Structure and Antibacterial Activity of Ambobactin, a New Telomycin-Like Cyclic Depsipeptide Antibiotic Produced by Streptomyces ambofaciens F3
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation
Ambobactin (1) | Telomycin | |||||
---|---|---|---|---|---|---|
δC (ppm) * | δH (ppm, J = Hz) * | HMBC | 1H, 1H-COSY | δC (ppm) * | δH (ppm) * | |
Aspartic Acid (Asp) | ||||||
COOH | 170.6 | 170.07 | ||||
Cα | 51.5 | 3.93 (m) | 170.6 | 2.33, 2.74 | 48.65 | 4.17 |
Cβ | 38.3 | 2.33 (d, J = 10.5 Hz) | 168.8 | 3.93 | 34.24 | 2.82 |
2.74 (t, J = 10.5 Hz) | 168.8 | |||||
COγ | 168.8 | 168.55 | ||||
Serine (Ser) | ||||||
CO | 169.0 | 170.70 | ||||
Cα | 57.8 | 4.11 (m) | 169.0 | 3.64, 3.74, 8.67 | 54.00 | 4.61 |
Cβ | 61.5 | 3.64, 3.74 (m) | 4.11, 4.46 | 61.66 | 3.46, 3.68 | |
NH | 8.67 (s) | 4.11 | 8.43 | |||
OH | 4.46 (s) | 3.64, 3.74 | ||||
Threonine1 (Thr1) | ||||||
CO | 168.9 | 168.28 | ||||
Cα | 57.9 | 4.46 (m) | 168.9 | 4.99, 7.76 | 58.3 | 4.25 |
Cβ | 71.2 | 4.99 (m) | - | 4.46, 1.15 | 71.0 | 4.98 |
Cγ | 15.9 | 1.15 (d, J = 6.0 Hz) | 57.9, 71.2 | 4.99 | 15.77 | 1.23 |
NH | 7.76 (d, J = 7.0 Hz) | 4.46 | 8.10 | |||
3-Hydroxy-l-Proline (3-HyP1) | ||||||
CO | 171.3 | |||||
C2 | 67.5 | 4.19 (m) | 73.6, 171.3 | 4.21 | 66.8 | 4.21 |
C3 | 73.6 | 4.21 (m) | 1.96, 2.16, 4.19, 5.78 | 73.07 | 4.22 | |
C4 | 33.9 | 1.96, 2.16 (m) | 3.52, 3.82, 4.21 | 33.32 | 2.00, 2.19 | |
C5 | 44.9 | 3.52, 3.82 (m) | 1.96, 2.16 | 44.32 | 3.49, 3.83 | |
OH | 5.78 (s) | 4.21 | ||||
α,β-Dehydrotryptophan (ΔTry) | ||||||
CO | 163.9 | 163.57 | ||||
C2 | 122.9 | - | 122.17 | |||
C3 | 122.9 | 7.46 (s) | 127.7, 163.9 | 7.62, 7.08 | 122.67 | |
C4 | 109.0 | - | 108.38 | |||
C5 | 128.2 | 7.95 (s) | 109.0, 127.7, 135.9 | 11.72 | 127.67 | 7.95 |
C6a | 135.9 | - | 135.34 | |||
C7 | 112.3 | 7.38 (d, J = 8.2 Hz) | 120.6, 127.7 | 7.14 | 111.73 | 7.38 |
C8 | 122.5 | 7.14 (t, J = 7.6 Hz) | 118.1, 127.7, 135.9 | 7.38 | 121.97 | 7.13 |
C9 | 120.6 | 7.08 (t, J = 7.6 Hz) | 112.3 | 7.62 | 120.08 | 7.08 |
C10 | 118.1 | 7.62 (d, J = 8.0 Hz) | 109.0, 122.5, 127.7, 135.9 | 7.08 | 117.54 | 7.60 |
C10a | 127.7 | - | 127.67 | |||
6-NH | 11.72 (s) | 109.0, 127.7, 135.9 | 11.70 | |||
NH | 10.08 (s) | 163.9, 122.5, 128.2 | 10.14 | |||
3-Methyl-Tryptophan (3-MeTry) | ||||||
CO | 171.8 | |||||
C2 | 60.2 | 4.46 (m) | 33.2, 171.8 | 7.56, 8.69 | 60.0 | 4.47 |
C3 | 33.2 | 3.65 (m) | 112.0 | 1.24, 4.46 | 32.49 | 3.61 |
C4 | 117.5 | - | - | 116.6 | ||
C5 | 123.3 | 7.08 (s) | 112.0, 117.5, 126.3, 137.2 | 10.75 | 122.87 | |
C6a | 137.2 | - | - | 136.56 | ||
C7 | 112.0 | 7.28 (d, J = 8.2 Hz) | 126.3, 118.7 | 10.75, 7.00 | 111.43 | 7.27 |
C8 | 121.2 | 7.00 (t, J = 7.6 Hz) | 119.5, 121.2, 126.3, 137.2 | 7.28 | 120.63 | 7.01 |
C9 | 118.7 | 6.93 (t, J = 7.6 Hz) | 112.0, 126.3 | 7.56 | 118.17 | 6.92 |
C10 | 119.5 | 7.56 (d, J = 8.2 Hz) | 117.5, 121.2, 126.3, 137.2 | 6.93 | 119.01 | 7.58 |
C10a | 126.3 | - | - | 125.56 | ||
C11 | 19.8 | 1.24 (d, J = 7.0 Hz) | 33.2, 60.2, 117.5 | 3.65 | 18.37 | |
6-NH | 10.75 (s) | 117.5, 126.3, 137.2 | 7.08, 7.28 | 10.75 | ||
NH | 8.69 (s) | 7.74 | ||||
