WO2017222078A1 - 褐変抑制用組成物及びその用途 - Google Patents
褐変抑制用組成物及びその用途 Download PDFInfo
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- WO2017222078A1 WO2017222078A1 PCT/JP2017/023317 JP2017023317W WO2017222078A1 WO 2017222078 A1 WO2017222078 A1 WO 2017222078A1 JP 2017023317 W JP2017023317 W JP 2017023317W WO 2017222078 A1 WO2017222078 A1 WO 2017222078A1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
Definitions
- the present invention relates to a composition for inhibiting browning and its use.
- the present invention also relates to a method for inhibiting browning of a composition containing polyphenol, a method for producing a food or drink, a method for inhibiting reduction of polyphenol in a composition containing polyphenol, a compound having a xanthylium structure in a composition containing polyphenol.
- the present invention relates to a method for inhibiting the production of aldehyde, a composition for capturing aldehyde, a method for capturing aldehyde, a composition for deodorization, a deodorizing method, a method for screening a compound having a browning-inhibiting action of a composition containing polyphenol, and the like.
- Tea drinks such as green tea, hojicha, and black tea are sold after being sterilized and filled in plastic bottles, cans, paper containers, and the like. It is known that these tea beverages may take a long time from production to drinking, and the liquid color may change to brown (hereinafter referred to as browning). Especially for green tea beverages, the color of the tea extract gradually changes from light green or light yellow to yellowish brown to reddish brown when stored at room temperature. . This browning of the tea beverage not only occurs at room temperature, but also proceeds when the tea extract is heat sterilized in the production of the beverage, and further proceeds during the storage period after the production.
- Patent Literature 1 discloses a flavonoid composition containing rutin and / or a rutin derivative and dihydroquercetin and / or a dihydroquercetin derivative as a technique for suppressing discoloration of food. It is described that it can exhibit functionality such as fading prevention.
- Patent Documents 2 and 3 when a seasoning containing rutin is used in an egg dish, the yellow color of the egg turns brown, but by using a specific flavonoid in the seasoning at a specific ratio, the color tone of the food It is described that the change is suppressed.
- Patent Document 4 describes a liquid seasoning containing a phosphate compound and a polyphenol having a catechol skeleton at a specific ratio as a seasoning in which coloring during cooking is suppressed.
- Non-Patent Documents 1 to 4 xanthylium salts produced by the reaction of catechin and glyoxylic acid derived from tartaric acid have been reported (Non-Patent Documents 1 to 4).
- Non-Patent Document 5 describes that xanthylium salts produced by the reaction of glyoxylic acid and catechin have multiple isomers.
- Patent Documents 1 to 4 discuss techniques for suppressing discoloration of foods and drinks, but do not discuss suppression of browning of green tea drinks.
- Non-patent documents 1 to 5 also do not discuss the suppression of browning of green tea beverages. There is a need for a technique that can effectively suppress browning of green tea beverages, but the cause of browning of green tea beverages has not been clarified.
- the present invention has been made to solve the above-mentioned problems, and mainly provides a composition for inhibiting browning and a method for inhibiting browning, which can suppress browning in a composition containing polyphenol such as a green tea beverage. With a purpose.
- the present inventors have found that xanthylium produced by the reaction of aldehydes produced by the decomposition of L-ascorbic acid (vitamin C) contained in green tea beverages and catechins. It has been found that a compound having a structure is a causative substance of browning.
- a compound having a structure is a causative substance of browning.
- browning of a composition containing polyphenol such as a green tea beverage can be suppressed. I found out that I can do it.
- the technique for suppressing browning by capturing aldehyde is a technique different from the technique for removing oxygen by adding an antioxidant or the like to suppress browning.
- the present inventors have further studied based on these findings and completed the present invention.
- composition for inhibiting browning of the present invention is characterized by containing a compound represented by the following general formula (1).
- R 21 , R 22 , R 23 , R 24 , R 26 and R 27 each independently represents a hydrogen atom or a substituent, and at least one of R 21 and R 23 is a hydrogen atom.
- R 23 represents a hydrogen atom
- at least one of R 22 and R 24 represents a substituent
- R 25 represents a hydrogen atom
- R 22 and R 23 , or R 23 and R 24 may be bonded to each other to form a ring together with the oxygen atom and carbon atom to which they are bonded
- R 25 and R 26 , or R 26 and R 27 may be bonded to each other to form a ring structure together with the carbon atom to which they are bonded
- X represents an oxygen atom or —CH 2 —
- a broken line represents that a double bond may be sufficient.
- the compound represented by the general formula (1) is also referred to as a compound (1).
- the carbon atom to which R 21 is bonded or the carbon atom to which R 23 is bonded react with the aldehyde.
- the said compound (1) is a compound which does not produce
- R ⁇ 11 >, R ⁇ 12 >, R ⁇ 13> , R ⁇ 14> , R ⁇ 15> , R ⁇ 16> , R ⁇ 17> , R ⁇ 18> and R ⁇ 19 > each independently represents a hydrogen atom or a substituent
- R ⁇ 11 > and R ⁇ 12> , R 12 and R 13 , or R 13 and R 14 may be bonded to each other to form a ring structure together with the carbon atom to which they are bonded
- R 18 and R 19 may be bonded together to form a ring structure together with the carbon atom to which they are bonded.
- the compound represented by the general formula (2) is also referred to as a compound (2).
- the general formula (1) it is preferable that none of the positions adjacent to the hydrogen atom bonded to the benzene ring (ortho position) is a hydroxyl group.
- one of the positions adjacent to the hydrogen atom bonded to the benzene ring (ortho position) is a hydroxyl group, and at least in the benzene ring
- One sterically hindered substituent is preferably bonded, and the position adjacent to the hydroxyl group (ortho position) is more preferably a sterically hindered substituent.
- R 21 represents a hydrogen atom
- R 22 and R 23 each independently represent a substituent
- R 23 preferably represents a hydrogen atom
- R 22 and R 24 each independently represent a substituent
- R 21 represents a hydrogen atom
- R 22 represents a hydrogen atom
- R 23 represents a sterically hindered substituent
- R 21 represents a sterically hindered substituent
- R 22 represents a hydrogen atom
- R 24 represents a substituent. Is preferably represented.
- R 23 represents a hydrogen atom
- OR 22 represents a sterically hindered substituent
- R 24 represents a hydrogen atom.
- the sterically hindered substituent is preferably an organic group having 6 to 30 carbon atoms having a ring structure or an organic group having a linear or branched structure having 10 to 30 carbon atoms.
- the substituent is preferably a hydroxyl group, an organic group having 1 to 50 carbon atoms, an amino group, a thiol group, a nitro group, or a halogen atom. More preferably, the substituent is a hydroxyl group or an organic group having 1 to 50 carbon atoms.
- composition for inhibiting browning of the present invention is suitably used for inhibiting browning of a composition containing polyphenol.
- the composition containing the polyphenol is a food or drink containing the polyphenol.
- the polyphenol is preferably a catechin.
- the composition containing the polyphenol is preferably a green tea beverage.
- the method for inhibiting browning of a composition containing a polyphenol of the present invention is characterized by mixing the compound represented by the general formula (1) with a composition containing a polyphenol.
- the composition containing the said polyphenol is food-drinks containing a polyphenol.
- the polyphenol is preferably a catechin.
- the composition containing the said polyphenol is a green tea drink.
- the manufacturing method of the food / beverage products of this invention mixes the compound represented by the said General formula (1), and the food / beverage products containing polyphenol, It is characterized by the above-mentioned.
- the compounding amount of the compound represented by the general formula (1) is preferably 0.001 to 10% by mass with respect to the food and drink.
- the polyphenol is preferably a catechin.
- the food / beverage products containing the said polyphenol are green tea drinks.
- the food / beverage products of this invention mix
- the compounding amount of the compound represented by the general formula (1) is preferably 0.001 to 10% by mass with respect to the food and drink.
- the food or drink of the present invention is preferably a green tea beverage. When the green tea beverage is stored at room temperature for 9 months, the rate of change in the area of the absorbance spectrum when measured using light having a wavelength between 400 and 600 nm, or the absorbance using light having a wavelength of 487 nm. It is preferable that the absorbance change rate when measured is less than 150%.
- the method for inhibiting polyphenol reduction in a composition containing polyphenol of the present invention is characterized by mixing a composition containing polyphenol and a compound represented by the above general formula (1).
- the composition containing the polyphenol and the compound represented by the general formula (1) are mixed. It is characterized by that.
- the aldehyde-trapping composition of the present invention is characterized by containing the compound represented by the general formula (1).
- the aldehyde scavenging composition of the present invention in the general formula (1), either the carbon atom to which R 21 is bonded or the carbon atom to which R 23 is bonded may react with the aldehyde. preferable.
- the said compound (1) is a compound which does not produce
- the deodorant composition of the present invention contains the aldehyde-trapping composition of the present invention.
- the deodorant composition of the present invention is preferably for deodorizing aldehyde-derived odors.
- the method for screening a compound having a browning-inhibiting action of a composition containing a polyphenol of the present invention comprises a step of preparing a sample solution containing a polyphenol, an aldehyde and a candidate compound, and the general formula (2) in the sample solution.
- the method includes the step of determining the browning-inhibiting effect of the candidate compound with the production of the compound represented as an index.
- the production of the compound represented by the general formula (2) is measured by measuring the absorbance spectrum of the sample solution using light having a wavelength of 400 to 600 nm, and the change in the area of the absorbance spectrum.
- the production of the compound represented by the general formula (2) is detected by measuring the absorbance of the sample solution using light having a wavelength of 487 nm and detecting the change in the absorbance.
- the present invention includes the following uses.
- Use of the compound represented by the general formula (1) for inhibiting browning Use of the compound represented by the general formula (1) for capturing an aldehyde.
- Use of the compound represented by the general formula (1) for deodorization A method for capturing an aldehyde, comprising contacting the compound represented by the general formula (1) with a gas or a liquid containing an aldehyde.
- the deodorizing method characterized by making the compound represented by the said General formula (1) contact the gas or liquid containing an aldehyde.
- the composition for browning suppression which can suppress the browning of the composition containing polyphenols, such as a green tea drink, the browning suppression method, etc. can be provided.
- the composition containing polyphenol such as a green tea drink which is hard to brown even if it stores for a long period of time, its manufacturing method, and the browning suppression method of the composition containing polyphenol can be provided.
- acquisition can be provided.
- FIG. 1 is a photograph showing the appearance of a green tea beverage in a PET bottle stored at room temperature for 6, 22, 5, 7, and 9 months.
- FIG. 2 is a view showing a visible absorption spectrum of each green tea beverage shown in FIG.
- FIG. 3 is a visible light absorption spectrum before and after a deterioration test of Condition 2 of a preparation solution containing 0.4 g / L of ascorbic acid.
- FIG. 4 is a view showing a visible absorption spectrum of each preparation solution after the deterioration test ((a): condition 1 (nitrogen substitution, 4 ° C. for 1 hour), (b): condition 2 (121 ° C., 14 minutes) ), (C): Condition 3 (after oxygen aeration, 30 minutes at 123 ° C.)).
- FIG. 1 is a photograph showing the appearance of a green tea beverage in a PET bottle stored at room temperature for 6, 22, 5, 7, and 9 months.
- FIG. 2 is a view showing a visible absorption spectrum of each green tea beverage shown
- FIG. 5 is a diagram showing the concentrations of epicatechin (EC), epigallocatechin (EGC), epicatechin gallate (ECg), and epigallocatechin gallate (EGCg) in green tea and a model liquid (mixed four catechins).
- EC epicatechin
- ECG epigallocatechin
- Eg epicatechin gallate
- ECCg epigallocatechin gallate
- ECCg epigallocatechin gallate
- FIG. 6 is a figure which shows the visible absorption spectrum of the green tea and model liquid (4 types of catechin mixing) before an accelerated deterioration test
- (b) is the change of the absorption before and after the accelerated deterioration of green tea and a model liquid. It is a figure which shows quantity ((DELTA) ABU).
- FIGS. 8A to 8D show epicatechin, a compound in which one molecule of epicatechin and one molecule of glyoxal are detected, and two molecules of epicatechin and one molecule of glyoxal that are detected in the accelerated green tea model.
- FIG. 8A shows epicatechin, a compound in which one molecule of epicatechin and one molecule of glyoxal are detected, and two molecules of epicatechin and one molecule of glyoxal that are detected in the accelerated green tea model.
- FIG. 3 is a diagram showing a chromatogram obtained by analyzing a compound having a xanthylium structure in the SIM mode by LC-MS
- FIG. 9 is a diagram showing changes in the visible absorption spectrum of the model solution due to the addition of baicalin.
- FIG. 9 is a diagram showing changes in the visible absorption spectrum of the model solution due to the addition of baicalin.
- FIG. 10 is a photograph and visible absorption showing the appearance after accelerated deterioration of a mixed solution of baicalin and glyoxal (B + G), a mixed solution of baicalin, epicatechin and glyoxal (B + C + G), and a mixed solution of epicatechin and glyoxal (C + G). It is a figure which shows a spectrum ((a): photograph, (b): visible absorption spectrum).
- FIG. 11 is a diagram showing the catechin remaining amount (mM) in the mixed solution (B + C + G) and the mixed solution (C + G) after accelerated deterioration.
- FIG. 12 is a diagram showing a chromatogram obtained by analyzing a compound detected in a solution obtained by accelerating deterioration of a mixed solution of baicalin and glyoxal in the SIM mode by LC-MS ((a): one molecule of glyoxal and one molecule of baicalin). And (b): baicalin).
- FIG. 13 is a chromatogram (SIM data) obtained by analyzing a fraction containing glycosylated baicalin in SIM mode by LC-MS.
- FIG. 14 is a diagram for explaining the Br value and the Xt value used for screening.
- FIG. 15 is a diagram showing the evaluation results of the browning inhibitory action of compounds (A-1) to (A-5).
- FIG. 16 is a diagram showing the evaluation results of the browning inhibiting action of scutellarin, chafuroside A and icariin.
