Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• prenyltransferase; Introduction Marine bacteria harbor an enormous potential to produce structurally diverse natural products, including prenylated aromatic metabolites [1][2]. Prenylation of metabolites most often confers increased biological activities due to enhanced lipophilicity, solubility, and improved

• biosynthetic repertoire of marine bacteria [14][15], the diversity of the encoded and yet often unexplored bacterial Ptases of Flavobacteria and Saccharomonospora strains sparked our interest. In this study we investigated three yet poorly described homologous Ptases within the UbiA superfamily and evaluated

• their substrate scope by heterologous production and enzymatic bioassays. Results of our study showcase that marine bacteria harbor still a broad unexplored enzymatic repertoire. Results and Discussion In silico analysis of Ptases in marine Flavobacteria and the genus Saccharomonospora In a first step

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• available on the secondary metabolites from this genus [17][18]. In our continuing search for bioactive compounds from underexplored marine bacteria [19][20][21], a Tenacibaculum strain, isolated from a stony coral, was found to produce three metabolites, which turned out to be new cytotoxic hydroxamate

A new glance at the chemosphere of macroalgal–bacterial interactions: In situ profiling of metabolites in symbiosis by mass spectrometry

• Marine Vallet,
• Filip Kaftan,
• Veit Grabe,
• Fatemeh Ghaderiardakani,
• Simona Fenizia,
• Aleš Svatoš,
• Georg Pohnert and
• Thomas Wichard

Beilstein J. Org. Chem. 2021, 17, 1313–1322, doi:10.3762/bjoc.17.91

• distributions of metabolites and identifying specific symbiotic bacteria. Keywords: algae; AP-SMALDI; ectoine; holobiont; high-resolution mass spectrometry; mass spectrometry imaging; marine bacteria; Ulva; Introduction In intertidal zones with high temporal and spatial ecosystem variations, bacteria and

• zwitterion dimethylsulphoniopropionate (DMSP), resulting in biofilm formation on the algal surrounding [9]. The bacterium subsequently uses the provided glycerol for growth and transforms DMSP into methanethiol and dimethyl sulphide [9]. The metabolic activities of marine bacteria and algae can be surveyed

• using mass spectrometry-based methods. For example, stable sulphur isotope (34S) labelled DMSP was used to track DMSP uptake and degradation by marine bacteria, and secondary ion mass spectrometry was applied to visualise it at the single-cell level [16]. The interaction between epibiotic bacteria on

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

• compounds, structural suggestions were made based on their mass spectrometric fragmentation pattern and confirmed by the synthesis of reference compounds. The results of the feeding experiments allowed to conclude on the substrate tolerance of DMSP degrading enzymes in marine bacteria. Keywords: Allium

• preferred gas-phase reaction. The ecology of marine bacteria in their interaction with algae is particularly interesting in which the bacteria can promote the algal growth, but can also kill their host [10][11]. For both processes, the phytohormone indole-3-acetic acid is used as a messenger molecule [10

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

• into sulfur volatiles [24][25]. Notably, DHPS is produced in large quantities by the marine diatom Thalassiosira pseudonana [26], and diatoms from this genus live in symbiotic relationship with bacteria of the roseobacter group [27]. Another interesting aspect of sulfur metabolism in marine bacteria

• relationship during which the antibiotic TDA and growth stimulants are produced to a pathogenic interaction promoted by lignin degradation products in fading algal blooms that induce roseobacticide biosynthesis [36]. All these examples demonstrate the importance of sulfur metabolism for marine bacteria from

Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of ¹J_C,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites

• Md. Rokon Ul Karim,
• Enjuro Harunari,
• Amit Raj Sharma,
• Naoya Oku,
• Kazuaki Akasaka,
• Daisuke Urabe,
• Mada Triandala Sibero and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222

• siderophores and modified peptides, are known from Kocuria and Micrococcus [19][20]. In our continuing investigation on secondary metabolites from marine bacteria, five alkanoylimidazoles were obtained from the culture extract of a Kocuria strain isolated from a stony coral. Alkanoylimidazoles are a new and

• members, nocarimidazoles C (1) and D (2), were obtained from a marine-derived actinomycete of the genus Kocuria. The exclusive origin of these metabolites from marine bacteria, as well as the distribution among phylogenetically distinct taxa imply their potential function in the adaptation of the

• are biosynthesized from ʟ-isoleucine [31][32]. However, we have previously shown that both the anteiso-branched secondary metabolites of marine bacteria, nocapyrone L [30] and bulbimidazole A (5) [22], are 2:3 and 9:91 mixtures of the R- and S-enantiomers, respectively. Again, we encountered

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• ]. Others can fix nitrogen [5], have phototrophy [6], or produce a plant hormone [7], and thus showing a higher metabolic versatility, which is also represented by 150 and more secondary metabolites discovered from this genus [8]. As part of our continuing study on the secondary metabolites of marine

• bacteria, Vibrio sp. SI9, isolated from the sea anemone Radianthus crispus, was found to produce a known ester 4 and its new congeners 1–3 (Figure 1). Compound 4 is the shortest among the five oligomers of O-isocrotonyl-oligo(3-hydroxybutyrate) (5) previously discovered from Vibrio [9]. In this study, we

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.

• Amit Raj Sharma,
• Enjuro Harunari,
• Tao Zhou,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2327–2332, doi:10.3762/bjoc.15.225

• . Compound 1 showed weak growth inhibition against Saccharomyces cerevisiae. Keywords: biosynthesis; fatty acid; marine bacteria; methylation; Microbulbifer; Introduction Marine microbial symbionts are currently recognized as a reservoir of new bioactive compounds [1]. The most well-studied host animal is

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

• 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

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

• ; 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

A new approach for the synthesis of bisindoles through AgOTf as catalyst

• Jorge Beltrá,
• M. Concepción Gimeno and
• Raquel P. Herrera

Beilstein J. Org. Chem. 2014, 10, 2206–2214, doi:10.3762/bjoc.10.228

• the synthesis of the interesting compound vibrindole A (Scheme 2), an isolated metabolite of the marine bacteria Vibrio parahaemolyticus, which is active against Bacillus subtilis, Staphylococcus aureus and Staphylococcus albus as has been previously demonstrated [43]. In order to prevent the loss of

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

• ]. DMSP is degraded by marine bacteria either under the formation of methanethiol (MeSH) or of dimethyl sulfide (DMS) with a large impact on both the global sulfur cycle and climate [12][13]. DMSP degradation to MeSH starts with the DmdA mediated demethylation to 3-(methylthio)propionate (Scheme 1A) [14

• compounds and synthetic selenium and tellurium analogues to wildtype and relevant mutant strains. A reinvestigation of DMTeP conversion by marine bacteria from the Roseobacter clade into methylated tellurium volatiles using a modified analytical technique is also presented. Results and Discussion Usage of

• [2H6]DMSP and DMTeP as synthetic probes to study DMSP degradation pathways in marine bacteria The volatiles released by agar-plate cultures of Phaeobacter gallaeciensis DSM 17395 and Ruegeria pomeroyi DSS-3 strains grown on half-strength MB2216 medium supplemented with [2H6]DMSP or DMTeP were collected

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

• ; 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