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研究生:林右晟
研究生(外文):You-Cheng Lin
論文名稱:肉質葉形軟珊瑚Lobophytum sarcophytoides所分離的二次代謝物及其生物活性之研究
論文名稱(外文):Isolation and Biological Activities of Secondary Metabolities from the Soft Coral Lobophytum sarcophytoides
指導教授:許志宏許志宏引用關係
指導教授(外文):Jyh-Horng Sheu
學位類別:碩士
校院名稱:國立中山大學
系所名稱:海洋生物科技暨資源學系研究所
學門:自然科學學門
學類:海洋科學學類
論文種類:學術論文
論文出版年:2009
畢業學年度:97
語文別:中文
論文頁數:151
中文關鍵詞:東沙群礁肉質葉形軟珊瑚
外文關鍵詞:polyhydroxylated steroidsLobophytum sarcophytoidescembrane-type diterpenoids
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針對台灣東沙群礁所採集的肉質葉形軟珊瑚Lobophytum sarcophytoides所具有的化學成分研究中,共分離出五個新的天然化合物1–5,其中四個為cembrane-type diterpenoids類化合物Sarcophytolins A–D (1–4),一個為 polyhydroxylated steroids 類化合物23, 24-Dimethyl-cholesta-5, 16-diene-3β, 20α-diol (5)及五個已知化合物 6–10。所有化合物的化學構造均由光譜數據的分析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決定。化合物5經由X-ray晶體繞射來證明其化合物之結構。
將化合物1–10進行癌細胞株的細胞毒殺測試。結果顯示化合物 8, 9和 10 對人類乳癌細胞(MCF-7)具有中等的抑制效果,而化合物 6 和 8 對人類結直腸腫瘤細胞(DLD-1)具有良好的細胞毒殺活性。將化合物1–10進行抗發炎活性試驗,結果發現化合物1, 2, 4 , 6 和10在濃度為10 μM 下可有效的抑制發炎蛋白質iNOS的表現。
Investigation on the chemical constituents of the EtOH extract of the soft coral Lobophytum sarcophytoides, collected off the coast of Dongsha Atoll, Taiwan, has led to the isolation of ten natural compounds 1–10, including four new cembrane-type diterpenoids, Sarcophytolins A–D (1–4) and one new polyhydroxylated steroid 23, 24-Dimethyl-cholesta-5, 16-diene-3β, 20α-diol (5) along with five know compounds 6–10。The structure of compounds 1–10 were established by detailed spectral data analysis (IR, MS, 1D, 2D NMR) and by comparison of the spectral data with those of the related known compounds. The relative stereochemistries of compound 5 was further confirmed by X-ray single-crystal diffraction analysis.
The cytotoxicity of compounds 1–10 against the Daoy (human medulloblastoma), Hep-2 (human laryngeal carcinoma), MCF-7 (human breast adenocarcinoma), CCRF-CEM (human T-cell acute lymphoblastic leukemia), and DLD-1/WiDr (human colon adenocarcinoma) tumor cell lines were determined. Compounds 6, 8, 9, and 10 exhibited moderate cytotoxicities against the tested tumor cells. Furthermore, compounds 1, 2, 4, 6, and 10 were found to show significant activity against the accumulation of the pro-inflammatory iNOS protein at 10 μM.
