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    請使用永久網址來引用或連結此文件: http://libir.tmu.edu.tw/handle/987654321/59403


    題名: ent-Kaurene衍生物之合成與活性評估
    Synthesis and biological evaluation of ent-kaurene derivatives
    作者: 蘇達騏
    Su, Ta-Chi
    貢獻者: 藥學系
    林淑娟
    關鍵詞: 菊糖醇
    steviol
    日期: 2015-07-09
    上傳時間: 2020-08-28
    摘要: Stevioside為天然的甜味劑，可由菊糖(Stevia rebaudiana Bertoni Bertoni)的葉子萃取而得。Stevioside具有降血壓、降血糖、抗發炎、抗癌及免疫調節等功能。就化學觀點及藥物發現，stevioside及其相關化合物具有高度的研究價值。Steviol及isosteviol皆為由stevioside衍生而得的四環雙萜化合物，具有多種生物活性，然而結構骨架卻不相同。Steviol為ent-kaurene雙萜，而isosteviol則是ent-beyerane雙萜。過去本實驗室以isosteviol為起始物，合成C4-amide及C4-ureido的衍生物，部分合成的衍生物具有抗B肝病毒的活性。由於steviol與isosteviol結構類似，以及為繼續尋找具新標的及作用機轉的抗B型肝炎病毒的化合物，許多具不同官能基取代於steviol C-4羧基的衍生物已被合成，所得化合物皆經由核磁共振光譜及高解析質譜鑑定其結構。初步抗B肝病毒活性測試發現，化合物 5具有比對照化合物lamivudine好的抑制病毒DNA 複製的活性；而化合物20、31、33和34亦具不錯的抑制病毒DNA 複製的活性，但比對照化合物lamivudine弱。
    Stevioside is a natural sweetener, which is obtained from the leaves of Stevia rebaudiana Bertoni Bertoni. Stevioside possesses bioactivities of anti-hypertensive, anti-hyperglycemic, anti-inflammatory, anti-tumor, and immunomodulatory. From a chemical view and drug discovery, stevioside and its related compounds have a great research value. Two tetracyclic diterpenoids, steviol and isosteviol, are derived from stevioside. However, their structural backbones are different. Steviol is an ent-kaurene diterpene, while isosteviol is an ent-beyerane diterpene. Both compounds possessed various bioactivities. In our lab, we have been used isosteviol as the starting material to synthesize C4-amide and C4-ureido derivatives. Some synthesized compounds possessed anti-hepatitis B virus activity. Due to steviol and isosteviol possessing similar structure and as a continuing to develop new anti-HBV agents with novel targets and mechanisms, several derivatives were prepared by replacing C4-COOH with different substituents at steviol. The structures of synthesized compounds are established on the basis of NMR and HRMS. The results of preliminary anti-hepatitis B virus show that compound 5 has a better potency on the inhibition of the replication of HBV DNA than the reference compound lamivudine. Compounds 20, 31,33, and 34 also show the inhibitory activity on HBV DNA replication, but less potent than lamivudine.
    描述: 碩士
    指導教授:林淑娟
    委員:陳國棟
    委員:張淑芬
    資料類型: thesis
    顯示於類別:[藥學系] 博碩士論文

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