Bioactivity of essential oil of Litsea cubeba from China and its main compounds against two stored product insects

During our screening program for agrochemicals from Chinese medicinal herbs and wild plants, the essential oil of Litsea cubeba fruits was found to possess strong contact toxicity against the cigarette beetle Lasioderma serricorne adults and the booklouse Liposcelis bostrychophila, with LD₅₀ values of 27.33 μg/adult and 71.56 μg/cm², respectively, and also showed strong fumigant toxicity against the two stored product insects with LC₅₀ values of 22.97 and 0.73 mg/L, respectively. The essential oil obtained by hydrodistillation was investigated by GC MS. The main components of the essential oil were identified to be E-citral (geranial) (27.49%), Z-citral (neral) (23.57%) and d-limonene (18.82%) followed by β-thujene (3.34%), β-pinene (2.85%), α-pinene (2.57%), 6-methyl-5-hepten-2-one (2.40%) and linalool (2.36%). Citral (Z/E-citral), d-limonene, β-pinene, α-pinene and linalool were separated and purified by silica gel column chromatography and preparative thin layer chromatography, and further identified by means of physicochemical and spectrometric analysis. Citral and linalool showed strong contact toxicity against L. serricorne and L. bostrychophila (LD₅₀ = 11.76, 12.74 μg/adult and 20.15, 99.97 μg/cm², respectively) and fumigant toxicity against L. serricorne and L. bostrychophila (16.54, 18.04 mg/L air and 0.14, 0.71 mg/L air, respectively). Otherwise, citral, d-limonene and linalool were strongly repellent against the cigarette beetle L. serricorne as the essential oil whereas β-pinene and α-pinene exhibited weaker repellency against the cigarette beetle compared with the positive control, DEET. Moreover, except α-pinene and linalool, the other three compounds as well as the essential oil exhibited comparable repellency against the booklouse relative to DEET.     

A Transient Receptor Potential Ion Channel in Chlamydomonas Shares Key Features with Sensory Transduction-Associated TRP Channels in Mammals

Sensory modalities are essential for navigating through an ever-changing environment. From insects to mammals, transient receptor potential (TRP) channels are known mediators for cellular sensing. Chlamydomonas reinhardtii is a motile single-celled freshwater green alga that is guided by photosensory, mechanosensory, and chemosensory cues. In this type of alga, sensory input is first detected by membrane receptors located in the cell body and then transduced to the beating cilia by membrane depolarization. Although TRP channels seem to be absent in plants, C. reinhardtii possesses genomic sequences encoding TRP proteins. Here, we describe the cloning and characterization of a C. reinhardtii version of a TRP channel sharing key features present in mammalian TRP channels associated with sensory transduction. In silico sequence-structure analysis unveiled the modular design of TRP channels, and electrophysiological experiments conducted on Human Embryonic Kidney-293T cells expressing the Cr-TRP1 clone showed that many of the core functional features of metazoan TRP channels are present in Cr-TRP1, suggesting that basic TRP channel gating characteristics evolved early in the history of eukaryotes.     

Plant essential oils: a substitute for conventional insecticides against Tribolium species (Coleoptera: Tenebrionidae)-achievements and challenges

Abstract

The literature on efficacy of plant essential oils and their constituents for the management of Tribolium spp. (T. castaneum and T. confusum), instigating infestation of a variety of stored grains and their products is reviewed here. Both species caused significant losses in the diverse food grains and their products through infestation. Essential oils of higher plants showed potential activity in the management of these infestation driven losses. Researchers have found that essential oils and their chemical constituents have significant toxicity against both the species of Tribolium via different modes of action like repellent, insecticidal, ovicidal, larvicidal, pupicidal, ovipositional and feeding deterrent actions. Concerning repellency and in vivo bioassays, few studies have been done with the essential oils against T. confusum, thus, more investigations are required to find the repellent agents against this insect. There are some essential oil-based botanical insecticides which have been proved effective for the protection of food grains from both beetles during storage. These botanical insecticides also exhibited behaviour altering properties against both beetles, thus, reducing the problem of pest resistance which is a problem with conventional insecticides. Therefore, essential oils-based botanical insecticides may be preferred option than conventional insecticides for protecting stored grains and their products against Tribolium infestation.     

