Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021
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. Antimicrobial Assays
3.5. Anti-Inflammatory Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Position | 1 a | 2 a | 3 a | 4 a | 5 a | 6 b |
---|---|---|---|---|---|---|
δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | δH (J in Hz) | |
1(NH) | 10.69 (s) | |||||
4 | 7.80 (d, 8.0) | 7.32 (d, 8.0) | 7.43 (d, 8.0) | 7.36 (d, 8.1) | 6.89 (d, 8.1) | 6.97 (d, 8.1) |
5 | 6.88 (d, 8.0) | 6.85 (d, 8.0) | 6.83 (d, 8.0) | 6.88 (d, 8.1) | 6.36 (d, 8.1) | 6.20 (d, 8.1) |
10 | 7.05 (s) | a 2.64 (d, 15.2) | 4.72 (s) | 4.12 (d, 1.2) | 5.75 (s) | a 2.72 (dd, 12.9, 7.0) |
b 2.05 (d, 15.2) | b 2.59 (m) | |||||
11 | 4.59 (dd, 11.9, 7.0) | |||||
14 | a 3.40 (m) | a 3.34 (m) | 3.36 (m) | 3.40 (t, 6.5) | a 3.40 (m) | 3.56 (m) |
b 3.34 (m) | b 3.29 (m) | b 3.30 (m) | ||||
15 | a 2.00 (m) | a 1.97 (m) | a 1.99 (m) | a 2.02 (m) | a 1.99 (m) | a 1.99 (m) |
b 1.84 (m) | b 1.81 (m) | b 1.81 (m) | b 1.85 (m) | b 1.86 (m) | b 1.90 (m) | |
16 | a 2.53 (m) | a 2.50 (m) | a 2.54 (m) | a 2.54 (m) | a 2.48 (m) | a 2.33 (m) |
b 1.83 (m) | b 1.83 (m) | b 1.81 (m) | b 1.85 (m) | b 1.80 (m) | b 2.10 (m) | |
19(NH) | 8.82 (s) | 7.52 (s) | 7.74 (s) | 7.87 (s) | 8.54 (s) | |
20 | a 2.21 (dd, 13.4, 10.2) | a 2.13 (m) | a 2.10 (dd, 13.2, 10.3) | a 2.02 (m) | a 2.04 (m) | a 3.64 (m) |
b 1.89 (m) | b 1.85 (m) | b 1.75 (m) | b 1.85 (m) | b 1.79 (m) | b 3.56 (m) | |
21 | 2.31 (dd, 10.2, 5. 6) | 2.13 (m) | 3.08 (dd, 10.3, 6.5) | 3.53 (dd, 10.1, 7.8) | 2.68 (dd, 10.2, 6.5) | 3.81 (dd, 7.6, 2.8) |
23 | 1.22 (s) | 1.34 (s) | 1.31 (s) | 1.15 (s) | 0.52 (s) | 1.29 (s) |
24 | 1.55 (s) | 1.54 (s) | 1.32 (s) | 1.30 (s) | 1.12 (s) | 0.82 (s) |
25 | 7.74 (d, 10.2) | 7.83 (d, 10.2) | 7.78 (d, 10.2) | 7.76 (d, 10.1) | 6.57 (d, 9.8) | 6.15 (d, 9.9) |
26 | 5.96 (d, 10.2) | 5.90 (d, 10.2) | 5.92 (d, 10.2) | 5.93 (d, 10.1) | 5.75 (d, 9.8) | 5.50 (d, 9.9) |
28 | 1.42 (s) | 1.39 (s) | 1.41 (s) | 1.42 (s) | 1.38 (s) | 1.37 (s) |
29 | 1.41 (s) | 1.39 (s) | 1.39 (s) | 1.40 (s) | 1.35 (s) | 1.35 (s) |
31 | 2.03 (s) | |||||
3-OH | 6.39 (s) | 6.31 (s) | 6.27 (d, 1.2) | |||
OMe-10 | 3.03 (s) | 3.31 (s) |
Position | 1 a | 2 a | 3 a | 4 a | 5 a | 6 b |
---|---|---|---|---|---|---|
δc, Type | δc, Type | δc, Type | δc, Type | δc, Type | δc, Type | |
2 | 145.4, C | 151.2, C | 153.3, C | 152.4, C | 176.3, C | 98.6, C |
3 | 132.7, C | 75.8, C | 78.5, C | 78.0, C | 64.3, C | 97.1, C |
4 | 121.7, CH | 121.9, CH | 123.1, CH | 124.2, CH | 125.0, CH | 125.2, CH |
5 | 116.3, CH | 116.7, CH | 116.1, CH | 116.9, CH | 108.7, CH | 108.0, CH |
6 | 155.1, C | 154.3, C | 154.2, C | 154.4, C | 152.5, C | 155.1, C |
7 | 111.4, C | 112.3, C | 112.0, C | 111.9, C | 104.8, C | 103.7, C |
8 | 139.6, C | 140.0, C | 140.9, C | 140.1, C | 138.0, C | 146.8, C |
9 | 117.6, C | 131.2, C | 129.3, C | 129.4, C | 124.6, C | 118.8, C |
10 | 121.8, CH | 36.0, CH2 | 76.9, CH | 76.1, CH | 74.1, CH | 38.9, CH2 |
