JPH0733649A - Anticarious agent - Google Patents
Anticarious agentInfo
- Publication number
- JPH0733649A JPH0733649A JP20045393A JP20045393A JPH0733649A JP H0733649 A JPH0733649 A JP H0733649A JP 20045393 A JP20045393 A JP 20045393A JP 20045393 A JP20045393 A JP 20045393A JP H0733649 A JPH0733649 A JP H0733649A
- Authority
- JP
- Japan
- Prior art keywords
- agent
- tooth
- oral composition
- blended
- mutans
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 9
- 239000004305 biphenyl Substances 0.000 claims abstract description 9
- -1 biphenyl compound Chemical class 0.000 claims abstract description 7
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
- 239000004075 cariostatic agent Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 241000194019 Streptococcus mutans Species 0.000 abstract description 10
- 208000002925 dental caries Diseases 0.000 abstract description 7
- 235000009508 confectionery Nutrition 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 229940034610 toothpaste Drugs 0.000 abstract description 4
- 239000000606 toothpaste Substances 0.000 abstract description 4
- 235000015218 chewing gum Nutrition 0.000 abstract description 3
- 229940112822 chewing gum Drugs 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 230000001419 dependent effect Effects 0.000 abstract description 2
- 239000002324 mouth wash Substances 0.000 abstract description 2
- 229940051866 mouthwash Drugs 0.000 abstract description 2
- 230000000845 anti-microbial effect Effects 0.000 abstract 2
- 235000020429 malt syrup Nutrition 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- BYTORXDZJWWIKR-UHFFFAOYSA-N Hinokiol Natural products CC(C)c1cc2CCC3C(C)(CO)C(O)CCC3(C)c2cc1O BYTORXDZJWWIKR-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000001013 cariogenic effect Effects 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical compound C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QXKAEQCGFVTAMN-UHFFFAOYSA-N 2-(2-hydroxy-3-methoxy-5-methylphenyl)-6-methoxy-4-methylphenol Chemical compound COC1=CC(C)=CC(C=2C(=C(OC)C=C(C)C=2)O)=C1O QXKAEQCGFVTAMN-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 240000000425 Chaenomeles speciosa Species 0.000 description 1
- 235000005078 Chaenomeles speciosa Nutrition 0.000 description 1
- 235000011511 Diospyros Nutrition 0.000 description 1
- 244000236655 Diospyros kaki Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 235000013502 Pyrus japonica Nutrition 0.000 description 1
- 244000111306 Torreya nucifera Species 0.000 description 1
- 235000006732 Torreya nucifera Nutrition 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、う蝕を誘発する病原菌
であるストレプトコッカス・ミュータンス(Streptococ
cus mutans、以下S.mutansと略記する)に対し強い抗菌
性及び発育阻害を有するビフェニル化合物に関するもの
である。TECHNICAL FIELD The present invention relates to Streptococcus mutans which is a pathogenic bacterium that induces dental caries.
cus mutans, hereinafter abbreviated as S. mutans) to a biphenyl compound having strong antibacterial properties and growth inhibition.
【0002】[0002]
【0003】う蝕の防止及び予防の一つとしてう蝕原因
菌を撲滅もしくは生育を防止する方法が従来より知られ
ている。例えば、ペニシリンやエリスルマイシン等の抗
生物質、う蝕原因菌であるS.mutansの細胞壁を溶解する
細胞壁溶解酵素やシクロヘキシウジン等の殺菌剤の使用
が試みられている。As one of the prevention and prevention of caries, a method of eradicating caries-causing bacteria or preventing growth thereof has been conventionally known. For example, attempts have been made to use antibiotics such as penicillin and erythromycin, cell wall lytic enzymes that dissolve the cell wall of S. mutans, which is a causative bacterium, and bactericides such as cyclohexidine.
【0004】また、植物抽出物を用いたう蝕予防剤とし
て、ニクズク等の抽出物(特開昭59−134729号
公報)や柿の葉,ケンポナシの果実の抽出物を用いた口
腔用組成物(特開平2−78609号公報)等が提案さ
れている。Further, as a caries preventive agent using a plant extract, an oral composition using an extract of Japanese nutmeg (Japanese Patent Laid-Open No. 59-134729), an extract of persimmon leaves, and fruits of Japanese quince (Japanese Patent Laid-Open No. 2-78609) and the like have been proposed.
【0005】さらに、特定のカルボン酸やラクトン構造
を有する合成香料を抗う蝕剤として用いる方法(特開昭
59−175423号公報)やマグノロール、ホオノキ
オールをう蝕予防剤として用いる方法(特開平1−15
1512号公報)等が提案されている。Further, a method of using a synthetic fragrance having a specific carboxylic acid or lactone structure as an anti-caries agent (Japanese Patent Laid-Open No. 175423/1984) or a method of using magnolol or honokiol as a caries preventive agent (Japanese Patent Laid-Open No. Hei 9 (1999) -58,091) 1-15
No. 1512) has been proposed.
