North American Species of Cerambycid Beetles in the GenusNeoclytusShare a Common Hydroxyhexanone-Hexanediol Pheromone Structural Motif

Abstract

Many species of cerambycid beetles in the subfamily Cerambycinae are known to use male-produced pheromones composed of one or a few components such as 3-hydroxyalkan-2-ones and the related 2,3-alkanediols. Here, we show that this pheromone structure is characteristic of the cerambycine genus Neoclytus Thomson, based on laboratory and field studies of 10 species and subspecies. Males of seven taxa produced pheromones composed of (R)-3-hydroxyhexan-2-one as a single component, and the synthetic pheromone attracted adults of both sexes in field bioassays, including the eastern North American taxa Neoclytus caprea (Say), Neoclytus mucronatus mucronatus (F.), and Neoclytus scutellaris (Olivier), and the western taxa Neoclytus conjunctus (LeConte), Neoclytus irroratus (LeConte), and Neoclytus modestus modestus Fall. Males of the eastern Neoclytus acuminatus acuminatus (F.) and the western Neoclytus tenuiscriptus Fall produced (2S,3S)-2,3-hexanediol as their dominant or sole pheromone component. Preliminary data also revealed that males of the western Neoclytus balteatus LeConte produced a blend of (R)-3-hydroxyhexan-2-one and (2S,3S)-2,3-hexanediol but also (2S,3S)-2,3-octanediol as a minor component. The fact that the hydroxyketone-hexanediol structural motif is consistent among these North American species provides further evidence of the high degree of conservation of pheromone structures among species in the subfamily Cerambycinae.

Next-generation sequencing to investigate existing and new insect associations with phytopathogenic fungal propagules

“…The first semiochemical combination (C6C8) contained ethanol, as well as aggregation pheromones of some longhorned beetles in the Cerambycinae subfamily [54]. The second semiochemical combination (UHR_E_AP) contained ethanol and alpha-pinene, which are attractive to a wide range of bark and wood-boring insects [49,55,56].…”

“…Supplementary C6C8 = Combination of three semiochemicals (racemic 3-hydroxyhexan-2-one, racemic 3-hydroxyoctan-2-one, and UHR ethanol). The first two chemicals are aggregation pheromones of some longhorned beetles in the Cerambycinae subfamily [54] but, the addition of UHR ethanol increases attraction to other wood-boring insects.…”

“…Semiochemicals are communication chemicals to induce inter-or intraspecific interactions between organisms (e.g., decaying trees produce a kairomone that attracts bark beetles) [53]. They have been extensively studied for their ability to attract specific insects [47,[54][55][56][57][58][59][60], especially for monitoring particular groups of beetles and the microorganisms associated with them. With the advances associated with next-generation sequencing (NGS), scientists have used the power of metagenomics for the diagnosis of phytoviruses [42], fungi, and oomycetes [61], and the detection of exotic fungi on asymptomatic live plant material imported into Canada [62].…”

Efficacy of semiochemical-baited traps for detection of Scolytinae species (Coleoptera: Curculionidae) in the Russian Far East

“…In the last decade or so, long-distance sex and aggregation pheromones have been identifi ed in several species of longhorn beetles in the subfamilies Cerambycinae (Fettköther et al, 1995;Allison et al, 2004;Lacey et al, 2004Lacey et al, , 2007Mitchell et al, 2015, Ray et al, 2015, Spondylidinae (Silk et al, 2007;Sweeney et al, 2010), Prioninae (Cervantes et al, 2006), Lamiinae (Fonseca et al, 2010, Pajares et al, 2010Teale et al, 2011;Allison et al, 2012;Fierke et al, 2012) and Lepturinae (Ray et al, 2011, and use of racemic blends as well as pure enantiomers in traps has signifi cantly increased the detection rate of several species of cerambycids Mitchell et al, 2011;Hanks & Miller, 2012Wong et al, 2012;Sweeney et al, 2014;Ray et al, 2015;Miller et al, 2015b). As a result, racemic blends of the cerambycinae pheromones, 3-hydroxyhexan-2-one and 3-hydroxyoctan-2-one, have been used in operational surveillance programs by the Canadian Food Inspection Agency from .…”

Aggregation-Sex Pheromones and Likely Pheromones of 11 South American Cerambycid Beetles, and Partitioning of Pheromone Channels

“…Accumulating evidence suggests that there is considerable parsimony among cerambycid species with regard to pheromone biosynthesis and use, with closely related species often sharing pheromone components, or even producing pheromones of apparently identical composition (e.g., Hanks et al, 2007;Mitchell et al, 2011Mitchell et al, , 2013Ray et al, 2012Ray et al, , 2015Hanks and Millar, 2013). For example, ∼60 species within the subfamily Cerambycinae have been shown to emit and are attracted to pheromone compounds with 6, 8, or 10 carbon chains, with carbonyl or hydroxyl groups on carbons 2 and/or 3 (listed in Table S1 of Hanks and Millar, 2016).…”