Oral care composition, Anti-inflammatory composition, and oral inflammation suppressant
Combining polyphosphate with arginine and fused polycyclic compounds in oral care compositions addresses the insufficient anti-inflammatory effect of polyphosphate, achieving superior inflammation suppression in the oral cavity.
Patent Information
- Application Number
- JP2024035386
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2024-03-07
- Publication Date
- 2025-09-19
AI Technical Summary
Polyphosphate alone may not provide a sufficient anti-inflammatory effect in the oral cavity.
A combination of a polyphosphate compound with an arginine compound and a fused polycyclic compound is used in oral care compositions to enhance anti-inflammatory effects.
The combination exhibits excellent inflammation-suppressing effects in the oral cavity, outperforming polyphosphate alone.
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Figure 2025136655000001 
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Abstract
Description
[Technical Field]
[0001] The present disclosure relates to oral care compositions, anti-inflammatory compositions, and oral inflammation suppressants. [Background technology]
[0002] In recent years, polyphosphate, which is believed to have a strong antibacterial effect, has been attracting attention as an ingredient used in oral care compositions. Polyphosphate is also known to have an anti-inflammatory effect (see, for example, Patent Document 1). [Prior art documents] [Patent documents]
[0003] [Patent Document 1] International Publication No. 2004 / 075906 Summary of the Invention [Problem to be solved by the invention]
[0004] As described above, polyphosphate has an anti-inflammatory effect (hereinafter also referred to as an inflammation suppressing effect), but polyphosphate alone may not be able to provide a sufficient inflammation suppressing effect in the oral cavity.
[0005] An object of one embodiment of the present disclosure is to provide an oral care composition, an anti-inflammatory composition, and an oral inflammation inhibitor that can exert an excellent inflammation inhibitory effect in the oral cavity. [Means for solving the problem]
[0006] Specific means for solving the above problems are as follows. <1> a polyphosphate compound (A) containing at least one of polyphosphoric acid and a salt of polyphosphoric acid; an arginine compound (B1) containing at least one compound selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine; and a compound (B2) containing at least one compound selected from the group consisting of a fused polycyclic compound containing a fused ring in which an aromatic ring and a heterocycle are fused; 1. An oral care composition comprising: <2> the polyphosphate compound (A) contains at least one of a polyphosphoric acid having a chain length, which is the number of repetitions of structural units derived from phosphoric acid, of 3 to 300 and a salt of the polyphosphoric acid; <1> The oral care composition according to claim 1. <3> the compound (B) comprises the arginine compound (B1), The arginine compound (B1) contains at least one of protamine and a salt of protamine. <1> or <2> The oral care composition according to claim 1. <4> the compound (B) contains the fused polycyclic compound (B2), The molecular weight of the condensed polycyclic compound (B2) is 120 to 1000. <1> ~ <3> 10. The oral care composition according to claim 9, wherein the oral care composition is a mixture of 2 or more of the above. <5> a mouthwash, oral moisturizer, or toothpaste; <1> ~ <4> 10. The oral care composition according to claim 9, wherein the oral care composition is a mixture of 2 or more of the above. <6> a polyphosphate compound (A) containing at least one of polyphosphoric acid and a salt of polyphosphoric acid; an arginine compound (B1) containing at least one compound selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine; and a compound (B2) containing at least one compound selected from the group consisting of a fused polycyclic compound containing a fused ring in which an aromatic ring and a heterocycle are fused; An anti-inflammatory composition comprising: <7> An oral inflammation inhibitor comprising an arginine compound (B1) containing at least one member selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine. [Effects of the Invention]
[0007] According to one aspect of the present disclosure, there are provided an oral care composition, an anti-inflammatory composition, and an oral inflammation inhibitor that can exert excellent inflammation suppressing effects in the oral cavity. DETAILED DESCRIPTION OF THE INVENTION
[0008] In the present disclosure, a numerical range indicated using "to" means a range that includes the numerical values before and after "to" as the minimum and maximum values, respectively. In the present disclosure, the term "process" includes not only an independent process but also a process that cannot be clearly distinguished from other processes as long as the intended purpose of the process is achieved. In the present disclosure, when there are multiple substances corresponding to each component, the amount of each component means the total amount of the multiple substances unless otherwise specified.
