Discovery of the Cyclic Lipopeptide Gacamide A by Genome Mining and Repair of the Defective GacA Regulator in <i>Pseudomonas fluorescens</i> Pf0-1

Jahanshah, Gahzaleh; Yan, Qingpi; Gerhardt, Heike; Pataj, Zoltán; Lämmerhofer, Michael; Pianet, Isabelle; Josten, Michaele; Sahl, Hans‐Georg; Silby, Mark W.; Loper, Joyce E.; Gross, Harald

doi:10.1021/acs.jnatprod.8b00747

Cited by 42 publications

(37 citation statements)

References 72 publications

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“…A similar split organization is found for entolysin (Vallet-Gely et al , 2010), xantholysin (Li et al, 2013), viscosin (De Bruijn and Raaijmakers, 2009), and poaeamide (Zachow et al, 2015). This is contrary to most CLPs which have three biosynthetic genes in the same NRPS cluster, including lokisin (this study), anikasin (Götze et al, 2017), bananamide (Nguyen et al, 2016), arthrofactin (Roongsawang et al, 2003), putisolvin (Dubern et al, 2008), orfamide (Ma et al, 2016a), and gacamide (Jahanshah et al, 2019) among others. WLIP-producing Pseudomonas species involved in this study were isolated from diverse ecologies in various countries; rhizosphere of crops (cocoyam and rice) in tropical rain forests of Cameroon (COW10), Nigeria (NSE1), and Sri Lanka (RW10S2).…”

Section: Discussionmentioning

confidence: 62%

Pseudomonas Cyclic Lipopeptides Suppress the Rice Blast Fungus Magnaporthe oryzae by Induced Resistance and Direct Antagonism

et al. 2019

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Beneficial Pseudomonas spp. produce an array of antimicrobial secondary metabolites such as cyclic lipopeptides (CLPs). We investigated the capacity of CLP-producing Pseudomonas strains and their crude CLP extracts to control rice blast caused by Magnaporthe oryzae , both in a direct manner and via induced systemic resistance (ISR). In planta biocontrol assays showed that lokisin-, white line inducing principle (WLIP)-, entolysin- and N3-producing strains successfully induced resistance to M. oryzae VT5M1. Furthermore, crude extracts of lokisin, WLIP and entolysin gave similar ISR results when tested in planta . In contrast, a xantholysin-producing strain and crude extracts of N3, xantholysin and orfamide did not induce resistance against the rice blast disease. The role of WLIP in triggering ISR was further confirmed by using WLIP-deficient mutants. The severity of rice blast disease was significantly reduced when M. oryzae spores were pre-treated with crude extracts of N3, lokisin, WLIP, entolysin or orfamide prior to inoculation. In vitro microscopic assays further revealed the capacity of crude N3, lokisin, WLIP, entolysin, xantholysin and orfamide to significantly inhibit appressoria formation by M. oryzae . In addition, the lokisin and WLIP biosynthetic gene clusters in the producing strains are described. In short, our study demonstrates the biological activity of structurally diverse CLPs in the control of the rice blast disease caused by M. oryzae . Furthermore, we provide insight into the non-ribosomal peptide synthetase genes encoding the WLIP and lokisin biosynthetic machineries.

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Section: Discussionmentioning

confidence: 62%

Pseudomonas Cyclic Lipopeptides Suppress the Rice Blast Fungus Magnaporthe oryzae by Induced Resistance and Direct Antagonism

et al. 2019

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“…Cyclic lipopeptides (CLPs) are a class of structurally diverse natural products mainly produced by a wide variety of microorganisms, including cyanobacteria, bacteria, actinobacteria, and fungi . They are generally composed of a fatty acid tail linked to the N terminus of a short oligopeptide and the C terminus of the oligopeptide forms a lactone or lactam with a hydroxy, phenol, or amino functional group of the side chains of peptide or part of the lipid moiety .…”

Section: Methodsmentioning

confidence: 99%

Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity

Zhao

Kaiser

et al. 2020

ChemBioChem

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A new cyclic lipopeptide, phototemtide A (1), was isolated from Escherichia coli expressing the biosynthetic gene cluster pttABC from Photorhabdus temperata Meg1. The structure of 1 was elucidated by HR‐ESI‐MS and NMR experiments. The absolute configurations of amino acids and 3‐hydroxyoctanoic acid in 1 were determined by using the advanced Marfey's method and comparison after total synthesis of 1, respectively. Additionally, three new minor derivatives, phototemtides B–D (2–4), were identified by detailed HPLC–MS analysis. Phototemtide A (1) showed weak antiprotozoal activity against Plasmodium falciparum, with an IC50 value of 9.8 μm. The biosynthesis of phototemtides A–D (1–4) was also proposed.

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“…Novel reports of CLPs by specific strains have been accompanied by both nuclear magnetic resonance (NMR) characterization and/or genetic analyses of the NRPS gene clusters. Examples of CLPs that have been characterized using NMR, genetic analysis, or both methods include xantholysin [21], WLIP [7,22,23], viscosin [24], poaeamide [25], massetolide [26,27], lokisin [7,23], anikasin [28], orfamide [6,29], arthrofactin [30,31], putisolvin [32,33], bananamides A-C [34], cocoyamide [9], and gacamide [35], among others.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2019

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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.

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Discovery of the Cyclic Lipopeptide Gacamide A by Genome Mining and Repair of the Defective GacA Regulator in Pseudomonas fluorescens Pf0-1

Cited by 42 publications

References 72 publications

Pseudomonas Cyclic Lipopeptides Suppress the Rice Blast Fungus Magnaporthe oryzae by Induced Resistance and Direct Antagonism

Pseudomonas Cyclic Lipopeptides Suppress the Rice Blast Fungus Magnaporthe oryzae by Induced Resistance and Direct Antagonism

Phototemtide A, a Cyclic Lipopeptide Heterologously Expressed from Photorhabdus temperata Meg1, Shows Selective Antiprotozoal Activity

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

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