Marine bacteria from the Roseobacter clade produce sulfur volatiles via amino acid and dimethylsulfoniopropionate catabolism

Brock, Nelson L.; Menke, Markus; Klapschinski, Tim A.; Dickschat, Jeroen S.

doi:10.1039/c4ob00719k

Cited by 32 publications

(42 citation statements)

References 23 publications

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“…We tested the stress-protective properties of DMSP, its natural selenium analogue DMSeP (Ansede and Yoch, 1997;Ansede et al, 1999) and six synthetic DMSP derivatives (Dickschat et al, 2010;Brock et al, 2014) ( Fig. 1) for B. subtilis cells that were continuously challenged either by extremes in salinity (1.2 M NaCl) or growth temperatures (13°C and 52°C).…”

Section: Stress Protection By Dmsp and Its Derivatives Against High Smentioning

confidence: 99%

Abiotic stress protection by ecologically abundant dimethylsulfoniopropionate and its natural and synthetic derivatives: insights fromBacillus subtilis

Broy

Chen

Hoffmann

et al. 2014

Environmental Microbiology

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Dimethylsulfoniopropionate (DMSP) is an abundant osmolyte and anti-stress compound produced primarily in marine ecosystems. After its release into the environment, microorganisms can exploit DMSP as a source of sulfur and carbon, or accumulate it as an osmoprotectant. However, import systems for this ecophysiologically important compatible solute, and its stress-protective properties for microorganisms that do not produce it are insufficiently understood. Here we address these questions using a well-characterized set of Bacillus subtilis mutants to chemically profile the influence of DMSP import on stress resistance, the osmostress-adaptive proline pool and on osmotically controlled gene expression. We included in this study the naturally occurring selenium analogue of DMSP, dimethylseleniopropionate (DMSeP), as well as a set of synthetic DMSP derivatives. We found that DMSP is not a nutrient for B. subtilis, but it serves as an excellent stress protectant against challenges conferred by sustained high salinity or lasting extremes in both low and high growth temperatures. DMSeP and synthetic DMSP derivatives retain part of these stress protective attributes, but DMSP is clearly the more effective stress protectant. We identified the promiscuous and widely distributed ABC transporter OpuC as a high-affinity uptake system not only for DMSP, but also for its natural and synthetic derivatives.

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Section: Stress Protection By Dmsp and Its Derivatives Against High Smentioning

confidence: 99%

Abiotic stress protection by ecologically abundant dimethylsulfoniopropionate and its natural and synthetic derivatives: insights fromBacillus subtilis

Broy

Chen

Hoffmann

et al. 2014

Environmental Microbiology

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“…Va riation of GC conditions,columns,and floral extraction methods did not aid detection, thus indicating that the limitation is either suboptimal chromatographic properties for these compounds (broad peaks) or problems related to the specific antennal receptors.F urthermore,G C-MS screening for cyclohexane-1,3-dione-and pyrazine-based compounds known in other Australian orchid/thynnine wasp pollination systems, [2] as well as structurally related compounds,r evealed none of these compounds.Afinal set of semiochemical candidates was defined by their presence in both the active lateral sepal tips (clubs,F igure 1) and female wasp extracts,b ut not in the inactive floral remains.H igh-resolution GC-MS (GC-HRMS) revealed compounds with molecular formulae Them ass spectra and molecular formulae indicated that all four candidates were phenols with sulfur-containing substituents.T he identification process was expedited by the occurrence of the mass spectrum of our simplest candidate in the NIST-11 mass spectral library.T his compound (1;F igure 2), previously found in bacteria, [6] was confirmed by co-injection of the biological extracts with ac ommercially available reference compound. Based on similarities in molecular formulae and mass spectra, we proposed several structurally related compounds for the remaining three candidates,i ncluding hydroxy,hydroxymethyl and formyl compounds,which were all prepared synthetically and from which the matching compounds were successfully identified.…”

mentioning

confidence: 97%

“…[6] Other aromatic sulfurous compounds identified from plants or animals,apart from orchids,a re limited to thiophenes, [10] thiazoles, [11] and benzyl methyl sulfide (Figure 1). [12] Sulfurous floral volatiles are typically rare [13] and their function often unknown.…”

