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研究生:張誌益
研究生(外文):Chang Chi-I
論文名稱:黃心柿莖部與臺灣杉樹皮之化學成份研究
論文名稱(外文):Studies on the Chemical Constituents of the Stem of Diospyros maritima Blume and the Bark of Taiwania cryptomerioides Hayata
指導教授:郭 悅 雄
指導教授(外文):Kuo Yueh-Hsiung
學位類別:博士
校院名稱:國立臺灣大學
系所名稱:化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:1999
畢業學年度:87
語文別:中文
論文頁數:374
中文關鍵詞:黃心柿莖部色層分析結構三帖類臺灣杉樹皮雙帖類
外文關鍵詞:Diospyros maritimaStemChromatographyStructureTriterpenoidTaiwania cryptomerioidesBarkDiterpenoid
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黃心柿 (Diospyros maritima Blume),俗名黃心仔,柿樹科 (Ebenaceae) 之常綠喬木,分佈於臺灣北部、恆春半島及蘭嶼。臺灣杉(Taiwania cryptomerioides Hayata),別名亞杉,常綠大喬木,特產於中央山脈海拔 1800-2000 公尺處。黃心柿莖材與臺灣杉樹皮分別以乙醇及丙酮萃取,以矽膠管柱色層分析、高壓液相層析或再結晶的方法純化,經由測其紅外線光譜、紫外線光譜、核磁共振光譜、質譜與化學反應等方法鑑定結構。
黃心柿莖材鑑定出六十五個化合物,其中三帖類有三十二個,naphthoquinone 類有十二個,芳香族類有十個,其他類有十一個,其中有二十九個新化合物: Dioslupecin (T5), 3-(Z)-Coumaroyllupeol (T6), 3-(E)-Feruloylbetulin (T11), 28-Acetyl-3-(E)-coumaroylbetulin (T12), 3-(E)-Coumaroyl-28-palmitoylbetulin (T13), 3-(Z)-Coumaroyl-28-palmitoylbetulin (T14), 3-(E)-Feruloyl-28-palmitoylbetulin (T15), 3-(E)-Coumaroylbetulinaldehyde (T17), [3-(E)-Coumaroylbetulin-28-yl] ethyl succinate (T22), [3-(E)-Coumaroylbetulin-28-yl] ethyl 3-hydroxysuccinate (T23), [3-(E)-Coumaroylbetulin-28-yl] ethyl nonanedioate (T24), Diospyrolide (T25), Diospyrolidone (T26), 3-Ethoxyisodiospyrin (N4), 2’-Ethoxyisodiospyrin (N5), 3’-Ethoxyisodiospyrin (N6), 2,2’-Diethoxyisodiospyrin (N7), 2,3’-Diethoxyisodiospyrin (N8), 3,2’-Diethoxyisodiospyrin (N9), 3,3’-Diethoxyisodiospyrin (N10), 2-Ethoxy-8’-hydroxyisodiospyrin (N12), 3-Ethoxy-8’-hydroxyisodiospyrin (N13), epi-Isoshinanolone (N15), 3-Ethoxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (A8), Bis(6-hydroxy-2,3,4-trimethylphen-1-yl)methane (A10), (+)-Diethyl-D-malate (O2), Butyl methyl succinate (O5), Maritolide (O7), 5,7-Dihydroxy-2-methylchromanone (O11)。
