Responsive image
博碩士論文 etd-0609100-163724 詳細資訊
Title page for etd-0609100-163724
論文名稱
Title
綠島產肥厚肉質、美麗肉質及花環肉質軟珊瑚 化學成分及癌細胞毒殺活性之研究
Chemical Constituents and Cytotoxicity of Soft Corals Sarcophyton crassocaule, Sarcophyton elegans and Sarcophyton trocheliophorum
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
131
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
1999-07-14
繳交日期
Date of Submission
2000-06-09
關鍵字
Keywords
癌細胞毒殺活性、肥厚肉質軟珊瑚、花環肉質軟珊瑚、美麗肉質軟珊瑚
Sarcophyton trocheliophorum, soft corals, Sarcophyton elegans, cytotoxicity, Sarcophyton crassocaule
統計
Statistics
本論文已被瀏覽 5719 次,被下載 2923
The thesis/dissertation has been browsed 5719 times, has been downloaded 2923 times.
中文摘要
綠島產肥厚肉質軟珊瑚 (Sarcophyton crassocaule) 之二氯甲烷萃取物分離純化後,共得到三個diterpenoid化合物,分別為:(1S*, 3R*, 4R*, 7E, 11E, 14R*)-3, 4-epoxycembra-7, 11, 15-trien-1, 14-olide (1)、(1R*, 3E, 7E,11R*, 12S*, 14R*)-11, 12-epoxycembra-3, 7, 15-trien-1, 14-olide (2)、(1R*, 2S*, 3E, 7S*, 8R*, 11S*, 12Z)-8, 11-epidioxy-7-acetoxycembra-3, 12, 15-trien-1, 2-olide (3),以及二個steroid化合物,分別為:(24S)-24-methylcholestane-3b, 5a, 6b-triol (4) 與24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5)。其中化合物1與2是新化合物,而化合物3為海洋天然物少見之含cyclic peroxide化合物。
綠島產美麗肉質 (S. elegans) 及花環肉質 (S. trocheliophorum) 軟珊瑚之二氯甲烷萃取物分離純化後,從美麗肉質軟珊瑚中分離到24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) 之steroid化合物,從花環肉質軟珊瑚中分離到 (+)-isosarcophine (6) 之diterpenoid化合物。
另外,由未知屬名之八放珊瑚 (編號CD01) 中,共分離到二個steroid化合物,分別為:cholesterol (7) 及 (22E, 24S)-24-methylcholesta- 5, 22-dien-3b-ol (8)。
上述之化合物經癌細胞毒殺活性測試後,化合物1-4、6及7對P388具有選擇性抑制作用,而化合物2和5則對HT-29有選擇性抑制。
Abstract
Chromatographic purification of a methylene chloride extract of Formosan soft coral Sarcophyton crassocaule (collected in Green island) led to the isolation of two new (1S*, 3R*, 4R*, 7E, 11E, 14R*)-3, 4-epoxycembra-7, 11, 15-trien-1, 14-olide (1) and (1R*, 3E, 7E,11R*, 12S*, 14R*)-11, 12-epoxycembra-3, 7, 15-trien-1, 14-olide (2) isomeric diterpenoids , a known cyclic peroxide diterpenoid (1R*, 2S*, 3E, 7S*, 8R*, 11S*, 12Z)-8, 11-epidioxy-7-acetoxycembra-3, 12, 15-trien-1, 2-olide (3), as well as two known (24S)-24-methylcholestane-3b, 5a, 6b-triol (4) and 24x-methyl-cholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) steroids.
Chromatographic fractionation of a methylene chloride extract of two Formosan soft corals Sarcophyton elegans (collected in Green island) led to the isolation of a known 24x-methylcholestane -3b, 5a, 6b, 25-tetrol 25-monoacetate (5) steroid, the methylene chloride extract of Sarcophyton trocheliophorum, on the other hand, afforded a known diterpenoid, (+)-isosarcophine (6).
Purification of a methylene chloride extract of Octocorallia soft coral (unidentified) led to the isolation of two known steroids, cholesterol (7) and (22E, 24S)-24-methylcholesta-5, 22-dien-3b-ol (8).
