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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 李水盛 | |
dc.contributor.author | Meng-Yao Ou | en |
dc.contributor.author | 歐孟堯 | zh_TW |
dc.date.accessioned | 2021-06-16T08:18:02Z | - |
dc.date.available | 2017-02-25 | |
dc.date.copyright | 2014-02-25 | |
dc.date.issued | 2014 | |
dc.date.submitted | 2014-02-10 | |
dc.identifier.citation | 1. Liao, J. C., Flora of Taiwan, second edition. Editorial Committee of the Flora of Taiwan: Taipei, 1996; Vol. 2, p 104.
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C., Triterpenoid Ketones from Lingnania chungii MOCLURE : Arborinone, Friedelin and Glutinone. Chemical & Pharmaceutical Bulletin 1992, 40 (3), 789-791. 26. Garg, V. K.; Nes, W. R., Occurrence of Δ5-sterols in plants producing predominantly Δ7-sterols: Studies on the sterol compositions of six cucurbitaceae seeds. Phytochemistry 1986, 25 (11), 2591-2597. 27. Chaurasia, N.; Wichtl, M., Sterols and Steryl Glycosides from Urtica dioica. Journal of Natural Products 1987, 50 (5), 881-885. 28. 涂, 秀玲. 臺灣赤楊化學成分之硏究(II):莖部部分 台灣大學碩士論文:Studies on the chemical constituents from Alnus formosana (II):stem part. 2002. 29. (a) Betancor, C.; Freire, R.; Gonzalez, A. G.; Salazar, J. A.; Pascard, C.; Prange, T., Three triterpenes and other terpenoids from Catha cassinoides. Phytochemistry 1980, 19 (9), 1989-1993; (b) Maldonado, E.; Bello, M.; Villaseñor, J. L.; Ortega, A., Acyclic diterpenes from perymenium HINTONII. Phytochemistry 1998, 49 (4), 1115-1118. 30. Moiteiro, C.; Marcelo Curto, M. J.; Mohamed, N.; Bailen, M.; Martinez-Diaz, R.; Gonzalez-Coloma, A., Biovalorization of friedelane triterpenes derived from cork processing industry byproducts. Journal of Agricultural and Food Chemistry 2006, 54 (10), 3566-3571. 31. Ramos, S. S.; Almeida, P.; Santos, L.; Motherwell, W. B.; Sheppard, T. D.; Costa, M. d. C., Functionalisation of terpenoids at C-4 via organopalladium dimers: cyclopropane formation during oxidation of homoallylic σ-organopalladium intermediates with lead tetraacetate. Tetrahedron 2007, 63 (51), 12608-12615. 32. Drefahl, G.; Huneck, S., Über die epimeren 3-Amino-friedelane. Chemische Berichte 1960, 93 (9), 1961-1967. 33. Gebauer-Henke, E.; Leitner, W.; Prokofieva, A.; Vogt, H.; Müller, T. E., Controlling selectivity in the reaction network of aldoxime hydrogenation to primary amines. Catalysis Science & Technology 2012, 2 (12), 2539. 34. Hutchins, R. O.; Lamson, D. 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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/58513 | - |
dc.description.abstract | 天然物於藥物發展中扮演相當重要的角色,研究報導三萜類化合物具有許多生物活性,其中friedelin於過去研究中發現其含有抗發炎、抗氧化、抗微生物及降血糖等活性。近年研究中更發現許多三萜類化合物,經化學修飾成含氮衍生物,不僅增加其水溶性,更具有多種細胞抗癌活性。因此本研究擬藉分離之friedelin,以之為起始物製備一系列含氮衍生物,進一步供生物活性之研究。
