Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysis and Structure Determination.
Identifieur interne : 001852 ( PubMed/Curation ); précédent : 001851; suivant : 001853Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysis and Structure Determination.
Auteurs : Jamie A. Freemont [Australie] ; Stuart W. Littler [Australie] ; Oliver E. Hutt [Australie] ; Stephanie Mauger [Australie] ; Adam G. Meyer [Australie] ; David A. Winkler [Australie] ; Maurice G. Kerr [Australie] ; John H. Ryan [Australie] ; Helen F. Cole [Australie] ; Peter J. Duggan [Australie]Source :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2016.
Descripteurs français
- KwdFr :
- MESH :
- isolement et purification : Insecticides, Pyréthrines.
- Chrysanthemum cinerariifolium, Insecticides, Oxydoréduction, Produits agricoles, Pyréthrines.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Insecticides, Pyrethrins.
- chemistry : Chrysanthemum cinerariifolium, Crops, Agricultural.
- chemical , isolation & purification : Insecticides, Pyrethrins.
- Oxidation-Reduction.
Abstract
Pyrethrum is a natural insecticide extracted from Tanacetum cinerariifolium. Six esters, the pyrethrins, are responsible for the extract's insecticidal activity. The oxidative degradation of pyrethrins through contact with aerial oxygen is a potential cause of pyrethrin losses during pyrethrum manufacture. Described here is the first investigation of the autoxidation chemistry of the six pyrethrin esters isolated from pyrethrum. It was found that pyrethrins I and II, the major pyrethrin esters present in pyrethrum, undergo autoxidation more readily than the minor pyrethrin esters, the jasmolins and cinerins. Chromatographic analysis of pyrethrin I and II autoxidation mixtures showed some correlation with a similar analysis performed on extracts from T. cinerariifolium crop, which had been stored for 12 weeks without added antioxidants. Two pyrethrin II autoxidation products were isolated, characterized, and shown to be present in extracts of stored T. cinerariifolium crop, confirming that autoxidation of pyrethrin esters does occur during crop storage.
DOI: 10.1021/acs.jafc.6b02959
PubMed: 27599033
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Duggan</name><affiliation wicri:level="1"><nlm:affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</nlm:affiliation><country xml:lang="fr">Australie</country><wicri:regionArea>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169</wicri:regionArea></affiliation></author></analytic><series><title level="j">Journal of agricultural and food chemistry</title><idno type="eISSN">1520-5118</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Chrysanthemum cinerariifolium (chemistry)</term><term>Crops, Agricultural (chemistry)</term><term>Insecticides (chemistry)</term><term>Insecticides (isolation & purification)</term><term>Oxidation-Reduction</term><term>Pyrethrins (chemistry)</term><term>Pyrethrins (isolation & purification)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Chrysanthemum cinerariifolium ()</term><term>Insecticides ()</term><term>Insecticides (isolement et purification)</term><term>Oxydoréduction</term><term>Produits agricoles ()</term><term>Pyréthrines ()</term><term>Pyréthrines (isolement et purification)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Insecticides</term><term>Pyrethrins</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Chrysanthemum cinerariifolium</term><term>Crops, Agricultural</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Insecticides</term><term>Pyrethrins</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Insecticides</term><term>Pyréthrines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Oxidation-Reduction</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Chrysanthemum cinerariifolium</term><term>Insecticides</term><term>Oxydoréduction</term><term>Produits agricoles</term><term>Pyréthrines</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Pyrethrum is a natural insecticide extracted from Tanacetum cinerariifolium. Six esters, the pyrethrins, are responsible for the extract's insecticidal activity. The oxidative degradation of pyrethrins through contact with aerial oxygen is a potential cause of pyrethrin losses during pyrethrum manufacture. Described here is the first investigation of the autoxidation chemistry of the six pyrethrin esters isolated from pyrethrum. It was found that pyrethrins I and II, the major pyrethrin esters present in pyrethrum, undergo autoxidation more readily than the minor pyrethrin esters, the jasmolins and cinerins. Chromatographic analysis of pyrethrin I and II autoxidation mixtures showed some correlation with a similar analysis performed on extracts from T. cinerariifolium crop, which had been stored for 12 weeks without added antioxidants. Two pyrethrin II autoxidation products were isolated, characterized, and shown to be present in extracts of stored T. cinerariifolium crop, confirming that autoxidation of pyrethrin esters does occur during crop storage.