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1 SUPPORTING INFORMATION FOR Cytotoxic bagremycins from Mangrove-derived Streptomyces sp. Q22 Lei Chen, Weiyun Chai, Wenling Wang, Tengfei Song, Xiao-Yuan Lian,*,, Zhizhen Zhang,*, *Corresponding Authors. Tel: Fax: and Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan , China, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou , China 1
2 CONTENT Table S1. Sequences producing significant alignments....page 3 Table S2. NMR data of bagremycins A (1) and B (2).. page 4 Figure S1. 16S rdna sequence of Streptomyces sp. Q page 5 Figure S2. Activity of bagremycins B and C against glioma U87MG, U251, SHG44, and C6 cells....page 6 Figure S3. Bagremycin C induced apoptosis in U87MG cells page 6 Figure S4. Bagremycin C arrested cell cycle in U87MG cells page 7 Figures S5 and S6. 1H NMR spectra of bagremycin A (1) page 8 Figures S7 and S8. 13C NMR spectra of bagremycin A (1)... page 9 Figures S9 and S10. 1H NMR spectra of bagremycin B (2).... page 10 Figures S11 S13. 13C NMR spectra of bagremycin B (2).... page 11 Figures S14 S16. 1H NMR spectra of bagremycin C (3). page 12 Figures S17 S20. 13C NMR spectra of bagremycin C (3) page 14 Figures S21 S23. HSQC spectra of bagremycin C (3). page 16 Figures S24 S26. HMBC spectra of bagremycin C (3) page 17 Figure S27. HRESIMS of bagremycin C (3)... page 19 Figures S28 and S29. 1H NMR spectra of bagremycin D (4) page 19 Figures S30 and S31. 12C NMR spectra of bagremycin D (4)... page 20 Figures S32 and S33. HSQC spectra of bagremycin D (4)... page 21 Figure S34. HMBC spectrum of bagremycin D (4)..... page 22 Figure S35. HRESIMS of bagremycin D (4)... page 23 Figures S36 and S37. 1H NMR spectra of bagremycin E (5).... page 23 Figures S38 and S39. 13C NMR spectra of bagremycin E (5)... page 24 Figures S40 and S41. HMBC spectra of bagremycin E (5)... page 25 Figure S42. HRESIMS of bagremycin E (5)... page 26 Figures S43 S45. 1H NMR spectra of bagrelactone A (6) page 27 Figures S46 and S47. 13C NMR spectra of bagrelactone A (6)..... page 28 Figures S48 and S49. HSQC spectra of bagrelactone A (6) page 29 Figures S50 S52. HMBC spectra of bagrelactone A (6) page 30 Figure S53. HRESIMS of bagrelactone A (6).. page 32 Figures S54 S56. 1H NMR spectra of compound 6S... page 32 Figure S57. HRESIMS of compound 6S..... page 34 Figures S58 S60. 1H NMR spectra of compound 6R... page 34 Figure S61. HRESIMS of compound 6R..... page 36 2
3 Table S1. Sequences producing significant alignments Accession KP Description Streptomyces sp. T9 (2015) 16S ribosomal RNA gene, partial sequence Max score 2518 Total score 2518 Query coverage 99% Evalue EU Streptomyces sp. F42 16S % % ribosomal RNA gene, partial sequence KC Streptomyces sp % % NEAU-YX9 16S ribosomal RNA gene, partial sequence JX Streptomyces sp. OAct % % 16S ribosomal RNA gene, partial sequence KF Streptomyces sp % % MUSC106T 16S ribosomal RNA gene, partial sequence NR_ Streptomyces filipinensis % % strain NBRC S ribosomal RNA gene, partial sequence KJ Streptomyces sp. FXJ % % 16S ribosomal RNA gene, complete sequence NR_ Streptomyces durhamensis % % strain NBRC S ribosomal RNA gene, partial sequence NR_ Streptomyces durhamensis % % strain CSSP538 16S ribosomal RNA gene, partial sequence HE Streptomyces sp. IMCr % % partial 16S rrna gene, strain IMCr Ident 99% 3
