JP6016342B2 - 口腔用組成物 - Google Patents
口腔用組成物 Download PDFInfo
- Publication number
- JP6016342B2 JP6016342B2 JP2011196314A JP2011196314A JP6016342B2 JP 6016342 B2 JP6016342 B2 JP 6016342B2 JP 2011196314 A JP2011196314 A JP 2011196314A JP 2011196314 A JP2011196314 A JP 2011196314A JP 6016342 B2 JP6016342 B2 JP 6016342B2
- Authority
- JP
- Japan
- Prior art keywords
- cinnamic acid
- acid
- biofilm formation
- caries
- biofilm
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 20
- 230000032770 biofilm formation Effects 0.000 claims description 47
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical group C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 39
- 208000002925 dental caries Diseases 0.000 claims description 31
- 241000194019 Streptococcus mutans Species 0.000 claims description 15
- ZYOPDNLIHHFGEC-FNORWQNLSA-N Trans-2, 3, 4-Trimethoxycinnamate Chemical compound COC1=CC=C(\C=C\C(O)=O)C(OC)=C1OC ZYOPDNLIHHFGEC-FNORWQNLSA-N 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 10
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 7
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- 239000002253 acid Substances 0.000 claims description 4
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- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
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Description
すなわち、本発明は、虫歯菌が虫歯バイオフィルムを形成するクオラムセンシングシステムを抑制することにより虫歯を予防するものであり、そのクオラムセンシング抑制剤をけい皮酸とその類縁体に見出したものである。
さらに、本発明は、少なくとも1種のけい皮酸またはその類縁体を含有するクオラムセンシング抑制剤に関し、けい皮酸が、少なくとも1つのメトキシ基を有するクオラムセンシング抑制剤に関する。
1.けい皮酸、類縁体の各個別の活性(図1)
2.けい皮酸、けい皮アルデヒド、けい皮酸メチルの用量変化による活性(図2)
3.けい皮酸、フェニルプロピオン酸の活性比較(図3)
4.けい皮酸の 置換基の相違による活性比較(図4)
5.3種のメトキシ基の置換位置が相違するジメトキシけい皮酸の活性(図5)
6.けい皮酸に導入されたメトキシ基の数による活性の差(図6)
(けい皮酸およびその類縁体のバイオフィルム形成抑制活性評価)
(1−1)披験物質
けい皮酸および類縁体として、披験物質のけい皮酸、バニリン、フェルラ酸、クロロゲン酸、カフェ酸、p-クマル酸、けい皮アルデヒド、けい皮酸メチル、フェニルプロピオン酸、2-メトキシけい皮酸、3-メトキシけい皮酸、4-メトキシけい皮酸、3-ブロモけい皮酸、3-フルオロけい皮酸、3-メチルけい皮酸、4-アセトキシけい皮酸、4-ブロモけい皮酸、4-エトキシけい皮酸、4-フルオロけい皮酸、3,4-ジメトキシけい皮酸、2,3-ジメトキシけい皮酸、2,5-ジメトキシけい皮酸、2,3,4-トリメトキシけい皮酸、3,4,5-トリメトキシけい皮酸は全て市販特級品を用いた。
