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系統識別號 U0007-1506201013024200
論文名稱(中文) 降血糖活性成分之探討:山茱萸與野生番石榴
論文名稱(英文) Studies on the Hypoglycemic Constituents:Fructus corni and Psidium guajava L.
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 98
學期 2
出版年 99
研究生(中文) 黃竹君
研究生(英文) Chu-Chun Huang
學號 M303097015
學位類別 碩士
語文別 中文
口試日期 2010-06-14
論文頁數 185頁
口試委員 委員-鄭瑞棠
委員-李美賢
委員-黃偉展
指導教授-徐鳳麟
共同指導教授-劉慧康
中文關鍵字 山茱萸  番石榴  降血糖 
英文關鍵字 Fructus corni  Psidium guajava L.  antiglycemic 
學科別分類
中文摘要 本研究探討山茱萸果實及野生番石榴葉之降血糖活性成分,山茱萸為降血糖藥物六味地黃丸之其中一味,野生番石榴則常被用為民間之降血糖藥物,故針對山茱萸果實及番石榴葉作進一步的活性成分探討。經各種層析管柱及不同溶媒系統分離純化後,共分離出二十八個化合物。山茱萸果實之70 % acetone/H2O萃取物於n-BuOH層分離出十一個化合物,分別為quercetin 3-O-β-D-glucuronide (1)、quercetin 3-O-β-D-(6″-n-butyl glucuronide) (2)、epicatechin 3-O-gallate (3)、loganin (4)、(7R)-n-butyl morroniside (5)、gallic acid (6)、caffeic acid (7)、caftaric acid monomethyl ester (8)、cornuside (11)、2-butoxybutandioic acid (12);於hexane層分離出兩個化合物oleanolic acid (9)、β-sitosterol (10),其中compound 8、12為首次由天然物中分離出之成分。另外,從野生番石榴葉之70 % acetone/H2O萃取物共分離十六個化合物,其中自乙酸乙酯層萃取物分離出quercetin (13)、quercerin 3-O-β-D-galactopytanoside (14)、quercetin 3-O-α-L-arabinofuranoside (15)、quercerin 3-O-β-D-xylopyranoside (16)、quercetin 3-O-β-D-glucuronide (17)、gallic acid (20)、protocatehuic acid (21)、p-coumaric acid (22)、ferulic acid (23)、strictinin (24)、isostrictinin (25)、casuarinin (26)、1,2,3,4,6-penta-O-galloyl-β-D-glucose (27)、1,2,3,6-tetra-O-galloyl-β-D-glucose (28);自n-BuOH層萃取物得到(+)-gallocatechin (18)、(+)-catechin (19)。另外,由山茱萸分離出之化合物中,compound 3、8、12能抑制PEPCK mRNA表現的活性;compound 3、5、9具有抑制β細胞產生NO 的能力;而compound 5、6能抑制β細胞被cytokine毒殺的能力。此外,自野生番石榴葉分離出之化合物,發現compound 13、17、18、19、20、21對glucose uptake有促進作用。其中compound 13、20已有文獻發表,compound 17、18、19、21則為首次發現具有glucose uptake的促進效果。
英文摘要 In this study, bioactive constituents of Fructus corni and Psidium guajava L. were investigated. Fructus corni is one of the component of Liuwei Dihuang Pills, and Psidium guajava L. is often used as an antiglycemic drug. Through a variety of chromatography, totaly 28 compounds were isolated. Twelve compounds which have been isolated from the n-BuOH and n-Hexane layer of 70 % acetone/H2O extract of Fructus corni including quercetin 3-O-β-D-glucuronide (1), quercetin 3-O-β-D-(6″-n-butyl glucuronide) (2), epicatechin 3-O-gallate (3), loganin (4), (7R)-n-butyl morroniside (5), gallic acid (6), caffeic acid (7), caftaric acid monomethyl ester (8), oleanolic acid (9), β-sitosterol (10), cornuside (11), and 2-butoxybutandioic acid (12). Among them, compounds 8, 12 were first isolated from the plant. In addition, sixteen compounds have been isolated from the ethyl acetate and n-BuOH layer of 70 % acetone/H2O extracts of Psidium guajava L. including quercetin (13), quercerin 3-O-β-D-galactopytanoside (14), quercetin 3-O-α-L-arabinofuranoside (15), quercerin 3-O-β-D-xylopyranoside (16), quercetin 3-O-β-D-glucuronide (17), (+)-gallocatechin (18), (+)-catechin (19), gallic acid (20), protocatehuic acid (21), p-coumaric acid (22), ferulic acid (23), strictinin (24), isostrictinin (25), casuarinin (26), 1,2,3,4,6-penta-O-galloyl-β-D-glucose (27), and 1,2,3,6-tetra-O-galloyl-β-D-glucose (28).
For Fructus corni, compounds 3、8、12 can inhibit the expression of PEPCK mRNA, compound 3、5、9 can inhibit NO production, and compound 5、6 can inhibit cytokine mediated cell death. On the other hand, compounds 13、17、18、19、20、21 form Psidium guajava L. can enhance glucose uptake in C2C12 cell. It was documental that compouns 13、20 can increase the glucose uptake. It’s the first time to find that compounds 17、18、19、21 can enhance glucose uptake.
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..................................................XIII
縮寫表..................................................XV