[0009] [Oral care composition] The oral care composition of the present disclosure comprises: a polyphosphate compound (A) containing at least one of polyphosphoric acid and a salt of polyphosphoric acid; an arginine compound (B1) containing at least one compound selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine; and a compound (B2) containing at least one compound selected from the group consisting of a fused polycyclic compound containing a fused ring in which an aromatic ring and a heterocycle are fused; Includes.
[0010] As mentioned above, polyphosphate is known to have an anti-inflammatory effect. However, the inventors' investigations have revealed that polyphosphoric acid or a salt thereof alone may not be sufficient to provide an anti-inflammatory effect in the oral cavity. Regarding this problem, the present inventors have conducted studies and found that not only the polyphosphate compound (A) but also the above-mentioned compound (B) exhibits an anti-inflammatory effect. Furthermore, it was found that the combination of compound (B) and polyphosphate compound (A) further improved the anti-inflammatory effect of compound (B) (see Examples below). Therefore, the oral care composition of the present disclosure, which contains a combination of compound (B) and polyphosphate compound (A), exhibits an excellent anti-inflammatory effect in the oral cavity.
[0011] <Polyphosphate compound (A)> The oral care composition of the present disclosure comprises a polyphosphate compound (A) comprising at least one of polyphosphoric acid and a salt of polyphosphoric acid. For polyphosphoric acid and salts of polyphosphoric acid, reference can be made to known documents such as International Publication No. WO 2004 / 075906, as appropriate.
[0012] As the salt of polyphosphate, alkali metal salts such as sodium salt and potassium salt, or alkaline earth metal salts such as magnesium salt and calcium salt are preferred, alkali metal salts are more preferred, and sodium salt (i.e., sodium polyphosphate) is even more preferred.
[0013] The polyphosphate compound (A) preferably contains at least one of a polyphosphoric acid having a chain length, which is the number of repeating structural units derived from phosphoric acid, of 3 to 300 (more preferably 3 to 150) and a salt of this polyphosphate.
[0014] The polyphosphate compound (A) may contain other components in addition to polyphosphoric acid and salts of polyphosphoric acid. Examples of other components include phosphoric acid compounds such as orthophosphoric acid (H3PO4), metaphosphoric acid, sodium dihydrogen phosphate, and disodium hydrogen phosphate. The total proportion of polyphosphoric acid and salts of polyphosphoric acid in the polyphosphate compound (A) is preferably 60% by mass to 100% by mass, more preferably 80% by mass to 100% by mass, and even more preferably 90% by mass to 100% by mass.
[0015] The content of the polyphosphate compound (A) relative to the total amount of the oral care composition of the present disclosure is preferably 0.01 ppm or more, more preferably 0.1 ppm or more, and even more preferably 1 ppm or more.
[0016] In this disclosure, the simple notation "ppm" means ppm on a mass basis (i.e., "ppm by mass").
[0017] The upper limit of the content of the polyphosphate compound (A) relative to the total amount of the oral care composition of the present disclosure is not particularly limited, but is, for example, 15% by mass, more preferably 5% by mass. When the oral care composition of the present disclosure mainly contains a solvent such as water, for example, as a mouthwash, the upper limit of the content of the polyphosphate compound (A) relative to the total amount of the oral care composition of the present disclosure may be 5 mass % or 2 mass %.
[0018] <Compound (B)> The oral care composition of the present disclosure contains an arginine compound (B1) containing at least one compound selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of this polyamino acid, arginine, and a salt of arginine, and at least one compound (B) selected from the group consisting of a fused polycyclic compound (B2) containing a fused ring in which an aromatic ring and a heterocycle are fused.
[0019] (Arginine Compound (B1)) The arginine compound (B1) as the compound (B) contains at least one member selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of this polyamino acid, arginine, and a salt of arginine.
[0020] Examples of polyamino acids containing structural units derived from arginine include protamine and polyarginine.
[0021] Examples of the salts of polyamino acids and salts of arginine include sulfates, hydrochlorides, acetates, phosphates, and glutamates.
[0022] The total proportion of the polyamino acid containing a structural unit derived from arginine, the salt of this polyamino acid, arginine, and the salt of arginine in the arginine compound (B1) is preferably 60% by mass to 100% by mass, more preferably 80% by mass to 100% by mass, and even more preferably 90% by mass to 100% by mass.
