JP5230152B2 - プロフィラグリン産生促進剤及びフィラグリン産生促進剤 - Google Patents
プロフィラグリン産生促進剤及びフィラグリン産生促進剤 Download PDFInfo
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- JP5230152B2 JP5230152B2 JP2007239859A JP2007239859A JP5230152B2 JP 5230152 B2 JP5230152 B2 JP 5230152B2 JP 2007239859 A JP2007239859 A JP 2007239859A JP 2007239859 A JP2007239859 A JP 2007239859A JP 5230152 B2 JP5230152 B2 JP 5230152B2
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- extract
- acteoside
- filaggrin
- inhibitor
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Description
本発明のマトリックスメタロプロテアーゼ−1阻害剤、マトリックスメタロプロテアーゼ−2阻害剤、エストロゲン様作用剤、プロフィラグリン産生促進剤、フィラグリン産生促進剤、抗肥満剤又はサイクリックAMPホスホジエステラーゼ阻害剤は、キンモクセイからの抽出物及び/又はアクテオシド(Acteoside)を有効成分として含有する。
キンモクセイの花部の粗粉砕物150gに50質量%エタノール(水とエタノールとの質量比=1:1)1500mLを加え、穏やかに攪拌しながら80℃にて2時間保ち、熱時濾過した。続いて、残渣に50質量%エタノール1500mLを加え、穏やかに攪拌しながら80℃にて2時間保ち、熱時濾過した。得られた濾液を合わせて減圧下にて濃縮し、減圧乾燥機で乾燥してキンモクセイ花部抽出物(71.4g,試料1)を得た。
製造例1により得られたキンモクセイ花部抽出物(試料1)8.9gをクロロホルム/メタノール/水=10:5:1の混合溶液に溶解し、シリカゲル(商品名:シリカゲル60,メルク社製)を充填したガラス製のカラム上部より流入して、シリカゲルに吸着させた。ガラス製のカラムに移動層としてクロロホルム/メタノール/水=10:5:1を流し、その溶出液を集め、溶媒を留去して、精製物(2.5g,試料2)を得た。
[M−H]− m/z 623(理論値:C29H36O15−H=623)
[M+Na]+ m/z 647(理論値:C29H36O15+Na=647)
6.69 (1H, d, J=2.0 Hz, H-2), 6.67 (1H, d, J=8.1 Hz, H-5), 6.55 (1H, dd, J=2.0, 8.1Hz, H-6), 2.78 (2H, t-like, H-7), 4.01 (1H, overlapped, H-8a), 3.70 (1H, overlapped, H-8b), 7.05 (1H, d, J=2.2 Hz, H-2’), 6.77 (1H, d, J=8.3 Hz, H-5’), 6.94 (1H, dd, J=2.2, 8.3Hz, H-6’), 7.58 (1H, d, J=15.9 Hz, H-7’), 6.27 (1H, d, J=15.9 Hz, H-8’), 4.36 (1H, d, J=7.8Hz, GlcH-1), 3.39 (1H, dd, J=7.8, 8.1Hz, GlcH-2), 3.80(1H, br.t, J=9.0 Hz, Glc H-3), 4.88 (1H, br.t, J=9.2 Hz, Glc H-4), 3.58 (1H, overlapped, Glc H-5), 3.48 (2H, overlapped, Glc H-6), 5.18( 1H, br.s, Rha H-1), 3.90 (1H, m, Rha H-2), 3.58 (2H, overlapped, Rha-H-3 and Rha H-5), 3.30(1H, overlapped, Rha-H-4), 1.08.(3H, d, J=6.1 Hz, Rha H-6)
131.1(s, C-1), 116.1(d, C-2), 146.5(s, C-3), 144.3(s, C-4), 116.8(d, C-5), 121.0(d, C-6), 36.4(t, C-7), 72.0(t, C-8), 127.3(s, C-1’), 114.9(d, C-2’), 145.8(s, C-3’), 149.4(s, C-4’), 116.2(d, C-5’), 122.9(d, C-6’), 147.7(d, C-7’), 114.4(d, C-8’), 167.9(s, C-9’), 103.9(d, Glc C-1), 75.9(d, Glc C-2), 81.4(d, Glc C-3), 70.7(d, Glc C-4), 75.8(d, Glc C-5), 62.1(t, Glc C-6), 102.7(d, Rha C-1), 72.1(d, Rha C-2), 71.8(d, Rha C-3), 73.5(d, Rha C-4), 70.2(d, RhaC-5), 18.3(q, Rha C-6)
