本研究主要是針對採自台灣東岸-基翬漁港的軟珊瑚 Sinularia nanolobata 的有機萃取物，從中尋找含有生物活性的化學成分。目前研究分離得到七個新的天然化合物 (1–7)，包含三個cubitane diterpenoid 類化合物 nanolobone A–C (1–3)、三個cembrane 類的化合物nanolobol A–C (4–6)和一個steroid glycoside 類的化合物24-methylenecholest-5-ene-3β, 11α,16β-diol-3-O-α-L-fucoside (7)以及十二個已知的化合物8–19。其中nanolobone A–C為不規則的12個碳數的cubitane環狀結構，這種骨架的化合物最早於1978年首次分離自東非Termite。另外這次也有分離到的nanolobol A–C屬於19號位置甲基被氧化的cembranoid類化合物，根據文獻之前並沒有在cembrane類型化合物中被發現過。
此次報告中的化合物均藉由光譜資料分析 (NMR、MS、IR、旋光) 及比對文獻上已知化合物的結構和數據資料來確立。並將所獲得的化合物2–5、7–19針對3種癌細胞株，分別是老鼠血癌細胞 (P-388)、人類慢性白血病细胞 (K-562)、人類大腸癌細胞 (HT-29) 的毒殺活性與抗發炎活性進行測試。結果顯示化合物16對於P-388、K-562和HT-29具有細胞毒殺活性，半數抑制濃度 (IC50) 的數值分別為15.54 ± 2.26, 15.83 ± 4.51 和 12.62 ± 3.27 μM。而在抗發炎的活性試驗中，針對2–19進行測試，同樣地化合物16對超氧化物和彈性蛋白酶有抑制的活性，半抑制濃度分別為14.87 ± 1.43和6.55 ± 1.01 μM。

Investigation on the chemical constituents of the ethyl acetate extract of the soft coral Sinularia nanolobata, led to the isolation of seven new compounds, including three new cubitane-type diterpenoids, nanolobones A–C (1–3), three new cembrane-type diterpenoids, nanolobols A–C (4–6) and a new steroid glycoside 24-methylenecholest-5-ene-3β,11α,16β-diol
-3-O-α-L-fucoside (7) along with twelfth know compounds. nanolobones A–C are new examples of diterpenoids of the irregular cubitane ring system, which was first isolated in 1978 from the East African termite. In addition, nanolobols A–C featured unusual 19-oxygenated functionalities, which are rarely found from cembranoid analogues.
The structures of these compounds were elucidated on the basis of spectroscopic methods and by comparison with those of the related known compounds. The cytotoxicity of compounds 2– 5, 7–19 against the growth of three cancer cell lines, including murine leukemia (P-388), human chronic myelogenous leukemia (K-562) and human colon carcinoma (HT-29) cell lines were determined. The results showed that compound 16 exhbited cytotoxic activity toward P-388, K-562, HT-29 cancer cell lines with IC50 values of 15.54 ± 2.26, 15.83 ± 4.51 and 12.62 ± 3.27 μM, respectively. The anti-inflammation activity of compounds 2–19 was also studied. Compound 16 was found to inhibit the production of superoxide anion and elastase with IC50 values of 14.87 ± 1.43 and 6.55 ± 1.01 μM, respectively.

目 錄 頁 次
論文審定書 i
謝辭 ii
中文摘要 iii
英文摘要 iv

化合物1−19化學結構 v

圖次 x

表次 xv

第一章、緒論 1
第一節、前言及研究動機 1
第二節、文獻回顧 5
第二章、生物材料與研究方法 49
第一節、Sinularia nanolobata 樣品採集時間、地點、分類地位及
實驗流程 49
第二節、Sinularia nanolobata的分離流程 52
第三節、實驗設備儀器及材料 53
2.3.1實驗設備儀器 53
2.3.2實驗材料 54
第三章、化合物之結構證明 56
第一節：軟珊瑚Sinularia nanolobata 所分離出之化合物的結構證明 56
(一)、Nanolobone A (1) 化合物構造之解析 56
(二)、Nanolobone B (2) 化合物構造之解析 66
(三)、Nanolobone C (3) 化合物構造之解析 79
(四)、Nanolobol A (4) 化合物構造之解析 89
(五)、Nanolobol B (5) 化合物構造之解析 99
(六)、Nanolobol C (6) 化合物構造之解析 109
(七)、24-Methylenecholest-5-ene-3β,11α,16β-diol-3-O-α-
L-fucoside (7) 化合物構造之解析 119
(八)、Calyculone I (8) 化合物構造之解析 130
(九)、Sinulariol C (9) 化合物構造之解析 134
(十)、24-Methylenecholest-5-ene-3β-diol-3-O-α-L-fucoside (10) 化合物構造之解析 138
(十一)、24-Methylenecholest-5-ene-3β,16β-diol-3-O-α-L-fucoside (11) 化合物構造之解析 142
(十二)、3β,11-Dihydroxy-5β,6β-epoxy-24-methylene-9, 11-secocholestan-9-one (12) 化合物構造之解析 146
(十三)、Crassarosterol A (13) 化合物構造之解析 150
(十四)、3β,7α- Dihydroxyergosta-5,24 (28)-diene (14) 化合物構造之解析 154
(十五)、3β,7α- Dihydroxyergosta-5,24 (28)-diene (15) 化合物構造之解析 159
(十六)、3β, 11-Dihydroxy-5β, 6β-epoxy-24-methylene-9, 11-
