(3.237.20.246) 您好!臺灣時間:2021/04/15 10:24
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:::

我願授權國圖
: 
twitterline
研究生:彭柏融
研究生(外文):Bo-Rong Peng
論文名稱:養殖型軟珊瑚Lobophytum crassum所含二次代謝物之研究
論文名稱(外文):Studies on the Secondary Metabolites from the Cultured Soft Coral Lobophytum crassum
指導教授:蘇瑞欣
指導教授(外文):Jui-Hsin Su
學位類別:碩士
校院名稱:國立東華大學
系所名稱:海洋生物研究所
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:2016
畢業學年度:104
論文頁數:160
中文關鍵詞:養殖型軟珊瑚隔板葉形軟珊瑚萜類化合物細胞毒殺
外文關鍵詞:Cultured soft coralLobophytum crassumTerpenoidsCytotoxicity
相關次數:
  • 被引用被引用:0
  • 點閱點閱:189
  • 評分評分:系統版面圖檔系統版面圖檔系統版面圖檔系統版面圖檔系統版面圖檔
  • 下載下載:0
  • 收藏至我的研究室書目清單書目收藏:0
摘要
隔板葉形軟珊瑚Lobophytum crassum,是亞太地區珊瑚礁中常見的珊瑚之一,其含有豐富的固醇類與萜類化合物,尤其是cembrane-type 的二萜類化合物,本實驗從養殖型L. crassum 的乙酸乙酯萃取物中分離得到14個化合物,包含一個新α-tocopherol類化合物 crassumtocopherol C (1),一個新cembranoid類化合物 culobophylin D (2)與一個新天然化合物 pseudoplexauric acid (3)以及11個已知化合物 cembrene (4)、lobophylin B (5)、crassocolide E (6) 、sarcocrassocolide (7) 、13-acetoxysarcocrassocolide (8) 、14-deoxycrassin (9)、lobocrassins B (10)和C (11)、sarcocrassocolides F (12), G (13) 和 M (14)。化合物1−14化學結構經由光譜數據分析及比對相關文獻資料而確認。
在生物活性方面,化合物5−8分別對6種癌細胞 K562、Molt-4、U937、Sup-T1、Ca9-22和Lncap進行細胞毒殺試驗,結果顯示化合物8對上述的6種細胞株皆具有良好的細胞毒殺活性 (IC50 =1.24、0.46、2.47、0.56、1.19和6.68 μg/mL),化合物6、7對 K562、Molt-4、U937、Sup-T1和Ca9-22五種細胞株具有良好的細胞毒殺活性 (IC50 =3.57、1.95、4.99、1.64和4.24; 5.73、2.66、1.38、2.63和8.63 μg/mL)。此外化合物9−14分別對4種血癌細胞株K562、Molt-4、U937和Sup-T1進行細胞毒殺試驗,結果顯示化合物9、10、12−14對上述4種血癌細胞皆具有良好的細胞活性。由細胞毒殺實驗結果可以推測化合物6−10、12−14 cembranoid類雙萜化合物的 C-1上α−methylene−γ−lactonec或是α−methylene−δ−lactone部位可能是細胞毒殺的主要功能性之片段結構。

Abstract
Lobophytum crassum, the alcyonacean coral, is one of the most common corals in reef flat communities in Asia-Pacific region. They are rich in steroids and terpenoids especially cembranoid diterpenes. We isolated fourteen compounds from the ethyl acetate extract of the cultured L. crassum. The isolated compounds included: a new α-tocopherol, crassumtocopherol C (1); a new cembranoid, culobophylin D (2); and a new natural product, pseudoplexauric acid (3), along with eleven known compounds, cembrene (4), lobophylin B (5), crassocolide E (6), sarcocrassocolide (7), 13-acetoxysarcocrassocolide (8), 14-deoxycrassin (9), lobocrassins B (10) and C (11), sarcocrassocolides F (12), G (13) and M (14).The structures of the isolates were elucidated using several spectroscopic techniques and by comparison of their spectroscopic data with those of the related metabolites.
The cytotoxic activity of 5−8 was evaluated against six cancer cell lines including K562, Molt-4, U937, Sup-T1, Ca9-22 and Lncap. Compound 8 exhibited the most potent cytotoxic activity against the tested six cancer cell lines (IC50 =1.24, 0.46, 2.47, 0.56, 1.19, 6.68 μg/mL), and 6−7 showed cytotoxicity against K562, Molt-4, U937, Sup-T1, Ca9-22 cancer cell lines (IC50 =3.57, 1.95, 4.99, 1.64, 4.24; 5.73, 2.66, 1.38, 2.63, 8.63 μg/mL). Moreover, the cytotoxic activity of 9−14 was evaluated against leukemia cell lines K562, Molt-4, U937, and Sup-T1. Compounds 9, 10, and 12−14 exhibited significant cytotoxicity against these leukemic cancer cell lines. Based on these results, it is suggested that the α−methylene−γ−lactone or α−methylene−δ−lactone moiety attached to C-1 in compounds 6−10 and 12−14 is critical for the cytotoxicity activity of these cembranoid diterpenes.

