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系統識別號 U0007-0208201118144500
論文名稱(中文) 番石榴莖部與大葉千斤拔根部:降血糖成分之探討
論文名稱(英文) Studies on the Hypoglycemic Constituents:Stem of Psidium guajava and Root of Flemingia macrophylla
校院名稱 臺北醫學大學
系所名稱(中) 生藥學研究所
系所名稱(英) Graduate Institute of Pharmacognosy
學年度 99
學期 2
出版年 100
研究生(中文) 吳宗儒
研究生(英文) Zong-Ru Wu
學號 M303098003
學位類別 碩士
語文別 中文
口試日期 2011-07-14
論文頁數 284頁
口試委員 委員-張溫良
委員-黃偉展
指導教授-徐鳳麟
中文關鍵字 番石榴莖  大葉千斤拔根  降血糖作用 
英文關鍵字 Psidium guajava  Flemingia macrophylla  antiglycemia 
學科別分類
中文摘要 糖尿病為常見之疾病,除了影響人們健康之外,亦衍生許多相關之病
症而造成社會問題,因此研發降血糖藥物,為目前非常迫切的需求。番石榴是台灣民間用於控制糖尿病的傳統中草藥,而大葉千斤拔最近也有文獻表示,在治療糖尿病上有顯著的效果,因此本研究選用這兩種植物,探討其中之活性成分。經由各種層析管柱及不同溶媒系統分離純化後,共分離到二十九個化合物,並根據物理數據、核磁共振光譜判定及文獻資料的比對,而確定其化學結構。從番石榴莖部70 % acetone/ H2O 之萃取物,於n-BuOH 層分離出八個化合物:gallic acid (1)、protocatechuic acid (2)、ferulic acid (3);quercetin (4)、myricetin (5)、(+)-catechin (6)、pedunculagin (7)、castalagin (8)。另外,從大葉千斤拔的根部之萃取物於ethyl acetate 層以及n-hexane 層,共分離出二十一個化合物:phloroglucinol (9)、4'-O-methyl-gallocatechin (10)、genistein (11)、prunetin (12)、genistin (13)、6'-O-acetylgenistin (14)、2'-hydroxygenistein (15)、dalbergioidin (16)、naringenine (17)、lespedezaflavanone A (18)、lespedezaflavanone B (19)、flemichin D (20)、khonklonginol H (21)、eriosematin (22)、iso-eriosematin
(23)、aureol (24)、5,7,2',4'-tetrahydroxy-3-arylcoumarin (25)、lupeol (26)、β-sitosterol (27)、β-stigmasterol (28) 及β-sitosterol-O-D-glucoside (29)。其中化合物9、14、16、21 等四個化合物為首次自千斤拔屬植物分離出,而化合物25 為新化合物。降血糖活性試驗中,使用TNF-α 誘導小鼠肝臟FL83B 細胞株產生胰島素阻抗,於化合物濃度10 μM 之下進行體外試驗,經由細胞攝入螢光葡萄糖 (2-NBDG) 染劑量,篩選出活性化合物。結果顯示,化合物1、3、4、5、6、10、11、12、14、15、16、17、25、26 具有較顯著促進胰島素阻抗之FL83B cell 之glucose uptake 的作用。
英文摘要 No matter in Taiwan perhaps overseas, chronic metabolic diseases such diabetes mellitus is gradually injure the health of our people. In order to improve their quality of life, there is an urgent need to discover new drugs
that effectively treat diabetes. Psidium guajava Linn. is often used as folk medicine to improve diabetes in Taiwan. Flemingia macrophylla (Willd.) O. Ktze. is also proved useful at controlling diabetes. This is the reason that we
choose such two plants to rsearch. Twenty nine compounds were isolated via various chromatographic techniques and their structures were further identified according to their physical data, NMR. Eight compounds have been isolated from the n-BuOH layer of 70 % acetone/H2O extract of P. guajava including gallic acid (1), protocatechuic acid (2), ferulic acid (3), quercetin (4), myricetin (5), (+)-catechin (6), pedunculagin (7), castalagin (8). In addition twenty-one compounds have been isolated from the ethyl acetate and n-hexane layer of extracts of F. macrophylla including phloroglucinol (9), 4'-O-methyl-gallocatechin (10), genistein (11), prunetin (12), genistin (13), 6'-O-acetylgenistin (14), 2'-hydroxygenistein (15), dalbergioidin (16), naringenine (17), lespedezaflavanone A (18), lespedezaflavanone B (19), flemichin D (20), khonklonginol H (21), eriosematin (22), iso-eriosematin
(23), aureol (24), 5,7,2',4'-tetrahydroxy-3-arylcoumarin (25), lupeol (26), β-sitosterol (27), β-stigmasterol (28), β-sitosterol-O-D-glucoside (29). Among them, compound (25) is a new compound, and compounds 9, 14, 16, 21 were
first found in Flemingia species. Tumor necrosis factor-alpha was used to induce insulin resistance of mouse liver FL83B cells. Compound was evaluated for their acute effects in vitro by measuring 2-NBDG uptake of the insulin-resistant cells at 10 μM dose. The results suggest that these compounds 1, 3, 4, 5, 6, 10, 11, 12, 14, 15, 16, 17, 25, 26 can enhance glucose.
uptake in insulin resistant cell.
