In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands.
Identifieur interne : 000741 ( Main/Exploration ); précédent : 000740; suivant : 000742In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands.
Auteurs : María I. Chavez [Chili] ; Mauricio Soto [Chili] ; Franco A. Cimino [Chili] ; Andrés F. Olea [Chili] ; Luis Espinoza [Chili] ; Katy Díaz [Chili] ; Lautaro Taborga [Chili]Source :
- International journal of molecular sciences [ 1422-0067 ] ; 2018.
Descripteurs français
- KwdFr :
- MESH :
- composition chimique : Antifongiques, Phénols.
- croissance et développement : Phytophthora.
- pharmacologie : Antifongiques, Phénols.
- synthèse chimique : Antifongiques, Phénols.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Antifungal Agents, Phenols.
- chemical , chemistry : Antifungal Agents, Phenols.
- chemical , pharmacology : Antifungal Agents, Phenols.
- growth & development : Phytophthora.
Abstract
A series of new and known geranylated phenol/methoxyphenol derivatives has been tested in vitro as inhibitor agents of mycelial growth of Phytophthora cinnamomi. The activity of tested compounds is correlated with the nature, number, and position of the substituent group on the aromatic ring. Results indicate that the most active geranylated derivatives are those having two hydroxyl groups (or one ⁻OH and one ⁻OCH₃) attached to the aromatic ring. Interestingly, these derivatives are as active as Metalaxil®, a commonly used commercial fungicide. Thus, our results suggest that some of these compounds might be of agricultural interest due to their potential use as fungicides against P. cinnamomi. The effect of structure on fungicide activity is discussed in terms of electronic distribution on both the aromatic ring and side geranyl chain. All tested compounds have been synthesized by direct coupling of geraniol and the respective phenol. Interestingly, new digeranylated derivatives were obtained by increasing the reaction time.
DOI: 10.3390/ijms19061601
PubMed: 29844282
PubMed Central: PMC6032260
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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Chavez</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. maria.chavez@usm.cl.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000</wicri:regionArea><wicri:noRegion>Valparaíso 2340000</wicri:noRegion></affiliation></author><author><name sortKey="Soto, Mauricio" sort="Soto, Mauricio" uniqKey="Soto M" first="Mauricio" last="Soto">Mauricio Soto</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. mauricio.sotoc.13@sansano.usm.cl.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Departamento de Química, Universidad Técnica Federico Santa María, Av. 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España No. 1680, Valparaíso 2340000, Chile. lautaro.taborga@usm.cl.</nlm:affiliation><country xml:lang="fr">Chili</country><wicri:regionArea>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000</wicri:regionArea><wicri:noRegion>Valparaíso 2340000</wicri:noRegion></affiliation></author></analytic><series><title level="j">International journal of molecular sciences</title><idno type="eISSN">1422-0067</idno><imprint><date when="2018" type="published">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antifungal Agents (chemical synthesis)</term><term>Antifungal Agents (chemistry)</term><term>Antifungal Agents (pharmacology)</term><term>Phenols (chemical synthesis)</term><term>Phenols (chemistry)</term><term>Phenols (pharmacology)</term><term>Phytophthora (growth & development)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antifongiques (composition chimique)</term><term>Antifongiques (pharmacologie)</term><term>Antifongiques (synthèse chimique)</term><term>Phytophthora (croissance et développement)</term><term>Phénols (composition chimique)</term><term>Phénols (pharmacologie)</term><term>Phénols (synthèse chimique)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antifungal Agents</term><term>Phenols</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antifungal Agents</term><term>Phenols</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antifungal Agents</term><term>Phenols</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Antifongiques</term><term>Phénols</term></keywords><keywords scheme="MESH" qualifier="croissance et développement" xml:lang="fr"><term>Phytophthora</term></keywords><keywords scheme="MESH" qualifier="growth & development" xml:lang="en"><term>Phytophthora</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antifongiques</term><term>Phénols</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antifongiques</term><term>Phénols</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of