JP2017105734A - 脂肪吸着作用を呈するメチル化フラボノール誘導体及びその製造方法 - Google Patents
脂肪吸着作用を呈するメチル化フラボノール誘導体及びその製造方法 Download PDFInfo
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Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1569869A (zh) * | 2004-05-10 | 2005-01-26 | 山东省医学科学院药物研究所 | 板栗花黄酮类化合物 |
JP2006515590A (ja) * | 2002-12-27 | 2006-06-01 | ハンコック ファーム.カンパニー インコーポレーティッド | 抗酸化及び老化抑制活性を有するハナズオウ抽出物及びそれを含む抗酸化、皮膚老化抑制及びシワ改善用化粧料組成物 |
JP2007518750A (ja) * | 2004-01-19 | 2007-07-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | シクロデキストリンとのフラボノイド錯体 |
WO2008100977A2 (en) * | 2007-02-14 | 2008-08-21 | N.V. Organon | Carbamates therapeutic release agents as amidase inhibitors |
WO2012055010A1 (en) * | 2010-10-25 | 2012-05-03 | Fédération Des Producteurs Acéricoles Du Québec | Maple tree-derived products and uses thereof |
JP2013132290A (ja) * | 2011-12-26 | 2013-07-08 | Satoshi Shinkawa | 脂肪分解作用を呈する有機酸誘導体の製造方法 |
JP2014070056A (ja) * | 2012-09-28 | 2014-04-21 | Oriza Yuka Kk | 脂肪蓄積抑制剤 |
JP2014070057A (ja) * | 2012-09-28 | 2014-04-21 | Oriza Yuka Kk | TNF−αによる活性酸素産生抑制剤及び線維芽細胞障害抑制剤 |
CN104592331A (zh) * | 2015-02-03 | 2015-05-06 | 天津科技大学 | 一种槲皮素衍生物及其制备工艺和应用 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006515590A (ja) * | 2002-12-27 | 2006-06-01 | ハンコック ファーム.カンパニー インコーポレーティッド | 抗酸化及び老化抑制活性を有するハナズオウ抽出物及びそれを含む抗酸化、皮膚老化抑制及びシワ改善用化粧料組成物 |
JP2007518750A (ja) * | 2004-01-19 | 2007-07-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | シクロデキストリンとのフラボノイド錯体 |
CN1569869A (zh) * | 2004-05-10 | 2005-01-26 | 山东省医学科学院药物研究所 | 板栗花黄酮类化合物 |
WO2008100977A2 (en) * | 2007-02-14 | 2008-08-21 | N.V. Organon | Carbamates therapeutic release agents as amidase inhibitors |
WO2012055010A1 (en) * | 2010-10-25 | 2012-05-03 | Fédération Des Producteurs Acéricoles Du Québec | Maple tree-derived products and uses thereof |
JP2013132290A (ja) * | 2011-12-26 | 2013-07-08 | Satoshi Shinkawa | 脂肪分解作用を呈する有機酸誘導体の製造方法 |
JP2014070056A (ja) * | 2012-09-28 | 2014-04-21 | Oriza Yuka Kk | 脂肪蓄積抑制剤 |
JP2014070057A (ja) * | 2012-09-28 | 2014-04-21 | Oriza Yuka Kk | TNF−αによる活性酸素産生抑制剤及び線維芽細胞障害抑制剤 |
CN104592331A (zh) * | 2015-02-03 | 2015-05-06 | 天津科技大学 | 一种槲皮素衍生物及其制备工艺和应用 |
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