JP7445908B2 - Oral composition containing curcuminoids and antibacterial method - Google Patents

Description

The present invention relates to a curcuminoid-containing oral composition and an antibacterial method. More specifically, the present invention relates to an oral composition containing a curcuminoid and a specific polyglycerin fatty acid ester, an agent for treating and/or preventing periodontal disease, and an antibacterial method.

Curcuminoids containing curcumin ((1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, C21H20O6: molecular weight approximately 368.38 g/mol) are It is a group of yellow polyphenol compounds contained in the rhizome of the plant turmeric, and is widely used not only as a spice or dye for curry, but also as a health food material with anti-inflammatory, anti-tumor, and antioxidant effects. Furthermore, in recent years, it has been expected to be used in oral hygiene agents (Non-Patent Document 1).

Generally, so-called good bacteria and bad bacteria exist in the oral cavity, and the balance of bacteria is said to be related to the occurrence of tooth decay and periodontal disease. General disinfectants kill bacteria without distinguishing between bad bacteria and good bacteria, and are not effective in maintaining this kind of bacterial balance.

Izui et al. , Antibacterial Activity of Curcumin Against Periodontopathic Bacteria.J Periodontol, 87(1):83-90, 2016

While curcuminoids suppress the growth of periodontal disease bacteria, they do not suppress the growth of resident bacteria, and can be said to be useful substances as oral hygiene agents. However, since curcuminoids are poorly water-soluble, the amount dissolved in oral hygiene agents is extremely small, making it difficult to fully demonstrate their antibacterial activity. Poorly water-soluble components are often dissolved using solubilizers such as surfactants, but antibacterial components may be incorporated into micelles, impairing their antibacterial properties. Furthermore, when using oral hygiene products that contain curcuminoids, which are pigments, toothbrushes, sinks, etc. may become discolored. Due to these issues, an oral hygiene agent with enhanced antibacterial activity is desired without increasing the amount of curcuminoids.

The present invention provides an oral composition that contains curcuminoids and is particularly effective in treating and/or preventing periodontal disease, an agent for treating and/or preventing periodontal disease, and an antibacterial method. With the goal.

The present inventors have made extensive studies to solve the above problems, and have found that by including polyglycerin fatty acid ester with an HLB of 14 or more together with curcuminoids, its antibacterial effect is enhanced, and it can be used for the treatment of periodontal disease. The inventors have discovered that the present invention is effective as a preventive agent and have achieved the present invention.

That is, the present invention relates to an oral composition, a therapeutic and/or preventive agent for periodontal disease, and a method for improving antibacterial properties as described below.
Item 1.
An oral composition for the treatment and/or prevention of periodontal disease, comprising (A) a curcuminoid; and (B) a polyglycerin fatty acid ester having an HLB of 14 or more.
Item 2.
Item 1. The composition for oral cavity according to Item 1, wherein the content of the component (A) is 0.00001 to 0.01% by mass, and the content of the component (B) is 0.001 to 5% by mass. thing.
Item 3.
Item 3. The oral composition according to item 1 or 2, which does not substantially contain polyoxyethylene hydrogenated castor oil.
Item 4.
A therapeutic and/or preventive agent for periodontal disease caused by Porphyromonas gingivalis, which contains (A) a curcuminoid; and (B) a polyglycerin fatty acid ester with an HLB of 14 or more.
Item 5.
Item 5. The periodontal disease treatment and/or prevention agent according to item 4, which does not substantially contain polyoxyethylene hydrogenated castor oil.
Item 6.
(A) A method of improving the antibacterial properties of a composition containing curcuminoids against Porphyromonas gingivalis by blending (B) a polyglycerin fatty acid ester with an HLB of 14 or more into the composition.

ADVANTAGE OF THE INVENTION The present invention provides a composition that has enhanced antibacterial action against specific bacteria in the mouth and is particularly effective as a therapeutic and/or preventive agent for periodontal disease.

The present invention
The present invention relates to an oral composition for treating and/or preventing periodontal disease, which contains (A) a curcuminoid; and (B) a polyglycerin fatty acid ester with an HLB of 14 or more.