4 Table S2. NMR data of bagremycins A (1) and B (2) (in DMSO-d6) No C, type 119.6, C 1 1 H (J, Hz) 1 3 C, type 117.7, C 2 1 H (J, Hz) , CH 7.40, d (2.2) 123.2, CH 8.66, d (2.0) , C 126.9, C , C 154.4, C , CH 6.79, d (8.2) 115.3, CH 6.95, d (8.5) , CH 7.27, dd (8.2, 2.2) 127.0, CH 7.71, dd (8.5, 2.0) , C 164.4, C , C 150.4, C , CH 7.17, d (8.6) 122.1, CH 7.19, d (8.5) , CH 7.52, d (8.6) 127.1, CH 7.54, d (8.5) , C 134.6, C , CH 7.52, d (8.6) 127.1, CH 7.64, d (8.5) , CH 7.17, d (8.6) 122.1, CH 7.19, d (8.5) , CH 6.73, dd (17.6, 11.0) 135.7, CH 6.74, dd (17.8, 11.0) , CH2 5.26, d (11.0); 5.80, d (17.6) 114.2, CH2 5.26, d (11.0); 5.82, d (17.8) , C , CH3 2.12, s NH , s 4
5 Figure S1. 16S rdna sequence of Streptomyces sp. Q22 GGGCCACCGGCTTCGGGTGTTACCGACTTTCGTGACGTGACGGGCGGTGTGTA CAAGGCCCGGGAACGTATTCACCGCAGCAATGCTGATCTGCGATTACTAGCGA CTCCGACTTCATGGGGTCGAGTTGCAGACCCCAATCCGAACTGAGACCGGCTT TTTGAGATTCGCTCCACCTCACGGTATCGCAGCTCATTGTACCGGCCATTGTAG CACGTGTGCAGCCCAAGACATAAGGGGCATGATGACTTGACGTCGTCCCCACC TTCCTCCGAGTTGACCCCGGCGGTCTCCTGTGAGTCCCCATCACCCCGAAGGG CATGCTGGCAACACAGAACAAGGGTTGCGCTCGTTGCGGGACTTAACCCAAC ATCTCACGACACGAGCTGACGACAGCCATGCACCACCTGTACACCGACCACA AGGGGGGCACTATCTCTAATGCTTTCCGGTGTATGTCAAGCCTTGGTAAGGTT CTTCGCGTTGCGTCGAATTAAGCCACATGCTCCGCCGCTTGTGCGGGCCCCCG TCAATTCCTTTGAGTTTTAGCCTTGCGGCCGTACTCCCCAGGCGGGGAACTTA ATGCGTTAGCTGCGGCACCGACGACGTGGAATGTCGCCAACACCTAGTTCCCA CCGTTTACGGCGTGGACTACCAGGGTATCTAATCCTGTTCGCTCCCCACGCTTT CGCTCCTCAGCGTCAGTAATGGCCCAGAGATCCGCCTTCGCCACCGGTGTTCC TCCTGATATCTGCGCATTTCACCGCTACACCAGGAATTCCGATCTCCCCTACCA CACTCTAGCTAGCCCGTATCGACTGCAGACTCGGGGTTAAGCCCCGAGCTTTC ACAATCGACGTGACAAGCCGCCTACGAGCTCTTTACGCCCAATAATTCCGGAC AACGCTTGCGCCCTACGTATTACCGCGGCTGCTGGCACGTAGTTAGCCGGCGC TTCTTCTGCAGGTACCGTCACTCTCGCTTCTTCCCTGCTGAAAGAGGTTTACAA CCCGAAGGCCGTCATCCCTCACGCGGCGTCGCTGCATCAGGCTTTCGCCCATT GTGCAATATTCCCCACTGCTGCCTCCCGTAGGAGTCTGGGCCGTGTCTCAGTC CCAGTGTGGCCGGTCGCCCTCTCAGGCCGGCTACCCGTCGTCGCCTTGGTGAG CCATTACCTCACCAACAAGCTGATAGGCCGCGGGCTCATCCTTCACCGCCGGA GCTTTACAGCCTCCCAGATGCCTGGGAGGCTCATATCCGGTATTAGACCCCGT TTCCAGGGCTTGTCCCAGAGTGAAGGGCAGATTGCCCACGTGTTACTCACCCG TTCGCCACTAATCCACCCCGAAGGGCTTCATCGTCGACTGC 5
6 Figure S2. Activity of bagremycins B and C against glioma U87MG, U251, SHG44, and C6 cells. Glioma cells were treated with bagremycins B and C at different concentrations for 72 h. DOX was used as a positive control. Values are means ± s.d. from five independent experiments Figure S3. Bagremycin C induced apoptosis in U87MG cells. U87MG cells were treated with bagremycin C (2.2 µm and 4.4µM) for 24 h, 48 h, and 72 h, stained with annexin-v FITC and PI, and then analyzed by flow cytometry. DOX (10.0 µm) was used as positive control (B1: necrotic cells; B2: late apoptotic cells; B3: normal glioma cells; B4: early apoptotic cells) 6