- composition for inhibiting browning of the present invention is characterized by containing a compound represented by the following general formula (1).
- R 21 , R 22 , R 23 , R 24 , R 26 and R 27 each independently represents a hydrogen atom or a substituent, and at least one of R 21 and R 23 is a hydrogen atom.
- R 23 represents a hydrogen atom
- at least one of R 22 and R 24 represents a substituent
- R 25 represents a hydrogen atom
- R 22 and R 23 , or R 23 and R 24 may be bonded to each other to form a ring together with the oxygen atom and carbon atom to which they are bonded
- R 25 and R 26 , or R 26 and R 27 may be bonded to each other to form a ring structure together with the carbon atom to which they are bonded
- X represents an oxygen atom or —CH 2 —
- a broken line represents that a double bond may be sufficient.
- the benzene ring to which R 21 and R 23 in the general formula (1) are bonded is also referred to as a benzene ring A.
- the composition for inhibiting browning of the present invention contains the compound (1) as an active ingredient.
- R 21 and R 23 each independently represents a hydrogen atom or a substituent. At least one of R 21 and R 23 is a hydrogen atom. That at least one of R 21 and R 23 is a hydrogen atom means that R 21 and / or R 23 is a hydrogen atom.
- R 22 and R 24 each independently represent a hydrogen atom or a substituent.
- R 23 represents a hydrogen atom
- at least one of R 22 and R 24 (R 22 and / or R 24 ) Represents a substituent.
- at least one of the positions adjacent to the hydrogen atom bonded to the benzene ring A (ortho position) is not a hydroxyl group.
- the compound (1) in the present invention is a compound that reacts with an aldehyde, and preferably reacts with an aldehyde in a solution having a pH of 5 to 9, for example. In one embodiment, it is also preferred that the compound (1) reacts with an aldehyde in a solution having a pH of 6 to 6.5.
- a carbon atom bonded to a hydrogen atom reacts with an aldehyde. This reaction is preferably a nucleophilic addition of an aldehyde to the carbonyl carbon.
- the position at which the benzene ring A can react with an aldehyde is one when either R 21 or R 23 is a hydrogen atom, and R 21 and R 23 are When it is a hydrogen atom, it is two, but preferably one.
- the number of hydrogen atoms bonded to the benzene ring A is one or two, but preferably one.
- at least one of the carbon atom to which R 21 is bonded and the carbon atom to which R 23 is bonded usually react with the aldehyde, but the carbon atom to which R 21 is bonded. or the carbon atom to which R 23 is bonded is preferably reacted with an aldehyde.
- the compound (1) in this invention is a compound which does not produce
- compound (2) represented by following General formula (2) by reaction with an aldehyde normally.
- the fact that compound (2) is not substantially produced by reaction with aldehyde means that compound (1) does not produce compound (2) by reaction with aldehyde, or even if compound (2) is produced. It means that the amount produced is an amount that does not substantially cause browning.
- the composition for browning suppression of this invention does not contain a compound (2) normally.
- R ⁇ 11 >, R ⁇ 12 >, R ⁇ 13> , R ⁇ 14> , R ⁇ 15> , R ⁇ 16> , R ⁇ 17> , R ⁇ 18> and R ⁇ 19 > each independently represents a hydrogen atom or a substituent
- R ⁇ 11 > and R ⁇ 12> , R 12 and R 13 , or R 13 and R 14 may be bonded to each other to form a ring structure together with the carbon atom to which they are bonded
- R 18 and R 19 may be bonded together to form a ring structure together with the carbon atom to which they are bonded.
- the compound (2) has a yellowish brown to reddish brown color due to the xanthylium structure represented by the general formula (2).
- the xanthylium structure in compound (2) has an absorption maximum around 440 nm near weak acidity (around pH 5), and has an absorption maximum around 486-487 nm at pH 6.0-8.9 (NE Es-Safi et al. Food Chem 88 (2004) 367-372). For this reason, browning advances when a compound (2) produces
- Compound (2) is usually produced by the reaction of polyphenols such as catechins and aldehydes.
- the following reaction scheme is an example of a reaction in which an example compound (2) is produced in a green tea beverage.
- an example of the reaction between epicatechin (EC) and aldehyde (R-CHO) is shown as an example of catechins contained in a green tea beverage.
- Compound 1 As shown above, first, one molecule of aldehyde and one molecule of epicatechin react to form Compound 1. This reaction is a reaction between the aldehyde and the benzene ring (A ring) of epicatechin. The aldehyde-derived portion of Compound 1 further reacts with another molecule of epicatechin (EC) to produce Compound 2 in which two catechin molecules are bonded via an aldehyde-derived structure (-CR-). This compound 2 is colorless. In Compound 2, a catechin-derived hydroxyl group undergoes a dehydration reaction and cyclizes to produce Compound 3 (colorless), and from Compound 3, Compound 4 having a xanthylium structure is produced. Compound 4 is compound (2) in the present invention and exhibits a yellowish brown color in a green tea beverage.
- the compound (2) produced by the reaction of two molecules of polyphenol and one molecule of aldehyde will be further described.
- the carbon atom to which R 15 is bonded is an aldehyde-derived carbon atom that has reacted with polyphenol.
- the substituent represented by R 15 is a residue derived from an aldehyde.
- R 15 is a hydrogen atom
- R 15 is a methyl group
- the aldehyde is glyoxal
- it is an aldehyde group (—CHO).
- the carbon atom to which R 15 is bonded and the portion other than R 15 are derived from the polyphenol reacted with the aldehyde.
- R 11 and R 19 are hydrogen atoms
- R 12 and R 18 are hydroxyl groups.
- the compound produced by the reaction of one molecule of compound (1) and one molecule of aldehyde (R—CHO) has a structure in which the hydrogen atom of benzene ring A is substituted with an aldehyde.
- the aldehyde-derived carbon atom in this compound may further react with the benzene ring A of another molecule of compound (1).
- a dimer of compound (1) in which two molecules of compound (1) are bonded via an aldehyde-derived structure (—CR—) is produced.
- the position adjacent to the bonding position with the aldehyde (the carbon atom to which R 21 or R 23 is bonded in the general formula (1)) (ortho In the dimer, the hydroxyl group may be condensed to produce the compound (2) when all of the positions are hydroxyl groups.
- the compound (1) reacts with the aldehyde. Does not substantially produce compound (2).
- the aldehyde can be captured and browning can be suppressed by the compound (1).
- the compound (1) captures the aldehyde, thereby reducing the reaction between the polyphenol and the aldehyde and suppressing the production of the compound (2).
- the compound (1) in the present invention is useful as an active ingredient of a composition for inhibiting browning.
- the compound (1) in the present invention may have one heterocyclic (C6-C3) structure including a benzene ring A represented by the general formula (1) in one molecule, and two or more It may be. Preferably, it has one said heterocyclic structure.
- Compound (1) does not have a benzene ring structure in which any of the carbon atoms constituting the benzene ring adjacent to the carbon atom bonded to the hydrogen atom (ortho position) is a hydroxyl group. Is preferred.
- the compound (1) is a compound that does not substantially produce the compound (2) by the reaction with the aldehyde, the aldehyde is captured and the production of the compound (2) is suppressed, Browning can be suppressed.
- the compound (1) in the present invention is preferably colorless at pH 2-13. When it is such a compound, the more excellent browning inhibitory effect can be exhibited.
- the substituents in the general formula (1) and the general formula (2) are not particularly limited.
- a hydroxyl group, an organic group having 1 to 50 carbon atoms, an amino group (—NH 2 ), a thiol group (—SH), nitro A group (—NO 2 ) or a halogen atom is preferred.
- the substituent is more preferably a hydroxyl group or an organic group having 1 to 50 carbon atoms.
- the organic group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 15 carbon atoms.
- the organic group is a group containing a carbon atom, and may contain an atom other than a carbon atom, for example, a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a halogen atom, or a phosphorus atom.
- an organic group in this invention the organic group which consists of a carbon atom, a hydrogen atom, and an oxygen atom, or the organic group which consists of a carbon atom and a hydrogen atom is more preferable.
- Examples of the organic group having 1 to 50 carbon atoms include alkyl group, alkenyl group, alkynyl group, alkoxy group, alkenyloxy group, alkylcarbonyl group, alkenylcarbonyl group, alkylthio group, alkylamino group, aryl group, arylalkyl group, aryl Examples include an oxy group, an arylcarbonyl group, an arylthio group, an arylamino group, an arylalkylthio group, a heterocyclic group, a heterocyclic oxy group, a cyano group, and a carboxyl group. These groups are substituted with one or more substituents. May be.
- the number of carbon atoms including the substituent is preferably in the above range. “Substituted by a substituent” means that a hydrogen atom in the organic group is substituted by a substituent.
- the organic group may have any of a linear structure, a branched structure, and a cyclic structure.
- the present invention includes any of the geometric isomers.
- the present invention relates to a compound in which each asymmetric carbon atom is in an R configuration, a compound in an S configuration, and a compound in any combination thereof. Include. Any of those racemates, racemic mixtures, single enantiomers, and diastereomeric mixtures are also included in the present invention.
- the compound (1) will be described in more detail.
- the reactivity between the benzene ring A and the aldehyde tends to increase as the number of oxygen atoms bonded to the benzene ring A increases.
- At least two oxygen atoms are bonded to the benzene ring A through OR 22 and OR 24 .
- the number of oxygen atoms bonded to the benzene ring A is preferably 3 or 4.
- Examples of such a compound include a compound in which X is an oxygen atom and / or R 21 or R 23 is a substituent represented by OR a1 (R a1 represents a hydrogen atom or a substituent). preferable.
- R 21 when R 21 is a hydrogen atom, X is preferably an oxygen atom and / or R 23 is a substituent represented by OR a1 (R a1 is as defined above).
- R 23 when R 23 is a hydrogen atom, X is an oxygen atom, and / or R 21 is a substituent represented by OR a1 (R a1 is as defined above). It is preferable.
- substituent for R a1 include those described above.
- the compound (1) it is preferable that none of the positions (ortho positions) adjacent to the hydrogen atom bonded to the benzene ring (benzene ring A) is a hydroxyl group.
- the carbon atom bonded to the hydrogen atom reacts with the aldehyde. Since none of the ortho positions that react with the aldehyde is a hydroxyl group, even if two molecules of the compound (1) react with one molecule of the aldehyde, the formation of the compound (2) usually does not occur. Therefore, the compound (1) can exhibit an excellent browning inhibitory effect.
- R 21 is a hydrogen atom
- R 22 is preferably a substituent.
- R 22 and R 24 are preferably each independently a substituent.
- a sterically hindered substituent means that when a carbon atom constituting the benzene ring A reacts with an aldehyde, the sterically hindered group is bonded to a carbon atom at a position adjacent to the reaction position with the aldehyde (ortho position). It means a group that decreases the reactivity between the hydroxyl group and other hydroxyl groups.
- the body may generate.
- the compound (1) in which the dimer is formed Even if each of the two molecules of the benzene ring A has a hydroxyl group at one ortho position of the bonding position with the aldehyde, at least one steric group is present in the benzene ring A.
- the hindering substituent is bonded, the condensation of two hydroxyl groups derived from the compound (1) is inhibited in the dimer.
- the position adjacent to the hydrogen atom bonded to the benzene ring A is a hydroxyl group
- the position adjacent to the hydroxyl group is a sterically hindered substituent.
- the condensation of two hydroxyl groups derived from the compound (1) is more sufficiently inhibited.
- the production of the compound (2) usually does not occur and browning is suppressed.
- R 21 is a hydrogen atom and R 22 is a hydrogen atom
- R 23 and / or OR 24 is preferably a sterically hindered substituent
- R 23 is a sterically hindered substituent. Is more preferable.
- the sterically hindered substituent may be any group that reduces the reactivity of the hydroxyl group.
- it is an organic group having 6 to 30 carbon atoms having a ring structure or an organic group having a linear or branched structure having 10 to 30 carbon atoms, more preferably an organic group having 6 to 30 carbon atoms having a ring structure.
- the ring structure is preferably a 6-membered ring.
- the carbon number of the organic group having 6 to 30 carbon atoms having a ring structure is preferably 6 to 20, more preferably 6 to 15.
- Examples of the organic group having 6 to 30 carbon atoms having a ring structure include a gallate group and a sugar (sugar residue).
- the sugar may be a monosaccharide or a polysaccharide (preferably disaccharide to pentasaccharide, more preferably disaccharide).
- R 21 or R 23 is preferably a hydrogen atom. Such a compound is preferable because of its high browning inhibitory effect.
- R 21 is a hydrogen atom and R 23 is a substituent, or a compound in which R 23 is a hydrogen atom and R 21 is a substituent is a compound (1) in the present invention. As preferred.
- R 21 represents a hydrogen atom, and R 22 and R 23 each independently represent a substituent;
- R 23 represents a hydrogen atom, and R 22 and R 24 each independently represent a substituent;
- R 21 represents a hydrogen atom, R 22 represents a hydrogen atom, and R 23 represents a sterically hindered substituent;
- R 23 represents a hydrogen atom, R 21 represents a sterically hindered substituent, R 22 represents a hydrogen atom, R 24 represents a substituent; or
- R 23 represents a hydrogen atom, OR 22 represents a sterically hindered substituent, and R 24 represents a hydrogen atom.
- R 21 is more preferably a hydrogen atom.
- the formation of the compound (2) usually does not occur due to the sterically hindered substituent.
- Such a compound (1) can exhibit an excellent browning inhibiting effect.
- the sterically hindered substituent and preferred embodiments thereof are as described above.
- the compounds (iii), (iv) and (v) are more preferred.
- a hydroxyl group or an organic group having 1 to 10 carbon atoms preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms
- the ring is preferably a 6-membered ring, The ring may be substituted with a substituent.
- R 25 is preferably an oxygen atom or a substituent.
- R 26 and R 27 each independently represent a hydrogen atom or a substituent.
- R 25 and R 26 , or R 26 and R 27 may be bonded to each other to form a ring structure together with the carbon atom to which they are bonded.