[0023] When compound (B) contains an arginine compound (B1), the proportion of the arginine compound (B1) in compound (B) is preferably 60% by mass to 100% by mass, more preferably 80% by mass to 100% by mass, and even more preferably 90% by mass to 100% by mass.
[0024] One preferred embodiment of compound (B) is an embodiment in which compound (B) contains an arginine compound (B1), and the arginine compound (B1) contains at least one of protamine and a salt of protamine.
[0025] (Fused polycyclic compound (B2)) The fused polycyclic compound (B2) as the compound (B) is a compound containing a fused ring in which an aromatic ring and a heterocycle are fused together. Here, the heterocyclic ring may be a heteroaromatic ring or a heteroaliphatic ring.
[0026] The condensed polycyclic compound (B2) is preferably a compound having a molecular weight of 120 to 1,000 (more preferably 120 to 600).
[0027] Examples of the condensed polycyclic compound (B2) include epicatechin, epicatechin gallate, epigallocatechin, theaflavin, scopoletin, coumarin, etc. The condensed polycyclic compound (B2) preferably contains at least one selected from the group consisting of epicatechin, epicatechin gallate, epigallocatechin, theaflavin, scopoletin, and coumarin.
[0028] When the compound (B) contains a fused polycyclic compound (B2), the proportion of the fused polycyclic compound (B2) in the compound (B) is preferably 60% by mass to 100% by mass, more preferably 80% by mass to 100% by mass, and even more preferably 90% by mass to 100% by mass.
[0029] One preferred embodiment of the compound (B) is one in which the compound (B) contains a condensed polycyclic compound (B2), and the molecular weight of the condensed polycyclic compound (B2) is 120 to 1,000 (more preferably 120 to 600).
[0030] The content of compound (B) relative to the total amount of the oral care composition of the present disclosure is preferably 0.01 ppm or more, more preferably 0.1 ppm or more, and even more preferably 1 ppm or more.
[0031] There is no particular upper limit to the content of compound (B) relative to the total amount of the oral care composition of the present disclosure, but it is, for example, 15% by mass, more preferably 5% by mass. When the oral care composition of the present disclosure mainly contains a solvent such as water, for example, as a mouthwash, the upper limit of the content of compound (B) relative to the total amount of the oral care composition of the present disclosure may be 5% by mass or 2% by mass.
[0032] In the oral care composition of the present disclosure, the mass ratio of polyphosphate compound (A) to compound (B) (i.e., mass ratio [polyphosphate compound (A) / compound (B)]) is preferably 0.01 to 1000, more preferably 0.02 to 500, even more preferably 0.03 to 300, and even more preferably 0.1 to 100.
[0033] The oral care composition of the present disclosure may contain other ingredients in addition to the arginine compound (B1) and compound (B). Other components include solvents (for example, water, ethanol, glycerin, propylene glycol, etc.), additives, and the like. For other components, reference can be made to known documents such as International Publication No. WO 2004 / 075906, as appropriate.
[0034] Oral care compositions of the present disclosure include, for example, mouthwashes, oral moisturizers, dentifrices, and the like.
[0035] The form of the oral care composition of the present disclosure is not particularly limited, and may be, for example, a gel, liquid, paste, or the like. The oral care composition of the present disclosure is preferably a mouthwash, oral moisturizer, or dentifrice.
[0036] [Anti-inflammatory composition] The anti-inflammatory composition of the present disclosure comprises: a polyphosphate compound (A) containing at least one of polyphosphoric acid and a salt of polyphosphoric acid; an arginine compound (B1) containing at least one compound selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine; and a compound (B2) containing at least one compound selected from the group consisting of a fused polycyclic compound containing a fused ring in which an aromatic ring and a heterocycle are fused; Includes.
[0037] The anti-inflammatory composition of the present disclosure contains a combination of polyphosphate compound (A) and the above-mentioned compound (B). These compounds have the same definitions and preferred ranges as the polyphosphate compound (A) and compound (B) contained in the oral care composition of the present disclosure. Therefore, the anti-inflammatory composition of the present disclosure also exhibits excellent anti-inflammatory effects in the oral cavity. Other preferred aspects of the anti-inflammatory composition of the present disclosure (e.g., the content of polyphosphate compound (A) and compound (B), other ingredients, etc.) are the same as the preferred aspects of the oral care composition of the present disclosure.
