JP2018536633A - アモルフィゲニを有効成分として含有する肌美白用組成物 - Google Patents
アモルフィゲニを有効成分として含有する肌美白用組成物 Download PDFInfo
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- JP2018536633A JP2018536633A JP2018518632A JP2018518632A JP2018536633A JP 2018536633 A JP2018536633 A JP 2018536633A JP 2018518632 A JP2018518632 A JP 2018518632A JP 2018518632 A JP2018518632 A JP 2018518632A JP 2018536633 A JP2018536633 A JP 2018536633A
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- Prior art keywords
- amorphigeni
- melanin
- composition
- present
- acid
- 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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Abstract
Description
1.アモルフィゲニ(amorphigeni)の分離及び抽出
アモルフィゲニを分離及び抽出するために、陰乾しした0.5kgのイタチハギの根に5Lのアセトンを添加して7日間抽出した。エキスを減圧濃縮して21gの濃縮物を得、製造した濃縮物をシリカゲルカラム(10×30cm)を用いて1段階の分離を施した。この時、溶離溶媒はヘキサン−アセトンを用い、ヘキサン−アセトン混合溶液を100:1から100%(v/v)アセトンまで極性を増大させつつ溶離させて7個の分画物(A〜G)を得た。目標の化合物であるアモルフィゲニが多く含有している分画物Cを濃縮して濃縮物1.3gを得、得られた濃縮物1.3gについてシリカゲルカラムクロマトグラフィをヘキサン−アセトン(4:1)混合溶媒の条件下で施して70%以上の純度の160mgのアモルフィゲニを得た。得られた分画物を80%(v/v)メタノールで溶離させるゲルクロマトグラフィ(Sephadex LH−20)を施して98%純度の29mgのアモルフィゲニを得た。得られた化合物の構造は1H−NMR、13C−NMR、2D−NMR、DEPT及び質量分析器を用いて明らかにした。
B16F10マウスメラノーマ細胞ラインはATCC(American Type of Culture Collection,USA)から提供してもらい、前記細胞は10%のFBS(fetal bovine serum)及び1%のペニシリン/ストレプトマイシン(Sigma−Aldrich,USA)が添加されたDME(Dulbecco’s Modified Eagle’s)培地に5%のCO2加湿培養器で37℃の条件の下で培養された。α−MSH(melanocyte−stimulating hormone)及び3−MA(3−methyladenine)はシグマ・アルドリッチ、チロシン−EDTAはロンザ(Lonza,USA)、及びMTT([3−(4,5−dimethylthiazol−2−yl)−2,5−diphenyl tetrazolium bromide)はアムレスコ(Amresco,USA)から購買して下記の実施例に使った。
B16F10細胞は96・ウェルプレートに24時間培養した後、前記細胞に多様な濃度のアモルフィゲニを処理して24時間培養した。次いで、前記細胞にMTT(5μg/mL)溶液を添加して3時間培養した後、培地を除去して細胞をDMSOで処理して20分間培養し、マイクロプレート・リーダ(Bio−Rad)を用いて595nmで吸光度を測定した。
メラニン含有量の測定は、ヤングら(Yang et al.,2006、Acta pharmacologica Sinica 27,pp.1467−73)の方法をやや変形して実施した。B16F10細胞を6・ウェルプレートに分注して24時間培養させた後、前記細胞にアモルフィゲニ及びα−MSHをそれぞれ1μMずつ処理して48時間培養した。培養された細胞はトリプシン処理法で65℃でDMSOが含まれている1N NaOHで24時間溶かして収穫し、マイクロプレート・リーダ(Bio−Rad)を用いて415nmでメラニン含有量を測定した。
チロシナーゼ活性はオグシら(Ohgushi et al.,2009,Biological&pharmaceutical bulletin 32,308−10)の方法をやや変形して測定した。B16F10細胞を6・ウェルプレートに分注して24時間培養させた後、前記細胞にアモルフィゲニ及びα−MSHをそれぞれ1μMずつ処理して48時間培養した後、培養された前記細胞を収穫して氷で1時間の間に1%のトリトンX−100溶液で溶解させた。タンパク質は4時間の間に5%のCO2加湿培養器で37℃条件の下で100μL(2mg/ml)のL−DOPAと共に培養し、次いで、マイクロプレート・リーダ(Bio−Rad)を用いて490nmで吸光度を測定した。
総RNAはRiboEX試薬(GeneAll Biotechnology Co.Ltd,Seoul,Korea)を用いて細胞から抽出し、cDNAは逆転写(Thermo Scientific,Waltham,MA,USA)を通じて2μgのRNAを用いて合成した。PCRは、SolgTM e−Taq DNAポリメラーゼキット(SolGent Co.Ltd,Daejeon,Korea)を用いて施し、下記の表1に示したように各プライマーを用いた。