第一章 緒論...........................................1
 第一節、研究背景及目的................................1
第二節、山茱萸的藥理性質及其化學相關研究..............8
第三節、野生番石榴的藥理性質及其化學相關研究..........17

第二章 山茱萸之實驗結果與討論..........................26
 第一節、實驗結果......................................26
2-1-1、抽提及分離..............................26
2-1-2、化合物之構造決定........................28
(1)Flavonoid類化合物
quercetin 3-O-β-D-glucuronide (1) 之結構解析.........,28
quercetin 3-O-β-D-(6″-n-butyl glucuronide) (2) 之結構解析......................................................32
epicatechin 3-O-gallate (3)之結構解析......................................................37
(3) Iridoid 類化合物
loganin (4) 之結構解析................................42
7-n-butylmorroniside (5) 之結構解析...................48
(4) Phenolic 類化合物
gallic acid (6) 之結構解析............................55
caffeic acid (7) 之結構解析...........................58
caftaric acid monomethyl ester (8) 之結構解析.........61
(5) Triterpenoid 類化合物
oleanolic acid (9) 之結構解析.........................66
β-sitosterol (10) 之結構解析..........................71
(6) 其他
cornuside (11) 之結構解析.............................78
2-butoxybutandioic acid (12) 之結構解析...............84
第二節、結論..........................................90
2-2-1、化學成分之探討...............................90
2-2-2、降血糖活性之評估.............................93
第三節、討論..........................................99

第三章 野生番石榴之實驗結果與討論......................101
 第一節、實驗結果......................................101
3-1-1、抽提及分離...................................101
3-1-2、化合物之構造決定.............................102
(1)Flavonoid類化合物
quercetin (13) 之結構解析.............................102
quercerin 3-O-β-D-galactopytanoside (14) 之結構解析...105
quercetin 3-O-α-L-arabinofuranoside (15) 之結構解析...109
quercerin 3-O-β-D-xylopyranoside (16) 之結構解析......113
(+)-gallocatechin (18) 之結構解析.....................118
(+)-catechin (19) 之結構解析..........................120
(2)Phenolic 類化合物
protocatehuic acid (21) 之結構解析....................123
p-coumaric acid (22) 之結構解析.......................127
ferulic acid (23) 之結構解析..........................130
(3)Ellagitannin 類化合物
strictinin (24) 之結構解析............................134
isostrictinin (25) 之結構解析.........................137
casuarinin (26) 之結構解析............................141
(4)Gallotannin 類化合物
1,2,3,4,6-penta-O-galloyl-β-D-glucose (27) 之結構解析.145
1,2,3,6-tetra-O-galloyl-β-D-glucose (28) 之結構解析...148
第二節、結論..........................................152
 3-2-1、化學成分之探討...............................152
3-2-2、降血糖活性之評估.............................156
 第三節、討論..........................................158

第四章 實驗部分........................................162
第一節、實驗材料與方法................................162
4-1-1、儀器.........................................162
4-1-2、層析法.......................................162
4-1-3、一般化學溶媒及試藥...........................163
4-1-4、活性實驗.....................................163
第二節、各化合物之物理數據............................165

參考文獻................................................177
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