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博碩士論文 etd-0805105-151526 詳細資訊
Title page for etd-0805105-151526
論文名稱
Title
臺灣產白穗軟珊瑚屬Nephthea chabrolii天然物之研究
Studies on the Natural Products of the Formosan Soft Coral Nephthea chabrolii
系所名稱
Department
畢業學年期
Year, semester
語文別
Language
學位類別
Degree
頁數
Number of pages
203
研究生
Author
指導教授
Advisor
召集委員
Convenor
口試委員
Advisory Committee
口試日期
Date of Exam
2005-07-06
繳交日期
Date of Submission
2005-08-05
關鍵字
Keywords
白穗軟珊瑚、天然物
Nephthea chabrolii
統計
Statistics
本論文已被瀏覽 5655 次,被下載 2970
The thesis/dissertation has been browsed 5655 times, has been downloaded 2970 times.
中文摘要
本研究針對台灣墾丁國家公園海域所採集的軟珊瑚Nephthea chabrolii所含有的化學成分進行探討,並分離純化出九個化合物,其中七個為新的天然化合物,分別為chabrolosteroid A (1)、chabrolosteroid B (2)、chabrolosteroid C (3)、chabrolosteroid D (4)、chabrolosteroid E (5)、chabrolosteroid F (6)、chabrolosteroid G (7),與兩個已知的化合物loliolide (8)、teuhetenone A (9)。化合物1–9之化學結構及相對立體構型均是以各種光譜解析(1D NMR、2D NMR、IR及MS)及文獻比對的方法加以確立。同時,並將所獲得之天然化合物進行癌細胞株的細胞毒殺活性測試。
Abstract
Investigation on the chemical constituent of a Formosan soft coral Nephthea chabrolii, collected along the coast off Kenting, has led to the isolation of nine marine natural products (1–9), including seven new compounds, chabrolosteroids A–G (1–7), and two known compounds, loliolide (8) and teuhetenone A (9). The structures of 1–9 were determined on the basis of spectroscopic analyses, including MS, IR, 1D NMR, and 2D NMR. Cytotoxicities of 1–9 against selected cancer cell lines were also measured.
目次 Table of Contents
目錄

頁次
中文摘要 XI
英文摘要 XII
壹、緒論
一、前言 1
二、研究動機 3
三、Nephthea屬軟珊瑚過去相關研究概要 6

貳、實驗程序與方法
一、生物樣品採集時間、地點與分類地位 22
二、萃取與分離純化步驟 23
三、實驗器材與溶劑 27

參考文獻 References
陸、參考文獻

1. Wallace, R. W. Mol. Med. Today 1997, 3, 277.
2. Gragg, G. M.; Newman, D. J.; Sander, K.M. “ Natural Products in Drug Discovery and Development ” J. Nat. Prod. 1997, 60, 52.
3. Harvey, A. L. TIPS 1999, 20, 196.
4. 方力行“珊瑚學-間論台灣的珊瑚資源”教育部大學聯合出版委員會,1989.
5. 江昆達、林全信,豐富的海洋資源,台灣書店,1998,117-126.
6. Coll, J. C.; Barre, S. L.; Sammacro, P. W.; Williams, W. T.; Bakus, G. J. Mar. Ecol. Prog. Ser. 1982, 8, 271-278.
7. Bucholder, P. R. “ The ecology of marine antibiotics and coral reefs. In biology and geology of coral reefs ” VOI. II:Biology I. 1973, Academic Press. pp. 117-176.
8. Ruggieri, G. D. “ Drugs from the Sea ” Science 1976, 194, 491-497.
9. 戴昌鳳“墾丁國家公園-珊瑚之美”;墾丁國家公園管理處員工消費合作社,1987.
10. Barre, S. L.; Coll, J. C. “ Movement in Soft Corals: An Interaction Between Nephthea brassica (Coelenterata: Octocorallia) and Acropora hyacinthus (Coelenterata: Scleractinia) ” Marine Biology 1982, 72, 119-124.
