The recent outbreak of the mountain pine beetle (Dendroctonus ponderosae; MPB) has affected over 20 M hectares of pine forests in western North America. During the colonization of host trees, female ...MPB release the aggregation pheromone (-)-trans-verbenol. (-)-trans-Verbenol is thought to be produced from the pine defense compound (-)-α-pinene by cytochrome P450 (P450) dependent hydroxylation. MPB may also use P450s for the detoxification of other monoterpenes of the pine defense system. Here we describe the functional characterization of MPB CYP6DE1. CYP6DE1, but not the closely related CYP6DE2, used the bicyclic monoterpenes (-)-α-pinene, (+)-α-pinene, (-)-β-pinene, (+)-β-pinene and (+)-3-carene as substrates. CYP6DE1 was not active with other monoterpenes or diterpene resin acids that were tested as substrates. trans-Verbenol is the major product of CYP6DE1 activity with (-)-α-pinene or (+)-α-pinene as substrates. When tested with blends of different ratios of (-)-α-pinene and (+)-α-pinene, CYP6DE1 produced trans-verbenol with an enantiomeric profile that was similar to that produced by female MPB exposed to the α-pinene enantiomers.
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•Synthesis of cerambycid pheromone: 3-hydroxy-2-hexanone and 2,3-hexanediol.•α-Hydroxylation of several alkylketones using (diacetoxyiodo)benzene.•Chiral synthesis of ...(R)-3-hydroxy-2-hexanone using l-proline as a catalyst.
The synthesis of 3-hydroxy-2-hexanone and 2,3-hexanediol, two components of the aggregation pheromone of several cerambycid species, is disclosed in here. Starting from 2-hexanone, through an α-hydroxylation using (diacetoxyiodo)benzene, 3-hydroxy-2-hexanone is obtained in good yield. Further reduction of this compound, gives 2,3-hexanediol in excellent yield. A study of the α-hydroxylation reaction of several alkylketones using an hypervalent iodine reagent is also disclosed in here. The synthesis of optically active compounds (R)- and (S)-3-hydroxy-2-hexanone was achieved starting from 2-hexanone with nitrosobenzene and l- and d-proline respectively, in several reaction media.
Insects use a diverse array of specialized terpene metabolites as pheromones in intraspecific interactions. In contrast to plants and microbes, which employ enzymes called terpene synthases (TPSs) to ...synthesize terpene metabolites, limited information from few species is available about the enzymatic mechanisms underlying terpene pheromone biosynthesis in insects. Several stink bugs (Hemiptera: Pentatomidae), among them severe agricultural pests, release 15-carbon sesquiterpenes with a bisabolene skeleton as sex or aggregation pheromones. The harlequin bug, Murgantia histrionica, a specialist pest of crucifers, uses two stereoisomers of 10,11-epoxy-1-bisabolen-3-ol as a male-released aggregation pheromone called murgantiol. We show that MhTPS (MhIDS-1), an enzyme unrelated to plant and microbial TPSs but with similarity to trans-isoprenyl diphosphate synthases (IDS) of the core terpene biosynthetic pathway, catalyzes the formation of (1S,6S,7R)-1,10-bisaboladien-1-ol (sesquipiperitol) as a terpene intermediate in murgantiol biosynthesis. Sesquipiperitol, a so-far-unknown compound in animals, also occurs in plants, indicating convergent evolution in the biosynthesis of this sesquiterpene. RNAi-mediated knockdown of MhTPS mRNA confirmed the role of MhTPS in murgantiol biosynthesis. MhTPS expression is highly specific to tissues lining the cuticle of the abdominal sternites of mature males. Phylogenetic analysis suggests that MhTPS is derived from a trans-IDS progenitor and diverged from bona fide trans-IDS proteins including MhIDS-2, which functions as an (E,E)-farnesyl diphosphate (FPP) synthase. Structure-guided mutagenesis revealed several residues critical to MhTPS and MhFPPS activity. The emergence of an IDS-like protein with TPS activity in M. histrionica demonstrates that de novo terpene biosynthesis evolved in the Hemiptera in an adaptation for intraspecific communication.
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•We modeled spatial patterns of bark beetle-killed forest patches after a storm.•Simulation models including beetle aggregation gave best fit with empirical data.•Beetles used most of ...the windthrows the two first seasons after the storm.•Later on new attack patches with hard-to-predict sizes developed outside windthrows.•Removal of windthrows the two first seasons may prevent a patch-driven outbreak.