Trade‐off between attraction to aggregation pheromones and repellent effects of spike lavender essential oil and its main constituent linalool in the flour beetle Tribolium confusum

Essential oils of aromatic plants and their individual volatile components have been tested in pest management strategies for their toxic and often repellent effects on target insects. When evaluating their possible effects on crucial behaviours of the pest insects, the olfactory environment including intraspecific communication cues has to be considered. We used the flour beetle Tribolium confusum du Val (Coleoptera: Tenebrionidae), a common stored‐product pest, to investigate the influence of oil of spike lavender, Lavandula spica Medik. (Labiaceae), and its main component, linalool, at various doses on olfactory‐guided behaviour. Using four‐way olfactometers, a dose‐dependent repellent effect of L. spica oil and linalool alone was revealed. On the other hand, we confirmed that T. confusum is attracted by conspecifics, by means of an aggregation pheromone and by 10 ng of one of its components, 1‐tetradecene. Twenty‐four hour pre‐exposure to 10 μl of L. spica oil abolished subsequent attraction to 1‐tetradecene and reduced attraction to five conspecifics. Simultaneous exposure to L. spica oil or linalool and five conspecifics reduced the repellent effect of the volatiles in a dose‐dependent manner, whereas simultaneous exposure to 1‐tetradecene at 10 ng abolished the repellent effect of L. spica oil only at a dose of 0.01 mg. These results indicate a dose‐dependent trade‐off between attractive and plant‐derived repellent volatiles, which may influence the effectiveness of such volatiles in their potential use in alternative pest management strategies.     

Insecticidal and Repellent Activity of Thymus quinquecostatus Celak. Essential Oil and Major Compositions against Three Stored-Product Insects

Thymus quinquecostatus Celak. of the Lamiaceae family has a long history of dual use of medicine and food with high economic value, and has been proved to have good antioxidative, antimicrobial, and antidiabetic activities. Essential oil (EO) extracted from the aerial part of T. quinquecostatus was obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC/MS) and GC. Totally 45 compounds were identified accounting for 98.5 % of the EO. The major constituents of the EO were linalool (52.003 %), borneol (10.911 %) and anethole (5.325 %). Fumigant, contact and repellent activity of T. quinquecostatus essential oil (EO) against Tribolium castaneum (Coleoptera: Tenebrionidae), Lasioderma Serricorne (Coleoptera: Anobiidae), Liposcelis bostrychophila (Psocoptera: Liposcelididae) were evaluated in this work. T. quinquecostatus EO and three major constituents showed varying degrees of insecticidal and repellent activities to three stored-product insects. Anethole stated the best fumigant and contact activity than others did to all three insect species. EO and compounds showed general repellent activity against three target insects. This work suggests that the EO of T. quinquecostatus has promising potential to be developed into botanical pesticides and repellents controlling pest damage in warehouses and grain stores.     

Volatile compounds from Liposcelis bostrychophila (Psocoptera: Liposcelididae) and their environment and their effects on settling behaviour

Headspace from above either Liposcelis bostrychophila Badonnel reared on powdered food; insects without food or from powdered food only were collected on five occasions over a period of four weeks. Volatiles were analysed by thermal desorption gas chromatography-mass spectrometry (TD-GCMS) to look for ecologically significant volatile compounds. Hexanoic acid (HA) was the major compound in the insect only and diet only volatiles (insect 25.6 ± 1.6%, diet 32.9 ± 1.13%). Isobutyric acid was the main compound detected in the volatiles from both insects and diet (35.3 ± 6%). Butyric acid (BA) and acetoin (HB) were also present at >2% of the total peak areas. HB was not detected in the insect only volatiles. Bioassays showed that hexanoic acid was the most repellent chemical. Mixtures of compounds representing the proportions of HA, BA, IBA, and HB in the volatiles did not have any prolonged effect on settling or selection by booklice in a two choice bioassay. L. bostrychophila can avoid individual volatile chemicals but the effects can be masked when they are incorporated into mixtures. As some volatile compounds can be detected by booklice they may govern dispersal, but further work is required to clarify their significance.     

