AustralieFrV1, Main, Exploration, bibRecord, 00DF06

Novel 2-ethyl-5-alkylpyrrolidines in the venom of an australian ant of the genus Monomorium

Identifieur interne : 00DF06 ( Main/Exploration ); précédent : 00DF05; suivant : 00DF07

Novel 2-ethyl-5-alkylpyrrolidines in the venom of an australian ant of the genus Monomorium

Auteurs : Tappey H. Jones [États-Unis] ; Murray S. Blum [Géorgie (pays)] ; Alan N. Andersen [Australie] ; Henry M. Fales [États-Unis] ; Pierre Escoubas [France]

Source :

Journal of Chemical Ecology [ 0098-0331 ] ; 1988-01-01.

RBID : ISTEX:00CF65AA25A7AA75773F949009BA30D244D52A00

English descriptors

Abstract

Abstract: Novel 2-ethyl-5-alkylpyrrolidines and their corresponding 1-pyrrolines have been identified as poison gland products from an unidentified Australian species ofMonomorium. The major alkaloids present in the venom of this ant aretrans-2-ethyl-5-undecylpyrrolidine andtrans-2-ethyl-5-(12-tridecen-1-yl)pyrrolidine. The position of the double bond in the latter was established from its dimethyl-disulfide adduct after the amine function had been protected, and the stereochemistry of the alkyl groups was determined by direct comparison with synthetic compounds. The corresponding 1-pyrrolines were also detected in varying amounts in this venom. The pyrrolidines and 1-pyrrolines possess considerable insecticidal activity when evaluated against termite workers. The alkaloidal venoms ofMonomorium appear to be an important factor contributing to the success of these small ants both as competitors and as predators.

Url:

https://api.istex.fr/document/00CF65AA25A7AA75773F949009BA30D244D52A00/fulltext/pdf

DOI: 10.1007/BF01022529

Affiliations:

Links toward previous steps (curation, corpus...)

to stream Istex, to step Corpus: 000017
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to stream Main, to step Merge: 00F143
to stream Main, to step Curation: 00DF06

Le document en format XML

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<author><name sortKey="Blum, Murray S" sort="Blum, Murray S" uniqKey="Blum M" first="Murray S." last="Blum">Murray S. Blum</name>
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<author><name sortKey="Andersen, Alan N" sort="Andersen, Alan N" uniqKey="Andersen A" first="Alan N." last="Andersen">Alan N. Andersen</name>
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<author><name sortKey="Fales, Henry M" sort="Fales, Henry M" uniqKey="Fales H" first="Henry M." last="Fales">Henry M. Fales</name>
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<series><title level="j">Journal of Chemical Ecology</title>
<title level="j" type="abbrev">J Chem Ecol</title>
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<term>Anhydrous mgso4</term>
<term>Australian monomorium</term>
<term>Authentic sample</term>
<term>Base peak</term>
<term>British museum</term>
<term>Chem</term>
<term>Chemical ecology</term>
<term>Chromatographic analysis</term>
<term>Chromatographic retention times</term>
<term>Corresponding pyrrolidine</term>
<term>Dimethyl disulfide</term>
<term>Dimethyl disulfide adduct</term>
<term>Direct comparison</term>
<term>Double bond</term>
<term>First report</term>
<term>Glass column</term>
<term>Important ions</term>
<term>Insecticides nicotine</term>
<term>Isomer</term>
<term>Isomeric mixture</term>
<term>Major component</term>
<term>Marie curie</term>
<term>Mass spectra</term>
<term>Mass spectrum</term>
<term>Mesh supelcoport</term>
<term>Methylene chloride extracts</term>
<term>Monomorium</term>
<term>Monomorium species</term>
<term>Monomorium workers</term>
<term>Nitrogen atmosphere</term>
<term>Organic phase</term>
<term>Other members</term>
<term>Pyridinium chlorochromate</term>
<term>Pyrrolidine</term>
<term>Reductive amination</term>
<term>Retention time</term>
<term>Retention times</term>
<term>Solenopsis</term>
<term>Synthetic methodology</term>
<term>Termite</term>
<term>Termite workers</term>
<term>Tetrahedron lett</term>
<term>Toxicity determinations</term>
<term>Trans</term>
<term>Trans isomers</term>
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<term>Base peak</term>
<term>British museum</term>
<term>Chem</term>
<term>Chemical ecology</term>
<term>Chromatographic analysis</term>
<term>Chromatographic retention times</term>
<term>Corresponding pyrrolidine</term>
<term>Dimethyl disulfide</term>
<term>Dimethyl disulfide adduct</term>
<term>Direct comparison</term>
<term>Double bond</term>
<term>First report</term>
<term>Glass column</term>
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<term>Mass spectrum</term>
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<term>Pyridinium chlorochromate</term>
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<term>Retention times</term>
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<term>Tetrahedron lett</term>
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<term>Trans isomers</term>
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<front><div type="abstract" xml:lang="en">Abstract: Novel 2-ethyl-5-alkylpyrrolidines and their corresponding 1-pyrrolines have been identified as poison gland products from an unidentified Australian species ofMonomorium. The major alkaloids present in the venom of this ant aretrans-2-ethyl-5-undecylpyrrolidine andtrans-2-ethyl-5-(12-tridecen-1-yl)pyrrolidine. The position of the double bond in the latter was established from its dimethyl-disulfide adduct after the amine function had been protected, and the stereochemistry of the alkyl groups was determined by direct comparison with synthetic compounds. The corresponding 1-pyrrolines were also detected in varying amounts in this venom. The pyrrolidines and 1-pyrrolines possess considerable insecticidal activity when evaluated against termite workers. The alkaloidal venoms ofMonomorium appear to be an important factor contributing to the success of these small ants both as competitors and as predators.</div>
</front>
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Novel 2-ethyl-5-alkylpyrrolidines in the venom of an australian ant of the genus Monomorium

Novel 2-ethyl-5-alkylpyrrolidines in the venom of an australian ant of the genus Monomorium

Source :

English descriptors

Abstract

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