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博碩士論文 etd-0302109-114410 詳細資訊
Title page for etd-0302109-114410
論文名稱
Title
軟珊瑚Nephthea erecta、Lobophytum durum 與Sarcophyton ehrenbergi 所含二次代謝物之研究
Studies on the Secondary Metabolites from the Soft Corals Nephthea erecta, Lobophytum durum, and Sarcophyton ehrenbergi
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
497
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
2009-02-21
繳交日期
Date of Submission
2009-03-02
關鍵字
Keywords
二次代謝物、軟珊瑚
Nephthea erecta, Lobophytum durum, Sarcophyton ehrenbergi
統計
Statistics
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中文摘要
為了尋找具有生物活性的新化合物,我們針對軟珊瑚Nephthea erecta、
Lobophytum durum 和Sarcophyton ehrenbergi 所含二次代謝物進行分析研
究。從軟珊瑚N. erecta 的有機萃取物中被分離出六個新的sesquiterpenoid
類化合物(1-6)、一個具有硫醇基(SH)的calamenene 骨架的化合物,
erectathiol (7)、一個新的tri-nor-eudesmadienone 類化合物(8)、二個已知
的sesquiterpenoid 類化合物(9 和10)、一個具有seco-germacrane 新骨架的
sesquiterpene 類化合物(11)、三個人造的C-19 氧化的固醇類化合物(12-14)
和十二個新的具有多個氫氧基(OH)的固醇類化合物(15-26)。從軟珊瑚L.
durum 的有機萃取物中被純化出十二個新的cembranolid 類化合物,
durumolides A-L (27-38),三個前所未見的擁有半縮酮基的cembranolide
類化合物,durumhemiketalolides A-C (39-41),六個已知的cembranolide
類化合物(42-47),以及一個已知的化合物,peridinin (48)。從軟珊瑚S.
ehrenbergi 的有機萃取物被分離出一個已知的ceramide 類化合物(49),兩
個新的cerebroside 類化合物,sarcoehrenosides A (50)和B (51),以及三個
已知的cerebroside 類化合物(52-54)。這些純化出的代謝物的結構鑑定是
透過其有機光譜的分析決定,而化合物10 和44 的相對結構更進一步藉
助X-ray 單晶繞射分析鑑定。再者,化合物24、25、29、34、38 和43-45
的絕對立體位向的決定是運用Mosher 的方法加以證明。針對這些代謝物
進行癌細胞毒殺、抗菌活性、抗發炎活性及人類疱疹病毒的抑制等離體
活性測試。
Abstract
In order to search for novel bioactive compounds, we have investigated the
secondary metabolites of the soft corals Nephthea erecta, Lobophytum durum,
and Sarcophyton ehrenbergi. Chemical examinations on the organic extracts
of N. erecta, have resulted in the isolation of six new sesquiterpenoids (1-6),
a new calamenene-type sesquiterpene with a mercaptan group, erectathiol (7),
a new tri-nor-eudesmadienone (8), two known sesquiterpenoids (9 and 10),
one novel seco-germacrane sesquiterpene (11), three unexpected artificial
19-oxygenated steroids (12-14), as well as twelve new polyhydroxylated
steroids (15-26). Furthermore, twelve new cembranolids, durumolides A-L
(27-38), three unprecedented hemiketal cembranoids, durumhemiketalolides
A-C (39-41), six previously described cembranolids (42-47), together with
one known metabolite, peridinin (48), were isolated from the acetone extracts
of L. durum. Chemical investigation of S. ehrenbergi, has led to the isolation
of a known ceramide (49), two new cerebrosides, sarcoehrenosides A (50) and
B (51), along with three previously characterized cerebrosides (52-54). The
structures of the isolated metabolites were elucidated through extensive
spectroscopic analyses, while the relative stereochemistry of 10 and 44 were
further confirmed by X-ray diffraction analyses. Moreover, the absolute
configurations of 24, 25, 29, 34, 38, and 43-45 were established by
application of modified Mosher’s method. The cytotoxicities, antibacterial
activities, anti-inflammatory effects, and inhibition assay of HCMV (human
cytomegalovirus) endonuclease activities of these isolated metabolites were
evaluated in vitro.