- Preferable substituents for R 25 , R 26 and R 27 include organic groups having 1 to 15 carbon atoms. As the organic group, an aryl group and the above sugar residue are preferable. In one embodiment, any of R 25 , R 26 and R 27 is preferably an aryl group.
- R 25 is an oxygen atom or an aryl group
- R 25 is an oxygen atom
- R 26 or R 27 is an aryl group.
- the aryl group may be substituted with one or more substituents, and for example, an aryl group having 6 to 15 carbon atoms that may be substituted with one or more substituents is preferable.
- the compounds in which R 25 , R 26 and R 27 are the above are examples of preferred embodiments of the compound (1) in the present invention.
- Examples of the compound (1) in the present invention include compounds of the following formulas (A-1), (A-2), (A-3), (A-4) and (A-5), baicalin and baicalin coordination.
- Examples include saccharides (for example, compounds in which 1 to 3 glucoses are bonded to the sugar moiety of baicalin), chafuroside A, icariin, scutellarin, and the like. These compounds are preferable as the compound (1) in the present invention.
- Examples of the compound (1) in the present invention also include compounds of the following formulas (A-6), (A-7), (A-8), and (A-9). Each compound of the formulas (A-6) to (A-9) is also an example of the compound (1).
- the compound (1) in the present invention is preferably dissolved by 0.01% by mass or more with respect to water. More preferably 0.01 to 50% by mass, still more preferably 0.1 to 40% by mass, particularly preferably 0.5 to 30% by mass, and most preferably 1 to 20% by mass.
- the solubility in water at 20 ° C. is in such a range. When the solubility in water is within the above range, the effect of inhibiting browning can be sufficiently exhibited in various foods and drinks.
- the composition for inhibiting browning of the present invention may contain one type of compound (1) or two or more types.
- the manufacturing method of the compound (1) in this invention is not specifically limited, It can manufacture by a well-known organic synthesis method. Moreover, a commercial item can also be used. It can also be isolated from natural products by known methods.
- the compound (1) may be used as it is as a composition for inhibiting browning (also referred to as a browning inhibitor).
- the composition for browning suppression of this invention may contain other components other than a compound (1) depending on necessity.
- Known components can be used as other components.
- other components include additives.
- additives for food and drink for example, bulking agents, antioxidants, pH adjusters, colorants, fragrances, flavoring agents, surfactants (emulsifiers), solubilizers, preservatives, sugars, sweeteners, acidulants And vitamins.
- composition for browning suppression of this invention can be provided in the form of an agent as an example, but are not limited to this form.
- the agent can be provided as it is as a composition or as a composition containing the agent.
- the form of the composition for inhibiting browning of the present invention is not particularly limited.
- it may be in the form of powder, granules, paste, solid, etc., or it may be liquid.
- the content of the compound (1) in the composition for inhibiting browning of the present invention is not particularly limited, but in one embodiment, for example, 0.01 to 99.9% by mass is preferable, and 1 to 50% by mass is more preferable.
- browning of the composition containing polyphenol can be suppressed.
- the composition for inhibiting browning of the present invention is suitably used for inhibiting browning of a composition containing polyphenol.
- the browning suppression method of the composition containing polyphenol which mixes a compound (1) and the composition containing polyphenol is also included by this invention.
- the composition containing polyphenol is preferably a food or drink containing polyphenol.
- the compound (1) foods and drinks and the like in which browning is suppressed can be produced.
- the manufacturing method of the food / beverage products which mix a compound (1) and the food / beverage products containing polyphenol are also included by this invention.
- a composition containing polyphenol for example, a food or drink
- an aldehyde is usually contained in a component such as a raw material or the component is decomposed over time to produce an aldehyde.
- Compound (1) can suppress browning by capturing this aldehyde.
- One type of compound (1) may be used, or two or more types may be used.
- the composition for inhibiting browning of the present invention described above is suitably used for a browning inhibiting method, a method for producing a food or drink, a food or drink described below, and the like.
- the food and drink includes food and drink raw materials.
- the polyphenol in the present invention is a polyphenol derived from a plant or a processed product thereof.
- the polyphenol means a phenol having two or more hydroxyl groups in the same benzene ring, and its glycoside is also included as a polyphenol.
- the compound (1) in this invention is not normally contained in the polyphenol in this invention.
- the polyphenol in this invention is a compound which produces
- Examples of such a polyphenol include a polyphenol having a benzene ring structure in which all the positions (ortho positions) adjacent to the carbon atom bonded to the hydrogen atom among the carbon atoms constituting the benzene ring are hydroxyl groups.
- polyphenols examples include flavonoids such as flavan-3-ols, flavones, isoflavones, flavonols, flavanones, flavonols, flavan-3,4-diols, and related compounds. Can do.
- flavonoid-related compounds include flavonoid glycosides.
- polyphenols contained in tea beverages include flavan-3-ols and related compounds such as epicatechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, gallocatechin, gallocatechin gallate, catechin, catechin gallate.
- Catechins such as theaflavins, theaflavin gallate A, theaflavin gallate B, theaflavins such as theaflavin digallate.
- catechins are preferable.
- Compound (1) is particularly preferably used for suppressing browning of a composition containing catechins.
- Foods and beverages containing polyphenols are not particularly limited, and green tea beverages, buckwheat tea beverages, barley tea beverages, tea beverages, Pu'er tea beverages, oolong tea beverages, hoji tea beverages, etc .; fruit juices such as grapes, apples, tangerines, peaches, Examples include soft drinks containing fruit juices; beverages such as the above-mentioned alcoholic drinks containing fruit juices or tea drinks; and soy products such as miso and soy milk drinks. Examples of alcoholic beverages containing fruit juices or tea beverages include alcoholic beverages such as beer, chuhai, liqueur, and cocktail blended with the above fruit juices or tea beverages.
- a compound (1) is used suitably in order to suppress the browning of the drink containing a polyphenol, is suitable for a tea drink, and is further suitable for a green tea drink.
- Tea drinks are teas (tea tree, Camellia sinensis) made mainly from leaves and stems, teas such as oolong tea, pu-erh tea and green tea, or brown tea, wheat and other various plants.
- a blend of raw materials can be obtained by extraction with hot water, hot water, cold water, ethanol, hydrous ethanol, or the like.
- browning of the extract occurs in any of the above tea beverages, the present invention is particularly useful for green tea beverages in which the change in liquid color due to browning is easily noticeable.
- the composition for inhibiting browning and the browning inhibiting method of the present invention are particularly preferably used for inhibiting browning of a green tea beverage.
- the manufacturing method of the food / beverage products of this invention is especially suitable for manufacture of a green tea drink.
- the green tea beverage in the present invention may be a tea beverage that contains a liquid obtained by extracting green tea.
- the timing which mixes a compound (1) is not specifically limited, You may mix a compound (1) in the manufacture stage of food / beverage products, The product can also be mixed with compound (1) after production.
- the method for mixing the compound (1) and the food or drink is not particularly limited.
- an example of a method for producing a tea beverage will be described as follows. After extracting the raw materials (tea leaves, etc.) with warm water or hot water, the tea husks and fine particles are removed by filtration or the like. Next, the extract is diluted to an appropriate concentration, and ascorbic acid or sodium ascorbate is added to the diluted solution.
- a pH adjuster such as sodium bicarbonate (sodium bicarbonate)
- sodium bicarbonate sodium bicarbonate
- This diluted tea extract solution to which ascorbic acid or sodium ascorbate is added is referred to as a preparation solution.
- the preparation liquid is preferably sterilized by heating, and is preferably sterilized by an ultra-high temperature heat treatment method (UHT method).
- UHT method ultra-high temperature heat treatment method
- the air in the head space can be replaced with nitrogen gas.
- compound (1) when compound (1) is mixed in the production of tea beverage, it is preferable to mix compound (1) before heat sterilization, and compound (1) is mixed with hot water or hot water for extraction. It may be mixed with the extract or mixed with the preparation, but preferably mixed with the preparation.
- a step of extracting a raw material containing tea leaves of green tea with warm water or hot water preferably 65 to 90 ° C.
- a step of filtering the extract a filtered extract Diluting with water, ascorbic acid or sodium ascorbate (preferably 0.1 to 1 g / L, more preferably 0.3 to 0.5 g / L), sodium bicarbonate (preferably 0.1 to 1 g / L, more preferably 0.3 to 0.4 g / L) and a compound (1) are mixed to obtain a preparation liquid, and the preparation liquid is heat sterilized (preferably 100 to 135 ° C., 10 to 10 ° C. 120 seconds), a method for producing a green tea beverage.
- a container-packed green tea drink can be manufactured by performing the process which fills containers, such as a PET bottle, with the heat-sterilized green tea drink.
- the compound (1) is also preferably used for a tea extract obtained by concentrating a tea extract.
- the tea extract before concentration and the compound (1) may be mixed, or may be mixed after concentration.
- this tea extract can be dried and powdered to produce a powder (powdered tea). If compound (1) is mix
- Tea extract or powder can be used as a beverage by diluting with water or the like.
- a tea extract and powder can also be used for food-drinks other than a tea drink. Even when a tea extract or powder is used in a food or drink, the browning inhibiting effect is maintained.
- the amount of compound (1) used is not particularly limited, and an effective amount may be used as appropriate.
- the compounding amount of the compound (1) is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass with respect to the composition containing polyphenol. A favorable browning inhibitory effect can be acquired as it is such a range.
- the composition containing polyphenol is a tea beverage, it is preferable to use 0.001 to 10% by mass, more preferably 0.01 to 1% by mass of the compound (1) based on the tea beverage. preferable.
- a beverage suitable for a transparent container such as a plastic bottle can be provided.
- air in the beverage head space may be replaced with nitrogen gas, or another browning inhibitor may be used in combination.
- a food or drink comprising the compound (1) is also one aspect of the present invention.
- the food / beverage products are not particularly limited, and examples thereof include the above-mentioned food / beverage products containing polyphenols, preferably beverages, more preferably tea beverages, and still more preferably green tea beverages.
- the beverages in the present invention are diluted with powdered soft drinks that are drinkable by dissolving them in water or the like at the appropriate concentration at the time of drinking in the form of powder at the time of beverage sales, or diluted with water, etc. Then, it may be a concentrated beverage that can be drunk.
- the compounding amount of the compound (1) is not particularly limited, but for example, the compounding amount of the compound (1) in the food or drink is preferably 0.001 to 10% by mass, and more preferably 0.01 to 1% by mass.
- the food / beverage product of the present invention is preferably a packaged beverage.
- containers used for container-packed beverages include molded containers mainly composed of polyethylene terephthalate (so-called PET bottles), metal cans, paper containers combined with metal foils and plastic films, and bottles.
- PET bottles polyethylene terephthalate
- the present invention is particularly useful for container-packed beverages using transparent containers such as PET bottles and glass bottles.
- the green tea beverage according to the present invention uses the rate of change of the area of the absorbance spectrum when measured using light having a wavelength between 400 and 600 nm or light having a wavelength of 487 nm when stored at room temperature for 9 months.
- the change rate of the absorbance is preferably less than 150%.
- the green tea beverage having the area change rate or absorbance change rate of less than 150% is preferable as a green tea beverage in which browning is suppressed.
- the normal temperature is usually 1 to 30 ° C., preferably 15 to 25 ° C.
- the absorbance is measured using the area change rate or light having a wavelength of 487 nm
- the above-mentioned change rate in absorbance is less than 150%
- Such a green tea beverage is also included in the present invention.
- the area change rate of the absorbance spectrum is the absorbance spectrum area of 400-600 nm of the green tea beverage before storage (S0) and the absorbance spectrum area of 400-600 nm after storing the green tea beverage at room temperature for 9 months (S1). ) And the following formula.
- Absorption spectrum area change rate (%) 100 ⁇ (S1 ⁇ S0) / S0
- the area change rate of the absorbance spectrum is preferably less than 50%.
- the rate of change in absorbance at a wavelength of 487 nm is obtained from the following formula from the absorbance at 487 nm (A0) of the green tea beverage before storage and the absorbance (A1) at 487 nm after storage of the green tea beverage at room temperature for 9 months. .
- Change rate of absorbance at wavelength of 487 nm (%) 100 ⁇ (A1 ⁇ A0) / A0
- the rate of change in absorbance at the wavelength of 487 nm is preferably less than 50%.
- the suppression of browning by the compound (1) is due to the capture of the aldehyde by the compound (1) as described above. Therefore, the compound (1) is useful as an active ingredient of the aldehyde scavenging composition.
- the composition for inhibiting browning of the present invention can also be used as a composition for capturing aldehydes.
- the aldehyde capturing composition of the present invention contains the compound (1).
- the aldehyde scavenging composition of the present invention contains compound (1) as an active ingredient.
- the composition for trapping aldehyde may contain one type of compound (1) or two or more types.
- a compound (1) and its preferable aspect are the same as the thing in the composition for browning suppression mentioned above.
- a compound (1) is a compound which does not produce
- the compound (1) may be used as it is as an aldehyde scavenging composition (also referred to as an aldehyde scavenger).
- an aldehyde scavenging composition also referred to as an aldehyde scavenger.
- blend components other components
- acquisition can be appropriately selected according to the usage form of the aldehyde-trapping composition, and examples thereof include additives.
- the content of the compound (1) in the composition for capturing aldehyde is, for example, preferably 0.01 to 99.9% by mass, and more preferably 1 to 50% by mass.
- the aldehyde-capturing composition is suitably used for capturing aldehydes, for example, in air or in solution.
- the aldehyde in the gas or liquid can be captured by bringing the composition for capturing aldehyde into contact with the gas or liquid containing the aldehyde.
- the aldehyde-trapping composition can be suitably used, for example, for deodorizing aldehyde-derived odors. It can also be used to capture aldehydes in the living body or to capture aldehydes that are the cause of sick house.
- the method for suppressing polyphenol reduction in a composition containing polyphenol of the present invention is characterized by mixing a composition containing polyphenol and compound (1).