new and known geranylated phenol/methoxyphenol derivatives has been tested in vitro as inhibitor agents of mycelial growth of <i>Phytophthora cinnamomi</i>. The activity of tested compounds is correlated with the nature, number, and position of the substituent group on the aromatic ring. Results indicate that the most active geranylated derivatives are those having two hydroxyl groups (or one ⁻OH and one ⁻OCH₃) attached to the aromatic ring. Interestingly, these derivatives are as active as Metalaxil<sup>®</sup>, a commonly used commercial fungicide. Thus, our results suggest that some of these compounds might be of agricultural interest due to their potential use as fungicides against <i>P. cinnamomi</i>. The effect of structure on fungicide activity is discussed in terms of electronic distribution on both the aromatic ring and side geranyl chain. All tested compounds have been synthesized by direct coupling of geraniol and the respective phenol. Interestingly, new digeranylated derivatives were obtained by increasing the reaction time.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">29844282</PMID><DateCompleted><Year>2018</Year><Month>09</Month><Day>26</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>14</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1422-0067</ISSN><JournalIssue CitedMedium="Internet"><Volume>19</Volume><Issue>6</Issue><PubDate><Year>2018</Year><Month>May</Month><Day>29</Day></PubDate></JournalIssue><Title>International journal of molecular sciences</Title><ISOAbbreviation>Int J Mol Sci</ISOAbbreviation></Journal><ArticleTitle>In Vitro Antifungal Activity of New and Known Geranylated Phenols against <i>Phytophthora cinnamomi</i> Rands.</ArticleTitle><ELocationID EIdType="pii" ValidYN="Y">E1601</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.3390/ijms19061601</ELocationID><Abstract><AbstractText>A series of new and known geranylated phenol/methoxyphenol derivatives has been tested in vitro as inhibitor agents of mycelial growth of <i>Phytophthora cinnamomi</i>. The activity of tested compounds is correlated with the nature, number, and position of the substituent group on the aromatic ring. Results indicate that the most active geranylated derivatives are those having two hydroxyl groups (or one ⁻OH and one ⁻OCH₃) attached to the aromatic ring. Interestingly, these derivatives are as active as Metalaxil<sup>®</sup>, a commonly used commercial fungicide. Thus, our results suggest that some of these compounds might be of agricultural interest due to their potential use as fungicides against <i>P. cinnamomi</i>. The effect of structure on fungicide activity is discussed in terms of electronic distribution on both the aromatic ring and side geranyl chain. All tested compounds have been synthesized by direct coupling of geraniol and the respective phenol. Interestingly, new digeranylated derivatives were obtained by increasing the reaction time.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Chavez</LastName><ForeName>María I</ForeName><Initials>MI</Initials><AffiliationInfo><Affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. maria.chavez@usm.cl.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Soto</LastName><ForeName>Mauricio</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. mauricio.sotoc.13@sansano.usm.cl.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cimino</LastName><ForeName>Franco A</ForeName><Initials>FA</Initials><AffiliationInfo><Affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. franco.cimino@alumnos.usm.cl.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Olea</LastName><ForeName>Andrés F</ForeName><Initials>AF</Initials><AffiliationInfo><Affiliation>Instituto de Ciencias Químicas Aplicadas, Facultad de Ingeniería, Universidad Autónoma de Chile, Santiago 8910339, Chile. andres.olea@uautonoma.cl.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Espinoza</LastName><ForeName>Luis</ForeName><Initials>L</Initials><Identifier Source="ORCID">0000-0002-4054-7487</Identifier><AffiliationInfo><Affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. luis.espinozac@usm.cl.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Díaz</LastName><ForeName>Katy</ForeName><Initials>K</Initials><AffiliationInfo><Affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. katy.diaz@usm.cl.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Taborga</LastName><ForeName>Lautaro</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>Departamento de Química, Universidad Técnica Federico Santa María, Av. España No. 1680, Valparaíso 2340000, Chile. lautaro.taborga@usm.cl.