JP5427894B2 - 新規化合物ラマリン及びその用途 - Google Patents
新規化合物ラマリン及びその用途 Download PDFInfo
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- JP5427894B2 JP5427894B2 JP2011535518A JP2011535518A JP5427894B2 JP 5427894 B2 JP5427894 B2 JP 5427894B2 JP 2011535518 A JP2011535518 A JP 2011535518A JP 2011535518 A JP2011535518 A JP 2011535518A JP 5427894 B2 JP5427894 B2 JP 5427894B2
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- ramarin
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Description
本発明の一実施例において、ラットのマクロファージ細胞にラマリンを処理した結果、ラマリンを処理した細胞でH2O2及びNO生成が確実に阻害されることを確認された(図9及び図10)。
本発明の化粧料組成物は、一般的な乳化剤形及び可溶化剤形の形態で製造することができる。乳化剤形の化粧品としては、栄養化粧水、クリーム、エッセンス等があって、可溶化剤形の化粧品としては柔軟化粧水がある。
[実施例1]クレブシエラ・ニューモニエ(Klebsiella pneumoniae)菌株によるグリセロールから3−ヒドロキシプロピオン酸の生産
[実施例1]ラマリナ・テレブラタの大量抽出
ラマリナ・テレブラタは、南極大陸キングジョージ島に群落を成し自生する地衣類であり、キングジョージ島で容易に採取することができる。
完全に凍結乾燥され、粉砕された地衣類ラマリナ・テレブラタサンプル672gをメタノール:水(70:30v/v)混合溶液を利用して室温で冷抽出した後、45〜50℃の水槽で熱抽出した。前記抽出物をろ過した後、溶媒を45℃の真空状態で蒸発させた。前記抽出過程を3回繰り返して、抽出可能な全ての化合物を抽出して、凍結乾燥を経て、最終的に83gの粗抽出物が得られ、前記粗抽出物は使用時まで−20℃に保管した。
実施例1で取得した粗抽出物を1Lの蒸溜水に溶かした後、1Lのヘキサンで3回抽出して、極性が低い色素を除去した。残った液相を1Lのクロロホルムで3回抽出して、極性が低いか極性が中間の化合物を除去した。残った水溶性抽出物は、DPPH自由ラジカルに対しIC50=9μg/mLの高い除去活性を示し、C18ODSカラム(150cm×3cm)を用いて、自動MPLC(mild pressure liquid chromatography)に適用させた。0%、20%、40%、60%、80%及び100%のメタノール(in water)溶液でグラジエント溶媒システムで行った結果、0%メタノールで多くのDPPH自由ラジカルに対する活性(IC50=8μg/mL)が示され、前記活性分画を、C18ODSカラム(250cm×10cm)を使った分取逆相HPLCに流速2mL/minで分取した。用いられた溶媒システムを表2に示す。
高分解能ES−MSの陽性モードと陰性モードを共に使って、化合物のフラグメンテーションパターン検出し、D2O+Acetone d6で1H NMRと13C NMR(400MHz)を行って、化合物の最終構造を確認した。
(1)DPPH自由ラジカル除去能
ラマリンのDPPH自由ラジカル除去能はBloisの方法(Blois, M.S., Nature, 26:1199, 1958)を変形した方法を使った。まず、1.1−diphenyl−2−picryl−hydazil 0.1mmol(in methanol)溶液を製造し、DPPH溶液250μLをいくつかの濃度(0〜10μg/mL)のラマリン(in methanol)溶液750μLと混合した。前記混合溶液を室温で30分間反応させ、DPPH自由ラジカルの含有量を測定するために、UV−Visibleスペクトロフォトメーター(SCINCO-AMERICA)を利用して、517nmで吸光度を測定した。陽性対照群としていくつかの濃度のBHAを使用し、反応混合物がない試験サンプルを陰性対照群として用いた。反応混合物の吸光度が減少するほど、抽出物が高い自由ラジカル除去活性を有する。全ての実験は3回繰り返し行った。
ABTS+除去能は、市販されている水溶性ビタミンE類似体のトロロクス(6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxilic acid)と比較して測定した(Rice-Evans, C. and Miller, N.J., Meth. Enzymol., 234:279, 1994)。0〜40μg/mL濃度のラマリンを抗酸化分析キット(Product code CS0790, Sigma, USA)プロトコルに記載された280μLの反応混合物を含有する自由ラジカル(陽イオン)生成システムに適用した。反応混合物の緑色発色量を、スペクトロフォトメーターを利用して405nmで測定した。実験は3回繰り返し行い、反応混合物がない試験サンプルを陰性対照群として使った。
ラマリンの還元能は、Oyzaizuの方法を少し変形して測定した(Oyaizu, M., Jpn. J. Nutr., 44:307-315, 1986)。0〜20μg/mLのラマリン溶液100μLを燐酸バッファー(0.2mol/L,pH6.6)250μL及びフェリシアン化カリウム(potassium ferricyanid)(10g/L)250μLと混合した。前記反応混合液を50℃で20分間反応させた後、150μLのトリクロロ核酸(trichloroacetic acid)(100g/L)を添加した。その後、FeCl3(1g/L)750μLを反応混合液添加した後、700nmで吸光度を測定した。BHTを陽性対照群として用いて、反応混合液がない試験サンプルを陰性対照群として使い、実験を3回繰り返し行った。
ラマリンのスーパーオキシド陰イオン(super oxide anion)除去能は、Beauchamp and Fridovichの方法に従っていくつかの濃度のBHAと比較して測定した(Beauchamp, C. and Fridovich, I., Anal. Biochem., 44:276, 1971)。
ラマリンのチロシナーゼ阻害能は、Higuchiの方法を少し変形して測定した(Higuchi, M. et al., Planta Med., 59:253, 1993)。0.1M燐酸バッファー(pH6.8)333μL、0.5mM L−DOPA溶液165μL、蒸留水333μL及び0〜10μgのラマリンで構成された反応混合液にマッシュルームチロシナーゼ(440U/mL)67μLを添加した。前記反応混合液を室温で5分間反応させた後、アジ化ナトリウム(sodium azide,1M)33μLを添加して反応を終了させて、471nmで吸光度を測定した。陽性対照群としてはコウジ酸を使い、反応混合液がない試験サンプルを陰性対照群として使い、実験を3回繰り返し行った。
過度な酸化ストレスは、マクロファージの異常機能を誘導して、細胞調節障害をもたらすため、ラマリンがマウスマクロファージで抗酸化能を示すのかを確認した。
H2O2の細胞内生産量をDHRを利用した方法(Roesler, C. et al., Int. J. Immunopharmacol, 13:27-37, 1991)で測定した。
前記LPSまたはPMAの存在または非存在下でラマリン(0.5μg/mL、1μg/mL及び2μg/mL)または10μMデキサメタゾンを含有するDMEMで培地を入れ替えて、さらに24時間培養させた。
Claims (8)
- 南極地衣類であるラマリナ・テレブラタ(Ramalina terebrata)から分離された請求項1に記載の化合物(ラマリン)。
- 前記機能性化粧品組成物は美白またはシワ改善用である請求項7に記載の機能性化粧品組成物(ラマリナ・テレブラタの抽出物を含むものを除く)。
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