臺灣博碩士論文加值系統

從南台灣海岸所採集到的軟珊瑚 Klyxum simplex中萃取分離出四個固醇類化合物，其中三個為cholanic acid型態之固醇類化合物，包含二個新的化合物，deoxycholic acid 3,12-diacetate (1)以及化合物1 的甲基酯類衍生物deoxycholic acid 3,12-diacetate-24-methylester (2) 和已知化合物3α,7α,
12α-triacetoxy-5β-cholanic acid (3)，以及另ㄧ個已知固醇類化合物gorgo-
sterol (4)。這些固醇類化合物 1-4之結構鑑定皆經由光譜分析方法加以確認。此次研究亦為首次從海洋生物中分離得到cholanic acid型態之固醇類化合物
此外，在對印尼產海綿Halichondria sp.的研究中，另純化分離出二個已知的isoquinoline quinone類化合物mimosamycin (5) 以及O-demethyl-reni-
erone (6) 和一個已知固醇類化合物24,28-didehydroaplysterol (7)。化合物 5-7的結構亦經由圖譜以及文獻比對方法加以建立。
生物活性試驗結果顯示化合物1、5和6對金黃色葡萄球菌 Staphylococcus aureus具有抑制效果。

In the study on the chemical constituents from the Formosan marine organisms, four steroids, including three cholanic acid type metabolites, deoxycholic acid 3,12-diacetate (1), deoxycholic acid 3,12-diacetate-24-methyl ester (2), 3α,7α,12α-triacetoxy-5β-cholanic acid (3), and a principal steroid, gorgosterol (4), were isolated from the soft coral Klyxum simplex, collected at southern Taiwan coast. The structures of steroids 1-4, were elucidated by extensive spectroscopic methods, particularly in 1D and 2D NMR experiments. To best of our knowledge, there is no report on the isolation of cholanic acid type steroids from any marine source. Based on detailed analysis, steroid 2 was found to be a new natural product and this is the first time to isolate steroid 1 from natural resource.
Furthermore, two known isoquinoline quinones, mimosamycin (5) and O-demethylrenierone (6) and a known steroid,24,28-didehydroaplysterol (7), were obtained from an Indonesian sponge belonging to the genus Halichondria (Halichondriidae). The structures of metabolites 5-7 were determined by spectral data analysis and by comparison with the spectral and physical data of other known compounds.
The antimicrobial activity of compounds 1-7 against Staphylococcus aureus were assayed. It was found that compounds 1, 5 and 6 showed antimicr-
obical activity toward Staphylococcus aureus.

壹、緒論 1
一、研究之重要性及目的 1
二、相關研究之文獻回顧 3
(一) Klyxum simplex 珊瑚之文獻回顧 3
(二) Halichondria sp. 海綿之文獻回顧 8
(三) Isoquinoline quinone 骨架化合物之文獻回顧 10
三、物種型態及分類地位 13
(一) Klyxum simplex 13
(二) Halichondria sp. 14
貳、生物材料與分離方法 15
一、生物樣品材料採集時間與地點 15
(一) Klyxum simplex 15
(二) Halichondria sp. 16
二、萃取與純化分離步驟 17
(一) Klyxum simplex 17
(二) Halichondria sp. 20
參、器材與實驗 23
一、主要使用儀器 23
目錄
二、試劑藥品 24
肆、結果與討論 25
一、天然化合物結構證明 25
(一) Klyxum simplex 25
Deoxycholic acid 3,12-diacetate (1) 25
Deoxycholic acid 3,12-diacetate-24-methylester (2) 35
3α,7α,12α-Triacetoxy-5β-cholanic acid (3) 44
Gorgosterol (4) 53
(二) Halichondria sp. 57
Mimosamycin (5) 57
O-Demethylrenierone (6) 62
24,28-Didehydroaplysterol (7) 67
二、生物活性試驗 71
(一) 生物活性測試步驟 71
(二) 生物活性測試結果 74
伍、結論 75
陸、實驗數據整理 77
柒、參考文獻 79

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