目錄
第一章、緒論 1
第一節、前言 1
第二節、文獻回顧 5
第二章、生物材料與研究方法 53
第一節、生物樣品採集與分類 53
第二節、生物樣品的萃取分離 55
第三節、實驗器材與材料 57
第三章、結果與討論 59
第一節、Lobophytum crassum 所含化合物之結構解析 59
(一)、Crassumtocopherol C (1) 之結構解析 61
(二)、Culobophylin D (2) 之結構解析 71
(三)、Pseudoplexauric acid (3) 之結構解析 81
(四)、Cembrene (4) 之結構解析 91
(五)、Lobophylin B (5) 之結構解析 97
(六)、Crassocolide E (6) 之結構解析 101
(七)、Sarcocrassocolide (7) 之結構解析 105
(八)、13-Acetoxysarcocrassocolide (8) 之結構解析 109
(九)、14-Deoxycrassin (9) 之結構解析 113
(十)、Lobocrassin B (10) 之結構解析 115
(十一)、Lobocrassin C (11) 之結構解析 119
(十二)、Sarcocrassocolide F (12) 之結構解析 123
(十三)、Sarcocrassocolide G (13) 之結構解析 127
(十四)、Sarcocrassocolide M(14) 之結構解析 131
第二節、新化合物實驗數據整理 135
第四章、生物活性試驗 137
第一節、細胞毒殺試驗 137
(一)、細胞培養 (Cell culture) 137
(二)、細胞冷凍保存 138
(三)、冷凍細胞活化 138
(四)、細胞毒殺活性試驗 (MTT assay) 138
(五)、Annexin V/ PI 雙重染色檢測細胞凋亡之程度 139
(六)、檢測細胞內粒線體膜電位之變化 139
第二節、生物活性試驗結果 141
(一)、細胞毒殺活性試驗結果 141
(二)、14-Deoxycrassin (9) Lobocrassin B (10)誘導Leukemia
cell 凋亡 142
第五章、結論 147
第六章、參考文獻 149

圖目錄
Figure 1-1. 海洋天然物及衍生物臨床用藥及其結構. 3
Figure 1-2. 2006−2011年各國發表新海洋天然物數量變化圖 4
Figure 2-1. Lobophytum crassum 隔板葉形軟珊瑚生態照I 54
Figure 2-2. Lobophytum crassum 隔板葉形軟珊瑚生態照II. 54
Figure 2-3. Lobophytum crassum分離流程. 56
Figure 3-1-1. The 1H-1H COSY and selected HMBC correlations for 1 62
Figure 3-1-2. Crassumtocopherol C相對立體結構 63
Figure 3-1-3. Crassumtocopherol A相對立體結構 63
Figure 3-1-4. 化合物 1 之低解析度ESIMS圖譜 65
Figure 3-1-5. 化合物 1 之高解析度ESIMS圖譜 65
Figure 3-1-6. 化合物 1 之IR圖譜 66
Figure 3-1-7. 化合物 1 之1H-NMR圖譜 66
Figure 3-1-8. 化合物 1 之1H-NMR放大圖譜 67
Figure 3-1-9. 化合物 1 之1H-NMR放大圖譜 67
Figure 3-1-10. 化合物 1 之13C-NMR圖譜 68
Figure 3-1-11. 化合物 1 之DEPT圖譜 68
Figure 3-1-12. 化合物 1 之HSQC圖譜 69
Figure 3-1-13. 化合物 1 之HMBC圖譜 69
Figure 3-1-14. 化合物 1 之COSY 圖譜 70
Figure 3-1-15. 化合物 1 之NOESY 圖譜 70
Figure 3-2-1. Selected 1H-1H COSY and HMBC correlations for 2 72
Figure 3-2-2. Selected NOESY correlation of 2 73
Figure 3-2-3. 化合物 2 之低解析度ESIMS圖譜 75
Figure 3-2-4. 化合物 2 之高解析度ESIMS圖譜 75
Figure 3-2-5. 化合物 2 之IR圖譜 76
Figure 3-2-6. 化合物 2 之1H-NMR圖譜 76
Figure 3-2-7. 化合物 2 之1H-NMR放大圖譜 77
Figure 3-2-8. 化合物 2 之1H-NMR放大圖譜 77
Figure 3-2-9. 化合物 2 之13C-NMR圖譜 79
Figure 3-2-10. 化合物 2 之DEPT圖譜 79
Figure 3-2-11. 化合物 2 之HSQC圖譜 80
Figure 3-2-12. 化合物 2 之HMBC圖譜 80
Figure 3-2-13. 化合物 2 之COSY 圖譜 81
Figure 3-2-14. 化合物 2 之NOESY 圖譜 81
Figure 3-3-1. 化合物 3 之低解析度ESIMS圖譜 83
Figure 3-3-2. 化合物 3 之高解析度ESIMS圖譜 83
Figure 3-3-3. 化合物 3 之IR圖譜 84
Figure 3-3-4. 化合物 3 之400 MHz 1H-NMR圖譜 84
Figure 3-3-5. 化合物 3 之500 MHz 1H-NMR圖譜 85
Figure 3-3-6. 化合物 3 之500 MHz 1H-NMR放大圖譜 85
Figure 3-3-7. 化合物 3 之500 MHz 1H-NMR放大圖譜 86
Figure 3-3-8. 化合物 3 之13C-NMR圖譜 86
Figure 3-3-9. 化合物 3 之DEPT圖譜 87
Figure 3-3-10. 化合物 3 之HSQC圖譜 87
