표제지
목차
Abbreviation 12
국문초록 14
Ⅰ. 서론 16
Ⅱ. 실험 재료 및 방법 19
1. 실험 재료 19
1) 실험 균주 19
2) 실험 기구 20
3) 시약 22
2. 실험 방법 23
1) 34종 Penicillium 균주의 배양 및 추출물 제조 23
2) 물질 분리를 위한 P. digitatum의 대량 배양 23
3) LC-MS/MS 시료 제조 및 측정 24
4) 데이터 분석 24
5) 분획 및 분리 24
Ⅲ. 실험 결과 및 고찰 30
1. β-sitosterol에 의한 34종 균주에서의 이차대사 변화 양상 관찰 30
2. P. digitatum에서 β-sitosterol에 의해 유도된 화합물의 분리 33
1) 화합물 1 37
2) 화합물 2 41
3) 화합물 3 47
4) 화합물 4, 5 52
3. 화합물 1-5의 생합성 경로 추정 56
Ⅳ. 요약 및 결론 59
Ⅴ. 참고문헌 61
ABSTRACT 65
Table 1. The list of 34 Penicillium strains used in this study 19
Table 2. ¹H (500 MHz) and ¹³C (125 MHz) NMR data of compounds 1 and 2 in DMSO-d₆ 28
Table 3. ¹H (600 MHz) and ¹³C (150 MHz) NMR data of compound 3 in CD₃OD 29
Figure 1. The structures of fungal secondary metabolites mentioned in the section 17
Figure 2. Isolation scheme of the extract of P. digitatum cultured with 33 µM β-sitosterol 25
Figure 3. The molecular network of 34 Penicillium strains in positive ion mode 31
Figure 4. The BPI chromatograms of the P. digitatum metabolome in positive ion mode (a) and negative ion mode (b)... 32
Figure 5. The MS/MS mirror plots, structures and EIC chromatograms of tryptoquivalines G (a) and Q (b), fumiquinazoline D (c)... 34
Figure 6. The predicted structures of compounds in β-sitosterol-elicited P. digitatum 35
Figure 7. The structure of compound 1 37
Figure 8. ¹H (500 MHz) and ¹³C (125 MHz) NMR spectra of compound 1 in DMSO-d₆ 38
Figure 9. HSQC spectrum of compound 1 in DMSO-d₆ 39
Figure 10. HMBC spectrum of compound 1 in DMSO-d₆ 39
Figure 11. ¹H-¹H COSY spectrum of compound 1 in DMSO-d₆ 40
Figure 12. NOESY spectrum of compound 1 in DMSO-d₆ 40
Figure 13. The MS spectra of compounds 1 and 2 in positive ion mode 41
Figure 14. The MS/MS spectra of compounds 1 and 2 in positive ion mode 43
Figure 15. The hypothetical MS/MS fragmentation pathway of compound 1 43
Figure 16. The structure of compound 2 45
Figure 17. ¹H NMR (500MHz) spectrum of compound 2 in DMSO-d₆ 45
Figure 18. ¹H-¹H COSY spectrum of compound 2 in DMSO-d₆ 46
Figure 19. The structure of compound 3 47
Figure 20. ¹H (600MHz) and ¹³C (150 MHz) NMR spectra of compound 3 in CD₃OD 48
Figure 21. HSQC spectrum of compound 3 in CD₃OD 49
Figure 22. HMBC spectrum of compound 3 in CD₃OD 49
Figure 23. ¹H-¹H COSY spectrum of compound 3 in CD₃OD 50
Figure 24. NOESY spectrum of compound 3 in CD₃OD 50
Figure 25. Key NOE correlations of compound 3 shown with its 3D structure. 51
Figure 26. The MS/MS spectra of compounds 3-5 in positive ion mode 53
Figure 27. The hypothetical MS/MS fragmentation pathway of compound 3 53
Figure 28. ¹H NMR (500MHz) spectra of compounds 3-5 in CD₃OD 54
Figure 29. The structures of aspertoryadin F (a), aspertoryadin G (b) and tryptoquialanine C (c) 55
Figure 30. Plausible biosynthetic pathway of compounds 1 and 2 57
Figure 31. Plausible biosynthetic pathway of compound 3 58