Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners
Myxobacteria represent a viable source of chemically diverse and biologically active secondary metabolites. The myxochelins are a well-studied family of catecholate-type siderophores produced by various myxobacterial strains. Here, we report the discovery, isolation, and structure elucidation of thr...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/16/4929 |
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| author | Nicolas A. Frank Márió Széles Sergi H. Akone Sari Rasheed Stephan Hüttel Simon Frewert Mostafa M. Hamed Jennifer Herrmann Sören M. M. Schuler Anna K. H. Hirsch Rolf Müller |
| author_facet | Nicolas A. Frank Márió Széles Sergi H. Akone Sari Rasheed Stephan Hüttel Simon Frewert Mostafa M. Hamed Jennifer Herrmann Sören M. M. Schuler Anna K. H. Hirsch Rolf Müller |
| author_sort | Nicolas A. Frank |
| collection | DOAJ |
| description | Myxobacteria represent a viable source of chemically diverse and biologically active secondary metabolites. The myxochelins are a well-studied family of catecholate-type siderophores produced by various myxobacterial strains. Here, we report the discovery, isolation, and structure elucidation of three new myxochelins N1–N3 from the terrestrial myxobacterium <i>Corallococcus</i> sp. MCy9049, featuring an unusual nicotinic acid moiety. Precursor-directed biosynthesis (PDB) experiments and total synthesis were performed in order to confirm structures, improve access to pure compounds for bioactivity testing, and to devise a biosynthesis proposal. The combined evaluation of metabolome and genome data covering myxobacteria supports the notion that the new myxochelin congeners reported here are in fact frequent side products of the known myxochelin A biosynthetic pathway in myxobacteria. |
| first_indexed | 2024-03-10T08:33:02Z |
| format | Article |
| id | doaj.art-4395dead086a41c4ae384a959f3c78ee |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T08:33:02Z |
| publishDate | 2021-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4395dead086a41c4ae384a959f3c78ee2023-11-22T08:54:06ZengMDPI AGMolecules1420-30492021-08-012616492910.3390/molecules26164929Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing CongenersNicolas A. Frank0Márió Széles1Sergi H. Akone2Sari Rasheed3Stephan Hüttel4Simon Frewert5Mostafa M. Hamed6Jennifer Herrmann7Sören M. M. Schuler8Anna K. H. Hirsch9Rolf Müller10Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyEvotec International GmbH, 37079 Göttingen, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyHelmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbrücken, GermanyMyxobacteria represent a viable source of chemically diverse and biologically active secondary metabolites. The myxochelins are a well-studied family of catecholate-type siderophores produced by various myxobacterial strains. Here, we report the discovery, isolation, and structure elucidation of three new myxochelins N1–N3 from the terrestrial myxobacterium <i>Corallococcus</i> sp. MCy9049, featuring an unusual nicotinic acid moiety. Precursor-directed biosynthesis (PDB) experiments and total synthesis were performed in order to confirm structures, improve access to pure compounds for bioactivity testing, and to devise a biosynthesis proposal. The combined evaluation of metabolome and genome data covering myxobacteria supports the notion that the new myxochelin congeners reported here are in fact frequent side products of the known myxochelin A biosynthetic pathway in myxobacteria.https://www.mdpi.com/1420-3049/26/16/4929myxobacteriamyxochelinnicotinic acidsecondary metabolitesnatural product discoveryprecursor-directed biosynthesis |
| spellingShingle | Nicolas A. Frank Márió Széles Sergi H. Akone Sari Rasheed Stephan Hüttel Simon Frewert Mostafa M. Hamed Jennifer Herrmann Sören M. M. Schuler Anna K. H. Hirsch Rolf Müller Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners Molecules myxobacteria myxochelin nicotinic acid secondary metabolites natural product discovery precursor-directed biosynthesis |
| title | Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners |
| title_full | Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners |
| title_fullStr | Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners |
| title_full_unstemmed | Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners |
| title_short | Expanding the Myxochelin Natural Product Family by Nicotinic Acid Containing Congeners |
| title_sort | expanding the myxochelin natural product family by nicotinic acid containing congeners |
| topic | myxobacteria myxochelin nicotinic acid secondary metabolites natural product discovery precursor-directed biosynthesis |
| url | https://www.mdpi.com/1420-3049/26/16/4929 |
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