Figure 3-3-11. 化合物 3 之HMBC圖譜 88
Figure 3-3-12 化合物 3 之COSY 圖譜 88
Figure 3-3-13 化合物 3 之NOESY 圖譜 89
Figure 3-4-1. 化合物 4 之1H-NMR圖譜 93
Figure 3-4-2. 化合物 4 之13C-NMR圖譜 93
Figure 3-4-3. 化合物 4 之DEPT圖譜 94
Figure 3-4-4. 化合物 4 之HSQC圖譜 94
Figure 3-4-5. 化合物 4 之HMBC圖譜 95
Figure 3-4-6. 化合物 4 之COSY圖譜 95
Figure 3-4-7. 化合物 4 之NOESY圖譜 96

1. Butler, M.S.; Robertson, A.A.B.; Cooper, M.A. Natural product and natural product derived drugs in clinical trials Nat. Prod. Rep. 2014, 31, 1612−1661.
2. Liu, C.-C.; Xu, X.-L.; Sun, Y.-L.; Zhang, X.-L.; Wang, C.; Zhuang, B.; Fan, Y.-F.; Zhang, G.-T.; Wang, C. Progress in the clinical development of small molecular marine-originated drugs. Chin. J. Mar. Drugs. 2015, 34, 73–89.
3. Martins, A.; Vieira, H.; Gaspar, H.; Santos, S. Marketed marine natural products in the pharmaceutical and cosmeceutical industries: tips for success. Mar. Drugs. 2014, 12, 1066−1101.
4. 邵廣昭; 彭鏡毅; 吳文哲,2008 臺灣物種多樣性–II. 物種名錄,行政院農業委員會林務局,2008。
5. Blunt, J.B.; Copp, B.R.; Keyzers, R.A.; Munroa, M.H.G.; Prinsep, M.R. Marine Nature Products. Nat. Prod. Rep. 2013, 30, 237–323.
6. Chen, N.-F.; Huang, S.-Y.; Lu, C.-H.; Chen, C.-L.; Feng, C.-W.; Chen, C.-H.; Lin, Y.-Y.; Sung, P.-J.; Sung, C.-S.; Yang, S.-N.; Wang, H.-M. David.; Chang, Y.-C.; Sheu, J.-H.; Chen, W.-F.; Wen, Z.-H. Flexibilide Obtained from Cultured Soft Coral Has Anti-Neuroinflammatory and Analgesic Effects through the Upregulation of Spinal Transforming Growth Factor-β1 in Neuropathic Rats. Mar. Drugs. 2014, 12, 3792–3817.
7. Lin, Y.-Y.; Lin, S.-C.; Feng, C.-W.; Chen, P.-C.; Su, Y.-D.; Li, C.-M.; Yang, S.-N.; Jean, Y.-H.; Sung, P.-J.; Duh, C.-Y.; Wen, Z.-H. Anti-Inflammatory and Analgesic Effects of the Marine-Derived Compound Excavatolide B Isolated from the Culture-Type Formosan Gorgonian Briareum excavatum. Mar. Drugs. 2015, 13, 2559–2579.
8. Su, C.-C.; Jeff, Chen, Y.-F.; Din, Z.-H.; Su, J.-H.; Yang, Z.-Y.; Chen, Y.-J.; Wang, Robert, Y.L.; Wu, Y.-J. 13-Acetoxysarcocrassolide Induces Apoptosis on Human Gastric Carcinoma Cells Through Mitochondria-Related Apoptotic Pathways: p38/JNK Activation and PI3K/AKT Suppression. Mar. Drugs. 2014, 12, 5295–5315.
9. Lin, J.-J.; Su, J.-H.; Tsai, C.-C.; Chen, Y.-J.; Liao M.-H.; Wu, Y.-J. 11-epi-Sinulariolide Acetate Reduces Cell Migration and Invasion of Human Hepatocellular Carcinoma by Reducing the Activation of ERK1/2, p38MAPK and FAK/PI3K/AKT/mTOR Signaling Pathways. Mar. Drugs. 2014, 12, 4783–4798.
10. Su, J.-Y.; Meng, Y.-H.; Zeng, L.-M. Lobocalone: a novel secondary metabolite from the soft coral Lobophytum caledonense. J. Nat. Prod. 1993, 56, 279–281.