目次 Table of Contents
中 文 摘 要
ABSTRACT
1. Introduction 1
2. Literature Review 5
2.1 Literature Review of the Genus Nephthea 5
2.2 Literature Review of the Genus Lobophytum 22
2.3 Literature Review of the Genus Sarcophyton 36
3. Experimental Section 63
3.1. General Experimental Procedures 63
3.2. Animal Materials 64
3.3. Extraction and Isolation 64
3.4. Cytotoxicity Testing 70
3.5. In Vitro Antimicrobial Activity 71
3.6. In Vitro Anti-inflammatory Assay 72
3.7. Inhibition of Endonuclease Activity Assay 73
3.8. Application of Modified Mosher’s Method for Secondary Alcohols 74
4. Results and Discussion 76
4.1 Structural Elucidation of Compound 1 76
4.2 Structural Elucidation of Compound 2 83
4.3 Structural Elucidation of Compound 3 90
4.4 Structural Elucidation of 8β-Hydroxyprespatane (4) 98
4.5 Structural Elucidation of 8β-Hydroperoxyprespatane (5) 105
4.6 Structural Elucidation of (+)-trans-Calamenen-13-al (6) 111
4.7 Structural Elucidation of Erectathiol (7) 119
4.8 Structural Elucidation of Compound 8 126
4.9 Identification of Kelsoene (9) 134
4.10 Identification of (−)-Aristolone (10) 136
4.11 Structural Elucidation of Compound 11 138
4.12 Structural Elucidation of Compound 12 146
4.13 Structural Elucidation of Compound 13 153
4.14 Structural Elucidation of Compound 14 161
4.15 Structural Elucidation of Erectasteroid F (15) 168
4.16 Structural Elucidation of Erectasteroid G (16) 175
4.17 Structural Elucidation of Erectasteroid C (17) 182
4.18 Structural Elucidation of Erectasteroid D (18) 189
4.19 Structural Elucidation of Erectasteroid E (19) 196
4.20 Structural Elucidation of Compound 20 203
4.21 Structural Elucidation of Erectasteroid H (21) 210
4.22 Structural Elucidation of Erectasteroid A (22) 217
4.23 Structural Elucidation of Erectasteroid B (23) 226
4.24 Structural Elucidation of Compound 24 233
4.25 Structural Elucidation of 5,24(28)-Ergostadien-3β,23S-diol (25) 241
4.26 Structural Elucidation of 5,24(28)-Ergostadien-3β,23R-diol (26) 250
4.27 Structural Elucidation of Durumolide A (27) 257
4.28 Structural Elucidation of Durumolide B (28) 265
4.29 Structural Elucidation of Durumolide C (29) 273
4.30 Structural Elucidation of Durumolide D (30) 283
4.31 Structural Elucidation of Durumolide E (31) 290
4.32 Structural Elucidation of Durumolide K (32) 297
4.33 Structural Elucidation of Durumolide L (33) 305
4.34 Structural Elucidation of Durumolide F (34) 313
4.35 Structural Elucidation of Durumolide G (35) 323
4.36 Structural Elucidation of Durumolide H (36) 331
4.37 Structural Elucidation of Durumolide I (37) 339
4.38 Structural Elucidation of Durumolide J (38) 347
4.39 Structural Elucidation of Durumhemiketalolide A (39) 357
4.40 Structural Elucidation of Durumhemiketalolide B (40) 365
4.41 Structural Elucidation of Durumhemiketalolide C (41) 372
4.42 Identification of Six Known Cembranolides (42−47) 379
4.43 Identification of Peridinin (48) 391
4.44 Identification of Compound 49 393
4.45 Structural Elucidation of Sarcoehrenoside A (50) 397
4.46 Structural Elucidation of Sarcoehrenoside B (51) 407
4.47 Identification of Three Known Cerebrosides (52−54) 416
4.48 Biological Activity of Metabolites 1−54 420
5. Conclusion 424
6. Cited Literature 428
APPENDICES 444
Appendix A. Crystal Data and Structure Refinement for Aristolone (10) 444
Appendix B. Crystal Data and Structure Refinement for 44 452
VITA 461
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