文化大學機構典藏 CCUR:Item 987654321/23138
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    题名: 合成含 2-Hydroxy-3-methylbut-3-enyl group 的 Chalcone 類天然物
    作者: 黃俊彰
    贡献者: 化學系
    关键词: Chalcone
    2-Hydroxy-3-methylbut-3-enyl group
    prenyl group
    Paratocarpus Venenosa
    Dorstenia barteri var.
    Subtriangularis
    Dorstenia angusticornis
    日期: 2011
    上传时间: 2012-10-11 10:21:59 (UTC+8)
    摘要: Paratocarpin D (1)、paratocarpin E (2)、bartericin A (3)、bartericin D (4)、angusticornin A (5)為分別從植物Paratocarpus Venenosa, Dorstenia barteri var.、 Subtriangularis及 Dorstenia angusticornis分離與鑑定出的chalcone類化合物，這五個天然物結構中都有2-hydroxy-3-methylbut-3-enyl基團，先前我們研究從補骨脂分離與鑑定出一個帶有2-hydroxy-3-methylbut-3-enyl基團的chalcone新成份，bavachalcone A，並發現此成份顯示很強的抗發炎生物活性，為了繼續進行相關研究，本論文主要是建立了一個簡易的合成方法，完成paratocarpin D、paratocarpin E、bartericin A、bartericin D、angusticornin A的全合成，並進一步探討這些化合物之抗發炎生物活性。
    生物活性結果顯示paratocarpin D、paratocarpin E、bartericin A都沒有活性，與bavachalcone A (EC50為7.41 M)比較發現在paratocarpin D、paratocarpin E、bartericin A結構中的3’-位置的烷基可能是導致活性減少的因素。
    Paratocarpin D (1), paratocarpin E (2), bartericin A (3), bartericin D (4), angusticornin A (5) were five naturally occurring chalcones isolated previously from Paratocarpus Venenosa, Dorstenia barteri var. Subtriangularis, and Dorstenia angusticornis, respectively. A 2-hydroxy-3-methylbut-3-enyl group is present in their structure. In our previous studies, bavachalcone A was isolated and characterized as a new chalcone containing 2-hydroxy-3-methylbut-3-enyl group from Psoralea corylifolia and showed strong anti-inflammatory effect. In order to continually study the structure and activity relationships regarding natural chalcones with 2-hydroxy-3-methylbut-3-enyl group, in this thesis, we established a simple method and finished the total synthesis of paratocarpin D, paratocarpin E, bartericin A, bartericin D, and angusticornin A. In addition, the anti-inflammatory effect of these compounds on LPS-induced NO production in RAW264.7 macrophages was also evaluated. An assay results showed that paratocarpin D, paratocarpin E, and bartericin A did not have any activity. Comparing to bavachalcone A, a similar compound with an IC50 value 7.41 M, an additional alkyl group in 3’-position in 1–3 could be the factor to diminish the activity.
    显示于类别:[化學系所] 博碩士論文

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    http___thesis.lib.pccu.edu.tw_cgi-bin_cdrfb3_gsweb2.pdf321KbAdobe PDF207检视/开启
    http___thesis.lib.pccu.edu.tw_cgi-bin_cdrfb3_gsweb3.pdf1162KbAdobe PDF341检视/开启
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    http___thesis.lib.pccu.edu.tw_cgi-bin_cdrfb3_gsweb5.pdf127KbAdobe PDF219检视/开启


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