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FORM5 to elucidate whether volatile formation is linked to the production of other, usually less volatile secondary metabolites and whether different compounds can be detected by headspace analysis [7] compared to commonly used solvent extraction or adsorption/extraction procedures.

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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.

The mass spectrum of compound 7 matched that of 2-pentylpyridine, present in public databases [14].

From these data we concluded that the unknown compound 12 might be a 2-(pentadienyl)pyridine with conjugated side chain and that the compounds 9–12 might be diastereomers.

Compound 8 should carry a pentenyl side chain, while compound 6 showed a mass spectrum identical to the known one of 2-propylpyridine.

Figure 2: Part of the total ion chromatogram of the headspace extract of Streptomyces sp.

FORM5 with the structures of 2-propylpyridine (6), 2-pentylpyridine (7), (E)-2-(pent-3-en-1-yl)pyridine (8), 2-((1Z,3E)-penta-1,3-dien-1-yl)pyridine (9), 2-((1Z,3Z)-penta-1,3-dien-1-yl)pyridine (10), 2-((1E,3Z)-penta-1,3-dien-1-yl)pyridine (11), 2-((1E,3E)-penta-1,3-dien-1-yl)pyridine (12).

Figure 3: Mass spectra of a) (E)-2-(pent-3-en-1-yl)pyridine (streptopyridine E, 8), b) (1Z,3E)-penta-1,3-dien-1-yl)pyridine (streptopyridine A, 9), c) 2-((1E,3E)-penta-1,3-dien-1-yl)pyridine (streptopyridine B, 12).

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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