Abenquines A–D: aminoquinone derivatives produced by Streptomyces sp. strain DB634

Abstract

New bioactive secondary metabolites, called abenquines, were found in the fermentation broth of Streptomyces sp. strain DB634, which was isolated from the soils of the Chilean highland of the Atacama Desert. They are composed of an amino acid linked to an N-acetyl-aminobenzoquinone. Isolation of the abenquines (1-4), their structure elucidation by NMR analysis and MS, as well as the kinetics of their production are presented. The abenquines show inhibitory activity against bacteria, dermatophytic fungi and phosphodiesterase type 4b. The amino acid attached to the quinone is relevant to the enzyme inhibitory activity. The Journal of Antibiotics (2011) INTRODUCTIONThe Northern Chilean highlands of the Atacama Desert comprise a number of extreme habitats, including permanent arid soils exposed to very high UV irradiation and strong fluctuations in temperature, various types of salt lakes differing in salinity and mineral salts composition and also geothermal-driven hot springs and geysers. These habitats make this area extraordinarily interesting for studies of microbial communities adapted to extreme environmental conditions. Previous studies have shown that salt lakes of this area harbor unique communities of anoxygenic phototrophic bacteria 1 and cyanobacteria. 2 Recently, we have isolated a number of actinobacteria from arid soils of the Atacama Desert and characterized them in regard to their potential to synthesize secondary metabolites. In this study, we present the secondary metabolite profile of one of the isolated Streptomyces strains.

Isolation and anti-HIV-1 integrase activity of lentzeosides A–F from extremotolerant lentzea sp. H45, a strain isolated from a high-altitude Atacama Desert soil

“…C38 and the cell invasion inhibitor chaxapeptin from S. leeuwenhoekii strain C58. [10][11][12][13][14][15][16] As part of our ongoing program to investigate the extremobiosphere as a source of new natural products, we have focused our attention on Lentzea sp. strain H45 which was isolated from a high-altitude Atacama Desert soil and shown to produce a specific pattern of secondary metabolites based on its liquid chromatography MS (LCMS) profile and associated NMR data.…”

Natural product diversity of actinobacteria in the Atacama Desert

“…Bioassay-guided isolation led to the discovery of new types of aminobenzoquinones, abenquines A, B1, B2, C and D (1-5) that featured a rare combination of benzoquinone and a range of amino acids (Schulz et al 2011). Compounds 1-5 were obtained from Streptomyces sp.…”

“…Compounds 1-5 were obtained from Streptomyces sp. strain DB634 isolated from the soils of the Chilean highland of the Atacama Desert and exhibited weak antibacterial and antifungal activities and moderate selective inhibitory activity against type 4 phosphodiesterase (PDE4b) that could be a promising target for the investigation of inflammatory diseases (Schulz et al 2011). A similar strategy led to the isolation of a new family of 22-membered macrolactones, atacamycins A-C (10-12) from Streptomyces leeuwenhoekii strain C38 isolated from a hyper-arid Atacama Desert salt lake sediment (Nachtigall et al 2011).…”

“…Abenquines A, B1, B2, C and D (1-5) are a group of aminoquinone-derived natural products that feature a rare combination of benzoquinone and a range of amino acids (Schulz et al 2011). Compounds 1-5 were isolated from Streptomyces sp.…”

“…This could be regarded as a promising scaffold for anti-inflammatory drug discovery. Compounds 1-5 also demonstrated weak antibacterial activity but no antifungal activity against the tested strains (Schulz et al 2011).…”