Escuzarmycins A–D, Potent Biofungicides to Control Septoria tritici Blotch

A study targeting novel antifungal metabolites identified potent in vitro antifungal activity against key plant pathogens in acetone extracts of Streptomyces sp. strain CA-296093. Feature-based molecular networking revealed the presence in this extract of antimycin-related compounds, leading to the...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of agricultural and food chemistry 2024-07, Vol.72 (27), p.15256-15264
Hauptverfasser:	Fernández-Pastor, Ignacio, González-Menéndez, Victor, González, Ignacio, Serrano, Rachel, Mackenzie, Thomas A., Benítez, Guillermo, Casares-Porcel, Manuel, Genilloud, Olga, Reyes, Fernando
Format:	Artikel
Sprache:	eng
Schlagworte:	Bioactive Constituents, Metabolites, and Functions
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	15264
container_issue	27
container_start_page	15256
container_title	Journal of agricultural and food chemistry
container_volume	72
creator	Fernández-Pastor, Ignacio González-Menéndez, Victor González, Ignacio Serrano, Rachel Mackenzie, Thomas A. Benítez, Guillermo Casares-Porcel, Manuel Genilloud, Olga Reyes, Fernando
description	A study targeting novel antifungal metabolites identified potent in vitro antifungal activity against key plant pathogens in acetone extracts of Streptomyces sp. strain CA-296093. Feature-based molecular networking revealed the presence in this extract of antimycin-related compounds, leading to the isolation of four new compounds: escuzarmycins A–D (1–4). Extensive structural elucidation, employing 1D and 2D NMR, high-resolution mass spectrometry, Marfey’s analysis, and NOESY correlations, confirmed their structures. The bioactivity of these compounds was tested against six fungal phytopathogens, and compounds 3 and 4 demonstrated strong efficacy, particularly against Zymoseptoria tritici, with compound 3 exhibiting the highest potency (EC50: 11 nM). Both compounds also displayed significant antifungal activity against Botrytis cinerea and Colletotrichum acutatum, with compound 4 proving to be the most potent. Despite moderate cytotoxicity against the human cancer cell line HepG2, compounds 3 and 4 emerge as promising fungicides for combating Septoria tritici blotch, anthracnose, and gray mold.
doi_str_mv	10.1021/acs.jafc.4c01303
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3073230329</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3073230329</sourcerecordid><originalsourceid>FETCH-LOGICAL-a219t-5d71149510c0d00878d86930ba07c82e06c4952508af837389b4d8e8d96ac623</originalsourceid><addsrcrecordid>eNp1kL1OwzAURi0EoqWwMyGPDE25tpvEGUspP1IlkOhuuY4DrpK42M5QJt6BN-RJcGlhw4uHe75P9x6EzgmMCFByJZUfrWSlRmMFhAE7QH2SUkhSQvgh6kNkEp5mpIdOvF8BAE9zOEY9xguWxtdH85lX3bt0zUaZ1uPJ18fnzRA_2aDbgK-Nrbr2xShTao-DxVPbBmdr_KzXwTojcXAmxDG-rm1Qr6foqJK112f7f4AWt7PF9D6ZP949TCfzRFJShCQtc0LGRUpAQRl3ynnJs4LBUkKuONWQqTilKXBZcZbHZZfjkmteFplUGWUDdLmrXTv71mkfRGO80nUtW207LxjkjEYbtIgo7FDlrPdOV2LtTCPdRhAQW4UiKhRbhWKvMEYu9u3dstHlX-DXWQSGO-AnajvXxlv_7_sGiKt8Pg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3073230329</pqid></control><display><type>article</type><title>Escuzarmycins A–D, Potent Biofungicides to Control Septoria tritici Blotch</title><source>American Chemical Society Journals</source><creator>Fernández-Pastor, Ignacio ; González-Menéndez, Victor ; González, Ignacio ; Serrano, Rachel ; Mackenzie, Thomas A. ; Benítez, Guillermo ; Casares-Porcel, Manuel ; Genilloud, Olga ; Reyes, Fernando</creator><creatorcontrib>Fernández-Pastor, Ignacio ; González-Menéndez, Victor ; González, Ignacio ; Serrano, Rachel ; Mackenzie, Thomas A. ; Benítez, Guillermo ; Casares-Porcel, Manuel ; Genilloud, Olga ; Reyes, Fernando</creatorcontrib><description>A study targeting novel antifungal metabolites identified potent in vitro antifungal activity against key plant pathogens in acetone extracts of Streptomyces sp. strain CA-296093. Feature-based molecular networking revealed the presence in this extract of antimycin-related compounds, leading to the isolation of four new compounds: escuzarmycins A–D (1–4). Extensive structural elucidation, employing 1D and 2D NMR, high-resolution mass spectrometry, Marfey’s analysis, and NOESY correlations, confirmed their structures. The bioactivity of these compounds was tested against six fungal phytopathogens, and compounds 3 and 4 demonstrated strong efficacy, particularly against Zymoseptoria tritici, with compound 3 exhibiting the highest potency (EC50: 11 nM). Both compounds also displayed significant antifungal activity against Botrytis cinerea and Colletotrichum acutatum, with compound 4 proving to be the most potent. Despite moderate cytotoxicity against the human cancer cell line HepG2, compounds 3 and 4 emerge as promising fungicides for combating Septoria tritici blotch, anthracnose, and gray mold.