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Colonization of hosts by bark beetles is generally mediated by aggregation pheromones. Species competing for the same resource can limit interspecific interactions and maintain reproductive isolation by using different pheromones. In the southern United States, 3 sympatric species of Ips breed in pine hosts, each with a different pheromone blend. Ips avulsus (Eichhoff) uses ipsdienol and lanierone; Ips calligraphus (Germar) uses ipsdienol, cis-verbenol, and trans-verbenol; and Ips grandicollis (Eichhoff) uses ipsenol. Different species can also minimize cross-attraction by using different enantiomeric ratios of the same pheromones. Studies on the enantiomeric ratio of ipsdienol used by I. avulsus have come to contradictory conclusions in part because of geographic and seasonal variation. There is growing evidence that semiochemical context, in the form of different co-baits used in trapping experiments, may also play a role in the responses of I. avulsus to enantiomeric ratios of ipsdienol. We conducted a trapping study at 2 locations with traps baited with (+)-ipsdienol or racemic ipsdienol and co-baited with ipsenol, lanierone, or both ipsenol and lanierone. We found context-dependent effects of both lanierone and ipsenol on the response of I. avulsus to ipsdienol. We suggest that responses to different bait and co-bait combinations may have been shaped by different types of interactions such as the absence of conspecifics or a related species, or the presence of beneficial or antagonistic interspecific interactions.

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RESUMEN

In 2006, we evaluated the effects of combining lures releasing pine host kairomones (ethanol + α-pinene) with lures releasing bark beetle pheromones (ipsenol + ipsdienol) on trap catches of predators associated with bark and woodboring beetles in Florida, Georgia, Louisiana, and Virginia. Catches in traps baited with all 4 compounds were greater than those in traps baited with either binary blend for the common predators Thanasimus dubius (F.) (Coleoptera: Cleridae), Temnoscheila virescens (F.) (Coleoptera: Trogossitidae), Aulonium tuberculatum LeConte (Coleoptera: Zopheridae), and Lasconotus spp. (Coleoptera: Zopheridae). The same was true for: Enoclerus nigripes (Say) (Coleoptera: Cleridae) at 2 of 3 locations; Platysoma cylindricum (Paykull) (Coleoptera: Histeridae) at 3 of 4 locations; and Corticeus spp. (Coleoptera: Tenebrionidae) at 2 of 6 locations. In contrast, the addition of ethanol + α-pinene to traps baited with ipsenol + ipsdienol reduced catches of Platysoma attenuatum LeConte (Coleoptera: Histeridae) at 2 of 4 locations.

RESUMEN

Chemical signals are important mediators of interactions within forest ecosystems. In insects, pheromone signals mediate intraspecific interactions such as mate location and acceptance. The evolution of pheromones in insects has been mostly studied from a theoretical perspective in the Lepidoptera. With this study, we aimed to broaden our understanding of pheromone communication in bark beetles. We first demonstrated that the enantiomeric ratios of ipsdienol produced by male I. avulsus, showed little variation. Subsequently, with field trapping trials we characterized the influence of the enantiomeric ratio of ipsdienol (pheromone component of I. avulsus) on I. avulsus captures and observed a great amount of variation in the receiver preference function. Most importantly, we demonstrated that responding individuals responded indiscriminately to all the enantiomeric ratios produced by the emitting individuals. These observations are consistent with the asymmetric tracking model which postulates that if the limiting sex is the emitting sex, responding individuals should not discriminate between emitted ratios. Consequently, responding individuals do not constrain the evolution of the signal. Our data suggest that, in I. avulsus, the composition of the aggregation pheromone signal might be more responsive to external selection forces, such as predation and metabolic constraints, as suggested by the asymmetric tracking model.

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Herein I present a review on the synthesis of ipsenol and ipsdienol, two aggregation pheromones of bark beetles, isolated from different species of genus Ips, and serious pests of conifer forests. I have covered the literature for around fifty years, since 1968 to 2020. This account has been divided in different sections and sub-sections, including a general and brief outlook on their isolation, structure and biological activity, to continue with the reported synthesis of racemic ipsenol and ipsdienol, including my own contribution to topic, and the presentation of reports describing the synthesis of enantiomerically pure ipsenol and ipsdienol. Particular attention has been devoted to identify and highlight racemic or enantiomerically pure "isoprene synthons", and isoprenylation methods employed in the synthesis of ipsenol and ipsdienol, of general interest for related terpene derivatives synthesis.

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Ips spp. bark beetles use ipsdienol, ipsenol, ipsdienone and ipsenone as aggregation pheromone components and pheromone precursors. For Ips pini, the short-chain oxidoreductase ipsdienol dehydrogenase (IDOLDH) converts (-)-ipsdienol to ipsdienone, and thus likely plays a role in determining pheromone composition. In order to further understand the role of IDOLDH in pheromone biosynthesis, we compared IDOLDH to its nearest functionally characterized ortholog with a solved structure: human L-3-hydroxyacyl-CoA dehydrogenase type II/ amyloid-ß binding alcohol dehydrogenase (hHADH II/ABAD), and conducted functional assays of recombinant IDOLDH to determine substrate and product ranges and structural characteristics. Although IDOLDH and hHADH II/ABAD had only 35% sequence identity, their predicted tertiary structures had high identity. We found IDOLDH is a functional homo-tetramer. In addition to oxidizing (-)-ipsdienol, IDOLDH readily converted racemic ipsenol to ipsenone, and stereo-specifically reduced both ketones to their corresponding (-)-alcohols. The (+)-enantiomers were never observed as products. Assays with various substrate analogs showed IDOLDH had high substrate specificity for (-)-ipsdienol, ipsenol, ipsenone and ipsdienone, supporting that IDOLDH functions as a pheromone-biosynthetic enzyme. These results suggest that different IDOLDH orthologs and or activity levels contribute to differences in Ips spp. pheromone composition.

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