Sulfur-containing natural hinduchelins derivatives as potential antifungal agents against Rhizoctonia solani.
Identifieur interne : 000046 ( Main/Exploration ); précédent : 000045; suivant : 000047Sulfur-containing natural hinduchelins derivatives as potential antifungal agents against Rhizoctonia solani.
Auteurs : Shaoyong Ke [République populaire de Chine] ; Wei Fang [République populaire de Chine] ; Wenbo Huang [République populaire de Chine] ; Zhigang Zhang [République populaire de Chine] ; Liqiao Shi [République populaire de Chine] ; Zhongyi Wan [République populaire de Chine] ; Kaimei Wang [République populaire de Chine] ; Chunxia Cao [République populaire de Chine] ; Daye Huang [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2020.
Abstract
Aryl-oxazole alkaloids are an important class of heterocyclic natural products, and which has been demonstrated to exhibit broad biological functions. During the course of our research for highly active compounds from natural products, the natural hinduchelins A-D with typical aryl-oxazole unit have been synthesized and investigated. So, in order to develop highly potential functional molecules, a series of novel sulfur-containing aryl-oxazole compounds derived from natural hinduchelins was designed and synthesized, and their in vitro fungicidal activities against four common plant pathogenic fungi (oomycetes Phytophthora capsici, ascomycetes Sclerotinia sclerotiorum, deuteromycetes Botrytis cinerea and basidiomycetes Rhizoctonia solani) were evaluated, the results demonstrated that compounds 7b and 7c displayed good selectivity and specificity in vitro against basidiomycetes R. solani. In addition, the in vivo antifungal activities also indicated compounds 7b and 7c can protect the horsebean against infection by R. solani, and the possible mechanism of antifungal action for these compounds has also been investigated.
DOI: 10.1016/j.bmcl.2020.127245
PubMed: 32389528
Affiliations:
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Cao</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Huang, Daye" sort="Huang, Daye" uniqKey="Huang D" first="Daye" last="Huang">Daye Huang</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China. 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Electronic address: shaoyong.ke@nberc.com.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Fang, Wei" sort="Fang, Wei" uniqKey="Fang W" first="Wei" last="Fang">Wei Fang</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Huang, Wenbo" sort="Huang, Wenbo" uniqKey="Huang W" first="Wenbo" last="Huang">Wenbo Huang</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Zhang, Zhigang" sort="Zhang, Zhigang" uniqKey="Zhang Z" first="Zhigang" last="Zhang">Zhigang Zhang</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Shi, Liqiao" sort="Shi, Liqiao" uniqKey="Shi L" first="Liqiao" last="Shi">Liqiao Shi</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Wan, Zhongyi" sort="Wan, Zhongyi" uniqKey="Wan Z" first="Zhongyi" last="Wan">Zhongyi Wan</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Wang, Kaimei" sort="Wang, Kaimei" uniqKey="Wang K" first="Kaimei" last="Wang">Kaimei Wang</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Cao, Chunxia" sort="Cao, Chunxia" uniqKey="Cao C" first="Chunxia" last="Cao">Chunxia Cao</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author><author><name sortKey="Huang, Daye" sort="Huang, Daye" uniqKey="Huang D" first="Daye" last="Huang">Daye Huang</name><affiliation wicri:level="1"><nlm:affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China. Electronic address: xiaohuangdaye@126.com.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Aryl-oxazole alkaloids are an important class of heterocyclic natural products, and which has been demonstrated to exhibit broad biological functions. During the course of our research for highly active compounds from natural products, the natural hinduchelins A-D with typical aryl-oxazole unit have been synthesized and investigated. So, in order to develop highly potential functional molecules, a series of novel sulfur-containing aryl-oxazole compounds derived from natural hinduchelins was designed and synthesized, and their in vitro fungicidal activities against four common plant pathogenic fungi (oomycetes Phytophthora capsici, ascomycetes Sclerotinia sclerotiorum, deuteromycetes Botrytis cinerea and basidiomycetes Rhizoctonia solani) were evaluated, the results demonstrated that compounds 7b and 7c displayed good selectivity and specificity in vitro against basidiomycetes R. solani. In addition, the in vivo antifungal activities also indicated compounds 7b and 7c can protect the horsebean against infection by R. solani, and the possible mechanism of antifungal action for these compounds has also been investigated.</div></front></TEI><pubmed><MedlineCitation Status="In-Process" Owner="NLM"><PMID Version="1">32389528</PMID><DateRevised><Year>2020</Year><Month>10</Month><Day>28</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3405</ISSN><JournalIssue CitedMedium="Internet"><Volume>30</Volume><Issue>13</Issue><PubDate><Year>2020</Year><Month>07</Month><Day>01</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg Med Chem Lett</ISOAbbreviation></Journal><ArticleTitle>Sulfur-containing natural hinduchelins derivatives as potential antifungal agents against Rhizoctonia solani.