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Journal: Journal of chemical ecology


The cowpea aphid Aphis craccivora that infests the black locust Robinia pseudoacacia shows toxicity to its predator, the multicolored Asian ladybird beetle, Harmonia axyridis. In contrast, the same aphid species that infests the common vetch, Vicia angustifolia, is suitable prey for H. axyridis larvae. Previously, it was reported that the toxicity of A. craccivora infesting R. pseudoacacia was due to canavanine and 2-aminoethanol, but there was some doubt about the toxicity of these compounds and their concentrations in the aphids. In the present study, we determined the concentrations of cyanamide, canavanine, and 2-aminoethanol in A. craccivora infesting the two host plants. In the extracts of A. craccivora that infested either of the host plants, canavanine was undetectable, and 2-aminoethanol was detected at the concentration of 3.0-4.0 μg/g fresh weight. Cyanamide was detected in the extract of A. craccivora that infested R. pseudoacacia (7.7 μg/g fresh weight) but not in that infesting V. angustifolia. The toxicity of canavanine, 2-aminoethanol, and cyanamide was evaluated against H. axyridis larvae in a bioassay by using an artificial diet containing these compounds at various concentrations. Cyanamide exhibited 10-100 times stronger toxicity than canavanine and 2-aminoethanol. These results indicate that the toxicity is at least partly due to cyanamide, which is present in the toxic A. craccivora that infests R. pseudoacacia but absent from the non-toxic A. craccivora that infests V. angustifolia.

Concepts: Insect, Toxicity, Fabaceae, Vicia, Aphid, Coccinellidae, Harmonia axyridis, Robinia pseudoacacia


Caddisfly larvae (Limnophilus spp.) are important predators of eggs of the rough-skinned newt (Taricha granulosa). Newts may possess extremely large quantities of the neurotoxin tetrodotoxin (TTX) in their skin, and females may provision this toxin in their eggs. Using a competitive inhibition enzymatic immunoassay, we examined TTX-resistant caddisflies, sympatric with the known most toxic population of newts, for the presence of TTX. We found that caddisflies sequester TTX after consuming eggs in the laboratory. Caddisfly larvae that were frozen immediately after collecting in the wild possessed TTX. Finally, wild-caught larvae reared on a TTX-free diet in the laboratory retained TTX for up to 134 days, through metamorphosis and into the adult stage.

Concepts: Insect, Larva, Predation, Frog, Newts, Tetrodotoxin, Newt, Rough-skinned newt


Plants produce a variety of secondary metabolites (PSMs) that may be selective against herbivores. Yet, specialist herbivores may use PSMs as cues for host recognition, oviposition, and feeding stimulation, or for their own defense against parasites and predators. This summarizes a dual role of PSMs: deter generalists but attract specialists. It is not clear yet whether specialist herbivores are a selective force in the evolution of PSM diversity. A prerequisite for such a selective force would be that the preference and/or performance of specialists is influenced by PSMs. To investigate these questions, we conducted an oviposition experiment with cinnabar moths (Tyria jacobaeae) and plants from an artificial hybrid family of Jacobaea vulgaris and Jacobaea aquatica. The cinnabar moth is a specialist herbivore of J. vulgaris and is adapted to pyrrolizidine alkaloids (PAs), defensive PSMs of these plants. The number of eggs and egg batches oviposited by the moths were dependent on plant genotype and positively correlated to concentrations of tertiary amines of jacobine-like PAs and some otosenine-like PAs. The other PAs did not correlate with oviposition preference. Results suggest that host plant PAs influence cinnabar moth oviposition preference, and that this insect is a potential selective factor against a high concentration of some individual PAs, especially those that are also involved in resistance against generalist herbivores.

Concepts: Insect, Plant, Animal, Alkaloids, Herbivore, Arctiidae, Jacobaea vulgaris, Cinnabar moth


