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研究生:古育華
研究生(外文):Yu-Hua Ku
論文名稱:大黃多酚配苷成分及其抗微生物作用之研究
論文名稱(外文):Studies of polyphenol glycosides of Rhei Rhizoma Radix and theirs antimicrobial activities
指導教授:王苑春王任賢 醫師
指導教授(外文):Yuan-Chuen Wang, Ph. D.Jen-Hsien Wang, M.D.
學位類別:碩士
校院名稱:國立中興大學
系所名稱:食品科學系
學門:農業科學學門
學類:食品科學類
論文種類:學術論文
論文出版年:2004
畢業學年度:92
語文別:中文
論文頁數:135
中文關鍵詞:大黃抗微生物
外文關鍵詞:Rhei Rhizoma Radixantimicrobial activities
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本研究探討由生藥大黃簡易快速製備出其中化合物之方法,以各種光譜儀器分析法分析鑑定化合物之結構,並探討這些化合物之相關生物活性。
首先生藥大黃以甲醇萃取,再以室溫攪拌處理、煮沸攪拌處理、沸騰回流處理及98 ℃熱水批式處理等,四種不同方式各處理五次,結果顯示以98 ℃熱水批式處理,可得到最佳之分離結果。以此再探討不同處理次數對分離效果之影響,其中以處理三次後之殘渣物有最佳之分離結果。將經98 ℃熱水批式處理三次後之殘渣,以冰醋酸萃取,萃取液以製備型C18-HPLC分離,結果得到九個單一吸收峰之區分。選取收率及純度高之五個區分,進行第二部分化合物之結構鑑定,以及第三部分生物活性之研究。
以核磁共振光譜儀、質譜儀進行五個純化區分之結構鑑定。由圖譜判讀之結果,依序鑑定為下列五種化合物:(1). 2-O-cinnamoyl-1-O- gallyol-β-D-glucopyranoside、(2). 2-O-cinnamoyl-1,6-di-O-galloyl-β-D- glucopyranoside、(3). chrysophanol-8-O--D-glucopyranoside、(4). chrysophanol-1-O--D-glucopyranoside及 (5). emodin-6-O--D- glucopyranoside。
將此五個分離自大黃中之化合物探討相關之抑菌活性及抗病毒活性。結果顯示出化合物 (1) ~ (5) 具有抑制金黃色葡萄球菌及幽門螺旋桿菌之作用,MICs值範圍分別為0.24~0.96 mg/mL及0.8~12.8 mg/mL。化合物 (1) ~ (4) 均顯示出抗單純抗疱疹病毒 (HSV) 之活性,其中以化合物 (4) 具有最佳抗HSV-1之活性,SI值為7.70,其次為化合物 (1) 及 (3)。進一步測試化合物加入時間點分析,結果顯示出化合物 (1)、(3) 及 (4) 不具有預防病毒感染細胞之作用,但是具有抑制病毒吸附細胞及在宿主細胞內複製之功能,在病毒感染後之24 h仍具有抑制活性。在此三個化合物中,以化合物 (4) 具最好之抗病毒活性,在濃度75及100 μg/mL時,在HSV-1感染細胞後24 h加入,化合物 (4) 仍能抑制100 %的病毒複製。

In this study, a rapid method for the isolation of compounds of Rhei Rhizoma Radix, identification of the structures of these compounds with NMR and MS, and bioactivities of the compounds were studies.
Rhei Rhizoma Radix was extracted with methanol, and was then subjected to treat with water by four methods, of which stirring with water at room temperature, stirring with boiling water, refluxing with 98℃ water, and batch treating with 98℃ water. The batch treating with 98℃ water for three times obtained good separation. The precipitate extracted with glacial acetic acid, then the supernatant was separated by preparative C18-HPLC. Nine fractions were obtained, of which five fractions giving high recoveries and purity were collected, and the structures and bioactivities of theses five fractions were studied.
Structures of five purified fractions were identified with NMR and MS. The five compounds were identified as (1), 2-O-cinnamoyl-1-O- galloyl-β-D-glucopyranoside, (2), 2-O-cinnamoyl-1,6-di-O-galloyl-β-D- glucopyranoside, (3), chrysophanol-8-O--D-glucopyranoside, (4), chrysophanol-1-O--D-glucopyranoside and (5), emodin-6-O--D- glucopyranoside.
Anitimicrobial and antiviral activities of these five compounds were examined. Compound (1) ~ (5) exhibited strong anitimicrobial activities against Staphylococcus aureus and Helicobacter pylori with 0.24 ~ 0.96 mg/mL and 0.8~12.8 mg/mL of MICs, respectively. Compound (1) ~ (4) showed anti-herpes simplex virus activities, of which compound 4 exhibited the highest anti-HSV-1 activity with 7.70 of SI value, and with descending order by compound (1) and (3). Furthermore, time of addition assay was examined. Compound (1), (3) and (4) didn’t observe prevented effect of viral infection, but showed inhibitory ability of viral adsorption and replication. After 24 h of viral infection, inhibitory activities of compound (1), (3) and (4) still observed. Of which after 24 h of infection of HSV-1, 100 % inhibition of replication of compound (4) was found at the concentration of 75 and 100 μg/mL.

