JP2018523678A - β−マンゴスチンを有効成分として含有する肌美白用組成物 - Google Patents
β−マンゴスチンを有効成分として含有する肌美白用組成物 Download PDFInfo
- Publication number
- JP2018523678A JP2018523678A JP2018508209A JP2018508209A JP2018523678A JP 2018523678 A JP2018523678 A JP 2018523678A JP 2018508209 A JP2018508209 A JP 2018508209A JP 2018508209 A JP2018508209 A JP 2018508209A JP 2018523678 A JP2018523678 A JP 2018523678A
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- Prior art keywords
- mangosteen
- composition
- melanin
- mangostin
- present
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- 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.)
- Granted
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Landscapes
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Abstract
Description
1.試料の準備
マンゴスチン(Garcinia mangostana)の果皮はベトナムから収集し、2009年8月ランシフード社(www.lansea.co.kr、韓国 ソウル)から提供してもらった。証拠標本は慶北大学(韓国)の植物標本室に保管した。
β−マンゴスチンを分離及び抽出するために、乾燥したマンゴスチンの果皮0.5kgを粉末化した後、常温でクロロホルムで抽出した。エキスは減圧濃縮器を用いて濃縮させ、暗赤色の残留物(65.6g)を得るために使った溶媒を完全に除去するために乾燥器に保管した。前記残留物の一部(5g)はn−ヘキサン/アセトンの段階的勾配として、シリカゲル(5×50cm、230〜400 mesh、500g)カラムクロマトグラフィ[30:1(1.5L)、15:1(1.5L)、10:1(1.5L)、8:1(1.5L)、6:1(1.5L)、4:1(1.5L)、1:1(1.5L)及びアセトン(2L)]方法を実施し、薄層クロマトグラフィ・プロファイルとの比較に基づいて5個の小分画物(CC1〜CC5)に区分した。β−マンゴスチン(252mg)を得る小分画物CC2は、ヘキサン/エチルアセテート勾配(30:1→1:1)を用いたフラッシュカラムクロマトグラフィ法、α−マンゴスチンの豊かな、α−マンゴスチン(2453mg)を得る小分画物CC3はヘキサン/エチルアセテート勾配(20:1→1:1)を用いたフラッシュカラムクロマトグラフィ法、及びγ−マンゴスチンの豊かな、γ−マンゴスチン(415mg)を得る小分画物CC4はヘキサン/エチルアセテート勾配(15:1→1:1)を用いたフラッシュカラムクロマトグラフィ法を実施した。精製された化合物は、下記の先行文献のデータと本発明の1H及び13C NMRデータとを比べることで確認した(Ryu et al.,2011,Phytochemistry 72,2148−54)。
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)、バフィロマイシンA1、3−MA(3−methyladenine)及びクロロキンはシグマ・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α−、β−、及びγ−マンゴスチンを処理して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β−マンゴスチン及び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β−マンゴスチン及び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、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)を用いて実施し、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。チロシナーゼ及びTRP−1に対する抗体はサンタクルーズ(Santa Cruz Biotechnology,USA)、LC3B、p62及びATG5はCST(Cell Signaling Technology,USA)、PMEL(premelanosome protein)に対する抗体はAbcam(UK)から購買し、信号感知は向上した化学発光(Bio−Rad)を通じて確認した。
B16F10細胞は、リポフェクタミン3000(Invitrogen,Carlsbad,CA,USA)を用いてmRFP−EGFP−LC3B(Kimura et al.,2007,Autophagy 3,452−60)に感染させ、前記細胞にβ−マンゴスチン(10μM)及びα−MSH(1μM)を処理して共焦点顕微鏡(FV1000,Olympus,Tokyo)を用いて分析した。
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、3種の食用キサントン系列であるα−、β−、及びγ−マンゴスチンをマンゴスチンの果皮から分離及び精製した(図1)。前記3種のキサントン系列の細胞毒性を確認するために、B16F10細胞に多様な濃度のα−、β−、及びγ−マンゴスチンを処理して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性を確認した。その結果、図2に示したようにアルファ及びγ−マンゴスチンを処理した場合、20μM及び40μMで強い細胞毒性を示した一方、β−マンゴスチンを処理した場合には40μMでも細胞毒性を示していないということが分かった。
