Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040

Sonnenschein, Eva C.; Stierhof, Marc; Goralczyk, Stephan; Vabre, Floriane M.; Pellissier, Léonie; Hanssen, Kine Østnes; Cruz, Mercedes de la; Díaz, Caridad; Witte, Peter de; Copmans, Daniëlle; Andersen, Jeanette Hammer; Hansen, Espen; Kristoffersen, Venke; Tormo, José R.; Ebel, Rainer; Milne, Bruce F.; Deng, Hai; Gram, Lone; Jaspars, Marcel; Tabudravu, Jioji N.

doi:10.1016/j.tet.2017.03.051

Cited by 20 publications

(21 citation statements)

References 38 publications

(51 reference statements)

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“…Not all bacteria are equally proficient in secondary metabolite production, and whereas some groups appear to produce few or no metabolites, others such as filamentous soil bacteria and marine vibrios, roseobacters and Pseudoalteromonas spp. produce an array of different bioactive compounds (Brinkhoff et al, 2004;Murphy et al, 2012;Rasmussen et al, 2014;Maansson et al, 2016;Sonnenschein et al, 2017b). Hence, if the role of these compounds is to eliminate competing microorganisms, proficient secondary metabolite producers should be strong drivers of microbial community composition in natural environments.…”

Section: Introductionmentioning

confidence: 99%

Impact of Phaeobacter inhibens on marine eukaryote‐associated microbial communities

Dittmann

Sonnenschein

Egan

et al. 2018

Environ Microbiol Rep

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Summary Bacteria–host interactions are universal in nature and have significant effects on host functionality. Bacterial secondary metabolites are believed to play key roles in such interactions as well as in interactions within the host‐associated microbial community. Hence, prominent secondary metabolite‐producing bacteria may be strong drivers of microbial community composition in natural host‐associated microbiomes. This has, however, not been rigorously tested, and the purpose of this study was to investigate how the secondary metabolite producer Phaeobacter inhibens affects the diversity and composition of microbiomes associated with the microalga Emiliania huxleyi and the European flat oyster, Ostrea edulis. Roseobacters were indigenous to both communities exhibiting relative abundances between 2.8% and 7.0%. Addition of P. inhibens caused substantial changes in the overall structure of the low‐complexity microbiome of E. huxleyi, but did not shape microbial community structure to the same degree in the more complex oyster microbiomes. Species‐specific interactions occurred in both microbiomes and specifically the abundances of other putative secondary metabolite‐producers such as vibrios and pseudoalteromonads were reduced. Thus, the impact of a bioactive strain like P. inhibens on host‐associated microbiomes depends on the complexity and composition of the existing microbiome.

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Section: Introductionmentioning

confidence: 99%

Impact of Phaeobacter inhibens on marine eukaryote‐associated microbial communities

Dittmann

Sonnenschein

Egan

et al. 2018

Environ Microbiol Rep

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“…3). High-performance liquid chromatography (HPLC) analysis showed the emergence of a new peak in the enzyme reaction, for which the high-resolution mass spectrometry (MS) and tandem mass spectrometry (MS/MS) data were consistent with pseudochelin A (21). When myxochelin B was incubated without 6ϫHis-MxcM, no further peak was detected.…”

Section: Resultsmentioning

confidence: 99%

“…A subsequent reduction reaction forms myxochelin A (compound 1), whereas the transamination of the aldehyde, catalyzed by an aminotransferase (MxcL), leads to myxochelin B (compound 2). Recently, a novel myxochelin derivative termed pseudochelin A (compound 3) was isolated from the marine bacterium Pseudoalteromonas piscicida S2040 (21). Pseudochelin A features a characteristic 4,5-dihydroimidazole moiety, putatively emerging from an intramolecular cyclization reaction of myxochelin B (Fig.…”

