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研究生:陳文陸
研究生(外文):Chen Wen-lu
論文名稱:層析在基原、胃腸液及生體介質中之應用
指導教授:許順吉許順吉引用關係
指導教授(外文):Sheu Shuenn-jyi
學位類別:碩士
校院名稱:國立臺灣師範大學
系所名稱:化學研究所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2002
畢業學年度:90
語文別:中文
論文頁數:133
中文關鍵詞:毛細管電泳高效液相層析基原薑黃大黃三黃
外文關鍵詞:CEHPLCsourcesCurcumae RhizomaRhei RhizomaOasis
相關次數:
  • 被引用被引用:3
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毛細管電泳(CE)及高效液相層析(HPLC)是目前最常用來測定中藥成分含量的分析方法。本研究開發薑黃之CE分析條件,並用HPLC鑑定大黃基原與檢測生體介質中大黃成份。
本研究分四個部分,第一部分為開發薑黃藥材的毛細管電泳分析方法。薑黃為常用之中藥材,為薑科植物薑黃 Curcuma longa Linn.的乾燥根莖,具有抗炎、抗菌、抗氧化、抗腫瘤、降血脂等作用。本研究利用毛細管電泳分析藥材中的α-turmerone、β-turmerone、ar-turmerone、 curcumin、demethoxycurcumin、bisdemethoxycurcumin、p-tolylmethyl carbinol、curcumenol等八個重要藥理活性成分。實驗結果顯示利用微胞電動力學毛細管層析(MEKC),以添加SC(sodium cholate)界面活性劑的硼酸鹽溶液為緩衝液,可在25分鐘內分析其中六個成分,而α-turmerone與β-turmerone因結構類似故無法分離。
第二部分為探討大黃sennoside B(SB), sennoside A(SA), rhein(RH), aloe-emodin(AE), emodin(EM), chryaphanol(CH)在不同萃取方式的三黃瀉心湯中的含量差異及大黃、黃芩、黃連以不同比例配置的三黃瀉心湯製劑在人工胃液、腸液中的大黃成分變化。大黃成分在人工胃液中幾不發生變化,但在人工腸液中,由於大黃成份會抑制黃芩配醣體成分水解,因此當有黃芩的存在或大黃藥材配伍的量愈多時,大黃各成份耗損的比例愈高,其中以大黃/黃芩/黃連=2/1/1配伍之三黃瀉心湯的結果最明顯,與等量藥材比較,各成分的萃出比值為SB 25%,SA 6%,RH 29%,AL 16%,EM 43%,CH 12%。
第三部分為比較不同三黃萃取浸膏在動物體內的吸收代謝差異,並開發適當的前處理方法,以便分析餵食後小白鼠血液、尿液中大黃成分的含量不同。本實驗使用Oasis® Cartridge作為前處理,能有效去除干擾物並濃縮樣品,各成分回收率除了AL為79%外,其餘成份均高於90%,經過前處理的血液與尿液,其LC層析圖譜中各波峰重疊較不嚴重,CH、RH、EM、AE波峰可明顯分辨,且管柱不易發生堵塞。本研究以水萃取、50%乙醇萃取、混煎之三黃浸膏等樣品作比較,發現餵食混煎三黃浸膏之老鼠尿液中各成份含量偏低。另外從各成份趨勢變化圖可發現餵食混煎三黃浸膏之老鼠血液各成份出現時間最早,存留時間最長,至12小時之後才有明顯降低之趨勢。
最後一部份收集馬蹄大黃(Rheum officinale Baillon)、掌葉大黃(Rheum palmatum Linne)與唐古特大黃(Rheum tanguticum Maxim)共31個樣品,利用HPLC分析大黃十九個組成成分,以建立大黃基原之化學辨識規則。結果顯示,以6 aloe-emodin-8-O-b-D- (6”-O-galloyl)—glucopyranoside, 12 aloe- emodin-ω-O-β-D-gluco-pyranoside, 13 physcion-8-O-β-D-glucopyranoside, 15 aloe-emodin, 16 rhein, 18 chrysophanol, 19 physcion與內標之波峰面積比值,可做為辨識大黃基原時的指標。研究發現馬蹄大黃的15/IS<0.24,16/IS<0.67,18/IS<0.38,19/IS<0.1。而同屬錦紋大黃的唐古特大黃與掌葉大黃其15/IS>0.25,16/IS>0.67,18/IS>0.49,19/IS>0.1。另外唐古特大黃與掌葉大黃的分辨方法為前者的6/IS>0.37,12/IS>0.08,13/IS>0.1,而後者的6/IS<0.36,12/IS<0.03,13/IS<0.07,(檢液為內標準品溶液0.504mg/mL的methyl 2,4-dihydroxybenzoate,取1mL與樣品液溶成50mL,再取10μL注入LC分析)。此外,唐古特大黃的16/6<3.3,18/6<2.0,19/6<0.5,而掌葉大黃的16/6>3.5,18/6>3.4,19/6>0.6。根據以上數據,可作為辨識大黃基原時的參考依據。
Capillary electrophoresis (CE) and high-performance liquid chromatography (HPLC) are currently the most commonly used methods for analyzing the contents of constituents of Chinese herb drugs. In this study we have developed the CE conditions for analyzing Curcumae Rhizoma and used HPLC to identify the source of Rhei Rhizoma and detect its constituents in the living body.
