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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 李水盛(Shoei-Sheng Lee) | |
dc.contributor.author | Anita Hsieh Hsu | en |
dc.contributor.author | 謝安安 | zh_TW |
dc.date.accessioned | 2021-07-11T15:11:43Z | - |
dc.date.available | 2022-08-28 | |
dc.date.copyright | 2019-08-28 | |
dc.date.issued | 2019 | |
dc.date.submitted | 2019-08-06 | |
dc.identifier.citation | References
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/78679 | - |
dc.description.abstract | 中文摘要
本論文分兩部分,第一部分為飛揚草地上部成分之研究,飛揚草為大戟科(Euphorbiaceae) 地錦草屬(Chamaesyce) 植物,是一種生長在台灣的藥用植物,除了具有抗菌,止瀉和利尿作用外,還抗焦慮,鎮痛,鎮靜,解熱和抗發炎等。此外,亞洲其他地區飛揚草之成分在過去已被研究,故本研究擬針對台灣飛揚草地上部之較高極性部分進行探討。 本植物地上部之乙醇萃取物,經極性分割得到乙酸乙酯可溶部分、正丁醇可溶部分和水可溶部分。正丁醇可溶部分經由凝膠管柱層析和逆相低壓管柱層析分離後,共得到八個化合物,包括三個黃酮醇糖苷:myricetin 3-O-α-L-rhamnoside (1)、quercetin 3-O-α-L-rhamnoside (2)、quercetin 3-O-β-D-glucuronide (4) ,三個苯丙烯酸類: chlorogenic acid (3) 、caffeic acid (5) 和 ferulic acid (8), 及 shikimic acid (6) 和n-docosanoic acid (7)。化合物的結構藉由分析核磁共振譜和電灑游離質譜而確認。其中化合物 (1、2及4) 被報導具抗發炎、抗氧化、抗瘧疾與止瀉等作用。 第二部分為野牡丹莖部成分之研究,野牡丹為野牡丹科(Melastomataceae) 野牡丹屬(Melastoma) 的植物,在台灣用於消除瘀滯,與毒素;外傷及細菌性痢疾等疾病。研究證實了野牡丹除對單胺氧化酶B有抑制作用外,還具有抗高血壓和抗菌作用。其葉子的化學成分已被研究,然而莖部之成分尚未被探討;故本研究擬針對野牡丹莖部之成分進行探討。 本植物莖部之乙醇萃取物,經極性分割得到二氯甲烷、乙酸乙酯、正丁醇和水可溶部分。正丁醇可溶部分經由凝膠管柱層析,逆相低壓管柱層析和矽膠柱層析分離後,共得到七個化合物,包括一個黃酮醇糖:quercetin 3-O-β-D-glucoside (9),一個黃酮類(2R, 3S)-catechin (10),和三個單寧類casuarinin (11),pendunculagin (12) 和castalagin (13) 及 shikimic acid (14) 和γ-aminobutyric acid (15)。化合物的結構藉由解析核磁共振譜和電灑游離質譜而確認。 本研究為第一個探討野牡丹莖部較高極性之成分,實驗結果證明melastoma屬植物富含黃酮類和單寧類化合物,其中化合物 (11、12和13) 被報導具有抗發炎、抗氧化、抗病毒和抗癌等活性。化合物14 更是被用於合成oseltamivir 的起始物,其化合物在正丁醇可溶部分含量較高(正丁醇層的7.47%),故以HPLC分析及建立其化合物在水層之含量(ca. 0.72%, w/w)。 | zh_TW |
dc.description.abstract | Abstract
This thesis contains two parts. Part I. Chemical constituents from the aerial parts of Euphorbia hirta L. Euphorbia hirta L. (Euphorbiaceae) is a medicinal herb that grows throughout Taiwan. This folk medicine has been used to treat anxiety, pain and inflammation diseases, besides its antibacterial, antidiarrheal and diuretic effects. Although chemical constituents of E. hirta from other areas have been reported, those distributed in Taiwan have not been explored yet. This study was dedicated to find out whether geographic factors will influence the content of its chemical constituents. The n-BuOH soluble fraction of the EtOH extract of Euphorbia hirta was repeatedly chromatographed on Sephadex LH-20 and Lobar Rp-18 columns, and semi-preparative HPLC. These efforts led to the isolation of eight compounds, including three flavonol glycosides, i.e., myricetin 3-O-α-L-rhamnoside (1), quercetin 3-O-α-L-rhamnoside (2), and quercetin 3-O-β-D-glucuronide (4), three phenylpropanoids, i.e., chlorogenic acid (3), caffeic acid (5) and ferulic acid (8), and two others, i.e., shikimic acid (6), and n-docosanoic acid (7). Their structures were elucidated on the basis of NMR spectroscopic analysis and ESI-MS data. Flavonol glycosides isolated in this study, compounds (1, 2 and 4), has been reported to possess anti-oxidant, anti-malarial, anti-diarrheal, and anti-inflammatory activities. Part.II Chemical constituents from the stem of Melastoma candidum D. Don Melastoma