[Oral composition for treatment and/or prevention of periodontal disease]
The oral composition of the present invention is an oral composition for treating and/or preventing periodontal disease, which contains (A) a curcuminoid; and (B) a polyglycerin fatty acid ester having an HLB of 14 or more.

((A) Curcuminoid)
The curcuminoids of component (A) used in the present invention typically include curcumin, demethoxycurcumin, and bisdemethoxycurcumin.
Among these, curcumin refers to (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione (C21H20O6: molecular weight 368.38 g/mol) . This compound undergoes keto-enol tautomerization and may be in any form.
Demethoxycurcumin is (E,E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (C20H18O5: molecular weight 338. 35g/mol).
Bisdemethoxycurcumin refers to (E,E)-1,7-bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (C19H16O4: molecular weight: 308.33 g/mol).
The curcuminoid may also be a solvent extract or powder of a plant containing curcuminoid, such as the rhizome of the plant turmeric. Here, the plant is not particularly limited, but the rhizome of turmeric can be used, and the type of turmeric, such as spring turmeric and autumn turmeric, is not particularly limited as long as the content of curcuminoid is a specified amount.
Various forms can be used, such as a solvent-based extract of turmeric rhizomes and finely ground turmeric powder.

Commercially available products may be used as curcumin, demethoxycurcumin, and bisdemethoxycurcumin. For example, examples of curcumin, demethoxycurcumin, or bisdemethoxycurcumin alone include curcumin reagent, demethoxycurcumin reagent, and bisdemethoxycurcumin reagent manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.; An example of the turmeric extract is turmeric extract BG manufactured by NOF Corporation, and an example of the turmeric powder is Aki turmeric powder 100% manufactured by Ito Kampo Pharmaceutical Co., Ltd.

The content of curcuminoid in the oral composition of the present invention is preferably 0.00001 to 0.01% by mass, more preferably 0.00003 to 0.003% by mass of the entire composition in terms of pure curcuminoid. Within this range, curcuminoids can fully exhibit their effects on oral bacteria.

((B) Polyglycerin fatty acid ester with HLB of 14 or more)
Component (B) used in the present invention is a polyglycerin fatty acid ester having an HLB of 14 or more. Here, HLB (Hydrophile Lipophile Balance) can be calculated from the saponification value and the acid value of the constituent fatty acids using the following formula.
HLB=20×(1-S/A)
S: saponification value, A: acid value of constituent fatty acids

Although the polyglycerin fatty acid ester is not limited as long as it has an HLB of 14 or more, it is preferably an ester of decaglycerin and a fatty acid with an average degree of polymerization of 10. Among these, more preferred is an ester of decaglycerin with an average degree of polymerization of 10 and a fatty acid having 12 to 16 carbon atoms, and even more preferred is an ester of decaglycerin with an average degree of polymerization of 10 and lauric acid or myristic acid. , most preferably polyglyceryl-10 myristate.

The content of polyglycerin fatty acid ester in the oral composition of the present invention is preferably 0.001 to 5% by mass, and 0.001 to 1.5% by mass from the viewpoint of exhibiting the effect of inhibiting bacterial growth, which is the effect of the present invention. Mass% is more preferred.

The content ratio of component (B) to component (A) is preferably 0.1 to 500,000 parts by mass, more preferably 1 to 10,000 parts by mass of component (B) per 1 part by mass of component (A). The proportion is preferably 3 to 5000 parts by weight, even more preferably 5 to 5000 parts by weight. By keeping the ratio within this range, a higher antibacterial effect can be exhibited, and furthermore, coloring of the object can be suppressed.

The oral composition of the present invention preferably does not substantially contain polyoxyethylene hydrogenated castor oil. Here, preferably no polyoxyethylene hydrogenated castor oil is contained.

