표제지
목차
Abbreviation 12
국문초록 13
Ⅰ. 서론 15
Ⅱ. 실험 재료 및 방법 18
1. 실험 재료 18
2. 실험 기구 및 시약 26
2.1. 실험 기구 26
2.2. 시약 27
2.3. 데이터 가공 및 처리 28
3. 실험방법 29
3.1. 산-염기 추출법 29
3.2. LC-MS/MS 시료의 제조 및 측정 30
3.3. 추출 및 분획 30
Ⅲ. 실험 결과 및 고찰 40
1. 275종의 LC-MS/MS 데이터 분자 네트워킹 40
1.1. 세 과에서의 MIA 분포 양상 분석 40
1.2. MS/MS spectrum 간 구조 다양성 분석 46
2. 시료 선정 및 화합물 분리 연구 52
2.1. 시료 선정 52
2.2. 화합물 분리 및 구조 규명 53
3. 활성 평가 86
3.1. 세포 독성 평가 86
3.2. 항진균 활성 평가 86
Ⅳ. 결론 87
Ⅴ. 참고문헌 88
ABSTRACT 93
Table 1. The plants list of 275 species 18
Table 2. ¹H (500 MHz) and ¹³C (125 MHz) spectroscopic data of compound 1 in CD₃OD 35
Table 3. ¹H NMR (500 MHz) data of compounds 2-6 36
Table 4. ¹³C NMR (125 MHz) data of compounds 2-6 37
Table 5. ¹H (500 MHz) and ¹³C (125 MHz) spectroscopic data of compounds 7, 8 in CD₃OD 38
Table 6. Related Mass2motif of identified compounds 46
Table 7. The IC₅₀ values of compounds 1-4 for three cell line 86
Figure 1. Three structural types of monoterpene indole alkaloids 15
Figure 2. Examples of MIAs 16
Figure 3. Extraction of alkaloid-rich fraction 29
Figure 4. Structures of compounds 1-8 39
Figure 5. A molecular network of alkaloids-rich fractions of 275 plants species 41
Figure 6. MIA molecular families related to Apocynaceae, Loganiaceae, and Rubiaceae 44
Figure 7. The peak intensity of 13 annotated MIA 45
Figure 8. (a) The MF of rauwolscine with Mass2motif (b) The MFs related rauwolscine 47
Figure 9. The MF of pubescine and isoreserpiline with Mass2motif and their fragmentation structure 48
Figure 10. The molecular family related vindoline 49
Figure 11. The MF of (-)-eburnamonine with Mass2motif and its fragmentation structure 50
Figure 12. The MF of tubotaiwine with Mass2motif 51
Figure 13. Predicted structure around nodes containing Uncaria scandens 52
Figure 14. The BPI chromatogram of alkaloids-rich fraction (positive ion mode) 53
Figure 15. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 1 in CD₃OD 55
Figure 16. HSQC spectrum of compound 1 in CD₃OD 56
Figure 17. HMBC spectrum of compound 1 in CD₃OD 56
Figure 18. ¹H-¹H COSY spectrum of compound 1 in CD₃OD 57
Figure 19. ROESY spectrum of compound 1 in CD₃OD 57
Figure 20. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 2 in CDCl₃ 59
Figure 21. HSQC spectrum of compound 2 in CDCl₃ 60
Figure 22. HMBC spectrum of compound 2 in CDCl₃ 60
Figure 23. ¹H-¹H COSY spectrum of compound 2 in CDCl₃ 61
Figure 24. NOESY spectrum of compound 2 in CDCl₃ 61
Figure 25. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 3 in CD₃OD 63
Figure 26. HSQC spectrum of compound 3 in CD₃OD 64
Figure 27. HMBC spectrum of compound 3 in CD₃OD 64
Figure 28. ¹H-¹H COSY spectrum of compound 3 in CD₃OD 65
Figure 29. NOESY spectrum of compound 3 in CD₃OD 65
Figure 30. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 4 in CD₃OD 67
Figure 31. HSQC spectrum of compound 4 in CD₃OD 68
Figure 32. HMBC spectrum of compound 4 in CD₃OD 68
Figure 33. ¹H-¹H COSY spectrum of compound 4 in CD₃OD 69
Figure 34. NOESY spectrum of compound 4 in CD₃OD 69
Figure 35. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 5 in CD₃OD 71
Figure 36. HSQC spectrum of compound 5 in CD₃OD 72
Figure 37. HMBC spectrum of compound 5 in CD₃OD 72
Figure 38. ¹H-¹H COSY spectrum of compound 5 in CD₃OD 73
Figure 39. NOESY spectrum of compound 5 in CD₃OD 73
Figure 40. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 6 in CD₃OD 75
Figure 41. HSQC spectrum of compound 6 in CD₃OD 76
Figure 42. HMBC spectrum of compound 6 in CD₃OD 76
Figure 43. ¹H-¹H COSY spectrum of compound 6 in CD₃OD 77
Figure 44. NOESY spectrum of compound 6 in CD₃OD 77
Figure 45. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 7 in CD₃OD 79
Figure 46. HSQC spectrum of compound 7 in CD₃OD 80
Figure 47. HMBC spectrum of compound 7 in CD₃OD 80
Figure 48. ¹H-¹H COSY spectrum of compound 7 in CD₃OD 81
Figure 49. ¹H NMR (500 MHz) and ¹³C NMR (125 MHz) spectra of compound 8 in CD₃OD 83
Figure 50. HSQC spectrum of compound 8 in CD₃OD 84
Figure 51. HMBC spectrum of compound 8 in CD₃OD 84
Figure 52. ¹H-¹H COSY spectrum of compound 8 in CD₃OD 85