- Compound (1) and preferred embodiments thereof are as described above.
- One type of compound (1) may be used, or two or more types may be used.
- the amount of the compound (1) used is not particularly limited and may be appropriately selected depending on the composition containing polyphenol. For example, 0.001 to 10% by mass is preferable with respect to the composition containing polyphenol. More preferably, the content is 0.01 to 1% by mass.
- the compound (1) is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass with respect to the tea beverage.
- the composition containing polyphenol is preferably a food or drink containing polyphenol. Further, the composition is preferably a composition containing catechins, more preferably a tea beverage, and further preferably a green tea beverage.
- the polyphenol reduction suppressing method of the present invention is useful as a method for suppressing catechin reduction in green tea beverages. For example, green tea beverages exhibit a refreshing bitterness immediately after production, but this refreshing bitterness may decrease when stored for long periods of time. One possible cause of this change in flavor is that catechins reacted with aldehydes during storage and decreased. ADVANTAGE OF THE INVENTION According to this invention, even if it stores for a long period of time, the reduction
- the method for suppressing the production of the compound represented by the general formula (2) in the composition containing the polyphenol of the present invention is characterized by mixing the composition containing the polyphenol and the compound (1).
- the compound (1) by using the compound (1), the production of the compound (2) in the composition containing polyphenol can be suppressed.
- Compound (1) and preferred embodiments thereof are as described above.
- One type of compound (1) may be used, or two or more types may be used.
- the amount of the compound (1) used is not particularly limited and may be appropriately selected depending on the composition containing polyphenol. For example, 0.001 to 10% by mass is preferable with respect to the composition containing polyphenol. More preferably, the content is 0.01 to 1% by mass.
- the compound (1) when the composition containing polyphenol is a tea beverage, the compound (1) is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass with respect to the tea beverage.
- the deodorizing composition of the present invention is characterized by containing the above-described aldehyde capturing composition of the present invention.
- the deodorizing composition of the present invention can effectively reduce the aldehyde-derived odor by capturing the aldehyde with the compound (1).
- the deodorizing composition of this invention is used suitably as a deodorizing composition of the odor derived from an aldehyde.
- Compound (1) is suitably used as an active ingredient of the deodorant composition.
- Compound (1) and preferred embodiments thereof are as described above.
- a compound (1) is a compound which does not produce
- the deodorant composition may contain 1 type of compound (1), and may contain 2 or more types.
- the deodorant composition of the present invention includes, for example, body odor (smell odor, foot odor, sweat odor, scalp odor, etc.), kitchen odor, refrigerator odor, fish and vegetable food odor, tobacco odor, clothing odor. It is effective against various odors such as shoe odor. Therefore, the deodorant composition of the present invention can be used as, for example, a deodorant composition for bad breath, body odor, kitchen, indoor use, daily life, in-vehicle use, industrial use, and the like.
- the compound (1) is a compound that does not substantially generate the compound (2) by the reaction with the aldehyde, no browning occurs even if the compound (1) captures the odorous component aldehyde. For this reason, even if it repeatedly uses the composition for deodorizing of this invention for cloth products, such as clothes and furniture, there exists an effect that a cloth product does not easily brown. For this reason, the composition for deodorizing of this invention is used suitably as a composition for deodorizing cloth, etc., for example.
- the aldehyde-trapping composition may be used as it is as a deodorizing composition.
- the compound (1) can be used as it is as a deodorant composition (also referred to as a deodorant).
- the content of the compound (1) in the deodorant composition is not particularly limited, and in one embodiment, for example, 0.01 to 99.9% by mass is preferable, and 1 to 50% by mass is more preferable.
- components other than the compound (1) for example, antioxidants, ultraviolet absorbers, antistatic agents, flame retardants, fungicides, fungicides, insect repellents, pigments, Common additives such as coloring agents and flavoring agents can be blended.
- the composition for deodorizing may be a spray, a gel form, a liquid form, or a solid form.
- known methods can be applied.
- a malodorous component particularly an aldehyde
- a malodorous component will be generated in a solid, gel or liquid of the deodorant composition of the present invention.
- the deodorant composition of the present invention may be applied by spraying.
- This invention also includes the screening method of the compound which has the browning inhibitory effect of the composition containing a polyphenol.
- the screening method of the present invention comprises a step of preparing a sample solution containing polyphenol, aldehyde and a candidate compound, and A step of determining the browning-inhibiting effect of the candidate compound with the production of the compound represented by the general formula (2) in the sample solution as an index.
- the compound represented by the general formula (2) (compound (2)) is as described above.
- the method for preparing the sample solution is not particularly limited.
- a method of preparing a solution containing polyphenol and a candidate compound and mixing the solution with an aldehyde is preferable.
- the polyphenol may be a compound that generates the compound (2) by reaction with an aldehyde, and may be appropriately selected according to the purpose.
- polyphenols such as catechins contained in the green tea beverage described above may be used.
- One type of polyphenol may be used, or two or more types may be used.
- An aldehyde is not specifically limited, What is necessary is just to select suitably according to the objective.
- Glyoxal when screening for a compound having a browning-inhibiting effect in a green tea beverage, for example, at least one selected from the group consisting of glyoxal, methyl-glyoxal, diacetyl, L-threonine and 3-deoxy-L-threonine is Glyoxal is preferable. Since these aldehydes are decomposed products of L-ascorbic acid that are usually added to green tea beverages, they are suitable for screening candidate compounds effective for suppressing browning in green tea beverages.
- the reaction is accelerated by placing the sample solution at a high temperature (for example, using an autoclave or the like at 50 to 120 ° C., preferably 60 to 110 ° C., more preferably 70 to 100 ° C.) by an acceleration test or the like. You can also.
- a high temperature for example, using an autoclave or the like at 50 to 120 ° C., preferably 60 to 110 ° C., more preferably 70 to 100 ° C.
- the method for detecting the production of compound (2) is not particularly limited, and can be carried out by liquid chromatography-mass spectrometry (LC-MS) of the sample solution, absorbance measurement, or the like. Since the operation is simple, it is preferable to perform the absorbance measurement. Since the compound (2) usually has an absorption maximum at 400 to 600 nm, the production of the compound (2) can be detected by measuring the absorbance at the above wavelength. For example, the production of the compound (2) can be detected by changing the spectral area value of 400 to 600 nm. Further, as described above, the compound (2) has a property that the maximum shifts depending on the pH.
- LC-MS liquid chromatography-mass spectrometry
- the compound (2) has an absorption maximum around 440 nm in the vicinity of weak acidity (around pH 5), and 486 to 487 nm in the pH 6.0 to 8.9. It has an absorption maximum in the vicinity (NE Es-Safi et al., Food Chem 88 (2004) 367-372). For this reason, it is preferable to set the wavelength used for the detection of the compound (2) as appropriate according to the pH of the solution.
- the detection of the compound (2) is preferably carried out at the maximum wavelength in the solution.
- a green tea beverage usually has a pH of 6-8. When screening for a compound having a browning-inhibiting effect in green tea beverages, it is preferable to measure the absorbance at 487 nm and detect the production of compound (2) by the change in absorbance at 487 nm.
- the production of the compound (2) is preferably detected by measuring the absorbance spectrum of the sample solution using light having a wavelength of 400 to 600 nm and changing the area of the absorbance spectrum. Moreover, it is also preferable to detect the production
- the amount of compound (2) produced in the sample solution and a control solution containing polyphenol and aldehyde and not containing a candidate compound it is preferable to compare the amount of compound (2) produced in the sample solution and a control solution containing polyphenol and aldehyde and not containing a candidate compound.
- the amount of compound (2) produced can be compared, for example, by comparing the amount of change in absorbance between the sample solution and the control solution using light having a wavelength between 400 and 600 nm.
- the amount of compound (2) produced is small (production is suppressed) compared to the case where the compound is not included (control solution), the sample solution is compared with the control solution.
- the amount of compound (2) produced is small), it is preferable to determine that the candidate compound has a browning suppressing effect.
- the amount of change in the absorbance spectrum area at 400 to 600 nm is small compared to the case where it is not included (in the sample solution, the amount of change in the absorbance spectrum area at 400 to 600 nm is smaller than that of the control solution). It is possible to determine that the used candidate compound has an effect of suppressing browning. For example, when screening for a compound having a browning-inhibiting effect in a green tea beverage, the amount of change in absorbance at 487 nm is small by including a candidate compound as compared with the case where the compound is not included (in the sample solution).
- the used candidate compound has a browning inhibitory effect and select it as a browning inhibitor.
- the substance determined to have a browning inhibitory effect by the screening method of the present invention can be used for the above-mentioned browning inhibition, for aldehyde capture, for deodorization, etc., for example, a composition for inhibiting browning, It is suitably used as an active ingredient of an aldehyde capturing composition and a deodorizing composition.
- the present invention includes the following uses of the compound (1).
- Use of the compound represented by the general formula (1) for inhibiting browning Use of the compound represented by the general formula (1) for producing a composition for inhibiting browning.
- Use of the compound represented by the general formula (1) for capturing an aldehyde Use of the compound represented by the general formula (1) for producing a composition for capturing aldehyde.
- Use of the compound represented by the general formula (1) for deodorization Use of the compound represented by the general formula (1) for producing a deodorant composition.
- Compound (1) and preferred embodiments thereof are as described above.
- the browning inhibition is preferably browning inhibition of the composition containing the polyphenol described above.
- Compound (1) is suitably used for deodorizing aldehyde-derived odors.
- UV-1700 manufactured by Shimadzu Corporation
- UV-1700 was used for the measurement of the visible absorption spectrum (400 to 700 nm).
- the visible absorption spectrum is also simply referred to as an absorption spectrum.
- LC-MS analysis a liquid chromatograph mass spectrometer LC-MS2020 (manufactured by Shimadzu Corporation) was used.
- ⁇ Test Example 1> A green tea beverage containing a 2 L plastic bottle was produced, stored at room temperature in an unopened state, and the change in color over time was confirmed by visual observation and measurement of a visible absorption spectrum.
- a 2L plastic bottled green tea beverage was produced by the following method. Green tea leaves were extracted with 30 times the amount of ion-exchanged water (70 ° C.) for 5 minutes. Stirring was performed at the timing of extraction 0 min, 1 min, 2 min, 3 min, and 4 min (5 times per cycle for 15 seconds). At the timing of 5 minutes of extraction time, the tea leaf extract was filtered through a 20 mesh filter to remove the tea leaf, and an “extract” was obtained. The extract was diluted with ion-exchanged water to the amount of ion-exchanged water used for extraction, and cooled to about 30 ° C. with running water.
- the cooled extract was centrifuged at 6000 rpm for 10 minutes, and the supernatant was collected to obtain a diluted solution of the extract.
- the diluted solution of the extract was passed through a Cunofilter (manufactured by 3M), ascorbic acid was added to the recovered solution, and sodium bicarbonate was added as a pH adjuster to adjust to pH 6.4. Furthermore, it diluted with ion-exchange water so that it might become a Brix value 0.21, and it was set as the "preparation liquid.” Ascorbic acid was added so that the concentration of ascorbic acid in the preparation solution was 0.4 g / L.
- the prepared solution was sterilized at 132.5 ° C. for 60 seconds using an ultra-high temperature heat treatment sterilizer (UHT sterilizer), and filled into a 2 L transparent PET bottle.
- UHT sterilizer ultra-high temperature heat treatment sterilizer
- FIG. 1 is a photograph of green tea beverages in PET bottles stored at room temperature for 6, 22, 5, 7, and 9 months.
- FIG. 2 is a view showing a visible absorption spectrum of each green tea beverage shown in FIG. From these results, it was decided to use the absorption intensity of 487 nm as an index of browning of the green tea beverage.
- the diluted solution of the extract was passed through a Cunofilter (manufactured by 3M), ascorbic acid was added to the recovered solution, and sodium bicarbonate was added as a pH adjuster to adjust to pH 6.4. Furthermore, it diluted with ion-exchange water so that it might become a Brix value 0.21, and it was set as the "preparation liquid.” Ascorbic acid was added so that the concentration of ascorbic acid in the preparation solution was 0, 0.04, 0.4, or 1.2 g / L.
- Condition 1 Nitrogen replacement, 1 hour at 4 ° C.
- Condition 2 121 ° C., 14 minutes
- Condition 3 After oxygen aeration, conditions 2 and 3 at 123 ° C. for 30 minutes are accelerated deterioration tests using an autoclave.
- Condition 2 is a condition that assumes sterilization when manufacturing a green tea beverage. In condition 2, oxygen and nitrogen substitution was not performed.
- Condition 3 is a condition that assumes a state in which the browning reaction proceeds to the maximum due to excessive oxygen.
- FIG. 3 is a diagram showing visible absorption spectra before and after a deterioration test under Condition 2 of a preparation solution containing 0.4 g / L of ascorbic acid.
- the solid line is the spectrum before the test under Condition 2
- the broken line is the spectrum after the test.
- FIG. 4 is a view showing a visible absorption spectrum of each preparation solution after the deterioration test ((a): condition 1 (nitrogen substitution, 4 ° C. for 1 hour), (b): condition 2 (121 ° C., 14 minutes) ), (C): Condition 3 (after oxygen aeration, 30 minutes at 123 ° C.)).
- the solid line indicates a preparation liquid with an ascorbic acid addition amount of 0 g / L; the broken line indicates a preparation liquid with an ascorbic acid addition amount of 0.04 g / L; the dotted line indicates ascorbine.
- Formulation solution with an acid addition amount of 0.4 g / L; the one-dot chain line is a visible absorption spectrum of a formulation solution with an addition amount of ascorbic acid of 1.2 g / L.
- FIG. 5 is a diagram showing the concentrations of epicatechin (EC), epigallocatechin (EGC), epicatechin gallate (ECg), and epigallocatechin gallate (EGCg) in green tea and a model liquid (mixed four catechins). These concentrations were measured by LC-MS.
