Data_Sheet_1_Stieleriacines, N-Acyl Dehydrotyrosines From the Marine Planctomycete Stieleria neptunia sp. nov..pdf
Bacteria of the phylum Planctomycetes occur ubiquitously in marine environments and play important roles in the marine nitrogen- and carbon cycle, for example as scavengers after phototrophic blooms. Here, we describe the isolation and characterization of the planctomycetal strain Enr13T isolated from a Posidonia sp. biofilm obtained from seawater sediment close to Panarea Island, Italy. Phylogenetic tree reconstruction based on 16S rRNA gene sequences and multi-locus sequence analysis supports the delineation of strain Enr13T from characterized species part of the phylum of Planctomycetes. HPLC-MS analysis of culture broth obtained from strain Enr13T revealed the presence of lipophilic metabolites, of which the major compound was isolated by preparative reversed-phase HPLC. The structure of this compound, named stieleriacine D (1), was elucidated utilizing HRESIMS, 1D- and 2D-NMR data as a new N-acylated dehydrotyrosine derivative. Its biosynthesis was proposed based on an in silico gene cluster analysis. Through analysis of the MS/MS spectrum of 1 and its minor derivative, stieleriacine E (2), it was possible to assign the structure of 2 without isolation. 1 showed antibacterial activity, however, the wide distribution of structurally related compounds indicates a potential role as a signaling molecule.
History
References
- https://doi.org//10.1007/s10482-013-9980-7
- https://doi.org//10.1021/ja0268985
- https://doi.org//10.1021/ol0509585
- https://doi.org//10.3389/fmars.2018.00499
- https://doi.org//10.1038/nature23874
- https://doi.org//10.1021/acs.jnatprod.5b00972
- https://doi.org//10.1038/s41564-018-0176-9
- https://doi.org//10.1007/s10482-013-0087-y
- https://doi.org//10.1016/j.ygeno.2017.10.007
- https://doi.org//10.1016/j.syapm.2014.12.001
- https://doi.org//10.1007/s10482-019-01259-7
- https://doi.org//10.3389/fmicb.2016.01241
- https://doi.org//10.1007/s10482-013-0007-1
- https://doi.org//10.3389/fmicb.2016.01242
- https://doi.org//10.1128/aem.05132-11
- https://doi.org//10.1128/jb.01325-12
- https://doi.org//10.1093/bioinformatics/btu031
- https://doi.org//10.1038/s42003-020-0993-2
- https://doi.org//10.1099/ijs.0.059774-0
- https://doi.org//10.1016/j.syapm.2019.126022
- https://doi.org//10.1073/pnas.0409727102
- https://doi.org//10.3389/fmicb.2014.00267
- https://doi.org//10.1016/j.jbiotec.2019.01.017
- https://doi.org//10.1021/acs.orglett.9b02710
- https://doi.org//10.1146/annurev-micro-090816-093449
- https://doi.org//10.1021/acschembio.9b00641
- https://doi.org//10.1128/jb.01688-14
- https://doi.org//10.3389/fmicb.2017.00202
- https://doi.org//10.1128/AEM.02645-17
- https://doi.org//10.3389/fmicb.2016.00914
- https://doi.org//10.1021/acs.orglett.9b01017
- https://doi.org//10.1007/s00726-014-1846-4
- https://doi.org//10.1021/np5010104
- https://doi.org//10.1038/s41564-019-0588-1
- https://doi.org//10.1093/femsre/fuy029
- https://doi.org//10.1038/s41429-018-0035-1
CC BY 4.0