跳到主要內容

臺灣博碩士論文加值系統

(44.210.21.70) 您好!臺灣時間:2022/08/15 07:48
字體大小: 字級放大   字級縮小   預設字形  
回查詢結果 :::

詳目顯示

: 
twitterline
研究生:簡士超
研究生(外文):Shih-Chao Chien
論文名稱:綠島產肥厚肉質與蜿蜒繖軟珊瑚化學成分及癌細胞毒殺活性之研究
論文名稱(外文):Chemical Constituents and Cytotoxicity of Formosan soft Corals Sarcophyton crassocaule an Xenia puerto-galerae
指導教授:杜昌益杜昌益引用關係
指導教授(外文):Cheng-Yeh Duh
學位類別:碩士
校院名稱:國立中山大學
系所名稱:海洋資源學系研究所
學門:自然科學學門
學類:海洋科學學類
論文種類:學術論文
論文出版年:2002
畢業學年度:90
語文別:中文
論文頁數:138
中文關鍵詞:癌症珊瑚
外文關鍵詞:Xenia puerto-galeraesoft CoralsSarcophyton crassocaulecancer
相關次數:
  • 被引用被引用:1
  • 點閱點閱:199
  • 評分評分:
  • 下載下載:29
  • 收藏至我的研究室書目清單書目收藏:1
綠島產肥厚肉質(Sarcophyton crassocule Von. Marenzeller)軟珊瑚之有機層萃取物經細胞活性測試,發現其對P-388、HT-29及A-549三種癌細胞有毒殺活性,以癌細胞毒殺活性為指標,再將二氯甲烷之萃取物以矽膠管柱層析進行分離純化後,得到四個cembrane diterpenoid化合物,分別是GN16-34 (1), GN16-35 (2), GN16-40 (3), GN16-62 (4),其中化合物4是新的新化合物。
綠島產蜿蜒繖(Xenia puerto-galerae Roxas)軟珊瑚之二氯甲烷層及丙酮層粗萃取物,以矽膠管柱層析及高效能液相色層分析儀(high-performance liquid chromatography, HPLC)進行分離純化後,得到六個cadinane sesquiterpenes化合物,分別為GN44-28 (5)、GN44-30 (6)、GN44-44 (7)、GN44-66 (8)、GN44-173 (9)、GN44-149 (10)及一個diterpenes,為GN44-199 (11),其中化合物5-10是新的合物。
上述化合物經癌細胞毒殺活性測試後,化合物3及4對P-388、HT-29及A-549細胞株均有顯著的抑制作用,化合物1及2對P-388細胞株有抑制作用,化合物5及7對A-549細胞株有顯著的抑制作用,化合物10對P-388及A-549細胞株均有抑制作用。
The methylene chloride extracts of Formosan soft coral Sarcophyton crassocule Von. Marenzeller (collected at Green Island off Taiwan) were found to exhibit significant cytotoxicity against P-388, HT-29, and A-549 cancer lines. Chromatographic separation led to the isolation of three known cembrane diterpenoids, GN16-34 (1), GN16-35 (2), GN16-40 (3), and a new cembrane, GN16-62 (4).
The methylene chloride and acetone extracts of Formosan soft coral Xenia puerto-galerae Roxas (collected at Green Island off Taiwan) were found to exhibit significant cytotoxicity against P-388 and A-549 cancer cell lines. Chromatographic separation resulted in the isolation of six new cadinane sesquiterpenes, GN44-28 (5), GN44-30 (6), GN44-44 (7), GN44-66 (8), GN44-173 (9), GN44-149 (10), and one known dicarbocyclic diterpenes with a bicyclic [4.3.1] ring system, GN44-199 (11).
Compounds 3 and 4 exhibited significant cytotoxicity against P-388, HT-29, and A-549 cancer cell lines. Compounds 1 and 2 exhibited significant cytotoxicity against P-388 cancer cell lines. Compounds 5 and 7 exhibited significant cytotoxicity against A-549 cancer cell line. compound 10 exhibited significant cytotoxicity against P-388 and A-549 cancer cell lines.
