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Derivatization of Natural Compound β-Pinene Enhances Its In Vitro Antifungal Activity against Plant Pathogens.

Identifieur interne : 000545 ( Main/Exploration ); précédent : 000544; suivant : 000546

Derivatization of Natural Compound β-Pinene Enhances Its In Vitro Antifungal Activity against Plant Pathogens.

Auteurs : Yunfei Shi [République populaire de Chine] ; Hongyan Si [République populaire de Chine] ; Peng Wang [République populaire de Chine] ; Shangxing Chen [République populaire de Chine] ; Shibin Shang [République populaire de Chine] ; Zhanqian Song [République populaire de Chine] ; Zongde Wang [République populaire de Chine] ; Shengliang Liao [République populaire de Chine]

Source :

RBID : pubmed:31470567

Descripteurs français

English descriptors

Abstract

BACKGROUND

The development of new antifungal agents has always been a hot research topic in pesticide development. In this study, a series of derivatives of natural compound β-pinene were prepared, and the antifungal activities of these derivatives were evaluated. The purpose of this work is to develop some novel molecules as promising new fungicides.

METHODS

Through a variety of chemical reactions, β-pinene was transformed into a series of β-pinene-based derivatives containing amide moieties and acylthiourea moieties. The antifungal activities of these derivatives against five plant pathogens including

RESULTS

Some derivatives exhibited moderate or significant antifungal activity due to the fusion of the amide moiety or the acylthiourea moiety with the pinane skeleton. The structure-activity relationship analysis showed that the fluorine atom and the strong electron withdrawing nitro group, or trifluoromethyl group on the benzene ring of the derivatives had a significant effect on the improvement of the antifungal activity against


DOI: 10.3390/molecules24173144
PubMed: 31470567
PubMed Central: PMC6749435


Affiliations:


