Responsive image
博碩士論文 etd-0901111-205759 詳細資訊
Title page for etd-0901111-205759
論文名稱
Title
台灣產軟珊瑚 Lemnalia philippinensis的化學成分及生物活性之研究
Chemical Constituents and Biological Activities of the Formosan Soft Coral Lemnalia philippinensis
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
156
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
2011-07-14
繳交日期
Date of Submission
2011-09-01
關鍵字
Keywords
eremophliane、lemnaphinolide、ylangene、5-cycloneolemnane、lemnaphilins、穗軟珊瑚、4、neolemnane
lemnaphilins, neolemnane, 5-cycloneolemnane, eremophliane, Lemnalia philippinensis, 4, lemnaphinolide, ylangene
統計
Statistics
本論文已被瀏覽 5668 次,被下載 387
The thesis/dissertation has been browsed 5668 times, has been downloaded 387 times.
中文摘要
我們研究台灣軟珊瑚 Lemnalia philippinensis 的化學組成,發現有七個新的化合物從穗軟珊瑚 L. philippinensis 中共分離出來,其中包含了三個 ylangene-type sesquiterpenoids的化合物 lemnaphilins A-C (1-3),兩個 eremophilane-type sesquiterpenoids的化合物lemnaphilins D-E (4-5),一個 neolemnane-type sesquiterpenoid的化合物lemnaphilin F (6),與一個4,5-cycloneolemnane-type sesquiterpenoid的化合物 lemnaphinolide (7),以及分離到八個已知化合物,分別為lemnalol (8) , 11,12-dihydroxy-6,10-eremopilaiene(9), 4(S*)-acetoxy,10(S*)-hydr-oxyl,5-oxo,l(S*),12(S*)neolemna-2(Z),8-diene(10), laevinone A (11), 2-oxolemnacarnol (12), lemnal-1(10)-ene-2,12-dione (13), 2,7-nardosinoxanedione (14), elongatol B (15)上述化合物的構造均是由光譜數據的分析(IR, MS, 1D、2D NMR)和比對文獻上已知化合物的光譜資料而決定。
本研究中亦對所獲得的化合物 1-15針對人類肝癌細胞(HepG2)、人類乳癌細胞(MDA-MB231),以及人類呼吸道表皮癌細胞(A549)進行細胞毒殺測試,發現只有lemnaphilin A其就有細胞毒殺的活性,所測得的IC50濃度各為15.99、16.31以及15.81 μg/mL.
Abstract
From the chemical investigation of a Formosan soft coral Lemnalia philippinensis, we had discovered seven new sesquiterpenoids, including three ylangene-type sesquiterpenoids lemnaphilins A-C ( 1-3 ), two eremophilane-type sesquiterpenoids lemnaphilins D-E ( 4-5 ), one neolemnane-type sesquiterpenoid lemnaphilin F (6), and one 4,5-cycloneolemnane-type sesquiterpenoid lemnaphinolide (7), along with eight known compounds, lemnalol(8) , 11,12-dihydroxy-6,10-eremopi
-laiene (9),4(S*)-acetoxy,10(S*)-hydroxy,5-oxo,l(S*),12(S*)neolemna–2(Z), 8–diene
(10), laevinone A (11), 2-oxolemnacarnol(12), lemnal-1(10)- ene-2,12-dione (13), 2,7
-nardosinoxanedione (14), elongatol B (15). The structures of these compounds were established by the detailed spectral analysis (IR, MS, 1D, 2D NMR) and by comparison of the spectral data with those of the related known compounds.
The cytotoxicity of fifteen compounds (1–15) against with three cell lines, including HepG2 (human liver hepatocellular carninoma cells)、MDA-MB231(human breast cancer cells) and A549(human respiratory epithelial cells)was also determined. Only lemnaphilin A exhibited cytotoxicity, with IC50 values 15.99、16.31and 15.81 μg/mL.
