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論文名稱 Title |
台灣產軟珊瑚Umbellulifera petasites之二次代謝物的研究 Secondary Metabolites from the Formosan Soft Coral Umbellulifera petasites |
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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 |
139 |
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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 |
2015-07-29 |
繳交日期 Date of Submission |
2015-08-20 |
關鍵字 Keywords |
軟珊瑚、中洲、穗珊瑚、海雞頭目、二次代謝物 petasite, polyoxygenated, Nephtheidae, steroid, Umbellulifera |
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統計 Statistics |
本論文已被瀏覽 5763 次,被下載 135 次 The thesis/dissertation has been browsed 5763 times, has been downloaded 135 times. |
中文摘要 |
本論文主要研究軟珊瑚(Umbellulifera petasites),對這此軟珊瑚以化學方式分析其乙酸乙酯萃取層中所含的成分。共分離出十一個固醇類的天然化合物,其中包含有三個新的固醇類的天然化合物,分別為12α-hydroxy-3-oxo-chol-1,4,22- trien-24-oate (1)、methyl-12α-acetyl-3-oxo-chol-1,4,22-trien-24-oate (2)及methyl-12α-acetyl-3-oxo-chol-1,4,22-trien-24-oate (3), 以及八個已知的固醇類的天然化合物,分別為5α-pregna-20-en-3-one (4)、5α-pregna-1,20-dien-3-one (5)、5α,8α- epidioxycholesta-6,22-dien-3-ol (6)、5α,8α-epidioxy-24(S)-methylcholesta-6,22-dien- 3-ol (7)、5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3-ol (8)、5α,8α-epidioxy cholest-6-en-3-ol (9)、5α,8α-epidioxy-24α-ethylcholesta-6,22-dien-3-ol (10)及5α,8α-epidioxy-24α-ethylcholesta-6-en-3-ol (11)。 上述化合物之化學結構與相對立體構型的鑑定,主要是由一維NMR圖譜(1H NMR, 13C NMR, DEPT)及二維NMR圖譜資料(HMQC, HMBC, COSY, NOESY),加上低解析質譜(LRESIMS)、高解析質譜(HRESIMS)和其他光譜資料(UV, IR, optical rotation)分析以及比對文獻後加以確定。 |
Abstract |
This thesis mainly discussed the investigation of soft corals (Umbellulifera petasite). The soft coral (Umbellulifera petasite) is extracted and purified with chemical methods. Eleven steroids were isolated and included three new coumpounds. Three new steroids are 12α-hydroxy-3-oxo-chol-1,4,22-trien-24-oate (1), methyl-12α-acetyl-3-oxo-chol-1,4,22-trien-24-oate (2), and methyl-12α-acetyl-3-oxo-chol-1,4, 22-trien-24-oate (3). Eight known steroids were 5α-pregna-20-en-3-one (4), 5α-pregna-1,20-dien-3-one (5), 5α,8α-epidioxy cholesta-6,22-dien-3-ol (6), 5α,8α-epidioxy- 24(S)-methylcholesta-6,22-dien-3-ol (7), 5α,8α-epidioxy-24(R)-methylcholesta-6,22- dien-3-ol (8), 5α,8α-epidioxycholest-6-en-3-ol (9), 5α,8α-epidioxy-24α-ethyl cholesta-6,22-dien-3-ol (10), and 5α,8α-epidioxy-24α-ethylcholesta-6-en-3-ol (11). The structures of these compounds were determined by extensive 1D (1H NMR, 13C NMR, DEPT) and 2D NMR (1H–1H COSY, HMQC, HMBC, and NOESY), as well as LRESIMS, HRESIMS, IR, UV and optical rotation values. Structural elucidation had been done by means of data comparison with those on the literature. |
目次 Table of Contents |
論文審定書 i 中文摘要 ii 英文摘要 iii 化合物化學結構 x 第一章 緒論 1 第一節 前言 1 第二節 研究目標與動機 2 第二章 文獻回顧 3 第三章 實驗材料與操作方法 21 第一節 實驗樣品採集與分類地位 21 第二節 實驗程序與方法 22 第三節 實驗儀器 26 第四節 藥品與試劑 27 第五節 結構之鑑定 28 第四章 結果與討論 29 穗珊瑚Umbellulifera petasites天然物之化學結構解析 29 (一) methyl-12α-hydroxy-3-oxo-chol-1,4,22-trien-24-oate (1)之結構解析 29 (二) methyl-12α-acetyl-3-oxo-chol-1,4,22-trien-24-oate (2)之結構解析 45 (三) methyl-12α-acetyl-3-oxo-chol-1,4,22-trien-24-oate (3)之結構解析 61 (四) 5α-pregna-20-en-3-one (4)之結構解析 77 (五) 5α-pregna-1,20-dien-3-one (5)之結構解析 82 (六) 5α,8α-epidioxycholesta-6,22-dien-3-ol (6)之結構解析 88 (七) 5α,8α-epidioxy-24(S)-methylcholesta-6,22-dien-3-ol (7)之結構解析 94 (八) 5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3-ol (8)之結構解析 100 (九) 5α,8α-epidioxycholest-6-en-3-ol (9)之結構解析 106 (十) 5α,8α-epidioxy-24α-ethylcholesta-6,22-dien-3-ol (10)之結構解析 112 (十一) 5α,8α-epidioxy-24α-ethylcholesta-6-en-3-ol (11)之結構解析 118 第五章 結論 124 參考文獻 125 |
參考文獻 References |
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