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Le document en format XML

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<term>Bicyclic Monoterpenes (chemical synthesis)</term>
<term>Bicyclic Monoterpenes (pharmacology)</term>
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<term>Fusarium (drug effects)</term>
<term>Fusarium (growth & development)</term>
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<term>Phytophthora (growth & development)</term>
<term>Plant Diseases (microbiology)</term>
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<term>Sordariales (drug effects)</term>
<term>Sordariales (growth & development)</term>
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<term>Colletotrichum (effets des médicaments et des substances chimiques)</term>
<term>Fongicides industriels (pharmacologie)</term>
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<term>Fusarium (effets des médicaments et des substances chimiques)</term>
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<term>Maladies des plantes (thérapie)</term>
<term>Phytophthora (croissance et développement)</term>
<term>Phytophthora (effets des médicaments et des substances chimiques)</term>
<term>Plantes (microbiologie)</term>
<term>Relation structure-activité (MeSH)</term>
<term>Sordariales (croissance et développement)</term>
<term>Sordariales (effets des médicaments et des substances chimiques)</term>
<term>Tests de sensibilité microbienne (MeSH)</term>
<term>Thiourée (composition chimique)</term>
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<term>Thiourée</term>
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<term>Alternaria</term>
<term>Colletotrichum</term>
<term>Fusarium</term>
<term>Phytophthora</term>
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<term>Colletotrichum</term>
<term>Fusarium</term>
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<term>Alternaria</term>
<term>Colletotrichum</term>
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<term>Phytophthora</term>
<term>Sordariales</term>
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<term>Alternaria</term>
<term>Colletotrichum</term>
<term>Fusarium</term>
<term>Phytophthora</term>
<term>Sordariales</term>
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<term>Maladies des plantes</term>
<term>Plantes</term>
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<term>Plants</term>
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<term>Plant Diseases</term>
</keywords>
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<keywords scheme="MESH" xml:lang="en">
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<term>Structure-Activity Relationship</term>
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<front>
<div type="abstract" xml:lang="en">
<p>
<b>BACKGROUND</b>
</p>
<p>The development of new antifungal agents has always been a hot research topic in pesticide development. In this study, a series of derivatives of natural compound β-pinene were prepared, and the antifungal activities of these derivatives were evaluated. The purpose of this work is to develop some novel molecules as promising new fungicides.</p>
</div>
<div type="abstract" xml:lang="en">
<p>
<b>METHODS</b>
</p>
<p>Through a variety of chemical reactions, β-pinene was transformed into a series of β-pinene-based derivatives containing amide moieties and acylthiourea moieties. The antifungal activities of these derivatives against five plant pathogens including </p>
</div>
<div type="abstract" xml:lang="en">
<p>
<b>RESULTS</b>
</p>
<p>Some derivatives exhibited moderate or significant antifungal activity due to the fusion of the amide moiety or the acylthiourea moiety with the pinane skeleton. The structure-activity relationship analysis showed that the fluorine atom and the strong electron withdrawing nitro group, or trifluoromethyl group on the benzene ring of the derivatives had a significant effect on the improvement of the antifungal activity against </p>
</div>
</front>
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<Day>10</Day>
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<ISSN IssnType="Electronic">1420-3049</ISSN>
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<Volume>24</Volume>
<Issue>17</Issue>
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<Title>Molecules (Basel, Switzerland)</Title>
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<ELocationID EIdType="doi" ValidYN="Y">10.3390/molecules24173144</ELocationID>
<Abstract>
<AbstractText Label="BACKGROUND" NlmCategory="BACKGROUND">The development of new antifungal agents has always been a hot research topic in pesticide development. In this study, a series of derivatives of natural compound β-pinene were prepared, and the antifungal activities of these derivatives were evaluated. The purpose of this work is to develop some novel molecules as promising new fungicides.</AbstractText>
<AbstractText Label="METHODS" NlmCategory="METHODS">Through a variety of chemical reactions, β-pinene was transformed into a series of β-pinene-based derivatives containing amide moieties and acylthiourea moieties. The antifungal activities of these derivatives against five plant pathogens including
<i>Colletotrichum gloeosporioides</i>
,
<i>Fusarium proliferatum</i>
,
<i>Alternaria kikuchiana</i>
,
<i>Phomopsis</i>
sp. and
<i>Phytophthora capsici</i>
were tested; preliminary structure-activity relationship was discussed.</AbstractText>
<AbstractText Label="RESULTS" NlmCategory="RESULTS">Some derivatives exhibited moderate or significant antifungal activity due to the fusion of the amide moiety or the acylthiourea moiety with the pinane skeleton. The structure-activity relationship analysis showed that the fluorine atom and the strong electron withdrawing nitro group, or trifluoromethyl group on the benzene ring of the derivatives had a significant effect on the improvement of the antifungal activity against
<i>Colletotrichum gloeosporioides</i>
,
<i>Fusarium proliferatum</i>
,
<i>Alternaria kikuchiana</i>
and
<i>Phomopsis</i>
sp. Meanwhile, the introduction of an ethyl group at the meta-position on the benzene ring of the derivatives could improve the antifungal activity against
<i>Phytophthora capsici</i>
. Compounds
<b>4e</b>
,
<b>4h</b>
,
<b>4q</b>
,
<b>4r</b>
exhibited broad-spectrum antifungal activity against the tested strains. Compound
<b>4o</b>
had significant antifungal activity against
<i>Phytophthora capsici</i>
(IC
<sub>50</sub>
= 0.18 μmol/L). These derivatives were expected to be used as precursor molecules for novel pesticide development in further research.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y">
<Author ValidYN="Y">
<LastName>Shi</LastName>
<ForeName>Yunfei</ForeName>
<Initials>Y</Initials>
<AffiliationInfo>
<Affiliation>College of Forestry, Jiangxi Agricultural University; National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; National Forestry and Grassland Bureau/Jiangxi Provincial Camphor Engineering Technology Research Center; Collaborative Innovation Center of Jiangxi Typical Trees Cultivation and Utilization, Nanchang 330045, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Si</LastName>
