JP2019147772A - ヘプシジン発現抑制剤、並びに鉄欠乏性貧血改善及び/又は予防用飲食品 - Google Patents
ヘプシジン発現抑制剤、並びに鉄欠乏性貧血改善及び/又は予防用飲食品 Download PDFInfo
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- JP2019147772A JP2019147772A JP2018034507A JP2018034507A JP2019147772A JP 2019147772 A JP2019147772 A JP 2019147772A JP 2018034507 A JP2018034507 A JP 2018034507A JP 2018034507 A JP2018034507 A JP 2018034507A JP 2019147772 A JP2019147772 A JP 2019147772A
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- hydrogen atom
- gallate
- general formula
- epigallocatechin
- Prior art date
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- XJOTXKZIRSHZQV-RXHOOSIZSA-N (3S)-3-amino-4-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[[(2S,3S)-1-[[(1R,6R,12R,17R,20S,23S,26R,31R,34R,39R,42S,45S,48S,51S,59S)-51-(4-aminobutyl)-31-[[(2S)-6-amino-1-[[(1S,2R)-1-carboxy-2-hydroxypropyl]amino]-1-oxohexan-2-yl]carbamoyl]-20-benzyl-23-[(2S)-butan-2-yl]-45-(3-carbamimidamidopropyl)-48-(hydroxymethyl)-42-(1H-imidazol-4-ylmethyl)-59-(2-methylsulfanylethyl)-7,10,19,22,25,33,40,43,46,49,52,54,57,60,63,64-hexadecaoxo-3,4,14,15,28,29,36,37-octathia-8,11,18,21,24,32,41,44,47,50,53,55,58,61,62,65-hexadecazatetracyclo[32.19.8.26,17.212,39]pentahexacontan-26-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-4-oxobutanoic acid Chemical compound CC[C@H](C)[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H](NC(=O)[C@@H](N)CC(O)=O)[C@@H](C)O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)[C@@H]4CSSC[C@H](NC(=O)[C@H](Cc5ccccc5)NC(=O)[C@@H](NC1=O)[C@@H](C)CC)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](Cc1cnc[nH]1)NC3=O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N2)C(=O)NCC(=O)N4)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O XJOTXKZIRSHZQV-RXHOOSIZSA-N 0.000 title claims abstract description 57
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Abstract
Description
[一般式(1)中、R1は水素原子又はアルキル基を示し、R2は水素原子又はガロイル基を示し、R3は水素原子、水酸基又は−OR1で表される基を示す。複数あるR1は互いに同一でも異なっていてもよい。R2が水素原子の場合、R3は水酸基又は−OR1で表される基であり、R3が水素原子の場合、R2はガロイル基である。ガロイル基中の水酸基の水素原子はアルキル基で置換されていてもよい。]
