New Azalomycin F Analogs from Mangrove Streptomyces sp. 211726 with Activity against Microbes and Cancer Cells
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation
Position | 1 | 2 | 3 | 6 | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | ||||
C-1 | 170.2 | - | 170.1 | - | 170.1 | - | 170.1 | - | |||
C-2 | 126.8 | - | 126.7 | - | 126.8 | - | 126.8 | - | |||
C-3 | 140.3 | 7.09 d (11.2) | 140.3 | 7.10 d (11.0) | 140.2 | 7.10 d (11.2) | 140.3 | 7.10 d (11.0) | |||
C-4 | 127.6 | 6.43 dd (11.5, 14.9) | 127.6 | 6.43 dd (11.5, 14.7) | 127.6 | 6.43 dd (11.9, 14.3) | 127.6 | 6.43 dd (11.5, 14.8) | |||
C-5 | 146.2 | 6.07 dd (15.1, 9.0) | 146.1 | 6.08 dd (14.8, 9.0) | 146.1 | 6.08 dd (14.0, 9.0) | 146.1 | 6.08 dd (14.9, 9.0) | |||
C-6 | 44.8 | 2.43 m | 44.7 | 2.44 m | 44.6 | 2.43 m | 44.7 | 2.44 m | |||
C-7 | 75.9 | 3.80 m | 75.8 | 3.77 m | 75.8 | 3.77 m | 75.8 | 3.77 m | |||
C-8 | 39.3 | 1.50 m, 1.78 m | 39.3 | 1.50 m, 1.78 m | 39.3 | 1.50 m, 1.77 m | 39.3 | 1.50 m, 1.78 m | |||
C-9 | 75.4 | 3.80 m | 75.2 | 3.80 m | 75.2 | 3.80 m | 75.2 | 3.80 m | |||
C-10 | 44.7 | 1.54 m | 44.6 | 1.53 m | 44.5 | 1.54 m | 44.6 | 1.53 m | |||
C-11 | 72.2 | 3.91 m | 72.2 | 3.87 m | 72.2 | 3.91 m | 72.2 | 3.87 m | |||
C-12 | 33.5 | 1.62 m, 1.38 m | 33.5 | 1.60 m, 1.38 m | 33.5 | 1.62 m, 1.37 m | 33.4 | 1.62 m, 1.37 m | |||
C-13 | 30.7 | 1.30 m, 1.45 m | 30.6 | 1.30 m, 1.42 m | 30.6 | 1.30 m, 1.43 m | 30.6 | 1.30 m, 1.43 m | |||
C-14 | 40.6 | 1.60 m | 40.5 | 1.61 m | 40.7 | 1.61 m | 40.5 | 1.61 m | |||
C-15 | 72.7 | 3.86 m | 72.7 | 3.87 m | 72.4 | 3.86 m | 72.7 | 3.87 m | |||
C-16 | 41.9 | 1.80 m | 41.8 | 1.81 m | 41.9 | 1.82 m | 41.8 | 1.81 m | |||
C-17 | 99.9 | - | 100.0 | - | 99.8 | - | 99.9 | - | |||
C-18 | 77.5 | 3.34 d (9.2) | 77.4 | 3.35 d (9.1) | 77.2 | 3.35 d (9.2) | 77.5 | 3.35 d (9.1) | |||
C-19 | 69.9 | 3.87 m | 69.9 | 3.88 m | 69.7 | 3.87 m | 69.8 | 3.88 m | |||
C-20 | 41.4 | 1.89 m, 1.30 m | 41.3 | 1.89 m, 1.30 m | 41.2 | 1.90 m, 1.31 m | 41.3 | 1.89 m, 1.31 m | |||
C-21 | 65.7 | 4.17 m | 66.2 | 4.16 m | 66.3 | 4.16 m | 66.3 | 4.16 m | |||
C-22 | 44.5 | 1.52 m | 41.9 | 1.82 m | 41.8 | 1.88 m | 41.9 | 1.81 m | |||
C-23 | 66.3 | 4.03 m | 70.9 | 5.29 m | 70.7 | 5.27 m | 70.9 | 5.29 m | |||
C-24 | 44.6 | 1.69 m | 44.0 | 1.70 m | 44.0 | 1.72 m | 44.1 | 1.76 m, 1.66 m | |||
C-25 | 70.8 | 5.28 m | 65.7 | 3.86 m | 65.6 | 3.87 m | 65.7 | 3.86 m | |||