Compounds 1-7 exhibited cytotoxicity against P388 cancer cell line. Compounds 2 and 5 were active against HT-29 cancer cell line.
目次 Table of Contents
壹、緒論…………………………………………………………………12
一、 前言…………………………………………………………12
二、 曾由Sarcophyton屬軟珊瑚中分離到之化合物……………     14
三、 過去由Sarcophyton屬軟珊瑚所分離到之有生物活性二次代謝物………………………………………………………25
四、 研究動機及目的……………………………………………26
貳、Sarcophyton crassocaule軟珊瑚化學成分之研究………………27
一、 採集及分類地位……………………………………………27
二、 Sarcophyton crassocaule軟珊瑚之萃取與分離…………28
三、 Sarcophyton crassocaule軟珊瑚化學成分之分離純化……31
(1) GN26-203 (1) 之分離純化…………………………….31
(2) GN26-204 (2) 之分離純化………………………………33
(3) GN26-206 (3) 之分離純化………………………………35
(4) GN26-16K (4) 之分離純化……………………………37
四、 Sarcophyton crassocaule軟珊瑚化學成分之結構解析……40
(1) GN26-203 (1) 之結構解析………………………………40
(2) GN26-204 (2) 之結構解析………………………………52
(3) GN26-206 (3) 之結構解析………………………………63
(4) GN26-16K (4) 之結構解析……………………………74
參、Sarcophyton elegans軟珊瑚化學成分之研究……………………79
一、 採集及分類地位……………………………………………79
二、 Sarcophyton elegans軟珊瑚之萃取與分離…………………80
三、 Sarcophyton elegans軟珊瑚化學成分之分離純化………….82
(1) GN07-53K (5) 之分離純化……………………………..82
四、 Sarcophyton elegans軟珊瑚化學成分之結構解析…………85
(1) GN07-53K (5) 之結構解析……………………………85
肆、Sarcophyton trocheliophorum軟珊瑚化學成分之研究……………90
一、 採集及分類地位……………………………………………90
二、 Sarcophyton trocheliophorum軟珊瑚之萃取與分離………91
三、 Sarcophyton trocheliophorum軟珊瑚化學成分之分離純化…………………………………………………………….93
(1) GN11-97 (6) 之分離純化………………………………93
四、 Sarcophyton trocheliophorum軟珊瑚化學成分之結構解析……………………………………………………………95
(1) GN11-97 (6) 之結構解析………………………………..95
伍、編號CD01八放珊瑚化學成分之研究……………………………99
一、 採集及分類地位……………………………………………..99
二、 編號CD01八放珊瑚之萃取與分離………………………100
三、 編號CD01八放珊瑚化學成分之分離純化……………….102
(1) CD01-104K (7) 之分離純化……………………………102
(2) CD01-106K (8) 之分離純化……………………………104
四、 編號CD01八放珊瑚化學成分之結構解析………………107
(1) CD01-104K (7) 之結構解析……………………………107
(2) CD01-106K (8) 之結構解析……………………………111
陸、化合物之癌細胞毒殺活性………………………………………115
柒、結論………………………………………………………………116
捌、參考文獻…………………………………………………………118
玖、附錄………………………………………………………………127
一、 使用儀器及藥品……………………………………………127
二、 癌細胞毒殺活性測試之分析方法…………………………129
三、 MTT分析原理……………………………………………130






圖目錄
頁次
圖一、本研究所分離到之成分…………………………………………3
圖二、Sarcophyton crassocaule軟珊瑚所分離到之化學成分………29
圖三、Sarcophyton crassocaule軟珊瑚之分離流程………………….. 30
圖四、GN26-203 (1) 之1H-NMR圖譜…………………………………44
圖五、GN26-203 (1) 之13C-NMR及DEPT圖譜……………………45
圖六、GN26-203 (1) 之HMQC圖譜…………………………………46
圖七、GN26-203 (1) 之COSY圖譜……………………………………47