[一般式(3)中、R6は水素原子又はアルキル基を示し、R7は水素原子、水酸基又は−OR6で表される基を示し、R8及びR9は、それぞれ独立に水素原子、水酸基又は−OR6で表される基を示す。複数あるR6は互いに同一でも異なっていてもよい。R7が水酸基又は−OR6で表される基である場合、R8及びR9の少なくとも一方が水素原子である。]
[一般式(1)中、R1は水素原子又はアルキル基を示し、R2は水素原子又はガロイル基を示し、R3は水素原子、水酸基又は−OR1で表される基を示す。複数あるR1は互いに同一でも異なっていてもよい。R2が水素原子の場合、R3は水酸基又は−OR3で表される基であり、R3が水素原子の場合、R2はガロイル基である。ガロイル基中の水酸基の水素原子はアルキル基で置換されていてもよい。]
[一般式(3)中、R6は水素原子又はアルキル基を示し、R7は水素原子、水酸基又は−OR6で表される基を示し、R8及びR9は、それぞれ独立に水素原子、水酸基又は−OR6で表される基を示す。複数あるR6は互いに同一でも異なっていてもよい。R7が水酸基又は−OR6で表される基である場合、R8及びR9の少なくとも一方が水素原子である。]
HepG2細胞(Riken BRC)をDMEM+10%FBS培地中、37℃、5%CO2インキュベーター内で培養した。ヘプシジン発現試験では、48ウェルプレートに播種したHepG2細胞を用いた。セミコンフルエント状態になった段階で、DMEM−FBS培地に交換し、100ppb(最終濃度)のIL−6及び20μM濃度の被験物質を添加した。その後CO2インキュベーター内で24時間培養し、細胞からRNAを抽出して発現解析に供した。予備試験としてHepG2細胞にIL−6を添加したところ、濃度依存的にヘプシジン発現の誘導が確認された。
サンプル添加及び培養後の細胞を滅菌PBSで2回洗浄し、0.25mLのTrizol試薬を添加後、ボルテックスミキサーを用いて攪拌した。細胞に0.05mLのクロロホルムを添加し、分配後に上清を新しいチューブに移し、等量のイソプロパノールの添加によってRNAを沈殿させた。遠心分離(20,000g、5分)して沈殿を得、沈殿を70%エタノール溶液で洗浄した後、風乾した。乾燥後のRNAを0.1mL RNaseフリー水で溶解し、さらに0.25mLのエタノール、0.01mLの3M NaOAcを添加してRNAを沈殿させた。沈殿したRNAを回収後に、滅菌蒸留水に再溶解して総RNAの吸光度を測定して、濃度及び純度を確認した。
hHepcidin_F:
TTTCCCACAACAGACGGGACAACT(配列番号1)
hHepcidin_R:
GGGCAGCAGGAATAAATAAGGAAGGG(配列番号2)
hActb_F:
AGGATGCAGAAGGAGATCACTG(配列番号3)
hActb_R:
GGGTGTAACGCAACTAAGTCATAG(配列番号4)
インターロイキン−6(IL−6、Sigma Aldrich、I1395−10UG)、Trizol試薬(invitorgen)、QuantiTect Reverse Transcription kit (Qiagen)、LightCycler 480 SYBR Green I Master(Roche)、(+)−カテキン(wako、038−23461)、(−)−エピガロカテキン(wako、059−08951)、(−)−エピガロカテキンガレート(wako、056−08961)、(+)−ガロカテキン(wako、075−06331)、(−)−カテキンガレート(長良サイエンス、NH021302)、(−)−ガロカテキンガレート(長良サイエンス、NH021402)、(−)−エピカテキン(wako、059−06751)、(−)−エピカテキンガレート(wako、052−06741)、ゲニステイン(wako、551−77451)、ダイゼイン(wako、308−05871)、ジヒドロミリセチン(フナコシ、1351−10mg)、ルテオリン(wako、10004161)、アピゲニン(wako、016−18911)、ナリンゲニン(TCI、N0072−5g)、ヘスペレチン(wako、320−93841)、イソキサントフモール(フナコシ、2529−5−5mg)、タキシフォリン(フナコシ、1036)、ケルセチン(Sigma Aldrich、Q4951)、ミリセチン(フナコシ、M9367)、ケンフェロール(フナコシ、0054)、フロレチン(wako、160−17781)、キサントフモール(Hop steiner)、イソリキリチゲニン(TCI、I0822)、(−)−エピガロカテキン−3−O−(4”−O−メチル)ガレート(EGCG4”Me、長良サイエンス、NH027201)、(−)−エピガロカテキン−3−O−(3”−O−メチル)ガレート(EGCG3”Me、長良サイエンス、NH023201)、ストリクチニン(長良サイエンス、NH026102)、タンニン酸(wako、201−06332)、没食子酸(TCI、G0011)。
