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

Bodner, Michaela; Vagalinski, Boyan; Makarov, Slobodan E.; Raspotnig, Günther

doi:10.1007/s00049-017-0242-4

Cited by 5 publications

(3 citation statements)

References 36 publications

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“…Members of the order Julida, together with spirostreptidans and spirobolidans, are traditionally classified as belonging to the category of “quinone millipedes” [ sensu Eisner, Alsop, Hicks, and Meinwald ()] because the most prominent compounds of their defensive secretion are quinones. Apart from quinones, defensive gland exudates of julidans can contain phenolics, alcohols, aldehydes, esters and anthranilate derivatives (Bodner & Raspotnig, ; Bodner, Vagalinski, Makarov, & Raspotnig, ; Bodner et al., ; Huth, ; Makarov et al., ; Sekulić et al., ; Vujisić et al., ; Wheaterston, Tyrell, & Percy, ; Wheeler, Meinwald, Hurst, & Eisner, ). The typical julidan defensive secretion is a blend of benzoquinones (as dominant compounds) and some of the mentioned compounds, but there are species within this order with an aberrant chemoprofile of defence compounds (Bodner et al., , ; Shimizu, Kuwahara, Yakamuru, & Tanabe, ).…”

Section: Introductionmentioning

confidence: 99%

Millipedes vs. pathogens: Defensive secretions of some julids (Diplopoda: Julida) as potential antimicrobial agents

Ilić

Dimkić

Unković

et al. 2018

J Applied Entomology

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In the light of growing interest in discovering new sources of natural antimicrobial agents, we extracted and tested the efficiency of julid defensive secretions in comparison with commercially used antibiotic and antimycotics. This work involved chemical characterization of the defensive secretions of Cylindroiulus boleti (C. L. Koch, 1847), Megaphyllum bosniense (Verhoeff, 1897) and M. unilineatum (C. L. Koch, 1838), as well as in vitro evaluation of their antimicrobial activity against 11 bacteria, one yeast and eight filamentous fungi. Compounds of the analysed defensive secretions included p‐benzoquinones, alkyl esters of fatty acids and ketones. Ketones were recorded for the first time in the order Julida, and they were detected in secretions of both Megaphyllum species. All three analysed defensive secretions showed antibacterial and antifungal potential against all of the tested pathogens. Staphylococcus aureus proved to be the most sensitive bacterial strain to all analysed secretions. Also, defensive secretion of M. unilineatum showed significant antibacterial potential against Bacillus subtilis. The most resistant bacterial strains in this study were Escherichia coli, Erwinia persicina and Pseudomonas syringae pv. tomato. Analysed defensive secretions achieved the strongest antifungal activity against Aspergillus parasiticus (secretions of all three millipede species), Penicillium griseofulvum (secretions of C. boleti and M. bosniense) and Cladosporium oxysporum (secretion of M. unilineatum). The most resistant mycromycetes were A. niger (to all tested defensive secretions), A. flavus (to secretion of M. unilineatum) and P. lanosum (to secretions of C. boleti and M. bosniense). Our results showed a generally lower level of activity compared to antibiotic and a significantly higher level compared to antimycotics. The results of this study elucidate and open opportunities for further research in the field of millipede chemical ecology.

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Section: Introductionmentioning

confidence: 99%

Millipedes vs. pathogens: Defensive secretions of some julids (Diplopoda: Julida) as potential antimicrobial agents

Ilić

Dimkić

Unković

et al. 2018

J Applied Entomology

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“…Meanwhile an impressive chemical repertoire has been reported from different millipede orders, including various quinones, esters, alcohols, cyanogenic compounds and unusual aromatic alkaloids (Shear, 2015;Bodner et al, 2018). Alkaloids arewith a few exceptions (Bodner et al, 2017) mainly found in the secretions of two groups of diplopods, Glomerida and Colobognatha. The chemistry of Glomerida appears to be predominated by two unique quinazoline alkaloids: glomerin and homoglomerin (Meinwald et al, 1966;Shear et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

Alkaloids from millipedes: a re-evaluation of defensive exudates from Polyzonium germanicum

Kunert,

Pferschy-Wenzig,

Orthaber

et al. 2023

Front. Ecol. Evol.

