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研究生:楊奕蕾
研究生(外文):Yi-Lea Yang
論文名稱:綠島海域脈指型軟珊瑚Sinulariagibberosa及Isishippuris所含天然物成分之研究.
論文名稱(外文):Studies on Cytotoxic Secondary Metabolities of the FormosanGorgonian Sinularia gibberosa and Isis hippuris.
指導教授:許志宏許志宏引用關係
指導教授(外文):J-H Sheu
學位類別:碩士
校院名稱:國立中山大學
系所名稱:海洋資源學系研究所
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:2001
畢業學年度:89
語文別:中文
論文頁數:123
中文關鍵詞:脈指型軟珊瑚竹珊瑚
外文關鍵詞:Sinularia gibberosaIsis hippuris
相關次數:
  • 被引用被引用:3
  • 點閱點閱:225
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  • 下載下載:22
  • 收藏至我的研究室書目清單書目收藏:0
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。
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.
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
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