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研究生:邱新嵐
研究生(外文):Shin-lan Chiu
論文名稱:台灣海域指型軟珊瑚Sinularia triangular所含活性成分研究
論文名稱(外文):Studies on the Bioactive Constituents from theFormosan Soft Coral Sinularia triangular
指導教授:蘇瑞欣
學位類別:碩士
校院名稱:美和技術學院
系所名稱:健康與生技產業研究所
學門:商業及管理學門
學類:醫管學類
論文種類:學術論文
論文出版年:2010
畢業學年度:98
語文別:中文
論文頁數:95
中文關鍵詞:指型軟珊瑚
外文關鍵詞:Bioactive
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針對台灣海域所採集的軟珊瑚Sinularia triangular所具有的化學成分研究中,共分離出8個天然化合物,其中有一個為新的quinone類化合物(8)與7個已知化合物分sinularin (1)、sinulariolide (2)、11-epi-sinulariolide acetate (3) 、querciformolide C (4)、sinulariolone (5)、11-dehydrosinulariolide (6)、(Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide (7)。化合物1□8之化學結構及相對立體構型均是以各種光譜解析(IR、 MS、 1D及2D NMR)及文獻比對的方法加以確立。同時,並將所獲得之天然化合物1□8進行癌細胞株的細胞毒殺活性測試,結果發現以上的化合物均對人類的四種癌細胞MCF-7、Daoy、Hela與Hep2均無細胞毒殺活性(IC50 > 20μg/mL)。
此外,化合物1–8進行抗發炎活性試驗,結果發現化合物1–3、6和8對於
在濃度為10 µM下對脂多醣(lipopolysaccharide,LPS)誘發的小鼠巨噬細胞株 RAW 264.7所產生發炎性蛋白質-一氧化氮合成酶(iNOS)之蛋白質表現情形具有抑制效果,在相同濃度下,化合物3也對於COX-2也具有良好的抑制效果。

The chemical constituents of the Formosan soft corals Sinularia triangular were studied. This study led to the isolation of eight natural products (1–8), including one new quinine type metabolite (8), along with seven known compounds, sinularin (1), sinulariolide (2), 11-epi-sinulariolide acetate (3), querciformolide C (4), sinulariolone (5), 11-dehydrosinulariolide (6) and (Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide (7) from the soft coral S. triangular. The structures of 1–8 were elucidated by spectroscopic evidences (1D NMR, 2D NMR, IR, and MS) and by the comparison of those of related metabolites in literatures. The cytotoxicity of 1–8 against four human cancer cell lines, Hela (cervical epitheloid carcinoma), Hep 2 (laryngeal carcinoma), Daoy (medulloblastoma) and MCF-7 (breast carcinoma), was assayed. The result showed that eight metabolites (1–8) were inactive (ED50’s >20 μg/mL) towards these cancer cell lines. Furthermore, the in vitro anti-inflammatory effect of compounds 1–8 was tested. In this assay, compounds 1–3, 6, and 8 significantly inhibited the accumulation of the pro-inflammatory iNOS protein of the LPS-stimulated RAW264.7 macrophage cells at 10 μM. At the same concentrations, compound 3 also could significantly inhibit the accumulation of the pro-inflammatory COX-2 protein.
目錄
頁次
中文摘要 VIII

英文摘要 IX

第一章、緒論 1
第一節、前言 1
第二節、研究背景與動機 6
第三節、文獻回顧 8
第二章、實驗方法與程序 34
第一節、生物樣品採集時間與地點 34
第二節、生物樣品的分類 35
第三節、實驗流程 35
第四節、實驗設備儀器與材料 36
第五節、Sinularia triangular的分離流程 37
第三章、化合物之結構證明
第一節、軟珊瑚Sinularia triangular所分離化合物的結構證明 39
(一)、Sinularin (1) 化合物構造之解析 39
(二)、Sinulariolide (2) 化合物構造之解析 45
(三)、11-Epi-Sinulariolide acetate (3) 化合物構造之解析 51
(四)、Quercifomolide C (4)之結構解析 57
(五)、Sinulariolone (5)之結構解析 62
(六)、11-Dehydrosinulariolide (6)之結構解析 67
(七)、(Z)-N-[2-(4-hydroxyphenyl)ethyl]-3-methyldodec-2-enamide (7)之結構解析 73
(八)、Triangulaquinone (8)之結構解析 75
第四章、生物活性試驗 81
第一節、細胞毒殺活性試驗方法 81
第二節、抗發炎活性試驗方法 82
第三節、生物活性試驗結果 85
(一)、細胞毒殺活性試驗結果
(二)、抗發炎活性試驗結果 85
86
第五章、結論 88
第六章、參考文獻 89









