Supporting information Cyclizidine-type Alkaloids from the Streptomyces sp. HNA39 Yong-Jun Jiang, Jia-Qi Li, Hao-Jian Zhang, Wan-Jing Ding, and Zhong-Jun Ma * Institute of Marine Biology, Ocean College, Zhejiang University, Zhoushan 316021, People s Republic of China; * Corresponding author E-mail: mazj@zju.edu.cn Table of Contents Figure S1-9. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 1 2-8 Figure S10-18. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 2 9-15 Figure S19-27. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 3 16-22 Figure S28. Experimental ECD spectrum and the calculated ECD spectra of 3. 23 Figure S29-37. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 4 24-30 Figure S38-46. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 5 31-37 Figure S47. Experimental ECD spectrum and the calculated ECD spectra of 5. 38 Figure S48-56. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 6 39-45 Figure S57. Experimental ECD spectrum and the calculated ECD spectra of 6. 46 Figure S58-66. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 7 47-53 Figure S67-75. 1D and 2D NMR, HRESIMS, IR, and UV spectra of 8 54-60 Figure S76. Experimental ECD spectra for 7 and 8 and the calculated ECD spectra of 7. 61 Figure S77-78. HRESIMS and ECD spectra of 9. 62 1
Figure S1. 1 H NMR spectrum of 1 2
Figure S2. 13 C NMR spectrum of 1 3
Figure S3. HSQC spectrum of 1 4
Figure S4. HMBC spectrum of 1 5
Figure S5. 1 H- 1 H COSY spectrum of 1 6
Figure S6. NOESY spectrum of 1 Figure S7. HRESIMS spectrum of 1 7
Figure S8. IR spectrum of 1. Figure S9. UV spectrum of 1. 8
Figure S10. 1 H NMR spectrum of 2 9
Figure S11. 13 C NMR spectrum of 2 10
Figure S12. HSQC spectrum of 2. 11
Figure S13. HMBC spectrum of 2. 12
Figure S14. 1 H- 1 H COSY spectrum of 2. 13
Figure S15. NOESY spectrum of 2. Figure S16. HRESIMS spectrum of 2 14
Figure S17. IR spectrum of 2 Figure S18. UV spectrum of 2. 15
Figure S19. 1 H NMR spectrum of 3. 16
Figure S20. 13 C NMR spectrum of 3. 17
Figure S21. HSQC spectrum of 3. 18
Figure S22. HMBC spectrum of 3. 19
Figure S23. 1 H- 1 H COSY spectrum of 3. 20
Figure S24. NOESY spectrum of 3 Figure S25. HRESIMS spectrum of 3. 21
Figure S26. IR spectrum of 3. Figure S27. UV spectrum of 3. 22
Figure S28. Experimental ECD spectrum and the calculated ECD spectra of 3. 23
Figure S29. 1 H NMR spectrum of 4. 24
Figure S30. 13 C NMR spectrum of 4. 25
Figure S31. HSQC spectrum of 4. 26
Figure S32. HMBC spectrum of 4. 27
Figure S33. 1 H- 1 H COSY NMR spectrum of 4. 28
Figure S34. NOESY spectrum of 4. Figure S35. HRESIMS spectrum of 4. 29
Figure S36. IR spectrum of 4. Figure S37. UV spectrum of 4. 30
Figure S38. 1 H NMR spectrum of 5. 31
Figure S39. 13 C NMR spectrum of 5. 32
Figure S40. HSQC spectrum of 5. 33
Figure S41. HMBC spectrum of 5. 34
Figure S42. 1 H- 1 H COSY spectrum of 5. 35
Figure S43. NOESY spectrum of 5. Figure S44. HRESIMS spectrum of 5. 36
Figure S45. IR spectrum of 5. Figure S46. UV spectrum of 5. 37
Figure S47. Experimental ECD spectrum and the calculated ECD spectra of 5. 38
Figure S48. 1 H NMR spectrum of 6. 39
Figure S49. 13 C NMR spectrum of 6. 40
Figure S50. HSQC spectrum of 6. 41
Figure S51. HMBC spectrum of 6. 42
Figure S52. 1 H- 1 H COSY spectrum of 6. 43
Figure S53. NOESY spectrum of 6. Figure S54. HRESIMS spectrum of 6. 44
Figure S55. IR spectrum of 6. Figure S56. UV spectrum of 6. 45
Figure S57. Experimental ECD spectrum and the calculated ECD spectra of 6. 46
Figure S58. 1 H NMR spectrum of 7. 47
Figure S59. 13 C NMR spectrum of 7. 48
Figure S60. HSQC spectrum of 7. 49
Figure S61. HMBC spectrum of 7. 50
Figure S62. 1 H- 1 H COSY spectrum of 7. 51
Figure S63. NOESY spectrum of 7. Figure S64. HRESIMS spectrum of 7. 52
Figure S65. IR spectrum of 7. Figure S66. UV spectrum of 7. 53
Figure S67. 1 H NMR spectrum of 8. 54
Figure S68. 13 C NMR spectrum of 8. 55
Figure S69. HSQC spectrum of 8. 56
Figure S70. HMBC spectrum of 8. 57
Figure S71. 1 H- 1 H COSY spectrum of 8. 58
Figure S72. NOESY spectrum of 8. Figure S73. HRESIMS spectrum of 8. 59
Figure S74. IR spectrum of 8. Figure S75. UV spectrum of 8. 60
Figure S76. Experimental ECD spectra for 7 and 8 and the calculated ECD spectra of 7. 61
Figure S77. HRESIMS spectrum of 9. Figure S78. Experimental ECD spectrum of 9. 62