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博碩士論文 etd-0208110-105924 詳細資訊
Title page for etd-0208110-105924
論文名稱
Title
台灣產肥厚肉質軟珊瑚 Sarcophyton crassocaule 所含Cembranoid 類化合物之研究
Study on Cembranoids from the Formosan Soft Coral Sarcophyton crassocaule
系所名稱
Department
畢業學年期
Year, semester
語文別
Language
學位類別
Degree
頁數
Number of pages
318
研究生
Author
指導教授
Advisor
召集委員
Convenor
口試委員
Advisory Committee
口試日期
Date of Exam
2010-01-22
繳交日期
Date of Submission
2010-02-08
關鍵字
Keywords
化合物、肥厚肉質軟珊瑚、活性
soft coral, Sarcophyton crassocaule, anti-inflammatory activity, cytotoxicity, cembranoids
統計
Statistics
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中文摘要
本研究主要是從肉質軟珊瑚 Sarcophyton crassocaule 的有機溶劑萃取物中尋找具有生物活性的化學成分。本研究總共分離得到26個cembranoids類的天然化合物1–26,其中1–18為新化合物,19–26為已知的化合物。所有化合物的化學構造均由光譜數據的分析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決定。化合物8、9和11並經由反應步驟確認其分子結構,而化合物1的絕對立體結構,則可經由Mosher’s酯化反應加以確定。
本研究中,將所獲得的化合物1–26進行癌細胞株的細胞毒殺與抗發炎活性測試,並且藉由活性的結果去探討與化合物結構之間的關係。在細胞毒殺活性測試結果顯示化合物3和9對人類髓母細胞(Daoy)、人類喉癌細胞(HEp-2)、人類乳癌細胞(MCF-7)和人類結腸癌細胞(WiDr) 都具有良好的細胞毒殺活性,而化合物18、19、20、22和24在對人類T淋巴細胞(CCRF-CEM)、人類結直腸腫瘤細胞(DLD-1)以及人類前骨髓性白血病細胞(HL-60)都具有良好的細胞毒殺活性。而化合物1–26對於在濃度為10 μM下可有效的抑制發炎蛋白質iNOS的表現,其中化合物9、17、19、22和24對於COX-2也具有良好的抑制效果。
Abstract
In order to search for bioactive compounds, we have studied the chemical constituents from the organic extracts of the soft coral Sarcophyton crassocaule. This study had led to the isolation of twenty-six natural cembrane-type diterpenoids, compounds 1–26, including eighteen new compounds, sarcocrassocolide A–R (1–18), along with six know compounds, crassocolide A, B, D, E, L, sarcocrassolide, sinularolide E and 13-acetoxysarcocrassolide (19–26). The structures of compounds 1–26 were established by detailed spectroscopic data analysis (IR, MS, 1D, 2D NMR) and by comparison of the spectral data with those of the related known compounds. The structures of 8, 9 and 11 were further established by orgamic methods, and the absolute configuration of 1 was determined using a modified Mosher’s method.
The cytotoxicity of compounds 1–17 and 19–21 against the Daoy (human medulloblastoma), HEp2 (human laryngeal carcinoma), MCF-7 (human breast adenocarcinoma), WiDr (human colon adenocarcinoma), DLD-1 (human colon adenocarcinoma), CCRF-CEM (human T-cell acute lymphoblastic leukemia), and HL-60 (human promyelocytic leukemia) tumor cell lines were determined, and structure-activity relationship was presented by statistic method. Compounds 3 and 9 showed significant activity toward the above Daoy, HEp2, MCF7 and WiDr, and compounds 18, 19, 20, 22 and 24 were found to show significant activity toward the above DLD-1, CCRF-CEM and HL-60. Compounds 1–26 were shown to exert significant anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells. Compounds 9, 17, 19, 22 and 24 also significantly inhibited the accumulation of pro-inflammatory COX-2 protein.
目次 Table of Contents
中文摘要 XVII
英文摘要 XVIII
化合物1-26化學結構 XIX
第一章、緒論 1
第一節、前言 1
第二節、研究動機 2
第三節、文獻回顧 4
第二章、生物材料與研究方法 40
第一節、研究流程 40
第二節、Sarcophyton crassocaule 物種的採集及分類地位 42
第三節、Sarcophyton crassocaule 的分離流程 42
第四節、實驗設備儀器及材料 45
第三章、生物活性試驗方法 48
第一節、細胞毒殺活性試驗方法 48
第二節、抗發炎活性試驗方法 50
第四章、化合物之結構證明 53
第一節、軟珊瑚Sarcophyton crassocaule 所分離出之化合物的結構解析 53
(一)、Sarcocrassocolide A (1) 化合物構造之解析 53
(二)、Sarcocrassocolide B (2) 化合物構造之解析 64
(三)、Sarcocrassocolide C (3) 化合物構造之解析 74
(四)、Sarcocrassocolide D (4) 化合物構造之解析 84
(五)、Sarcocrassocolide E (5) 化合物構造之解析 94
(六)、Sarcocrassocolide F (6) 化合物構造之解析 104
(七)、Sarcocrassocolide G (7) 化合物構造之解析 114
(八)、Sarcocrassocolide H (8) 化合物構造之解析 124
(九)、Sarcocrassocolide I (9) 化合物構造之解析 133
(十)、Sarcocrassocolide J (10) 化合物構造之解析 142
(十一)、Sarcocrassocolide K (11) 化合物構造之解析 151
(十二)、Sarcocrassocolide L (12) 化合物構造之解析 160
(十三)、Sarcocrassocolide M (13) 化合物構造之解析 170
(十四)、Sarcocrassocolide N (14) 化合物構造之解析 180
(十五)、Sarcocrassocolide O (15) 化合物構造之解析 190
(十六)、Sarcocrassocolide P (16) 化合物構造之解析 200
(十七)、Sarcocrassocolide Q (17) 化合物構造之解析 210
(十八)、Sarcocrassocolide R (18) 化合物構造之解析 220
(十九)、Crassocolide A (19) 化合物構造之解析 230
(二十)、Crassocolide B (20) 化合物構造之解析 234
(二十一)、Crassocolide D (21) 化合物構造之解析 238
(二十二)、Crassocolide E (22) 化合物構造之解析 242
(二十三)、Crassocolide L (23) 化合物構造之解析 246
(二十四)、Sarcocrassolide (24) 化合物構造之解析 250
(二十五)、Sinularolide E (25) 化合物構造之解析 254
(二十六)、13-Acetoxysarcocrassolide (26) 化合物構造之解析 258
第二節、化學反應步驟 262
第三節、化合物物理性質及圖譜數據整理 264
第五章、生物活性試驗結果 269
第一節、細胞毒殺活性試驗結果 269
第二節、抗發炎活性試驗結果 274
第六章、結論 278
第七章、參考文獻 287
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