臺灣產軟珊瑚 Cespitularia hypotentaculata 的丙酮/二氯甲烷 (1:1) 萃取物以矽膠管柱層析及高效能液相層析 (HPLC) 進行分離純化，總共分離得到 9 個化合物，分別為 verticillane skeleton 的cespitularin I (1)，norverticillane skeleton 的 cespitularin J (2)，而 cespitularin K (3)、6-acetoxycespitularin F (4) 跟 cespitularin L (5) 為 cespitularane skeleton，(24S)-3β,11-dihydroxy-5β,6β-epoxy-24-methyl-9,11-secocholestan-9-one (6)、3β,11-dihydroxy-5β,6β-epoxy-9,11-secocholestan-9-one (7) 及 3β-hydroxy-5β,6β-epoxy-9-oxo-9,11-secogorgostan-11-ol (8) 是 secosterols，與 xenia diterpene 的cespolide A (9)，其中化合物 1、2、3、4、5、7、8、9 為新化合物。所有化合物的結構皆由 1D 與 2D 光譜分析所確立，同時也對這些化合物進行癌細胞毒殺活性測試。經癌細胞毒殺活性測試顯示化合物 1 對P-388 具有不錯的抑制作用，而化合物 5-7 對 HT-29 的癌細胞毒殺活性值為 ED50 < 4.0 mg/mL。

Eight new metabolites (1-5 and 7-9) and one known compound were isolated from the acetone/methylene chloride (1:1)extracts of the Formosan soft coral Cespitularia hypotenta-culata. These compounds can be divided into five groups: cespitularin I (1), having the verticillane skeleton, cespitularin J (2), that possesses the norverticillane skeleton, cespitularin K (3)、6-acetoxycespitularin F (4) and cespitularin L (5), possessing the cespitularane skeleton, (24S)-3β,11-dihydroxy-5β,6β-epoxy-24-methyl-9,11-secocholestan-9-one (6), 3β,11-dihydroxy-5β,6β-epoxy-9,11-secocholestan-9-one (7), and 3β-hydroxy-5β,6β-epoxy-9-oxo-9,11-secogorgo-stan-11-ol (8) are secosterols, and xenia diterpene, cespolide A (9). All of these structures were elucidated by extensive spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.

目 錄
頁次
壹、緒論--------------------------------------------------------------------------------------1
一、前言-------------------------------------------------------------------------------------1
二、Cespitularia 屬軟珊瑚之天然物化學研究回顧-------------------------------3
三、研究動機與目的---------------------------------------------------------------------8
貳、軟珊瑚 Cespitularia hypotentaculata 化學成分研究--------------------------9
一、材料採集與鑑定---------------------------------------------------------------------9
二、軟珊瑚 Cespitularia hypotentaculata 之分類地位-----------------------------9
三、軟珊瑚 Cespitularia hypotentaculata 之萃取與分離------------------------10
四、軟珊瑚 Cespitularia hypotentaculata 化學成分之分離純化--------------12
(1) GN67-520 (1) 之分離純化--------------------------------------------------------12
(2) GN67-478 (2) 之分離純化--------------------------------------------------------15
(3) GN67-291 (3) 之分離純化--------------------------------------------------------18
(4) GN67-490 (4) 之分離純化--------------------------------------------------------21
(5) GN67-414 (5) 之分離純化--------------------------------------------------------24
(6) GN67-361 (6) 之分離純化--------------------------------------------------------27
(7) GN67-391 (7) 之分離純化--------------------------------------------------------30
(8) GN67-393 (8) 之分離純化--------------------------------------------------------33
(9) GN67-223 (9) 之分離純化--------------------------------------------------------36
五、軟珊瑚 Cespitularia hypotentaculata 化學成分之結構解析--------------39
(1) GN67-520 (1) 之結構解析--------------------------------------------------------39
(2) GN67-678 (2) 之結構解析--------------------------------------------------------50
(3) GN67-291 (3) 之結構解析--------------------------------------------------------60
(4) GN67-490 (4) 之結構解析--------------------------------------------------------71
(5) GN67-414 (5) 之結構解析--------------------------------------------------------81
(6) GN67-361 (6) 之結構解析--------------------------------------------------------91
(7) GN67-391 (7) 之結構解析------------------------------------------------------101
(8) GN67-393 (8) 之結構解析------------------------------------------------------109
(9) GN67-223 (9) 之結構解析------------------------------------------------------118
參、化合物之細胞毒殺活性--------------------------------------------------------128
肆、結論----------------------------------------------------------------------------------129
伍、參考文獻----------------------------------------------------------------------------131
陸、附錄----------------------------------------------------------------------------------136
一、儀器及材料------------------------------------------------------------------------136
二、癌細胞毒殺活性測試之分析方法-------------------------------------------138
三、MTT 分析原理--------------------------------------------------------------------139