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Millipedes are known to produce various sets of chemical compounds in exocrine defensive glands to protect themselves against predators and microorganisms. Here, we reanalyzed the gland secretion of Polyzonium germanicum, a millipede of the order Polyzoniida, by using a combination of analytical techniques such as GC-MS, LC-HRMS and high field 1D and 2D NMR spectroscopy. Previously only one compound (polyzonimine, 1) had been described, but our approach allowed us to add six compounds to the defensive chemistry of this species. Besides polyzonimine (1), we found nitropolyzonamine (2) and five new compounds: 3 (2,3-dimethyl-7’-nitro-2’,3’,5’,6’,7’,7a’-hexahydrospiro[cyclopent-2-ene-1,1’-pyrrolizine]), 4 (2,3-dimethyl-7’-nitro-2’,3’,5’,6’,7’,7a’-hexahydrospiro[cyclopentane-1,1’-pyrrolizin]-2-ene), 5 ((1Z)-8,9-dimethyl-1-(nitromethylidene)-2-azaspiro[4.4]non-8-en-7-one), and not fully identified compounds A, B. For compounds 3–5 we were able to determine the molecular constitution, for two of them (4, 5) we were able to give relative configurations. Overall, the combination of advanced analytical techniques applied herein allowed detailed insights into the defensive chemistry of P. germanicum with a low number of individuals needed for analysis and without prior compound isolation.

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“…One of the hallmarks of the millipede order Julida (as well as their closest relatives Spirobolida and Spirostreptida) is the synthesis of quinone-based defensive secretions [14–17]. Exudates of julidan defensive glands are cocktails made of different compounds–benzoquinones, phenolics, alcohols, aldehydes, esters, anthranilate derivatives, and ketones ([16] and references therein).…”

Section: Introductionmentioning

confidence: 99%

Multifaceted activity of millipede secretions: Antioxidant, antineurodegenerative, and anti-Fusarium effects of the defensive secretions of Pachyiulus hungaricus (Karsch, 1881) and Megaphyllum unilineatum (C. L. Koch, 1838) (Diplopoda: Julida)

et al. 2019

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Members of the millipede order Julida rely on dominantly quinonic defensive secretions with several minor, non-quinonic components. The free radical-scavenging activities of ethanol, methanol, hexane, and dichloromethane extracts of defensive secretions emitted by Pachyiulus hungaricus (Karsch, 1881) and Megaphyllum unilineatum (C. L. Koch, 1838) were investigated using the ABTS, DPPH, and total reducing power (TRP) tests. The obtained extracts were also tested for inhibition of acetylcholinesterase and tyrosinase activity. Finally, the antifungal potential of both julid extracts was evaluated against seven Fusarium species. Secretions of both species showed activity against free radicals, acetylcholinesterase, tyrosinase, and all of the selected fungal species. The secretions of P. hungaricus exhibited a more potent antioxidative effect than did those of M. unilineatum, while there were no significant differences of antiacetylcholinesterase activity between the tested extracts. Only the hexane extract of M. unilineatum showed an effect on tyrosinase activity stronger than that of P. hungaricus. Fusarium sporotrichioides, F. graminearum, and F. verticillioides were the fungi most resistant to secretions of both julids. The Fusarium species most susceptible to the secretion of P. hungaricus was F. avenaceum, while the concentrations of M. unilienatum extracts needed to inhibit and completely suppress fungal growth were lowest in the case of their action on F. lateritium. Our data support previous findings that julid defensive secretions possess an antimicrobial potential and reveal their antioxidative and antineurodegenrative properties. Bearing in mind the chemical complexity of the tested defensive secretions, we presume that they can also exhibit other biological activities.

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

Cited by 5 publications

References 36 publications

Millipedes vs. pathogens: Defensive secretions of some julids (Diplopoda: Julida) as potential antimicrobial agents

Millipedes vs. pathogens: Defensive secretions of some julids (Diplopoda: Julida) as potential antimicrobial agents

Alkaloids from millipedes: a re-evaluation of defensive exudates from Polyzonium germanicum

Multifaceted activity of millipede secretions: Antioxidant, antineurodegenerative, and anti-Fusarium effects of the defensive secretions of Pachyiulus hungaricus (Karsch, 1881) and Megaphyllum unilineatum (C. L. Koch, 1838) (Diplopoda: Julida)

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