(moisture)
The oral composition of the present invention can contain water. The water used in the present invention may be any water that does not impair the effects of the present invention, and preferably includes purified water, distilled water, ion-exchanged water, and RO water.
The content of water contained in the oral composition of the present invention is preferably 10 to 99.9988% by mass, more preferably 20 to 99% by mass, and even more preferably 30 to 90% by mass. The presence of water allows the components (A) and (B) to be stably dissolved, making it possible to sufficiently distribute the components in the oral cavity.

(Other ingredients)
The oral composition of the present invention can optionally contain other components in addition to (A) curcuminoids and (B) polyglycerin fatty acid esters with an HLB of 14 or more. Here, other ingredients include, but are not limited to, wetting agents, preservatives, cleaning agents (abrasives), binders, pH adjusters, flavoring agents, medicinal ingredients, foaming agents, cooling agents, flavoring agents, In addition to sweeteners, it also contains moisturizers, colorants, etc.

Examples of wetting agents include sorbitol, glycerin, concentrated glycerin, propylene glycol, butylene glycol, polyethylene glycol, and the like. Wetting agents may be used alone or in combination of two or more. Although not limited, it is preferable to include at least propylene glycol and sorbitol, and a combination of propylene glycol and sorbitol can also be used. For example, sorbitol is preferably 0.05 to 40 parts by weight, more preferably 0.1 to 20 parts by weight, even more preferably 0.1 to 10 parts by weight, and even more preferably 0.5 to 10 parts by weight, per 1 part by weight of propylene glycol. Parts by weight are most preferred.

The content of such wetting agents is not limited, but when included, the total amount of wetting agents is 1 to 60% by mass, more preferably 5 to 50% by mass, and even more preferably 10 to 40% by mass. But it's possible. By including the wetting agent, components (A) and (B) are stably dissolved, and the appearance stability of the composition is improved. Furthermore, it is possible to improve the flavor, such as the balance of sweetness and bitterness, and to provide an appropriate moisturizing feeling without feeling sticky after use.

Although not limited, the content of propylene glycol may preferably be 0.1 to 20% by weight, 1 to 20% by weight, 5 to 20% by weight, etc.

Although not limited, the content of sorbitol may preferably be 0.1 to 40% by weight, 1 to 40% by weight, 5 to 30% by weight, etc.

Examples of preservatives include paraoxybenzoic acid esters such as sodium benzoate, methylparaben, ethylparaben, and butylparaben. The preservatives may be used alone or in combination of two or more. The content of such preservatives is not limited, but is preferably 0.01 to 5% by weight, more preferably 0.05 to 3% by weight, and even more preferably 0.01 to 2% by weight.

Cleaning agents (abrasives) include calcium carbonate, heavy calcium carbonate, aluminum hydroxide, alumina, magnesium carbonate, tribasic magnesium phosphate, zirconium silicate, tribasic calcium phosphate, hydroxyapatite, quaternary calcium phosphate, and synthetic resins. Examples include abrasives and the like. The cleaning agents may be used alone or in combination of two or more.

Examples of the binder include sodium carboxymethyl cellulose, xanthan gum, silicic anhydride, carrageenan, alginic acid and its salts. The binder may be used alone or in combination of two or more.

Examples of pH adjusters include sodium citrate, citric anhydride, acetic acid, hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, malic acid, gluconic acid, maleic acid, succinic acid, glutamic acid, sodium hydroxide, potassium hydroxide, sodium acetate, Examples include sodium carbonate, sodium phosphate, sodium dihydrogen phosphate, and the like. The pH adjusters may be used alone or in combination of two or more.

Examples of flavoring agents include natural flavors such as essential oils (ginger oleoresin, ginger mint), synthetic flavors, and the like.

Medicinal ingredients include sodium monofluorophosphate, sodium fluoride, dipotassium glycyrrhizinate, and the like. The medicinal ingredients may be used alone or in combination of two or more.

Examples of the blowing agent include sodium lauroylmethyltaurate, sodium lauryl sulfate, and sodium polyoxyethylene lauryl ether sulfate. The foaming agents may be used alone or in combination of two or more.