secocholestan-9-one (16) 化合物構造之解析 164
(十七)、Crassarosterol A (17) 化合物構造之解析 168
(十八)、3β, 7α- Dihydroxyergosta-5, 24 (28)-diene (18) 化合物構造之解析 172
(十九)、3β, 7α- Dihydroxyergosta-5, 24 (28)-diene (19) 化合物構造之解析 176

第二節：化合物物理性質及圖譜數據整理 180
第四章、生物活性試驗方法 184
第一節：生物活性試驗方法 184
第二節：生物活性試驗結果 188
第五章、結論 191
第六章、參考文獻 194



圖 次
Figure 1-1. 核苷類化合物的結構圖 2
Figure 2-1-1. Sinularia nanolobata 圖 51
Figure 2-1-2.實驗流程圖 51
Figure 2-2-1. Sinularia nanolobata 軟珊瑚的分離流程(A) 52
Figure 2-2-2. Sinularia nanolobata 軟珊瑚的分離流程(B) 52
Figure 2-2-3. Sinularia nanolobata 軟珊瑚的分離流程(C) 53
Figure 3-1-1. 1H-1H COSY and HMBC correlations for 1. 57
Figure 3-1-2. Selective NOE correlations for 1. 58
Figure 3-1-3. IR spectrum of 1. 60
Figure 3-1-4. ESIMS spectrum of 1. 60
Figure 3-1-5. HRESIMS spectrum of 1. 61
Figure 3-1-6. 1H-NMR spectrum of 1 in CDCl3. 61
Figure 3-1-7. 1H-NMR (2.6~6.3 ppm) spectrum of 1 in CDCl3. 62
Figure 3-1-8. 13C-NMR spectrum of 1 in CDCl3. 62
Figure 3-1-9. DEPT spectrum of 1 in CDCl3. 63
Figure 3-1-10. HMQC spectrum of 1 in CDCl3. 63
Figure 3-1-11. 1H-1H COSY spectrum of 1 in CDCl3. 64
Figure 3-1-12. HMBC spectrum of 1 in CDCl3. 64
Figure 3-1-13. NOESY spectrum of 1 in CDCl3. 65
Figure 3-2-1. 1H-1H COSY and HMBC correlations for 2. 67
Figure 3-2-2. Selective NOE correlations for 2. 68
Figure 3-2-3. 化合物2的立體異構物 70
Figure 3-2-4. IR spectrum of 2. 73
Figure 3-2-5. ESIMS spectrum of 2. 73
Figure 3-2-6. HRESIMS spectrum of 2. 74
Figure 3-2-7. 1H-NMR spectrum of 2 in CDCl3. 74
Figure 3-2-8. 1H-NMR spectrum of 2 in CDCl3. 75
Figure 3-2-9. 1H-NMR spectrum of 2 in CDCl3. 75
Figure 3-2-10. 13C-NMR spectrum of 2 in CDCl3. 76
Figure 3-2-11. DEPT spectra of 2 in CDCl3. 76
Figure 3-2-12. HMQC spectrum of 2 in CDCl3.21 77
Figure 3-2-13. 1H-1H COSY spectrum of 2 in CDCl3. 77
Figure 3-2-14. HMBC spectrum of 2 in CDCl3. 78
Figure 3-2-15. NOESY spectrum of 2 in CDCl3. 78
Figure 3-3-1. 1H–1H COSY and HMBC correlations for 3. 80
Figure 3-3-2. Selective NOESY correlations for 3. 81
Figure 3-3-3. IR spectrum of 3. 83
Figure 3-3-4. ESIMS spectrum of 3. 83
Figure 3-3-5. HRESIMS spectrum of 3. 84
Figure 3-3-6. 1H-NMR spectrum of 3 in CDCl3. 84
Figure 3-3-7. 1H-NMR (3.5~6.7 ppm) spectrum of 3 in CDCl3. 85
Figure 3-3-8. 13C-NMR spectrum of 3 in CDCl3. 85
Figure 3-3-9. DEPT spectra of 3 in CDCl3. 86
Figure 3-3-10. HMQC spectrum of 3 in CDCl3. 86
Figure 3-3-11. 1H–1H COSY spectrum of 3 in CDCl3. 87
Figure 3-3-12. HMBC spectrum of 3 in CDCl3. 87
Figure 3-3-13. NOESY spectrum of 3 in CDCl3. 88
Figure 3-4-1. 1H–1H COSY and selective HMBC correlations of 4. 90
Figure 3-4-2. Selected NOESY correlations of 4. 91
Figure 3-4-3. IR spectrum of 4. 93
Figure 3-4-4. ESIMS spectrum of 4. 93
Figure 3-4-5. HRESIMS spectrum of 4. 94
Figure 3-4-6. 1H-NMR spectrum of 4 in CDCl3. 94
Figure 3-4-7. 1H-NMR (5.3~7.4 ppm) spectrum of 4 in CDCl3. 95
Figure 3-4-8. 1H-NMR (2.8~6.5 ppm) spectrum of 4 in CDCl3. 95
Figure 3-4-9. 13C-NMR spectrum of 4 in CDCl3. 96
Figure 3-4-10. DEPT spectra of 4 in CDCl3. 96
Figure 3-4-11. HMQC spectrum of 4 in CDCl3. 97
Figure 3-4-12. 1H–1H COSY spectrum of 4 in CDCl3. 97
Figure 3-4-13. HMBC spectrum of 4 in CDCl3. 98
Figure 3-4-14. NOESY spectrum of 4 in CDCl3. 98
Figure 3-5-1. 1H–1H COSY and HMBC correlations of 5. 100
Figure 3-5-2. Selected NOE correlations for 5 101
Figure 3-5-3. IR spectrum of 5. 103
Figure 3-5-4. ESIMS spectrum of 5. 103
