New Cyclic Pentapeptides from the Mangrove-Derived Aspergillus fumigatus GXIMD 03099
Abstract
1. Introduction
2. Results
2.1. Structural Elucidation
2.2. Biological Activity
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Material, Isolation, and Purification
3.3. X-ray Crystallographic Analyses of Compound 5
3.4. Acid Hydrolysis and Marfey’s Analysis Methods
3.5. Insecticidal Activities
3.6. Antibacterial Activities
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
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1 a | 2 b | ||||||
---|---|---|---|---|---|---|---|
Unit | Position | δH, (J in Hz) | δC, Type | Unit | Position | δH, (J in Hz) | δC, Type |
Pro | 1 | 173.5 (C) | Pip | 1 | 173.7 (C) | ||
2 | 4.88, dd, (8.5, 3.0) | 56.7 (CH) | 2 | 4.86, t (6.0) | 51.7 (CH) | ||
3 | 2.11, m; 1.39, m | 28.1 (CH2) | 3 | 1.69, m; 1.34, m | 23.1 (CH2) | ||
4 | 1.85, m | 24.6 (CH2) | 4 | 1.49, m; 1.30, m | 17.6 (CH2) | ||
5 | 3.63, m; 3.29, m | 50.1 (CH2) | 5 | 1.62, m | 22.4 (CH2) | ||
6 | 3.57, m; 3.40, m | 44.9 (CH2) | |||||
Ant | 1 | 167.4 (C) | Ant | 1 | 171.9 (C) | ||
2 | 135.7 (C) | 2 | 136.4 (C) | ||||
3 | 7.52, d, (7.5) | 127.5 (CH) | 3 | 7.35, dd, (8.0, 1.6) | 127.9 (CH) | ||
4 | 7.16, d, (7.5) | 123.2 (CH) | 4 | 7.18, dd, (8.0, 8.0) | 123.4 (CH) | ||
5 | 7.47, t, (8.0) | 130.9 (CH) | 5 | 7.48, dd, (8.0, 8.0) | 131.2 (CH) | ||
6 | 8.38, d, (8.5) | 120.0 (CH) | 6 | 8.40, dd, (8.0, 1.6) | 120.2 (CH) | ||
7 | 123.9 (C) | 7 | 122.7 (C) | ||||
NH | 9.62, s | NH | 9.27, s | ||||
Ile | 1 | 168.9 (C) | Ile | 1 | 168.8 (C) | ||
2 | 4.38, dd, (8.5, 4.5) | 58.1 (CH) | 2 | 4.23, dd, (7.1, 4.2) | 58.4 (CH) | ||
3 | 2.01, m | 36.2 (CH) | 3 | 2.01, m | 35.8 (CH) | ||
4 | 1.37, m; 1.20, m | 24.1 (CH2) | 4 | 1.39, m; 1.26, m | 24.5 (CH2) | ||
5 | 0.83, t, (7.0) | 11.7 (CH3) | 5 | 0.84, t, (9.4) | 11.8 (CH3) | ||
3′ | 0.86, d, (7.0) | 15.7 (CH3) | 3′ | 0.85, d, (6.8) | 15.6 (CH3) | ||
NH | 7.20, d, (9.0) | NH | 7.26, d, (9.0) | ||||
Gly | 1 | 169.4 (C) | Ala | 1 | 172.2 (C) | ||
2 | 4.26, dd, (17.0, 8.0) 3.66, dd, (9.5, 3.5), | 42.6 (CH2) | 2 | 4.56, m | 47.7 (CH) | ||
3 | 1.30, d, (7.2) | 17.5 (CH3) | |||||
NH | 7.78, dd, (7.5, 4.0) | NH | 7.29, d, (7.5) | ||||
N-Me-Phe | 1 | 169.9 (C) | N-Me-Phe | 1 | 168.9 (C) | ||
2 | 5.30, dd, (12.0, 4.5) | 58.8 (CH) | 2 | 5.58, dd, (12.4, 4.4) | 57.2 (CH) | ||
3 | 3.40, dd, (15.5, 4.5) 3.10, dd, (15.5, 12.5) | 32.5 (CH2) | 3 | 3.44, m; 3.05, m | 31.9 (CH2) | ||
4 | 137.7 (C) | 4 | 137.8 (C) | ||||
5, 9 | 7.25, m | 128.3 (CH) | 5, 9 | 7.21, d (12.0) | 128.2 (CH) | ||
6, 8 | 7.31, m | 128.3 (CH) | 6, 8 | 7.28, d, (7.2) | 128.3 (CH) | ||
7 | 7.22, m | 126.4 (CH) | 7 | 7.21, t, (7.2) | 126.3 (CH2) | ||
N-Me | 3.00, s | 31.6 (CH3) | N-Me | 2.97, s | 30.6 (CH3) |
3 c | 4 d | ||||||
---|---|---|---|---|---|---|---|
Unit | Position | δH, (J in Hz) | δC, Type | Unit | Position | δH, (J in Hz) | δC, Type |
Pro | 1 | 173.5 (C) | Pro | 1 | 176.6 (C) | ||
