本論文主要的目標在利用各種色層分析方式分離白蘆莖柳珊瑚(Junceella fragilis)與皮柳珊瑚(Briareum violacea)這兩種台灣產軟珊瑚之有機溶劑萃取物，並利用核磁共振實驗與各種物理化學方法鑑定所含的化學成分，整理分析其數值資料，共計分離得八十四個天然化合物，其中有五十個為新化合物，並檢測與評估其生物活性。
在研究期間從白蘆莖柳珊瑚(J. fragilis)中分離出十五個新briarane雙萜類化合物 Frajunolides E-S (1-15) 與十九個已知briarane雙萜類化合物Junceellin、Junceellolides A-E、Junceellolide K、11α,20α-epoxy-4-deacetoxyjuncellolide D、Umbraculolide A、Junceellonoid A、Juncin P、Juncins Y-ZI、Frajunolides A-D與Praelolide，以及一個已知固醇類化合物，Ergosterol peroxide。由皮柳珊瑚(Briareum violacea)中分離出三十五個新briarane雙萜類化合物，Briaviolides A-Z (16-41)、Viobrianolides A-I (42-50) 以及伴隨著十四個已知化合物，Stylatulide lactone、Excavatolide A、9-deacetylstylatulide lactone、4β-acetoxy-9-deacetylstylatulide lactone、 Brianthein Z、Renillafoulin A、Braexcavatolide E、Braexcavatolide I、Minabein-4、Minabein-6、Milolide K、Solenolide A、Solenolides D-E。
上述所有化合物的結構均是利用各種物理數據 (紅外線、質譜、紫外線、旋光值)，並配合各種1D、2D核磁共振圖譜，以及比對文獻上相關化合物的數據來定立的。此外，化合物 16, 32, Praelolide等三個化合物的結構與相對立體結構更經由 X-ray 單晶繞射解析做更近一步的證明。另外，化合物32-38 利用其 CD 光譜來決定其絕對立體結構，確認其Me-20之絕對立體位向。
細胞毒殺活性方面，化合物Junceellin、Junceellolide B與Juncin ZI對Hep2 (Human laryngeal carcinoma)、Doay (Human medulloblastoma)、WiDr (Human colon adenocarcinoma)、Hela (Human cervical epitheloid carcinoma)四種癌細胞株具有微弱的毒殺活性。針對抑制elastase release與過氧離子的產生在人類嗜中性白血球之抗免疫活性檢測方面，化合物1在10 μg/mL具有微弱的活性。其餘化合物之生物活性正在送測中。

This dissertation mainly presented the investigation of natural products from two different Formosan gongonian soft corals, Briareum violacea and Junceella fragilis. Their extracts were examined by intensive chromatographic methods. Eighty-four compounds including fifty new briaranes were isolated, and parts of their biological activities were studied.
Natural products investigation of the Taiwanese gorgonian octocoral Junceella fragilis found fifteen new briarane-type diterpenes, namely frajunolides E-S (1-15), ninteen known briaranes, eg. junceellin, junceellolides A-E、junceellolide K, 11α,20α-epoxy-4-deacetoxyjuncellolide D, umbraculolide A, junceellonoid A, juncin P, juncins Y-ZI, frajunolides A-D and praelolide, and a sterol, ergosterol peroxide. Soft coral B. violacea (Quoy and Gaimard) of Taiwan has isolated thirty-five new briarane-type diterpenoids, briaviolides A-Z (16-41) and viobrianolides A-I (42-50), in addition to fourteen known diterpene lactones, stylatulide lactone, excavatolide A, 9-deacetylstylatulide lactone, 4β-acetoxy-9-deacetylstylatulide lactone、 Brianthein Z、, renillafoulin A, braexcavatolide E, braexcavatolide I, minabein-4, minabein-6, milolide K, solenolide A, and solenolides D-E.
Structures of all above compounds were examined by physical and spectroscopic analyses including mass, IR, UV spectra, optical rotation and 1D, 2D NMR, as well as in comparison with the published data. Moreover, the structures of compounds 16, 32 and prarlolide were further confirmed by single X-ray crystallographic analysis. The stereochemistry of these compounds was investigated by NOESY method, and the configuration of compounds 32-38 were determined by Circular Dichroism spectroscopic analysis.
Cytotoixcity and in vitro anti-inflammatory activities were studied by Dr. Kuo, Yao-Haur and Dr. Hwang, Tsong-Long, respectively. Junceellin, junceellolide B and juncin ZI exhibited weak cytotoxicity against Hep2 (Human laryngeal carcinoma), Doay (Human medulloblastoma), WiDr (Human colon adenocarcinoma), Hela (Human cervical epitheloid carcinoma). The in vitro anti-inflammatory activities of 1-7 were evaluated for inhibition of elastase release and for the generation of superoxide anion, as tested on human neutrophils. Compounds 1 and 6 exhibited weak inhibition of elastase release and superoxide anion at 10 μg/mL. The biological activity analysis of compounds 16-50 are in progress.