Figure 3-5-5. HRESIMS spectrum of 5. 104
Figure 3-5-6. 1H-NMR spectrum of 5 in CDCl3. 104
Figure 3-5-7. 1H-NMR (2.5~6.5 ppm) spectrum of 5 in CDCl3. 105
Figure 3-5-8. 13C NMR spectrum of 5 in CDCl3. 105
Figure 3-5-9. DEPT spectrum of 5 in CDCl3. 106
Figure 3-5-10. HMQC spectrum of 5 in CDCl3. 106
Figure 3-5-11. 1H–1H COSY spectrum of 5 in CDCl3. 107
Figure 3-5-12. HMBC spectrum of 5 in CDCl3. 107
Figure 3-5-13. NOESY spectrum of 5 in CDCl3. 108
Figure 3-6-1. 1H–1H COSY and selective HMBC correlations of 6. 110
Figure 3-6-2. Selected NOESY correlations of 6. 111
Figure 3-6-3. IR spectrum of 6. 113
Figure 3-6-4. ESIMS spectrum of 6. 113
Figure 3-6-5. HRESIMS spectrum of 6. 114
Figure 3-6-6. 1H-NMR spectrum of 6 in CDCl3. 114
Figure 3-6-7. 1H-NMR (1.5~3.0 ppm) spectrum of 6 in CDCl3. 115
Figure 3-6-8. 1H-NMR (3.0~6.0 ppm) spectrum of 6 in CDCl3. 115
Figure 3-6-9. 13C-NMR spectrum of 6 in CDCl3. 116
Figure 3-6-10. DEPT spectra of 6 in CDCl3. 116
Figure 3-6-11. HSQC spectrum of 6 in CDCl3. 117
Figure 3-6-12. 1H–1H COSY spectrum of 6 in CDCl3. 117
Figure 3-6-13. HMBC spectrum of 6 in CDCl3. 118
Figure 3-6-14. NOESY spectrum of 6 in CDCl3. 118
Figure 3-7-1. 1H–1H COSY and selective HMBC correlations of 7. 120
Figure 3-7-2. Selected NOESY correlations of 7. 121
Figure 3-7-3. IR spectrum of 7. 123
Figure 3-7-4. ESIMS spectrum of 7. 124
Figure 3-7-5. HRESIMS spectrum of 7. 124
Figure 3-7-6. 1H-NMR spectrum of 7 in CDCl3 125
Figure 3-7-7. 1H-NMR (0.8~2.8 ppm) spectrum of 7 in CDCl3 125
Figure 3-7-8. 1H-NMR (3.4~5.8 ppm) spectrum of 7 in CDCl3 126
Figure 3-7-9. 13C-NMR spectrum of 7 in CDCl3 126
Figure 3-7-10. DEPT spectra of 7 in CDCl3. 127
Figure 3-7-11. HSQC spectrum of 7 in CDCl3. 127
Figure 3-7-12. 1H–1H COSY spectrum of 7 in CDCl3. 128
Figure 3-7-13. HMBC spectrum of 7 in CDCl3. 128
Figure 3-7-14. NOESY spectrum of 7 in CDCl3. 129
Figure 3-8-1. ESIMS spectrum of 8. 132
Figure 3-8-2. 1H NMR spectrum of 8. 132
Figure 3-8-3. 13C NMR spectrum of 8. 133
Figure 3-9-1. ESIMS spectrum of 9. 136
Figure 3-9-2. 1H-NMR spectrum of 9. 136
Figure 3-9-3. 13C-NMR spectrum of 9. 137
Figure 3-10-1. ESIMS spectrum of 10. 140
Figure 3-10-2. 1H-NMR spectrum of 10. 140
Figure 3-10-3. 13C-NMR spectrum of 10. 141
Figure 3-11-1. ESIMS spectrum of 11. 144
Figure 3-11-2. 1H-MR spectrum of 11. 144
Figure 3-11-3. 13C-MR spectrum of 11. 145
Figure 3-12-1. ESIMS spectrum of 12. 148
Figure 3-12-2. 1H-NMR spectrum of 12. 148
Figure 3-12-3. 13C-NMR spectrum of 12. 149
Figure 3-13-1. ESIMS spectrum of 13. 152
Figure 3-13-2. 1H-NMR spectrum of 13. 152
Figure 3-13-3. 13C-NMR spectrum of 13. 153
Figure 3-14-1. ESIMS spectrum of 14. 157
Figure 3-14-2. 1H-NMR spectrum of 14. 157
Figure 3-14-3. 13C-NMR spectrum of 14. 158
Figure 3-15-1. ESIMS spectrum of 15. 162
Figure 3-15-2. 1H-NMR spectrum of 15. 162
Figure 3-15-3. 13C-NMR spectrum of 15. 163
Figure 3-16-1. ESIMS spectrum of 16. 166
Figure 3-16-2. 1H-NMR spectrum of 16. 167
Figure 3-16-3. 13C-NMR spectrum of 16. 167
Figure 3-17-1. ESIMS spectrum of 17. 170
Figure 3-17-2. 1H-NMR spectrum of 17. 171
Figure 3-17-3. 13C-NMR spectrum of 17. 171
Figure 3-18-1. ESIMS spectrum of 18. 174
Figure 3-18-2. 1H-NMR spectrum of 18. 174
Figure 3-18-3. 13C-NMR spectrum of 18. 175
Figure 3-19-1. ESIMS spectrum of 19. 178
Figure 3-19-2. 1H-NMR spectrum of 19. 179
Figure 3-19-3. 13C-NMR spectrum of 19. 179

