Intrageneric differences in the four stereoisomers of stenusine in the rove beetle genus, Stenus (Coleoptera, Staphylinidae)

Lusebrink, Inka; Burkhardt, Dirk; Gedig, Thomas; Dettner, Konrad; Mosandl, Armin; Seifert, Karlheinz

doi:10.1007/s00114-006-0172-4

Cited by 11 publications

(7 citation statements)

References 12 publications

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“…In line with our result, potential functions of the pygidial gland components of this necrophagous beetle can be attributed to pressures associated with food's characteristics, such as its degree of decomposition, contamination by fungi and bacterias (Favila and Díaz 1996;Favila 1993). Recent investigations on rove beetles have demonstrated that pygidial gland components are capable of deterring predators and protecting the beetles from infestation with microorganisms (Betz 1999;Lusebrink et al 2007;Schierling et al 2013). In this regard, the composition of pygidial secretion from Canthon c. cyanellus might have antimicrobial properties.…”

Section: Discussionsupporting

confidence: 65%

Chemical diversity and potential biological functions of the pygidial gland secretions in two species of Neotropical dung roller beetles

et al. 2015

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Dung roller beetles of the genus Canthon (Coleoptera: Scarabaeinae) emit an odorous secretion from a pair of pygidial glands. To investigate the chemical composition of these secretions, we used stir bar sorptive extraction (SBSE), coupled with gas chromatography-mass spectrometry (GC-MS) for analysis of extracts of pygidial gland secretions secreted by the dung roller beetles Canthon femoralis femoralis and Canthon cyanellus cyanellus. Chemical analyses of volatiles collected from pygidial gland secretions comprise a great diversity of the functional groups. Chemical profile comparisons showed high intra-and interspecific variability. The pygidial gland secretion of Canthon f. femoralis was dominated by sesquiterpene hydrocarbons, whereas the profile of Canthon c. cyanellus was dominated by carboxylic acids. The different pygidial secretions have a high diversity of chemical compounds suggesting a multifunctional nature involving some key functions in the biology. We discuss the biological potential of these compounds found in the pygidial glands of each species with respect to their ecological and behavioral relevance.

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Section: Discussionsupporting

confidence: 65%

Chemical diversity and potential biological functions of the pygidial gland secretions in two species of Neotropical dung roller beetles

et al. 2015

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“…The ratio of these four stereoisomers shows intrageneric differences (Lusebrink et al 2007). The antimicrobial effect of stenusine may change with changing stereoisomer ratio, or just one enantiomer may be sufficient to inhibit the growth of microorganisms.…”

Section: Discussionmentioning

confidence: 99%

“…The ecological significance of alkaloids in animals is probably the use as a defence against predators and microorganisms (Schlee 1985). Earlier studies have hypothesised that the pygidial gland secretion of Stenus beetles may act against microorganisms (Dettner 1993;Betz 1999;Lusebrink et al 2007).…”

Section: Introductionmentioning

confidence: 99%

Stenusine, an antimicrobial agent in the rove beetle genus Stenus (Coleoptera, Staphylinidae)

Lusebrink

Dettner

Seifert

2008

Naturwissenschaften

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Stenusine is well known as the alkaloid, discharged by the rove beetle, genus Stenus Latreille (Coleoptera, Staphylinidae). The Stenus beetles employ the alkaloid as an escape mechanism when on water surfaces. In the case of danger, they lower their abdomen and emit stenusine from their pygidial glands. Stenusine shows a low surface tension and therefore a high spreading pressure; these properties propel the beetle quickly over the water. Many Steninae do not live in habitats with open waters, but in detritus, leaf litter, mosses, etc. This raises the possibility that stenusine might also have another function, e.g., as antibiotic or fungicide. Stenus beetles show an intense grooming behaviour. With gas chromatography-mass spectrometry analyses we could prove that they cover themselves with their secretion. To tests its antimicrobial properties we conducted agar diffusion tests with stenusine and norstenusine, another substance that is abundant in most Stenus species. Both compounds have an antimicrobial effect on entomopathogenic bacteria and fungi. Stenusine not only allows for an extraordinary method of locomotion on water surfaces, it also protects the Steninae from being infested with microorganisms.

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“…In an earlier study we showed that the ratio of the four stereoisomers of the alkaloid stenusine (4) differs with species (Lusebrink et al, 2007). The stereoisomeric ratio [(2'R,3R)-, (2'S,3R)-, (2'S,3S)-and (2'R,3S)-stenusine] of the German (GER) and Canadian (CDN) S. comma (subgenus Stenus) differs enormously: GER 17%:37%:43%:3% vs. CDN 0%:0%:55%:45%.…”

Section: Detection Structure Elucidation and Synthesis Of The Pyridmentioning

confidence: 99%

New Pyridine Alkaloids from Rove Beetles of the Genus Stenus (Coleoptera: Staphylinidae)

Lusebrink

Dettner

Schierling

et al. 2009

Zeitschrift Für Naturforschung C

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Intrageneric differences in the four stereoisomers of stenusine in the rove beetle genus, Stenus (Coleoptera, Staphylinidae)

Cited by 11 publications

References 12 publications

Chemical diversity and potential biological functions of the pygidial gland secretions in two species of Neotropical dung roller beetles

Chemical diversity and potential biological functions of the pygidial gland secretions in two species of Neotropical dung roller beetles

Stenusine, an antimicrobial agent in the rove beetle genus Stenus (Coleoptera, Staphylinidae)

New Pyridine Alkaloids from Rove Beetles of the Genus Stenus (Coleoptera: Staphylinidae)

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