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研究生: 留添億
論文名稱: (25R)-3β-胺基-5-螺甾稀與(25R)-3β-胺基-5-螺甾之合成作為皮膚美白活化劑
Synthesis of Antillaridine and Isojurubidine as Skin Lightening Agents
指導教授: 胡紀如
口試委員:
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2005
畢業學年度: 93
語文別: 中文
論文頁數: 23
中文關鍵詞: 皮膚美白
外文關鍵詞: skin lightening
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  • Antillaridine ((25R)-3β-amino-5-spirostene)與isojurubidine((25R)-3β- amino-spirostane)皆為具有螺甾骨架的胺類天然物,是由茄屬植物所單離出來。在2001年,由日本資生堂公司所發表的專利中,isojurubidine可作為抑制黑色素生成、沉澱之皮膚美白活化劑。
    我們利用皂甘素(diosgenin)為起始物,經二次Mitsunobu反應作為關鍵步驟,成功合成antillaridine,總產率為20%。再經由一次氫化步驟合成出isojurubidine,產率為80%。再者,Antillaridine 為isojurubidine之前趨物,推測antillaridine亦可能具有美白活性之潛力。


    The natural products antillaridine and isojurubidine were isolated from Solanum plants by Coll et al. In 2001, Shiseido company in Japan was granted a patent, in which isojurubidine was reported as a skin lightening agent with bleaching effect on pigmention. We successfully synthesized antillaridine in 20% over all yield by using diosgenin as a starting material and Mitsunobu reaction as the key step. Then antillaridine was hydrogenated with 10% Pd/C to give isojurubidine in 80% yield. Antillaridine is the precursor of isojurubidine; we expect antillaridine could also exhibit skin lightening effect.

    中文摘要 ………………………………………………………… i 英文摘要 ………………………………………………………… ii 謝誌 ……………………………………………………………… iii 目錄 ……………………………………………………………… iv 緒論 ……………………………………………………………… 1 結果 ……………………………………………………………… 8 討論 ……………………………………………………………… 11 結論 ……………………………………………………………… 14 實驗部份 ……………………………………………………… 15 參考文獻 ……………………………………………………… 21

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