1. 楊秀偉，天然藥物化學發展的歷史性變遷，北京大學學報（醫學版），2004，36，9-11。
2. Sertürner, F. W. “The inventor of morphine.” Orv Hetil. 1966, 107, 895-897.
3. Kijjoa, A.; Sawangwong, P. “Drugs and cosmetics from the sea.” Mar. Durgs. 2004, 2, 73–82.
4. Simmons, T. L.; Andrianasolo, E.; McPhail, K.; Flatt, P.; Gerwick,
W. H. “Marine natural products as anticancer drugs.” Mol. Cancer. Ther. 2005, 4, 333–342.
5. 戴昌鳳，台灣珊瑚圖鑑，貓頭鷹出版，2009年，4–7。
6. Yamada, K.; Ujiie, T.; Yoshida, K.; Miyamoto, T.; Higuchi, T.“Sinulobatins A ~ D, New Amphilectane-type Diterpenoids from the Japanese Soft Coral Sinularia nanolobata.” Tetrahedron. 1997, 53, 4569-4578.
7. Ahmed, A. F.; Su, J.-H.; Shiue, R.-T.; Pan, X.-J.; Dai, C.-F.; Kuo,
Y.-H.; Sheu, J.-H. “New -Caryophyllene-Derived Terpenoids from the Soft Coral Sinularia nanolobata.” J. Nat. Prod. 2004, 67,592-597.
8. Thebtaranonth, C.; Thebtaranonth, Y.; Wanauppathamkul, S.;
Yuthavong, Y. “Antimalarial sesquiterpenes from tubers of Cyperus rotundus: structure of 10,12-Peroxycalamenene, a sesquiterpeneendoperoxide.” Phytochemistry, 1995, 40, 125-128.
9. Tseng, Y.-J.; Wen, Z.-H.; Dai, C.-F.; Chiang, M.-Y.; Sheu, J.-H.“Nanolobatolide, a New C18 Metabolite from the Formosan Soft Coral Sinularia nanolobata.” Org. Lett. 2009, 11, 5030-5032.
10. Tseng, Y.-J.; Wang, S.-K.; Duh, C.-Y. “Secosteroids and
Norcembranoids from the Soft Coral Sinularia nanolobata.” Mar.Drugs. 2013, 11, 3288-3296.
11. 許復芸，台灣海域軟珊瑚Sinularia nanolobata所含二次代謝物之研究，國立中山大學海洋資源學系碩士論文，2013年。
12. Chen, S.-P.; Su, J.-H.; Ahmed, A. F; Dai, C.-F.; Wu, Y.-C.; Sheu,J.-H. “Xeniaphyllane-Derived Terpenoids from the Formosan Soft
Coral Sinularia gibberosa.” Chem. Pharm. Bull. 2007, 55,1471—1475.
13. Huang, S. X.; Yang, J.; Xiao, W. L.; Zhu, Y. L.; Li, R. T.; Li, L. M.; Sun, H. D. “Three Novel Terpenoids from Schisandra pubescens var. pubinervis.” Helvetica chimica acta. 2006, 89, 1169-1175.
14. Lakshmi, V.; Kumar, R. “Metabolites from Sinularia species.” Nat. Prod. Res. 2009, 23, 801–850.
15. Tursch, B.; Braekman, J.C.; Daloze, D.; Herin, M.; Karlsson, R.; Losman, D. “Chemical studies of marine invertebrates XI.
Sinulariolide, a new cembranolide diterpene from the soft coral
Sinularia flexibilis.” Tetrahedron. 1975, 31, 129–133.
16. Missakian, M.G.; Burreson, B.J.; Scheuer, P.J. “Pukalide, a
furanocembranolide from the soft coral Sinularia abrupta.” Tetrahedron. 1975, 31, 2513–2515.
17. Herin, M.; Colin, M.; Tursch, B. “Cembranoid constituents from the Australian collection of soft coral.” Bull. Soc. Chim. Belges. 1976, 85, 801–803.
18. Herin, M.; Tursch, B. “Studies of Australian soft corals XXIV. Two cembranoid diterpenes from the soft coral Sinularia facile.” Bull. Soc. Chim. Belges. 1976, 85, 707–719.
19. Kashman, Y.; Bonder, M.; Loya, Y.; Benayahu, Y. “A new sesquiterpene hydrocarbon from Sinularia polydactyla.” Isr. J. Chem. 1977, 16, 16–19.
20. Weinheimer, A.J.; Matson, A.J.; Hossain, M.B.; Van der Helm, D. “Marine anticancer agent: Sinularin and dihydrosinularin, new
cembranolides from the soft coral Sinularia flexibilis.” Tetrahedron Lett. 1977, 34, 2923–2926.
21. Kazlauskas, R.; Murthy, P.T.; Wells, R.J.; Schonholzer, P.; Coll, J.C. “Cembranoid constituents from an Australian collection of soft coral Sinularia flexibilis.” Aust. J. Chem. 1978, 31, 1817–1824.
22. Bruce, F.; Coll, J.C.; Hicks, W.; Kazlauskas, R.; Mitchell, S.J. “Studies of Australian soft corals X. The isolation of
epoxyisoneocembrene-A from Sinularia grayi and isoneocembrene-A from Sarchophyton Chrenberghi.” Aust. J. Chem. 1978, 31,2707–2712.
23. Bowden, B.F.; Coll, J.C.; Mitchell, S.J.; Mulder, J.; Stokie, G.J.“Studies of Australian soft corals IX. A novel nor-diterpene from the soft coral Sinularia leptoclados.” Aust. J. Chem. 1978, 31, 2049–2056.
