本論文主要是在研究Cespitularia hypotentaculata Roxas、C. taeniata May與Junceella juncea等三種台灣產軟珊瑚以及台灣產紅花八角Illicium arborescens Hayata。對這些樣本，利用各種色層分析方式進行分離純化，並分析鑑定所含的化學組成成分，共計分離得到三十五個天然物，其中包括二十個新化合物，並對分離到的化合物進行其抗癌活性分析。

在研究期間中由Cespitularia hypotentaculata與C. taeniata共分離出二十個化合物，其中包括十個新的雙萜類化合物，將其命名為cespihypotins B、W-Z (6, 1-4)、cespihypotone (5)、cespitaenins A、F-H (10、7-9)以及十四個已知化合物 (21-34)。其中C. hypotentaculata所分離出的化合物1-3為norverticillane骨架，化合物4-6為verticillane骨架；C. taeniata所分離出的化合物7與10為norverticillane骨架，化合物8-9為verticillane骨架，並且化合物8為少見之C-9/C-10斷鍵之化合物。對Junceella juncea共分離出四個化合物，包括三個新的化合物 juncenolides L-N (11-13)與一個已知化合物(35)，這些化合物皆屬於briarane骨架的diterpene類化合物。

在紅花八角（Illicium arborescens Hayata）中，共分離出七個新化合物，其中包括兩個新的phytoquinoid立體異構物，2,3-Didehydro-5-O-methyl-11-epi-illi-
funone E (14)與2,3-Didehydro-5-O-methylillifunone E (15)，以及五個新的sesquiterpene lactones (8,9-secoprezizaane-type sesquiterpenes)(16-20)。

上述所有化合物的結構均是由IR、Mass、UV與旋光值等物理數據，配合各種NMR圖譜，並且比對文獻上相關化合物的數據來定立的。在細胞毒殺活性方面，由國立中國醫藥研究所郭曜豪老師實驗室及長庚大學黃聰龍老師進行測試，
針對人類乳癌細胞 (MCF-7)、人類骨髓癌細胞 (Daoy)、人類結腸癌細胞 (WiDr)與人類子宮頸癌細胞 (Hela) 四種癌細胞株以及針對MLP/CB誘導之人類中性白血球的超氧化離子產生(superoxide anion generation)與彈性蛋白酶釋出(elastase release)進行活性測試，其中化合物9-12針對FMLP/CB誘導之人類中性白血球的超氧化離子產生(superoxide anion generation)具有微弱活性，其在10 μg/mL 下的抑制表現依序為6.19、6.72、7.56、6.72，化合物14及19針對人類乳癌細胞 (MCF-7)、人類骨髓癌細胞 (Daoy)、人類結腸癌細胞 (WiDr) 與人類子宮頸癌細胞 (Hela)具有中度活性，化合物14針對上述四種細胞株的IC50值分別為9.0、7.1、11.2、10.9 μg/mL，化合物19針對上述四種細胞株的IC50值分別為5.1、6.3、10.9、6.24 μg/mL。

This dissertation mainly discussed the investigation of three different kinds of Formosan soft corals, Cespitularia hypotentaculata Roxas, C. taeniata May and Junceella juncea, as well as Formosan star-anise, Illicium arborescens Hayata. Their EtOAc extracts were investigated by intensive chromatography. Twenty new natural products were isolated and purified and their biological activities were studied.

The chemical investigation of soft coral Cespitularia hypotentaculata and C. taeniata resulted in the isolation of twenty natural products, including ten new natural products, designated as cespihypotins B, W–Z (6, 1 – 4), cespihypotone (5), cespitaenins A (10) and F-H (7-9) as well as fourteen know compounds (21-34). Compounds 1-3 were nor-verticillane-type nor-diterpenes. Compounds 4-6 were verticillane-type diterpenes. Cespitaenins A and F (10 & 7) were nor-verticillane-type nor-diterpenes. Cespitaenins G and H (8 & 9) were verticillane-type diterpenes. Three new briarane-type natural products, juncenolides L-N（11-13） toghther with and one know compound (35) were isolated from Junceella juncea.