- FIG. 6 is a figure which shows the visible absorption spectrum of the green tea and model liquid (4 types of catechin mixing) before an accelerated deterioration test
- (b) is the change of the absorption before and after the accelerated deterioration of green tea and a model liquid. It is a figure which shows quantity ((DELTA) ABU).
- a solid line is green tea
- a broken line is a model liquid (4 types of catechins are mixed).
- the solution which mixed the additive ascorbic acid (0.4g / L) and baking soda (0.37g / L) used for a green tea drink was prepared.
- the solution was subjected to an accelerated deterioration test under Condition 3 of Test Example 2 (after oxygen aeration, at 123 ° C. for 30 minutes), and the resulting aldehydes were analyzed by LC-MS.
- Aldehydes were derivatized with o- (4-cyano-2-ethoxybenzyl) hydroxylamine (CNET) sulfate and detected by LC-MS.
- Derivatization with CNET sulfate was carried out by adding 0.5 mL of 1% CNET sulfate aqueous solution (Hayashi Junyaku Kogyo Co., Ltd., product name CNET glyoxal standard solution) to 5 mL of sample and reacting at room temperature for 2 hours. .
- the solution after the reaction was filtered through a filter (0.2 ⁇ ) and subjected to LC-MS under the following conditions.
- the LC-MS measurement results are shown in FIG.
- FIG. 7 shows a chromatogram (SCAN data) obtained by analyzing a decomposition product of CNET-derivatized ascorbic acid in a scan mode by LC-MS and a chromatogram (SIM data) obtained by analyzing in a SIM (selective ion monitoring) mode. It is a figure ((a): SCAN data, (b): SIM data). It was qualitatively confirmed that the detected peak was CNET derivatized glyoxal. From this result, it was found that glyoxal, an aldehyde, was produced from ascorbic acid in green tea.
- FIGS. 8A to 8D show epicatechin, a compound in which one molecule of epicatechin and one molecule of glyoxal are detected, and two molecules of epicatechin and one molecule of glyoxal that are detected in the accelerated green tea model.
- FIG. 3 is a diagram showing a chromatogram obtained by analyzing a compound having a xanthylium structure in the SIM mode by LC-MS ((a): epicatechin chromatogram, (b): compound in which one epicatechin molecule and one glyoxal molecule are bound to each other.
- Example 1 It was found that the browning phenomenon of green tea was caused by the reaction between catechins and aldehydes. It was clarified from another experiment that this reaction with aldehyde also occurs in compounds having a flavonoid skeleton other than catechins. Utilizing the properties of the compound having a flavonoid skeleton, a flavonoid compound that reacts with an aldehyde even in competition with catechin in green tea and the product does not exhibit color was searched for.
- the compound of xanthylium structure (brown color) detected in Test Example 5 is a catechin-derived hydroxyl group (carbon atom reacted with aldehyde) in the carboxymethine cross-linked dimer of catechin produced by the reaction of 1 molecule of aldehyde and 2 molecules of catechin. (Hydroxyl group bonded to a carbon atom adjacent to) was formed by dehydration and ring closure.
- a compound having a browning inhibitory effect in the case of a compound having a flavone skeleton, a compound in which a hydroxyl group bonded to the carbon atom at the ortho position of the carbon atom of the A ring that reacts with an aldehyde is protected was considered effective.
- a compound having the following general formula (I) was considered as an example of a candidate compound.
- the broken line represents that it may be a double bond.
- at least the 8-position of the A ring is a position where it reacts with the aldehyde.
- R A1 is a substituent.
- the 7-position hydroxyl group adjacent to the 8-position which reacts with the aldehyde is protected (OR A1 ).
- R A2 is a hydrogen atom or a substituent.
- R A3 is a substituent.
- R A4 is a hydrogen atom, an oxygen atom or a substituent.
- R A5 and R A6 are each independently a hydrogen atom, a substituent, or the like.
- baicalin (Wako Pure Chemical Industries, Ltd.) as a flavonoid having the above structure.
- the structural formula of baicalin is shown below.
- Baicalin (0.5 g / L) was added to a model solution in which epicatechin (0.5 g / L) and glyoxal (0.01 g / L) were mixed. Accelerated deterioration was performed under Condition 3 of Test Example 2 (after oxygen aeration, at 123 ° C. for 30 minutes), and a change ⁇ ABU in the visible absorption spectrum before and after the accelerated deterioration was calculated.
- FIG. 9 is a diagram showing changes in the visible absorption spectrum of the model solution due to the addition of baicalin. From FIG. 9, compared with the case where baicalin is not added (solid line), the amount of change ⁇ ABU in the visible absorption spectrum before and after accelerated deterioration was significantly reduced by the addition of baicalin (broken line).
- Example 2 The following three types of solutions were prepared.
- B + G Mixed solution of baicalin (0.5 g / L) and glyoxal (0.01 g / L)
- B + C + G baicalin (0.5 g / L), epicatechin (0.5 g / L) and glyoxal (0.01 g / L) )
- B + C + G baicalin (0.5 g / L), epicatechin (0.5 g / L) and glyoxal (0.01 g / L) )
- C + G epicatechin (0.5 g / L) and glyoxal (0.01 g / L) mixed solution
- the above solution was held at 121 ° C. for 15 minutes in an autoclave for accelerated deterioration. After accelerated deterioration, the color change was visually confirmed, and the visible absorption spectrum was further measured. The results are shown in FIG.
- FIG. 10 shows a photograph and a visible absorption spectrum after accelerated deterioration of a mixed solution of baicalin and glyoxal (B + G), a mixed solution of baicalin, epicatechin and glyoxal (B + C + G), and a mixed solution of epicatechin and glyoxal (C + G).
- FIG. 10B shows a photograph and a visible absorption spectrum after accelerated deterioration of a mixed solution of baicalin and glyoxal (B + G), a mixed solution of baicalin, epicatechin and glyoxal (B + C + G), and a mixed solution of epicatechin and glyoxal (C + G).
- FIG. 10B shows a photograph and a visible absorption spectrum after accelerated deterioration of a mixed solution of baicalin and glyoxal (B + G), a mixed solution of baicalin, epicatechin and glyoxal (B + C + G), and
- FIG. 11 shows the remaining amount of catechin (mM) in the mixed solution (B + C + G) and the mixed solution (C + G) after accelerated deterioration. From FIG. 11, it was found that the amount of residual catechin in the solution was increased by the addition of baicalin.
- Example 3 The mechanism was verified about the browning suppression effect by baicalin.
- the LC-MS measurement conditions are the same as in Test Example 5.
- FIG. 12 is a diagram showing a chromatogram obtained by analyzing a compound detected in an accelerated deterioration solution of a mixed solution of baicalin and glyoxal in the SIM mode by LC-MS ((a): one molecule of glyoxal and one molecule of baicalin). And (b): baicalin).
- the peak indicated by the arrow in FIG. 12A was baicalin (unreacted baicalin).
- the peak indicated by the arrow in (b) of FIG. 12 was a compound of the following structural formula (II) in which one molecule of baicalin and one molecule of glyoxal were bonded.
- the reaction and reaction product of glyoxal and baicalin are shown below.
- a baicalin glycoside was prepared by the following method. 2.5 g of sodium ascorbate was dissolved in 500 mL of distilled water. 20 mL of 1N NaOH was added to this, and it adjusted to pH 12, and prepared the sodium ascorbate aqueous solution. 500 mL of the above sodium ascorbate aqueous solution was added to 500 mg of baicalin (Wako Pure Chemical Industries, Ltd.) and 2500 mg of dextrin (derived from corn).
- DL voltage / Q-array voltage default value SIM: m / z 447 (Positive) baicalin m / z 609 (Positive) baicalin monoglucoside m / z 771 (Positive) baicalin diglucoside m / z 933 (Positive) baicalin triglucoside
- Mass (g) in Table 1 is “solid content” for each fraction.
- the amount of baicalin glycoside was determined by subtracting the “baicalin amount” from the “solid content” of the fraction in which baicalin or baicalin glycoside was qualitatively confirmed.
- the 80% ethanol fraction contains unreacted baicalin (m / z 447) and a glycoside of baicalin (compound with 1 to 3 glucose bound to the sugar moiety of baicalin: baicalin monoglucoside (m / z 609), baicalin di Glucoside (m / z 771), baicalin triglucoside (m / z 933)) were included.
- FIG. 13 is a chromatogram (SIM data) obtained by analyzing a fraction containing baicalin glycosides in SIM mode by LC-MS. Each peak in FIG. 13 is baicalin triglucoside (m / z 933), baicalin diglucoside (m / z 771), baicalin monoglucoside (m / z 609), baicalin (m / z 447) from the left.
- Example 4 Screening for aldehyde scavengers was performed.
- the model aldehyde was glyoxal, the reaction substrate was epicatechin, and the ability to suppress browning was evaluated by how much the candidate substance added to this could suppress browning. Distilled water was used for the negative control.
- fractions 6, 7 and 8 mixturetures containing baicalin and baicalin glycoside (a compound in which 1 to 3 glucoses were bound to the sugar moiety of baicalin) obtained in Preparation Example 1 were used.
- Glyoxal aqueous solution (39% (v / v)) and epicatechin were used as reagents.
- the sample solution was prepared by dissolving the candidate substance in water and adjusting the total phenol amount derived from the candidate substance to 600 ppm.
- the total phenol amount was measured by the foreign beis method using gallic acid as a standard substance.
- the usage-amount (total phenol amount) of a candidate substance was set by making the amount 5 times the density
- a 1 mg / mL aqueous solution of epicatechin was prepared and used as solution A.
- 100 ⁇ L of an aqueous glyoxal solution (39% v / v) was diluted to 300 mL with distilled water to obtain a solution B.
- a 96-well microplate was dispensed in the order of 60 ⁇ L of solution A, 10 ⁇ L of sample solution, 50 ⁇ L of distilled water, and 60 ⁇ L of solution B.
- a plate seal (BMPCR-TS (manufactured by BMBio)) was attached to the plate without any gap. After accelerated degradation at 70 ° C. for 16 hours, a spectral area value of 400 to 600 nm and an absorbance of 487 nm were measured.
- FIG. 14 is a diagram for explaining the Br value and the Xt value used for screening.
- the solid line indicates the absorbance when a substance having an aldehyde capturing action (substance having a browning inhibitory action) is added, and the broken line is the absorbance of the negative control. The larger the Br value and the Xt value compared to the negative control, the higher the aldehyde scavenging ability and the higher the browning inhibitory effect.
- FIG. 15 shows the evaluation results of the browning inhibitory action of the compounds (A-1) to (A-5). The results are shown as a ratio of the Br value and Xt value of the candidate compound when the Br value and Xt value of the negative control are 1.
- FIG. C. Is a negative control
- P.I. C. Is a positive control (baicalin and baicalin glycosides).
- the black bar represents the Br value and the white bar represents the Xt value.
- Example 5 As candidate substances, compounds of chafuroside A, icariin (manufactured by Ark Pharm, Inc.) and scutellarin (manufactured by Sigma-Aldrich) were used. Except this, the aldehyde scavenging ability and browning inhibitory action were evaluated in the same manner as in Example 4.
- Chafloside A is a compound of the following formula (B-1)
- icariin is a compound of the following formula (B-2)
- scutellarin is a compound of the following formula (B-3).
- the evaluation result of the browning inhibitory effect of scutellarin, chafuroside A and icariin is shown in FIG.
- the results are shown as a ratio of the Br value and Xt value of the candidate compound when the Br value and Xt value of the negative control are 1.
- the results in FIG. 16 are average values of three tests. In FIG. 16, black bars represent Br values and white bars represent Xt values.
- Suc is scutellarin
- ChaA is chafuroside A
- Ica is icariin.
- P.I. C. Is a positive control baicalin and baicalin glycosides).
- the present invention is useful in the field of food and drink.
