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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 沈雅敬(Ya-Ching Shen) | |
dc.contributor.author | Priyanka Jagannath Patil | en |
dc.contributor.author | 帕雅佳 | zh_TW |
dc.date.accessioned | 2021-06-16T17:29:25Z | - |
dc.date.available | 2012-09-19 | |
dc.date.copyright | 2012-09-19 | |
dc.date.issued | 2012 | |
dc.date.submitted | 2012-08-16 | |
dc.identifier.citation | References:
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Novel type secoiridoid glucosides, hydrangenoside B, C, and D from Hydrangea macrophylla. Chem. Pharm. Bull. 1981, 29, 3421-3424. 50. Inouye, H. Uesato, S.; Hashimoto, T.; Takeda, Y. New secoiridoid glucosides, hydrangenoside E, F, and G from Hydrangea scandens. Chem. Pharm. Bull. 1981, 30, 4222-4225. 51. Ohmoto, T.; Yamaguchi, K. Constituents of pollen.XV. Constituents of Biota orientalis (L.) ENDL. Chem. Pharm. Bull. 1988, 36, 807-809. 52. Markham, K. R.; Ternai, B.; Stanley, R.; Geiger, H.; Mabry, T. J. Carbon -13 NMR studies of flavonoids-III. Naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahydron 1978, 34, 1389-1397. 53. Yoshikawa, M.; Murakami, T.; Ueda, T.; Shimoda, H.; Yamahara, Y.; Matsuda, H. Heterocycles 1999, 50, 411-418. | |
dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/64086 | - |
dc.description.abstract | This research consists of isolation and structural elucidation of chemical constituents from Hydrangea angustipetala Hayata. Four known secoiridoid glycosides called hydrangenosides C, D, E, and F (1, 2, 3, 4); 5-O-p-coumaroylquinic acid methyl ester (5) and one kaempferol diglycoside called nicotiflorin (6) were isolated from the ethanol extract of leaves and twigs of Hydrangea angustipetala Hayata by using extensive column chromatography.
Based on the spectroscopic methods such as 1H-NMR and 13C-NMR, including 2D NMR (COSY, HMQC, HMBC and NOESY) experiments, and physical methods such as optical rotation, IR, UV, HRESIMS, the structures of the compounds 1-6 were identified. All the isolated secoiridoid glycosides sent for bioactivity viz. cytotoxicity, anti-inflammatory, antiviral activity. They did not show any significant activity. | en |
dc.description.provenance | Made available in DSpace on 2021-06-16T17:29:25Z (GMT). No. of bitstreams: 1 ntu-101-R98423028-1.pdf: 3038932 bytes, checksum: 87a9bdbcf0414e1957ab392f9030914a (MD5) Previous issue date: 2012 | en |
dc.description.tableofcontents | Table of content
Master thesis certification by Oral Defense Committee....i Abstract................................................ii List of compounds isolated from Hydrangea angustipetala.iii Acknowledgement.........................................iv Table of content.........................................v Chapter 1. INTRODUCTION..................................1 1.1 Objective of the research............................1 1.2 Introduction to genus Hydrangea......................3 1.3 Previous chemical investigation on genus Hydrangea...4 1.4 Introduction to Hydrangea angustipetala Hayata.......24 1.5 Previous chemical investigation of Hydrangea angustipetala Hayata.....................................26 Chapter 2. EXPERIMENTAL SECTION..........................27 2.1 Apparatus and materials..............................27 2.1.1 Apparatus..........................................27 2.1.2 Solvents and reagents..............................28 2.2 Experimental procedure...............................30 2.2.1. Extraction of the leaves and twigs of Hydrangea angustipetala............................................30 2.2.2 Fractionation of n-butanol soluble fraction........30 2.2.3 Isolation of pure compounds........................30 Chapter 3. RESULTS AND DISCUSSION........................34 3.1 Structural elucidation of hydrangenoside C (1).......34 3.2 Structural elucidation of hydrangenoside D (2).......45 3.3 Structural elucidation of hydrangenoside E (3).......56 3.4 Structural elucidation of hydrangenoside F (4).......67 3.5 Structural elucidation of 5-O-p-coumaroylquinic acid methyl etser (5).........................................78 3.6 Structural elucidation of nicotiflorin (6)...........88 3.7 Conclusion...........................................98 REFERENCES...............................................99 List of Figures Figure 1. Hydrangea angustipetala Hayata................25 Figure 2. The key HMBC and COSY correlations of hydrangenoside C (1).....................................35 Figure 3. The key NOESY correlations of hydrangenoside C (1)......................................................36 Figure 4. 