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

Yunfan Zou; Jocelyn G. Millar; J. Scott Blackwood; Ryan Van Duzor; Lawrence M. Hanks; Judith A. Mongold-Diers; Joseph C.H. Wong; Ann M. Ray

doi:10.1007/s10886-015-0603-9

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

Yunfan Zou, Jocelyn G. Millar, J. Scott Blackwood, Ryan Van Duzor, Lawrence M. Hanks, Judith A. Mongold-Diers, Joseph C.H. Wong, Ann M. Ray

Entomology

Research output: Contribution to journal › Article

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.

Original language	English (US)
Pages (from-to)	670-677
Number of pages	8
Journal	Journal of Chemical Ecology
Volume	41
Issue number	7
DOIs	https://doi.org/10.1007/s10886-015-0603-9
State	Published - Jul 7 2015

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Keywords

3-hydroxy-4-octen-2-one
Aggregation pheromone
Cerambycinae
Longhorned beetle
Semiochemical

ASJC Scopus subject areas

Ecology, Evolution, Behavior and Systematics
Biochemistry

Cite this

Zou, Y., Millar, J. G., Blackwood, J. S., Van Duzor, R., Hanks, L. M., Mongold-Diers, J. A., Wong, J. C. H., & Ray, A. M. (2015). (2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus. Journal of Chemical Ecology, 41(7), 670-677. https://doi.org/10.1007/s10886-015-0603-9

(2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus. / Zou, Yunfan; Millar, Jocelyn G.; Blackwood, J. Scott; Van Duzor, Ryan; Hanks, Lawrence M.; Mongold-Diers, Judith A.; Wong, Joseph C.H.; Ray, Ann M.

In: Journal of Chemical Ecology, Vol. 41, No. 7, 07.07.2015, p. 670-677.

Research output: Contribution to journal › Article

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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.",

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10.1007/s10886-015-0603-9