11. Minh, C.V.; Kiem, P.V.; Nhiem, N.X.; Cuong, N.X.; Thao, N.P.; Nam, N.H.; Anh, H.L.T.; Thung, D.C.; Thuy, D.T.T.; Kang, H.-K.; Jang, H.-D., Kim, Y.H. Cytotoxic and antioxidant activities of diterpenes and sterols from the Vietnamese soft coral Lobophytum compactum. Bioorg. Med. Chem. Lett. 2011, 21, 2155–2159.
12. Ahond, A.; Bowden, B.F.; Coll, J.C.; Fourneron, J.-D.; Mitchell, S.J. Futher cembranolide diterpenes from Lobophytum crassospiculatum and a correction of a previous stereochemical assignment. Aust. J. Chem. 1979, 32, 1273–1280.
13. Bowden, B.F.; Brittle, J.A.; Coll, J.C.; Liyanage, N.; Mitchell, S.J.; Stokie, G.J. A new cembranolide diterpene from the soft coral Lobophytum crassum. Tetrahedron Lett. 1977, 41, 3661−3662.
14. Kashman, Y.; Carmely, S.; Groweiss, A. Further cembranoid derivatives from the red sea soft corals Alcyonium flaccidum and Lobophytum crassum. J. Org. Chem. 1981, 46, 3592−3596.
15. Venkateswalu, Y.; Rao, M.R.; Ramesh, P. A new polyhydroxy sterol from the soft coral Lobophytum crassum. J. Nat. Prod. 1997, 60, 1301−1302.
16. Matthée, G.F.; König, G.M.; Wright, A.D. Three new diterpenes from the marine soft coral Lobophytum crassum. J. Nat. Prod. 1998, 61, 237−240.
17. Rao, M.R.; Venkatesham, U.; Reddy, M.V.R.; Venkateswarlu, Y. An unusual novel C29 steroid from the soft coral Lobophytum crassum. J. Nat. Prod. 1999, 62, 785−786.
18. Duh, C.-Y.; Wang, S.-K.; Huang, B.-T.; Dai, C.-F. cytotoxic cembrenolide diterpenes from the formosan soft coral Lobophytum crassum. J. Nat. Prod. 2000, 63, 884−885.
19. Yin, S.-W.; Shi, Y.-P.; Li, X.-M.; Wang, B.-G. A novel hydroperoxyl substituted cembranolide diterpene from marine soft coral Lobophytum crassum. Chinese Chem. Lett. 2005, 16, 1498−1491.
20. Yin, S.-W.; Shi, Y.-P.; Li, X.-M.; Wang, B.-G. A new cembranoid diterpene and other related metabolites from the south-china-sea soft coral Lobophytum crassum. Helv. Chim. Acta. 2006, 89, 567−572.
21. Chao, C.-H.; Huang, H.-C.; Wu, Y.-C.; Lu, C.-K.; Dai, C.-F.; Sheu, J.-H. Glycolipids from the formosan soft coral Lobophytum crassum. Chem. Pharm. Bull. 2007, 55, 1720−1723.
22. Zhang, W.; Krohn, K.; Ding, J.; Miao, Z.-H.; Zhou, X.-H.; Chen, S.-H.; Pescitelli, G.; Salvadori, P.; Kurtan, T.; Guo, Y.-W. Structural and stereochemical studies of α-methylene-γ-lactone-bearing cembrane diterpenoids from a south china sea soft coral Lobophytum crassum. J. Nat. Prod. 2008, 71, 961−966.
23. Chao, C.-H.; Wen, Z.-H.; Wu, Y.-C.; Yeh, H.-C.; Sheu, J.-H. Cytotoxic and anti-inflammatory cembranoids from the soft coral Lobophytum crassum. J. Nat. Prod. 2008, 71, 1819−1824.
24. Lin, S.-T.; Wang, S.-K.; Cheng, S.-Y.; Duh, C.-Y. Lobocrasol, a new diterpenoid from the soft coral Lobophytum crassum. Org. Lett. 2009, 11, 3012−3014.
25. Wanzola, M.; Furuta, T.; Kohno, Y. Fukumitsu, S.; Yasukochi, S.; Watari, K.; Tanaka, C.; Higuchi, R.; Miyamoto, T. Four new cembrane diterpenes isolated from an okinawan soft coral Lobophytum crassum with inhibitory effects on nitric oxide production. Chem. Pharm. Bull. 2010, 58, 1203−1209.
26. Liao, Z.-J.; Su, H.-J.; Shyue, Y.-C.; Wen, Z.-H.; Sheu, J.-H.; Su, J.-H. Two new cembranoids from the soft coral Lobophytum crassum. Bull. Chem. Soc. Jpn. 2011, 84, 653−655.
27. Cheng, S.-Y.; Lin, S.-T.; Wang, S.-K.; Duh, C.-Y. α-Tocopherols from the formosan soft coral Lobophytum crassum. Bull. Chem. Soc. Jpn. 2011, 84, 783−787.
