PoplarV1, Main, Exploration, bibRecord, 001B02

The maize cytochrome P450 CYP79A61 produces phenylacetaldoxime and indole-3-acetaldoxime in heterologous systems and might contribute to plant defense and auxin formation.

Identifieur interne : 001B02 ( Main/Exploration ); précédent : 001B01; suivant : 001B03

The maize cytochrome P450 CYP79A61 produces phenylacetaldoxime and indole-3-acetaldoxime in heterologous systems and might contribute to plant defense and auxin formation.

Auteurs : Sandra Irmisch [Allemagne] ; Philipp Zeltner [Allemagne] ; Vinzenz Handrick [Allemagne] ; Jonathan Gershenzon [Allemagne] ; Tobias G. Köllner [Allemagne]

Source :

BMC plant biology [ 1471-2229 ] ; 2015.

RBID : pubmed:26017568

Descripteurs français

KwdFr :
- Acides aminés (métabolisme), Acides indolacétiques (métabolisme), Animaux (MeSH), Cytochrome P-450 enzyme system (composition chimique), Cytochrome P-450 enzyme system (génétique), Cytochrome P-450 enzyme system (métabolisme), Données de séquences moléculaires (MeSH), Feuilles de plante (parasitologie), Gènes de plante (MeSH), Herbivorie (MeSH), Indoles (composition chimique), Indoles (métabolisme), Isomérie (MeSH), Larve (MeSH), Oximes (composition chimique), Oximes (métabolisme), Phylogenèse (MeSH), Protéines végétales (génétique), Protéines végétales (métabolisme), Régulation de l'expression des gènes végétaux (MeSH), Saccharomyces cerevisiae (métabolisme), Sorghum (enzymologie), Spodoptera (physiologie), Spécificité du substrat (MeSH), Séquence d'acides aminés (MeSH), Tabac (génétique), Volatilisation (MeSH), Végétaux génétiquement modifiés (MeSH), Zea mays (enzymologie), Zea mays (génétique), Zea mays (immunologie), Zea mays (métabolisme).
MESH :
- composition chimique : Cytochrome P-450 enzyme system, Indoles, Oximes.
- enzymologie : Sorghum, Zea mays.
- génétique : Cytochrome P-450 enzyme system, Protéines végétales, Tabac, Zea mays.
- immunologie : Zea mays.
- métabolisme : Acides aminés, Acides indolacétiques, Cytochrome P-450 enzyme system, Indoles, Oximes, Protéines végétales, Saccharomyces cerevisiae, Zea mays.
- parasitologie : Feuilles de plante.
- physiologie : Spodoptera.
- Animaux, Données de séquences moléculaires, Gènes de plante, Herbivorie, Isomérie, Larve, Phylogenèse, Régulation de l'expression des gènes végétaux, Spécificité du substrat, Séquence d'acides aminés, Volatilisation, Végétaux génétiquement modifiés.

English descriptors

KwdEn :
- Amino Acid Sequence (MeSH), Amino Acids (metabolism), Animals (MeSH), Cytochrome P-450 Enzyme System (chemistry), Cytochrome P-450 Enzyme System (genetics), Cytochrome P-450 Enzyme System (metabolism), Gene Expression Regulation, Plant (MeSH), Genes, Plant (MeSH), Herbivory (MeSH), Indoleacetic Acids (metabolism), Indoles (chemistry), Indoles (metabolism), Isomerism (MeSH), Larva (MeSH), Molecular Sequence Data (MeSH), Oximes (chemistry), Oximes (metabolism), Phylogeny (MeSH), Plant Leaves (parasitology), Plant Proteins (genetics), Plant Proteins (metabolism), Plants, Genetically Modified (MeSH), Saccharomyces cerevisiae (metabolism), Sorghum (enzymology), Spodoptera (physiology), Substrate Specificity (MeSH), Tobacco (genetics), Volatilization (MeSH), Zea mays (enzymology), Zea mays (genetics), Zea mays (immunology), Zea mays (metabolism).
MESH :
- chemical , chemistry : Cytochrome P-450 Enzyme System, Indoles, Oximes.
- chemical , genetics : Cytochrome P-450 Enzyme System, Plant Proteins.
- chemical , metabolism : Amino Acids, Cytochrome P-450 Enzyme System, Indoleacetic Acids, Indoles, Oximes, Plant Proteins.
- enzymology : Sorghum, Zea mays.
- genetics : Tobacco, Zea mays.
- immunology : Zea mays.
- metabolism : Saccharomyces cerevisiae, Zea mays.
- parasitology : Plant Leaves.
- physiology : Spodoptera.
- Amino Acid Sequence, Animals, Gene Expression Regulation, Plant, Genes, Plant, Herbivory, Isomerism, Larva, Molecular Sequence Data, Phylogeny, Plants, Genetically Modified, Substrate Specificity, Volatilization.

