Divergolides T–W with Apoptosis-Inducing Activity from the Mangrove-Derived Actinomycete Streptomyces sp. KFD18
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General Experimental Procedure
3.2. Strain and Fermentation
3.3. Extraction and Isolation
3.4. Bioassays for Cytotoxic and Apoptosis-Inducing Activity
4. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Position | 1 | 2 | 3 | 4 |
---|---|---|---|---|
δC | δC | δC | δC | |
1 | 177.2, C | 177.1, C | 177.2, C | 176.8, C |
2 | 55.2, CH | 55.3, CH | 55.8, CH | 55.3, CH |
3 | 131.7, CH | 132.9, CH | 126.7, CH | 132.5 CH |
4 | 136.8, C | 136.1, C | 138.4, C | 135.0, C |
4a | 22.0, CH3 | 22.1, CH3 | 21.4, CH3 | 13.5, CH3 |
5 | 168.0, C | 167.7, C | 169.5, C | 167.9, C |
6 | 74.6, CH | 76.7, CH | 74.5, CH | 74.0, CH |
7 | 36.1, CH2 | 70.5, CH | 36.6, CH2 | 36.3, CH2 |
8 | 125.1, CH | 128.2, CH | 126.3, CH | 125.3, CH |
9 | 139.6, CH | 136.1, CH | 138.8, CH | 138.6, CH |
10 | 46.0, CH | 45.9, CH | 44.2, CH | 43.2, CH |
10a | 26.9, CH2 | 27.0, CH2 | 29.3, CH2 | 25.6, CH2 |
10b | 13.2, CH3 | 13.2, CH3 | 12.7, CH3 | 11.1, CH3 |
11 | 31.7, CH2 | 31.5, CH2 | 34.8, CH2 | 31.6, CH2 |
12 | 40.5, CH2 | 40.5, CH2 | 42.5, CH2 | 42.0, CH2 |
13 | 212.4, C | 212.4, C | 212.1, C | 212.1, C |
14 | 130.1, C | 130.2, C | 127.8, C | 130.6, C |
15 | 153.5, C | 153.5, C | 153.4, C | 152.9, C |
16 | 132.6, C | 132.9, C | 133.1, C | 133.4, C |
16a | 17.0, CH3 | 17.0, CH3 | 17.0, CH3 | 16.9, CH3 |
17 | 130.8, CH | 130.8, CH | 132.8, CH | 131.9, CH |
18 | 134.3, C | 136.1, C | 134.3, C | 135.0, C |
19 | 73.7, C | 73.8, C | 73.6, C | 75.2, C |
20 | 164.8, C | 164.7, C | 164.6, C | 164.6, C |
21 | 103.9, CH | 104.0, CH | 103.4, CH | 104.3, CH |
22 | 185.4, C | 185.4, C | 185.7, C | 185.7, C |
23 | 129.8, C | 129.9, C | 130.4, C | 130.6, C |
24 | 42.6, CH2 | 38.4, CH2 | 41.5, CH2 | 41.9, CH2 |
25 | 25.5, CH | 25.7, CH | 25.3, CH | 25.6, CH |
26 | 22.7, CH3 | 22.2, CH3 | 22.1, CH3 | 22.4, CH3 |
27 | 23.0, CH3 | 23.8, CH3 | 23.7, CH3 | 23.6, CH3 |
Position | 1 | 2 | 3 | 4 |
---|---|---|---|---|
δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | |
2 | 4.74, d (10.9) | 4.84, d (10.6) | 4.09, d (10.9) | 4.06, d (8.4) |
3 | 6.60, dq (10.9, 1.6) | 6.67, dq (10.6, 1.6) | 6.36, dq (10.8, 1.6) | 5.89, dq (8.4, 1.6) |
4a | 2.20, d (1.6) | 2.21, d (1.6) | 2.17, d (1.6) | 2.08, d (1.0) |
6 | 5.05, m | 4.99, m | 5.04, m | 4.87, m |
7 | 1.96, m | 3.90, ddd (2.74, 2.6, 2.6) | 2.15, m | 2.25, m |
2.15, m | 2.15, m | 2.14, m | ||
8 | 3.93, ddd (15.3, 10.2, 3.6) | 4.06, dd (15.6, 2.8) | 3.78, ddd (15.6, 6.0, 6.0) | 4.77, ddd (15.6, 9.1, 4.9) |