3-Hydroxy-Leucine (3-HyLeu) | ||||||
CO | 171.6 | |||||
Cα | 52.4 | 4.49 (m) | 171.6 | 3.32, 6.62 | 51.60 | 4.54 |
Cβ | 75.2 | 3.32 (m) | - | 1.94, 4.49, 4.74 | 75.18 | 3.29 |
Cγ | 29.2 | 1.94 (m) | - | 0.79, 0.84, 3.32 | 28.78 | 1.94 |
Cδ1 | 20.6 | 0.84 (d, J = 6.6 Hz) | 16.5, 29.2, 75.2 | 1.94 | 19.63 | 0.87 |
Cδ2 | 16.5 | 0.79 (d, J = 6.6 Hz) | 20.6, 29.2, 75.2 | 1.94 | 17.19 | 0.84 |
OH | 4.74 (s) | 3.32 | ||||
NH | 6.62 (s) | 4.49 | ||||
3-Hydroxy-l-Proline (3-HyP2) | ||||||
CO | 169.4 | |||||
C2 | 62.2 | 4.67 (m) | 169.4 | 4.71 | 63.02 | 4.61 |
C3 | 69.5 | 4.71 (m) | 1.76, 2.03, 4.67, 4.49 | 69.35 | 4.61 | |
C4 | 32.1 | 1.76, 2.03 (m) | 3.74, 3.93, 4.71 | 33.43 | 1.90 | |
C5 | 45.0 | 3.74, 3.93 (m) | 1.76, 2.03 | 45.25 | 3.61 | |
OH | 4.49 (s) | 4.71 | ||||
Glycine (Gly) | ||||||
CO | 169.1 | |||||
Cα | 41.5 | 3.80, 4.44 (m) | 169.1 | 8.86 | 41.0 | 3.84, 4.42 |
NH | 8.86 (s) | 3.80, 4.44 | 8.66 | |||
Alanine (Ala) | ||||||
CO | 172.4 | 171.4 | ||||
Cα | 48.5 | 4.45 (m) | 172.4 | 1.05, 7.73 | 47.85 | 4.45 |
Cβ | 17.5 | 1.05 (d, J = 6.0 Hz) | 48.5, 172.4 | 4.45 | 17.05 | 1.02 |
NH | 7.73 (d, J = 7.0 Hz) | 4.45 | 8.05 | |||
Threonine2 (Thr2) | ||||||
CO | 169.3 | |||||
Cα | 58.8 | 4.09 (m) | 67.2, 169.3 | 3.82, 7.42 | 57.22 | 4.22 |
Cβ | 67.2 | 3.82 (m) | 1.07, 4.09 | 66.91 | 3.64 | |
Cγ | 21.5 | 1.07 (d, J = 6.0 Hz) | 67.2, 58.8 | 3.82 | 20.65 | 1.00 |
NH | 7.42 (s) | 4.09 | 7.53 |
Derivatives | Time (min) | ||||||
---|---|---|---|---|---|---|---|
Asp | Ser | 3-HyLeu | Thr | Ala | 3-HyP | 3-MeTry | |
L-FDAA | 10.62 | 7.12 | 21.36 | 7.93 | 18.86 | 10.47 | 44.11 |
D-FDAA | 12.21 | 7.55 | 34.95 | 8.68 | 26.99 | 12.13 | 41.59 |
2.2. Antibacterial Activity
Compounds | MIC (μg/mL) | ||||||||
---|---|---|---|---|---|---|---|---|---|
BS | BC | SA | EC | PA | ErC | PS | AS | XO | |
Ambobactin | 3.13 | 25 | 25 | 6.25 | >100 | 6.25 | 6.25 | 6.25 | 6.25 |
Ampicillin | 1.56 | 6.25 | 6.25 | 3.13 | >100 | 6.25 | 6.25 | 6.25 | 6.25 |
3. Experimental Section
3.1. General Experimental Procedures
3.2. Microorganism and Fermentation
3.3. Extraction and Isolation
3.4. Acid Hydrolysis and Advanced Marfey’s Analysis
3.5. HPLC-UV/MS Analysis
3.6. Tandem MS Analysis
3.7. Antibacterial Activity
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Wei, S.; Zhang, W.; Ji, Z. Structure and Antibacterial Activity of Ambobactin, a New Telomycin-Like Cyclic Depsipeptide Antibiotic Produced by Streptomyces ambofaciens F3. Molecules 2015, 20, 16278-16289. https://doi.org/10.3390/molecules200916278
Wei S, Zhang W, Ji Z. Structure and Antibacterial Activity of Ambobactin, a New Telomycin-Like Cyclic Depsipeptide Antibiotic Produced by Streptomyces ambofaciens F3. Molecules. 2015; 20(9):16278-16289. https://doi.org/10.3390/molecules200916278
Chicago/Turabian StyleWei, Shaopeng, Wenhao Zhang, and Zhiqin Ji. 2015. "Structure and Antibacterial Activity of Ambobactin, a New Telomycin-Like Cyclic Depsipeptide Antibiotic Produced by Streptomyces ambofaciens F3" Molecules 20, no. 9: 16278-16289. https://doi.org/10.3390/molecules200916278