Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635
Abstract
1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Material
3.3. Fermentation, Extraction, and Isolation
3.4. ECD Calculation
3.5. Virtual Screening Against COVID-19 Main Protease
3.5.1. Protein and Ligand Preparation
3.5.2. Virtual Screening
3.6. Cell Culture and Cell Viability Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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No. | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δC | δH, Mult. (J in Hz) | δC | δH, Mult. (J in Hz) | δC | δH, Mult. (J in Hz) | |
1 | 165.9 | - | 166.8 | - | 166.2 | - |
2 | - | 9.01, s | - | 9.43, s | - | 8.93, s |
3 | 125.3 | - | 125.9 | - | 126.2 | - |
4 | 158.9 | - | 161.1 | - | 158.4 | - |
6a | 86.7 | 5.59, dd (5.7, 1.7) | 85.4 | 5.35, dd (2.8, 1.7) | 54.4 | 3.32, m |
6b | - | - | - | - | - | 3.75, dd (12.7, 4.5) |
7a | 29.6 | 1.75, dddd (13.4, 8.4, 5.0, 1.7) | 30.7 | 1.92, m | 66.6 | 4.35, t (4.5) |
7b | 1.97, m | - | ||||
8a | 25.9 | 2.13, dddd (12.2, 9.7, 6.7, 5.0) | 24.5 | 1.92, m | 37.6 | 1.98, ddd (12.7, 11.5, 4.5) |
8b | 2.27, m | 2.10, m | 2.12, dd (12.7, 6.0) | |||
9 | 56.5 | 4.57, dd (8.9, 6.7) | 58.7 | 4.44, m | 57.0 | 4.65, dd (11.5, 6.0) |
10 | 111.9 | 6.98, s | 113.2 | 7.05, s | 110.7 | 6.92, s |
11 | 103.9 | - | 104.3 | - | 103.8 | - |
12 | 125.9 | - | 125.8 | - | 126.0 | - |
13 | 119.6 | 7.29, d (8.0) | 119.7 | 7.23, d (8.0) | 119.4 | 7.29, d (8.0) |
14 | 119.4 | 6.99, m | 119.3 | 6.99, ddd (8.0, 7.0, 1.2) | 119.3 | 7.00, m |
15 | 120.7 | 7.08, ddd (8.0, 7.0, 1.2) | 120.7 | 7.07, ddd (8.0, 7.0, 1.2) | 120.7 | 7.08, ddd (8.0, 7.0, 1.2) |
16 | 111.5 | 7.41, d (8.0) | 111.6 | 7.41, m | 111.4 | 7.41, d (8.0) |
17 | 135.1 | - | 135.1 | - | 135.1 | - |
18 | 11.06, s | - | 11.06, s | - | 11.03, s | |
19 | 144.3 | - | 144.7 | - | 144.0 | - |
20 | 39.0 | - | 39.1 | - | 39.0 | - |
21 | 145.1 | 6.07, dd (17.4, 10.5) | 145.1 | 6.09, dd (17.1, 10.8) | 145.2 | 6.08, dd (17.3, 10.5) |
22 | 111.7 | 5.05, m | 111.7 | 5.06, m | 111.6 | 5.04, m |
23 | 27.4 | 1.45, s | 27.5 | 1.47, s | 27.4 | 1.46, s |
24 | 27.8 | 1.49, s | 27.9 | 1.51, s | 27.7 | 1.50, s |
6-OEt | 63.6 | 3.65, m | 64.3 | 3.60, m | - | - |
15.2 | 1.13, t (7.1) | 15.4 | 1.09, t (7.1) | - | - |
No. | 4 | 5 | 6 | |||
---|---|---|---|---|---|---|
δ | δH, Mult. (J in Hz) | δC | δH, Mult. (J in Hz) | δC | δH, Mult. (J in Hz) | |
1 | 163.1 | - | - | - | - | - |
2 | - | 9.43, s | 83.9 | 5.27, d (4.7) | 78.3 | 6.40, d (4.3) |
3 | 125.5 | - | 146.9 | - | 151.1 | - |
4 | 159.4 | - | - | - | - | |
5 | - | - | 146.7 | - | 139.0 | - |
6 | 45.1 | 3.62, dd (8.6, 5.8) | 127.8 | 7.74, d (8.0) | 122.9 | 8.23, d, (8.0) |
7a | 19.5 | 1.92, m | 134.9 | 7.79, t (8.0) | 136.7 | 7.91, t (8.0) |
7b | 1.96, m | |||||
8a | 32.4 | 2.02, m | 128.0 | 7.53, t (8.0) | 129.7 | 7.66, t (8.0) |
8b | 2.33, m | |||||
9 | 91.0 | - | 127.0 | 8.24, d (8.0) | 127.9 | 8.23, d, (8.0) |
10 | 112.7 | 7.02, s | 120.8 | - | 119.1 | - |
11 | 103.9 | - | 160.3 | - | 157.4 | - |
12 | 126.3 | - | - | - | - | - |
13 | 119.1 | 7.21, d (8.0) | 57.4 | 5.53, dd (8.8, 6.5) | 58.1 | 5.54, t (7.8) |
14 | 119.0 | 7.00, m | 170.0 | - | 167.6 | - |
15 | 120.7 | 7.09, m | 40.0 | 3.43, m | 39.9 | 3.48, m |
16 | 111.6 | 7.43, d (8.0) | 135.9 | - | 134.9 | - |
17 | 135.1 | - | 129.8 | 7.29, m | 129.7 | 7.24, m |
18 | 11.10, s | 128.6 | 7.28, m | 128.8 | 7.24, m | |
19 | 144.4 | - | 127.0 | 7.24, m | 127.7 | 7.20, m |
20 | 39.0 | - | 128.6 | 7.28, m | 128.8 | 7.24, m |
21 | 145.2 | 6.09, ddd (17.1, 10.8, 1.6) | 129.8 | 7.29, m | 129.7 | 7.24, m |
22 | 111.7 | 5.06, m | - | - | - | - |
23 | 27.4 | 1.47, s | - | - | - | - |
24 | 27.8 | 1.50, s | - | - | - | - |
9-OEt | 59.2 | 3.53, qd (7.0, 3.9) | - | - | - | - |
- | 15.2 | 1.22, td (7.0, 1.5) | - | - | - | - |
2-OMe/ 2-OEt | - | - | 56.0 | 3.53, s | 66.2 | 4.04, dt (9.0, 7.0) |
4.11, dt (9.0, 7.0) | ||||||
- | - | - | - | 15.4 | 1.35, t (7.0) |
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Ding, Y.; Zhu, X.; Hao, L.; Zhao, M.; Hua, Q.; An, F. Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635. Mar. Drugs 2020, 18, 338. https://doi.org/10.3390/md18070338
Ding Y, Zhu X, Hao L, Zhao M, Hua Q, An F. Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635. Marine Drugs. 2020; 18(7):338. https://doi.org/10.3390/md18070338
Chicago/Turabian StyleDing, Yi, Xiaojing Zhu, Liling Hao, Mengyao Zhao, Qiang Hua, and Faliang An. 2020. "Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635" Marine Drugs 18, no. 7: 338. https://doi.org/10.3390/md18070338
APA StyleDing, Y., Zhu, X., Hao, L., Zhao, M., Hua, Q., & An, F. (2020). Bioactive Indolyl Diketopiperazines from the Marine Derived Endophytic Aspergillus versicolor DY180635. Marine Drugs, 18(7), 338. https://doi.org/10.3390/md18070338