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See detailNew linear lipopeptides produced by pseudomonas cichorii SF1-54 are involved in virulence, swarming motility, and biofilm formation
Pauwelyn, E.; Huang, C. J.; Ongena, Marc ULg et al

in Molecular Plant-Microbe Interactions [=MPMI] (2013), 26(5), 585-598

Pseudomonas cichorii is the causal agent of lettuce midrib rot, characterized by a dark-brown to green-black discoloration of the midrib. Formation of necrotic lesions by several plant-pathogenic ... [more ▼]

Pseudomonas cichorii is the causal agent of lettuce midrib rot, characterized by a dark-brown to green-black discoloration of the midrib. Formation of necrotic lesions by several plant-pathogenic pseudomonads is associated with production of phytotoxic lipopeptides, which contribute to virulence. Therefore, the ability of P. cichorii SF1-54 to produce lipopeptides was investigated. A cell-free culture filtrate of SF1-54 showed surfactant, antimicrobial, and phytotoxic activities which are typical for lipopeptides. High-performance liquid chromatography analysis of P. cichorii SF1-54 culture filtrate revealed the presence of seven compounds with lipopeptide characteristics. Two related lipopeptides, named cichofactin A and B, were studied in more detail: they are linear lipopeptides with a decanoic and dodecanoic lipid chain, respectively, connected to the N-terminus of an eight-amino-acid peptide moiety. Both cichofactins are new members of the syringafactin lipopeptide family. Furthermore, two nonribosomal peptide synthethase-encoding genes, cifA and cifB, were identified as responsible for cichofactin biosynthesis. A cifAB deletion mutant no longer produced cichofactins and was impaired in swarming motility but showed enhanced biofilm formation. Upon spray inoculation on lettuce, the cichofactindeficient mutant caused significantly less rotten midribs than the wild type, indicating that cichofactins are involved in pathogenicity of P. cichorii SF1-54. Further analysis revealed that P. cichorii isolates vary greatly in swarming motility and cichofactin production. © 2013 The American Phytopathological Society. [less ▲]

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See detailAmino Acids, Iron, and Growth Rate as Key Factors Influencing Production of the Pseudomonas Putida Btp1 Benzylamine Derivative Involved in Systemic Resistance Induction in Different Plants
Ongena, MARC ULg; Jourdan, Emmanuel ULg; Adam, Akram et al

in Microbial Ecology (2008), 55(2), 280-92

The biological control bacterium Pseudomonas putida BTP1 exerts its protective effect mostly by inducing an enhanced state of resistance in the host plant against pathogen attack [induced systemic ... [more ▼]

The biological control bacterium Pseudomonas putida BTP1 exerts its protective effect mostly by inducing an enhanced state of resistance in the host plant against pathogen attack [induced systemic resistance (ISR)]. We previously reported that a specific compound derived from benzylamine may be involved in the elicitation of the ISR phenomenon by this Pseudomonas strain. In this article, we provide further information about the N,N-dimethyl-N-tetradecyl-N-benzylammonium structure of this determinant for ISR and show that the benzylamine moiety may be important for perception of the molecule by root cells of different plant species. We also investigated some regulatory aspects of elicitor production with the global aim to better understand how in situ expression of these ISR elicitors can be modulated by physiological and environmental factors. The biosynthesis is clearly related to secondary metabolism, and chemostat experiments showed that the molecule is more efficiently produced at low cell growth rate. Interestingly, the presence of free amino acids in the environment is necessary for optimal production, and a specific positive effect of phenylalanine was evidenced in pulsed continuous cultures. The influence of other abiotic factors, such as mineral content, oxygen concentration, or pH, on elicitor production is also reported and discussed with respect to the specific conditions that the producing strain undergoes in the rhizosphere environment. [less ▲]

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See detailOrnicorrugatin, A New Siderophore From Pseudomonas Fluorescens Af76
Matthijs, S.; Budzikiewicz, H.; Schafer, M. et al

in Zeitschrift für Naturforschung. C, Journal of Biosciences (2008), 63(1-2),

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See detailIsolation of an n-alkylated benzylamine derivative from Pseudomonas putida BTP1 as elicitor of induced systemic resistance in bean
Ongena, MARC ULg; Jourdan, Emmanuel ULg; Schafer, M. et al

in Molecular Plant-Microbe Interactions (2005), 18(6), 562-569

Root treatment of Phaseolus vulgaris with the nonpathogenic Pseudomonas putida BTP1 led to significant reduction of the disease caused by the pathogen Botrytis cinerea on leaves. The molecular determinant ... [more ▼]

