臺灣博碩士論文加值系統

針對台灣墾丁海域所採集的軟珊瑚Sinularia gibberosa 所具有的化學成分研究中，共分離出七個新發現的Cembranoid類化合物 gibberorenes A-G（2-8），及三個Sterols 類化合物gibberoketosterol B（10）、gibberoepoxysterol（11）、gibberoketosterol C（12），與兩個已知化合物 (1Z,3E,7E,11S,12S,14S)-11,12-epoxycembra-1,3,7-trien-14-ol（1）、gibberoketosterol（9）。化合物1-12之化學結構及相對立體構型均是以各種光譜解析（IR、 MS、 1D及2D NMR）及文獻比對的方法加以確立。同時，並將所獲得之天然化合物1-12進行癌細胞株的細胞毒殺活性測試，其中化合物9、11對MCF-7、A549、MDA-MB-231與HepG2具有中等的細胞毒殺活性。此外，化合物9、10亦進行抗發炎活性測試，其中化合物9具有抑制iNOS 及COX-2的活性。

Investigation on the chemical constituents of the Formosan soft coral Sinularia gibberosa, collected by hand using scuba off the coast of Kenting, had led to the isolation of seven new cembranoids , gibberorenes A-G（2-8）, three new sterols, gibberoketosterol B（10）, gibberoepoxysterol（11）, gibberoketosterol C （12） along with two known compounds, (1Z,3E,7E,11S,12S,14S)-11,12-epoxycembra-1,3,7
-trien-14-ol（1）and gibberoketosterol（9）. The structures of 1-12 were elucidated on the basis of extensive spectroscopic analysis, including IR, MS, 1D, and 2D NMR. Cytotoxicities of 1-12 against a limited panel of cancer cell lines were also evaluated. Among these metablites, compounds 9 and 11 were found to exhibit moderate cytotoxicity toward MCF-7, A549, MDA-MB-231, and HepG2 tumor cells. The ability of 9 and 10 to inhibit the pro-inflammatory iNOS and COX-2 expression of LPS-stimulated RAW264.7 macrophage cells has been also estimated.

中文摘要 XI
英文摘要 XII
第一章 緒論 1
一、前言 1
二、研究動機 2
三、過去相關研究概要 4
(一)、軟珊瑚Sinularia gibberosa 之文獻回顧 4
(二)、具有1,3-diene cembrane 類化合物之文獻回顧 7
(三)、Sterols 類之文獻回顧 14
第二章 實驗程序與方法 18
一、生物樣品採集時間、地點、物種型態與分類地位 18
(一)、Sinularia gibberosa 採集時間與地點 18
(二)、Sinularia gibberosa 物種型態及生物學上分類地位 18
二、萃取與分離純化步驟 19
三、實驗器材與溶劑 22
(一)、使用器材 22
(二)、使用溶劑 23
第三章 細胞毒殺活性測試 24
一、生物活性實驗 24
(一)、細胞毒殺活性測試之檢測原理 24
(二)、細胞毒殺活性測試之檢測方法之一 25
(三)、細胞毒殺活性測試之檢測方法之二 26
(四)、抗發炎活性測試之檢測原理 27
(五)、抗發炎活性測試之檢測方法 28
二、實驗採用之癌細胞株 28
第四章 實驗結果與討論 29
一、軟珊瑚Sinularia gibberosa 所分離出之化合物結構解析 29
(一)、(1Z,3E,7E,11S,12S,14S)-11,12-epoxycembra-1,3,7-trien-14-ol（1）之結構解析 29
(二)、Gibberorene A（2）之結構解析 39
(三)、Gibberorene B（3）之結構解析 49
(四)、Gibberorene C（4）之結構解析 60
(五)、Gibberorene D（5）之結構解析 69
(六)、Gibberorene E（6）之結構解析 80
(七)、Gibberorene F（7）之結構解析 91
(八)、Gibberorene G（8）之結構解析 101
(九)、Gibberoketosterol（9）之結構解析 111
(十)、Gibberoketosterol B（10）之結構解析 120
(十一)、Gibberoepoxysterol（11）之結構解析 132
(十二)、Gibberoketosterol C（12）之結構解析 145
二、純化之天然化合物細胞毒殺活性 157
三、純化之天然化合物抗發炎活性 158
第五章 結論 159
第六章 參考文獻 161

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