Evolutionary shifts in pollination systems within a plant genus are commonly associated with changes in floral scent, reflecting selection mediated through the sensory systems of various pollinators. The most common cetoniine beetle pollinator of grassland Protea species in South Africa, Atrichelaphinis tigrina, previously has been shown to have a strong preference for the fruity floral scent of these plants over the weak scent of their bird-pollinated congeners. However, it is not known which of the many compounds found in the scent of beetle pollinated Protea species play a role for pollinator attraction. Electroantennograms (EAG) from A. tigrina beetles were recorded in response to 15 compounds emitted by Protea flower heads. EAG responses to all 15 compounds were significantly greater than those to the paraffin solvent in which they were diluted. The greatest responses were observed for aromatics (anisole, methyl benzoate, methyl salicylate, benzaldehyde) followed by the monoterpene β-linalool, which can comprise up to 66 % of fruity Protea scents. Five compounds that elicited EAG responses (benzaldehyde, β-linalool, (E/Z)-linalool oxide (furanoid), methyl benzoate, and methyl salicylate) were tested in commercially available yellow bucket traps in the field to test their attractiveness to beetles. Traps baited with methyl benzoate, β-linalool, (E/Z)-linalool oxide (furanoid), and methyl salicylate caught significantly more insects than did those containing paraffin only. Methyl benzoate also was more specifically attractive to A. tigrina than was (E/Z)-linalool oxide (furanoid) and paraffin baited controls. A second field experiment using a combination of linalool vs. paraffin baited yellow or green traps showed that trap color had a significant effect on the number of trapped beetles. Yellow traps yielded a ten-fold higher number of insect catches than did green traps. However, the combination of yellow color and the scent compound linalool yielded the highest number of catches. This study has shown that the cetoniine beetle A. tigrina can detect a variety of floral compounds and is attracted to compounds comprising a large proportion of the blend that makes up fruity Protea scents, adding support for the hypothesis that change in scent chemistry during the shift from bird to cetoniine beetle pollination in this genus were mediated by beetle sensory preferences.

Concepts: Insect, Pollination, Flower, Pollinator decline, Pollen, Benzoic acid, Pollinator, Flavors


Intercropping and rotating banana (Musa spp.) with Chinese chive (Allium tuberosum Rottler) has been used as an effective method to control Panama disease (Fusarium wilt) of banana in South China. However, the underlying mechanism is unknown. In this study, we used aqueous leachates and volatiles from Chinese chive to evaluate their antimicrobial activity on Fusarium oxysporum f. sp. cubense race 4 (FOC), the causal agent of Panama disease in banana, and identified the antifungal compounds. Both leaf and root leachates of Chinese chive displayed strong inhibition against FOC, but the concentrated leachates showed lower inhibition than the original leachates. In a sealed system volatiles emitted from the leaves and roots of Chinese chive inhibited mycelial growth of FOC. Volatile compounds emitted from the intact growing roots mimicking natural environment inhibited spore germination of FOC. We identified five volatiles including 2-methyl-2-pentenal and four organosulfur compounds (dimethyl trisulfide, dimethyl disulfide, dipropyl disulfide, and dipropyl trisulfide) from the leaves and roots of Chinese chive. All these compounds exhibited inhibitory effects on FOC, but 2-methyl-2-pentenal and dimethyl trisulfide showed stronger inhibition than the other three compounds. 2-Methyl-2-pentenal at 50-100 μl/l completely inhibited the mycelial growth of FOC. Our results demonstrate that antifungal volatiles released from Chinese chive help control Panama disease in banana. We conclude that intercropping and rotating banana with Chinese chive can control Panama disease and increase cropland biodiversity.

Concepts: Fusarium, Garlic, Allium, Fusarium oxysporum, Plant pathogens and diseases, Volatile, Banana, Dimethyl sulfide


The cigarette beetle, Lasioderma serricorne, is a serious global pest that preys on stored food products. Larvae of the beetle cannot grow on roasted coffee beans or dried black or green tea leaves, although they oviposit on such products. We investigated oviposition by the beetles on MeOH extracts of the above products. The number of eggs laid increased with an increase in dose of each extract, indicating that chemical factors stimulate oviposition by the beetles. This was especially true for \ coffee bean extracts, which elicited high numbers of eggs even at a low dose (0.1 g bean equivalent/ml) compared to other extracts. Coffee beans were extracted in hexane, chloroform, 1-butanol, MeOH, and 20 % MeOH in water. The number of eggs laid was higher on filter papers treated with chloroform, 1-butanol, MeOH, and 20 % MeOH in water extracts than on control (solvent alone) papers. The chloroform extract was fractionated by silica-gel column chromatography. Nine compounds were identified by gas chromatography/mass spectrometry from an active fraction. Of these compounds, only a significant ovipositional response to catechol was observed.

