Algicidal lactones from the marine <i>Roseobacter</i> clade bacterium <i>Ruegeria pomeroyi</i>

Riclea, Ramona; Gleitzmann, Julia; Bruns, Hilke; Junker, Corina; Schulz, Barbara; Dickschat, Jeroen S.

doi:10.3762/bjoc.8.106

Cited by 34 publications

(33 citation statements)

References 33 publications

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“…Indole (35), present in almost all investigated strains,i sw ell known as ab acterial metabolite, especially from Escherichia coli, [56] although it is also released by severalo ther bacteria. [57] Extracellular indole serves as as ignal.…”

Section: Discussionmentioning

confidence: 99%

“…Almost all strainsp roduced indole (35), ak nown signaling compound in several bacteria. [45][46] [47] Large amountsw ere emitted especially by strain Litoreibacter sp.…”

Section: Other Compoundsmentioning

confidence: 99%

“…[34] Some of the latter (e.g.,l actone 13,p roduced by R. pomeroyi) showed inhibitory effects at high concentrations against freshwater algae. [35] Compared to the Actinobacteria or Cyanobacteria, the number of known secondary metabolites is quite small for the Roseobacter clade,b ut certainly not fully explored yet. [36] Roseobacters seem to lack the large geneticd iversity of biosynthetic genes for secondary metabolite production found in those groups.…”

Section: Introductionmentioning

confidence: 99%

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Homoserine Lactones, Methyl Oligohydroxybutyrates, and Other Extracellular Metabolites of Macroalgae‐Associated Bacteria of the Roseobacter Clade: Identification and Functions

et al. 2015

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Twenty-four strains of marine Roseobacter clade bacteria were isolated from macroalgae and investigated for the production of quorum-sensing autoinducers, N-acylhomoserine lactones (AHLs). GC/MS analysis of the extracellular metabolites allowed us to evaluate the release of other small molecules as well. Nineteen strains produced AHLs, ranging from 3-OH-C10:0-HSL (homoserine lactone) to (2E,11Z)-C18:2-HSL, but no specific phylogenetic or ecological pattern of individual AHL occurrence was observed when cluster analysis was performed. Other identified compounds included indole, tropone, methyl esters of oligomers of 3-hydroxybutyric acid, and various amides, such as N-9-hexadecenoylalanine methyl ester (9-C16:1-NAME), a structural analogue of AHLs. Several compounds were tested for their antibacterial and antialgal activity on marine isolates likely to occur in the habitat of the macroalgae. Both AHLs and 9-C16:1-NAME showed high antialgal activity against Skeletonema costatum, whereas their antibacterial activity was low.

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Section: Discussionmentioning

confidence: 99%

“…Almost all strainsp roduced indole (35), ak nown signaling compound in several bacteria. [45][46] [47] Large amountsw ere emitted especially by strain Litoreibacter sp.…”

Section: Other Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Homoserine Lactones, Methyl Oligohydroxybutyrates, and Other Extracellular Metabolites of Macroalgae‐Associated Bacteria of the Roseobacter Clade: Identification and Functions

et al. 2015

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“…Previous reports have demonstrated that many bacteria have a significant algicidal effect on several harmful algal bloom species (10,11,14,17). Most algicidal bacteria isolated from the environment are characterized as belonging to the genera Cytophaga, Saprospira, Pseudoalteromonas, and Alteromonas (55 Four types of these metabolites, surfactin and polyketides (difficidin, macrolactin, and bacillaene), are known for their antibacterial activity (24,30).…”

Section: Discussionmentioning

confidence: 99%

“…(14,15), ␤-cyano-L-alanine from Vibrio spp. (16), and lactones produced by Ruegeria pomeroyi (17). Recent studies have demonstrated that Bacillus spp.…”

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Bacilysin from Bacillus amyloliquefaciens FZB42 Has Specific Bactericidal Activity against Harmful Algal Bloom Species

