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研究生:蘇尹帝
研究生(外文):Yin-di Su
論文名稱:台灣產皮軟珊瑚Briareum sp.與柳羽珊瑚Pinnigorgia sp.化學成分及其生物活性之研究
論文名稱(外文):Studies on the Chemical Constituents and Their Biological Activities from the Formosan Corals Briareum sp. and Pinnigorgia sp.
指導教授:宋秉鈞許志宏許志宏引用關係
指導教授(外文):Ping-Jyun SungJyh-Horng Sheu
學位類別:博士
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:2016
畢業學年度:104
語文別:中文
論文頁數:416
中文關鍵詞:彈性纖維蛋白酶超氧自由基離子柳羽珊瑚皮軟珊瑚環氧化酶-2一氧化氮合成酶
外文關鍵詞:PinnigorgiaBriareumsuperoxide anionelastaseiNOSCOX-2
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本研究針對臺灣南部海域採集之皮軟珊瑚Briareum sp.所含二次代謝物進行研究,共分離純化共得三十七個化合物,包含二十四個新briarane-type的雙萜化合物briarenolides H–Y (1–18)、ZI–ZVI (19–24) 與13個已知化合物briaexcavatolides H (25)、F (28)、G (29)、P (32)、solenolides A (26)、C (27)、brianolide (30)、briaexcavatins P (31)、K (34)、N (35)、excavatolides M (33)、Z (36)、2β-acetoxy-2-(debutyryloxy) stecholide E (37),其中briarenolide J (3) 是第一個分別在C-6和C-12位置上接有氯原子的briarane類化合物。另外,從柳羽珊瑚Pinnigorgia sp. 中分離出三個新的固醇類化合物 pinnigorsterols A (38)、B (39)與pinnisterol A (40),其中化合物38為具有一組雙鍵位於C-8與C-9的固醇類化合物,化合物39與40則為9,11 secosteroid 類型化合物,化合物1–40的結構均是經由光譜資料分析和比對相關文獻化合物建立。
在抗發炎反應實驗中,化合物3、5、39與40具有顯著的抑制人類嗜中性白血球釋放超氧自由基離子 (superoxide anion) (IC50 = 7.73, 7.14, 3.12,1.70 μg/mL)與彈性蛋白酶 (elastase) (IC50 = 5.14, 6.86, 2.40, 1.02 μg/mL) 的活性,其中化合物38對彈性蛋白酶有專一性的顯著抑制效果 (IC50 = 4.47 μg/mL),並進一步發現化合物9、15與38–40對於脂多糖 (lipopolysaccharide, LPS) 誘發小鼠巨噬細胞 (RAW 264.7) 所產生的發炎性蛋白一氧化氮合成酶 (iNOS) (47.3, 41.9, 16.3, 14.5, 19.8%) 與環氧化酶-2 (COX-2) (35.6, 26.1, 37.1, 44.4 , 59.0%) 具有顯著抑制活性。
Studies on the secondary metabolites of the octocoral Briareum sp. collected off the coast of Southern Taiwan had led to the isolation of twenty-four new briarane analogues, including briarenolides H–Y (1–18) and ZI–ZVI (19–24), along with thirteen known compounds, briaexcavatolides H (25), F (28), G (29), P (32), solenolides A (26), C (27), brianolide (30), briaexcavatins P (31), K (34), N (35), excavatolides M (33), Z (36), and 2β-acetoxy-2-(debutyryloxy) stecholide E (37). It is worth noting that briarenolide J (3) is the first dichlorobriarane found to possess a chlorine atom at C-12. In addition, one new steroid pinnigorsterol A (38) and two new 9,11-secosterols pinnigorsterol B (39) and pinnisterol A (40) were obtained from a gorgonian identified as Pinnigorgia sp. The structures of metabolites 1–40 were established by spectroscopic methods and by comparison of the spectroscopic data with those of related metabolites.
In the in vitro anti-inflammatory experiments, metabolites 3, 5, 39, and 40 have displayed significant inhibitory effects on superoxide anion generation (IC50 = 7.73, 7.14, 3.12, and 1.70 μg/mL) and elastase release (IC50 = 5.14, 6.86, 2.40, and 1.02 μg/mL) by human neutrophils. Sterol 38 showed an inhibitory effect on human neutrophil elastase release (IC50 = 4.47 μg/mL). Furthermore, compounds 9, 15 and 38–40 were found to inhibit the accumulation of the pro-inflammatory iNOS protein (47.3, 41.9, 16.3, 14.5, and 19.8%) and COX-2 protein (35.6, 26.1, 37.1, 44.4, and 59.0%) in the LPS- stimulated RAW264.7 macrophage cells.