24. Bowden, B.F.; Coll, J.C.; Mitchell, S.J.; Kazlauskas, R. “Studies of Australian soft corals XXXIV. Two cembranoid diterpenes from the soft coral Sinularia facile.” Aust. J. Chem. 1981, 34, 1551–1556.
25. Uchio, Y.; Nabeya, H.; Nakayama, M.; Hayashi, S.; Hase, T. “Cebrenene and mayol, two new cembranoid diterpenes from the soft coral Sinularia mayi.” Tetrahedron Lett. 1981, 22,1689–1690.
26. Long, K.; Longmei, Z.; Haihong, Z. “Studies on chemical
constituents of the Chinese soft coral V.” Zhongshan Daxue Xuebao, Ziran, Kexueben. 1981, 4, 105.
27. Mori, K.; Suzuki, S.; Iguchi, K.; Yamad, Y. “8,11-Epoxy bridged cembranolide diterpene from the soft coral Sinularia flexibilis.” Chem. Lett. 1983, 10, 1515–1516.
28. Aoki, M.; Kato, T.; Uchio, Y.; Nakayama, M.; Kadoma, M.“Characterization of 13-hydroxyneocembrene from soft corals.” Bull. Chem. Soc. Jpn. 1985, 58, 779–780.
29. Sato, A.; Fenical, W.; Qi-Tai, Z.; Clardy, J. “Norcembrene
diterpenoids from pacific soft corals of the genus Sinularia
(Alcyonacea, octocorallia).” Tetrahedron. 1985, 41, 4303–4308.
30. Lakshmi, V.; Schmitz, F.J . “Metabolites from two soft corals from Guam: Sinularia leptoclados and Sinularia gyrosa.” J. Nat. Prod.
1986, 49, 728–730.
31. Kobayashi, M.; Ishizaka, T.; Miura, N.; Mitsuhashi, H. “Marine
terpenes and terpenoids III, Isolation and structures of two cembrane diols from the soft coral Sinularia mayi.” Chem. Pharm. Bull. 1987, 35, 2314–2318.
32. Kusumi, T.; Ontani, I.; Inouye, Y.; Kakisawa, H. “Absoluteconfigurations of cytotoxic marine cembranolides, consideration of Mosher’s method.” Tetrahedron Lett. 1988, 29, 4731–4734.
33. Kobayashi, M. “Marine terpenes and terpenoids IV. Isolation of new cembranoids and secocembranoid lactones from the soft coral Sinularia mayi.” Chem. Pharm. Bull. 1988, 36, 488–494.
34. Kusumi, T.; Yauada, K.; Ishitsuka, M.O.; Fujita, Y.; Kakisawa, H.“New cembranoids from Okinawan soft coral Sinularia mayi.” Chem. Lett. 1990, 8, 1315–1318.
35. Iguchi, K.; Shimura, H.; Yamada, Y. “New cembrane type diterpenoids from the Okinawan soft coral Sinularia species.” J. Nat. Prod. 1992, 55, 1779–1782.
36. Iguchi, K.; Nishimura, K.; Yamazaki, K.; Iwashima, M.; Yamada, Y. “New cembranolide diterpenes with a dimethyl amino group from the Okinawan soft coral (Sinularia species).” Chem. Lett. 1992, 1,127–130.
37. Kobayashi, M.; Isizaka, T. “Marine terpenes and terpenoids, Part XV. Dimethylamine adducts of -methylene-γ-lactonic marine
cembranoids.” J. Chem. Res., Synop. 1992, 10, 340–341.
38. Duh, C.-Y.; Hou, R.-S.; Wang, S.-K.; Chang, T.-T.; Wang, Y.; Lee, G.-H. “Formosan soft coral III Cytotoxic norcembrene diterpenes from the soft coral Sinularia polydactyla.” Zhonghua Yaoxue Zazhi. 1993, 45, 399–407.
39. Anjaneyulu, A.S.R.; Raju, K.V.S.; Prakash, C.V.S. “Sinulariadione, a rare cembranolide from an Indian soft coral of the genus Sinularia.” Nat. Prod. Lett. 1993, 3, 149–153.
40. Duh, C.-Y.; Wang, S.-K.; Soong, K.; Fary, L.-S. “Cytotoxic
norcembrene diterpenes from the soft coral Sinularia inexplicita.” Chinese Pharmacology Journal. 1994, 46, 423–428.
41. Hou, R.-S.; Duh, C.-Y.; Chiang, M.-Y.; Lin, C.-N. “Sinnugibberal, a new cytotoxic cembranoid diterpene from the soft coral Sinularia
gibberosa.” J. Nat. Prod. 1995, 58, 1126–1130.
42. Duh, C.-Y.; Hou, R.-S.; Liu, C.-H.; Soong, K. “Potential anticancer cembranoid diterpenes from a Formosan soft coral.”
Acta Oceanogr Taiwan. 1995, 34, 71–78.
43. Guerrero, P.P.; Read, R.W.; Bateley, M.; Janairo, G.C. “The structure of novel cembranoid diterpene from a Phillipine collection of soft coral Sinularia flexibilis.” J. Nat. Prod. 1995, 58, 1185–1191.
44. Anjaneyulu, A.S.R.; Sagar, K.S.; Venugopal, M.J.R.V. “Terpenoid and steroid constituents of the Indian Ocean soft coral Sinularia
marima.” Tetrahedron. 1995, 51, 10997–11010.
45. Anjaneyulu, A.S.R.; Sagar, K.S. “Two new 5a, 8a-epidioxy sterols
from the Indian Ocean soft coral Sinularia maxima.” J. Chem. Res.
Synop. 1995, 4, 142–143.
