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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 李水盛 | |
| dc.contributor.author | Po-Hung Hsieh | en |
| dc.contributor.author | 謝伯鴻 | zh_TW |
| dc.date.accessioned | 2021-06-14T16:42:51Z | - |
| dc.date.available | 2008-09-11 | |
| dc.date.copyright | 2008-09-11 | |
| dc.date.issued | 2008 | |
| dc.date.submitted | 2008-08-01 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/40219 | - |
| dc.description.abstract | 甲型葡萄糖水解酶抑制劑是作用在腸道酵素的一種口服降血糖藥物，藉由干擾碳水化合物之代謝進而降低飯後血糖，達到治療糖尿病之功效。近日發現天然物苯丙醯黃酮鼠李糖苷類化合物對此酵素具良好抑制活性，故本研究對此類化合物進行結構活性關係之探討。選用松醇和橙皮苷作為起始物，以肉桂酸和肉桂基溴 (cinnamyl bromide) 進行酯化和醚化反應製備一系列類似物，再利用催化性氫化反應合成相對應之非共軛系統衍生物。
甲型葡萄糖水解酶試驗顯示松醇類衍生物不具此酵素抑制活性，但可增強胰島素促進葡萄糖吸收之活性，其中以 IIC-4 效果最好 (0.97 uM, S.I. = 13.64)。在鹼性條件下橙皮苷開環形成查爾酮 (chalcone) 類化合物 (IVA-2)，此類化合物可些微抑制甲型葡萄糖水解酶，其中在橙皮苷之葡萄糖二號位置和肉桂基溴進行醚化反應可增強產物抑制活性 (IVA-4, IC50 = 136.8 uM)。以 IB-1 在正常老鼠進行葡萄糖耐受性試驗後，發現可顯著降低血糖值，再分別以松醇和肉桂酸給藥進行相同試驗，顯示此效果可能是其水解產物松醇和肉桂酸之功效。而橙皮苷和肉桂基溴之醚化產物其相關活性仍待進一步探討。 | zh_TW |
| dc.description.abstract | α-Glucosidase inhibitors (AGH) are one type of oral antihyperglycemic drugs targeting on the enzymes in the small intestine. They block the metabolism of the carbohydrates and lower postprandial glucose level to achieve therapeutic control of diabetes. According to the recent finding of natural flavonol O-acylated rhamnosides to be potent α-glucosidase inhibitors, the structure and activity relationship of such type compounds were explored in this study. Pinitol and hesperidin were chosen as starting materials. Esterification and etherification were undertaken to prepare a series of phenylpropenoyl- and O-phenylpropenyl- pinitols, and hesperidin derivatives. The corresponding non-conjugated derivatives of these compounds were also prepared via catalytical hydrogenation.
Bioassay against α-glucosidase showed that cinnamyl- and dihydrocinnamyl- pinitols have no inhibitory activity. However, they could enhance insulin to stimulate glucose uptake, especially compound IIC-4. Dihydro-1,2-seco-hesperidin (IVA-2) showed weak inhibition activity; nevertheless, etherification with cinnamyl bromide at 2-position of the glucosyl residue could increase activity (IVA-4, IC50 = 136.8 uM). Intravenous glucose tolerance test on normal rats indicated that compound IB-1 could reduce the blood glucose level significantly. This could be attributable to the function of pinitol and cinnamic acid, the hydrolytic products of IB-1. The bioactivity of O-cinnamyl- and O-dihydrocinnamyl- hesperidins remains to be disclosed. | en |
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| dc.description.tableofcontents | 誌謝...............................................................................................................................II
