Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge Lissodendoryx papillosa
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation and Structure Elucidation
2.2. Proposed Biosynthetic Pathways for the Formation of Stonikacidin A (1)
2.3. Study of the Biological Activity of Stonikacidin A (1)
2.3.1. Antimicrobial Assay
2.3.2. Cytotoxic Activity
3. Materials and Methods
3.1. General Procedures
3.2. Animal Material
3.3. Extraction and Isolation
3.4. Compounds Characterization Data
3.5. Alkaline Hydrolysis Followed by Acetylation of Stonikacidin A (1)
3.6. Synthesis of D-Idose
3.7. Synthesis of L-Idose
3.8. Synthesis of Acetylated Methyl Aldonates
3.9. Determination of Absolute Configurations of the Idonic Acid Residue in Stonikacidin A (1)
3.10. Bioactivity Assay
3.10.1. Antimicrobial Action
Microbial Strains and Antimicrobial Assays
Sortase A Activity Inhibition Assay
Molecular Docking
3.10.2. Cytotoxic Activity Assay
Reagents and Antibodies for Biological Experiments
Cell Lines and Culture Conditions
MTT Assay
Statistical Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No. | δH, mult (J in Hz) | δC, a Type |
---|---|---|
1 | 172.8, C | |
2 | 5.65, d (1.6) | 73.6, CH |
3 | 6.27, dd (1.6, 9.0) | 72.8, CH |
4 | 5.61, dd (1.6, 9.0) | 73.0, CH |
5 | 4.27, m | 68.4, CH |
6a | 4.10, dd (6.0, 10.0) | 64.6, CH2 |
6b | 4.28, m | |
2′ | 123.3, C | |
3′ | 6.90, d (1.6) | 125.03, b CH |
4′ | 98.1, C | |
5′ | 6.80, d (1.6) | 118.9, CH |
6′ | 160.6, C | |
2″ | 123.5, C | |
3″ | 6.88, d (1.6) | 124.7, CH |
4″ | 98.0, C | |
5″ | 6.76, d (1.6) | 118.8, CH |
6″ | 160.1, C | |
2‴ | 123.6, C | |
3‴ | 7.01, d (1.6) | 125.05, b CH |
4‴ | 98.3, C | |
5‴ | 6.98, d (1.6) | 119.0, CH |
6‴ | 160.7, C | |
2⁗ | 122.9, C | |
3⁗ | 6.67, dd (1.4, 3.6) | 117.2, CH |
4⁗ | 6.12, dd (2.4, 3.6) | 110.8, CH |
5⁗ | 6.91, dd (1.4, 2.4) | 124.9, b CH |
6⁗ | 162.1, C |
Cluster | ∆G, kcal/mol | Energy, kcal/mol | H-Bond, Å | Hydrophobic Interactions |
---|---|---|---|---|
PDB ID 1T2P | ||||
0 | −8.939546 | −24.9548 | H18 … Pro163, 2.333 | Br … Ala92 Br … Val201, Val166, Val168 Gly167, Ile199, Ala104, Ile182, Leu169, Thr180 |
1 | −8.263234 | −9.9639 | H4 … Glu105, 2.260 | Br … Cys184, Gly192, Trp194 Br … Ala92, Leu97 Ala92, Cys184, Ala104, Ile182, Ile199 |
PDB ID 1UAE | ||||
28 | −7.1534557 | 6.28514 | Lys88 … O, 2.825 | Br … Cys115, Br … Cys115, Br … Thr166 Gly118, Lys88, Ala119, Leu111 |
0 | −8.188495 | −17.8594 | H … Cys115, 2.005 H … Gly114, 2.022 | Br … Leu111 Gly114, Lys88, Gly113, Ala119, Gly118 |
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Tabakmakher, K.M.; Makarieva, T.N.; Sabutski, Y.E.; Kokoulin, M.S.; Menshov, A.S.; Popov, R.S.; Guzii, A.G.; Shubina, L.K.; Chingizova, E.A.; Chingizov, A.R.; et al. Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge Lissodendoryx papillosa. Mar. Drugs 2024, 22, 396. https://doi.org/10.3390/md22090396
Tabakmakher KM, Makarieva TN, Sabutski YE, Kokoulin MS, Menshov AS, Popov RS, Guzii AG, Shubina LK, Chingizova EA, Chingizov AR, et al. Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge Lissodendoryx papillosa. Marine Drugs. 2024; 22(9):396. https://doi.org/10.3390/md22090396
Chicago/Turabian StyleTabakmakher, Kseniya M., Tatyana N. Makarieva, Yuri E. Sabutski, Maxim S. Kokoulin, Alexander S. Menshov, Roman S. Popov, Alla G. Guzii, Larisa K. Shubina, Ekaterina A. Chingizova, Artur R. Chingizov, and et al. 2024. "Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge Lissodendoryx papillosa" Marine Drugs 22, no. 9: 396. https://doi.org/10.3390/md22090396