Supporting information

Supporting information Antimicrobial Metabolites from Streptomyces sp. SN0280 Hui Tian, Jamil Shafi, Mingshan Ji,, Yuhui Bi, and Zhiguo Yu *,, College of Plant Protection, Shenyang Agricultural University, Shenyang 110866, People s Republic of China Engineering & Technological Research Center of Biopesticide for Liaoning Province, Shenyang 110866, People s Republic of China

List of contents 16S ribosomal DNA gene sequence data of SN0280... 3 Phylogenetic tree of SN028... 4 Figure S1. 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of chloroindole (1).... 5 Figure S2. 13 C NMR (600 MHz, DMSO-d 6 ) spectrum of chloroindole (1).... 5 Figure S3. 1 H- 1 H COSY spectrum of chloroindole (1) in DMSO-d 6... 6 Figure S4. HSQC spectrum of chloroindole (1) in DMSO-d 6.... 6 Figure S5. HMBC spectrum of chloroindole (1) in DMSO-d 6... 7 Figure S6. HRESIMS spectrum of chloroindole (1).... 7 Figure S7. 1 H NMR (600 MHz, CDCl 3 ) spectrum of streptoone A (2).... 8 Figure S8. 13 C NMR (150 MHz, CDCl 3 ) spectrum of streptoone A (2).... 8 Figure S9. 1 H- 1 H COSY spectrum of streptoone A (2) in CDCl 3... 9 Figure S10. HSQC spectrum of streptoone A (2) in CDCl 3.... 9 Figure S11. HMBC spectrum of streptoone A (2) in CDCl 3.... 10 Figure S12. NOESY spectrum of streptoone A (2) in CDCl 3... 10 Figure S13. HRESIMS spectrum of streptoone A (2)... 11 Figure S14. 1 H NMR (600 MHz, CDCl3) spectrum of streptoone B (3).... 11 Figure S15. 13 C NMR (150 MHz, CDCl3) spectrum of streptoone B (3)... 12 Figure S16. 1 H- 1 H COSY spectrum of streptoone B (3) in CDCl 3... 12 Figure S17. HSQC spectrum of streptoone B (3) in CDCl 3.... 13 Figure S18. HMBC spectrum of streptoone B (3) in CDCl 3.... 13 Figure S19. NOESY spectrum of streptoone B (3) in CDCl 3... 14 1

Figure S20. HRESIMS spectrum of streptoone B (3).... 14 Figure S21. 1 H NMR (600 MHz, CDCl 3 ) spectrum of streptoone C (4)... 15 Figure S22. 13 C NMR (150 MHz, CDCl 3 ) spectrum of streptoone C (4)... 15 Figure S23. 1 H- 1 H COSY spectrum of streptoone C (4) in CDCl 3... 16 Figure S24. HSQC spectrum of streptoone C (4) in CDCl 3.... 16 Figure S25. HMBC spectrum of streptoone C (4) in CDCl 3.... 17 Figure S26. NOESY spectrum of streptoone C (4) in CDCl 3... 17 Figure S27. HRESIMS spectrum of streptoone C (4).... 18 Table S1. Assignments of the 1 H (600 MHz) and 13 C (150 MHz) NMR data of the known compound X-14952B (5) in CDCl 3.... 18 Analytical data of the known compound X-14952B (5)... 19 2