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">27599033</PMID><DateCreated><Year>2016</Year><Month>09</Month><Day>28</Day></DateCreated><DateCompleted><Year>2017</Year><Month>04</Month><Day>26</Day></DateCompleted><DateRevised><Year>2017</Year><Month>04</Month><Day>26</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-5118</ISSN><JournalIssue CitedMedium="Internet"><Volume>64</Volume><Issue>38</Issue><PubDate><Year>2016</Year><Month>Sep</Month><Day>28</Day></PubDate></JournalIssue><Title>Journal of agricultural and food chemistry</Title><ISOAbbreviation>J. Agric. Food Chem.</ISOAbbreviation></Journal><ArticleTitle>Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysis and Structure Determination.</ArticleTitle><Pagination><MedlinePgn>7134-41</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jafc.6b02959</ELocationID><Abstract><AbstractText>Pyrethrum is a natural insecticide extracted from Tanacetum cinerariifolium. Six esters, the pyrethrins, are responsible for the extract's insecticidal activity. The oxidative degradation of pyrethrins through contact with aerial oxygen is a potential cause of pyrethrin losses during pyrethrum manufacture. Described here is the first investigation of the autoxidation chemistry of the six pyrethrin esters isolated from pyrethrum. It was found that pyrethrins I and II, the major pyrethrin esters present in pyrethrum, undergo autoxidation more readily than the minor pyrethrin esters, the jasmolins and cinerins. Chromatographic analysis of pyrethrin I and II autoxidation mixtures showed some correlation with a similar analysis performed on extracts from T. cinerariifolium crop, which had been stored for 12 weeks without added antioxidants. Two pyrethrin II autoxidation products were isolated, characterized, and shown to be present in extracts of stored T. cinerariifolium crop, confirming that autoxidation of pyrethrin esters does occur during crop storage.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Freemont</LastName><ForeName>Jamie A</ForeName><Initials>JA</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Littler</LastName><ForeName>Stuart W</ForeName><Initials>SW</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hutt</LastName><ForeName>Oliver E</ForeName><Initials>OE</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Mauger</LastName><ForeName>Stephanie</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Institut de Recherche de Chimie Paris, CNRS - Chimie ParisTech , 11 rue Pierre et Marie Curie, 75005 Paris, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Meyer</LastName><ForeName>Adam G</ForeName><Initials>AG</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Winkler</LastName><ForeName>David A</ForeName><Initials>DA</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>School of Chemical and Physical Sciences, Flinders University , Adelaide, South Australia 5042, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kerr</LastName><ForeName>Maurice G</ForeName><Initials>MG</Initials><AffiliationInfo><Affiliation>Botanical Resources Australia , 44-46 Industrial Drive, Ulverstone, Tasmania 7315, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ryan</LastName><ForeName>John H</ForeName><Initials>JH</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cole</LastName><ForeName>Helen F</ForeName><Initials>HF</Initials><AffiliationInfo><Affiliation>Botanical Resources Australia , 44-46 Industrial Drive, Ulverstone, Tasmania 7315, Australia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Duggan</LastName><ForeName>Peter J</ForeName><Initials>PJ</Initials><AffiliationInfo><Affiliation>CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>School of Chemical and Physical Sciences, Flinders University , Adelaide, South Australia 5042, Australia.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>09</Month><Day>19</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Agric Food Chem</MedlineTA><NlmUniqueID>0374755</NlmUniqueID><ISSNLinking>0021-8561</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007306">Insecticides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011722">Pyrethrins</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D011723" MajorTopicYN="N">Chrysanthemum cinerariifolium</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018556" MajorTopicYN="N">Crops, Agricultural</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007306" MajorTopicYN="N">Insecticides</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010084" MajorTopicYN="N">Oxidation-Reduction</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011722" MajorTopicYN="N">Pyrethrins</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Tanacetum cinerariifolium</Keyword><Keyword MajorTopicYN="N">autoxidation</Keyword><Keyword MajorTopicYN="N">degradation</Keyword><Keyword MajorTopicYN="N">pyrethrins</Keyword><Keyword MajorTopicYN="N">pyrethrum</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>9</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>9</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2017</Year><Month>4</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27599033</ArticleId><ArticleId IdType="doi">10.1021/acs.jafc.6b02959</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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