Chemical Constituents and Insecticidal Activities of Ajania fruticulosa Essential Oil

The insecticidal activity and chemical constituents of the essential oil from Ajania fruticulosa were investigated. Twelve constituents representing 91.0% of the essential oil were identified, and the main constituents were 1,8‐cineole ( 41.40% ), (+)‐camphor ( 32.10% ), and myrtenol (8.15%). The essential oil exhibited contact toxicity against Tribolium castaneum and Liposcelis bostrychophila adults with LD₅₀ values of 105.67 μg/adult and 89.85 μg/cm², respectively. The essential oil also showed fumigant toxicity against two species of insect with LC₅₀ values of 11.52 and 0.65 mg/l, respectively. 1,8‐Cineole exhibited excellent fumigant toxicity (LC₅₀ = 5.47 mg/l) against T. castaneum. (+)‐Camphor showed obvious fumigant toxicity (LC₅₀ = 0.43 mg/l) against L. bostrychophila. Myrtenol showed contact toxicity (LD₅₀ = 29.40 μg/cm²) and fumigant toxicity (LC₅₀ = 0.50 mg/l) against L. bostrychophila. 1,8‐Cineole and (+)‐camphor showed strong insecticidal activity to some important insects, and they are main constituents of A. fruticulosa essential oil. The two compounds may be related to insecticidal activity of A. fruticulosa essential oil against T. castaneum and L. bostrychophila.     

Contact Toxicity and Repellency of the Essential Oil of Dictamnus dasycarpus Roots from China against Two Stored‐Product Insects

During our screening program for new agrochemicals from traditional medicinal herbs, Dictamnus dasycarpus was found to possess contact toxicity and repellent activity against the cigarette beetle Lasioderma serricorne and the booklouse Liposcelis bostrychophila. The essential oil obtained by hydrodistillation of D. dasycarpus roots was characterized by GC‐FID and GC/MS analyses, and the main components identified were syn‐7‐hydroxy‐7‐anisylnorbornene ( 1 , 49.9%), 1,3,4,5,6,7‐hexahydro‐2H‐inden‐2‐one ( 2 , 11.6%), 5,6‐diethenyl‐1‐methylcyclohexene ( 3 , 7.4%), and 3,9‐dimethyltricyclo[4.2.1.1^2,5]dec‐3‐en‐9‐ol ( 4 , 6.35%). The D. dasycarpus root oil exhibited strong contact toxicity against L. serricorne adults and L. bostrychophila, with LD₅₀ values of 12.4 μg/adult and 27.2 μg/cm², respectively. Moreover, the essential oil also showed strong repellency against both stored‐product insects tested.     

Repellent and Contact Toxicity of Alpinia officinarum Rhizome Extract against Lasioderma serricorne Adults

The repellent and contact toxicities of Alpinia officinarum rhizome extract on Lasioderma serricorne adults, and its ability to protect stored wheat flour from L. serricorne adults infestation were investigated. The A. officinarum extract exhibited strong repellent and contact toxicities against L. serricorne adults. The toxicities enhanced significantly with the increasing treatment time and treatment dose. The mean percentage repellency value reached 91.3% at class V at the dose of 0.20 μL/cm² after 48 h of exposure. The corrected mortality reached over 80.0% at the dose of 0.16 μL/cm² after 48 h of exposure. The A. officinarum extract could significantly reduce L. serricorne infestation level against stored wheat flour. Particularly, the insect infestation was nil in wheat flour packaged with kraft paper bags coated with the A. officinarum extract at the dose of above 0.05 μL/cm². The naturally occurring A. officinarum extract could be useful for integrated management of L. serricorne.     

Insect feeding deterrent activity of bisabolangelone and of some sesquiterpenes of eremophilane type

The insect feeding deterrent activity of some sesquiterpenes of furanoeremophilane type and of the related eremophilanolide type were tested towards three selected storage pests: Sitophilus granarius, Tribolium confusum and Trogoderma granarium. The results were compared with the biogenetically related compound of bakkenolide type, known as a potent antifeedant. Bisabolangelone, tested on the same insects, exhibited the strongest activity, and may be included in the class of very good insect feeding deterrents. The antifeeding activity of bisabolangelone and bakkenolide A towards larvae of Leptinotarsa decemlineata was also observed.     