9 | 5.01, dd (15.3, 9.3) | 5.24, dd (15.6, 9.3) | 4.87, dd (15.6, 9.4) | 5.24, dd (15.6, 7.7) |
10 | 1.32, overlap | 1.37, overlap | 1.46, overlap | 1.78, m |
10a | 0.89, m | 0.92, m | 1.02, m | 1.43, overlap |
0.89, m | 1.49, overlap | 1.34, overlap | 1.18, overlap | |
10b | 0.66, t (7.4) | 0.65, t (7.4) | 0.73, t (7.4) | 0.77, t (7.5) |
11 | 1.35, m | 1.37, overlap | 1.68, m | 1.29, overlap |
1.46, overlap | 1.49, overlap | 1.25, m | 1.57, m | |
12 | 2.61, m | 2.62, m | 2.64, ddd (14.0, 11.3, 2.8) | 2.46, m |
2.90, m | 2.99, m | 2.46, ddd (14.0, 7.4, 2.9) | 2.77, m | |
16a | 2.22, s | 2.21, s | 2.30, s | 2.31, s |
17 | 7.41, s | 7.38, s | 7.57, s | 7.28, s |
21 | 5.82, s | 5.82, s | 5.80, s | 5.85, s |
24 | 1.13, m | 1.14, m | 1.15, m | 1.20, overlap |
1.32, overlap | 1.31, overlap | 1.32, overlap | 1.30, overlap | |
25 | 1.46, overlap | 1.49, overlap | 1.47, overlap | 1.45, overlap |
26 | 0.81 d (6.6) | 0.83 d (6.6) | 0.88 d (6.5) | 0.88 d (6.6) |
27 | 0.81, d (6.6) | 0.79, d (6.6) | 0.82, d (6.5) | 0.83, d (6.6) |
Compound | IC50 (μM) | |||
---|---|---|---|---|
SGC-7901 | K562 | Hela | A549 | |
1 | 2.8 | 6.6 | 9.6 | 14.9 |
2 | 9.8 | 9.0 | >50 | 24.7 |
3 | 4.7 | 7.6 | 14.1 | 20.9 |
4 | 20.9 | 16.3 | 29.5 | 33.2 |
5 | >50 | >50 | >50 | >50 |
6 | >50 | >50 | >50 | >50 |
Imatinib | 86.8 | 0.2 | 18.8 | 45.6 |
Adriamycin | 6.9 | 10.7 | 11.4 | 5.5 |
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Zhou, L.-M.; Kong, F.-D.; Xie, Q.-Y.; Ma, Q.-Y.; Hu, Z.; Zhao, Y.-X.; Luo, D.-Q. Divergolides T–W with Apoptosis-Inducing Activity from the Mangrove-Derived Actinomycete Streptomyces sp. KFD18. Mar. Drugs 2019, 17, 219. https://doi.org/10.3390/md17040219
Zhou L-M, Kong F-D, Xie Q-Y, Ma Q-Y, Hu Z, Zhao Y-X, Luo D-Q. Divergolides T–W with Apoptosis-Inducing Activity from the Mangrove-Derived Actinomycete Streptomyces sp. KFD18. Marine Drugs. 2019; 17(4):219. https://doi.org/10.3390/md17040219
Chicago/Turabian StyleZhou, Li-Man, Fan-Dong Kong, Qing-Yi Xie, Qing-Yun Ma, Zhong Hu, You-Xing Zhao, and Du-Qiang Luo. 2019. "Divergolides T–W with Apoptosis-Inducing Activity from the Mangrove-Derived Actinomycete Streptomyces sp. KFD18" Marine Drugs 17, no. 4: 219. https://doi.org/10.3390/md17040219
APA StyleZhou, L. -M., Kong, F. -D., Xie, Q. -Y., Ma, Q. -Y., Hu, Z., Zhao, Y. -X., & Luo, D. -Q. (2019). Divergolides T–W with Apoptosis-Inducing Activity from the Mangrove-Derived Actinomycete Streptomyces sp. KFD18. Marine Drugs, 17(4), 219. https://doi.org/10.3390/md17040219