As a refreshing agent, menthol such as l-menthol, N-ethyl-p-menthane-3-carboxamide, N-(ethoxycarbonylmethyl)-3-p-menthanecarboxamide, N,2,3-trimethyl-2- Isopropyl butanamide, 3-(L-methoxy)propane-1,2-diol, menthyl lactate (menthyl lactate), monomenthyl succinate, menthone glycerin acetal, 3-l-menthoxypropane-1,2-diol, menthyl glycerin Examples include ether, spilanthol, monomenthyl succinate, and the like. The refreshing agent may be used alone or in combination of two or more.

Examples of flavoring agents include sodium chloride.

Examples of sweeteners include xylitol, sodium saccharin, stevioside, neohesperidin hydrochalcone, glycyrrhizin, thaumatin, palatinose, maltitol, arabitol, and the like. The sweeteners may be used alone or in combination of two or more.

(Form of oral composition)
The form of the oral composition of the present invention may be liquid, semi-solid, or solid. Semi-solids include pastes or gels. The preferred form of the oral composition of the present invention is liquid, paste, or gel.

When the oral composition of the present invention is a liquid, the pH at 25° C. is preferably 4.5 to 9, more preferably 5 to 8.5, and even more preferably 6 to 8.

(Applications of oral composition)
The oral composition of the present invention can be used, for example, in dentifrices such as toothpastes, liquid dentifrices, and gel toothpastes, mouthwashes, gargles, mouth fresheners, oral liniments, or foods. can. Foods include chewing gum, candy tablets, troches, and the like. The oral composition of the present invention can be used particularly as a therapeutic and/or preventive agent for periodontal disease caused by Porphyromonas gingivalis. In particular, it is possible to obtain the effects of inhibiting biofilm formation in the mouth and inhibiting the adhesion of toxin vesicles caused by Porphyromonas gingivalis.

(Container for oral composition)
The material of the container for storing the oral composition of the present invention is not particularly limited, and containers used for common dentifrices, mouthwashes, etc., such as polypropylene, polyethylene, polyethylene terephthalate, and aluminum, can be selected. The shape of the storage container is not particularly limited either, and examples thereof include tubes, bottles, packs, potions, and the like.

[Treatment and/or prevention agent for periodontal disease caused by Porphyromonas gingivalis]
The present invention also includes a therapeutic and/or preventive agent for periodontal disease caused by Porphyromonas gingivalis, which contains (A) a curcuminoid; and (B) a polyglycerin fatty acid ester with an HLB of 14 or more. In the therapeutic and/or preventive agent for periodontal disease of the present invention, each component and its content, as well as other components and their content, are in accordance with the contents described in the oral cavity composition. Furthermore, it is preferable that the therapeutic and/or preventive agent for periodontal disease does not substantially contain polyoxyethylene hydrogenated castor oil.

[Method for improving antibacterial properties against Porphyromonas gingivalis]
The present invention also includes a method of improving the antibacterial properties of a composition containing (A) curcuminoid against Porphyromonas gingivalis by blending (B) a polyglycerin fatty acid ester with an HLB of 14 or more into the composition. . In the method of the present invention, each component and its content, as well as other components and their content, are in accordance with those described for the oral composition. Furthermore, also in the method of the present invention, it is preferable that the composition does not substantially contain polyoxyethylene hydrogenated castor oil.

Hereinafter, the content of the present invention will be specifically explained using the following examples, but the present invention is not limited to these in any way.