Root treatment of Phaseolus vulgaris with the nonpathogenic Pseudomonas putida BTP1 led to significant reduction of the disease caused by the pathogen Botrytis cinerea on leaves. The molecular determinant of P putida BTP1 mainly responsible for the induced systemic resistance (ISR) was isolated from cell-free culture fluid after growth of the strain in the iron-poor casamino acid medium. Mass spectrometry analyses performed on both the bacterial product and synthetic analogues revealed a polyalkylated benzylamine structure, with the quaternary ammonium substituted by methyl, ethyl, and C-13 aliphatic groups responsible for the relative hydrophobicity of the molecule. The specific involvement of the N-alkylated benzylamine derivative (NABD) in ISR elicitation was first evidenced by testing the purified compound that mimicked the protective effect afforded by crude supernatant samples. The evidence was supported by the loss of elicitor activity of mutants impaired in NABD biosynthesis. Our experiments also showed that other iron-regulated metabolites secreted by the strain are not involved in ISR stimulation. Thus, these results indicate a wider variety of Pseudomonas determinants for ISR than reported to date. [less ▲]

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See detailStudy of a novel elicitor produced by Pseudomonas putida BTP1 in the ISR on bean
Jourdan, Emmanuel ULg; Ongena, Marc ULg; Schaffer, M. et al

Poster (2004, December 17)

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See detailThe Pyoverdins Of Pseudomonas Syringae And Pseudomonas Cichorii
Bultreys, A.; Gheysen, I.; Wathelet, Bernard ULg et al

in Zeitschrift Fur Naturforschung C-A Journal of Biosciences (2004), 59(9-10),

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See detailFluorescent Pseudomonas mainly produce the dihydro form of pyoverdine at low specific growth rate.
Jacques, Philippe ULg; Ongena, MARC ULg; Bernard, F. et al

in Letters in Applied Microbiology (2003), 36(5), 259-62

AIMS: To analyse the influence of cell growth rate and iron concentration on the production of pyoverdines (PVDs) and of their reduced dihydro forms by three fluorescent Pseudomonas strains (P. putida ... [more ▼]

AIMS: To analyse the influence of cell growth rate and iron concentration on the production of pyoverdines (PVDs) and of their reduced dihydro forms by three fluorescent Pseudomonas strains (P. putida BTP16, P. fluorescens BTP7 and P. aeruginosa 7NSK2). METHODS: PVD and dihydropyoverdine (DHPVD) productions were determined by LC ESI-MS and spectrophotometry during batch and chemostat culture at different dilution rates. SIGNIFICANCE: The relatively high PVD-to-DHPVD ratio (0.57) observed in pH-controlled batch cultures suggested that a base-catalysed chemical oxidation of the dihydroform is not the prime mechanism involved in generating PVDs. Interestingly, in chemostat cultures the PVD-to-DHPVD ratio was significantly reduced at low specific growth rate. Our results suggest that the oxidation of DHPVD to PVD is catalysed by an iron-dependent enzymatic reaction rather than a chemical oxidation. [less ▲]

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See detailDihydropyoverdine production by Pseudomonas putida in transient state and steady-state cultivations.
Jacques, Ph.; Ongena, Marc ULg; Bernard, F. et al

Poster (2001, September)

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See detailIsolation of new metabolites from Pseudomonas putida involved in plant resistance induction
Ongena, Marc ULg; Budzikiewicz, H.; Jacques, Ph. et al

Poster (2001, September)

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See detailInfluence of culture conditions on lipopeptide production by Bacillus subtilis
Akpa, E.; Jacques, Philippe ULg; Wathelet, Bernard ULg et al

in Applied Biochemistry and Biotechnology (2001), 91-3

Bacillus subtilis produces various families of lipopeptides with different homologous compounds. To produce "new molecules" with improved activities and to select strains that produced a reduced number of ... [more ▼]

Bacillus subtilis produces various families of lipopeptides with different homologous compounds. To produce "new molecules" with improved activities and to select strains that produced a reduced number of homologs or isomers, we studied the effects of different media on the nature of the synthesis of fatty; acid chains for each lipopeptide family. This study focused on two B. subtilis strains cultivated in flasks. Optimized medium for lipopeptide production and Landy medium modified by replacing glutamic acid with other alpha -amino acids were used. We found that the intensity of production of homologous compounds depends on the strain and the culture medium. Analysis of these lipopeptides by high-performance liquid chromatography showed that the strain R. subtilis NT02 yielded various homologous compounds when cultivated in Landy medium (L-Glu), but primarily one homologous product in hi,oh relative amounts when cultivated in the optimized medium. Mass spectrometric analysis and determination of the amino acid composition of this molecule enabled us to identify it as Bacillomycine L c15. [less ▲]

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See detailThe Pyoverdin Of Pseudomonas Fluorescens Btp2, A Novel Structural Type
Ongena, MARC ULg; Jacques, Philippe ULg; Thonart, Philippe ULg et al

in Tetrahedron Letters (2001), 42(34),

Abstract—From Pseudomonas fluorescens BTP2 a pyoverdin was isolated which contained the so far not encountered Val in its peptide chain. Its structure could be elucidated by chemical degradation and ... [more ▼]

