Isolation and Structural Elucidation of Nitrogenous Secondary Metabolites from Terrestrial and Marine Streptomyces spp

Abstract

Screening and chromatography of extracts from a terrestrial and a marine-derived streptomycete yielded two new nitrogenous benzene derivatives, namely (S)-N-[3-hydroxy-1-(4-hydroxyphenyl)-propyl]-acetamide (1a), and (R)-2-(1-methyl-2-oxopropylamino)-benzoic acid (2). Additionally, eight known compounds were isolated, 2-acetamidophenol, phenazine-1-carboxylic acid, phenazine-1-carboxylic acid methyl ester, perlolyrin, tyrosol, uracil, and anthranilic acid. The structures of the new compounds were deduced from high resolution mass, 1D and 2D NMR spectra and by comparison with related compounds from the literature. The absolute configuration of 1a and 2 was determined by comparison of experimental and calculated CD and ORD data.

Keywords

Streptomycetes N-Acetyl-ß-homotyrosol N-Alkylanthranilic acid Absolute configuration DFT calculations

References

Casein Medium: Casein (10 g), yeast extract (5 g), NaCl (10 g), and glucose (5 g) were dissolved in tap water (1 L) and adjusted to pH 7.8 before sterilization; M₂ Medium: Malt extract (10 g), yeast extract (4 g), and glucose (4 g) were dissolved in 1 L tap water. Before sterilization, the pH was adjusted to 7.8 by addition of 2N NaOH; M₂⁺ Medium: Malt extract (10 g), yeast extract (4 g), and glucose (4 g) were dissolved in artificial seawater (0.5 L) and tap water (0.5 L). Before sterilization, the pH was adjusted to 7.8 by addition of 2N NaOH; LB-medium +Glucose: Trypton (10 g), yeast extract (4 g), glucose (4 g), NaCl (10 g) were dissolved in artificial sea water (0.5 L) and tap water (0.5 L). Before sterilization, the pH was adjusted to 7.8 by addition of 2N NaOH.

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