Supporting Information Bafilomycins and Odoriferous Sesquiterpenoids from Streptomyces albolongus Isolated from Elephas maximus Feces Nan Ding,, Yi Jiang, Li Han, Xiu Chen, Jian Ma, Xiaodan Qu, Yu Mu, Jiang Liu, Liya Li, Chenglin Jiang, Xueshi Huang, Institute of Microbial Pharmaceuticals, College of Life and Health Sciences, Northeastern University, Shenyang 110819, P. R. China Laboratory of Metabolic Disease Research and Drug Development, China Medical University, Shenyang 110001, P. R. China Yunnan Institute of Microbiology, Yunnan University, Kunming 650091, P. R. China *To whom correspondence should be addressed. Tel: 0086-24-83656122. Fax: 0086-24-83656122. E-mail: huangxs@mail.neu.edu.cn. i
Figure S1. HRESI-MS spectrum of the new compound 1 Figure S2. 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of the new compound 1 Figure S3. 13 C NMR (150 MHz, DMSO-d 6 ) spectrum of the new compound 1 Figure S4. HSQC spectrum of the new compound 1 Figure S5. HMBC spectrum of the new compound 1 Figure S6. COSY spectrum of the new compound 1 Figure S7. NOESY spectrum of the new compound 1 Figure S8. HRESI-MS spectrum of the new compound 2 Figure S9. 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of the new compound 2 Figure S10. 13 C NMR (150 MHz, DMSO-d 6 ) spectrum of the new compound 2 Figure S11. HSQC spectrum of the new compound 2 Figure S12. HMBC spectrum of the new compound 2 Figure S13. COSY spectrum of the new compound 2 Figure S14. NOESY spectrum of the new compound 2 Figure S15. HRESI-MS spectrum of the new compound 3 Figure S16. 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of the new compound 3 Figure S17. 13 C NMR (150 MHz, DMSO-d 6 ) spectrum of the new compound 3 Figure S18. HSQC spectrum of the new compound 3 ii
Figure S19. HMBC spectrum of the new compound 3 Figure S20. COSY spectrum of the new compound 3 Figure S21. NOESY spectrum of the new compound 3 Figure S22. HRESI-MS spectrum of the new compound 10 Figure S23. 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of the new compound 10 Figure S24. 13 C NMR (150 MHz, DMSO-d 6 ) spectrum of the new compound 10 Figure S25. HSQC spectrum of the new compound 10 Figure S26. HMBC spectrum of the new compound 10 Figure S27. COSY spectrum of the new compound 10 Figure S28. NOESY spectrum of the new compound 10 Figure S29. HRESI-MS spectrum of the new compound 11 Figure S30. 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of the new compound 11 Figure S31. 13 C NMR (150 MHz, DMSO-d 6 ) spectrum of the new compound 11 Figure S32. HSQC spectrum of the new compound 11 Figure S33. HMBC spectrum of the new compound 11 Figure S34. COSY spectrum of the new compound 11 Figure S35. NOESY spectrum of the new compound 11 iii
Figure S1. HRESI-MS spectrum of the new compound 1 1
Figure S2. 1 H NMR (600 MHz, DMSO-d6) spectrum of the new compound 1 2 1.33 1.33 1.27 3.71 1.24 1.27 2.60 2.60 1.00 3.08 1.45 3.77 2.21 1.21 7.89 7.50 6.96 6.99 6.48 6.49 6.50 6.52 6.53 6.53 5.71 5.73 5.82 5.83 5.12 5.13 5.15 5.18 4.87 4.88 4.89 4.28 4.30 3.94 3.96 4.08 3.54 3.56 3.31 14.00 3.23 2.98 3.12 2.53 1.53 5.95 1.24 1.40 8.18 6.75 1.11 1.86 3.26 6.15 16.91 7.86 2.39 2.40 2.41 2.22 1.53 1.70 1.77 1.90 1.98 1.42 0.75 0.75 0.76 0.78 0.82 0.84 0.85 0.86 0.87 0.87 0.88 0.88 0.90 0.94 0.95 0.98 0.99 1.23
Figure S3. 13 C NMR (150 MHz, DMSO-d 6 ) spectrum of the new compound 1 3
Figure S4. HSQC spectrum of the new compound 1 4
Figure S5. HMBC spectrum of the new compound 1 5
Figure S6. COSY spectrum of the new compound 1 6
