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研究生:陳慧芳
研究生(外文):Hui-Fang Chen
論文名稱:山刈葉根皮之化學及血小板凝集成分之研究
論文名稱(外文):Chemical Constituents and Antiplatelet Aggregation Principles of the Root Bark of Melicope semecarpifolia
指導教授:陳益昇陳益昇引用關係
指導教授(外文):Ih-Sheng Chen
學位類別:碩士
校院名稱:高雄醫學大學
系所名稱:天然藥物研究所
學門:醫藥衛生學門
學類:藥學學類
論文種類:學術論文
論文出版年:2000
畢業學年度:88
語文別:中文
論文頁數:220
中文關鍵詞:山刈葉芸香科根皮furoquinoline2-quinolone香豆素類黃酮抗血小板凝集
外文關鍵詞:Melicope semecarpifoliaRutaceaeroot barkfuroquinoline2-quinolonecoumarinflavoneanti-platelet aggregation
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  對山刈葉 [Melicope semecarpifolia (Merr.) Hartley] 根皮進行化學成分研究,至目前共得到29種化合物,經光譜分析證實屬於生物鹼者有14種,其中包括12種furoquinoline alkaloids: evolitrine (1), pteleine (2), (R)-(+)-platydesmine (3), (S)-(-)-7,8-dimethoxyplatydesmine (4), cis-(+)-7,8-dimethoxymyrtopsine (5), 2-acetylevolitrine (8), 2-acetylpteleine (9), confusameline (10), dictamnine (18), kokusaginine (19), skimmianine (20) 及 haplopine (21); 1個2-quinolone alkaloid: semecarpifoline (7); 及1個pyranoquinoline alkaloid: (3R)-(-)-8,9-dimethoxygeibalansine (6)。另外有6個香豆素: osthenol (12), osthole (13), 7-O-prenylumbelliferone (14), xanthyletin (26), anisocoumarin H (28) 及umbelliferone (29); 1個黃酮類: ayanin (11); 3個steroids: -sitosterol (15), stigmasterol (16) 及 campesterol (17); 3個benzenoids: methyl vanillate (22), syringic acid (23) 及 tetracosyl ferulate (24),另外尚有methyl oleate (25) 及5-hydroxymethylfurfural (27)。
已知成分之1, 2, 4, 5, 6, 7, 8, 9, 13, 14, 18, 22, 23, 24, 25, 26, 27 及28 等18個化合物係屬首次自本植物分離得到。而semecarpifoline (7), 2-acetylevolitrine (8) 及 2-acetylpteleine (9), 此3個是天然首次分離得到之新化合物。而(S)-(-)-7,8-dimethoxyplatydesmine (4), cis-(+)-7,8-dimethoxymyrtopsine (5) 及 (R)-(-)-8,9-dimethoxygeibalansine (6),本研究首次測定其 []D 值,或決定其立體組態。
分離時配合抗血小板凝集體外篩選,得到下列化合物1, 3, 10, 12, 13, 18, 19, 20, 21, 28對血小板之凝集有抑制作用,在濃度100μg/ml時,化合物 1 及 13 各對arachidonic acid, collagen及PAF所引起的血小板凝集具有完全的抑制作用。在相同濃度時,化合物 20 對arachidonic acid 及 collagen所引起的血小板凝集具有完全的抑制作用,而化合物 10, 18, 19 及 21 則對AA所引起的血小板凝集具有完全的抑制作用。另外在濃度100μg/ml時, 3, 12 及 28 對collagen所引起的血小板凝集具有完全的抑制作用。
In a series of studies on the constituents of Formosan rutaceous plants, twenty-nine compounds have been isolated from the root bark of Melicope semecarpifolia (Merr.) Hartley and their structures were elucidated by spectral analysis. Among them, fourteen are alkaloids: evolitrine (1), pteleine (2), (R)-(+)-platydesmine (3), (R)-(-)-7,8-dimethoxyplatydesmine (4), cis-(+)-7,8-dimethoxymyrtopsine (5), (R)-(-)-8,9-dimethoxygeibalansine (6), semecarpifoline (7), 2-acetylevolitrine (8), 2-acetylpteleine (9), confusameline (10), dictamnine (18), kokusaginine (19), skimmianine (20) and haplopine (21); six are coumarins: osthenol (12), osthole (13), 7-O-prenylumbelliferone (14), xanthyletin (26), anisocoumarin H (28) and umbelliferone (29); one is flavonoid: ayanin (11) and other compounds are -sitosterol (15), stigmasterol (16), campesterol (17), methyl vanillate (22), syringic acid (23), tetracosyl ferulate (24), methyl oleate (25) and 5-hydroxymethylfurfural (27).