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2018</Year><Month>05</Month><Day>29</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Int J Mol Sci</MedlineTA><NlmUniqueID>101092791</NlmUniqueID><ISSNLinking>1422-0067</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000935">Antifungal Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010636">Phenols</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000935" MajorTopicYN="Y">Antifungal Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010636" MajorTopicYN="Y">Phenols</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010838" MajorTopicYN="N">Phytophthora</DescriptorName><QualifierName UI="Q000254" MajorTopicYN="Y">growth & development</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Oomycetes</Keyword><Keyword MajorTopicYN="N">Phytophthora cinnamomi</Keyword><Keyword MajorTopicYN="N">antifungal activity</Keyword><Keyword MajorTopicYN="N">fungicide</Keyword><Keyword MajorTopicYN="N">geranylated phenols</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2018</Year><Month>04</Month><Day>23</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2018</Year><Month>05</Month><Day>16</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2018</Year><Month>05</Month><Day>23</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2018</Year><Month>5</Month><Day>31</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2018</Year><Month>5</Month><Day>31</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2018</Year><Month>9</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>epublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">29844282</ArticleId><ArticleId IdType="pii">ijms19061601</ArticleId><ArticleId IdType="doi">10.3390/ijms19061601</ArticleId><ArticleId IdType="pmc">PMC6032260</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>J Agric Food Chem. 2015 Aug 12;63(31):6890-6</Citation><ArticleIdList><ArticleId IdType="pubmed">26196664</ArticleId></ArticleIdList></Reference><Reference><Citation>Food Chem Toxicol. 2017 Nov;109(Pt 2):827-835</Citation><ArticleIdList><ArticleId IdType="pubmed">28528250</ArticleId></ArticleIdList></Reference><Reference><Citation>Molecules. 2013 Feb 05;18(2):2029-51</Citation><ArticleIdList><ArticleId IdType="pubmed">23385340</ArticleId></ArticleIdList></Reference><Reference><Citation>Int J Mol Sci. 2015 Aug 14;16(8):19130-52</Citation><ArticleIdList><ArticleId IdType="pubmed">26287171</ArticleId></ArticleIdList></Reference><Reference><Citation>Molecules. 2014 Jan 27;19(2):1512-26</Citation><ArticleIdList><ArticleId IdType="pubmed">24473210</ArticleId></ArticleIdList></Reference><Reference><Citation>J Nat Prod. 1994 Dec;57(12):1711-6</Citation><ArticleIdList><ArticleId IdType="pubmed">7714539</ArticleId></ArticleIdList></Reference><Reference><Citation>Chem Biol Interact. 2016 Mar 5;247:22-9</Citation><ArticleIdList><ArticleId IdType="pubmed">26826267</ArticleId></ArticleIdList></Reference><Reference><Citation>J Org Chem. 2011 Nov 4;76(21):9151-6</Citation><ArticleIdList><ArticleId IdType="pubmed">21958335</ArticleId></ArticleIdList></Reference><Reference><Citation>Molecules. 2013 Aug 29;18(9):10413-24</Citation><ArticleIdList><ArticleId IdType="pubmed">23994968</ArticleId></ArticleIdList></Reference><Reference><Citation>Pharm Res. 2006 Jan;23(1):70-81</Citation><ArticleIdList><ArticleId IdType="pubmed">16320003</ArticleId></ArticleIdList></Reference></ReferenceList></PubmedData></pubmed><affiliations><list><country><li>Chili</li></country></list><tree><country name="Chili"><noRegion><name sortKey="Chavez, Maria I" sort="Chavez, Maria I" uniqKey="Chavez M" first="María I" last="Chavez">María I. Chavez</name></noRegion><name sortKey="Cimino, Franco A" sort="Cimino, Franco A" uniqKey="Cimino F" first="Franco A" last="Cimino">Franco A. Cimino</name><name sortKey="Diaz, Katy" sort="Diaz, Katy" uniqKey="Diaz K" first="Katy" last="Díaz">Katy Díaz</name><name sortKey="Espinoza, Luis" sort="Espinoza, Luis" uniqKey="Espinoza L" first="Luis" last="Espinoza">Luis Espinoza</name><name sortKey="Olea, Andres F" sort="Olea, Andres F" uniqKey="Olea A" first="Andrés F" last="Olea">Andrés F. Olea</name><name sortKey="Soto, Mauricio" sort="Soto, Mauricio" uniqKey="Soto M" first="Mauricio" last="Soto">Mauricio Soto</name><name sortKey="Taborga, Lautaro" sort="Taborga, Lautaro" uniqKey="Taborga L" first="Lautaro" last="Taborga">Lautaro Taborga</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i -Sk "pubmed:29844282" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \
| NlmPubMed2Wicri -a PhytophthoraV1
| This area was generated with Dilib version V0.6.38. |  |