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研究生:詹于誼
研究生(外文):Chan Yu Yi
論文名稱:馬兜鈴屬植物之成分與生物活性研究及ProtosappaninA合成研究
論文名稱(外文):Studies on the Constituents and Biological Activity of Aristolochia Plants and the Synthesis of Protosappanin A
指導教授:吳天賞吳天賞引用關係
指導教授(外文):Prof. Wu Tian-Shung
學位類別:博士
校院名稱:國立成功大學
系所名稱:化學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:1999
畢業學年度:87
語文別:中文
論文頁數:325
中文關鍵詞:馬兜鈴屬台灣馬兜鈴瓜葉馬兜鈴綿毛馬兜鈴Protosappanin A
外文關鍵詞:AristolochiaAristolochia heterophyllaAristolochia cucurbitifoliaAristolochia mollissimaProtosappanin A
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從臺灣馬兜鈴葉部、根莖部、綿毛馬兜鈴葉部、根莖部與瓜葉馬兜鈴根莖部共分離得到140種化合物,經光譜方法、化學反應及與文獻比對光譜資料後,其中103種為已知化合物,36種為天然界首次分離得到的新化合物及1種疑為分離過程中產生之人工產物,分別為aristophyllides-A, -B, -C, -D, aristoloterpenates-II, -III, -IV, madolins-A, -B, -C, -D, -E, -F, -G, -H, -I, -J, -K, -L, -M, -N, -O, -Q, -R, -S, -T, -U, -V, -W, -X, -Y, -Z, aristolides-A, -B, sodium aristolochate-VII, aristolactam-CIV及aristophyll-C。其中aristophyllides-A, ~ -D的倍半之部份結構及madolins-F, -G, -H, -W, -Z分別屬於三種類型之新骨架的化合物。
經藥理測試後,由結果中發現C-3, 4含羥基或甲氧基等取代基的菲類衍生物對AA、Collagen或PAF所引起的血小板凝集皆有明顯的抑制活性。而馬兜鈴屬植物中主要的倍半類化合物aristolactone與manshurolide在100g/ml的濃度下,則對AA所引起的血小板凝集分別有91.7%及100%的抑制活性。另外,新化合物aristolide-A在100g/ml的濃度下,亦對AA所引起的血小板凝集有100%的抑制活性。而在細胞毒活性測試方面發現aristolochic acid-I對HT-29有很強的細胞毒活性,ED50值達8.3x10-4 g/ml。
我們亦將中西香爾教授的丙烯基與苯甲酯方法以決定帶羥基的掌性化合物的絕對組態之CD法加以改進,延伸多一個亞甲基間隔亦能用以決定其絕對組態。
另外我們亦進行protosappanin A的合成研究,已完成其中間產物之合成。
由本研究之結果亦提供馬兜鈴屬植物之化學分類的重要依據。
Thirty-six new compounds, one artificial product and 103 known compounds were isolated and characterized from Aristolochia heterophylla, A. mollissima and A. cucurbitifolia. Their structures were determined by spectral analysis and chemical transformation. The new compounds included aristophyllides-A, -B, -C, -D, aristoloterpenates-II, -III, -IV, madolins-A, -B, -C, -D, -E, -F, -G, -H, -I, -J, -K, -L, -M, -N, -O, -R, -S, -T, -U, -V, -W, -X, -Y, -Z, aristolides-A, -B, sodium aristolochate-VII, aristolactam-CIV, aristophyll-C, and an artificial compound, madolin-Q. Furthermore, the sesquiterpene moiety of aristophyllides-A, ~ -D and madolins-F, -G, -H, -W, -Z belong to three kinds of the novel skeleton sesquiterpenes
The isolated compounds were subjected to evaluate the bioactivities. The results showed that phenanthroids were substituted by hydroxyl or methoxyl groups at C-3 and C-4 to be inhibited platelet aggregation which induced by AA, Collagen or PAF. Aristolactone and manshurolide (100g/ml) which were the major sesquiterpene in the Aristolochia genus showed the 91.7 and 100% inhibition activities of antiplatelet aggregation induced by AA. In addition, aristolide-A also exhibited the 100% inhibition activities. Aristolochic acid-I showed significant cytotoxicity against HT-29 at ED50=8.3x10-4 g/ml.
The Professor Nakanishi’s CD method based on the allylic and benzoate chirality method, which can use to determine the absolute configuration of chiral compounds with hydroxy substitution, was modified to be based on the allylic and benzoate chirality with one more methylene group.