目次 Table of Contents
中文摘要 i
英文摘要 ii
第一章、緒論
第一節、前言 1
第二節、研究背景及目的 2
第三節、文獻回顧 5
第四節、珊瑚型態與分布 23
第二章、生物材料採集、鑑種與研究方法 24
第三章、化合物之結構證明
第一節、軟珊瑚Lemnalia philippinensis 所分離出之化合物的結構之解析 28
(一)、Lemnaphilin A (1) 結構之解析 28
(二)、Lemnaphilin B (2) 結構之解析 37
(三)、Lemnaphilin C (3) 結構之解析 46
(四)、Lemnaphilin D (4) 結構之解析 55
(五)、Lemnaphilin E (5) 結構之解析 64
(六)、Lemnaphilin F (6) 結構之解析 72
(七)、Lemnaphinolide (7) 結構之解析 81
(八)、Lemnalol (8) 結構之解析 90
(九)、11,12-dihydroxy-6,10-eremopilaiene (9) 結構之解析 94
(十)、4(S*)-acetoxy,10(S*)-hydroxy,5-oxo,l(S*),12(S*)
(十一)、Laevinone A (11) 結構之解析 102
(十二)、2-Oxolemnacarnol (12) 結構之解析 106
(十三)、Lemnal-1(10)-ene-2,12-dione (13) 結構之解析 110
(十四)、2,7-nardosinoxanedione (14) 結構之解析 114
(十四)、Elongatol B (15) 結構之解析 118
第二節、生合成路徑 122
第三節、化合物物理性質及圖譜數據整理 125
第四章、生物活性試驗 127
第五章、結論 128
第六章、實驗相關部分
第一節、儀器與材料 133
第二節、珊瑚的分離與純化 135
第三節、生物活性的方法與步驟 136
第七章、參考文獻 138

參考文獻 References
1.江昆達、林全信,豐富的海洋資源,臺灣書店,1998,117–126。
2.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,1987,9-16。
3.Newman, D. J.; Cragg, G. M. “Marine Natural Products and Related Compounds in Clinical and Advenced Preclinical Trials” J. Nat. Prod. 2004, 67, 1216–1238.
4.Kijjoa, A,; Sawangwong, P. “Drugs and Cosmetics from the Sea” Mar. Durgs. 2004, 2, 73–82.
5.Benayahu, Y.;Jeng, M.-S.;Perkol-Finkel, S.;Dai, C.-F. “Soft Corals(Octocorallia: Alcyonacea) from Southern Taiwan.Ⅱ.Species Diversity and Distributional Patterns”Zoological Studies. 2004,43, 548-560.
6.Kikuchi, H.; Tsukitani, Y.; Yamada, Y.; Iguchi, K.; Drexler, S. A.; Clardy, J. “Lemnalol, A New Sesquiterpenoid from the Soft Coral Lemnalia tenuis Verseveldt” Tetrahedron Lett. 1982, 23, 1063–1066.
7.Kikuchi, H.; Manda, T.; Kobayashi, K.; Yamada, Y.; Iguchi K. “Anti-tumor Activity of Lemnalol Isolated from the Soft Coral Lemnalia tenuis Verseveldt ” Chem. Pharm. Bull. 1983, 31, 1086-1088.
8.Jean, Y.-H.; Chen, W.-F.; Duh, C.-Y.; Huang, S.-Y.; Hsu, C.-H.; Lin, C.-S.; Sung, C.-S.; Chen, I.-M.; Wen, Z.-H. “ Inducibe Nitric Oxide Synthase and Cyclooxygenase-2 Participate in Anti- inflammatory and Analgestic Effects of the Natural Marine Compound Lemnalol from Formosan Soft coral Lemnalia cervicorni” European Journal of Pharmacology. 2008, 578, 323–331.
9.Duh, C.-Y.; El-Gamal, A. A. H.; Song, P.-Y.; Wang, S.-K.; Dai, C.-F. “Steroids and Sesquiterpenoids from the Soft Corals Dendronephthya gigantean and Lemnalia cervicorni” J. Nat. Prod. 2004, 67, 1650–1653.
