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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 張嘉銓(Chia-Chuan Chang) | |
| dc.contributor.author | Chi-Heng Wang | en |
| dc.contributor.author | 王智恆 | zh_TW |
| dc.date.accessioned | 2021-06-15T11:26:04Z | - |
| dc.date.available | 2021-08-26 | |
| dc.date.copyright | 2016-08-26 | |
| dc.date.issued | 2016 | |
| dc.date.submitted | 2016-08-18 | |
| dc.identifier.citation | 1. Juan, Y.-C.; Chang, C.-C.; Tsai, W.-J.; Lin, Y.-L.; Hsu, Y.-S.; Liu, H.-K. Pharmacological evaluation of insulin mimetic novel suppressors of PEPCK gene transcription from Paeoniae Rubra Radix. J. Ethnopharmacol. 2011, 137 (1), 592–600.
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/49380 | - |
| dc.description.abstract | 赤芍(Paeoniae Rubra Radix)為芍藥科 (Paeoniaceae) 芍藥屬 (Paeonia) 之植物的帶皮乾燥根，是傳統中藥中的一種重要草藥，常用於治療糖尿病之方劑中。赤芍的乙醇萃取物經液─液萃取以極性劃分成正己烷、二氯甲烷和水可溶部分，水可溶部分進一步利用Sephadex LH-20、silica gel、Lobar RP-18和半製備HPLC等管柱分離純化，化合物結構透過NMR與質譜技術判定。共計得到10個化合物，包括5個單萜類 (monoterpenoids) 成分：paeoniflorin (1) 、 oxypaeoniflorin (2)、benzylpaeoniflorin (3)、4-O-methyl paeoniflorin (4)、paeonidanin (5)、 1個黃酮類 (flavonoid) 成分：ent-catechin (6); 1個苷類 (glycoside) 成分：1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose (7); 以及3個苯甲酸類 (benzoic acids) 成分：benzoic acid (8)、4-hydroxybenzoic acid (9)、vanillic acid (10) 。其中化合物7屬於可水解單寧類 (hydrolyzable tannin)，具有擬胰島素 (insulin－mimetic) 的活性1，能使胰島素受器磷酸化而活化胰島素訊號傳遞路徑，達到降低血糖的效果，因此具有極高的藥物發展潛力。此篇研究中化合物7由赤芍之分離方法，較其他種類或分離方法4, 66, 67提升了赤芍中取得化合物7的量高1.6~4.1倍。本研究使用之分離方法可進一步研究以對可水解單寧之分離純化有更多進展。
多酚類成分常見於天然植物中，屬於次級代謝物，在抵抗外部病菌侵入發揮了重要功用，因此具有極高的藥物研發潛力。本研究探討赤芍乙醇萃取物經高多孔性樹脂Diaion HP20吸附後，以極性切割劃分為乙酸乙酯可溶部分、水可溶部分以及沉澱物NPF (non－PGG fraction)。NPF經過三氟乙酸進行酸水解反應後，以液─液萃取法將水解產物為乙酸乙酯及水可溶部分。將兩部分與縮合單寧、可水解單寧分別進行顯色反應以比較其特性，在使用三氯化鐵 (FeCl3, 1%)、溴水 (Br2, 3%)、四乙酸鉛 [Pb(C2H3O2)4, 1%] 及硫酸亞鐵胺 [FeNH4 (SO4)2, 1%] 等試劑反應後，得到此NPF之化學性質與縮合單寧有類似之實驗結果，以香草醛─鹽酸法檢驗不同批次生產之NPF，判斷含縮合單寧比例分別為25.8%與32.1%。其後以兩種硫化物試劑反應後，確立了以苄硫醇(benzyl mercaptan) 試劑進行聚合性多酚之硫解反應，可得到具再現性之液相層析圖譜，並以Lobar B type製備管柱純化，得到T−1、T−2、T−3、T−4、T−5五個化合物，其中T-2之化學結構以NMR與質譜技術判定，推測為(−)-epicatechin 4β-benzylthioether，可得知NPF之部分縮合單寧結構。 | zh_TW |
| dc.description.abstract | Paeoniae Rubra Radix (PRR), the dried root with bark of Paeoniaceae, is an important traditional Chinese medicine often used in anti-diabetic drugs. Ethanol extract of PRR was divided into fractions soluble in n-hexane, dichloromethane (DCM) and water via liquid−liquid partitioning process, The water-soluble fractions was separated by chromatographic methods including Sephadex LH-20, Silica gel, Lobar RP-18 column and semi-preparative HPLC to afford 10 compounds (1-10).