壹、緒論
一、前言
二、Sarcophyton屬軟珊瑚之天然物化學研究回顧
三、Xenia 屬軟珊瑚之天然物化學研究回顧
四、研究動機及目的
貳、肥厚肉質軟珊瑚化學成分之研究
一、材料採集與鑑定
二、肥厚肉質軟珊瑚之分類地位
三、肥厚肉質軟珊瑚之萃取與分離
四、肥厚肉質軟珊瑚化學成分之分離純化
(1)GN16-34 (1)之分離純化
(2)GN16-35 (2)之分離純化
(3)GN16-40 (3)之分離純化
(4)GN16-62 (4)之分離純化
五、肥厚肉質軟珊瑚化學成分之結構解析
(1)GN16-34 (1)之結構解析
(2)GN16-35 (2)之結構解析
(3)GN16-40 (3)之結構解析
(4)GN16-62 (4)之結構解析
參、蜿蜒繖軟珊瑚化學成分之研究
一、材料採集與鑑定
二、蜿蜒繖軟珊瑚之分類地位
三、蜿蜒繖軟珊瑚之萃取與分離
四、蜿蜒繖軟珊瑚化學成分之分離純化
(1)GN44-28 (5)之分離純化
(2)GN44-30 (6)之分離純化
(3)GN44-44 (7)之分離純化
(4)GN44-66 (8)之分離純化
(5)GN44-173 (9)之分離純化
(6)GN44-149 (10)之分離純化
(7)GN44-199 (11)之分離純化
五、蜿蜒繖軟珊瑚化學成分之結構解析
(1)GN44-28 (5)之解構解析
(2)GN44-30 (6)之解構解析
(3)GN44-44 (7)之解構解析
(4)GN44-66 (8)之解構解析
(5)GN44-173 (9)之解構解析
(6)GN44-149 (10)之解構解析
(7)GN44-199 (11)之解構解析
肆、化合物之細胞毒殺活性
伍、結論
陸、參考文獻
柒、附錄
一、儀器及材料
二、癌細胞毒殺活性測試之分析方法
三、MTT分析原理
1.李永適,1999,消失中的台灣珊瑚礁。大地別冊。2.U. Shmeuli, E. Zadock, and Y. Kashman, “Sarcophine, A New Epoxy Cembranolide from Marine Origin”, Tetrahedron, 1974, 30, 2817- 2824.3.E. Arie, and N. Ishak, “Inhibition of Phosphofructokinase by the Toxic Chembranolide Sarcophine isolated from the Soft-Bodied Coral Sarcophyton glaucum”, Toxicon, 1977, 15, 207-215.4. J. C. Coll, G. B. Hawes, N. Liyanage, W. Oberhansli, and R. J. Wells, “Studies of Australian Soft Corals. A New Cembrenoid Diterpene from a Sarcophyton Species”, Aust. J. Chem., 1977, 30, 1305-1309. 5. J. A. Toth, B. J. Burreson, J. Clardy, J. Finermoore, and P. J. Scheuer, “Emblide, A New Polyfunctional Cembranolide from the Soft Coral Sarcophyton Glaucum”, Tetrahedron, 1980, 36, 1307-1309.6. J. M. Frincke, D. J. Faulkner, and D. E. Mcintyre, “Deoxosarcophine from a Soft Coral, Sarcophyton Sp.”, Tetahedron Lett., 1980, 21, 735- 738. 7. B. F. Bowden, J. C. Coll, and S. J. Mitchell,“Studies of Australian Soft Corals.XVIII Further Cembranoid Diterpenes from Soft Corals of Genus Sarcophyton”, Aust. J. Chem., 1982, 33, 879-884. 8. S. Carmely, A. Groweiss, and Y. Kashman, “Decaryiol, a New Cembrane Diterpene from the Marine Soft Coral Sarcophyton decaryi”, J. Org. chem., 1981, 46, 4279-4284.9. R. Kazlauskas, J. A. Bairdlambert, P. T. Murphy, and R. J. Wells, “Two New Cembrane Diterpenes from a Soft Coral (Sarcophyton Species)”, Aust. J. Chem., 1982, 35, 61-68.10. A. J. Blackman, B. F. Bowden, J.C Coll, B. Frick, M. Mahendran, and S. J. Mitchell, “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, 1873-1880.11. B. F. Bowden, J. C. Coll, and R. H.Willis, “Studies of Australian Soft Corals .XXVII. Two Novel Diterpenes from Sarcophyton glaucum”, Aust. J. Chem., 1982, 35, 621-627. 