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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 沈雅敬(Ya-Ching Shen) | |
| dc.contributor.author | Khongorzul Mendbayar | en |
| dc.contributor.author | 蒙貝佳 | zh_TW |
| dc.date.accessioned | 2021-06-15T07:02:54Z | - |
| dc.date.available | 2011-03-03 | |
| dc.date.copyright | 2011-03-03 | |
| dc.date.issued | 2011 | |
| dc.date.submitted | 2011-01-12 | |
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| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/48576 | - |
| dc.description.abstract | Phytochemical investigation of Schisandra sphenanthera (Schisandraceae) from dichloromethane partition of the acetone extracts led to the isolation of four new sesquiterpenes called schisansphenins A, B, C and D (1, 2, 3, 4) and eleven known compounds such as macelignan (5), 1-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-2,3-dimethylbutane (6), chicanine (7), meso-dimethyl dihydroguaraeitic acid (8), schisantherin D (9), 6-O-benzoylgomisin O (10), erythro-austrobailignan-6 (11), gomisin B (12), schisantherin A (13), gomisin G (14) and gomisin C (15).
Structural elucidations for the found compounds were based on spectroscopic analyses such as 1H- and 13C-NMR, including 2D NMR (1H-1H COSY, HMQC, HMBC and NOESY) experiments, and by comparison of their spectroscopic data with those of related metabolites. The isolated compounds had been tested by dipeptidyl peptidase-4 (DPP-4) inhibition assay. Except erythro-austrobailignan-6 (11), the rest isolated compounds did not show any significant inhibition. | en |
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| dc.description.tableofcontents | Master thesis certification by Oral Defense Committee …………………………...…………ii
Abstract……………………………………………………………………………….............iii List of compounds isolated from S. sphenanthera……………………………………...…….iv Acknowledgement……………………………………………………………………………..v Chapter 1. INTRODUCTION…………………………………………………………….…1 1.1 Objective of the research………………………………………………...………………...1 1.2 Introduction to Schisandra sphenanthera …………………………………...……….……3 1.3 Previous chemical investigation on Schisandra sphenanthera…………...………………6 1.4 Introduction to type II diabetes……………………………..…………………………....20 1.5 Inhibition of dipeptidyl peptidase-4 (DPP-4) for the treatment of type II diabetes……...23 Chapter 2. EXPERIMENTAL SECTION …………………….……………….…………24 2.1 Apparatus and materials…………………….……………………………….…………...24 2.1.1 Apparatus………………….…………………………………………………………..24 2.1.2 Solvents and reagents……………………………………………………………….…25 2.2 DPP-4 Inhibition Assay…………………………………………………………….…..26 2.2.1. Experimental procedure of DPP-4 Inhibition Assay……………………………….....28 2.3. Experimental procedure……………………………………………….………………..28 2.3.1. Extraction of the fruits of Schisandra sphenanthera………………….……………...28 2.3.2 Fractionation of CH2Cl2 soluble fraction…………………………….……………….29 2.3.2.1 Isolation of macelignan (5), schisansphenin A (1), schisansphenin B (2)………….29 2.3.2.2 Isolation of 1-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl) -2,3-dimethylbutane (6), chicanine (7), meso - dimethyl dihydroguaraeitic acid (8), schisantherin D (9)………………………………………………………………………………...….…….29 2.3.2.3 Isolation of schisansphenin C (3), 6-O-benzoylgomisin O (10) and schisansphenin D (4) ………………………………………………………………….………..….…….…….29 2.3.2.4 Isolation of erythro-austrobailignan-6 (11), gomisin B (12), schisantherin A (13) and gomisin G (14)……… …………………….……………………………….…………...30 2.3.2.5 Isolation of gomisin C (15)………………………………………………..…………30 Chapter 3. RESULTS AND DISCUSSION…………………………………..…………..32 3.1 Structure elucidation of schisansphenin A (1)……………………………..……..