延續臺灣蘭嶼海域粗枝竹珊瑚Isis hippuris之研究，分離出四個固醇類化合物1–4，其中化合物1–2為C-3酮基取代的固醇類新化合物。另由文獻中指出，已進行化學成分研究的Sinularia 屬聚指軟珊瑚主要化學成分有類固醇類、倍半萜類和雙萜類，其中一些化學成分具有較好的藥理活性，為了尋找具有生物活性的新化合物，本論文主要針對臺東三仙台海域之聚指軟珊瑚Sinularia numerosa的二次代謝物進行色層分析。經由各種層析，從軟珊瑚S. numerosa之有機萃取物中分離得到四個新的cembrene diterpenoid類化合物 5–8、七個已知的化合物 9–13、15和16、二個新的steroid類化合物14和17，以及一個為天然物首次發現以α-生育酚與β-木醣接合形式存在之新化合物18。為了探究海洋微生物天然活性物質，本論文亦對墾丁萬里桐附近採集而來的菌株Microbulbifer sp.經初步活性檢測後進行大量培養並以乙酸乙酯萃取，接著藉由各種層析技術而分離出一個新天然物化合物19，以上這些二次代謝物的結構是藉由各種有機光譜分析 (紅外線光譜、紫外線光譜、質譜、比旋光值、一維及二維NMR) 以及與已知化合物之文獻的光譜資料比對而決定，其中化合物6之絕對立體位向的決定是運用Mosher方法得到證實。
化合物1–2、5–8、13–14和17–19以人類肺癌細胞 (A-549)、人類直腸癌細胞 (HT-29) 與老鼠血癌細胞 (P-388) 進行細胞毒殺活性實驗，化合物5–6和17–18亦進行抗人類巨細胞病毒(HCMV)測試，發現化合物13和19對P-388有毒殺活性，其ED50值分別為4.3和3.9 μg/mL。

Continued studies on the secondary metabolites of the Formosan octocoral Isis hippuris collected at Orchid Island have led to the isolation of two new steroids 1–2, along with two known compounds 3–4. In addition, the coral species of the genus Sinularia (Alcyoniidae) are widespread in the different coral reefs all over the world, and were reported to contain a variety of secondary metabolites, comprising steroids, sesquiterpenoids, and diterpenoids. Chromatographic separation of organic extracts of S. numerosa resulted in the purification and structural elucidation of four new cembranoid derivatives 5–8, seven known compounds 913, 15 and 16, two new steroids 14 and 17, as well as one new α-tocopherol derivative 18. In continuing search for bioactive natural compounds from microorganisms, dimethyl pyridine-2,6-dicarboxylate 19 was isolated from marine bacterium Microbulbifer sp.. The structures of these metabolites were elucidated on the basis of extensive spectroscopic analysis (IR, UV, ESI-MS, specific optical rotation, 1D and 2D NMR) and by comparison of their spectral data with those of literature reports. Moreover, the absolute configuration of 6 was established by application of modified Mosher's method.
The cytotoxicity against A-549 (human lung epithelial carcinoma), HT-29 (human colon adenocarcinoma) and P-388 (mouse lymphocytic leukemia) cells activity of 1–2, 5–8, 13–14 and 17–19 as well as the anti-HCMV (human cytomegalovirus) activities of 5–6 and 17–18 were evaluated in vitro. Compounds 13 and 19 displayed cytotoxicity against P-388 cell line with ED50 values of 4.3 and 3.9 μg/mL, respectively.