於過去研究發現,殼斗科植物含有許多三萜類化合物成分,其中殼斗科柯屬植物-大葉石櫟(Pasania kawakamii (Hayata) Schottky)為一台灣特有種植物。本研究自大葉石櫟葉部之乙醇萃取物,經極性分割得正己烷、乙氰、正丁醇及水可溶部分,其中正己烷可溶部分經初步分離得到friedelin (2)、squalene (1)、β-sitosterol (3)及epifriedelanol (4)。以2為起始物,形成酮肟化合物,經鉑催化還原反應及還原性胺化作用共得14個含氮及含氮苄基衍生物,供未來生物活性之研究。 阿朴芬型生物鹼-海罌粟鹼(glaucine)具有多種生物活性,本實驗室亦有許多其化學結構修飾之研究。文獻報導此類化合物於氮上作取代反應時,易行Hofmann elimination而得到開環之產物。以去氫化反應得6a,7-didehydroglaucine,避免開環反應之產生。本研究利用6a,7-didehydroglaucine與酸酐進行反應,以吡啶作為溶劑及催化劑,可得到氮上去甲基之醯胺化產物,透過SN2'之作用機轉,進而產生去甲基醯胺化反應。然而產率並不理想,未來需進一步提升其產率。 | zh_TW |
dc.description.abstract | Natural products play an important role in drug development, and it has reported triterpenoids have many bioactivities. Friedelin, a triterpene, has been demonstrated possess anti-inflammatory, antioxidant, antimicrobial, and hypoglycemic activities. Recent studies indicate some amino-triterpenes, prepared from chemical modification, not only increase water solubility but also enhance cytotoxicity. Therefore, this study was aimed to use friedelin as the starting material to prepare a series of aminofriedelans for further biological evaluation.
Past chemical investigations revealed that Fagaceaus plants contain triterpenoids such as friedelin (2). In this study, friedelin was isolated from Pasania kawakamii (Hayata) Schottky. The ethanol extract of its leaves was divided into the n-hexane, acetonitrile, n-butanol, and water soluble fractions via liquid-liquid partition. Friedelin (2), along with squalene (1), β-sitosterol (3) and epifriedelanol (4) was isolated from the n-hexane soluble fraction. Starting from 2, 14 aminofriedelans were prepared via three step reaction, i.e. reaction with hydroxylamine to form oximinofriedelan, catalytic hydrogenation to give 3β-aminofriedelan, and reductive amination. Glaucine is an aporphine alkaloid with a variety of biological activity. Some chemical modifications have been undertaken in our lab. Of these, N-demethylation by general methods will accompany with Hofmann elimination. 6a,7-Didehydroglaucine (20) might avoid the ring-opening reaction during N-demethylation. Thus this study, 6a,7-didehydroglaucine was used as key intermediate. Reaction of 6a,7-didehydroglaucine (20) with anhydrides in pyridine yields the corresponding N-acyl products through SN2' mechanism. The yields, however, are poor. Optimization of reaction conditions is required. | en |
dc.description.provenance | Made available in DSpace on 2021-06-16T08:18:02Z (GMT). No. of bitstreams: 1 ntu-103-R00423020-1.pdf: 9729565 bytes, checksum: 9b454e4ff06aa1de4fc9724027fd65fe (MD5) Previous issue date: 2014 | en |
dc.description.tableofcontents | 口試委員審定書 i