β−マンゴスチンが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、B16F10細胞をα−MSH及びβ−マンゴスチンで処理して72時間培養した。その結果、図3に示したようにα−MSHのみで処理した場合に細胞ペレットが黒色に変わったが、β−マンゴスチンと共に処理した場合にペレットの色が黒色から白色に変わった。すなわち、β−マンゴスチンがα−MSHによって誘導された色素沈着を抑制した。また、3種のキサントン系列であるα−、β−、及びγ−マンゴスチンのメラニン含有量の低減効果を比べた結果、α−マンゴスチン及びα−MSHで共に処理した場合、α−MSHで単独処理した時より約20%のメラニン含有量を低減させ、γ−マンゴスチンはメラニン含有量をさらに増加させた(図4A)。一方、本発明のβ−マンゴスチンは濃度依存的にメラニン含有量及びL−DOPA酸化度を効果的に低減させた(図4B)。特に、α−マンゴスチンと同じ濃度である5μMを処理した場合に約40%のメラニン含有量を低減させたため、α−マンゴスチンより美白活性が顕著であるということが分かった。また、前記実施例1で調べたように、α−マンゴスチンは細胞毒性が強いため、産業的に有用な美白活性成分としてはα−マンゴスチンよりβ−マンゴスチンがさらに有用であるということが分かる。
β−マンゴスチンの美白効果を確認するために、チロシナーゼ及びTRP−1についてRT−PCR及びウエスタンブロッティング分析を行った。その結果、図5に示したように、β−マンゴスチンはα−MSHによって誘導されたチロシナーゼ及びTRP−1の発現量を効果的に低減させた。
オートファジーは、オートファゴソームとリソゾームとの融合過程を通じて起きるものであり、β−マンゴスチンで誘導された脱色効果が前記オートファジー過程中にリソゾームに依存的なタンパク質分解を通じて起きるかどうかを確認するために、B16F10細胞にβ−マンゴスチン、α−MSH及びリソゾーム活性を阻害するバフィロマイシンA1(液胞タイプのH+−ATPase抑制剤)を処理した。その結果、図7に示したように前記条件の下でバフィロマイシンA1はβ−マンゴスチンで誘導されたチロシナーゼの発現抑制を阻害した。すなわち、バフィロマイシンA1はオートファゴソーム及びリソゾームの融合を抑制するということが分かった。また、他のオートファジー抑制剤であるクロロキン(CQ)及び3−メチルアデニン(3−MA)もβ−マンゴスチンで誘導されたチロシナーゼの発現抑制を阻害し、オートファジー抑制剤のマーカーであるp62及びPMELの発現抑制を阻害するということが分かり、3−MAを処理したグループでβ−マンゴスチンにより低減したメラニン含有量が再び増加するということが分かった(図8)。
メラニン細胞刺激ホルモンであるα−MSHによって既に生成されているメラニンを除去するβ−マンゴスチンの活性を確認するために、B16F10細胞を2日間α−MSH処理した後、メラニンを合成した後で本発明のβ−マンゴスチン及びオートファジー抑制剤である3−MAで処理した。その結果、図11に示したように本発明のβ−マンゴスチンが相当量のチロシナーゼ及びPMELの発現量を低減させるだけではなく、既に生成されているメラニン含有量も効果的に低減させるということが分かった。
Claims (10)
- 下記の化学式1で表示されるβ−マンゴスチン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β−マンゴスチンは、マンゴスチンの果皮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β−マンゴスチンは、マンゴスチン果皮をクロロホルムで抽出して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、チロシナーゼまたはTRP−1(tyrosinase−related protein−1)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か、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で表示されるβ−マンゴスチン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、茶色点もしくは黒点、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もしくは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7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7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で表示されるβ−マンゴスチン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予防または改善用の健康機能食品組成物。
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CN103393576A (zh) * | 2013-08-07 | 2013-11-20 | 伽蓝(集团)股份有限公司 | 一种山竹提取物及其应用 |
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KR101721917B1 (ko) | 2017-03-31 |
EP3354254A4 (en) | 2019-03-27 |
US20180256486A1 (en) | 2018-09-13 |
EP3354254A1 (en) | 2018-08-01 |
US11882858B2 (en) | 2024-01-30 |
WO2017052155A1 (ko) | 2017-03-30 |
CN107920980B (zh) | 2021-06-11 |
JP6681974B2 (ja) | 2020-04-15 |
KR20170034678A (ko) | 2017-03-29 |
MY196718A (en) | 2023-05-02 |
EP3354254B1 (en) | 2020-04-01 |
CN107920980A (zh) | 2018-04-17 |
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