目 錄 頁 次
中文摘要 Ⅷ
英文摘要 Ⅸ
化合物1−10 化學結構 Ⅹ
第一章、緒論 1
第一節、前言 1
第二節、研究背景與動機 2
第三節、文獻回顧 4
第二章、生物材料與研究方法 23
第一節、研究流程 23
第二節、Lobophytum sarcophytoides 樣品採集時間、地點、分類地
位及分離流程
25
2.2.1 Lobophytum sarcophytoides 樣品採集時間、地點、
分類地位
25
2.2.2 Lobophytum sarcophytoides 樣品的萃取分離 26
第三節、實驗設備儀器及材料 28
2.3.1 實驗設備儀器 28
2.3.2 實驗材料 29
第三章、軟珊瑚Lobophytum sarcophytoides 所分離出之化合物
的結構證明
30
第一節:化合物構造之解析與證明 30
(一)、Sarcophytolin A (1) 化合物構造之解析 30
(二)、Sarcophytolin B (2) 化合物構造之解析 40
(三)、Sarcophytolin C (3) 化合物構造之解析 50
(四)、Sarcophytolin D (4) 化合物構造之解析 60
(五)、23, 24-Dimethyl-cholesta-5, 16-diene-3β, 20α-diol (5)
化合物構造之解析
70
(六)、Isocembrol A (6) 化合物構造之解析 79
(七)、Sarcophytoxide (7) 化合物構造之解析 83
(八)、 5α, 8α-Epidioxy-24-methylcholesta-6-en-3β-ol (8)
化合物構造之解析
87
(九)、5α, 8α-Epidioxy-22, 23-methylene-24-methylcholest-6-en-
3β-ol (9) 化合物構造之解析
91
(十)、(Z)-N-[2-(4-Hydroxyphenyl)ethyl]-3-methyldodec-2-enamide
(10) 化合物構造之解析
96
第二節:化學反應步驟 100
第三節:化合物物理性質及圖譜數據整理
101
第四章、生物活性試驗 103
第一節、生物活性試驗方法 103
(一)、抗發炎活性試驗方法 103
(二)、細胞毒殺活性試驗方法 105
第二節、生物活性試驗結果 108
(一)、抗發炎活性試驗結果 108
(二)、細胞毒殺活性試驗結果 111
第五章、結論 113
第六章、參考文獻 116
附錄、化合物 5 之X-ray 實驗數據 122
圖 目 錄
Figure 2-1. Lobophytum sarcophytoides 圖 25
Figure 2-2. Lobophytum sarcophytoides 軟珊瑚的分離流程 27
Figure 3-1-1. 1H–1H COSY and selective HMBC correlations of 1 31
Figure 3-1-2. Selected NOESY correlations of 1 32
Figure 3-1-3. IR spectrum of 1. 34
Figure 3-1-4. ESIMS spectrum of 1. 34
Figure 3-1-5. HRESIMS spectrum of 1. 35
Figure 3-1-6. 1H NMR spectrum of 1. 35
Figure 3-1-7. 1H NMR (4.4~6.2 ppm) spectrum of 1. 36
Figure 3-1-8. 13C NMR spectrum of 1. 36
Figure 3-1-9. DEPT spectra of 1. 37
Figure 3-1-10. HMQC spectrum of 1. 37
Figure 3-1-11. COSY spectrum of 1. 38
Figure 3-1-12. HMBC spectrum of 1. 38
Figure 3-1-13. NOESY spectrum of 1. 39
Figure 3-2-1. 1H–1H COSY and selective HMBC correlations of 2. 42
Figure 3-2-2. Selected NOESY correlations of 2. 42
Figure 3-2-3. IR spectrum of 2. 44
Figure 3-2-4. ESIMS spectrum of 2. 44
Figure 3-2-5. HRESIMS spectrum of 2. 45
Figure 3-2-6. 1H NMR spectrum of 2. 45
Figure 3-2-7. 1H NMR (3.1~6.7 ppm) spectrum of 2. 46
Figure 3-2-8. 1H NMR (1.1~3.0 ppm) spectrum of 2. 46
Figure 3-2-9. 13C NMR spectrum of 2. 47
Figure 3-2-10. DEPT spectra of 2. 47
Figure 3-2-11. HMQC spectrum of 2. 48
Figure 3-2-12. COSY spectrum of 2. 48
Figure 3-2-13. HMBC spectrum of 2. 49
Figure 3-2-14. NOESY spectrum of 2. 49
Figure 3-3-1. 1H–1H COSY and selective HMBC correlations of 3. 51
Figure 3-3-2. Selected NOESY correlations of 3. 52
Figure 3-3-3. IR spectrum of 3. 54