誌謝 ii 中文摘要 iii Abstract iv 目錄 vi 表目錄 (List of Tables) ix 流程目錄 (List of Schemes) x 圖及光譜圖目錄 (List of Figures and Spectra Appendices) xi 第一章 緒論 1 1.1柯屬植物大葉石櫟之簡介 1 1.2 柯屬植物大葉石櫟成分之研究 2 1.4 Friedelin生物活性之研究 9 1.5 Glaucine(海罌粟鹼)介紹 10 1.6 Glaucine之結構修飾 10 1.7 研究目的 11 第二章 實驗結果與討論 13 2.1 大葉石櫟葉部之成分初步分離 13 2.1.1 Squalene (角鯊烯) (1)之結構解析 14 2.1.2 Friedelin (2)之結構解析 16 2.1.3 β-Sitosterol (β-谷固醇) (3)之結構解析 18 2.1.4 Epifriedelanol (4)之結構解析 20 2.2 Friedelin之結構修飾研究 20 2.2.1 化合物3-hydroximinofriedelan (5)之製備 22 2.2.2 化合物3β-aminofriedelan (6)之製備 25 2.2.3 化合物7之製備 26 2.2.4 化合物8-19之製備 27 2.3 6a,7-Didehydroglaucine (20)之製備與結構修飾研究 31 2.3.1 化合物21之製備 32 2.3.2 化合物22-24之製備 33 2.4 結論 34 第三章 實驗方法 36 3.1 儀器與材料 36 3.1.1 理化性質測定儀器 36 3.1.2 成分分離之方法與材料 36 3.1.3 溶劑與試藥 37 3.2 大葉石櫟葉部成分之萃取與分離 38 3.2.1 化合物1-3之分離 39 3.2.2 化合物2之分離 40 3.3 大葉石櫟化合物1-3之物理數據 41 3.4 Friedelin衍生物之製備與物理數據 43 3.4.1 化合物friedelin (2)之製備 43 3.4.2 化合物3-hydroximinofriedelan (5)之製備 43 3.4.3 化合物3β-aminofriedelan (6)之製備 44 3.4.4 化合物7-19之製備與物理數據 45 3.4.4.1 3β-Dimethylaminofriedelan (7)之製備 45 3.4.4.2 3β-(Propylamino)-friedelan (8)之製備 46 3.4.4.3 3β-(Butylamino)-friedelan (9)之製備 47 3.4.4.4 3β-(Isobutylamino)-friedelan (10)之製備 48 3.4.4.5 3β-(Benzylamino)-friedelan (11)之製備 49 3.4.4.6 3β-(4-Hydroxybenzylamino)-friedelan (12)之製備 51 3.4.4.7 3β-(3-hydroxybenzylamino)-friedelan (13)之製備 52 3.4.4.8 3β-(3,4-Dihydrobenzylamino)-friedelan (14)之製備 53 3.4.4.9 3β-(4-Methoxybenzylamino)-friedelan (15)之製備 54 3.4.4.10 3β-(3,5-Di-tert-butyl-4-hydroxybenzylamino)-friedelan (16)之製備 55 3.4.4.11 3β-(4-Dimethylaminobenzylamino)-friedelan (17)之製備 56 3.4.4.12 3β-(4-Nitrobenzylamino)-friedelan (18)之製備 57 3.4.4.13 3β-(4-Chlorobenzylamino)-friedelan (19)之製備 58 3.5 6a,7-Didehydroglaucine (20)衍生物之製備與物理數據 59 3.5.1 6a,7-Didehydroglaucine (20)之製備 59 3.5.2化合物21之製備 60 3.5.3 化合物22-24之製備與物理數據 61 3.5.3.1 N-Acetyl-6a,7-didehydro-norglaucine (22)之製備 61 3.5.3.2 N-Propionyl-6a,7-didehydro-norglaucine (23)之製備 62 3.5.3.3 N-Benzoyl-6a,7-didehydro-norglaucine (24)之製備 63 參考文獻 65 附圖 (Spectra Appendices) 70 表目錄 (List of Tables) Table 1. Chemical constituents isolated from plants of the genus Pasania 3 Table 2. 1H and 13C NMR data of compound 1 and squalene (CDCl3) 15 Table 3. 1H and 13C NMR data of compound 2 and friedelin (CDCl3) 17 Table 4. 1H and 13C NMR data of compound 3 and β-sitosterol (CDCl3) 19 Table 5. 1H and 13C NMR data of compound 5 (CDCl3) 24 Table 6. The MS and NMR data of compounds 8–10 29 Table 7. The MS and NMR data of compounds 11–19 30 Table 8. The MS and NMR data of compounds 22–24 34 流程目錄 (List of Schemes) Scheme 1. Preparation of 3-hydroximinofriedelan (5) 22 Scheme 2. Preparation of compound 6 25 Scheme 3. Preparation of compound 7 26 Scheme 4. Preparation of compounds 8–19 27 Scheme 5. Preparation of 6a,7-didehydroglaucine (20) 31 Scheme 6. Preparation of compound 21 32 Scheme 7. Preparation of compounds 22–24 33 Scheme 8. Extraction and liquid-liquid partition of Pasania kawakamii leaf 39 Scheme 9. Separation of compounds 1–3 from the hexane soluble part of Pasania kawakamii leaf 40 Scheme 10. Large-scale separation of 2 from the hexane