【0006】しかしながら、抗生物質には副作用の問
題、合成香料には特異臭の問題、マグノロールやホオノ
キオールには安定性に問題があるなど、何れも改善の必
要性があった。However, antibiotics have side effects, synthetic fragrances have a peculiar odor problem, and magnolol and honokiol have stability problems.
【0007】[0007]
【発明が解決しようとする課題】本発明者等は、上記事
情を鑑み鋭意検討した結果、特定のビフェニル化合物
が、う蝕原因菌であるS.mutansに対して強い抗菌作用を
有していることを見いだした。DISCLOSURE OF THE INVENTION As a result of intensive studies made by the present inventors in view of the above circumstances, a specific biphenyl compound has a strong antibacterial action against S. mutans which is a cariogenic bacterium. I found a thing.
【0008】したがって、本発明者の目的は、う蝕原因
菌であるS.mutansに対して強い抗菌作用を有する化合物
を提供することにある。[0008] Therefore, an object of the present inventor is to provide a compound having a strong antibacterial action against S. mutans which is a cariogenic bacterium.
【0009】[0009]
【課題を解決するための手段】即ち、本発明は下記一般
式Means for Solving the Problems That is, the present invention has the following general formula:
【0010】[0010]
【化2】 [Chemical 2]
【0011】(但しRは水素原子もしくは炭素数1から
8の直鎖及び分岐鎖状の飽和炭化水素基)で表されるビ
フェニル化合物からなる抗う蝕剤に関するものである。(Wherein R is a hydrogen atom or a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms) and relates to an anticaries agent comprising a biphenyl compound.
【0012】本発明に使用されるビフェニル化合物の一
部は公知の物質が含まれ、その合成方法について報告さ
れている(日本化学雑誌第87巻、第6号、603頁、
1966年)。また、公知以外の化合物も同様の合成方
法によって得ることが出来る。A part of the biphenyl compound used in the present invention includes known substances, and a method for synthesizing the same has been reported (Japan Chemical Journal Vol. 87, No. 6, p. 603,
1966). Also, compounds other than known compounds can be obtained by the same synthetic method.
【0013】本発明の抗う蝕剤は、例えば練り歯磨き、
粉歯磨き、水歯磨き、マウスウォッシュ、トローチ等の
口腔用組成物やチューインガム、キャンディー、飴等に
配合することが出来る。The anti-caries agent of the present invention is, for example, a toothpaste,
It can be added to oral compositions such as toothpaste, toothpaste, mouthwash, troche, etc., chewing gum, candy, candy and the like.
【0014】その配合量は使用する系によって異なり、
一概には言えないが、以下の実施例から明らかなよう
に、既存のこの種の物質と同等でよい。The blending amount depends on the system used,
Although it cannot be generally stated, as is clear from the following examples, it may be equivalent to the existing substances of this type.
【0015】次に、本発明のビフェニル化合物によるS.
mutansに対する抗菌作用の効果を明らかにするための実
施例を示す。Next, S.
An example for clarifying the effect of antibacterial action against mutans will be shown.
【0016】[0016]
【実施例】 以下実施
例により本発明を更に詳細に説明する。尚、以下におけ
る%表示は、特に指定しない限り、容量%を示す。実施
例におけるビフェニル化合物の名称を前記一般式のRの
違いにより以下の如く略記する。ビフェニル化合物1
(R=CH3 )、ビフェニル化合物2(R=C
2 H5 )、ビフェニル化合物3(R=C3 H7 )、ビフ
ェニル化合物4(R=iso−C3H7 )、ビフェニル
化合物5(R=C8 H17)、ビフェニル化合物6(R=
H)。また、構造の異なるビフェニル化合物であるデヒ
ドロジオイゲノール、デヒドロジクレオソールを対照と
して用いた。EXAMPLES The present invention will be described in more detail with reference to the following examples. In addition, unless otherwise specified, the percentage display in the following shows the percentage by volume. The names of the biphenyl compounds in the examples are abbreviated as follows depending on the difference in R in the general formula. Biphenyl compound 1
(R = CH 3 ), biphenyl compound 2 (R = C
2 H 5), biphenyl compounds 3 (R = C 3 H 7 ), biphenyl compounds 4 (R = iso-C 3 H 7), biphenyl compounds 5 (R = C 8 H 17 ), biphenyl compounds 6 (R =
H). In addition, dehydrodioigenol and dehydrodicresol, which are biphenyl compounds having different structures, were used as controls.