……..32 3.2 Structure elucidation of schisansphenin B (2)………………………..……….…………36 3.3 Structure elucidation of schisansphenin C (3)…………………………………..………39 3.4 Structure elucidation of schisansphenin D (4)………………...…………..…………….43 3.5 Structure elucidation of macelignan (5)……………………………………..………….48 3.6 Structure elucidation of 1-(3,4- dimethoxyphenyl)-4-(3,4- methylenedioxyphenyl)- 2,3-dimethylbutane (6) ……………………………………………………………..……………49 3.7 Structure elucidation of chicanine (7)………………….….…….………...…………….50 3.8 Structure elucidation of meso-dimethyl dihydroguaiaretic acid (8)….……..…….….….51 3.9 Structure elucidation of schisantherin D (9)…….……………………….……….…..…..52 3.10 Structure elucidation of 6-O-benzoylgomisin O (10)…………….………………….….53 3.11 Structure elucidation of erythro-austrobailignan-6 (11)…………………………..……54 3.12 Structure elucidation of gomisin B (12)……………………………………..………….55 3.13. Structure elucidation of schisantherin A (13)………………………………...………..56 3.14 Structure elucidation of gomisin G (14) ………………………………..………………57 3.15 Structure elucidation of gomisin C (15)……………………………………..………...58 3.16. Biogenetic pathways of the isolated sesquiterpenes………………………...………….59 3.17. Effect of compounds 1-15 on DPP-4 inhibition assay…………………………..……..63 3.18. Conclusion……………………………………………...………………………………64 APPENDIX…………………………….…………..………………………………………...66 REFERENCES…………………………………………………...…………………………..86 List of Figures Figure 1. Schisandra sphenanthera Rehder & E.H.Wils-hua zhong wu wei zi 5 Figure 2. Insulin concentration and binding in normal and overweight subjects 20 Figure 3. The causes of diabetes mellitus and difference between type I and II. 21 Figure 4. DPP-4 inhibitors working mechanism to reduce blood glucose 24 Figure 5. Important physiological effects of GLP-1 24 Figure 6. The key HMBC and COSY correlations of schisansphenin A (1) 34 Figure 7. The Key NOESY correlations of schisansphenin A (1) 35 Figure 8. The Key HMBC and COSY correlations of schisansphenin B (2) 37 Figure 9. The Key NOESY correlations of schisansphenin B (2) 37 Figure 10. The Key HMBC and COSY correlations of schisansphenin C (3) 40 Figure 11. The Key NOESY correlations of schisansphenin C (3) 42 Figure 12. Cuparane type sesquiterpenoids which showed R and S chiralities 44 Figure 13. The Key HMBC and COSY correlations of schisansphenin D (4) 46 Figure 14. The Key NOESY correlations of schisansphenin D (4) 47 Figure 15. Compounds 1-15 on DPP-4 inhibition assay 63 Figure 16. 1H-NMR spectrum of schisansphenin A (1) ( 400MHz) 66 Figure 17. 13C-NMR spectrum of schisansphenin A (1) ( 400MHz) 66 Figure 18. 13C-NMR, DEPT-135, 90 spectra of schisansphenin A (1) ( 400MHz) 67 Figure 19. HMQC spectrum of schisansphenin A (1) ( 400MHz) 67 Figure 20. COSY spectrum of schisansphenin A (1) ( 400MHz) 68 Figure 21. HMBC spectrum of schisansphenin A (1) ( 400MHz) 68 Figure 22. NOESY spectrum of schisansphenin A (1) ( 400MHz) 69 Figure 23. 1H-NMR spectrum of schisansphenin B (2) ( 400MHz) 70 Figure 24. 13C-NMR spectrum of schisansphenin B (2) ( 400MHz) 70 Figure 25. 13C-NMR, DEPT-135, 90 spectra of schisansphenin B (2) ( 400MHz) 71 Figure 26. HMQC spectrum of schisansphenin B (2) ( 400MHz) 71 Figure 27. COSY spectrum of schisansphenin B (3) ( 400MHz) 72 Figure 28. HMBC spectrum of schisansphenin B (2) (400MHz) 72 Figure 29. NOESY spectrum of schisansphenin B (2) ( 400MHz) 73 Figure 30. 1H-NMR spectrum of schisansphenin C (3) ( 400MHz) 74 Figure 31. 13C-NMR spectrum of schisansphenin C (3) ( 400MHz) 74 Figure 32. 13C-NMR, DEPT-135, 90 spectra of schisansphenin C (3) ( 400MHz) 75 Figure 33. HMQC spectrum of schisansphenin C (3) ( 400MHz) 75 Figure 34. COSY spectrum of schisansphenin C (3) ( 400MHz) 76 Figure 35. HMBC spectrum of schisansphenin C (3) ( 400MHz) 76 Figure 36. NOESY spectrum of schisansphenin C (3) ( 400MHz) 77 Figure 37. 