(-)-Adaline from the Genus of Ladybirds Is a Potent Antagonist of Insect and Specific Mammalian Nicotinic Acetylcholine Receptors.

Ladybird beetles (Coleoptera: Coccinellidae) possess strong chemical defences that are secreted in response to stress and are also found on the coating of eggs, which are rich in alkaloids that are responsible for their toxicity to other species. Recent studies have shown that alkaloids from several species of ladybird beetle can target nicotinic acetylcholine receptors (nAChRs) acting as receptor antagonists. Here, we have explored the actions of (-)-adaline, found in the 2-spot () and 10-spot () ladybirds, on both mammalian (α1β1γδ, α7, α4β2, α3β4) and insect nAChRs using patch-clamp of TE671 cells and locust brain neurons natively expressing nAChRs, as well as two-electrode voltage clamp of oocytes recombinantly expressing nAChRs.

Mutations in DIIS5 and the DIIS4-S5 linker of Drosophila melanogaster sodium channel define binding domains for pyrethroids and DDT.

Mutations in the DIIS4-S5 linker and DIIS5 have identified hotspots of pyrethroid and DDT interaction with the Drosophila para sodium channel. Wild-type and mutant channels were expressed in Xenopus oocytes and subjected to voltage-clamp analysis. Substitutions L914I, M918T, L925I, T929I and C933A decreased deltamethrin potency, M918T, L925I and T929I decreased permethrin potency and T929I, L925I and I936V decreased fenfluthrin potency.

Use of pyrethroid analogues to identify key structural features for enhanced esterase resistance in Helicoverpa armigera (Hübner) (Lepidoptera: Noctuidae).

It has been reported previously that the major resistance mechanism to pyrethroid insecticides by the cotton bollworm Helicoverpa armigera (Hübner) in Australia is a consequence of overproduction of esterase isoenzymes. This paper reports structure-activity relationships that support such a view, based on in vivo bioassays conducted with a range of pyrethroid structures containing a variety of acid and alcohol moieties and the correlation with in vitro esterase inhibition assays against the same structures, and identifies the critical regions of the molecule with regard to esterase inhibition, and hence resistance. The implications of this work in terms of possible resistance management are evaluated and discussed.

Modelling insecticide-binding sites in the voltage-gated sodium channel.

A homology model of the housefly voltage-gated sodium channel was developed to predict the location of binding sites for the insecticides fenvalerate, a synthetic pyrethroid, and DDT an early generation organochlorine. The model successfully addresses the state-dependent affinity of pyrethroid insecticides, their mechanism of action and the role of mutations in the channel that are known to confer insecticide resistance. The sodium channel was modelled in an open conformation with the insecticide-binding site located in a hydrophobic cavity delimited by the domain II S4-S5 linker and the IIS5 and IIIS6 helices.

Sensitivity of the Drosophila para sodium channel to DDT is not lowered by the super-kdr mutation M918T on the IIS4-S5 linker that profoundly reduces sensitivity to permethrin and deltamethrin.

DDT inhibits Na channel inactivation and deactivation, promotes Na channel activation and reduces the resting potential of Xenopus oocytes expressing the Drosophila para Na channel. These changes are only marginally influenced by the single mutation M918T (super-kdr) but are reduced approximately 10-fold by either the single mutation L1014F (kdr) or the double mutation L1014F+M918T, both of which confer resistance to the pyrethroids permethrin and deltamethrin. We conclude that DDT binds either to or in the region of L1014 on IIS6 but only weakly to M918 on the IIS4-S5 linker, which is part of a high-affinity binding site for permethrin and deltamethrin.

Effects of plant-derived compounds on larvae of a blow fly species that causes secondary myiases: laboratory studies.

No-choice and binary-choice bioassays were used to test the effect of a range of plant-derived insecticides on the behaviour of larvae of the black blow fly Phormia regina (Meigen). Azadirachtin (100 and 10 ppm), pyrethrum extract (10 ppm) and the naphthoquinone BTG 505 (1000 ppm) acted as deterrents for P. regina larvae.

A new insecticidal protolimonoid from Aegle marmelos.

Bioassay-directed fractionation of the ethyl acetate extracts of the stem bark of Aegle marmelos Correa (Rutaceae) afforded a new compound, named skimmiarepin C, along with skimmiarepin A. The latter is a known compound but isolation from A. marmelos is new.

Mode of action and pesticidal activity of the natural product dunnione and of some analogues.

This paper reports the investigation of the insecticidal and fungicidal activity of dunnione, a natural product obtained inadvertently as a by-product of a synthesis programme. Dunnione exhibits no insecticidal activity but has an unusually broad spectrum of antifungal activity. In vitro and in vivo (preventative) activities were comparable to those of several long-established fungicides (eg carbendazim).

Insecticidal 2-hydroxy-3-alkyl-1,4-naphthoquinones: correlation of inhibition of ubiquinol cytochrome c oxidoreductase (complex III) with insecticidal activity.