7 Figure S4. Bagremycin C arrested cell cycle in U87MG cells. U87MG cells were incubated with bagremycin C (2.2, 4.4, and 8.8 µm) and DOX (0.8 µm) for 12 h and then stained with PI and subjected to flow cytometric analysis for cell distribution at each phase of cell cycle. Percentage of cells at each stage of the cell cycle was shown. The proportion of cells in the G0/G1 phase of the cell cycle increased (G0: cell cycle Gap 0 phase; G1: cell cycle Gap 1 phase; S: cell cycle synthesis phase; G2: cell cycle Gap 2 phase; M: cell cycle mitosis phase) 7
8 Figure S5. 1H NMR spectrum of bagremycin A (1) Figure S6. 1H NMR spectrum of bagremycin A (1) 8
9 Figure S7. 13C NMR spectrum of bagremycin A (1) Figure S8. 13C NMR spectrum of bagremycin A (1) 9
10 Figure S9. 1H NMR spectrum of bagremycin B (2) Figure S10. 1H NMR spectrum of bagremycin B (2) 10
11 Figure S11. 13C NMR spectrum of bagremycin B (2) Figure S12. 13C NMR spectrum of bagremycin B (2) 11
12 Figure S13. 13C NMR spectrum of bagremycin B (2) Figure S14. 1H NMR spectrum of bagremycin C (3) 12
13 Figure S15. 1H NMR spectrum of bagremycin C (3) Figure S16 1H NMR spectrum of bagremycin C (3) 13
14 Figure S17. 13C NMR spectrum of bagremycin C (3) Figure S18. 13C NMR spectrum of bagremycin C (3) 14
15 Figure S19. 13C NMR spectrum of bagremycin C (3) Figure S20. 13C NMR spectrum of bagremycin C (3) 15
16 Figure S21. HSQC spectrum of bagremycin C (3) Figure S22. HSQC spectrum of bagremycin C (3) 16
17 Figure S23. HSQC spectrum of bagremycin C (3) Figure S24. HMBC spectrum of bagremycin C (3) 17
18 Figure S25. HMBC spectrum of bagremycin C (3) Figure S26. HMBC spectrum of bagremycin C (3) 18
19 Figure S27. HRESIMS of bagremycin C (3 Figure S28. 1H NMR spectrum of bagremycin D (4) 19
20 Figure S29. 1H NMR spectrum of bagremycin D (4) Figure S30. 13C NMR spectrum of bagremycin D (4) 20
21 Figure S31. 13C NMR spectrum of bagremycin D (4) Figure S32. HSQC spectrum of bagremycin D (4) 21
22 Figure S33. HSQC spectrum of bagremycin D (4) Figure S34. HMBC spectrum of bagremycin D (4) 22
23 Figure S35. HRESIMS of bagremycin D (4) Figure S36. 1H NMR spectrum of bagremycin E (5) 23
24 Figure S37. 1H NMR spectrum of bagremycin E (5) Figure S38. 13C NMR spectrum of bagremycin E (5) 24
25 Figure S39. 13C NMR spectrum of bagremycin E (5) Figure S40. HMBC spectrum of bagremycin E (5) 25
26 Figure S41. HMBC spectrum of bagremycin E (5) Figure S42. HRESIMS of bagremycin E (5) 26
27 Figure S43. 1H NMR spectrum of bagrelactone A (6) Figure S44. 1H NMR spectrum of bagrelactone A (6) 27
28 Figure S45. 1H NMR spectrum of bagrelactone A (6) Figure S46. 13C NMR spectrum of bagrelactone A (6) 28
29 Figure S47. 13C NMR spectrum of bagrelactone A (6) Figure S48. HSQC spectrum of bagrelactone A (6) 29
30 Figure S49. HSQC spectrum of bagrelactone A (6) Figure S50. HMBC spectrum of bagrelactone A (6) 30
31 Figure S51. HMBC spectrum of bagrelactone A (6) Figure S52. HMBC spectrum of bagrelactone A (6) 31
32 Figure S53. HRESIMS of bagrelactone A (6) Figure S54. 1H NMR spectrum of compound 6S 32
33 Figure S55. 1H NMR spectrum of compound 6S Figure S56. 1H NMR spectrum of compound 6S 33
34 Figure S57. HRESIMS of compound 6S Figure S58. 1H NMR spectrum of compound 6R 34
35 Figure S59. 1H NMR spectrum of compound 6R Figure S60. 1H NMR spectrum of compound 6R 35
36 Figure S61. 1H NMR spectrum of compound 6R 36
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