圖八、GN26-203 (1) 之HMBC圖譜…………………………………...48
圖九、GN26-203 (1) 之HMBC關聯圖………………………………...49
圖十、GN26-203 (1) 之NOESY圖譜…………………………………50
圖十一、GN26-203 (1) 之NOESY關聯圖……………………………51
圖十二、GN26-204 (2) 之1H-NMR圖譜………………………………55
圖十三、GN26-204 (2) 之13C-NMR及DEPT圖譜……………………56
圖十四、GN26-204 (2) 之HMQC圖譜………………………………..57
圖十五、GN26-204 (2) 之COSY圖譜…………………………………58
圖十六、GN26-204 (2) 之HMBC圖譜………………………………59
圖十七、GN26-204 (2) 之HMBC關聯圖……………………………60
圖十八、GN26-204 (2) 之NOESY圖譜………………………………61
圖十九、GN26-204 (2) 之NOESY關聯圖……………………………62
圖二十、GN26-206 (3) 之1H-NMR圖譜………………………………66
圖二十一、GN26-206 (3) 之13C-NMR及DEPT圖譜…………………67
圖二十二、GN26-206 (3) 之HMQC圖譜…………………………….68
圖二十三、GN26-206 (3) 之COSY圖譜………………………………69
圖二十四、GN26-206 (3) 之HMBC圖譜………………………….…70
圖二十五、GN26-206 (3) 之HMBC關聯圖……………………….…71
圖二十六、GN26-206 (3) 之NOESY圖譜………………………….…72
圖二十七、GN26-206 (3) 之NOESY關聯圖…………………………73
圖二十八、GN26-16K (4) 之1H-NMR圖譜………………………….76
圖二十九、GN26-16K (4) 之13C-NMR及DEPT圖譜…………….…77
圖三十、Sarcophyton elegans軟珊瑚所分離到之化學成分………….80
圖三十一、Sarcophyton elegans軟珊瑚之分離流程………………….81
圖三十二、GN07-53K (5) 之1H-NMR圖譜…………………………87
圖三十三、GN26-18K (5) 之1H-NMR圖譜……………………….…88
圖三十四、GN07-53K (5) 之13C-NMR及DEPT圖譜………………89
圖三十五、Sarcophyton trocheliophorum軟珊瑚所分離到之化學成分………………………………………………………….91
圖三十六、Sarcophyton trocheliophorum軟珊瑚之分離流程………..92
圖三十七、GN11-97 (6) 之1H-NMR圖譜……………………………..97
圖三十八、GN11-97 (6) 之13C-NMR及DEPT圖譜…………………..98
圖三十九、編號CD01八放珊瑚所分離到之化學成分…………100
圖四十、編號CD01八放珊瑚之分離流程……………………….101
圖四十一、CD01-104K (7) 之1H-NMR圖譜………………………109
圖四十二、CD01-104K (7) 之13C-NMR及DEPT圖譜……………110
圖四十三、CD01-106K (8) 之1H-NMR圖譜………………………113
圖四十四、CD01-106K (8) 之13C-NMR及DEPT圖譜……………114














表目錄
頁次
表一、曾由Sarcophyton屬分離到之Cembranoids…………………….14表二、曾由Sarcophyton屬分離到之Steroids………………………….17
表三、化合物4及文獻之13C-NMR化學位移表……………………78
表四、化合物1-8之癌細胞毒殺活性值………………………115
參考文獻 References
1. 林全信等人編著 "豐富的海洋資源",台灣書店,1997年初版,93-133頁。
2. Kobayashi, M.; Nakano, E. "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.
3. Bowden, B. F.; Coll, J. C.; Willis, R. H. "Two novel diterpenes from Sarcophyton glaucum", Aust. J. Chem., 1982, 35, 621.
4. Coll, J. C.; Hawes, G. B.; Liyabage, N.; Oberhansli, W.; Wella, R. J. "A new cembranoid diterpene from a Sarcophyton species", Aust. J. Chem., 1977, 30, 1305.
5. Bowden, B. F.; Coll, J. C.; Mitchell, S. J. "Further cembranoid diterpenes from soft corals of the genus Sarcophyton" Aust. J. Chem., 1980, 33, 879.
