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論文名稱 Title |
台灣產軟珊瑚 Lemnalia philippinensis的化學成分及生物活性之研究
Chemical Constituents and Biological Activities of the Formosan Soft Coral Lemnalia philippinensis |
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系所名稱 Department |
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畢業學年期 Year, semester |
語文別 Language |
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學位類別 Degree |
頁數 Number of pages |
156 |
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研究生 Author |
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指導教授 Advisor |
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召集委員 Convenor |
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口試委員 Advisory Committee |
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口試日期 Date of Exam |
2011-07-14 |
繳交日期 Date of Submission |
2011-09-01 |
關鍵字 Keywords |
eremophliane、lemnaphinolide、ylangene、5-cycloneolemnane、lemnaphilins、穗軟珊瑚、4、neolemnane lemnaphilins, neolemnane, 5-cycloneolemnane, eremophliane, Lemnalia philippinensis, 4, lemnaphinolide, ylangene |
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統計 Statistics |
本論文已被瀏覽 5668 次,被下載 387 次 The thesis/dissertation has been browsed 5668 times, has been downloaded 387 times. |
中文摘要 |
我們研究台灣軟珊瑚 Lemnalia philippinensis 的化學組成,發現有七個新的化合物從穗軟珊瑚 L. philippinensis 中共分離出來,其中包含了三個 ylangene-type sesquiterpenoids的化合物 lemnaphilins A-C (1-3),兩個 eremophilane-type sesquiterpenoids的化合物lemnaphilins D-E (4-5),一個 neolemnane-type sesquiterpenoid的化合物lemnaphilin F (6),與一個4,5-cycloneolemnane-type sesquiterpenoid的化合物 lemnaphinolide (7),以及分離到八個已知化合物,分別為lemnalol (8) , 11,12-dihydroxy-6,10-eremopilaiene(9), 4(S*)-acetoxy,10(S*)-hydr-oxyl,5-oxo,l(S*),12(S*)neolemna-2(Z),8-diene(10), laevinone A (11), 2-oxolemnacarnol (12), lemnal-1(10)-ene-2,12-dione (13), 2,7-nardosinoxanedione (14), elongatol B (15)上述化合物的構造均是由光譜數據的分析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決定。 本研究中亦對所獲得的化合物 1-15針對人類肝癌細胞(HepG2)、人類乳癌細胞(MDA-MB231),以及人類呼吸道表皮癌細胞(A549)進行細胞毒殺測試,發現只有lemnaphilin A其就有細胞毒殺的活性,所測得的IC50濃度各為15.99、16.31以及15.81 μg/mL. |
Abstract |
From the chemical investigation of a Formosan soft coral Lemnalia philippinensis, we had discovered seven new sesquiterpenoids, including three ylangene-type sesquiterpenoids lemnaphilins A-C ( 1-3 ), two eremophilane-type sesquiterpenoids lemnaphilins D-E ( 4-5 ), one neolemnane-type sesquiterpenoid lemnaphilin F (6), and one 4,5-cycloneolemnane-type sesquiterpenoid lemnaphinolide (7), along with eight known compounds, lemnalol(8) , 11,12-dihydroxy-6,10-eremopi -laiene (9),4(S*)-acetoxy,10(S*)-hydroxy,5-oxo,l(S*),12(S*)neolemna–2(Z), 8–diene (10), laevinone A (11), 2-oxolemnacarnol(12), lemnal-1(10)- ene-2,12-dione (13), 2,7 -nardosinoxanedione (14), elongatol B (15). The structures of these compounds were established by the detailed spectral analysis (IR, MS, 1D, 2D NMR) and by comparison of the spectral data with those of the related known compounds. The cytotoxicity of fifteen compounds (1–15) against with three cell lines, including HepG2 (human liver hepatocellular carninoma cells)、MDA-MB231(human breast cancer cells) and A549(human respiratory epithelial cells)was also determined. Only lemnaphilin A exhibited cytotoxicity, with IC50 values 15.99、16.31and 15.81 μg/mL. |
目次 Table of Contents |
中文摘要 i 英文摘要 ii 第一章、緒論 第一節、前言 1 第二節、研究背景及目的 2 第三節、文獻回顧 5 第四節、珊瑚型態與分布 23 第二章、生物材料採集、鑑種與研究方法 24 第三章、化合物之結構證明 第一節、軟珊瑚Lemnalia philippinensis 所分離出之化合物的結構之解析 28 (一)、Lemnaphilin A (1) 結構之解析 28 (二)、Lemnaphilin B (2) 結構之解析 37 (三)、Lemnaphilin C (3) 結構之解析 46 (四)、Lemnaphilin D (4) 結構之解析 55 (五)、Lemnaphilin E (5) 結構之解析 64 (六)、Lemnaphilin F (6) 結構之解析 72 (七)、Lemnaphinolide (7) 結構之解析 81 (八)、Lemnalol (8) 結構之解析 90 (九)、11,12-dihydroxy-6,10-eremopilaiene (9) 結構之解析 94 (十)、4(S*)-acetoxy,10(S*)-hydroxy,5-oxo,l(S*),12(S*) (十一)、Laevinone A (11) 結構之解析 102 (十二)、2-Oxolemnacarnol (12) 結構之解析 106 (十三)、Lemnal-1(10)-ene-2,12-dione (13) 結構之解析 110 (十四)、2,7-nardosinoxanedione (14) 結構之解析 114 (十四)、Elongatol B (15) 結構之解析 118 第二節、生合成路徑 122 第三節、化合物物理性質及圖譜數據整理 125 第四章、生物活性試驗 127 第五章、結論 128 第六章、實驗相關部分 第一節、儀器與材料 133 第二節、珊瑚的分離與純化 135 第三節、生物活性的方法與步驟 136 第七章、參考文獻 138 |
參考文獻 References |
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