[0038] [Oral inflammation suppressant] The oral inflammation inhibitor of the present disclosure comprises an arginine compound (B1) containing at least one selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of this polyamino acid, arginine, and a salt of arginine. The arginine compound (B1) is the same as the arginine compound (B1) that may be contained in the oral care composition of the present disclosure. Therefore, the oral inflammation inhibitor of the present disclosure also exhibits excellent inflammation suppression effects in the oral cavity.
[0039] Other preferred aspects of the oral inflammation inhibitor of the present disclosure (for example, the content of the arginine compound (B1), other ingredients, etc.) are the same as the preferred aspects of the oral care composition of the present disclosure. The oral inflammation inhibitor of the present disclosure may further contain the fused polycyclic compound (B2) and / or the polyphosphate compound (A) described above as components of the oral care composition of the present disclosure. [Example]
[0040] Examples of the present disclosure will be shown below, but the present disclosure is not limited to the following examples.
[0041] [Synthesis Example 1] <Synthesis of sodium polyphosphate as polyphosphate compound (A)> Polyphosphate Na (ie, sodium polyphosphate) as the polyphosphate compound (A) was synthesized as follows. Sodium dihydrogen phosphate (manufactured by Shimonoseki Mitsui Chemicals) and disodium hydrogen phosphate (manufactured by Shimonoseki Mitsui Chemicals) were mixed in a ratio such that the molar ratio of Na to P (i.e., the molar ratio [Na / P]) was 1.3, thereby obtaining a mixture that would serve as a raw material for sodium polyphosphate. The resulting mixture (i.e., raw material) was placed in a crucible and melted in this state in a melting furnace heated to 900°C. The resulting melt was dropped onto a pair of metal rollers and rapidly cooled, yielding flaky sodium polyphosphate. The obtained sodium polyphosphate was analyzed by NMR under the following conditions, and it was found that the average chain length of the sodium polyphosphate was 15. Furthermore, measurement using gel permeation chromatography (GPC) under the following conditions confirmed that the sodium polyphosphate contained sodium polyphosphate molecules with chain lengths of 3 to 60.
[0042] (NMR measurement conditions) Equipment: JEOL ECA500 nuclear magnetic resonance spectrometer Measurement nucleus: 31P (202MHz) Measurement mode: Single pulse proton broadband decoupling Pulse width: 30° (3.79 μsec) Number of points: 64k Observation range: 400 ppm (-200 to 200 ppm) Repeat time: 26.0 seconds Number of times accumulated: 256 Measurement solvent: deuterium Sample concentration: ca. 50 mg / 0.6 mL Measurement temperature: room temperature Window function: exponential (BF: 0.50Hz) Chemical shift reference: Maximum peak -23.87 ppm <How to calculate the average chain length> Average chain length=2×α / β+2 (Definition of the symbols "α" and "β" above) α: Peak area derived from P within the sodium polyphosphate chain (P other than that of the terminal structural unit) (chemical shift: -23.87 ppm) β: Peak area derived from P in the terminal structural unit of the sodium polyphosphate chain (chemical shift: -10 to 12 ppm)
[0043] (GPC analysis conditions) -Sample pretreatment- The sample was weighed into a 30 mL vial, 10 mL of mobile phase for GPC analysis was added per 10 mg of sample, and the vial was sealed and left to stand overnight at room temperature for dissolution. The solution was filtered through a 0.45 μm hydrophilic PTFE membrane filter cartridge (Millex-LCR 33 mm; Merck), and the filtrate was used for analysis. -Measurement conditions- Column / Temperature: Two OHpak SB-806M HQ (particle size 13 μm, inner diameter 8.0 mm, length 300 mm, manufactured by Shodex) connected in series / 40°C Mobile phase: 0.1M NaCl aqueous solution Flow rate: 1.0mL / min Injection volume: 100μL Detection method: RI (Refractive Index) Column calibration: EasiVial PEG / PEO polyethylene glycol oxide (Agilent Technologies) Molecular weight calibration: Relative calibration method (PEG / PEO conversion) Equipment: KP-22-13 dual pump (FROM), 717plus automatic injection device (Nihon Waters), RI-101 differential refractive index detector (Shodex)