10.Cheng, S.-H.; Lin, E.-H.; Huang, J.-S.; Wen, Z.-H.; Duh, C.-Y. “Ylangene-Type and Nardosine-Type Sesquiterpeniods from the Soft Coral Lemnalia flava and Paralemanalia thyrsoides ” Chem. Pharm. Bull. 2010, 58, 381-385.
11.Oyarzun, M. L.; Garbarino, J. A. “Sesquiterpenoids from Pilgerodendron uvífera” Phytochemstry, 1988, 27, 1121-1123.
12.Izac, R. R.; Fenical, W.; Tagle, B.; Clardy, J. “Neolemnane and Eremophilane Sesquiterpenoids from the Pacific Soft Coral Lemnalia Africana” Tetrahedron 1981, 37, 2569–2573.
13.Jurek, J.; Scheuer, P. J.; “Sesquiterpenoids and Norsesquiterpenoids from the Soft Coral Lemnalia aficana” J. Nat. Prod. 1993, 56, 508–513.
14.黃和全,綠島產軟珊瑚Paralemnalia thyrsoides 所含天然物之研究,國立中山大學海洋資源學系博士論文,中華民國96年。
15.El-Gamal, A. A. H.; Chiu, E.-P.; Li, C.-H.; Cheng, S.-Y.; Dai, C.-F.; Duh, C.-Y. “Sesquiterpenoids and Norsesquiterpenoids from the Formosan Soft Coral Lemnalia laevis” J. Nat. Prod. 2005, 68, 1749–1753.
16.Ahmed, A. A. “ Eremophilanes from Senecio Desfotainei” J. Nat. Prod. 1991, 54, 271-272
17.Zhoa, Y.; Peng, H.; Jia Z. “Six Eremophilane Derivatives from Two Ligularia species” J. Nat. Prod. 1994, 57, 1626–1630.
18.Zhao, Y.; Jia, Z.; Peng, H. “Eight New Eremophilane Derivatives from the Roots of Ligularia przewalskii” J. Nat. Prod. 1995, 58, 1358-1364.
19.Lin, Y.-L.; Mei, C.-H.; Huang, S.-L.; Kuo, Y.-H. “Four New Sesquiterpenes from Petasites formosanus” J. Nat. Prod. 1998, 61, 887-890
20.Garduňo-Ramírez, M. L.; Trejo, A.; Navarro, V.; Bye, R.; Linares, E.; Dalgado, G. “New Modified Eremophilanes from the Roots of Psacalium radulifolium” J. Nat. Prod. 2001, 64, 432-435.
21.Tursch, B.; Colin, M.; Daloze, D.; Losman, D.; Karlsson, R. “Lemnacarnol, a Noval Sesquiterpene from the Soft Coral Lemnalia carnosa” Bull. Soc. Chim. Belg. 1975, 84, 81–82.
22.Karlsson R.; Losman D. “Structure and Absolute Configuration of Sesquiterpene Lemnacarnol ” Acta Cryst. 1976, B32, 1614.
23.Karlsson R.; Losman D.; Sheldrick G. M. “2-Deoxy-12-oxolemnacarnol; A Case of Twinning” Acta Cryst. 1977, B33, 1959–1962.
24.Carney, J. R.; Pham, A. T.; Yoshida, W. Y.; Scheuer, P. J. “Napalilactone, a New Halogenated Norsesquiterpenoid from the Soft Coral Lemnalia africana” Tetrahedron Lett. 1992, 33, 7115–7118.
25.Bowden, B.F.; Coll, J. C.; Mitchell, S. J. “Studies of Australian Soft Coral XXIII. The Co-occurrence of Bicyclogermacrene and Lemnacanol Derivatives in Parerythropodium fulvum” Tetrahedron Lett. 1980, 21, 3105–3108.
26.Daloze, D.; Braekman, J. C.; Georget, P.; Tursch, B. “Two Novel Sesquiterpenes from Paralemnalia Thyrsoides” Bull. Soc. Chim. Belg.1977, 86, 47-54.