【0017】〔抗菌作用試験方法〕ストレプトコッカス
・ミュータンスに対する抗菌作用を試験する方法として
ペーパーディスク法を用いて行った。寒天培地に、別に
同液体培地で培養しておいたS.mutans培養液を混合
(0.1ml/100ml培地)し、10mlをシャー
レに分注固化した。シャーレの中央にペーパーディスク
を置き、試料の無水エタノール溶液50μlを滴下し
た。5℃にて24時間静置した後、32℃にて48時間
培養した。ペーパーディスクのまわりに形成された阻止
円の直径を測定する事により、抗菌力を調べた。測定に
用いたサンプル濃度は1.25、0.625、0.31
3および0.156%で行った。[Test Method for Antibacterial Action] As a method for testing the antibacterial action against Streptococcus mutans, a paper disk method was used. The agar medium was mixed with the S. mutans culture solution that had been separately cultured in the same liquid medium (0.1 ml / 100 ml medium), and 10 ml was dispensed and solidified in a petri dish. A paper disk was placed in the center of the petri dish, and 50 μl of an absolute ethanol solution of the sample was dropped. After standing at 5 ° C. for 24 hours, it was cultured at 32 ° C. for 48 hours. The antibacterial activity was investigated by measuring the diameter of the inhibition circle formed around the paper disc. The sample concentrations used for measurement are 1.25, 0.625, 0.31.
3 and 0.156%.
【0018】[0018]
【表1】 [Table 1]
【0019】表1の結果から、本発明のビフェニル化合
物は、濃度依存的にS.mutansに対して抗菌作用を有し、
しかも低濃度で効果のあることがわかった。From the results shown in Table 1, the biphenyl compound of the present invention has an antibacterial action against S. mutans in a concentration-dependent manner,
Moreover, it was found that it was effective at low concentrations.
【0020】[0020]
【発明の効果】以上記載の如く、本発明が低濃度でS.mu
tansに対して強い抗菌作用を有することから、う蝕を防
止もしくは予防するための口腔用組成物やチューインガ
ム、キャンディー、飴等への配合が可能な抗う蝕剤を提
供することは明かである。INDUSTRIAL APPLICABILITY As described above, according to the present invention, S.mu
Since it has a strong antibacterial action against tans, it is obvious to provide an anti-caries agent which can be incorporated into an oral composition for preventing or preventing dental caries and chewing gum, candy, candy and the like.
Claims (1)
からなる抗う蝕剤。 【化1】 (但しRは水素原子もしくは炭素数1から8の直鎖及び
分岐鎖状の飽和炭化水素基)1. An anticaries agent comprising a biphenyl compound represented by the following general formula. [Chemical 1] (However, R is a hydrogen atom or a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20045393A JPH0733649A (en) | 1993-07-19 | 1993-07-19 | Anticarious agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20045393A JPH0733649A (en) | 1993-07-19 | 1993-07-19 | Anticarious agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0733649A true JPH0733649A (en) | 1995-02-03 |
Family
ID=16424560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20045393A Pending JPH0733649A (en) | 1993-07-19 | 1993-07-19 | Anticarious agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0733649A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09165727A (en) * | 1995-04-18 | 1997-06-24 | Tadashi Ito | Wave-absorbing block with pierced hole, seawater exchanging type breakwater, and seawater genetration type wave-absorbing block embankment |
| WO2006071654A1 (en) | 2004-12-29 | 2006-07-06 | Colgate-Palmolive Company | Oral compositions containing biphenol antibacterial compounds |
| US7211700B2 (en) * | 2000-12-20 | 2007-05-01 | Mcneil-Ppc, Inc. | Non-halogenated phenyl substituted phenols, antimicrobial compositions containing the same, and methods of using the same |
| US8313733B2 (en) | 2005-03-18 | 2012-11-20 | Colgate-Palmolive Company | Antibacterial 5,5′-disubstituted 3,3′ dialkoxy-2,2′-dihydroxy-1,1′-biphenyl |
| US8425881B2 (en) | 2005-03-18 | 2013-04-23 | Colgate-Palmolive Company | Antibacterial 3′,5-disubstituted 2,4′-dihydroxybiphenyl compounds, derivatives and related methods |
| JP2013520518A (en) * | 2010-02-24 | 2013-06-06 | コルゲート・パーモリブ・カンパニー | Oral care composition |
| JP2014062097A (en) * | 2007-10-01 | 2014-04-10 | Colgate Palmolive Co | Anti-bacterial pyrocatechols and related methods |
| US20140314688A1 (en) * | 2011-12-02 | 2014-10-23 | Colgate-Palmolive Company | Oral care compositions |