6. Toth, J. A.; Burreson, B. J.; Scheuer, P.; Finer-Moore, J.; Clardy, J. "Emblide, a new polyfunctional cembranolide from the soft coral Sarcophyton glaucum", Tetrahedron, 1980, 36, 1307.
7. Carmely, S.; Croweiss, A.; Kashman, Y. J. Org. Chem., 1981, 46, 4291.
8. Bowden, B. F.; Coll, J. C.; Hichs, W.; Kazlauskas, R.; Mitchell, S. J. "The isolation of epoxyisoneocembrene-A from Sinularia grayi and isoneocembrene-A from Sarcophyton ehrenberg", Aust. J. Chem., 1978, 31, 2707.
9. Bowden, B. F.; Coll, J. C.; Heaton, A.; Konig, G.; Bruck, M. A.; Cramer, B. E.; Scheuer, P. J. "The structures of four isomeric dihydrofuran-containing cembranoid diterpenes from several species of soft coral", J. Nat. Prod, 1987, 50 (4), 650,.
10. Wu, Y.-C.; Hsieh, P.-W.; Duh, C.-Y.; Soog, S.-K.; Fang, L.-S. "Studies on the Formosan soft coral I-cytotoxic cembrane diterpenes from Sarcophyton trocheliophorum", J. Chin. Chem. Soc., 1992, 39, 355.
11. Uchio, Y.; Nitta, M.; Nakayama, M.; Iwagawa, T.; Hase, T. "Ketoemblid and sarcophytolide, two new cembranoides with e-lactone function from the soft coral Sarcophyta elegans", Chem. Lett., 1983, 613.
12. Kazlauskas, R.; Baird-Lambert, J. A.; Murphy, P. T.; Wells, R. J. "Two new cembrane diterpenes from a soft coral (Sarcophyton sp.)", Aust. J. Chem., 1982, 35, 61.
13. Kobayashi, J.; Ohizumi, Y.; Nakamura, H.; Yamakado, T.; Matsuzaki, T.; Hirata, Y. "Ca-antagonistic substance from soft coral of the genus Sarcophyton", Experientia, 1983, 39, 67.
14. Bernstein, J.; Shmeuli, U.; Zadock, E.; Kashman, Y.; Neeman, I. "Sarcophine, a new epoxy cembranolide from marine origin", Tetrahadron, 1974, 30, 2817.
15. Kobayashi, M.; Osabe, K. "Minor cembranoid derivatives, structurally related to the potent anti-tumor-promoter sarcophytol A, from the soft coral Sarcophyton glaucum", Chem. Pharm. Bull., 1989, 37 (3), 631.
16. Nakagawa, T.; Kobayashi, M.; Hayashi, K.; Mitsuhashi, H. "Structures of three cembrane-type diterpenes, sarcophytol-C, sarcophytol-D, and sarcophytol-E, from the soft coral", Sarcophyton glaucum”, Chem. Pharm. Bull., 1981, 29 (1), 82.
17. Kobayashi, M.; Iesaka, T.; Nakano, E. "Structures of six new cembranoids, sarcophytols F, K, P, Q, R and S, from the soft coral Sarcophyton glaucum", Chem. Pharm. Bull., 1989, 37 (8), 2053.
18. Kobayashi, M.; Osabe, K. "Transannular cyclization of 3, 4-epoxy-1, 7, 11-cembratiene systems", Chem. Pharm. Bull., 1989, 37 (5), 1192.
19. Kobayashi, M.; Nakagawa, T.; Mitsuhashi, H. "Structures of four cembrane-type diterpenes; sarcophytol-A, sarcophytol-A acetate, sarcophytol-B, and sarcophytonin-A, from the soft coral, Sarcophyton glaucum", Chem. Pharm. Bull., 1979, 27, 2382.
20. Kobayashi, M.; Hirase, T. "Structures of new dihydrofurano- cembranoids isolated from a Sarcophyton sp. soft coral of Okinawa", Chem. Pharm. Bull., 1990, 38 (9), 2442.
