Anti-Mycobacterial Nucleoside Antibiotics from a Marine-Derived Streptomyces sp. TPU1236A
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structure of Streptcytosine A (1)
C# | δC | δH, mult. (J in Hz) | HMBC |
---|---|---|---|
2 | 157.4 | ||
4 | 165.0 | ||
5 | 99.1 | 7.58, d, (7.5) | 6 |
6 | 146.7 | 8.21, d, (7.5) | 2, 4, 5, 1′ |
8 | 168.4 | ||
9 | 131.6 | ||
10 | 130.8 | 8.10, d, (8.8) | 8, 11, 12, 14 |
11 | 120.6 | 7.87, d, (8.8) | 10, 13 |
12 | 142.0 | ||
13 | 120.6 | 7.87, d, (8.8) | 11, 14 |
14 | 130.8 | 8.10, d, (8.8) | 8, 10, 12, 13 |
16 | 172.2 | ||
17 | 68.3 | ||
19 | 66.1 | (a) 3.83, d, (11.6) | 16, 17 |
(b) 4.03. d, (11.6) | 16 | ||
20 | 17.6 | 1.57, s | 16, 17, 19 |
21 | 61.1 | 5.28, br s | 16, 17 |
1′ | 84.9 | 5.79, d, (7.8) | |
2′ | 31.1 | (a) 2.19, br d, (9.0) | 4′ |
(b) 1.71, m | 4′ | ||
3′ | 28.1 | (a) 1.71, m | 1′ |
(b) 2.41, m | |||
4′ | 76.7 | 3.46, m | |
5′ | 78.4 | 3.77, dq, (9.0, 6.0) | 4′ |
6′ | 19.3 | 1.39, d, (6.0) | 4′, 5′ |
1″ | 96.8 | 5.03, d, (3.6) | 4′, 3″, 5″ |
2″ | 74.0 | 3.56, dd, (9.1, 3.6) | 3″ |
3″ | 68.1 | 3.98, dd, (11.0, 9.1) | 2″, 4″ |
4″ | 72.1 | 3.12, dd (11.0, 10.0) | 3″, 5″, 6″, 7″, 8″ |
5″ | 64.2 | 4.10, dq, (10.0, 6.2) | |
6″ | 19.1 | 1.47, d, (6.2) | 4″, 5″ |
7″ | 42.6 | 3.01, s | 4″, 8″ |
8″ | 42.6 | 3.01, s | 4″, 7″ |
2.2. Structures of Streptcytosines B–E (2–5)
2 | 3 | 4 | 5 | |||||
---|---|---|---|---|---|---|---|---|
C# | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) | δC | δH, mult. (J in Hz) |
2 | 156.6 | 155.5 | 154.2 | 157.8 | ||||
4 | 164.6 | 164.2 | 164.3 | 164.8 | ||||
5 | 98.4 | 7.34, d (7.5) | 98.3 | 7.30, d (7.6) | 98.2 | 7.26, d (7.5) | 99.2 | 7.47, br d (7.6) |
6 | 146.8 | 8.19, d (7.5) | 147.5 | 8.23, d (7.6) | 147.0 | 8.21, d (7.5) | 146.7 | 8.12, d (7.6) |
8 | 166.2 | 171.3 | 168.2 | 176.5 | ||||
9 | 115.7 | 6.07, d (14.6) | 133.5 | 118.7 | 5.95, qq (1.3, 1.3) | 47.3 | 2.32, d (7.2) | |
10 | 150.7 | 8.01, d (14.6) | 137.4 | 6.71, q (7.0) | 161.3 | 27.1 | 2.10, m | |
11 | 14.7 | 2.42, s | 14.7 | 1.89, d (7.0) | 28.0 | 1.99, d (1.2) | 22.7 | 0.99, d (6.7) |
12 | –– | –– | 12.2 | 1.90, s | 20.8 | 2.24, d (1.2) | 22.7 | 0.99, d (6.7) |
1′ | 85.0 | 5.71, dd (9.9, 2.1) | 85.0 | 5.71, dd (10.1, 2.2) | 84.9 | 5.71, dd (10.0, 2.2) | 84.9 | 5.70, dd (9.9, 1.8) |
2′ | 32.4 | (a) 2.15, m (b) 1.67, m | 32.4 | (a) 2.16, m (b) 1.67, m | 32.4 | (a) 2.15, m (b) 1.67, m | 32.4 | (a) 2.15, m (b) 1.66, m |
3′ | 31.7 | (a) 1.67, m (b) 2.13, m | 31.7 | (a) 1.67, m (b) 2.13, m | 31.6 | (a) 1.67, m (b) 2.12, m | 31.7 | (a) 1.66, m (b) 2.12, m |
4′ | 71.8 | 3.28, m | 71.7 | 3.28, m | 71.8 | 3.27, m | 71.8 | 3.28, m |
5′ | 80.7 | 3.51, dq (9.1, 6.1) | 80.7 | 3.51, dq (9.2, 6.2) | 80.6 | 3.51, dq (9.1. 6.1) | 80.6 | 3.50, dq (9.2, 6.2) |
6′ | 18.6 | 1.34, d (6.1) | 18.6 | 1.34, d (6.2) | 18.6 | 1.33, d (6.1) | 18.6 | 1.33, d (6.2) |
2.3. Anti-Mycobacterial Activity of Compounds 1–11
Compound | 5 μg/disc | 10 μg/disc | MIC (μg/mL) |
---|---|---|---|
1 | 9 | 12 | 32 |
2 | –– a | –– | n.d.b |
3 | –– | –– | n.d. |
4 | –– | –– | n.d. |
5 | –– | –– | n.d. |
6 | –– | –– | n.d. |
7 | 9 | 13 | 32 |
8 | 18 | 24 | 16 |
9 | 21 | 26 | 8 |
10 | –– | 12 | >64 |
11 | 9 | 12 | 64 |
streptomycin sulfate | 30 | 38 | 0.50 |
3. Experimental Section
3.1. General Experimental Procedures
3.2. Isolation, Identification, and Fermentation of Producing Bacterium
3.3. Extraction and Isolation of Compounds 1–11
3.4. Anti-Mycobacterial Assay
4. Conclusions
Acknowledgments
Authors Contribution
Conflicts of Interest
References
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Bu, Y.-Y.; Yamazaki, H.; Ukai, K.; Namikoshi, M. Anti-Mycobacterial Nucleoside Antibiotics from a Marine-Derived Streptomyces sp. TPU1236A. Mar. Drugs 2014, 12, 6102-6112. https://doi.org/10.3390/md12126102
Bu Y-Y, Yamazaki H, Ukai K, Namikoshi M. Anti-Mycobacterial Nucleoside Antibiotics from a Marine-Derived Streptomyces sp. TPU1236A. Marine Drugs. 2014; 12(12):6102-6112. https://doi.org/10.3390/md12126102
Chicago/Turabian StyleBu, Ying-Yue, Hiroyuki Yamazaki, Kazuyo Ukai, and Michio Namikoshi. 2014. "Anti-Mycobacterial Nucleoside Antibiotics from a Marine-Derived Streptomyces sp. TPU1236A" Marine Drugs 12, no. 12: 6102-6112. https://doi.org/10.3390/md12126102