Section: Communicationsmentioning

confidence: 99%

The Spider Orchid Caladenia crebra Produces Sulfurous Pheromone Mimics to Attract its Male Wasp Pollinator

et al. 2017

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One of the most intriguing natural observations is the pollination of orchids by sexual deception. Chemicals underpin this interaction between the orchida nd its sexually attracted male insect pollinator,with the signaling compounds involved, called semiochemicals,p redicted to mimic the chemical composition of the sex pheromone.W ei dentified floral semiochemicals from Caladenia (spider orchids) for the first time.W ef urther demonstrate that C. crebra attracts its single pollinator species with aunique system of (methylthio)-phenols,three of whichare new natural products.Furthermore, as predicted, the same compounds constitute the sex pheromone of the pollinator,t he thynnine wasp Campylothynnus flavopictus,r epresenting the first occurrence of sulfurous sex pheromones in Hymenoptera.While studies of plant-pollinator communities show that many plant species attract multiple pollinators, [1] numerous highly specialized pollination systems have been discovered that are underpinned by chemistry.[2a-c] Pollination through sexual deception is ah ighly specialized pollination strategy, primarily known from orchids,w here chemical mimicry of courting female insects leads to the attraction of male pollinators.[2] So far there have only been af ew studies where the compounds involved have been elucidated and confirmed with field bioassays.These include either blends of alkanes and alkenes,o rh ydroxy-and keto acids in Ophrys orchids,c yclohexane-1,3-diones in Chiloglottis orchids,a nd pyrazines in Drakaea orchids. [3] Caladenia is ad iverse genus of Australian terrestrial orchids,comprising over 360 species.[4] Thegenus is unique in that it employs multiple pollination strategies including food reward, food deception, and more than 100 cases of sexual deception.[5] Until now,t he identity of the chemicals for signaling between organisms (semiochemicals) involved in sexual deception has remained elusive for any Caladenia species,a lthough given that many different wasp genera are exploited, multiple chemical systems are expected to operate. Thus,d etailed studies of the chemistry of this genus,b eyond the promise of revealing new natural products,a lso offers au nique opportunity to better understand the role of floral volatiles in the evolution of sexual deception as apollination strategy.In this work, we investigated the chemistry of sexual deception in Caladenia crebra A.S.George.B yc ombining chemical ecology,analytical chemistry,and organic chemistry methods,wedemonstrate that in C. crebra,pollination by the thynnine wasp Campylothynnus flavopictus (Smith, 1859) requires as pecific blend of unique aromatic sulfurous compounds in precise ratios.I nt he exceptional mating behavior of thynnine wasps,t he larger,w inged males carry the smaller, wingless females in copula to af ood source for mating and feeding.[3a] While conducting field bioassays with artificially presented orchid flowers,o nt hree occasions, thynnine wasp pairs were observed arriving at the flower in copula, ab ehavior not previously rep...

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“…[101][102][103] These compounds were easily prepared by the HCl catalysed Michael addition of dialkyl chalcogenides to acrylic acid (28). [101][102][103] These compounds were easily prepared by the HCl catalysed Michael addition of dialkyl chalcogenides to acrylic acid (28).…”

Section: Bacterial Conversion Of Dmsp Analogsmentioning

confidence: 99%

“…Interestingly, DMSeP was also efficiently demethylated, as indicated by the formation of various MeSeH derived volatiles, whereas no volatiles were detected from DMTeP. 103 Accordingly, the production of EtSH-derived volatiles from DESP could be observed, but was poor.…”

Section: Bacterial Conversion Of Dmsp Analogsmentioning

confidence: 99%

The chemical biology of dimethylsulfoniopropionate

2015

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Dimethylsulfoniopropionate is a highly abundant sulfur metabolite in marine ecosystems. Its biosynthesis by different organisms including plants, marine algae and dinoflagellates is discussed. Furthermore, the accumulated knowledge about bacterial uptake systems and its climatically relevant degradation by marine bacteria to methanethiol or dimethylsulfide is presented. Finally, uptake and degradation of synthetic DMSP analogs are addressed.

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Marine bacteria from the Roseobacter clade produce sulfur volatiles via amino acid and dimethylsulfoniopropionate catabolism

Cited by 32 publications

References 23 publications

Abiotic stress protection by ecologically abundant dimethylsulfoniopropionate and its natural and synthetic derivatives: insights fromBacillus subtilis

Abiotic stress protection by ecologically abundant dimethylsulfoniopropionate and its natural and synthetic derivatives: insights fromBacillus subtilis

The Spider Orchid Caladenia crebra Produces Sulfurous Pheromone Mimics to Attract its Male Wasp Pollinator

The chemical biology of dimethylsulfoniopropionate

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