JP2011504467A - スチルベンポリフェノール誘導体を含む組成物、並びに生体の老化及び老化に影響を及ぼす疾患に対抗するためのそれらの使用 - Google Patents
スチルベンポリフェノール誘導体を含む組成物、並びに生体の老化及び老化に影響を及ぼす疾患に対抗するためのそれらの使用 Download PDFInfo
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Abstract
Description
− R1は、アルキル基、又は前記で定義されたようなRにより表される、植物油の脂肪酸のアシル基であり、
− R2は、水素、又はR”におけるまたは別の構成単位のR2への連結点であり、
− R3は、水素、又はR”におけるまたは別の構成単位のR4における連結点であり、
− R4は、アルキル基、又は前記で定義されたようなRにより表される、植物油の脂肪酸のアシル基、又は別の構成単位のR3における連結点であり、
− R”は、H又は別の構成単位のR2若しくはR3における連結点を表し、
− R’は、水素、又は、前記で定義されたようなRによって表される植物油の脂肪酸のO−アシル基である)
の化合物およびこれらの部分のジアステレオマー及び位置異性体であることを特徴とする組成物に関する。
− 第1工程において、分子あたり少なくとも1個、好ましくは1〜2個のフェノール性OH基の水素に対するアルキル基の置換を許容する条件下にアルキル化剤と、
− 第2工程において、アルキル化後に依然としてフリーである−OH基の水素に対する、アシル化剤により遊離されるアシル基−COR(Rは前記で定義された通りである)の混合物による置換を許容する条件下に、アシル化剤、特に酸無水物又は酸塩化物と、反応させることを含む方法により得られる。
− 植物油のグリセリドをけん化し、次いで酸性化し、
− 脱水(アシル化剤は酸無水物である)又は塩素化(アシル化剤は酸塩化物である)により活性化することを含む方法により植物油から調製されるが、同一の活性化効果を付与する他の誘導体が用いられてもよい(必要に応じて、エステル交換、酵素的アシル化)。
− 塩素化に用いられる溶媒は、アルコールにより安定化されないという条件で、例えば、ジクロロメタン又はクロロホルムであり、
− 塩素化剤は、例えば、塩化チオニル又は塩化オキサリルであり、
− 触媒はジメチルホルムアミドであってよく、
− 塩化アシルは、「ボールオーブン」(クーゲルロール)中、高真空下の蒸留により精製される。
フロログルシノール1.560g(12.3ミリモル)を、上端に冷却器を備え付けた二口フラスコ中の無水アセトン20mLに溶解させる。アルゴン雰囲気下に撹拌しながら、炭酸カリウム(K2CO3)1.685g(12.3ミリモル、2化学当量)の存在下、ヨウ化メチル766μL(=1.746g;25℃においてd=2.28g/mL、すなわち、12.3ミリモル=レスベラトロールに対して1モル当量)を加える。反応物を3時間にわたって還流加熱する。
レスベラトロール450mg(1.97ミリモル)を、上端に冷却器を備え付けた二口フラスコ中の無水アセトン10mLに溶解させる。アルゴン雰囲気下に撹拌しながら、炭酸カリウム(K2CO3)270mg(1.97ミリモル、2化学当量)の存在下、ヨウ化メチル123μL(=280mg;25℃においてd=2.28g/mL、すなわち、1.97ミリモル=レスベラトロールに対して1モル当量)を加える。反応物を3時間にわたり還流加熱する。
特許FR 2 766 176の方法により得られるようなスチルベノイドポリフェノール抽出物10.08g(44ミリモル)について操作が行われ、アセトン50mLに溶解させられる。活性化K2CO312.25g(88ミリモル=4化学当量)、次いでアルキル化剤、この場合は硫酸ジメチル(dimethyl sulfate :DMS)3.15mL(33ミリモル、1.5化学当量)を、アルゴン雰囲気下、撹拌しながら加える。
(工程1:オリーブ油のけん化)
冷却器を備えた丸底フラスコ内に収容された「バージン」オリーブ油50.46g(57ミリモル=171当量)を、エタノール2.5mL及び水50mL中の水酸化カリウム16.08g(285ミリモル、1.67当量)の溶液と混合する。反応物を5時間にわたって還流する。反応物を、周囲温度で更に14時間にわたって撹拌する。
工程1から得られたフリーな酸41.5g(147.1ミリモル)のクロロホルム溶液232mL(アミレン上で安定化される)を、アルゴン雰囲気中、丸底フラスコ内で攪拌し、これを、氷浴によって冷却する。滴下漏斗を用い、塩化オキサリル13.8mL(162mM=1.1当量)を30分間かけて滴下して導入する。ジメチルホルムアミド(DMF)1mLを導入し、氷浴上で5分間にわたり撹拌を続ける。次いで、減圧下における反応混合物の濃縮により(過剰量のクロロホルム及び塩化オキサリル)、わずかに黄色の着色のある油状残渣44.3gを得る(粗収率=100%)。
