臺灣博碩士論文加值系統

本次研究是採集澎湖海域的軟珊瑚Cladiella hirsuta, 將其所含的
天然化合物進行分離､純化, 共得到十個新的化合物: hirsutalins A-D (1,
2, 3, 5), hirsutosterols A-F (6, 7, 8, 9, 10, 11) 及一個已知的化合物:
3-butanoyloxycladiell-11(17)-en-6,7-diol (4)。
所有化合物的化學結構均由光譜資料分析(NMR､IR､MS) 以及
比對文獻上已知化合物的結構､數據資料來決定, 化合物1 的絕對立
體構造並經由Mosher’s 酯化反應加以確定。
在細胞毒殺活性試驗方面, 採用人類的六種癌細胞株: HepG2(肝
癌細胞)､Hep3B(肝癌細胞)､Ca9-22(口腔癌細胞)､A549(肺癌細胞)､
MCF7(乳腺癌細胞)､MDA-MB-231(乳腺癌細胞), 其中化合物5 對
HepG2 具有顯著的毒殺活性，化合物 7 對上述六種癌細胞株皆具有中
度的毒殺活性, 化合物 6､8､10 也對Hep3B､Ca9-22 兩種癌細胞具
有中度的毒殺活性; 而化合物 6､7 水解後的產物6a､7a, 其IC50 與
原化合物6､7 並無顯著差異。
在抗發炎活性試驗方面, 化合物2對於被誘發出的iNOS蛋白質與
COX-2 蛋白質具有良好的抑制活性, 化合物3 對於被誘發出的iNOS
蛋白質具有良好的抑制活性。

Chemical investigation of the soft coral Cladiella hirsuta, collected off
the coast of Penghu Islands, has led to the isolation of natural products
including ten new compounds hirsutalins A-D (1, 2, 3, 5) and
hirsutosterols A-F (6, 7, 8, 9, 10, 11), and one known compound
3-butanoyloxycladiell-11(17)-en-6,7-diol (4).
All of the chemical structures were established by detailed spectral
data analysis (NMR, IR, MS) and by comparison of the spectral data with
those of the related known compounds. The absolute structure of
compound 1 was determined applying a modified Mosher’s method.
On the part of the cytotoxicity assay with six human cancer cell lines,
HepG2 (liver cancer cell), Hep3B (liver cancer cell), Ca9-22 (mouth cavity
cancer cell), A549 (lung cancer cell), MCF7 (breast cancer cell) and
MDA-MB-231 (breast cancer cell), compound 5 showed the significant
cytotoxicity against the cancer cell line HepG2; compound 7 showed the
moderate cytotoxicity against all of the above cancer cell lines; compounds
6, 8 and 10 also showed the moderate cytotoxicity against two of them,
Hep3B and Ca9-22. The products 6a and 7a , obtained by hydorlysis of 6
and 7, respectively, did not show obvious difference in cytotoxity by
comparison of the IC50 values of compounds 6 and 7.
On the part of anti-inflammation assay, compound 2 showed the
effectively inhibiting activity against the induced iNOS and COX-2
proteins. Compound 3 showed nearly the same activity against the induced
iNOS protein as that of 2.

中文摘要 1
英文摘要 2
化合物 1-11 之結構圖 3
第一章､緒論 4
第一節､前言 4
第二節､研究背景與動機 4
第三節､文獻回顧 5
第二章､實驗程序與方法 13
第一節､生物樣品的採集時間與地點 13
第二節､生物樣品的分類 13
第三節､萃取與分離的純化步驟 14
第四節､實驗器材 17
1､實驗儀器 17
2､實驗材料與溶劑 17
第三章､實驗結果與討論 19
第一節､軟珊瑚Cladiella hirsuta 所分離化合物之結構解析 19
(一)､hirsutalin A (1) 之結構解析 19
(二)､hirsutalin B (2) 之結構解析 31
(三)､hirsutalin C (3) 之結構解析 42
(四)､3-butanoyloxycladiell-ll(17)-
en-6,7-diol (4) 之結構解析 53
(五)､hirsutalin D (5) 之結構解析 56
(六)､hirsutosterol A (6) 之結構解析 67
(七)､hirsutosterol B (7) 之結構解析 78
(八)､hirsutosterol C (8) 之結構解析 89
(九)､hirsutosterol D (9) 之結構解析 102
(十)､hirsutosterol E (10) 之結構解析 113
(十一)､hirsutosterol F (11) 之結構解析 124
第二節､化學反應步驟 135
(一)､Mosher’s 酯化反應 135
(二)､酯類水解反應 136
第四章､生物活性試驗 137
第一節､細胞毒殺活性試驗 137
第二節､抗發炎活性試驗 138
第三節､細胞毒殺活性試驗結果 141
第四節､抗發炎活性試驗結果 141
第五章､結論 144
參考文獻 145

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