Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5
| Autor: | Michael Maczka, Stefan Schulz, Jeroen S. Dickschat, Ulrike Groenhagen |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
natural products
Streptomyces Full Research Paper lcsh:QD241-441 Agar plate chemistry.chemical_compound Adsorption lcsh:Organic chemistry Pyridine Organic chemistry volatile compounds lcsh:Science Solvent extraction streptazolin biology Organic Chemistry Total synthesis biology.organism_classification pyridine derivatives Chemistry chemistry headspace analysis lcsh:Q polyketide biosynthesis Streptazolin Bacteria |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 10, Iss 1, Pp 1421-1432 (2014) |
| ISSN: | 1860-5397 |
| DOI: | 10.3762/bjoc.10.146 |
| Popis: | Streptomyces sp. FORM5 is a bacterium that is known to produce the antibiotic streptazolin and related compounds. We investigated the strain for the production of volatiles using the CLSA (closed-loop stripping analysis) method. Liquid and agar plate cultures revealed the formation of new 2-alkylpyridines (streptopyridines), structurally closely related to the already known 2-pentadienylpiperidines. The structures of the streptopyridines A to E were confirmed by total synthesis. The analysis of the liquid phase by solvent extraction or extraction with an Oasis adsorbent showed that streptazolin and 2-pentadienylpiperidine are the major compounds, while the streptopyridines are only minor components. In the gas phase, only the streptopyridines could be detected. Therefore, an orthogonal set of analysis is needed to assess the metabolic profile of bacteria, because volatile compounds are obviously overlooked by traditional analytical methods. The streptopyridines are strain specific volatiles that are accompanied by a broad range of headspace constituents that occur in many actinomycetes. Volatiles might be of ecological importance for the producing organism, and, as biosynthetic intermediates or shunt products, they can be useful as indicators of antibiotic production in a bacterium. |
| Databáze: | OpenAIRE |
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