soluble part of Pasania kawakamii leaf 41 圖及光譜圖目錄 (List of Figures and Spectra Appendices) Figure 1. Pasania kawakamii (Hayata) Schottky (Fagaceae) 1 Figure 2. Biosynthesis of friedelin 8 Figure 3. Mechanism of ring-opening reaction 11 Figure 4. Mechanism of enamine addition reaction 11 Figure 5. The bioactivities for amino derivatives of triterpenoids 12 Figure 6. Proposed SN2' mechanism for formation of N-acyldehydroglaucine 12 Figure 7. Structures of compounds (1–4) isolated from Pasania kawakamii 13 Figure 8. (A) Chemical structure, (B) conformation structure and (C) crystal structure of friedelin 20 Figure 9. Mechanism of reductive amination 21 Figure 10. Retrosynthetic analysis of ketone (2) to amines (6–19) 22 Figure 11. Mechanism of ketone (2) to ketoxime (5) 22 Figure 12. Partial structure of compound 5 23 Figure 13. Mechanism of catalytic hydrogenation of oxime 5 25 Figure 14. Mechanism of Eschweiler-Clarke reaction 26 Figure 15. Equilibrium of reductive amination 28 Figure 16. Expanded 1H-NMR spectrum for H-1' of compound 8 28 Figure 17. Expanded 1H-NMR spectrum for H-1' of compound 11 29 Figure 18. Mechanism of glaucine to 6a,7-didehydroglaucine (20) 32 Figure 19. Mechanism of 10-O-demethylation 32 Figure 20. N-acylation and N-demethylation of 20 via SN2' mechanism 33 Figure 21. 1H NMR spectrum of 1 (CDCl3, 400 MHz) 71 Figure 22.13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 1 (CDCl3, 50 MHz) 72 Figure 23. 1H NMR spectrum of 2 (CDCl3, 400 MHz) 73 Figure 24. 1H NMR spectrum of 2 (CDCl3, 400 MHz) 74 Figure 25. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 2 (CDCl3, 50 MHz) 75 Figure 26. 1H NMR spectrum of 3 (CDCl3, 400 MHz) 76 Figure 27. 1H NMR spectrum of mixture 2 and 4 (CDCl3, 200 MHz) 77 Figure 28. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of mixture 2 and 4 (CDCl3, 50 MHz) 78 Figure 29. 1H NMR spectrum of 5 (CDCl3, 400 MHz) 79 Figure 30. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 6 (CDCl3, 50 MHz) 80 Figure 31. 1H NMR spectrum of 6 (CDCl3, 400 MHz) 81 Figure 32. 1H NMR spectrum of 6 (CDCl3, 400 MHz) 82 Figure 33. 1H NMR spectrum of 6 (CDCl3 + D2O, 400 MHz) 83 Figure 34. 1H NMR spectrum of 6 (CDCl3 + D2O, 400 MHz) 84 Figure 35. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 6 (CDCl3, 50 MHz) 85 Figure 36. 1H NMR spectrum of 7 (CDCl3, 200 MHz) 86 Figure 37. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 7 (CDCl3, 50 MHz) 87 Figure 38. 1H NMR spectrum of 8 (CDCl3, 200 MHz) 88 Figure 39. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 8 (CDCl3, 50 MHz) 89 Figure 40. 1H NMR spectrum of 9 (CDCl3, 200 MHz) 90 Figure 41. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 9 (CDCl3, 50 MHz) 91 Figure 42. 1H NMR spectrum of 10 (CDCl3, 200 MHz) 92 Figure 43. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 10 (CDCl3, 50 MHz) 93 Figure 44. 