1H-NMR spectrum of hydrangenoside C (1) (400MHz).................................................38 Figure 5. 13C-NMR spectrum of hydrangenoside C (1) (400MHz).................................................39 Figure 6. 13C-NMR, DEPT-135, 90 spectra of hydrangenoside C (1) (400MHz).............................................40 Figure 7. COSY spectrum of hydrangenoside C (1) (400MHz).41 Figure 8. HMQC spectrum of hydrangenoside C (1) (400MHz).41 Figure 9. HMBC spectrum of hydrangenoside C (1) (400MHz).42 Figure 10. NOESY spectrum of hydrangenoside C (1)(400MHz)42 Figure 11. HRESIMS of hydrangenoside C (1)...............43 Figure 12. IR spectrum of hydrangenoside C (1)...........43 Figure 13. UV spectrum of hydrangenoside C (1)...........44 Figure 14. The key HMBC and COSY correlations of hydrangenoside D (2).....................................46 Figure 15. The key NOESY correlations of hydrangenoside D (2)......................................................47 Figure 16. 1H NMR spectrum of hydrangenoside D (2) (400MHz).................................................49 Figure 17. 13C-NMR spectrum of hydrangenoside D (2) (400MHz).................................................50 Figure 18. 13C-NMR, DEPT-135, 90 spectra of hydrangenoside D (2) (400MHz)...........................................51 Figure 19. COSY spectrum of hydrangenoside D (2) (400MHz)52 Figure 20. HMQC spectrum of hydrangenoside D (2) (400MHz)52 Figure 21. HMBC spectrum of hydrangenoside D (2) (400MHz)53 Figure 22. NOESY spectrum of hydrangenoside D (2)(400MHz)53 Figure 23. HRESIMS of hydrangenoside D (2)...............54 Figure 24. IR spectrum of hydrangenoside D (2)...........54 Figure 25. UV spectrum of hydrangenoside D (2)...........55 Figure 26. The key HMBC and COSY correlations of hydrangenoside E (3).....................................57 Figure 27. The key NOESY correlations of hydrangenoside E (3)......................................................58 Figure 28. 1H-NMR spectrum of hydrangenoside E (3) (400MHz).................................................60 Figure 29. 13C-NMR spectrum of hydrangenoside E (3) (400MHz).................................................61 Figure 30. 13C-NMR, DEPT-135, 90 spectra of hydrangenoside E (3) (400MHz)...........................................62 Figure 31. COSY spectrum of hydrangenoside E (3) (400MHz)63 Figure 32. HMQC spectrum of hydrangenoside E (3) (400MHz)63 Figure 33. HMBC spectrum of hydrangenoside E (3) (400MHz)64 Figure 34. NOESY spectrum of hydrangenoside E (3)(400MHz)64 Figure 35. ESIMS of hydrangenoside E (3).................65 Figure 36. IR spectrum of hydrangenoside E (3)...........65 Figure 37. UV spectrum of hydrangenoside E (3)...........66 Figure 38. The key HMBC and COSY correlations of hydrangenoside F (4).....................................68 Figure 39. The key NOESY correlations of hydrangenoside F (4)......................................................69 Figure 40. 1H-NMR spectrum of hydrangenoside F (4) (400MHz).................................................71 Figure 41. 13C-NMR spectrum of hydrangenoside F (4) (400MHz).................................................72 Figure 42. 