Defensive secretion ofTenebrio molitor (Coleoptera: Tenebrionidae)

Attygalle, Athula B.; Blankespoor, Curtis L.; Meinwald, Jerrold; Eisner, Thomas

doi:10.1007/bf00994202

Cited by 32 publications

(20 citation statements)

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“…3-Methylphenol (Tschinkel 1969;Attygalle et al 1991;Villaverde et al 2007;Geiselhardt et al 2009;), 3-ethylphenol (Tschinkel 1969;Geiselhardt et al 2009), 2-methylhydroquinone (Happ 1968;Wahrendorf and Wink 2006;Villaverde et al 2007;Geiselhardt et al 2009), and 2-ethylhydroquinone (Happ 1968;Hodges et al 1996;Wahrendorf and Wink 2006;Geiselhardt et al 2009) have all been detected in the defensive secretions of other tenebrionid beetles, although quinones are more ubiquitous 3-Methylphenol, 2-methylhydroquinone, and methyl-pbenzoquinone are thought to be sequential members of a biosynthetic pathway that originates with 6-methylsalicylic acid (Gnanasunderam et al 1984), itself formed from acetate (or malonate) units (Birch et al 1955). Similarly, 3-ethylphenol, 2-ethylhydroquinone, and ethyl-p-benzoquinone are likely derived from 6-ethylsalicylic acid (Gnanasunderam et al 1984), which differs in its synthesis by the use of a propionate unit in place of an acetate (or malonate) unit, as evidenced by isotope tracing experiments on ethyl-pbenzoquinone (Meinwald et al 1966).…”

Section: Discussionmentioning

confidence: 99%

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

et al. 2009

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Forked fungus beetles, Bolitotherus cornutus, feed, mate, and live on the brackets of several species of shelf fungus that grow on decaying logs. In response to the specific threat stimulus of mammalian breath, B. cornutus beetles produce a volatile defensive secretion. We tested beetles collected from different host fungi to determine whether defensive secretion blends varied with host type. Using solid phase microextraction and gas chromatographymass spectrometry, we detected large amounts of the alkylated benzoquinones, methyl-p-benzoquinone (toluquinone) and ethyl-p-benzoquinone, and smaller quantities of p-benzoquinone, 3-methylphenol (m-cresol), 3-ethylphenol, 2-methylhydroquinone, and 2-ethylhydroquinone in secretions. Volatile composition did not differ between male and female beetles. Secretions did differ between beetles collected from two species of fungus, Ganoderma applanatum and Fomes fomentarius, with the relative amount of pbenzoquinone secreted being the most important factor. Other relationships among the volatile components are discussed.

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Section: Discussionmentioning

confidence: 99%

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

et al. 2009

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“…Mass spectrometry, particularly in conjunction with gas chromatography, is one of the most powerful techniques for investigating trace amounts of mixtures. However, it is known that mass spectrometry is not as efficient as infrared spectroscopy in differentiating isomers (Attygalle et al 1991). On the other hand, the combination of GC-MS and GC-IR analyses provides an opportunity to identify closely related volatile compounds in minute amounts of mixtures efficiently.…”

Section: Introductionmentioning

confidence: 99%

Hydroquinones from defensive secretion of a giant Pacific millipede, Acladocricus setigerus (Diplopoda: Spirobolida)

Buden

Attygalle

2007

Chemoecology

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The presence of considerable quantities of hydroquinones including hydroquinone, 2-methylhydroquinone, 2,3-dimethoxyhydroquinone, 2-methoxy-3-methylhydroquinone, and 2,3-dimethoxy-5-methylhydroquinone renders the defensive secretion of Acladocricus setigerus (Silvestri, 1897) significantly different from that of other quinone-producing millipedes. In addition, two hitherto undescribed compounds, namely, 2,3-dimethoxy-5-methylhydroquinone and 2-methyl-3,4-methylenedioxyphenol, were characterized from the defensive secretion. However, it is uncertain if the latter compound is formed after the release of the secretion. The two major compounds, 2-methyl-1,4-benzoquinone and 2-methoxy-3-methyl-1,4-benzoquinone, constitute about 75% of the defensive fluid. Furthermore, hydrocarbons, which are typically present in the secretions of most other arthropods that use benzoquinones as repellents, are notably absent in the secretion of A. setigerus.

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“…All these substances have already been reported from other darkling beetles. Phenols are produced in the pygidial defensive gland of tenebrionids of different subfamilies (Attygalle et al 1991;Brown et al 1992), as well as in the prothoracic defensive gland of Zophobas rugipes (Tschinkel 1969). 2-Tridecanone is secreted by Blaps mucronata (Peschke and Eisner 1987) and 2-pentadecanone by Uloma tenebrionoides, together with 2-heptadecanone and unsaturated 2-ketones (Gnanasunderam et al 1985).…”

Section: Chemical Compositions Of the Defensive Secretionsmentioning

confidence: 99%

“…Besides these two major classes several compounds belonging to other chemical classes are found in minor amounts. These are monoterpene hydrocarbons (Brown et al 1992;Geiselhardt et al 2006a;Gnanasunderam et al 1981), ketones (Gnanasunderam et al 1985;Peschke and Eisner 1987;Tschinkel 1975b), and phenols (Attygalle et al 1991;Brown et al 1992;Lloyd et al 1978;Tschinkel 1969).…”

Section: Introductionmentioning

confidence: 99%

Chemical composition and pheromonal function of the defensive secretions in the subtribe Stizopina (Coleptera, Tenebrionidae, Opatrini)

2009

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The chemical composition of the defensive secretions of 52 species from 15 genera of the tenebrionid subtribe Stizopina was analyzed. The secretions of all species contained 1,4-benzoquinones, 1-alkenes, and monoterpene hydrocarbons, only one species was lacking the latter. Methyl-and ethyl-1,4-benzoquinone were ubiquitous, mostly accompanied by smaller amounts of 1,4-benzoquinone as well as isopropyl-and propyl-1,4-benzoquinone. 1-Alkenes were dominated by 1-undecene with varying admixtures of other 1-alkenes. The monoterpene hydrocarbons always consisted of a mixture of a-pinene, camphene, b-pinene and limonene, but also p-cymene, a-terpinene or a-phellandrene were found in some species. Furthermore, some species synthesized additional compounds such as phenols, ketones, 2,5-dihydroxy-6-methylbenzoate, 2-hydroxy-4-methoxyacetophenone and naphthoquinones. Bioassays showed that the defensive secretion co-functioned as an aggregation pheromone in the subtribe Stizopina. All nine tested species from six genera were attracted to defensive secretion of Stizopina species, but they did not distinguish between defensive secretions of different Stizopina species. This lack of discrimination might be the initial step for the formation of interspecific aggregations and the evolution of cleptoparasitism within the Stizopina.

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Defensive secretion ofTenebrio molitor (Coleoptera: Tenebrionidae)

Cited by 32 publications

References 3 publications

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

Hydroquinones from defensive secretion of a giant Pacific millipede, Acladocricus setigerus (Diplopoda: Spirobolida)

Chemical composition and pheromonal function of the defensive secretions in the subtribe Stizopina (Coleptera, Tenebrionidae, Opatrini)

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