目錄
頁次
中文摘要..........................................................i
英文摘要..........................................................ii
圖目錄............................................................vii
表目錄............................................................xvi
第一章 緒論......................................................1
第一節 前言..................................................1
第二節 研究動機..............................................4
第三節 Briareum屬所含天然物之文獻回顧.......................10
第四節 9,11-secosteroid天然物之文獻回顧.........................48
第二章 生物材料與分離流程.......................................60
第一節  生物樣品採集與分類.....................................60
第二節  生物樣品萃取與實驗流程…...............................62
第三章 實驗器材與有機溶劑.......................................68
第一節  儀器...................................................68
第二節  藥品試劑...............................................69
第四章 生物活性試驗 ............................................70
第一節 細胞毒殺測試...........................................70
第二節  抗發炎測試Ⅰ...........................................73
第三節 抗發炎測試Ⅱ...........................................76
第五章 結果與討論................................................78
  第一節皮軟珊瑚Briareum sp.所含化學成分之結構解析.............78
(一)Briarenolide H (1) 之結構解析..............................78
(二)Briarenolide I (2) 之結構解析..............................88
(三)Briarenolide J (3) 之結構解析..............................98
(四)Briarenolide K (4) 之結構解析.............................108
(五)Briarenolide L (5) 之結構解析.............................118
(六)Briarenolide M (6) 之結構解析.............................128
(七)Briarenolide N (7) 之結構解析.............................138
(八)Briarenolide O (8) 之結構解析.............................148
(九)Briarenolide P (9) 之結構解析.............................158
(十)Briarenolide Q (10) 之結構解析............................168
(十一)Briarenolide R (11) 之結構解析..........................179
(十二)Briarenolide S (12) 之結構解析..........................189
(十三)Briarenolide T (13) 之結構解析..........................199
(十四)Briarenolide U (14) 之結構解析..........................209
(十五)Briarenolide V (15) 之結構解析..........................219
(十六)Briarenolide W (16) 之結構解析......................... 230
(十七)Briarenolide X (17) 之結構解析..........................241
(十八)Briarenolide Y (18) 之結構解析..........................251
(十九)Briarenolide ZI(19) 之結構解析......................... 261
(二十)Briarenolide ZII (20) 之結構解析........................271
(二十一)Briarenolide ZIII (21) 之結構解析.....................281
(二十二)Briarenolide ZIV (22) 之結構解析......................291
(二十三)Briarenolide ZV (23) 之結構解析.......................301
(二十四)Briarenolide ZVI (24) 之結構解析......................311
第二節 皮軟珊瑚Briareum sp.所含化學成分之已知化合物.........321
第三節 柳羽珊瑚Pinnigorgia sp.所含化學成分之結構解析........322
(三十八)Pinnigorsterol A (38) 之結構解析..................... 322
(三十九)Pinnigorsterol B (39) 之結構解析..................... 331
(四十)Pinnisterol A (40) 之結構解析...........................340
第四節 化合物實驗數據整理..................................349
第五節 化合物生物活性試驗結果..............................354
第六章 結論....................................................360
第七章 參考文獻................................................374
第八章 附錄....................................................389
圖目錄
Figure 1-2-1 2006年統計抗癌藥物來源示意圖。.............................4
Figure 1-2-2 海洋無脊椎動物所分離出的新化合物數量變化趨勢。.............6
Figure 1-2-3 刺絲胞動物門中所分離出具有生物活性的海洋化合物類別的比例。.7
Figure 1-2-4 Marine drugs on the market and conditions treated..........7
Figure 2-1-1 野生型皮軟珊瑚Briareum sp.之生態圖片......................60
Figure 2-1-2 野生型柳羽珊瑚Pinnigorgia sp.之生態圖片...................61
Scheme 2-2-1 Briareum sp. 皮軟珊瑚的分離流程 (I).......................63
Scheme 2-2-2 Briareum sp. 皮軟珊瑚的分離流程 (II.......................64
Scheme 2-2-3 Briareum sp. 皮軟珊瑚的分離流程 (III).....................65
Scheme 2-2-4 Pinnigorgia sp. 柳羽珊瑚的分離流程........................67
Figure 4-1-1 MTT轉變成formazan示意圖...................................72
Figure 4-2-1 抗發炎之Degranulation 試驗之實驗流程......................74
Figure 4-2-2 抗發炎之Superoxide anion試驗之實驗流程....................75
Figure 5-1-1-1 The 1H–1H COSY and selective HMBC correlations of 1......79
Figure 5-1-1-2 Selective NOESY correlations of 1.........................81
Figure 5-1-1-3 化合物1之IR圖譜...........................................83
Figure 5-1-1-4 化合物1之低解析ESIMS圖譜..................................83
Figure 5-1-1-5 化合物1之高解析ESIMS圖譜..................................84
Figure 5-1-1-6 化合物1之1H NMR圖譜.......................................84
Figure 5-1-1-7 化合物1之13C NMR圖譜......................................85
Figure 5-1-1-8 化合物1之DEPT圖譜.........................................85
Figure 5-1-1-9 化合物1之HSQC圖譜.........................................86
Figure 5-1-1-10 化合物1之1H–1H COSY圖譜..................................86
Figure 5-1-1-11 化合物1之HMBC圖譜.........................................87
Figure 5-1-1-12 化合物1之NOESY圖譜........................................87
Figure 5-1-2-1 The 1H–1H COSY and selective HMBC correlations of 2......89
Figure 5-1-2-2 Selective NOESY correlations of 2.........................91
Figure 5-1-2-3 化合物2之IR圖譜...........................................93
