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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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 |
doi_str_mv | 10.1111/lam.13207 |
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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. In the future investigation for novel dithiolopyrrolone discovery, fermentation duration should be regarded as a key parameter as well.</description><identifier>ISSN: 0266-8254</identifier><identifier>EISSN: 1472-765X</identifier><identifier>DOI: 10.1111/lam.13207</identifier><identifier>PMID: 31424588</identifier><language>eng</language><publisher>England: Oxford University Press</publisher><subject>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</subject><ispartof>Letters in applied microbiology, 2019-10, Vol.69 (4), p.294-301</ispartof><rights>2019 The Society for Applied Microbiology</rights><rights>2019 The Society for Applied Microbiology.</rights><rights>Copyright © 2019 The Society for Applied Microbiology</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4227-18bbf79e022c9734f3dcd84a48787423388961a910705a162ed97f2b425088713</citedby><cites>FETCH-LOGICAL-c4227-18bbf79e022c9734f3dcd84a48787423388961a910705a162ed97f2b425088713</cites><orcidid>0000-0002-2740-7834 ; 0000-0003-0970-4082 ; 0000-0003-3071-9561 ; 0000-0002-5032-4746</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Flam.13207$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Flam.13207$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,780,784,885,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31424588$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-03135645$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Merrouche, R.</creatorcontrib><creatorcontrib>Yekkour, A.</creatorcontrib><creatorcontrib>Coppel, Y.</creatorcontrib><creatorcontrib>Bouras, N.</creatorcontrib><creatorcontrib>Zitouni, A.</creatorcontrib><creatorcontrib>Lebrihi, A.</creatorcontrib><creatorcontrib>Mathieu, F.</creatorcontrib><creatorcontrib>Sabaou, N.</creatorcontrib><title>A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium</title><title>Letters in applied microbiology</title><addtitle>Lett Appl Microbiol</addtitle><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 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.</description><subject>Actinobacteria - metabolism</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Antibiotics</subject><subject>Anticancer properties</subject><subject>Antifungal activity</subject><subject>antimicrobial activity</subject><subject>Antitumor activity</subject><subject>Bioactive compounds</subject><subject>Biosynthesis</subject><subject>Cancer</subject><subject>Chemical and Process Engineering</subject><subject>Chemical engineering</subject><subject>Chemical Sciences</subject><subject>dithiolopyrrolone antibiotics</subject><subject>Engineering Sciences</subject><subject>Fermentation</subject><subject>Fungi</subject><subject>Fungi - drug effects</subject><subject>Fungicides</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>High-performance liquid chromatography</subject><subject>Liquid chromatography</subject><subject>long fermentation</subject><subject>Microbial Sensitivity Tests</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Purification</subject><subject>Pyrroles - pharmacology</subject><subject>Saccharothrix algeriensis</subject><subject>Sorbic acid</subject><subject>Sorbic Acid - metabolism</subject><subject>Spectrometry</subject><subject>Yeast</subject><subject>Yeasts</subject><issn>0266-8254</issn><issn>1472-765X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kd9OFDEUhxujkRW94AVIE2_0YqD_ZtpergTFZIAEMPGu6XQ6uyUz7dLOgHvnG-gz-iR2WcCExN6c5PTL13P6A2APowOcz2GvhwNMCeIvwAwzTgpeld9fghkiVVUIUrId8Cala4SQwES-BjsUM8JKIWbg1xx6ewdbNy5d6MNqHWMu3kLtR9e4MDoDx-gWCxttC5s11DBfL2Bn42D9qEcXPAwdvNTGLHUM4zK6H1D3mXfWJ5fg2cVFDT_9-fmbMEw5dB6mEJus1ca1ua2zp83uwbZuGt6CV53uk333UHfBt8_HV0cnRX3-5evRvC4MI4QXWDRNx6VFhBjJKetoa1rBNBNccEYoFUJWWEuMOCo1rohtJe9Iw0iJhOCY7oKPW-9S92oV3aDjWgXt1Mm8VpseopiWFStvN-yHLbuK4WayaVSDS8b2vfY2TEnlgUrJpOQio--foddhij5vkqnNbAKJ6t_jJoaUou2eJsBIbRJVOVF1n2hm9x-MU5O_6Il8jDADh1vgzvV2_X-TquenW-VfOk2qTA</recordid><startdate>201910</startdate><enddate>201910</enddate><creator>Merrouche, R.