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Abstract
Description
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。)
本明細書中、上記一般式(1)で表される化合物を、化合物(1)ともいう。
本明細書中、上記一般式(2)で表される化合物を、化合物(2)ともいう。
本発明の実施態様の別の一例においては、上記一般式(1)において、ベンゼン環に結合している水素原子に隣接する位置(オルト位)の一方が水酸基であり、かつ、ベンゼン環に少なくとも1つ立体障害性置換基が結合していることが好ましく、上記水酸基に隣接する位置(オルト位)が、立体障害性置換基であることがより好ましい。
本発明において、上記立体障害性置換基は、環構造を有する炭素数6~30の有機基又は炭素数10~30の直鎖若しくは分岐状構造を有する有機基であることが好ましい。
本発明の製造方法において、上記一般式(1)で表される化合物の配合量は、上記飲食品に対して0.001~10質量%であることが好ましい。上記ポリフェノールは、カテキン類であることが好ましい。本発明の製造方法においては、上記ポリフェノールを含有する飲食品が、緑茶飲料であることが好ましい。
上記一般式(1)で表される化合物の配合量は、上記飲食品に対して0.001~10質量%であることが好ましい。本発明の飲食品は、好ましくは緑茶飲料である。
上記緑茶飲料は、常温で9か月保管したときに、400~600nmの間の波長の光を用いて測定した場合の吸光度スペクトルの面積変化率、又は、487nmの波長の光を用いて吸光度を測定した場合の、上記吸光度の変化率が150%未満であることが好ましい。
本発明のポリフェノールを含有する組成物における上記一般式(2)で表される化合物の生成抑制方法は、ポリフェノールを含有する組成物と、上記一般式(1)で表される化合物とを混合することを特徴とする。
本発明のアルデヒド捕捉用組成物においては、上記一般式(1)において、上記R21が結合している炭素原子及びR23が結合している炭素原子のいずれかが、アルデヒドと反応することが好ましい。また、上記化合物(1)が、アルデヒドとの反応で、上記一般式(2)で表される化合物を実質的に生成しない化合物であることが好ましい。
本発明の消臭用組成物は、本発明のアルデヒド捕捉用組成物を含有することを特徴とする。
本発明の消臭用組成物は、アルデヒド由来の臭いの消臭用であることが好ましい。
本発明のスクリーニング方法においては、上記一般式(2)で表される化合物の生成を、400~600nmの間の波長の光を用いて試料溶液の吸光度スペクトルを測定し、上記吸光度スペクトルの面積変化量により検出する、又は487nmの波長の光を用いて試料溶液の吸光度を測定し、上記吸光度の変化量により検出することが好ましい。
より好ましくは、上記一般式(2)で表される化合物の生成を、487nmの波長の光を用いて試料溶液の吸光度を測定し、上記吸光度の変化により検出する。
褐変抑制のための、上記一般式(1)で表される化合物の使用。
アルデヒドを捕捉するための、上記一般式(1)で表される化合物の使用。
消臭のための、上記一般式(1)で表される化合物の使用。
上記一般式(1)で表される化合物を、アルデヒドを含む気体又は液体と接触させることを特徴とするアルデヒドの捕捉方法。
上記一般式(1)で表される化合物を、アルデヒドを含む気体又は液体と接触させることを特徴とする消臭方法。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。)
本明細書中、一般式(1)中のR21及びR23が結合しているベンゼン環を、ベンゼン環Aともいう。
本発明の褐変抑制用組成物は、上記化合物(1)を有効成分として含有する。
ベンゼン環Aにおいて、R21が結合している炭素原子に隣接するオルト位の少なくとも一方は水酸基ではない。R22及びR24は、それぞれ独立して、水素原子又は置換基を表すが、R23が水素原子を表す場合には、少なくともR22及びR24のいずれか(R22及び/又はR24)は置換基を表す。
このように、化合物(1)では、ベンゼン環Aに結合している水素原子に隣接する位置(オルト位)の少なくとも一方は水酸基ではない。
なお、本発明の褐変抑制用組成物は、通常、化合物(2)を含まない。
本発明における化合物(1)は、pH2~13で無色であることが好ましい。このような化合物であると、より優れた褐変抑制効果を発揮することができる。
化合物(1)においては、ベンゼン環Aに結合している酸素原子の数が多いほど、ベンゼン環Aとアルデヒドとの反応性が高くなる傾向がある。ベンゼン環Aには、OR22及びOR24により、少なくとも2個の酸素原子が結合している。一態様において、ベンゼン環Aに結合している酸素原子は、3個又は4個が好ましい。このような化合物として、例えば、Xが酸素原子である、及び/又は、R21又はR23がORa1(Ra1は、水素原子又は置換基を表す)で表される置換基である化合物が好ましい。例えば、R21が水素原子である場合、Xが酸素原子である、及び/又は、R23がORa1(Ra1は、上記と同義である)で表される置換基であることが好ましい。別の一態様において、R23が水素原子である場合、Xが酸素原子である、及び/又は、R21がORa1(Ra1は、上記と同義である)で表される置換基であることが好ましい。Ra1における置換基としては上述したものが挙げられる。
立体障害性置換基とは、ベンゼン環Aを構成する炭素原子がアルデヒドと反応した場合に、その立体障害により、該アルデヒドとの反応位置に隣接する位置(オルト位)の炭素原子に結合している水酸基と、他の水酸基との反応性を低下させる基を意味する。
例えば、R21が水素原子であり、R22が水素原子の場合には、R23及び/又はOR24が立体障害性置換基であることが好ましく、R23が立体障害性置換基であることがより好ましい。
一般式(1)において、
(i)R21が水素原子を表し、R22及びR23がそれぞれ独立して置換基を表す;
(ii)R23が水素原子を表し、R22及びR24が、それぞれ独立して置換基を表す;
(iii)R21が水素原子を表し、R22が水素原子を表し、R23が立体障害性置換基を表す;
(iv)R23が水素原子を表し、R21が立体障害性置換基を表し、R22が水素原子を表し、R24が置換基を表す;又は
(v)R23が水素原子を表し、OR22が立体障害性置換基を表し、R24が水素原子を表す。
上記(i)及び(ii)の化合物では、アルデヒドと反応する位置のオルト位がいずれも水酸基でないことにより、化合物(1)がアルデヒドと反応しても、通常化合物(2)の生成が起こらない。(ii)の化合物は、より好ましくはR21が水素原子である。(iii)、(iv)及び(v)の化合物では、立体障害性置換基により通常化合物(2)の生成が起こらない。このような化合物(1)は、優れた褐変抑制効果を発揮することができる。立体障害性置換基やその好ましい態様は、上述したとおりである。(iii)、(iv)及び(v)の化合物の中で、(iii)、(iv)の化合物がより好ましい。
(i)~(v)における置換基の一例として、水酸基又は炭素数1~10(炭素数は好ましくは1~8、より好ましくは1~6)の有機基が好ましい。
R26及びR27は、それぞれ独立して、水素原子又は置換基を表す。R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよい。
R25、R26及びR27における好ましい置換基として、炭素数1~15の有機基が挙げられる。該有機基として、アリール基、上記の糖残基が好ましい。一態様においては、R25、R26及びR27のいずれかが、アリール基であることが好ましい。好ましい態様の一例として、R25が酸素原子又はアリール基であり、R25が酸素原子である場合、R26又はR27がアリール基であることが挙げられる。アリール基は、1又は2以上の置換基により置換されていてもよく、例えば、1又は2以上の置換基により置換されていてもよい炭素数6~15のアリール基が好ましい。
上記の(i)~(v)の化合物において、R25、R26及びR27が上記である化合物は、本発明における化合物(1)の好ましい態様の一例である。
本発明における化合物(1)の製造方法は特に限定されず、公知の有機合成法により製造することができる。また、市販品を使用することもできる。天然物から公知の方法により単離することもできる。
本発明の褐変抑制用組成物、並びに、後述するアルデヒド捕捉用組成物及び消臭用組成物は、一例として、剤の形態で提供することができるが、本形態に限定されるものではない。当該剤をそのまま組成物として、又は、当該剤を含む組成物として提供することもできる。
本発明の褐変抑制用組成物中の化合物(1)の含量は特に限定されないが、一態様において、例えば、0.01~99.9質量%が好ましく、1~50質量%がより好ましい。
化合物(1)と、ポリフェノールを含有する組成物とを混合するポリフェノールを含有する組成物の褐変抑制方法も、本発明に包含される。
例えば、茶飲料に含まれるポリフェノールとして、フラバン-3-オール類及びその関連化合物が挙げられ、エピカテキン、エピカテキンガレート、エピガロカテキン、エピガロカテキンガレート、ガロカテキン、ガロカテキンガレート、カテキン、カテキンガレート等のカテキン類;テアフラビン、テアフラビンガレートA、テアフラビンガレートB、テアフラビンジガレート等のテアフラビン類を挙げることができる。
本発明におけるポリフェノールとしては、カテキン類が好ましい。化合物(1)は、カテキン類を含有する組成物の褐変の抑制に特に好適に使用される。
例えば、茶飲料の製造方法の一例を説明すると、以下の通りである。
原料(茶葉等)を温水又は熱水で抽出した後、濾過等により茶殻や微粒子を取り除く。次いで、抽出液を適当な濃度に希釈し、希釈液にアスコルビン酸又はアスコルビン酸ナトリウムを添加する。希釈液には、アスコルビン酸又はアスコルビン酸ナトリウムに加えて、重曹(炭酸水素ナトリウム)等のpH調整剤を添加することが好ましい。このアスコルビン酸又はアスコルビン酸ナトリウムを添加した茶抽出液の希釈液を、調合液と呼ぶ。なお、抽出液を希釈する前にアスコルビン酸又はアスコルビン酸ナトリウムを添加して調合液を調製してもよい。調合液は、加熱殺菌することが好ましく、超高温加熱処理法(UHT法)により殺菌することも好ましい。容器としてペットボトル等を使用する場合には、容器に充填する前に調合液の加熱殺菌を行うことが好ましい。一方、缶等に充填する場合には、充填後の容器ごと加熱殺菌を行うことが好ましい。また、充填の際には、ヘッドスペース中の空気を窒素ガスで置換することもできる。
例えば、茶飲料の製造において化合物(1)を混合する場合には、加熱殺菌までに化合物(1)を混合することが好ましく、化合物(1)を抽出用の温水又は熱水と混合しておいてもよく、抽出液と混合してもよく、調合液と混合してもよいが、好ましくは、調合液と混合する。
化合物(1)と、ポリフェノールを含有する緑茶飲料等とを混合することにより、ペットボトル等の透明容器に適した飲料を提供することができる。化合物(1)を使用する際に、さらに飲料のヘッドスペース中の空気を窒素ガスと置換したり、他の褐変抑制剤を併用したりしてもよい。
また、本発明における飲料は、希釈せずにそのまま飲用できるもの以外にも、飲料販売時には粉末の形態で飲用時に適宜の濃度に水等に溶解して飲用する粉末清涼飲料や、水等で希釈して飲用する濃縮タイプの飲料であってもよい。
化合物(1)の配合量は特に限定されないが、例えば、飲食品中に化合物(1)の配合量が0.001~10質量%が好ましく、0.01~1質量%がより好ましい。
上記吸光度スペクトルの面積変化率は、保管前の緑茶飲料の400~600nmの吸光度スペクトルの面積(S0)と、該緑茶飲料を常温で9か月保管後の400~600nmの吸光度スペクトルの面積(S1)とから、下記式により求められる。
吸光度スペクトルの面積変化率(%)=100×(S1-S0)/S0
上記吸光度スペクトルの面積変化率は、好ましくは50%未満である。
487nmの波長の吸光度の変化率は、保管前の緑茶飲料の487nmの吸光度(A0)と、該緑茶飲料を常温で9か月保管後の487nmの吸光度(A1)とから、下記式により求められる。
487nmの波長の吸光度の変化率(%)=100×(A1-A0)/A0
上記487nmの波長の吸光度の変化率は、好ましくは50%未満である。
本発明においては、化合物(1)をそのままアルデヒド捕捉用組成物(アルデヒド捕捉剤ということもできる)として用いてもよい。アルデヒド捕捉用組成物には、本発明の効果を損なわない限り、所望により化合物(1)以外の成分(他の成分)を配合してもよい。他の成分は、アルデヒド捕捉用組成物の使用形態等に応じて適宜選択することができ、一例として添加剤等が挙げられる。
一態様において、アルデヒド捕捉用組成物中の化合物(1)の含量は、例えば、0.01~99.9質量%が好ましく、1~50質量%がより好ましい。
アルデヒド捕捉用組成物は、例えば、空気中、溶液中等のアルデヒドを捕捉するために好適に使用される。例えば、アルデヒド捕捉用組成物を、アルデヒドを含む気体又は液体と接触させることにより、該気体又は液体中のアルデヒドを捕捉することができる。アルデヒド捕捉用組成物は、例えば、アルデヒド由来の臭いの消臭用等として好適に使用することができる。また、生体内のアルデヒドを捕捉するためや、シックハウスの原因物質であるアルデヒドの捕捉にも使用することができる。
ポリフェノールを含有する組成物と、化合物(1)とを混合すると、該組成物中のポリフェノールとアルデヒドとの反応が抑制され、該組成物中のポリフェノールの減少を抑制することができる。
化合物(1)の使用量は特に限定されず、ポリフェノールを含有する組成物に応じて適宜選択すればよいが、例えば、ポリフェノールを含有する組成物に対して0.001~10質量%が好ましく、0.01~1質量%がより好ましい。例えば、ポリフェノールを含有する組成物が茶飲料であれば、茶飲料に対して化合物(1)が0.001~10質量%が好ましく、0.01~1質量%がより好ましい。
例えば、緑茶飲料は、製造直後には爽快な苦味を呈するが、長期間貯蔵すると、この爽快な苦味が減少することがある。この香味の変化の原因の1つとして、貯蔵中にカテキン類がアルデヒドと反応して減少したことが考えられる。本発明によれば、長期間貯蔵しても、カテキン類の減少が抑制され、香味の変化及び褐変が抑制された緑茶飲料を提供することができる。
化合物(1)及びその好ましい態様は、上述した通りである。化合物(1)は、1種使用してもよく、2種以上を使用してもよい。
化合物(1)の使用量は特に限定されず、ポリフェノールを含有する組成物に応じて適宜選択すればよいが、例えば、ポリフェノールを含有する組成物に対して0.001~10質量%が好ましく、0.01~1質量%がより好ましい。例えば、ポリフェノールを含有する組成物が茶飲料であれば、茶飲料に対して化合物(1)が0.001~10質量%が好ましく、0.01~1質量%がより好ましい。
本発明の消臭用組成物は、化合物(1)によりアルデヒドを捕捉して、アルデヒド由来の臭いを効果的に低減させることができる。このため本発明の消臭用組成物は、アルデヒド由来の臭いの消臭用組成物として好適に使用される。化合物(1)は、消臭用組成物の有効成分として好適に使用される。
化合物(1)及びその好ましい態様は、上述した通りである。例えば、一般式(1)において、R21が結合している炭素原子及びR23が結合している炭素原子のいずれかが、アルデヒドと反応することが好ましい。また、化合物(1)が、アルデヒドとの反応で、化合物(2)を実質的に生成しない化合物であることが好ましい。消臭用組成物は、化合物(1)を1種含んでもよく、2種以上を含んでもよい。
消臭用組成物には、必要に応じて、化合物(1)以外の成分、例えば、酸化防止剤、紫外線吸収剤、帯電防止剤、難燃剤、殺菌剤、防カビ剤、防虫剤、顔料、着色剤、着香料等の一般的な添加剤を配合することができる。
上記試料溶液における上記一般式(2)で表される化合物の生成を指標として、上記候補化合物の褐変抑制効果を判定する工程を含む。
一般式(2)で表される化合物(化合物(2))は、上述したとおりである。