Figure 5-1-2-4 化合物2之低解析ESIMS圖譜..................................93
Figure 5-1-2-5 化合物2之高解析ESIMS圖譜..................................94
Figure 5-1-2-6 化合物2之1H NMR圖譜.......................................94
Figure 5-1-2-7 化合物2之13C NMR圖譜......................................95
Figure 5-1-2-8 化合物2之DEPT圖譜.........................................95
Figure 5-1-2-9 化合物2之HSQC圖譜.........................................96
Figure 5-1-2-10 化合物2之1H–1H COSY圖譜..................................96
Figure 5-1-2-11 化合物2之HMBC圖譜.........................................97
Figure 5-1-2-12 化合物2之NOESY圖譜........................................97
Figure 5-1-3-1 The 1H–1H COSY and selective HMBC correlations of 3.....100
Figure 5-1-3-2 Selective NOESY correlations of 3........................101
Figure 5-1-3-3 化合物3之IR圖譜..........................................103
Figure 5-1-3-4 化合物3之低解析ESIMS圖譜.................................103
Figure 5-1-3-5 化合物3之高解析ESIMS圖譜.................................104
Figure 5-1-3-6 化合物3之1H NMR圖譜......................................104
Figure 5-1-3-7 化合物3之13C NMR圖譜.....................................105
Figure 5-1-3-8 化合物3之DEPT圖譜........................................105
Figure 5-1-3-9 化合物3之HSQC圖譜........................................106
Figure 5-1-3-10 化合物3之1H–1H COSY圖譜.................................106
Figure 5-1-3-11 化合物3之HMBC圖譜........................................107
Figure 5-1-3-12 化合物3之NOESY圖譜.......................................107
Figure 5-1-4-1 The 1H–1H COSY and selective HMBC correlations of 4.....109
Figure 5-1-4-2 Selective NOESY correlations of 4........................111
Figure 5-1-4-3 化合物4之IR圖譜..........................................113
Figure 5-1-4-4 化合物4之低解析ESIMS圖譜.................................113
Figure 5-1-4-5 化合物4之高解析ESIMS圖譜.................................114
Figure 5-1-4-6 化合物4之1H NMR圖譜......................................114
Figure 5-1-4-7 化合物4之13C NMR圖譜.....................................115
Figure 5-1-4-8 化合物4之HSQC圖譜........................................115
Figure 5-1-4-9 化合物4之1H–1H COSY圖譜.................................116
Figure 5-1-4-10 化合物4之HMBC圖譜........................................116
Figure 5-1-4-11 化合物4之NOESY圖譜.......................................117
Figure 5-1-5-1 The 1H–1H COSY and selective HMBC correlations of 5.....120
Figure 5-1-5-2 Selective NOESY correlations of 5........................121
Figure 5-1-5-3 化合物5之IR圖譜..........................................123
Figure 5-1-5-4 化合物5之低解析ESIMS圖譜.................................123
Figure 5-1-5-5 化合物5之高解析ESIMS圖譜.................................124
Figure 5-1-5-6 化合物5之1H NMR圖譜......................................124
Figure 5-1-5-7 化合物5之13C NMR圖譜.....................................125
Figure 5-1-5-8 化合物5之HSQC圖譜........................................125
Figure 5-1-5-9 化合物5之1H–1H COSY圖譜.................................126
Figure 5-1-5-10 化合物5之HMBC圖譜........................................126
Figure 5-1-5-11 化合物5之NOESY圖譜.......................................127
Figure 5-1-6-1 The 1H–1H COSY and selective HMBC correlations of 6.....129
Figure 5-1-6-2 Selective NOESY correlations of 6........................131
Figure 5-1-6-3 化合物6之IR圖譜..........................................133
Figure 5-1-6-4 化合物6之低解析ESIMS圖譜.................................133
Figure 5-1-6-5 化合物6之高解析ESIMS圖譜.................................134
Figure 5-1-6-6 化合物6之1H NMR圖譜......................................134
Figure 5-1-6-7 化合物6之13C NMR圖譜.....................................135
Figure 5-1-6-8 化合物6之DEPT圖譜........................................135
Figure 5-1-6-9 化合物6之HSQC圖譜........................................136
Figure 5-1-6-10 化合物6之1H–1H COSY圖譜.................................136
Figure 5-1-6-11 化合物6之HMBC圖譜........................................137
Figure 5-1-6-12 化合物6之NOESY圖譜.......................................137
Figure 5-1-7-1 The 1H–1H COSY and selective HMBC correlations of 7.....140
Figure 5-1-7-2 Selective NOESY correlations of 7........................141
Figure 5-1-7-3 化合物7之IR圖譜..........................................143
Figure 5-1-7-4 化合物7之低解析ESIMS圖譜.................................143
Figure 5-1-7-5 化合物7之高解析ESIMS圖譜.................................144
Figure 5-1-7-6 化合物7之1H NMR圖譜......................................144
Figure 5-1-7-7 化合物7之13C NMR圖譜.....................................145
Figure 5-1-7-8 化合物7之HSQC圖譜........................................145
Figure 5-1-7-9 化合物7之1H–1H COSY圖譜.................................146
Figure 5-1-7-10 化合物7之HMBC圖譜........................................146
Figure 5-1-7-11 化合物7之NOESY圖譜.......................................147
Figure 5-1-8-1 The 1H–1H COSY and selective HMBC correlations of 8.....150
Figure 5-1-8-2 Selective NOESY correlations of 8........................151
Figure 5-1-8-3 化合物8 IR圖譜...........................................153
Figure 5-1-8-4 化合物8低解析ESIMS圖譜...................................153
Figure 5-1-8-5 化合物8之高解析ESIMS圖譜.................................154
Figure 5-1-8-6 化合物8之1H NMR圖譜......................................154
Figure 5-1-8-7 化合物8之13C NMR圖譜.....................................155