</ArticleTitle><Pagination><MedlinePgn>127245</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0960-894X(20)30350-4</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmcl.2020.127245</ELocationID><Abstract><AbstractText>Aryl-oxazole alkaloids are an important class of heterocyclic natural products, and which has been demonstrated to exhibit broad biological functions. During the course of our research for highly active compounds from natural products, the natural hinduchelins A-D with typical aryl-oxazole unit have been synthesized and investigated. So, in order to develop highly potential functional molecules, a series of novel sulfur-containing aryl-oxazole compounds derived from natural hinduchelins was designed and synthesized, and their in vitro fungicidal activities against four common plant pathogenic fungi (oomycetes Phytophthora capsici, ascomycetes Sclerotinia sclerotiorum, deuteromycetes Botrytis cinerea and basidiomycetes Rhizoctonia solani) were evaluated, the results demonstrated that compounds 7b and 7c displayed good selectivity and specificity in vitro against basidiomycetes R. solani. In addition, the in vivo antifungal activities also indicated compounds 7b and 7c can protect the horsebean against infection by R. solani, and the possible mechanism of antifungal action for these compounds has also been investigated.</AbstractText><CopyrightInformation>Copyright © 2020 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ke</LastName><ForeName>Shaoyong</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China. Electronic address: shaoyong.ke@nberc.com.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Fang</LastName><ForeName>Wei</ForeName><Initials>W</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Huang</LastName><ForeName>Wenbo</ForeName><Initials>W</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>Zhigang</ForeName><Initials>Z</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Shi</LastName><ForeName>Liqiao</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wan</LastName><ForeName>Zhongyi</ForeName><Initials>Z</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Kaimei</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cao</LastName><ForeName>Chunxia</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Huang</LastName><ForeName>Daye</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, People's Republic of China. Electronic address: xiaohuangdaye@126.com.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>05</Month><Day>05</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem Lett</MedlineTA><NlmUniqueID>9107377</NlmUniqueID><ISSNLinking>0960-894X</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">Antifungal activity</Keyword><Keyword MajorTopicYN="Y">Hinduchelins derivatives</Keyword><Keyword MajorTopicYN="Y">Natural products</Keyword><Keyword MajorTopicYN="Y">Sulfur-containing derivatives</Keyword></KeywordList><CoiStatement>Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.</CoiStatement></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>03</Month><Day>16</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>04</Month><Day>28</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>05</Month><Day>02</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>5</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>5</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>5</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32389528</ArticleId><ArticleId IdType="pii">S0960-894X(20)30350-4</ArticleId><ArticleId IdType="doi">10.1016/j.bmcl.2020.127245</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>République populaire de Chine</li></country><region><li>Hubei</li></region><settlement><li>Wuhan</li></settlement></list><tree><country name="République populaire de Chine"><region name="Hubei"><name sortKey="Ke, Shaoyong" sort="Ke, Shaoyong" uniqKey="Ke S" first="Shaoyong" last="Ke">Shaoyong Ke</name></region><name sortKey="Cao, Chunxia" sort="Cao, Chunxia" uniqKey="Cao C" first="Chunxia" last="Cao">Chunxia Cao</name><name sortKey="Fang, Wei" sort="Fang, Wei" uniqKey="Fang W" first="Wei" last="Fang">Wei Fang</name><name sortKey="Huang, Daye" sort="Huang, Daye" uniqKey="Huang D" first="Daye" last="Huang">Daye Huang</name><name sortKey="Huang, Wenbo" sort="Huang, Wenbo" uniqKey="Huang W" first="Wenbo" last="Huang">Wenbo Huang</name><name sortKey="Shi, Liqiao" sort="Shi, Liqiao" uniqKey="Shi L" first="Liqiao" last="Shi">Liqiao Shi</name><name sortKey="Wan, Zhongyi" sort="Wan, Zhongyi" uniqKey="Wan Z" first="Zhongyi" last="Wan">Zhongyi Wan</name><name sortKey="Wang, Kaimei" sort="Wang, Kaimei" uniqKey="Wang K" first="Kaimei" last="Wang">Kaimei Wang</name><name sortKey="Zhang, Zhigang" sort="Zhang, Zhigang" uniqKey="Zhang Z" first="Zhigang" last="Zhang">Zhigang Zhang</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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