為了找尋具有生物活性的二次代謝物，本研究持續探討從2013年在臺灣東海岸基翬漁港所採集到的葉形軟珊瑚Lobophytum varium的乙酸乙酯萃取物中的化學成分。本次的研究中總共分離出10個天然化合物，其中包含1個新的lobane-type diterpenoid類化合物lobovarol L (1) 以及5個新的prenyleudesmane-
type diterpenoids 類化合物lobovarol M─Q (2─6)，以及4個已知的化合物：lobatrienolide (7)、loba-8,10,13(15)-triene-14,17,18-triol 14-acetate (8)、loba-8,10,13(15)-triene-14,17,18-triol 14,17-diacetate (9)、lobovarol I (10)。所分離到的天然化合物1─10均透過光譜數據 (IR、MS、1D、2D NMR) 分析建立其化學結構，以及比對已知的二萜類化合物之光譜資料進行確認。
　　將化合物1─10分別對P388 (老鼠血癌細胞)、DLD-1 (人類大腸癌細胞)、CCD-966SK (人類皮膚纖維母細胞) 等三株細胞株進行細胞毒殺活性試驗。結果顯示化合物2對CCD-966SK具有毒殺活性，IC50為15.5 μg/mL。在抗發炎活性試驗中，當化合物濃度為1 μM，針對受到fMLF/CB刺激的嗜中性白血球，抑制其產生超氧陰離子與彈性蛋白酶的釋放，所有化合物皆未表現出顯著的抗發炎活性。

In order to discover bioactive secondary metabolites, we continued the chemical investigation of the ethyl acetate extract of a Formosan soft coral Lobophytum varium, collected from the Jihui Fishing Port, Taitung, Taiwan in 2013. This study further led to the isolation of ten natural products, including one new lobane-type diterpenoid lobovarol L (1) and five new prenyleudesmane-type diterpenoids lobovarols M─Q (2─6), along with four known compounds: lobatrienolide (7), loba-8,10,13(15)-triene-
14,17,18-triol 14-acetate (8), loba-8,10,13(15)-triene-14,17,18-triol 14,17-diacetate (9), lobovarol I (10). The chemical structures of compounds 1─10 were elucidated on the basis of spectroscopic methods (IR, MS, 1D and 2D NMR), and by comparison of the spectroscopic data with the related known diterpenoids.
The cytotoxicity of compounds 1─10 against P388 (mouse lymphocytic leukemia), DLD-1 (human colon adenocarcinoma), CCD-966SK (human skin fibroblast) cell lines were evaluated. The results showed that compounds 2 exhibited cytotoxicity against CCD-966SK cell line with an IC50 value of 15.5 μg/mL. In anti-inflammatory assay, none of compounds show significant anti-inflammatory activity by inhibiting superoxide anion generation and elastase release in fMLF/CB-stimulated human neutrophils at 1 μM .

