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研究生:周宗賢
研究生(外文):Tsung-Hsien Chou
論文名稱:福建賽衛矛莖部與根部之化學成分及細胞毒活性之研究
論文名稱(外文):Studies on the Chemical Constituents and Cytotoxic Activities from the Stem and Root of Microtropis fokienensis
指導教授:陳日榮
指導教授(外文):Jih-Jung Chen
學位類別:碩士
校院名稱:大仁科技大學
系所名稱:製藥科技研究所
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2006
畢業學年度:94
語文別:中文
論文頁數:132
中文關鍵詞:抗癌衛矛科福建賽衛矛
外文關鍵詞:Microtropis fokienensis DunnCelastraceaeantitumoragarofuran sesquiterpene
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福建賽衛矛(衛矛科) 是一種生長在中國南部及台灣高海拔森林中的小灌木。Sesquiterpene alkaloids, dihydroagarofuranoid sesqui- terpenes, triterpenes, 及其衍生物廣泛的分布在衛矛科植物中。釵h衛矛科植物之分離成分具有多樣化的生物活性,包括免疫抑制、殺蟲、抗炎、抗腫瘤及抗愛滋病等作用。然而,福建賽衛矛的化學成分及其生物活性過去尚未被研究。約1000種台灣產植物已進行細胞毒活性篩選,福建賽衛矛是其中一種具有活性的植物。由福建賽衛矛莖部乙酸乙酯可溶部已分離出4個具dihydro--agarofuran骨架的新sesquiterpene polyesters化合物:fokienagarofuran A (1), fokienagarofuran B (2), fokienagarofuran C (3) 及fokienagarofuran D (4);及9個已知化合物:triptogelin G-2 (5), mutangin (6), syringic acid (7), vanillic acid (8), 2,6-dimethoxy-p-benzoquinone (9), vanillin (10), p-hydroxybenzaldehyde (11), -sitosterol (12)及-sitostenone (13)。此外,從福建賽衛矛根部乙酸乙酯可溶部分離出4個具dihydro-- agarofuran骨架的新sesquiterpene polyesters化合物: (1), (2), (3), fokienagarofuran E (14) 及1個具benzylbenzaldehyde骨架的新化合物: 2-hydroxy-5-(4-hydroxybenzyl)benzaldehyde (15) 及12個已知化合物:(5), (6), (7), (8), (10), (11), (12), (13), orbiculin G (16), p-hydroxy- benzoic acid (17), 1-tetracosanol (18)及1-hexacosanol (19)。這些新化合物之結構經由各種圖譜分析,包括2D NMR實驗予以確認。在細胞毒活性試驗方面,fokienagarofuran A (1), fokienagarofuran B (2) , fokienagarofuran C (3), fokienagarofuran D (4), 2,6-dimethoxy-p- benzoquinone (9)及p-hydroxybenzaldehyde (11)對P-388呈現良好的細胞毒活性,其IC50值分別為0.032, 0.043, 0.051, 0.036, 0.82及0.42 g/mL; 此外fokienagarofuran A (1), fokienagarofuran B (2) , fokien- agarofuran C (3)及fokienagarofuran D (4)對HT-29亦具有顯著的細胞毒活性,其IC50值分別為0.054, 0.071, 0.082及0.058 g/mL。
Abstract