Abstract—From Pseudomonas fluorescens BTP2 a pyoverdin was isolated which contained the so far not encountered Val in its peptide chain. Its structure could be elucidated by chemical degradation and spectroscopic data. [less ▲]

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See detailInfluence of the culture conditions on lipopeptide production by Bacillus subtilis
Akpa, E.; Jacques, Ph.; Fuchs, R. et al

Poster (2000, May)

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See detailThe structure of two fengycins from Bacillus subtilis S499.
Schneider, J.; Taraz, K.; Budzikiewicz, H. et al

in Zeitschrift für Naturforschung. C, Journal of Biosciences (1999), 54(11), 859-66

The structures of the two fengycins, lipopeptides from Bacillus subtilis, were elucidated by spectroscopic methods and chemical degradation. They show a close structural relationship to the plipastatins ... [more ▼]

The structures of the two fengycins, lipopeptides from Bacillus subtilis, were elucidated by spectroscopic methods and chemical degradation. They show a close structural relationship to the plipastatins from Bacillus cereus differing only in the stereochemistry of the Tyr residues. [less ▲]

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See detailCyclosporin C Is the Main Antifungal Compound Produced by Acremonium Luzulae
Moussaif, M.; Jacques, P.; Schaarwachter, P. et al

in Applied and Environmental Microbiology (1997), 63(5), 1739-43

A strain of Acremonium luzulae (Fuckel) W. Gams was selected in screening new microorganisms for biological control of fruit postharvest diseases, especially gray and blue mold diseases on apples and ... [more ▼]

A strain of Acremonium luzulae (Fuckel) W. Gams was selected in screening new microorganisms for biological control of fruit postharvest diseases, especially gray and blue mold diseases on apples and strawberries. This strain manifests a very strong activity against a large number of phytopathogenic fungi. In this work, the product responsible for this antifungal activity was isolated from modified Sabouraud dextrose broth cultures of A. luzulae. It was purified to homogeneity by reverse-phase column chromatography. On the basis of UV, infrared, and 1H and 13C nuclear magnetic resonance spectra, mass spectral analysis, and the amino acid composition of the acid hydrolysates, the antibiotic was determined to be cyclosporin C. Cyclosporin C showed a broad-spectrum activity against filamentous phytopathogenic fungi but no activity against bacteria or yeasts. Its antifungal activity is only fungistatic. In contrast to Tolypocladium inflatum, another cyclosporin-producing strain, A. luzulae, did not produce additional cyclosporins. This was confirmed by in vivo-directed biosynthesis. [less ▲]

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See detailCell factories for the production of bioactive peptides from Bacillus subtilis and Pseudomonas.
Vater, J.; Venema, G.; Thonart, Philippe ULg et al

Poster (1997, April)

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See detailA 5,6-Dihydro-Isopyoverdin From Azomonas Macrocytogenes
Michalke, R.; Taraz, K.; Budzikiewicz, H. et al

in Zeitschrift Fur Naturforschung C-A Journal of Biosciences (1997), 52(11-12),

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See detailBacterial Constituents .71. Absolute Configuration Of The Isopyoverdin Chromophore
Michalke, R.; Taraz, K.; Budzikiewicz, H. et al

in Zeitschrift Fur Naturforschung C-A Journal of Biosciences (1997), 52(7-8),

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See detailStructure and characterization of isopyoverdin from Pseudomonas putida BTP1 and its relation to the biogenetic pathway leading to pyoverdins.
Jacques, Philippe ULg; Ongena, MARC ULg; Gwose, I. et al

in Zeitschrift für Naturforschung. C, Journal of Biosciences (1995), 50(9-10), 622-9

Pyoverdin type siderophores produced by six fluorescent Pseudomonas strains isolated from different rhizospheres were purified and characterized. The purified ferri-pyoverdins were tested for their ... [more ▼]

Pyoverdin type siderophores produced by six fluorescent Pseudomonas strains isolated from different rhizospheres were purified and characterized. The purified ferri-pyoverdins were tested for their ability to promote the growth of other strains grown under iron deficiency conditions. Only the one obtained from Pseudomonas putida BTP1 did not act as a growth promoter. The structure of the BTP1 siderophore was elucidated by spectroscopic methods and degradation studies. It turned out that it contains a chromophore which differs from the one typical for pyoverdins insofar as it carries the carboxyl group in 3- rather than in 1-position ((3S)-5-amino-1,2-dihydro-8,9-dihydroxy-3H-pyrimido[1,2a]quinoline-3- carboxylic acid). The amino group of the chromophore is substituted with the 5-carboxyl group of L-glutamic acid and its carboxyl group with the N-terminus of the peptide L-Asp-L-Ala-L-Asp-D-N5-Ac-N5-OH-Orn-L-Ser-L-c-N5-OH-Orn. This isopyoverdin fits into the biogenetic scheme which postulates ferribactins as the precursors of pyoverdins. [less ▲]

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