<i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i>
<i>Pseudomonas</i> species are metabolically robust, with capacity to produce secondary metabolites including cyclic lipopeptides (CLPs). Herein we conducted a chemical analysis of a crude CLP extract from the cocoyam rhizosphere-derived biocontrol strain <i>Pseudomonas</i> s...
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| Language: | English |
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MDPI AG
2019-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/22/4170 |
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| author | Olumide Owolabi Omoboye Niels Geudens Matthieu Duban Mickaël Chevalier Christophe Flahaut José C. Martins Valérie Leclère Feyisara Eyiwumi Oni Monica Höfte |
| author_facet | Olumide Owolabi Omoboye Niels Geudens Matthieu Duban Mickaël Chevalier Christophe Flahaut José C. Martins Valérie Leclère Feyisara Eyiwumi Oni Monica Höfte |
| author_sort | Olumide Owolabi Omoboye |
| collection | DOAJ |
| description | <i>Pseudomonas</i> species are metabolically robust, with capacity to produce secondary metabolites including cyclic lipopeptides (CLPs). Herein we conducted a chemical analysis of a crude CLP extract from the cocoyam rhizosphere-derived biocontrol strain <i>Pseudomonas</i> sp. COW3. We performed in silico analyses on its whole genome, and conducted in vitro antagonistic assay using the strain and purified CLPs. Via LC-MS and NMR, we elucidated the structures of four novel members of the bananamide group, named bananamides D-G. Besides variability in fatty acid length, bananamides D-G differ from previously described bananamides A-C and MD-0066 by the presence of a serine and aspartic acid at position 6 and 2, respectively. In addition, bananamide G has valine instead of isoleucine at position 8. Kendrick mass defect (KMD) allowed the assignment of molecular formulae to bananamides D and E. We unraveled a non-ribosomal peptide synthetase cluster <i>banA, banB</i> and <i>banC</i> which encodes the novel bananamide derivatives. Furthermore, COW3 displayed antagonistic activity and mycophagy against <i>Pythium myriotylum,</i> while it mainly showed mycophagy on <i>Pyricularia oryzae.</i> Purified bananamides D-G inhibited the growth of <i>P. myriotylum</i> and <i>P. oryzae</i> and caused hyphal distortion. Our study shows the complementarity of chemical analyses and genome mining in the discovery and elucidation of novel CLPs. In addition, structurally diverse bananamides differ in their antimicrobial activity. |
| first_indexed | 2024-12-16T09:02:14Z |
| format | Article |
| id | doaj.art-2e2b8aa3ec4f44ebb03b7b4a7ca60885 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-16T09:02:14Z |
| publishDate | 2019-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2e2b8aa3ec4f44ebb03b7b4a7ca608852022-12-21T22:37:08ZengMDPI AGMolecules1420-30492019-11-012422417010.3390/molecules24224170molecules24224170<i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i>Olumide Owolabi Omoboye0Niels Geudens1Matthieu Duban2Mickaël Chevalier3Christophe Flahaut4José C. Martins5Valérie Leclère6Feyisara Eyiwumi Oni7Monica Höfte8Laboratory of Phytopathology, Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, BelgiumNMR and Structure Analysis Unit, Department of Organic and Macromolecular Chemistry, Faculty of Science, Ghent University, Krijgslaan 281, B-9000 Gent, BelgiumUniv. Lille, INRA, ISA, Univ. Artois, Univ. Littoral Côte d’Opale, EA 7394-ICV- Institut Charles Viollette, F-59000 Lille, FranceUniv. Lille, INRA, ISA, Univ. Artois, Univ. Littoral Côte d’Opale, EA 7394-ICV- Institut Charles Viollette, F-59000 Lille, FranceUniv. Lille, INRA, ISA, Univ. Artois, Univ. Littoral Côte d’Opale, EA 7394-ICV- Institut Charles Viollette, F-59000 Lille, FranceNMR and Structure Analysis Unit, Department of Organic and Macromolecular Chemistry, Faculty of Science, Ghent University, Krijgslaan 281, B-9000 Gent, BelgiumUniv. Lille, INRA, ISA, Univ. Artois, Univ. Littoral Côte d’Opale, EA 7394-ICV- Institut Charles Viollette, F-59000 Lille, FranceLaboratory of Phytopathology, Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, BelgiumLaboratory of Phytopathology, Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium<i>Pseudomonas</i> species are metabolically robust, with capacity to produce secondary metabolites including cyclic lipopeptides (CLPs). Herein we conducted a chemical analysis of a crude CLP extract from the cocoyam rhizosphere-derived biocontrol strain <i>Pseudomonas</i> sp. COW3. We performed in silico analyses on its whole genome, and conducted in vitro antagonistic assay using the strain and purified CLPs. Via LC-MS and NMR, we elucidated the structures of four novel members of the bananamide group, named bananamides D-G. Besides variability in fatty acid length, bananamides D-G differ from previously described bananamides A-C and MD-0066 by the presence of a serine and aspartic acid at position 6 and 2, respectively. In addition, bananamide G has valine instead of isoleucine at position 8. Kendrick mass defect (KMD) allowed the assignment of molecular formulae to bananamides D and E. We unraveled a non-ribosomal peptide synthetase cluster <i>banA, banB</i> and <i>banC</i> which encodes the novel bananamide derivatives. Furthermore, COW3 displayed antagonistic activity and mycophagy against <i>Pythium myriotylum,</i> while it mainly showed mycophagy on <i>Pyricularia oryzae.</i> Purified bananamides D-G inhibited the growth of <i>P. myriotylum</i> and <i>P. oryzae</i> and caused hyphal distortion. Our study shows the complementarity of chemical analyses and genome mining in the discovery and elucidation of novel CLPs. In addition, structurally diverse bananamides differ in their antimicrobial activity.https://www.mdpi.com/1420-3049/24/22/4170non-ribosomal peptide synthetases (nrps)kendrick mass defectin silico analysishyphal leakageextensive branchingvacuolizationmycophagy<i>pseudomonas koreensis</i> groupnmr spectroscopy<i>magnaporthe oryzae</i> |
| spellingShingle | Olumide Owolabi Omoboye Niels Geudens Matthieu Duban Mickaël Chevalier Christophe Flahaut José C. Martins Valérie Leclère Feyisara Eyiwumi Oni Monica Höfte <i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i> Molecules non-ribosomal peptide synthetases (nrps) kendrick mass defect in silico analysis hyphal leakage extensive branching vacuolization mycophagy <i>pseudomonas koreensis</i> group nmr spectroscopy <i>magnaporthe oryzae</i> |
| title | <i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i> |
| title_full | <i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i> |
| title_fullStr | <i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i> |
| title_full_unstemmed | <i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i> |
| title_short | <i>Pseudomonas</i> sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against <i>Pythium myriotylum</i> and <i>Pyricularia oryzae</i> |
| title_sort | i pseudomonas i sp cow3 produces new bananamide type cyclic lipopeptides with antimicrobial activity against i pythium myriotylum i and i pyricularia oryzae i |
| topic | non-ribosomal peptide synthetases (nrps) kendrick mass defect in silico analysis hyphal leakage extensive branching vacuolization mycophagy <i>pseudomonas koreensis</i> group nmr spectroscopy <i>magnaporthe oryzae</i> |
| url | https://www.mdpi.com/1420-3049/24/22/4170 |
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