中文摘要........................................................................................................................1 英文摘要........................................................................................................................2 表目錄 (List of Tables)……………………………………………………………….9 流程圖目錄 (List of Schemes)…...…………………………………………………10 圖及附圖目錄 (List of Figures and Spectra Appendices)…………………………..11 詞彙 (Glossary)……………………………………………………………………...15 第一章 序論………………………………………………………………………..16 1.1 糖尿病簡介……………………………………………………………….16 1.1.1 糖尿病………………………………………………………………16 1.1.2 糖尿病的機制………………………………………………………16 1.2 糖尿病之治療藥物……………………………………………………….18 1.2.1 臨床上使用之甲型葡萄糖水解酶抑制劑及其發展………………21 1.2.2 近年來新發現之甲型葡萄糖水解酶抑制劑………………………23 1.3 研究目的………………………………………………………………….27 1.4 苯丙烯黃酮鼠李糖苷類化合物之活性研究…………………………….27 1.5 Pinitol之結構修飾研究…………………………………………………..29 1.6 Hesperidin之結構修飾研究……………………………………………...29 第二章 實驗結果與討論…………………………………………………………..31 2.1 Phenylpropenoylpinitols 與 phenylpropanoylpinitols 之製備………….31 2.1.1 Pinitol peracetonide (IA-1) 之製備………………………………..31 2.1.2 4-O-Cinnamoyl-pinitol (IIA-3) 與 4-O-dihydrocinnamoyl-pinitol (IIA-4) 之製備……………………………………………………..32 2.1.3 4-O-(2-Hydroxycinnamoyl)-pinitol (IIC-4) 之製備……………….35 2.1.4 4-O-(3-Hydroxycinnamoyl)-pinitol (IID-5) 與 4-O-(3-hydroxydihydrocinnamoyl)- pinitol (IID-6) 之製備………36 2.1.5 4-O-Caffeoyl-pinitol (IIE-4) 之製備………………………………37 2.1.6 Peracylated pinitol (IB-1) 之製備…………………………………38 2.1.7 4-O-Cinnamyl-, 4-O-dihydrocinnamyl-pinitol (IIIA-3, IIIA-5) 之製備…………………………………………………………………..39 2.1.8 2,4,5-Tri-O-cinnamyl-, 2,4,5-tri-O-dihydrocinnamyl-pinitol (IIIB-1, IIIB-2) 之製備……………………………………………………..41 2.1.9 Pinitol 保護基之合成研究………………………………………...42 2.2 Hesperidin analogues 之製備……………………………………………44 2.2.1 3’,5,9-Tribenzyl-1,2-seco-hesperidin (IVA-1) 之製備…………….45 2.2.2 Dihydro-1,2-seco-hesperidin (IVA-2) 之製備……………………..48 2.2.3 3’,5,9-Tri-benzyl-2-O-cinnamyl-1,2-seco-hesperidins (IVA-3a, 3b) 之製備……………………………………………………………..49 2.2.4 2-O-Dihydrocinnamyl-dihydro-1,2-seco-hesperidin(IVA-4)之製備.53 2.2.5 3’,5,9-Tri-benzyl-1,2-seco-hesperidin-2’’’,3’’’-acetonode (IVC-1) 之製備………………………………………………………………..55 2.2.6 Hepta-O-cinnamylhesperidin (IVD-1) 與 per-O-cinnamylhesperidin (IVE-1) 之製備………………………58 2.2.7 Silylated hesperidins (IVF-1) 之製備……………………………..59 2.3 藥物活性測試…………………………………………………………….60 2.3.1 甲型葡萄糖水解酶之活性試驗結果………………………………60 2.3.2 六碳糖輸送之活性試驗結果………………………………………62 2.3.3 動物體內活性試驗結果……………………………………………63 第三章 實驗方法…………………………………………………………………..65 3.1 儀器與材料……………………………………………………………….65 3.1.1 理化性質測定儀器…………………………………………………65 3.1.2 反應器………………………………………………………………65 3.1.3 成份分離之儀器及材料……………………………………………65 3.1.4 