JPWO2017034011A1 - 腸内有用菌増殖剤 - Google Patents
腸内有用菌増殖剤 Download PDFInfo
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- JPWO2017034011A1 JPWO2017034011A1 JP2017536483A JP2017536483A JPWO2017034011A1 JP WO2017034011 A1 JPWO2017034011 A1 JP WO2017034011A1 JP 2017536483 A JP2017536483 A JP 2017536483A JP 2017536483 A JP2017536483 A JP 2017536483A JP WO2017034011 A1 JPWO2017034011 A1 JP WO2017034011A1
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- bacteria
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- amino acid
- cyclodipeptide
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Abstract
Description
によって表される、同一の又は異なるアミノ酸のシクロジペプチド化合物の少なくとも1種、少なくとも2種又は少なくとも3種を有効成分として含んでなる、腸内有用菌の増殖剤。
[17]前記[1]〜[15]のいずれかに記載の増殖剤又は前記[16]に記載の化合物を飲食品又は飼料に添加することを含む、被験体の腸内において有用菌を増加もしくは増殖させる性質を飲食品又は飼料に付与する方法。
1.シクロジペプチド化合物
本発明の増殖剤の有効成分である化合物は、下記の式(1)及び式(2):
によって表される、同一の又は異なるアミノ酸のシクロジペプチド化合物である。式(2)の化合物は、D−もしくはL−プロリンと、プロリン以外のD−もしくはL−アミノ酸又はグリシンとのシクロジペプチドを表す。
2.腸内有用菌増殖剤
本発明はまた、上記のシクロジペプチド化合物の少なくとも1種、少なくとも2種又は少なくとも3種を有効成分として含む、腸内有用菌を増殖(もしくは増加)させるための増殖剤(又は、増殖用組成物)を提供する。
3.飲食品又は飼料
本発明はさらに、上記の化合物又は上記の増殖剤(もしくは添加物)を含む、被験体の腸内において有用菌を増加もしくは増殖させるための飲食品又は飼料からなる組成物を提供する。
4.スクリーニング方法
本発明はさらに、本発明に関する上記知見に基づき、シクロジペプチド化合物について、とりわけ、腸内細菌であるビフィズス菌及び/又は乳酸菌を増加又は増殖させることに優れた化合物をスクリーニングするための方法を提供する。
5.被験体における腸内有用菌の増加又は増殖方法
本発明はさらに、被験体に上記シクロジペプチド化合物又は上記増殖剤の有効量を投与する、又は摂取させる、ことを含む、被験体において腸内有用菌を増加又は増殖させる方法を提供する。
[実施例1]
<シクロジペプチドの合成>
X. Sun et al., Tetrahedron Letters 5582014) 1905−1908に記載されるシクロジジペプチド化合物の合成法を用いて、シクロ(L−Leu−L−Val)、シクロ(L−Ile−L−Val)、シクロ(D−Ile−D−Val)、シクロ(D−Ile−L−Val)、シクロ(L−Leu−D−Val)、シクロ(L−Ile−D−Val)、シクロ(L−Tyr−L−Pro)、シクロ(L−His−L−Pro)、シクロ(L−Ile−L−Pro)、シクロ(L−Val−L−Pro)、及びシクロ(L−Leu−L−Pro)を合成した。
カラム:CHIRALPAK(登録商標)AS−3R(46×150mm、ダイセル社)
移動相:MilliQ/アセトニトリル=1/99(v/v)
流速:0.8ml/min
カラム温度:25℃
検出波長:200nm
<保持時間>
<ビフィズス菌又は有害菌の増殖試験>
増殖試験の手順は以下のとおりである。