46. Anjaneyulu, V.; Rao, K.N.; Radhika, P.; Kobayashi, M. “Isolation of 24-methylcholest-5-ene-3-, 25-diol-3-o--D-arabinopyranoside
from Sinularia grandilobata of Andaman and Nicobar Islands.
”Indian J.Chem.Sect B. 1996, 35, 757–759.
47. Anjaneyulu, A.S.R.; Rao, G.V.; Rao, K.V.S. “Sesqui and diterpenoids of the soft coral Sinularia hirta of the Andaman and Nicobar Islands.” Indian J.Chem.Sect B. 1996, 35, 815–818.
48. Duh, C.-Y.; Hou, R.-S. “Cytotoxic cembranoids from the soft coral
Sinularia gibberosa and Sarchophyton trocheliophorum.” J. Nat.
Prod. 1996, 59, 595–598.
49. Anjaneyulu, A.S.R.; Sagar, K.S.; Rao, G.V. “New cembranoid lactones from the Indian Ocean soft coral Sinularia flexibilis.” J. Nat. Prod. 1997, 60, 9–12.
50. Duh, C.-Y.; Wang, S.-W.; Tseng, H.-K.; Sheu, J.-H. “A novel
cytotoxic biscemranoid from the Formosan soft coral Sinularia
flexibilis.” Tetrahedron Lett. 1998, 39, 7121–7122.
51. Rudi, A.; Dayan, T.L.A.; Aknin, M.; Gaydou, E.M.; Kashman, Y. “Several new isoprenoid from soft coral Sinularia erecta.” J. Nat. Prod. 1998, 61, 872–875.
52. Su, J.-Y.; Ruolin, K.-Y.; Zeng, L. “A new cembranolide from soft
coral Sinularia capillosa.” J. Nat. Prod. 2000, 63, 1543–1545.
53. Ramesh, P.; Venkateswarlu, Y. “Unusual terpenoid constituents of the soft coral Sinularia dissecta.” J. Chem. Res., Synop. 2000, 1, 48–50.
54. Sheu, J.-H.; Ahmad, A.F.; Shiue, R.-T.; Dai, C.-F.; Kuo, Y.-H. “Scrabolides A-D, four new norditerpenoid isolated from the soft coral Sinularia scabra.” J. Nat. Prod. 2002, 65, 1904–1908.
55. Ahmed, A.F.; Shiue, R.-T.; Wang, G.-H.; Dai, C.-F.; Kuo, Y.-H.;
Sheu, J.-H. “Five novel cembranoids from Sinularia leptoclados and Sinularia parva.” Tetrahedron. 2003, 290, 7337–7344.
56. Rao, C.B.; Satyanarayana, C.; Rao, D.S.; Fany, E.; Faulkner, D.J. “Metabolites of the soft coral Sinularia ovispiculata from the Indian Ocean.” J. Nat. Prod. 1993, 56, 2003–2007.
57. Ahmed, A.F.; Su, J.-H.; Kuo, Y.-H.; Sheu, J.-H. “Scrabolides E–G, three new norditerpenoids from the soft coral Sinularia scabra. .” J. Nat. Prod. 2004, 67, 2079–2082.
58. Kamel, H. N.; Ferreira, D.; Garcia-Fernandez, L. F.; Slattery, M. “Cytotoxic diterpenoids from the hybrid soft coral Sinularia
maxima× Sinularia polydactyla.” J. Nat. Prod. 2007, 70, 1223-1227.
59. Ahmed, A.F. “Notandolide, a new cembranolide isolated from a soft coral sinularia notanda, and the role of lactone in the cytotoxic
activity of lactone in the cytotoxic activity of cemabranoids mans.” Mansoura J. Pharm. Sci. 2007, 23, 27-38.
60. Ahmed, A. F.; Wen, Z.-H.; Su, J.-H.; Hsieh, Y.-T.; Wu, Y.-C.; Hu,W.-P.; Sheu, J.-H. “Oxygenated cembranoids from a Formosan soft coral Sinularia gibberosa.” J. Nat. Prod. 2008, 71, 179-185.
61. Ahmed, A. F.; Tai, S.-H.; Wen, Z.-H.; Su, J.-H.; Wu, Y.-C.; Hu, W.-P.; Sheu, J.-H. “A C-3 methylated isocembranoid and
10-oxocembranoids from a Formosan soft coral, Sinularia
grandilobata.” J. Nat. Prod. 2008, 71, 946-951.
62. Wen, T.; Ding, Y.; Deng, Z.; Ofwegen, L.; Proksch, P.; Peter, L. “Sinulaflexiolides A-K, cembrande-type diterpenoids from the
chinese soft coral Sinularia flexibilis.” J. Nat. Prod. 2008, 71: 1133–1140.
63. Li, G.; Zhang, Y.; Deng, Z.; van Ofwegen, L.; Proksch, P.; Lin, W.“Cytotoxic Cembranoid Diterpenes from a Soft Coral Sinularia
gibberosa.”J. Nat. Prod. 2005, 68, 649-652.
64. Lu, Y.; Huang, C.-Y.; Lin, Y.-F.; Wen, Z.-H.; Su, J.-H.; Kuo, Y.-H. Chiang, M.-Y.; Sheu, J.-H. “Anti-inflammatory cembranoids from the soft corals Sinularia querciformis and Sinularia granosa.” J. Nat. Prod. 2008, 71, 1754-1759.
65. Grote, D.; Dahse, H. M.; Seifert, K. “Furanocembranoids from the
soft corals Sinularia asterolobata and Litophyton arboreum.” Chem Biodivers. 2008, 5, 2449-2456.
66. Qin, S.; Huang, H.; Guo, Y.-W. “A new cembranoid from the Hainan soft coral Sinularia sp.” J. Asian Nat. Prod. Res. 2008, 10,1075-1079.