試劑、材料及溶劑…………………………………………………..66 3.2 Phenylpropenoylpinitols 與 phenylpropanoylpinitols 之製備…………67 3.2.1 Pinitol peracetonide (IA-1) 之製備………………………………..68 3.2.2 4-O-Cinnamoyl-pinitol (IIA-3) 與 4-O-dihydrocinnamoyl-pinitol (IIA-4) 之製備……………………………………………………..68 3.2.2.1 4-O-Cinnamoyl-pinitol peracetonide (IIA-2) 之製備………...68 3.2.2.2 4-O-Cinnamoyl-pinitol (IIA-3) 之製備……………………….69 3.2.2.3 4-O-Dihydrocinnamoyl-pinitol (IIA-4) 之製備………………70 3.2.2.4 Dihydrocinnamic acid (IIB-1) 之製備………………………...71 3.2.2.5 4-O-Dihydrocinnamoyl-pinitol peracetonide (IIB-2) 之製備...72 3.2.3 4-O-(2-Hydroxycinnamoyl)-pinitol (IIC-4) 之製備……………….72 3.2.3.1 2-Acetyloxycinnamic acid (IIC-2) 之製備……………………72 3.2.3.2 4-O-(2-Acetyloxycinnamoyl)-pinitol peracetonide (IIC-3) 之製備………………………………………………………………..73 3.2.3.3 4-O-(2-Hydroxycinnamoyl)-pinitol (IIC-4) 之製備…………..74 3.2.4 4-O-(3-Hydroxycinnamoyl)-pinitol (IID-5) 之製備……………….75 3.2.4.1 3-Acetyloxycinnamic acid (IID-2) 之製備……………………75 3.2.4.2 4-O-(3-Acetyloxycinnamoyl)-pinitol peracetonide (IID-3) 之製備………………………………………………………………..75 3.2.4.3 4-O-(3-Hydroxycinnamoyl)-pinitol peracetonide (IID-4) 之製備………………………………………………………………..76 3.2.4.4 4-O-(3-Hydroxycinnamoyl)-pinitol (IID-5) 之製備…………..77 3.2.4.5 4-O-(3-Hydroxydihydrocinnamoyl)-pinitol (IID-6) 之製備….78 3.2.5 4-O-Caffeoyl-pinitol (IIE-4) 之製備………………………………79 3.2.5.1 Diacetylcaffeic acid (IIE-2) 之製備…………………………..79 3.2.5.2 4-O-(Diacetylcaffeoyl)-pinitol peracetonide (IIE-3) 之製備…79 3.2.5.3 4-O-Caffeoyl-pinitol (IIE-4) 之製備………………………….80 3.2.5.4 Caffeic acid acetonide (IIE-1a) 之製備……………………....81 3.2.6 Acetylation of other cinnamic acid analogues……………………...82 3.2.7 Peracylated pinitol (IB-1) 之製備………………………………….83 3.3 4-O-Cinnamyl-, 4-O-dihydrocinnamyl- 與 2,4,5-tri-O-cinnamyl- , 2,4,5-tri-O-dihydrocinnamyl pinitol 之製備……………………………...83 3.3.1 4-O-Cinnamyl-pinitol peracetonide (IIIA-2) 之製備.......................83 3.3.2 4-O-Cinnamyl-pinitol (IIIA-3) 之製備……………………………84 3.3.3 4-O-Dihydrocinnamyl-pinitol peracetonide (IIIA-4) 之製備……..85 3.3.4 4-O-Dihydrocinnamyl-pinitol (IIIA-5) 之製備……………………86 3.3.5 2,4,5-Tri-O-cinnamyl-pinitol (IIIB-1) 之製備…………………….87 3.3.6 2,4,5-Tri-O-dihydrocinnamyl-pinitol (IIIB-2) 之製備…………….88 3.4 Pinitol 保護基之合成研究………………………………………………88 3.4.1 Tetra-tBDMS-pinitols (ID-1) 之製備………………………………88 3.4.2 2,5-Di-tBDMS-pinitol (IC-1) 之製備……………………………...89 3.4.3 2,5-Di-tBDMS-1,4,6-triacetyl pinitol (IC-2) 之製備………………90 3.5 Hesperidin analogues 之製備……………………………………………91 3.5.1 3’,5,9-Tribenzyl-1,2-seco-hesperidin (IVA-1) 之製備…………….91 3.5.1.1 Dihydro-1,2-seco-hesperidin (IVA-2) 之製備………………...92 3.5.1.2 3’,5,9-Tri-benzyl-2-O-cinnamyl-1,2-seco-hesperidins (IVA-3a, 3b) 之製備……………………………………………………93 3.5.1.3 2-O-Dihydrocinnamyl-dihydro-1,2-seco-hesperidin (IVA-4) 