圖目錄


頁次
圖一、軟珊瑚 Cespitularia hypotentaculata 之分離流程-----------------------11
圖二、GN67-520 (1) 之 1H-NMR 圖譜--------------------------------------------44
圖三、GN67-520 (1) 之 13C-NMR 圖譜-------------------------------------------45
圖四、GN67-520 (1) 之 HSQC 圖譜------------------------------------------------46
圖五、GN67-520 (1) 之 HMBC 圖譜------------------------------------------------47
圖六、GN67-520 (1) 之 COSY 圖譜------------------------------------------------48
圖七、GN67-520 (1) 之 NOESY 圖譜----------------------------------------------49
圖八、GN67-478 (2) 之 1H-NMR 圖譜---------------------------------------------54
圖九、GN67-478 (2) 之 13C-NMR 及 DEPT 圖譜--------------------------------55
圖十、GN67-478 (2) 之 HSQC 圖譜-------------------------------------------------56
圖十一、GN67-478 (2) 之 HMBC 圖譜---------------------------------------------57
圖十二、GN67-478 (2) 之 COSY 圖譜---------------------------------------------58
圖十三、GN67-478 (2) 之 NOESY 圖譜--------------------------------------------59
圖十四、GN67-291 (3) 之 1H-NMR 圖譜------------------------------------------65
圖十五、GN67-291 (3) 之 13C-NMR 及 DEPT 圖譜---------------------------66
圖十六、GN67-291 (3) 之 HSQC 圖譜---------------------------------------------67
圖十七、GN67-291 (3) 之 HMBC 圖譜---------------------------------------------68
圖十八、GN67-291 (3) 之 COSY 圖譜---------------------------------------------69
圖十九、GN67-291 (3) 之 NOESY 圖譜--------------------------------------------70
圖二十、GN67-490 (4) 之 1H-NMR 圖譜------------------------------------------75
圖二十一、GN67-490 (4) 之 13C-NMR 及 DEPT圖譜--------------------------76
圖二十二、GN67-490 (4) 之 HSQC 圖譜-------------------------------------------77
圖二十三、GN67-490 (4) 之 HMBC 圖譜-------------------------------------------78
圖二十四、GN67-490 (4) 之 COSY 圖譜-------------------------------------------79
圖二十五、GN67-490 (4) 之 NOESY 圖譜------------------------------------------80
圖二十六、GN67-414 (5) 之 1H-NMR 圖譜----------------------------------------85
圖二十七、GN67-414 (5) 之 13C-NMR 圖譜---------------------------------------86
圖二十八、GN67-414 (5) 之 HSQC 圖譜------------------------------------------ 87
圖二十九、GN67-414 (5) 之 HMBC 圖譜-------------------------------------------88
圖三十、GN67-414 (5) 之 COSY 圖譜-----------------------------------------------89
圖三十一、GN67-414 (5) 之 NOESY 圖譜------------------------------------------90
圖三十二、GN67-361 (6) 之 1H-NMR 圖譜----------------------------------------94
圖三十三、GN67-361 (6) 之 13C-NMR 及 DEPT 圖譜--------------------------95
圖三十四、GN67-361 (6) 之 13C-NMR 及 DEPT 圖譜局部放大圖----------96
圖三十五、GN67-361 (6) 之 HSQC 圖譜--------------------------------------------97
圖三十六、GN67-361 (6) 之 HMBC 圖譜--------------------------------------------98
圖三十七、GN67-361 (6) 之 COSY 圖譜--------------------------------------------99
圖三十八、GN67-361 (6) 之 NOESY 圖譜------------------------------------------100
圖三十九、GN67-391 (7) 之 1H-NMR 圖譜-----------------------------------------103
圖四十、GN67-391 (7) 之 13C-NMR 及 DEPT 圖譜------------------------------104
圖四十一、GN67-391 (7) 之 HSQC 圖譜--------------------------------------------105
圖四十二、GN67-391(7) 之 HMBC 圖譜--------------------------------------------106
圖四十三、GN67-391 (7) 之 COSY 圖譜--------------------------------------------107
圖四十四、GN67-391 (7) 之 NOESY 圖譜------------------------------------------108
圖四十五、GN67-393 (8) 之 1H-NMR 圖譜----------------------------------------112
圖四十六、GN67-393 (8) 之 13C-NMR 及 DEPT 圖譜--------------------------113
圖四十七、GN67-393 (8) 之 HSQC 圖譜-------------------------------------------114
圖四十八、GN67-393 (8) 之 HMBC 圖譜------------------------------------------115
圖四十九、GN67-393 (8) 之 COSY 圖譜-------------------------------------------116
圖五十、GN67-393 (8) 之 NOESY 圖譜--------------------------------------------117
圖五十一、GN67-223 (9) 之 1H-NMR 圖譜---------------------------------------122
圖五十二、GN67-223 (9) 之 13C-NMR 及 DEPT 圖譜-------------------------123
圖五十三、GN67-223 (9) 之 HSQC 圖譜-------------------------------------------124
圖五十四、GN67-223 (9) 之HMBC圖譜--------------------------------------------125
圖五十五、GN67-223 (9) 之COSY圖譜---------------------------------------------126
圖五十六、GN67-223 (9) 之NOESY 圖譜------------------------------------------127

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