28. Tseng, Y.-J.; Wen, Z.-H.; Hsu, C.-H.; Dai, C.-F.; Sheu, J.-H. Bioactive cembranoids from the dongsha atoll soft coral Lobophytum crassum. Bull. Chem. Soc. Jpn. 2011, 84, 1102−1106.
29. Kao, C.-Y.; Su, J.-H.; Lu, M.-C.; Hwang, T.-L.; Wang, W.-H.; Chen, J.-J.; Sheu, J.-H.; Kuo, Y.-H.; Weng, C.-F.; Fang, L.-S.; Wen, Z.-H.; Sung, P.-J. Lobocrassins A–E: new cembrane-type diterpenoids from the soft coral Lobophytum crassum. Mar. Drugs. 2011, 9, 1319−1331.
30. Lee, N.-L.; Su, J.-H. Tetrahydrofuran cembranoids from the cultured soft coral Lobophytum crassum. Mar. Drugs. 2011, 9, 2526−2536.
31. Lin, S.-T.; Wang, S.-K.; Duh, C.-Y. Cembranoids from the dongsha atoll soft coral Lobophytum crassum. Mar. Drugs. 2011, 9, 2705−2716.
32. Lee, C.-H.; Kao, C.-Y.; Kao, S.-Y.; Chang, C.-H.; Su, J.-H.; Hwang T.-L.; Kuo, Y.-H.; Wen, Z.-H.; Sung, P.-J. Terpenoids from the octocorals Menella sp. (Plexauridae) and Lobophytum crassum (Alcyonacea) Mar. Drugs. 2012, 10, 427−438.
33. Thao, N.P.; Nam, N.H.; Cuong, N.X.; Nhiem, N.X.; Tung, P.T.; Quang, T.H.; Ngan, N.T.T.; Kiem, P.V.; Minh, C.V.; Kim, Y.H. A new sterol from the soft coral Lobophytum crassum. Bull. Korean Chem. Soc. 2013, 34, 249−251.
34. Thao, N.P.; Luyen, B.T.T.; Ngan, N.T.T.; Song, S.B.; Cuong, N.X; Nam, N.H.; Kiem, P.V.; Kiem, Y.H.; Minh, C.V. New anti-inflammatory cembranoid diterpenoids from the vietnamese soft coral Lobophytum crassum. Bioorg. Med. Chem. Lett. 2014, 24, 228−232.
35. Cuong, N.X.; Thao, N.P.; Luyen, B.T.T.; Ngan, N.T.T.; Thuy, D.T.T.; Song, S.B.; Nam, N.H.; Kiem, P.V.; Kim, Y.H.; Minh, C.V. Cembranoid diterpenes from the soft coral Lobophytum crassum and their anti-inflammatory activities. Chem. Pharm. Bull. 2014, 62, 203−208.
36. Cheng, S.-Y.; Wang, S.-K.; Duh, C.-Y. Secocrassumol, a seco-cembranoid from the dongsha atoll soft coral Lobophytum crassum. Mar. Drugs. 2014, 12, 6028−6037.
37. Tursch, B.; Braekman, J.C.; Daloze, D.; Herin, M.; Karlsson, R. Lobophtolide, A new cembranolide diterpene from the soft coral Lobophytum cristagalli (Coelenterata, Octocorallia, Alycyonacea). Tetrahedron Lett. 1974, 43, 3376−3772.
38. Bowden, B.F.; Coll, J.C.; Costa, M.S.L.; Mackay, M.F.; Mahendran, M.; Silva, E.D.; Wills, R.H. The structure determination of a new cembranolide diterpene from the soft coral Lobophytum cristigalli (Coelenterata, Octocorallia, Alcyonacea). Aust. J. Chem. 1984, 37, 545−552.
39. Li, L.; Sheng, L.; Wang, C.-Y.; Zhou, Y.-B.; Huang, H.; Li, X.-B.; Li, J.; Mollo, E.; Gavagnin, M.; Guo, Y.-W. Diterpenes from the hainan soft coral Lobophytum cristatum tixier-durivault. J. Nat. Prod. 2011, 74, 2089−2094.
40. Uchio, Y.; Eguchi, S.; Kuramoto, J.; Nakayama, M.; Hase, T. Denticulatolide, an ichthyotoxic peroxide-containing cembranolide from the soft coral Lobophytum denticulatum. Tetrahedron Lett. 1985, 26, 4487−4490.
41. Uchio, Y.; Eguchi, S.; Fukazawa, Y.; Kodama, M. 7-Epidenticulatolide, a new cembranolide with a cyclic peroxide function from the soft coral Lobophytum denticulatum. Bull. Chem. Soc. Jpn. 1992, 65, 1182−1184.
42. Carmely, S.; Kashman, Y. New prostaglandin (PGF) derivatives from the soft coral Lobophytum depressum. Tetrahedron Lett. 1980, 21, 875−878.