The components used in the examples are as follows.
Curcuminoids: Curcumin (Fujifilm Wako Pure Chemical Industries, Ltd.), Turmeric Extract BG (NOF Corporation)
Hinokitiol: Hinokitiol (Tokyo Kasei Kogyo Co., Ltd.)
Thymol: Thymol (Tokyo Kasei Kogyo Co., Ltd.)
Catechin: Epigallocatechin gallate (BioVerde Co., Ltd.)
Polyglyceryl-10 laurate: Decaglyn 1-L (Nikko Chemicals Co., Ltd.), HLB 15.5
Polyglyceryl myristate-10: Decaglyn 1-M (Nikko Chemicals Co., Ltd.), HLB 14.0
Glyceryl caprate: Sunsoft No. 760-C (Taiyo Kagaku Co., Ltd.), HLB 6.5
Polyoxyethylene hydrogenated castor oil: NIKKOL HCO-60Y (Nikko Chemicals Co., Ltd.), HLB 14.0
Propylene glycol: Japanese Pharmacopoeia Propylene Glycol (ADEKA Co., Ltd.)
Sorbitol: Sorbitol S (Bussan Food Science Co., Ltd.)
Concentrated glycerin: Concentrated glycerin (IOI ACIDCHEM)
Methylparaben: Meccins-M (Ueno Pharmaceutical Co., Ltd.)
Sodium carboxymethylcellulose: CMC Daicel 1380 (Daicel Millize Co., Ltd.)
Xanthan gum: Keldent SFT (DSP Gokyo Food & Chemical Co., Ltd.)

[Example of evaluation of naturally derived ingredients]
The antibacterial properties of the naturally derived ingredients shown in Table 1 below were investigated.
Specifically, first, an evaluation preparation was prepared in which 1% of naturally derived ingredients were dissolved in dimethyl sulfoxide (DMSO). This evaluation preparation was added to each liquid medium so that the final concentration of naturally-derived components in the preparation was 0.05%, and further diluted 2-fold using the liquid medium. 0.1 mL of each diluted solution was added to a 96-well plate, and 0.01 mL of each test bacterial solution was added.

After culturing Porphyromonas gingivalis under anaerobic conditions at 37°C for 2 days, and other bacteria overnight at 37°C, the presence or absence of turbidity of the culture solution was confirmed, and the minimum inhibitory concentration was determined.

The test bacterial solutions of each bacteria used in this protocol were prepared as follows.

Using a Porphyromonas gingivalis bacterial suspension preparation plate medium, the cells were cultured at 37° C. under anaerobic conditions for 2 days. Colonies were suspended in 10 mL of liquid medium and cultured overnight at 37°C under anaerobic conditions.
Plate medium: CDC sheep blood agar medium for anaerobic bacteria (manufactured by BD)
Liquid medium:
Trypticase Soy Broth (BD Company) 3w/v%
Yeast Extract (BD Company) 0.1w/v%
Hemin (Fujifilm Wako Pure Chemical Industries, Ltd.) 0.0005w/v%
Menadione (Fujifilm Wako Pure Chemical Industries, Ltd.) 0.0001w/v%
Purified water residue

The cells were cultured at 37° C. for 2 days using a Streptococcus mutans bacterial suspension preparation plate medium. Colonies were suspended in 10 mL of liquid medium and cultured overnight at 37°C.
Plate medium: Brain heart infusion broth (manufactured by Nissui Pharmaceutical Co., Ltd.) + 1.5 w/v% agar Liquid medium: Brain heart infusion broth (manufactured by Nissui Pharmaceutical Co., Ltd.)

The cells were cultured at 37° C. for 2 days using a bacterial liquid preparation plate medium of Streptococcus gordonii and Streptococcus oralis. Colonies were suspended in 10 mL of liquid medium and cultured overnight at 37°C.
Plate medium: THB medium (manufactured by BD) + 2w/v% agarose Liquid medium: THB medium (manufactured by BD)

Based on the following evaluation criteria, the level of antibacterial properties was evaluated based on the minimum inhibitory concentration, and the presence or absence of selective antibacterial properties of each naturally derived ingredient was verified.
〇 15.6μg/mL or less△ More than 15.6μg/mL and 62.5μg/mL or less × More than 62.5μg/mL

In the table, P. gingivalis stands for Porphyromonas gingivalis ATCC33277, which is S. gingivalis. mutans stands for Streptococcus mutans JCM5705, S. gordonii stands for Streptococcus gordonii DL-1; oralis stands for Streptococcus oralis ATCC9811.

