(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 › peer-review

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

Keywords

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

ASJC Scopus subject areas

Ecology, Evolution, Behavior and Systematics
Biochemistry

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(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 › peer-review

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title = "(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.",

keywords = "3-hydroxy-4-octen-2-one, Aggregation pheromone, Cerambycinae, Longhorned beetle, Semiochemical",

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

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AU - Millar, Jocelyn G.

AU - Blackwood, J. Scott

AU - Van Duzor, Ryan

AU - Hanks, Lawrence M.

AU - Mongold-Diers, Judith A.

AU - Wong, Joseph C.H.

AU - Ray, Ann M.

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AB - 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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KW - Longhorned beetle

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

Abstract

Keywords

ASJC Scopus subject areas

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