Chen

et al. 2014

Appl Environ Microbiol

106

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bHarmful algal blooms, caused by massive and exceptional overgrowth of microalgae and cyanobacteria, are a serious environmental problem worldwide. In the present study, we looked for Bacillus strains with sufficiently strong anticyanobacterial activity to be used as biocontrol agents. Among 24 strains, Bacillus amyloliquefaciens FZB42 showed the strongest bactericidal activity against Microcystis aeruginosa, with a kill rate of 98.78%. The synthesis of the anticyanobacterial substance did not depend on Sfp, an enzyme that catalyzes a necessary processing step in the nonribosomal synthesis of lipopeptides and polyketides, but was associated with the aro gene cluster that is involved in the synthesis of the sfp-independent antibiotic bacilysin. Disruption of bacB, the gene in the cluster responsible for synthesizing bacilysin, or supplementation with the antagonist N-acetylglucosamine abolished the inhibitory effect, but this was restored when bacilysin synthesis was complemented. Bacilysin caused apparent changes in the algal cell wall and cell organelle membranes, and this resulted in cell lysis. Meanwhile, there was downregulated expression of glmS, psbA1, mcyB, and ftsZ-genes involved in peptidoglycan synthesis, photosynthesis, microcystin synthesis, and cell division, respectively. In addition, bacilysin suppressed the growth of other harmful algal species. In summary, bacilysin produced by B. amyloliquefaciens FZB42 has anticyanobacterial activity and thus could be developed as a biocontrol agent to mitigate the effects of harmful algal blooms. Eutrophication of surface waters has many undesirable effects and can lead to major water quality issues in freshwater and coastal systems (1). This phenomenon results in blooms of harmful algal species in freshwater lakes and brackish waters throughout the world. Moreover, the excessive growth of harmful algae, such as microalgae and cyanobacteria, often increases the production of inherent toxins such as microcystins and nodularins that cause acute poisonings of fish, birds, and mammals, including humans (2). For example, dogs died after they were exposed to a cyanobacterial bloom of Microcystis aeruginosa in Lake Amstelmeer (The Netherlands), and the concentration of microcystin in this lake was up to 5.27 ϫ 10 3 g g Ϫ1 of dry weight (3). In recent years, harmful algal blooms of eutrophic water in China have occurred frequently, including in Lake Taihu and Lake Chaohu, and Microcystis is thought to be the dominant bloom genera (4).Many control techniques have been used to prevent and mitigate bloom problems, including yellow loess (5), clay (6), and chemical agents such as copper sulfate and hydrogen peroxide (7). However, each of the physical and chemical methods available to remediate eutrophic water is associated with certain disadvantages (8). Therefore, there is still a pressing need for environmentally friendly, cost-effective, and convenient bactericidal agents directed against cyanobacterial blooms in eutrophic lakes. Biological control agents such as bact...

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Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica

et al. 2016

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Terrestrial bacteria, especially actinomycetes, are known to be prolific producers of volatile compounds. We show here that bacteria from ocean sediments can also release complex bouquets of volatiles. The actinomycete Salinispora tropica produces novel cyclohexenyl compounds, such as methyl cyclohex-2-ene-1-carboxylate (9), methyl 2-(cyclohex-2-en-1-yl)acetate (10), methyl (E/Z)-2-(cyclohex-2-en-1-ylidene)acetate (11, 12), and related alcohols (8, 13). These compounds were identified by GC/MS and confirmed by synthesis. In addition, rare spiroacetals, aromatic compounds, short chain acids and esters, alcohols, and various cyclic compounds were produced by the bacteria. The biosynthesis of the cyclohexenyl compounds is closely coupled to that of cyclohexenylalanine (4), a building block of salinosporamide A, a proteasome inhibitor produced by S. tropica. Analysis of S. tropica strains that harbor knockouts of the salinosporamide biosynthetic genes salX and salD, coupled with feeding experiments, revealed that 3-(cyclohex-2-en-1-yl)-2-oxopropanoic acid (60) and 3-(cyclohex-2-en-1-ylidene)-2-oxopropanoic acid (61, 62) are important intermediates in the biosynthesis of salinosporamide A, 4, and 8–13.

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Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

Cited by 34 publications

References 33 publications

Homoserine Lactones, Methyl Oligohydroxybutyrates, and Other Extracellular Metabolites of Macroalgae‐Associated Bacteria of the Roseobacter Clade: Identification and Functions

Homoserine Lactones, Methyl Oligohydroxybutyrates, and Other Extracellular Metabolites of Macroalgae‐Associated Bacteria of the Roseobacter Clade: Identification and Functions

Bacilysin from Bacillus amyloliquefaciens FZB42 Has Specific Bactericidal Activity against Harmful Algal Bloom Species

Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica

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