From this result, curcumin is found in Porphyromonas gingivalis.
A selective growth-inhibiting effect was confirmed. On the other hand, hinokitiol does not have such selectivity, and no effect was observed with thymol or catechin at concentrations similar to those of curcumin, which was effective.

[Example 1]
The compositions shown in Table 2 were prepared, and these compositions were evaluated for their growth inhibitory effects on Porphyromonas gingivalis.

(Preparation method)
The amount of each component was adjusted so that the final concentration of component (A) and component (B) or comparative component, that is, the concentration at the time of action on bacteria, was the concentration shown in Table 2.
Each surfactant component shown in Table 2 was heated to melting temperature, and curcuminoids were added and mixed. Furthermore, water was added little by little while stirring to prepare an oral composition.

(Evaluation method)
The antibacterial properties of oral compositions prepared such that the final concentrations of component (A) and component (B) or comparative components were as shown in Table 2 were evaluated. Antibacterial properties were evaluated as follows.
Porphyromonas gingivalis ATCC33277 was inoculated into a liquid medium (same as described in the above [Example of Evaluation of Naturally Derived Components]), and precultured overnight at 37°C. This culture solution was diluted 10 times with a liquid medium and used as a test bacterial solution. 1 mL of the 10-fold concentrated oral composition shown in Table 2 was added to 9 mL of the test bacterial solution, and the absorbance at a wavelength of 600 nm was measured as turbidity with a SHIMADZU ultraviolet/visible spectrophotometer UV-1200 immediately after preparation and 48 hours later.
The results were evaluated as the enhancement rate of the growth inhibitory effect based on the following evaluation criteria.
Example 1-1, Example 1-2, Comparative Example 1-1, and Comparative Example 1-2 were evaluated based on Reference Example 1-1.
Growth inhibitory effect enhancement rate (%) = 100 - {(turbidity of each composition after 48 hours - turbidity of each composition immediately after preparation) / (turbidity of Reference Example 1-1 after 48 hours - Turbidity immediately after preparation of Reference Example 1-1) x 100}
Example 1-3, Comparative Example 1-3, and Comparative Example 1-4 were evaluated based on Reference Example 1-2.
Growth inhibitory effect enhancement rate (%) = 100 - {(turbidity of each composition after 48 hours - turbidity of each composition immediately after preparation) / (turbidity of Reference Example 1-2 after 48 hours - Turbidity immediately after preparation of Reference Example 1-2) x 100}
×: Enhancement rate of growth inhibitory effect is 49% or less △: Enhancement rate of growth inhibitory effect is 50% or more and 74% or less ○: Enhancement rate of growth inhibitory effect is 75% or more

As a result of this verification, polyglyceryl-10 laurate and polyglyceryl-10 myristate, when containing 0.0002% curcuminoid, enhanced the growth-inhibiting effect of curcuminoid alone by 75% or more. Furthermore, even when polyglyceryl-10 myristate contained 0.001% curcuminoid, the enhancement rate of the growth inhibitory effect was remarkable at 75% or more. On the other hand, for glyceryl caprate and polyoxyethylene hydrogenated castor oil, the enhancement rate of the growth inhibitory effect was 49% or less when the curcuminoid content was 0.0002% or 0.001%.

[Example 2]
As shown in Table 3, curcuminoids, polyglycerin fatty acid esters, and various components were prepared according to the following methods and tested on 18 test subjects.

(Preparation method)
Each surfactant component shown in Table 3 was heated to melting temperature, and curcuminoids and propylene glycol were added and mixed. Further, other ingredients and water were added little by little while stirring to prepare an oral composition.