Concepts: Coffee, Solvent, Caffeine, Tea, Coffea, Coffee bean, Anobiidae, Lasioderma serricorne


Queensland fruit fly, Bactrocera tryoni (Q-fly), is a major pest of horticultural crops in eastern Australia. Lures that attract male Q-fly are important for detection of incursions and outbreaks, monitoring of populations, and control by mass trapping and male annihilation. Cuelure, an analog of naturally occurring raspberry ketone, is the standard Q-fly lure, but it has limited efficacy compared with lures that are available for some other fruit flies such as methyl eugenol for B. dorsalis. Melolure is a more recently developed raspberry ketone analog that has shown better attraction than cuelure in some field studies but not in others. A novel fluorinated analog of raspberry ketone, raspberry ketone trifluoroacetate (RKTA), has been developed as a potential improvement on cuelure and melolure. RKTA placed on laboratory cages containing 2-week-old Q-flies elicited strong behavioral responses from males. Quantification of Q-fly responses in these cages, using digital images to estimate numbers of flies aggregated near different lures, showed RKTA attracted and arrested significantly more flies than did cuelure or melolure. RKTA shows good potential as a new lure for improved surveillance and control of Q-fly.

Concepts: Better, Flies, Bactrocera, Tephritidae, Raspberry, Acalyptratae, Dacinae, Bactrocera tryoni


The composition of plant secondary metabolites (PSMs) extensively impacts ecosystem functioning. It is vital that we understand temporal patterns in the plants' allocation of resources to PSMs, particularly those influenced by human activity. Existing data are insufficient in the long-term perspective of perennial plants (age or ontogeny). We analysed phenolic concentrations in foliage from birch (Betula pubescens Ehr.) considered to be undamaged and growing on 5, 10 and 15 years old clear-cuts in two boreal forest landscapes in Norway, sampled at the peak of the growing season. In sum, low molecular weight phenolic concentrations decreased with age. Apart from one apigenin glycoside, the low molecular weight phenolics co-varied similarly at all ages, suggesting a lack of temporal compound-specific prioritisation of this group. In contrast, the concentration of MeOH-soluble condensed tannins increased with age. The compositional shift fits well with several hypotheses that may provide proximate explanations for age patterns in PSM allocations, including both resource constraints and external pressures. Regardless of these explanations, our study adds an important perennial perspective (plant age) to temporal PSM patterns already well-known in boreal plant phenology (foliage age).

Concepts: Plant, Perennial plant


There is growing evidence of a substantial decline in pollinators within Europe and North America, most likely caused by multiple factors such as diseases, poor nutrition, habitat loss, insecticides, and environmental pollution. Diesel exhaust could be a contributing factor to this decline, since we found that diesel exhaust rapidly degrades floral volatiles, which honey bees require for flower recognition. In this study, we exposed eight of the most common floral volatiles to diesel exhaust in order to investigate whether it can affect volatile mediated plant-pollinator interaction. Exposure to diesel exhaust altered the blend of common flower volatiles significantly: myrcene was considerably reduced, β-ocimene became undetectable, and β-caryophyllene was transformed into its cis-isomer isocaryophyllene. Proboscis extension response (PER) assays showed that the alterations of the blend reduced the ability of honey bees to recognize it. The chemically reactive nitrogen oxides fraction of diesel exhaust gas was identified as capable of causing degradation of floral volatiles.

Concepts: Insect, Honey bee, Beekeeping, Pollination, Flower, Pollinator decline, Bee, Bumblebee


(Z)-4-undecenal (Z4-11Al) is the volatile pheromone produced by females of the vinegar fly Drosophila melanogaster. Female flies emit Z4-11Al for species-specific communication and mate-finding. A sensory panel finds that synthetic Z4-11Al has a characteristic flavour, which can be perceived even at the small amounts produced by a single female fly. Since only females produce Z4-11Al, and not males, we can reliably distinguish between single D. melanogaster males and females, according to their scent. Females release Z4-11Al at 2.4 ng/h and we readily sense 1 ng synthetic Z4-11Al in a glass of wine (0.03 nmol/L), while a tenfold concentration is perceived as a loud off-flavour. This corroborates the observation that a glass of wine is spoilt by a single D. melanogaster fly falling into it, which we here show is caused by Z4-11Al. The biological role of Z4-11Al or structurally related aldehydes in humans and the basis for this semiochemical convergence remains yet unclear.

Concepts: Insect, Model organism, Drosophila melanogaster, Drosophila