Abstract

BACKGROUND

Plants produce a group of aldoxime metabolites that are well known as volatiles and as intermediates in cyanogenic glycoside and glucosinolate biosynthesis in particular plant families. Recently it has been demonstrated that aldoximes can also accumulate as part of direct plant defense in poplar. Cytochrome P450 enzymes of the CYP79 family were shown to be responsible for the formation of aldoximes from their amino acid precursors.

RESULTS

Here we describe the identification and characterization of maize CYP79A61 which was heterologously expressed in yeast and Nicotiana benthamiana and shown to catalyze the formation of (E/Z)-phenylacetaldoxime and (E/Z)-indole-3-acetaldoxime from L-phenylalanine and L-tryptophan, respectively. Simulated herbivory on maize leaves resulted in an increased CYP79A61 transcript accumulation and in elevated levels of L-phenylalanine and (E/Z)-phenylacetaldoxime. Although L-tryptophan levels were also increased after the treatment, (E/Z)-indole-3-acetaldoxime could not be detected in the damaged leaves. However, simulated herbivory caused a significant increase in auxin concentration.

CONCLUSIONS

Our data suggest that CYP79A61 might contribute to the formation of (E/Z)-phenylacetaldoxime in maize. Since aldoximes have been described as toxic compounds for insect herbivores and pathogens, the increased accumulation of (E/Z)-phenylacetaldoxime after simulated herbivory indicates that this compound plays a role in plant defense. In addition, it is conceivable that (E/Z)-indole-3-acetaldoxime produced by recombinant CYP79A61 could be further converted into the plant hormone indole-3-acetic acid after herbivore feeding in maize.

DOI: 10.1186/s12870-015-0526-1
PubMed: 26017568
PubMed Central: PMC4446944

Affiliations:

