發現新奇的化學結構並且具有特殊生物活性的二次代謝物，是天然
物研究者的重要課題。Sinularia 屬之軟珊瑚在過去研究中被發現其二
次代謝物的化學成分結構非常的多樣化，其中包括 sesquiterpenoids,
diterpenoids, 和 steroids 等多種骨架化合物且具有生物活性。我們從
採集自東沙群島的軟珊瑚Sinularia capillosa 中，分離出十個天然二次
代謝物，其中五個新的化合物(1–5)中包括一個含有quinone 取代的
diterpene (tetraprenylbenzoquinone) (1) ， 兩個同時含有furan 和
hydroquinone 取代的化合物 (2 和3)，一個具有furan 取代的
sesquiterpene (4)，且一個從未被發現過的sesquiterpene 類的新骨架
(5)，以及五個已知的二次代謝物(6–10)包括一個furanosesquiterpene
類的化合物 (6)，兩個furanobenzoquinone 類的化合物 (7 和 8)，一
個六環接γ-lactone ring 的結構loliolide (9) 和一個bicyclic
sesquiterpene 類的化合物 (10)。我們利用1H-NMR、13C-NMR、
COSY、HSQC、HMBC、NOESY、IR、UV、CD、質譜及旋光來進
行化學結構解析。針對這些代謝物我們也進行了癌細胞毒殺、抗發炎
活性及人類巨細胞病毒的抑制等活性測試。

To discover novel and bioactive secondary metabolites is a main
mission for natural product researchers. Soft corals of the genus Sinularia
were proved to yield a wide variety of secondary metabolites including
sesquiterpenoids, diterpenoids and steroids. In the thesis, the chemical
examinations on the organic extracts of the soft coral Sinularia capillosa
(collected at Dongsha Islands) resulted in the isolation of ten secondary
metabolites (1–10) including five new secondary metabolites (1–5) and
five known metabolites (6–10). The new secondary metabolites included
one new tetraprenylbenzoquinone (1), two furanobenzosesquiterpene (2,
3), one furanosesquiterpene (4), and a novel sesquiterpene (5). The
known metabolites included an acid-substituted furanosesquiterpene (6),
two furanobenzosesquiterpenes (7, 8), loliolide (9), and the known
sesequiterpene (10). The structures of the isolated secondary metabolites
were elucidated by 1H-NMR, 13C-NMR, COSY, HSQC, HMBC, NOESY,
IR, UV, CD, MS, and optical rotation. The cytotoxicities against cancer
cells, anti-inflammatory effects, and anti-HCMV (human
cytomegalovirus) activities of these isolated metabolites were evaluated.

1. Introduction 1
2. Literature Review 3
2.1 Literature Review of Sinularia capillosa 3
2.2 Literature Review of Marine Meroterpenoids 6
2.3 Literature Review of Marine Furanosesquiterpenoids 10
3. Experimental Section 12
3.1 General Experimental Procedures 12
3.2 Animal Materials 13
3.3 Extraction and Isolation 14
3.4 Cytotoxicity Testing 17
3.5 In Vitro Anti-inflammatory Assay 18
3.6 Plaque reduction assay 20
4. Results and Discussion 21
4.1 Structural Elucidation of Capilloquinone (1) 21
4.2 Structural Elucidation of Capillobenzopyranol (2) 36
4.3 Structural Elucidation of Capillobenzofuranol (3) 55
4.4 Structural Elucidation of Capillofuranocarboxylate (4) 71
4.5 Structural Elucidation of Capillosanol (5) 85
4.6 Identification of Known Compound 6 100
4.7 Identification of Known Compound 7 116
4.8 Identification of Known Compound 8 135
4.9 Identification of Known Compound 9 151
4.10 Identification of Known Compound 10 167
4.11 Biological Activity of Metabolites 1−10 181
5. Conclusion 184
6. Cited Literatures 186

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