Figure 5-1-8-8 化合物8之DEPT圖譜........................................155
Figure 5-1-8-9 化合物8之HSQC圖譜........................................156
Figure 5-1-8-10 化合物8之1H–1H COSY圖譜.................................156
Figure 5-1-8-11 化合物8之HMBC圖譜........................................157
Figure 5-1-8-12 化合物8之NOESY圖譜.......................................157
Figure 5-1-9-1 The 1H–1H COSY and selective HMBC correlations of 9.....160
Figure 5-1-9-2 Selective NOESY correlations of 9........................161
Figure 5-1-9-3 化合物9之IR圖譜..........................................163
Figure 5-1-9-4 化合物9之低解析ESIMS圖譜.................................163
Figure 5-1-9-5 化合物9之高解析ESIMS圖譜.................................164
Figure 5-1-9-6 化合物9之1H NMR圖譜......................................164
Figure 5-1-9-7 化合物9之13C NMR圖譜.....................................165
Figure 5-1-9-8 化合物9之DEPT圖譜........................................165
Figure 5-1-9-9 化合物9之HSQC圖譜........................................166
Figure 5-1-9-10 化合物9之1H–1H COSY圖譜.................................166
Figure 5-1-9-11 化合物9之HMBC圖譜........................................167
Figure 5-1-9-12 化合物9之NOESY圖譜.......................................167
Figure 5-1-10-1 The 1H–1H COSY and selective HMBC correlations of 10....170
Figure 5-1-10-2 Selective NOESY correlations of 10.......................172
Figure 5-1-10-3 化合物10之IR圖譜.........................................174
Figure 5-1-10-4 化合物10之低解析ESIMS圖譜................................174
Figure 5-1-10-5 化合物10之高解析ESIMS圖譜................................175
Figure 5-1-10-6 化合物10之1H NMR圖譜.....................................175
Figure 5-1-10-7 化合物10之13C NMR圖譜....................................176
Figure 5-1-10-8 化合物10之DEPT圖譜.......................................176
Figure 5-1-10-9 化合物10之HSQC圖譜.......................................177
Figure 5-1-10-10化合物10之1H–1H COSY圖譜................................177
Figure 5-1-10-11化合物10之HMBC圖譜.......................................178
Figure 5-1-10-12化合物10之NOESY圖譜......................................178
Figure 5-1-11-1 The 1H–1H COSY and selective HMBC correlations of 11....181
Figure 5-1-11-2 Selective NOESY correlations of 11.......................182
Figure 5-1-11-3 化合物11之IR圖譜.........................................184
Figure 5-1-11-4 化合物11之低解析ESIMS圖譜................................184
Figure 5-1-11-5 化合物11之高解析ESIMS圖譜................................185
Figure 5-1-11-6 化合物11之1H NMR圖譜.....................................185
Figure 5-1-11-7 化合物11之13C NMR圖譜....................................186
Figure 5-1-11-8 化合物11之DEPT圖譜.......................................186
Figure 5-1-11-9 化合物11之HSQC圖譜.......................................187
Figure 5-1-11-10化合物11之1H–1H COSY圖譜................................187
Figure 5-1-11-11化合物11之HMBC圖譜.......................................188
Figure 5-1-11-12化合物11之NOESY圖譜......................................188
Figure 5-1-12-1 The 1H–1H COSY and selective HMBC correlations of 12....191
Figure 5-1-12-2 Selective NOESY correlations of 12.......................192
Figure 5-1-12-3 化合物12之IR圖譜.........................................194
Figure 5-1-12-4 化合物12之低解析ESIMS圖譜................................194
Figure 5-1-12-5 化合物12之高解析ESIMS圖譜................................195
Figure 5-1-12-6 化合物12之1H NMR圖譜.....................................195
Figure 5-1-12-7 化合物12之13C NMR圖譜....................................196
Figure 5-1-12-8 化合物12之HSQC圖譜.......................................196
Figure 5-1-12-9 化合物12之1H–1H COSY圖譜................................197
Figure 5-1-12-10化合物12之HMBC圖譜.......................................197
Figure 5-1-12-11化合物12之NOESY圖譜......................................198
Figure 5-1-13-1 The 1H–1H COSY and selective HMBC correlations of 13....201
Figure 5-1-13-2 Selective NOESY correlations of 13.......................202
Figure 5-1-13-3 化合物13之IR圖譜.........................................204
Figure 5-1-13-4 化合物13之低解析ESIMS圖譜................................204
Figure 5-1-13-5 化合物13之高解析ESIMS圖譜................................205
Figure 5-1-13-6 化合物13之1H NMR圖譜.....................................205
Figure 5-1-13-7 化合物13之13C NMR圖譜....................................206
Figure 5-1-13-8 化合物13之DEPT圖譜.......................................206
Figure 5-1-13-9 化合物13之HSQC圖譜.......................................207
Figure 5-1-13-10化合物13之1H–1H COSY圖譜................................207
Figure 5-1-13-11化合物13之HMBC圖譜.......................................208
Figure 5-1-13-12化合物13之NOESY圖譜......................................208
Figure 5-1-14-1 The 1H–1H COSY and selective HMBC correlations of 14....210
Figure 5-1-14-2 Selective NOESY correlations of 14.......................212
Figure 5-1-14-3 化合物14之IR圖譜.........................................214
Figure 5-1-14-4 化合物14之低解析ESIMS圖譜................................214
Figure 5-1-14-5 化合物14之高解析ESIMS圖譜................................215
Figure 5-1-14-6 化合物14之1H NMR圖譜.....................................215
Figure 5-1-14-7 化合物14之13C NMR圖譜....................................216