目 錄 頁碼
論文審定書 i
謝辭 ii
中文摘要 iii
英文摘要 iv
圖次 vii
表次 xii
化合物1─10化學結構 xiii
第一章、緒論 1
第一節、前言 1
第二節、研究背景與目的 2
第三節、文獻回顧 3
第二章、生物材料與研究方法 64
第一節、研究流程 64
第二節、Lobophytum varium物種的採集及分類地位 66
第三節、Lobophytum varium的分離流程 67
第四節、實驗設備儀器及材料 70
(一)、實驗設備儀器 70
(二)、實驗材料 71
第三章、化合物之結構解析 72
第一節：軟珊瑚Lobophytum varium所含化合物之結構解析 72
　　(一)、Lobovarol L (1) 之結構解析 72
　　(二)、Lobovarol M (2) 之結構解析 82
　　(三)、Lobovarol N (3) 之結構解析 92
　　(四)、Lobovarol O (4) 之結構解析 102
　　(五)、Lobovarol P (5) 之結構解析 112
(六)、Lobovarol Q (6) 之結構解析 123
　　(七)、Lobatrienolide (7) 之結構解析 133
　　(八)、Loba-8,10,13(15)-trien-14,17,18-triol-14-acetate (8) 之結構解析 138
　　(九)、Loba-8,10,13(15)-trien-14,17,18-triol-14,17-diacetate (9) 之
結構解析 144
　　(十)、Lobovarol I (10) 之結構解析 150
第二節：化合物1—10物理性質及圖譜數據整理 155
第四章、生物活性試驗方法 157
第一節：生物活性試驗方法 157
(一)、細胞毒殺活性試驗 157
(二)、抗發炎活性試驗 159
第二節：生物活性試驗結果 160
(一)、細胞毒殺活性試驗結果 160
(二)、抗發炎活性試驗結果 161
第五章、結論 162
第六章、參考文獻 164

圖 次
頁碼
Figure 3-1-1. Biosynthesis of the lobane-type and prenyleudesmane-type skeleton. 61
Figure 2-2. Soft coral Lobophytum varium. 66
Figure 2-3-1. The isolated processes of the soft coral Lobophytum varium (A). 68
Figure 2-3-2. The isolated processes of the soft coral Lobophytum varium (B). 68
Figure 2-3-3. The isolated processes of the soft coral Lobophytum varium (C). 69
Figure 3-1-1. 1H–1H COSY and selective HMBC correlations of 1. 73
Figure 3-1-2. Selective NOESY correlations of 1. 74
Figure 3-1-3. ESIMS spectrum of 1. 76
Figure 3-1-4. HRESIMS spectrum of 1. 76
Figure 3-1-5. IR spectrum of 1. 77
Figure 3-1-6. UV spectrum of 1. 77
Figure 3-1-7. 1H-NMR spectrum of 1 in CDCl3. 78
Figure 3-1-8. 1H-NMR (4.0~7.0 ppm) spectrum of 1 in CDCl3. 78
Figure 3-1-9. 13C-NMR spectrum of 1 in CDCl3. 79
Figure 3-1-10. DEPT spectrum of 1 in CDCl3. 79
Figure 3-1-11. HSQC spectrum of 1 in CDCl3. 80
Figure 3-1-12. 1H–1H COSY spectrum of 1 in CDCl3. 80
Figure 3-1-13. HMBC spectrum of 1 in CDCl3. 81
Figure 3-1-14. NOESY spectrum of 1 in CDCl3. 81
Figure 3-2-1. 1H–1H COSY and selective HMBC correlations of 2. 83
Figure 3-2-2. Selective NOESY correlations of 2. 84
Figure 3-2-3. ESIMS spectrum of 2. 86
Figure 3-2-4. HRESIMS spectrum of 2. 86
Figure 3-2-5. IR spectrum of 2. 87
Figure 3-2-6. 1H-NMR spectrum of 2 in (CD3)2CO. 87
Figure 3-2-7. 1H-NMR (3.0~5.9 ppm) spectrum of 2 in (CD3)2CO. 88
Figure 3-2-8. 13C-NMR spectrum of 2 in (CD3)2CO. 88
Figure 3-2-9. DEPT spectrum of 2 in (CD3)2CO. 89
Figure 3-2-10. HSQC spectrum of 2 in (CD3)2CO. 89
Figure 3-2-11. COSY spectrum of 2 in (CD3)2CO. 90
Figure 3-2-12. HMBC spectrum of 2 in (CD3)2CO. 90
Figure 3-2-13. NOESY spectrum of 2 in (CD3)2CO. 91