43. Carmely, S.; Kashman, Y. Five new C28 polyoxygenated sterols from the red sea soft coral Lobophytum depressum. Tetrahedron. 1981, 37, 2397−2403.
44. Cheng, S.-Y.; Wen, Z.-H.; Chiou, S.-F.; Hsu, C.-H.; Wang, S.-K.; Dai, C.-F.; Chiang, M.Y.; Duh, C.-Y. Durumolides A-E, anti-inflammatory and antibacterial cembranolides from the soft coral Lobophytum durum. Tetrahedron. 2008, 64, 9698−9704.
45. Cheng, S.-Y.; Wen, Z.-H.; Wang, S.-K.; Chiou, S.-F.; Hsu, C.-H.; Dai, C.-F.; Duh, C.-Y. Anti-inflammatory cembranolides from the soft coral Lobophytum durum. Bioorg. Med. Chem. 2009, 17, 3763−3769.
46. Cheng, S.-Y.; Wen, Z.-H.; Chiou, S.-F.; Hsu, C.-H.; Wang, S.-K.; Dai, C.-F.; Chiang, M.Y.; Duh, C.-Y. Unprecedented hemiketal cembranolides with anti-inflammatory activity from the soft coral Lobophytum durum. J. Nat. Prod. 2009, 72, 152−155.
47. Cheng, S.-Y.; Chen, P.-W.; Chen, H.-P.; Wang, S.-K.; Duh, C.-Y. New cembranolides from the Dongsha Atoll soft coral Lobophytum durum. Mar. Drugs. 2011, 9, 1307−1318.
48. Bowden, B.F.; Coll, J.C.; Liyanage, N.; Mitchell, S.J.; Stokie, G.J.; Altena, I.A.V. A noval bicyclic diterpene from Lobophytum hedleyi. Aust. J. Chem. 1978, 31, 163−170.
49. Uchio, Y.; Toyota, J.; Nozaki, H.; Nakayama, M. Lobohedlide and (7Z)-lobohedlide, new cembranolides from the soft coral Lobophytum hedleyi whitelegge. Tetrahedron Lett. 1981, 22, 4089−4092.
50. Quang, T.H.; Ha, T.T.; Minh, C.V.; Kiem, P.V.; Huong, H.T.; Ngan, N.T.T.; Nhiem, N.X.; Tung, N.H.; Tai, B.H.; Thuy, D.T.T.; Song, S.B.; Kang, H.-K.; Kim, Y.H. Cytotoxic and anti-inflammatory cembranoids from the Vietnamese soft coral Lobophytum laevigatum. Bioorg. Med. Chem. 2011, 19, 2625−2632.
51. Coll, J.C.; Mitchell, S.J.; Stokie, G.J. A novel cembrenoid diterpene from Lobophytum michaelae. Aust. J. Chem. 1977, 30, 1859−1863.
52. Wang, S.-K.; Duh, C.-Y.; Wu, Y.-C.; Wang, Y.; Cheng, M.-C.; Soong, K.; Fang, L.-S. Cytotoxic cembranolides from the soft coral Lobophytum michaelae. J. Nat. Prod. 1992, 55, 1430−1435.
53. Wang, L.-T.; Wang, S.-K.; Soong, K.; Duh, C.-Y. New cytotoxic cembranolides from the soft coral Lobophytum michaelae. Chem. Pharm. Bull. 2007, 55, 766−770.
54. Wang, S.-K.; Duh, C.-Y. New cytotoxic cembranolides from the soft coral Lobophytum michaelae. Mar. Drugs. 2012, 10, 306−318.
55. Tursch, B.; Hootelé, C.; Kaisin, M. Structure and absolute configuration of lobosterol, a novel polyoxygenated sterol from the alcyonacean Lobophytum pauciflorum (Coelenterata, Octocorallia). Steroids. 1976, 27, 137−142.
56. Yamada, Y.; Suzuki, S.; Iguchi, K.; Kikuchi, H.; Tsukitani, Y.; Horiai, H.; Nakanishi, H. New polyhydroxylated sterols from soft coral Lobophytum pauciflorum (Ehrenberg). Chem. Pharm. Bull. 1980, 28, 473−478.
57. Yamada, Y.; Suzuki, S.; Iguchi, K.; Kikuchi, H.; Tsukitani, Y.; Horiai, H. Two new cembranolides from the soft coral Lobophytum pauciflorum (Ehrenberg). Chem. Pharm. Bull. 1980, 28, 2035−2038.
58. Yamada, Y.; Suzuki, S.; Iguchi, K.; Kikuchi, H.; Tsukitani, Y.; Horiai, H.; Shibayama, F. The stereochemistry of 13-membered carbocyclic cembranolide diterpenes from the soft coral Lobophytum pauciflorum (Ehrenberg). Tetrahedron. Lett. 1980, 21, 3911−3914.
