Ketone components in the contact sex pheromone of the white‐spotted longicorn beetle, Anoplophora malasiaca, and pheromonal activity of synthetic ketones

Abstract

Two active fractions were found during the isolation of contact sex pheromone of female elytra of the white‐spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae), in addition to fraction of hydrocarbons that had previously been identified. One fraction was essential to evoke a series of precopulatory behaviors of males toward a glass dummy when coated together with the hydrocarbon blend. The other fraction enhanced this activity when added to the mixture. From the latter synergistic fraction, we isolated five novel compounds and identified them as 10‐heptacosanone, (Z)‐18‐heptacosen‐10‐one, (18Z,21Z)‐heptacosa‐18,21‐dien‐10‐one, (18Z,21Z,24Z)‐heptacosa‐18,21,24‐trien‐10‐one, and 12‐heptacosanone by GC‐MS and NMR analyses. A blend of four of these synthetic ketones, without 12‐heptacosanone, in the ratio and concentration found in female elytra extract (250 : 400 : 1000 : 180 ng FE−1) showed greater synergistic effect than the natural fraction containing the ketones. This effect was canceled out by further addition of 12‐heptacosanone (100 ng FE−1), which was still comparable to the effect of the natural ketone fraction.

Host plant chemicals serve intraspecific communication in the white-spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae)

“…In subfamily Lamiinae, female attraction by males was observed in Monochamus alternatus (Fauziah et al, 1987) and male-specific compounds were identified in Anoplophora glabripennis (Zhang et al, 2002). However, we have no behavioral evidence for female-or male-specific sex attractant pheromone released by females or males in Psacothea hilaris (Pascoe) (Fukaya and Honda, 1992, 1995, 1996aFukaya et al, 1996Fukaya et al, , 1997Fukaya, 2004) and A. malasiaca (Fukaya et al, 1999(Fukaya et al, , 2000(Fukaya et al, , 2004a(Fukaya et al, , b, 2005aAkino et al, 2001;Yasui et al, 2003). In a previous study, we reported that the male elytra extracts facilitate female mate location before contact (Fukaya et al, 2005b).…”

“…The white-spotted longicorn beetle Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae: Lamiinae) is a serious pest of citrus, and mating behavior has been intensively studied (Fukaya et al, 1999(Fukaya et al, , 2000(Fukaya et al, , 2004a(Fukaya et al, , b, 2005aAkino et al, 2001;Yasui et al, 2003). When a male encounters a female, he holds and mounts her back and then usually attempts to bend his abdominal tip towards her abdomen (Fukaya et al, 1999).…”

“…When a male encounters a female, he holds and mounts her back and then usually attempts to bend his abdominal tip towards her abdomen (Fukaya et al, 1999). The male frequently touches the back of the female for recep-tion of a contact sex pheromone that includes a number of hydrocarbons, ketones and lactones (Fukaya et al, 2000;Yasui et al, 2003Yasui et al, , 2007. However, the males can also orientate toward a female body, as well as a glass-rod model treated with female extract, even before contact through antennae and/or tarsi (Fukaya et al, 2004a).…”

Recent Advances in Sex Pheromone Studies on the White-Spotted Longicorn Beetle, Anoplophora malasiaca

“…Our finding in A. malasiaca, that the blending of cuticular hydrocarbons and polar components is essential to reveal the pheromonal activity had not been reported in other longicorn beetles (our study is the only one in the world to provide an analysis of the contact pheromone in the longicorn beetle). We detected 2 or more groups of pheromonally active components, and the identification of their chemical structure is in progress (Recently 4 ketone compounds have been identified: Yasui et al, 2003) 23 .…”

Female orientation to the male in the white-spotted longicorn beetle, Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae) by visual and olfactory cues

“…The female white-spotted longicorn beetle Anoplophora malasiaca (Thomson) (Coleoptera: Cerambycidae, Lamiinae) produces a sex pheromone on her body and evokes sequential copulating behaviors in males through direct contact with antennae, palpi, or tarsi (Fukaya et al, 1999(Fukaya et al, , 2000Akino et al, 2001;Fukaya, 2003;Yasui et al, 2003). Recently, we reported that a female volatile chemical mediates short distance mate location in A. malasiaca by males, and that visual stimuli in association with female substances are also involved (Fukaya et al, 2004).…”