合成含 2-Hydroxy-3-methylbut-3-enyl group 的 Chalcone 類天然物

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Title:	合成含 2-Hydroxy-3-methylbut-3-enyl group 的 Chalcone 類天然物
Authors:	黃俊彰
Contributors:	化學系
Keywords:	Chalcone 2-Hydroxy-3-methylbut-3-enyl group prenyl group Paratocarpus Venenosa Dorstenia barteri var. Subtriangularis Dorstenia angusticornis
Date:	2011
Issue Date:	2012-10-11 10:21:59 (UTC+8)
Abstract:	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.
Appears in Collections:	[Department of Chemistry & Graduate Institute of Applied Chemistry ] thesis

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