之 製備……………………………………………………………..94 3.5.2 Dibenzyl-1,2-seco-hesperidin (IVB-1) 之製備……………………94 3.5.3 3’,5,9-Tri-benzyl-1,2-seco-hesperidin-2’’’,3’’’-acetonode (IVC-1) 之 製備…………………………………………………………………95 3.5.4 Hepta-O-cinnamylhesperidin (IVD-1) 之製備…………………….96 3.5.5 Per-O-cinnamylhesperidin (IVE-1) 之製備……………………….96 3.5.6 Silylated hesperidins (IVF-1) 之製備……………………………...97 3.6 甲型葡萄糖水解酶之活性試驗 (α-Glucosidase assay)............................97 3.6.1 原理…………………………………………………………………97 3.6.2 試劑配製……………………………………………………………98 3.6.3 實驗步驟……………………………………………………………98 3.6.4 IC50 之計算.......................................................................................99 3.7 動物體內活性試驗 ……………………………………………………...99 3.7.1 口服劑型之配製……………………………………………………99 3.7.2 實驗方法 (intravenous glucose tolerance test, IVGTT)…………...100 3.8 六碳糖輸送之活性試驗 (hexose transport assay)……………………..100 3.8.1 目的………………………………………………………………..100 3.8.2 細胞培養與脂肪細胞之分化……………………………………..101 3.8.3 六碳糖輸送………………………………………………………..101 參考文獻……………………………………………………………………………103 附圖 (Spectra Appendices)…………………………………………………………110 表目錄 (List of Tables) Table 1. 胰島素製劑………………………………………………………………...18 Table 2. 口服抗高血糖藥物………………………………………………………...19 Table 3. 各種治療第二型糖尿病藥物對於病理生理之影響……………………...20 Table 4. 臨床使用之甲型葡萄糖水解酶抑制劑…………………………………...21 Table 5. 具甲型葡萄糖水解酶抑制活性之成分…………………………………...23 Table 6. 1H and 13C NMR data, COSY and HMBC correlations of hesperidin and IVA-1 (Pyridine-d5, Bruker AV-400)……………………………………….45 Table 7. 1H and 13C NMR data of compound IVA-2 (Bruker AV400)……………….48 Table 8. 1H and 13C NMR data of compound IVA-1, IVA-3a (Pyridine-d5, Bruker AV-400)…………………………………………………………………….50 Table 9. 1H and 13C NMR data of compound IVA-3a, IVA-3b (Bruker AV-400)…..52 Table 10. 1H data of compound IVA-2, IVA-3a, IVA-4 (Pyridine-d5, Bruker AV-400).........................................................................................................54 Table 11. 1H and 13C NMR data of compound IVA-1, IVC-1 (Pyridine-d5, Bruker AV-400)…………………………………………………………………….56 流程圖目錄 (List of Schemes) Scheme 1. Preparation of IA-1……………………………………………………….31 Scheme 2. Preparation of IIA-2~4. ………………………………………………….32 Scheme 3. Preparation of IIB-1 and IIB-2…………………………………………..34 Scheme 4. Preparation of IIC-2~4. ………………………………………………….35 Scheme 5. Preparation of IID-2~6…………………………………………………...36 Scheme 6. Preparation of IIE-1a and IIE-2~4............................................................37 Scheme 7. Preparation of IB-1……………………………………………………….39 Scheme 8. Preparation of IIIA-2~5…………………………………………………..40 Scheme 9. Preparation of IIIB-1 and IIIB-2………………………………………...42 Scheme 10. Preparation of ID-1, IC-1 and IC-2.........................................................43 Scheme 11. Preparation