Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp.
Marine cyanobacteria are known to produce structurally diverse bioactive specialized metabolites during bloom occurrence. These ecologically active allelochemicals confer chemical defense for the microalgae from competing microbes and herbivores. From a collection of a marine cyanobacterium, cf. Lyn...
| Main Authors: | , , , , , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2023
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| Online Access: | https://hdl.handle.net/10356/169458 |
| _version_ | 1826119784951971840 |
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| author | Salleh, Nurul Farhana Wang, Jiale Kundukad, Binu Oluwabusola, Emmanuel T. Goh, Delia Xin Yin Phyo, Ma Yadanar Tong, Jasmine Jie Lin Kjelleberg, Staffan Tan, Lik Tong |
| author2 | School of Biological Sciences |
| author_facet | School of Biological Sciences Salleh, Nurul Farhana Wang, Jiale Kundukad, Binu Oluwabusola, Emmanuel T. Goh, Delia Xin Yin Phyo, Ma Yadanar Tong, Jasmine Jie Lin Kjelleberg, Staffan Tan, Lik Tong |
| author_sort | Salleh, Nurul Farhana |
| collection | NTU |
| description | Marine cyanobacteria are known to produce structurally diverse bioactive specialized metabolites during bloom occurrence. These ecologically active allelochemicals confer chemical defense for the microalgae from competing microbes and herbivores. From a collection of a marine cyanobacterium, cf. Lyngbya sp., a small quantity of a new cyclopropane-containing molecule, benderadiene (2), and lyngbyoic acid (1) were purified and characterized using spectroscopic methods. Using live reporter quorum-sensing (QS) inhibitory assays, based on P. aeruginosa PAO1 lasB-gfp and rhlA-gfp strains, both compounds were found to inhibit QS-regulated gene expression in a dose-dependent manner. In addition to lyngbyoic acid being more active in the PAO1 lasB-gfp biosensor strain (IC50 of 20.4 µM), it displayed anti-biofilm activity when incubated with wild-type P. aeruginosa. The discovery of lyngbyoic acid in relatively high amounts provided insights into its ecological significance as a defensive allelochemical in targeting competing microbes through interference with their QS systems and starting material to produce other related analogs. Similar strategies could be adopted by other marine cyanobacterial strains where the high production of other lipid acids has been reported. Preliminary evidence is provided from the virtual molecular docking of these cyanobacterial free acids at the ligand-binding site of the P. aeruginosa LasR transcriptional protein. |
| first_indexed | 2024-10-01T05:05:47Z |
| format | Journal Article |
| id | ntu-10356/169458 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:05:47Z |
| publishDate | 2023 |
| record_format | dspace |
| spelling | ntu-10356/1694582023-07-20T15:30:24Z Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp. Salleh, Nurul Farhana Wang, Jiale Kundukad, Binu Oluwabusola, Emmanuel T. Goh, Delia Xin Yin Phyo, Ma Yadanar Tong, Jasmine Jie Lin Kjelleberg, Staffan Tan, Lik Tong School of Biological Sciences National Institute of Education Singapore Centre for Environmental Life Sciences and Engineering (SCELSE) Science::Biological sciences Marine Cyanobacterium Cyclopropane-Containing Metabolites Marine cyanobacteria are known to produce structurally diverse bioactive specialized metabolites during bloom occurrence. These ecologically active allelochemicals confer chemical defense for the microalgae from competing microbes and herbivores. From a collection of a marine cyanobacterium, cf. Lyngbya sp., a small quantity of a new cyclopropane-containing molecule, benderadiene (2), and lyngbyoic acid (1) were purified and characterized using spectroscopic methods. Using live reporter quorum-sensing (QS) inhibitory assays, based on P. aeruginosa PAO1 lasB-gfp and rhlA-gfp strains, both compounds were found to inhibit QS-regulated gene expression in a dose-dependent manner. In addition to lyngbyoic acid being more active in the PAO1 lasB-gfp biosensor strain (IC50 of 20.4 µM), it displayed anti-biofilm activity when incubated with wild-type P. aeruginosa. The discovery of lyngbyoic acid in relatively high amounts provided insights into its ecological significance as a defensive allelochemical in targeting competing microbes through interference with their QS systems and starting material to produce other related analogs. Similar strategies could be adopted by other marine cyanobacterial strains where the high production of other lipid acids has been reported. Preliminary evidence is provided from the virtual molecular docking of these cyanobacterial free acids at the ligand-binding site of the P. aeruginosa LasR transcriptional protein. Nanyang Technological University Published version The facilities and equipment support were provided by the National Institute of Education, NTU and Singapore Centre for Environmental Life Sciences Engineering, NTU. This research is funded by NIE AcRF grant RI 2/20/TLT. 2023-07-19T05:07:19Z 2023-07-19T05:07:19Z 2023 Journal Article Salleh, N. F., Wang, J., Kundukad, B., Oluwabusola, E. T., Goh, D. X. Y., Phyo, M. Y., Tong, J. J. L., Kjelleberg, S. & Tan, L. T. (2023). Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp.. Molecules, 28(9), 3965-. https://dx.doi.org/10.3390/molecules28093965 1420-3049 https://hdl.handle.net/10356/169458 10.3390/molecules28093965 37175374 2-s2.0-85159599709 9 28 3965 en RI 2/20/TLT Molecules © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/). application/pdf |
| spellingShingle | Science::Biological sciences Marine Cyanobacterium Cyclopropane-Containing Metabolites Salleh, Nurul Farhana Wang, Jiale Kundukad, Binu Oluwabusola, Emmanuel T. Goh, Delia Xin Yin Phyo, Ma Yadanar Tong, Jasmine Jie Lin Kjelleberg, Staffan Tan, Lik Tong Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp. |
| title | Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp. |
| title_full | Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp. |
| title_fullStr | Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp. |
| title_full_unstemmed | Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp. |
| title_short | Cyclopropane-containing specialized metabolites from the marine cyanobacterium cf. Lyngbya sp. |
| title_sort | cyclopropane containing specialized metabolites from the marine cyanobacterium cf lyngbya sp |
| topic | Science::Biological sciences Marine Cyanobacterium Cyclopropane-Containing Metabolites |
| url | https://hdl.handle.net/10356/169458 |
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