[0044] Example 1 In Example 1, inflammation was induced in cells using LPS (lipopolysaccharide) derived from Escherichia coli (hereinafter also referred to as "E. coli"), and the protein expression level of IL-8, a type of inflammatory cytokine, was measured to evaluate the inflammation-suppressing effect of a composition containing polyphosphate compound (A) and compound (B) (hereinafter referred to as "experimental sample"), and compound (B) alone (hereinafter referred to as "comparative sample"). The outline of the operation of Example 1 is as follows. first, an aqueous solution of sodium polyphosphate as the aqueous solution of the polyphosphate compound (A); a protamine sulfate solution as a solution of compound (B) (specifically, arginine compound (B1)); and LPS solution containing E. coli-derived LPS for cell stimulation were prepared, respectively. Next, the cells were cultured under each of the following conditions (i) to (vi), and the protein expression level of IL-8, a type of inflammatory cytokine, was measured to evaluate the inflammation suppression effect. (i) A "negative control" in which neither sodium polyphosphate aqueous solution nor protamine sulfate solution was applied, nor LPS stimulation was performed. (ii) "Positive control" with LPS stimulation only (iii) "Experimental sample" (i.e., "with polyphosphate compound (A); (A) + (B)") in which sodium polyphosphate aqueous solution and protamine sulfate solution were applied and LPS stimulation was performed. (vi) "Comparative sample" (i.e., "without polyphosphate compound (A); (B) alone") in which only protamine sulfate solution was applied and LPS stimulation was performed without applying sodium polyphosphate aqueous solution. The operation of Example 1 will be described in detail below.
[0045] 1. Preparation of Sodium Polyphosphate Aqueous Solution The sodium polyphosphate obtained in Synthesis Example 1 (containing sodium polyphosphate molecules with a chain length of 3 to 60) was diluted with endotoxin-free water to prepare an aqueous sodium polyphosphate solution with a sodium polyphosphate concentration of 50,000 ppm (5% by mass).
[0046] 2. Preparation of Protamine Sulfate Solution Salmon-derived protamine sulfate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was diluted with dimethyl sulfoxide to prepare a protamine sulfate solution with a protamine sulfate concentration of 10,000 ppm (1% by mass). This salmon-derived protamine sulfate is the main component of protein extracted from fish testes and contains approximately 60% arginine.
[0047] 3. Preparation of LPS Solution E. coli-derived LPS (Sigma-Aldrich) was diluted with endotoxin-free water to prepare an LPS solution with an LPS concentration of 50,000 ppm (5% by mass).
[0048] 4. Test Cell Preparation Ca9-22 cells, human oral squamous cell carcinoma cells, were dispersed in MEM medium supplemented with 10% fetal bovine serum (SERANA EUROPE GMBH) and seeded at 105 cells / well in a 24-well plate. They were then cultured in a CO2 incubator (CO2: 5%, 37°C) for 2-3 days until they reached 90-100% confluence. The medium was then replaced with serum-free MEM medium and cultured for 1 day to prepare the test cells.
[0049] 5. Cultivation of test cells and collection of culture supernatant (1) Next, test cells were cultured under the following four conditions (i) to (vi). (i) "Negative control" The serum-free MEM medium containing the test cells was cultured for 24 hours in a CO2 incubator (CO2: 5%, 37°C) without adding anything. (ii) "Positive control" An LPS solution was added to the serum-free MEM medium containing the test cells so that the final LPS concentration was 35 ppm, and the cells were then cultured in a CO2 incubator (CO2: 5%, 37°C) for 24 hours. (iii) "Experimental sample" (i.e., "with polyphosphate compound (A) or with polyphosphate compound (A) and compound (B)") Aqueous sodium polyphosphate solution, protamine sulfate solution, and LPS solution were added to serum-free MEM medium containing the test cells so that the final concentrations of sodium polyphosphate, protamine sulfate, and LPS were 10 ppm, 10 ppm, and 35 ppm, respectively, and the cells were then cultured in a CO2 incubator (CO2: 5%, 37°C) for 24 hours. (vi) "Comparative sample" (i.e., "No polyphosphate compound (A); Compound (B) alone") Protamine sulfate solution and LPS solution were added to serum-free MEM medium containing the test cells so that the final concentration of protamine sulfate was 10 ppm and the final concentration of LPS was 35 ppm, and the cells were then cultured in a CO2 incubator (CO2: 5%, 37°C) for 24 hours. (2) After culturing under each of the conditions (i) to (vi) above, the culture supernatant was collected and centrifuged, and the resulting supernatant was used to evaluate the inflammation suppression effect (inflammation suppression rate (%)) for each of the experimental and comparative samples.