This study is divided into four parts. The first part is on the development of CE analysis method. Curcumae Rhizoma is a commonly used Chinese herb drug derived from the dried rhizome of the Zingiberaceous plant Curcuma long L. The drug possesses antiphlogistic, antibacterial, antioxidation, antitumor and hypoglycemic effects. This study used CE to analyze the eight important pharmacologically active constituents, a-turmerone, b-tumerone, ar-turmerone, curcumin, demethoxycurcumin, bisdemethoxycurcumin, p-tolymethyl carbinol and curcumenol. Experimental results show that by means of the micellar electrokinetic capillary chromatography (MEKC) with the addition of the borate acid solution containing the surfactant SC (sodium cholate) as a buffer, we are able to analyze six of the constituents within 25 min. Whereas, a-turmerone and b-tumerone are inseparable because of their similarity in structure.
The second part discusses the differences of contents of sennoside B (SB), sennoside A (SA), rhein (RH), aloe-emodin (AE), emodin (EM) and chrysophanol (CH) in the formula Coptis and Rhubarb Combination extracted by different methods; and changes of Rhei Rhizoma constituents in artificial gastric fluid and artificial intestinal fluid for different compositions of the formula made up of the ingredients Rhei Rhizoma, Scutellariae Radix and Coptidis Rhizoma in different ratios. The constituents of Rhei Rhizoma undergo almost no changes in artificial gastric fluid. However, in artificial intestinal fluid, the Rhei Rhizoma constituents can inhibit the hydrolysis of the glycosides from Scutellariae Radix. Hence, in the presence of Scutellariae Radix, or when a larger amount of Rhei Rhizoma is incorporated in the formula, the various constituents of Rhei Rhizoma are consumed in a higher rate. This condition is most conspicuous in the formula composed of Rhei Rhizoma/Scutellariae Radix/Coptidis Rhizoma in the ratios of 2 : 1 : 1. Compared on the basis of equal amount of drug material, the extraction-yield ratios of the various constituents are SB 25%, SA 6%, RH 29%, AE 16%, EM 43% and CH 12%.
The third part compares the absorption and metabolism conditions with the formula extracted by different methods, and develops some suitable pretreatment method for the formula to be fed to mice whose blood and urine are then sampled and analyzed for differences in the contents of the various constituents of Rhei Rhizoma. This study uses Oasisâ Cartridge for the pretreatment, by which interfering substances can be effectively eliminated and the sample condensed. The recovery rates of the constituents are all above 90%, except AL, which is 79%. After pretreatment, the blood and urine samples have various LC peaks that do not present serious overlapping. The peaks corresponding to CH, RH, EM and AE can be clearly identified, and the column does not get clogged so easily. This study compares the formula extracted with water, 50% ethanol and mixed-decoction, and has found that the formula extracted by the mixed-decoction mode yields lower contents of the various constituents in the urine of the mice. Moreover, the tendency (pharmacokinetic) graphs of the various constituents show that the constituents from the formula prepared by mixed concoction appear earliest in the blood stream of the mice and remain there for the longest time, showing a prominent tendency of decline only after 12 hours.
