivation step of sterilizing and inactivating enzymes is carried out. As a result, although protease is contained in the fermented and decomposed eggshell membrane liquid even after filtration, by carrying out the inactivation step, further decomposition of peptides can be prevented, the growth of koji mold can be stopped, and spoilage by miscellaneous bacteria can be prevented.

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

[0147] Thus, in Example 3, in the method for producing a fermented and decomposed eggshell membrane, by providing a configuration including an inactivation step of sterilizing and inactivating enzymes after the eggshell membrane fermentation step, it is possible to prevent further decomposition of proteins or peptides by the protease contained in the filtered decomposition liquid.

[0148] [Example 4] Example 4 is different from Example 3 in that it includes a solid content removal step of obtaining a fermented and decomposed eggshell membrane liquid with solid content removed from the inactivated fermented and decomposed eggshell membrane liquid after the inactivation step.

[0149] In Example 4, after the inactivation step, a solid content removal step of obtaining a fermented and decomposed eggshell membrane liquid with solid content removed from the inactivated fermented and decomposed eggshell membrane liquid is carried out. Thereby, undecomposed eggshell membrane, which is a solid content unnecessary as a cosmetic raw material, and the cells of koji mold can be removed.

[0150] Specifically, in the solid content removal step, it can be carried out by putting the fermented and decomposed eggshell membrane liquid into a cloth bag or the like and squeezing it. Or, it may be filtered with filter paper or the like, or the solid content may be removed by a centrifuge.

[0151] Thus, in Example 4, in the method for producing a fermented and decomposed eggshell membrane, after the inactivation step, a solid content removal step of removing the solid content from the fermented and decomposed eggshell membrane liquid is provided, so that undecomposed eggshell membranes and Aspergillus oryzae cells, which are solid contents unnecessary as cosmetic raw materials, can be removed.

[0152] [Example 5] Example 5 is different from Example 4 in that it includes a drying step of drying the fermented and decomposed eggshell membrane liquid after the solid content has been removed by the solid content removal step.

[0153] In Example 5, a drying step of drying the fermented and decomposed eggshell membrane liquid after the solid content has been removed by the solid content removal step is carried out. In the drying step, it can be carried out by a known method such as the spray drying method. By the drying step, a user-friendly powdery fermented and decomposed eggshell membrane can be obtained.

[0154] Thus, in Example 5, a configuration including a drying step of drying the fermented and decomposed eggshell membrane liquid after the solid content has been removed by the solid content removal step enables a user-friendly powdery fermented and decomposed eggshell membrane to be obtained.

[0155] [Comparative Example] (Manufacture of hydrolyzed eggshell membrane) In order to compare with the fermented and decomposed eggshell membrane produced by the method for producing a fermented and decomposed eggshell membrane in Example 1, a hydrolyzed eggshell membrane was produced by the following conventional method.

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

[0157] After that, in the acid addition step, hydrochloric acid was added to adjust the pH to 7.1. Then, the supernatant after standing overnight was taken (6.8 g), and the hydrolyzed eggshell membrane was recovered by desalting treatment. The residue was 0.07 g. This pale yellow powder was designated as the hydrolyzate of eggshell membrane. 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 From the measurement results of MALDI-TOF MS (Figure 1, etc.), two series of periodic peaks were observed between 300 Da and 2,000 Da. The periodic intervals of this series of peaks were repetitive at approximately 162.0 Da and approximately 176.0 Da. Therefore, it was found that the chemical structure contained sugar chains such as glucose, galactose, mannose, and fructose. In addition, a signal at 150.8 Da was the starting point of a series of peaks, and this value 2-amino-3-phenylpropyloxy group (phenylalaninol) (compounds represented by formula (2a1) described in ● of Figure 1, compounds represented by formula (2g2)), 2-amino-1-hydroxy-3-phenylpropyloxy group (compounds represented by formula (2a2) described in ■ of Figure 1, compounds represented by formula (2g2)), 2-amino-3-(4-hydroxyphenyl)propyloxy group (compounds represented by formula (2a3) described in ■ of Figure 1, and compounds represented by formula (2g3)), etc., generally corresponded to the molecular weights of amino acid-derived structures. As described above, since it is presumed that the structure contains sugar chains, these peaks had an amino acid-derived structure such as phenylalaninol at the terminal, and a structure in which two types of sugar chains were alternately bonded to the hydroxyl group part. In addition, a series of peaks were also observed at positions approximately 16 Da larger than the main series of peaks (compounds described in ■ of Figure 1). Since 16 Da corresponded to the molecular weight of an oxygen atom, it was presumed to be the chemical structure represented by formula (2a2), formula (2g2), formula (2a3), and formula (2g3) in Figure 1(C). Therefore, 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, having 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, a 2-amino-1-hydroxy-3-(4-hydroxyphenyl)propyl group, etc., containing one or more repeating units derived from hexasaccharides and / or one or more repeating units derived from uronic acids, wherein the hexasaccharide is at least one selected from the group consisting of glucose, galactose, mannose, and fructose; and the uronic acid is glucuronic acid. It was found to be a sugar compound. Note that FIGS. 1(C), 2, and 5 represent, for convenience of the drawing, as representative examples, compounds in which the chemical structure derived from an amino acid and the repeating unit derived from the hexasaccharide or the repeating unit derived from glucuronic acid are bonded at the 4-position or the 1-position of the repeating unit derived from the hexasaccharide. However, the chemical structure derived from an amino acid may be bonded not only at the 4-position or the 1-position but also at the 2-position, 3-position, or 6-position of the sugar. Also, it was presumed that the bond in the sugar moiety may be an α-bond or a β-bond. In summary, from the measurement results, it was identified that the compound is a sugar compound or a salt thereof represented by the above general formula (1) or (2).

Industrial Applicability

[0162] The sugar compound or a salt thereof in 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 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 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. 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 bracketed 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 sugar compound or a salt thereof,

2. 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 2】 (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 bracketed 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 a salt thereof according to claim 1 ,

3. 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 3】 (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 bracketed 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 a salt thereof according to claim 1 ,

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

5. A functional food composition comprising the sugar compound or its salt according to claim 1.

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