11. Coll, J. C.; Bowden, B. F.; Tapiolas, D. M. “ In Situ Isolation of Allelochemicals Released from Soft Corals (Coelenterata: Octocorallia): a Totally Submersible Sampling Apparatus ” J. Exp. Mar. Biol. Ecol. 1982, 60, 293-299.
12. Bakus, G. J. “ Chemical Defense Mechanisms on the Great Barrier Reef, Australia ” Science 1981, 211, 497-499.
13. Schmitz, F. J.; Vanderah, D. J.; Ciereszko, L. S. “ Marine Natural Products: Nephthenol and Epoxynephthenol Acetate, Cembrene Derivatives from a Soft Coral ” J. Chem. Soc. Chem.Commun. 1974, 407-408.
14. Vanderah, D. J.; Rutledge, N.; Schmitz, F. J.; Ciereszko, L. S. “ Marine Natural Products: Cembrene-A and Cembrene-C from a Soft Coral, Nephthea sp. ” J. Org. Chem. 1978, 43, 1614-1616.
15. Bowden, B. F.; Coll, J. C.; Mitchell, S. J. “ Studies of Australian Soft Corals. XXI A New Sesquiterpene from Nephthea chabrolii and an Investigation of the Common Clam Tridacna maxima ” Aust. J. Chem. 1980, 33, 1833-1839.
16. Ahond, A.; Bowden, B. F.; Coll, J. C. “ Studies of Australian Soft Corals. XXV Several Caryophyllene-Based Diterpenes from a Nephthea Species ” Aust. J. Chem. 1981, 34, 2657-2664.
17. Bowden, B. F.; Coll, J. C. “ Studies of Australian Soft Corals. XXVI Tetraprenylbenzoquinone Derivatives from a Nephthea Species of Soft Coral (Octocorallia, Alcyonacea) ” Aust. J. Chem. 1981, 34, 2677-2681.
18. Poet, S. E.; Ravi, B. N. “ Three New Diterpenes from a Soft Coral Nephthea Species ” Aust. J. Chem. 1982, 35, 77-83.
19. Blackman, A. J.; Bowden, B. F.; Coll, J. C.; Frick, B.; Mahendran, M.; Mitchell, S. J. “ Studies of Australian Soft Corals. XXIX Several New Cembranoid Diterpenes from Nephthea brassica and Related Diterpenes from a Sarcophyton Species ” Aust. J. Chem. 1982, 35, 1873–1880.
20. Coll, J. C.; Bowden, B. F.; Tapiolas, D. M.; Willis, R. H.; Djura, P.; Streamer, M.; Trott, L. “ Studies of Australian Soft Corals-XXXV The Terpenoid Chemistry of Soft Corals and Its Implications ” Tetrahedron 1985, 41, 1085-1092.
21. Kitagawa, I.; Cui, Z.; Son, B. W.; Kobayashi, M.; Kyogoku, Y. “ Marine Natural Products. XVII. Nephtheoxydiol, a New Cytotoxic Hydroperoxy- Germacrane Sesquiterpene, and Related Sesquiterpenoids from an Okinawan Soft Coral of Nephthea sp. (Nephtheidae) ” Chem. Pharm. Bull. 1987, 35, 124-135.
22. Handayani, D.; Edrada, R. A.; Proksch, P.; Wray, V.; Witte, L.; Ofwegen, L. V.; Kunzmann, A. “ New Oxygenated Sesquiterpenes from the Indonesian Soft Coral Nephthea chabrolii ” J. Nat. Prod. 1997, 60, 716-718.
23. Duh, C.-Y.; Wang, S.-K.; Chu, M.-J.; Sheu, J.-H. “ Cytotoxic Sterols from the Soft Coral Nephthea erecta ” J. Nat. Prod. 1998, 61, 1022-1024.