</creator><creator>Yekkour, A.</creator><creator>Coppel, Y.</creator><creator>Bouras, N.</creator><creator>Zitouni, A.</creator><creator>Lebrihi, A.</creator><creator>Mathieu, F.</creator><creator>Sabaou, N.</creator><general>Oxford University Press</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7ST</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>SOI</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-2740-7834</orcidid><orcidid>https://orcid.org/0000-0003-0970-4082</orcidid><orcidid>https://orcid.org/0000-0003-3071-9561</orcidid><orcidid>https://orcid.org/0000-0002-5032-4746</orcidid></search><sort><creationdate>201910</creationdate><title>A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium</title><author>Merrouche, R. ; Yekkour, A. ; Coppel, Y. ; Bouras, N. ; Zitouni, A. ; Lebrihi, A. ; Mathieu, F. ; Sabaou, N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4227-18bbf79e022c9734f3dcd84a48787423388961a910705a162ed97f2b425088713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Actinobacteria - metabolism</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>Antibiotics</topic><topic>Anticancer properties</topic><topic>Antifungal activity</topic><topic>antimicrobial activity</topic><topic>Antitumor activity</topic><topic>Bioactive compounds</topic><topic>Biosynthesis</topic><topic>Cancer</topic><topic>Chemical and Process Engineering</topic><topic>Chemical engineering</topic><topic>Chemical Sciences</topic><topic>dithiolopyrrolone antibiotics</topic><topic>Engineering Sciences</topic><topic>Fermentation</topic><topic>Fungi</topic><topic>Fungi - drug effects</topic><topic>Fungicides</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>High-performance liquid chromatography</topic><topic>Liquid chromatography</topic><topic>long fermentation</topic><topic>Microbial Sensitivity Tests</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Purification</topic><topic>Pyrroles - pharmacology</topic><topic>Saccharothrix algeriensis</topic><topic>Sorbic acid</topic><topic>Sorbic Acid - metabolism</topic><topic>Spectrometry</topic><topic>Yeast</topic><topic>Yeasts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Merrouche, R.</creatorcontrib><creatorcontrib>Yekkour, A.</creatorcontrib><creatorcontrib>Coppel, Y.</creatorcontrib><creatorcontrib>Bouras, N.</creatorcontrib><creatorcontrib>Zitouni, A.</creatorcontrib><creatorcontrib>Lebrihi, A.</creatorcontrib><creatorcontrib>Mathieu, F.</creatorcontrib><creatorcontrib>Sabaou, N.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Letters in applied microbiology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Merrouche, R.</au><au>Yekkour, A.</au><au>Coppel, Y.</au><au>Bouras, N.</au><au>Zitouni, A.</au><au>Lebrihi, A.</au><au>Mathieu, F.</au><au>Sabaou, N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new dithiolopyrrolone antibiotic triggered by a long fermentation of Saccharothrix algeriensis NRRL B‐24137 in sorbic acid‐amended medium</atitle><jtitle>Letters in applied microbiology</jtitle><addtitle>Lett Appl Microbiol</addtitle><date>2019-10</date><risdate>2019</risdate><volume>69</volume><issue>4</issue><spage>294</spage><epage>301</epage><pages>294-301</pages><issn>0266-8254</issn><eissn>1472-765X</eissn><abstract>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 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.</abstract><cop>England</cop><pub>Oxford University Press</pub><pmid>31424588</pmid><doi>10.1111/lam.13207</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-2740-7834</orcidid><orcidid>https://orcid.org/0000-0003-0970-4082</orcidid><orcidid>https://orcid.org/0000-0003-3071-9561</orcidid><orcidid>https://orcid.org/0000-0002-5032-4746</orcidid><oa>free_for_read</oa></addata></record> |
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source | MEDLINE; Oxford University Press Journals All Titles (1996-Current); EZB-FREE-00999 freely available EZB journals; Wiley Online Library All Journals; Alma/SFX Local Collection |
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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