中文摘要
台灣綠島海域所採集的柳珊瑚Isis hippuris (Isididae)的正己烷粗萃取物經初步的生物活性測試發現對於P-388、A-549及HT-29體外培養之癌細胞有顯著的細胞毒殺活性，故依此生物活性為指標進行正己烷粗萃取層分離得到9個sesquiterpenes，一個已知化合物為suberosenone (1)，還有五個為新化合物(骨架屬於suberosanane類)，分別為suberosanone (2)、suberosenol A (3)、suberosenol B (4)、suberosenol A acetate (5)、suberosenol B acetate (6)，此外還有2個新骨架的化合物isishippuric acid A (7)和isishippuric acid B (8)，及已知的三個化合物subergorgic acid (9)、3-hexadecyl-5-hydroxy-5-methyl-5-hydrofuran-2-one (10) 與prenga-1,4-diene-3,20-dione (11)。純化後之化合物2-6和8進行癌細胞株毒殺活性測試，結果顯示對於P-388、A-549及HT-29癌細胞株均有相當強之毒殺活性。

Abstract
The n-hexane extract of Formosan gorgonian coral Isis hippuris (Isididae) collected from Green Island was found to exhibit significant cytotoxicity against P-388, A-549 and HT-29 cell lines. Cytotocicity-guided fractionation of this extract led to isolation of a known subersenone (1), five new suberosanane analogues, suberosanone (2), suberosenol A (3), suberosenol B (4), suberosenal A acetate (5) and suberosenol B acetate (6), two sesquiterpenes of novel skeletons, isishippuric acid A (7) and B (8). Three known compounds, subergorgic acid (9). 3-hexadecyl-5-hydroxy- 5-methyl-5-hydrofuran-2-one (10) and prenga-1,4-diene-3,20-dione (11) were also isolated along with the novel compound. Compounds 2-6 and 8 showed potent cytotoxicities against P-388, A-549 and HT-29 cells.

目錄
頁次
壹、 緒論
一、 前言 1
二、 柳珊瑚Isis hippuris天然物化學文獻調查 2
三、 柳珊瑚Suber suberosa天然物化學文獻調查 3
四、 研究動機 10
貳、 生物材料與分離方法
一、 生物樣品材料採集時間與地點 11
二、 生物樣品的型態與分類 11
三、 萃取與純化分離步驟 12
參、 器材與實驗
一、 儀器 19
二、 溶劑藥品 20
三、 實驗程序 21
肆、 結果與討論
一、 化合物結構解析 25
(一)、化合物subersenone (1) 25
(二)、化合物subersanone (2) 30
(三)、化合物subersenol A (3) 42
(四)、化合物subersenol B (4) 54
(五)、化合物subersenol acetate A (5) 65
(六)、化合物subersenol acetate B (6) 77
(七)、化合物isihippuric acid A (7) 89
(八)、化合物isihippuric acid B (8) 101
(九)、化合物subergorgic acid (9) 113
(十)、化合物3-hexadecyl-5-hydroxy-5-methyl-5-hydrofuran-2-one (10) 117
(十一)、化合物prenga-1,4-diene-3,20-dione (11) 125
二、 化合物之癌細胞毒殺活性 129
伍、 結論 130
陸、 參考文獻 134