臺灣杉樹皮部份鑑定出六十五個化合物,其中雙帖類有五十三個,木酚素類有六個,芳香族類有一個,類固醇類有五個,其中有二十三個新化合物: 11-Hydroxyabieta-8,11,13-trien-7-one (D6), 11,12,14-Trihydroxyabieta-8,11,13-trien-7-one (D9), 6β,7α-Diacetoxyroyleanone (D20), 7β-Hydroxymanoyl oxide (D24), 9α-Hydroxyisopimara-8(14),15-dien-7-one (D29), Taiwaniaquinol C (D30), Taiwaniaquinol D (D31), Taiwaniaquinol E (D33), Taiwaniaquinol F (D35), Taiwaniaquinone F (D38), Taiwaniaquinone G (D39), Taiwaniaquinone H (D41), 14-Hydroxy-13-methoxy-8,11,13-podocarpatrien-7-one (D42), 13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (D43), 13-Hydroxy-12-methoxy-8,11,13-podocarpatriene (D45), 12-Hydroxy-13-methoxy-8,11,13-podocarpatriene (D46), 14-Hydroxy-13-methoxy-8,11,13-podocarpatriene (D47), 13-Hydroxy-8,11,13-podocarpatriene (D48), 13-Hydroxy-12-methoxy-8,11,13-podocarpatrien-3-one (D49), 14-Hydroxy-13-methoxy-1,8,11,13-podocarpatetraen-3-one (D50), 1β,14-Dihydroxy-13-methoxy-8,11,13-podocarpatriene (D51), 1β,14-Dihydroxy-13-methoxy-6,8,11,13-podocarpatetraene (D52), 13-Methoxy-11,14-dioxo-8,11-podocarpadiene (D53)。
The stem of Diospyros maritima was extracted with EtOH. The extract was evaporated in vacuo, yielding a black residue, which was suspended in H2O, and then partitioned with n-hexane. The aqueous layer was partitioned again with n-BuOH. The combined n-BuOH extract was purified by column chromatography and recrystallized to afford sixty-five compounds including twenty-nine new compounds. Their structures were eluciated on the basis of spectral and chemical evidence. These new compounds are as followed : Dioslupecin (T5), 3-(Z)-Coumaroyllupeol (T6), 3-(E)-Feruloylbetulin (T11), 28-Acetyl-3-(E)-coumaroylbetulin (T12), 3-(E)-Coumaroyl-28-palmitoylbetulin (T13), 3-(Z)-Coumaroyl-28-palmitoylbetulin (T14), 3-(E)-Feruloyl-28-palmitoylbetulin (T15), 3-(E)-Coumaroylbetulinaldehyde (T17), [3-(E)-Coumaroylbetulin-28-yl] ethyl succinate (T22), [3-(E)-Coumaroylbetulin-28-yl] ethyl 3-hydroxysuccinate (T23), [3-(E)-Coumaroylbetulin-28-yl] ethyl nonanedioate (T24), Diospyrolide (T25), Diospyrolidone (T26), 3-Ethoxyisodiospyrin (N4), 2’-Ethoxyisodiospyrin (N5), 3’-Ethoxyisodiospyrin (N6), 2,2’-Diethoxyisodiospyrin (N7), 2,3’-Diethoxyisodiospyrin (N8), 3,2’-Diethoxyisodiospyrin (N9), 3,3’-Diethoxyisodiospyrin (N10), 2-Ethoxy-8’-hydroxyisodiospyrin (N12), 3-Ethoxy-8’-hydroxyisodiospyrin (N13), epi-Isoshinanolone (N15), 3-Ethoxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (A8), Bis(6-hydroxy-2,3,4-trimethylphen-1-yl)methane (A10), (+)-Diethyl-D-malate (O2), Butyl methyl succinate (O5), Maritolide (O7), 5,7-Dihydroxy-2-methylchromanone (O11).
