Japonamides A and B, Two New Cyclohexadepsipeptides from the Marine-Sponge-Derived Fungus Aspergillus japonicus and Their Synergistic Antifungal Activities
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experimental Procedures
2.2. Fungal Material, Fermentation, and Extraction
2.3. Molecular Networking Analyses and Compound Isolation
2.4. Absolute Configurations of Amino Acids by the Advanced Marfey’s Analysis
2.5. In Vitro Activities of Compounds 1 and 2 in Combination with Antibiotics against Candida albicans SC5314
3. Results and Discussion
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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1 | 2 | ||||
---|---|---|---|---|---|
Position | Units | δC | δH (mult, J in Hz) | δC | δH (mult, J in Hz) |
l-Pro-1 | |||||
1 | CO | 169.3 | 169.3 | ||
2 | α-CH | 57.3 | 4.62 (dd, 8.8, 3.5) | 57.2 | 4.62 (dd, 8.8, 3.4) |
3 | β-CH2 | 27.4 | 1.71 (m) | 27.5 | 1.72 (m) |
2.16 (m) | 2.15 (m) | ||||
4 | γ-CH2 | 23.9 | 1.85 (m) | 23.9 | 1.84 (m) |
1.89 (m) | 1.90 (m) | ||||
5 | δ-CH2 | 47.1 | 3.57 (dt, 14.0, 8.0) | 47.2 | 3.61 (m) |
3.82 (dt, 14.0, 8.0) | 3.85(ddd,10.0,8.1,5.2) | ||||
l-Pro-2 | |||||
6 | CO | 172.2 | 172.2 | ||
7 | α-CH | 54.5 | 4.31 (dd, 8.0, 5.4) | 54.5 | 4.31 (dd, 8.0, 5.4) |
8 | β-CH2 | 28.0 | 0.73 (m) | 28.0 | 0.72 (m) |
1.01 (m) | 1.01 (m) | ||||
9 | γ-CH2 | 25.0 | 1.63 (m) | 25.0 | 1.62 (m) |
1.88 (m) | 1.89 (m) | ||||
10 | δ-CH2 | 46.8 | 3.44 (dt, 14.0, 7.0) | 46.8 | 3.44 (dt, 10.0, 7.1) |
3.64 (dt, 14.0, 7.0) | 3.63 (m) | ||||
N-Me-O-Me-l-Tyr | |||||
11 | CO | 169.6 | 169.7 | ||
12 | α-CH | 61.8 | 4.79 (dd, 11.6, 3.5) | 61.8 | 4.80 (dd, 11.5, 3.5) |
13 | β-CH2 | 32.2 | 2.73 (dd, 14.5, 11.6) | 32.2 | 2.73 (dd, 14.5, 11.5) |
2.99 (dd, 14.5, 3.5) | 2.99 (dd, 14.5, 3.5) | ||||
14 | γ-C | 129.8 | 129.8 | ||
15 or 19 | δ-CH | 130.4 | 7.10 (d, 8.9) | 130.4 | 7.10 (d, 8.5) |
16 or 18 | ε-CH | 113.9 | 6.85 (d, 8.9) | 113.9 | 6.84 (d, 8.5) |
17 | ζ-C | 158.1 | 158.1 | ||
20 | N-CH3 | 28.2 | 2.23 (s) | 28.2 | 2.23 (s) |
21 | OCH3 | 55.1 | 3.70 (s) | 55.1 | 3.70 (s) |
l-Tyr | |||||
22 | CO | 170.7 | 170.7 | ||
23 | α-CH | 55.7 | 4.25 (td, 8.7, 6.0) | 55.7 | 4.26(ddd,10.0,8.5,5.0) |
24 | β-CH2 | 36.3 | 2.84 (m) | 36.3 | 2.86 (m) |
25 | γ-C | 127.8 | 127.9 | ||
26 or 30 | δ-CH | 130.1 | 6.95 (d, 8.5) | 130.1 | 6.95 (d, 8.5) |
