(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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)670-677
Number of pages8
JournalJournal of Chemical Ecology
Volume41
Issue number7
DOIs
StatePublished - Jul 7 2015

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attractant
Pheromones
Beetles
attractants
pheromone
pheromones
beetle
Coleoptera
Bioassay
gender
North America
Biological Assay
native species
bioassay
chemistry
indigenous species
bioassays
2-hydroxyoct-4-en-3-one

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

(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 journalArticle

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. / (2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus. In: Journal of Chemical Ecology. 2015 ; Vol. 41, No. 7. pp. 670-677.
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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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