Figure 3-3-1. 1H–1H COSY and selective HMBC correlations of 3. 93
Figure 3-3-3. Selective NOESY correlations of 3. 94
Figure 3-3-4. ESIMS spectrum of 3. 96
Figure 3-3-5. HRESIMS spectrum of 3. 96
Figure 3-3-6. IR spectrum of 3. 97
Figure 3-3-7. UV spectrum of 3. 97
Figure 3-3-8. 1H-NMR spectrum of 3 in CDCl3. 98
Figure 3-3-9. 13C-NMR spectrum of 3 in CDCl3. 98
Figure 3-3-10. DEPT spectrum of 3 in CDCl3. 99
Figure 3-3-11. HSQC spectrum of 3 in CDCl3. 99
Figure 3-3-12. COSY spectrum of 3 in CDCl3. 100
Figure 3-3-13. HMBC spectrum of 3 in CDCl3. 100
Figure 3-3-14. NOESY spectrum of 3 in CDCl3. 101
Figure 3-4-1. 1H–1H COSY and selective HMBC correlations of 4. 103
Figure 3-4-2. Selective NOESY correlations of 4. 104
Figure 3-4-3. Lobatrienolide. 106
Figure 3-4-4. ESIMS spectrum of 4. 107
Figure 3-4-5. HRESIMS spectrum of 4. 107
Figure 3-4-6. IR spectrum of 4. 108
Figure 3-4-7. 1H-NMR spectrum of 4 in CDCl3. 108
Figure 3-4-8. 13C-NMR spectrum of 4 in CDCl3. 109
Figure 3-4-9. DEPT spectrum of 4 in CDCl3. 109
Figure 3-4-10. HSQC spectrum of 4 in CDCl3. 110
Figure 3-4-11. COSY spectrum of 4 in CDCl3. 110
Figure 3-4-12. HMBC spectrum of 4 in CDCl3. 111
Figure 3-4-13. NOESY spectrum of 4 in CDCl3. 111
Figure 3-5-1. 1H–1H COSY and HMBC correlations of 5. 113
Figure 3-5-3. Selective NOESY correlations of 5. 114
Figure 3-5-4. Loba-8,10,13(15)-triene-14,17,18-triol 14-acetate. 116
Figure 3-5-5. ESIMS spectrum of 5. 117
Figure 3-5-6. HRESIMS spectrum of 5. 117
Figure 3-5-7. IR spectrum of 5. 118
Figure 3-5-8. 1H-NMR spectrum of 5 in CDCl3. 118
Figure 3-5-9. 1H-NMR (3.3~5.7 ppm) spectrum of 5 in CDCl3. 119
Figure 3-5-10. 13C-NMR spectrum of 5 in CDCl3. 119
Figure 3-5-11. DEPT spectrum of 5 in CDCl3. 120
Figure 3-5-12. HSQC spectrum of 5 in CDCl3. 120
Figure 3-5-13. COSY spectrum of 5 in CDCl3. 121
Figure 3-5-14. HMBC spectrum of 5 in CDCl3. 121
Figure 3-5-15. NOESY spectrum of 5 in CDCl3. 122
Figure 3-6-1. 1H–1H COSY and HMBC correlations of 6. 124
Figure 3-6-2. Selective NOESY correlations of 6. 125
Figure 3-6-3. ESIMS spectrum of 6. 127
Figure 3-6-4. HRESIMS spectrum of 6. 127
Figure 3-6-5. IR spectrum of 6. 128
Figure 3-6-6. 1H-NMR spectrum of 6 in CDCl3. 128
Figure 3-6-7. 1H-NMR (2.4~5.7 ppm) spectrum of 6 in CDCl3. 129
Figure 3-6-8. 13C-NMR spectrum of 6 in CDCl3. 129
Figure 3-6-9. DEPT spectrum of 6 in CDCl3. 130
Figure 3-6-10. HSQC spectrum of 6 in CDCl3. 130
Figure 3-6-11. COSY spectrum of 6 in CDCl3. 131
Figure 3-6-12. HMBC spectrum of 6 in CDCl3. 131
Figure 3-6-13. NOESY spectrum of 6 in CDCl3. 132
Figure 3-7-1. ESIMS spectrum of 7. 135
Figure 3-7-2. IR spectrum of 7. 135
