JP2006022095A - リパーゼ阻害剤 - Google Patents
リパーゼ阻害剤 Download PDFInfo
- Publication number
- JP2006022095A JP2006022095A JP2005171561A JP2005171561A JP2006022095A JP 2006022095 A JP2006022095 A JP 2006022095A JP 2005171561 A JP2005171561 A JP 2005171561A JP 2005171561 A JP2005171561 A JP 2005171561A JP 2006022095 A JP2006022095 A JP 2006022095A
- Authority
- JP
- Japan
- Prior art keywords
- lipase
- isothiisanoside
- thiisanoside
- acne
- skin
- 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.)
- Granted
Links
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- JVLBOZIUMGNKQW-UHFFFAOYSA-N 1-hydroxy-3,4-seco-4(23),20(29)-lupadien-3,11-olid-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1->4)-O-beta-D-glucopyranosyl-(1->6)-O-beta-D-glucopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1C(CO)OC(OCC2C(C(O)C(O)C(OC(=O)C34C(C(CC3)C(C)=C)C3C(C5(C)CCC(C6(C)C(O)CC(=O)OC(C56)C3)C(C)=C)(C)CC4)O2)O)C(O)C1O JVLBOZIUMGNKQW-UHFFFAOYSA-N 0.000 abstract description 16
- WIDAUXGFFXJZKU-HVLVMTFESA-N Chiisanoside Natural products C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC[C@H]3O[C@@H](OC(=O)[C@]45CC[C@H]([C@@H]4[C@H]6C[C@H]7OC(=O)C[C@@H](O)[C@@H]8[C@@H](CC[C@](C)([C@H]78)[C@]6(C)CC5)C(=C)C)C(=C)C)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H]2CO)[C@H](O)[C@H](O)[C@H]1O WIDAUXGFFXJZKU-HVLVMTFESA-N 0.000 abstract description 16
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Abstract
【解決手段】チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含む医薬、リパーゼ阻害剤、脂質吸収阻害剤、抗肥満剤、高脂血症改善剤、ニキビ改善剤、食品、化粧料。
【選択図】なし
Description
H NMR:表2、表3参照。
実験方法赤血球懸濁液の調製
ラットより採取した血液10mlにACD溶液0.5mlを加えて遠心分離(3000rpm、5min)を行い、赤血球を取り出した。遠心分離後、沈査に等張食塩水(8.9g/L)20mlを加えて遠心分離(3000rpm、5min)を行った。等張食塩水で2回洗浄した後、沈査に等張食塩水を加えて20mlにメスアップした。この赤血球懸濁液0.5mlに1%界面活性剤、TRITON:10g/L、4.5mlを加え撹拌し、遠心分離(3000rpm、5min)を行った。遠心分離後、上清を540nmでの吸光度を測定し、吸光度が0.8〜0.9になるように赤血球懸濁液を調製した。
溶血活性の測定
等張食塩水4.5mlに上記で調製した赤血球懸濁液0.5mlを加えゆっくり撹拌し、その後本発明のサポニンを加えてゆっくり撹拌し、インキュベーション(37℃、20min)した。次いで遠心分離(3000rpm、5min)を行い、得られた上清を540nmでの吸光度を測定した。なお、本試験では陽性対照群として大豆由来のサポニンを用いた。
結果
図3に示したように、陽性対照群としての大豆サポニンは濃度依存的に溶血活性を示し、200μg/mlでほぼ全ての赤血球が破壊された。
一方、本発明のサポニンである11-デオキシイソチイサノサイド、イソチイサノサイド、チイサノサイドは200μg/mlの濃度においても溶血活性はほとんど認められなかった。以上のことから、本発明のサポニンである11-デオキシイソチイサノサイド、イソチイサノサイド、チイサノサイドは溶血活性が弱いことがわかる。
アミラーゼ活性の阻害作用は、Bernfeld. Pの方法(Methods Enzymol., 1, 147-158 (1955))に従って、3,5-ジニトロサリチル酸を用いて反応液中の還元糖の量を定量することにより行った。
すなわち、膵液10μgを酵素として用い、基質として澱粉2mgを用い、反応により生成した還元糖の量を535nmでの吸光度を測定することにより求めた。
なお、比較対照群として、一般的にタンパク質である酵素と水素結合することにより不溶化を起こすことで酵素活性を阻害することが知られているタンニン酸(Loomis, W. D., Methods Enzymol., 16, 528-544 (1974))を用いた。