C-26 | 44.0 | 1.61 m, 1.83 m | 46.3 | 1.51 m | 46.4 | 1.51 m | 46.3 | 1.51 m | |||
C-27 | 65.7 | 3.88 m | 65.8 | 4.04 m | 65.6 | 4.04 m | 65.8 | 4.04 m | |||
C-28 | 44.2 | 1.78 m | 44.1 | 1.54 m | 44.1 | 1.53 m | 44.1 | 1.63 m | |||
C-29 | 74.2 | 4.18 m | 74.2 | 4.18 m | 74.2 | 4.18 m | 74.2 | 4.18 m | |||
C-30 | 140.2 | - | 140.1 | - | 140.1 | - | 140.1 | - | |||
C-31 | 125.3 | 5.98 d (10.4) | 125.3 | 5.98 d (10.7) | 125.2 | 5.98 d (10.5) | 125.3 | 5.98 d (10.7) | |||
C-32 | 128.6 | 6.22 dd (10.9, 14.5) | 128.5 | 6.23 dd (10.9, 14.9) | 128.6 | 6.22 dd (10.9, 14.9) | 128.5 | 6.23 dd (10.9, 14.8) | |||
C-33 | 136.3 | 5.43 m | 136.3 | 5.44 m | 136.2 | 5.45 m | 136.3 | 5.44 m | |||
C-34 | 41.0 | 2.57 m | 40.7 | 2.57 m | 41.0 | 2.57 m | 40.9 | 2.57 m | |||
C-35 | 80.9 | 4.78 dd (7.6, 4.0) | 80.9 | 4.79 dd (7.7, 4.1) | 80.8 | 4.78 dd (7.8, 3.9) | 80.9 | 4.79 dd (7.6, 4.1) | |||
C-36 | 35.3 | 1.82 m | 35.3 | 1.82 m | 35.2 | 1.81 m | 35.3 | 1.82 m | |||
C-37 | 34.4 | 1.15 m, 1.35 m | 34.4 | 1.15 m, 1.35 m | 34.5 | 1.15 m, 1.35 m | 34.4 | 1.15 m, 1.35 m | |||
C-38 | 27.9 | 1.42 m | 27.8 | 1.42 m | 27.9 | 1.41 m | 27.9 | 1.42 m | |||
C-39 | 33.6 | 1.99 m | 33.6 | 1.99 m | 33.6 | 1.99 m | 33.6 | 1.99 m | |||
C-40 | 132.6 | 5.44 m | 132.5 | 5.44 m | 132.6 | 5.44 m | 132.6 | 5.44 m | |||
C-41 | 130.3 | 5.44 m | 130.3 | 5.44 m | 130.1 | 5.50 m | 130.2 | 5.44 m | |||
C-42 | 30.7 | 2.07 m | 30.4 | 2.07 m | 30.8 | 2.07 m | 30.6 | 2.07 m | |||
C-43 | 29.9 | 1.67 m | 29.8 | 1.64 m | 29.8 | 1.64 m | 29.8 | 1.64 m | |||
C-44 | 42.2 | 3.17 t (7.3) | 42.0 | 3.15 t (7.1) | 42.0 | 3.15 t (7.0) | 42.0 | 3.15 t (7.1) | |||
C-45 | 12.9 | 1.92 s | 12.9 | 1.92 s | 12.9 | 1.92 s | 12.9 | 1.92 s | |||
C-46 | 17.1 | 1.11 d (6.8) | 17.1 | 1.12 d (6.8) | 17.1 | 1.11 d (6.8) | 17.1 | 1.12 d (6.8) | |||
C-47 | 10.5 | 0.89 d (6.9) | 10.5 | 0.89 d (6.9) | 10.5 | 0.89 d (6.9) | 10.5 | 0.89 d (6.9) | |||
C-48 | 15.2 | 0.91 d (6.7) | 15.3 | 0.92 d (6.7) | 15.3 | 0.91 d (6.7) | 15.3 | 0.92 d (6.7) | |||
C-49 | 13.1 | 1.65 s | 13.1 | 1.65 s | 13.3 | 1.65 s | 13.1 | 1.65 s | |||
C-50 | 17.8 | 1.01 d (6.7) | 17.9 | 1.00 d (6.7) | 17.9 | 1.00 d (6.6) | 17.9 | 1.00 d (6.8) | |||
C-51 | 14.4 | 0.94 d (6.7) | 14.5 | 0.95 d (6.7) | 14.4 | 0.94 d (6.7) | 14.5 | 0.94 d (6.7) | |||
C-52 | 157.4 | - | 157.4 | - | 158.7 | - | 158.3 | - | |||
C-53a | 28.4 | 2.85 s | 28.4 | 2.85 s | 28.4 | 2.84 s | |||||
C-53b | 28.4 | 2.85 s | 28.4 | 2.85 s | |||||||