The final part is on the collection of 31 samples derived from Rheum officinale Baillon, R. palmatum L. and R. tanguticum Maxim. which were analyzed with HPLC for nineteen constituents from these samples in order to establish a rule for identifying the sources of Rhei Rhizoma. The results show that the peak area ratios between the internal standard (IS) and 6 aloe-emodin-8-O-b-D-(6”-O-galloyl)- glucopyranoside, 12 aloe-emodin-w-O-b-D-gluco-pyranoside, 13 physcion-8-O-b-D- glucopyranoside, 15 aloe-emodin, 16 rhein, 18 chrysophanol and 19 physcion can serve as an indicator in identifying the source of Rhei Rhizoma, whereby we have found that the horse-hoof Rhei Rhizoma (Rheum officinale) has 15/IS < 0.24, 16/IS < 0.67, 18/IS < 0.38 and 19/IS < 0.1.While the Tangutic Rhei Rhizoma (Rheum tanguticum) and the palm-leafed Rhei Rhizoma (Rheum palmatum), which along with the horse-hoof Rhei Rhizoma all belong to the same grade known as “silk-grained Rhei Rhizoma”, have 15/IS > 0.25, 16/IS > 0.67, 18/IS > 0.49 and 19/IS > 0.08. The way to discriminate the Tungutic from the palm-leafed Rhei Rhizoma is that the former has 6/IS . 0.37, 12/is > 0.08 and 13/is > 0.1; and the latter, 6/IS < 0.36, 12/IS < 0.03 and 13/IS < 0.07 (The internal standard is prepared mixing 1 ml of 0.504 mg/ml methyl-2,4-dihydroxybenzoate solution with 0.2 g of sample in 45 ml of 70% methanol and making to 50ml. A 10-ml aliquot of the solution is then injected into LC for analysis). In addition, the Tungutic Rhei Rhizoma has 16/6 < 3.3, 18/6 < 2.0, 19/6 < 0.5; and the palm-leafed Rhei Rhizoma has 16/6 > 3.5, 18/6 > 3.4 and 19/6 > 0.6. Based on the above data, we are able to identify the sources of Rhei Rhizoma samples.
圖目錄…………………………………………………………II
表目錄……………………………………………………...….V
中文摘要……………………………………………………..VII
英文摘要………………………………………………...……IX
第一章 緒論
第一節 前言……………………………………………………………1
第二節 高效能液相層析法……………………………………………3
第三節 毛細管電泳分析法……………………………………………5
第四節 分析條件參數及適宜性之評估……………………………..14
第五節 化學指紋圖譜………………………………………………..18
第二章 薑黃成份之毛細管電泳
第一節 前言……………………..……………………………………20
第二節 實驗部份……………………………………………………..23
第三章 胃液腸液中大黃成份之定量研究
第一節 前言…………………………………………………………..43
第二節 實驗部份……………………………………………………..46
第三節 結果與討論……………………………………..……………53
第四節 實驗條件之選擇…………………………………………..…59
第四章 血液尿液中大黃成份之定量研究
第一節 前言………………………..…………………………………70
第二節 實驗部分………………………..……………………………71
第三節 結果與討論………………………..…………………………76
第五章 大黃之基原鑑定
第一節 前言………………………………..…………………………85
第二節 實驗部分…………………………..…………………………93
第三節 結果與討論……………………….………………………….96
第六章 結論…………………………………………………………….111
參考資料…………………………………………….…………………116
附錄一 薑黃分析成份UV圖…………………………………….123
附錄二 自分離薑黃成份IR、NMR、MS圖…………………125
附錄三 大黃分析成份圖…………………………………………… 129
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