Figure S7. NOESY spectrum of the new compound 1 7
Figure S8. HRESI-MS spectrum of the new compound 2 8
Figure S9. 1 H NMR (600 MHz, DMSO-d6) spectrum of the new compound 2 9 2.25 1.00 1.03 0.92 2.32 1.13 0.99 1.18 0.91 2.70 6.49 6.51 6.52 6.53 5.69 5.71 5.81 5.82 5.32 5.32 4.90 5.10 4.02 4.16 4.17 4.47 4.48 4.49 4.49 4.89 3.52 3.53 3.56 3.94 3.30 4.91 3.14 2.96 2.49 1.52 1.07 2.47 5.08 5.88 1.02 2.38 1.36 2.31 2.90 6.33 10.72 4.72 2.49 2.41 2.40 2.03 2.39 2.02 2.00 1.56 1.70 1.79 1.40 0.69 0.71 0.73 0.74 0.75 0.76 0.76 0.77 0.79 0.80 0.81 0.83 0.84 0.85 0.85 0.86 0.86 0.87 0.88 0.94 0.95 1.23
13.99 16.80 17.56 19.58 21.02 7.21 8.85 10.94 180 170 160 150 140 130 120 110 100 90 80 Figure S10. 13 C NMR (150 MHz, DMSO-d6) spectrum of the new compound 2 10 70 60 50 40 30 20 10 0-10 164.78 141.28 143.03 144.44 131.01 132.08 132.40 124.28 125.98 97.63 83.44 75.74 77.82 78.83 70.30 59.72 55.53 55.61 37.49 38.79 39.49 39.63 39.77 39.90 25.48 28.09 28.41 30.20 31.94
Figure S11. HSQC spectrum of the new compound 2 11
Figure S12. HMBC spectrum of the new compound 2 12
Figure S13. COSY spectrum of the new compound 2 13
Figure S14. NOESY spectrum of the new compound 2 14
Figure S15. HRESI-MS spectrum of the new compound 3 15
2.01 1.00 1.00 2.01 0.99 1.02 1.02 2.97 1.36 6.48 6.49 6.50 6.52 6.53 5.71 5.73 5.82 5.83 5.13 5.14 5.15 5.18 4.88 4.89 4.14 4.15 3.95 3.96 3.29 3.39 3.53 3.56 4.12 3.14 3.90 2.49 2.96 2.97 1.28 1.09 1.90 2.05 2.07 2.38 2.39 2.40 2.41 6.25 6.36 2.54 2.79 3.54 13.63 6.22 0.74 0.75 0.80 0.81 0.82 0.83 0.85 0.86 0.87 0.88 0.90 0.92 0.94 0.94 0.95 0.96 1.23 1.33 1.34 1.41 1.71 1.77 1.84 Figure S16. 1 H NMR (600 MHz, DMSO-d6) spectrum of the new compound 3 16
Figure S17. 13 C NMR (150 MHz, DMSO-d 6 ) spectrum of the new compound 3 17
Figure S18. HSQC spectrum of the new compound 3 18
Figure S19. HMBC spectrum of the new compound 3 19
Figure S20. COSY spectrum of the new compound 3 20
Figure S21. NOESY spectrum of the new compound 3 21
Figure S22. HRESI-MS spectrum of the new compound 10 22
1.00 0.95 5.38 5.38 4.75 4.75 1.04 3.27 3.27 3.28 3.28 3.31 1.03 1.03 1.87 1.89 2.19 2.20 2.21 2.22 2.49 2.49 2.50 1.76 1.64 2.17 3.16 1.15 1.28 2.86 1.10 2.92 1.35 1.38 1.51 1.61 1.13 0.70 0.71 0.75 0.75 0.78 0.89 Figure S23. 1 H NMR (600 MHz, DMSO-d6) spectrum of the new compound 10 23
75.13 75.96 39.48 39.56 39.62 39.76 39.90 40.04 40.18 40.32 34.31 28.75 30.08 30.56 25.54 20.27 20.64 21.21 15.32 Figure S24. 13 C NMR (150 MHz, DMSO-d6) spectrum of the new compound 10 24
15 20 25 30 35 40 45 50 55 60 65 70 75 80 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 Figure S25. HSQC spectrum of the new compound 10 25
Figure S26. HMBC spectrum of the new compound 10 26
Figure S27. COSY spectrum of the new compound 10 27
Figure S28. NOESY spectrum of the new compound 10 28
Figure S29. HRESI-MS spectrum of the new compound 11 29
1.00 0.98 0.99 1.00 1.08 1.12 5.40 5.41 4.79 4.79 4.20 4.20 3.96 3.97 3.50 1.94 2.23 2.26 2.49 2.49 2.49 2.50 2.50 3.15 3.16 3.25 3.25 3.32 2.10 1.09 1.03 2.90 2.70 1.27 3.30 1.03 2.66 0.73 0.74 0.75 0.98 1.12 1.27 1.30 1.41 1.44 1.46 1.66 1.91 1.91 Figure S30. 1 H NMR (600 MHz, DMSO-d6) spectrum of the new compound 11 30
75.37 75.74 65.51 36.91 39.42 39.48 39.62 39.76 39.90 40.03 40.17 33.85 23.08 25.58 27.87 28.90 15.42 Figure S31. 13 C NMR (150 MHz, DMSO-d6) spectrum of the new compound 11 31
Figure S32. HSQC spectrum of the new compound 11 32
Figure S33. HMBC spectrum of the new compound 11 33
Figure S34. COSY spectrum of the new compound 11 34
Figure S35. NOESY spectrum of the new compound 11 35