candidum D. Don (Melastomataceae) has been used as folk medicine to detoxify the serum, treat injuries, diarrhea, leucorrhoea, and dysentery. It has been demonstrated to possess antihypertensive, antibacterial, and anti-monoamine oxidase B activities. Chemical constituents of its leaves have been reported, but not those of its stem. Thus, this research focused on chemical investigation of the stem part, especially those of higher polarity. The n-BuOH soluble fraction of the EtOH extract of its stem was repeatedly chromatographed on Sephadex LH-20, silica gel and Lobar Rp-18 columns, and semi-preparative HPLC. These efforts led to the isolation of seven compounds, including a flavonol glycoside, i.e., quercetin 3-O-β-D-glucoside (9), a flavanol, i.e., (2R, 3S)-catechin (10), and three ellagitannin, i.e., casuarinin (11), pedunculagin (12), and castalagin (13), and two others, i.e., shikimic acid (14) and γ-aminobutyric acid (15). Their structures were elucidated on the basis of NMR spectroscopic analysis and ESI-MS data. Compounds 11, 12 and 13 was reported to possess anti-oxidant, anti-viral, anti-inflammatory, and anti-cancer effects. Moreover, compound 14 is used as starting material in the synthesis of oseltamivir, because of its high content in the BuOH soluble layer (7.47% of the BuOH soluble layer), the content of 14 in H2O soluble layer was also explored by HPLC analysis, (ca. 0.72%, w/w, H2O soluble layer). | en |
dc.description.provenance | Made available in DSpace on 2021-07-11T15:11:43Z (GMT). No. of bitstreams: 1 ntu-108-R06423029-1.pdf: 8243799 bytes, checksum: 67bfed8cf26a32c6ca4e32bf2871413c (MD5) Previous issue date: 2019 | en |
dc.description.tableofcontents | List of Contents
Verification letter from the Oral Examination Committee ……………………………….I Acknowledgments ………………………………………………………………………II Chinese abstract (中文摘要) ……………………………………………...…………...III Abstract …………………………………………………………………...……………IV List of Contents ………………………………………………………………………..VI List of Table ………………………………………………………...………………..X List of Figures ………………………………………………………...………………..XI List of Schemes ……………………………………………………….……………XIV Glossary ……………………………………………………………….………………XV Part 1: Chemical constituents from the aerial part of Euphorbia hirta L. Chapter 1 ˴ Preface ………………………………………………………………...…….1 1.1 Research aim …………...……………………………………………...……..1 1.2 Introduction ………………………………………………………...……….. 2 1.2.1 Euphorbia hirta L…………………………………………………………...2 1.2.2 Biological activities of chemical constituents of E. hirta ...……….………...3 1.2.3 Reported chemical constituents from E. hirta…………………..…………...4 Chapter 2 ˴ Result and Discussion ………………………………………....………... 9 2.1 Chemical constituents isolated from E. hirta in current study………………9 2.2 Structure elucidation ……………………………………………...………11 2.2.1 Myricetin 3-O-α-L-rhamnoside (1) …………………………….………11 2.2.2 Quercetin 3-O-α-L-rhamnoside (2) ………………………………….…13 2.2.3 Chlorogenic acid (3) ……..……………………………………..………15 2.2.4 Quercetin 3-O-β-D-glucuronide (4) …………………….………………17 2.2.5 Caffeic acid (5) …………………………………………………………19 2.2.6 Shikimic acid (6) ……………………………………………………….21 2.2.7 n-Docosanoic acid (7) ……………………………………………….….23 2.2.8 Ferulic acid (8) …………………………………………………………25 2.3 Conclusion …………………………………………………………..