本研究主要是從兩種指型軟珊瑚 Sinularia granosa 與Sinularia leptoclados 的有機萃取物中尋找具有生物活性的化學成分。從這兩種珊瑚的研究中共得到二十一個天然化合物1–21，其中從軟珊瑚S. granosa中分離出六個新的化合物，其中五個為cembrane-type diterpenoids類化合物querciformolide B (1)、granosolides A–D (2, 3, 5, 6)，一個為 secosteroid 類化合物3β,11-dihydroxy-5β,6β-expoxy-24-
methylene-9,11-secocholestan-9-one (11)及七個已知化合物 4, 7–10, 12,
13。從軟珊瑚S. leptoclados 中分離出四個新化合物，其中兩個為
oppositol-type sesquiterpenoids 類化合物 leptocladolin A, B (14, 15)，兩
個為 steroid 類化合物24-methylenecholestan-3β,5α,6β-triol 11-acetate
(18)、24(S*)-24-methylcholestan-3β,5α,6β-triol 11-acetate (19)及四個已
知化合物(16, 17, 20, 21)。所有化合物的化學構造均由光譜數據的分
析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決
定。化合物1, 7, 14 和16 並經由X-ray 晶體繞射來證明其化合物之結
構，而化合物1–3 和14–17 的絕對立體構造，可經由Mosher’s 酯化
反應及比對的方式加以確定。
本研究中將所獲得的化合物1–17 和19–21 進行癌細胞株的細胞
毒殺與抗發炎活性測試。在細胞毒殺活性測試結果顯示化合物9、19
及21 對人類髓母細胞瘤癌細胞(Daoy)、人類喉癌細胞(Hep2)、人類乳
癌細胞(MCF-7)、人類子宮頸癌細胞(Hela)、人類急性淋巴細胞白血病
T 淋巴細胞(CCRF-CEM)和人類結直腸腫瘤細胞(DLD-1)都具有中等
的細胞毒殺活性。而化合物11 和17 對於在濃度為10 μM 下可有效的抑制發炎蛋白質iNOS 與COX-2 的表現。

In order to search for bioactive compounds, we have studied the
chemical constituents from the organic extracts of two soft corals
Sinularia granosa and Sinularia leptoclados. This study had led to the
isolation of twenty-one natural compounds 1–21, including five new
cembrane-type diterpenoids, querciformolide B (1), granosolides A–D (2, 3,
5, and 6) and one new secosteroid 3β,11-dihydroxy-5β,6β-expoxy-24-
methylene-9,11-secocholestan-9-one (11) along with seven know
compounds from S. granosa, and two new oppositol–type sesquiterpenoids
leptocladolins A and B (14 and 15), and two new steroid
24-methylenecholestan-3β,5α,6β-triol 11-acetate (18)、24(S*)-24-
methylcholestan-3β,5α,6β-triol 11-acetate (19) along with four known
compounds (16, 17, 20 and 21) from S. leptoclados. The structure of
compounds 1–21 were established by detailed spectral data analysis (IR,
MS, 1D, 2D NMR) and by comparison of the spectral data with those ofthe related known compounds. The relative stereochemistries of
compounds 1, 7, 14, and 15 were further confirmed by X-ray
single-crystal diffraction analysis. The absolute configurations of 1–3 and
14–17 were determined using a modified Mosher’s method.
The cytotoxicity of compounds 1–17 and 19–21 against the Daoy
(human medulloblastoma), Hep2 (human laryngeal carcinoma), MCF-7
(human breast adenocarcinoma), Hela (human cervical epitheloid carcinoma)
CCRF-CEM (human T-cell acute lymphoblastic leukemia), and DLD-1
(human colon adenocarcinoma) tumor cell lines were determined.
Compounds 9, 19, and 21 showed moderate activity toward the above five
tumor cells. Furthermore, compounds 11 and 17 were found to show
significant activity against the accumulation of the pro-inflammatory iNOSand COX-2 protein at 10 μM.