21. Kobayashi, M.; Hirase, T. "Isolation of a new dihydrofurano- cembranoid, sarcophytonin E from the Sarcophyton sp. soft coral of Okinawa", Chem. Pharm. Bull., 1991, 39 (11), 3055.
22. Coll, J. C.; Bowden, R. F.; Tapiolas, D. M.; Willis, R. H.; Djura, P.; Streamer, M.; Trott, L. "The terpenoid chemistry of soft corals and its implications", Tetrahedron, 1985, 41, 1085.
23. Frincke, J. M.; Mcintyre, D. E.; Faulkner, D. J. "Deoxosarcophine from a soft coral, Sarcophyton sp.", Tetrahedron Lett., 1980, 21, 735.
24. Iwagawa, T.; Nakamura, S.; Masuda, T.; Okamura, H.; Nakatani, M.; Siro, M. "Irregular cembranoids containing a 13-membered carbocyclic skeleton isolated from a soft coral, Sarcophyton species", Tetrahedron, 1995, 51 (18), 5291.
25. Zhang, M.; Long, K.; Ma, K.; Huang, X.; Wu, H. "A novel diterpenoid from the soft coral Sarcophyton solidum", J. Nat. Prod., 1995, 58 (3), 414.
26. Miyaoka, H.; Taira, S.; Mitome, H.; Iguchi, K.; Matsumoto, K.; Yokoo, C.; Yamada, Y. "Two new cembrane-type diterpenoids from Okinawan soft coral of the genus, Sarcophyton", Chem. Lett., 1996, 239.
27. Zhang, M.; Long, K.; Huang, S.; Shi, K.; Mak, T. C. W. "A novel diterpenolide from the soft coral Sarcophyton solidum", J. Nat. Prod., 1992, 55 (11), 1672.
28. Anthoni, U.; Bock, K.; Christophersen, C.; Duus, J. ψ. ; Kjar, E. B. Nielsen, P. H. "Structure of a novel antifouling epoxy cembrenoid diterpene from a Sarcophyton sp.", Tetrahedron Lett., 1991, 32 (24), 2825.
29. Konig, G. M.; Wright, A. D. "New cembranoid diterpenes from the soft coral Sarcophyton ehrenbergi", J. Nat. Prod., 1998, 61, 494.
30. Duh, C.-Y.; Hou, R.-S. "Cytotoxic cembranoids from the soft corals Sinularia gibberosa and Sarcophyton trocheliophorum", J. Nat. Prod., 1996, 59, 595.
31. Fridkovsky, E.; Rudi, A.; Benayahu, Y.; Kashman, Y. "Sarcoglane, a new cytotoxic diterpene from Sarcophyton glaucum", Tetrahedron Lett., 1996, 37(38), 6909.
32. Sugano, M.; Shindo, T.; Sato, A.; Iijima, Y.; Oshima, T.; Kuwano, H.; Hata, T. "Chatancin, a PAF antagonist from a soft coral Sarcophyton sp.", J. Org. Chem., 1990, 55 (23), 5803.
33. Iwagawa, T.; Nakamura, S.; Okamura, H.; Nakatani, M. "Ichthyotoxic cembranoids from the soft coral, Sarcophyton sp.", Bull. Chem. Soc. Jpn., 1996, 69, 3543.
34. Leone, P. A.; Bowden, B. F.; Carroll, A. R.; Coll, J. C.; Meehan, G. V. "Studies of Australian soft corals, XLIX. A new biscembranoid and its probable biosysthetic precursors from the soft coral Sarcophyton tortuosum", J. Nat. Prod., 1993, 56 (4), 521.
35. Jingyu, S.; Kanghou, L.; Tangsheng P. "The structure of methyl isosartortuoate, a novel tetracyclic tetraterpenoid from the soft coral Sarcophyton tortuosum", J. Am. Chem. Soc., 1986, 108, 177.
36. Kusumi, T.; Igari, M.; Ishitsuka, M. O.; Ichikawa, A.; Itezono, Y.; Nakayama, N.; Kakisawa, H. "A novel chlorinated biscembranoid from the marine soft coral Sarcophyton glaucum", J. Org. Chem., 1990, 55, 6286.