of IVA-1……………………………………………………45 Scheme 12. Preparation of IVA-2……………………………………………………48 Scheme 13. Preparation of IVA-3a and IVA-3b……………………………………..50 Scheme 14. Preparation of IVA-4……………………………………………………54 Scheme 15. Preparation of IVC-1……………………………………………………56 Scheme 16. Preparation of IVD-1 and IVE-1………………………………………..58 Scheme 17. Preparation of IVF-1……………………………………………………59 圖及附圖目錄 (List of Figures and Spectra Appendices) Figure 1. 脂肪組織內的慢性發炎會誘導骨骼肌的胰島素耐受性發生………….17 Figure 2. 臨床上使用之甲型葡萄糖水解酶抑制劑和其衍生物之結構………….22 Figure 3. 具甲型葡萄糖水解酶抑制活性成分之結構…………………………….25 Figure 4. 樟科楨楠屬所分離之苯丙醯黃酮鼠李糖苷類化合物結構…………….27 Figure 5. 松醇 (D-pinitol)、肉桂酸 (cinnamic acid) 和橙皮苷 (hesperidin) …….28 Figure 6. Structure of pinitol…………………………………………………………31 Figure 7. Catalytic function of 1-hydroxybenzotriazole (HOBt) in esterification…...33 Figure 8. Structure of hesperidin……………………………………………………..44 Figure 9. Hesperidin 開環之可能機制……………………………………………...47 Figure 10. Structure of IVA-2 and IVA-4……………………………………………60 Figure 11. α-Glucosidase assay of IVA-2 and IVA-4………………………………...61 Figure 12. Structure of IIA-3, IIC-4, IIE-4………………………………………….62 Figure 13. Hexose transport assay of IIA-3, IIC-4, IIE-4…………………………..62 Figure 14. In vivo assay of IB-1……………………………………………………...63 Figure 15. In vivo assay of cinnamic acid……………………………………………64 Figure 16. 96 孔微量測試盤樣品配置……………………………………………..99 Figure 17. 1H-NMR spectrum of I-1 (D2O, 400 MHz)……………………………..110 Figure 18. 13C-NMR spectrum of I-1 (D2O, 100 MHz)…………………………….111 Figure 19. 1H-NMR spectrum of IA-1 (CDCl3, 200 MHz)…………………………112 Figure 20. 13C-NMR spectrum of IA-1 (CDCl3, 50 MHz)………………………...113 Figure 21. 1H-NMR spectrum of IIA-2 (CDCl3, 200 MHz)………………………..114 Figure 22. 13C-NMR spectrum of IIA-2 (CDCl3, 50 MHz)……………………….115 Figure 23. 1H-NMR spectrum of IIA-3 (CD3OD, 200 MHz)………………………116 Figure 24. 13C-NMR spectrum of IIA-3 (CD3OD, 50 MHz)……………………….117 Figure 25. 1H-NMR spectrum of IIA-4 (CD3OD, 400 MHz)………………………118 Figure 26. 13C-NMR spectrum of IIA-4 (CD3OD, 100 MHz)……………………...119 Figure 27. 1H-NMR spectrum of IIB-1 (CDCl3, 200 MHz)………………………..120 Figure 28. 1H-NMR spectrum of IIB-1 (CDCl3, 200 MHz)………………………..121 Figure 29. 13C-NMR spectrum of IIB-1 (CDCl3, 50 MHz)………………………...122 Figure 30. 1H-NMR spectrum of IIC-2 (CDCl3, 200 MHz)……………………..…123 Figure 31. 1H-NMR spectrum of IIC-3 (CDCl3, 400 MHz)………………………..124 Figure 32. 13C-NMR spectrum of IIC-3 (CDCl3, 100 MHz)……………………….125 Figure 33. 1H-NMR spectrum of IIC-4 (CD3OD, 400 MHz)………………………126 Figure 34. 13C-NMR spectrum of IIC-4 (CD3OD, 100 MHz)……………………...127 Figure 35. 1H-NMR spectrum of IID-2 (CDCl3, 200 MHz)………………………..128 Figure 36. 1H-NMR spectrum of IID-3 (CDCl3, 400 MHz)………………………..129 Figure 37. 