Allemagne

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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino Acid Sequence (MeSH)</term>
<term>Amino Acids (metabolism)</term>
<term>Animals (MeSH)</term>
<term>Cytochrome P-450 Enzyme System (chemistry)</term>
<term>Cytochrome P-450 Enzyme System (genetics)</term>
<term>Cytochrome P-450 Enzyme System (metabolism)</term>
<term>Gene Expression Regulation, Plant (MeSH)</term>
<term>Genes, Plant (MeSH)</term>
<term>Herbivory (MeSH)</term>
<term>Indoleacetic Acids (metabolism)</term>
<term>Indoles (chemistry)</term>
<term>Indoles (metabolism)</term>
<term>Isomerism (MeSH)</term>
<term>Larva (MeSH)</term>
<term>Molecular Sequence Data (MeSH)</term>
<term>Oximes (chemistry)</term>
<term>Oximes (metabolism)</term>
<term>Phylogeny (MeSH)</term>
<term>Plant Leaves (parasitology)</term>
<term>Plant Proteins (genetics)</term>
<term>Plant Proteins (metabolism)</term>
<term>Plants, Genetically Modified (MeSH)</term>
<term>Saccharomyces cerevisiae (metabolism)</term>
<term>Sorghum (enzymology)</term>
<term>Spodoptera (physiology)</term>
<term>Substrate Specificity (MeSH)</term>
<term>Tobacco (genetics)</term>
<term>Volatilization (MeSH)</term>
<term>Zea mays (enzymology)</term>
<term>Zea mays (genetics)</term>
<term>Zea mays (immunology)</term>
<term>Zea mays (metabolism)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Acides aminés (métabolisme)</term>
<term>Acides indolacétiques (métabolisme)</term>
<term>Animaux (MeSH)</term>
<term>Cytochrome P-450 enzyme system (composition chimique)</term>
<term>Cytochrome P-450 enzyme system (génétique)</term>
<term>Cytochrome P-450 enzyme system (métabolisme)</term>
<term>Données de séquences moléculaires (MeSH)</term>
<term>Feuilles de plante (parasitologie)</term>
<term>Gènes de plante (MeSH)</term>
<term>Herbivorie (MeSH)</term>
<term>Indoles (composition chimique)</term>
<term>Indoles (métabolisme)</term>
<term>Isomérie (MeSH)</term>
<term>Larve (MeSH)</term>
<term>Oximes (composition chimique)</term>
<term>Oximes (métabolisme)</term>
<term>Phylogenèse (MeSH)</term>
<term>Protéines végétales (génétique)</term>
<term>Protéines végétales (métabolisme)</term>
<term>Régulation de l'expression des gènes végétaux (MeSH)</term>
<term>Saccharomyces cerevisiae (métabolisme)</term>
<term>Sorghum (enzymologie)</term>
<term>Spodoptera (physiologie)</term>
<term>Spécificité du substrat (MeSH)</term>
<term>Séquence d'acides aminés (MeSH)</term>
<term>Tabac (génétique)</term>
<term>Volatilisation (MeSH)</term>
<term>Végétaux génétiquement modifiés (MeSH)</term>
<term>Zea mays (enzymologie)</term>
<term>Zea mays (génétique)</term>
<term>Zea mays (immunologie)</term>
<term>Zea mays (métabolisme)</term>
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<term>Oximes</term>
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<keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Cytochrome P-450 Enzyme System</term>
<term>Plant Proteins</term>
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<keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Amino Acids</term>
<term>Cytochrome P-450 Enzyme System</term>
<term>Indoleacetic Acids</term>
<term>Indoles</term>
<term>Oximes</term>
<term>Plant Proteins</term>
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<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Cytochrome P-450 enzyme system</term>
<term>Indoles</term>
<term>Oximes</term>
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<keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Sorghum</term>
<term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Sorghum</term>
<term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Tobacco</term>
<term>Zea mays</term>
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<keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Cytochrome P-450 enzyme system</term>
<term>Protéines végétales</term>
<term>Tabac</term>
<term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="immunologie" xml:lang="fr"><term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="immunology" xml:lang="en"><term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Saccharomyces cerevisiae</term>
<term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Acides aminés</term>
<term>Acides indolacétiques</term>
<term>Cytochrome P-450 enzyme system</term>
<term>Indoles</term>
<term>Oximes</term>
<term>Protéines végétales</term>
<term>Saccharomyces cerevisiae</term>
<term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="parasitologie" xml:lang="fr"><term>Feuilles de plante</term>
</keywords>
<keywords scheme="MESH" qualifier="parasitology" xml:lang="en"><term>Plant Leaves</term>
</keywords>
<keywords scheme="MESH" qualifier="physiologie" xml:lang="fr"><term>Spodoptera</term>
</keywords>
<keywords scheme="MESH" qualifier="physiology" xml:lang="en"><term>Spodoptera</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term>
<term>Animals</term>
<term>Gene Expression Regulation, Plant</term>
<term>Genes, Plant</term>
<term>Herbivory</term>