37. Moldowan, J. M.; Tursch, B. M.; Djerassi, C. Steroids, 1974, 24, 387.
38. Moldowan, J. M.; Tan, W. L.; Djerassi, C. Steroids, 1975, 26, 107.
39. Kobayashi, M.; Tomioka, A.; Hayashi, T.; Mitsuhashi, H. "Isolation of 23-methylcholesta-5, 22-dien-3b-ol from the soft coral Sarcophyton glaucum", Chem. Pharm. Bull., 1979, 27 (8), 1951.
40. Kobayashi, M.; Hayashi, T.; Nakajima, F.; Mitsuhashi, H. Steroids, 1979, 34, 285.
41. Kobayashi, M.; Hayashi, T.; Hayashi, K.; Tanabe, M.; Nakagawa, T.; Mitsuhashi, H. "Marine steroids. XI. Polyhydroxysterols of the soft coral Sarcophyton glaucum: Isolation and synthesis of 5a-cholestane-1b, 3b, 5, 6b-tetrol", Chem. Pharm. Bull., 1983, 31 (6), 1848.
42. Kobayashi, M.; Ishizaka, T.; Mitsuhashi, H. "Isolation of 5a, 6-dihydroglaucasterol, a new marine C27 sterol with a 24, 26-cyclized side chain, from the soft coral Sarcophyton glaucum", Chem, Pharm. Bull., 1983, 31 (5), 1803.
43. Kobayashi, M.; Mitsuhashi, H. "Marine sterols. XIV. Isolation of (24S)-24-methyl-5a-cholestane-3b, 5, 6b, 25x, 26-pentol from the soft coral Sarcophyton glaucum", Chem. Pharm. Bull., 1983, 31 (11), 4127.
44. Raju, B. L.; Subbaraju, G. V.; Reddy, M. C.; Rao, D. V.; Rao, C. B.; Raju, V. S. "Polyhydroxysterols from the soft coral Sarcophyton subviride of Andaman and Nicobar Coasts", J. Nat. Prod., 1992, 55 (7), 904.
45. Su, J.; Peng, T.; Long, K.; Zeng, L. "24x-methyl 5a-cholestane-3a, 6b, 9a, 25-tetrol 25-monoacetate, a novel polyhydroxylated steroid from the soft coral Sarcophyton tortuosum", Steroids, 1986, 48, 233.
46. Umeyama, A.; Shoji, N.; Ozeki, M.; Arihara, S. "Sarcoaldesterols A and B, two new polyhydroxylated sterols from the soft coral Sarcophyton sp.", J. Nat. Prod., 1996, 59, 894.
47. Kobayashi, M.; Tomioka, A.; Mitsuhashi, H. "Marine sterols 8. Isolation and structure of sarcosterol, a new sterol with a 17(20)-double bond from the soft coral Sarcophyton glaucum", Steroids, 1979, 34, 237.
48. Kobayashi, M.; Tomioka, A.; Mitsuhashi, H. Steroids, 1979, 34, 273.
49. Yamada, Y.; Suzuki, S. Iguchi, K.; Kikuchi, H.; Tsukitani, Y.; Horiai, H.; Nakanishi, H. "Studies on marine natural products. II. New polyhydroxylated sterols from the soft coral Lobophytum pauciflorum (Ehrenberg)", Chem. Pharm. Bull., 1980, 28 (2), 473.
50. Lang, R. W.; Djerassi, C. "42. Stereochemical aspects of acid-catalyzed cyclopropane ring-opening reactions. A stereospecific pathway to crinosterol and brassicasterol", Helv. Chim. Acta, 1982, 65, 407.
51. Rubinstein, L.; Goad, L. D. "Occurrence of (24S)-24-methylcholesta-5, 22 E-dien-3b-ol in the diatom Phaeodactylum tricornutum", Phyto-chemistry, 1974, 13, 485.
52. Kitagawa, I.; Kobayashi, M.; Cui, Z.; Kiyota, Y.; Ohnishi, M. "Marine natural products. XV. Chemical constituents of an Okinawan soft coral of Xenia sp. (Xeniidae)", Chem. Pharm. Bull., 1986, 34 (11), 4590.