結果
図4(A)に示したように、タンニン酸はアミラーゼ及びリパーゼの何れにおいても活性阻害作用を有することがわかるが、図4(B)に示したように、本発明のサポニンの一つであるチイサノサイドはリパーゼ活性は阻害するもののアミラーゼ活性は阻害しないことから、本発明のサポニンであるチイサノサイドはリパーゼ活性を特異的に阻害していることがわかる。
<有効成分高含有ウコギ葉エキス(SF)の調製>
有効成分高含有ウコギ葉エキス(SF)の調製は、ウコギ葉熱水抽出物(AE)を2種の吸着樹脂(HP-20、SP-825)カラムクロマトグラフィーを組み合わせることにより調製した。すなわち、AE15.3kgを30%エタノール76.5Lを加え、80℃で30分間、加温溶解させ、放冷後、珪藻土ろ過した。これをHP-20吸着樹脂15.3L(コンディショニング:30%エタノール)を充填せしめたカラムクロマトグラフィーに供し、非吸着画分、30%エタノール溶出画分、65%エタノール溶出画分及び90%エタノール溶出画分をそれぞれ集めた。次に、上記で得られた65%エタノール画分580gを60%エタノール5.8Lに溶解させ、SP-825吸着樹脂5Lを充填せしめたカラムクロマトグラフィー(コンディショニング:60%エタノール)に供し、非吸着画分、60%エタノール溶出画分及び90%エタノール溶出画分をそれぞれ集め、60%エタノール溶出画分をロータリーエバポレーターにて減圧濃縮乾固することによりSFを得た。
上記で得られたSF中の有効成分であるチイサノサイド、11-デオキシイソチイサノサイド、イソチイサノサイド及びセシロサイドの含有量を高速液体クロマトグラフィー質量分析計(HPLC-MS)により定量を行ったところ、それぞれ、42.57、2.58、1.21及び2.40%(重量%)であった。
<HPLC‐MS条件>
HPLC:HP-1100 series(Agilent Technologies)
MS:LCQ Advantage (Thermo-Finnigan)
カラム:TSK gel ODS-80Ts (Φ4.6mm×L75mm)
カラム温度:40℃
流速:500μL/分
注入量:10μL
検出:(UV)203nm
(MS)ESI positive(m/z 400-2000)、ESI negative (m/z 300-2000)
移動相:A;0.1%TFA/aq. B;0.1%TFA/MeCN
0-3 min A:B=75:25(v/v) 3-20 min A:B=75:25(v/v)→ A:B=40:60 (v/v)
20-30 min A:B=40:60 (v/v) post run 10min by A:B=75:25(v/v)
<肥満抑制試験>
肥満抑制試験は、K. Yoshizumiらの方法(Proceeding of International Joint Meeting on Food Factors and Free Radicals in Health & Disease, p.108, 2003)に従って行った。すなわち、マウスに普通食(脂肪:4.5%)、高脂肪食(脂肪:60%)あるいはこの高脂肪食にSFを0.5、1.0%添加したものを17日間摂取させ、2又は3日おきに体重及び摂餌量を測定した。
処方例1
[錠剤の製造]
実施例1で得られたチイサノサイド(chiisanoside)を用いて、常法に従って、下記の組成の錠剤を製造した。
(組 成) (配合:重量%)
チイサノサイド 24
乳糖 63
コーンスターチ 12
グァーガム 1
[ジュースの製造]
実施例1で得られたイソチイサノサイド(isochiisanoside)を用いて、常法に従って、下記の組成のジュースを製造した。
(組 成) (配合:重量%)
冷凍濃縮温州みかん果汁 5.0
果糖ブドウ糖液糖 11.0
クエン酸 0.2
L-アスコルビン酸 0.02
香料 0.2
色素 0.1
イソチイサノサイド 0.2
水 83.28
[フェイスクリームの製造]
実施例1で得られたチイサノサイド(chiisanoside)を用いて、常法に従って、下記の組成のフェイスクリームを製造した。
(組 成) (配合:重量%)
イソステアリン酸イソプロピル 8.0
ホホバ油 6.0
セタノール 8.0
ステアリルアルコール 2.0
ポリオキシエチレンラウリルエーテル 1.5
プロピレングリコール 6.0
ソルビトール 1.0
パラベン 0.4
チイサノサイド 0.5
ビタミンE 0.5
香料 0.1
精製水 66.0
Claims (8)
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含む医薬
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含むリパーゼ阻害剤。
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含む脂質吸収阻害剤。
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含む抗肥満剤。
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含む高脂血症改善剤。
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含むニキビ改善剤。
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含む食品。
- チイサノサイド、11−デオキシイソチイサノサイド、イソチイサノサイドから選ばれる1種以上を含む化粧料。
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