These compounds were characterized as five monoterpenoids: paeoniflorin (1), oxypaeoniflorin (2), benzoylpaeoniflorin (3), 4-O-methylpaeoniflorin (4), paeonidanin (5); one flavonoids: ent-catechin (6); one glycoside: 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose (7); and three benzoic acid derivates: benzoic acid (8), 4-hydroxybenzoic acid (9), vanillic acid (10). In terms of its anti-diabetic activity, Compound 7 have insulin-mimetic activity1, which enables the phosphorylation of insulin receptors, and activate the insulin signal transmission path, thereby achieve the function of lowering blood sugar, thus, Compound 7 has high potential for drugs development. The method of extraction and isolation in this study4, 66, 67 enhance the yield of 7 about 1.6~4.1 times from peony plants, this method is expected to further develop for hydrolyzed tannin purification. Polyphenols are common second metabolites found in a number of plants, These compounds play important roles against herbivory and infections of bacteria, and therefore being high potential for the development of anti-diabetic drug. This study was to evaluate the dried Paeoniae Rubra Radix ethanol extracts, after adsorbed with high porous Diaion HP20, the Diaion HP20 absorbate were suspended in water and partitioned with ethyl acetate, then divided into fractions soluble in EtOAc, water and the precipitate via liquid−liquid partitioning process. The precipitate was hydrolyzed by trifluoroacetic acid, and divided hydrolysates into water-soluble fraction and ethyl acetate fration, then the two fractions and condensed tannins, hydrolyzable tannins were subjected to colormetric analysis to compare its chemical characteristic, the reagents include: ferric chloride (FeCl3, 1%), bromine (Br2, 3%), lead(IV) acetate [Pb(C2H3O2)4, 1%] and iron(II) ammonium sulfate, the results show that the precipitate has similar chemical characteristics to condensed tannins in this experiment, and the results of Vanillin−HCl assay, examing two different batch of NPF, show 25.8%, 32.1% of the content of condensed tannin respectively. Followed by acid hydrolysis with different concentration and two thiolysis reagent, the method was established by using benzyl mercaptan to thiolyze the polymeric polyphenols, and the liquid chromatography spectrum of the thiolysate shows high reproducibility, after that, use Lobar RP-18 B type to separate thiolysate of the polyphenols to afford 5 compounds: T−1、T−2、T−3、T−4、T−5. Wherein T-2 was analysed by NMR and mass spectrometry, the chemical structure is presumed to be (−)-epicatechin 4β -benzylthioether, that can be part of the NPF condensed tannin structure. | en |