Figure 5-1-14-8 化合物14之DEPT圖譜.......................................216
Figure 5-1-14-9 化合物14之HSQC圖譜.......................................217
Figure 5-1-14-10化合物14之1H–1H COSY圖譜................................217
Figure 5-1-14-11化合物14之HMBC圖譜.......................................218
Figure 5-1-14-12化合物14之NOESY圖譜......................................218
Figure 5-1-15-1 The 1H–1H COSY and selective HMBC correlations of 15....221
Figure 5-1-15-2 Selective NOESY correlations of 15.......................223
Figure 5-1-15-3 化合物15之IR圖譜.........................................225
Figure 5-1-15-4 化合物15之低解析ESIMS圖譜................................225
Figure 5-1-15-5 化合物15之高解析ESIMS圖譜................................226
Figure 5-1-15-6 化合物15之1H NMR圖譜.....................................226
Figure 5-1-15-7 化合物15之13C NMR圖譜....................................227
Figure 5-1-15-8 化合物15之DEPT圖譜.......................................227
Figure 5-1-15-9 化合物15之HSQC圖譜.......................................228
Figure 5-1-15-10化合物15之1H–1H COSY圖譜................................228
Figure 5-1-15-11化合物15之HMBC圖譜.......................................229
Figure 5-1-15-12化合物15之NOESY圖譜......................................229
Figure 5-1-16-1 The 1H–1H COSY and selective HMBC correlations of 16....232
Figure 5-1-16-2 Selective NOESY correlations of 16.......................234
Figure 5-1-16-3 化合物16之IR圖譜.........................................236
Figure 5-1-16-4 化合物16之低解析ESIMS圖譜................................236
Figure 5-1-16-5 化合物16之高解析ESIMS圖譜................................237
Figure 5-1-16-6 化合物16之1H NMR圖譜.....................................237
Figure 5-1-16-7 化合物16之13C NMR圖譜....................................238
Figure 5-1-16-8 化合物16之HSQC圖譜.......................................238
Figure 5-1-16-9 化合物16之1H–1H COSY圖譜................................239
Figure 5-1-16-10化合物16之HMBC圖譜.......................................239
Figure 5-1-16-11化合物16之NOESY圖譜......................................240
Figure 5-1-17-1 The 1H–1H COSY and selective HMBC correlations of 17....242
Figure 5-1-17-2 Selective NOESY correlations of 17.......................244
Figure 5-1-17-3 化合物17之IR圖譜.........................................246
Figure 5-1-17-4 化合物17之低解析ESIMS圖譜................................246
Figure 5-1-17-5 化合物17之高解析ESIMS圖譜................................247
Figure 5-1-17-6 化合物17之1H NMR圖譜.....................................247
Figure 5-1-17-7 化合物17之13C NMR圖譜....................................248
Figure 5-1-17-8 化合物17之HSQC圖譜.......................................248
Figure 5-1-17-9 化合物17之1H–1H COSY圖譜................................249
Figure 5-1-17-10化合物17之HMBC圖譜.......................................249
Figure 5-1-17-11化合物17之NOESY圖譜......................................250
Figure 5-1-18-1 The 1H–1H COSY and selective HMBC correlations of 18....253
Figure 5-1-18-2 Selective NOESY correlations of 18.......................254
Figure 5-1-18-3 化合物18之IR圖譜.........................................256
Figure 5-1-18-4 化合物18之低解析ESIMS圖譜................................256
Figure 5-1-18-5 化合物18之高解析ESIMS圖譜................................257
Figure 5-1-18-6 化合物18之1H NMR圖譜.....................................257
Figure 5-1-18-7 化合物18之13C NMR圖譜....................................258
Figure 5-1-18-8 化合物18之DEPT圖譜.......................................258
Figure 5-1-18-9 化合物18之HSQC圖譜.......................................259
Figure 5-1-18-10化合物18之1H–1H COSY圖譜................................259
Figure 5-1-18-11化合物18之HMBC圖譜.......................................260
Figure 5-1-18-12化合物18之NOESY圖譜......................................260
Figure 5-1-19-1 The 1H–1H COSY and selective HMBC correlations of 19....263
Figure 5-1-19-2 Selective NOESY correlations of 19.......................264
Figure 5-1-19-3 化合物19之IR圖譜.........................................266
Figure 5-1-19-4 化合物19之低解析ESIMS圖譜................................266
Figure 5-1-19-5 化合物19之高解析ESIMS圖譜................................267
Figure 5-1-19-6 化合物19之1H NMR圖譜.....................................267
Figure 5-1-19-7 化合物19之13C NMR圖譜....................................268
Figure 5-1-19-8 化合物19之DEPT圖譜.......................................268
Figure 5-1-19-9 化合物19之HSQC圖譜.......................................269
Figure 5-1-19-10化合物19之1H–1H COSY圖譜................................269
Figure 5-1-19-11化合物19之HMBC圖譜.......................................270
Figure 5-1-19-12化合物19之NOESY圖譜......................................270
Figure 5-1-20-1 The 1H–1H COSY and selective HMBC correlations of 20....273
Figure 5-1-20-2 Selective NOESY correlations of 20.......................274
Figure 5-1-20-3 化合物20之IR圖譜.........................................276
Figure 5-1-20-4 化合物20之低解析ESIMS圖譜................................276
Figure 5-1-20-5 化合物20之高解析ESIMS圖譜................................277
Figure 5-1-20-6 化合物20之1H NMR圖譜.....................................277
Figure 5-1-20-7 化合物20之13C NMR圖譜....................................278
Figure 5-1-20-8 化合物20之HSQC圖譜.......................................278
Figure 5-1-20-9 化合物20之1H–1H COSY圖譜................................279
