Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

• Anuj Kumar Chhalodia and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

• -(allylmethylsulfonio)propanoate (AllMSP), were synthesized and fed to marine bacteria from the Roseobacter clade. These bacteria are able to degrade DMSP into dimethyl sulfide and methanethiol. The DMSP analogues were also degraded, resulting in the release of allylated sulfur volatiles known from garlic. For unknown

• sativum; allyl sulfides; 3-(dimethylsulfonio)propanoate; Roseobacter; volatiles; Introduction The name of the allyl group has been introduced by Wertheim in 1844 when he investigated the constituents of garlic oil and derives from the botanical name of garlic (Allium sativum) [1]. During that time, the

• ]. For the macroalga Ulva mutabilis the presence of bacteria from the Roseobacter group is even mandatory for proper algal development, and 3-(dimethylsulfonio)propanoate (DMSP) is used as a chemotactic signal by the bacteria attracting them towards the algal host [12]. Many bacteria and fungi also

Identification of volatiles from six marine Celeribacter strains

• Anuj Kumar Chhalodia,
• Jan Rinkel,
• Dorota Konvalinkova,
• Jörn Petersen and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

• Celeribacter strains are capable of methionine and DMSP degradation to widespread sulfur volatiles, but the analysis of trace compounds in natural samples must be taken with care. Keywords: GC–MS; isotopes; Roseobacter; sulfur metabolism; volatiles; Introduction Bacteria from the roseobacter group belong to

• marine organisms, e.g., Thalassococcus halodurans DSM 26915T has been isolated from the marine sponge Halichondria panicea [5], and Phaeobacter gallaeciensis DSM 26640T is an isolate from the scallop Pecten maximus [6]. Important interactions are also observed between bacteria from the roseobacter group

• and various types of marine algae, e.g., the first described organisms Roseobacter litoralis DSM 6996T and R. denitrificans DSM 7001T were obtained from seaweed [7], while Dinoroseobacter shibae DSM 16493T and Marinovum algicola DSM 10251T are both isolates from the dinoflagellate Prorocentrum lima [8

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

• Hilke Bruns,
• Lisa Ziesche,
• Nargis Khakin Taniwal,
• Laura Wolter,
• Thorsten Brinkhoff,
• Jennifer Herrmann,
• Rolf Müller and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

• Roseobacter group (Rhodobacteraceae) are important members of many marine ecosystems. Similar to other Gram-negative bacteria many roseobacters produce N-acylhomoserine lactones (AHLs) for communication by quorum sensing systems. AHLs regulate different traits like cell differentiation or antibiotic

• spectra often reveal key structural features. Furthermore, the availability of large cross-platform databases useful for dereplication allows focussing on new compounds. We are interested in natural compounds from Roseobacter group bacteria, an abundant class of marine bacteria occurring in diverse

• knowledge on their biosynthesis, the underlying gene organization, as well as their function in many bacteria [11][12][13]. In the Roseobacter group, AHLs are involved, e.g., in antibiotic production [9] or cell differentiation [10]. Although many other bacterial signalling compounds must exist, only few of

Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria

• Lisa Ziesche,
• Jan Rinkel,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 1309–1316, doi:10.3762/bjoc.14.112

• /bjoc.14.112 Abstract N-Acylhomoserine lactones (AHLs) are important bacterial messengers, mediating different bacterial traits by quorum sensing in a cell-density dependent manner. AHLs are also produced by many bacteria of the marine Roseobacter group, which constitutes a large group within the marine

• ; fatty acid composition; N-acylhomoserine lactones; quorum sensing; Phaeobacter inhibens; Introduction The Roseobacter group, a subgroup of the Rhodobacteraceae family, constitutes an important class of Gram-negative marine bacteria, occurring in many different habitats [1][2], in fresh water as well as

• regulate several physiological traits regulated by cell density, the ‘quorum’ [11][12][13][14][15][16], in roseobacters, e.g., in the production of the antibiotic tropodithietic acid in Phaeobacter inhibens [15] and cell differentiation in Dinoroseobacter shibae [14]. Roseobacter group AHLs are

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

• Patrick Rabe,
• Tim A. Klapschinski,
• Nelson L. Brock,
• Christian A. Citron,
• Paul D’Alvise,
• Lone Gram and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2014, 10, 1796–1801, doi:10.3762/bjoc.10.188

• of Denmark, Matematiktorvet bldg. 301, 2800 Kongens Lyngby, Denmark 10.3762/bjoc.10.188 Abstract Tropodithietic acid (TDA) is a structurally unique sulfur-containing antibiotic from the Roseobacter clade bacterium Phaeobacter inhibens DSM 17395 and a few other related species. We have synthesised

• the bioactivity of the natural product. The synthesis of this compound and of several analogues is presented and the bioactivity of the synthetic compounds is discussed. Keywords: antibiotics; natural products; Roseobacter; SAR study; tropodithietic acid; tropone; Introduction Tropodithietic acid

• . inhibens or other TDA-producing bacteria from the Roseobacter clade as promising candidates to be used as probiotics in aquacultures [12]. The mode of action of TDA is unknown, but it is difficult to select resistant and tolerant strains from long-term exposures to sub inhibitory concentrations of TDA

Isotopically labeled sulfur compounds and synthetic selenium and tellurium analogues to study sulfur metabolism in marine bacteria

• Nelson L. Brock,
• Christian A. Citron,
• Claudia Zell,
• Martine Berger,
• Irene Wagner-Döbler,
• Jörn Petersen,
• Thorsten Brinkhoff,
• Meinhard Simon and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 942–950, doi:10.3762/bjoc.9.108

• , Germany 10.3762/bjoc.9.108 Abstract Members of the marine Roseobacter clade can degrade dimethylsulfoniopropionate (DMSP) via competing pathways releasing either methanethiol (MeSH) or dimethyl sulfide (DMS). Deuterium-labeled [2H6]DMSP and the synthetic DMSP analogue dimethyltelluriopropionate (DMTeP

• ) were used in feeding experiments with the Roseobacter clade members Phaeobacter gallaeciensis DSM 17395 and Ruegeria pomeroyi DSS-3, and their volatile metabolites were analyzed by closed-loop stripping and solid-phase microextraction coupled to GC–MS. Feeding experiments with [2H6]DMSP resulted in the

• methaneselenol-derived volatiles via reduction and methylation. The pathway of selenate/selenite reduction, however, proved to be strictly separated from sulfate reduction. Keywords: dimethylsulfoniopropionate; Roseobacter clade; selenium metabolism; sulfur metabolism; volatiles; Introduction The Roseobacter

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

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

Beilstein J. Org. Chem. 2012, 8, 941–950, doi:10.3762/bjoc.8.106

• Braunschweig, Germany 10.3762/bjoc.8.106 Abstract Volatiles released by the marine Roseobacter clade bacterium Rugeria pomeroyi were collected by use of a closed-loop stripping headspace apparatus (CLSA) and analysed by GC–MS. Several lactones were found for which structural proposals were derived from their

• investigate their activity against several bacteria, fungi, and algae. A specific algicidal activity was observed that may be important in the interaction between the bacteria and their algal hosts in fading algal blooms. Keywords: bacteria-algae symbiosis; lactones; Roseobacter; synthesis; volatiles

• ; Introduction Bacteria of the Roseobacter clade form one of the most abundant lineages of marine bacteria that occur globally in marine ecosystems from polar to tropical regions [1][2]. They are present in costal and open ocean environments, in surface waters and in the water column; are found as algal