……27 Chapter 3 ˴ Experimental section …………………………………………………...28 3.1 Materials and methods……………………………………………………28 3.1.1 Instruments………………………………………………………….……28 3.1.2 Chromatography…………………………………………………………28 3.1.3 Chemicals and reagents …………………………………………..…...29 3.2 Plant material ……………………………………………………………...30 3.3 Extraction and isolation ……………………………..…………………….30 3.3.1 Isolation of compound 3 …….……………..…………………………….32 3.3.2 Isolation of compound 1 ……….…………………………………………32 3.3.3 Isolation of compound 2 ………………………...………………………..32 3.3.4 Isolation of compound 4 ……………………...………..…………………32 3.3.5 Isolation of compounds 5, 6 and 8 …………...…..………………………..32 3.3.6 Isolation of compound 7 ……….…………………………………………33 3.4 Physical Data ………………………………………………………………35 Part 2. Chemical constituents from the stem of Melastoma candidum D. Don Chapter 1 ˴ Preface …………………………………………………………………….38 1.1 Research aim ……….…………………….……………………………….38 1.2 Introduction …………...………………….……………………………….39 1.2.1 Melastoma candidum D. Don………………………………..…………..39 1.2.2 Biological activities of chemical constituents of M. candidum ......……..40 1.2.3 Reported chemical constituents of the genus Melastoma………………..41 Chapter 2 ˴ Result and Discussion …………………………………………………...48 2.1 Chemical constituents isolated from M. candidum ….……..……………48 2.2 Structure elucidation ………………………….…………………..………50 2.2.1 Quercetin 3-O-β-D-glucoside (9) ......………………………...……...…50 2.2.2 (2R, 3S)-Catechin (10) ………………….………………………..……52 2.2.3 Casuarinin (11) …………………………………………………………54 2.2.4 Pendunculagin (12) ……………………………………………………57 2.2.5 Castalagin (13) ……...……..……………………………………………59 2.2.6 Shikimic acid (14).….…………..…………………………………….…61 2.2.7 γ-Aminobutyric acid (15) ………...……………………………..………63 2.3 Quantification of shikimic acid (14) in the H2O soluble layer by HPLC.....65 2.4 Conclusion.………………………………………………….…………..…66 Chapter 3 ˴ Experimental section ……………………………………………………...67 3.1 Materials and methods……………………………………………………67 3.1.1 Instruments…………………………………………………………..…67 3.1.2 Chromatography……………………...…………………………………67 3.1.3 Chemicals and reagents……………………………………………....….68 3.2 Plant material ……………………………………………………………..69 3.3 Extraction and isolation ……………………………………………………69 3.3.1 Isolation of compound 14 …………………….……………....………….69 3.3.2 Isolation of compounds 9 and 10 ………..….……………………………71 3.3.3 Isolation of compounds 11, 12 and 13 ………………………..…………71 3.3.4 Isolation of compound 15 …………..……………………………..……..71 3.3.5 Quantification of shikimic acid (14) in the H2O soluble layer by HPLC.....72 3.4 Physical Data ……………….……………………………………………74 References …………………………………………………………………………….76 Appendix ……………………………………………………………...……………..…86 List of Tables Table 1. Reported chemical constituents of E. hirta L. (I).……….………………………4 Table 2. Reported chemical constituents of E. hirta L. (II) ………………………………5 Table 3. 1H (400 MHz) and13C-NMR (50 MHz) data of 1 (CD3OD) ……..………….…12 Table 4. 1H (400 MHz) and 13C-NMR (50 MHz) data of 2 (CD3OD) …………………...14 Table 5. 1H (400 MHz) and 13C-NMR (50 MHz) data of 3 (CD3OD) …………………...16 Table 6. 1H (400 MHz) and 13C-NMR (50 MHz) data of 4 (CD3OD) …………………...18 Table 7. 1H (600 MHz) and 13C-NMR (150 MHz) data of 5 (CD3OD) ………….....……20 Table 8. 