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研究生:陳怡秀
研究生(外文):Yi-Shiou Chen
論文名稱:臺灣產硬齒獼猴桃莖部抗結核活性及化學成分之研究
論文名稱(外文):Antitubercular Activity and Chemical Constituents from the Stems of Formosan Actinidia callosa var. callosa
指導教授:蔡烟力
學位類別:碩士
校院名稱:高雄醫學大學
系所名稱:天然藥物研究所碩士班
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:2006
畢業學年度:94
語文別:中文
論文頁數:324
中文關鍵詞:獼猴桃科硬齒獼猴桃抗結核菌活性
外文關鍵詞:ActinidiaceaeActinidia callosa Lindl. var. callosaantitubercular activity
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中文摘要
硬齒獼猴桃為獼猴桃科的高大攀緣性植物,分佈於南亞,主要產於中國南部、印尼、印度、馬來西亞和台灣的中低海拔灌木叢。其莖部甲醇抽出物對Mycobacterium tuberculosis 90-221387體外試驗顯示具有抗結核菌活性。甲醇抽出物經分配後的正己烷可溶部、氯仿可溶部及水可溶部顯現抗結核菌活性。由本植物之正己烷可溶部,共分離出28個化合物,包括16種三萜類化合物: ??-amyrinyl palmitate (1)、taraxerol (7)、lupeol (8)、taraxasteryl palmitate (10)、pseudo-taraxasteryl palmitate (11)、ursolic acid acetate (14)、3??-acetoxy-12-ursen-11-one (15)、3??-acetoxy-11-ursen-13??,30-olide (16)、3??-acetylurs-28,13-olide (18)、oleanolic acid (20)。混合物??-amyrenonol (23)與??-amyrenonol (24)、ursolic acid (25)、callosandiol (26)、actinidenic acid (27)、callosenol (28),5種固醇類化合物: ??-sitosterone (12)、??-sitosterol (13)、5??-stigmastan-3,6-dione (17)、6??-hydroxystigmast-4-en-3-one (21)、ergosterol-5,8-endoperoxide (22),2種維他命E衍生物類: ??-tocopherol (2)、??-tocospirol B (9),以及5種長鏈脂肪族類: methyl oleate (3)、(6Z,9Z,12Z,15Z)-methyloctadeca-6,9,12,15-tetraenoate (4)與(13Z,16Z,19Z,22Z)-methylpentacosa-13,16,19,22-tetraenoate (5)的混合物,methyl linoleate (6),(Z)-hexacos-13-enoic acid (19)。
本植物氯仿層可溶部,共分離出4個化合物,包括1種三萜類化合物:asiatic acid (29),1種固醇類化合物:stigmasterol (30),1種phenylpropanoid類化合物:trans-coniferyl aldehyde (31),1種coumarin類化合物:umbelliferone (32)。
這些分離得到化合物中,callosandiol (26),actinidenic acid (27)和callosenol (28)為新化合物,並利用光譜數據解析其結構。化合物14、25、29與其乙醯化產物29a顯示對Mycobacterium tuberculosis 90-221387具有抗結核菌活性。
Abstract
Actinidia callosa Lindl. var. callosa (Actinidiaceae) is a tall climbing tree, and MeOH extract of its stems showed significant antitubercular activity against Mycobacterium tuberculosis 90-221387 (clinical isolate) in vitro. The MeOH extract was partitioned into n-hexane-, CHCl3-, n-BuOH and H2O-soluble fractions, and showed significant antitubercular activity except n-BuOH-soluble fraction. The investigation of the n-hexane-soluble fraction led to the isolation of twenty-eight compounds, including sixteen triterpenoids: ??-amyrinyl palmitate (1), taraxerol (7), lupeol (8), taraxasteryl palmitate (10), pseudo-taraxasteryl palmitate (11), ursolic acid acetate (14), 3??-acetoxy-12-ursen-11-one (15), 3??-acetoxy-11-ursen-13??,30-olide (16), 3??-acetoxyurs-28,13-olide (18), oleanolic acid (20), mixture of ??-amyrenonol (23) and ??-amyrenonol (24), ursolic acid (25), callosandiol (26), actinidenic acid (27), callosenol (28), five steroids: ??-sitosterone (12), ??-sitosterol (13), 5??-stigmastan-3,6-dione (17), 6??-hydroxy- stigmast-4-en-3-one (21), ergosterol-5,8-endoperoxide (22), two tocopherols: ??-tocopherol (2), ??-tocospirol B (9), five aliphatic long-chain compounds: methyl oleate (3), mixture of (6Z,9Z,12Z,15Z)-methyloctadeca-6,9,12,15-tetraenoate (4) and (13Z,16Z,19Z,22Z)-methylpentacosa-13,16,19,22-tetraenoate (5), methyl linoleate (6), and (Z)-hexacos-13-enoic acid (19), respectively.