<term>Isomerism</term>
<term>Larva</term>
<term>Molecular Sequence Data</term>
<term>Phylogeny</term>
<term>Plants, Genetically Modified</term>
<term>Substrate Specificity</term>
<term>Volatilization</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Données de séquences moléculaires</term>
<term>Gènes de plante</term>
<term>Herbivorie</term>
<term>Isomérie</term>
<term>Larve</term>
<term>Phylogenèse</term>
<term>Régulation de l'expression des gènes végétaux</term>
<term>Spécificité du substrat</term>
<term>Séquence d'acides aminés</term>
<term>Volatilisation</term>
<term>Végétaux génétiquement modifiés</term>
</keywords>
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<front><div type="abstract" xml:lang="en"><p><b>BACKGROUND</b>
</p>
<p>Plants produce a group of aldoxime metabolites that are well known as volatiles and as intermediates in cyanogenic glycoside and glucosinolate biosynthesis in particular plant families. Recently it has been demonstrated that aldoximes can also accumulate as part of direct plant defense in poplar. Cytochrome P450 enzymes of the CYP79 family were shown to be responsible for the formation of aldoximes from their amino acid precursors.</p>
</div>
<div type="abstract" xml:lang="en"><p><b>RESULTS</b>
</p>
<p>Here we describe the identification and characterization of maize CYP79A61 which was heterologously expressed in yeast and Nicotiana benthamiana and shown to catalyze the formation of (E/Z)-phenylacetaldoxime and (E/Z)-indole-3-acetaldoxime from L-phenylalanine and L-tryptophan, respectively. Simulated herbivory on maize leaves resulted in an increased CYP79A61 transcript accumulation and in elevated levels of L-phenylalanine and (E/Z)-phenylacetaldoxime. Although L-tryptophan levels were also increased after the treatment, (E/Z)-indole-3-acetaldoxime could not be detected in the damaged leaves. However, simulated herbivory caused a significant increase in auxin concentration.</p>
</div>
<div type="abstract" xml:lang="en"><p><b>CONCLUSIONS</b>
</p>
<p>Our data suggest that CYP79A61 might contribute to the formation of (E/Z)-phenylacetaldoxime in maize. Since aldoximes have been described as toxic compounds for insect herbivores and pathogens, the increased accumulation of (E/Z)-phenylacetaldoxime after simulated herbivory indicates that this compound plays a role in plant defense. In addition, it is conceivable that (E/Z)-indole-3-acetaldoxime produced by recombinant CYP79A61 could be further converted into the plant hormone indole-3-acetic acid after herbivore feeding in maize.</p>
</div>
</front>
</TEI>
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<DateCompleted><Year>2016</Year>
<Month>01</Month>
<Day>26</Day>
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<DateRevised><Year>2018</Year>
<Month>11</Month>
<Day>13</Day>
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<PubDate><Year>2015</Year>
<Month>May</Month>
<Day>29</Day>
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<Title>BMC plant biology</Title>
<ISOAbbreviation>BMC Plant Biol</ISOAbbreviation>
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<ArticleTitle>The maize cytochrome P450 CYP79A61 produces phenylacetaldoxime and indole-3-acetaldoxime in heterologous systems and might contribute to plant defense and auxin formation.</ArticleTitle>
<Pagination><MedlinePgn>128</MedlinePgn>
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<ELocationID EIdType="doi" ValidYN="Y">10.1186/s12870-015-0526-1</ELocationID>
<Abstract><AbstractText Label="BACKGROUND" NlmCategory="BACKGROUND">Plants produce a group of aldoxime metabolites that are well known as volatiles and as intermediates in cyanogenic glycoside and glucosinolate biosynthesis in particular plant families. Recently it has been demonstrated that aldoximes can also accumulate as part of direct plant defense in poplar. Cytochrome P450 enzymes of the CYP79 family were shown to be responsible for the formation of aldoximes from their amino acid precursors.</AbstractText>
<AbstractText Label="RESULTS" NlmCategory="RESULTS">Here we describe the identification and characterization of maize CYP79A61 which was heterologously expressed in yeast and Nicotiana benthamiana and shown to catalyze the formation of (E/Z)-phenylacetaldoxime and (E/Z)-indole-3-acetaldoxime from L-phenylalanine and L-tryptophan, respectively. Simulated herbivory on maize leaves resulted in an increased CYP79A61 transcript accumulation and in elevated levels of L-phenylalanine and (E/Z)-phenylacetaldoxime. Although L-tryptophan levels were also increased after the treatment, (E/Z)-indole-3-acetaldoxime could not be detected in the damaged leaves. However, simulated herbivory caused a significant increase in auxin concentration.</AbstractText>