Figure 5-1-20-10化合物20之HMBC圖譜.......................................279
Figure 5-1-20-11化合物20之NOESY圖譜......................................280
Figure 5-1-21-1 The 1H–1H COSY and selective HMBC correlations of 21....283
Figure 5-1-21-2 Selective NOESY correlations of 21.......................284
Figure 5-1-21-3 化合物21之IR圖譜.........................................286
Figure 5-1-21-4 化合物21之低解析ESIMS圖譜................................286
Figure 5-1-21-5 化合物21之高解析ESIMS圖譜................................287
Figure 5-1-21-6 化合物21之1H NMR圖譜.....................................287
Figure 5-1-21-7 化合物21之13C NMR圖譜....................................288
Figure 5-1-21-8 化合物21之DEPT圖譜.......................................288
Figure 5-1-21-9 化合物21之HSQC圖譜.......................................289
Figure 5-1-21-10化合物21之1H–1H COSY圖譜................................289
Figure 5-1-21-11化合物21之HMBC圖譜.......................................290
Figure 5-1-21-12化合物21之NOESY圖譜......................................290
Figure 5-1-22-1 The 1H–1H COSY and selective HMBC correlations of 22....293
Figure 5-1-22-2 Selective NOESY correlations of 22.......................294
Figure 5-1-22-3 化合物22之IR圖譜.........................................296
Figure 5-1-22-4 化合物22之低解析ESIMS圖譜................................296
Figure 5-1-22-5 化合物22之高解析ESIMS圖譜................................297
Figure 5-1-22-6 化合物22之1H NMR圖譜.....................................297
Figure 5-1-22-7 化合物22之13C NMR圖譜....................................298
Figure 5-1-22-8 化合物22之DEPT圖譜.......................................298
Figure 5-1-22-9 化合物22之HSQC圖譜.......................................299
Figure 5-1-22-10化合物22之1H–1H COSY圖譜................................299
Figure 5-1-22-11化合物22之HMBC圖譜.......................................300
Figure 5-1-22-12化合物22之NOESY圖譜......................................300
Figure 5-1-23-1 The 1H–1H COSY and selective HMBC correlations of 23....303
Figure 5-1-23-2 Selective NOESY correlations of 23.......................304
Figure 5-1-23-3 化合物23之IR圖譜.........................................306
Figure 5-1-23-4 化合物23之低解析ESIMS圖譜................................306
Figure 5-1-23-5 化合物23之高解析ESIMS圖譜................................307
Figure 5-1-23-6 化合物23之1H NMR圖譜.....................................307
Figure 5-1-23-7 化合物23之13C NMR圖譜....................................308
Figure 5-1-23-8 化合物23之HSQC圖譜.......................................308
Figure 5-1-23-9 化合物23之1H–1H COSY圖譜................................309
Figure 5-1-23-10化合物23之HMBC圖譜.......................................309
Figure 5-1-23-11化合物23之NOESY圖譜......................................310
Figure 5-1-24-1 The 1H–1H COSY and selective HMBC correlations of 24....312
Figure 5-1-24-2 Selective NOESY correlations of 24.......................314
Figure 5-1-24-3 化合物24之IR圖譜.........................................316
Figure 5-1-24-4 化合物24之低解析ESIMS圖譜................................316
Figure 5-1-24-5 化合物24之高解析ESIMS圖譜................................317
Figure 5-1-24-6 化合物24之1H NMR圖譜.....................................317
Figure 5-1-24-7 化合物24之13C NMR圖譜....................................318
Figure 5-1-24-8 化合物24之HSQC圖譜.......................................318
Figure 5-1-24-9 化合物24之1H–1H COSY圖譜................................319
Figure 5-1-24-10化合物24之HMBC圖譜.......................................319
Figure 5-1-24-11化合物24之NOESY圖譜......................................320
Figure 5-2-38-1 The 1H–1H COSY and selective HMBC correlations of 38....323
Figure 5-2-38-2 The 13C-NMR chemical shifts of the side-chain of pinnigorsterol A (38),
(22E,24S)-24-methyl-cholest-5-en-3-ol (A), and (22E,24R)-24-methylcholest-5-en-3-ol (B)....324
Figure 5-2-38-3 Selective NOESY correlations of 38.......................324
Figure 5-2-38-4 化合物38之IR圖譜.........................................326
Figure 5-2-38-5 化合物38之低解析ESIMS圖譜................................326
Figure 5-2-38-6 化合物38之高解析ESIMS圖譜................................327
Figure 5-2-38-8 化合物38之13C NMR圖譜....................................328
Figure 5-2-38-9 化合物38之DEPT圖譜.......................................328
Figure 5-2-38-10化合物38之HSQC圖譜.......................................329
Figure 5-2-38-11化合物38之1H–1H COSY圖譜................................329
Figure 5-2-38-12化合物38之HMBC圖譜.......................................330
Figure 5-2-38-13化合物38之NOESY圖譜......................................330
Figure 5-2-39-1 The 1H–1H COSY and selective HMBC correlations of 39....332
Figure 5-2-39-2 The 13C-NMR chemical shifts of the side-chain of pinnigorsterol B (39),
(24S)-24-methyl-cholest-5-en-3-ol (A), and (24R)-24-methylcholest-5-en-3-ol (B)............333
Figure 5-2-39-3 Selective NOESY correlations of 39.......................333
Figure 5-2-39-4 化合物39之IR圖譜.........................................335
Figure 5-2-39-5 化合物39之低解析ESIMS圖譜................................335
Figure 5-2-39-6 化合物39之高解析ESIMS圖譜................................336
Figure 5-2-39-7 化合物39之1H NMR圖譜.....................................336
Figure 5-2-39-8 化合物39之13C NMR圖譜....................................337