12. M. Kobayashi, K. Hayashi, T.Hayashi, H. Mitsuhashi, T.Nakagawa, and M. Tanabe, “Marine Sterols .XI. Polyhydroxysterols of the Soft Coral Sarcophyton glaucum : Isolation and Synthesis of 5a- Cholesta-ne-1b, 3-b, 5,6-b -Tetrol”, Chem. Pharm. Bull., 1983, 31, 1848-1855.13. S. Jingyu, P. Tangsheng, L. Kanghou, and Z. Longmei, “24e- Sigma - Methyl 5a-Cholestane-3a, 6b, 9a, 25-Tetrol 25-Monoacetate, a Novel Polyhydroxylated Steroid from the Soft Coral SarcophytonTortuosum”, Steroids, 1986, 48, 233-238.14. J. Y. Su, J. Clardy, C. H. He, K. H. Long, and T. S. Pang, “The Structure of Methyl Isosartortuoate, a Novel Tetracyclic Tetraterpenoid from the Soft Coral Sarcophyton tortuosum”, J. Am. Chem. Soc., 1986, 108, 177-178.15. H. Fujiki, F. O. Cope, and O. G. Issinger, “Sarcophyton A, a potent tumor promoter inhibitor, prevents phosphorylation of a proteolytic fragment of C23 induced by the non-tpa type tumor promoter, okadaic acid”, Proceedings of the American Association of cancer Research, 1998, 29, 155.16. T. Kusumi, M. Igari, M. O. Ishitsuka, A. Ichikawa, Y. Itezono, N. Nakayama, and H. Kakisawa, “A Novel Chlorinated Biscembranoid from the Marine Soft Coral Sarcophyton glaucum”, J. Org. chem., 1990, 55, 6286-6289.17. M. Sugano, T. Shindo, A. Sato, Y.Iijima, T. Oshima, H. Kuwano, T. Hata, “Chatancin, a PAF Antagonist from a Soft Coral, Sarcophyton sp.”, J. Org. chem., 1990, 55, 5803-5805.18 M. Kobayashi, and E. Nakano, “Stereochemical Course of the Transannular Cyclization, in Chloroform, of Epoxycembranoids Derived from the Geometrical-Isomers of (14S)-14-Hydroxy - 1, 3, 7, 11-Cembratetraenes”, J. Org. chem., 1990, 55, 1947-1951.19 M. O. Ishitsuka, T. Kusumi, and H. Kakisawa, “Isolation of a Monomeric Counterpart of the Marine Biscembranoids, a Biogenetic Diels-Alder Precursor”, Tetahedron Lett., 1991, 32, 25, 2917-2918.20. U. Anthoni, K. Bock, C. Christophersen, J. O. Duus, E. B. Kjaer, and P. H. Nielsen, “Structure of a Novel Antifouling Epoxy Cembrenoid Diterpene from a Sarcophyton Sp.”, Tetahedron Lett., 1991, 32, 2825-2826. 21. P. A. Leone, B. F. Bowden, A. R. Carroll, J. C. Coll, and G. V. Meehan, “Studies of Australian Soft Corals, XLIX. A New Biscembranoid and Its Probable Biosynthetic Precursors from the Soft Coral Sarcophyton Tortuosum”, J. Nat. prod., 1993, 56, 521- 526. 22. T. Iwagawa, Y. Shibata, H. Okamura, M. Nakatani, and M. Shiro, “Novel Cembranoids with a 13-Membered Carbocyclic Skeleton from a Soft Coral, Sarcophyton Species”, Tetahedron Lett., 1994, 35, 8415- 8416.23. G. J. Greenland and B. F. Bowden, “Cembranoid Diterpenes Related to Sarcophytol-A from the Soft Coral Sarcophyton trocheliophorum”, Aust. J. Chem., 1994, 47, 2013-2021. 24. M. Zhang, K. H. Long, K. Ma, X. L. Huang, and H. M. Wu, “A Novel Diterpenoid from the Soft Coral Sarcophyton Solidum”, J. Nat. prod., 1995, 58, 414-418. 