67. Li, Y.; Gao, A.-H.; Huang, H.; Li, J.; Mollo, E.; Gavagnin, M.; Cimino, G.; Yu-Cheng Gu, Y.-C.; Guo, Y. W. “Diterpenoids from the Hainan soft coral Sinularia parva.” Helvetica Chimica Acta. 2009,92, 1341-1348.
68. Su, J.-H.; Lin, Y.-F.; Lu, Y.; Yeh, H.-C.; Wang, W.-H.; Fan, T.-Y.;
Sheu, J.-H. “Oxygenated cembranoids from the cultured and wild-type soft corals Sinularia flexibilis.” Chem. Pharm. Bull.
2009, 57, 1189-1192.
69. Lai, D.-W.; Li, Y.-X.; Xu, M.-J.; Deng, Z.-W.; Ofwegen, L. V.; Qian, P.-Y.; Proksch, P.; Lin, W.-H. “Sinulariols A-S, 19-oxygenated cembranoids from the Chinese soft coral Sinularia rigida.” Tetrahedron. 2011, 67, 6018–6029.
70. Cheng, S.-Y.; Chuang, C.-T.; Wen, Z.-H., Wang, S.-K.; Chiou, S.-F.; Hsu, C.-H.; Dai, C.-F.; Duh, C.-Y. “Bioactive norditerpenoids from the soft coral Sinularia gyrosa.” Bioorg. Med. Chem. 2010, 18, 3379-3386.
71. Lo, K. L.; Khalil, A. T.; Chen, M. H.; Shen, Y. C. “New cembrane
diterpenes from Taiwanese soft coral Sinularia flexibilis.” Helv Chim Acta. 2010, 93, 1329-1335.
72. Chen, B.-W.; Chao, C.-H.; Su, J.-H.; Huang, C.-Y.; Dai, C.-F.; Wen, Z.-H.; Sheu, J.-H. “A novel symmetric sulfur-containing
biscembranoid from the Formosan soft coral Sinularia flexibilis.” Tetrahedron Lett. 2010, 51, 5764-5766.
73. Su, J.-H.; Wen, Z.-H. “Bioactive cembrane-based diterpenoids from the soft coral Sinularia triangular.” Mar. drugs. 2011, 9, 944-951.
74. Fattorusso, E.; Luciano, P.; Putra, M. Y.; Taglialatela-Scafati, O.;
Ianaro, A.; Panza, E.; Bavestrello, G.; Cerrano, C. “Chloroscabrolides, chlorinated norcembranoids from the Indonesian soft coral Sinularia sp.” Tetrahedron. 2011, 67, 7983-7988.
75. Lin, Y.-S.; Lee, N.-L.; Lu, M.-C.; Su, J.-H. “Two new
cembrane-based diterpenoids from the marine soft coral Sinularia
crassa.” Molecules. 2012, 17, 5422-5429.
76. Qin, M.-L.; Li, X.-M.; Wang, B.-G. “Cembranoid, Steroid, and
Sesquiterpenoid Derivatives from the South China Sea Soft Coral Sinularia numerosa.” Chinese Journal of Chemistry. 2012, 30, 1278-1282.
77. Yen, W.-H.; Hu, L.-C.; Su, J.-H.; Lu, M.-C.; Twan, W.-H.; Yang, S.-Y.; Kuo, Y.-C.; Weng, C.-F.; Lee, C.-H.; Kuo, Y.-H.; Sung, P.-J. “Norcembranoidal diterpenes from a Formosan soft coral Sinularia sp.” Molecules. 2012, 17, 14058-14066.
78. Yang, B.; Zhou, X.; Huang, H.; Yang, X.-W.; Liu, J.; Lin, X.; Li, X.; Peng, Y.; Liu, Y. “New cembrane diterpenoids from a Hainan soft coral Sinularia sp.” Mar. drugs. 2012, 10, 2023-2032.
79. Shih, H.-J.; Tseng, Y.-J.; Huang, C.-Y.; Wen, Z.-H.; Dai, C.-F.; Sheu, J.-H. “Cytotoxic and anti-inflammatory diterpenoids from the
Dongsha Atoll soft coral Sinularia flexibilis.” Tetrahedron. 2012, 68, 244-249.
80. Nguyen, H. N. “Diterpenoids from the Soft Coral Sinularia maxima and Their Inhibitory Effects on Lipopolysaccharide‐Stimulated
Production of Proinflammatory Cytokines in Bone Marrow‐Derived Dendritic Cells.” Chem Inform. 2013, 44.
81. Shen, S.; Zhu, H.; Chen, D.; Liu, D.; Ofwegen, L. V.; Proksch, P.; Lin, W. “Pavidolides A–E, new cembranoids from the soft coral Sinularia pavida.” Tetrahedron Lett. 2012, 53, 5759-5762.
82. Hu, L.-C.; Su, J.-H.; Chiang, M. Y.-N.; Lu, M.-C.; Hwang, T.-L.; Chen, Y.-H.; Hu, W.-P.; Lin, N.-C.; Wang, W.-H.; Fang, L.-S.; Kuo, Y.-H.; Sung, P.-J. “Flexibilins A–C, New Cembrane-Type Diterpenoids from the Formosan Soft Coral, Sinularia flexibilis.” Mar. drugs. 2013, 11, 1999-2012.
83. Chen, K.-H.; Dai, C.-F.; Lu, M.-C.; Li, J.-J.; Chen, J.-J.; Chang, Y.-C.; Sung, P.-J. “Secondary Metabolites from the Soft Coral Sinularia
arborea.” Mar. drugs. 2013, 11, 3372-3380.
