(2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus

Abstract

We report the identification of a novel pheromone structure from males of the cerambycid beetle Tylonotus bimaculatus Haldeman (Cerambycinae: Hesperophanini), a species native to eastern North America. Volatiles collected from adult males contained (2S,4E)-2-hydroxyoct-4-en-3-one (71%), (3R,4E)-3-hydroxyoct-4-en-2-one (15%), (E)-4-octen-2,3-dione (13%), and 2,3-octanedione (1.5%). Four independent field bioassays with synthetic compounds confirmed that adults of both sexes were attracted by the racemate of the major component, (E)-2-hydroxyoct-4-en-3-one. No other cerambycid species were attracted in significant numbers. Attraction of both sexes is consistent with the male-produced pheromones of many other species in the subfamily Cerambycinae, but T. bimaculatus is unusual in having a pheromone chemistry that is so far unique among species in that subfamily.

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

“…The pheromone components of most North American cerambycines studied to date have been identified as six carbon hydroxyketones and alkanediols. Exceptions include (E)-2-hydroxyoct-4-en-3-one and related compounds, which are produced by males of the eastern species Tylonotus bimaculatus Haldeman (Zou et al 2015) and (Z)-3-decenyl (E)-2-hexenoate produced by males of the western Rosalia funebris Motschulsky (Ray et al 2009a). Another apparent exception is the cerambycine Megacyllene caryae (Gahan), males of which produce isomers of 2,3-hexanediols as minor components but also at least eight other chemicals that are better known as floral and wood volatiles (Lacey et al 2008;R.F.M.…”

Isolation and identification of a male-produced aggregation-sex pheromone for the velvet longhorned beetle, Trichoferus campestris

“…Our results also show how knowledge of the pheromone chemistry and biology of related species can expedite the identification of novel pheromone structures. In particular, from the taxonomic placement of VLB in the subfamily Cerambycinae and the tribe Hesperophanini, we hypothesized that pheromones would likely be produced by adult males and might conform to the well-known hydroxyketone or 2,3-alkanediol structural motifs, consistent with many other species in the same subfamily and tribe 37,43 . The presence of male-specific prothoracic pores and glands was also consistent with a likely male-produced pheromone 19,37 .…”

Effect of semiochemicals and trap height on catch of Neocerambyx raddei in Jilin province, China

“…None of the pheromones identified as attractive to other longhorned beetles that we tested, including those known to be emitted by several species of Cerambycinae (e.g., hydroxyketones, hexanediols), were attractive to N. raddei. However, the pheromone compounds that we tested by no means exhausted the many types of pheromone structures recently discovered for species of Cerambycinae, e.g., (2S,4E)-2-hydroxy-4-octen-3-one (Zou et al, 2015), 1-(1H-pyrrol-2-yl)-1,2-propanedione , and 10-methydodecanal (Silva et al, 2016). Ginzel & Hanks (2005) hypothesized that mate location in species of Cerambycinae involved three sequential behavioural stages: both sexes are attracted to hosts by plant volatiles, males then attract females over shorter distances with pheromones, and finally males recognize females by contact pheromones in the female's epicuticular wax layer.…”