Figure 3-3-4. ESIMS spectrum of 3. 54
Figure 3-3-5. HRESIMS spectrum of 3. 55
Figure 3-3-6. 1H NMR spectrum of 3. 55
Figure 3-3-7. 1H NMR (3.0~6.1 ppm) spectrum of 3. 56
Figure 3-3-8. 13C NMR spectrum of 3. 56
Figure 3-3-9. DEPT spectra of 3. 57
Figure 3-3-10. HMQC spectrum of 3. 57
Figure 3-3-11. COSY spectrum of 3. 58
Figure 3-3-12. HMBC spectrum of 3. 58
Figure 3-3-13. NOESY spectrum of 3. 59
Figure 3-4-1. 1H–1H COSY and selective HMBC correlations of 4. 61
Figure 3-4-2. Selected NOESY correlations of 4. 62
Figure 3-4-3. IR spectrum of 4. 64
Figure 3-4-4. ESIMS spectrum of 4. 64
Figure 3-4-5. HRESIMS spectrum of 4. 65
Figure 3-4-6. 1H NMR spectrum of 4. 65
Figure 3-4-7. 1H NMR (4.5~7.6 ppm) spectrum of 4. 66
Figure 3-4-8. 13C NMR spectrum of 4. 66
Figure 3-4-9. DEPT spectra of 4. 67
Figure 3-4-10. HMQC spectrum of 4. 67
Figure 3-4-11. COSY spectrum of 4. 68
Figure 3-4-12. HMBC spectrum of 4. 68
Figure 3-4-13. NOESY spectrum of 4. 69
Figure 3-5-1. 1H–1H COSY and selective HMBC correlations of 5. 71
Figure 3-5-2. X-ray crystal structure for 5. 72
Figure 3-5-3. IR spectrum of 5. 74
Figure 3-5-4. ESIMS spectrum of 5. 74
Figure 3-5-5. HRESIMS spectrum of 5. 75
Figure 3-5-6. 1H NMR spectrum of 5. 75
Figure 3-5-7. 1H NMR (1.8~5.5 ppm) spectrum of 5. 76
Figure 3-5-8. 13C NMR spectrum of 5. 76
Figure 3-5-9. DEPT spectra of 5. 77
Figure 3-5-10. HMQC spectrum of 5. 77
Figure 3-5-11. COSY spectrum of 5. 78
Figure 3-5-12. HMBC spectrum of 5. 78
Figure 3-6-1. ESIMS spectrum of 6. 81
Figure 3-6-2. 1H NMR spectrum of 6. 81
Figure 3-6-3. 13C NMR spectrum of 6. 82
Figure 3-7-1. ESIMS spectrum of 7. 85
Figure 3-7-2. 1H NMR spectrum of 7. 85
Figure 3-7-3. 13C NMR spectrum of 7. 86
Figure 3-8-1. ESIMS spectrum of 8. 89
Figure 3-8-2. 1H NMR spectrum of 8. 89
Figure 3-8-3. 13C NMR spectrum of 8. 90
Figure 3-9-1. 1H NMR Chemical shifts of the side-chain methyl groups of
9 and synthetic of demethylgorgosterols
92
Figure 3-9-2. ESIMS spectrum of 9. 94
Figure 3-9-3. 1H NMR spectrum of 9. 94
Figure 3-9-4. 1H-NMR (1.1~4.1 ppm) spectrum of 9. 95
Figure 3-9-5. 13C NMR spectrum of 9. 95
Figure 3-10-1. ESIMS spectrum of 10. 98
Figure 3-10-2. 1H NMR spectrum of 10. 98
Figure 3-10-3. 13C NMR spectrum of 10. 99
Reaction 3-3-1. 由化合物1 進行乙醯化反應,得到化合物2 100
Figure 4-1. 化合物 1–10 之濃度為10 μM 時,抑制LPS 誘發老鼠巨
噬細胞(macrophage, RAW264.7)產生iNOS (inducible
nitric oxide synthase)之抗發炎活性篩檢結果
108
Figure 4-2. 化合物 1–10 之濃度為10 μM 時,抑制LPS 誘發老鼠巨
噬細胞(macrophage, RAW264.7) 產生COX-2
(cyclooygenase-II)之抗發炎活性篩檢結果
109