1H (400 MHz) and 13C-NMR (150 MHz) data of 6 (CD3OD) ………….....……22 Table 9. 1H (200 MHz) and 13C-NMR (150 MHz) data of 7 (CDCl3) ……….…......……24 Table 10. 1H (200 MHz) and 13C-NMR (150 MHz) data of 8 (CD3OD) ………….....…26 Table 11. Reported chemical constituents of the Melastoma plants (I)…………...……41 Table 12. Reported chemical constituents of the Melastoma plants (II) ……….....……42 Table 13. Reported chemical constituents of the Melastoma plants (III) ………….……43 Table 14. 1H (200 MHz) and 13C-NMR (150 MHz) data of 9 (CD3OD) …….…….……51 Table 15. 1H (400 MHz) and 13C-NMR (150 MHz) data of 10 (CD3OD) …………....…53 Table 16. 1H-NMR (600 MHz) data of compound 11 (CD3OD).…….....................……55 Table 17. 13C-NMR (150 MHz) data of compound 11 (CD3OD) …...………………….56 Table 18. 1H-NMR (600 MHz) data of compound 12 (CD3OD) ……...……………..…58 Table 19. 1H-NMR (600 MHz) data of compound 13 ………………………....…..……60 Table 20. 1H (200 MHz) and 13C-NMR (150 MHz) data of 14 (CD3OD) ………...……62 Table 21. 1H-NMR (200 MHz) data of 15 (CD3OD) ……………………………...……64 Table 22. Parameters for the regression equations of the HPLC results for (14)…..……65 List of Figures Figure 1. Euphorbia hirta L. ……………………………………………………………..2 Figure 2. Structures of E1-E9 …………………………………………………………..6 Figure 3. Structures of E10-E19 …………………………………………………..……..7 Figure 4. Structures of E20-E25 ……………………………………………..…………..8 Figure 5. Compounds isolated from the aerial part of Euphorbia hirta. …..…………..10 Figure 6. Melastoma candidum D. Don ……………………………………………….39 Figure 7. Structures of M1-M14 ……………………………………………………….44 Figure 8. Structures of M15-M22 ……………………………………..……………….45 Figure 9. Structures of M23-M29 …………………………………………………….46 Figure 10. Structures of M30-M40 ………………………………………….………….47 Fig 11. Structures of the compounds isolated from M. candidum stem...…………..….49 Figure 12. Key HMBC of 11. …………………………………………………………55 Figure 13. Linear regression lines of the HPLC results………………………………..65 Figure 14. HPLC chromatogram of shikimic acid (standard)………………………….72 Figure 15. ESI-MS spectra of 1…...….……..……………………...………………87 Figure 16. 1H-NMR spectrum of 1 (CD3OD, 400 MHz) ……………..……...…..……88 Figure 17. 13C-NMR spectrum of 1 (CD3OD, 50 MHz) …………..…..……..…..……89 Figure 18. ESI-MS spectrum of 2………………..……………………....……....…….90 Figure 19. 1H-NMR spectrum of 2 (CD3OD, 400 MHz) ………….....…..….....…...…91 Figure 20. 13C-NMR spectrum of 2 (CD3OD, 50 MHz) …………..........…....………92 Figure 21. ESI-MS & MS/MS spectra of 3….…….…………..…………....…....…….93 Figure 22. 1H-NMR spectrum of 3 (CD3OD, 400 MHz) …………………...…………94 Figure 23. 13C-NMR spectrum of 3 (CD3OD, 50 MHz) ………………..…....…………95 Figure 24. ESI-MS & MS/MS spectra of 4…………….…………..…….….………….96 Figure 25. 1H-NMR spectrum of 4 (CD3OD, 400 MHz) ………………..…..…...….…..97 Figure 26. 13C-NMR spectrum of 4 (CD3OD, 50 MHz) …………………..……..………98 Figure 27. ESI-MS spectra of 5………………..…………………….....…….……….....99 Figure 28. 1H-NMR spectrum of 5 (CD3OD, 600 MHz) …………….....……..…..……100 Figure 29. 13C-NMR spectrum of 5 (CD3OD, 150 MHz) …………...…........……..……101 Figure 30. ESI-MS spectra of 6………………..…………………......…….…………102 Figure 31. 1H-NMR spectrum of 6 (CD3OD, 400 MHz) ………………..……..….……103 Figure 32. 13C-NMR spectrum of 6 (CD3OD, 150 MHz) ……………….....