84. Thao, N. P.; Nam, N. H.; Cuong, N. X.; Luyen, B. T. T.; Tai, B. H.;
Kim, J. E.; Kim, Y. H. “Inhibition of NF-κB transcriptional activation in HepG2 cells by diterpenoids from the soft coral Sinularia maxima.” Arch. Pharm. Res. 2014, 37, 706-712.
85. Prestwich, G. D.; Wiemer, D. F.; Meinwald, J.; Clardy, J. “Cubitene: An Irregular Twelve-Membered-Ring Diterpene from a Termite
Soldier.” J. Am. Chem. Soc. 1978, 100, 2560-2561.
86. Tempesta, M. S.; Pawlak, J. K.; Iwasita, T.; Naya, Y.; Nakanishi, K.; Prestwich, G. D. “Cubugene, a Diterpenoid with a Novel Carbon
Skeleton from a Termite Soldier (Isoptera Termitidae Termitinae).”
J. Org. Chem. 1984, 49, 2077-2079.
87. Look, S. A.; Fenical, W.; Zheng, Q. T.; Clardy, J. “Calyculones, New Cubitane Diterpenoids from the Caribbean Gorgonian Octocoral Eunicea calyculata.” J. Org. Chem. 1984, 49, 1417-1423.
88. Shin, J.; Fenical, W. “New Diterpenoids from the Caribbean Gorgonian Eunicea calyculata. Photochemical Interconversion of the Cembrene and Cubitene Skeletons.” J. Org. Chem. 1991, 56,
1227-1233.
89. Marville, K. I.; Reynolds, W. F.; Sealy, R. L.; Tinto, W. F. “Terpenoid metabolites of the marine octocoral Eunicea laciniata.” Heterocycles. 2004, 63, 107-113.
90. Schöttner, E.; Wiechoczek, M..; Jones, P. G.; Lindel, T.
“Enantiospecific Synthesis of the Cubitane Skeleton.” Org. Lett.
2010, 12, 784-787.
91. Lu, M.-C.; Lee, N.-L.; Tseng, S.-W.; Su, J.-H. “Sinutriangulin A, a novel diterpenoid from the soft coral Sinularia triangula.”
Tetrahedron Lett. 2011, 52, 5869-5871.
92. Wei, X.; Nieves, K.; Rodríguez, A. D. “Bioactive cubitane diterpenoids from a Colombian gorgonian species of the genus
Eunicea.” Pure Appl. Chem. 2012, 84, 1847-1855.
93. Su, H.-J.; Lee, N.-L.; Lu, M.-C.; Su, J.-H. “Triangulene C, a New Cubitane-based Diterpenoid from the Soft Coral Sinularia triangula.” Nat Prod Commun. 2012, 7, 479-480.
94. Cheng, C.-H.; Lin, Y.-S.; Wen, Z.-H.; Su, J.-H. “A New Cubitane Diterpenoid from the Soft Coral Sinularia crassa.” Molecules. 2012, 17, 10072-10078.
95. Anjaneyulu, V.; Rao, K. N.; Babu, J. S.; Kobayashi, M. “Isolation of 24-methylenecholesterol-3- O-α-L- fucopyranoside and 24-methylenecholest-7- ene-3β,6α,9α,11α-tetrol from a soft coral of the Andaman and Nicobar Islands.” Indian J. Chem. Sect B. 1994,
33B, 144-147.
96. Kobayashi, M.; Kanda, F.; Rao, D. S.; Rao, D. V.; Rao, C. B. “Marine Sterols.XVII. Polyhydroxysterols of the Soft Corals of theAndaman and Nicobar Coasts. Isolation and structures of three 116β-hydroxy steroidal glycosides from an Alcyonium sp. Soft
Coral.” Chem. Pharm. Bull. 1990, 38, 2400-2403.
97. Vanisree, M.; Subbaraju, G. V.; Rao, C. B. “Alcyonacean metabolites: Part 6 - Steroid glycosides from a new species
of Sinularia genus of the Andaman and Nicobar coasts.” Indian J. Chem. Sect B. 1999, 38B, 394-396.
98. Su, J.-H.; Tseng, Y.-J.; Huang, H.-H.; Ahmed, A. F.; Lu, C.-K.; Wu, Y.-C.; Sheu, J. H. “9,11-Secosterols from the Soft Corals Sinularia lochmodes and Sinularia leptoclados.” J. Nat. Prod. 2006, 69,
850-852.
99. Chao, C.-H.; Chou, K.-J.; Huang, C.-Y.; Wen, Z.-H.; Hsu, C.-H.; Wu, Y.-C.; Sheu, J.-H. “Steroids from the Soft Coral Sinularia crassa.” Mar. drugs. 2012, 10, 439-450.
100. De Riccardis, F.; Minale, L.; Iorizzi, M.; Debitus, C.; Lévi,C. “Marine sterols. Side-chain-oxygenated sterols, possibly of abiotic origin, from the new Caledonian sponge Stelodoryx chlorophylla.” J. Nat. Prod. 1993, 56, 282-287.
101. Cantrell, C. L.; Lu, T.; Fronczek, F. R.; Fischer, N. H. “Antimycobacterial Cycloartanes from Borrichia frutescens” J. Nat. Prod. 1996, 59, 1131–1136.
102. Hwang, T.-L.; Leu, Y.-L.; Kao, S.-H.; Tang, M.-C.; Chang H.-L.“Viscolin, a new chalcone from Viscum coloratum, inhibits human
neutrophilsuperoxide anion and elastase release via a cAMP-
dependent pathway. ” Free Radical Biol. Med. 2006, 41, 1433–1441.