(1)評価菌種として、いずれも腸内細菌である、ビフィズス菌(Bifidibactrerium adolescentis)と有害菌(Clostridium perfinges, Escherichia coli, Bacteroides fragilis, Enterobacter aerogenes, Staphylococcus aureus, Enterococcus faecium)の基準株を前培養した。
(2)TPY寒天培地を滅菌後、エタノールのみを添加した培地(ネガティブコントロール:N)、エタノールに溶解したサンプルを終濃度0.1μg/mL添加した培地を作製した。
(3)前培養した評価菌種を10倍希釈で5段階希釈し、培地に塗布後、48時間、37℃で培養した。
(4)培養終了後、5mLの滅菌生理食塩水をプレートに入れ、コロニーを回収した。
(5)回収液を10倍希釈し、OD600を測定した。
[実施例3]
<各種シクロジペプチドのビフィズス菌又は乳酸菌増殖活性>
1)評価菌種
テストした腸内細菌であるビフィズス菌及び乳酸菌は次のとおりである。
Bifidobacterium adolescentis T (CP233)、Bifidobacterium catenulatum T (CP1230)、Bifidobacterium pseudocatenulatum T (CP1233)、Bifidobacterium breve (CP240)、Bifidobacterium longum T (CP1179)、Bifidobacterium longum (CP1651)、Lactobacillus salivarius T (CP12)、Lactobacillus reuteri T(CP729)、Lactobacillus crispatus T(CP796)、及びLactobacillus amylovorus T (CP1544)。
2)実験方法
以下の手順で各種シクロジペプチドによる各菌株の増殖活性を測定した。
(i) 評価菌種を前培養した。
(ii)TPY寒天培地(ビフィズス菌評価培地)又は1/3に希釈したMRS寒天培地(乳酸菌評価培地)を滅菌後、エタノールのみを添加した培地(ネガティブコントロール:N)、エタノールに溶解した評価物質(シクロジペプチド)を終濃度0.1μg/ml添加した培地を作成した。
(iii)前培養した評価菌種を10倍希釈で4段階または5段階希釈し、培地に塗布後、48時間嫌気培養した。
(iv)培養終了後、5mLの滅菌生理食塩水をプレート上に入れ、コロニーを回収後、回収液の濁度を測定した。
3)結果
ビフィズス菌及び乳酸菌の増殖割合について、NのOD600を100%としたときの増加率(%)を図4に示した(N=3の平均値)。その結果、テストしたシクロペプチドは、ビフィズス菌又は乳酸菌の少なくとも1種を増殖した。
[実施例4]
<シクロジペプチド(c(LV)又はc(IV))のビフィズス菌の増殖活性>
1)評価菌種
テストした腸内細菌であるビフィズス菌は次のとおりである。
Bifidobacterium adolescentis (CP233)、Bifidobacterium catenulatum(CP1230)、Bifidobacterium pseudocatenulatum(CP1233)及びBifidobacterium breve(CP240)。
2)実験方法
以下の手順で各種シクロジペプチドによる各菌株の増殖活性を測定した。
(i)評価菌種を前培養した。
(ii)TPY寒天培地を滅菌後、エタノールのみを添加した培地(ネガティブコントロール:N)、エタノールに溶解した評価物質を終濃度0.1μg/ml添加した培地を作成した。
(iii)前培養した評価菌種を10倍希釈で4段階または5段階希釈し、培地に塗布後、48時間嫌気培養した。
(iv)培養終了後、5mLの滅菌生理食塩水をプレート上に入れ、コロニーを回収後、回収液の濁度を測定した。
3)結果
ビフィズス菌の増殖割合について、NのOD600を100%としたときの増加率(%)を図5に示した(N=3の平均値)。その結果、テストしたシクロペプチドは、ビフィズス菌を増殖した。
[実施例5]
<シクロジペプチド(c(LV)又はc(IV))の乳酸菌の増殖活性>
1)評価菌種
テストした腸内細菌である乳酸菌は次のとおりである。
Lactobacillus reuteri(CP729)及びLactobacillus amylovorus(CP1544)。
2)実験方法