13C-NMR spectrum of IID-3 (CDCl3, 100 MHz)……………………….130 Figure 38. 1H-NMR spectrum of IID-4 (CD3OD, 400 MHz)………………………131 Figure 39. 1H-NMR spectrum of IID-5 (CD3OD, 200 MHz)………………………132 Figure 40. 13C-NMR spectrum of IID-5 (CD3OD, 50 MHz)……………………….133 Figure 41. 1H-NMR spectrum of IID-6 (CD3OD, 200 MHz)………………………134 Figure 42. 13C-NMR spectrum of IID-6 (CD3OD, 50 MHz)……………………….135 Figure 43. 1H-NMR spectrum of IIE-2 (CDCl3, 200 MHz)………………………..136 Figure 44. 1H-NMR spectrum of IIE-3 (CDCl3, 400 MHz)………………………..137 Figure 45. 13C-NMR spectrum of IIE-3 (CDCl3, 100 MHz)……………………….138 Figure 46. 1H-NMR spectrum of IIE-4 (CD3OD, 200 MHz)………………………139 Figure 47. 13C-NMR spectrum of IIE-4 (CD3OD, 50 MHz)……………………….140 Figure 48. 1H-NMR spectrum of IIE-1a (CDCl3, 200 MHz)………………………141 Figure 49. 13C-NMR spectrum of IIE-1a (CDCl3, 50 MHz)……………………….142 Figure 50. 1H-NMR spectrum of IIF-2 (CDCl3, 200 MHz)………………………..143 Figure 51. 1H-NMR spectrum of IIG-2 (CDCl3, 200 MHz)………………………..144 Figure 52. 1H-NMR spectrum of IB-1 (CDCl3, 400 MHz)…………………………145 Figure 53. 13C-NMR spectrum of IB-1 (CDCl3, 100 MHz)………………………...146 Figure 54. 1H-NMR spectrum of IIIA-2 (CDCl3, 200 MHz)………………………147 Figure 55. 13C-NMR spectrum of IIIA-2 (CDCl3, 50 MHz)……………………….148 Figure 56. 1H-NMR spectrum of IIIA-3 (CD3OD, 400 MHz)……………………..149 Figure 57. 13C-NMR spectrum of IIIA-3 (CD3OD, 100 MHz)…………………….150 Figure 58. 1H-NMR spectrum of IIIA-4 (CDCl3, 200 MHz)………………………151 Figure 59. 13C-NMR spectrum of IIIA-4 (CDCl3, 50 MHz)……………………….152 Figure 60. 1H-NMR spectrum of IIIA-5 (CD3OD, 400 MHz)……………………..153 Figure 61. 13C-NMR spectrum of IIIA-5 (CD3OD, 100 MHz)…………………….154 Figure 62. 1H-NMR spectrum of IIIB-1 (CDCl3, 200 MHz)………………………155 Figure 63. 13C-NMR spectrum of IIIB-1 (CDCl3, 50 MHz)……………………….156 Figure 64. 1H-NMR spectrum of IIIB-2 (CDCl3, 200 MHz)……………………….157 Figure 65. 13C-NMR spectrum of IIIB-2 (CDCl3, 50 MHz)……………………….158 Figure 66. 1H-NMR spectrum of ID-1 (CDCl3, 200 MHz) ………………………..159 Figure 67. 13C-NMR spectrum of ID-1 (CDCl3, 50 MHz) ………………………...160 Figure 68. 1H-NMR spectrum of IC-1 (CDCl3, 200 MHz) ………………………..161 Figure 69. 13C-NMR spectrum of IC-1 (CDCl3, 50 MHz) ………………………...162 Figure 70. 1H-NMR spectrum of IC-2 (CDCl3, 200 MHz) ………………………..163 Figure 71. 13C-NMR spectrum of IC-2 (CDCl3, 50 MHz) ………………………...164 Figure 72. 1H-NMR spectrum of IV-1 (Pyridine-d5, 400 MHz) …………………...165 Figure 73. 13C-NMR spectrum of IV-1 (Pyridine-d5, 100 MHz) …………………..166 Figure 74. 1H-NMR spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………….167 Figure 75. 