The investigation of the CHCl3-soluble fraction led to the isolation of four compounds, including one triterpenoid: asiatic acid (29), one steroid: stigmasterol (30), one phenylpropanoid: trans-coniferyl aldehyde (31), one coumarin: umbelliferone (32), respectively.
Among these isolates, 26, 27, and 28 are new compounds. The structures of these isolates were established by spectroscopic analyses. Compounds 14, 25, 29 and its acetate 29a showed antitubercular activity against Mycobacterium tuberculosis 90-221387。
總目錄
誌謝
總目錄 I
圖目錄 IV
表目錄 XII
中文摘要 i
英文摘要 ii
第一章 、緒言 1
第二章 、研究動機與目的 5
第三章 、獼猴桃屬植物過去成分的回顧 7
第四章 、過去抗結核菌植物研究概要………………………………..30
第五章、結果與討論 ………48
第一節 莖部之抽取與分離 48
第二節 ??-Amyrinyl palmitate (1)之結構解析………………..58
第三節 ??-Amyrin (1a)之結構解析 63
第四節 ??-Tocopherol (2)之結構解析 66
第五節 Methyl oleate (3)之結構解析 .. 71
第六節 (6Z,9Z,12Z,15Z)-Methyl octadeca-6,9,12,15-tetraenoate
(4) and (13Z,16Z,19Z,22Z)-Methylpentacosa-13,16,19, 22-tetraenoate (5)之結構解析… 75
第七節 Methyl linolate (6) 之結構解析 ……………..79
第八節 Taraxerol (7) 之結構解析 ……………...83
第九節 Lupeol (8) 之結構解析 ………………87
第十節 ??-Tocophspiro B.(9) .之結構解析 ………………90
第十一節 Taraxasteryl palmitate (10)之結構解析 ……………...95
第十二節 Pseudo-Taraxasteryl palmitate (11)之結構解析 ……..99
第十三節 ??-Sitostenone (12)之結構解析 …………104
第十四節 ??-Sitosterol (13)之結構解析 …………109
第十五節 Ursolic acid acetate (14)之結構解析 ……………114
第十六節 3??-Acetoxy-12-ursen-11-one (15)之結構解析……...118
第十七節 3??-Acetoxy-11-ursen-13??,30-olide (16)
之結構解析 133
第十八節 5??-Stigmastan-3,6-dione (17)之結構解析 ………….147
第十九節 3??-Acetoxyurs-28,13-olide (18)之結構解析……….152
第二十節 Hexacos-13-enoic acid (19)之結構解析……………158
第二十一節 Oleanolic acid (20)之結構解析……………………..162
第二十二節 6??-Hydroxystigmast-4-en-3-one (21)之結構解析….166
第二十三節 Ergosterol-5,8-endoperoxide (22)之結構解析..…….171
第二十四節 ??-Amyrenonol (23) and ??-Amyrenonol (24)
之結構解析…………………………………………176
第二十五節 Ursolic acid (25)之結構解析………………………..184
第二十六節 Callosandiol (26)之結構解析……………………….188
第二十七節 Actinidenic acid (27)之結構解析…………………...203
第二十八節 Callosenol (28)之結構解析…………………............218
第二十九節 Asiatic acid (29)之結構解析………………………..234
第三十節 Asiatic acid triacetate (29a)之結構解析……………247
第三十一節 ??-Sitosterol (13) and Stigmasterol (30)
之結構解析................................................................258
第三十二節 trans-Coniferyl aldehyde (31)之結構解析………….261
第三十三節 Umbelliferone (32)之結構解析……………………..266
第六章、 抗結核活性之研究………………………………………..270
第一節 .前言………………………………………………….270
第二節 .實驗方法及步驟…………………………………….271
第三節 .抗結核活性評估…………………………………….272
第七章、結論………………………………………………………..274
第八章、實驗部分 ..277
第一 節 .儀器與材料 ..277
第二 節 .莖部之抽取與分離………………………………….279
第三 節 .正己烷可溶部之分離 ……………………………….279第四 節 .氯仿可溶部之分離………………………………….292
第五 節 .化合物之實驗數據………………………………….295
參考文獻 314
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