本研究主要針對養殖型皮軟珊瑚Briareum stechei所含天然物成分進行分析，並從中分離純化出二十個briarane類的雙萜化合物，其中包括八個新化合物briarenols M-T (1-8) 與十二個已知化合物minabein-8 (9); solenolides A (10)、E (11); excavatolide A (12); briaviolide C (13); briarenolides S (14)、R (15)、M (16); brianolide (17); briaexcavatolides F (18)、I (19)、P (20)。化合物1-20的結構皆透過光譜資料分析與文獻資料比對的方式加以解析而建立，並經由X-ray單晶繞射確認化合物12、17、18之絕對立體構型。
在化合物的抗發炎活性測試中，briaexcavatolide P (20) 在10 μM時，對由脂多醣 (Lipopolysaccharide, LPS) 所誘發小鼠巨噬細胞RAW 264.7產生一氧化氮合成酶 (inducible nitric oxide synthase, iNOS) 與第二型環氧化酶(cyclooxygenase-2, COX-2) 具有抑制效果，表現率分別為50.92 ± 4.99%以及67.44 ± 1.42%。而同樣於10 μM的濃度下，solenolide A (10) 卻有顯著促進COX-2的效果 (204.76 ± 17.08%)。

This study aims to investigate the natural products from a cultured octocoral Briareum stechei. Twenty briarane-type diterpenoids, including eight new compounds, briarenols M-T (1-8) along with twelve known compounds, minabein-8 (9), solenolides A (10), and E (11), excavatolide A (12), briaviolide C (13), briarenolides S (14), R (15), and M (16), brianolide (17), and briaexcavatolides F (18), I (19), and P (20) were isolated. The structures of metabolites 1-20 were established by using spectroscopic methods and comparing the spectroscopic data with those of related compounds. The absolute configurations of excavatolide A (12), brianolide (17), and briaexcavatolide F (18) were further determind by using single-crystal X-ray diffraction analysis.
In the anti-inflammatory activity test, briaexcavatolide P (20) inhibited the expression of iNOS and COX-2 protein induced by LPS to 50.92 ± 4.99% and 67.44 ± 1.42%, respectively, and solenolide A (10) enhanced the release of COX-2 protein to 204.76 ± 17.08%, at a concentration of 10 μM.

中文摘要 I
Abstract III
目錄 VII
圖目錄 IX
表目錄 XV
第一章、緒論 1
第一節、前言與研究動機 1
第二節、Briareum屬所含天然物之文獻回顧 3
第二章、生物材料與分離流程 33
第一節、生物樣品採集與分類 33
第二節、生物樣品的萃取與分離 34
第三章、實驗器材與有機溶劑 37
第一節、儀器 37
第二節、其他材料與有機溶劑 39
第四章、生物活性試驗 41
第一節、抗發炎活性測試-Ⅰ 41
第二節、抗發炎活性測試-Ⅱ 43
第五章、結果與討論 45
第一節、養殖型皮軟珊瑚 Briareum stechei 所含天然物之結構解析 45
(一)、 Briarenol M (1) 之結構解析 45
(二)、 Briarenol N (2) 之結構解析 57
(三)、 Briarenol O (3) 之結構解析 71
(四)、 Briarenol P (4) 之結構解析 83
(五)、 Briarenol Q (5) 之結構解析 97
(六)、 Briarenol R (6) 之結構解析 107
(七)、 Briarenol S (7) 之結構解析 117
(八)、 Briarenol T (8) 之結構解析 129
(九)、 Minabein-8 (9) 之結構解析 139
(十)、 Solenolide A (10) 之結構解析 145
(十一)、 Solenolide E (11) 之結構解析 151
(十二)、 Excavatolide A (12) 之結構解析 157
(十三)、 Briaviolide C (13) 之結構解析 163
(十四)、 Briarenolide S (14) 之結構解析 169
(十五)、 Briarenolide R (15) 之結構解析 175
(十六)、 Briarenolide M (16) 之結構解析 181
(十七)、 Brianolide (17) 之結構解析 187
(十八)、 Briaexcavatolide F (18) 之結構解析 193
(十九)、 Briaexcavatolide I (19) 之結構解析 199
(二十)、 Briaexcavatolide P (20) 之結構解析 205
第二節、化合物數據實驗整理 211
第三節、化合物活性試驗數據 215
第六章、結論 219
第七章、參考文獻 221
第八章、附錄 229
附錄一、X-ray解析資料 229
1. Excavatolide A (12) (CCDC: 1961870) 229
2. Brianolide (17) (CCDC: 1966097) 237
3. Briaexcavatolide F (18) (CCDC: 1982252) 245

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