59. Lu, Q.; Faulkner, D.J. Two 11α-acetoxysterols from the Palauan soft coral Lobophytum pauciflorum. Nat. Prod. Lett. 1997, 10, 231−237.
60. Edrada, R.A.; Proksch, P.; Wary, V.; Witte, L.; Ofwegen, L.V. Four new bioactive Lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines. J. Nat. Prod. 1998, 61, 358−361.
61. Yan, P.; Lv, Y.; Ofwegen, L.V.; Proksch, P.; Lin, W. Lobophytones A-G, new isobiscembranoids from the soft coral Lobophytum pauciflorum. Org. Lett. 2010, 12, 2484−2487.
62. Yan, P.; Lv, Y.; Ofwegen, L.V.; Proksch, P.; Lin, W. Lobophytones H—N, biscembranoids from the chinese soft coral Lobophytum pauciflorum. Chem. Pharm. Bull. 2010, 58, 1591−1595.
63. Yan, P.; Deng, Z.; Ofwegen, L.V.; Proksch, P.; Lin, W. Lobophytones O–T, new biscembranoids and cembranoid from soft coral Lobophytum pauciflorum. Mar. Drugs. 2010, 8, 2837−2848.
64. Yan, P.; Deng, Z.; Ofwegen, L.V.; Proksch, P.; Lin, W. Lobophytones U–Z1, biscembranoids from the chinese soft coral Lobophytum pauciflorum. Chem. Biodives. 2011, 8, 1724−1734.
65. Govindam, S.V.S.; Yoshioka, Y.; Kanamoto, A.; Fujiwara, T.; Okamoto, T.; Ojika, M. Cyclolobatriene, a novel prenylated germacrene diterpene, from the soft coral Lobophytum pauciflorum. Bioorg. Med. Chem. 2012, 20, 687−692.
66. Lu, Y.; Lin, Y.-C.; Wen, Z.-H.; Su, J.-H.; Sung, P.-J.; Hsu, C.-H.; Kuo, Y.-H.; Chiang, M.Y.; Dai, C.-F.; Sheu, J.-H. Steroid and cembranoids from the Dongsha atoll soft coral Lobophytum sarcophytoides. Tetrahedron. 2010, 66, 7129−7135.
67. Yamada, K.; Ryu, K.; Miyamoto, T.; Higuchi, R. Bioactive terpenoids from octocorallia. 4. three new cembrane-type diterpenoids from the soft coral Lobophytum schoedei. J. Nat. Prod. 1997, 60, 798−801.
68. Bowden, B.F.; Coll, J.C.; Mitchell, S.J.; Stokie, G.J. Two new diterpenes from an unknown species of soft coral (Genus Lobophytum). Aust. J. Chem. 1978, 31, 1303−1312.
69. Bowden, B.F.; Coll, J.C.; Tapiolas, D.M. New cembranoid diterpenes from a Lobophytum species. Aust. J. Chem. 1983, 36, 2289−2295.
70. Subrahmanyam, C.; Rao, C.V.; Anjaneyulu, V.; Satyanarayana, P.; Rao, P.V.S. New diterpenes from a new species of Lobophytum soft coral of the south Andaman Coast. Tetrahedron. 1992, 48, 3111−3120.
71. Raju, B.L.; Subbaraju, G.V.; Rao, C.B.; Trimurtulu, G. Two new oxygenated lobanes from a soft coral of Lobophytum species of the Andaman and Nicobar Coasts. J. Nat. Prod. 1993, 56, 961−966.
72. Morris, L.A.; Christie, E.M.; Jaspars, M.; Ofwegen, L.P.V. A bioactive secosterol with an unusual a- and b-ring oxygenation pattern isolated from an Indonesian soft coral Lobophytum sp. J. Nat. Prod. 1998, 61, 538−541.
73. Rashid, M.A.; Gustafson, K.R.; Boyd, M.R. HIV-inhibitory cembrane derivatives from a philippines collection of the soft coral Lobophytum species. J. Nat. Prod. 2000, 63, 531−533.
74. Radhika, P.; Rao, V.L.; Laatschi, H. Chemical constituents of a marine soft coral of the genus Lobophytum. Chem. Pharm. Bull. 2004, 52, 1345−1348.
75. Muralidhar, P.; Kumar, M.M.; Krishina, N.; Rao, C.B.; Rao, D.V. New sphingolipids and a sterol from a Lobophytum species of the Indian ocean. Chem. Pharm. Bull. 2005, 53, 168−171.
76. Chen, S.-H.; Huang, H.; Guo, Y.-W. Four new cembrane diterpenes from the Hainan soft coral Lobophytum sp. Chin. J. Chem. 2008, 26, 2223−2227.
77. Chen, S.-H.; Guo, Y.-W.; Huang, H.; Cimono, G. Six new cembranolides from the Hainan soft coral Lobophytum sp. Helv. Chim. Acta. 2008, 91, 873−880.
78. Chen, S.-H.; Huang, H.; Guo, Y.-W. A new diterpenoid from the south China sea soft coral Lobophytum sp. J. Asian. Nat. Prod. Res. 2008, 10, 965−969.
