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作者:曾宣融
作者(英文):Hsuan-Jung Tseng
論文名稱:臺灣產指型軟珊瑚Sinularia sp.所含雙萜類化合物之研究
論文名稱(英文):Studies on Diterpenoids from a Formosan Soft Coral Sinularia sp.
指導教授:宋秉鈞
郭傑民
指導教授(英文):Ping-Jyun Sung
Jimmy Kuo
口試委員:蘇瑞欣
宋秉鈞
郭傑民
口試委員(英文):Jui-Hsin Su
Ping-Jyun Sung
Jimmy Kuo
學位類別:碩士
校院名稱:國立東華大學
系所名稱:海洋生物研究所
學號:611063012
出版年(民國):112
畢業學年度:111
語文別:中文
論文頁數:128
關鍵詞:八放珊瑚指形軟珊瑚雙萜菸草烷細胞毒殺構效關係
關鍵詞(英文):octocoralSinulariaditerpenoidcembranecytotoxicitySAR
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本研究主要針對臺灣海域所採集之指形軟珊瑚Sinularia sp. 所含天然物成分進行分析,並從中分離純化出五個雙萜類化合物,包含一個新骨架化合物sinulariaone A (1) 和三個cembrane類的新化合物chlorofurancembranoids A、B (2、3)、bisepoxycembrene A (4),以及一個已知的capnosane骨架化合物lobophytrol C (5)。利用NMR圖譜解析、量子力學計算以及文獻資料比對方式分析化合物的平面結構以及相對立體構型;並且透過X-ray單晶體繞射實驗進一步確定了化合物1–4的絕對立體構型。
在細胞毒殺試驗中化合物3對HL-60具有細胞毒殺作用,IC50值為3.67 μM。
This study foucus on the natural products from a soft coral identified as Sinularia sp. which was collected from the waters of Taiwan. Five diterpenoids were isolated, including a novel diterpenoid sinulariaone A (1), three new cembrane-type diterpenoids chlorofurancembranoids A (2), B (3) and bisepoxycembrene A (4), along with a known capnosane-type compound lobophytrol C (5). Using NMR spectrum analysis, quantum mechanical calculation and literature comparison to establish the structures of compounds 1−5. The absolute configurations of compounds 1–4 were further confirmed by single X-ray crystal diffraction analysis.
In the cytotoxicity test, compound 3 showed cytotoxic effect on HL-60 cells with an IC50 values of 3.67 μM.
謝詞 I
中文摘要 III
Abstract V
化合物總圖1–5 VII
目錄 IX
圖目錄 XI
表目錄 XV
第一章、緒論 1
第一節、前言與研究動機 1
第二節、軟珊瑚所含特定結構之雙萜類天然物文獻回顧 2
第二章、生物材料與分離流程 11
第一節、生物樣本採集與分類 11
(一)、指形軟珊瑚Sinularia sp.樣品採集資料 11
(二)、指形軟珊瑚Sinularia sp.生物鑑種與分類 11
第二節、生物樣品萃取與分離流程 14
(一)、指形軟珊瑚Sinularia sp.生物樣品萃取與分離流程 14
第三章、實驗器材與有機溶劑 17
第一節、儀器 17
第二節、層析材料 18
第三節、有機溶劑 18
第四章、結果與討論 19
第一節、指形軟珊瑚Sinularia sp. 所含化合物之結構解析 19
(一)、Sinulariaone A (1) 之結構解析 19
(二)、Chlorofurancembranoid A (2) 之結構解析 33
(三)、Chlorofurancembranoid B (3) 之結構解析 45
(四)、Bisepoxycembrene A (4) 之結構解析 59
(五)、Lobophytrol C (5) 之結構解析 71
第二節、化合物實驗數據整理 81
第五章、生物活性試驗 83
第六章、結論 85
參考文獻 87
附錄、X-ray 解析資料 91
(一)、Sinulariaone A (1) (CCDC: 2226689) 91
(二)、Chlorofurancembranoid A (2) (CCDC:2160557) 98
(三)、Chlorofurancembranoid B (3) (CCDC:2208811) 110
(四)、Bisepoxycembrene A (4) (CCDC:2105023) 122
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