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.

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