Figure 5-2-39-9 化合物39之DEPT圖譜.......................................337
Figure 5-2-39-10化合物39之HSQC圖譜.......................................338
Figure 5-2-39-11化合物39之1H–1H COSY圖譜................................338
Figure 5-2-39-12化合物39之HMBC圖譜.......................................339
Figure 5-2-39-13化合物39之NOESY圖譜......................................339
Figure 5-2-40-1 The 1H–1H COSY and selective HMBC correlations of 40....341
Figure 5-2-40-2 Selective NOESY correlations of 40.......................342
Figure 5-2-40-3 化合物40之IR圖譜.........................................344
Figure 5-2-40-4 化合物40之低解析ESIMS圖譜................................344
Figure 5-2-40-5 化合物40之高解析ESIMS圖譜................................345
Figure 5-2-40-6 化合物40之1H NMR圖譜.....................................345
Figure 5-2-40-7 化合物40之13C NMR圖譜....................................346
Figure 5-2-40-8 化合物40之DEPT圖譜.......................................346
Figure 5-2-40-9 化合物40之HSQC圖譜.......................................347
Figure 5-2-40-10化合物40之1H–1H COSY圖譜................................347
Figure 5-2-40-11化合物40之HMBC圖譜.......................................348
Figure 5-2-40-12化合物40之NOESY圖譜......................................348
表目錄
Table 1-2-1Six marine natural products and fourteen marine natural products inspired compounds that are FDA-approved agents or in clinical trial with details of their collected source, predicted biosynthetic source, molecular target, and disease treated......................8
Table 1-3-1 Briareum asbestinum珊瑚的文獻回顧..............................................................10
Table 1-3-2 Briareum excavatum珊瑚的文獻回顧...............................................................14
Table 1-3-3 Briareum polyanthes珊瑚的文獻回顧..............................................................30
Table 1-3-4 Briareum stechei珊瑚的文獻回顧.................................................................31
Table 1-3-5 Briareum violacea珊瑚的文獻回顧................................................................35
Table 1-3-6 Briareum sp.珊瑚的文獻回顧.....................................................................36
Table 1-3-7 9,11-secosteroid類天然化合物文獻回顧...........................................................48
Table 5-1-1-1 The calculated distances (A) between selected protons with key NOESY correlations for 1....81
Table 5-1-1-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for1.................................82
Table 5-1-2-1 The calculated distances (A) between selected protons with key NOESY correlations for 2....91
Table 5-1-2-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 2................................92
Table 5-1-3-1 The calculated distances (A) between selected protons with key NOESY correlations for 3...101
Table 5-1-3-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 3...............................102
Table 5-1-4-1 The calculated distances (A) between selected protons with key NOESY correlations for 4...111
Table 5-1-4-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 4...............................112
Table 5-1-5-1 The calculated distances (A) between selected protons with key NOESY correlations for 5...121
Table 5-1-5-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 5...............................122
Table 5-1-6-1 The calculated distances (A) between selected protons with key NOESY correlations for 6...131
Table 5-1-6-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 6...............................132
Table 5-1-7-1 The calculated distances (A) between selected protons with key NOESY correlations for 7...141
Table 5-1-7-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 7...............................142
Table 5-1-8-1 The calculated distances (A) between selected protons with key NOESY correlations for 8...151
Table 5-1-8-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 8...............................152
Table 5-1-9-1 The calculated distances (A) between selected protons with key NOESY correlations for 9...161
Table 5-1-9-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 9...............................162
Table 5-1-10-1 The calculated distances (A) between selected protons with key NOESY correlations for10...172
Table 5-1-10-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 10..............................173
Table 5-1-11-1 The calculated distances (A) between selected protons with key NOESY correlations for 11..182
Table 5-1-11-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 11..............................183
Table 5-1-12-1 The calculated distances (A) between selected protons with key NOESY correlations for 12..192
Table 5-1-12-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 12..............................193
Table 5-1-13-1 The calculated distances (A) between selected protons with key NOESY correlations for 13..202
Table 5-1-13-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 13..............................203
Table 5-1-14-1 The calculated distances (A) between selected protons with key NOESY correlations for 14..212
Table 5-1-14-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 14..............................213