ポリフェノールとしては、アルデヒドとの反応により化合物(2)を生成する化合物であればよく、目的に応じて適宜選択すればよい。例えば、緑茶飲料において褐変抑制効果を有する化合物をスクリーニングする場合には、上述した緑茶飲料に含まれるカテキン類等のポリフェノールを使用すればよい。ポリフェノールは1種使用してもよく、2種以上を使用してもよい。
アルデヒドは特に限定されず、目的に応じて適宜選択すればよい。例えば、緑茶飲料における褐変抑制効果を有する化合物をスクリーニングする場合には、例えば、グリオキサール、メチル-グリオキサール、ジアセチル、L-トレオニン及び3-デオキシ-L-トレオニンからなる群より選択される少なくとも1種が好ましく、グリオキサールがより好ましい。これらのアルデヒドは、緑茶飲料に通常添加されるL-アスコルビン酸の分解物であるため、緑茶飲料における褐変抑制に有効な候補化合物のスクリーニングに好適である。
化合物(2)は、通常400~600nmに吸収極大を有するため、上記波長の吸光度を測定することにより、化合物(2)の生成を検出することができる。例えば、400~600nmのスペクトル面積値の変化により、化合物(2)の生成を検出することができる。また、上述したように化合物(2)は、pHによって極大がシフトする性質があり、例えば弱酸性付近(pH5付近)では440nmあたりに吸収極大をもち、pH6.0~8.9では486~487nm付近に吸収極大を有する(NE Es-Safi et al., Food Chem 88(2004) 367-372)。このため、溶液のpHに応じて、適宜化合物(2)の検出に使用する波長を設定することが好ましい。化合物(2)の検出は、該溶液における極大波長とすることが好ましい。例えば緑茶飲料は、通常pHが6~8である。緑茶飲料における褐変抑制効果を有する化合物をスクリーニングする場合には、487nmの吸光度を測定し、487nmの吸光度の変化により化合物(2)の生成を検出することが好ましい。
本発明のスクリーニング方法により褐変抑制効果を有すると判定された物質は、上述した褐変抑制のため、アルデヒド捕捉のため、消臭のため等に使用することができ、例えば、褐変抑制用組成物、アルデヒド捕捉用組成物、消臭用組成物の有効成分として好適に使用される。
褐変抑制のための、上記一般式(1)で表される化合物の使用。
褐変抑制用組成物を製造するための、上記一般式(1)で表される化合物の使用。
アルデヒドを捕捉するための、上記一般式(1)で表される化合物の使用。
アルデヒド捕捉用組成物を製造するための、上記一般式(1)で表される化合物の使用。
消臭のための、上記一般式(1)で表される化合物の使用。
消臭用組成物を製造するための、上記一般式(1)で表される化合物の使用。
ポリフェノールを含有する組成物におけるポリフェノールの減少抑制ための、上記一般式(1)で表される化合物の使用。
ポリフェノールを含有する組成物における上記一般式(2)で表される化合物の生成抑制ための、上記一般式(1)で表される化合物の使用。
上記一般式(1)で表される化合物を、アルデヒドを含む気体又は液体と接触させる、アルデヒド捕捉方法。
上記一般式(1)で表される化合物を、アルデヒドを含む気体又は液体と接触させる、消臭方法。
化合物(1)及びその好ましい態様等は、上述した通りである。褐変抑制は、好ましくは、上述したポリフェノールを含有する組成物の褐変抑制である。化合物(1)は、アルデヒド由来の臭いの消臭に好適に使用される。
実施例中、可視吸収スペクトルを、単に吸収スペクトルともいう。
LC-MS分析には、液体クロマトグラフ質量分析計 LC-MS2020((株)島津製作所製)を使用した。
2Lペットボトル入りの緑茶飲料を製造し、未開封の状態で室温で貯蔵して、目視及び可視吸収スペクトルの測定により、経時的な色の変化を確認した。
緑茶葉を30倍量のイオン交換水(70℃)にて5分間抽出した。抽出0分、1分、2分、3分、4分のタイミングで、撹拌(1回あたり5回を15秒で撹拌)を行った。抽出時間5分のタイミングで、20メッシュのフィルターで茶葉抽出液を濾過して茶葉を除去して、「抽出液」を得た。この抽出液を、イオン交換水を用いて、抽出に用いたイオン交換水の量までメスアップし、流水で30℃程度まで冷却した。冷却した抽出液を6000rpm、10分遠心分離し、上清を回収し、抽出液の希釈液とした。抽出液の希釈液をキュノフィルター(3M社製)に通し、回収した溶液にアスコルビン酸を添加し、pH調整剤として重曹を加え、pH6.4に調整した。さらに、Brix値0.21となるようにイオン交換水で希釈して、「調合液」とした。アスコルビン酸は、調合液中のアスコルビン酸濃度が0.4g/Lとなるように添加した。調合液を超高温加熱処理殺菌機(UHT殺菌機)により132.5℃で60秒間殺菌し、2Lの透明なペットボトルに充填した。
緑茶葉を30倍量のイオン交換水(70℃)にて5分間抽出した。抽出0分、1分、2分、3分、4分のタイミングで、撹拌(1回あたり5回を15秒で撹拌)を行った。抽出時間5分のタイミングで、20メッシュのフィルターで茶葉抽出液を濾過して茶葉を除去して、「抽出液」を得た。この抽出液を、イオン交換水を用いて、抽出に用いたイオン交換水の量までメスアップし、流水で30℃程度まで冷却した。冷却した抽出液を6000rpm、10分遠心分離し、上清を回収し、抽出液の希釈液とした。抽出液の希釈液をキュノフィルター(3M社製)に通し、回収した溶液にアスコルビン酸を添加し、pH調整剤として重曹を加え、pH6.4に調整した。さらに、Brix値0.21となるようにイオン交換水で希釈して、「調合液」とした。アスコルビン酸は、調合液中のアスコルビン酸濃度が0、0.04、0.4又は1.2g/Lとなるように添加した。
条件1:窒素置換、4℃で1時間
条件2:121℃、14分
条件3:酸素曝気後、123℃で30分
条件2及び3は、オートクレーブを使用した加速劣化試験である。条件2は、緑茶飲料製造時の殺菌を想定した条件である。条件2は、酸素、窒素置換はしなかった。条件3は、酸素過多で褐変反応が最大まで進んだ状態を想定した条件である。
図3は、アスコルビン酸を0.4g/L添加した調合液の条件2の劣化試験前後の可視吸光スペクトルを示す図である。図3中、実線が条件2の試験前のスペクトル、破線が試験後のスペクトルである。
図4の(a)~(c)において、実線は、アスコルビン酸の添加量が0g/Lの調合液;破線は、アスコルビン酸の添加量が0.04g/Lの調合液;点線は、アスコルビン酸の添加量が0.4g/Lの調合液;一点鎖線は、アスコルビン酸の添加量が1.2g/Lの調合液の可視吸収スペクトルである。
図4の(a)から、条件1(窒素置換、4℃)では、400~450nmにおける吸収の差はあるものの、吸収極大を示すスペクトルを示さなかった。
サンプルの目視確認においてもアスコルビン酸無添加の調合液のみが顕著に赤色を呈していることから、緑茶由来の成分どうしが反応して赤色の化合物が生成すると考えられた。
サンプルの目視確認においてもアスコルビン酸添加に応じて、黄褐色を呈していることから、アスコルビン酸を基質として黄褐色の化合物が生成すると考えられた。
アスコルビン酸の濃度が0.4g/L以上の調合液も、さらに酸素曝気と加熱を行えば、最終的には同じ状態に近づくと考えられた。
これらの結果から、加速劣化に関しては高温条件により時間短縮ができ、褐変現象をトレースできることが示された。一方で、アスコルビン酸が、色調劣化に大きく寄与していることと、褐変の評価指標として使用する487nmの吸収極大(黄褐色化)の増加に寄与する基質であることが判明した。
緑茶飲料の褐変を生じる反応において、アスコルビン酸が基質であることが示されたことから、別の実験にてそのアスコルビン酸と反応し、黄褐色化を担うもう一方の化合物を天然物化学的な手法を用い、探索した。その結果、ポリフェノールの一種であるカテキン類が挙げられた。カテキン類はエピカテキン(EC)、エピガロカテキン(EGC)、エピカテキンガレート(ECg)及びエピガロカテキンガレート(EGCg)の4種が候補として挙がった。尚、加熱殺菌することでこれらはエピメル化を起こし、異性体であるカテキン(C)、ガロカテキン(GC)、カテキンガレート(Cg)及びガロカテキンガレート(GCg)を生じる。
以下のモデル実験を行い、緑茶の褐変を化合物レベルで検証した。
LC
カラム:2.5 Cholester(ナカライテスク製)(100mmL.×2.0I.D.)
移動相:
A:0.1%ギ酸/H2O
B:0.1%ギ酸/CH3CN
グラジエント溶出法
タイムプログラム(B液濃度は体積%):B5%(0-0.5分)→B32%(20分)→B100%(25-27.5分)→B5%(27.51-30分)
流量:0.25mL/分
カラム温度:40℃
試料注入量:2μL
プローブ電圧:+4.5kV(ESI Positive Mode)
-3.5kV(ESI Negative Mode)
ネプライザーガス流量:1.5L/分
ドライングガス流量:20L/分
DL温度:250℃
DL電圧/Q-aray電圧:デフォルト値
SIM:m/z289(Negative)(EC)
m/z305(Negative)(EGC)
m/z441(Negative)(ECg)
m/z457(Negative)(EGCg)
オートクレーブを用い、試験例2の条件3(酸素曝気後、123℃で30分)で緑茶及びモデル液(カテキン4種混合)を加速劣化し、可視吸収スペクトルの挙動を観察した。
図6の(a)及び(b)に示すように、加速劣化前後の緑茶とカテキン4種混合のモデル液のスペクトルを比較すると、加速劣化前後の変化量ΔABUがほぼ一致した。また、487nm吸収極大が増加する現象としても一致度が高いことから、モデル液により緑茶の褐変反応に近いものを再現できたといえる。これらの結果より、緑茶中の褐変を担う成分群としてカテキン類とアスコルビン酸(と重曹)が見出された。
アスコルビン酸の分解経路として、酸化によってデヒドロアスコルビン酸を経てアルデヒドが生じる経路と、非酸化的にデヒドロアスコルビン酸を経ずアルデヒドが生じる経路の二種類存在する。いずれの経路においても、分解物として、グリオキサール、メチル-グリオキサール、ジアセチル、L-トレオニン、3-デオキシ-L-トレオニン等のアルデヒドが生じることが報告されている(A Schulz et al., Int J Mass Spec 262(2007)169-173)。
実際に、アスコルビン酸及び重曹の存在下において、どのようなアルデヒドが生じるかを検証した。
LC
カラム:C18M 2D(Shodex製)(100mmL.×2.0I.D.)
移動相:
A:0.1%ギ酸/H2O
B:0.1%ギ酸/CH3CN
グラジエント溶出法
タイムプログラム(B液濃度は体積%):B5%(0-2分)→B60%(7.5分)→B100%(17-21分)→B5%(22-30分)
流量:0.2mL/分
カラム温度:40℃
試料注入量:2μL
プローブ電圧:+1.6kV(ESI Positive Mode)
-1.6kV(ESI Negative Mode)
ネプライザーガス流量:1.5L/分
ドライングガス流量:20L/分
DL温度:250℃
DL電圧/Q-aray電圧:デフォルト値
SIM:m/z195(Negative)
m/z249(Negative)
m/z407(Positive)
試験例1~4の結果から、反応基質としてカテキン類とアスコルビン酸から生じるグリオキサールとの反応によって生じる化合物が緑茶褐色物質である可能性が高いと考えられた。その検証実験を行うこととした。
LC
カラム:2.5 Cholester(ナカライテスク製)(100mmL.×2.0I.D.)
移動相:
A:0.1%ギ酸/H2O
B:0.1%ギ酸/CH3CN
グラジエント溶出法
タイムプログラム(B液濃度は体積%):B5%(0-0.5分)→B32%(20分)→B100%(25-27.5分)→B5%(27.51-30分)
流量:0.25mL/分
カラム温度:40℃
試料注入量:2μL
プローブ電圧:+4.5kV(ESI Positive Mode)
-3.5kV(ESI Negative Mode)
ネプライザーガス流量:1.5L/分
ドライングガス流量:20L/分
DL温度:250℃
DL電圧/Q-aray電圧:デフォルト値
SCAN:m/z100-800(Positive, Negative)
SIM:m/z289(Negative)(EC)
m/z347(Negative)
m/z601(Negative)
この結果より、緑茶の褐変反応を、化合物をモデルとし、トレースすることができた。
このキサンチリウム構造の化合物は、緑茶飲料のpHである中性付近では487nm付近に吸収極大を有する(NE Es-Safi et al., Food Chem 88(2004) 367-372)。従って、緑茶飲料等のpHが中性付近の溶液におけるキサンチリウム構造の化合物の生成(褐変)は、487nmの吸収の変化により評価することができる。
緑茶の褐変現象がカテキン類とアルデヒド類との反応によって生じることが判明した。このアルデヒドとの反応は、カテキン類以外のフラボノイド骨格をもつ化合物でも起こることが別の実験から明らかになった。
このフラボノイド骨格を有する化合物の性質を利用し、緑茶中のカテキンとの競合下でもアルデヒドと反応し、生成物が色を呈さないようなフラボノイドの化合物を探索した。
上記構造を有するフラボノイドとして、バイカリン(和光純薬工業(株))を使用して実験を行った。バイカリンの構造式を以下に示す。
図9より、バイカリンを添加しない場合(実線)と比較して、バイカリン添加(破線)により、加速劣化前後の可視吸収スペクトルの変化量ΔABUが有意に減少した。
以下の3種類の溶液を調製した。
B+G:バイカリン(0.5g/L)及びグリオキサール(0.01g/L)の混合液
B+C+G:バイカリン(0.5g/L)、エピカテキン(0.5g/L)及びグリオキサール(0.01g/L)の混合液
C+G:エピカテキン(0.5g/L)及びグリオキサール(0.01g/L)の混合液
上記の溶液を、オートクレーブで121℃で15分保持して加速劣化させた。加速劣化後、目視により色の変化を確認し、さらに可視吸収スペクトルを測定した。図10に結果を示す。
混合液(B+G)と(B+C+G)と(C+G)の色を目視により確認すると、(B+G)は薄黄色であり、(C+G)は褐色であった。このときの混合液(B+C+G)は(B+G)と(C+G)の間の黄褐色であった。図10の(b)の混合液(B+C+G)と(C+G)との比較から、バイカリンの添加により、487nmの吸収が顕著に減少することが分かる。このことから、バイカリンにより、エピカテキンとアルデヒドから生じる褐変を抑制されたといえる。
実施例1及び実施例2の上記結果から、バイカリンによる褐変抑制効果が証明された。
図11に、加速劣化後の混合液(B+C+G)及び混合液(C+G)中のカテキン残存量(mM)を示す。図11より、バイカリン添加により、溶液中のカテキン残存量が増加することが分かった。
バイカリンによる褐変抑制効果について、メカニズムを検証した。
バイカリン(0.5g/L)及びグリオキサール(0.01g/L)の混合液を、試験例2の条件3(酸素曝気後、123℃で30分)で加速劣化させ、LC-MSにより分析を行った。LC-MS測定条件は、試験例5と同じである。
バイカリンの水への溶解性を上げるため、以下の方法によりバイカリン配糖体を作製した。
アスコルビン酸ナトリウム2.5gを蒸留水500mLに溶解させた。これに1N NaOHを20mL加え、pH12に調整し、アスコルビン酸ナトリウム水溶液を調製した。バイカリン(和光純薬工業(株))500mg及びデキストリン(トウモロコシ由来)2500mgに上記のアスコルビン酸ナトリウム水溶液500mLを加えた。これに1N HClを4mL加えてpH7.0にした後、糖転移酵素(コンチザイム、天野エンザイム)を100U添加した。68℃で35時間反応させた後、95℃で30分加熱して酵素を失活させた。
反応液を、ダイヤイオンHP20(三菱化学(株))1000mLを充填したカラム(予め、食添用エタノール2Lを通液後、蒸留水2Lを通液したもの)に通液し、次いで蒸留水2Lを通液後、80%エタノール2Lで溶出させた。80%エタノール画分をエバポレータにて濃縮し、凍結乾燥した。また、80%エタノール画分(フラクションNo.1~8)を下記条件でLC-MSに供して分析し、バイカリンを定量した。80%エタノール画分(フラクションNo.1~8)中のバイカリン配糖体(配糖化されたバイカリン)収量を表1に示す。
LC
カラム:C18M 2D(Shodex製)(100mmL.×2.0I.D.)