13C-NMR spectrum of IVA-1 (Pyridine-d5, 100 MHz) ………………...168 Figure 76. COSY (1) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………...169 Figure 77. COSY (2) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………...170 Figure 78. COSY (3) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………...171 Figure 79. HMQC (1) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..172 Figure 80. HMQC (2) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..173 Figure 81. HMQC (3) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..174 Figure 82. HMBC (1) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..175 Figure 83. HMBC (2) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..176 Figure 84. HMBC (3) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..177 Figure 85. HMBC (4) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..178 Figure 86. HMBC (5) spectrum of IVA-1 (Pyridine-d5, 400 MHz) ………………..179 Figure 87. 1H-NMR spectrum of IVA-2 (Pyridine-d5, 400 MHz) ………………….180 Figure 88. 13C-NMR spectrum of IVA-2 (Pyridine-d5, 100 MHz) ………………...181 Figure 89. 1H-NMR spectrum of IVA-3a (Pyridine-d5, 400 MHz) ………………...182 Figure 90. 13C-NMR spectrum of IVA-3a (Pyridine-d5, 100 MHz) ……………….183 Figure 91. 1H-NMR spectrum of IVA-3b (Pyridine-d5, 400 MHz) ………………..184 Figure 92. 1H-NMR spectrum of IVA-4 (Pyridine-d5, 400 MHz) ………………….185 Figure 93. 1H-NMR spectrum of IVC-1 (Pyridine-d5, 400 MHz) …………………186 Figure 94. 13C-NMR spectrum of IVC-1 (Pyridine-d5, 100 MHz) ………………...187 | |
| dc.language.iso | zh-TW | |
| dc.subject | 抑制物 | zh_TW |
| dc.subject | 甲型葡萄糖水解酶 | zh_TW |
| dc.subject | 松醇 | zh_TW |
| dc.subject | 肉桂酸 | zh_TW |
| dc.subject | 肉桂基溴 | zh_TW |
| dc.subject | 苯丙醯黃酮鼠李糖苷 | zh_TW |
| dc.subject | 查爾酮 | zh_TW |
| dc.subject | 橙皮苷 | zh_TW |
| dc.subject | 類化合物 | zh_TW |
| dc.subject | pinitol | en |
| dc.subject | cinnamic acid | en |
| dc.subject | cinnamyl bromide | en |
| dc.subject | seco-hesperidin | en |
| dc.subject | natural flavonol O-acylated rhamnosides | en |
| dc.subject | hesperidin | en |
| dc.subject | α-glucosidase inhibitor | en |
| dc.title | 苯丙醯黃酮鼠李糖苷類化合物之製備作抑制甲型葡萄糖水解酶之研究 | zh_TW |
| dc.title | Preparation of acylated rhamnosyl flavonoid analogs as α-glucosidase inhibitors | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 96-2 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 陳春雄,李安榮,林雲蓮 | |
| dc.subject.keyword | 甲型葡萄糖水解酶,抑制物,苯丙醯黃酮鼠李糖苷,類化合物,松醇,橙皮苷,肉桂酸,肉桂基溴,查爾酮, | zh_TW |
| dc.subject.keyword | α-glucosidase inhibitor,natural flavonol O-acylated rhamnosides,pinitol,hesperidin,seco-hesperidin,cinnamyl bromide,cinnamic acid, | en |
| dc.relation.page | 187 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2008-08-01 | |
| 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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