</description><identifier>ISSN: 0021-8561</identifier><identifier>ISSN: 1520-5118</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.4c01303</identifier><identifier>PMID: 38935555</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Bioactive Constituents, Metabolites, and Functions</subject><ispartof>Journal of agricultural and food chemistry, 2024-07, Vol.72 (27), p.15256-15264</ispartof><rights>2024 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a219t-5d71149510c0d00878d86930ba07c82e06c4952508af837389b4d8e8d96ac623</cites><orcidid>0000-0003-1607-5106 ; 0000-0002-4202-1219 ; 0000-0003-1729-0860</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jafc.4c01303$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jafc.4c01303$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38935555$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fernández-Pastor, Ignacio</creatorcontrib><creatorcontrib>González-Menéndez, Victor</creatorcontrib><creatorcontrib>González, Ignacio</creatorcontrib><creatorcontrib>Serrano, Rachel</creatorcontrib><creatorcontrib>Mackenzie, Thomas A.</creatorcontrib><creatorcontrib>Benítez, Guillermo</creatorcontrib><creatorcontrib>Casares-Porcel, Manuel</creatorcontrib><creatorcontrib>Genilloud, Olga</creatorcontrib><creatorcontrib>Reyes, Fernando</creatorcontrib><title>Escuzarmycins A–D, Potent Biofungicides to Control Septoria tritici Blotch</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>A study targeting novel antifungal metabolites identified potent in vitro antifungal activity against key plant pathogens in acetone extracts of Streptomyces sp. strain CA-296093. Feature-based molecular networking revealed the presence in this extract of antimycin-related compounds, leading to the isolation of four new compounds: escuzarmycins A–D (1–4). Extensive structural elucidation, employing 1D and 2D NMR, high-resolution mass spectrometry, Marfey’s analysis, and NOESY correlations, confirmed their structures. The bioactivity of these compounds was tested against six fungal phytopathogens, and compounds 3 and 4 demonstrated strong efficacy, particularly against Zymoseptoria tritici, with compound 3 exhibiting the highest potency (EC50: 11 nM). Both compounds also displayed significant antifungal activity against Botrytis cinerea and Colletotrichum acutatum, with compound 4 proving to be the most potent. Despite moderate cytotoxicity against the human cancer cell line HepG2, compounds 3 and 4 emerge as promising fungicides for combating Septoria tritici blotch, anthracnose, and gray mold.</description><subject>Bioactive Constituents, Metabolites, and Functions</subject><issn>0021-8561</issn><issn>1520-5118</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kL1OwzAURi0EoqWwMyGPDE25tpvEGUspP1IlkOhuuY4DrpK42M5QJt6BN-RJcGlhw4uHe75P9x6EzgmMCFByJZUfrWSlRmMFhAE7QH2SUkhSQvgh6kNkEp5mpIdOvF8BAE9zOEY9xguWxtdH85lX3bt0zUaZ1uPJ18fnzRA_2aDbgK-Nrbr2xShTao-DxVPbBmdr_KzXwTojcXAmxDG-rm1Qr6foqJK112f7f4AWt7PF9D6ZP949TCfzRFJShCQtc0LGRUpAQRl3ynnJs4LBUkKuONWQqTilKXBZcZbHZZfjkmteFplUGWUDdLmrXTv71mkfRGO80nUtW207LxjkjEYbtIgo7FDlrPdOV2LtTCPdRhAQW4UiKhRbhWKvMEYu9u3dstHlX-DXWQSGO-AnajvXxlv_7_sGiKt8Pg</recordid><startdate>20240710</startdate><enddate>20240710</enddate><creator>Fernández-Pastor, Ignacio</creator><creator>González-Menéndez, Victor</creator><creator>González, Ignacio</creator><creator>Serrano, Rachel</creator><creator>Mackenzie, Thomas A.