以下の手順で各種シクロジペプチドによる各菌株の増殖活性を測定した。
(i)評価菌種を前培養した。
(ii)MRS培地を1/3に希釈した寒天培地を滅菌後、エタノールのみを添加した培地(ネガティブコントロール:N)、エタノールに溶解した評価物質を終濃度0.1μg/ml添加した培地を作成した。
(iii)前培養した評価菌種を10倍希釈で4段階または5段階希釈し、培地に塗布後、48時間嫌気培養した。
(iv)培養終了後、5mLの滅菌生理食塩水をプレート上に入れ、コロニーを回収後、回収液の濁度を測定した。
3)結果
乳酸菌の増殖割合について、NのOD600を100%としたときの増加率(%)を図6に示した(N=3の平均値)。その結果、テストしたシクロジペプチドは、乳酸菌を増殖した。
<シクロジペプチド(c(XP)、ここでX=V,T,H)のビフィズス菌の増殖活性>
1)評価菌種
テストした腸内細菌であるビフィズス菌は次のとおりである。
Bifidobacterium adolescentis (CP2238)、Bifidobacterium catenulatum(CP1230)、Bifidobacterium pseudocatenulatum(CP1233)及びBifidobacterium breve(CP240)。
2)実験方法
実施例4と同様の手順で各種シクロジペプチドによる各菌株の増殖活性を測定した。
3)結果
ビフィズス菌の増殖割合について、NのOD600を100%としたときの増加率(%)を図7に示した(N=3の平均値)。その結果、テストしたシクロペプチドは、ビフィズス菌を増殖した。
[実施例7]
<シクロジペプチド(c(XP) 、ここでX=I,L)のビフィズス菌の増殖活性>
1)評価菌種
テストした腸内細菌であるビフィズス菌は次のとおりである。
Bifidobacterium adolescentis (CP2238)、Bifidobacterium breve(CP240)、及びBifidobacterium longum(CP1179)。
2)実験方法
実施例4と同様の手順で各種シクロジペプチドによる各菌株の増殖活性を測定した。
3)結果
ビフィズス菌の増殖割合について、NのOD600を100%としたときの増加率(%)を図8に示した(N=3の平均値)。その結果、テストしたシクロペプチドは、ビフィズス菌を増殖した。
<シクロジペプチド(c(WY)又はc(FW))の乳酸菌の増殖活性>
1) 評価菌種
テストした腸内細菌であるビフィズス菌は次のとおりである。
Bifidobacterium catenulatum(CP1230)、Bifidobacterium pseudocatenulatum(CP1233)、Bifidobacterium breve(CP240)
括弧内は、本出願人が保有する菌株の名称を示す。
2) 実験方法
実施例4と同様の手順で各種シクロジペプチドによる各菌株の増殖活性を測定した。
3) 結果
ビフィズス菌の増殖割合について、NのOD600を100%としたときの増加率(%)を図9に示した(N=3の平均値)。その結果、テストしたシクロペプチドは、ビフィズス菌を増殖した。
Claims (23)
- 前記有用菌が、ビフィズス菌又は乳酸菌である、請求項1に記載の増殖剤。
- 腸内有害菌を本質的に増加させない、請求項1又は2に記載の増殖剤。
- 前記有用菌の増殖率が、対照と比べて1.1倍以上、1,2倍以上、又は1.5倍〜6倍もしくはそれ以上である、請求項1〜3のいずれか1項に記載の増殖剤。
- 前記シクロジペプチド化合物が、異なる2つのアミノ酸の結合体である、請求項1〜4のいずれか1項に記載の増殖剤。
- 前記シクロジペプチドを構成するアミノ酸は、D−もしくはL−アラニン、D−もしくはL−バリン、D−もしくはL−ロイシン、D−もしくはL−イソロイシン、D−もしくはL−メチオニン、D−もしくはL−プロリン、D−もしくはL−フェニルアラニン、D−もしくはL−チロシン、D−もしくはL−トリプトファン、D−もしくはL−ヒスチジン、グリシン、D−もしくはL−セリン、D−もしくはL−トレオニン、D−もしくはL−グルタミン酸、D−もしくはL−グルタミン、D−もしくはL−アスパラギン酸、及びD−もしくはL−アスパラギンからなる群から選択される、請求項1〜5のいずれか1項に記載の増殖剤。