Microtropis fokienensis Dunn(Celastraceae) is a small shrub growing in high altitude forests throughout southern China and Taiwan. Sesquiterpene alkaloids, dihydroagarofuranoid sesquiterpenes, triterpenes, and their derivatives are widely distributed in plants of the family Celastraceae. Many of these compounds exhibit immunosuppressive, insecticidal, antiinflammatory, antitumor, and anti-AIDS activities. However, the chemical constituents and biological activities of M. fokienensis have not been studied. Approximately 1000 species of Formosan plants have been screened for cytotoxicity and M. fokienensis was shown to be one of the active species. Investigation on an EtOAc-soluble fraction of the stem of M. fokienensis has led to the isolation of four new dihydro-��-agarofuran sesquiterpene polyesters, fokienagarofuran A (1), fokienagarofuran B (2), fokienagarofuran C (3) and fokienagarofuran D (4), together with nine known compounds, triptogelin (5), mutangin (6), syringic acid (7), vanillic acid (8), 2,6-dimethoxy-p-benzoquinone (9), vanillin (10), p-hydroxybenz- aldehyde (11), ��-sitosterol (12), and ��-sitostenone (13). In addition, investigation on an EtOAc-soluble fraction of the root of M. fokienensis has led to the isolation of four new dihydro-��-agarofuran sesquiterpene polyesters, (1), (2), (3), fokienagarofuran E (14) and a new benzylbenzaldehyde, 2-hydroxy-5-(4-hydroxybenzyl)benzaldehyde (15), together with twelve known compounds, (5), (6), (7), (8), (10), (11), (12), (13), orbiculin G (16), p-hydroxybenzoic acid (17), 1-tetracosanol (18) and 1-hexacosanol(19). The structure of those new compounds were determined through spectral analyses including extensive 2D NMR data. Among the isolates, fokienagarofuran A (1), fokienagarofuran B (2), fokienagarofuran C (3), fokienagarofuran D (4), 2,6-dimethoxy-p- benzoquinone (9), and p-hydroxybenzaldehyde (11) exhibited significant cytotoxicities with IC50 = 0.032, 0.043, 0.051, 0.036, 0.82, and 0.42 �慊/mL, respectively, against P-388 cell line. In addition, fokienagarofuran A (1), fokienagarofuran B (2), fokienagarofuran C (3) and fokienagarofuran D (4) also exhibited significant cytotoxicities with IC50 = 0.054, 0.071, 0.082, and 0.058 �慊/mL, respectively, against HT-29 cell line.
目 錄

頁次
誌謝..……………………..............................................……………...………...………………….....Ⅰ
目錄.....……………………..........................................……………..…………………...…………...Ⅲ
圖表目錄....……………............................................………………..……………………………..VI
中文摘要..…………..............................................………………...………………………………XII
Abstract..…………................................................…………………………………...…………...XXI
第一章 緒言..…..……............................................…………………………………………….......1
第二章 研究動機與目的..…........................................…………………………………………4
第三章 台灣產衛矛科植物過去成分研究概要..……..…………………………………5
第四章 抽出與分離..……………...............................…………………………...…...……..….12
第一節 福建賽衛矛莖部之成分抽出與分離..…………............................………..15
第二節 福建賽衛矛根部之成分抽出與分離..……............................……………..18
第五章 結果與討論...………….........................................……………………………………..21
第ㄧ部分 福建賽衛矛莖部 .....................................………………………………....21
第一節 Fokienagarofuran A (1)之結構研究..……............................………...21
第二節 Fokienagarofuran B (2)之結構研究……….........................................31
第三節 Fokienagarofuran C (3)之結構研究…………….....…... ...............….38
第四節 Fokienagarofuran D (4)之結構研究.................................................…45
第五節 Triptogelin G-2 (5)之結構研究………......................………………....52
第六節 Mutangin (6)之結構研究…………........................ ........……………….57
第七節 Syringic acid (7)之結構研究……...…………...........................…….…61
第八節 Vanillic acid (8)之結構研究………...............................……………….64
第九節 2,6-Dimethoxy-1,4-benzoquinone (9)之結構研究………………67
第十節 Vanillin (10)之結構研究…………………………………..….................70
第十一節 4-Hydroxybenzaldehyde (11)之結構研究………….........................73
第十二節 ��-Sitosterol (12)之結構研究……………………………...............……76
第十三節 ��-Sitostenone (13)之結構研究…...………………............................…79
第二部分 福建賽衛矛根部 .....................................………………………………....82
第十四節 Fokienagarofuran E (14)之結構研究...................................................82
第十五節 2-Hydroxy-5-(4-hydroxybenzyl)benzaldehyde (15)之結構研究.........................................................................................................................89
第十六節 Orbiculin G (16)之結構研究…......................…..........…………….......93
第十七節 p-Hydroxybenzoic acid (17)之結構研究……...........................…..100
第十八節 1-Tetracosanol (18)及1-Hexacosanol (19)之結構研究.…..................................................................................................................103
第六章 細胞毒活性之研究….…………….............................…...…………………...……106
第七章 結論…………………........................................…………..…….……………………109
第八章 實驗部分 ……………….....................................……………...………………………110
第一節 儀器與材料……………..................................…………....……………………...110
第二節 抽取與分離………………................................………...…..……………………112
2.1 福建賽衛矛莖部乙酸乙酯可溶部之分離…..…...........................……….113
2.2 福建賽衛矛根部乙酸乙酯可溶部之分離………….....................……….115
第三節 細胞毒活性之實驗方法………..........................................……..……...……117
第四節 各化合物之實驗數據…………..............................……………...…………...119
第九章 參考文獻…………………..................................……………...………...……………127
第十章 已發表之研究成果…………….....................................……………...……………132
第九章參考文獻

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