S. mutans UA159株を5mlのBrain Heart Infusion(BHI)液体培地にて37℃で10時間嫌気培養し、3000rpmで10分間遠心分離して集めた細菌を、PBSにてOD550nm=0.5に調製し、これを供試菌懸濁液とした。バイオフィルム形成は、96穴マイクロプレートを用いて試験を行った。各ウェルに、バイオフィルム形成阻害サンプル60μl、CSP20μl、S. mutans供試菌懸濁液20μl、0.1% Sucrose添加 Todd Hewitt Broth 100μlを添加し、37℃で5%CO2条件下で16時間培養を行った。
上記培養後の上清を取り除き、PBSにて2回各ウェルの洗浄を行った。洗浄後、各ウェルに0.25%サフラニン溶液を添加し15分間静置後余剰サフラニン溶液を取り除き、PBSにて2回各ウェルの洗浄を行った。洗浄後各ウェルにエタノールを添加し、30分間振盪することで染色させたサフラニンを溶出させ、マイクロプレートリーダーを用いて492nmの吸光度を測定し、バイオフィルム形成量を定量した。
バイオフィルム形成量は、サンプルを添加していないときの形成量を100としたときの割合で示した。
けい皮酸および類似化合物について:
けい皮酸およびけい皮酸類似構造化合物のバイオフィルム形成抑制効果を図1に示した。けい皮酸、p-クマル酸、カフェ酸を添加したときに、バイオフィルム形成量は約20%低下した。一方、クロロゲン酸、フェルラ酸、バニリンを添加したときにはバイオフィルム形成量は変わらず、類似構造化合物でも挙動が異なることが確認された。
また、けい皮酸に着目してみると、構造中にカルボン酸を含むけい皮酸ではバイオフィルム形成抑制活性が濃度依存的に認められていたが、エステルであるけい皮酸メチルやけい皮アルデヒドなどの類縁体では、バイオフィルム形成抑制活性は認められなかった。さらに、フェニルプロピオン酸にも活性が認められなかった。このことから、バイオフィルム形成抑制活性を示すためには、けい皮酸構造中にカルボン酸と二重結合が必要であることが示唆された(図2、3)。
各種置換基による活性への影響を確認したところ、メトキシ基が付与したときにのみ、バイオフィルム形成抑制活性を示した。付与する位置についての検討を行ったところ、3位の位置でのみ活性が認められ、2位、4位に付与した場合には、むしろバイオフィルム形成量は増加する傾向が確認された(図4)。また、ジメトキシけい皮酸を用いて、メトキシ基の位置と活性の強弱との相関を確認したところ、3位にメトキシ基が付与した、3,4-ジメトキシけい皮酸と2,3-ジメトキシけい皮酸添加時には濃度依存的なバイオフィルム形成抑制が確認されたが、2,5-ジメトキシけい皮酸では活性は認められなかった(図5)。
メトキシ基の付与する数とバイオフィルム形成抑制活性との関連を調べるため、けい皮酸、メトキシけい皮酸、ジメトキシけい皮酸、トリメトキシけい皮酸を用いて活性を比較した。その結果、メトキシ基の数に比例してバイオフィルム形成量が低下しており、付与するメトキシ基の数がバイオフィルム形成抑制活性に影響を与えていることが確認された(図6)。
下記処方に従って含そう剤を製造した。
エタノール 2.0重量%
2,3,4−トリメトキシけい皮酸 1.0
香料 1.0
水 残
100.0
下記処方に従って練り歯磨きを製造した。
炭酸カルシウム 50.0重量%
グリセリン 19.0
2,3,4−トリメトキシけい皮酸 1.0
カルボオキシメチルセルロース 2.0
ラルリル硫酸ナトリウム 2.0
香料 1.0
サッカリン 0.1
クロルヘキシジン 0.01
水 残
100.0
下記処方に従って口臭用スプレーを製造した。
エタノール 10.0重量%
グリセリン 5.0
2,3,4−トリメトキシけい皮酸 1.0
香料 0.05
着色料 0.001
水 残
100.0
下記処方に従ってトローチを製造した。
2,3,4−トリメトキシけい皮酸 92.3重量%
アラビアガム 6.0
香料 1.0
モノフルオロリン酸ナトリウム 0.7
100.0
下記処方に従ってチューインガムを製造した。
ガムベース 20.0重量%
キシリトール 54.7
マルトース 15.0
ソルビトール 9.3
香料 0.5
2,3,4−トリメトキシけい皮酸 0.5
100.0
下記処方に従ってキャンディを製造した。
砂糖 50.0重量%
還元水あめ 33.0
クエン酸 1.0
香料 0.2
L-メントール 1.0
2,3,4−トリメトキシけい皮酸 0.4
水 残
100.0
下記処方に従って錠菓を製造した。
砂糖 74.7重量%
乳糖 18.9
2,3,4−トリメトキシけい皮酸 2.0
ショ糖脂肪酸エステル 0.15
水 4.25
100.0
下記処方に従ってグミゼリーを製造した。
ゼラチン 60.0重量%
還元水あめ 32.4
2,3,4−トリメトキシけい皮酸 0.5
植物油脂 4.5
リンゴ酸 2.0
香料 0.5
