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

Author:
Bodner, Michaela, Vagalinski, Boyan, Makarov, Slobodan E., Raspotnig, Günther
Source:
Chemoecology 2017 v.27 no.4 pp. 171-175
ISSN:
0937-7409
Subject:
Glomerida, Julida, benzoquinones, biosynthesis, branching, chemical defenses, chemistry, defensive secretions, secretion
Abstract:
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.
Agid:
5762648