製造例1にて得られたキンモクセイ花部抽出物(試料1)及び製造例2にて得られたアクテオシド(Acteoside,試料2)について、以下のようにして間オリックスメタロプロテアーゼ−1(MMP−1)阻害作用を試験した。
式中、Aは「試料無添加、酵素添加での波長320nmにおける吸光度」を表し、Bは「試料無添加、酵素無添加での波長320nmにおける吸光度」を表し、Cは「試料添加、酵素添加での波長320nmにおける吸光度」を表し、Dは、「試料添加、酵素無添加での波長320nmにおける吸光度」を表す。
結果を表1に示す。
製造例1にて得られたキンモクセイ花部抽出物(試料1)及び製造例2にて得られたアクテオシド(Acteoside,試料2)について、以下のようにしてマトリックスメタロプロテアーゼ−2(MMP−2)阻害作用を試験した。
ヒトMMP−2 cDNAを、下記の5'PCRプライマー及び3'PCRプライマーを用い、MMP−2の3.3kb cDNA断片を含むpSG−GelAを鋳型としてPCR反応を行った。得られた30Alaから474Valまでをコードする1.3kb PCR断片をBam Hl/Sallで消化し、pTH−72発現ベクター(pTH−MMP2−PC)のBam Hl/Sall部位にクローン化した。
5'PCRプライマー:5'-ggcggatccatggcgccgtcgcccatcatc-3'
3'PCRプライマー:3'-gccgtcgactacaatgtcctgtttgcagat-5'
試料を蒸留水に溶解させて8.0mg/mLとした後、蒸留水にて4.0mg/mL、2.0mg/mLに希釈し、懸濁物を除くため濾過した。MMP−2阻害活性の測定は、活性型MMP−2 40μL、試料溶液(試料濃度は表2を参照)20μL、アッセイバッファー(500mMのトリス−塩酸緩衝液(pH7.5)、1.5Mの塩化ナトリウム、100mMの塩化カルシウム、500μMの硫酸亜鉛、30mMのアジ化ナトリウム、0.05%のBrij35)20μLを、37℃で15分間プレインキュベーションした後、MOCAc/DNP peptide120μL(4.16μM)を添加し、37℃で2時間反応させ、その後EDTA10μL(200mM)を添加した。反応液中の生成物について高速液体クロマトグラフィー分析によるピーク面積を測定した。試料溶液の代わりに蒸留水を加えた反応液の生成物を100%として試料のMMP−2阻害率(%)を算出した。
結果を表2に示す。
製造例1にて得られたキンモクセイ花部抽出物(試料1)及び製造例2にて得られたアクテオシド(Acteoside,試料2)について、以下のようにしてエストロゲン様作用を試験した。
式中、Aは「試料溶液添加時の吸光度」を表し、Bは「試料溶液無添加時の吸光度」を表す。
結果を表3に示す。
製造例1にて得られたキンモクセイ花部抽出物(試料1)及び製造例2にて得られたアクテオシド(Acteoside,試料2)について、以下のようにしてプロフィラグリン産生促進作用及びフィラグリン産生促進作用を試験した。
10μg/列に調整したサンプルをSDS−PAGEにより展開し、PVDF膜に転写した。5%スキムミルクを含むPBS(−)でブロッキングを行った後、抗ヒトフィラグリンモノクローナル抗体(Harbor Bio-Products)、ビオチン標識抗マウスIg(Whole Ab,Amersham Biosciences社製)及びストレプトアビジンーペルオキシダーゼ複合体(CALBIOCHEM社製)を、0.1%Tween20、0.3%スキムミルクを含むPBS(−)で1000倍に希釈して順次反応させ、ECL Western blotting detection reagents and analysis system(Amersham Biosciences社製)の発光によりプロフィラグリン及びフィラグリンを検出した。検出したバンドをKODAK 1D Image Analysis Software EDAS290 Version3.5にて定量的に測定した。
上記式において、Aは「試料添加時のNet intensity(プロフィラグリン及びフィラグリンの合計値)」を、Bは「試料無添加時(コントロール)のNet intensity」を表す。
結果を表4に示す。
製造例1にて得られたキンモクセイ花部抽出物(試料1)及び製造例2にて得られたアクテオシド(Acteoside,試料2)について、以下のようにしてサイクリックAMPホスホジエステラーゼ阻害作用を試験した。
Column : Wakosil C18-ODS 5μm(和光純薬工業社製)
Mobil phase : 1mM TBAP in 25mM KH2PO4 : CH3CN = 90 : 10
Flow rate : 1.0mL/min
Detector : 260nm
Atten : 32〜64
式中、Aは「試料添加時のcAMPのピーク面積」を表し、Bは「試料無添加時のcAMPのピーク面積」を表す。
結果を表5に示す。
Claims (2)
- アクテオシド(Acteoside)を有効成分として含有することを特徴とするプロフィラグリン産生促進剤(シワ形成抑制の用途を除く)。
- アクテオシド(Acteoside)を有効成分として含有することを特徴とするフィラグリン産生促進剤(シワ形成抑制の用途を除く)。
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