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Pseudomonas sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against Pythium myriotylum and Pyricularia oryzae

1
Laboratory of Phytopathology, Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium
2
Department of Microbiology, Obafemi Awolowo University, Ile-Ife 220005, Osun State, Nigeria
3
NMR and Structure Analysis Unit, Department of Organic and Macromolecular Chemistry, Faculty of Science, Ghent University, Krijgslaan 281, B-9000 Gent, Belgium
4
Univ. Lille, INRA, ISA, Univ. Artois, Univ. Littoral Côte d’Opale, EA 7394-ICV- Institut Charles Viollette, F-59000 Lille, France
*
Author to whom correspondence should be addressed.
These authors share senior authorship.
Academic Editor: Kira J. Weissman
Molecules 2019, 24(22), 4170; https://doi.org/10.3390/molecules24224170
Received: 14 October 2019 / Revised: 12 November 2019 / Accepted: 15 November 2019 / Published: 17 November 2019
(This article belongs to the Section Natural Products Chemistry)
Pseudomonas 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 Pseudomonas 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 banA, banB and banC which encodes the novel bananamide derivatives. Furthermore, COW3 displayed antagonistic activity and mycophagy against Pythium myriotylum, while it mainly showed mycophagy on Pyricularia oryzae. Purified bananamides D-G inhibited the growth of P. myriotylum and P. oryzae 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. View Full-Text
Keywords: non-ribosomal peptide synthetases (NRPS); Kendrick mass defect; in silico analysis; hyphal leakage; extensive branching; vacuolization; mycophagy; Pseudomonas koreensis group; NMR spectroscopy; Magnaporthe oryzae non-ribosomal peptide synthetases (NRPS); Kendrick mass defect; in silico analysis; hyphal leakage; extensive branching; vacuolization; mycophagy; Pseudomonas koreensis group; NMR spectroscopy; Magnaporthe oryzae
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Omoboye, O.O.; Geudens, N.; Duban, M.; Chevalier, M.; Flahaut, C.; Martins, J.C.; Leclère, V.; Oni, F.E.; Höfte, M. Pseudomonas sp. COW3 Produces New Bananamide-Type Cyclic Lipopeptides with Antimicrobial Activity against Pythium myriotylum and Pyricularia oryzae. Molecules 2019, 24, 4170.

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