<AbstractText Label="CONCLUSIONS" NlmCategory="CONCLUSIONS">Our data suggest that CYP79A61 might contribute to the formation of (E/Z)-phenylacetaldoxime in maize. Since aldoximes have been described as toxic compounds for insect herbivores and pathogens, the increased accumulation of (E/Z)-phenylacetaldoxime after simulated herbivory indicates that this compound plays a role in plant defense. In addition, it is conceivable that (E/Z)-indole-3-acetaldoxime produced by recombinant CYP79A61 could be further converted into the plant hormone indole-3-acetic acid after herbivore feeding in maize.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Irmisch</LastName>
<ForeName>Sandra</ForeName>
<Initials>S</Initials>
<AffiliationInfo><Affiliation>Department of Biochemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, 07745, Jena, Germany. sirmisch@ice.mpg.de.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Zeltner</LastName>
<ForeName>Philipp</ForeName>
<Initials>P</Initials>
<AffiliationInfo><Affiliation>Department of Biochemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, 07745, Jena, Germany. zeltner.philipp@googlemail.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Handrick</LastName>
<ForeName>Vinzenz</ForeName>
<Initials>V</Initials>
<AffiliationInfo><Affiliation>Department of Biochemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, 07745, Jena, Germany. vhandrick@ice.mpg.de.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Gershenzon</LastName>
<ForeName>Jonathan</ForeName>
<Initials>J</Initials>
<AffiliationInfo><Affiliation>Department of Biochemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, 07745, Jena, Germany. gershenzon@ice.mpg.de.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Köllner</LastName>
<ForeName>Tobias G</ForeName>
<Initials>TG</Initials>
<AffiliationInfo><Affiliation>Department of Biochemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll Straße 8, 07745, Jena, Germany. koellner@ice.mpg.de.</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>2015</Year>
<Month>05</Month>
<Day>29</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>BMC Plant Biol</MedlineTA>
<NlmUniqueID>100967807</NlmUniqueID>
<ISSNLinking>1471-2229</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000596">Amino Acids</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D007210">Indoleacetic Acids</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D007211">Indoles</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D010091">Oximes</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D010940">Plant Proteins</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="C467098">indole-3-acetaldoxime</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>7028-48-0</RegistryNumber>
<NameOfSubstance UI="C408881">phenylacetaldoxime</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>9035-51-2</RegistryNumber>
<NameOfSubstance UI="D003577">Cytochrome P-450 Enzyme System</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D000595" MajorTopicYN="N">Amino Acid Sequence</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000596" MajorTopicYN="N">Amino Acids</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D003577" MajorTopicYN="N">Cytochrome P-450 Enzyme System</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName>
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</MeshHeading>
<MeshHeading><DescriptorName UI="D018506" MajorTopicYN="N">Gene Expression Regulation, Plant</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D017343" MajorTopicYN="N">Genes, Plant</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D060434" MajorTopicYN="N">Herbivory</DescriptorName>
</MeshHeading>
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<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
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<MeshHeading><DescriptorName UI="D007536" MajorTopicYN="N">Isomerism</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D007814" MajorTopicYN="N">Larva</DescriptorName>
</MeshHeading>
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<affiliations><list><country><li>Allemagne</li>
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<tree><country name="Allemagne"><noRegion><name sortKey="Irmisch, Sandra" sort="Irmisch, Sandra" uniqKey="Irmisch S" first="Sandra" last="Irmisch">Sandra Irmisch</name>
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<name sortKey="Gershenzon, Jonathan" sort="Gershenzon, Jonathan" uniqKey="Gershenzon J" first="Jonathan" last="Gershenzon">Jonathan Gershenzon</name>
<name sortKey="Handrick, Vinzenz" sort="Handrick, Vinzenz" uniqKey="Handrick V" first="Vinzenz" last="Handrick">Vinzenz Handrick</name>
<name sortKey="Kollner, Tobias G" sort="Kollner, Tobias G" uniqKey="Kollner T" first="Tobias G" last="Köllner">Tobias G. Köllner</name>
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The maize cytochrome P450 CYP79A61 produces phenylacetaldoxime and indole-3-acetaldoxime in heterologous systems and might contribute to plant defense and auxin formation.

The maize cytochrome P450 CYP79A61 produces phenylacetaldoxime and indole-3-acetaldoxime in heterologous systems and might contribute to plant defense and auxin formation.

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