台灣東海岸產Xenia sp. (GN47) 軟珊瑚之二氯甲烷及丙酮層粗萃物，以open column矽膠管柱層析與高壓液相層析儀(high-pressure
liquid chromatography, HPLC) 進行分離純化，得到六個diterpenoid與二個cadinane sesquiterpenes，分別為13-epi-9-desacetylxenicin (1)、
xenione (2)、13-epi-7,8-epoxide-9-des-acetylxenicin (3)、isoxeniolide-A (4)、7,8-epoxide-4,12Z-isoxeniolide-A (5)、4,12Z-9-deoxyisoxeniolide-A (6)等diterpenoid化合物與xenitorins B (7)、xenitorins A (8) 等cadinane
sesquiterpenes化合物，其中4,12Z-9-deoxyxeniolide-A (6)是新化合物，化合物3過去未定立體化學，化合物2之過去文獻上之結構錯誤，本論文在此一起訂正之。

Formosan soft coral Xenia sp. (GN47) (collected at east coast of Taiwan) was extracted with methylene chloride and acetone. Chromatographic separation of the organic extract resulted in the isolation of six diterpenoids, 13-epi-9-desacetylxenicine (1), xenicinone (2), 13-epi-7,8-epoxide-9-des-
acetylxenicine (3), isoxeniolide-A (4), 7,8-epoxide-4,12Z-iso-xeniolide-A (5), 4,12Z-9-deoxy-isoxeniolide-A(6) as well as two cadinane sesquiterpenes, xenitorins B (7) and xenitorins A (8).
Compound 6 is a new compound. We revised structure of compound 2 and determined the stereochemistry of compound 3.

目 錄
頁次
壹、緒論 1
一、前言 1
二、Xenia屬軟珊瑚之天然物化學研究回顧 2-27
三、研究動機與目的 28
貳、GN47傘軟珊瑚化學成分之研究 28
一、材料採集與鑑定 29
二、GN47傘軟珊瑚之分類地位 29
三、GN47傘軟珊瑚之萃取與分離 30
四、GN47傘軟珊瑚化學成分之分離純化 32
(1) GN47-301(1)之分離純化 32-34
(2) GN47-264(2)之分離純化 35-37
(3) GN47-275(3)之分離純化 38-40
(4) GN47-314(4)之分離純化 41-43
(5) GN47a-47(5)之分離純化 44-46
(6) GN47-24-C(6)之分離純化 47-49
(7) GN47-51(7)之分離純化 50-51
(8) GN47-9(8)之分離純化 52-53
五、GN47傘軟珊瑚化學成分之結構解析 54
(1) GN47-301(1)之結構解析 54-58
(2) GN47-264(2)之結構解析 66-70
(3) GN47-275(3)之結構解析 78-83
(4) GN47-314(4)之結構解析 91-93
(5) GN47a-47(5)之結構解析 96-100
(6) GN47-24-C(6)之結構解析 108-112
(7) GN47-51(7)之結構解析 120
(8) GN47-9(8)之結構解析 122
參、化合物之細胞毒殺活性 124
肆、結論 125
伍、參考文獻 126-131陸、附錄 132
一、儀器及材料 132-133
二、癌細胞毒殺活性測試之分析方法 134
三、MTT分析原理 135
圖目錄
頁次
圖一、Xenia sp. (GN47)傘軟珊瑚所分離到之化學成分 i-ii
圖二、Xenia sp. (GN47)軟珊瑚之分離流程 31
圖三、GN47-301(1)之1H-NMR圖譜 59
圖四、GN47-301(1)之13C NMR及DEPT圖譜 60
圖五、GN47-301(1)之HSQC圖譜 61
圖六、GN47-301(1)之COSY圖譜 62
圖七、GN47-301(1)之HMBC圖譜 63
圖八、GN47-301(1)之NOESY圖譜 64
圖九、GN47-301(1)之NOESY關連圖譜 65
圖十、GN47-264(2)之1H-NMR圖譜 71
圖十一、GN47-264(2)之13C NMR及DEPT圖譜 72
圖十二、GN47-264(2)之HSQC圖譜 73
圖十三、GN47-264(2)之COSY圖譜 74
圖十四、GN47-264(2)之HMBC圖譜 75
圖十五、GN47-264(2)之NOESY圖譜 76
圖十六、GN47-264(2)之NOESY關連圖譜 77
圖十七、GN47-275(3)之1H-NMR圖譜 84
圖十八、GN47-275(3)之13C NMR及DEPT圖譜 85
圖十九、GN47-275(3)之HSQC圖譜 86
圖二十、GN47-275(3)之COSY圖譜 87
圖二十一、GN47-275(3)之HMBC圖譜 88
圖二十二、GN47-275(3)之NOESY圖譜 89
圖二十三、GN47-275(3)之NOESY關連圖譜 90
圖二十四、GN47-314(4)之1H-NMR圖譜 95
圖二十五、GN47-314(4)之13C NMR及DEPT圖譜 96
圖二十六、GN47a-47(5)之1H-NMR圖譜 101
圖二十七、GN47a-47(5)之13C NMR及DEPT圖譜 102
圖二十八、GN47a-47(5)之HSQC圖譜 103
圖二十九、GN47a-47(5)之COSY圖譜 104
圖三十、GN47a-47(5)之HMBC圖譜 105
圖三十一、GN47a-47(5)之NOESY圖譜 106
圖三十二、GN47a-47(5)之NOESY關連圖譜 107
圖三十三、GN47-24-C(6)之1H-NMR圖譜 113
圖三十四、GN47-24-C(6)之DEPT圖譜 114
圖三十五、GN47-24-C(6)之HSQC圖譜 115
圖三十六、GN47-24-C(6)之COSY圖譜 116
圖三十七、GN47-24-C(6)之HMBC圖譜 117
圖三十八、GN47-24-C(6)之NOESY圖譜 118
圖三十九、GN47-24-C(6)之NOESY關連圖譜 120
圖四十、GN47-51(7)之1H-NMR圖譜 122
圖四一、GN47-9(8)之1H-NMR圖譜 123

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