Supporting information

Transcription

1 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 , People s Republic of China Engineering & Technological Research Center of Biopesticide for Liaoning Province, Shenyang , People s Republic of China

2 List of contents 16S ribosomal DNA gene sequence data of SN Phylogenetic tree of SN 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) Figure S3. 1 H- 1 H COSY spectrum of chloroindole (1) in DMSO-d Figure S4. HSQC spectrum of chloroindole (1) in DMSO-d Figure S5. HMBC spectrum of chloroindole (1) in DMSO-d Figure S6. HRESIMS spectrum of chloroindole (1) 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) Figure S9. 1 H- 1 H COSY spectrum of streptoone A (2) in CDCl Figure S10. HSQC spectrum of streptoone A (2) in CDCl Figure S11. HMBC spectrum of streptoone A (2) in CDCl Figure S12. NOESY spectrum of streptoone A (2) in CDCl Figure S13. HRESIMS spectrum of streptoone A (2) Figure S14. 1 H NMR (600 MHz, CDCl3) spectrum of streptoone B (3) Figure S C NMR (150 MHz, CDCl3) spectrum of streptoone B (3) Figure S16. 1 H- 1 H COSY spectrum of streptoone B (3) in CDCl Figure S17. HSQC spectrum of streptoone B (3) in CDCl Figure S18. HMBC spectrum of streptoone B (3) in CDCl Figure S19. NOESY spectrum of streptoone B (3) in CDCl

3 Figure S20. HRESIMS spectrum of streptoone B (3) Figure S21. 1 H NMR (600 MHz, CDCl 3 ) spectrum of streptoone C (4) Figure S C NMR (150 MHz, CDCl 3 ) spectrum of streptoone C (4) Figure S23. 1 H- 1 H COSY spectrum of streptoone C (4) in CDCl Figure S24. HSQC spectrum of streptoone C (4) in CDCl Figure S25. HMBC spectrum of streptoone C (4) in CDCl Figure S26. NOESY spectrum of streptoone C (4) in CDCl 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 Analytical data of the known compound X-14952B (5)

4 16S ribosomal DNA gene sequence data of SN0280 Primers 27F:5 -AGAGTTTGATCCTGGCTCAG R: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

5 Phylogenetic tree of SN028 4

6 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

7 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

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

9 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

10 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

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

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

13 Figure S 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

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

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

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

17 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

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

19 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) , C , CH 1.76, m , CH 2 H a : 2.62, d (16.8) , CH 3.51, m H b : 2.55, d (16.8) , C , CH 2.64, m , CH , overlap , C , CH 5.45, m , CH , q (7.2) , C , CH , t (7.2) , CH 4.42, m , CH , d (6.7) , C , CH , d (6.8) , CH 5.41, dd (10.7, 4.2) , CH , d (6.7) , CH 2 H a : 2.07, m , CH , d (6.7) H b : 1.84, m , CH , m , CH 2 H a : 1.59, overlap H b : 1.51, overlap , CH 2 H a : 1.58, m , CH , t (7.4) H b : 1.42, m , CH 3.91, m , CH , s , CH 5.52, dd (15.3, 8.6) , CH , s , CH 5.21, dd (15.3, 9.5) , CH 4.53, dd (9.8, 1.7) , CH 2.11, overlap , CH 2 H a : 2.23, m H b : 1.64, m , CH 3.28, brd (8.5) , CH 4.61, ddd (11.8, 8.9, 5.3) , CH 1.96, m , CH 3.18, t (8.9) , CH 4.83, dd (8.9, 1.7) , CH 3.24, m , CH 1.76, m , CH , d (6.0) , CH 2 H a : 1.19, m H b : 0.96, m 3 -OCONH , C 18

20 Analytical data of the known compound X-14952B (5) White amorphous powder; [α] 24 D (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 [M H] (calcd for C 42 H 68 NO 12, ). 19