</creator><creator>Benítez, Guillermo</creator><creator>Casares-Porcel, Manuel</creator><creator>Genilloud, Olga</creator><creator>Reyes, Fernando</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1607-5106</orcidid><orcidid>https://orcid.org/0000-0002-4202-1219</orcidid><orcidid>https://orcid.org/0000-0003-1729-0860</orcidid></search><sort><creationdate>20240710</creationdate><title>Escuzarmycins A–D, Potent Biofungicides to Control Septoria tritici Blotch</title><author>Fernández-Pastor, Ignacio ; González-Menéndez, Victor ; González, Ignacio ; Serrano, Rachel ; Mackenzie, Thomas A. ; Benítez, Guillermo ; Casares-Porcel, Manuel ; Genilloud, Olga ; Reyes, Fernando</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a219t-5d71149510c0d00878d86930ba07c82e06c4952508af837389b4d8e8d96ac623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Bioactive Constituents, Metabolites, and Functions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fernández-Pastor, Ignacio</creatorcontrib><creatorcontrib>González-Menéndez, Victor</creatorcontrib><creatorcontrib>González, Ignacio</creatorcontrib><creatorcontrib>Serrano, Rachel</creatorcontrib><creatorcontrib>Mackenzie, Thomas A.</creatorcontrib><creatorcontrib>Benítez, Guillermo</creatorcontrib><creatorcontrib>Casares-Porcel, Manuel</creatorcontrib><creatorcontrib>Genilloud, Olga</creatorcontrib><creatorcontrib>Reyes, Fernando</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fernández-Pastor, Ignacio</au><au>González-Menéndez, Victor</au><au>González, Ignacio</au><au>Serrano, Rachel</au><au>Mackenzie, Thomas A.</au><au>Benítez, Guillermo</au><au>Casares-Porcel, Manuel</au><au>Genilloud, Olga</au><au>Reyes, Fernando</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Escuzarmycins A–D, Potent Biofungicides to Control Septoria tritici Blotch</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2024-07-10</date><risdate>2024</risdate><volume>72</volume><issue>27</issue><spage>15256</spage><epage>15264</epage><pages>15256-15264</pages><issn>0021-8561</issn><issn>1520-5118</issn><eissn>1520-5118</eissn><abstract>A study targeting novel antifungal metabolites identified potent in vitro antifungal activity against key plant pathogens in acetone extracts of Streptomyces sp. strain CA-296093. Feature-based molecular networking revealed the presence in this extract of antimycin-related compounds, leading to the isolation of four new compounds: escuzarmycins A–D (1–4). Extensive structural elucidation, employing 1D and 2D NMR, high-resolution mass spectrometry, Marfey’s analysis, and NOESY correlations, confirmed their structures. The bioactivity of these compounds was tested against six fungal phytopathogens, and compounds 3 and 4 demonstrated strong efficacy, particularly against Zymoseptoria tritici, with compound 3 exhibiting the highest potency (EC50: 11 nM). Both compounds also displayed significant antifungal activity against Botrytis cinerea and Colletotrichum acutatum, with compound 4 proving to be the most potent. Despite moderate cytotoxicity against the human cancer cell line HepG2, compounds 3 and 4 emerge as promising fungicides for combating Septoria tritici blotch, anthracnose, and gray mold.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38935555</pmid><doi>10.1021/acs.jafc.4c01303</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-1607-5106</orcidid><orcidid>https://orcid.org/0000-0002-4202-1219</orcidid><orcidid>https://orcid.org/0000-0003-1729-0860</orcidid></addata></record>
fulltext	fulltext
identifier	ISSN: 0021-8561
ispartof	Journal of agricultural and food chemistry, 2024-07, Vol.72 (27), p.15256-15264
issn	0021-8561 1520-5118 1520-5118
language	eng
recordid	cdi_proquest_miscellaneous_3073230329
source	American Chemical Society Journals
subjects	Bioactive Constituents, Metabolites, and Functions
title	Escuzarmycins A–D, Potent Biofungicides to Control Septoria tritici Blotch
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-11T01%3A12%3A52IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Escuzarmycins%20A%E2%80%93D,%20Potent%20Biofungicides%20to%20Control%20Septoria%20tritici%20Blotch&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Ferna%CC%81ndez-Pastor,%20Ignacio&rft.date=2024-07-10&rft.volume=72&rft.issue=27&rft.spage=15256&rft.epage=15264&rft.pages=15256-15264&rft.issn=0021-8561&rft.eissn=1520-5118&rft_id=info:doi/10.1021/acs.jafc.4c01303&rft_dat=%3Cproquest_cross%3E3073230329%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3073230329&rft_id=info:pmid/38935555&rfr_iscdi=true