1H-NMR spectrum of schisansphenin D (4) ( 400MHz) 78 Figure 38. 13C-NMR spectrum of schisansphenin D (4) ( 400MHz) 78 Figure 39. 13C-NMR, DEPT-135, 90 spectra of schisansphenin D (4) ( 400MHz) 79 Figure 40. HMQC spectrum of schisansphenin D (4) ( 400MHz) 79 Figure 41. COSY spectrum of schisansphenin D (4) ( 400MHz) 80 Figure 42. HMBC spectrum of schisansphenin D (4) ( 400MHz) 80 Figure 43. NOESY spectrum of schisansphenin D (4) ( 400MHz) 81 Figure 44. HRESIMS of schisansphenin A (1) 82 Figure 45. IR spectrum of schisansphenin A (1) 82 Figure 46. HRESIMS of schisansphenin B (2) 83 Figure 47. IR spectrum of schisansphenin B (2) 83 Figure 48. HRESIMS of schisansphenin C (3) 84 Figure 49. IR spectrum of schisansphenin C (3) 84 Figure 50. HRESIMS of schisansphenin D (4) 85 Figure 51. IR spectrum of schisansphenin D (4) 85 List of Tables Table 1. Chemical constituents from S. sphenanthera 6 Table 2. Structures and biological activities of isolated compounds 7 Table 3. Current therapeutic agents for Type II diabetes other than DPP-4 inhibitors 22 Table 4. Main advantages and concerns of DPP-4 inhibitors 25 Table 5.1H and 13C-NMR data of schisansphenin A (1) (measured in CDCl3) 483 Table 6. 1H and 13C-NMR data of schisansphenin B (2) (measured in CDCl3) 38 Table 7. 1H and 13C-NMR data of schisansphenin C (3) (measured in CDCl3) 41 Table 8. 1H and 13C-NMR data of schisansphenin D (4) (4) (measured in CDCl3) 49 Table 9. 1H and 13C-NMR data of macelignan (5) (measured in CDCl3) 50 Table 10. 1H and 13C-NMR data of 1-(3,4- dimethoxyphenyl)-4-(3,4 methylenedioxyphenyl)- 2,3-dimethylbutane (6) (measured in CDCl3) 51 Table 11. 1H and 13C-NMR data of hicanine (7) (measured in CDCl3) 50 Table 12. 1H and 13C-NMR data of meso-dimethyl dihydroguaiaretic acid (8) (measured in CDCl3) 51 Table 13. 1H and 13C-NMR data of schisantherin D (9) (measured in CDCl3 ) 52 Table 14. 1H and 13C-NMR data of 6-O-benzoylgomisin O (10) (measured in CDCl3) 53 Table 15. 1H and 13C-NMR data of erythro-austrobailignan-6 (11) (measured in CDCl3) 54 Table 16. 1H and 13C-NMR data of gomisin B (12) (measured in CDCl3 ) 55 Table 17. 1H and 13C-NMR data of schisantherin A (13) (measured in CDCl3) 56 Table 18. 1H and 13C-NMR data of gomisin G (14) (measured in CDCl3) 57 Table 19. 1H and 13C-NMR data of gomisin C (15) (measured in CDCl3) 58 List of Schemes Scheme 1. Isolation of compound 1-15 from the CH2Cl2 soluble fraction 31 Scheme 2. Biogenetic pathway of sesquiterpenes 60 Scheme 3. Plausible biogenetic pathway of compound 1 61 Scheme 4. Plausible biogenetic pathway of compound 2 61 Scheme 5. Plausible biogenetic pathway of compound 3 62 Scheme 6. Plausible biogenetic pathway of compound 4 62 | |
| dc.language.iso | en | |
| dc.subject | 華中五味子 | zh_TW |
| dc.subject | sesquiterpenes | en |
| dc.subject | Schisandra sphenanthera | en |
| dc.subject | lignans | en |
| dc.subject | DPP-4 inhibition assay | en |
| dc.title | 華中五味子之果實成分研究 | zh_TW |
| dc.title | Studies on the Constituents of Fruits from Schisandra sphenanthera Rehd. et Wils | en |
| dc.type | Thesis | |
| dc.date.schoolyear | 99-1 | |
| dc.description.degree | 碩士 | |
| dc.contributor.oralexamcommittee | 周宏農(Hong-Nong Chou),蔣丙煌(Been-Huang Chiang) | |
| dc.subject.keyword | 華中五味子, | zh_TW |
| dc.subject.keyword | Schisandra sphenanthera,sesquiterpenes,lignans,DPP-4 inhibition assay, | en |
| dc.relation.page | 95 | |
| dc.rights.note | 有償授權 | |
| dc.date.accepted | 2011-01-12 | |
| 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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