Figure 4-3. 化合物 1–10 之濃度為10 μM 時,抑制LPS 誘發老鼠巨
噬細胞產生iNOS 與COX-2 實驗之內標準β-actin 蛋白質
之表現 110
表 目 錄 頁次
Table 1-1. Cembranoids from the soft coral Lobophytum crassum 4
Table 1-2. Cembranoids from the soft coral Lobophytum pauciflorum 6
Table 1-3. Cembranoids from the soft coral Lobophytum hedleyi 7
Table 1-4. Cembranoids from the soft coral Lobophytum michaelae 8
Table 1-5. Cembranoids from the soft coral Lobophytum denticulatum 9
Table 1-6. Cembranoids from the soft coral Lobophytum cristigalli 10
Table 1-7. Cembranoids from the soft coral Lobophytum strictum 10
Table 1-8. Cembranoids from the soft coral Lobophytum crassospiculatum 11
Table 1-9. Cembranoids from the soft coral Lobophytum schoedei 11
Table 1-10. Cembranoids from the soft coral Lobophytum catalai 12
Table 1-11. Cembranoids from the soft coral Lobophytum sp. 13
Table 1-12. Polyhydroxylated steroids from the soft coral Lobophytum crassum 16
Table 1-13. Polyhydroxylated steroids from the soft coral
Lobophytum pauciflorum
17
Table 1-14. Polyhydroxylated steroids from the soft coral
Lobophytum strictum
18
Table 1-15. Polyhydroxylated steroids from the soft coral
Lobophytum hirsutum
19
Table 1-16. Polyhydroxylated from the soft coral
Lobophytum catalai
19
Table 1-17. Polyhydroxylated from the soft coral
Lobophytum microlobulatum
20
Table 1-18. Polyhydroxylated from the soft coral
Lobophytum depressum
21
Table 1-19. Polyhydroxylated from the soft coral
Lobophytum sp.
21
Table 3-1. 1H and 13C NMR Data; 1H–1H COSY and HMBC correlations of 1. 33
Table 3-2. 1H and 13C NMR Data; 1H–1H COSY and HMBC correlations of 2. 43
Table 3-3. 1H and 13C NMR Data; 1H–1H COSY and HMBC correlations of 3. 53
Table 3-4. 1H and 13C NMR Data; 1H–1H COSY and HMBC correlations of 4. 63
Table 3-5. 1H and 13C NMR Data; 1H–1H COSY and HMBC correlations of 5. 73
Table 3-6 1H and 13C NMR Data of 6. 80
Table 3-7 1H and 13C NMR Data of 7. 84
Table 3-8 1H and 13C NMR Data of 8. 88
Table 3-9 1H and 13C NMR Data of 9. 93
Table 3-10. 1H and 13C NMR Data of 10. 97
Table 4-1. 化合物 1–10 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)抗發炎活性篩檢結果之數據整理
108
Table 4-2. 化合物1–10 均為 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)
抗發炎活性篩檢結果之數據整理
109
Table 4-3. 化合物1–10 均為10 μΜ 抑制 LPS 誘發老鼠巨噬細胞(mouse
macrophage cell line, RAW 264.7)產生iNOS 與COX-2實驗之內控
制β–actin 蛋白質表現之數據整理
110
Table 4-4. Cytotoxicity (ED50 μg/mL) of compounds 1–10. 111
Table 4-5. Cytotoxicity (ED50 μg/mL) of compounds 1–10. 112
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