Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)

The defensive secretion of the julid diplopod Typhloiulus orpheus contains methyl N-methylanthranilate (MNMA), an ester of N-methylanthranilic acid that comprises more than 99% of secretion of this species. MNMA is accompanied by small amounts of methyl anthranilate and two benzoquinones (2-methyl-1...

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Autores principales: Bodner, Michaela, Vagalinski, Boyan, Makarov, Slobodan E., Raspotnig, Günther
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2017
Materias:
Short Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5533857/
https://www.ncbi.nlm.nih.gov/pubmed/28804216
http://dx.doi.org/10.1007/s00049-017-0242-4
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author Bodner, Michaela
Vagalinski, Boyan
Makarov, Slobodan E.
Raspotnig, Günther
author_facet Bodner, Michaela
Vagalinski, Boyan
Makarov, Slobodan E.
Raspotnig, Günther
author_sort Bodner, Michaela
collection PubMed
description The defensive secretion of the julid diplopod Typhloiulus orpheus contains methyl N-methylanthranilate (MNMA), an ester of N-methylanthranilic acid that comprises more than 99% of secretion of this species. MNMA is accompanied by small amounts of methyl anthranilate and two benzoquinones (2-methyl-1,4-benzoquinone and 2-ethyl-1,4-benzoquinone, respectively). MNMA is a known intermediate in the biosynthesis of both benzoquinones (as present in defensive secretions of juliformians) and glomerin-like quinazolines (chemical defense in Glomerida). The compound may have evolved independently in the pathway to glomeridan chemistry, or may even represent a pivotal branching point in the pathway to different chemical classes of diplopod defensive chemistry.
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spelling pubmed-55338572017-08-11 Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida) Bodner, Michaela Vagalinski, Boyan Makarov, Slobodan E. Raspotnig, Günther Chemoecology Short Communication The defensive secretion of the julid diplopod Typhloiulus orpheus contains methyl N-methylanthranilate (MNMA), an ester of N-methylanthranilic acid that comprises more than 99% of secretion of this species. MNMA is accompanied by small amounts of methyl anthranilate and two benzoquinones (2-methyl-1,4-benzoquinone and 2-ethyl-1,4-benzoquinone, respectively). MNMA is a known intermediate in the biosynthesis of both benzoquinones (as present in defensive secretions of juliformians) and glomerin-like quinazolines (chemical defense in Glomerida). The compound may have evolved independently in the pathway to glomeridan chemistry, or may even represent a pivotal branching point in the pathway to different chemical classes of diplopod defensive chemistry. Springer International Publishing 2017-07-24 2017 /pmc/articles/PMC5533857/ /pubmed/28804216 http://dx.doi.org/10.1007/s00049-017-0242-4 Text en © The Author(s) 2017 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Short Communication
Bodner, Michaela
Vagalinski, Boyan
Makarov, Slobodan E.
Raspotnig, Günther
Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
title Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
title_full Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
title_fullStr Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
title_full_unstemmed Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
title_short Methyl N-methylanthranilate: major compound in the defensive secretion of Typhloiulus orpheus (Diplopoda, Julida)
title_sort methyl n-methylanthranilate: major compound in the defensive secretion of typhloiulus orpheus (diplopoda, julida)
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5533857/
https://www.ncbi.nlm.nih.gov/pubmed/28804216
http://dx.doi.org/10.1007/s00049-017-0242-4
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