Table 5-1-15-1 The calculated distances (A) between selected protons with key NOESY correlations for 15..223
Table 5-1-15-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 15..............................224
Table 5-1-16-1 The calculated distances (A) between selected protons with key NOESY correlations for 16..234
Table 5-1-16-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 16..............................235
Table 5-1-17-1 The calculated distances (A) between selected protons with key NOESY correlations for 17..244
Table 5-1-17-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 17..............................245
Table 5-1-18-1 The calculated distances (A) between selected protons with key NOESY correlations for 18..254
Table 5-1-18-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 18..............................255
Table 5-1-19-1 The calculated distances (A) between selected protons with key NOESY correlations for 19..264
Table 5-1-19-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 19..............................265
Table 5-1-20-1 The calculated distances (A) between selected protons with key NOESY correlations for 20..274
Table 5-1-20-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 20..............................275
Table 5-1-21-1 The calculated distances (A) between selected protons with key NOESY correlations for 21..284
Table 5-1-21-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 21..............................285
Table 5-1-22-1 The calculated distances (A) between selected protons with key NOESY correlations for 22..294
Table 5-1-22-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 22..............................295
Table 5-1-23-1 The cal47culated distances (A) between selected protons with key NOESY correlations for 23.304
Table 5-1-23-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 23...............................305
Table 5-1-24-1 The calculated distances (A) between selected protons with key NOESY correlations for 24...314
Table 5-1-24-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 24...............................315
Table 5-2-38-1 The calculated distances (A) between selected protons with key NOESY correlations for 38...324
Table 5-2-38-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 38...............................325
Table 5-2-39-1 The calculated distances (A) between selected protons with key NOESY correlations for 39...333
Table 5-2-39-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for39................................334
Table 5-2-40-1 The calculated distances (A) between selected protons with key NOESY correlations for 40...342
Table 5-2-40-2 1H and 13C NMR data, 1H-1H COSY and HMBC correlations for 40...............................343
Table 5-4-1 Cytotoxic activity of compounds 1–24 and 38–40 for various human cancer cell lines for 72hr...............................................355
Table 5-4-2 Effect of compounds 1–24 and 38–40 on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB........357
Table 5-4-3 Effect of compounds 1–24 and 38–40 on pro-inflammatory iNOS and COX-2 protien expression in LPS-stimulated murine marcrophage cell line RAW264.7................................................................................................................................................359
Table 6-1 NMR chemical shifts for H-2, H-3, H-4 and C-2, C-3, C-4, C-5, C-16 of 2-hydroxybriaranes possessing (A) a Δ3,5(16) conjugated diene moiety.........................................................................................................................................361
Table 6-2 NMR chemical shifts for H-2, H-3, H-4 and C-2, C-3, C-4, C-5, C-6 of 2-hydroxybriaranes possessing (B) a Δ3,5 conjugated diene moiety. ........................................................................................................................................................362
Table 6-3 NMR chemical shifts for H-2, and C-2, C-3, C-4, C-5, C-16 of 2-acetoxybriaranes possessing (C) a Δ3,5(16) conjugated diene moiety. ........................................................................................................................................................362
Table 6-4 NMR chemical shifts for H-2, and C-2, C-3, C-4, C-5, C-6 of 2-acetoxybriaranes possessing (D) a Δ3, 5 conjugated diene moiety..................................................................................................................................................363
Table 6-5 13C NMR chemical shifts for natural briaranes possessing a CH3-20 group in α form....................................................................................................................................................365
Table 6-6 Table 6-6 13C NMR chemical shifts for natural briaranes possessing a CH3-20 group in β form....................................................................................................................................................365
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