臺灣博碩士論文加值系統

本論文主要研究台灣產海綿Ircinia formosana之甲醇/二氯甲烷之萃取物，以矽膠管柱層析和高壓液態層析儀純化後，分離出八個化合物，皆屬於linear C-22-sesterterpenoid骨架，其中包含六個新的天然物，將其命名為irciformonins E~J (1~6)，與兩個已知化合物，經比對文獻後得知為irciformonins A和B。
所有化合物的結構解析是利用ㄧ維及二維核磁共振圖譜(1D-NMR and 2D-NMR)、旋光(optical rotation)、紅外光光譜(IR)、紫外光光譜(UV)及高解析質譜(high resolution mass spectrum)和比對相關文獻來鑑定。立體結構的判定則是以MM2、NOESY圖譜和比對相關文獻來判定的。
所有化合物主要的構造有一個furan環、五元環內酯和三組甲基訊號。化合物1和2是幾何學上的同分異構物，僅甲氧基的取代與一組雙鍵位置不同，甲氧基的取代分別位於C-10和C-12位上，雙鍵則分別位於C-11/C-12和C-10/C-11上。化合物3和6在結構上只差羥基的取代與一組雙鍵位置不同，化合物3在C-12位上多了一個羥基的取代，化合物3與6的雙鍵則分別位於C-10/C-11和C-11/C-12上。化合物4於C-12~C-15位上為一五元環結構，C-10位上則氧化成酮基。¬而化合物5於C-10、C-15位上有兩個乙醯基的取代。

Six new compounds, irciformonins E~J (1~6), were isolated from CH2Cl2/MeOH extract of the sponge Ircinia formosana collected in Taiwan, toghther with two known compounds, irciformonins A and B. These compounds possess a linear C-22-sesterterpenoids type skeleton.
The structures of all compounds were elucidated by spectroscopic analysis including 1D and 2D-NMR, optical rotation, IR, UV and high resolution mass spectra, as well as comparison with those in references. The stereochemistry of these compounds were determined by NOESY experiments, MM2 minimized energy, as well as comparison with those in references.
The structures of all compounds possess a furan ring, a five membered lactone ring , and three methyl groups. Compounds 1 and 2 are geometric isomers. The differences between them are the substituents of the methoxyl group and the double bond. Compounds 1 and 2 possess substituents of the methoxyl group at C-10 and C-12 and have the double bond at C-11/C-12 and C-10/C-11. The differences between compounds 3 and 6 are the functional groups of the acetyl moeity and the double bond. Compound 3 has an acetyl group at C-12. Compounds 3 and 6 contain two double bonds at C-10/C-11 and C-11/C-12. Compound 4 has a cyclopentane between C-12~C-15 and a ketone group at C-10 while compound 5 possesses two acetyl groups at C-10 and C-15 positions.

壹、 緒論
ㄧ、前言 1
二、文獻回顧 3
三、研究動機 17
貳、 材料與方法
ㄧ、樣品採集 18
二、分離流程 19
三、化學結構鑑定26
參、 實驗結果
ㄧ、化合物結構解析 28
1. Irciformonin E (1)之化學結構解析 28
2. Irciformonin F (2)之化學結構解析 38
3. Irciformonin G (3)之化學結構解析 47
4. Irciformonin H (4)之化學結構解析 56
5. Irciformonin I (5)之化學結構解析 65
6. Irciformonin J (6)之化學結構解析 74
肆、結論 82
伍、參考文獻 86
陸、附錄
ㄧ、化合物1之八種MM2最低能量模型排列 88
二、化合物1~6之物理資料 92

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