<ForeName>Hongyan</ForeName>
<Initials>H</Initials>
<AffiliationInfo>
<Affiliation>College of Forestry, Jiangxi Agricultural University; National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; National Forestry and Grassland Bureau/Jiangxi Provincial Camphor Engineering Technology Research Center; Collaborative Innovation Center of Jiangxi Typical Trees Cultivation and Utilization, Nanchang 330045, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Wang</LastName>
<ForeName>Peng</ForeName>
<Initials>P</Initials>
<AffiliationInfo>
<Affiliation>College of Forestry, Jiangxi Agricultural University; National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; National Forestry and Grassland Bureau/Jiangxi Provincial Camphor Engineering Technology Research Center; Collaborative Innovation Center of Jiangxi Typical Trees Cultivation and Utilization, Nanchang 330045, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Chen</LastName>
<ForeName>Shangxing</ForeName>
<Initials>S</Initials>
<AffiliationInfo>
<Affiliation>College of Forestry, Jiangxi Agricultural University; National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; National Forestry and Grassland Bureau/Jiangxi Provincial Camphor Engineering Technology Research Center; Collaborative Innovation Center of Jiangxi Typical Trees Cultivation and Utilization, Nanchang 330045, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Shang</LastName>
<ForeName>Shibin</ForeName>
<Initials>S</Initials>
<AffiliationInfo>
<Affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Song</LastName>
<ForeName>Zhanqian</ForeName>
<Initials>Z</Initials>
<AffiliationInfo>
<Affiliation>Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Wang</LastName>
<ForeName>Zongde</ForeName>
<Initials>Z</Initials>
<AffiliationInfo>
<Affiliation>College of Forestry, Jiangxi Agricultural University; National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; National Forestry and Grassland Bureau/Jiangxi Provincial Camphor Engineering Technology Research Center; Collaborative Innovation Center of Jiangxi Typical Trees Cultivation and Utilization, Nanchang 330045, China. zongdewang@163.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y">
<LastName>Liao</LastName>
<ForeName>Shengliang</ForeName>
<Initials>S</Initials>
<Identifier Source="ORCID">0000-0002-1622-563X</Identifier>
<AffiliationInfo>
<Affiliation>College of Forestry, Jiangxi Agricultural University; National Forestry and Grassland Bureau Woody Spice (East China) Engineering Technology Research Center; National Forestry and Grassland Bureau/Jiangxi Provincial Camphor Engineering Technology Research Center; Collaborative Innovation Center of Jiangxi Typical Trees Cultivation and Utilization, Nanchang 330045, China. liaosl@jxau.edu.cn.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<GrantList CompleteYN="Y">
<Grant>
<GrantID>31800493</GrantID>
<Agency>National Natural Science Foundation of China</Agency>
<Country></Country>
</Grant>
</GrantList>
<PublicationTypeList>
<PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic">
<Year>2019</Year>
<Month>08</Month>
<Day>29</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo>
<Country>Switzerland</Country>
<MedlineTA>Molecules</MedlineTA>
<NlmUniqueID>100964009</NlmUniqueID>
<ISSNLinking>1420-3049</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000577">Amides</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000081008">Bicyclic Monoterpenes</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D005659">Fungicides, Industrial</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>4MS8VHZ1HJ</RegistryNumber>
<NameOfSubstance UI="C010789">beta-pinene</NameOfSubstance>
</Chemical>
<Chemical>
<RegistryNumber>GYV9AM2QAG</RegistryNumber>
<NameOfSubstance UI="D013890">Thiourea</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList>
<MeshHeading>
<DescriptorName UI="D000528" MajorTopicYN="N">Alternaria</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
<QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D000577" MajorTopicYN="N">Amides</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D000081008" MajorTopicYN="N">Bicyclic Monoterpenes</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D020231" MajorTopicYN="N">Colletotrichum</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
<QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005659" MajorTopicYN="N">Fungicides, Industrial</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D005670" MajorTopicYN="N">Fusarium</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
<QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D010838" MajorTopicYN="N">Phytophthora</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
<QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D010935" MajorTopicYN="N">Plant Diseases</DescriptorName>
<QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName>
<QualifierName UI="Q000628" MajorTopicYN="N">therapy</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D010944" MajorTopicYN="N">Plants</DescriptorName>
<QualifierName UI="Q000382" MajorTopicYN="N">microbiology</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D020037" MajorTopicYN="N">Sordariales</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
<QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
<MeshHeading>
<DescriptorName UI="D013890" MajorTopicYN="N">Thiourea</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM">
<Keyword MajorTopicYN="N">acylthiourea</Keyword>
<Keyword MajorTopicYN="N">amide</Keyword>
<Keyword MajorTopicYN="N">antifungal activity</Keyword>
<Keyword MajorTopicYN="N">myrtanyl acid</Keyword>
<Keyword MajorTopicYN="N">pinene</Keyword>
</KeywordList>
</MedlineCitation>
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<History>
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<Year>2019</Year>
<Month>07</Month>
<Day>22</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised">
<Year>2019</Year>
<Month>08</Month>
<Day>24</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted">
<Year>2019</Year>
<Month>08</Month>
<Day>28</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez">
<Year>2019</Year>
<Month>9</Month>
<Day>1</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed">
<Year>2019</Year>
<Month>9</Month>
<Day>1</Day>
<Hour>6</Hour>
<Minute>0</Minute>
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<PubMedPubDate PubStatus="medline">
<Year>2020</Year>
<Month>2</Month>
<Day>1</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
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<PublicationStatus>epublish</PublicationStatus>
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</region>
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<name sortKey="Chen, Shangxing" sort="Chen, Shangxing" uniqKey="Chen S" first="Shangxing" last="Chen">Shangxing Chen</name>
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<name sortKey="Wang, Peng" sort="Wang, Peng" uniqKey="Wang P" first="Peng" last="Wang">Peng Wang</name>
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