文化大學機構典藏 CCUR:Item 987654321/25879
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    题名: Evodiagenine的合成與生物活性研究
    Synthesis and Biological Activity of Evodiagenine
    作者: 賴岩君
    Lai, Yen-Chung
    贡献者: 化學系應用化學碩士班
    关键词: 吳茱萸
    Evodiagenine
    日期: 2013-01
    上传时间: 2013-10-31 14:57:15 (UTC+8)
    摘要: 吳茱萸(Evodia rutaecarpa)屬於芸香科，其未成熟乾燥果實中醫常用於治療頭痛、腹痛、痢疾、產後出血及閉經等疾病。吳茱萸含有多種生物鹼，其中吳茱萸鹼、吳茱萸次鹼、去氫吳茱萸鹼為三個主要的成份，先前的報告指出這些生物鹼具有許多不同的藥理活性如降血壓、血管舒張、抗發炎、抗癌等活性。
    Evodiagenine (1)是最近由吳茱萸分離出來的新吲哚生物鹼天然物，且這個天然物到目前為止並未有合成與生物活性之報導，為了進一步探討其結構與活性間之關係，在本研究中，建立了一個有效的合成方法來合成evodiagenine及類似物。
    從1,2,3,4-tetrahydro-1-oxo--carboline為起始物經由五個步驟完成evodiagenine的全合成，使用同樣方式數個類似物也被合成出來。
    這些合成的化合物使用DPPH方法檢測其抗氧化活性，結果顯示都沒有很好的清除自由基的活性，只有化合物17-methoxy-demethylevodiagenine (23)具有中等的活性，EC50值為61.9 g/mL。
    The dried fruit of Evodia rutaecarpa has been used in traditional Chinese medicine for the treatment of headache, gastrointestinal disorders, and dysentery. Evodiamine, rutaecarpine, and dehydroevodiamine have been isolated as three main alkaloids from E. rutaecarpa. Early reports indicated that those alkaloids have a variety of biological/pharmacological activities in vitro and in vivo such as antihypertension, vessel relaxation, antiinflammatory effect, and anticancer activity.
    Recently, evodiagenine (1) was isolated and characterized as a new indole alkaloid from E. rutaecarpa. Until now, the total synthesis and biological activity of evodiagenine was not reported yet. In order to obtain more material for further study the biological activities, in this study, the synthesis of evodiagenine and analogues was investigated.
    Starting from 1,2,3,4-tetrahydro--carboline-1-one, evodiagenine were successfully synthesized in five steps. Using the same strategy several analogues were prepared.
    The antioxidative activity of synthesized compounds using DPPH method was evaluated. Among the tested compounds, 17-methoxy-demethylevodiagenine (23) showed moderate DPPH radical scavenging activity, and the EC50 value of 23 was 61.9 g/mL.
    显示于类别:[化學系所] 博碩士論文

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