A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium

Saccharothrix algeriensis NRRL B‐24137 is an actinobacterium isolated from Algerian Saharan soil. It produces bioactive compounds belonging to the dithiolopyrrolone class of antibiotics, which are characterized by the possession of a unique pyrrolinonodithiole nucleus. Dithiolopyrrolones are known f...

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Veröffentlicht in:Letters in applied microbiology 2019-10, Vol.69 (4), p.294-301
Hauptverfasser: Merrouche, R., Yekkour, A., Coppel, Y., Bouras, N., Zitouni, A., Lebrihi, A., Mathieu, F., Sabaou, N.
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container_issue 4
container_start_page 294
container_title Letters in applied microbiology
container_volume 69
creator Merrouche, R.
Yekkour, A.
Coppel, Y.
Bouras, N.
Zitouni, A.
Lebrihi, A.
Mathieu, F.
Sabaou, N.
description Saccharothrix algeriensis NRRL B‐24137 is an actinobacterium isolated from Algerian Saharan soil. It produces bioactive compounds belonging to the dithiolopyrrolone class of antibiotics, which are characterized by the possession of a unique pyrrolinonodithiole nucleus. Dithiolopyrrolones are known for their strong antibacterial and antifungal activities. This class of antibiotics generated great interest after the discovery of their anticancer properties. In this study, an antibiotic named PR11, produced after a long bacterial fermentation (11 days) in sorbic acid‐containing culture broth, was characterized as a new dithiolopyrrolone derivative. After HPLC analysis and purification, the chemical structure of this antibiotic was determined by 1H‐ and 13C‐nuclear magnetic resonance, mass and UV‐visible data. PR11 was thus characterized as an iso‐hexanoyl‐pyrrothine, a novel dithiolopyrrolone derivative. The minimum inhibitory concentrations of the new induced antibiotic were determined against several pathogenic micro‐organisms. A moderate to strong activity was noted against all Gram‐positive bacteria, filamentous fungi and yeasts tested. Significance and Impact of the Study Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. In the future investigation for novel dithiolopyrrolone discovery, fermentation duration should be regarded as a key parameter as well. Significance and Impact of the Study: Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation du
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It produces bioactive compounds belonging to the dithiolopyrrolone class of antibiotics, which are characterized by the possession of a unique pyrrolinonodithiole nucleus. Dithiolopyrrolones are known for their strong antibacterial and antifungal activities. This class of antibiotics generated great interest after the discovery of their anticancer properties. In this study, an antibiotic named PR11, produced after a long bacterial fermentation (11 days) in sorbic acid‐containing culture broth, was characterized as a new dithiolopyrrolone derivative. After HPLC analysis and purification, the chemical structure of this antibiotic was determined by 1H‐ and 13C‐nuclear magnetic resonance, mass and UV‐visible data. PR11 was thus characterized as an iso‐hexanoyl‐pyrrothine, a novel dithiolopyrrolone derivative. The minimum inhibitory concentrations of the new induced antibiotic were determined against several pathogenic micro‐organisms. A moderate to strong activity was noted against all Gram‐positive bacteria, filamentous fungi and yeasts tested. Significance and Impact of the Study Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. In the future investigation for novel dithiolopyrrolone discovery, fermentation duration should be regarded as a key parameter as well. Significance and Impact of the Study: Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. 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It produces bioactive compounds belonging to the dithiolopyrrolone class of antibiotics, which are characterized by the possession of a unique pyrrolinonodithiole nucleus. Dithiolopyrrolones are known for their strong antibacterial and antifungal activities. This class of antibiotics generated great interest after the discovery of their anticancer properties. In this study, an antibiotic named PR11, produced after a long bacterial fermentation (11 days) in sorbic acid‐containing culture broth, was characterized as a new dithiolopyrrolone derivative. After HPLC analysis and purification, the chemical structure of this antibiotic was determined by 1H‐ and 13C‐nuclear magnetic resonance, mass and UV‐visible data. PR11 was thus characterized as an iso‐hexanoyl‐pyrrothine, a novel dithiolopyrrolone derivative. The minimum inhibitory concentrations of the new induced antibiotic were determined against several pathogenic micro‐organisms. A moderate to strong activity was noted against all Gram‐positive bacteria, filamentous fungi and yeasts tested. Significance and Impact of the Study Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. In the future investigation for novel dithiolopyrrolone discovery, fermentation duration should be regarded as a key parameter as well. Significance and Impact of the Study: Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. 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It produces bioactive compounds belonging to the dithiolopyrrolone class of antibiotics, which are characterized by the possession of a unique pyrrolinonodithiole nucleus. Dithiolopyrrolones are known for their strong antibacterial and antifungal activities. This class of antibiotics generated great interest after the discovery of their anticancer properties. In this study, an antibiotic named PR11, produced after a long bacterial fermentation (11 days) in sorbic acid‐containing culture broth, was characterized as a new dithiolopyrrolone derivative. After HPLC analysis and purification, the chemical structure of this antibiotic was determined by 1H‐ and 13C‐nuclear magnetic resonance, mass and UV‐visible data. PR11 was thus characterized as an iso‐hexanoyl‐pyrrothine, a novel dithiolopyrrolone derivative. The minimum inhibitory concentrations of the new induced antibiotic were determined against several pathogenic micro‐organisms. A moderate to strong activity was noted against all Gram‐positive bacteria, filamentous fungi and yeasts tested. Significance and Impact of the Study Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. In the future investigation for novel dithiolopyrrolone discovery, fermentation duration should be regarded as a key parameter as well. Significance and Impact of the Study: Given the strong activities of dithiolopyrrolones against diverse prokaryotic and eukaryotic micro‐organisms including potent selective‐anticancer activity, the discovery of new‐related derivatives draw continuous attention for therapeutic research. Depending on nature and concentration of added precursor, Saccharothrix algeriensis NRRL B‐24137 produce several dithiolopyrrolone coumpounds. In this study, sorbic acid addition combined to long fermentation duration was shown to induce the biosynthesis of a novel dithiolopyrrolone derivative. After purification and full spectroscopic and spectrometric study, the compound was characterized as iso‐hexanoyl‐pyrrothine. 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subjects Actinobacteria - metabolism
Anti-Infective Agents - pharmacology
Antibiotics
Anticancer properties
Antifungal activity
antimicrobial activity
Antitumor activity
Bioactive compounds
Biosynthesis
Cancer
Chemical and Process Engineering
Chemical engineering
Chemical Sciences
dithiolopyrrolone antibiotics
Engineering Sciences
Fermentation
Fungi
Fungi - drug effects
Fungicides
Gram-Positive Bacteria - drug effects
High-performance liquid chromatography
Liquid chromatography
long fermentation
Microbial Sensitivity Tests
NMR
Nuclear magnetic resonance
Organic chemistry
Purification
Pyrroles - pharmacology
Saccharothrix algeriensis
Sorbic acid
Sorbic Acid - metabolism
Spectrometry
Yeast
Yeasts
title A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium
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