FT−IR(図7)及びプロトンNMR(図8)のスペクトルは、これらの塩化物の排他的形成と完全に一致する:塩化アシルの特徴である1798cm−1におけるバンド。
実施例3によるO−アルキル化レスベラトロールオリゴマー8.4g(35ミリモル)を、トリエチルアミン9.3mL(70ミリモル)と混合したヘキサン106mLに懸濁させ、アルゴン雰囲気下に撹拌する。実施例4において調製された塩化物10.65gをヘキサン45mLで希釈したもの(35.1ミリモル、1当量)を滴下して加える。
− ATRモード(図9)で得られるフーリエ変換赤外スペクトルにより、フェノールエステルのカルボキシの特徴である1764cm−1における強いバンドの出現と、これと同時に、フリーなフェノールヒドロキシに相当する3350cm−1を中心とする広いバンドの消失が示される。
Claims (30)
- 構成単位あたりの−O−アルキル基の数は、構成単位あたりに平均して存在するヒドロキシルの数と等しくないことを特徴とする請求項1〜3のいずれか1つに記載の組成物。
- 構成単位あたりに平均して存在するヒドロキシルの数は、1又は2個であることを特徴とする請求項4に記載の組成物。
- 1種以上のアルキル基は、メチル、イソプロピル又はtert−ブチル基であることを特徴とする請求項1〜5のいずれか1つに記載の組成物。
- 前記エステルは、植物油の脂肪酸エステルであることを特徴とする請求項1〜6のいずれか1つに記載の組成物。
- 前記エステルは、ステアリン酸のような飽和脂肪酸、オレイン酸のような一不飽和脂肪酸、リノール酸及びリノレン酸のような必須多不飽和脂肪酸に相当するアシル基Rを含むことを特徴とする請求項7に記載の組成物。
- 前記植物油は、オリーブ油又はブドウ種子油から選択されることを特徴とする請求項7又は8に記載の組成物。
- 請求項1、2及び4〜9のいずれか1つに記載の組成物であって、前記誘導体は、式(IV):
− R1は、アルキル基、又は請求項8において定義されたようなRにより表される、植物油の脂肪酸のアシル基であり、
− R2は、水素、又はR”における若しくは他の構成単位のR2への連結点であり、
− R3は、水素、又はR”における若しくは他の構成単位のR4における連結点であり、
− R4は、アルキル基、又は請求項8において定義されたようなRにより表される、植物油の脂肪酸のアシル基、又は他の構成単位のR3における連結点であり、
− R”は、H又はR2における若しくは他の構成単位のR3における連結点を表し、
− R’は、水素、又は前記で定義されたようなRにより表される、植物油の脂肪酸のO−アシル基である)
およびこれらの部分のジアステレオマーおよび位置異性体と一致することを特徴とする組成物。 - 前記誘導体は、植物抽出物の、安定化され、かつアルキル化された誘導体に相当することを特徴とする請求項1〜11のいずれか1つに記載の組成物。
- 前記植物抽出物が、ブドウの木の抽出物であることを特徴とする請求項12に記載の組成物。
- 前記ブドウの木の抽出物は、ブドウの木の新芽及び/又は茎から得られることを特徴とする請求項13に記載の組成物。
- 前記植物抽出物は、タデ抽出物であることを特徴とする請求項12に記載の組成物。
- 前記植物抽出物は、例えば、桑からの果実抽出物であることを特徴とする請求項12に記載の組成物。
- 請求項1〜17のいずれか1つに記載の組成物の調製方法であって、
前記で定義された植物抽出物ポリフェノール組成物は、
− 第1工程において、各分子の構成モノマー単位あたり少なくとも1個、好ましくは1〜2個のフェノール性OH基の水素に対してアルキル基の置換を許容する条件下にアルキル化剤と、
− 第2工程において、アルキル化後に依然としてフリーである−OH基の水素に対して、アシル化剤により遊離させられるアシル基−COR(Rは請求項8において定義された通りである)の混合物による置換を許容する条件下に、アシル化剤、特に酸無水物又は酸塩化物と、反応させられることを特徴とする方法。 - 前記アシル化剤は、
− 植物油のグリセリドをけん化し、次いで酸性化し、
− 脱水(アシル化剤が酸無水物である場合)又は塩素化(アシル化剤が酸塩化物である場合)により活性化することを含む方法により植物油から得られることを特徴とする請求項18に記載の方法。 - 皮膚老化に対抗するために有効な量の、請求項1〜19のいずれか1つに記載のポリフェノール誘導体の1つ以上の組成物を、外用に適した不活性な賦形剤と組み合わせて含むことを特徴とする化粧品組成物。
