Abstract
Terpene synthases are widely distributed in Actinobacteria. Genome sequencing of Streptomyces sp. NRRL S-4 uncovered a biosynthetic gene cluster (BGC) that putatively synthesizes pentalenolactone type terpenes. Guided by genomic information, the S-4 strain was chemically investigated, resulting in the isolation of two new sesquiterpenoids, 1-deoxy-8α-hydroxypentalenic acid (1) and 1-deoxy-9β-hydroxy-11-oxopentalenic acid (2), as shunt metabolites of the pentalenolactone (3) biosynthesis pathway. Their structures and absolute configurations were elucidated by analyses of HRESIMS and NMR spectroscopic data as well as time-dependent density functional theory/electronic circular dichroism (TDDFT/ECD) calculations. Compounds 1 and 2 exhibited moderate antimicrobial activities against Gram-positive and Gram-negative bacteria. These results confirmed that the pentalenolactone pathway was functional in this organism and will facilitate efforts for exploring Actinobacteria using further genome mining strategies.
Highlights
Whole-genome sequencing and bioinformatics analyses reveal an enormous number of secondary metabolite biosynthetic gene clusters (BGCs) in Actinobacteria [1]
Genome mining approaches have greatly enhanced the discovery of secondary metabolites from Actinobacteria [3]
We chemically investigated the organic extracts of S-4 fermentation and discovered two new sesquiterpenoids, 1-deoxy-8α-hydroxypentalenic acid
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. Whole-genome sequencing and bioinformatics analyses reveal an enormous number of secondary metabolite biosynthetic gene clusters (BGCs) in Actinobacteria [1]. Genome mining approaches have greatly enhanced the discovery of secondary metabolites from Actinobacteria [3]. NRRL S-4 (S-4) was selected for the exploration of secondary metabolite profiles. Previous studies of this strain resulted in the discovery of thiostreptamides and venturicidins [6,7]. S-4 contained 25 BGCs including six BGCs that putatively synthesized the terpenoids [6]. We chemically investigated the organic extracts of S-4 fermentation and discovered two new sesquiterpenoids, 1-deoxy-8α-hydroxypentalenic acid (1) and 1-deoxy-9β-hydroxy-11-oxopentalenic acid (2).
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