24. Geran, R. I.; Greenberg, N. H.; MacDonald, M. M.; A. M.Schumacher, A. M.; Abbott, B. J. Cancer Chemother. Rep. 1972, 3, 1-91.
25. Duh, C.-Y.; Wang, S.-K.; Weng, Y.-L.; Chiang, M. Y.; Dai, C.-F. “ Cytotoxic Terpenoids from the Formosan Soft Coral Nephthea brassica ” J. Nat. Prod. 1999, 62, 1518-1521.
26. Rao, M. R.; Venkatesham, U.; Venkateswarlu, Y. “ Two New 19-Oxygenated Steroids from the Soft Coral Nephthea chabroli ” J. Nat. Prod. 1999, 62, 1584-1585.
27. Duh, C.-Y.; Wang, S.-K.; Weng, Y.-L. “ Brassicolene, a novel cytotoxic diterpenoid from the Formosan soft coral Nephthea brassica ” Tetrahedron Letters 2000, 41, 1401-1403.
28. Rao, M. R.; Sridevi, K. V.; Venkatesham, U.; Rao, T. P.; Lee, S. S.; Venkateswarlu, Y. “ Four new sesquiterpenoids from the soft coral Nephthea chabrolii ” J. Chem. Research (S) 2000, 11, 245-247.
29. Zhang, W.-H.; Williams, I. D.; Che, C.-T. “ Chabrolols A, B and C, three new norditerpenes from the soft coral Nephthea chabroli ” Tetrahedron Letters 2001, 42, 4681-4685.
30. Shao, Z.-Y.; Zhu, D.-Y.; Guo, Y.-W. “ Nanjiols A-C, New Steroids from the Chinese Soft Coral Nephthea bayeri ” J. Nat. Prod. 2002, 65, 1675-1677.
31. Zhang, W.; Liu, W. K.; Che, C.-T. “ Polyhydroxylated Steroids and Other Constituents of the Soft Coral Nephthea chabroli ” Chem. Pharm. Bull. 2003, 51, 1009-1011.
32. Sheu, J.-H.; Su, J.-H.; Sung, P.-J.; Wang, G.-H.; Dai, C.-F. “ Novel Meroditerpenoid-Related Metabolites from the Formosan Soft Coral Nephthea chabrolii ” J. Nat. Prod. 2004, 67, 12, 2048-2052.
33. Ali. A. H. El-Gamal; Wang, S.-K.; Dai, C.-F.; Duh, C.-Y. “ New Nardosinanes and 19-Oxygenated Ergosterols from the Soft Coral Nephthea armata Collected in Taiwan ” J. Nat. Prod. 2004, 67, 1455-1458.
34. Ali. A. H. El-Gamal; Wang, S.-K.; Dai, C.-F.; Chen, I.-G.; Duh, C.-Y. “ Prenylbicyclogermacrane Diterpenoids from the Formosan Soft Coral Nephthea pacifica ” J. Nat. Prod. 2005, 68, 74-77.
35. Ali. A. H. El-Gamal; Li, C.-H.; Dai, C.-F.; Chen, I.-G.; Duh, C.-Y. “ Bioactive Secondary Metabolites from the Formosan Soft Coral Nephthea elongata ” 發表於2005年第二十屆天然藥物研討會。
36. Abraham, W.-R.; Guillermo, S.-H. “ (24S)-3β-hydroxy-ergost-5-en-6-one from Cyttaria johowii ” Phytochemistry 1994, 36, 459-461.
37. Wright, A. D.; Goclik, E.; Konig, G. M. “ Oxygenated Analogues of Gorgosterol and Ergosterol from the Soft Coral Capnella lacertiliensis ” J. Nat. Prod. 2003, 66, 157-160.
38. Wu, S.-L.; Wang, G.-H.; Dai, C.-F.; Sheu, J.-H. “ Pregnane-Based Steroids from a Formosan Gorgonian Subergorgia mollis ” J. Chin. Chem. Soc. 2004, 51, 205-208.