2 | 4.90, dd, (9.0, 3.5) | 56.8 (CH) | 2 | 4.88, m | 57.9 (CH) | ||
3 | 2.11, m; 1.37, m | 28.1 (CH2) | 3 | 2.03, m; 1.40, m | 29.5 (CH2) | ||
4 | 1.84, m | 24.5 (CH2) | 4 | 2.08, m; 1.89, m | 26.1 (CH2) | ||
5 | 3.63, m; 3.28, m | 50.1 (CH2) | 5 | 3.80, m; 3.52, m | 52.6 (CH2) | ||
Ant | 1 | 167.4 (C) | Ant | 1 | 170.4 (C) | ||
2 | 135.6 (C) | 2 | 138.8 (C) | ||||
3 | 7.52, d, (6.5) | 127.4 (CH) | 3 | 7.58, dd (7.5, 1.5) | 129.6(CH) | ||
4 | 7.18, t, (7.0) | 123.2 (CH) | 4 | 7.23, t (7.0) | 127.8(CH) | ||
5 | 7.47, td, (8.5, 1.0) | 130.9 (CH) | 5 | 7.48, td (7.5, 1.5) | 132.9(CH) | ||
6 | 8.35, d, (8.0) | 120.1 (CH) | 6 | 8.50, dd (8.5, 1.0) | 121.6(CH) | ||
7 | 124.1 (C) | 7 | 123.6(C) | ||||
NH | 9.62, s | Abu | 1 | 171.7 (C) | |||
Val | 1 | 168.9 (C) | 2 | 4.42, dd (10.0, 4.0) | 57.6 (CH) | ||
2 | 5.29, dd, (12.0, 4.5) | 58.7 (CH) | 3 | 2.13, m; 1.73, m | 25.1 (CH2) | ||
3 | 2.31, m | 29.4 (CH) | 4 | 1.00, t (7.0) | 11.1 (CH3) | ||
4 | 0.88, d, (7.0) | 19.0 (CH3) | Ala | 1 | 174.8 (C) | ||
5 | 0.86, d, (7.0) | 16.9 (CH3) | 2 | 4.81, dd (14.5, 7.0) | 49.6 (CH) | ||
NH | 7.12, d, (9.0) | 3 | 1.44, d (7.0) | 18.2 (CH3) | |||
Gly | 1 | 169.4 (C) | N-Me-Phe | 1 | 172.1 (C) | ||
2 | 4.24, dd, (17.0, 8.0), 3.67, dd, (17.0, 4.5), | 42.6 (CH2) | 2 3 4 | 5.73, dd (12.0, 4.5) 3.63, dd (15.0, 4.0), 3.06, dd (15.0, 12.5) | 59.6 (CH) 33.9 (CH2) 138.2 (C) | ||
3 | 3.63, dd (15.0, 4.0), 3.06, dd (15.0, 12.5) | 33.9 (CH2) | |||||
NH | 7.79, dd, (8.0, 4.5) | 5, 9 | 129.5 (CH) | ||||
N-Me-Phe | 1 | 170.0 (C) | 7 | 124.4 (CH) | |||
2 | 4.36, dd, (9.0, 4.5) | 58.7 (CH) | 6, 8 | 129.5 (CH) | |||
3 | 3.41, dd, (15.5, 4.5); 3.12, dd, (15.0, 12.0), | 32.5 (CH2) | N-Me | 32.1 (CH3) | |||
4 | 137.6 (C) | ||||||
5, 9 | 7.31, m; 7.25, m | 128.3(CH) | |||||
6, 8 | 7.31, m; 7.25, m | 128.4(CH) | |||||
7 | 7.23, t, (7.5) | 126.4 (CH) | |||||
N-Me | 3.01, s | 31.5 (CH3) |
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Wang, Y.; Cao, G.; Gan, Y.; Lin, X.; Yi, X.; Zhao, L.; Liu, Y.; Gao, C.; Bai, M. New Cyclic Pentapeptides from the Mangrove-Derived Aspergillus fumigatus GXIMD 03099. Mar. Drugs 2024, 22, 282. https://doi.org/10.3390/md22060282
Wang Y, Cao G, Gan Y, Lin X, Yi X, Zhao L, Liu Y, Gao C, Bai M. New Cyclic Pentapeptides from the Mangrove-Derived Aspergillus fumigatus GXIMD 03099. Marine Drugs. 2024; 22(6):282. https://doi.org/10.3390/md22060282
Chicago/Turabian StyleWang, Yu, Guangping Cao, Yuman Gan, Xiao Lin, Xiangxi Yi, Longyan Zhao, Yonghong Liu, Chenghai Gao, and Meng Bai. 2024. "New Cyclic Pentapeptides from the Mangrove-Derived Aspergillus fumigatus GXIMD 03099" Marine Drugs 22, no. 6: 282. https://doi.org/10.3390/md22060282
APA StyleWang, Y., Cao, G., Gan, Y., Lin, X., Yi, X., Zhao, L., Liu, Y., Gao, C., & Bai, M. (2024). New Cyclic Pentapeptides from the Mangrove-Derived Aspergillus fumigatus GXIMD 03099. Marine Drugs, 22(6), 282. https://doi.org/10.3390/md22060282