The purpose of this study is to increase the basic understanding of outbreak dynamics in order to improve the management of bark beetle outbreaks. The spruce bark beetle Ips typographus is a major disturbance agent of European forests and is the continent’s most economically and environmentally damaging bark beetle. Outbreaks of the spruce bark beetle are often triggered by large windfall episodes, and we have utilized a unique opportunity to study a Slovakian outbreak where little salvage logging was performed in some areas after a 2.5millionm3 storm-felling in 2004.
Our analyses focused on the first five years after the windfall, and we used a combination of empirical data and simulation models to understand the spatial patterns of beetle-killed forest patches developing during the outbreak. The univoltine beetle population used an increasing proportion of the windfelled trees during the two first seasons after the storm, but from the third season onwards our comparisons of inter-patch distance distributions indicated a transition from beetle production largely in windfall areas to a self-sustaining outbreak with infestation patches developing independently of the windthrows. The size of new infestation patches formed after this transition was modeled as a function of beetle pressure, estimated by the proportion of a circle area surrounding new patches that was covered by infestation patches the previous year. Our model results of patch size distribution did not correspond well with the empirical data if patch formation was modeled as a pure dispersal–diffusion process. However, beetle aggregation on individual trees appears to be important for patch development, since good correspondence with empirical data was found when beetle aggregation was incorporated in the modeled dispersal process. The strength of correspondence between the beetle aggregation model and the empirical data varied with the density of aggregation trees in the modeled landscape, and reached a maximum of 83% for a density of three aggregation trees per infestation patch.
Our results suggest that efficient removal of windfelled trees up until the start of the second summer after a major windfall is important to avoid a transition into a patch-driven bark beetle outbreak that is very difficult to manage. Our results also indicate that the outcome of a patch-driven outbreak is difficult to predict, since the development of new infestation patches is not a simple function of beetle pressure but is also affected by beetle behavior and local forest conditions.
The phlebotomine sandfly,
, a major vector of the
parasite, uses terpene pheromones to attract conspecifics for mating. Examination of the
genome revealed a putative terpene synthase (TPS), ...which-upon heterologous expression in, and purification from,
-yielded a functional enzyme. The TPS, termed
TPS, converted geranyl diphosphate (GPP) into a mixture of monoterpenes with low efficiency, of which β-ocimene was the major product. (
)-farnesyl diphosphate (FPP) principally produced small amounts of (
)-β-farnesene, while (
)- and (
)-FPP yielded a mixture of bisabolene isomers. None of these mono- and sesquiterpenes are known volatiles of
. Notably, however, when provided with (
)-geranylgeranyl diphosphate (GGPP),
TPS gave sobralene as its major product. This diterpene pheromone is released by certain chemotypes of
, in particular those found in the Ceará state of Brazil. Minor diterpene components were also seen as products of the enzyme that matched those seen in a sandfly pheromone extract.
In an attempt to improve semiochemical-based treatments for protecting forest stands from bark beetle attack, we compared push-pull versus push-only tactics for protecting lodgepole pine (Pinus ...contortaDouglas ex Loudon) and whitebark pine (Pinus albicaulisEngelm.) stands from attack by mountain pine beetle (Dendroctonus ponderosae Hopkins) in two studies. The first was conducted on replicated 4.04-ha plots in lodgepole pine stands (California, 2008) and the second on 0.81-ha plots in whitebark pine stands (Washington, 2010). In both studies, D. ponderosae population levels were moderate to severe. The treatments were 1) push-only (D. ponderosae antiaggregant semiochemicals alone); 2) push-pull (D. ponderosae antiaggregants plus perimeter traps placed at regular intervals, baited with four-component D.ponderosae aggregation pheromone); and 3) untreated controls. We installed monitoring traps baited with two-component D. ponderosae lures inside each plot to assess effect of treatments on beetle flight. In California, fewer beetles were collected in push-pull treated plots than in control plots, but push-only did not have a significant effect on trap catch. Both treatments significantly reduced the rate of mass and strip attacks by D.ponderosae, but the difference in attack rates between push-pull and push-only was not significant. In Washington, both push-pull and push-only treatments significantly reduced numbers of beetles caught in traps. Differences between attack rates in treated and control plots in Washington were not significant, but the push-only treatment reduced attack rates by 30% compared with both the control and push-pull treatment. We conclude that, at these spatial scales and beetle densities, push-only may be preferable for mitigating D.ponderosae attack because it is much less expensive, simpler, and adding trap-out does not appear to improve efficacy.