25. T. Iwagawa, S. Nakamura, T. Masuda, H. Okamura, M. Nakatani, and M. Siro, “Irregular Cembranoids Containing a 13-Membered Carbocyclic Skeleton Isolated from a Soft Coral, Sarcophyton Species”, Tetahedron, 1995, 51, 5291-5298.26. E. Fridkovsky, A. Rudi, Y. Benayahu, Y. Kashman, and M. Schleyer, “Sarcoglane, A New Cytotoxic Diterpene from Sarcophyton glaucum”, Tetahedron Lett., 1996, 37, 6909-6910. 27. T. Iwagawa, S. Nakamura, H. Okamura, and M. Nakatani “ Ichthyotoxic Cembranoids from the Soft Coral, Sarcophyton sp.”, Bull. Chem. Soc. Jpn, 1996, 69, 3543-3549. 28. C. Y. Duh, and R. S. Hou, “Cytotoxic Cembranoids from the Soft Corals Sinularia gibberosa and Sarcophyton trocheliophorum”, J. Nat. prod., 1996, 59, 595-598.29. A. S. R. Anjaneyulu, M. J. R. V. Venugopal, P. Sarada, G. V. Rao, J. Clardy, and E. Lobkovsky, “Sarcophytin, a Novel Tetracyclic Diterpenoid from the Indian-Ocean Soft Coral Sarcophyton Elegans”, Tetahedron Lett., 1998, 39, 135-138.30. G. M. Konig, and A. D. Wright, “New Cembranoid Diterpenes from the Soft Coral Sarcophyton Ehrenbergi”, J. Nat. prod., 1998, 61, 494-496. 31. T. Iwagawa, R. Nakashima, K. Takayama, H.Okamura, M. Nakatani, M. Doe, K. Shibata, “New Cembranes from the Soft Coral Sarcophyton Species”, J. Nat. prod., 1999, 62, 1046-1049. 32. H. Dong, Y. L. Gou, R. M Kini, H. X. Xu, S. X. Chen, S. L. M.Teo, and P. P. H. But, “A New Cytotoxic Polyhydroxysterol from Soft Coral Sarcophyton trocheliophorum”, Chem. Pharm. Bull., 2000, 48, 1087-1089. 33. C.Y Duh, S. K Wang, S. G Chung, G. C. Chou, and C.F. Dai, “Cytotoxic Cembrenolides and Steroids from the Formosan Soft Coral Sarcophyton Crassocaule ”, J. Nat. Prod., 2000, 63, 1634-1637.34. M. Yasumoto, K. Mada, T. Ooi, and T. Kusumi, “New Terpenoid Components from the Volatile Oils of the Soft Corals Clavularia-Viridis and Sarcophyton Acutangulum, J. Nat. Prod., 2000, 63, 1534-1536.35. A. S. R. Anjaneyulu, M. V. R. K. Murthy, P. M. Gowri, M. T. R. V. Venugopal, H. Laatsch, “A Rare Prostaglandin from the Soft Coral Sarcophyton Crassocaule of the Indian-Ocean”, J. Nat. Prod., 2000, 63, 1425-1426.36. V. Anjaneyulu, T. N. Makarieva, S. G. Ilyin, A. S. Dmitrenok, P. Radhika, P. V. Subbarao, V. V. Nesterov, M. Y. Antipin, and V. A. Stonik, “Two New Diterpenoids, Sarcophytin-B and Sarcophytin-C, from the Indian-Ocean Soft Coral Sarcophyton Species”, J. Nat. Prod., 2000, 63, 109-111.37. A. S. R. Anjaneyulu, M. V. R. K. Murthy, and P. M. Gowri, “Novel Epoxy Steroids from the Indian-Ocean Soft Coral Sarcophyton crassocaule” , J. Nat. Prod., 2000, 63, 112-118.38. D. J. Vanderash, P. A. Steudler, L. S. Ciereszko, F. J. Schmitz, J. D. Ekstrand, and