[0050] 6. Evaluation of the anti-inflammatory effects of the experimental and comparative samples The amount of IL-8 in each of the supernatants under the above conditions (i) to (vi) was determined using an IL-8 Human Uncoated ELISA Kit (Invitrogen). Specifically, anti-IL-8 antibody was first immobilized on a plate, and the supernatant was then added. Next, horseradish peroxidase (HRP)-labeled antibody was added, followed by a colorimetric reagent containing the substrate for the 3,3',5,5'-tetramethylbenzidine (TMB)-labeled enzyme. The amount of IL-8 in the supernatant was then determined by colorimetry using a multiplate reader. Based on the amount of IL-8 in the supernatant under each of the above conditions (i) to (vi), the inflammation inhibition rate (%) of the experimental sample and the inflammation inhibition rate (%) of the comparative sample were calculated using the following formula. The results are shown in Table 1. where: An inflammation inhibition rate (%) of 100% means that the amount of IL-8 in the experimental sample or comparative sample was reduced to the same amount as the amount of IL-8 in the negative control (i.e., the inflammation inhibition effect was extremely high). An inflammation inhibition rate (%) of 0% means that the amount of IL-8 in the experimental sample or comparative sample was the same as the amount of IL-8 in the positive control (i.e., there was no inflammation inhibition effect).
[0051] Inflammation suppression rate (%) of experimental specimens = 100 - 100 × (IL-8 level in experimental sample - IL-8 level in negative control) / (IL-8 level in positive control - IL-8 level in negative control) Inflammation suppression rate (%) of control sample = 100 - 100 × ("IL-8 amount in the comparison sample" - "IL-8 amount in the negative control") / ("IL-8 amount in the positive control" - "IL-8 amount in the negative control")
[0052] Example 2 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was replaced with L-(+)-arginine (final concentration 100 ppm) as compound (B) (specifically, arginine compound (B1)). The results are shown in Table 1. In this example, an aqueous solution of L-(+)-arginine with a concentration of 50,000 ppm (5% by mass) was used, which was obtained by diluting L-(+)-arginine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) with endotoxin-free water.
[0053] Example 3 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was changed to (-)-epicatechin (hereinafter, epicatechin) (final concentration 2 ppm) as compound (B) (specifically, condensed polycyclic compound (B2)). The results are shown in Table 1. In this example, an epicatechin solution with a concentration of 10,000 ppm (1% by mass) obtained by diluting epicatechin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) with dimethyl sulfoxide was used.
[0054] Example 4 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was changed to (-)-epicatechin gallate (hereinafter, epicatechin gallate) (final concentration 2 ppm) as compound (B) (specifically, condensed polycyclic compound (B2)). The results are shown in Table 1. In this example, an epicatechin gallate solution with a concentration of 10,000 ppm (1% by mass) obtained by diluting epicatechin gallate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) with dimethyl sulfoxide was used.
[0055] Example 5 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was changed to (-)-epigallocatechin (hereinafter referred to as epigallocatechin) (final concentration 0.1 ppm) as compound (B) (specifically, condensed polycyclic compound (B2)). The results are shown in Table 1. In this example, an epigallocatechin solution with a concentration of 10,000 ppm (1% by mass) obtained by diluting epigallocatechin (manufactured by Tokyo Chemical Industry Co., Ltd.) with dimethyl sulfoxide was used.
[0056] Example 6 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was changed to theaflavin (final concentration 2 ppm) as compound (B) (specifically, condensed polycyclic compound (B2)). The results are shown in Table 1. In this example, a theaflavin solution with a concentration of 10,000 ppm (1% by mass) obtained by diluting theaflavin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) with dimethyl sulfoxide was used.
[0057] Example 7 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was changed to scopoletin (final concentration 0.1 ppm) as compound (B) (specifically, condensed polycyclic compound (B2)). The results are shown in Table 1. In this example, a scopoletin solution with a concentration of 10,000 ppm (1% by mass) obtained by diluting scopoletin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) with dimethyl sulfoxide was used.
[0058] Example 8 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was changed to coumarin (final concentration 0.1 ppm) as compound (B) (specifically, condensed polycyclic compound (B2)). The results are shown in Table 1. In this example, a coumarin solution with a concentration of 10,000 ppm (1% by mass) obtained by diluting coumarin (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) with dimethyl sulfoxide was used.