- クリーム、軟膏、乳剤、ゲル、リポソーム、ローションのような局所投与に適切な形態をとることを特徴とする請求項20に記載の組成物。
- 0.5〜5%、好ましくは2〜3%の活性生成物を含むことを特徴とする請求項20又は21に記載の組成物。
- 栄養学における、請求項1〜16のいずれか1つに記載の組成物の適用。
- 前記組成物は、液状又は顆粒等、ゲル又はペースト状で、例えば果汁、強壮飲料のような飲料、バターのような乳製品及びその派生物に加えられ、例えば、フルーツガム、キャンディ、チューインガムのような菓子類に組み込まれていることを特徴とする請求項23に記載の適用。
- 医薬としての使用のための、請求項1〜16のいずれか1つに記載の組成物。
- 請求項1〜16のいずれか1つに記載の少なくとも1つの組成物の治療的有効量を、薬学的に許容される賦形剤と組み合わせて含むことを特徴とする医薬組成物。
- 経口、局所又は非経口投与に適切な形態をとることを特徴とする請求項25又は26に記載の組成物。
- 溶液、シロップ、錠剤、ゲルカプセルのような、経口投与のための形態をとることを特徴とする請求項27に記載の組成物。
- クリーム、軟膏、ゲル、ローション又はパッチのような、局所投与のための形態をとることを特徴とする請求項27に記載の組成物。
- 無菌又は滅菌可能な注射溶液のような、非経口投与のための形態をとることを特徴とする請求項27に記載の組成物。
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FR0708020A FR2923717B1 (fr) | 2007-11-15 | 2007-11-15 | Compositions de derives polyphenoliques stilbeniques et leurs applications pour lutter contre les pathologies et le veillissement des organismes vivants |
PCT/IB2008/054818 WO2009063440A1 (fr) | 2007-11-15 | 2008-11-17 | Compositions de dérivés polyphénoliques stilbeniques et leurs applications pour lutter contre les pathologies et le vieillissement des organismes vivants |
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CN102173983A (zh) * | 2011-03-17 | 2011-09-07 | 中南大学 | 一种反-3,4′,5-三甲氧基二苯乙烯的合成方法 |
CN102408893A (zh) * | 2011-09-21 | 2012-04-11 | 浙江大学 | 一种桑枝抗氧化剂的制备方法 |
AU2012348700B2 (en) | 2011-12-06 | 2015-08-27 | Unilever Plc | Skin anti-ageing composition |
FR2989270B1 (fr) * | 2012-04-12 | 2016-12-30 | Soc La Biochimie Appliquee | Composition cosmetique cutanee anti-age contenant des activateurs de l'aconitase mitochondriale |
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PT2222294E (pt) | 2014-08-22 |
EP2222294A1 (fr) | 2010-09-01 |
FR2923717B1 (fr) | 2015-01-16 |
CA2705840A1 (fr) | 2009-05-22 |
FR2923717A1 (fr) | 2009-05-22 |
ES2482115T3 (es) | 2014-08-01 |
CN101977601A (zh) | 2011-02-16 |
RU2491063C2 (ru) | 2013-08-27 |
WO2009063440A1 (fr) | 2009-05-22 |
PL2222294T3 (pl) | 2014-09-30 |
RU2010123790A (ru) | 2013-01-20 |
US20100310615A1 (en) | 2010-12-09 |
EP2222294B1 (fr) | 2014-05-07 |
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