1H NMR spectrum of 11 (CDCl3, 200 MHz) 94 Figure 45. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 11 (CDCl3, 50 MHz) 95 Figure 46. 1H NMR spectrum of 12 (CDCl3, 200 MHz) 96 Figure 47. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 12 (CDCl3, 50 MHz) 97 Figure 48. 1H NMR spectrum of 13 (CDCl3, 200 MHz) 98 Figure 49. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 13 (CDCl3, 50 MHz) 99 Figure 50. 1H NMR spectrum of 14 (CD3OD & CDCl3 (1:1), 200 MHz) 100 Figure 51. 1H NMR spectrum of 15 (CDCl3, 200 MHz) 101 Figure 52. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 15 (CDCl3, 50 MHz) 102 Figure 53. 1H NMR spectrum of 16 (CDCl3, 200 MHz) 103 Figure 54. 1H NMR spectrum of 16 (CDCl3 + D2O, 400 MHz) 104 Figure 55. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 16 (CDCl3, 50 MHz) 105 Figure 56. 1H NMR spectrum of 17 (CDCl3, 200 MHz) 106 Figure 57. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 17 (CDCl3, 50 MHz) 107 Figure 58. 1H NMR spectrum of 18 (CDCl3 + D2O, 200 MHz) 108 Figure 59. 1H NMR spectrum of 19 (CDCl3, 200 MHz) 109 Figure 60. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 19 (CDCl3, 50 MHz) 110 Figure 61. 1H NMR spectrum of 20 (CDCl3, 200 MHz) 111 Figure 62. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 20 (CDCl3, 50 MHz) 112 Figure 63. 1H NMR spectrum of 21 (CDCl3, 200 MHz) 113 Figure 64. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 21 (CDCl3, 50 MHz) 114 Figure 65. 1H NMR spectrum of 22 (CDCl3, 200 MHz) 115 Figure 66. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 22 (CDCl3, 50 MHz) 116 Figure 67. HSQC spectrum of compound 22 (CDCl3, 600MHz) 117 Figure 68. 1H NMR spectrum of 23 (CDCl3, 200 MHz) 118 Figure 69. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 23 (CDCl3, 50 MHz) 119 Figure 70. 1H NMR spectrum of 24 (CDCl3, 200 MHz) 120 Figure 71. 13C NMR spectra (BBD, bottom;DEPT 135, middle;DEPT 90, top) of 24 (CDCl3, 50 MHz) 121 | |
dc.language.iso | zh-TW | |
dc.title | "第一部分:Friedelin之分離及含氮衍生物之製備;第二部分:6a,7-Didehydroglaucine衍生物之製備" | zh_TW |
dc.title | Part 1. Isolation of friedelin and preparation of
aminofriedelan derivatives;Part 2. Preparation of 6a,7-didehydroglaucine derivatives | en |
dc.type | Thesis | |
dc.date.schoolyear | 102-1 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 陳繼明,林雲蓮,張嘉銓 | |
dc.subject.keyword | Firedelin,含胺基friedelin衍生物,大葉石櫟,去氫海罌粟鹼,氮上去甲基醯胺化, | zh_TW |
dc.subject.keyword | Friedelin,aminofriedelan derivatives,Pasania kawakamii,6a,7-didehydroglaucine,N-demethylation acylation, | en |
dc.relation.page | 121 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2014-02-11 | |
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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ntu-103-1.pdf 目前未授權公開取用 | 9.5 MB | Adobe PDF |
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