Effects of Essential Oil from Hinoki Cypress,Chamaecyparis obtusa,on Physiology and Behavior of Flies

Phytoncides, which are volatile substances emitted from plants for protection against plant pathogens and insects, are known to have insecticidal, antimicrobial, and antifungal activities. In contrast to their negative effects on microorganisms and insects, phytoncides have been shown to have beneficial effects on human health. Essential oil from Hinoki cypress (Chamaecyparis obtusa) is mostly used in commercial products such as air purifiers. However, the physiological/behavioral impact of essential oil from C. obtusa on insects is not established. In this study, we tested the effects of essential oil extracted from C. obtusa on the physiologies and behaviors of Drosophila melanogaster and Musca domestica. Exposure to essential oil from C. obtusa decreased the lifespan, fecundity, locomotive activity, and developmental success rate of D. melanogaster. In addition, both fruit flies and house flies showed strong repellent behavioral responses to the essential oil, with duration times of about 5 hours at 70 μg/ml. These results suggest that essential oil from C. obtusa can be used as a ‘human-friendly’ alternative insect repellent.     

Fumigant toxicity of Lavandula spica essential oil and linalool on different life stages of Tribolium confusum (Coleoptera: Tenebrionidae)

The confused flour beetle, Tribolium confusum, is a common and severe pest of stored products. Here, using fumigation tests during four different exposure times, we evaluated the toxicity of different doses of essential oil of spike lavender, Lavandula spica and one of its major constituents, linalool, on different life stages of T. confusum under laboratory conditions. The toxicity of the L. spica oil and linalool varied as a function of the developmental stage and treatment duration. Young larvae (L1) were the most susceptible to toxic effects, with LC₅₀ = 19.535 μl/L of air for L. spica oil and LC₅₀ = 14.198 μl/L of air for linalool after 24 h of exposure, whereas older larvae (L8) were affected only very little by fumigation. Linalool caused higher egg mortality than L. spica oil at equivalent doses, but lower mortality in pupae and adults. Emergence of intact adult insects from surviving eggs, larvae and pupae was further reduced as a function of dose and exposure time to both L. spica oil and linalool compared to control-treated insects. Our results show that L. spica oil and linalool might be suitable for biological control of T. confusum, but tests at a larger scale are necessary to confirm our results.     

Neurotoxicity and Mode of Action of N,N-Diethyl-Meta-Toluamide (DEET)

Recent studies suggest that N, N-diethyl-meta-toluamide (DEET) is an acetylcholinesterase inhibitor and that this action may result in neurotoxicity and pose a risk to humans from its use as an insect repellent. We investigated the mode of action of DEET neurotoxicity in order to define the specific neuronal targets related to its acute toxicity in insects and mammals. Although toxic to mosquitoes (LD₅₀ ca. 1.5 µg/mg), DEET was a poor acetylcholinesterase inhibitor (<10% inhibition), even at a concentration of 10 mM. IC₅₀ values for DEET against Drosophila melanogaster, Musca domestica, and human acetylcholinesterases were 6–12 mM. Neurophysiological recordings showed that DEET had excitatory effects on the housefly larval central nervous system (EC₅₀: 120 µM), but was over 300-fold less potent than propoxur, a standard anticholinesterase insecticide. Phentolamine, an octopamine receptor antagonist, completely blocked the central neuroexcitation by DEET and octopamine, but was essentially ineffective against hyperexcitation by propoxur and 4-aminopyridine, a potassium channel blocker. DEET was found to illuminate the firefly light organ, a tissue utilizing octopamine as the principal neurotransmitter. Additionally, DEET was shown to increase internal free calcium via the octopamine receptors of Sf21 cells, an effect blocked by phentolamine. DEET also blocked Na⁺ and K⁺ channels in patch clamped rat cortical neurons, with IC₅₀ values in the micromolar range. These findings suggest DEET is likely targeting octopaminergic synapses to induce neuroexcitation and toxicity in insects, while acetylcholinesterase in both insects and mammals has low (mM) sensitivity to DEET. The ion channel blocking action of DEET in neurons may contribute to the numbness experienced after inadvertent application to the lips or mouth of humans.     