39. Kobayashi, M.; Haribabu, B.; Anjaneyulu, V. “ Marine Sterols. XXI. Isolation of (24S)-3β-Hydroxyergost-5-en-21-oic Acid from a Sclerophytum sp. of Soft Coral ” Chem. Pharm. Bull. 1992, 40, 233-234.
40. Sheu, J.-H.; Chang, K.-C.; Sung, P.-J.; Duh, C.-Y.; Shen, Y.-C. “ Chemical Constituents of a Formosan Soft Coral Sinularia sp. ” J. Chin. Chem. Soc. 1999, 46, 253-257.
41. Duh, C.-Y.; Ali. A. H. El-Gamal; Song, P.-Y.; Wang, S.-K.; Dai, C.-F. “ Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya gigantea and Lemnalia cervicorni ” J. Nat. Prod. 2004, 67, 1650-1653.
42. Iorizzi, M.; Bryan, P.; Mcclintock, J.; Minale, L.; Palagiano, E.; Maurelli, S.; Riccio, R.; Zollo, F. “ Chemical and Biological Investigation of the Polar Constituents of the Starfish Luidia clathrata, Collected in the Gulf of Mexico ” J. Nat. Prod. 1995, 58, 653-671.
43. Wang, W.; Jang, H.; Hong, J.; Lee, C.-O.; Im, K. S.; Bae, S.-J.; Jung, J. H. “ Additional Cytotoxic Sterols and Saponins from the Starfish Certonardoa semiregularis ” J. Nat. Prod. 2004, 67, 1654-1660.
44. Greca, M. D.; Fiorentino, A.; Pinto, G.; Pollio, A.; Previtera, L. “ Rearrangements of Exogenus 17β-Hydroxy-17α-methylandrosta-1, 4-dien-3-one in Cultures of the Green Alga T76 Scenedesmus quadricauda ” J. Org. Chem. 1996, 61, 7178-7179.
45. Shirasaki, Y.; Inada, K.; Inoue, J.; Nakamura, M. “ Isolation and structure elucidation of the major photodegradation products of loteprednol etabonate ” Steroids 2004, 69, 23-34.
46. Schmitz, F. J.; Vanderah, D. J.; Hollenbeak, K. H.; Carol E. L. Enwall; Gopichand, Y. “ Metabolites from the Marine Sponge Tedania ignis. A New Atisanediol and Several Known Diketopiperazines ” J. Org. Chem. 1983, 48, 3941-3945.
47. Okada, N.; Shirata, K.; Niwano, M.; Koshino, H.; Uramoto, M. “ Immunosuppressive Activity of a Monoterpene from Eucommia ulmoides ” Phytochemistry 1994, 37, 281-282.
48. Kimura, J.; Maki, N. “ New Loliolide Derivatives from the Brown Alga Undaria pinnatifida ” J. Nat. Prod. 2002, 65, 57-58.
49. Kuba, M.; Furuichi, N.; Katsumura, S. “ Stereocontrolled Syntheses of Carotenoid Oxidative Metabolites, (-)-Loliolide, (-)-Xanthoxin, and Their Stereoisomers ” Chemistry Letters 2002, 12, 1248-1249.
50. Hammoumi, A.; Revial, G.; D’Angelo, J.; Girault, J. P.; Azerad, R. “ Microbial Hydroxylation and Functionalization of Synthetic Bicyclic Enones ” Tetrahedron Letters 1991, 32, 651-654.
51. Hammoumi, A.; Girault, J. P.; Azerad, R. “ Microbial Hydroxylation and Functionalization of Synthetic Polycyclic Enones ” Tetrahedron:Asymmetry 1993, 4, 1295-1306.
52. Fraga, B. M.; Hernandez, M. G.; Mestres, T.; Terrero, D.; Arteaga, J. M. “ Nor-sesquiterpenes from Teucrium heterophyllum ” Phytochemistry 1995, 39, 617-619.
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