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• W1014517817 abstract "This thesis is divided in four separate sections. The first part deals with the synthesis and chemical analysis of novel biofilm inhibitors as a part of a joint research project for the identification of novel biofilm inhibitors from metagenomes. The quorum sensing molecules autoinducer AI-1 (AI-1) and autoinducer AI-2 (AI-2) were synthesized by total synthesis and purification after enzymatical preparation for biochemical investigations in sufficient amounts and without toxic by-products. Furthermore the quorum quenching activity of metagenome-derived clones (bpiB genes) which inhibited the formation of biofilms was verified as lactonase activity by HPLC-ESI-MS analysis.The second topic of this thesis is about the Streptomyces sp. strain JP90, isolated as an associated bacterium from marine invertebrates (cooperation with Prof. Dr. J. Piel, Bonn). The secondary metabolite cinnamoylphosphoramide comprises an unusual phosphoramide methyl ester moiety which is rare among natural products. It matches the Schrader`s formula for insecticidal organophosphates. To investigate the biological activity cinnamoylphosphoramide and its fundamental water-soluble carboxylic acid analogue were synthesized (cooperation with Prof. Dr. P. v. Zezschwitz, Marburg). A further part of this topic is the isolation and structure elucidation of two spirotetronates and biosynthetic studies of selected metabolites. By feeding of 13C-labeled precursors to the producer strain JP90 followed by 13C-NMR analysis of the observed labeling pattern the high structural similarity of the spirotetronates to chlorothricin was verified due to consistent labeling patterns. Furthermore, the monoterpene rosiridol which is until now only known as a metabolite from plants, was isolated from JP90. The biosynthetic origin of its carbon skeleton was studied by feeding experiments with 13C-labeled precursors and 13C-NMR spectroscopy. All results revealed a biosynthesis via the non-mevalonate pathway. The observed labeling pattern from the feeding experiment of [U-13C3]glycerol also indicated a small proportion of biosynthetic formation of rosiridol via the mevalonate pathway.Within the third section of the thesis the production of a new glycopeptide by a streptomycetes was investigated. The research group of Prof. Dr. U. Hentschel (Würzburg) identified the biosynthetic gene cluster of this novel secondary metabolite. Based on silico analysis a novel glycopeptide of the vancomycin-type was postulated. Its structure shall comprise at least one sulfate substituent. During optimization of the cultivation parameters and feeding of various putative precursors, it was observed by HPLC-ESI-MS that the production of vancomycin was increased. However, no further specific chlorine containing substitution pattern was found indicating the presence of the postulated novel glycopeptide. As the production of this novel metabolite could not be proven, the isolated biosynthetic gene cluster is a silent one.The fourth topic of this thesis deals with the structure elucidation of isolated secondary metabolites from the fungus Aspergillus nidulans. An extract of this showed a high cytotoxicity, when it was investigated by the Department of Occupational Health/University of Göttingen (PD M. Müller). The high cytotoxicity found, could not traced back to the amount of sterigmatocystin in the extract. Hence the mycotoxin which was responsible for the cytotoxicity should be isolated and its structure identified. Within this thesis the structure of the novel cycloisoemericellinol derivative was elucidated and its native origin was verified. Additionally three further known secondary metabolites were identified." @default.
• W1014517817 created "2016-06-24" @default.
• W1014517817 creator A5017098192 @default.
• W1014517817 date "2022-02-20" @default.
• W1014517817 modified "2023-10-01" @default.
• W1014517817 title "Neue Biofilminhibitoren mittels Metagenom-Strategie und marine Streptomyceten, neue Naturstoffe, Synthesen und Biosynthesen" @default.
• W1014517817 doi "https://doi.org/10.53846/goediss-2117" @default.
• W1014517817 hasPublicationYear "2022" @default.
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