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博碩士論文 etd-0727101-153250 詳細資訊
Title page for etd-0727101-153250
論文名稱
Title
綠島海域脈指型軟珊瑚Sinularia gibberosa及Isis hippuris所含天然物成分之研究.
Studies on Cytotoxic Secondary Metabolities of the Formosan Gorgonian Sinularia gibberosa and Isis hippuris.
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
123
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
2001-06-19
繳交日期
Date of Submission
2001-07-27
關鍵字
Keywords
脈指型軟珊瑚、竹珊瑚
Sinularia gibberosa, Isis hippuris
統計
Statistics
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中文摘要
從綠島產竹珊瑚Isis hippuris之乙酸乙酯萃取物中分離出三個新的多氧化態固醇類化合物: 3α,11β-dihydroxy-24-methyl-22,25epoxy- 5α-furostan-18,20β-lactone (1), 3-acetyl-2-deacetyl-hippurin-1 (2) 及 hippuristerone F (3) 與四個已知化合物: hippurin-1 (4), 22-epi- hippurin-1 (5), 3-acetyl-2-desacetyl-22-epi-hippurin-1 (6) 及2-desacetyl- 22-epi-hippurin-1 (7)。
此外, 從綠島產的脈指型軟珊瑚Sinularia gibberosa的乙酸乙酯萃取物中分離出三個皆屬於9,11-seco類的已知固醇類化合物,分別為: 3β,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (8), 3β,11- dihydroxy-24-methyl-9,11-secocholest-5-en-9-one (9), 3β-hydroxy-11- acetoxy-24-methylene-9,11-secocholest-5-en-9-one (10)。 化合物1-10的結構及相對立體構型均是經由圖譜解析及文獻比對的方法加以建立。
在生物活性方面, 化合物9, 10對P-388癌細胞具有顯著的細胞毒殺活性, 化合物6和8對癌細胞P-388及HT-29具有細胞毒殺活性, 化合物2, 4和5對癌細胞P-388, A-549及HT-29具有細胞毒殺活性。
Abstract
In our continuing study on the chemical constituents of Taiwanese soft corals, the EtOAc extracts of a gorgonian coral Isis hippuris and a alcyonarian coral Sinularia gibberosa were investigated, respectively. Seven compounds, including 3α,11β-dihydroxy-24-methyl-22,25epoxy-5α- furostan-18,20β-lactone (1), 3-acetyl-2-deacetyl-22R-hippurin-1 (2), hippuristerone F (3), hippurin-1 (4), 22-epi-hippurin-1 (5), 3-acetyl-2- desacetyl-22-epi-hippurin-1 (6) and 2-desacetyl-22-epi-hippurin-1 (7) were isolated from I. hippuris. Three metabolites, 3β,11-dihydroxy-24- methylene-9,11-secocholest-5-en-9-one (8), 3β,11-dihydroxy-24-methyl-9, 11-secocholest-5-en- 9-one (9) and 3β-hydroxy-11-acetoxy-24-methylene-9, 11-secocholest-5-en-9-one (10) were isolated from S. gibberosa. Among them, compounds 1–3, are new products. All metabolites 1–10 are steroids.
The structures of 1–10 were determined by physical and spectral analysis, including IR, MS, 1D NMR (1H, 13C) and 2D NMR ( 1H-1H COSY, HMQC, HMBC and NOESY ) and by comparison with the related physical and spectral data of the known compounds.
The cytotoxicity of the isolates against the P-388 ( mouse lymphocytic leukemia ), A-549 ( human lung adenocarcinoma ) and HT-29 ( human colon adenocarcinoma ) cancer cell lines were studied. Compound 9 and 10 showed significant cytotoxicity against P-388 cancer cell line. Metabolites 6 and 8 showed significant cytotoxicity against P-388 and HT-29 cancer cell lines. Compound 2, 4 and 5 exhibited potent cytotoxicity against the growth of P-388, A-549 and HT-29 cancer cell lines.
目次 Table of Contents
壹、 緒論
一、 前言 4
二、 9,11-secosterols的文獻回顧 5
三、 Isis hippuris的文獻回顧 11

貳、 材料與方法
一、 生物採樣時間與地點 17
二、 物種型態及分類地位 17
三、 研究動機 18
四、 萃取分離與純化步驟 19

參、 器材與實驗
一、 使用溶劑 27
二、 使用儀器 27
三、 相關實驗 28

肆、 結果與討論
一、 結構解析 31
(一)、3,11β-dihydroxy-24-methyl-22,25epoxy -5-furostan-18,20β-lactone (1) 31
(二)、3-acetyl-2-deacetyl-22R-hippurin-1 (2) 36
(三)、hippuristerine C (3) 41
(四)、hippurin-1 (4) 46
(五)、22-epi-hippurin-1 (5) 50
(六)、3-acetyl-2-desacetyl-22-epi- hippurin-1 (6) 52
(七)、2-desacetyl-22-epi-hippurin-1 (7) 55
(八)、3β,11-dihydroxy-24-methylene-9,11- secocholest-5-en-9-one (8) 57
(九)、3β,11-dihydroxy-24-methyl-9,11- secocholest-5-en-9-one (9) 59
(十)、3β-hydroxy-11-acetoxy-24-methylene- 9,11-secocholest-5-en-9-one (10) 62二、 化合物之癌細胞毒殺活性 66

伍、 結論 65

陸、 參考文獻 68
參考文獻 References
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