Insecticidal and Repellent Activities of the Essential Oil of Callistemon citrinus (Myrtaceae) Against Callosobruchus maculatus (F.) (Coleoptera: Bruchidae)

The essential oil of Callistemon citrinus (Curtis) leaves was extracted by hydro distillation and tested on female and male adults of Callosobruchus macullatus (F.) for insecticidal and repellent effects. GC-MS analysis was used to identify and quantify the volatile composition of the essential oil. Results showed that 1,8-cineole (34.2%) and α-pinene (29.0%) were the major components of the oil. Callistemon citrinus oil was found to be toxic to adult insects when applied by fumigation. Responses varied according to the gender of the insect and exposure time. LC₅₀ values were 12.88 and 84.4 μL.?L^?1 for males and females, respectively. An increase in exposure time from 3 to 24 h caused an increase in mortality from 50% to 100% in males and from 15.5% to 85.2% in females, at the highest concentration (500 μL.?L^?1). The essential oil also had a repellent effect against C. macullatus in a filter paper arena test. After 2 and 4 h, 86% and 94%, respectively, repellent effects were demonstrated at the highest concentration of 0.4 μL?.cm^?2. These observations suggest that C. citrinus essential oil may be usefully applied to control storage pests.     

Antibacterial Characterization of Novel Synthetic Thiazole Compounds against Methicillin-Resistant Staphylococcus pseudintermedius

Staphylococcus pseudintermedius is a commensal organism of companion animals that is a significant source of opportunistic infections in dogs. With the emergence of clinical isolates of S. pseudintermedius (chiefly methicillin-resistant S. pseudintermedius (MRSP)) exhibiting increased resistance to nearly all antibiotic classes, new antimicrobials and therapeutic strategies are urgently needed. Thiazole compounds have been previously shown to possess potent antibacterial activity against multidrug-resistant strains of Staphylococcus aureus of human and animal concern. Given the genetic similarity between S. aureus and S. pseudintermedius, this study explores the potential use of thiazole compounds as novel antibacterial agents against methicillin-sensitive S. pseudintermedius (MSSP) and MRSP. A broth microdilution assay confirmed these compounds exhibit potent bactericidal activity (at sub-microgram/mL concentrations) against both MSSA and MRSP clinical isolates while the MTS assay confirmed three compounds (at 10 μg/mL) were not toxic to mammalian cells. A time-kill assay revealed two derivatives rapidly kill MRSP within two hours. However, this rapid bactericidal activity was not due to disruption of the bacterial cell membrane indicating an alternative mechanism of action for these compounds against MRSP. A multi-step resistance selection analysis revealed compounds 4 and 5 exhibited a modest (two-fold) shift in activity over ten passages. Furthermore, all six compounds (at a subinihibitory concentration) demonstrated the ability to re-sensitize MRSP to oxacillin, indicating these compounds have potential use for extending the therapeutic utility of β-lactam antibiotics against MRSP. Metabolic stability analysis with dog liver microsomes revealed compound 3 exhibited an improved physicochemical profile compared to the lead compound. In addition to this, all six thiazole compounds possessed a long post-antibiotic effect (at least 8 hours) against MRSP. Collectively the present study demonstrates these synthetic thiazole compounds possess potent antibacterial activity against both MSSP and MRSP and warrant further investigation into their use as novel antimicrobial agents.     