The insecticidal and in vitro activities of four homologous series of 2-hydroxy and acetoxy-3-substituted-1,4-naphthoquinones have been measured and correlated with their (Log) octanol/water partition coefficients (Log Ko/w). In vitro activity against mitochondrial complex III was only exhibited by 2-hydroxy-3-alkyl-1,4-naphthoquinones, indicating that the 2-acetoxy compounds act as proinsecticides. Good correlation was observed between in vivo activity against the two-spotted spider mite, Tetranychus urticae and inhibition of complex III isolated from blowfly flight muscle.

Herbicidal action of 2-hydroxy-3-alkyl-1,4-naphthoquinones.

The main mode of herbicidal activity of 2-hydroxy-3-alkyl-1,4-naphthoquinones is shown to be inhibition of photosystem II (PSII). The herbicidal and in vitro activities have been measured and correlated with their (Log)octanol/water partition coefficients (Log Ko/w). The length of the 3-n-alkyl substituent for optimal activity differed between herbicidal and in vitro activity.

An insecticidal mixture of tetramethylcyclohexenedione isomers from Kunzea ambigua and Kunzea baxterii.

A mixture of isomers, all 4-[1-(5,7-dihydroxy-6-methyl-4-oxo-2-phenyl-chroman-8-yl)-3-methyl-butyl]-5-hydroxy-2,2,6,6-tetramethyl-cyclohex-4-en-1,3-diones, which comprises a pair of epimers, each of which is a pair of conformers, has been isolated from the hexane extract of the aerial parts of Kunzea ambigua and K. baxterii (Myrtaceae). The mixture exhibits moderate insecticidal activity in comparison with natural pyrethrum extract.

Negative cross-resistance between dihydropyrazole insecticides and pyrethroids in houseflies, Musca domestica.

A series of insecticidal dihydropyrazoles and related compounds have been shown to exhibit negative cross-resistance to a resistant (super-kdr) strain of houseflies with site-insensitivity to pyrethroids. The level of cross-resistance is similar to that observed previously for a range of N-alkylamides against the same strain.

METI-acaricide resistance in Tetranychus urticae does not confer resistance to the naphthoquinones.

The naphthoquinones and the METI group of compounds act on sites associated with mitochondrial respiration, but METI-resistant strains of two-spotted spider mite from Japan and the UK exhibited no cross-resistance to the naphthoquinones. The potential for developing commercial naphthoquinones therefore remains high.

Insect growth inhibition, antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes.

Fresh rhizomes of Zingiber officinale (ginger), when subjected to steam distillation, yielded ginger oil in which curcumene was found to be the major constituent. The thermally labile zingiberene-rich fraction was obtained from its diethyl ether extract. Column chromatography of ginger oleoresin furnished a fraction from which [6]-gingerol was obtained by preparative TLC.

Isolation, characterization, and biological activity of naphthoquinones from Calceolaria andina L.

Two compounds recognized as responsible for the insecticidal activity of extracts of Calceolaria andina L. (Scrophulariaceae) have been isolated and characterized as 2-(1, 1-dimethylprop-2-enyl)-3-hydroxy-1,4-naphthoquinone and the corresponding acetate, 2-acetoxy-3-(1,1-dimethylprop-2-enyl)-1, 4-naphthoquinone. Their activities against 29 pest species and 9 beneficial species of arthropod from a total of 11 orders have been determined.

A new insecticidal pyranocyclohexenedione from kunzea ericifolia.

A new compound (1), named ericifolione, has been isolated from the hexane extract of the aerial parts of Kunzea ericifolia Rehb. (Myrtaceae) by bioassay-guided fractionation. It exhibits moderate insecticidal activity in comparison with natural pyrethrum extract.

Screening of medicinal plants from Trinidad and Tobago for antimicrobial and insecticidal properties.

Antibacterial activity in 51 extracts from 29 plant species currently used in traditional medicine in Trinidad and the neighbouring Caribbean islands was tested for by the agar dilution streak method using six bacteria: Escherichia coli, Pseudomonas aeruginosa. Salmonella tophimurium, Staphylococcus aureus, Staphylococcus epidermidis and Enterococcus faecalis. The extracts from eight of the plants tested showed significant activity against one or more micro-organisms and the most susceptible bacterium was Staphylococcus aureus.

Analysis of autoxidized fats by gas chromatography-mass spectrometry: II. Methyl linoleate.

The gas chromatography-mass spectrometry (GC-MS) approach developed in the preceding paper was applied for qualitative and quantitative investigations of autoxidation products of methyl linoleate. A GC-MS computer summation method was standardized with synthetic 9- and 13-hydroxyoctadecanoate. Equal amounts of 9- and 13-hydroperoxides were found in all samples of linoleate autoxidized at different temperatures and peroxide levels.

Analysis of autoxidized fats by gas chromatography-mass spectrometry: I. Methyl oleate.

A structural investigation of autoxidation products of methyl oleate was carried out by gas chromatography-mass spectrometry (GC-MS) of trimethylsilyl (TMS) ether derivatives. GC-MS using computer plots of selected masses afforded structural assignments of GC peaks due to incompletely resolved mixtures. This method provided evidence of epoxy and keto esters which are not completely separated from the main components consisting of the TMS derivatives of the allylic hydroxy esters.