…..…..……104 Figure 33. ESI-MS spectrum of 7………………….……………………....….………...105 Figure 34. 1H-NMR spectrum of 7 (CDCl3 & D2O, 200 MHz) ……………..…..………106 Figure 35. 13C-NMR spectrum of 7 (CDCl3, 150 MHz) ……………..……..…..……107 Figure 36. ESI-MS spectra of 8………………..……...……….....…….……………...108 Figure 37. 1H-NMR spectrum of 8 (CD3OD, 200 MHz) ……….……..……...…..……109 Figure 38. 13C-NMR spectrum of 8 (CD3OD, 150 MHz) ……………..…..……..……110 Figure 39. ESI-MS spectra of 9………………….…………………….……………...111 Figure 40. 1H-NMR of 9 (CD3OD, 200 MHz) ………………..…..…………………...112 Figure 41. 13C-NMR of 9 (CD3OD, 150 MHz) ………………....……………………..113 Figure 42. ESI-MS spectra of 10……………..……………...……….…………...…..114 Figure 43. 1H-NMR of 10 (CD3OD, 400 MHz) …………………..…………………...115 Figure 44. 13C-NMR of 10 (CD3OD, 150 MHz) ………………..…...………………...116 Figure 45. ESI-MS spectra of 11.……………...……...………….…….……………..117 Figure 46. 1H-NMR of 11 (CD3OD, 600 MHz) ………………..…..……..…………...118 Figure 47. 13C-NMR of 11 (CD3OD, 150 MHz) ………………..…..…….…………...119 Figure 48. COSY spectrum of 11 (CD3OD, 600 MHz) …………….……..…………...120 Figure 49. HSQC spectrum of 11 (CD3OD, 600 MHz) …………………...…………...121 Figure 50. HMBC spectrum of 11 (CD3OD, 600 MHz) ………………..…....………...122 Figure 51. ESI-MS spectra of 12.……………….…………………….….…………...123 Figure 52. 1H-NMR of 12 (CD3OD, 600 MHz) ………………..…………...................124 Figure 53. 1H-NMR of 12 with solvent suppression (CD3OD, 600 MHz) …………...125 Figure 54. ESI-MS spectra of 13..……………….…………………….……………...126 Figure 55. 1H-NMR of 13 (CD3OD, 600 MHz) …………….......................................127 Figure 56. 1H-NMR of 13 (D2O, 600 MHz) ……………...........................................128 Figure 57. ESI-MS spectra of 14..……………….…………………….……………...129 Figure 58. 1H-NMR of 14 (CD3OD, 200 MHz) …………….......................................130 Figure 59. 13C-NMR of 14 (CD3OD, 150 MHz) ……………......................................131 Figure 60. ESI-MS spectrum of 15..…………..……………………….……………132 Figure 61. 1H-NMR of 15 (CD3OD, 200 MHz) …………….......................................133 Figure 62. COSY spectrum of 15 (CD3OD, 600 MHz) ……………............................134 List of Schemes Scheme 1. Extraction and fractionation of the aerial parts of E. hirta.....………………..31 Scheme 2. Isolation of compounds 1-8 from n-BuOH soluble fraction of E. hirta …...34 Scheme 3. Extraction and fractionation of the stems of M. candidum …………………70 Scheme 4. Isolation of compounds 9-15 from n-BuOH soluble fraction of M. candidu…73 | |
dc.language.iso | en | |
dc.title | 飛揚草地上部暨野牡丹莖部之成分研究 | zh_TW |
dc.title | Chemical constituents from the aerial part of Euphorbia hirta L. and the stem of Melastoma candidum D. Don | en |
dc.type | Thesis | |
dc.date.schoolyear | 107-2 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 李安榮(An-Rong Lee),張溫良(Wen-Liang Chang) | |
dc.subject.keyword | 飛揚草,野牡丹, | zh_TW |
dc.subject.keyword | Euphorbia hirta,Euphorbiaceae,Melastoma candidum,Melastomataceae,flavonoids,ellagitannins, | en |
dc.relation.page | 134 | |
dc.identifier.doi | 10.6342/NTU201902576 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2019-08-06 | |
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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