27 or 29 | ε-CH | 115.0 | 6.65 (d, 8.5) | 115.1 | 6.61 (d, 8.5) |
28 | ζ-C | 155.9 | 155.9 | ||
NH | 8.66 (d, 8.7) | 8.67 (d, 8.5) | |||
OH | 9.22 (s) | 9.23 (s) | |||
N-Ac-l-Thr | |||||
31 | CO | 167.7 | 167.6 | ||
32 | α-CH | 54.5 | 4.71 (dd, 9.1, 4.5) | 54.4 | 4.72 (dd, 9.1, 4.5) |
33 | β-CH | 69.9 | 4.96 (qd, 6.6, 4.5) | 69.9 | 4.94 (dd, 6.6, 4.5) |
34 | γ-CH3 | 15.2 | 1.21 (d, 6.6) | 15.2 | 1.21 (d, 6.6) |
35 | CO | 170.0 | 169.9 | ||
36 | CH3 | 22.7 | 1.98 (s) | 22.7 | 1.98 (s) |
NH | 7.78 (d, 9.1) | 7.78 (d, 9.1) | |||
d-Ile or Val | |||||
37 | CO | 169.8 | 169.8 | ||
38 | α-CH | 54.5 | 4.42 (t, 8.9) | 55.8 | 4.32 (d, 8.8) |
39 | β-CH | 36.3 | 1.70 (m) | 29.8 | 1.90 (m) |
40 | γ1-CH2 or γ1-CH3 | 25.2 | 1.07 (m) | 18.7 | 0.85 (d, 5.2) |
1.31 (m) | |||||
41 | γ2-CH3 | 14.7 | 0.82 (d, 6.7) | 18.6 | 0.86 (d, 5.2) |
42 | δ-CH3 | 11.6 | 0.85 (t, 7.4) | ||
NH | 7.35 (d, 8.9) | 7.40 (d, 8.8) |
Drugs | Antifungal MICs (μM) | Synergistic Antifungal MICs (μM) | FICI a | Definition b |
---|---|---|---|---|
Rapamycin | 0.5 | 0.002 | − | − |
1 | >100 | 3.125 | 0.03 | HS |
2 | >100 | 3.125 | 0.03 | HS |
Fluconazole | 0.25 | 0.063 | − | − |
1 | >100 | 12.5 | 0.25 | S |
2 | >100 | 12.5 | 0.25 | S |
Ketoconazole | 0.016 | 0.002 | − | − |
1 | >100 | 6.25 | 0.125 | S |
2 | >100 | 6.25 | 0.125 | S |
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Wang, H.; Zhang, R.; Ma, B.; Wang, W.; Yu, C.; Han, J.; Zhu, L.; Zhang, X.; Dai, H.; Liu, H.; et al. Japonamides A and B, Two New Cyclohexadepsipeptides from the Marine-Sponge-Derived Fungus Aspergillus japonicus and Their Synergistic Antifungal Activities. J. Fungi 2022, 8, 1058. https://doi.org/10.3390/jof8101058
Wang H, Zhang R, Ma B, Wang W, Yu C, Han J, Zhu L, Zhang X, Dai H, Liu H, et al. Japonamides A and B, Two New Cyclohexadepsipeptides from the Marine-Sponge-Derived Fungus Aspergillus japonicus and Their Synergistic Antifungal Activities. Journal of Fungi. 2022; 8(10):1058. https://doi.org/10.3390/jof8101058
Chicago/Turabian StyleWang, Haifeng, Rui Zhang, Ben Ma, Wenzhao Wang, Chong Yu, Junjie Han, Lingjuan Zhu, Xue Zhang, Huanqin Dai, Hongwei Liu, and et al. 2022. "Japonamides A and B, Two New Cyclohexadepsipeptides from the Marine-Sponge-Derived Fungus Aspergillus japonicus and Their Synergistic Antifungal Activities" Journal of Fungi 8, no. 10: 1058. https://doi.org/10.3390/jof8101058