D. van der Helm, “Marine Natural Products. Xenicin: a Diterpenoid Possessing a Nine-Membered Ring from the Soft Coral, Xenia elongata”, J. Am. Chem. Soc., 1976, 12, 5780-5784.39. Y. Kashman, and A. Groweiss, “Xeniolide-A and Xeniolide-B, Two new diterpenoids from the Soft Coral Xenia Macrospiculata”, Tetahedron Lett., 1978, 48, 4833-4836.40 Y. Kashman, and A. Groweiss, “New Diterpenoids from the Soft Corals Xenia macrospiculata and Xenia obscuronata”, J. Org. Chem., 1980, 45, 3814-3824. 41. B. F. Bowden, J. C. Coll, E. Ditzel, S. J. Mitchell, W. T. Robinson, “Studies of Australian Soft Corals. XXVIII. The Structure Determination of Two New Diterpenes from the Genus Xenia (Alcyonacea)”, Aust. J. Chem., 1982, 35, 5997-1002. 42. A. Groweiss, and Y. Kashman, “Eight New Xenia Diterpenoids from Three Soft Corals of the Red Sea”, Tetahedron, 1983, 39, 3385-3396.43. M. Kobayashi, Y. Kyogoku, I. Kitagawa, C. Yang, and C. Zheng, “Xeniolone and Isoxeniolone two New Diterpenes Having a Perhydroazulene Skeleton from an Okinawan Soft Coral of Xenia Sp.”, Chem. Pharm. Bull., 1985, 33, 1309-1312. 44. B. F. Bowden, J. C. Coll, and R. H. Willis, “Studies of Australian Soft Corals. XXXIX. New Sesquiterpene Metabolites from Several Xenia Species.”, Aust. J. Chem., 1986, 39, 1717-1722.45. I. Kitagawa, Z. Cui, Y. Kiyota, M. Kobayashi, and M. Ohnishi, “Marine Natural-Products .XV. Chemical-Constituents of an Okinawan Soft Coral of Xenia Sp (Xeniidae).”, Chem. Pharm. Bull., 1986, 34, 4590-4596. 46. I. Kitagawa, Y. Cai, Z. Cui, M. Kobayashi, and Y. Kyogoku, “Marine Natural-Products .XVI. Structures of Five New Diterpenes from an Okinawan Soft Coral of Xenia Sp”, Chem. Pharm. Bull., 1986, 34, 4641-4652. 47. B. F. Bowden, J. C. Coll, L. M. Engelhardt, A. Heaton, and A. H. White, “Studies of Australian Soft Corals. XLI. Structure Determination of a New Sesquiterpene from Xenia novae- britanniae and an Investigation of a Xenia Species”, Aust. J. Chem, 1987, 40, 1483-1489. 48. H. Lelong, A. Ahond, A. Chiaroni, P. Laboute, J. L. Menou, P. Potier, C. Poupat, J. Pusset, M. Pusset and C. Riche, “ New-Caledonian Lagoon Marine-Invertebrates .VIII. Terpene Metabolites from Xenia membranacea”, J. Nat. prod., 1987, 50, 203-210. 49. G. M. Konig, J. M.Gulbis, B. F. Bowden, D. Laurent, M. F. Mackay, S. C. Labarre, and J. C. Coll, “The Structure Determination of a Xenicane Diterpene from Xenia Garciae”, J. Nat. prod., 1989, 52, 294-299 50. T. Iwagawa, J. Kawasaki, T. Hase, C. M. Yu, J. A. Walter, and J. L. C. Wright, “A New-Tricarbocyclic Diterpene Structure from the Soft Coral Xenia Florida”, J. Chem. Commun., 1994, 18, 2073 -2074. 