論文審定書 i
謝辭 ii
中文摘要 iii
英文摘要 iv
化合物1–19之化學結構 v
目錄 vi
表次 x
圖次 xii
縮寫對照表 xxiii

壹、緒論 1
　一、前言、研究動機與目的 1
　二、粗枝竹珊瑚Isis hippuris之hippuristerone類二次代謝物研究回顧 3
　三、聚指軟珊瑚Sinularia numerosa之二次代謝物研究回顧 7
　 1. Cembrene diterpenoid類二次代謝物研究回顧 7
　 2. Polyhydroxylated steroid類二次代謝物研究回顧 9
　 3. Africane sesquiterpenoid類二次代謝物研究回顧 12
　 4. Oxylipin類二次代謝物研究回顧 13
　四、海洋細菌Microbulbifer sp.之二次代謝物研究回顧 14
　 1. Paraben類二次代謝物研究回顧 15
貳、材料與研究方法 17
　一、Isis hippuris樣品採集及分離流程 17
　　　　1. Isis hippuris樣品採集時間、地點與鑑定 17
　　　　2. Isis hippuris之分類地位 17
　　　　3. Isis hippuris之萃取與分離流程 18
　　　　4. Isis hippuris各化學成分之分離純化 20
　　　　 (1) LY19-27DM-6C-1 (1)、LY19-27DM-6C-2 (2)、LY19-27DM-6C-4
　　　　 (3)與LY19-27DM-6C-5 (4)之純化分離 20
　二、Sinularia numerosa樣品採集及分離流程 22
　　　　1. Sinularia numerosa樣品採集時間、地點與鑑定 22
　　　　2. Sinularia numerosa之分類地位 22
　　　　3. Sinularia numerosa之萃取與分離流程 23
　　　　4. Sinularia numerosa各化學成分之分離純化 25
　　　　 (1) SST12-19-2-6-21 (5)之純化分離 25
　　　　 (2) SST12-24-WE2-18 (6)之純化分離 26
　　　　 (3) SST12-23-2-10 (7)之純化分離 27
　　　　 (4) SST12-23-2-16 (8)之純化分離 27
　　　　 (5) SST12-23-3-33 (9)之純化分離 28
　　　　 (6) SST12-24-1E-1A (10)之純化分離 28
　　　　 (7) SST12-23-1-D (11)之純化分離 29
　　　　 (8) SST12-23-7-2 (12)、SST12-23-7 (13)與SST12-23-7-3 (14)之純化
　　　　 分離 30
　　　　 (9) SST12-23-4-9 (15)之純化分離 31
(10) SST12-24-3-3E-WASH (16)與SST12-24-3-3E-22 (17)之純化分離 32
　　　　(11) SST12-24-WEW-18 (18)之純化分離 33
　三、Microbulbifer sp.樣品培養及分離流程 35
　　　　1. Microbulbifer sp.樣品採集來源、地點與初步鑑定 35
　　　　2. Microbulbifer sp.之分類地位 35
　　　　3. Microbulbifer sp.之萃取與分離流程 35
　　　　4. Microbulbifer sp.各化學成分之分離純化 36
　　　　 (1) Coral07-A3-2 (19)之純化分離 38
参、化學成分之結構證明 39
　一、粗枝竹珊瑚Isis hippuris之化學成分的結構證明 39
　　　　1. LY19-27DM-6C-1 (1)之結構解析 39
　　　　2. LY19-27DM-6C-1 (2)之結構解析 59
　　　　3. LY19-27DM-6C-4 (3)之結構解析 79
　　　　4. LY19-27DM-6C-5 (4)之結構解析 84
　二、聚指軟珊瑚Sinularia numerosa之化學成分的結構證明 89
　　　　1. SST12-19-2-6-21 (5)之結構解析 89
　　　　2. SST12-24-WE2-18 (6)之結構解析 107
　　　　3. SST12-23-2-10 (7)之結構解析 137
　　　　4. SST12-23-2-16 (8)之結構解析 155
　　　　5. SST12-23-3-33 (9)之結構解析 173
　　　　6. SST12-24-1E-1A (10)之結構解析 183
　　　　7. SST12-23-1-D (11)之結構解析 195
　　　　8. SST12-23-7-2 (12)之結構解析 206
　　　　9. SST12-23-7 (13)之結構解析 219
10. SST12-23-7-3 (14)之結構解析 231
11. SST12-23-4-9 (15)之結構解析 253
12. SST12-24-3-3E-WASH (16)之結構解析 261
13. SST12-24-3-3E-22 (17)之結構解析 265
14. SST12-24-WEW-18 (18)之結構解析 283
　三、海洋細菌Microbulbifer sp.之化學成分的結構證明 308
　　　　1. Coral07-A3-2 (19)之結構解析 308
肆、生物活性之測試 318
　一、細胞毒殺試驗方法 318
　二、MTT分析原理 318
　三、抗HCMV病毒的測試方法 319
　四、活性試驗結果 319
伍、結論 321
陸、參考文獻 324
柒、附錄 338
　一、Mosher醯化反應的原理與製備 338
　二、實驗設備儀器及材料 338
　　　　1.實驗設備儀器 340
　　　　2.實驗材料 340

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