Claims (12)
- 下記一般式(1)で表される化合物、下記一般式(2)で表される化合物、下記一般式(3)で表される化合物及びこれらの塩からなる群から選ばれる少なくとも1種を有効成分として含む、ヘプシジン発現抑制剤。
[一般式(1)中、R1は水素原子又はアルキル基を示し、R2は水素原子又はガロイル基を示し、R3は水素原子、水酸基又は−OR1で表される基を示す。複数あるR1は互いに同一でも異なっていてもよい。R2が水素原子の場合、R3は水酸基又は−OR1で表される基であり、R3が水素原子の場合、R2はガロイル基である。ガロイル基中の水酸基の水素原子はアルキル基で置換されていてもよい。]
[一般式(2)中、R4は水素原子又はアルキル基を示し、R5は水素原子、水酸基又は−OR4で表される基を示す。複数あるR4は互いに同一でも異なっていてもよい。]
[一般式(3)中、R6は水素原子又はアルキル基を示し、R7は水素原子、水酸基又は−OR6で表される基を示し、R8及びR9は、それぞれ独立に水素原子、水酸基又は−OR6で表される基を示す。複数あるR6は互いに同一でも異なっていてもよい。R7が水酸基又は−OR6で表される基である場合、R8及びR9の少なくとも一方が水素原子である。] - 前記化合物が、(−)−ガロカテキンガレート、(−)−エピガロカテキンガレート、(−)−カテキンガレート、(+)−ガロカテキン、(−)−エピガロカテキン、(−)−エピカテキンガレート、(−)−エピガロカテキン−3−O−(4”−O−メチル)ガレート、(−)−エピガロカテキン−3−O−(3”−O−メチル)ガレート、ルテオリン、アピゲニン、ジヒドロミリセチン、ケルセチン及びケンフェロールからなる群から選ばれる少なくとも1種である、請求項1に記載のヘプシジン発現抑制剤。
- 前記一般式(1)で表される化合物が、(−)−ガロカテキンガレート及び/又は(−)−エピガロカテキンガレートである、請求項1に記載のヘプシジン発現抑制剤。
- ガロタンニン、エラジタンニン及びこれらの塩からなる群から選ばれる少なくとも1種を有効成分として含む、ヘプシジン発現抑制剤。
- 前記有効成分がストリクチニン又はその塩である、請求項4に記載のヘプシジン発現抑制剤。
- 没食子酸又はその塩を有効成分として含む、ヘプシジン発現抑制剤。
- 下記一般式(1)で表される化合物、下記一般式(2)で表される化合物、下記一般式(3)で表される化合物及びこれらの塩からなる群から選ばれる少なくとも1種を有効成分として含む、鉄欠乏性貧血改善及び/又は予防用飲食品。
[一般式(1)中、R1は水素原子又はアルキル基を示し、R2は水素原子又はガロイル基を示し、R3は水素原子、水酸基又は−OR1で表される基を示す。複数あるR1は互いに同一でも異なっていてもよい。R2が水素原子の場合、R3は水酸基又は−OR1で表される基であり、R3が水素原子の場合、R2はガロイル基である。ガロイル基中の水酸基の水素原子はアルキル基で置換されていてもよい。]
[一般式(2)中、R4は水素原子又はアルキル基を示し、R5は水素原子、水酸基又は−OR4で表される基を示す。複数あるR4は互いに同一でも異なっていてもよい。]
[一般式(3)中、R6は水素原子又はアルキル基を示し、R7は水素原子、水酸基又は−OR6で表される基を示し、R8及びR9は、それぞれ独立に水素原子、水酸基又は−OR6で表される基を示す。複数あるR6は互いに同一でも異なっていてもよい。R7が水酸基又は−OR6で表される基である場合、R8及びR9の少なくとも一方が水素原子である。] - 前記化合物が、(−)−ガロカテキンガレート、(−)−エピガロカテキンガレート、(−)−カテキンガレート、(+)−ガロカテキン、(−)−エピガロカテキン、(−)−エピカテキンガレート、(−)−エピガロカテキン−3−O−(4”−O−メチル)ガレート、(−)−エピガロカテキン−3−O−(3”−O−メチル)ガレート、ルテオリン、アピゲニン、ジヒドロミリセチン、ケルセチン及びケンフェロールからなる群から選ばれる少なくとも1種である、請求項7に記載の鉄欠乏性貧血改善及び/又は予防用飲食品。
- 前記一般式(1)で表される化合物が、(−)−ガロカテキンガレート及び/又は(−)−エピガロカテキンガレートである、請求項7に記載の鉄欠乏性貧血改善及び/又は予防用飲食品。
- ガロタンニン、エラジタンニン及びこれらの塩からなる群から選ばれる少なくとも1種を有効成分として含む、鉄欠乏性貧血改善及び/又は予防用飲食品。
- 前記有効成分がストリクチニン又はその塩である、請求項10に記載の鉄欠乏性貧血改善及び/又は予防用飲食品。
- 没食子酸又はその塩を有効成分として含む、鉄欠乏性貧血改善及び/又は予防用飲食品。
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