[0059] Comparative Example 1 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) was not used as compound (B) (specifically, arginine compound (B1)). The results are shown in Table 1.
[0060] Comparative Example 2 The same procedure as in Example 1 was carried out, except that protamine sulfate (final concentration 10 ppm) as compound (B) (specifically, arginine compound (B1)) was changed to polylysine (final concentration 10 ppm), which is a comparative compound not corresponding to compound (B). The results are shown in Table 1. In this example, a polylysine solution with a concentration of 10,000 ppm (1% by mass) obtained by diluting polylysine (manufactured by JNC Corporation) with dimethyl sulfoxide was used.
[0061] [Table 1]
[0062] The structure of the compound (B) in Examples 2 to 8 and the structure of the polylysine in Comparative Example 2 are as follows:
[0063] [ka]
[0064] In Table 1, a comparison of Examples 1 to 8 with Comparative Example 1 reveals that arginine compound (B1) containing at least one compound selected from the group consisting of polyamino acids containing structural units derived from arginine, salts of polyamino acids, arginine, and salts of arginine, and compound (B) which is at least one compound selected from the group consisting of fused polycyclic compounds (B2) containing a fused ring in which an aromatic ring and a heterocycle are fused, exhibits an anti-inflammatory effect. From Examples 1 to 8 in Table 1, it can be seen that compositions containing compound (B) and polyphosphate compound (A) (experimental samples) have a superior anti-inflammatory effect compared to compound (B) alone (comparative sample). In contrast, in Comparative Example 2, in which polylysine, a comparative compound, was used instead of compound (B), it was found that the anti-inflammatory effect was impaired when polylysine and polyphosphate compound (A) were used in combination.
[0065] From the above results, it can be seen that an oral inflammation inhibitor containing an arginine compound (B1) containing at least one selected from the group consisting of polyamino acids containing structural units derived from arginine, salts of polyamino acids, arginine, and salts of arginine exhibits excellent inflammation inhibitory effects. It is also found that an oral care composition or anti-inflammatory composition containing a polyphosphate compound (A) containing at least one of polyphosphoric acid and a salt of polyphosphate, an arginine compound (B1) containing at least one selected from the group consisting of polyamino acids containing structural units derived from arginine, salts of polyamino acids, arginine, and salts of arginine, and a compound (B) which is at least one selected from the group consisting of fused polycyclic compounds (B2) containing a fused ring in which an aromatic ring and a heterocycle are fused, exhibits excellent anti-inflammatory effects.
Claims
1. a polyphosphate compound (A) containing at least one of polyphosphoric acid and a salt of polyphosphoric acid; an arginine compound (B1) containing at least one compound selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine; and a compound (B2) containing at least one compound selected from the group consisting of a fused polycyclic compound containing a fused ring in which an aromatic ring and a heterocycle are fused; 1. An oral care composition comprising:
2. 2. The oral care composition according to claim 1, wherein the polyphosphate compound (A) comprises at least one of a polyphosphate having a chain length, which is the number of repeating structural units derived from phosphoric acid, of 3 to 300 and a salt of the polyphosphate.
3. the compound (B) contains the arginine compound (B1), The arginine compound (B1) contains at least one of protamine and a salt of protamine. The oral care composition of claim 1 .
4. the compound (B) contains the fused polycyclic compound (B2), The molecular weight of the condensed polycyclic compound (B2) is 120 to 1000. The oral care composition of claim 1 .
5. 10. The oral care composition of claim 1, which is a mouthwash, oral moisturizer, or dentifrice.
6. a polyphosphate compound (A) containing at least one of polyphosphoric acid and a salt of polyphosphoric acid; an arginine compound (B1) containing at least one compound selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine; and a compound (B2) containing at least one compound selected from the group consisting of a fused polycyclic compound containing a fused ring in which an aromatic ring and a heterocycle are fused; An anti-inflammatory composition comprising:
7. An oral inflammation inhibitor comprising an arginine compound (B1) containing at least one member selected from the group consisting of a polyamino acid containing a structural unit derived from arginine, a salt of the polyamino acid, arginine, and a salt of arginine.
Citation Information
Patent Citations
Antiinflammtory agent and antiinflammatory medical material
WO2004075906A1