13C-NMR, DEPT-135, 90 spectra of hydrangenoside F (4) (400MHz)...........................................73 Figure 43. COSY spectrum of hydrangenoside F (4) (400MHz)74 Figure 44. HMQC spectrum of hydrangenoside F (4) (400MHz)74 Figure 45. HMBC spectrum of hydrangenoside F (4) (400MHz)75 Figure 46. NOESY spectrum of hydrangenoside F (4)(400MHz)75 Figure 47. ESIMS spectrum of hydrangenoside F (4)........76 Figure 48. IR spectrum of hydrangenoside F (4)...........76 Figure 49. UV spectrum of hydrangenoside F (4)...........77 Figure 50. The key HMBC and COSY correlations of 5-O-p-coumaroylquinic acid methyl ester (5)....................79 Figure 51. 1H-NMR spectrum of 5-O-p-coumaroylquinic acid methyl ester (5) (400MHz)................................81 Figure 52. 13C-NMR spectrum of 5-O-p-coumaroylquinic acid methyl ester (5) (400MHz)................................82 Figure 53. 13C-NMR, DEPT-135, 90 spectra of 5-O-p-coumaroylquinic acid methyl ester (5) (400MHz)...........83 Figure 54. COSY spectrum of 5-O-p-coumaroylquinic acid methyl ester (5) (400MHz)................................84 Figure 55. HMQC spectrum of 5-O-p-coumaroylquinic acid methyl ester (5) (400MHz)................................84 Figure 56. HMBC spectrum of 5-O-p-coumaroylquinic acid methyl ester (5) (400MHz)................................85 Figure 57. NOESY spectrum of 5-O-p-coumaroylquinic acid methyl ester (5) (400MHz)................................85 Figure 58. ESIMS of 5-O-p-coumaroylquinic acid methyl ester (5)......................................................86 Figure 59. IR spectrum of 5-O-p-coumaroylquinic acid methyl ester (5)................................................86 Figure 60. UV spectrum of 5-O-p-coumaroylquinic acid methyl ester (5)................................................87 Figure 61. The key HMBC and COSY correlations of nicotiflorin (6).........................................89 Figure 62. 1H-NMR spectrum of nicotiflorin (6) (400MHz)..91 Figure 63. 13C-NMR spectrum of nicotiflorin (6) (400MHz).92 Figure 64. 13C-NMR, DEPT-135, 90 spectra of nicotiflorin (6) (400MHz).............................................93 Figure 65. COSY spectrum of nicotiflorin (6) (400MHz)....94 Figure 66. HMQC spectrum of nicotiflorin (6) (400MHz)....94 Figure 67. HMBC spectrum of nicotiflorin (6) (400MHz)....95 Figure 68. NOESY spectrum of nicotiflorin (6) (400MHz)...95 Figure 69. ESIMS of nicotiflorin (6).....................96 Figure 70. IR spectrum of nicotiflorin (6)...............96 Figure 71. UV spectrum of nicotiflorin (6)...............97 List of Tables Table 1. Literature reported bio-activities of the plant species belonging to genus Hydrangea......................4 Table 2. Chemical constituents of the plant species belonging to genus Hydrangea..............................6 Table 3. 1H and 13C-NMR data of hydrangenoside C (1) (in pyridine d5)..............................................37 Table 4. 1H and 13C-NMR data of hydrangenoside D (2) (in pyridine d5)..............................................48 Table 5. 1H and 13C-NMR data of hydrangenoside E (3) (in pyridine d5)..............................................59 Table 6. 1H and 13C-NMR data of hydrangenoside F (4) (in pyridine d5)..............................................70 Table 7. 1H and 13C-NMR data of 5-O-p-coumaroylquinic acid methyl ester (5) (in methanol d4).........................80 Table 8. 1H and 13C-NMR data of nicotiflorin (6) (measured in methanol d4)...........................................90 List of Schemes Scheme 1. Fractionation of Hydrangea angustipetala........32 Scheme 2. Isolation of compounds 1-6 from n-butanol layer of H. angustipetala.......................................33 | |
dc.language.iso | en | |
dc.title | 狹瓣華八仙枝葉之成分研究 | zh_TW |
dc.title | Studies on the Constituents from Leaves and Twigs of Hydrangea angustipetala Hayata | en |
dc.type | Thesis | |
dc.date.schoolyear | 100-2 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 周宏農(Hung-Non Chou),謝珮文(Pei-Wen Hsieh) | |
dc.subject.keyword | 狹瓣華八仙,裂環烯醚萜,苷,山柰酚苷, | zh_TW |
dc.subject.keyword | Hydrangea angustipetala Hayata,secoiridoid glycosides,kaempferol diglycoside, | en |
dc.relation.page | 104 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2012-08-16 | |
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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