Biosynthetic origin of benzoquinones in the explosive discharge of the bombardier beetle Brachinus elongatulus

Attygalle, Athula B.; Xu, Sihang; Moore, Wendy; McManus, Reilly; Gill, Amanjit

doi:10.1007/s00114-020-01683-0

Cited by 12 publications

(7 citation statements)

References 45 publications

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“…Time–intensity profiles for m / z 129 and 133 ions, extracted from the acquired GC-MS data, confirmed the presence of an additional chromatographic peak for a compound that eluted slightly before the quinoline peak (Figure F). In fact, it is well known that deuteriated isotopologues elute earlier than their nonlabeled counterparts under GC conditions. − Evidently, the earlier eluting peak we observed represented a deuterio-isotopologue of quinoline. By following a careful background subtraction protocol, we were able to obtain a representative mass spectrum for the deuteriated compound (Figure ).…”

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confidence: 48%

Biosynthesis of Quinoline by a Stick Insect

et al. 2021

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The Peruvian stick insect Oreophoetes peruana is the only known animal source for unsubstituted quinoline in nature. When disturbed, these insects discharge a defensive secretion containing quinoline. Analysis of samples obtained from L-[2′,4′,5′,6,′7′-2 H 5 ]tryptophan-fed stick insects demonstrated that the insects convert it to [5,6,7, H 4 ]quinoline by removing the 2′-CH moiety in the indole ring of tryptophan. Analogous experiments using L-[1′-15 N]tryptophan and L-[1′-15 N, 15 NH 2 ]tryptophan showed that the indole-N atom is retained while the α-amino group is eliminated during the biosynthesis. Mass spectra recorded from quinoline derived from [2-13 C 1 ]tryptophan-fed insects indicated that the αcarbon atom of tryptophan is incorporated as the C-2 atom of the quinoline ring.

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confidence: 48%

Biosynthesis of Quinoline by a Stick Insect

et al. 2021

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“…In this study, we used 16S metagenomic amplicon sequencing to quantify the bacterial diversity hosted by three carabid species under several dietary treatments. Each host species produces distinct primary defensive compounds: Anisodactylus similis produces formic acid, Pterostichus serripes carboxylic acids, and Brachinus elongatulus quinones [29] [Will & Attygalle, unpublished data]. Anisodactylus similus has a distinct natural feeding preference from the other two species, so together these three species represent two different trophic types.…”

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confidence: 99%

Persistence of the ground beetle (Coleoptera: Carabidae) microbiome to diet manipulation

et al. 2021

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Host-associated microbiomes can play important roles in the ecology and evolution of their insect hosts, but bacterial diversity in many insect groups remains poorly understood. Here we examine the relationship between host environment, host traits, and microbial diversity in three species in the ground beetle family (Coleoptera: Carabidae), a group of roughly 40,000 species that synthesize a wide diversity of defensive compounds. This study used 16S amplicon sequencing to profile three species that are phylogenetically distantly related, trophically distinct, and whose defensive chemical secretions differ: Anisodactylus similis LeConte, 1851, Pterostichus serripes (LeConte, 1875), and Brachinus elongatulus Chaudoir, 1876. Wild-caught beetles were compared to individuals maintained in the lab for two weeks on carnivorous, herbivorous, or starvation diets (n = 3 beetles for each species-diet combination). Metagenomic samples from two highly active tissue types—guts, and pygidial gland secretory cells (which produce defensive compounds)—were processed and sequenced separately from those of the remaining body. Bacterial composition and diversity of these ground beetles were largely resilient to controlled changes to host diet. Different tissues within the same beetle harbor unique microbial communities, and secretory cells in particular were remarkably similar across species. We also found that these three carabid species have patterns of microbial diversity similar to those previously found in carabid beetles. These results provide a baseline for future studies of the role of microbes in the diversification of carabids.

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“…At the same time, αα 500 elicits the highest indecision; it is characterized by a simple chromatographic profile, with few significant peaks and its unicity is confirmed by the distance shown on PCA. The presence of hydroquinone and maltol could be strictly linked with the higher repellency elicited by CELL 300, CELL 500 and MIX2 [75,76].…”

Section: Discussionmentioning

confidence: 91%

Biochar-Derived Smoke Waters Affect Bactrocera oleae Behavior and Control the Olive Fruit Fly under Field Conditions

et al. 2022

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Bactrocera oleae is the key pest of olive production. Several attempts have been carried out over time to control it using biological solutions but with results rarely comparable to those obtained with chemical applications. The purpose of this work was to identify and test new compounds from samples of various Smoke Waters (SWs) for their effect on the fly, and given their low impact on the environment. SWs obtained from different feedstocks were used in in vitro and open field applications. SWs were shown to alter B. oleae fitness, acting on its microbiome, particularly on the presence and activity of the primary endosymbiont “Ca. Erwinia dacicola”, and also to affect the behavior of the adult flies, altering the attractiveness of the drupes susceptible to attack. The effects recorded were concentration-dependent and varied among repulsion, up to 87% towards females, indecision, up to 70% towards males, and attraction, comparable to fresh green olives, based on the starting materials. These responses were confirmed in electroantennography trials and during two-years of field trials carried out in South and Central Italy. Gas Chromatography–Mass Spectrometry highlighted the presence of compounds such as guaiacol and hydroquinone as potentially important for the observed activity. Principal Component Analyses confirmed the proximity among SWs obtained from similar feedstocks. In controlled conditions, females appear to be more sensitive to the SW treatments. Field trials have shown how the effects of SWs can lead depression of infestation levels obtainable with other well-known compounds, such as kaolin clay and isopropyl-myristate (repulsive), or pheromones (attractive).

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Biosynthetic origin of benzoquinones in the explosive discharge of the bombardier beetle Brachinus elongatulus

Cited by 12 publications

References 45 publications

Biosynthesis of Quinoline by a Stick Insect

Biosynthesis of Quinoline by a Stick Insect

Persistence of the ground beetle (Coleoptera: Carabidae) microbiome to diet manipulation

Biochar-Derived Smoke Waters Affect Bactrocera oleae Behavior and Control the Olive Fruit Fly under Field Conditions

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