Synthesis and insecticidal activity studies of novel phenylpyrazole derivatives containing arylimine or carbimidate moiety

Phenylpyrazole insecticides are successful for crop protection and public hygiene by blocking gamma-aminobutyric acid (GABA)-gated chloride channels and glutamate-gated chloride (GluCl) channels. A series of novel phenylpyrazoles containing arylimine or 1-methoxyaryl groups were designed and synthesized. The addition reaction of methanol to the imines 1–11 was investigated and the cayno addition products 13–15 were obtained. The compounds 1–15 were confirmed by ¹H NMR and elemental analysis. The results of bioassay indicated that some compounds exhibited comparable bioactivity to fipronil against a broad spectrum of insects such as bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), diamondback moth (Plutella xylostella) and Oriental armyworm (Mythimna separata). Especially, the foliar contact activity against bean aphid of compound 7 at 10 µg mL⁻¹ was 68%, the larvacidal activity against mosquito of compounds 5, 13 and 15 at 0.0025 µg mL⁻¹ was 100%, the larvacidal activity against diamondback moth of compounds 9 and 11 at 0.05 µg mL⁻¹ was 100%, the larvacidal activity against Oriental armyworm of compound 9 at 1 µg mL⁻¹ was 100%. The 3-cayno moiety on pyrazole ring was essential for the high insecticidal activities against bean aphid, diamondback moth and Oriental armyworm, while the 3-carbimidate moiety on pyrazole ring was crucial to the excellent high insecticidal activities against mosquito.     

Cytoskeletal and scaffolding proteins as structural and functional determinants of TRP channels

Transient receptor potential (TRP) channels are six transmembrane-spanning proteins, with variable selectivity for cations, that play a relevant role in intracellular Ca^2 + homeostasis. There is a large body of evidence that shows association of TRP channels with the actin cytoskeleton or even the microtubules and demonstrating the functional importance of this interaction for TRP channel function. Conversely, cation currents through TRP channels have also been found to modulate cytoskeleton rearrangements. The interplay between TRP channels and the cytoskeleton has been demonstrated to be essential for full activation of a variety of cellular functions. Furthermore, TRP channels have been reported to take part of macromolecular complexes including different signal transduction proteins. Scaffolding proteins play a relevant role in the association of TRP proteins with other signaling molecules into specific microdomains. Especially relevant are the roles of the Homer family members for the regulation of TRPC channel gating in mammals and INAD in the modulation of Drosophila TRP channels. This article is part of a Special Issue entitled: Reciprocal influences between cell cytoskeleton and membrane channels, receptors and transporters. Guest Editor: Jean Claude Hervé.     

Biological evaluation of tetracationic compounds based on two 1,4-diazabicyclo[2.2.2]octane moieties connected by different linkers

A series of 1,4-diazabicyclo[2.2.2]octane derivatives differing by linker moiety was evaluated for activity against several strains of both Gram-positive and Gram-negative bacteria including drug-resistant strains, one strain of fungus and influenza virus A/Puerto Rico/8/34 (H1N1). All compounds exhibited high antibacterial activity against all bacteria except Proteus vulgaris. The minimum inhibitory concentrations (MICs) of compound 1c with an o-phenylenebismethyl linker and compound 1e with a propylene aliphatic linker were found to be low and were comparable or better to the reference drug ciprofloxacin for Pseudomonas aeruginosa and Staphylococcus aureus. Additionally, a time-kill assay was performed to examine the bactericidal kinetics. Compounds 1c and 1e displayed rapid killing effects against St. aureus and Ps. aeruginosa after 2 h. Furthermore, compounds 1a–c with aromatic linkers and compound 1e showed the highest antiviral activity.     

Comparison of the feeding deterrent activity of some sesquiterpene lactones and a lignan lactone towards selected insect storage pests

Four sesquiterpene lactones isolated from Eurpatorium cannabinum, Homogyne alpina and Petasites albus (all Compositae), together with two of their adducts, as well as one lignan lactone of dibenzylbutanolide type from Libocedrus yateensis (Cupressaceae), were tested for their feeding deterrent activity against the adults of Sitophilus granarius and Tribolium confusum, as well as against the larvae of Tribolium confusum and Trogoderma granarium. The strongest deterrent activity against all species was exhibited by the lignan lactone yatein and the sesquiterpene spirolactone bakkenolide A. Both may be included to the class of very good insect feeding deterrents. The comparison presented here showed that the conjugated α-exomethylene moiety of the lactone ring was not the decisive factor for the deterrent activity in the investigated test model.