Figure 3-7-3. 1H-NMR spectrum of 7 in CDCl3. 136
Figure 3-7-4. 13C-NMR spectrum of 7 in CDCl3. 136
Figure 3-7-5. DEPT spectrum of 7 in CDCl3. 137
Figure 3-7-6. HSQC spectrum of 7 in CDCl3. 137
Figure 3-8-1. ESIMS spectrum of 8. 140
Figure 3-8-2. IR spectrum of 8. 140
Figure 3-8-3. 1H NMR spectrum of 8 in CDCl3. 141
Figure 3-8-4. 1H-NMR (3.4~5.9 ppm) spectrum of 8 in CDCl3. 141
Figure 3-8-5. 13C NMR spectrum of 8 in CDCl3. 142
Figure 3-8-6. DEPT spectrum of 8 in CDCl3. 142
Figure 3-8-7. HSQC spectrum of 8 in CDCl3. 143
Figure 3-9-1. ESIMS spectrum of 9. 146
Figure 3-9-2. IR spectrum of 9. 146
Figure 3-9-3. 1H-NMR spectrum of 9 in CDCl3. 147
Figure 3-9-4. 1H-NMR (4.5~5.9 ppm) spectrum of 9 in CDCl3. 147
Figure 3-9-5. 13C-NMR spectrum of 9 in CDCl3. 148
Figure 3-9-6. DEPT spectrum of 9 in CDCl3. 148
Figure 3-9-7. HSQC spectrum of 9 in CDCl3. 149
Figure 3-10-1. ESIMS spectrum of 10. 152
Figure 3-10-2. IR spectrum of 10. 152
Figure 3-10-3. 1H-NMR spectrum of 10 in CDCl3. 153
Figure 3-10-4. 13C-NMR spectrum of 10 in CDCl3. 153
Figure 3-10-5. DEPT spectrum of 10 in CDCl3. 154
Figure 3-10-6. HSQC spectrum of 10 in CDCl3. 154
Figure 4-1. Alamar Blue reduction. 157


表 次 頁碼
Table 1-3-1. Literature review of the genus Lobophytum. 3
Table 1-3-2. Literature review of lobane-type and prenyleudesmane-type diterpenoids. 51
Table 3-1. 1H and 13C NMR Data, 1H–1H COSY, and HMBC Correlations of 1. 75
Table 3-2. 1H and 13C NMR Data, 1H–1H COSY, and HMBC Correlations of 2. 85
Table 3-3. 1H and 13C NMR Data, 1H–1H COSY, and HMBC Correlations of 3. 95
Table 3-4-1. 1H and 13C NMR Data, 1H–1H COSY, and HMBC Correlations of 4. 105
Table 3-4-2. 1H and 13C NMR Data of 4 and lobatrienolide. 106
Table 3-5-1. 1H and 13C NMR Data, 1H–1H COSY, and HMBC Correlations of 5. 115
Table 3-5-2. 1H and 13C NMR Data of 5 and loba-8,10,13(15)-triene-14,17,18-triol 14-acetate. 116
Table 3-6. 1H and 13C NMR Data, 1H–1H COSY, and HMBC Correlations of 6. 126
Table 3-7. 1H and 13C NMR Data of 7 and lobatrienolide. 134
Table 3-8. 1H and 13C NMR Data of 8 and loba-8,10,13(15)-triene-14,17,18-triol 14-acetate. 139
Table 3-9. 1H and 13C NMR Data of 9 and loba-8,10,13(15)-triene-14,17,18-triol
14,17-diacetate. 145
Table 3-10. 1H and 13C NMR Data of 10 and lobovarol I. 151
Table 4-2-1. Cytotoxicity data of compounds 1—10. 160
Table 4-2-2. Effects of compounds 1–10 on superoxide anion generation
in fMLF/CB-induced human neutrophils. 161
Table 4-2-3. Effects of compounds 1–10 on elastase release in fMLF/CB-induced
human neutrophils. 161

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