| US20140328772A1 (en) * | 2011-12-15 | 2014-11-06 | Colgate-Palmolive Company | Solubilized magnolol analogs |
| US20140341818A1 (en) * | 2011-12-15 | 2014-11-20 | Colgate-Palmolive Company | Solubilized magnolol analogs |
| US20150004104A1 (en) * | 2012-03-02 | 2015-01-01 | Colgate-Palmolive Company | Oral care compositions |
| US9439843B2 (en) | 2011-12-02 | 2016-09-13 | Colgate-Palmolive Company | Oral care compositions |
| CN110668981A (en) * | 2019-09-20 | 2020-01-10 | 广东省禾基生物科技有限公司 | Magnolol derivative and preparation method and application thereof |
-
1993
- 1993-07-19 JP JP20045393A patent/JPH0733649A/en active Pending
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09165727A (en) * | 1995-04-18 | 1997-06-24 | Tadashi Ito | Wave-absorbing block with pierced hole, seawater exchanging type breakwater, and seawater genetration type wave-absorbing block embankment |
| US7211700B2 (en) * | 2000-12-20 | 2007-05-01 | Mcneil-Ppc, Inc. | Non-halogenated phenyl substituted phenols, antimicrobial compositions containing the same, and methods of using the same |
| WO2006071654A1 (en) | 2004-12-29 | 2006-07-06 | Colgate-Palmolive Company | Oral compositions containing biphenol antibacterial compounds |
| AU2005322192B2 (en) * | 2004-12-29 | 2009-07-23 | Colgate-Palmolive Company | Oral compositions containing biphenol antibacterial compounds |
| EP2266666A1 (en) * | 2004-12-29 | 2010-12-29 | Colgate-Palmolive Company | Oral compositions containing biphenol antibacterial compounds |
| US8071077B2 (en) | 2004-12-29 | 2011-12-06 | Colgate-Palmolive Company | Oral compositions containing biphenol antibacterial compounds |
| CN103720678B (en) * | 2004-12-29 | 2016-08-31 | 高露洁-棕榄公司 | Oral cavity composition containing biphenol antibacterial compounds |
| US8652444B2 (en) | 2004-12-29 | 2014-02-18 | Colgate-Palmolive Company | Oral compositions containing biphenol antibacterial compounds |
| CN103720678A (en) * | 2004-12-29 | 2014-04-16 | 高露洁-棕榄公司 | Oral compositions containing biphenol antibacterial compounds |
| US8313733B2 (en) | 2005-03-18 | 2012-11-20 | Colgate-Palmolive Company | Antibacterial 5,5′-disubstituted 3,3′ dialkoxy-2,2′-dihydroxy-1,1′-biphenyl |
| US8425881B2 (en) | 2005-03-18 | 2013-04-23 | Colgate-Palmolive Company | Antibacterial 3′,5-disubstituted 2,4′-dihydroxybiphenyl compounds, derivatives and related methods |
| JP2014062097A (en) * | 2007-10-01 | 2014-04-10 | Colgate Palmolive Co | Anti-bacterial pyrocatechols and related methods |
| JP2015212274A (en) * | 2010-02-24 | 2015-11-26 | コルゲート・パーモリブ・カンパニーColgate−Palmolive Company | Oral care composition |
| US8956592B2 (en) | 2010-02-24 | 2015-02-17 | Colgate-Palmolive Company | Oral care compositions |
| JP2013520518A (en) * | 2010-02-24 | 2013-06-06 | コルゲート・パーモリブ・カンパニー | Oral care composition |
| JP2015500233A (en) * | 2011-12-02 | 2015-01-05 | コルゲート・パーモリブ・カンパニーColgate−Palmolive Company | Oral care composition |
| US20140314688A1 (en) * | 2011-12-02 | 2014-10-23 | Colgate-Palmolive Company | Oral care compositions |
| US9370475B2 (en) * | 2011-12-02 | 2016-06-21 | Colgate-Palmolive Company | Oral care compositions |
| US9439843B2 (en) | 2011-12-02 | 2016-09-13 | Colgate-Palmolive Company | Oral care compositions |
| US20140328772A1 (en) * | 2011-12-15 | 2014-11-06 | Colgate-Palmolive Company | Solubilized magnolol analogs |
| US20140341818A1 (en) * | 2011-12-15 | 2014-11-20 | Colgate-Palmolive Company | Solubilized magnolol analogs |
| US9414587B2 (en) * | 2011-12-15 | 2016-08-16 | Cologne-Palmolive Company | Solubilized magnolol analogs |
| US20150004104A1 (en) * | 2012-03-02 | 2015-01-01 | Colgate-Palmolive Company | Oral care compositions |
| US9795548B2 (en) | 2012-03-02 | 2017-10-24 | Colgate-Palmolive Company | Oral care compositions |
| CN110668981A (en) * | 2019-09-20 | 2020-01-10 | 广东省禾基生物科技有限公司 | Magnolol derivative and preparation method and application thereof |
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