53. Anjaneyulu, V.; Rao, K. N. "(24S)-24-methylcholest-4-ene-3b, 6b-diol from a gorgonian (Rumphella aggregata) of the Andaman and Nicobar Islands", Indian J. Chem., 1995, 34B, 78.
54. Yamada, Y.; Suzuki, S.; Iguchi, K.; Kikuchi, H.; Tsukitani, Y.; Horiai, H. "Studies on marine natural products. III. Two new cembranolides from the soft coral Lobophytum pauciflorum (Ehrenberg)", Chem. Pharm. Bull., 1980, 28 (7), 2035.
55. Tursch, B.; Braekman, J. C.; Daloze, D.; Herin, D.; Karlsson, R. "Chemical studies of marine invertebrates. X. Lobophytolide, a new cembranolide diterpene from the soft coral Lobophytum cristagalli", Tetrahedron Lett., 1974, 43, 3769.
56. Marshall, J. A.; Andrews, R. C.; Lebioda, L. "Synthetic studies on cembranolides. Stereoselective total synthesis of isolobophytolide", J. Org. Chem., 1987, 52, 2378.
57. Bowden, B. F.; Coll, J. C.; Engelhardt, L. M.; Meehan, G. V.; Pegg, G. G.; Tapiolas, D. M.; White, A. H.; Willis, R. H. "Studies of Australian soft corals. XXXVII. The structure determination of two cembranolide diterpenes from soft corals of the genus Efflatounaria", Aust. J. Chem., 1986, 39, 123.
58. 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 (6), 2314.
59. Bowden, B. F.; Coll, J. C. "Studies of Australlan soft corals. XLV. Epoxidation reactions of cembranoid diterpenes : Stereochemical outcomes", Heterocycles, 1989, 28 (2), 669.
60. Rao, C. B.; Ramana, K V ; Kalidindi, R. S H S N ; Rao, D S.; Rao, D V. "Cembane diterpenes from a new species of the genus Lobophytum of the Indian Ocean", Indian J. Chem., 1994, 33B, 1004.
61. Morales, J. J.; Espina, J. R.; Rodriguez, A. D. "The structure of euniolide, a new cembranoid diterpene from the Caribbean gorgonians Eunicea succinea and Eunicea mammosa", Tetrahedron, 1990, 46 (17), 5889.
62. Erman, A.; Neeman, I. "Inhibition of phosphofructokinase by the toxic cembranolide sarcophine isolated from the soft-bodied coral Sarcophyton glaucum", Toxicon, 1977, 15, 207.
63. Weinheimer, A. J.; Matson, J. A.; Hossain, M. B.; Helm, D. van der "Marine anticancer agents: Sinularia and dihydrosinularin, new cembranolides from the soft coral, Sinularia flexibilis", Tetrahedron Lett., 1977, 2923.
64. Kusumi, T.; Igari, M.; Ishitsuka, M. O.; Ichikawa, A.; Itezono, Y.; Nakayama, N.; Kakisawa, H. "A novel chlorinated biscembranoid from the marine soft coral Sarcophyton glaucum", J. Org. Chem., 1990, 55, 6286.
65. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. "Spectrometric identification of organic compounds", New York: Wiley, 1991, 265.
66. Mosmann, T. "Rapid colorimetric assay for cellular growth and survial : Application to proliferation and cytotoxicity assays", J. Immu. Method, 1983, 65, 55.

電子全文 Fulltext
本電子全文僅授權使用者為學術研究之目的,進行個人非營利性質之檢索、閱讀、列印。請遵守中華民國著作權法之相關規定,切勿任意重製、散佈、改作、轉貼、播送,以免觸法。
論文使用權限 Thesis access permission:校內校外完全公開 unrestricted
開放時間 Available:
校內 Campus: 已公開 available
校外 Off-campus: 已公開 available


紙本論文 Printed copies
紙本論文的公開資訊在102學年度以後相對較為完整。如果需要查詢101學年度以前的紙本論文公開資訊,請聯繫圖資處紙本論文服務櫃台。如有不便之處敬請見諒。
開放時間 available 已公開 available

QR Code