The bark of Taiwania cryptomerioides was extracted with acetone. Using a similar method, Sixty-five compounds including twenty-three new compounds had been isolated from EtOAc soulble fraction. These new compounds are as followed : 11-Hydroxyabieta-8,11,13-trien-7-one (D6), 11,12,14-Trihydroxyabieta-8,11,13-trien-7-one (D9), 6β,7α-Diacetoxyroyleanone (D20), 7β-Hydroxymanoyl oxide (D24), 9α-Hydroxyisopimara-8(14),15-dien-7-one (D29), Taiwaniaquinol C (D30), Taiwaniaquinol D (D31), Taiwaniaquinol E (D33), Taiwaniaquinol F (D35), Taiwaniaquinone F (D38), Taiwaniaquinone G (D39), Taiwaniaquinone H (D41), 14-Hydroxy-13-methoxy-8,11,13-podocarpatrien-7-one (D42), 13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (D43) 13-Hydroxy-12-methoxy-8,11,13-podocarpatriene (D45), 12-Hydroxy-13-methoxy-8,11,13-podocarpatriene (D46), 14-Hydroxy-13-methoxy-8,11,13-podocarpatriene (D47), 13-Hydroxy-8,11,13-podocarpatriene (D48), 13-Hydroxy-12-methoxy-8,11,13-podocarpatrien-3-one (D49), 14-Hydroxy-13-methoxy-1,8,11,13-podocarpatetraen-3-one (D50), 1β,14-Dihydroxy-13-methoxy-8,11,13-podocarpatriene (D51), 1β,14-Dihydroxy-13-methoxy-6,8,11,13-podocarpatetraene (D52), 13-Methoxy-11,14-dioxo-8,11-podocarpadiene (D53).
摘要
第一章 緒論
1-1 緒言.....................................................1
1-2 植物介紹與成份研究歷史...................................2
1-3 研究目的.................................................9
第二章 結果與討論
2-1 萃取與分離.............................................11
2-2 三帖類 Lupane 型新化合物構造鑑定
2-2-1 化合物 T5 T6 之構造鑑定.................................28
2-2-3 化合物 T11 之構造鑑定...................................39
2-2-4 化合物 T12 之構造鑑定...................................45
2-2-5 化合物 T13, T14, T15 之構造鑑定.........................52
2-2-5 化合物 T17 之構造鑑定...................................70
2-2-6 化合物 T22, T23, T24 之構造鑑定.........................76
2-2-7 化合物 T25 T26 之構造鑑定...............................94
2-3 naphthoquinone 類新化合物構造鑑定
2-3-1 化合物 N4, N5, N6 之構造鑑定...........................108
2-3-2 化合物 N7, N8, N9, N10 之構造鑑定......................124
2-3-3 化合物 N12, N13 之構造鑑定.............................138
2-4 芳香族及其他類新化合物構造鑑定
2-4-1 化合物 A8 之構造鑑定...................................151
2-4-2 化合物 A10 之構造鑑定..................................157
2-4-3 化合物 O5 之構造鑑定...................................164
2-4-4 化合物 O7 之構造鑑定...................................170
2-5 雙帖類新化合物構造鑑定
2-5-1 Abietane 型
2-5-1-1 化合物 D6 之構造鑑定.............................175
2-5-1-2 化合物 D9 之構造鑑定.............................182
2-5-1-3 化合物 D20 之構造鑑定................................189
2-5-2 Manoyl oxide 型化合物 D24 之構造鑑定...................196
2-5-3 Isopimarane 型化合物 D29 之構造鑑定....................202
2-5-4 Taiwaniaquinol 型化合物 D30, D31, D33, D35 之構造鑑定..209
2-5-5 Taiwaniaquinone 型化合物 D38, D39, D41 之構造鑑定......236
2-5-6 Podocarpane 型化合物之構造鑑定
2-5-6-1 化合物 D42, D43 之構造鑑定.....................257
2-5-6-2 化合物 D45, D46, D47, D49 之構造鑑定...........271
2-5-6-3 化合物 D49, D50, D51, D52 之構造鑑定...........297
2-5-6-4 化合物 D53 之構造鑑定..........................323
第三章 實驗部分
3-1 實驗使用之儀器與藥品..................................330
3-2 實驗步驟.................................................332
3-3 化合物數據..............................................337
第四章 結論
4-1 化合物之氫核磁共振光譜特徵.............................341
4-2 抗癌藥理實驗...........................................342
4-3 化合物分佈狀況與生合成.................................346
4-4 黃心柿及臺灣杉各部分成份比較...........................348
參考文獻.....................................................350
已發表之文獻.................................................374
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