In addition, we also studied the synthesis of protosappanin A, and have finished the synthesis of its intermediates.
The results of this study also provided the important guides of the chemotaxonomy of Aristolochia plants.
封面
目 錄
中文摘要
英文摘要
第一章 緒論
第一節 緒論
第二節 植物形態
第二章 馬兜鈴屬植物之研究概況
第一節 馬兜鈴屬植物之成分研究回顧
第二節 馬兜鈴屬植物生物活性之研究概況
第三節 生合成路徑之研究
第二章 抽取與分離
第一節 台灣馬兜鈴根部及莖部之抽取與分離
第二節 台灣馬兜鈴葉部之抽與分離
第三節 瓜葉馬兜鈴根部及莖部之抽取與分離
第四節 綿毛馬兜鈴葉部之抽取與分離
第五節 綿毛馬兜鈴葉部之抽取與分離
第三章 化學構造研究
第一節 Aristophyllide-A(401)之構造研究
第二節 Aristophyllide-B(402)之構造研究
第三節 Aristophyllide-C(403)之構造研究
第四節 Aristophyllide-D(404)之構造研究
第五節 Aristoloterpenate-I(338)之構造研究
第六節 Aristoloterpenate-II(405)之構造研究
第七節 Aristoloterpenate-III(406)之構造研究
第八節 Aristoloterpenate-IV(407)之構造研究
第九節 Modolin-A(338)之構造研究
第十節 Modolin-B(389)之構造研究
第十一節 Modolin-C(445)之構造研究
第十二節 Modolin-D(446)之構造研究
第十三節 Modolin-E(390)之構造研究
第十四節 Modolin-F(391)之構造研究
第十五節 Modolin-G(392)之構造研究
第十六節 Madolin-H(393)之構造研究
第十七節 Madolin-I(394)之構造研究
第十八節 Madolin-H(395)之構造研究
第十九節 Madolin-K(397)之構造研究
第二十節 Madolin-L(397)之構造研究
第二十一節 Madolin-M(398)之構造研究
第二十二節 Madolin-N(427)之構造研究
第二十三節 Madolin-O(428)之構造研究
第二十四節 Madolin-Q(399)之構造研究
第二十五節 Madolin-R(458)之構造研究
第二十六節 Madolin-S(459)之構造研究
第二十七節 Madolin-T(460)之構造研究
第二十八節 Madolin-U(461)之構造研究
第二十九節 Madolin-V(462)之構造研究
第三十節 Madolin-W(463)之構造研究
第三十一節 Madolin-X(464)之構造研究
第三十二節 Madolin-Y(465)之構造研究
第三十三節 Madolin-Z(466)之構造研究
第三十四節 Aristophyll-C(438)之構造研究
第三十五節 Aristophyll-A(422)之構造研究
第三十六節 Aristophyll-B(423)之構造研究
第三十七節 Aristophyll-CIV(415)之構造研究
第三十八節 Sodium aristolochate-VII(410)之構造研究
第三十九節 Aromadenrane-4β,10β-diol(387)之構造研究
第四十節 其他已知化合物之構造決定
第四章 生合成的推演與其立體結構之探討
第五節 藥理試驗
第一節 抗血小板凝集活性
第二節 細胞毒活性
第六章 Protosappanin A的合成
第一節 研究動機
第二節 合成策略
第三節 結果與討論
(A)1-(2,3-ePOXYPROPOXY)-3-METHOXYMETHOXYBENZENE(478)之合成
(B)4-bROMO-1,2-DI-METHOXYMETHOXBENZENE(480)之合成
(C)化合物(483) 之合成
第七章 結論
第八章 實驗部份
第一節 本實驗所使用之儀器和藥品
第二節 植物之採集與鑑定
第三節 台灣馬兜鈴根部及莖部成分之萃取與分離
第四節 台灣馬兜鈴葉部成分之萃取與分離
第五節 瓜葉馬兜鈴根部及莖部成分之萃取與分離
第六節 綿毛馬兜鈴葉部成分之萃取與分離
第七節 綿毛馬兜鈴葉部成分之萃取與分離
第八節 抗血小板凝集活性試驗
第九節 細胞毒活性試驗
第十節 合成步驟
光譜數據
參考文獻
與本論文相關已發表之著作
已發表之論文
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