•Monitoring efficacy of mountain pine beetle attractants in the expanded range.•Beetle response varied with release rate of beetle pheromone and population density.•Manipulating release rates of ...beetle pheromone may help mitigation strategy.
Mountain pine beetle has expanded its host range into naïve lodgepole pine forests in western Canada and killed a large number of pine trees. Synthetic attractants mainly bark beetle pheromones and host monoterpenes attached to traps are typically used to monitor beetle populations within its range. Despite well-established differences in beetle host selection behavior between endemic and outbreak population densities, the influence of population density on the response of mountain pine beetle to the synthetic attractants is poorly understood. Over three years, we tested the effects of different release rates of female mountain pine beetle aggregation pheromone (trans-verbenol) and two host monoterpenes (terpinolene and mycrene) and local beetle population density on trap catches of mountain pine beetle. We estimated local mountain pine beetle population densities using the number of dead trees observed in the previous year’s aerial detection survey. During the first three weeks of the flight period, the lures with low release rates of all components captured more mountain pine beetle with increasing beetle population density and the lures with a high release rate of trans-verbenol plus a low release rate of host monoterpenes were preferred by beetles in low population density sites. We also found a temporal shift in attraction patterns. As the flight period progressed, the preference for low trans-verbenol release rate lures was less pronounced at high mountain pine beetle densities. No sex-specific responses of mountain pine beetles, along with number of competitor and predatory beetles of mountain pine beetle, were found for a particular attractant. These results provide evidence that mountain pine beetle has a density dependent response to attractants and can assess available semiochemicals cues to ensure successful host colonization depending on their density and the flight period. Overall, this study can improve the efficacy of current semiochemical-based monitoring tools, which are essential to implementing informed mitigation strategies for mountain pine beetle especially while they are in a sub-outbreak stage in the expanded distribution.
Premise
Angiosperms distributed over a large geographical area may display considerable phenotypic variation that can be recognized at morphological and micromorphological levels. Here, we ...investigate the pollination biology and the presence of floral rewards in Brazilian populations of the widely distributed orchid, Brasiliorchis picta. Based on the new data presented here this study investigates the evolution of floral rewards in Maxillariinae, and tests for the occurrence of convergent evolution of food‐hairs in this subtribe.
Methods
Micromorphological and histochemical analyses of the labellar tissues were conducted, together with chemical analysis of fragrance and experiments involving the use of chemical baits. The evolution of floral rewards in Maxillariinae were addressed.
Results
Microscopy revealed that B. picta offers food‐hairs as a reward. Fragrance is produced by abaxially located labellar epidermal papillae. The main compound present in our samples (2‐phenylethanol) also occurs in the aggregation pheromone produced by the mandible glands of pollinators, Meliponini bees. Our analyses indicate a high diversity of flower rewards and pollinators displayed by members of Maxillariinae, and support that edible trichomes evolved independently five times in the subtribe.
Conclusions
The high diversity of floral rewards and pollinators displayed by members of Maxillariinae suggests that different pollinator pressures are involved in the evolution of this neotropical subtribe. In addition, the offering of food‐hairs, which are generally infrequently encountered in Orchidaceae, arose by convergent evolution in Maxillariinae.
Since the first report in 1993 in Korea, the western flower thrips, Frankliniella occidentalis, has been found in various crops throughout the country. Although more than 20 different chemical ...insecticides are registered to control this insect pest, its outbreaks seriously damage crop yields, especially in greenhouses. This study developed a non-chemical technique to control F. occidentalis infesting hot peppers cultivated in greenhouses. The method was based on behavioral control using an alarm pheromone ("Push") to prevent the entry of the thrips into greenhouses and an aggregation pheromone ("Pull") for mass trapping inside the greenhouses. The greenhouse fences were treated with a wax formulation of the alarm pheromone and a yellow CAN trap covered with sticky material containing the aggregation pheromone was constructed and deployed inside the greenhouses. Field assay demonstrated the efficacy of the push-pull tactics by reducing thrips density in flowers of the hot peppers as well as in the monitoring traps. Especially, the enhanced mass trapping to the CAN trap compared to the conventional yellow sticky trap led to significant reduction in the thrips population. This novel push-pull technique would be applicable to effectively control F. occidentalis in field conditions.
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