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作者:黃義棋
作者(英文):Yi-Qi Huang
論文名稱:蘭嶼海域粗枝竹節珊瑚Isis hippuris固醇類天然物之研究
論文名稱(英文):Studies on the Steroids from the Lanyu Isis hippuris
指導教授:宋秉鈞
郭傑民
指導教授(英文):Ping-Jyun Sung
Jimmy Kuo
口試委員:蘇瑞欣
宋秉鈞
郭傑民
口試委員(英文):Jui-Hsin Su
Ping-Jyun Sung
Jimmy Kuo
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
學號:611063013
出版年(民國):112
畢業學年度:111
語文別:中文
論文頁數:245
關鍵詞:粗枝竹節珊瑚固醇類縮酮環細胞毒性
關鍵詞(英文):Isis hippurissterolketal ringcytotoxicity
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本論文之研究主要由臺灣蘭嶼海域所採集的粗枝竹節珊瑚Isis hippuris含有的天然物成分進行分析,並從其萃取物中純化分離得到十二個固醇類化合物,其中包含二個新化合物 hippuristeroketal B (1)、24-dehydrohippuristanol (2) 與一個首次從自然界中獲得的化合物 hippuristanol 11-one (3),以及九個已知化合物hippuristerone A (4)、hippuristerone I (5)、hippuristanol (6)、22-epi-hippuristanol (7)、hippurin-1 (8)、22-epi-hippurin-1 (9)、3-acetyl-22-epi-hippurin-1 (10)、3α-acetoxy-11β-hydroxy-24-methyl-22,25-epoxy-5α-furostan-18,20β-lact- one (11)、(22S)-3α-acetoxy-11β,18α-dihydroxy-24-methyl-18,-20β;22,25-diepoxy-5α-furostane (12)。這些天然化合物的結構皆是經由各種光譜的資料分析與文獻比對後確認,其中化合物1、4−7、9、11和12 的絕對立體構型經由X-ray單晶體繞射實驗分析而確定。
化合物2對人類結腸癌細胞DLD-1和LoVo都顯示出具有細胞毒殺效果,IC50分別為5.54、6.89 μM。
This study focus on the nature products from the octocoral Isis hippuris collected from the waters near Lanyu (Orchid Island), Taiwan. Twelve steroids, including two new compounds hippuristeroketal B (1) and 24-dehydrohippuristanol (2), one new natural product hippuristanol 11-one (3) as well as nine known compounds hippuristerone A (4), hippuristerone I (5), hippuristanol (6), 22-epi-hippuristanol (7), hippurin-1 (8), 22-epi-hippurin-1 (9), 3-acetyl-22-epi-hippurin-1 (10), 3α-acetoxy-11β-hydroxy-24-methyl-22,25-epoxy-5α-furostan-18,20β-lactone (11) and (22S)-3α-acetoxy-11β, 18α-dihydroxy-24-methyl-18,-20β;22,25-diepoxy-5α-furostane (12) were isolated from Isis hippuris. The structures of steroids 1–12 were confirmed by spectroscopic methods and literature comparison. The absolute configurations of steroids 1, 4−7, 9, 11 and 12 were determined by single X-ray crystal diffraction analysis.
Compound 2 New spiroketal steroid 1 exhibited cytotoxic effects against DLD-1 and LoVo cancer cells with IC50 values of 5.54 and 6.89 μM, respectively.
謝詞 I
中文摘要 III
Abstract V
化合物總圖1–12 VII
目錄 IX
圖目錄 XI
表目錄 XV
第一章、緒論 1
第一節、前言與研究動機 1
第二節、粗枝竹節珊瑚Isis hippuris 所含天然物文獻回顧 2
第二章、生物材料與分離流程 15
第一節、生物樣本採集與分類 15
(一)、粗枝竹節珊瑚Isis hippuris 樣品採集資料 15
(二)、珊瑚Isis hippuris 生物分類 (Linnaeus, 1758) 15
第二節、生物樣品萃取與分離流程 17
(一)、粗枝竹節珊瑚Isis hippuris生物樣品萃取與分離流程 17
第三章、實驗器材與有機溶劑 19
第一節、儀器 19
第二節、層析材料 20
第三節、有機溶劑 20
第四章、結果與討論 21
第一節、粗枝竹節珊瑚Isis hippuris所含化合物之結構解析 21
(一)、Hippuristeroketal B (1) 之結構解析 21
(二)、24-Dehydrohippuristanol (2) 之結構解析 33
(三)、Hippuristanol 11-one (3) 之結構解析 45
(四)、Hippuristerone A (4) 之結構解析 55
(五)、Hippuristerone I (5) 之結構解析 61
(六)、Hippuristanol (6) 之結構解析 67
(七)、22-Epi-hippuristanol (7) 之結構解析 73
(八)、Hippurin-1 (8) 之結構解析 79
(九)、22-Epi-hippurin-1 (9) 之結構解析 85
(十)、3-Acetyl-22-epi-hippurin-1 (10) 之結構解析 91
(十一)、3α-Acetoxy-11β-hydroxy-24-methyl-22,25-epoxy-5α-furostan-18,20β-lactone (11) 之結構解析 97
(十二)、(22S)-3α-Acetoxy-11β,18α-dihydroxy-24-methyl-18,-20β;22,25-diepoxy-5α-furostane (12) 之結構解析 103
第二節、化合物實驗數據整理 109
第五章、生物活性試驗 111
第一節、化合物的抗癌活性 111
第二節、化合物的構效關係(Structure-Activity Relationship, SAR) 112
第六章、結論 115
參考文獻 117
附錄、X-ray 解析資料 121
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