| dc.description.provenance | Made available in DSpace on 2021-06-15T11:26:04Z (GMT). No. of bitstreams: 1 ntu-105-R02423015-1.pdf: 5793168 bytes, checksum: 30f3e7dcb7ad4e9a0fdbda5a878aaee0 (MD5) Previous issue date: 2016 | en |
| dc.description.tableofcontents | 1. 緒論及研究目的 1
1.1 研究目的 1 1.2 赤芍之簡介 2 1.3 芍藥屬(Paeonia)成分之文獻回顧 3 2. 實驗結果與討論 26 2.1 赤芍之高極性化學成分 28 2.1.1 單萜類 (Monoterpenoids) 28 2.1.1.1 Paeoniflorin (1) 之結構解析 28 2.1.1.2 Oxypaeoniflorin (2) 之結構解析 30 2.1.1.3 Benzoylpaeoniflorin (3) 之結構解析 32 2.1.1.4 4-O-methylpaeoniflorin (4) 之結構解析 34 2.1.1.5 Paeonidanin (5) 之結構解析 36 2.1.2 黃酮類 (Flavonoids) 38 2.1.2.1 ent-Catechin (6) 之結構解析 38 2.1.3 苷類 (Glycoside) 40 2.1.3.1 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose (7) 之結構解析 40 2.1.4 苯甲酸衍生物 (Benzoic acid derivatives) 42 2.1.4.1 Benzoic acid (8) 之結構解析 42 2.1.4.2 4-Hydroxybenzoic acid (9) 之結構解析 42 2.1.4.3 Vanillic acid (10) 之結構解析 42 2.2 赤芍降血糖多酚 (NPF) 之研究 44 2.2.1 NPF之質譜 (ESI/MS) 解析 44 2.2.2 酸水解法 44 2.2.3 顯色反應法(Colormetric Analysis) 45 2.2.4 香草醛─鹽酸法 (Vanillin−HCl assay) 46 2.2.5 聚合性多酚之降解方法開發 47 2.2.5.1 2-巰基乙醇 (2-mercaptoethanol, 2-ME) 硫解法 47 2.2.5.2 芐硫醇 (benzyl mercaptan) 硫解法 48 2.2.6 NPF硫解產物之圖譜解析與原聚合物化學結構特徵推判 49 2.2.6.1 硫解產物T-1之圖譜解析 49 2.2.6.2 硫解產物T-2之結構解析 51 2.2.6.3 硫解產物T-3, T-4之結構解析 53 2.2.6.4 硫解產物T-5之結構解析 54 2.3 討論 56 2.3.1 PGG之產率討論 56 2.3.2 NPF之質譜離子強度討論 56 2.4 結論 57 3. 實驗部分 58 3.1 儀器與材料 58 3.1.1 理化性質測定儀器 58 3.1.2 成分分離之儀器及材料 58 3.1.3 試劑與溶媒 59 3.1.4 薄層層析展開系統 59 3.2 赤芍材料來源 59 3.2.1 NPF來源 59 3.3 赤芍成分萃取與純化 60 3.3.1 赤芍高極性化學成分萃取與純化 60 3.3.1.1 水可溶部分之分離 61 3.3.2 赤芍縮合單寧純化 63 3.4 實驗方法 64 3.4.1.1 NPF之酸水解法 64 3.4.1.2 顯色法 64 3.4.1.3 香草醛─鹽酸法 64 3.4.1.4 NPF之硫解反應法I 64 3.4.1.5 NPF之硫解反應法II 64 3.4.1.6 NPF硫解產物之純化 64 3.5 物理性質 65 參考文獻 67 附 圖 77 | |
| dc.language.iso | zh-TW | |
| dc.subject | 單寧 | zh_TW |
| dc.subject | 赤芍 | zh_TW |
| dc.subject | 多酚 | zh_TW |
| dc.subject | 降血糖 | zh_TW |
| dc.subject | 五?食子醯葡萄糖 | zh_TW |
| dc.subject | Hypoglycemic | en |
| dc.subject | tannin | en |
| dc.subject | 6-O-petna-galloyl-β-D-glucopyranose | en |
| dc.subject | Paeoniae Rubra Radix | en |
| dc.subject | polyphenols | en |
| dc.title | 赤芍之高極性化學成分及降血糖多酚之研究 | zh_TW |
| dc.title | Chemical Investigation of Polar Constituents and Hypoglycemic Polyphenols from Paeoniae Rubra Radix | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 104-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 李水盛(Shoei-Sheng Lee),林雲蓮(Yun-Lian Lin),劉慧康(Hui-Kang Liu) | |
| dc.subject.keyword | 赤芍,多酚,降血糖,五?食子醯葡萄糖,單寧, | zh_TW |
| dc.subject.keyword | Paeoniae Rubra Radix,polyphenols,Hypoglycemic,1,2,3,4,6-O-petna-galloyl-β-D-glucopyranose,tannin, | en |
| dc.relation.page | 114 | |
| dc.identifier.doi | 10.6342/NTU201603104 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2016-08-18 | |
| dc.contributor.author-college | 醫學院 | zh_TW |
| dc.contributor.author-dept | 藥學研究所 | zh_TW |
| 顯示於系所單位： | 藥學系 | |
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