中文摘要 I
英文摘要 III
化合物1-51之結構 V
第一章、緒論
第一節、前言------------------------------------------------------------------------------1
第二節、研究動機、目的與展望------------------------------------------------------5
第三節、軟珊瑚之Briarane-type天然物文獻結構回顧--------------------------7

第二章、實驗材料與方法
第一節、實驗程序----------------------------------------------------------------------71
第二節、軟珊瑚樣品採集與分類地位
(一)、白蘆莖柳珊瑚(Junceella fragilis)---------------------------------------72
(二)、皮柳珊瑚(Briareum violacea)--------------------------------------------73
第三節、天然物之萃取、分離與純化
(一)、白蘆莖柳珊瑚(Junceella fragilis) --------------------------------------76
(二)、皮柳珊瑚(Briareum violacea) -------------------------------------------80
第四節、實驗設備儀器、溶劑與藥品
(一)、實驗設備-----------------------------------------------------------------84
(二)、矽膠與溶劑部分--------------------------------------------------------85
(三)、軟體部分-----------------------------------------------------------------86
第五節、生物活性測試方法
(一)、細胞毒殺活性測試-----------------------------------------------------87

第三章、實驗結果與結論
第一節、白蘆莖柳珊瑚(Junceella fragilis)部分
Frajunolides E (1)、J (6)、L (8)之結構解析--------------------------89
Frajunolide F (2)之結構解析--------------------------------------------108
Frajunolides G (3)、K (7)、M (9)之結構解析-----------------------117
Frajunolides H (4)、I (5)、N (10)之結構解析-----------------------139
Frajunolide O (11)之結構解析------------------------------------------160
Frajunolide P (12)之結構解析------------------------------------------169
Frajunolide Q (13)之結構解析-----------------------------------------175
Frajunolides R (14)、S (15)之結構解析------------------------------182
第二節、皮柳珊瑚(Briareum violacea)部分
Briaviolides A-C (16-18)與Benzoyl briaviolide A (51)之結構解析
---------------------------------------------------------------------------------195
Briaviolides D-F (19-21)之結構解析----------------------------------218
Briaviolides G-K (22-26)之結構解析----------------------------------238
Briaviolides L-P (27-31)之結構解析-----------------------------------267
Briaviolides Q-W (32-38)之結構解析---------------------------------296
Briaviolides X-Z (39-41)之結構解析----------------------------------339
Viobrianolides A-B (42-43)之結構解析-------------------------------359
Viobrianolide C (44)之結構解析---------------------------------------371
Viobrianolide D (45)之結構解析---------------------------------------377
Viobrianolide E (46)之結構解析----------------------------------------384
Viobrianolide F (47)之結構解析----------------------------------------391
Viobrianolide G (48)之結構解析---------------------------------------397
Viobrianolide H (49)之結構解析---------------------------------------405
Viobrianolide I (50)之結構解析----------------------------------------413
第三節、活性測試結果
(一)、白蘆莖柳珊瑚(Junceella fragilis)---------------------------------420
(二)、皮柳珊瑚(Briareum violacea)-------------------------------------422
第四節、結論與討論-------------------------------------------------------------------423

第四章、參考文獻----------------------------------------------------------------------------427

附錄、研究成果目錄-------------------------------------------------------------------------440

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