Benzo- and hydroquinones in the defence secretions of Blaps sulcata and Blaps wiedemanni

doi:10.1016/0022-1910(70)90089-2

Journal of Insect Physiology

Volume 16, Issue 11, November 1970, Pages 2201-2206

https://doi.org/10.1016/0022-1910(70)90089-2 Get rights and content

Abstract

Examination of the defence secretions of males and females of Blaps sulcata and Blaps wiedemanni by TLC, i.r. and u.v. spectrophotometry, NMR, and mass spectrometry revealed the presence of the following quinones: 1,4-benzoquinone, 2-methylbenzoquinone and 2-ethylbenzoquinone. These quinones are accompanied by smaller amounts of the corresponding hydroquinones as well as glucose. The function of these compounds in the defence secretion of Blaps is discussed.

References (16)

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Cited by (10)

Conversion of tyrosine to phenolic derivatives by Taiwan cobra venom
1998, Toxicon
We have examined the ability of Taiwan cobra (Naja naja atra) venom to transform in vitro the amino acid tyrosine to phenolic oxidation products via 4-hydroxyphenylpyruvate. This amino acid can be released from neuropeptide substrates by oligopeptidases present in the venom. Using a variety of analytical techniques to probe a complicated series of reactions, we confirm that the l-amino acid oxidase present in the venom initially releases the keto form of 4-hydroxyphenylpyruvic acid and hydrogen peroxide after reacting with the tyrosine. Thereafter, there is evidence that a tautomerase in the venom promotes a partial conversion of the keto-form 4-hydroxyphenylpyruvic acid into an enol form. The enol is oxidised primarily to 4-hydroxybenzaldehyde and 4-hydroxyphenol (hydroquinone). The keto form is oxidised through to 4-hydroxyphenylacetic acid by the hydrogen peroxide co-released by the l-amino acid oxidase. The venom promotes both these spontaneous oxidation routes and also generates traces of other phenolics, some of which are as yet unidentified. We propose that reactions between the precursors of the major oxidation products may be responsible for generating unusual short-lived phenolics, possibly giving rise to special bioactivities that are relevant to venom action.
The toxic effects of phenoloxidase from the haemolymph of tenebrionid beetles
1973, Journal of Insect Physiology
The injection of haemolymph originating from several species of tenebrionid beetles into blowfly larvae caused a gradual paralysis accompanied by colour changes in the haemolymph of the injected test insects. It was found that the lethal effect of the haemolymph of the beetle Blaps sulcata was due to phenoloxidase. The enzyme was activated by the exposure and incubation of the haemolymph at room temperature.
The identity between the toxic factor and phenoloxidase in the beetle's haemolymph was demonstrated by the following data: (1) A correlation between the rate of lethal and phenoloxidase activities during the activation process of the toxic haemolymph. (2) Phenylthiourea, a well-known inhibitor of phenoloxidase, inhibited both the enzymatic and the toxic action of the beetle's haemolymph. (3) A commercial preparation of phenoloxidase (originating from mushrooms) imitated the lethal effects and the accompanying symptoms of the toxic haemolymph. (4) Sephadex G-100 column separation of the Blaps haemolymph revealed a complete overlap between the enzymatic and lethal regions of the elution pattern.
The possible effects of phenoloxidase on the haemolymph of the injected insects are discussed.
The chemistry of the defensive secretion of the beetle, Drusilla canaliculata
1973, Journal of Insect Physiology
The tergal gland of the beetle, Drusilla canaliculata, contains defensive products which exhibit an extraordinary chemical diversity. This glandular exudate is fortified with alkanes, alkenes, saturated and unsaturated aliphatic aldehydes, 1,4-quinones, and hydroquinones. The aldehydes, n-dodecanal, n-tetradecanal, n-tetradec-5-enal, and n-tetradeca-5,8-dienal, constitute a major group of components. In addition, a new constituent in arthropod defensive secretions, 2-hydroxy-3-methylhydroquinone, has been identified as a minor component in this exocrine exudate.
Antiparasitic effects of potentially toxic beetles (Tenebrionidae and meloidae) from steppe zones
2021, Toxins
Verification of Argentine ant defensive compounds and their behavioral effects on heterospecific competitors and conspecific nestmates
2018, Scientific Reports
Harvestman phenols and benzoquinones: Characterisation and biosynthetic pathway
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Journal of Insect Physiology

Abstract

References (16)

Quinone and hydrocarbon production in the defensive glands of Eleodes longicollis and Tribolium castaneum (Coleoptera, Tenebrionidae)

J. Insect Physiol.

Separation of carbohydrates on borate-impregnated silica gel G plates

J. Chromatogr.

The occurrence of para-quinones in some arthropods, with emphasis on the quinone-secreting tracheal glands of Diploptera punctata (Blattaria)

J. Insect Physiol.

The excretion of ethylquinone by the flour beetle

Biochem. J.

Studies in mass spectrometry—V. Mass spectra of benzoquinones

J. chem. Soc. (B)

Observations on the mechanism of a tanning reaction in Periplaneta and Blatta

Paper chromatography of phenolic substances

Nature, Lond.

Defense mechanisms of arthropods—XV. Morphology of the quinone-producing glands of a tenebrionid beetle (Eleodes longicollis Lec.)

J. Morph.

Cited by (10)

Conversion of tyrosine to phenolic derivatives by Taiwan cobra venom

The toxic effects of phenoloxidase from the haemolymph of tenebrionid beetles

The chemistry of the defensive secretion of the beetle, Drusilla canaliculata

Antiparasitic effects of potentially toxic beetles (Tenebrionidae and meloidae) from steppe zones

Verification of Argentine ant defensive compounds and their behavioral effects on heterospecific competitors and conspecific nestmates

Harvestman phenols and benzoquinones: Characterisation and biosynthetic pathway