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研究生: 饒真瑋
Jao, Chen-Wei
論文名稱: 細距鶴頂蘭的成分研究
Constituents of Phaius mishmensis
指導教授: 吳培琳
Wu, Pei-Lin
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系
Department of Chemistry
論文出版年: 2006
畢業學年度: 94
語文別: 中文
論文頁數: 110
中文關鍵詞: 蘭科細距鶴頂蘭細胞毒抗癌
外文關鍵詞: Phaius mishmensis, cytotoxicity, anticancer, Orchidaceae
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  •  細距鶴頂蘭為蘭科鶴頂蘭屬。經送國家衛生研究院生物活性篩選測試,發現此植物具有探討其抗癌成分之價值。全草經蔭乾、粉碎後為3.5公斤,以甲醇萃取、濃縮後加水,依序以正己烷、氯仿、乙酸乙酯萃取,經管柱層析、薄層層析共分離到47個純化合物,其中17個化合物為天然界首次發現,分別為2-methoxycarbonylindolin-3-one (3)、phaindirubinol (5)、phaindolanthranilate (7)、1H,3H-quinazoline-2,4-dione (8)、3-(2'-hydroxyphenyl)-3H-quinazolin-4-one (9)、phaitanthrin-A (11)、phaitanthrin-B (12)、phaitanthrin-C (13)、phaitanthrin-D (14)、phaitanthrin-E (15)、phainanthrene-A (17)、(7'R,8'R)-phainanthrene-B (18)、methyl hematinate (20)、2-aminobenzonitrile (21)、2-(N-methoxycarbonylamino)benzamide (22)、3-hydroxy-4,5-dimethoxypropiophenone (24)與methyl 7-hydroxydihydroferulate (34)。其餘30個已知化合物為isatin (1)、3,3-dimethoxyisatin (2)、indirubin (4)、3-methoxycarbonylindole (6)、tryptanthrin (10)、candidine (16)、3-ethyl-4-methylpyrrole-2,5-dione (19)、methyl anthranilate (23)、benzoic acid (25)、4-hydroxybenzaldehyde (26)、methyl 4-hydroxybenzoate (27)、4-oxyacetophenon (28)、vanillaldehyde (29)、vanillic acid (30)、methyl vanillate (31)、syringaldehyde (32)、2-methyl-4-nitrophenol (33)、dihydrocinnamic acid (35)、p-dihydrocoumaric acid (36)、methyl p-dihydrocoumarate (37)、ficusol (38)、cinnamic acid (39)、trans-p-coumaric acid (40)、methyl trans-p-courmarate (41)、ferulic acid (42)、methyl ferulate (43)、methyl cis-p-courmarate (44)、3-oxo-α-ionol (45)、dehydrovamifoliol (46)與methyl hydrogen succinate (47)。

     其中化合物trypthanthrin (10)對MCF-7乳癌細胞、NCI-H460肺癌細胞及SF-268中樞神經癌細胞具有不錯的細胞毒活性;phaitanthrin-B (12)對MCF-7乳癌細胞及NCI-H460肺癌細胞亦有相當活性。

     Phaius mishmensis belongs to Orchidaceae. According to the preliminary screening result by National Health Research Institutes, we found that P. mishmensis is a valuable material to investigate the anticancer active principles. The methanolic extract of dry Phaius mishmensis (3.5 kg) was suspended in water then partitioned with n-hexane, chloroform, and ethyl acetate successively. After extensive column chromatography and thin-layer chromatography, 17 new compounds, 2-methoxycarbonylindolin-3-one (3), phaindirubinol (5), phaindolanthranilate (7), 1H,3H-quinazoline-2,4-dione (8), 3-(2'-hydroxyphenyl)-3H-quinazolin-4-one (9), phaitanthrin-A (11), phaitanthrin-B (12), phaitanthrin-C (13), phaitanthrin-D (14), phaitanthrin-E (15), phainanthrene-A (17), (7'R,8'R)-phainanthrene-B (18), methyl hematinate (20), 2-aminobenzonitrile (21), 2-(N-methoxycarbonylamino)benzamide (22), 3-hydroxy-4,5-dimethoxypropiophenone (24), and methyl (S)-7-hydroxydihydroferulate (34), as well as 30 known compounds, isatin (1), 3,3-dimethoxyisatin (2), indirubin (4), 3-methoxycarbonylindole (6), tryptanthrin (10), candidine (16), 3-ethyl-4-methylpyrrole-2,5-dione (19), methyl anthranilate (23), benzoic acid (25), 4-hydroxybenzaldehyde (26), methyl 4-hydroxybenzoate (27), 4-oxyacetophenon (28), vanillaldehyde (29), vanillic acid (30), methyl vanillate (31), syringaldehyde (32), 2-methyl-4-nitrophenol (33), dihydrocinnamic acid (35), p-dihydrocoumaric acid (36), methyl p-dihydrocoumarate (37), ficusol (38), cinnamic acid (39), trans-p-coumaric acid (40), methyl trans-p-courmarate (41), ferulic acid (42), methyl ferulate (43), methyl cis-p-courmarate (44), 3-oxo-α-ionol (45), dehydrovamifoliol (46), and methyl hydrogen succinate (47) were isolated.

     Among them, trypthanthrin (10) showed strong cytotoxic activity against MCF-7, NCI-H460, and SF-268 cell lines and phaitanthrin-B (12) also showed strong cytotoxicity against MCF-7 and NCI-H460 cell lines.

    中文摘要 I 英文摘要 II 誌謝 III 第一章 緒論 1  第一節 前言 1  第二節 植物型態 2 第二章 細距鶴頂蘭全草之抽取與分離 3 第三章 構造解析 12  第一節 2-Methoxycarbonylindolin-3-one (3)之構造解析 12  第二節 Phaindirubinol (5)之構造解析 16  第三節 Phaindolanthranilate (7)之構造解析 20  第四節 1H,3H-Quinazoline-2,4-dione (8)之構造解析 25  第五節 3-(2'-Hydroxyphenyl)-3H-quinazolin-4-one (9)之構造解析 29  第六節 Tryptanthrin (10)之構造解析 33  第七節 Phaitanthrin-A (11)之構造解析 37  第八節 Phaitanthrin-B (12)之構造解析 41  第九節 Phaitanthrin-C (13)之構造解析 45  第十節 Phaitanthrin-D (14)之構造解析 49  第十一節 Phaitanthrin-E (15)之構造解析 53  第十二節 Phainanthrene-A (17)之構造解析 57  第十三節 (7'R,8'R)-phainanthrene-B (18)之構造解析 61  第十四節 Methyl hematinate (20)之構造解析 66  第十五節 2-Aminobenzonitrile (21)之構造解析 70  第十六節 2-(N-Methoxycarbonylamino)benzamide (22)之構造解析 74  第十七節 3-Hydroxy-4,5-dimethoxypropiophenone (24)之構造解析 79  第十八節 Methyl (S)-7-hydroxydihydroferulate (34)之構造解析 83 第四章 細胞毒活性測試 87 第五章 結論 89 第六章 實驗部分 91  第一節 實驗儀器 91  第二節 抽取與分離 92  第三節 細胞毒活性測試 95  第四節 光譜數據 96 參考文獻 109

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