Roseochelin B, an Algaecidal Natural Product Synthesized by the <i>Roseobacter Phaeobacter inhibens</i> in Response to Algal Sinapic Acid

Wang, Rurun; Seyedsayamdost, Mohammad R.

doi:10.1021/acs.orglett.7b02424

Cited by 31 publications

(33 citation statements)

References 28 publications

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“…The rapid decline in maximum quantum yield and loss of chlorophyll observed in the C-and S-type cultures at 8-10 days (Figure 2) is consistent with the physiological response of E. huxleyi to roseobacticides, which causes cell membrane blebbing, chloroplast loss, and lysis of N-type cells (Seyedsayamdost et al, 2011b). Roseobacticides are produced by P. inhibens when supplied with p-coumaric acid (pCA) (Seyedsayamdost et al, 2011b) and other lignin precursors (Wang and Seyedsayamdost, 2017). pCA is produced by E. huxleyi and hypothesized to be made during senescence (Seyedsayamdost et al, 2011b) where it is an intermediary of the lignin and flavonoid pathways .…”

Section: Are Roseobacticides Responsible For Death Of C-and S-type Cesupporting

confidence: 71%

“…P. inhibens is a member of the roseobacter clade that is frequently identified within E. huxleyi blooms (González et al, 2000;Green et al, 2015;Segev et al, 2016). This bacterium produces a number of novel bioactives, including the antibiotic tropodithetic acid (TDA) (Geng et al, 2008;Berger et al, 2011;Thole et al, 2012) and potent algaecides called roseobacticides (Seyedsayamdost et al, 2011b(Seyedsayamdost et al, , 2014 and roseochelins (Wang and Seyedsayamdost, 2017). These bioactives might allow P. inhibens to live a duplicitous lifestyle as both a beneficial symbiont and as a pathogen.…”

Section: Introductionmentioning

confidence: 99%

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The Bacterial Symbiont Phaeobacter inhibens Shapes the Life History of Its Algal Host Emiliania huxleyi

et al. 2018

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Marine microbes form host-associated biofilm communities that are shaped by complex interactions between bacteria and their host. The roseobacter Phaeobacter inhibens exploits both symbiotic and pathogenic niches while interacting with its microalgal host Emiliania huxleyi. During co-cultivation over extended periods with E. huxleyi, we show that P. inhibens selectively kills two host cell types, the diploid calcifying strain and the haploid flagellated strain. Meanwhile, various non-calcifying diploid strains are resistant to this pathogen or the pathogen is avirulent to this cell type. This differential pathogenesis has the potential of dramatically altering the composition of E. huxleyi blooms, which are typically dominated by the roseobacter-susceptible calcifying strain. This cell type makes calcite plates, which are an important sink in the marine carbon cycle and forms part of the marine paleobotanic record. P. inhibens kills the haploid cells, which have been proposed as critical to the survival of the algae, as they readily escape both eukaryotic predation and viral infection. Consequently, bacteria such as P. inhibens could influence E. huxleyi's life history by selective pathogenesis, thereby altering the composition of cell types within E. huxleyi populations and its bloom-bust lifestyle.

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Section: Are Roseobacticides Responsible For Death Of C-and S-type Cesupporting

confidence: 71%

Section: Introductionmentioning

confidence: 99%

The Bacterial Symbiont Phaeobacter inhibens Shapes the Life History of Its Algal Host Emiliania huxleyi

et al. 2018

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“…Strains from the closely related genera Pseudophaeobacter and Leisingera as well as TDA‐producers from the genera Ruegeria and Pseudovibrio did not produce roseobacticides under the tested conditions. This confirmed previous roseobacticide analyses of the strains DSM 17395 (BS107), 2.10, 27‐4 and TM1040, and adds DSM 16374 as a roseobacticide producer although not detected previously (Seyedsayamdost et al ., ; Wang and Seyedsayamdost, ). Thus, the ability of roseobacticide production appears to be limited to a phylogenetic subgroup within the Roseobacter group including the species P. inhibens , P. gallaeciensis and P. piscinae (with type strains of these species being included in the analysis, Fig.…”