移動相:
A:0.1%ギ酸/H2O
B:0.1%ギ酸/CH3CN
グラジエント溶出法
タイムプログラム(B液濃度は体積%):B5%(0-2分)→B28%(10分)→B50%(15分)→B100%(18分)→B5%(20-26分)
流量:0.2mL/分
カラム温度:25℃
試料注入量:2μL
インタフェース DUIS(ESI&APCI)
ネプライザーガス流量:1.5L/分
ドライングガス流量:20L/分
DL温度:250℃
DL電圧/Q-aray電圧:デフォルト値
SIM:m/z447(Positive)(バイカリン)
バイカリン配糖体のLC-MS分析条件
LC
カラム:C18M 2D(Shodex製)(100mmL.×2.0I.D.)
移動相:
A:0.1%ギ酸/H2O
B:0.1%ギ酸/CH3CN
グラジエント溶出法
タイムプログラム(B液濃度は体積%):B12.5%(0-0.5分)→B25%(10分)→B50%(20-22分)→B12.5%(24-26分)
流量:0.2mL/分
カラム温度:25℃
試料注入量:2μL
MS
インタフェース DUIS(ESI&APCI)
ネプライザーガス流量:1.5L/分
ドライングガス流量:20L/分
DL温度:250℃
DL電圧/Q-aray電圧:デフォルト値
SIM:m/z447(Positive) バイカリン
m/z609(Positive) バイカリンモノグルコシド
m/z771(Positive) バイカリンジグルコシド
m/z933(Positive) バイカリントリグルコシド
アルデヒド捕捉物質のスクリーニングを行った。
(アッセイ系の構築)
モデルアルデヒドをグリオキサール、反応基質をエピカテキンとし、これに加える候補物質がどれだけ褐変を抑制できるかにより、アルデヒド捕捉能を評価した。ネガティブコントロールには、蒸留水を使用した。また、ポジティブコントロールとして、調製例1で得たフラクション6、7及び8(バイカリン及びバイカリン配糖体(バイカリンの糖部分にグルコースが1~3個結合した化合物)を含む混合物)を使用した。
試薬には、グリオキサール水溶液(39%(v/v))及びエピカテキンを使用した。
サンプル液は、候補物質を水に溶解させ、該候補物質由来のトータルフェノール量が600ppmとなるように調整して作製した。トータルフェノール量は、没食子酸を標準物質として使用し、フォーリン・デニス法により測定した。なお、候補物質の使用量(トータルフェノール量)は、ポジティブコントロールが褐変抑制活性を示す濃度の5倍量を目安として設定した。
70℃で16時間加速劣化させ、400~600nmのスペクトル面積値、487nmの吸光度を測定した。
加速劣化前後における可視吸光度変化を算出した。褐変抑制の活性値の指標として、Br値(Browning)とXt値(キサンチリウム)の2つを設定した。Br値は400~600nmのスペクトル面積値の変化量Δを示し、Xt値は487nmの吸光度変化量Δを示している。図14は、スクリーニングに使用したBr値及びXt値を説明するための図である。図14中、実線がアルデヒド捕捉作用を有する物質(褐変抑制作用を有する物質)を添加した場合の吸光度であり、破線がネガティブコントロールの吸光度である。
ネガティブコントロールに比べてBr値及びXt値が大きいほど、アルデヒド捕捉能が高く、褐変抑制作用が高いことを意味する。
化合物(A-1)~(A-5)は、いずれもアルデヒド捕捉能を有し、褐変抑制作用を示すことが分かった。
候補物質として、チャフロサイドA、イカリイン(Ark Pharm, Inc.製)及びスクテラリン(Sigma-Aldrich製)の各化合物を用いた。これ以外は、実施例4と同じ方法でアルデヒド捕捉能及び褐変抑制作用を評価した。チャフロサイドAは下記式(B-1)の化合物であり、イカリインは、下記式(B-2)の化合物であり、スクテラリンは、下記式(B-3)の化合物である。
チャフロサイドA、イカリイン及びスクテラリンについてアルデヒド捕捉効果を確認した。なお、これら化合物は本法の濃度では難水溶性を示し、溶け切らなかったものはフィルターにて除去した。
Claims (45)
- 下記一般式(1)で表される化合物を含有することを特徴とする褐変抑制用組成物。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 前記一般式(1)において、前記R21が結合している炭素原子及びR23が結合している炭素原子のいずれかが、アルデヒドと反応する請求項1に記載の褐変抑制用組成物。
- 前記一般式(1)において、ベンゼン環に結合している水素原子に隣接する位置(オルト位)がいずれも水酸基ではない請求項1~3のいずれかに記載の褐変抑制用組成物。
- 前記一般式(1)において、ベンゼン環に結合している水素原子に隣接する位置(オルト位)の一方が水酸基であり、かつ、ベンゼン環に少なくとも1つ立体障害性置換基が結合している請求項1~3のいずれかに記載の褐変抑制用組成物。
- 前記水酸基に隣接する位置(オルト位)が、立体障害性置換基である請求項5に記載の褐変抑制用組成物。
- 前記一般式(1)において、R21が水素原子を表し、R22及びR23がそれぞれ独立して置換基を表す請求項1~4のいずれかに記載の褐変抑制用組成物。
- 前記一般式(1)において、R23が水素原子を表し、R22及びR24が、それぞれ独立して置換基を表す請求項1~4のいずれかに記載の褐変抑制用組成物。
- 前記一般式(1)において、R21が水素原子を表し、R22が水素原子を表し、R23が立体障害性置換基を表す請求項1~3及び5~6のいずれかに記載の褐変抑制用組成物。
- 前記一般式(1)において、R23が水素原子を表し、R21が立体障害性置換基を表し、R22が水素原子を表し、R24が置換基を表す請求項1~3及び5~6のいずれかに記載の褐変抑制用組成物。
- 前記一般式(1)において、R23が水素原子を表し、OR22が立体障害性置換基を表し、R24が水素原子を表す請求項1~3及び5のいずれかに記載の褐変抑制用組成物。
- 前記立体障害性置換基が、環構造を有する炭素数6~30の有機基又は炭素数10~30の直鎖若しくは分岐状構造を有する有機基である請求項5~6及び9~11のいずれかに記載の褐変抑制用組成物。
- 前記置換基が、水酸基、炭素数1~50の有機基、アミノ基、チオール基、ニトロ基又はハロゲン原子である請求項1~12のいずれかに記載の褐変抑制用組成物。
- 前記置換基が、水酸基又は炭素数1~50の有機基である請求項1~13のいずれかに記載の褐変抑制用組成物。
- ポリフェノールを含有する組成物の褐変を抑制するために使用される請求項1~14のいずれかに記載の褐変抑制用組成物。
- 前記ポリフェノールを含有する組成物が、ポリフェノールを含有する飲食品である請求項15に記載の褐変抑制用組成物。
- 前記ポリフェノールが、カテキン類である請求項15又は16に記載の褐変抑制用組成物。
- 前記ポリフェノールを含有する組成物が、緑茶飲料である請求項15~17のいずれかに記載の褐変抑制用組成物。
- 下記一般式(1)で表される化合物と、ポリフェノールを含有する組成物とを混合することを特徴とするポリフェノールを含有する組成物の褐変抑制方法。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 前記ポリフェノールを含有する組成物が、ポリフェノールを含有する飲食品である請求項19に記載の方法。
- 前記ポリフェノールが、カテキン類である請求項19又は20に記載の方法。
- 前記ポリフェノールを含有する組成物が、緑茶飲料である請求項19~21のいずれかに記載の方法。
- 下記一般式(1)で表される化合物と、ポリフェノールを含有する飲食品とを混合することを特徴とする飲食品の製造方法。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 前記一般式(1)で表される化合物の配合量が、前記飲食品に対して0.001~10質量%である請求項23に記載の製造方法。
- 前記ポリフェノールが、カテキン類である請求項23又は24に記載の製造方法。
- 前記ポリフェノールを含有する飲食品が、緑茶飲料である請求項23~25のいずれかに記載の製造方法。
- 下記一般式(1)で表される化合物を配合してなることを特徴とする飲食品。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 前記一般式(1)で表される化合物の配合量が、飲食品に対して0.001~10質量%である請求項27に記載の飲食品。
- 緑茶飲料である請求項27又は28に記載の飲食品。
- 前記緑茶飲料は、常温で9か月保管したときに、400~600nmの間の波長の光を用いて測定した場合の吸光度スペクトルの面積変化率、又は、487nmの波長の光を用いて吸光度を測定した場合の、前記吸光度の変化率が150%未満である請求項29に記載の飲食品。
- ポリフェノールを含有する組成物と、下記一般式(1)で表される化合物とを混合することを特徴とする前記ポリフェノールを含有する組成物におけるポリフェノールの減少抑制方法。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - ポリフェノールを含有する組成物と、下記一般式(1)で表される化合物とを混合することを特徴とする前記ポリフェノールを含有する組成物における下記一般式(2)で表される化合物の生成抑制方法。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。)
- 下記一般式(1)で表される化合物を含有することを特徴とするアルデヒド捕捉用組成物。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 前記一般式(1)において、前記R21が結合している炭素原子及びR23が結合している炭素原子のいずれかが、アルデヒドと反応する請求項33に記載のアルデヒド捕捉用組成物。
- 請求項33~35のいずれかに記載のアルデヒド捕捉用組成物を含有することを特徴とする消臭用組成物。
- アルデヒド由来の臭いの消臭用である請求項36に記載の消臭用組成物。
- ポリフェノール、アルデヒド及び候補化合物を含有する試料溶液を調製する工程、及び、
前記試料溶液における下記一般式(2)で表される化合物の生成を指標として、前記候補化合物の褐変抑制効果を判定する工程を含むことを特徴とするポリフェノールを含有する組成物の褐変抑制作用を有する化合物のスクリーニング方法。
- 前記一般式(2)で表される化合物の生成を、400~600nmの間の波長の光を用いて試料溶液の吸光度スペクトルを測定し、前記吸光度スペクトルの面積変化量により検出する、又は487nmの波長の光を用いて試料溶液の吸光度を測定し、前記吸光度の変化量により検出する請求項38に記載のスクリーニング方法。
- 前記一般式(2)で表される化合物の生成を、487nmの波長の光を用いて試料溶液の吸光度を測定し、前記吸光度の変化により検出する請求項38又は39に記載のスクリーニング方法。
- 褐変抑制のための、下記一般式(1)で表される化合物の使用。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - アルデヒドを捕捉するための、下記一般式(1)で表される化合物の使用。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 消臭のための、下記一般式(1)で表される化合物の使用。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 下記一般式(1)で表される化合物を、アルデヒドを含む気体又は液体と接触させることを特徴とするアルデヒドの捕捉方法。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。) - 下記一般式(1)で表される化合物を、アルデヒドを含む気体又は液体と接触させることを特徴とする消臭方法。
R23が水素原子を表す場合には、少なくともR22及びR24のいずれかは置換基を表し、
R25は、水素原子、酸素原子又は置換基を表し、
R22及びR23、又は、R23及びR24は、互いに結合してそれらが結合している酸素原子及び炭素原子と共に環を形成していてもよく、
R25及びR26、又は、R26及びR27は、互いに結合してそれらが結合している炭素原子と共に環構造を形成していてもよく、
Xは、酸素原子又は-CH2-を表し、
破線は、二重結合であってもよいことを表す。)
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CN111675719B (zh) * | 2020-04-01 | 2021-05-18 | 华中科技大学 | 一种黄酮类化合物及其制备方法和应用 |
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AU2017282545B9 (en) | 2022-05-05 |
EP3476227A4 (en) | 2020-02-05 |
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