11 | 60.3, C | 61.7, C | 62.1, C | 62.3, C | 68.9, C | 63.4, CH |
12 | 168.2, C | 168.4, C | 168.7, C | 168.5, C | 168.1, C | 167.1, C |
14 | 44.2, CH2 | 44.0, CH2 | 44.3, CH2 | 44.4, CH2 | 43.9, CH2 | 45.3, CH2 |
15 | 24.4, CH2 | 24.3, CH2 | 24.6, CH2 | 24.5, CH2 | 24.9, CH2 | 21.0, CH2 |
16 | 29.0, CH2 | 28.9, CH2 | 29.0, CH2 | 29.1, CH2 | 28.1, CH2 | 31.6, CH2 |
17 | 66.5, C | 66.8, C | 66.9, C | 66.8, C | 69.3, C | 93.6, C |
18 | 172.1, C | 172.4, C | 172.4, C | 172.2, C | 172.5, C | 165.4, C |
20 | 30.5, CH2 | 31.8, CH2 | 29.2, CH2 | 30.5, CH2 | 27.9, CH2 | 61.8, CH2 |
21 | 46.3, CH | 48.7, CH | 42.0, CH | 50.0, CH | 51.1, CH | 91.1, CH |
22 | 35.6, C | 38.6, C | 36.8, C | 36.6, C | 47.2, C | 46.7, C |
23 | 17.5, CH3 | 21.2, CH3 | 14.3, CH3 | 13.5, CH3 | 25.6, CH3 | 21.2, CH3 |
24 | 23.4, CH3 | 27.0, CH3 | 22.9, CH3 | 22.8, CH3 | 21.3, CH3 | 18.2, CH3 |
25 | 115.8, CH | 116.3, CH | 116.0, CH | 115.9, CH | 117.2, CH | 116.6, CH |
26 | 133.7, CH | 133.2, CH | 133.3, CH | 133.5, CH | 130.8, CH | 129.1, CH |
27 | 77.1, C | 76.5, C | 76.6, C | 76.7, C | 76.3, C | 76.0, C |
28 | 27.9, CH3 | 27.8, CH3 | 27.9, CH3 | 27.9, CH3 | 28.8, CH3 | 28.2, CH3 |
29 | 27.9, CH3 | 27.8, CH3 | 27.8, CH3 | 27.9, CH3 | 27.9, CH3 | 27.6, CH3 |
30 | 170.0, C | |||||
31 | 21.0, CH3 | |||||
10-OMe | 61.8, CH3 | 60.0, CH3 |
No. | Bacteria | Fungi | |||||||
---|---|---|---|---|---|---|---|---|---|
Xe | Xa | Et | Va | Ah | Vp | Rs | Fo | Cg | |
1 | 50 | 12.5 | 16 | 8 | 32 | 16 | 100 | >100 | >100 |
5 | >100 | >100 | — | — | — | — | 25 | >100 | >100 |
9 | >100 | >100 | — | — | — | — | 25 | >100 | >100 |
10 | >100 | >100 | — | — | — | — | 25 | >100 | >100 |
Chloromycetin | 12.5 | 12.5 | 2 | 0.5 | 2 | 2 | — | — | — |
Ketoconazole | — | — | — | — | — | — | 0.78 | 100 | 12.5 |
No. | THP-1 Cells | P. acnes | |
---|---|---|---|
IC50 (μM) | SC (μM) | MIC (μM) | |
1 | 1.46 ± 0.21 | 0–5 | >5 |
5 | 30.5 ± 0.2 | 0–40 | >40 |
6 | 37.2 ± 3.1 | 0–50 | >50 |
9 | 41.6 ± 1.3 | 0–50 | >50 |
10 | 46.2 ± 2.2 | 0–50 | >50 |
12 | 34.3 ± 1.6 | 0–50 | >50 |
Tretinoin | 3.38 ± 0.28 | 0–50 | >50 |
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Yang, J.; Gong, L.; Guo, M.; Jiang, Y.; Ding, Y.; Wang, Z.; Xin, X.; An, F. Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021. Mar. Drugs 2021, 19, 157. https://doi.org/10.3390/md19030157
Yang J, Gong L, Guo M, Jiang Y, Ding Y, Wang Z, Xin X, An F. Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021. Marine Drugs. 2021; 19(3):157. https://doi.org/10.3390/md19030157
Chicago/Turabian StyleYang, Jin, Lizhi Gong, Miaomiao Guo, Yu Jiang, Yi Ding, Zhijie Wang, Xiujuan Xin, and Faliang An. 2021. "Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021" Marine Drugs 19, no. 3: 157. https://doi.org/10.3390/md19030157
APA StyleYang, J., Gong, L., Guo, M., Jiang, Y., Ding, Y., Wang, Z., Xin, X., & An, F. (2021). Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021. Marine Drugs, 19(3), 157. https://doi.org/10.3390/md19030157