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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.

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FORM5 was investigated and several new 2-alkylated pyridines were identified using the closed-loop stripping analysis (CLSA) [7] headspace technique followed by GC–MS analysis and synthesis of the target compounds for structure verification.

Agar plate cultures and liquid cultures were investigated and the liquid phase analyzed for the presence of secondary metabolites.

Apart from pyrazines, indole, and a few strain specific compounds [2] such as methyl pyrrole-2-carboxylate, emitted by Stackebrandtia nassauensis, or 2-acetylpyrrole from Saccharopolyspora erythraea, volatile alkaloids are rarely produced by actinomycetes.

We became interested in the strain Streptomyces sp.

Nevertheless, the major compounds (compounds 8, 9, 11, and 12 in Figure 2) attracted our interest, because they were unknown, thus giving room for the discovery of new volatile secondary metabolites.

High resolution GC–MS revealed a molecular composition of CN (found 147.10428, calcd 147.10475) for the minor component 8.

The results showed that by headspace analysis new secondary metabolites can be found that eluded earlier analysis.

The separate analysis of headspace and liquid phase is complementary and in combination allows better evaluation of the metabolic potential of an investigated microorganism.

The mass spectrum (Figure 3) of the major compound pointed to the presence of an extended aromatic and conjugated π-system and the formation of a stable [M − 1] indicated the presence of a methyl group in the compound.

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