16S ribosomal DNA gene sequence data of SN0280 Primers 27F:5 -AGAGTTTGATCCTGGCTCAG-3 1492R:5 -TACGGCTACCTTGTTACGACTT-3 GGGTTGGGCCACCGGCTTCGGGTGTTACCGACTTTCGTGACGTGACGG GCGGTGTGTACAAGGCCCGGGAACGTATTCACCGCAGCAATGCTGATCTGC GATTACTAGCGACTCCGACTTCATGGGGTCGAGTTGCAGACCCCAATCCGA ACTGAGACCGGCTTTTTGAGATTCGCTCCACCTCGCGGTATCGCAGCTCATT GTACCGGCCATTGTAGCACGTGTGCAGCCCAAGACATAAGGGGCATGATGA CTTGACGTCGTCCCCACCTTCCTCCGAGTTGACCCCGGCAGTCTCCTGTGA GTCCCCATCACCCCGAAGGGCATGCTGGCAACACAGGACAAGGGTTGCGC TCGTTGCGGGACTTAACCCAACATCTCACGACACGAGCTGACGACAGCCAT GCACCACCTGTACACCGACCACAAGGGGGCACCCATCTCTGGATGTTTCCG ATGTATGTCAAGCCTTGGTAAGGTTCTTCGCGTTGCGTCGAATTAAGCCACA TGCTCCGCCGCTTGTGCGGGCCCCCGTCAATTCCTTTGAGTTTTAGCCTTGC GGCCGTACTCCCCAGGCGGGGAACTTAATGCGTTAGCTGCGGCACGGACA ACGTGGAATGTCGCCCACACCTAGTTCCCAACGTTTACGGCGTGGACTACC AGGGTATCTAATCCTGTTCGCTCCCCACGCTTTCGCTCCTCAGCGTCAGTAT CGGCCCAGAGATCCGCCTTCGCCACCGGTGTTCCTCCTGATATCTGCGCATT TCACCGCTACACCAGGAATTCCGATCTCCCCTACCGAACTCTAGCCTGCCC GTATCGAATGCAGACCCGGGGTTAAGCCCCGGGCTTTCACATCCGACGCGA CAAGCCGCCTACGAGCTCTTTACGCCCAATAATTCCGGACAACGCTCGCGC CCTACGTATTACCGCGGCTGCTGGCACGTAGTTAGCCGGCGCTTCTTCTGCA GGTACCGTCACTTGCGCTTCTTCCCTGCTGAAAGAGGTTTACAACCCGAAG GCCGTCATCCCTCACGCGGCGTCGCTGCATCAGGCTTGCGCCCATTGTGCA ATATTCCCCACTGCTGCCTCCCGTAGGAGTCTGGGCCGTGTCTCAGTCCCA GTGTGGCCGGTCGCCCTCTCAGGCCGGCTACCCGTCGTCGCCTTGGTAGGC CATCACCCCACCAACAAGCTGATAGGCCGCGGGCTCATCCTGCACCGCCGG AGCTTTCCACCCGGTAAGATGCCTCACCAGGTCATATCCGGTATTAGACCCC GTTTCCAGGGCTTGTCCCAGAGTGCAGGGCAGATTGCCCACGTGTTACTCA CCCGTTCGCCACTAATCCACCACCGAAGCGGCTTCATCGTTCGACTGC 3

Phylogenetic tree of SN028 4

Figure S1. 1 H NMR (600 MHz, DMSO-d 6 ) spectrum of chloroindole (1). Figure S2. 13 C NMR (600 MHz, DMSO-d 6 ) spectrum of chloroindole (1). 5

Figure S3. 1 H- 1 H COSY spectrum of chloroindole (1) in DMSO-d 6. Figure S4. HSQC spectrum of chloroindole (1) in DMSO-d 6. 6

Figure S5. HMBC spectrum of chloroindole (1) in DMSO-d 6. Figure S6. HRESIMS spectrum of chloroindole (1). 7

Figure S7. 1 H NMR (600 MHz, CDCl 3 ) spectrum of streptoone A (2). Figure S8. 13 C NMR (150 MHz, CDCl 3 ) spectrum of streptoone A (2). 8

Figure S9. 1 H- 1 H COSY spectrum of streptoone A (2) in CDCl 3. Figure S10. HSQC spectrum of streptoone A (2) in CDCl 3. 9

Figure S11. HMBC spectrum of streptoone A (2) in CDCl 3. Figure S12. NOESY spectrum of streptoone A (2) in CDCl 3. 10

Figure S13. HRESIMS spectrum of streptoone A (2). Figure S14. 1 H NMR (600 MHz, CDCl3) spectrum of streptoone B (3). 11