目 錄 頁 次
中文摘要 XII
英文摘要 XIII
化合物1−13 化學結構 XIV
化合物14−21 化學結構 XV
第一章、緒論 1
第一節、前言 1
第二節、研究背景及目的 2
第三節、文獻回顧 4
第二章、生物材料與研究方法 20
第一節、研究流程 20
第二節、Sinularia granosa 樣品採集時間、地點、分類地位及
分離流程
22
2.2.1 Sinularia granosa 樣品採集時間、地點、分類地位 22
2.2.2 Sinularia granosa 樣品的萃取分離 22
第三節、Sinularia leptoclados 樣品採集時間、地點、分類地位及
分離流程 25
2.3.1 Sinularia leptoclados 樣品採集時間、地點、分類地位 25
2.3.2 Sinularia leptoclados 樣品的萃取分離 26
第四節、實驗設備儀器及材料 28
2.4.1 實驗設備儀器 28
2.4.2 實驗材料 29
第三章、化合物之結構證明 30
第一節：軟珊瑚Sinularia granosa 所分離出之化合物的結構證明 30
(一)、Querciformolide B (1) 化合物構造之解析 30
(二)、Granosolide A (2) 化合物構造之解析 39
(三)、Granosolide B (3) 化合物構造之解析 49
(四)、Dendronpholide F (4) 化合物構造之解析 58
(五)、Granosolide C (5) 化合物構造之解析 68
(六)、Granosolide D (6) 化合物構造之解析 76
(七)、11-Epi-sinulariolide acetate (7) 化合物構造之解析 86
(八)、 3,4:8,11-Bisepoxy-7-acetoxycembra-15(17)-en-1,12-olide (8)
化合物構造之解析
91
(九)、11-Dehydrosinulariolide (9) 化合物構造之解析 95
(十)、Querciformolide F (10) 化合物構造之解析 99
(十一)、3β,11-Dihydroxy-5α,6α-expoxy-24-methylene-
9,11-secocholestan-9-one (11) 化合物構造之解析
107
(十二)、3β,11-Dihydroxy-5β,6β-expoxy-24-methylene-
9,11-secocholestan-9-one (12) 化合物構造之解析
117
(十三)、(Z)-N-[2-(4-Hydroxyphenyl)ethyl]-3-methyldodec-
2-enamide (13) 化合物構造之解析
121
第二節：軟珊瑚Sinularia leptoclados 所分離出之化合物的結構證明 125
(十四)、Leptocladolin A (14) 化合物構造之解析 125
(十五)、Leptocladolin B (15) 化合物構造之解析 134
(十六)、1β-Hydroxy-6α-acetoxy-eudesm-4(15)-ene (16)
化合物構造之解析
144
(十七)、1β,6α-Dihydroxy-eudesm-4(15)-ene (17)
化合物構造之解析
149
(十八)、24-Methylenecholestan-3β,5α,6β -triol-11-acetate (18)
化合物構造之解析
153
(十九)、24(S*)-24-Methylcholestan-3β,5α,6β-triol-11-acetate (19)
化合物構造之解析
163
(二十)、Sinuleptolide (20) 化合物構造之解析 174
(二十一)、5-Epi-sinuleptolide (21) 化合物構造之解析 178
第三節:化學反應步驟 182
第四節:化合物物理性質及圖譜數據整理
186
第四章、生物活性試驗 191
第一節、生物活性試驗方法 191
(一)、細胞毒殺活性試驗方法 191
(二)、抗發炎活性試驗方法 193
第二節、生物活性試驗結果 196
(一)、細胞毒殺活性試驗結果 196
(二)、抗發炎活性試驗結果 198
第五章、結論 201
第六章、參考文獻 207
附錄(一)、化合物 7 之X-ray 實驗數據 213
附錄(二)、化合物 14 之X-ray 實驗數據 223
附錄(三)、化合物 16 之X-ray 實驗數據 231

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