- 前記シクロジペプチド化合物を構成するアミノ酸の一方が、疎水性アミノ酸である、請求項1〜6のいずれか1項に記載の増殖剤。
- 前記シクロジペプチド化合物を構成するアミノ酸の一方が、分岐鎖アミノ酸である、請求項1〜7のいずれか1項に記載の増殖剤。
- 前記分岐鎖アミノ酸が、D−もしくはL−バリン、D−もしくはL−ロイシン、又は、D−もしくはL−イソロイシンである、請求項8に記載の増殖剤。
- 前記シクロジペプチド化合物を構成するアミノ酸の一方が、D−もしくはL−バリンである、請求項7又は8に記載の増殖剤。
- 前記シクロジペプチド化合物を構成するアミノ酸の一方が、D−もしくはL−プロリンである、請求項1〜7のいずれか1項に記載の増殖剤。
- 前記シクロジペプチド化合物を構成するアミノ酸の一方が、D−もしくはL−芳香族アミノ酸である、請求項1〜6のいずれか1項に記載の増殖剤。
- 前記芳香族アミノ酸がD−もしくはL−トリプトファンである、請求項12に記載の増殖剤。
- 前記シクロジペプチド化合物を構成するアミノ酸の一方が、L−アミノ酸であり、かつ、他方が、D−アミノ酸又はL−アミノ酸である、請求項1〜13のいずれか1項に記載の増殖剤。
- 前記化合物が、シクロ(D−イソロイシル−L−バリル)、シクロ(L−イソロイシル−D−バリル)、シクロ(D−イソロイシル−D−バリル)、シクロ(L−ロイシル−L−バリル)、シクロ(L−ロイシル−D−バリル)、シクロ(D−ロイシル−L−バリル)、シクロ(D−ロイシル−D−バリル)、シクロ(L−チロシル−L−プロリル)、シクロ(L−ヒスチジル−L−プロリル)、シクロ(L−イソロイシル−L−プロリル)、シクロ(L−バリル−L−プロリル)、シクロ(L−ロイシル−L−プロリル)、シクロ(L−イソロイシル−L−バリル)、シクロ(L−トレオニル−L−プロリル)、シクロ(L−トリプトファニル−L−チロシル)、シクロ(D−トリプトファニル−L−チロシル)、シクロ(D−アラニル−L−バリル)、シクロ(D−ヒスチジル−L−プロリル)、シクロ(L−フェニルアラニル−L−トリプトファニル)、シクロ(L−グルタミル−L−グルタミル)、シクロ(L−セリル−L−セリル)、シクロ(L−セリル−L−チロシル)、シクロ(L−メチオニル−L−プロリル)、シクロ(L−メチオニル−L−メチオニル)、シクロ(グリシル−グリシル)、シクロ(L−フェニルアラニル−L−プロリル)、シクロ(L−ロイシル−L−トリプトファニル)、シクロ(L−ロイシル−L−フェニルアラニル)、シクロ(L−アラニル−L−ヒスチジル)、シクロ(L−アラニル−L−セリル)、シクロ(L−アラニル−L−グルタミニル)、及びシクロ(L−アラニル−L−グルタミル)からなる群から選択される、請求項1〜14のいずれか1項に記載の増殖剤。
- 請求項1〜15のいずれか1項に記載の増殖剤又は請求項16に記載の化合物を飲食品又は飼料に添加することを含む、被験体の腸内において有用菌を増加もしくは増殖させる性質を飲食品又は飼料に付与する方法。
- 請求項1〜15のいずれか1項に記載の増殖剤又は請求項16に記載の化合物を飲食品又は飼料に添加することを含む、被験体の腸内において有用菌を増加もしくは増殖させる性質を備えた飲食品又は飼料の製造方法。
- 請求項1〜15のいずれか1項に記載の増殖剤又は請求項16に記載の化合物を含む、被験体の腸内において有用菌を増加もしくは増殖させるための飲食品又は飼料からなる組成物。
- 腸内有害菌を本質的に増加させない、請求項19に記載の組成物。
- ビフィドバクテリウム属細菌、ラクトバチルス属細菌、ラクトコッカス属細菌、バチルス属細菌、又は少なくとも2種の該細菌の混合菌、或いは該細菌又は該混合菌の発酵物をさらに含む、請求項19又は20に記載の組成物。
- ビフィズス菌もしくは乳酸菌又はその発酵物の製造における、請求項1〜15のいずれか1項に記載の増殖剤又は請求項16に記載の化合物の使用。
- 発酵物が発酵乳又はサイレージである、請求項22に記載の使用。
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CN114805364A (zh) * | 2022-04-12 | 2022-07-29 | 常州工程职业技术学院 | 四氢吡咯和哌嗪二酮的并环化合物及其制备和在药学上的用途 |
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