51. Y. Kashman, M. Saltoun, A. Rudi, and Y. Benayahu, “Xeniafaraunol- A and Xeniafaraunol-B, and Faraunatin ; Three New Cytotoxic Diterpenes from the Soft Coral Xenia Faraunensis”, Tetahedron Lett., 1994, 35, 8855-8858. 52. T. Miyamoto, Y. Takenaka, K. Yamada, and R. Higuchi, “Bioactive Diterpenoids from Octocorallia .2. Deoxyxeniolide-B, a Novel Ichthyotoxic Diterpenoid from the Soft Coral Xenia Elongata”, J. Nat. prod., 1995, 58, 924-928. 53. C. Vervoort, and W. Fenical, “Antibacterial Diterpenoids from an Undescribed Soft Coral of the genus Xenia”, J. Nat. Prod. Lett., 1995, 6, 49-55.54. T. Iwagawa, Y. Amano, T. Hase, and M. Shiro, “New Xenia Diterpenoids from a Soft Coral Xenia Species”, Tetahedron, 1995, 51, 11111-11118.55. T. Iwagawa, Y. Amano, M. Nakatani, and Hase-T, “New Xenia Diterpenoids from a Soft Coral, Xenia Species Containing Fatty Acyl Side-Chains”, Bull. Chem. Soc. Jpn., 1996, 69, 1309-1312. 56. T. Iwagawa, J. Kawasaki, T. Hase, and J. L. C. Wright, “New Dicarbocyclic and Tricarbocyclic Diterpenes Possessing a Bicyclic [4.3.1] Ring System Isolated from the Soft Coral “, Xenia Florida”, Tetahedron, 1997, 53, 6809-6816.57. T. Iwagawa, J. Kawasaki, and T. Hase, “New Xenia Diterpenes Isolated from the Soft Coral, Xenia Florida”, J. Nat. Prod., 1998, 61, 1513-1515.58. H. Miyaoka, M. Nakano, K. Iguchi, Y. Yamada, “Three New Xenicane Diterpenoids from Okinawan Soft Coral of the Genus, Xenia”, Tetahedron, 1999, 55, 12977-12982.59. T. Iwagawa, K Nakamura, T. Hirose, H. Okamura, M. Nakatani, “New Xenicane Diterpenes Isolated from the Acetone Extract of the Soft Coral Xenia Florida”, J. Nat. Prod., 2000, 63, 468-472. 60. H. Miyaoka, H. Mitome, M. Nakano, and Y. Yamada, “Xeniaoxolane : A New Xenicane-Type Diterpenoid from the Okinawan Soft Coral, Xenia Sp. ; Absolute-Configurations of Xeniaoxolane, Xeniolide-A and Xenialactol. Tetahedron, 2000, 56, 7737-7740.61. 戴昌鳳 “台灣的珊瑚” 台灣省政府教育廳科學教育資料叢書(XVIII),台灣省政府教育廳,中華民國七十八年。62. M. Iwagawa, Y. Matsumoto, H. Takahashi, and K. Iguchi, “New Marine Cembrane-type Diterpenoids from the Okinawan Soft Coral Clavularia koellikeri”, J. Nat. Prod., 2000, 63, 1647-1652.63. M. Bordoloi, V. S. Shukla, S. C. Nath, and R.Sharma, “Naturally Occurring Cadinenes”, Phytochemistry, 1989, 28, 2007-2037.
QRCODE
 
 
 
 
 
                                                                                                                                                                                                                                                                                                                                                                                                               
第一頁 上一頁 下一頁 最後一頁 top