圖目錄
頁次
Figure 2-1、Sinularia triangular的分離流程圖 38
Figure 3-1-1、1H-NMR spectrum of 1 41
Figure 3-1-2、13C-NMR spectrum of 1 41
Figure 3-1-3、DEPT spectrum of 1 42
Figure 3-1-4、COSY spectrum of 1 42
Figure 3-1-5、HMQC spectrum of 1 43
Figure 3-1-6、HMBC spectrum of 1 43
Figure 3-1-7、NOESY spectrum of 1 44
Figure 3-2-1、1H-NMR spectrum of 2 47
Figure 3-2-2、13C-NMR spectrum of 2 47
Figure 3-2-3、DEPT spectrum of 2 48
Figure 3-2-4、COSY spectrum of 2 48
Figure 3-2-5、HMQC spectrum of 2 49
Figure 3-2-6、HMBC spectrum of 2 49
Figure 3-2-7、NOESY spectrum of 2 50
Figure 3-3-1、1H-NMR spectrum of 3 53
Figure 3-3-2、13C-NMR spectrum of 3 53
Figure 3-3-3、DEPT spectrum of 3 54
Figure 3-3-4、COSY spectrum of 3 54
Figure 3-3-5、HMQC spectrum of 3 55
Figure 3-3-6、HMBC spectrum of 3 55
Figure 3-3-7、NOESY spectrum of 3 56
Figure 3-4-1、1H-NMR spectrum of 4 59
Figure 3-4-2、13C-NMR spectrum of 4 59
Figure 3-4-3、COSY spectrum of 4 60
Figure 3-4-4、HMQC spectrum of 4 60
Figure 3-4-5、HMBC spectrum of 4 61
Figure 3-5-1、1H-NMR spectrum of 5 64
Figure 3-5-2、13C -NMR spectrum of 5 64
Figure 3-5-3、DEPT spectrum of 5 65
Figure 3-5-4、COSY spectrum of 5 65
Figure 3-5-5、HMQC spectrum of 5 66
Figure 3-5-6、HMBC spectrum of 5 66
Figure 3-6-1、1H-NMR spectrum of 6 69
Figure 3-6-2、13C -NMR spectrum of 6 69
Figure 3-6-3、DEPT spectrum of 6 70
Figure 3-6-4、COSY spectrum of 6 70
Figure 3-6-5、HMQC spectrum of 6 71
Figure 3-6-6、HMBC spectrum of 6 71
Figure 3-6-7、NOESY spectrum of 6 72
Figure 3-7-1、1H-NMR spectrum of 7 74
Figure 3-7-2、13C-NMR spectrum of 7 74
Figure 3-8-1、1H-1H COSY and HMBC correlations of 8 76
Figure 3-8-2、1H-NMR spectrum of 8 78
Figure 3-8-3、13C -NMR spectrum of 8 78
Figure 3-8-4、DEPT spectrum of 8 79
Figure 3-8-5、COSY spectrum of 8 79
Figure 3-8-6、HMQC spectrum of 8 80
Figure 3-8-7、HMBC spectrum of 8 80
Figure 4-1、化合物 1–8 濃度在 10 µM 抑制 LPS 誘發老鼠巨噬細胞(mouse macrophage cell line, RAW 264.7)產生iNOS (inducible nitric oxide synthase)之抗發炎活性篩檢結果 86
Figure 4-2、化合物1–8 濃度在 10 µΜ 抑制 LPS 誘發老鼠巨噬細胞(mouse macrophage cell line, RAW 264.7)產生COX-2 (cyclooxygenase-II)之抗發炎活性篩檢結果 87

表目錄
頁次
Table 1-3-1、台灣產的軟珊瑚Sinularia flexibilis所含天然物的文獻報告 8
Table 1-3-2、台灣產的軟珊瑚Sinularia gibberosa所含天然物的文獻報告 11

Table 1-3-3、台灣產的軟珊瑚Sinularia grandilobata所含天然物的文獻報告 16
Table 1-3-4、台灣產的軟珊瑚Sinularia inelegans所含天然物的文獻報告 17
Table 1-3-5、台灣產的軟珊瑚Sinularia lochmodes所含天然物的文獻報告 18
Table 1-3-6、台灣產的軟珊瑚Sinularia leptolados所含天然物的文獻報告 19
Table 1-3-7、台灣產的軟珊瑚Sinularia nanolobata所含天然物的文獻報告 22
Table 1-3-8、台灣產的軟珊瑚Sinularia polydactyla所含天然物的文獻報告 23
Table 1-3-9、台灣產的軟珊瑚Sinularia parva所含天然物的文獻報告 23
Table 1-3-10、台灣產的軟珊瑚Sinularia scabra所含天然物的文獻報告 24
Table 1-3-11、台灣產的軟珊瑚Sinularia querciformis所含天然物的文獻報告 25
Table 1-3-12、台灣產的軟珊瑚Sinularia granosa所含天然物的文獻報告 27
Table 1-3-13、台灣產的軟珊瑚Sinularia capillosa所含天然物的文獻報告 28
Table 1-3-14、台灣產的軟珊瑚Sinularia gyrosa所含天然物的文獻報告 28
Table 1-3-15、台灣產的軟珊瑚Sinularia facile所含天然物的文獻報告 29
Table 1-3-16、台灣產的軟珊瑚Sinularia manaarensis所含天然物的文獻報告 30
Table 1-3-17、台灣產的軟珊瑚Sinularia sp.所含天然物的文獻報告 31
Table 3-1、The 1H and 13C NMR Data of Compound 1 40
Table 3-2、The 1H and 13C NMR Data of Compound 2 46
Table 3-3、The 1H and 13C NMR Data of Compound 3 52
Table 3-4、The 1H and 13C NMR Data of Compound 4 58
Table 3-5、The 1H and 13C NMR Data of Compound 5 63
Table 3-6、The 1H and 13C NMR Data of Compound 6 68
Table 3-8、The 1H and 13C NMR Data of Compound 8 77
Table 4-1、Cytotoxicity (ED50 μg/mL) of compounds 1–8 85

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