The study of Formosan star anise, Illicium arborescens Hayata has afforded seven new compounds (14-20). Two of them were stereoisomer, named 2,3-dide-
hydro-5-O-methyl-11-epiillifunone E (14) and 2,3-Didehydro-5-O-methylillifunone E (15). The others were 8,9-secoprezizaane-type sesquiterpenes (16-20).

All the structures of above compounds were elucidated by physical and spectroscopic analyses (IR, mass, UV, optical rotation and NMR), and also by comparisions with the published data. Cytotoxicity and in vitro anti-inflammatory activities were measured by Dr. Yao-Haur Kuo of National Research Institute of Chinese Medicine and Dr. Tsong-Long Hwang of Chang Gung University. The biological activities of compounds against MCF-7 (Human breast adenocarcinoma), Doay (Human medulloblastoma), WiDr (Human colon adenocarcinoma), Hela (Human cervical epitheloid carcinoma) cell lines and effects of compounds on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB. were tested. The effects of compounds 9-12 on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB were 6.19, 6.72, 7.56 and 6.72 respectively. The IC50 of compounds 14 and 19 against MCF-7, Doay, WiDr and Hela were 9.0, 7.1, 11.2, 10.9 and 5.1, 6.3, 10.9, 6.24 μg/mL, respectively.

目 錄
摘要 III
英文摘要 V
第一章、台灣產叢羽軟珊瑚與紅蘆莖軟珊瑚之天然物成份研究
壹、緒論
一、前言 1
二、相關化合物文獻回顧
第一節 Cespitularia 屬 4
第二節 Junceella屬 16
三、研究動機與目的 28
貳、材料與方法
一、物種型態 30
二、分類地位
第一節 Cespitularia sp.珊瑚之分類地位 32
第二節 Junceella juncea 珊瑚之分類地位 32
三、分離與純化
第一節Cespitularia sp. 軟珊瑚 33
第二節Junceella juncea 柳珊瑚 37
參、研究結果
一、Cespitularia hypotentaculata與C. taeniata的成份研究
Cespihypotin W (1)之結構解析 40
Cespihypotin X (2)之結構解析 47
Cespihypotin Y (3)之結構解析 54
Cespihypotin Z (4)之結構解析 61
Cespihypotone (5)之結構解析 68
Cespihypotin B (6)之結構解析 75
Cespitaenin F (7)之結構解析 78
Cespitaenin G (8)之結構解析 85
Cespitaenin H (9)之結構解析 94
Cespitaenin A (10)之結構解析 101
二、紅蘆莖柳珊瑚 Junceella juncea 的成分研究
Juncenolide M (11) 之結構解析 109
Juncenolide N (12) 之結構解析 117
Juncenolide O (13) 之結構解析 124

第二章、台灣產紅花八角之天然物研究
壹、緒論
一、前言 132
二、相關化合物文獻回顧 134
三、研究動機與目的 147
貳、材料與方法
一、物種型態 148
二、分類地位
Illicium arborescens之分類地位 149
三、分離與純化 150

參、研究結果
2,3-Didehydro-5-O-methyl-11-epiillifunone E (14)之結構解析 153
2,3-Didehydro-5-O-methylillifunone E (15)之結構解析 160
14-O-Benzoylminwanensin (16) 之結構解析 167
3-O-Acetyl-14-O-benzoylminwanensin (17) 之結構解析 174
(3β)-14-O-Benzoyl-10-deoxy-3-hydroxyfloridanolide (18) 之結構解析 181
3-O-Acetyl-14-O-benzoyl-10-deoxyfloridanolide (19) 之結構解析 189
7-O-Acetyldunnianin (20) 之結構解析 196
第三章、結論 203
第四章、參考文獻 206
附錄一 Mosher’s method 216
附錄二 個人著作 217
附錄三 專有名詞縮寫與全稱對照 218

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