Figure S15. 13 C NMR (150 MHz, CDCl3) spectrum of streptoone B (3). Figure S16. 1 H- 1 H COSY spectrum of streptoone B (3) in CDCl 3. 12

Figure S17. HSQC spectrum of streptoone B (3) in CDCl 3. Figure S18. HMBC spectrum of streptoone B (3) in CDCl 3. 13

Figure S19. NOESY spectrum of streptoone B (3) in CDCl 3. Figure S20. HRESIMS spectrum of streptoone B (3). 14

Figure S21. 1 H NMR (600 MHz, CDCl 3 ) spectrum of streptoone C (4). Figure S22. 13 C NMR (150 MHz, CDCl 3 ) spectrum of streptoone C (4). 15

Figure S23. 1 H- 1 H COSY spectrum of streptoone C (4) in CDCl 3. Figure S24. HSQC spectrum of streptoone C (4) in CDCl 3. 16

Figure S25. HMBC spectrum of streptoone C (4) in CDCl 3. Figure S26. NOESY spectrum of streptoone C (4) in CDCl 3. 17

Figure S27. HRESIMS spectrum of streptoone C (4). Table S1. Assignments of the 1 H (600 MHz) and 13 C (150 MHz) NMR data of the known compound X-14952B (5) in CDCl 3. position δ C, type δ H (J in Hz) position δ C, type δ H (J in Hz) 1 173.6, C 22 32.7, CH 1.76, m 2 43.5, CH 2 H a : 2.62, d (16.8) 23 76.8, CH 3.51, m H b : 2.55, d (16.8) 3 94.2, C 24 55.3, CH 2.64, m 4 35.2, CH 2 2.11, overlap 25 217.3, C 5 117.0, CH 5.45, m 26 38.1, CH 2 2.48, q (7.2) 6 133.0, C 27 7.4, CH 3 1.01, t (7.2) 7 80.2, CH 4.42, m 28 17.3, CH 3 0.90, d (6.7) 8 134.9, C 29 5.6, CH 3 0.87, d (6.8) 9 129.4, CH 5.41, dd (10.7, 4.2) 30 16.0, CH 3 0.81, d (6.7) 10 27.2, CH 2 H a : 2.07, m 31 12.8, CH 3 0.83, d (6.7) H b : 1.84, m 11 26.1, CH 2 1.22, m 32 22.8, CH 2 H a : 1.59, overlap H b : 1.51, overlap 12 35.2, CH 2 H a : 1.58, m 33 11.9, CH 3 0.85, t (7.4) H b : 1.42, m 13 82.4, CH 3.91, m 34 10.9, CH 3 1.36, s 14 134.2, CH 5.52, dd (15.3, 8.6) 35 19.3, CH 3 1.45, s 15 134.4, CH 5.21, dd (15.3, 9.5) 1 98.4, CH 4.53, dd (9.8, 1.7) 16 42.2, CH 2.11, overlap 2 36.9, CH 2 H a : 2.23, m H b : 1.64, m 17 77.9, CH 3.28, brd (8.5) 3 75.4, CH 4.61, ddd (11.8, 8.9, 5.3) 18 34.7, CH 1.96, m 4 75.1, CH 3.18, t (8.9) 19 82.1, CH 4.83, dd (8.9, 1.7) 5 72.1, CH 3.24, m 20 33.5, CH 1.76, m 6 17.9, CH 3 1.28, d (6.0) 21 37.1, CH 2 H a : 1.19, m H b : 0.96, m 3 -OCONH 2 157.6, C 18

Analytical data of the known compound X-14952B (5) White amorphous powder; [α] 24 D +77.9 (c 1.0, MeOH); IR (KBr) v max: 3450, 2969, 2844, 1716cm -1 ; 1 H (600 MHz, CDCl 3 ) and 13 C (150 MHz, CDCl 3 ) NMR data of 5 see Table S1; HRESIMS m/z 778.4757 [M H] (calcd for C 42 H 68 NO 12, 778.4741). 19