100.0
下記処方に従って飲料を製造した。
オレンジ果汁 30.0重量%
2,3,4−トリメトキシけい皮酸 0.5
クエン酸 0.1
ビタミンC 0.04
香料 0.1
水 残
100.0
Claims (11)
- カフェ酸、p-クマル酸、けい皮酸メチル、3-メトキシけい皮酸、3,4-ジメトキシけい皮酸、2,3-ジメトキシけい皮酸、2,3,4-トリメトキシけい皮酸、または3,4,5-トリメトキシけい皮酸から選択される少なくとも1種のけい皮酸類縁体を含有するバイオフィルム形成抑制剤。
- 前記請求項1記載のけい皮酸類縁体を含有する虫歯バイオフィルム形成抑制剤。
- 前記請求項1記載のけい皮酸類縁体を含有するストレプトコッカス・ミュータンス(Streptococcus mutans)に特異的なバイオフィルム形成抑制剤。
- 前記請求項1記載のけい皮酸類縁体を含有するクオラムセンシング抑制剤。
- 前記請求項1記載のけい皮酸類縁体を含有するストレプトコッカス・ミュータンス(Streptococcus mutans) CSPに特異的なクオラムセンシング抑制剤。
- 3-メトキシけい皮酸、2,3-ジメトキシけい皮酸、または2,3,4-トリメトキシけい皮酸から選択される少なくとも1種以上のけい皮酸類縁体を含有する口腔用組成物。
- 請求項6に記載の口腔用組成物からなる含そう剤。
- 請求項6に記載の口腔用組成物からなる練り歯磨き剤。
- 請求項6に記載の口腔用組成物からなる吸入剤。
- 請求項6に記載の口腔用組成物からなるトローチ剤。
- 請求項6に記載の口腔用組成物を含有する食品。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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JP2011196314A JP6016342B2 (ja) | 2011-09-08 | 2011-09-08 | 口腔用組成物 |
KR1020147008975A KR101969610B1 (ko) | 2011-09-08 | 2012-09-06 | 구강용 조성물 |
PCT/JP2012/005657 WO2013035331A1 (ja) | 2011-09-08 | 2012-09-06 | 口腔用組成物 |
CN201280043570.8A CN103813777A (zh) | 2011-09-08 | 2012-09-06 | 口腔用组合物 |
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JP2011196314A JP6016342B2 (ja) | 2011-09-08 | 2011-09-08 | 口腔用組成物 |
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JP2016142335A Division JP6389212B2 (ja) | 2016-07-20 | 2016-07-20 | 口腔用組成物 |
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JP7080203B2 (ja) | 2019-06-28 | 2022-06-03 | 三菱電機株式会社 | ロボットシステム、組立体の組立方法、組立体の検査方法、電動ハンドの検査方法および電動ハンド性能検査治具 |
US11459445B2 (en) | 2018-02-13 | 2022-10-04 | Sumitomo Chemical Company, Limited | Composition and molded body |
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CN106306979A (zh) * | 2016-08-18 | 2017-01-11 | 华南农业大学 | 香辛料提取物在食源性致病菌生物膜抑制和清除上的应用 |
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US11459445B2 (en) | 2018-02-13 | 2022-10-04 | Sumitomo Chemical Company, Limited | Composition and molded body |
JP7080203B2 (ja) | 2019-06-28 | 2022-06-03 | 三菱電機株式会社 | ロボットシステム、組立体の組立方法、組立体の検査方法、電動ハンドの検査方法および電動ハンド性能検査治具 |
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