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研究生:許毓琳
研究生(外文):Yu-Lin Shu
論文名稱:姬書帶蕨的成分研究和1-苯基異喹啉的合成
論文名稱(外文):The Constituents of Vittaria anguste-elongate Hayata and The Synthesis of 1-Phenylisoquinoline
指導教授:吳培琳
指導教授(外文):Pei-Lin Wu
學位類別:碩士
校院名稱:國立成功大學
系所名稱:化學系碩博士班
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:2004
畢業學年度:92
語文別:中文
論文頁數:167
中文關鍵詞:成分分析合成姬書帶蕨
外文關鍵詞:1-PhenylisoquinolineVittaria anguste-elongate HayataConstituentsSynthesis
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第一部份 姬書帶蕨的成分研究
姬書帶蕨為書帶蕨科書帶蕨屬。其全草粗萃物對胃癌細胞與鼻咽癌細胞均有很強的細胞毒活性;且目前並無文獻報導任何書帶蕨屬甚至於書帶蕨科植物的成份研究,引發我們進行姬書帶蕨的成分分析。
由姬書帶蕨全草分離得到39個化合物。經光譜方法、化學反應與文獻比對光譜資料後,其中11個為天然界首次發現之新化合物,分別為vittarin-A (1)、vittarin-C (2)、vittarin-D (3)、vittarin-E (4)、vittarin-F (5)、methyl 4-O-coumaroylquinate (8)、3-O-acetylniduloic acid (10)、ethyl 3-O-acetylniduloate (11)、vittariflavone (15)、vittarilide-A (23)、vittarilide-B (24);至於其他28個已知化合物為methyl 4-O-caffeoylquinate (6)、ethyl 4-O-caffeoylquinate (7)、 methyl 5-O-caffeoylquinate (9)、apigenin (12)、vitexin (13)、5,7-dihydroxy-3,4,5-
trimethoxyflavone (14)、amentoflavone (16)、friedelene-(3) (17) 、phytol (18)、��-carotene (19)、 lutein (20)、 pheophytin-a (21)、 132-hydroxy(132-R)pheophytin-a (22)、trans-p-coumaric acid (25)、methyl trans-p-coumarate (26)、methyl caffeate (27)、ferulic acid (28)、p-cresol (29)、4-hydroxybenzaldehyde (30)、4-hydroxybenzoic acid (31)、4-hydroxybenzoic acid methyl ester (32)、protocatechualdehyde (33)、protocatecheuic acid (34)、protocatecheuic acid methyl ester (35)、vanillin (36)、vanillic acid (37)、a mixture of β-sitosterol and stigmasterol (38) 和 β-sitosteryl-β-D-glucoside (39)。而ethyl 4-O-caffeoylquinate (7) 為天然物首次分離得到之純化合物。
經細胞毒與抗氧化活性測試後,發現化合物5,7-dihydroxy-3,4,5-
trimethoxyflavone (14) 對NCH460肺癌細胞及SF268中樞神經癌細胞均有不錯的細胞毒活性。而化合物ethyl 4-O-caffeoylquinate (7)、vittarilide-A (23)、vittarilide-B (24)與ferulic acid (28) 具有比維他命E還強的抗氧化活性。

第二部分 1-苯基異喹啉的合成
目前有機發光二極體三原色的發展中,藍光和綠光材料的發展已超過目標值,只有紅光還未達到。因此,增加紅光材料的效率及色純度是未來的課題。
異喹啉之銥金屬錯合物為紅色磷光發光摻雜材料,此異喹啉配位子上官能基的改變會對其發光性質、色純度產生影響。在此更換(piq)2Ir(acac) (17) 中的苯基異喹啉上之官能基,以期找到一具有飽和色純度且有好的發光強度和效率的紅光材料。
而苯基異喹啉的前驅物為異喹啉酮。將肉桂酸疊氮化後經熱環合來合成異喹啉酮,其環合是利用本實驗室所開發的催化劑醋酸汞,來降低反應的溫度及提高反應產率,之後將異喹啉酮氯化後再與格林納試劑反應合成所需之苯基異喹啉化合物 (26)。另外用類似的合成步驟,也合成了2,3-二苯基喹啉 (39) 的苯基喹啉化合物。
所合成之苯基異喹啉及苯基喹啉化合物將委託孫老師實驗室分別與銥金屬配位形成錯合物後,希望可找出做為紅光的實用摻雜材料。而銥錯合物之合成與OLED元件測試正在進行中。
Part 1. The Constituents of Vittaria anguste-elongate Hayata