Section: Resultsmentioning

confidence: 99%

“… Ros., roseobacticides; TDA, tropodithietic acid; NA, not available; unpub, unpublished. *, strains that were also previously analyzed for roseobacticide production (Seyedsayamdost et al ., ; Wang and Seyedsayamdost, ).…”

Section: Resultsmentioning

confidence: 99%

“…Possibly, these modes are interlinked genetically, or metabolically, and depend on exterior factors such as nutrient supply. This scenario was proposed for the interaction between Emiliania huxleyi , a globally important, bloom‐forming haptophyte (Read et al ., ) and the alphaproteobacterium Phaeobacter inhibens (Seyedsayamdost et al ., ; Segev et al ., ; Wang et al ., ; Wang and Seyedsayamdost, ). The bacterium belongs to the Roseobacter group, one of the most common and widespread marine bacterial groups and a group often co‐appearing with microalgae (Sapp et al ., ; Luo and Moran, ; Tan et al ., ; Sonnenschein et al ., ,b).…”

Section: Introductionmentioning

confidence: 99%

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Phylogenetic distribution of roseobacticides in the Roseobacter group and their effect on microalgae

Sonnenschein

Phippen

Bentzon-Tilia

et al. 2018

Environ Microbiol Rep

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The Roseobacter-group species Phaeobacter inhibens produces the antibacterial tropodithietic acid (TDA) and the algaecidal roseobacticides with both compound classes sharing part of the same biosynthetic pathway. The purpose of this study was to investigate the production of roseobacticides more broadly in TDA-producing roseobacters and to compare the effect of producers and non-producers on microalgae. Of 33 roseobacters analyzed, roseobacticide production was a unique feature of TDA-producing P. inhibens, P. gallaeciensis and P. piscinae strains. One TDA-producing Phaeobacter, 27-4, did not produce roseobacticides, possibly due to a transposable element. TDA-producing Ruegeria and Pseudovibrio did not produce roseobacticides. Addition of roseobacticide-containing bacterial extracts affected the growth of the microalgae Rhodomonas salina, Thalassiosira pseudonana and Emiliania huxleyi, while growth of Tetraselmis suecica was unaffected. During co-cultivation, growth of E. huxleyi was initially stimulated by the roseobacticide producer DSM 17395, while the subsequent decline in algal cell numbers during senescence was enhanced. Strain 27-4 that does not produce roseobacticides had no effect on algal growth. Both bacterial strains, DSM 17395 and 27-4, grew during co-cultivation presumably utilizing algal exudates. Furthermore, TDA-producing roseobacters have potential as probiotics in marine larviculture and it is promising that the live feed Tetraselmis was unaffected by roseobacticides-containing extracts.

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Structural Elucidation of Cryptic Algaecides in Marine Algal‐Bacterial Symbioses by NMR Spectroscopy and MicroED

Park

Moon

et al. 2021

Angewandte Chemie

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Microbial secondary metabolite discovery is often conducted in pure monocultures. In a natural setting, however, where metabolites are constantly exchanged, biosynthetic precursors are likely provided by symbionts or hosts. In the current work, we report eight novel and architecturally unusual secondary metabolites synthesized by the bacterial symbiont Phaeobacter inhibens from precursors that, in a native context, would be provided by their algal hosts. Three of these were produced at low titres and their structures were determined de novo using the emerging microcrystal electron diffraction method. Some of the new metabolites exhibited potent algaecidal activity suggesting that the bacterial symbiont can convert algal precursors, tryptophan and sinapic acid, into complex cytotoxins. Our results have important implications for the parasitic phase of algal‐bacterial symbiotic interactions.

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Roseochelin B, an Algaecidal Natural Product Synthesized by the Roseobacter Phaeobacter inhibens in Response to Algal Sinapic Acid

Cited by 31 publications

References 28 publications

The Bacterial Symbiont Phaeobacter inhibens Shapes the Life History of Its Algal Host Emiliania huxleyi

The Bacterial Symbiont Phaeobacter inhibens Shapes the Life History of Its Algal Host Emiliania huxleyi

Phylogenetic distribution of roseobacticides in the Roseobacter group and their effect on microalgae

Structural Elucidation of Cryptic Algaecides in Marine Algal‐Bacterial Symbioses by NMR Spectroscopy and MicroED

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