表目錄…………………………………………………………………...V
圖目錄…………………………………………………………………..VI
中文摘要…………………………………………………………….…..1英文摘要…………………………………………………………….…...3
壹、前言…………………………………………………………….…...5
貳、文獻整理……………………………………………………….….. 6
一、大黃之文獻整理…………………………………………………6
(一) 大黃及其生藥……………………………………………..….6
(二) 大黃生藥之歷代評議與傳統藥效…………………………...6
(三) 大黃生藥之化學組成分……………………………………...7
(四) 大黃在傳統中藥上之藥理功能……………………………. 11
(五) 近年來大黃生理活性之文獻整理………………………….12
二、單純疱疹病毒及腸病毒之分類及其抗病毒藥物之研究……..18
(一) 病毒的一般構造………………………………………….....18
(二) 單純疱疹病毒的種類及引起的臨床症狀……………..…...21
(三) 抗單純疱疹病毒藥物之研究…………………………...…..23
(四) 腸病毒的種類及引起的臨床症狀……………………...…..27
(五) 抗腸病毒藥物之研究…………………………………...…..30
參、材料與方法………………………………………………………..32
一、材料……………………………………………………………..32
(一) 大黃………………………………………………………….32
(二) 測試微生物………………………………………………….32
(三) 微生物培養基……………………………………………….33
(四) 化學試劑及藥品…………………………………………….34
(五) 儀器設備…………………………………………………….35
二、方法………………………………………………………….….36
第一部分:大黃化合物快速簡易分離方法之探討…………….….36
(一) 甲醇萃取…………………………………………………….36
(二) 去離子水處理………………………………………….……36
1. 室溫攪拌處理……………………………………………….36
2. 煮沸攪拌處理……………………………………………….36
3. 沸騰回流處理……………………………………………….37
4. 98 ℃熱水批式處理………………………………………….37
(三) 處理次數探討………………………………………….……37
(四) HPLC分析 (一)……………………………………………..38
(五) 製備型HPLC……………………………………………..…38
1. 樣品前處理………………………………………………….38
2. 製備型HPLC分離條件…………………………………….39
(六) HPLC分析 (二)………………………………………..…….39
(七) 大黃化合物快速簡易分離流程概要…………………….…40
第二部分:大黃化合物結構鑑定之研究…………………………..40
(一) 核磁共振光譜儀分析……………………………………….40
(二) 質譜儀分析…………………………………………………..42
1. ESI-MS………………………………………………………..42
2. FAB-MS……………………………………………………….42
(三) UV/VIS spectrophotometer光譜儀掃描……………….…..43
第三部份:大黃化合物生物活性之研究………………………..…43
(一) 抗菌活性………………………………………………….…43
1. 菌株培養…………………………………………………….43
2. 最低抑菌濃度測定………………………………………….44
(二) 抗病毒活性…………………………………………….........44
1. 細胞培養與計數…………………………………………….44
2. 病毒增殖…………………………………………………….46
3. 化合物之配製……………………………………………….46
4. 細胞毒性試驗……………………………………………….47
5. 50 %抑制濃度測定…………………………………………..48
6. 選擇指數之測定…………………………………………….52
7. 病毒感染時間效應………………………………………….52
肆、結果與討論………………………………………………………..54
第一部分:大黃化合物快速簡易分離方法之探討………………..54
(一) 甲醇萃取…………………………………………………….54
(二) 去離子水處理……………………………………………….54
(三) 處理次數探討……………………………………………….56
(四) 製備型HPLC分離……………………………………….…59
(五) 分離流程概要及收率…………………………………….…62
第二部分:大黃化合物結構鑑定之研究……………………….….67
(一) 圖譜討論…………………………………………………….67
1. 化合物 (1) ……………………...….……………………….67
2. 化合物 (2) ……………………….………………...……….72
3. 化合物 (3) ……………………….....………………………78
4. 化合物 (4) ...………………………..………………………84
5. 化合物 (5) ……………………….…...…………………….90
(二) 圖譜結果…………………………………………………….95
第三部份:大黃化合物生物活性之研究…………………….……100
(一) 抗菌活性…………………………………………………...100
(二) 抗病毒活性………………………………………………...102
1. 細胞毒性試驗……………………………………………...102
2. 病毒50 %抑制濃度測定…………………………………..104
3. 選擇指數之評估…………………………………………...108
4. 病毒感染時間效應………………………………………...110
五、結論…………………………………………………………….....118
陸、參考文獻………………………………………………….…….…121

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