Vittaria anguste-elongata Hayata belongs to Vittariaceae and showed significant cytotoxicity toward NUGC-3 and HONE-1 cancer cell lines. There is no report about the constitution of the genus of vittaria, even the family of Vittariaceae. Therefore, we chose Vittaria anguste-elongata as the subject under investigation.
Thirty-nine compounds were isolated and characterized from the whole plant of Vittaria anguste-elongata Hayata. They included eleven new compounds: vittarin-A (1), vittarin-C (2), vittarin-D(3), vittarin-E (4), vittarin-F (5), methyl 4-O-coumaroylquinate (8), 3-O-acetylniduloic acid (10), ethyl 3-O-acetylniduloate (11), vittariflavone (15), vittarilide-A (23),and vittarilide-B (24), as well as twenty-eight known compounds: methyl 4-O-caffeoylquinate (6), ethyl 4-O-caffeoylquinate (7), methyl 5-O-caffeoylquinate (9), apigenin (12), vitexin (13), 5,7-dihydroxy-3,4,5-trimethoxyflavone (14), amentoflavone (16), friedelene-(3) (17) , phytol (18), ��-carotene (19), lutein (20), pheophytin-a (21), 132-hydroxy(132-R)pheophytin-a (22), trans-p-
coumaric acid (25), methyl trans-p-coumarate (26), methyl caffeate (27), ferulic acid (28), p-cresol (29), 4-hydroxybenzaldehyde (30), 4-hydroxybenzoic acid (31), 4-hydroxybenzoic acid methyl ester (32), protocatechualdehyde (33), protocatecheuic acid (34), protocatecheuic acid methyl ester (35), vanillin (36), vanillic acid (37), a mixture of β-sitosterol and stigmasterol (38) and β-sitosteryl-β-D-glucoside (39). Among them, ethyl 4-O-caffeoylquinate (7) was isolated the first time as pure compound from natural source.
Some of the isolated compounds were subjected to evaluate their pharmacological activities. Compound 5,7-Dihydroxy-3,4,5-
trimethoxyflavone (14) showed significant cytotoxicity toward NCH460 and SF268 cancer cell lines. Compound ethyl 4-O-caffeoylquinate (7)、vittarilide-A (23)、vittarilide-B (24) and ferulic acid (28) exhibited stronger antioxidant activity than vitamin E.

Part 2. The Synthesis of 1-Phenylisoquinoline

The three primary colors of light in organic light-emitting devices are blue, green and red. Blue and green emission materials have achieved the objective, but red emission material hasn’t. The current research is interested in increasing luminous efficiency and color purity of red emission material.
The iridium complexes of isoquinoline were red phosphorescent emission compounds. Different substituent on isoquinoline ligands would be influence the property of emission and the purity of color. We hope to find an iridium complexes with better pure-red emission, strong luminous intensity and higher efficiency red phosphorescent based on the complex, 1-phenylisoquinolinato at (piq)2Ir(acac) (17).
Isoquinoline ligands were synthesized by the corresponding isoquinolin-1-one. The cinnamoyl azide was thermally cyclized into isoquinolin-1-one. Under a special catalyst mercury(II) acetate. The reaction temperature of cyclization was decreased and the yield of isoquinolin-1-ones was increased. Then, isoquinolin-1-ones were chlorized into 1-chloroisoquinoline followed by reaction with phenyl Grignard reagent to form the corresponding 1-phenylisoquinoline 26. Using the similar synthesis strategy, quinoline 39 was also synthesized
The iridium complexes with isoquinoline or quinoline were synthesized by Professor Sun’s group now. We hope to find a practical pure-red emission material in the future.
目錄....................................................................Ⅰ
表目錄..................................................................Ⅲ
圖目錄................................................................. IV
中文摘要................................................................V
英文摘要................................................................VII
第一部份
第一章 緒論..............................................................1
第一節 前言..........................................................1
第二節 植物型態......................................................7
第二章 姬書帶蕨全草之抽取與分離..........................................8
第三章 化學構…….......................................................17
第一節 Vittarin-A (1) 之構造研究....................................17
第二節 Vittarin-C (2) 之構造研究....................................22
第三節 Vittarin-D (3) 之構造研究....................................28
第四節 Vittarin-E (4) 之構造研究................................... 33
第五節 Vittarin-F (5) 之構造研究....................................38
第六節 Methyl 4-O-caffeoylquinate (6) 之構造研究....................43
第七節 Ethyl 4-O-caffeoylquinate (7) 之構造研究.....................48
第八節 Methyl 4-O-coumaroylquinate (8) 之構造研究...................53
第九節3-O-acetylniduloic acid (10) 之構造研究...................... 58
第十節 Ethyl 3-O-acetylniduloate (11) 之構造研究................... 63
第十一節 Vittariflavone (15) 之構造研究............................ 68
第十二節 Vittarilide-A (23) 之構造研究............................. 73
第十三節 Vittarilide-B (24) 之構造研究............................. 78
第四章 藥理試驗........................................................ 83
第一節 細胞毒活性.......................................................83
第二節 抗氧化活.........................................................84
第五章 結論............................................................ 86
第六章 實驗部分.........................................................88
第一節 本實驗所使用之儀器.......................................... 88
第二節 萃取與分離.................................................. 90
第三節 生理活性試驗部分之實驗步驟.......................................94
第四節 光譜數據.................................................... 96
參考文獻...............................................................108

第二部分
第一章 緒論........................................................... 110
第一節 有機發光二極體的元件結構與發光機制......................... 110
第二節 主體發光材料與摻雜發光材料..................................112
第三節 目前各色摻雜物材料的發展........................................115
第四節 異喹啉系列之紅色摻雜材料........................................121
第五節 研究動機........................................................124
第二章 結果與討論......................................................126
第一節 不同取代基之苯基異喹啉化合物的合成..............................126
1. 肉桂醯基疊氮化合物的合成..................................127
2. 異喹啉酮的合成............................................128
3. 苯基異喹啉的合成..........................................130
第二節 2,3-二苯基喹啉的合成........................................... 132
第三節 銥金屬錯合物的合成..............................................134
第四節 有機發光二極體元件裝置..........................................136
第三章 結論............................................................137
第四章 實驗部分....................................................... 138
第一節 本實驗所使用之儀器..........................................138
第二節 化合物之合成方法............................................139
參考文獻...............................................................151
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