論文目次 中文摘要............................................................................................................I
英文摘要……..................................................................................................II
總目錄............................................................................................................ IV
圖目錄..........................................................................................................VIII
表目錄..........................................................................................................XVI
縮寫表...........................................................................................................XX
第一章 緒論.....................................................................................................1
第一節、番石榴之簡介.............................................................................1
1-1-1. 植物介紹..................................................................................1
1-1-2. 番石榴相關藥理研究之文獻回顧..........................................3
1-1-3. 番石榴相關化學成分研究之文獻回顧...............................10
第二節、大葉千斤拔之簡介...................................................................32
1-2-1. 植物介紹................................................................................32
1-2-2. 大葉千斤拔相關藥理研究之文獻回顧................................34
1-2-3. 千斤拔屬植物相關化學成分研究之文獻回顧....................40
第三節、糖尿病簡介..............................................................................56
1-3-1. 糖尿病分類.............................................................................56
1-3-2. 糖尿病藥物.............................................................................57
第四節、研究背景.....................................................................................64
第二章 番石榴莖部之研究結果與討論
第一節、PGS-1∼PGS-8 化合物之構造決定.......................................65
(1) Phenolic acids
PGS-1︰gallic acid (1)之結構解析.............................................65
PGS-2:protocatechuic acid (2)之結構解析................................67
PGS-3:ferulic acid (3)之結構解析.............................................69
(2) Flavonoid
1. Flavonol
PGS-4:quercetin (4)之結構解析..............................................73
PGS-5:myricetin (5)之結構解析..............................................77
2. Flavan-3-ols
PGS-6:(+)-catechin (6)之結構解析..........................................79
(3) Ellagitannins
PGS-7:pedunculagin (7)之結構解析..........................................83
PGS-8:castalagin (8)之結構解析...............................................88
第二節、番石榴莖部化學成分之探討.................................................93
第三節、番石榴莖部降血糖活性之評估.............................................95
2-3-1. 番石榴莖部化合物對於細胞葡萄糖攝入之影響...............95
第四節、討論.........................................................................................97
第五節、結論.........................................................................................97
第三章 大葉千斤拔之研究結果與討論.......................................................99
第一節、FM-1∼FM-20 化合物之構造決定.........................................99
(1) Phenolic compounds
FM-1:phloroglucinol (9)之結構解析.........................................99
(2) Flavonoid
1. Flavan-3-ols
FM-2:4'-O-methyl-gallocatechin (10)之結構解析..................102
2. Isoflavones
FM-3:genistein (11)之結構解析..............................................107
FM-4:prunetin (12)之結構解析...............................................111
FM-5:genistin (13)之結構解析...............................................117
FM-6:6'-O-acetylgenistin (14)之結構解析.............................120
FM-7:2'-hydroxygenistein (15)之結構解析............................127
3. Isoflavanones
FM-8:dalbergioidin (16)之結構解析......................................132
4. Flavanones
FM-9:naringenin (17)之結構解析...........................................140
FM-10:lespedezaflavanone A (18)之結構解析.......................146
FM-11:lespedezaflavanone B (19)之結構解析.......................153
FM-12:flemichin D (20)之結構解析......................................161
FM-13:khonklonginol H (21)之結構解析..............................168
(3) Chromones
FM-14:eriosematin (22)之結構解析.......................................178
FM-15:iso-eriosematin (23)之結構解析.................................185
(4) Coumestans
FM-16:aureol (24)之結構解析................................................193
(5) Coumarins
FM-17:5,7,2',4'-tetrahydroxy-3-arylcoumarin (25)之結構解
析................................................................................201
(6) Triterpenoids
FM-18:lupeol (26)之結構解析..............................................212
(7) Stigmastane Steroids
FM-19:β-sitosterol (27)與β-stigmasterol (28)之結構解析....................................................................................218
FM-20:β-sitosterol-3-O-β-D-glucoside (29)之結構解析
....................................................................................222
第二節、大葉千斤拔化學成分之探討..............................................229
第三節、大葉千斤拔降血糖活性之評估..........................................234
第四節、討論......................................................................................237
第五節、結論......................................................................................239
第四章 實驗部分.........................................................................................241
第一節、實驗材料與方法................................................................241
4-1-1. 儀器.....................................................................................241
4-1-2. 層析法.................................................................................241
4-1-3. 一般化學溶媒及試藥.........................................................242
4-1-4. 降血糖之活性評估.............................................................243
第二節、抽提及分離
4-2-1. 番石榴莖部.........................................................................245
4-2-2. 大葉千斤拔.........................................................................247
第三節、PGS-1∼PGS-8 及FM-1∼FM-20 各化合物之物理數
據.......................................................................................248
參考文獻......................................................................................................266
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