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研究生:盧詣
研究生(外文):Yi Lu
論文名稱:台灣產指形軟珊瑚Sinularia querciformis所含Cembranoids之天然化合物研究
論文名稱(外文):Study on Cembranoids from the Formosan Soft Coral Sinularia querciformis
指導教授:許志宏許志宏引用關係
指導教授(外文):Jyh-Horng Sheu
學位類別:碩士
校院名稱:國立中山大學
系所名稱:海洋生物科技暨資源學系研究所
學門:自然科學學門
學類:海洋科學學類
論文種類:學術論文
論文出版年:2008
畢業學年度:96
語文別:中文
論文頁數:189
中文關鍵詞:Sinularia querciformis
外文關鍵詞:Sinularia querciformis
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為了從台灣產軟珊瑚開發新的藥物,從Sinularia querciformis的有機萃取物中尋找去有生物活性的化學成分。從這次軟珊瑚的研究中共發現得到十七個cembrane 類的化合物(1–17),其中包含十個新化合物(1–10),即 querciformolides A–F和querciformilins A–D以及七個已知的化合物(10–17)。化合物1–17的化學結構包括立體化學可藉由光譜資料的分析(IR, MS, 1D, 及2D NMR)和比對文獻上已知化合物的光譜資料而確立。化合物2由X-ray晶體繞射來證明其化合物之結構,化合物1和11經由Mosher的酯化反應,確立了化合物1–4, 11和12的絕對立體組態。
上述化合物在生物活性試驗中,化合物14和17對四種人類癌細胞 Daoy (髓母細胞瘤癌細胞)、Hep 2 (喉癌細胞)、MCF-7(乳癌細胞)和Hela (子宮頸癌細胞)具有細胞毒殺活性,而化合物3–7, 11–17 在濃度為10 µM下可有效的抑制致發炎蛋白質iNOS的表現,又化合物3, 11, 12, 16和17在濃度為 10 µM下可有效的抑制致發炎蛋白質COX-2有表現。
In order to discover and develop new drug from soft corals of Taiwan, we have searched the bioactive metabolites from the organic extracts of a soft coral Sinularia querciformis. This study had led to the isolation of seventeen cembrane-type compounds (1–17), including ten new natural compounds (1-10), along with seven known compounds (11-17). The structures of metabolites 1–17, including their stereochemistries have been established by spectroscopic analyses (IR, MS, 1D, and 2D NMR) and by comparison of the related physical and spectral data with those of other known compounds. The relative configuration of compound 2 was further confirmed by X-ray single-crystal diffraction analysis. The absolute configurations of 1–4, 11 and 12 were determined using a modified Mosher’s method for 1 and 11.
In above metabolites, compounds 14 and 17 were found to exhibit inhibition against the growth of cervical epitheloid (Hela), laryngeal (Hep 2), medulloblastoma (Daoy) and breast (MCF-7) carcinoma cells. Furthermore, compounds 3–7 and 11–17 were found to significantly inhibit the accumulation of the pro–inflammatory iNOS protein at 10 μM, and compounds 3, 11, 12, 16, and 17 were also found to significantly inhibit the accumulation of the pro–inflammatory COX-2 protein at 10 μM.
中文摘要 XIII
英文摘要 XIV
化合物1–17的結構 XV
壹、緒論 1
一、前言 1
二、研究動機及目的 2
Sinularia屬軟珊瑚所含cembranoids類天然化合物及其生物活性之回顧 4
貳、實驗程序與方法 18
一、生物樣品採集時間、地點與分類地位 18
二、生物樣品的分類 18
三、萃取與分離純化步驟 19
四、實驗器材與溶劑 22
(一)、儀器 22
(二)、試劑藥品 23
參、生物活性測試 24
一、生物活性試驗方法 24
(一)、細胞毒殺活性試驗方法 24
(二)、抗發炎活性試驗方法 26
肆、實驗結果與討論 29
一、Sinularia querciformis 化合物之結構解析 29
(一)、Querciformolide A (1) 化合物構造之解析 29
(二)、Querciformolide B (2) 化合物構造之解析 39
(三)、Querciformolide C (3) 化合物構造之解析 47
(四)、Querciformolide D (4) 化合物構造之解析 55
(五)、Querciformolide E (5) 化合物構造之解析 64
(六)、Querciformolide F (6) 化合物構造之解析 74
(七)、Querciformilin A (7) 化合物構造之解析 85
(八)、Querciformilin B (8) 化合物構造之解析 95
(九)、Querciformilin C (9) 化合物構造之解析 103
(十)、Querciformilin D (10) 化合物構造之解析 111
(十一)、Sinulariolone (11) 化合物構造之解析 121
(十二)、Sinulariolone acetate (12) 化合物構造之解析 126
(十三)、3,4:8,11-Bisepoxy-7-hydroxycembra
-15(17)-en-1,12-olide (13) 化合物構造之解析 130

(十四)、3,4:8,11-Bisepoxy-7-acetoxycembra
-15(17)-en-1,12-olide (14) 化合物構造之解析 134
(十五)、Sinulariolide (15) 化合物構造之解析 138
(十六)、11-Epi-sinulariolide acetate (16) 化合物構造之解
析 142
(十七)、Dihydrosinulariolide (17) 化合物構造之解析 146
二、化學反應步驟 150
三、化合物物理性質及圖譜數據整理 154
伍、生物活性試驗結果 158
一、細胞毒殺活性試驗結果 158
二、抗發炎活性試驗結果 159
陸、結論 162
柒、參考資料 167
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