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confidence: 99%

Engineering Pseudochelin Production in Myxococcus xanthus

Korp

Winand

Sester

et al. 2018

Appl Environ Microbiol

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Myxobacteria utilize the catechol natural products myxochelin A and B in order to maintain their iron homeostasis. Recently, the production of these siderophores was reported from the marine bacterium S2040, along with a new myxochelin derivative named pseudochelin A. The latter features a characteristic imidazoline moiety, which was proposed to originate from an intramolecular condensation reaction of the β-aminoethyl amide group in myxochelin B. To identify the enzyme catalyzing this conversion, we compared the myxochelin regulons of two myxobacterial strains, which solely produce myxochelin A and B, with S2040. This approach revealed a gene exclusive to the myxochelin regulon in S2040, coding for an enzyme of the amidohydrolase superfamily. To prove that this enzyme is indeed responsible for the postulated conversion, the reaction was reconstituted using a hexahistidyl-tagged recombinant protein made in and myxochelin B as substrate. To test the production of pseudochelin A under conditions, the amidohydrolase gene was cloned into the myxobacterial plasmid pZJY156 and placed under the control of a copper-inducible promoter. The resulting vector was introduced into the myxobacterium DSM16526, a native producer of myxochelin A and B. Following the induction with copper, the myxobacterial expression strain was found to synthesize small quantities of pseudochelin A. Replacement of the copper-inducible promoter with the constitutive promoter led to increased production levels in , which facilitated the isolation and subsequent structural verification of the heterologously produced compound. In this study, an enzyme for imidazoline formation in pseudochelin biosynthesis was identified. Evidence for the involvement of this enzyme in the postulated reaction was obtained after reconstitution. Furthermore, the function of this enzyme was also demonstrated by transferring the corresponding gene into the bacterium , which thereby became a producer of pseudochelin A. Aside from clarifying the molecular basis of imidazoline formation in siderophore biosynthesis, we describe the heterologous expression of a gene in a myxobacterium without its chromosomal integration. Due to its metabolic proficiency, represents an interesting alternative to established host systems for the reconstitution and manipulation of biosynthetic pathways. Since the plasmid used in this study is easily adaptable for the expression of other enzymes as well, we expand the conventional expression strategy for myxobacteria, which is based on the integration of biosynthetic genes into the host genome.

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“…Another strain, P . piscicida S2040, was recently reported to produce several siderophores (pseudochelin and myxochelins) and the anti‐cancer molecule, alteramide A (Sonnenschein et al., ). To assess whether secondary metabolite production by P .…”

Section: Resultsmentioning

confidence: 99%

“…P. piscicida JCM 20779 is predicted to encode nine biosynthetic gene clusters based on antiSMASH 4.0 analysis (Supporting Information Table S1); however, the only natural products characterized for this strain are the alterochromide family of lipopeptides (Ross et al, 2015). Another strain, P. piscicida S2040, was recently reported to produce several siderophores (pseudochelin and myxochelins) and the anti-cancer molecule, alteramide A (Sonnenschein et al, 2017). To assess whether secondary metabolite production by P. piscicida JCM 20779 is affected by adding a solid support, we grew the strain in liquid media in the presence and absence of a cotton scaffold.…”

Section: Pseudoalteromonas Piscicida Jcm20779mentioning

confidence: 99%

Culturing marine bacteria from the genus Pseudoalteromonas on a cotton scaffold alters secondary metabolite production

et al. 2018

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The discovery of secondary metabolites from marine microorganisms is beset by numerous challenges including difficulties cultivating and subsequently eliciting expression of biosynthetic genes from marine microbes in the laboratory. In this paper, we describe a method of culturing three species from the marine bacterial genus Pseudoalteromonas using cotton scaffold supplemented liquid media. This simple cultivation method was designed to mimic the natural behavior of some members of the genus wherein they form epibiotic/symbiotic associations with higher organisms such as sponges and corals or attach to solid structures as a biofilm. Our scaffolded cultivation is highly effective at stimulating an attachment/biofilm phenotype and causes large changes to metabolite profiles for the microbes investigated. Metabolite changes include alteration to the production levels of known molecules such as violacein, thiomarinol A, and the alterochromide and prodiginine families of molecules. Finally and critically, our technique stimulates the production of unknown compounds that will serve as leads for future natural product discovery. These results suggest our cultivation approach could potentially be used as a general strategy for the activation of silent gene clusters in marine microbes to facilitate access to their full natural product biosynthetic capacity.

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Pseudochelin A, a siderophore of Pseudoalteromonas piscicida S2040

Cited by 20 publications

References 38 publications

Impact of Phaeobacter inhibens on marine eukaryote‐associated microbial communities

Impact of Phaeobacter inhibens on marine eukaryote‐associated microbial communities

Engineering Pseudochelin Production in Myxococcus xanthus

Culturing marine bacteria from the genus Pseudoalteromonas on a cotton scaffold alters secondary metabolite production

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