79. Fattorusso, E.; Romano, A.; Taglialatela-Scafati, O.; Achmad, M.J.; Bavestrello, G.; Cerrano, C. Lobozoanthamine, a new zoanthamine-type alkaloid from the Indonesian soft coral Lobophytum sp. Tetrahedron. Lett. 2008, 49, 2189−2192.
80. Fattorusso, E.; Romano, A.; Taglialatela-Scafati, O.; Irace, C.; Mafettone, C.; Bavestrello, G.; Cerrano, C. Oxygenated cembranoids of the decaryiol type from the Indonesian soft coral Lobophytum sp. Tetrahedron. 2009, 65, 2898−2904.
81. Tung, N.H.; Minh, C.V.; Keim, P.V.; Huong, H.T.; Nam, N.H.; Cuong, N.X.; Quang, T.H.; Nhiem, N.X.; Hyun, J.-H.; Kang, H.-K.; Kim, Y.H. Chemical components from the Vietnamese soft coral Lobophytum sp. Arch. Pharm. Res. 2010, 33, 503−508.
82. Bonnard, I.; Jhaumeer-Laulloo, S.B.; Bontemps, N.; Banaigs, B.; Aknin, M. New lobane and cembrane diterpenes from two Comorian soft corals. Mar. Drugs. 2010, 8, 359−372.
83. Hegazy, M.E.F.; Su, J.-H.; Sung, P.-J.; Sheu, J.-H. Cembranoids with 3,14-ether linkage and a secocembrane with bistetrahydrofuran from the Dongsha Atoll soft coral Lobophytum sp. Mar. Drugs. 2011, 9, 1243−1253.
84. Zhao, M.; Li, X.-B.; Zhao, F.; Cheng, S.-M.; Xiang, Z.; Dong, J.-Y.; Huang, K.-X.; Yan, P.-C. Four new 7,8-epoxycembranoids from a chinese soft coral Lobophytum sp. Chem. Pharm. Bull. 2013, 61, 1323−1328.
85. Zhao, M.; Yin, J.; Jiang, W.; Ma, M.-S.; Lei, X.-X.; Xiang, Z.; Dong, J.-Y.; Huang, K.; Yan, P.-C. Cytotoxic and antibacterial cembranoids from a south China sea soft coral, Lobophytum sp. Mar. Drugs. 2013, 11, 1162−1172.
86. 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出版,屏東,中華民國,1987,pp. 9−16。
87. Rodríguez, A.D.; Li, Y.; Dhasmanna, H. New marine cembeane diterpenoids isolated from the Carbbean gorgonian Eunicea mammosa. J. Nat. Prod. 1993, 56, 1101−1113.
88. Takagi, Y.; Fujimori, T.; Kanneko, H.; Kato, K. Cembrene, from Japanese tobacco, Nicotiana tabacum cv. Suifu. Agric. Biol. Chem. 1980, 44, 467−468.
89. Huang, H.-C.; Ahmed, A.F.; Su, J.-H.; Chao, C.-H.; Wu, Y.-C.; Chiang, M.Y.; Sheu, J.-H. Crassocolides A-F, cembranoids with a trans-fused lactone from the soft coral Sarcophyton crassocaule. J. Nat. Prod. 2006, 69, 1554−1559.
90. Duh, C.-Y.; Wang, S.-K.; Chung, S.-G.; Chou, G.-C.; Dai, C.-F. Cytotoxic cembrenolides and steroids from the formosan soft coral Sarcophyton crassocaule. J. Nat. Prod. 2000, 63, 1634−1637.
91. Rodríguez, A.D.; Martínez, N. Marine antitumor agents: 14-deoxycrassin and pseudoplexaurol, new cembranoid diterpenes from the Caribbean gorgonian Pseudoplexaura porosa. Experientia. 1993, 49, 179−181.
92. Lin, W.-Y.; Lu, Y.; Su, J.-H.; Wen, Z.-H.; Dai, C.-F.; Kuo, Y.-H.; Sheu, J.-H. Bioactive cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule. Mar. Drugs. 2011, 9, 994−1006.
93. Lin, W.-Y.; Lu, Y.; Chen, B.-W.; Huang, C.-Y.; Su, J.-H.; Wen, Z-H.; Dai, C.-F.; Kuo, Y.-H.; Sheu, J.-H. Sarcocrassocolides M–O, bioactive cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule. Mar. Drugs. 2012, 10, 617−626.

連結至畢業學校之論文網頁點我開啟連結
註: 此連結為研究生畢業學校所提供,不一定有電子全文可供下載,若連結有誤,請點選上方之〝勘誤回報〞功能,我們會盡快修正,謝謝!
QRCODE
 
 
 
 
 
                                                                                                                                                                                                                                                                                                                                                                                                               
第一頁 上一頁 下一頁 最後一頁 top
系統版面圖檔 系統版面圖檔