近年來，從軟珊瑚中已分離出許多具有生物活性的二次代謝物，
為了尋找更多具有生物活性的二次代謝物，我們針對軟珊瑚Sinularia
gyrosa 有機萃取層的化學成分進行研究，從中分離得到六個新的
norcembranoid 類化合物，命名為gyrosolides A–F (1–6)和兩個新的
diterpenoid 類化合物，命名為gyrosanols A–B (7 和8)，及十一個已知
的norcembranoid 類化合物(9–19)。這些純化的化合物結構鑑定是透
過各種光譜(一維1H 和 13C NMR、二維1H–1H、COSY、二維HMQC、
二維HMBC、二維NOESY、紫外線光譜、紅外線光譜、CD 光譜及
質譜等)及物理性質(旋光等)的分析，配合Chem Draw 3D 的MM2
去計算最低能階，並且與相關文獻之數據比對來決定。我們透過
NOESY 及3D Chem Draw MM2 force field calculations 將化合物14 的
結構重新解析。針對這些代謝物進行抗發炎活性、老鼠血癌細胞
(P-388)和人類大腸癌細胞(HT-29)以及人類肺腺癌細胞(A-549)的癌細
胞毒殺活性、人類巨細胞病毒(HCMV)的抑制等活性測試，我們發現
代謝物9 對抗發炎、老鼠血癌細胞及人類巨細胞病毒皆具有顯著的活
性。

Numerous bioactive secondary metabolites have been isolated from the
soft coral in recent years. In order to search for more bioactive secondary
metabolites, we have investigated the chemical constituents of the organic
extracts soft coral Sinularia gyrosa, collected at Dongsha island.
Chromatography separation have led to the isolation of six new
norcembranoid compounds, gyrosolides A–F (1–6), and two new
diterpenoids, gyrosanols A and B (7 and 8), as well as eleven known
norcembranoids (9–19). The chemical structures and configurations of
pure compounds were determined by NMR spectroscopic (1H NMR, 13C
NMR, 1H–1H COSY, HMQC, HMBC, NOESY, UV, IR, CD, and mass
spectra) and physical data (optical rotations), 3D Chem Draw MM2 force
field calculations, as well as comparison with the spectroscopic data
reported by literature. The structure of known compound 14 was revised
by NOESY and 3D Chem Draw MM2 force field calculations. The
anti-inflammatory effects, cytotoxicity aganist of P-388 (mouse
lymphocytic leukemia), HT-29 (human colon adenocarcinoma), and
A-549 (human lung epithelial carcinoma) cells, and anti-HCMV (human
cytomegalovirus) activity of these secondary metabolites were evaluated.
Metabolite 9 exhibited significant activity against HCMV and
cytotoxicity against A-549 cell lines, and significantly exhibited the
COX-2 protein expression by LPS stimulation.

1. Introduction 1
2. Literature Review 3
2.1 Literature review of secondary metabolites from the Sinularia gyrosa 3
2.2 Literature review of the marine norditerpenes from the genus Sinularia 3
2.3 Literature review of the marine lobane diterpenes 10
3. Experimental Section 15
3.1. General Experimental Procedures 15
3.2. Solvent for Chromatography 16
3.3. Animal Materials 16
3.4. Extraction and Isolation 17
3.5. In Vitro Anti-inflammatory Assay 21
3.6. Cytotoxicity Testing 22
3.7. Plaque reduction assay 24
4. Results and Discussion 25
4.1 Structural Elucidation of Gyrosolide A (1) 25
4.2 Structural Elucidation of Gyrosolide B (2) 40
4.3 Structural Elucidation of Gyrosolide C (3) 55
4.4 Structural Elucidation of Gyrosolide D (4) 69
4.5 Structural Elucidation of Gyrosolide E (5) 84
4.6 Structural Elucidation of Gyrosolide F (6) 101
4.7 Structural Elucidation of Gyrasanol A (7) 119
4.8 Structural Elucidation of Gyrosanol B (8) 138
4.9 Identification of Known Compound 9 159
ix
4.10 Identification of Known Compound 10 166
4.11 Identification of Known Compound 11 173
4.12 Identification of Known Compound 12 181
4.13 Identification of Known Compound 13 188
4.14 Structure Revision of Known Compound 14 195
4.15 Identification of Known Compound 15 202
4.16 Identification of Known Compound 16 209
4.17 Identification of Known Compound 17 216
4.18 Identification of Known Compound 18 223
4.19 Identification of Known Compound 19 230
4.20 Biological Activity of Metabolites 1-19 237
5. Conclusion 240
6. Cited Literatures 242

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