陸、參考文獻
1. Ruggieri, G. D.; “Drugs from the Sea”; Science, 1976, 194, 491-497.
2. 方力行；“珊瑚學”，教育部大學聯合出版委員會，1989，34-37。
3. 戴昌鳳；“台灣的軟珊瑚”；台灣省政府教育廳，1989。
4. 戴昌鳳；“我國珊瑚生物學研究發展”；生命科學簡訊，1993，2-6。
5. Higa, T.; Tachibana, K.; Tanaka, J.; “18-Oxygenated Polyfunctional Steroids from the Gorgonian Isis hippuris”; Tetrahedron Lett., 1981, 22, 2777-2780.
6. Higa, T.; Kikuchi, H.; Tanaka, J.; Tsukitani, Y.; “Hippuristanols, Cyto-Toxic Polyoxygenated Steroids from the Gorgonian Isis hippuris”; Chemistry Lett., 1981, 11, 1647-1650.
7. Tanaka, J.; Higa, T.; Iwashita,T.; Tachibana, K.; “ Polyfunctional Marine Steroids .3. Gorgost-5-Ene-3-Beta,7-Alpha,11-Alpha,12-Beta-Tetraol 12-Monoacetate, a New Marine Sterol from the Gorgonian Isis hippuris”; Chemistry Lett., 1982, 8, 1295-1296.
8. Rao, C. B.; Rao, D. V.; Ramana, K. V.; Fahy, E.; Faulkner, D. J.; “Metabolites of the Gorgonian Isis hippuris from India”; J. Nat. Prod., 1988, 22, 2777-2780.
9. Groweissz, A.; Fenical, W.; Cun-heng, H.; Clardy, J.; Zhongde, W.; and Kanghpu, L.; “Subergorgic Acid, A Novel Tricyclopentanoid Cardiotoxic From the Pacific Gorgonian Coral Subergorgia suberosa”; Tetraheadron Lett., 1985, 26, 2379-2382.
10. Parameswaran, P. S.; Naik, C. G.; Kamat, S. Y.; Puar, M. S.; Das, P.; and Hegde, V. R.; “Studies on the Secondary Metabolites from the Indian Gorgonian Subergorgia suberosa : Isolation and Characterization of Four Analogues of the Cardiotoxin Subergorgic Acid”; J. Nat. Prod., 1998, 61, 832-834,1074.
11. Bokesch, H. R.; Mckee, T. C.; Cardellina II, J. H.; Boyd, M. R.; “Suberosenone, a New Cytotoxin from Subergorgia suberosa”; Tetrahedron Lett., 1996, 37, 3259-3262.
12. Ranieri, R. L.; Calton, G. J.; Crace & Co, W, R.; “Quadrone, a New Antitumor Agent from Aspergillus terreus”; Tetrahedron Lett., 1978, 6, 499-502.
13. Nakagawa, M.; Hirota, A.; Sakai, H.; “Terrecyclic Acid A, A New Antibiotic from Aspergillus Terreus : I. Taxonomy, production, and Biological Properties”; J. Antibiotics., 1982, 35, 778-782.
14. Hirota, A.; Nakagawa, M.; Sakai, H.; “Terrecyclic Acid A, A New Antibiotic from Aspergillus Terreus : II. Structure of Terrecyclic Acid A”; J. Antibiotics., 1982, 35, 783-787.
15. Hirota, A.; Nakagawa, M.; “Terrecyclic Acid A, A New Antibiotic from Aspergillus Terreus : IV. Absolute Stereochemistry of Terrecyclic Acid A”; J. Antibiotics., 1986, 39, 149-152.
16. Gane, D. E.; Whittle, Y. G.; Liang, T-C.; “The Biosynthesis of Quadrone and Terrecyclic Acid”; Tetrahedron Lett., 1984, 25, 1119-1122.
17. Beale, J. M.; Chapman, R. L.; Rosazza, J. P. N.; “Studies on The Biosynthesis Terrecyclic Acid A, An Antitumor Antibiotic from Aspergillus Terreus”; J. Antibiotics., 1984, 39, 1376-1381.
18. Hirota, A.; Nakagawa, M.; Sakai, H.; “Studies on The Biosynthesis of Terrecyclic Acid A III Confirmation of The Cyclization Mechanism and Hydrogen Shifts Using [2-2H3]Acetate and [2-13C2H3]Acetate”; Tetrahedron Lett., 1985, 26, 3845-3848.
19. Aknin, M.; Costantino, A.; Fattorusso, E.; Gaydou, E. M.; “New 9,11-secosterols from gorgongia Subergorgia suberosa of the Indian Ocean”; Steroids, 1998, 63, 575-578.
20. Anjaneyulu, A. S. R.; Kameswara Rao, N. S.; Venkateswara Rao, G.; “A new secosteroid from the gorgonian Subergorgia suberosa Pallas of the Indian Ocean” Indian. J. Chem. Sec., 1997, 36B, 418-423.
21. Bokesch, H. R.; Blunt, J. W.; Westergarrd, C. K.; Cardellina II, J. H.; Johnson, T. R.; Michael, J. A.; Mckee, T. C.; Hollingshead, M. G.; Boyd, M. R.; “Altertenone, a Dimer of Suberosenone from Isis hippuris”; J. Nat. Prod., 1999, 62, 633-635.
22. Alley, M. C.; Scudiero, Monks, D. A.; A.; Hursey, M. L.; Czerwonski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemark, R. H.; Boyd, M. R.; “ Feasibility of Drug Screening with Panels of Human Tumor Cell Lines Using a Microcultuer Tetrazolium Assay”; Cancer Res., 1988, 48, 589-601.
23. Mosmann, T.; “ Rapid Colorimetric Assay for Celluar Growth and Survival : Application to Proliferation and Cytotoxicity Assays”; J. Immu. Method., 1983, 65, 55-63.
24. Coates, R. M.; Ho, J. Z.; Klobus, M.; Zhu, L.; “Carbocationic Rearrangements of Silphinane Derivatives”; J. Org. Chem. 1998, 63, 9166-9176.
25. Kikuchi, K.; Tsukitani, Y.; Nakanishi, H.; Shimizu, I.; Saitoh, S.; “Studies on Marine Product. VIII. New Butenolides from the Gorgonian Euplexaura flava (Nutting)”; Chem. Pharm. Bull., 1983, 31, 1172-1176.
26. Barton, D. H. R.; Boivin, J.; Hill, C. H.; “Functionalisation of Saturated Hydrocarbons. Part 6. Selective Oxidation of Steroids and Related Compounds ”; J. Chem.Soc. Perkin Trans. I, 1986, 1797-1804.