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N-acetyl-cysteinylated streptophenazines from Streptomyces
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Vind, Kristiina, Maffioli, Sonia, Fernandez Ciruelos, Blanca, Waschulin, Valentin, Brunati, Cristina, Simone, Matteo, Sosio, Margherita and Donadio, Stefano (2022) N-acetyl-cysteinylated streptophenazines from Streptomyces. Journal of Natural Products, 85 (5). pp. 1239-1247. doi:10.1021/acs.jnatprod.1c01123 ISSN 0163-3864.
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WRAP-N-acetyl-cysteinylated-streptophenazines-from-Streptomyces-Waschulin-22.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution 4.0. Download (2277Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.jnatprod.1c01123
Abstract
Here, we describe two N-acetyl-cysteinylated streptophenazines (1 and 2) produced by the soil-derived Streptomyces sp. ID63040 and identified through a metabolomic approach. These metabolites attracted our interest due to their low occurrence frequency in a large library of fermentation broth extracts and their consistent presence in biological replicates of the producer strain. The compounds were found to possess broad-spectrum antibacterial activity while exhibiting low cytotoxicity. The biosynthetic gene cluster from Streptomyces sp. ID63040 was found to be highly similar to the streptophenazine reference cluster in the MIBiG database, which originates from the marine Streptomyces sp. CNB-091. Compounds 1 and 2 were the main streptophenazine products from Streptomyces sp. ID63040 at all cultivation times but were not detected in Streptomyces sp. CNB-091. The lack of obvious candidates for cysteinylation in the Streptomyces sp. ID63040 biosynthetic gene cluster suggests that the N-acetyl-cysteine moiety derives from cellular functions, most likely from mycothiol. Overall, our data represent an interesting example of how to leverage metabolomics for the discovery of new natural products and point out the often-neglected contribution of house-keeping cellular functions to natural product diversification.
Item Type: | Journal Article | ||||||||
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Subjects: | Q Science > QD Chemistry Q Science > QR Microbiology Q Science > QR Microbiology > QR180 Immunology |
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Life Sciences (2010- ) | ||||||||
Library of Congress Subject Headings (LCSH): | Streptomyces, Phenazine, Microbial metabolites, Drug resistance in microorganisms | ||||||||
Journal or Publication Title: | Journal of Natural Products | ||||||||
Publisher: | ACS | ||||||||
ISSN: | 0163-3864 | ||||||||
Official Date: | 27 May 2022 | ||||||||
Dates: |
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Volume: | 85 | ||||||||
Number: | 5 | ||||||||
Page Range: | pp. 1239-1247 | ||||||||
DOI: | 10.1021/acs.jnatprod.1c01123 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 31 May 2022 | ||||||||
Date of first compliant Open Access: | 1 June 2022 | ||||||||
RIOXX Funder/Project Grant: |
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