C-1′ | 171.9 | - | 174.1 | - | 175.5 | - | 175.4 | - | |||
C-2′ | 46.0 | 3.22 m | 61.7 | 3.44 d (4.0) | 35.0 | 2.36 t (7.4) | 35.0 | 2.36 t (7.5) | |||
C-3′ | 173.9 | - | 30.8 | 2.28 m | 26.0 | 1.62 m | 26.0 | 1.61 m | |||
3′-CH3 | 17.9 | 1.02 d (6.8) | |||||||||
C-4′ | 19.2 | 1.07 d (6.8) | 30.4 | 1.42 m | 30.3 | 1.35 m | |||||
C-5′ | 40.3 | 1.18 m | 30.4 | 1.31 m | |||||||
C-6′ | 29.2 | 1.29 m | 30.8 | 1.30 m | |||||||
6′-CH3 | 23.8 | 0.88 d (6.6) | |||||||||
C-7′ | 23.7 | 0.88 d (6.6) | 28.5 | 1.29 m | |||||||
C-8′ | 40.3 | 1.17 m | |||||||||
C-9′ | 29.2 | 1.31 m | |||||||||
9′-CH3 | 23.1 | 0.89 d (6.8) | |||||||||
C-10′ | 23.1 | 0.89 d (6.8) |
2.2. Biological Assays
Compounds | MICs (μg/mL) | IC50 (μg/mL) | |||
---|---|---|---|---|---|
Candida albicans ATCC 10231 | Staphylococcus aureus S014 | Bacillus subtilis S028 | Eschzerichia coli S002 | HCT-116 | |
1 | 3.13 | 0.39 | 0.20 | 3.13 | 5.00 |
2 | 6.25 | 1.56 | 0.39 | 6.25 | 1.95 |
3 | 3.13 | 0.78 | 0.39 | 3.13 | 2.46 |
4 | 1.56 | 1.56 | 0.20 | 6.25 | 2.45 |
5 | 1.56 | 0.78 | 0.78 | 12.5 | 1.81 |
6 | 3.13 | 0.39 | 0.39 | 25.00 | 1.54 |
7 | 3.13 | 0.39 | 0.39 | 3.13 | 2.46 |
Positive controls * | 2.0 | 0.50 | 0.20 | 2.0 | 0.18 |
2.3. Discussion
3. Experimental Section
3.1. General Experimental Procedures
3.2. Actinomycetes Material and Fermentation
3.3. Extract and Isolation
3.4. Biological Assays
4. Conclusions
Acknowledgments
References and Notes
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Yuan, G.; Hong, K.; Lin, H.; She, Z.; Li, J. New Azalomycin F Analogs from Mangrove Streptomyces sp. 211726 with Activity against Microbes and Cancer Cells. Mar. Drugs 2013, 11, 817-829. https://doi.org/10.3390/md11030817
Yuan G, Hong K, Lin H, She Z, Li J. New Azalomycin F Analogs from Mangrove Streptomyces sp. 211726 with Activity against Microbes and Cancer Cells. Marine Drugs. 2013; 11(3):817-829. https://doi.org/10.3390/md11030817
Chicago/Turabian StyleYuan, Ganjun, Kui Hong, Haipeng Lin, Zhigang She, and Jia Li. 2013. "New Azalomycin F Analogs from Mangrove Streptomyces sp. 211726 with Activity against Microbes and Cancer Cells" Marine Drugs 11, no. 3: 817-829. https://doi.org/10.3390/md11030817
APA StyleYuan, G., Hong, K., Lin, H., She, Z., & Li, J. (2013). New Azalomycin F Analogs from Mangrove Streptomyces sp. 211726 with Activity against Microbes and Cancer Cells. Marine Drugs, 11(3), 817-829. https://doi.org/10.3390/md11030817