27.Kapojos, M. M.; Mangindaan, P. E. P.; Nakazawa, T.; Oda, T.; Ukai, K.; Namikoshi, M. “Three New Nardosinane Type Sesquiterpenes from an Indonesian Soft Coral Nephthea sp.” Chem. Pharm. Bull. 2008, 56, 332-334.
28.Ahond, A.; Chiaroni, A.; Coll, J. C.; Fourneron, J. D.; Riche, C. “New Sesquiterpenes from Soft Coral Paralemnalia digitiformis” Bull. Soc. Chim. Belg. 1979, 88, 313-324.
29.Bowden, B. F.; Coll, J. C.; Mitchell, S. J. “Studies of Australian Soft Corals. XIX Two New Sesquiterpenes with the Nardosinane Skeleton from A Paralemnalia species” Aust. J. Chem. 1980, 33, 885-890
30.Bishara, A.; Yeffet, D.; Sisso, M.; Shmul, G.; Schleyer, M.; Benayahu, Y.; Rudi, A.; Kashman, Y. “Nardosinanols A-I and Lemnafricanol Sesquiterpenes from Several Soft Corals, Lemnalia sp., Paralemnalia clavata, Lemnalia africana, and Rhytisma fulvum fulvum” J. Nat. Prod. 2008, 71, 375–380.
31.Ali A. H. El-Gamal.; Wang, S.-K.; Dai, C.-F.; Duh, C.-Y. “New Nardosinanes and 19-Oxygenated Ergosterols from Soft Coral Nephthea armata Collected in Taiwan” J. Nat. Prod. 2004, 67, 1455–1458.
32..Bowden, B. F.; Coll, J. C.; Mitchell, S. J.; Skelton, B. W; White, A. H. “Studies of Australian Soft Corals. XXII the Structures of Two Novel Sesquiterpenes and a Nor Sesquiterpene from Lemnalia africana, Confirmed by a Single-Crystal X-ray Study” Aust. J. Chem. 1980, 33, 2737-2747.
33.Lu, Y.; Li, P.-J.; Hung, W.-Y.; Su, J.-H.; Wen, Z.H.; Hsu, C.-H.; Dai, C.F.; Chiang, M.-Y.; Sheu, J.-H. “Nardosinane Sesquiterpenoids from the Formosan Soft Coral Lemnalia flava” J. Nat. Prod. 2011, 74, 169-174.
34.李柏儒,台灣產軟珊瑚 Sinularia scabra 與 Lemnalia flava 所含二次代謝物及 Lobohedleolide 化合物之化學修飾之研究,國立中山大學海洋資源學系碩士論文,中華民國98年。
35.Blunt, J. W.; Copp, B. B.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. “Marine Natural Products” Nat. Prod. Rep. 2010, 27, 165-237.
36.洪文瑜,台灣產軟珊瑚Lemnalia flava 所含Sesquiterpenoids類化合物之研究,國立中山大學海洋生物科技暨資源學系碩士論文,中華民國99年。
37.Wang, S.-K.;Duh, C.-Y. “Nardosinane Sesquiterpenoids from the Formosan Soft Coral Nephthea elongata” Chem. Pharm. Bull. 2007, 55, 762-765.
38.Viala, J.; Santelli, M. “Hydrolysis Oxirylcarbinyl Tosylates” Tetrahedron. 1978, 34, 2327-2330.
39.Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M.L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemker, R. H.; Boyd, M. R. “Feasiblity of Drug Sceening with Panels of Human Tumor Cell Lines Using A Microculture Tetrazolium Assay” Cancer Res, 1988, 48, 589-601.
40.Scudiero, D. A.; Shoemker, R. H.; Paull, K. D.; Monks, A.; Tierney, S.; Nofziger, T. H.; Currens, M. J.; Seniff, D.; Boyd, M. R. “Evalution of A Soluble Tetrazolium/Formazam Assay for Cell Growth and Drug Sensitivity in Culture Using Human and OtherTumor Cell Lines” Cancer Res. 1988, 48, 4827-4833.
.









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:自定論文開放時間 user define
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