(Evaluation method)
The oral composition prepared with the composition shown in Table 3 was used twice a day (morning and evening) for two weeks.
Before and after the test, dental plaque was collected from specific interdental spaces and suspended in PBS buffer. The sample from which the PBS buffer was removed by centrifugation was used as a test sample. The test specimen was suspended in an enzyme solution (0.12 mL of 5 mg/mL lysozyme (manufactured by Fuji Film Wako Pure Chemical Industries, Ltd.), 0.022 mL of 5000 U/mL mutanolysin (manufactured by Sigma-Aldrich)), and treated at 50° C. for 1 hour. After processing, the bacterial genome was extracted from the processed specimen according to the instructions for using the "Wizard (registered trademark) Genomic DNA Purification kit (manufactured by Promega Corporation)" and then extracted using Nanodrop ND-1000 (manufactured by Thermo Fisher Scientific). The amount of nucleic acid was confirmed using Using the obtained genome as a template, a universal primer targeting the 16s rRNA gene and Por
Real-time PCR was performed using a primer/probe set specific to Phyromonas gingivalis (reagent: Thunderbird Probe qPCR Mix (manufactured by Toyobo Co., Ltd.), detector: Rotergene Q). A calibration curve was created from the Ct value and the amount of nucleic acid, and the proportion of Porphyromonas gingivalis to the total number of bacteria contained in each sample was calculated. As primers for PCR, Kuboniwa M et al. , Quantitative detection of periodontal pathogens using real-time polymerase chain reaction with Taqman probes. , Oral Microbiology Immunology, vol. 19, p168-p176, 2004, were used.

The effect of reducing the proportion of Porphyromonas gingivalis in dental plaque was evaluated based on the criteria shown below.
×: The proportion of Porphyromonas gingivalis decreased in 0 to 9% of subjects. △: The proportion of Porphyromonas gingivalis decreased in 10 to 29% of subjects. 〇: The proportion of Porphyromonas gingivalis decreased in 30 to 49% of subjects. Wow ◎: The proportion of Porphyromonas gingivalis decreased in 50% or more of the subjects.

As a result, with the compositions of Examples, whether in the form of mouthwash or gel, a certain percentage or more of subjects showed a decrease in the proportion of Porphyromonas gingivalis in dental plaque.
Furthermore, the compositions of Examples had good stability in appearance, no coloring of objects, and a good feeling of use such as a moisturizing feeling.
The compositions of each comparative example did not show as much effect as the compositions of the examples.

[Composition example]
An oral composition of the present invention was prepared based on the formulation shown below.

<Composition Example 1> Liquid dentifrice curcuminoid 0.0002% by mass
Polyglyceryl myristate-10 0.5% by mass
Propylene glycol 5% by mass
Sorbitol 10% by mass
Methylparaben 0.1% by mass
Dipotassium glycyrrhizinate 0.1% by mass
Sodium lauroylmethyltaurate 0.1% by mass
Sodium citrate 0.3% by mass
Fragrance 0.5% by mass
water residue

<Composition Example 2> Toothpaste curcuminoid 0.001% by mass
Polyglyceryl myristate-10 1.5% by mass
Propylene glycol 10% by mass
Sorbitol 20% by mass
Methylparaben 0.1% by mass
Dipotassium glycyrrhizinate 0.1% by mass
Sodium lauroylmethyltaurine 0.5% by mass
Citric acid 0.2% by mass
Carboxymethylcellulose sodium 3% by mass
Silicic anhydride 5% by mass
Calcium carbonate 25% by mass
Fragrance 0.5% by mass
water residue

<Composition Example 3> Gel dentifrice curcuminoid 0.001% by mass
Polyglyceryl myristate-10 0.2% by mass
Propylene glycol 10% by mass
Sorbitol 10% by mass
Methylparaben 0.1% by mass
Dipotassium glycyrrhizinate 0.1% by mass
Sodium lauroylmethyltaurine 0.2% by mass
Sodium citrate 0.3% by mass
Carboxymethylcellulose sodium 3% by mass
Fragrance 0.5% by mass
water residue

Claims (1)

A method for improving the antibacterial properties of a composition containing (A) curcuminoid against Porphyromonas gingivalis by blending (B) a polyglycerin fatty acid ester with an HLB of 14 or more into a composition containing (A) curcuminoid. A method, wherein the curcuminoid concentration is 0.00001 to 0.01% by mass; and the concentration of the (B) polyglycerin fatty acid ester having an HLB of 14 or more is 0.001 to 5% by mass .