総タンパク質は、RIPA溶解バッファ(50mM Tris−HCl(pH8.0)、150mM NaCl、1%のNP−40、0.5%のデオキシコール酸塩及び0.1%のSDS)を用いて抽出した。前記タンパク質は10〜15%のSDS−PAGE上で分離した後、PVDFメンブレイン(Millipore,Billerica,MA,USA)に移入した。前記メンブレインは0.1%のツイン20を含有するTBS(tris−buffer saline)に1時間の間に5%のスキムミルク及び一次抗体と共に培養させた。チロシナーゼに対する抗体はサンタクルーズ(Santa Cruz Biotechnology,USA)、ATG5はCST(Cell Signaling Technology,USA)、PMEL(premelanosome protein)に対する抗体はAbcam(UK)から購買した。
マウスATG5 siRNAに好適なsiRNAはジェノリューション(Seoul,Korea)から合成し、B16F10細胞は製造会社(Invitrogen社)の指示に従ってリポフェクタミン3000(Invitrogen,Carlsbad,CA,USA)を用いてsiATG5に感染させた後、前記細胞にアモルフィゲニ(10μM)及びα−MSH(1μM)を48時間処理した後、その結果を確認した。
すべてのデータはunpaired Student’s t−testを用いて分析し、結果はP<0.05である場合に統計的に有意であると見なした。
本実施例1ではメラニン細胞で脱色を誘導する機能的植物代謝産物を探すために、アモルフィゲニをイタチハギの根から分離した(図1)。前記アモルフィゲニの細胞毒性を確認するために、B16F10細胞を多様な濃度のアモルフィゲニで処理して24時間培養し、MTT(3−(4,5−dimethylthiazol−2−yl)−2,5−diphenyltetrazolium bromide)分析を通じて細胞生存率を確認した。その結果、図2に示したようにアモルフィゲニの100〜1600nMで低い細胞毒性を示した一方、細胞死滅を誘導していないということが分かった(図3)。
アモルフィゲニがα−MSHによって誘導された色素沈着を抑制できるかどうかを調べるために、B16F10細胞をα−MSH及びアモルフィゲニでそれぞれまたは同時に処理して72時間培養した。その結果、図4に示したようにα−MSHのみで処理した場合にはメラニン含有量及びL−DOPA酸化度をよほど増加させた一方、アモルフィゲニ及びα−MSHで共に処理した場合にはメラニン含有量及びL−DOPA酸化度を低減させる傾向を示した。すなわち、本発明のアモルフィゲニがメラニン含有量を低減させて色素沈着を抑制させるということが分かった。
B16F10メラニン細胞をα−MSHで処理するか、またはα−MSH及びアモルフィゲニと共に48時間処理した後、チロシナーゼ(TYR)及びPMELのタンパク質発現レベルをそれぞれウエスタンブロットを通じて測定した。その結果、図5に示したように、本発明のアモルフィゲニはα−MSHによって増加したチロシナーゼ及びPMELのタンパク質発現量を効果的に低減させた。
アモルフィゲニがオートファジーを誘導してチロシナーゼ及びPMELタンパク質を破壊するかどうかを確認するために、B16F10メラニン細胞をα−MSH、アモルフィゲニ及びオートファジー抑制剤である3MA(3−methyladenine)で共に48時間処理した。次いで、チロシナーゼ及びPMELのタンパク質発現レベルをウエスタンブロットを通じて測定した。その結果、図7に示したようにα−MSH、アモルフィゲニ及び3MAで共に処理した細胞では、α−MSH及びアモルフィゲニで共に処理した時に減少したチロシナーゼ及びPMELのタンパク質発現量を再び増加させた。
アモルフィゲニがα−MSHによって既に生成されているメラノソームを破壊するかどうかを調べるために、B16F10メラニン細胞をα−MSHで48時間処理してメラノソームを合成した後、アモルフィゲニを48時間処理した後でメラニン含有量を測定した。その結果、図10に示したように既に生成されているメラニン含有量を効果的に低減させるということが分かった。
Claims (9)
- 下記の化学式1で示されるアモルフィゲニ(amorphigeni)または化粧品学的に許容可能なその塩を有効成分として含有する、肌美白用化粧料の組成物。
- 前記アモルフィゲニは、イタチハギの根から分離したものであることを特徴とする、請求項1に記載の肌美白用化粧料の組成物。
- 前記組成物は、チロシナーゼの活性を阻害することを特徴とする、請求項1に記載の肌美白用化粧料の組成物。
- 前記組成物はメラニンの生成を抑制する、または既に生成されているメラニンを除去することを特徴とする、請求項1に記載の肌美白用化粧料の組成物。
- 前記組成物は溶液、懸濁液、乳濁液、ペースト、ゲル、クリーム、ローション、パウダー、せっけん、界面活性剤を含有しているクレンジング・オイル、粉末ファウンデーション、ファウンデーション、ワックス・ファウンデーション及びスプレーのうち選択されたいずれか一つの剤形であることを特徴とする、請求項1に記載の肌美白用化粧料の組成物。
- 下記の化学式1で示されるアモルフィゲニ(amorphigeni)または薬学的に許容可能なその塩を有効成分として含有する、メラニン色素の過多沈着疾患の予防または治療用の薬学組成物。
- 前記メラニン色素の過多沈着疾患は、そばかす、老人性斑点、肝斑、シミ、茶色点または黒点、日光色素斑、緑黒皮症、薬物使用後の過多色素沈着、妊娠肝斑、または擦り傷及び火傷などの傷や皮膚炎による炎症後の過多色素沈着であることを特徴とする、請求項6に記載のメラニン色素の過多沈着疾患の予防または治療用の薬学組成物。
- 前記組成物は、注射剤、クリーム、パッチ、噴霧剤、軟膏剤、硬膏剤、ローション剤、リニメント剤、パスタ剤及びカタプラズマ剤のうち選択されたいずれか一つの剤形に製造されることを特徴とする、請求項6に記載のメラニン色素の過多沈着疾患の予防または治療用の薬学組成物。
- 下記の化学式1で示されるアモルフィゲニ(amorphigeni)または薬学的に許容可能なその塩を有効成分として含有する、メラニン色素の過多沈着の予防または改善用の健康機能食品組成物。
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