1, 2, 4, 5, 6, 7, 8, 9, 13, 14, 18, 22, 23, 24, 25, 26, 27 and 28 were known compounds and isolated for the first time from this plant. Semecarpifoline (7), 2-acetylevolitrine (8) and 2-acetylpteleine (9) are new compounds in nature. In addition, (S)-(-)-7,8-dimethoxyplatydesmine (4), cis-(+)-7,8-dimethoxymyrtopsine (5) and (R)-(-)-8,9-dimethoxygeibalansine (6) were determined the []D or their configuration in this study.
Bioassay-guided fractionation has resulted in the isolation of ten compounds with antiplatelet aggregation activities in vitro. Compounds 1 and 13 showed completely inhibitory activity at 100μg/ml on platelet aggregation induced by arachidonic acid, collagen and PAF in vitro. Compuond 20 showed completely inhibitory activity at 100μg/ml on platelet aggregation induced by arachidonic acid and collagen in vitro. Compuond 10, 18, 19 and 21 showed completely inhibitory activity at 100μg/ml on platelet aggregation induced by arachidonic acid in vitro. Compuond 3, 12 and 28 showed completely inhibitory activity at 100 μg/ml on platelet aggregation induced by collagen in vitro.
目錄
中文摘要 ----------------------------------------- 1
英文摘要 ----------------------------------------- 3
第一章 緒言----------------------------------------------------- 5
第二章 研究動機與目的-------------------------------------- 6
第三章 過去成分研究概要----------------------------------- 7
第四章 結果與討論-------------------------------------------- 28
第一節 根皮部之抽出與分離-------------------------------- 28
第二節 Evolitrine (1) 之結構研究-------------------------- 32
第三節 Pteleine (2) 之結構研究---------------------------- 35
第四節 (R)-(+)-Platydesmine (3) 之結構研究----------- 38
第五節 (S)-(-)-7,8-Dimethoxyplatydesmine (4) 之結構研究----------------------------------------------------- 47
第六節 cis-(+)-7,8-Dimethoxymyrtopsine (5) 之結構研究-------------------------------------------------------- 54
第七節 (R)-(-)-8,9-Dimethoxygeibalansine (6) 之結構研究----------------------------------------------------- 64
第八節 Semecarpifoline (7) 之結構研究------------------ 70
第九節 2-Acetylevolitrine (8) 之結構研究--------------- 79
第十節 2-Acetylpteleine (9) 之結構研究----------------- 89
第十一節 Confusameline (10) 之結構研究------------------ 93
第十二節 Ayanin (11) 之結構研究--------------------------- 97
第十三節 Osthenol (12) 之結構研究-------------------------- 102
第十四節 Osthole (13) 之結構研究--------------------------- 105
第十五節 7-O-Prenylumbelliferone (14) 之結構研究----- 109
第十六節 β-Sitosterol (15) & Stigmasterol (16) & Campesterol (17) 之結構研究--------------------- 112
第十七節 Dictamnine (18) 之結構研究---------------------- 118
第十八節 Kokusaginine (19) 之結構研究-------------------- 122
第十九節 Skimmianine (20) 之結構研究-------------------- 132
第二十節 Haplopine (21) 之結構研究------------------------ 138
第二十一節 Methyl vanillate (22) 之結構研究----------------- 142
第二十二節 Syringic acid (23) 之結構研究--------------------- 146
第二十三節 Tetracosyl ferulate (24) 之結構研究-------------- 150
第二十四節 Methyl oleate (25) 之結構研究-------------------- 156
第二十五節 Xanthyletin (26) 之結構研究--------------------- 160
第二十六節 5-Hydroxymethylfurfural (27) 之結構研究------ 164
第二十七節 Anisocoumarin H (28) 之結構研究--------------- 170
第二十八節 Umbelliferone (29) 之結構研究------------------- 176
第五章 抗血小板凝集活性之研究-------------------------- 181
第六章 結語----------------------------------------------------- 184
第七章 實驗部分----------------------------------------------- 186
第一節 儀器與材料-------------------------------------------- 186
第二節 根皮之抽取與分離----------------------------------- 188
第三節 三級非酚性鹽基部 (Fr. A) 之處理--------------- 189
第四節 三級酚性鹽基部 (Fr. B) 之處理------------------ 190
第五節 中性氯仿層 (Fr. C) 之處理------------------------ 191
第六節 乙酸乙酯層 (Fr. D) 之處理------------------------ 194
第七節 正丁醇層 (Fr. E) 之處理--------------------------- 195
第八節 水層 (Fr. F) 之處理--------------------------------- 196
第九節 各化合物之實驗數據-------------------------------- 197
第十節 血小板凝集活性之實驗----------------------------- 211
參考文獻 ----------------------------------------------------------- 213
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